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Grossman PPAP Database

Polycyclic polyprenylated acylphloroglucinols (bicyclo[3.3.1]nonane derivatives).
Compiled by Prof. Robert B. Grossman, University of Kentucky.

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Showing 1554 compounds in 452 structures.  |  Alphabetical index  |  Footnotes  |  All references

Structure and Index R and X group(s) Common Name Source [a] [α]D (°) [b] Reference(s)
Structure 1: prolifenone B, hyperevolutin A, olympiforin B and others — A, bicyclononanes, exo
1
1.1 R1 = i-Pr
R2 = H
R3 = H
R4 = prenyl
R5 = geranyl		 prolifenone B H. prolificum[a] −0.58 (1.30, m)[b] G. E. Henry 2006
1.2 R1 = i-Pr
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyperevolutin A H. revolutum[a] Vahl +84.4 (0.5, m)[b] L. A. Decosterd 1989
1.3 R1 = i-Pr
R2 = prenyl
R3 = H
R4 = prenyl
R5 = prenyl		 olympiforin B[c] H. olympicum[a] L. +9.8 (0.116, m)[b] Y. Ilieva 2023
1.4 R1 = i-Pr
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 hyperibine J, a.k.a. adhyperfirin, a.k.a. hyperpolyphyllirin H. maculatum[a] Crantz, H. perforatum, H. polyphyllum, H. triquetrifolium[a] +7.2 (1, m)[b], OMe: +7 (0.10, m)[b] E. C. Tatsis 2007, A. Porzel 2014, K. P. Mitsopoulou 2015, P. T. Nedialkov 2015
1.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 secohyperforin H. perforatum[a] NR A. Charchoglyan 2007, B. A. Sparling 2015
1.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyperforin[c] H. perforatum, H. attenuatum[a] +41 (5, e)[b] A. I. Gurevich 1971 (includes translation), N. S. Bystrov 1975, N. S. Bystrov 1978, N. S. Bystrov 1978 (translation), D. Li 2015a
1.7 R1 = i-Pr
R2 = prenyl
R3 = CH2CH2CMe2OH
R4 = prenyl
R5 = H		 garcinielliptone A G. subelliptica[a] −33 (0.6)[b] J.-R. Weng 2003a
1.8 R1 = i-Bu
R2 = H
R3 = geranyl
R4 = prenyl
R5 = H		 garcicosin G. verrucosa[a] −10 (0.3)[b] M. Rajaonarivelo 2016
1.9 R1 = s-Bu
R2 = H
R3 = H
R4 = prenyl
R5 = geranyl		 prolifenone A[e] H. prolificum[a] +13.3 (0.145, m)[b] G. E. Henry 2006
1.10 R1 = s-Bu
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyperevolutin B[e] H. revolutum[a] Vahl NR L. A. Decosterd 1989
1.11 R1 = (S)-s-Bu
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 olympiforin A[c] H. olympicum[a] L. +20.97 (0.102, m)[b] Y. Ilieva 2023
1.12 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 adsecohyperforin[e] H. perforatum[a] NR A. Charchoglyan 2007
1.13 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 adhyperforin[e] H. perforatum[a] NR P. Maisenbacher 1992
1.14 R1 = s-Bu
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H		 garcinielliptone D[e] G. subelliptica[a] −22 (0.1)[b] J.-R. Weng 2003a
1.15 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 nemorosone[d] Cuban propolis, C. rosea, C. grandiflora, C. insignis, C. nemorosa[a] +113 (0.1)[b]; OMe: +150 (0.8, m)[b] and +49 (1.4)[b] C. M. A. de Oliveira 1996, C. M. A. de Oliveira 1999, J. Lokvam 2000, O. Cuesta Rubio 2001a, B. A. Sparling 2015
1.16 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 bzhyperforin[c] H. forestii[a] −66 (0.2, m)[b] W.-J. Lu 2020
1.17 R1 = Ph
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 chamone I[e] C. grandiflora[a] NR J. Lokvam 2000
1.18 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 hydroxynemorosone C. nemorosa[a] OMe: +143 (0.7, m)[b] C. M. A. de Oliveira 1996, R. Ciochina 2006
1.19 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (S)-isolavandulyl[g]
R5 = H		 garcinialiptone D G. subelliptica[a] −79.1 (7.83, m)[b] L.-J. Zhang 2010
Structure 2: 7-epi-secohyperforin, no name, plukenetione D and others — A, bicyclononanes, endo
2
2.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl		 7-epi-secohyperforin[d] H. sampsonii[a] NR L. Ernst 2024
2.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl		 no common name H. sampsonii[a] NR L. Ernst 2024
2.3 R1 = Ph
R2 = prenyl
R3 = prenyl		 plukenetione D, a.k.a. 7-epi-nemorosone, and tautomer plukenetione E[d] C. nemorosa, C. plukenetii, H. sampsonii[a] OAc: +34.5 (0.03)[b], −37.6 (0.1)[b]; OMe: +10.7 (3.1)[b] G. E. Henry 1999, C. M. A. de Oliveira 1999, R. B. Grossman 2000, X.-W. Yang 2017a, L. Ernst 2024
2.4 R1 = Ph
R2 = prenyl
R3 = (E)-4-acetoxyprenyl		 insignone C. insignis[a] OMe: +92.7 (1.6)[b] A. L. M. Porto 2000
2.5 R1 = Ph
R2 = geranyl
R3 = prenyl		 nemosampsone[d] H. sampsonii[a] NR L. Ernst 2024
Structure 3: hyperfirin — A, bicyclononanes, noC7
3
3.1 hyperfirin H. perforatum[a] NR E. C. Tatsis 2007
Structure 4: hyphenone A, hypseudone C, hypseudone D and others — A, bicyclononanes, exo
4
4.1 R1 = i-Pr
R2 = CH2CH2COMe
R3 = prenyl		 hyphenone A H. henryi[a] +13 (0.22, m)[b] N.-N. Jiang 2019
4.2 R1 = i-Pr
R2 = (E)-CH2CH=CMeCHO
R3 = prenyl		 hypseudone C[c] H. pseudohenryi[a] +25.5 (0.157, m)[b] N.-N. Jiang 2025
4.3 R1 = i-Pr
R2 = (E)-CH2CH=CMeCH(OMe)2
R3 = prenyl		 hypseudone D[c] H. pseudohenryi[a] +31.2 (0.078, m)[b] N.-N. Jiang 2025
4.4 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH2CH=CMeCHO		 hyperkouytone B[c] H. kouytchense[a] +41.2 (0.23, m)[b] H.-Y. Lou 2024
4.5 R1 = s-Bu
R2 = (E)-CH2CH=CMeCHO
R3 = prenyl		 hypseudone B[c][e] H. pseudohenryi[a] +34.9 (0.094, m)[b] N.-N. Jiang 2025
Structure 5: dorstenpictanone — A, bicyclononanes, exo
5
5.1 dorstenpictanone Dorstenia picta NR H. Hussain 2011
Structure 6: hyperkouytone C — A, bicyclononanes, exo
6
6.1 hyperkouytone C[c] H. kouytchense[a] −96.0 (0.5, m)[b] H.-Y. Lou 2024
Structure 7: deoxyfurohyperforin A, furohyperforin A, mixture of epimers, hyperwilsone B and others — A, bicyclononanes, exo
7
7.1 R1 = i-Pr
R2 = prenyl
X1 = H
X2 = H		 deoxyfurohyperforin A H. perforatum[a] +42 (0.018, mc)[b] V. Vajs 2003
7.2 R1 = i-Pr
R2 = prenyl
X1 = OH/H
X2 = H/OH		 furohyperforin A, mixture of epimers H. perforatum[a] NR S. Trifunović 1998, V. Vajs 2003
7.3 R1 = i-Pr
R2 = prenyl
X1 = OMe
X2 = H		 hyperwilsone B[c] H. wilsonii[a] +114.1 (0.2, acn)[b] Y. Duan 2021c
7.4 R1 = i-Pr
R2 = prenyl
X1 = H
X2 = OMe		 hyperwilsone A[c] H. wilsonii[a] +25.7 (0.2, acn)[b] Y. Duan 2021c
7.5 R1 = (S)-s-Bu
R2 = prenyl
X1 = H
X2 = OMe		 lancasteroid F[c] H. lancasteri[a] +5.8 (0.3, m)[b] J.-Q. You 2025
7.6 R1 = (S)-s-Bu
R2 = prenyl
X1 = OMe
X2 = H		 lancasteroid E[c] H. lancasteri[a] +115.7 (0.3, m)[b] J.-Q. You 2025
7.7 R1 = Ph
R2 = H
X1 = H
X2 = H		 hyperscabrone B[c] H. scabrum[a] −39 (0.1, m)[b] W. Gao 2016a
7.8 R1 = Ph
R2 = H
X1 = H
X2 = OMe		 lancasteroid G[c] H. lancasteri[a] −62.1 (0.3, m)[b] J.-Q. You 2025
7.9 R1 = Ph
R2 = H
X1 = OMe
X2 = H		 lancasteroid H[c] H. lancasteri[a] +1.7 (0.3, m)[b] J.-Q. You 2025
7.10 R1 = Ph
R2 = prenyl
X1 = H
X2 = H		 hyphenrone X[c] H. henryi[a] H. Lév & Vaniot −23 (0.18, m)[b] Y. Liao 2016
7.11 R1 = Ph
R2 = prenyl
X1 = OH
X2 = H		 hypulatone F[c] H. patulum[a] –23 (0.1, m)[b] Y.-F. Qiu 2026
7.12 R1 = Ph
R2 = prenyl
X1 = OMe
X2 = H		 hypseudohenrin F[c] H. pseudohenryi[a] +22.2 (0.86, m)[b] H. Sun 2021b
7.13 R1 = Ph
R2 = prenyl
X1 = H
X2 = OMe		 hypseudohenrin G[c] H. pseudohenryi[a] −14.0 (0.57, m)[b] H. Sun 2021b
Structure 8: hyperforatin F, garsubellin A, hyperhimatin G and others — A, bicyclononanes, exo
8
8.1 R1 = Me
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatin F[c] H. perforatum[a] +52 (0.4, m)[b] Y. Guo 2017
8.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 garsubellin A G. subelliptica[a] −21 (e, 1.1)[b] Y. Fukuyama 1997, Y. Fukuyama 1998
8.3 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CH(OH)CMe2OH
R4 = H
X = OH		 hyperhimatin G[c] H. himalaicum[a] +48.4 (0.5, m)[b] H. Cheng 2022b
8.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hypercohin G H. cohaerens[a] +42.4 (0.20, m)[b] X. Liu 2013a
8.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 furohyperforin H. perforatum, H. attenuatum[a] +62.4 (0.9)[b], +81.9 (0.9, m)[b], +68 (0.2)[b] S. Trifunović 1998, L. Verotta 1999, D. Li 2015a
8.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OOH		 33-deoxy-33-hydroperoxyfurohyperforin H. perforatum[a] +75 (1.2)[b] L. Verotta 2000
8.7 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = acetonyl		 hyperpatuone J[c] H. patulum[a] −15.00 (0.3, m)[b] F. Zhang 2026
8.8 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
X = OH		 scabrumione F, a.k.a. hyperioxide F[c] H. scabrum, H. perforatum[a] +38.7 (0.04, m)[b], +7.2 (0.1, m)[b] Z.-B. Zhou 2022a, X.-G. Pan 2025
8.9 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH
X = OH		 hyperkouytone H, a.k.a. hyperioxide E[c] H. kouytchense, H. perforatum[a] +62.7 (0.3, m)[b], +8.1 (0.1, m)[b] H.-Y. Lou 2024, X.-G. Pan 2025
8.10 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-2,3-epoxy-3-methylbutyl
X = OH		 hyperkouytone J H. kouytchense[a] +33.92 (0.25, m)[b] H.-Y. Lou 2024
8.11 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CHOHCMe=CH2
X = OH		 hyperforatin E[c] H. perforatum[a] +66 (0.3, m)[b] Y. Guo 2017
8.12 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe=CH2
X = OH		 32-epi-hyperforatin E[c] H. perforatum[a] +81 (0.3, m)[b] Y. Guo 2017
8.13 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = CH2C(=O)CHMe2
X = OH		 hyperforatin G[c] H. perforatum[a] +48 (0.6, m)[b] Y. Guo 2017
8.14 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = CH2C(=O)CMe=CH2
X = OH		 hyperioxide D[c] H. perforatum[a] +15.3 (0.1, m)[b] X.-G. Pan 2025
8.15 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CHOHCMe2OH
X = OH		 17R,18-dihydroxyfurohyperforin H. perforatum, H. scabrum[a] +26.6 (0.25, m)[b] R.-D. Liu 2014, H. Bridi 2018, Y. C. Xiao 2018
8.16 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OH
X = OH		 attenuatumione G[c] H. attenuatum[a] +40.5 (0.19)[b] Z.-B. Zhou 2016a
8.17 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CHOHCMe2OMe
X = OH		 hyperfol G, a.k.a. curvisepalumione A[c] H. curvisepalum, H. perforatum[a] +117.0 (0.3, m)[b] H. Lou 2020b, Z.-B. Zhou 2022b
8.18 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OMe
X = OH		 curvisepalumione B[c] H. curvisepalum[a] +78.8 (0.17, m)[b] Z.-B. Zhou 2022b
8.19 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OEt
X = OH		 hyperioxide C[c] H. perforatum[a] +6.6 (0.1, m)[b] X.-G. Pan 2025
8.20 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe=CH2
R4 = prenyl
X = OH		 hyperforatin Q[c] H. perforatum[a] +87.7 (0.6, m)[b] Y. Guo 2019b
8.21 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X = OH		 hyperformitin I[c] H. perforatum[a] +59 (0.2, m)[b] Y. Guo 2021a
8.22 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OOH
R4 = prenyl
X = OH		 hyperkouytone G H. kouytchense[a] +47.38 (0.3, m)[b] H.-Y. Lou 2024
8.23 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = prenyl
X = OH		 hyperioxide B[c] H. perforatum[a] +60.0 (0.02, m)[b] X.-G. Pan 2025
8.24 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl
X = OH		 no common name H. himalaicum[a] +88.4 (0.2, m)[b] G.-H. Liu 2025
8.25 R1 = i-Pr
R2 = (E)-CH2CH=C(Me)CHO
R3 = prenyl
R4 = prenyl
X = OH		 hyperhookerione E[c] H. hookerianum[a] +140.2 (0.5, m)[b] Z. Guo 2025b
8.26 R1 = i-Pr
R2 = (R)-CH2CHOHCMe=CH2
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatin S[c] H. perforatum[a] +62.2 (0.6, m)[b] Y. Guo 2019b
8.27 R1 = i-Pr
R2 = (S)-CH2CHOHCMe=CH2
R3 = prenyl
R4 = prenyl
X = OH		 hypericumoxide J H. scabrum[a] +3.4 (0.06, m)[b] R. Liu 2017, Y. Guo 2019b
8.28 R1 = i-Pr
R2 = CH2C(=O)CHMe2
R3 = prenyl
R4 = prenyl
X = OH		 hypericum E[c] H. lagarocladum +54.9 (0.1, acn)[b] S. Du 2026
8.29 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
R4 = prenyl
X = OH		 hyperfol F[c] H. perforatum[a] +31.35 (0.17, m)[b] H. Lou 2020b
8.30 R1 = i-Pr
R2 = (E)-CH=CHCMe2OOH
R3 = prenyl
R4 = prenyl
X = OH		 hyperkouytone I H. kouytchense[a] +28.38 (0.17, m)[b] H.-Y. Lou 2024
8.31 R1 = i-Pr
(18R,39R)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatone B[c] H. perforatum[a] +53.0 (0.5, m)[b] Y. Guo 2018
8.32 R1 = i-Pr
(18R,39S)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin D H. cohaerens[a] +81.5 (0.10, m)[b] X. Liu 2013a
8.33 R1 = i-Pr
(18S,39R)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin B[c] H. cohaerens[a] +30.8 (0.15, m)[b] X. Liu 2013a
8.34 R1 = i-Pr
(18S,39S)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatone A[c] (one of two by that name) H. perforatum[a] +31.8 (0.3, m)[b] Y. Guo 2018, W.-Y. Liu 2025a
8.35 R1 = i-Pr
(18S,39R)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OOH		 hyperforatone D[c] H. perforatum[a] +26.1 (0.4, m)[b] Y. Guo 2018
8.36 R1 = i-Pr
(27R,37R)-R2 = hypericumoxideSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hypericumoxide K H. scabrum[a] +65.2 (0.07, m)[b] R. Liu 2017
8.37 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 garsubellin B[d][e] G. subelliptica[a] −36 (0.6, e)[b] Y. Fukuyama 1998, Y. Ma 2022b
8.38 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 hyperacmosin S[c][e] (enantiomer) G. acmosepalum[a] +32.3 (0.52, e)[b]; +92.3 (0.05, m)[b] Y. Ma 2022b
8.39 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hyperforcinol J, a.k.a. hyperiforin A[c][e] H. forrestii[a] +70 (0.4, m)[b], +77.3 (0.1, m)[b] W.-J. Lu 2021, J.-F. Zong 2021
8.40 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 furoadhyperforin[e] H. perforatum[a] NR S. Vugdelija 2000
8.41 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OOH		 hyperichoisin A[e] H. choisianum[a] +45.78 (0.075, m)[b] H.-B. Zhang 2021
8.42 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = acetonyl		 hyperpatuone K[c][e] H. patulum[a] −35 (0.3, m)[b] F. Zhang 2026
8.43 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe=CH2
X = OH		 hyperforatin T[c][e] H. perforatum[a] +45.5 (0.2, m)[b] Y. Guo 2019b
8.44 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe=CH2
X = OH		 hyperforatin U[c][e] H. perforatum[a] +57.3 (0.3, m)[b] Y. Guo 2019b
8.45 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OH
X = OH		 uralione P[c][e] H. uralum[a] +27.2 (0.1, m)[b] X. Li 2017
8.46 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OMe
X = OH		 scabrumione G[c][e] H. scabrum[a] +5.7 (0.1, m)[b] H. Zeng 2026
8.47 R1 = s-Bu
R2 = prenyl
R3 = (R)-CH2CH(OH)CMe=CH2
R4 = prenyl
X = OH		 hyperforatin R[c][e] H. perforatum[a] +36.0 (0.3, m)[b] Y. Guo 2019b
8.48 R1 = s-Bu
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = H
X = OH		 hyperhimatin H[c][e] H. himalaicum[a] +44.0 (0.5, m)[b] H. Cheng 2022b
8.49 R1 = s-Bu
R2 = CH(Pr)CH2CO2H
R3 = prenyl
R4 = H
X = OH		 sundaicumone B[e] Calophyllum sundaicum +48 (0.1, e)[b] S. Cao 2006
8.50 R1 = s-Bu
R2 = CH(Pr)CH2CO2H
R3 = CH2CHOHCMe2OH
R4 = H
X = OH		 sundaicumone A[e] Calophyllum sundaicum +52 (0.2, e)[b] S. Cao 2006
8.51 R1 = s-Bu
(18R,39S)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hypericumoxide L[e] H. scabrum[a] +28.6 (0.02, m)[b] R. Liu 2017
8.52 R1 = s-Bu
(18S,39R)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatone C[c][e] H. perforatum[a] +21.5 (0.5, m)[b] Y. Guo 2018
8.53 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = H		 hypermacone C[d] H. maclarenii[a] –78.08 (0.094, m)[b] W.-L. Meng 2026
8.54 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 hyperibone G H. scabrum[a] −29.3 (0.9)[b] M. Matsuhisa 2002
8.55 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 propolone D (enantiomer) Cuban propolis +48.5 (0.7)[b] I. M. Hernandez 2005
8.56 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hypercohin H H. cohaerens[a] −19.0 (0.11, m)[b] X. Liu 2013a
8.57 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 uraloidin A, a.k.a. uralodin A H. henryi [a]subsp. uraloides −55.0 (0.10, m)[b] N. Guo 2008, X.-Q. Chen 2010
8.58 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OOH		 hyperforcinol H, a.k.a. hyperiforin B[c] H. forrestii[a] −20 (0.1, m)[b], −7.3 (0.1, m)[b] W.-J. Lu 2021, J.-F. Zong 2021
8.59 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe=CH2
X = OH		 hyperpatulone B[c] H. patulum[a] +41.7 (1.0, m)[b] Z.-N. Wu 2019
8.60 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe=CH2
X = OH		 hyperpatulone A[c] H. patulum[a] +39.6 (1.0, m)[b] Z.-N. Wu 2019
8.61 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe2OH
X = OH		 hyperpatulone D[c] (one of two by that name) H. patulum[a] +51.8 (1.0, m)[b] Z.-N. Wu 2019
8.62 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OH
X = OH		 hyperpatulone C[c] (one of two by that name) H. patulum[a] +56.6 (1.0)[b] Z.-N. Wu 2019
8.63 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCHO
X = OH		 hyperpatuone L[c] H. patulum[a] +11.67 (0.3, m)[b] F. Zhang 2026
8.64 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = (E)-CH=CHCMe2OH
X = OH		 kiiacylphnol F[c] H. przewalskii[a] Maxim −12 (0.3, m)[b] Y. Duan 2022a
8.65 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = geranyl
X = OH		 kiiacylphnol E[c] H. przewalskii[a] Maxim +2 (0.2, m)[b] Y. Duan 2022a
8.66 R1 = Ph
R2 = prenyl
R3 = geranyl
R4 = H
X = OOH		 trijapin E Triadenum japonicum −150 (0.2, m)[b] A. Oya 2015
8.67 R1 = Ph
R2 = CH2CHOHCMe=CH2
R3 = prenyl
R4 = H
X = OH		 hyperibone D[e] H. scabrum[a] −61.9 (0.7)[b] M. Matsuhisa 2002
8.68 R1 = Ph
(18S,39R)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin C H. cohaerens[a] −43.6 (0.10, m)[b] X. Liu 2013a
8.69 R1 = Ph
R2 = CH2COCHMe2
R3 = prenyl
R4 = prenyl
X = OH		 kiiacylphnol D[c] H. przewalskii[a] Maxim −9 (0.2, m)[b] Y. Duan 2022a
Structure 9: hypercohin E, garcinielliptone C, hyperhimatin F and others — A, bicyclononanes, exo
9
9.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin E H. cohaerens[a] +17.9 (0.10, m)[b] X. Liu 2013a
9.2 R1 = i-Pr
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = H
X = OH		 garcinielliptone C G. subelliptica[a] −40 (0.2)[b] J.-R. Weng 2003a
9.3 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = H
X = OH		 hyperhimatin F[c] H. himalaicum[a] −14.0 (0.5, m)[b]; H. Cheng 2022b
9.4 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin F[e] H. cohaerens[a] +18.6 (0.15, m)[b] X. Liu 2013a
9.5 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 hyperscabrone M[c] H. scabrum[a] −29.0 (0.1, m)[b] W. Gao 2016a
9.6 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OOH		 hyperscabrone A[c] H. scabrum[a] −37 (0.1, m)[b] W. Gao 2016a
9.7 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 uralione E H. uralum[a] −30 (0.2)[b] Z.-B. Zhou 2016b
9.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CHOHCMe2OH
X = OH		 uralione Q[c] H. uralum[a] −23.4 (0.1, m)[b] X. Li 2017
9.9 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OH
X = OH		 uralione R[c] H. uralum[a] −32.0 (0.1, m)[b] X. Li 2017
Structure 10: hypseudohenrin L — A, bicyclononanes, exo
10
10.1 hypseudohenrin L[c] H. pseudohenryi[a] +22.4 (0.71, m)[b] Y.-h. Ma 2022
Structure 11: hyperacmosin J, hyperhimatin J, hyperioxide A and others — A, bicyclononanes, endo
11
11.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 hyperacmosin J[n] H. acmosepalum[a] −122 (0.18, m)[b] X. Wang 2020b
11.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = H		 hyperhimatin J[c] H. himalaicum[a] +116.7 (0.5, m)[b] H. Cheng 2022b
11.3 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = prenyl		 hyperioxide A[c] H. perforatum[a] +70.0 (0.02, m)[b] X.-G. Pan 2025
11.4 R1 = i-Pr
R2 = prenyl
R3 = (2R)-5-oxo-2-methyltetrahydrofuran-2-yl
R4 = prenyl
R5 = H		 hyperhookerione F[d] H. hookerianum[a] −128.8 (0.5, m)[b] Z. Guo 2025b
11.5 R1 = i-Pr
R2 = prenyl
R3 = (2S)-5-oxo-2-methyltetrahydrofuran-2-yl
R4 = prenyl
R5 = H		 hyperhookerione G[d] H. hookerianum[a] −146.2 (0.5, m)[b] Z. Guo 2025b
11.6 R1 = i-Pr
R2 = prenyl
R3 = (R)-2-hydroxy-6-methyl-5-hepten-2-yl
R4 = (R)-CH2CH(OH)CMe2OH
R5 = H		 no common name H. himalaicum[a] −32.0 (0.1, m)[b] G.-H. Liu 2025
11.7 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 hyperacmosin B[c] H. acmosepalum[a] −53.0 (0.502, m)[b] J. Wang 2019, J. Wang 2022
11.8 R1 = i-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 hypercoretion F[c] H. kouytchense +85.2 (0.1, m)[b] Z. Dong 2026b
11.9 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 hypercoretion G[c][e] H. kouytchense +79.3 (0.1, m)[b] Z. Dong 2026b
11.10 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = H		 hyperhimatin L[c] H. himalaicum[a] +71.3 (0.5, m)[b] H. Cheng 2022b
11.11 R1 = Ph
R2 = prenyl
R3 = H
R4 = prenyl
R5 = H		 hypersampsone R, a.k.a. hyperattenin B[d] (one of two by the first name) H. attenuatum[a] Choisy, H. sampsonii[a] +22.0 (0.3)[b], +43.9 (0.19)[b] W.-J. Tian 2014c, D. Li 2015a
11.12 R1 = Ph
R2 = prenyl
R3 = OH
R4 = prenyl
R5 = H		 hyperattenin A[d] H. attenuatum[a] Choisy +38.3 (0.92)[b] D. Li 2015a
11.13 R1 = Ph
R2 = prenyl
R3 = OEt
R4 = prenyl
R5 = H		 hyperadditionciol B[d] H. addingtionii[a] +34 (0.05, m)[b] J. Chen 2026
11.14 R1 = Ph
R2 = prenyl
R3 = C(=O)Me
R4 = prenyl
R5 = H		 hypersampsonone I[d] H. sampsonii[a] +17.5 (1.0, m)[b] Y. Li 2023
11.15 R1 = Ph
R2 = prenyl
R3 = i-Pr
R4 = prenyl
R5 = prenyl		 hypermacone B[c] H. maclarenii[a] +8.65 (0.074, m)[b] W.-L. Meng 2026
11.16 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 sampsonione L H. sampsonii[a] +55 (0.06)[b] L.-H. Hu 2000
11.17 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = (E)-CH=CHCMe2OH
R5 = H		 hyperibone F H. scabrum[a] −31.0 (0.2)[b] M. Matsuhisa 2002, R. Ciochina 2006
11.18 R1 = Ph
R2 = prenyl
R3 = (S)-2-hydroxy-6-methyl-5-hepten-2-yl
R4 = prenyl
R5 = H		 sampsonione K H. sampsonii[a] −5.6 (1.1)[b] L.-H. Hu 2000, Z.-B. Zhou 2014
11.19 R1 = Ph
R2 = prenyl
R3 = (R)-2-hydroxy-6-methyl-5-hepten-2-yl
R4 = prenyl
R5 = H		 attenuatumione C H. attenuatum[a] +20.9 (0.15)[b] Z.-B. Zhou 2014
11.20 R1 = Ph
R2 = prenyl
R3 = (R)-2-hydroxy-6-methyl-5-hepten-2-yl
R4 = (S)-CH2CH(OH)CMe2OH
R5 = H		 no common name H. himalaicum[a] +37.3 (0.1, m)[b] G.-H. Liu 2025
11.21 R1 = Ph
R2 = prenyl
R3 = (R)-5-oxo-2-methyltetrahydrofuran-2-yl
R4 = prenyl
R5 = H		 hyperisampsin I[d] H. sampsonii[a] +42 (0.2)[b] H. Zhu 2015b
11.22 R1 = Ph
R2 = prenyl
R3 = (S)-5-oxo-2-methyltetrahydrofuran-2-yl
R4 = prenyl
R5 = H		 hyperisampsin H[d] H. sampsonii[a] +4 (0.2)[b] H. Zhu 2015b
11.23 R1 = Ph
R2 = prenyl
(3R,6S)-R3 = hyperisampsinSideChain side-chain structure
R4 = prenyl
R5 = H
X = OH		 hyperisampsin J[d] H. sampsonii[a] +21 (0.3, m)[b] H. Zhu 2015b
11.24 R1 = Ph
R2 = prenyl
(3R,6S)-R3 = hyperisampsinSideChain side-chain structure
R4 = prenyl
R5 = H
X = OOH		 hyperisampsin K[d] H. sampsonii[a] +12 (0.4)[b] H. Zhu 2015b
11.25 R1 = Ph
R2 = prenyl
(3S,6R)-R3 = hyperisampsinSideChain side-chain structure
R4 = prenyl
R5 = H
X = OH		 hyperadditionciol C[d] H. addingtonii[a] –58 (0.05, m)[b] J. Chen 2026
11.26 R1 = Ph
R2 = prenyl
(3S,6R)-R3 = hyperisampsinSideChain side-chain structure
R4 = prenyl
R5 = H
X = OOH		 hyperisampsin L[d] H. sampsonii[a] +9 (0.1, m)[b] H. Zhu 2015b
11.27 R1 = Ph
R2 = CH2CHOHCMe=CH2
R3 = CMe2OH
R4 = (E)-CH=CHCMe2OH
R5 = H		 hyperibone E[e] H. scabrum[a] −56.0 (0.2)[b] M. Matsuhisa 2002, R. Ciochina 2006
Structure 12: hyperscabin H, hyperhimatin I, hyperhimatin D and others — A, bicyclononanes, endo
12
12.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = prenyl		 hyperscabin H[d] H. scabrum[a] +21.5 (0.11, mc)[b] J. Ma 2021b
12.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = H		 hyperhimatin I[c] H. himalaicum[a] +40.2 (0.5, m)[b] H. Cheng 2022b
12.3 R1 = i-Pr
R2 = CH2CO2H
R3 = CMe2OH
R4 = prenyl
R5 = H		 hyperhimatin D[c] H. himalaicum[a] +6.2 (0.5, m)[b] H. Cheng 2022b
12.4 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 hyperacmosin A[c] H. acmosepalum[a] +87.8 (0.337, m)[b] J. Wang 2019, J. Wang 2022
12.5 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = prenyl		 hyperscabin I[d][e] H. scabrum[a] +23.1 (0.10, mc)[b] J. Ma 2021b
12.6 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = H		 hyperhimatin K[c][e] H. himalaicum[a] +37.7 (0.5, m)[b] H. Cheng 2022b
12.7 R1 = s-Bu
R2 = CH2CO2H
R3 = CMe2OH
R4 = prenyl
R5 = H		 hyperhimatin E[c][e] H. himalaicum[a] +20.0 (0.5, m)[b] H. Cheng 2022b
12.8 R1 = Ph
R2 = prenyl
(19R,22R)-R3 = hypersamponolSideChain side-chain structure
R4 = prenyl
R5 = H		 hypersamponol E[d] H. sampsonii[a] –9.66 (0.041, m)[b] U. Kim 2026
12.9 R1 = Ph
R2 = prenyl
(19R,22S)-R3 = hypersamponolSideChain side-chain structure
R4 = prenyl
R5 = H		 hypersamponol F[d] H. sampsonii[a] +19.31 (0.041, m)[b] U. Kim 2026
12.10 R1 = Ph
R2 = prenyl
(19S,22R)-R3 = hypersamponolSideChain side-chain structure
R4 = prenyl
R5 = H		 hypersamponol G[d] H. sampsonii[a] +9.36 (0.019, m)[b] U. Kim 2026
12.11 R1 = Ph
R2 = prenyl
(19S,22S)-R3 = hypersamponolSideChain side-chain structure
R4 = prenyl
R5 = H		 hypersamponol H[d] H. sampsonii[a] +19.42 (0.021, m)[b] U. Kim 2026
12.12 R1 = Ph
R2 = prenyl
R3 = OEt
R4 = prenyl
R5 = H		 hyperadditionciol A[d] H. addingtonii +14 (0.05, m)[b] J. Chen 2026
12.13 R1 = Ph
R2 = CH2CH2CMe2OH
R3 = CMe2OH
R4 = prenyl
R5 = prenyl		 hypercoretion H[d] H. kouytchense –55.8 (0.1, m)[b] Z. Dong 2026b
Structure 13: otogirinin E — A, bicyclononanes, endo
13
13.1 otogirinin E[e] H. erectum[a] Thunb. NR Y. Ishida 2010
Structure 14: hyperwilsone J, hyperwilsone K — A, bicyclononanes, exo
14
14.1 R = i-Pr hyperwilsone J[c] H. wilsonii[a] −44.8 (0.4, m)[b] Y. Duan 2021c
14.2 R = s-Bu hyperwilsone K[c][e] H. wilsonii[a] −6.96 (0.4, m)[b] Y. Duan 2021c
Structure 15: kiiacylphnol A, kiiacylphnol B — A, bicyclononanes, exo
15
15.1 R = i-Pr kiiacylphnol A[c] H. przewalskii[a] Maxim +13 (0.1, m)[b] Y. Duan 2022a
15.2 R = s-Bu kiiacylphnol B[c][e] H. przewalskii[a] Maxim +22 (0.6, m)[b] Y. Duan 2022a
Structure 16: hypermongone D, garcinielliptone L, hyperformitin L and others — A, bicyclononanes, exo
16
16.1 R1 = i-Pr
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone D[c] H. monogynum[a] +69 (0.3, m)[b] W.-J. Xu 2015
16.2 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 garcinielliptone L[d] G. subelliptica[a] −41 (0.3)[b] J.-R. Weng 2004, X.-W. Yang 2017a, Y. Guo 2021a
16.3 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperformitin L[c] (enantiomer) H. perforatum[a] +60 (0.2, m)[b] Y. Guo 2021a
16.4 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furohyperforin isomer 2, a.k.a. attenuatumione E[c] H. attenuatum, H. perforatum[a] +39.7 (0.13)[b] J.-y. Lee 2006, C. Hashida 2008, Z.-B. Zhou 2014, X.-W. Yang 2018, Y.-F. Qiu 2023
16.5 R1 = i-Pr
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypertum H[c] H. perforatum[a] +85.7 (0.05, m)[b] W.-Y. Liu 2025b
16.6 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = OH
X2 = H		 hyperforatin B[c] H. perforatum[a] +106 (0.3, m)[b] Y. Guo 2017
16.7 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hyperformitin E, a.k.a. scabrumione D[c] H. perforatum, H. scabrum[a] +63 (0.6, m)[b], +61.5 (0.1, m)[b] Y. Guo 2021a, Z.-B. Zhou 2022a, Y.-F. Qiu 2023
16.8 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OMe
X1 = H
X2 = H		 15-epi-hyperforatin D[c] H. perforatum[a] +54 (0.6, m)[b] Y. Guo 2017
16.9 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 32-epi-hyperforatin A[c] H. perforatum[a] +78 (0.6, m)[b] Y. Guo 2017
16.10 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 hyperforatin A[c] H. perforatum[a] +84 (0.5, m)[b] Y. Guo 2017
16.11 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 curvisepalumione C[c] H. himalaicum, H. curvisepalum[a] N. Robson +37.1 (0.1, m)[b], +32.1 (0.5, m)[b] G.-H. Liu 2025, M.-M. Cao 2025
16.12 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 no common name H. himalaicum[a] +36.7 (0.1, m)[b] G.-H. Liu 2025
16.13 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = OH		 hyperuraline B[c] H. uralum[a] +14.1 (0.10)[b] J. Hu 2025
16.14 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (3R)-2,3-epoxy-3-methylbutyl
X1 = H
X2 = OH		 hypersampine A[c] H. sampsonii[a] +20.9 (NR, m)[b] X.-P. Wang 2024
16.15 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 hyperformitin A, a.k.a. scabrumione A[c] H. perforatum, H. scabrum[a] +162 (0.3, m)[b], +147.6 (0.1, m)[b] Y. Guo 2021a, Z.-B. Zhou 2022a, Y.-F. Qiu 2023
16.16 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (R)-CH2CHOHCMe=CH2
R5 = prenyl
X1 = H
X2 = H		 hyperforatin O[c] H. perforatum[a] +57.5 (0.3, m)[b] Y. Guo 2019b
16.17 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (S)-CH2CHOHCMe=CH2
R5 = prenyl
X1 = H
X2 = H		 hyperforatin P[c] H. perforatum[a] +14.2 (0.1, m)[b] Y. Guo 2019b
16.18 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = (S)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 scabrumione J[c] H. scabrum[a] +9.8 (0.1, m)[b] H. Zeng 2026
16.19 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (R)-CH2CHOHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 uralione O[c] H. uralum[a] +28.6 (0.1, m)[b] X. Li 2017, Y.-F. Qiu 2023
16.20 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hyperiscabrol B[c] H. scabrum[a] +6.7 (0.08, m)[b] L.-P. Teng 2026
16.21 R1 = i-Pr
R2 = CMe2OH
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperformitin C, a.k.a. scabrumione C[c] H. perforatum, H. scabrum[a] +94 (0.5, m)[b], +103.0 (0.1, m)[b] Y. Guo 2021a, Z.-B. Zhou 2022a, Y.-F. Qiu 2023
16.22 R1 = i-Pr
R2 = CMe2OH
R3 = (S)-CH2CH(OH)CMe2OH
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperiscabrol A[c] H. scabrum[a] +6.3 (0.1, m)[b] L.-P. Teng 2026
16.23 R1 = i-Pr
R2 = CMe2OH
R3 = CH2CH(OH)CMe2OH
R4 = prenyl
R5 = (R)-2,3-epoxy-3-methylbutyl
X1 = H
X2 = H		 hyperuraline A[e] H. uralum[a] +19.8 (0.10)[b] J. Hu 2025
16.24 R1 = i-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 ascynol L[c] H. ascyron[a] +20 (0.1, m)[b] Y.-L. Hu 2025
16.25 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone B[c] H. ascyron, H. monogynum[a] +80 (0.2, m)[b] W.-J. Xu 2015, L.-M. Kong 2017
16.26 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer 2a[e] H. perforatum[a] +66 (0.08, m)[b] J.-B. Yang 2016
16.27 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperascyrin E[c] H. ascyron[a] +16 (0.1, m)[b] J.-W. Hu 2018
16.28 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = OH
X2 = H		 hyperascyrin H[c] H. ascyron[a] +28 (0.2, m)[b] J.-W. Hu 2018
16.29 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 hyperascyrin G[c] H. ascyron[a] +12 (0.2, m)[b] J.-W. Hu 2018
16.30 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperibrin F[c] H. scabrum[a] −50.8 (0.07, m)[b] J. Hu 2017
16.31 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 propolone C, a.k.a. garcinielliptone K[d] (enantiomer) Cuban propolis, G. subelliptica[a] +35.7 (0.2)[b], +27 (0.3)[b] J.-R. Weng 2004, I. M. Hernandez 2005, X.-W. Yang 2017a
16.32 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 ascyronine A[c] H. ascyron[a] −15.5 (0.1, m)[b] E.-H. Zhang 2023
16.33 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 ascyronone F, a.k.a. uralione G[c] H. ascyron, H. uralum[a] +36.5 (0.1, m)[b], +17 (0.1)[b] Z. P. Li 2019, Z.-B. Zhou 2016b, Y.-F. Qiu 2023
Structure 17: hypermacone E, hypermacone D, hypermongone C and others — A, bicyclononanes, exo
17
17.1 R1 = i-Pr
R2 = i-Pr
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermacone E[c] H. maclarenii[a] −9.21 (0.089, m)[b] W.-L. Meng 2026
17.2 R1 = i-Pr
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermacone D[c] H. maclarenii[a] +7.84 (0.102, m)[b] W.-L. Meng 2026
17.3 R1 = i-Pr
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone C[c] H. monogynum[a] −8 (0.2, m)[b] W.-J. Xu 2015
17.4 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 garcinielliptone M[d] G. subelliptica[a] +73 (0.2)[b] J.-R. Weng 2004, X.-W. Yang 2017a, Y. Guo 2021a
17.5 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperformitin M[c] (enantiomer) H. perforatum[a] −48 (0.1, m)[b] Y. Guo 2021a
17.6 R1 = i-Pr
R2 = CMe2OH
R3 = (R)-CH2CH(OH)CMe2OH
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperhimatin P[c] H. himalaicum[a] −44.7 (0.5, m)[b] H. Cheng 2022b
17.7 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 attenuatumione F, a.k.a. hyperscabin G[c] H. attenuatum, H. scabrum[a] +19.6 (0.18)[b], +28.4 (0.1, mc)[b] Z.-B. Zhou 2014, J. Ma 2021b, Y.-F. Qiu 2023
17.8 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = OH
X2 = H		 hyperforatin C[c] H. perforatum[a] +12 (0.5, m)[b] Y. Guo 2017
17.9 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = 2,3-epoxy-3-methylbutyl
X1 = H
X2 = H		 hypericumoxide A[e] H. scabrum[a] +12.5 (0.06, m)[b] R. Liu 2017, Y.-F. Qiu 2023
17.10 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hyperformitin F[c] H. perforatum[a] +10 (0.1, m)[b] Y. Guo 2021a
17.11 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OMe
X1 = H
X2 = H		 hyperforatin D[c] H. perforatum[a] +12 (0.5, m)[b] Y. Guo 2017
17.12 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 hyperforatin L[c] H. perforatum[a] −7.5 (0.6, m)[b] Y. Guo 2019b
17.13 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 hyperforatin M[c] H. perforatum[a] +5.2 (0.3, m)[b] Y. Guo 2019b
17.14 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hypericumoxide B[c] H. scabrum[a] −12.5 (0.08, m)[b] R. Liu 2017, Y.-F. Qiu 2023
17.15 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 scabrumione K[c] H. scabrum[a] –0.2 (0.1, m)[b] H. Zeng 2026
17.16 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe=CH2
R5 = prenyl
X1 = H
X2 = H		 hyperforatin N[c] H. perforatum[a] +35.0 (0.2, m)[b] Y. Guo 2019b
17.17 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = H
X1 = H
X2 = H		 hyperhimatin O[c] H. himalaicum[a] −6.2 (0.5, m)[b] H. Cheng 2022b
17.18 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 hyperformitin B[c] H. perforatum[a] +70 (0.3, mc)[b] Y. Guo 2021a
17.19 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 27-epi-hyperiscabrol B[c] H. scabrum[a] +2.6 (0.1, m)[b] L.-P. Teng 2026
17.20 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = (S)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 27-epi-scabrumione J[c] H. scabrum[a] +2.8 (0.1, m)[b] H. Zeng 2026
17.21 R1 = i-Pr
R2 = CMe2OH
R3 = (R)-CH2CH(OH)CMe2OH
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypericumoxide C[c] H. scabrum[a] +14.7 (0.03, m)[b] R. Liu 2017, Y.-F. Qiu 2023
17.22 R1 = i-Pr
R2 = CMe2OH
R3 = (S)-CH2CH(OH)CMe2OH
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 uralione K[c] H. uralum[a] +6 (0.1)[b] Z.-B. Zhou 2016b, Y.-F. Qiu 2023
17.23 R1 = i-Pr
R2 = CMe2OH
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperformitin D, a.k.a. scabrumione B[c] H. perforatum, H. scabrum[a] +31 (0.3, m)[b], +61.5 (0.1, m)[b] Z.-B. Zhou 2016b, Y. Guo 2021a, Y.-F. Qiu 2023
17.24 R1 = i-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 ascynol M[c] H. ascyron[a] −15 (0.21, m)[b] Y.-L. Hu 2025
17.25 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone A[c] H. monogynum[a] +9 (0.2, m)[b] W.-J. Xu 2015
17.26 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer 2b[c] H. scabrum, H. cohaerens[a] +24 (0.06, m)[b] J.-B. Yang 2016
17.27 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperascyrin F[c] H. ascyron[a] −48 (0.4, m)[b] J.-W. Hu 2018
17.28 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 hyperascyrin I[c] H. ascyron[a] −35 (0.1, m)[b] J.-W. Hu 2018
17.29 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperibrin C[c] H. scabrum[a] +92.5 (0.10, m)[b] W. Gao 2016c
17.30 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 uralione F[c] H. uralum[a] −32 (0.3)[b] Z.-B. Zhou 2016b, Y.-F. Qiu 2023
17.31 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = prenyl
R4 = (S)-isolavandulyl[g]
R5 = H
X1 = H
X2 = H		 garcinialiptone C G. subelliptica[a] −94.0 (0.86, m)[b] L.-J. Zhang 2010
Structure 18: hypercoretion I, hypercoretion J, sampsonione N and others — A, bicyclononanes, endo
18
18.1 R1 = i-Pr
R2 = prenyl		 hypercoretion I[c] H. kouytchense +32.7 (0.1, m)[b] Z. Dong 2026b
18.2 R1 = i-Bu
R2 = prenyl		 hypercoretion J[c] H. kouytchense +21.5 (0.1, m)[b] Z. Dong 2026b
18.3 R1 = Ph
R2 = prenyl		 sampsonione N H. sampsonii[a] +22.0 (0.090)[b] Z. Y. Xiao 2007, Y.-F. Qiu 2023
18.4 R1 = Ph
R2 = geranyl		 hyperacmosin O, a.k.a. hypersampsonone H[d] H. acmosepalum, H. sampsonii[a] −1.5 (0.1, m)[b], + 7.5 (1.0, m)[b] M.-x. Sun 2021b, Y. Li 2023
Structure 19: sampsonione M, garcimultiflorone M — A, bicyclononanes, endo
19
19.1 R = geranyl
X = H		 sampsonione M H. sampsonii[a] +55 (0.04)[b] L.-H. Hu 2000
19.2 R = (R)-lavandulyl[f]
X = OMe		 garcimultiflorone M[c][t][u][x] G. multiflora[a] −32.8 (0.060, m)[b] Z.-Q. Wang 2018
Structure 20: lathrophytoic acid B — A, bicyclononanes, endo
20
20.1 lathrophytoic acid B Kielmeyera lathrophyton NR M. F. de Almeida 2011
Structure 21: hypermongone H, garsubellin C, hyperformitin K and others — A, bicyclononanes, exo
21
21.1 R1 = i-Pr
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone H[c] H. monogynum[a] +61 (0.2, m)[b] W.-J. Xu 2015
21.2 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 garsubellin C[d] G. subelliptica[a] +39 (0.4, e)[b] Y. Fukuyama 1997, Y. Fukuyama 1998, Y. Guo 2021a
21.3 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperformitin K[c] (enantiomer) H. perforatum[a] −56 (0.4, e)[b] Y. Guo 2021a
21.4 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 18-epi-furohyperforin isomer 1[r] H. perforatum[a] +15 (0.3, m)[b] C. Hashida 2008, X.-W. Yang 2018
21.5 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = OH
X2 = H		 hyperforatin K[c] H. perforatum[a] −13 (0.5, m)[b] Y. Guo 2017
21.6 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = OEt
X2 = H		 hyperacmosin P[c] H. acmosepalum[a] −19.2 (0.1, m)[b] M.-x. Sun 2021b
21.7 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 uralione L[c] H. uralum[a] −29.0 (0.1, m)[b] X. Li 2017
21.8 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 15-epi-hyperforatin I[c] H. perforatum[a] −28 (0.3, m)[b] Y. Guo 2017
21.9 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hyperidione F[c] H. perforatum[a] −30.0 (0.010, m)[b] X.-G. Pan 2024
21.10 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 curvisepalumione D[c] H. curvisepalum[a] N. Robson −23.3 (0.5, m)[b] M.-M. Cao 2025
21.11 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hyperidione E[c] H. perforatum[a] +1.5 (0.033, m)[b] X.-G. Pan 2024
21.12 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe2OH
R5 = prenyl
X1 = H
X2 = H		 hyperidione C[c] H. perforatum[a] +20.0 (0.020, m)[b] X.-G. Pan 2024
21.13 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OH
R5 = prenyl
X2 = H
X2 = H		 no common name H. himalaicum[a] +29.7 (0.1, m)[b] G.-H. Liu 2025
21.14 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 hyperformitin H[c] H. perforatum[a] +88 (0.3, m)[b] Y. Guo 2021a
21.15 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hyperiscabrol C[c] H. scabrum[a] +0.8 (0.04, m)[b] L.-P. Teng 2026
21.16 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = (R)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 scabrumione H[c] H. scabrum[a] +0.2 (0.1, m)[b] H. Zeng 2026
21.17 R1 = i-Pr
R2 = CMe2OH
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypericumoxide D H. scabrum[a] +9.8 (0.07, m)[b] R. Liu 2017
21.18 R1 = i-Pr
R2 = CMe2OH
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 ascyronine B[c] H. ascyron[a] +13.9 (0.1, m)[b] E.-H. Zhang 2023
21.19 R1 = i-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 ascynol N[c] H. ascyron[a] +44 (0.2, m)[b] Y.-L. Hu 2025
21.20 R1 = i-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperwilsone E[c] H. wilsonii[a] −16.8 (0.6, m)[b] Y. Duan 2021c
21.21 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone F[c] H. monogynum[a] −44 (0.1, m)[b] W.-J. Xu 2015
21.22 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer B[e][s] H. perforatum[a] +14 (1.5)[b] C. Hashida 2008, X.-W. Yang 2018
21.23 R1 = Ph
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermacone A[c] H. maclarenii[a] –65.71 (0.07, m)[b] W.-L. Meng 2026
21.24 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperascyrin A[c] H. ascyron[a] −80 (0.1, m)[b] J.-W. Hu 2018
21.25 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 hyperascyrin C[c] H. ascyron[a] −67 (0.2, m)[b] J.-W. Hu 2018
21.26 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperibone A H. scabrum[a] +57 (0.2)[b], +63.7 (0.4)[b] M. Matsuhisa 2002, I. M. Hernandez 2005
21.27 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 garcinielliptone I (enantiomer) G. subelliptica[a] −37.7 (1.1)[b] J.-R. Weng 2003b, R. Ciochina 2006
21.28 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 uralodin B H. henryi [a]subsp. uraloides −24.6 (0.075, m)[b] X.-Q. Chen 2010
21.29 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = OH
X2 = H		 hypercohin J H. cohaerens[a] −4.8 (0.09, m)[b] X. Liu 2013a, X.-W. Yang 2018
21.30 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 hyperbeanin D[c] H. beanii[a] +0.9 (0.11, m)[b] Y. Ma 2022a
21.31 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 dihroxuralodin H. petiolulatum[a] −27.9 (0.10, m)[b] T. Rui 2017
Structure 22: hyperwilsone C — A, bicyclononanes, exo
22
22.1 hyperwilsone C[c] H. wilsonii[a] −36.3 (0.3, m)[b] Y. Duan 2021c
Structure 23: hypermongone G, hypermongone I, garsubellin D and others — A, bicyclononanes, exo
23
23.1 R1 = i-Pr
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone G[c] H. monogynum[a] +34 (0.3, m)[b] W.-J. Xu 2015
23.2 R1 = i-Pr
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = (S)-CH2CHOHCMe2OH
X1 = H
X2 = H		 hypermongone I[c] H. monogynum[a] +6 (0.1, m)[b] W.-J. Xu 2015
23.3 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 garsubellin D[d] G. subelliptica[a] −12 (0.4, e)[b] Y. Fukuyama 1998, Y. Guo 2021a
23.4 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperformitin J[c] (enantiomer) H. perforatum[a] +18 (0.4, e)[b] Y. Guo 2021a
23.5 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = OH		 garcinielliptone P G. subelliptica[a] −2 (1.6)[b] K.-W. Lin 2011
23.6 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furohyperforin isomer 1[r] H. perforatum[a] +50 (0.7)[b] J.-y. Lee 2006, C. Hashida 2008, X.-W. Yang 2018
23.7 R1 = i-Pr
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypertum I[c] H. perforatum[a] +60.3 (0.04, m)[b] W.-Y. Liu 2025b
23.8 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = OH
X2 = H		 hyperforatin J[c] H. perforatum[a] +44 (0.5, m)[b] Y. Guo 2017
23.9 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hypericumoxide F H. scabrum[a] +10.7 (0.09, m)[b] R. Liu 2017
23.10 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 uralione M[c] H. uralum[a] +28.6 (0.1, m)[b] X. Li 2017
23.11 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 uralione N[c] H. uralum[a] +38.8 (0.1, m)[b] X. Li 2017
23.12 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 scabrumione I[c] H. uralum[a] +3.8 (0.1, m)[b] H. Zeng 2026
23.13 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 17-epi-scabrumione I[c] H. uralum[a] +4.2 (0.1, m)[b] H. Zeng 2026
23.14 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = CH2C(=O)CHMe2
X1 = H
X2 = H		 hyperforatin H[c] H. perforatum[a] +34 (0.5, m)[b] Y. Guo 2017
23.15 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 hyperforatin I[c] H. perforatum[a] +23 (0.4, m)[b] Y. Guo 2017
23.16 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = H
X1 = H
X2 = H		 hyperhimatin M[c] H. himalaicum[a] +37.8 (0.5, m)[b] H. Cheng 2022b
23.17 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 hyperformitin G[c] H. perforatum[a] +17 (0.3, m)[b] Y. Guo 2021a
23.18 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OH
R5 = H
X1 = H
X2 = H		 hyperhimatin N[c] H. himalaicum[a] +27.1 (0.5, m)[b] H. Cheng 2022b
23.19 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe2OH
R5 = prenyl
X1 = H
X2 = H		 hypericumoxide E[c] H. scabrum[a] +9.8 (0.07, m)[b] R. Liu 2017
23.20 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH
R5 = (S)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hyperidione A[c] H. perforatum[a] +20.0 (0.025, m)[b] X.-G. Pan 2024
23.21 R1 = i-Pr
R2 = CMe2OH
R3 = CH2CH(OH)CMe2OH
R4 = prenyl
R5 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 ascyronine C[c][e] H. ascyron[a] +11.9 (0.1, m)[b] E.-H. Zhang 2023
23.22 R1 = i-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 ascynol O[c] H. ascyron[a] −55 (0.1, m)[b] Y.-L. Hu 2025
23.23 R1 = i-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperwilsone D[c] H. wilsonii[a] +37.6 (0.4, m)[b] Y. Duan 2021c
23.24 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone E[c] H. monogynum[a] +9 (0.2, m)[b] W.-J. Xu 2015
23.25 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = (R)-CH2CHOHCMe2OH
X1 = H
X2 = H		 hypermongone J[c] H. monogynum[a] +6 (0.1, m)[b] W.-J. Xu 2015
23.26 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 garsubellin E[e] G. subelliptica[a] −7 (e, 0.4)[b] Y. Fukuyama 1998
23.27 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer A[e][s] H. perforatum[a] +34 (0.9)[b] C. Hashida 2008, X.-W. Yang 2018
23.28 R1 = (R)-s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CHOHCMe2OH
X1 = H
X2 = H		 hyperidione B[c] H. perforatum[a] +120.0 (0.010, m)[b] X.-G. Pan 2024
23.29 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperascyrin B[c] H. ascyron[a] −5 (0.2, m)[b] J.-W. Hu 2018
23.30 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 hyperascyrin D[c] H. ascyron[a] +3 (0.2, m)[b] J.-W. Hu 2018
23.31 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperibone B H. scabrum[a], Cuban propolis −20.8 (0.5)[b], −42.2 (0.1)[b] M. Matsuhisa 2002, I. M. Hernandez 2005
23.32 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 ochrocarpinone C[o][p] (perhaps enantiomer) Ochrocarpos punctatus +0.21 (0.38)[b] V. S. P. Chaturvedula 2002
23.33 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 uralodin C H. henryi [a]subsp. uraloides −55.0 (0.010, m)[b] X.-Q. Chen 2010
23.34 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hypersampine B[c] H. sampsonii[a] +13.9 (0.10, m)[b] X.-P. Wang 2024
23.35 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = prenyl
R4 = (R)-lavandulyl[f]
R5 = H
X1 = H
X2 = H		 garcinielliptone FB G. subelliptica[a] −66 (0.2)[b] C.-C. Wu 2005
Structure 24: hyperidione D, scabrumione E, hyperwilone D and others — A, bicyclononanes, endo
24
24.1 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = prenyl
X = H		 hyperidione D[c] H. perforatum[a] +26.0 (0.050, m)[b] X.-G. Pan 2024
24.2 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X = H		 scabrumione E H. scabrum[a] +4.5 (0.04, m)[b] Z.-B. Zhou 2022a
24.3 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = prenyl
X = H		 hyperwilone D[d] H. wilsonii[a] +50.0 (0.74)[b] J. Hao 2021
24.4 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hypersampsone U[d] H. sampsonii[a] +28.2 (0.50)[b] W.-J. Tian 2016
24.5 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OMe		 garcimultinone G[d] G. multiflora[a] +159.26 (0.02, m)[b] H. Teng 2021
24.6 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X = H		 hyperibone C H. scabrum[a] −27.3 (0.3)[b] M. Matsuhisa 2002, R. Ciochina 2006
24.7 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = prenyl
X = H		 hyperattenin C[d] H. attenuatum[a] Choisy −8.4 (0.13, m)[b] D. Li 2015a
24.8 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = prenyl
X = OEt		 hyperattenin D[d] H. attenuatum[a] Choisy +100.4 (0.42, m)[b] D. Li 2015a
24.9 R1 = Ph
R2 = (S)-lavandulyl[f]
R3 = prenyl
R4 = prenyl
X = H		 garcimultinone F[d] G. multiflora[a] +186.27 (0.02, m)[b] H. Teng 2021
24.10 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = prenyl
R4 = prenyl
X = H		 garcinielliptone GC[e] G. multiflora[a] +159.4 (0.27, m)[b] H. Yang 2020
Structure 25: sampsonione O, otogirinin D — A, bicyclononanes, endo
25
25.1 R = prenyl sampsonione O H. sampsonii[a] +87.9 (0.073)[b] Z. Y. Xiao 2007
25.2 R = geranyl otogirinin D H. erectum[a] Thunb., H. attenuatum[a] +160.0 (0.03, m)[b] Y. Ishida 2010, D. Li 2015a
Structure 26: papuaforin B, scrobiculatone B, hyperscabrone K and others — A, bicyclononanes, exo
26
26.1 R1 = i-Pr
R2 = Me		 papuaforin B H. papuanum[a] NR K. Winkelmann 2001a
26.2 R1 = Ph
R2 = prenyl		 scrobiculatone B[c] C. scrobiculata[a] +44.7 (0.2)[b] A. L. M. Porto 2000
26.3 R1 = Ph
R2 = prenyl		 hyperscabrone K[d] (enantiomer) H. scabrum[a] −57.2 (0.1, m)[b] W. Gao 2016b, X.-W. Yang 2018
26.4 R1 = Ph
R2 = lavandulyl		 chamone II[e] C. grandiflora[a] NR J. Lokvam 2000
Structure 27: plukenetione F, hypersampsone F, garcimultine A and others — A, bicyclononanes, endo
27
27.1 R1 = prenyl
R2 = H		 plukenetione F C. plukenetii[a] −53.6 (0.03)[b] G. E. Henry 1999
27.2 R1 = prenyl
R2 = prenyl		 hypersampsone F H. sampsonii[a] +30 (0.2)[b] Y.-L. Lin 2003, R. Ciochina 2006
27.3 R1 = lavandulyl
R2 = H		 garcimultine A[e]
(equilibrates rapidly with regioisomer garcimultine B)		 G. multiflora[a] mixture with garcimultine B: +79.4 (0.336, m)[b] H. Liu 2017
27.4 R1 = (S)-CH2CH(CMe2OH)CH2CH=CMe2
R2 = H		 garcimultinone H[d] G. multiflora[a] +35.0 (0.02, m)[b] H. Teng 2021
27.5 R1 = (2R,3E)-CH2CH(CMe=CH2)CH=CHCMe2OH
R2 = H		 garcimultiflorone K[c][t][u][x] (one of two by that name) G. multiflora[a] −1.1 (0.090, m)[b] Z.-Q. Wang 2018
Structure 28: bellumone B, hyperscabin F, uralione A and others — A, bicyclononanes, exo
28
28.1 R1 = i-Pr
R2 = Me
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = H		 bellumone B[c] H. bellum[a] +6 (0.05, m)[b] X. Zhou 2021
28.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = H		 hyperscabin F, a.k.a. hyperpatin E[c] H. patulum, H. scabrum[a] +66.4 (0.12, mc)[b], +76.0 (0.10, m)[b] J. Ma 2021b, J.-C. Huang 2025
28.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = CH2–prenyl
X1 = OH
X2 = H		 uralione A[c] H. uralum[a] +49 (0.2)[b] Z.-B. Zhou 2016b
28.4 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = Me
X1 = OH
X2 = H		 hyperhimatin C[c] H. himalaicum[a] −11.8 (0.5, m)[b] H. Cheng 2022b
28.5 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = CH2–prenyl
X1 = OH
X2 = H		 hypericumoxide M[c] H. scabrum[a] +19.8 (0.07, m)[b] R. Liu 2017
28.6 R1 = i-Pr
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl
R4 = CH2–prenyl
X1 = OH
X2 = H		 attenuatumione H[c] H. attenuatum[a] +34.6 (0.1)[b] Z.-B. Zhou 2016a
28.7 R1 = s-Bu
R2 = Me
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = H		 bellumone A[c][e] H. bellum[a] +10 (0.1, m)[b] X. Zhou 2021
28.8 R1 = s-Bu
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = Me
X1 = H
X2 = OH		 hyperhimatin B[c][e] H. himalaicum[a] −4.0 (0.5, m)[b] H. Cheng 2022b
28.9 R1 = s-Bu
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = Me
X1 = OH
X2 = H		 hyperhimatin A[c][e] H. himalaicum[a] −6.7 (0.5, m)[b] H. Cheng 2022b
28.10 R1 = Ph
R2 = Me
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = OH		 hyperacmosin I[c][ee] H. acmosepalum[a] −122 (0.25, m)[b] X. Wang 2020b
28.11 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = H		 hyperkouytone D, a.k.a. hyperpatin A[c] H. kouytchense, H. patulum[a] −57.0 (0.38, m)[b], −35.0 (0.10, m)[b] H.-Y. Lou 2024, J.-C. Huang 2025
28.12 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = OH		 uralione B H. uralum[a] −28 (0.1)[b] Z.-B. Zhou 2016b
28.13 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH2–prenyl
X1 = OH
X2 = H		 uralione C H. uralum[a] −41 (0.1)[b] Z.-B. Zhou 2016b
28.14 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hyperpatin B[c] H. patulum[a] −58.5 (0.10, m)[b] J.-C. Huang 2025
28.15 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2=CHCH=O
X1 = H
X2 = H		 hyperpatin C[c] H. patulum[a] −16.0 (0.10, m)[b] J.-C. Huang 2025
28.16 R1 = Ph
R2 = (R)-CH2CH(OH)CMe2OH
R3 = prenyl
R4 = Me
X1 = OH
X2 = H		 propolone B Cuban propolis +38.2 (0.6)[b] I. M. Hernandez 2005, W. Gao 2016b
28.17 R1 = Ph
R2 = (S)-CH2CH(OH)CMe2OH
R3 = prenyl
R4 = Me
X1 = OH
X2 = H		 hyperscabrone J[c] H. scabrum[a] −58.5 (0.1, m)[b] W. Gao 2016b
28.18 R1 = Ph
R2 = (S)-CH2CH(OH)CMe2OH
R3 = prenyl
R4 = CH2–prenyl
X1 = OH
X2 = H		 hyperkouytone E[c] H. kouytchense[a] −49.3 (0.25, m)[b] H.-Y. Lou 2024
28.19 R1 = Ph
R2 = (S)-CH2CH(OH)CMe2OH
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = OH		 uralione D[c] H. uralum[a] −28 (0.1, m)[b] Z.-B. Zhou 2016b
28.20 R1 = Ph
R2 = (S)-CH2CH(OH)CMe2OH
R3 = prenyl
R4 = (R)-CH2CH2CH(OH)CMe2OH
X1 = H
X2 = OH		 hypertonii C[c] H. addingtonii[a] N. Robson +25.4 (0.1, acn)[b] Q. Feng 2025
28.21 R1 = Ph
R2 = (S)-CH2CH(OH)CMe2OH
R3 = prenyl
R4 = (S)-CH2CH2CH(OH)CMe2OH
X1 = H
X2 = OH		 hypertonii D[c] H. addingtonii[a] N. Robson +18.6 (0.1, acn)[b] Q. Feng 2025
28.22 R1 = Ph
R2 = (R)-(2,4,4-trimethyl-2-cyclohexenyl)methyl
R3 = prenyl
R4 = Me
X1 = H
X2 = H		 garcinuntin B[c] G. nuntasaenii[a] −62.8 (1.0)[b] S. Chaturonrutsamee 2018
28.23 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = Me
X1 = H
X2 = H		 hyperscabrone N[c] G. multiflora[a] −62.0 (0.1, m)[b] J. Cao 2024
28.24 R1 = 3,4-dihydroxyphenyl
R2 = (S)-lavandulyl[f]
R3 = prenyl
R4 = Me
X1 = H
X2 = H		 garcimultinone J[d] G. multiflora[a] −5.07 (0.05, m)[b] H. Teng 2021
28.25 R1 = 3,4-dihydroxyphenyl
R2 = 2,2,6,6-tetramethyl-3-oxanylmethyl
R3 = prenyl
R4 = Me
X1 = H
X2 = H		 hyperscabrone O[c][e] G. multiflora[a] −40.0 (0.1, m)[b] J. Cao 2024
28.26 R1 = 3,4-dihydroxyphenyl
R2 = (S)-2,2,6,6-tetramethyl-3-oxanylmethyl
R3 = CH2CH2CMe2OH
R4 = Me
X1 = H
X2 = H		 garpedvinin M[d] G. pedunculata[a] Roxb. +30.8 (0.10, m)[b] D.-L. Zou 2025
Structure 29: hyperpatin D — A, bicyclononanes, exo
29
29.1 hyperpatin D[c] H. patulum[a] −42.0 (0.10, m)[b] J.-C. Huang 2025
Structure 30: hypersampsone T, 15,16-dihydro-16-hydroperoxyplukenetione F, hypersampsone H and others — A, bicyclononanes, endo
30
30.1 R = prenyl
X = H		 hypersampsone T[d] H. sampsonii[a] +62.8 (0.50)[b] W.-J. Tian 2016
30.2 R = prenyl
X = OOH		 15,16-dihydro-16-hydroperoxyplukenetione F[e] C. havetiodes[a] var. stenocarpa +24.7 (0.3)[b] O. E. Christian 2001
30.3 R = geranyl
X = H		 hypersampsone H H. sampsonii[a] +44.37 (0.222)[b] Y. H. Zeng 2009, W.-J. Tian 2016, X.-W. Yang 2018
30.4 R = (S)-lavandulyl[f]
X = H		 garcimultinone I[d] G. multiflora[a] +73.90 (0.09, m)[b] H. Teng 2021
Structure 31: hypersamponol I — A, bicyclononanes, endo
31
31.1 hypersamponol I[d] H. sampsonii[a] –26.25 (0.046, m)[b] U. Kim 2026
Structure 32: papuaforin A, papuaforin E, garcinielliptone F and others — A, bicyclononanes, exo
32
32.1 R1 = i-Pr
R2 = Me
R3 = H		 papuaforin A H. papuanum[a] +13 (0.1, m)[b] K. Winkelmann 2001a
32.2 R1 = i-Pr
R2 = Me
R3 = prenyl		 papuaforin E H. papuanum[a] +41 (0.1, m)[b] K. Winkelmann 2001a
32.3 R1 = i-Pr
R2 = prenyl
R3 = H		 garcinielliptone F, a.k.a. garsubelone B[d] G. subelliptica[a] −23 (0.09)[b], −90.8 (0.08, m)[b] J.-R. Weng 2003b, Y.-L. Wang 2019, Y.-G. Fu 2025
32.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl		 pyrano[7,28-b]hyperforin H. perforatum[a] +83.5 (0.3)[b] M. D. Shan 2001
32.5 R1 = s-Bu
R2 = Me
R3 = H		 papuaforin C[e] H. papuanum[a] +23 (0.1, m)[b] K. Winkelmann 2001a
32.6 R1 = s-Bu
R2 = Me
R3 = prenyl		 papuaforin D[e] H. papuanum[a] +64 (0.1, m)[b] K. Winkelmann 2001a
32.7 R1 = s-Bu
R2 = prenyl
R3 = H		 garsubelone C[d][e] G. subelliptica[a] +6 (0.06, m)[b] Y.-G. Fu 2025
32.8 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hypercohin I[e] H. cohaerens[a] +60.0 (0.22, m)[b] X. Liu 2013a
32.9 R1 = Ph
R2 = prenyl
R3 = H		 scrobiculatone A C. scrobiculata[a] +44.7 (0.2)[b] A. L. M. Porto 2000, K. Winkelmann 2001a
32.10 R1 = Ph
R2 = (R)-(2,4,4-trimethyl-2-cyclohexenyl)methyl
R3 = H		 garcinuntin C[c] G. nuntasaenii[a] −112.3 (0.33)[b] S. Chaturonrutsamee 2018
Structure 33: hyperselancin B, hyperselancin A, androforin A and others — A, bicyclononanes, endo
33
33.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl		 hyperselancin B[c] H. lanceolatum[a] −9 (0.2)[b] S. A. T. Fobofou 2016, Y.-G. Fu 2025
33.2 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hyperselancin A[c][e] H. lanceolatum[a] −1 (0.3)[b] S. A. T. Fobofou 2016, Y.-G. Fu 2025
33.3 R1 = s-Bu
R2 = prenyl
R3 = geranyl		 androforin A[e] H. androsaemum[a] −59.3 (0.23, MeOH)[b] K. Wang 2012
33.4 R1 = Ph
R2 = prenyl
R3 = prenyl		 plukenetione G C. plukenetii[a] NR G. E. Henry 1999
33.5 R1 = Ph
R2 = lavandulyl
R3 = prenyl		 garcimultine B[e]
(equilibrates rapidly with regioisomer garcimultine A)		 G. multiflora[a] mixture with garcimultine A: +79.4 (0.336, m)[b] H. Liu 2017
Structure 34: bellumone C, garcinielliptone B, hyperpatin F and others — A, bicyclononanes, exo
34
34.1 R1 = i-Pr
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 bellumone C[c] H. bellum[a] +13 (0.1, m)[b] X. Zhou 2021
34.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 garcinielliptone B G. subelliptica[a] −23 (0.1)[b] J.-R. Weng 2003a
34.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hyperpatin F, a.k.a. hypertum J[c] H. patulum, H. perforatum, H. scabrum[a] +13.0 (0.10, m)[b], +7.8 (0.1, m)[b] J.-C. Huang 2025, W.-Y. Liu 2025b
34.4 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = OH
X2 = H		 hyperwilsone I[c][e] H. wilsonii[a] +13.6 (0.4, m)[b] Y. Duan 2021c
34.5 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = OH
X2 = H		 hyperascyrin J[c] H. ascyron[a] −68 (0.2, m)[b] J.-W. Hu 2018
34.6 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = OH		 hyperacmosin H[c] H. acmosepalum[a] −478 (0.25, m)[b] X. Wang 2020b
34.7 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 propolone A Cuban propolis, H. attenuatum[a] +40 (0.1)[b] O. Cuesta Rubio 1999, D. Li 2015a
34.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hyperforcinol I, a.k.a. hyperpatin G[c] H. forrestii, H. patulum[a] −37 (0.1, m)[b], −48.0 (0.10, m)[b] W.-J. Lu 2021, J.-C. Huang 2025
34.9 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = OH
X2 = H		 hyperbeanin E[c] H. beanii[a] −30.0 (0.10, m)[b] Y. Ma 2022a
34.10 R1 = Ph
R2 = (R)-(2,4,4-trimethyl-2-cyclohexenyl)methyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 garcinuntin A[c] G. nuntasaenii[a] −96.3 (0.30)[b] S. Chaturonrutsamee 2018
34.11 R1 = 3,4-dihydroxyphenyl
R2 = (S)-2,2,6,6-tetramethyl-3-oxanylmethyl
R3 = CH2CH2CMe2OH
R4 = H
X1 = H
X2 = H		 garpedvinin N[d] G. pedunculata[a] Roxb. +40.9 (0.10, m)[b] D.-L. Zou 2025
Structure 35: ochrocarpinone A — A, bicyclononanes, exo
35
35.1 ochrocarpinone A[e][o] Ochrocarpos punctatus +8.7 (0.15)[b] V. S. P. Chaturvedula 2002
Structure 36: hypersampsone K, garcimultiflorone L — A, bicyclononanes, endo
36
36.1 R = geranyl hypersampsone K H. sampsonii, H. attenuatum[a] +31.7 (0.376)[b] Y. H. Zeng 2012, D. Li 2015a
36.2 R = (R)-lavandulyl[f] garcimultiflorone L[c] G. multiflora[a] +65.4 (0.040, m)[b] Z.-Q. Wang 2018
Structure 37: hyperpatin H — A, bicyclononanes, exo
37
37.1 hyperpatin H[c] H. patulum[a] −105.0 (0.10, m)[b] J.-C. Huang 2025
Structure 38: garcimultinone D, garcimultinone E — A, bicyclononanes, exo
38
38.1 R = Ph garcimultinone D[d] G. multiflora[a] +186.27 (0.02, m)[b] H. Teng 2021
38.2 R = 3,4-dihydroxyphenyl garcimultinone E[d] G. multiflora[a] +11.22 (0.15, m)[b] H. Teng 2021
Structure 39: garcimultiflorone A — A, bicyclononanes, endo
39
39.1 garcimultiflorone A G. multiflora[a] −173 (0.12)[b] J.-J. Chen 2009
Structure 40: no name — A, bicyclononanes, endo
40
40.1 no common name C. obdeltifolia[a] +30.9 (0.3)[b] J. S. A. R. Teixeira 2005
Structure 41: hypersampsonone A — A, bicyclononanes, endo
41
41.1 hypersampsonone A[d] H. sampsonii[a] +46.1 (0.59)[b] J.-S. Zhang 2016
Structure 42: hypersampsone S — A, bicyclononanes, endo
42
42.1 hypersampsone S[d] (one of two by that name) H. sampsonii[a] +62.0 (0.50)[b] W.-J. Tian 2016
Structure 43: hypercohone D, ascynol P — A, bicyclononanes, exo
43
43.1 R1 = i-Pr
R2 = prenyl		 hypercohone D H. cohaerens[a] −97.0 (0.07, m)[b] J.-J. Zhang 2014a
43.2 R1 = i-Bu
R2 = Me		 ascynol P[c] H. ascyron[a] −130 (0.1, m)[b] Y.-L. Hu 2025
Structure 44: oxepahyperforin, uralione J, hyperforatone F and others — A, bicyclononanes, exo
44
44.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl		 oxepahyperforin H. perforatum[a] −73.7 (0.8)[b] L. Verotta 2000
44.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OH		 uralione J[c] H. uralum[a] −48 (0.1, m)[b] Z.-B. Zhou 2016b
44.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 hyperforatone F H. perforatum[a] −70.0 (0.3, m)[b] Y. Guo 2018
44.4 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = prenyl		 hypericumoxide I[c] H. scabrum[a] −67.3 (0.06, m)[b] R. Liu 2017
44.5 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl		 hyperforatone G[c] H. perforatum[a] −77.5 (0.3, m)[b] Y. Guo 2018
44.6 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = prenyl		 hypericumoxide G[c] H. scabrum[a] −60.3 (0.07, m)[b] R. Liu 2017
44.7 R1 = i-Pr
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl
R4 = prenyl		 hypericumoxide H[c] H. scabrum[a] −43.5 (0.06, m)[b] R. Liu 2017
44.8 R1 = i-Pr
(18S,39R)-R2 = hypercohinSideChain side-chain structure
R3 = prenyl
R4 = prenyl		 hyperforatone E H. perforatum[a] −93.6 (0.9, m)[b] Y. Guo 2018
44.9 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyphenrone E[c] H. henryi[a] −117.6 (0.20, m)[b] X.-W. Yang 2014, X.-W. Yang 2015
44.10 R1 = s-Bu
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl		 hyperforatone H[c][e] H. perforatum[a] −90.3 (0.9, m)[b] Y. Guo 2018
44.11 R1 = s-Bu
R2 = (E)-CH=CHCH2OOH
R3 = prenyl
R4 = prenyl		 uralin C[c][e] H. uralum[a] −82 (0.2, m)[b] Q.-Q. Fang 2021
44.12 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl		 hyperascyrin K[c] H. ascyron[a] −201 (0.2, m)[b] J.-W. Hu 2018
44.13 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hypercohone F, a.k.a. uralione H H. cohaerens, H. uralum[a] −240.8 (0.17, m)[b], −210 (0.2)[b] J.-J. Zhang 2014a, Z.-B. Zhou 2016b
44.14 R1 = Ph
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl		 uralione I[c] H. uralum[a] −139 (0.1, m)[b] Z.-B. Zhou 2016b
44.15 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCH2OH
R4 = prenyl		 kiiacylphnol H[c] H. przewalskii[a] Maxim −115 (0.4, m)[b] Y. Duan 2022a
Structure 45: hyperscabrone C, hypercohone E, ascynol Q and others — A, bicyclononanes, exo
45
45.1 R1 = i-Pr
R2 = Me		 hyperscabrone C[c] H. scabrum[a] −124 (0.1, m)[b] W. Gao 2016a
45.2 R1 = i-Pr
R2 = prenyl		 hypercohone E H. cohaerens[a] −42.8 (0.12, m)[b] J.-J. Zhang 2014a
45.3 R1 = i-Bu
R2 = Me		 ascynol Q[c] H. ascyron[a] −112 (0.1, m)[b] Y.-L. Hu 2025
45.4 R1 = (R)-s-Bu
R2 = Me		 hyperscabrone D[c] H. scabrum[a] −75 (0.1, m)[b] W. Gao 2016a
45.5 R1 = s-Bu
R2 = prenyl		 hyperibrin H[c][e] H. scabrum[a] NR W. Xu 2021
45.6 R1 = Ph
R2 = prenyl		 kiiacylphnol G[c] H. przewalskii[a] Maxim −125 (0.4, m)[b] Y. Duan 2022a
Structure 46: hyperkouytone A — A, bicyclononanes, caged
46
46.1 hyperkouytone A[d] H. kouytchense[a] −24.8 (0.21, m)[b] H.-Y. Lou 2024
Structure 47: hyperhookerione A — A, bicyclononanes, exo
47
47.1 hyperhookerione A[c] H. hookerianum[a] +127.8 (0.5, m)[b] Z. Guo 2025b
Structure 48: bellumone D, hyperibone J, subellinone and others — A, bicyclononanes, exo
48
48.1 R1 = i-Pr
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = H		 bellumone D[c] H. bellum[a] −11 (0.1, m)[b] X. Zhou 2021
48.2 R1 = i-Pr
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 hyperibone J, a.k.a. hyperfoliatin H. scabrum, H. ascyron, H. perfoliatum[a] L. +16.9 (0.3)[b], +17 (1, m)[b] N. Tanaka 2004, N. Benkiki 2014, L.-M. Kong 2017
48.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 subellinone, a.k.a. garcinielliptin oxide G. subelliptica[a] −2.8 (1.0, e)[b]; +1 (0.3)[b] Y. Fukuyama 1993, C.-N. Lin 1996, R. B. Grossman 2020
48.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 8-hydroxyhyperforin-8,1-hemiacetal H. perforatum[a] +34 (1.0)[b] L. Verotta 2000
48.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CHOHCMe2OH		 hyperfol C[c] H. perforatum[a] −9.18 (0.05, m)[b] H. Lou 2020b
48.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CHOHCMe2OH		 hyperfol D[c] H. perforatum[a] −43.12 (0.12, m)[b] H. Lou 2020b
48.7 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CHOHCMe2OMe		 hyperfol E[c] H. perforatum[a] −27.09 (0.09, m)[b] H. Lou 2020b
48.8 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl		 hyphenrone W H. henryi[a] H. Lév & Vaniot +6 (0.08, m)[b] Y. Liao 2016
48.9 R1 = i-Pr
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H		 garcinielliptone E G. subelliptica[a] −51 (0.2)[b] J.-R. Weng 2003a, R. B. Grossman 2020
48.10 R1 = i-Pr
R2 = geranyl
R3 = Me
R4 = prenyl
R5 = H		 bellumone E[c] H. bellum[a] −9 (0.1, m)[b] X. Zhou 2021
48.11 R1 = i-Bu
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 ascyronone D H. ascyron[a] −3 (0.18, m)[b] L.-M. Kong 2017
48.12 R1 = i-Bu
R2 = prenyl
R3 = prenyl
R4 = (E)-4-oxoprenyl
R5 = H		 spiranthenone A Spiranthera odoratissima +11 (0.19)[b] L. C. Albernaz 2012, X.-W. Yang 2018
48.13 R1 = (S)-s-Bu
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 hyperscabrone G[c] H. ascyron, H. scabrum[a] +7 (0.1, m)[b] W. Gao 2016a, L.-M. Kong 2017
48.14 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 garcinielliptone T[e] G. subelliptica[a] +32 (0.09, m)[b] R. B. Grossman 2020
48.15 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyphenrone G[c] H. henryi[a] +26 (0.4, m)[b] X.-W. Yang 2015
48.16 R1 = s-Bu
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl		 hyperforcinol G[c][e] H. forrestii[a] +54 (0.3, m)[b] W.-J. Lu 2021
Structure 49: hyperhookerione B, hyperhookerione C — A, bicyclononanes, exo
49
49.1 R = i-Pr hyperhookerione B[c] H. hookerianum[a] +221.6 (0.5, m)[b] Z. Guo 2025b
49.2 R = s-Bu hyperhookerione C[c][e] H. hookerianum[a] +33.3 (0.5, m)[b] Z. Guo 2025b
Structure 50: kiiacylphnol C, hyperhookerione D, hypseudohenrin I and others — A, bicyclononanes, exo
50
50.1 R = i-Pr
X = OH		 kiiacylphnol C[c] H. przewalskii[a] Maxim +61 (0.5, m)[b] Y. Duan 2022a
50.2 R = i-Pr
X = OMe		 hyperhookerione D[c] H. hookerianum[a] +77.8 (0.5, m)[b] Z. Guo 2025b
50.3 R = i-Pr
X = OEt		 hypseudohenrin I[c] H. pseudohenryi[a] +21.5 (20.6, m)[b] H.-R. Sun 2021a
50.4 R = s-Bu
X = OH		 hyperforcinol F[c][e] H. forrestii[a] +113 (0.2, m)[b] W.-J. Lu 2021
50.5 R = s-Bu
X = OEt		 hypseudohenrin J[c][e] H. pseudohenryi[a] +40.6 (0.71, m)[b] H.-R. Sun 2021a
Structure 51: przewalcyrone E, przewalcyrone F, hyphenrone T and others — A, bicyclononanes, exo
51
51.1 R1 = i-Pr
R2 = prenyl
R3 = H
X1 = H
X2 = OH		 przewalcyrone E[c] H. przewalskii[a] −88.18 (0.44, m)[b] Y. Duan 2019
51.2 R1 = i-Pr
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 przewalcyrone F[c] H. przewalskii[a] −47.25 (0.13, m)[b] Y. Duan 2019
51.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = H
X2 = OH		 hyphenrone T[c] H. henryi[a] H. Lév & Vaniot −118 (0.09, m)[b] Y. Liao 2016
51.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyphenrone U H. henryi[a] H. Lév & Vaniot −46 (0.16, m)[b] Y. Liao 2016
51.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = O
X2 = O		 hypseudohenrin K[c] H. pseudohenryi[a] −18.6 (1.13, m)[b] H.-R. Sun 2021a
51.6 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe=CH2
X1 = H
X2 = OH		 hyperforatone J[c] H. perforatum[a] −59.5 (0.2, m)[b] Y. Guo 2018
51.7 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe=CH2
X1 = H
X2 = OH		 hyperforatone I[c] H. perforatum[a] −40.0 (0.4, m)[b] Y. Guo 2018
51.8 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OMe
X1 = H
X2 = OH		 hyperforatone O[c] H. perforatum[a] −22.0 (0.3, m)[b] Y. Guo 2018
51.9 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OMe
X1 = H
X2 = OH		 hyperforatone N[c] H. perforatum[a] −52.7 (0.4, m)[b] Y. Guo 2018
51.10 R1 = i-Pr
R2 = (R)-CH2CHOHCMe=CH2
R3 = prenyl
X1 = H
X2 = OH		 hyperforatone K[c] H. perforatum[a] −35.4 (0.5, m)[b] Y. Guo 2018
51.11 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
X1 = H
X2 = OH		 hyperforatone L[c] H. perforatum[a] −66.3 (0.3, m)[b] Y. Guo 2018
51.12 R1 = i-Pr
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl
X1 = H
X2 = OH		 hyperforatone M[c] H. perforatum[a] −10.4 (0.3, m)[b] Y. Guo 2018
51.13 R1 = i-Bu
R2 = prenyl
R3 = H
X1 = H
X2 = OH		 przewalcyrone C[c] H. przewalskii[a] −80.33 (0.3, m)[b] Y. Duan 2019
51.14 R1 = i-Bu
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 przewalcyrone D[c] H. przewalskii[a] −67.70 (0.18, m)[b] Y. Duan 2019
51.15 R1 = (S)-s-Bu
R2 = prenyl
R3 = H
X1 = H
X2 = OH		 przewalcyrone A[c] H. przewalskii[a] −109.29 (0.43, m)[b] Y. Duan 2019
51.16 R1 = (S)-s-Bu
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 przewalcyrone B[c] H. przewalskii[a] −132.38 (0.3, m)[b] Y. Duan 2019
51.17 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperwilsone F[c] H. wilsonii[a] −36.8 (0.4, m)[b] Y. Duan 2021c
51.18 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X1 = H
X2 = OH		 hyphenrone V H. henryi[a] H. Lév & Vaniot −38 (0.16, m)[b] Y. Liao 2016
51.19 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperwilsone G[c] H. wilsonii[a] −44.0 (0.3, m)[b] Y. Duan 2021c
51.20 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = H
X2 = OH		 hyperwilsone H[c] H. wilsonii[a] −60.6 (0.5, m)[b] Y. Duan 2021c
Structure 52: hyperhookerione H — A, bicyclononanes, exo
52
52.1 hyperhookerione H[c] H. hookerianum[a] −110 (0.5, m)[b] Z. Guo 2025b
Structure 53: hyperhookerione I — A, bicyclononanes, exo
53
53.1 hyperhookerione I[c] H. hookerianum[a] −163 (0.5, m)[b] Z. Guo 2025b
Structure 54: garcinielliptone H — A, bicyclononanes, exo
54
54.1 garcinielliptone H G. subelliptica[a] −14.3 (0.1)[b] J.-R. Weng 2003b
Structure 55: ascynol G — A, bicyclononanes, exo
55
55.1 ascynol G[c] H. ascyron[a] +78 (0.1, m)[b] Y.-L. Hu 2025
Structure 56: garcinielliptone G — A, bicyclononanes, exo
56
56.1 garcinielliptone G G. subelliptica[a] −53 (0.1)[b] J.-R. Weng 2003b, Y.-G. Fu 2025
Structure 57: hyperscabin D — A, bicyclononanes, exo
57
57.1 hyperscabin D[c] H. scabrum[a] +71.4 (0.08, mc)[b] J. Ma 2021b
Structure 58: hyperforone A — A, bicyclononanes, caged
58
58.1 hyperforone A[c] (one of two by that name) H. perforatum[a] −10.1 (0.1, m)[b] Y. Guo 2021b
Structure 59: hyperforone B — A, bicyclononanes, exo
59
59.1 hyperforone B[c] (one of two by that name) H. perforatum[a] −144.4 (0.5, m)[b] Y. Guo 2021b
Structure 60: hyperforone C — A, bicyclononanes, exo
60
60.1 hyperforone C[c] (one of two by that name) H. perforatum[a] −29.2 (0.3, m)[b] Y. Guo 2021b
Structure 61: hyperforone D — A, bicyclononanes, exo
61
61.1 hyperforone D[c] H. perforatum[a] +68.9 (0.9, m)[b] Y. Guo 2021b
Structure 62: hyperforone E — A, bicyclononanes, exo
62
62.1 hyperforone E[c] H. perforatum[a] −66.4 (0.3, m)[b] Y. Guo 2021b
Structure 63: hyperforone F — A, bicyclononanes, exo
63
63.1 hyperforone F[c] H. perforatum[a] −30.0 (0.8, m)[b] Y. Guo 2021b
Structure 64: hyperforone G — A, bicyclononanes, exo
64
64.1 hyperforone G[c] H. perforatum[a] −15.2 (0.4, m)[b] Y. Guo 2021b
Structure 65: hyperforone H — A, bicyclononanes, exo
65
65.1 hyperforone H[c] H. perforatum[a] −22.3 (0.9, m)[b] Y. Guo 2021b
Structure 66: hyperatin A — A, bicyclononanes, exo
66
66.1 hyperatin A[c] H. perforatum[a] +64.3 (0.1, m)[b] Y. Guo 2024
Structure 67: hyperatin D, hyperatin C, hyperatin B — A, bicyclononanes, exo
67
67.1 R = i-Pr
X = OH		 hyperatin D[c] H. perforatum[a] −24.5 (0.1, m)[b] Y. Guo 2024
67.2 R = i-PrO
X = OH		 hyperatin C[c] H. perforatum[a] −1.8 (0.2, m)[b] Y. Guo 2024
67.3 R = i-PrO
X = OMe		 hyperatin B[c] H. perforatum[a] −5.3 (0.2, m)[b] Y. Guo 2024
Structure 68: hyperacmose A, hyperacmose B — A, bicyclononanes, exo
68
68.1 R = i-Pr hyperacmose A[c] H. acmosepalum[a] +11.11 (2.8, m)[b] Z. Hu 2026
68.2 R = s-Bu hyperacmose B[c][e] H. acmosepalum[a] +8.63 (1.9, m)[b] Z. Hu 2026
Structure 69: hyperacmose C — A, bicyclononanes, exo
69
69.1 hyperacmose C[c] H. acmosepalum[a] +21.43 (0.56, m)[b] Z. Hu 2026
Structure 70: hypericumoxide N — A, bicyclononanes, exo
70
70.1 hypericumoxide N[d] H. scabrum[a] −24.2 (0.09, m)[b] R. Liu 2017
Structure 71: hyperpatone A — A, bicyclononanes, exo
71
71.1 hyperpatone A[c] H. patulum[a] −54.18 (0.3, m)[b] F. Zhang 2023
Structure 72: garcinielliptone J, norhyperpalum G, soulattrone A and others — A, bicyclononanes, exo
72
72.1 R1 = i-Pr
R2 = H		 garcinielliptone J G. subelliptica[a] −166 (0.2)[b] J.-R. Weng 2003b
72.2 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH		 norhyperpalum G[c] H. patulum[a] +107.6 (0.5, m)[b] Y. Duan 2021b
72.3 R1 = (S)-s-Bu
R2 = H		 soulattrone A Calophyllum soulattri +157.3 (0.19, e)[b] S. K. Nigam 1988
72.4 R1 = s-Bu
R2 = (E)-CH=CHCMe2OH		 norhyperpalum F[c][e] H. patulum[a] +92.0 (0.6, m)[b] Y. Duan 2021b
Structure 73: hyphenrone A, perforatumone, hyperuralone C and others — A, bicyclononanes, exo
73
73.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyphenrone A[c] H. henryi[a] −23.8 (0.25, m)[b] X.-W. Yang 2014
73.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl		 perforatumone[d] (prob. enantiomer) H. perforatum[a] +153 (2.9, a)[b] J. Wu 2004, X.-W. Yang 2015
73.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 hyperuralone C H. uralum[a] +3 (0.25, m)[b] J.-J. Zhang 2015
73.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH		 hyperuralone E H. uralum[a] +2 (0.11, m)[b] J.-J. Zhang 2015
73.5 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl		 attenuatumione B H. attenuatum[a] +4.8 (0.19)[b] Z.-B. Zhou 2014, J.-J. Zhang 2015
73.6 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
R4 = prenyl		 hyphenrone Y (one of two by that name) H. henryi[a] +10 (0.2, m)[b] F. Hu 2023
73.7 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyphenrone H[c] H. henryi[a] −4 (0.1, m)[b] X.-W. Yang 2015
73.8 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 hyperuralone D[e] H. uralum[a] +4 (0.09, m)[b] J.-J. Zhang 2015
73.9 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH		 hyperuralone F[e] H. uralum[a] +2 (0.11, m)[b] J.-J. Zhang 2015
73.10 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyphenrone B[c] H. henryi[a] −39.8 (0.09, m)[b] X.-W. Yang 2014
Structure 74: hyperfol H — A, bicyclononanes, exo
74
74.1 hyperfol H[c][dd] H. perforatum[a] −203 (0.3, m)[b] H. Lou 2020b
Structure 75: hyperfol B — A, bicyclononanes, exo
75
75.1 hyperfol B[c] H. perforatum[a] −33.24 (0.09, m)[b] H.-Y. Lou 2020a
Structure 76: hyperkouytone N — A, bicyclononanes, exo
76
76.1 hyperkouytone N[c] H. kouytchense[a] −14.2 (0.24, m)[b] H.-Y. Lou 2024
Structure 77: hyperuralone G, hyperuralone H — A, bicyclononanes, endo
77
77.1 R = i-Pr hyperuralone G H. uralum[a] −37 (0.11, m)[b] J.-J. Zhang 2015
77.2 R = s-Bu hyperuralone H[e] H. uralum[a] −38 (0.3, m)[b] J.-J. Zhang 2015
Structure 78: hyphenrone C, hyphenrone I — A, bicyclononanes, exo
78
78.1 R = i-Pr hyphenrone C[c] H. henryi[a] −32.9 (0.10, m)[b] X.-W. Yang 2014, X.-W. Yang 2015
78.2 R = (S)-s-Bu hyphenrone I[c] H. henryi[a] +22 (0.1, m)[b] X.-W. Yang 2015
Structure 79: ascynol H — A, bicyclononanes, exo
79
79.1 ascynol H[c] H. ascyron[a] −22 (0.3, m)[b] Y.-L. Hu 2025
Structure 80: hyphenrone D — A, bicyclononanes, exo
80
80.1 hyphenrone D[c] H. henryi[a] −62.5 (0.10, m)[b] X.-W. Yang 2014
Structure 81: hyperlanin A — A, bicyclononanes, exo
81
81.1 hyperlanin A, a.k.a. hyperforatone A[c] (one of two by the second name) H. lancasteri[a] −18.0 (0.3, m)[b] J.-Q. You 2024, W.-Y. Liu 2025a
Structure 82: hyperfol A — A, bicyclononanes, exo
82
82.1 hyperfol A[c] H. perforatum[a] −202.49 (0.3, m)[b] H.-Y. Lou 2020a
Structure 83: ascynol J, hyphenrone F, hyperpatuone M and others — A, bicyclononanes, exo
83
83.1 R1 = i-Pr
R2 = H
R3 = Me
R4 = (E)-CH=CHCMe2OH		 ascynol J[c] H. ascyron[a] −30 (0.1, m)[b] Y.-L. Hu 2025
83.2 R1 = i-Pr
R2 = H
R3 = prenyl
R4 = prenyl		 hyphenrone F[c] H. henryi[a] −140 (0.10, m)[b] X.-W. Yang 2014
83.3 R1 = i-Pr
R2 = CO2Me
R3 = prenyl
R4 = prenyl		 hyperpatuone M[c] H. patulum[a] −52 (0.3, m)[b] F. Zhang 2026
83.4 R1 = s-Bu
R2 = H
R3 = Me
R4 = (E)-CH=CHCMe2OH		 ascynol K[c][e] H. ascyron[a] −24 (0.1, m)[b] Y.-L. Hu 2025
83.5 R1 = Ph
R2 = H
R3 = Me
R4 = prenyl		 ascyronone C H. ascyron[a] −151 (0.30, m)[b] L.-M. Kong 2017
83.6 R1 = Ph
R2 = H
R3 = Me
R4 = (E)-CH=CHCMe2OH		 ascynol I[c] H. ascyron[a] −149 (0.1, m)[b] Y.-L. Hu 2025
Structure 84: hyperforen A — A, bicyclononanes, exo
84
84.1 hyperforen A[c] H. perforatum[a] +9.53 (0.05, m)[b] H. Lou 2022
Structure 85: ascyronone A, hyperforcinol K, ascyronone B and others — A, bicyclononanes, exo
85
85.1 R1 = i-Pr
R2 = Me		 ascyronone A H. ascyron[a] +87 (0.04, m)[b] L.-M. Kong 2017
85.2 R1 = i-Pr
R2 = prenyl		 hyperforcinol K[c] H. forrestii[a] +57 (0.9, m)[b] W.-J. Lu 2021
85.3 R1 = s-Bu
R2 = Me		 ascyronone B[e] H. ascyron[a] +108 (0.11, m)[b] L.-M. Kong 2017
85.4 R1 = s-Bu
R2 = prenyl		 hyperforcinol E[c][e] H. forrestii[a] +70 (0.3, m)[b] W.-J. Lu 2021
Structure 86: uralin B — A, bicyclononanes, exo
86
86.1 uralin B[c] H. uralum[a] +63 (0.3, m)[b] Q.-Q. Fang 2021
Structure 87: hypsampsone A — B, bicyclononanes, endo
87
87.1 hypsampsone A[d] H. sampsonii[a] +71.49 (0.7, m)[b] Z.-Z. Zhang 2021
Structure 88: hypersampone A — A, bicyclononanes, exo
88
88.1 hypersampone A[d] H. sampsonii[a] −70.01 (1.7, m)[b] L. Huang 2022
Structure 89: hypersampone B, hypersampone C — A, bicyclononanes, exo
89
89.1 R = OBz hypersampone B[d] H. sampsonii[a] −67.93 (1.8, m)[b] L. Huang 2022
89.2 R = Bz hypersampone C[d] H. sampsonii[a] −21.54 (1.9, m)[b] L. Huang 2022
Structure 90: hyreptaone B, hyreptaone A, hyreptaone C — A, bicyclononanes, endo
90
90.1 R = i-Pr hyreptaone B[c] H. reptans[a] –75 (0.276, m)[b] Y. Zhou 2026
90.2 R = i-Bu hyreptaone A[c] H. reptans[a] –96 (0.046, m)[b] Y. Zhou 2026
90.3 R = (R)-s-Bu hyreptaone C[c] H. reptans[a] –78 (0.167, m)[b] Y. Zhou 2026
Structure 91: hyperadditionciol I — A, bicyclononanes, endo
91
91.1 hyperadditionciol I[d] H. addingtonii[a] –94 (0.05, m)[b] J. Chen 2026
Structure 92: hyperadditionciol J — A, bicyclononanes, endo
92
92.1 hyperadditionciol J[d] H. addingtonii[a] –10 (0.05, m)[b] J. Chen 2026
Structure 93: hyreptaone D, hyreptaone E — A, bicyclononanes, endo
93
93.1 R = i-Bu hyreptaone D[c] H. reptans[a] +46 (0.125, m)[b]  Y. Zhou 2026
93.2 R = (S)-s-Bu hyreptaone E[c] H. reptans[a] +61 (0.193, m)[b]  Y. Zhou 2026
Structure 94: hyperscabin A, norhyperpalum E — A, bicyclononanes, exo
94
94.1 R = i-Pr hyperscabin A[c] H. scabrum[a] +37.9 (0.05, mc)[b] J. Ma 2021a
94.2 R = s-Bu norhyperpalum E[c][e] H. patulum[a] +55.1 (0.3, m)[b] Y. Duan 2021b
Structure 95: hyperscabin B, hyperscabin C, norhyperpalum D — A, bicyclononanes, exo
95
95.1 R = i-Pr hyperscabin B[c] H. scabrum[a] +75.6 (0.18, mc)[b] J. Ma 2021a
95.2 R = s-Bu hyperscabin C[c][e] H. scabrum[a] +66.2 (0.08, mc)[b] J. Ma 2021a
95.3 R = Ph norhyperpalum D[c] H. patulum[a] −47.1 (0.2, m)[b] Y. Duan 2021b
Structure 96: hyperacmosin K, norhyperpalum B — A, bicyclononanes, exo
96
96.1 R = i-Pr hyperacmosin K[c] H. acmosepalum[a] +109.4 (0.1115, m)[b] M. Sun 2021a
96.2 R = Ph norhyperpalum B[c] H. patulum[a] −14.7 (0.6, m)[b] Y. Duan 2021b
Structure 97: hyperacmosin L, norhyperpalum C — A, bicyclononanes, exo
97
97.1 R = i-Pr hyperacmosin L[c] H. acmosepalum[a] +133.8 (0.068, m)[b] M. Sun 2021a
97.2 R = Ph norhyperpalum C[c] H. patulum[a] +3.3 (0.3, m)[b] Y. Duan 2021b
Structure 98: norhyperpalum A — A, bicyclononanes, endo
98
98.1 norhyperpalum A[d] H. patulum[a] −53.7 (0.3, m)[b] Y. Duan 2021b
Structure 99: hyperscabin E — A, bicyclononanes, endo
99
99.1 hyperscabin E[c] H. scabrum[a] +103.2 (0.14, mc)[b] J. Ma 2021b
Structure 100: hypertum A — A, bicyclononanes, exo
100
100.1 hypertum A[c] H. perforatum[a] −8.5 (0.05, m)[b] W.-Y. Liu 2025b
Structure 101: hyperhexanone F, hyperhexanone A, hyperacmosin M — A, bicyclononanes, endo
101
101.1 R1 = prenyl
R2 = Me		 hyperhexanone F[c] H. sampsonii[a] −40 (0.3, m)[b] Z.-Z. Zhang 2021
101.2 R1 = geranyl
R2 = Me		 hyperhexanone A[c] H. sampsonii[a] −13.3 (0.30)[b] H. Zhu 2016
101.3 R1 = geranyl
R2 = Et		 hyperacmosin M[c] H. acmosepalum[a] −54.5 (0.044, m)[b] M. Sun 2021a
Structure 102: hyperforcinol D — A, bicyclononanes, endo
102
102.1 hyperforcinol D[c] H. forrestii[a] +4 (0.7, m)[b] W.-J. Lu 2021
Structure 103: hyperadditionciol G — A, bicyclononanes, endo
103
103.1 hyperadditionciol G[c] H. addingtonii[a] +10 (0.05, m)[b] J. Chen 2026
Structure 104: hyperacmosin D, hyperacmosin C — A, bicyclononanes, endo
104
104.1 R = i-Pr hyperacmosin D[c] H. acmosepalum[a] −25.45 (0.22, m)[b] X.-y. Suo 2021a
104.2 R = (S)-s-Bu hyperacmosin C[c] H. acmosepalum[a] −12.30 (0.26, m)[b] X.-y. Suo 2021a
Structure 105: hyperadditionciol H — A, bicyclononanes, endo
105
105.1 hyperadditionciol H[c] H. addingtonii[a] –16 (0.05, m)[b] J. Chen 2026
Structure 106: hyperbenzone A — A, bicyclononanes, endo
106
106.1 hyperbenzone A[c] H. beanii[a] −4 (0.2, m)[b] W. Lu 2021
Structure 107: hyperbenzone B — A, bicyclononanes, endo
107
107.1 hyperbenzone B[c] H. beanii[a] +12 (0.1, m)[b] W. Lu 2021
Structure 108: spirohypolactone A — A, bicyclononanes, exo
108
108.1 spirohypolactone A[c] H. perforatum[a] +65.6 (0.6, m)[b] Y. Guo 2019a
Structure 109: spirohypolactone B, norhyperpalum H, hyperisenin B — A, bicyclononanes, exo
109
109.1 R1 = i-Pr
R2 = CH2CH2CH=CMe2		 spirohypolactone B[c] H. perforatum[a] +43.5 (0.6, m)[b] Y. Guo 2019a
109.2 R1 = s-Bu
R2 = CH2CH2CH=CMe2		 norhyperpalum H[c][e] H. patulum[a] +44.3 (0.5, m)[b] Y. Duan 2021b
109.3 R1 = Ph
R2 = (E)-CH=CHCH=CMe2		 hyperisenin B[c] H. seniawinii[a] +48.8 (0.3, m)[b] Y. Duan 2025
Structure 110: norhyperpalum I, hyperhexanone C, hyperhexanone D — A, bicyclononanes, exo
110
110.1 R = i-Pr
X = H		 norhyperpalum I[c] H. patulum[a] −9.6 (0.6, m)[b] Y. Duan 2021b
110.2 R = i-Pr
X = OH		 hyperhexanone C[c] H. perforatum[a] −17.8 (0.6, m)[b] Y. Guo 2019a
110.3 R = s-Bu
X = OH		 hyperhexanone D[c][e] H. perforatum[a] −30.3 (0.4, m)[b] Y. Guo 2019a
Structure 111: hyperhexanone E — A, bicyclononanes, endo
111
111.1 hyperhexanone E[c] H. perforatum[a] −139.0 (0.3, m)[b] Y. Guo 2019a
Structure 112: norsampsone A, norsampsone C, norgarmultinone A — A, bicyclononanes, endo
112
112.1 R = prenyl norsampsone A[c] H. sampsonii[a] +23.4 (0.50)[b] W.-J. Tian 2014a
112.2 R = geranyl norsampsone C[c] H. sampsonii[a] +26.0 (0.50)[b] W.-J. Tian 2014a
112.3 R = lavandulyl norgarmultinone A[c][e] G. multiflora[a] +77.78 (0.02, m)[b] H. Teng 2020
Structure 113: norsampsone B, norsampsone D — A, bicyclononanes, endo
113
113.1 R = prenyl norsampsone B[c] H. sampsonii[a] −28.6 (0.50)[b] W.-J. Tian 2014a
113.2 R = geranyl norsampsone D[c] H. sampsonii[a] −28.2 (0.50)[b] W.-J. Tian 2014a
Structure 114: norwilsonnol B — A, bicyclononanes, exo
114
114.1 norwilsonnol B[d] H. wilsonii[a] +111.0 (0.5, m)[b] S. Xie 2021
Structure 115: hyperisenin A — A, bicyclononanes, exo
115
115.1 hyperisenin A[d] H. seniawinii[a] +42.0 (0.1, m)[b] Y. Duan 2025
Structure 116: hypertum B — A, bicyclononanes, exo
116
116.1 hypertum B[c] H. perforatum[a] −9.5 (0.15, m)[b] W.-Y. Liu 2025b
Structure 117: norwilsonnol A — A, bicyclononanes, exo
117
117.1 norwilsonnol A[c] H. wilsonii[a] −174.0 (0.7, m)[b] S. Xie 2021
Structure 118: hyperwilsol A — A, bicyclononanes, exo
118
118.1 hyperwilsol A[c] H. wilsonii[a] −5.55 (0.08, m)[b] Z.-X. Wang 2025
Structure 119: hypseudohenrin H — A, bicyclononanes, exo
119
119.1 hypseudohenrin H[c] H. wilsonii[a] −8.56 (1.29, m)[b] M.-X. Sun 2024
Structure 120: hypertum C — A, bicyclononanes, exo
120
120.1 hypertum C[c] H. perforatum[a] −26.8 (0.05, m)[b] W.-Y. Liu 2025b
Structure 121: hypertum D, hypertum E — A, bicyclononanes, exo
121
121.1 X1 = OMe
X2 = H		 hypertum D[c] H. perforatum[a] mixture with hypertum E: −40.1 (0.1, m)[b] W.-Y. Liu 2025b
121.2 X1 = H
X2 = OMe		 hypertum E[c] H. perforatum[a] mixture with hypertum D: −40.1 (0.1, m)[b] W.-Y. Liu 2025b
Structure 122: norgarmultinone B — A, bicyclononanes, exo
122
122.1 norgarmultinone B[c] G. multiflora[a] +43.37 (0.07, m)[b] H. Teng 2020
Structure 123: hypseudohenrin C — A, bicyclononanes, endo
123
123.1 hypseudohenrin C[c] H. pseudohenryi[a] +10.5 (1.14, m)[b] H. Sun 2021b
Structure 124: hyperwilsol D — A, bicyclononanes, exo
124
124.1 hyperwilsol D[c] H. wilsonii[a] −81.55 (0.04, m)[b] Z.-X. Wang 2025
Structure 125: hypseudohenrin D — A, bicyclononanes, endo
125
125.1 hypseudohenrin D[c] H. pseudohenryi[a] +10.9 (1.29, m)[b] H. Sun 2021b
Structure 126: garcinielliptone O, no name, hyperwilsol C and others — A, bicyclononanes, exo
126
126.1 R1 = i-Pr
R2 = H		 garcinielliptone O G. subelliptica[a] −277 (0.16)[b] J.-R. Weng 2004
126.2 R1 = i-Pr
R2 = prenyl		 no common name H. perforatum[a] +95.5 (1.1)[b] M. D. Shan 2001
126.3 R1 = (R)-s-Bu
R2 = prenyl		 hyperwilsol C[c] H. wilsonii[a] +93.99 (0.05, m)[b] Z.-X. Wang 2025
126.4 R1 = Ph
R2 = H		 hyperibrin G[d] H. scabrum[a] +80.2 (0.06, m)[b] J. Hu 2017
Structure 127: hypertum F, hypertum G — A, bicyclononanes, exo
127
127.1 R = i-Pr hypertum F[c] H. perforatum[a] +40.2 (0.02, m)[b] W.-Y. Liu 2025b
127.2 R = (S)-s-Bu hypertum G[c] H. perforatum[a] +49.5 (0.02, m)[b] W.-Y. Liu 2025b
Structure 128: spirohypertone B — A, bicyclononanes, exo
128
128.1 spirohypertone B[c] H. patulum[a] −15.2 (0.1, m)[b] Y. Duan 2024b
Structure 129: hypseudohenrin A, hypseudohenrin B — A, bicyclononanes, exo
129
129.1 R = CO2Me hypseudohenrin A[c] H. pseudohenryi[a] +9.8 (1.43, m)[b] H. Sun 2021b
129.2 R = H hypseudohenrin B[c] H. pseudohenryi[a] +12.9 (1.86, m)[b] H. Sun 2021b
Structure 130: hyperibrin A, hyperibrin B, hyperscabrone H and others — A, bicyclononanes, seco
130
130.1 R1 = i-Pr
R2 = Me
R3 = prenyl
X = H		 hyperibrin A[c] H. scabrum[a] +37.0 (0.05, m)[b] W. Gao 2016c
130.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = OH		 hyperibrin B, a.k.a. hypermonone I[c] H. monogynum, H. scabrum[a] +53.2 (0.08, m)[b], +46.03 (0.08, m)[b] W. Gao 2016c, X. Wang 2021b, Y.-R. Zeng 2021c
130.3 R1 = i-Pr
R2 = Me
R3 = prenyl
X = OOH		 hyperscabrone H[c] H. scabrum[a] +8.3 (0.1, m)[b] W. Gao 2016a, X. Wang 2021b
130.4 R1 = i-Pr
R2 = prenyl
R3 = H
X = H		 garcinielliptone N G. subelliptica[a] −42 (0.38)[b] J.-R. Weng 2004
130.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X = H		 no common name H. perforatum[a] +18.3 (1.8)[b] M. D. Shan 2001
130.6 R1 = i-Bu
R2 = Me
R3 = (E)-CH=CHCMe2OH
X = H		 ascynol F[c] H. ascyron[a] +22 (0.1, m)[b] Y.-L. Hu 2025
130.7 R1 = s-Bu
R2 = Me
R3 = prenyl
X = H		 hypermonone H[c] H. monogynum[a] +7.88 0.24, m) Y.-R. Zeng 2021c
130.8 R1 = s-Bu
R2 = Me
R3 = prenyl
X = OOH		 hyperscabrone I[c][e] H. scabrum[a] +24 (0.1, m)[b] W. Gao 2016a, X. Wang 2021b
130.9 R1 = Ph
R2 = Me
R3 = prenyl
X = H		 norascyronone C H. ascyron[a] +15 (0.1, m)[b] Y.-L. Hu 2019
130.10 R1 = Ph
R2 = prenyl
R3 = prenyl
X = H		 hypseudohenrin E[c] H. pseudohenryi[a] +4.96 (3.43, m)[b] H. Sun 2021b
130.11 R1 = Ph
R2 = geranyl
R3 = H
X = H		 hyperhexanone B[c] H. sampsonii[a] −14.6 (0.15)[b] H. Zhu 2016
Structure 131: hyperscabrin A, hyperscabin K, hyperscabin L — A, bicyclononanes, seco
131
131.1 R1 = i-Pr
R2 = H		 hyperscabrin A[c] H. scabrum[a] −85.1 (0.06, mc)[b] J. Ma 2012
131.2 R1 = i-Pr
R2 = prenyl		 hyperscabin K[d] H. scabrum[a] −198.3 (0.17, mc)[b] J. Ma 2021b
131.3 R1 = s-Bu
R2 = prenyl		 hyperscabin L[d][e] H. scabrum[a] −178.4 (0.19, mc)[b] J. Ma 2021b
Structure 132: hyperscabin J — A, bicyclononanes, seco
132
132.1 hyperscabin J[c] H. scabrum[a] +36.6 (0.07, mc)[b] J. Ma 2021b
Structure 133: hyperscabrin B, hyperscabrin C — A, bicyclononanes, seco
133
133.1 R = i-Pr hyperscabrin B[c] H. scabrum[a] +27.6 (0.08, mc)[b] J. Ma 2012
133.2 R = s-Bu hyperscabrin C[c][e] H. scabrum[a] +22.4 (0.10, mc)[b] J. Ma 2012
Structure 134: norhypersampsone A — A, bicyclononanes, seco
134
134.1 norhypersampsone A H. sampsonii[a] −40.0 (0.5)[b] J.-S. Zhang 2017
Structure 135: yezo'otogirin C, yezo'otogirin A, ascynol E and others — A, bicyclononanes, caged
135
135.1 R1 = i-Pr
R2 = Me		 yezo'otogirin C[c] H. yezoense[a] −57.2 (0.05)[b] N. Tanaka 2009b
135.2 R1 = i-Pr
R2 = prenyl		 yezo'otogirin A[c] H. yezoense[a] −168.2 (0.25)[b] N. Tanaka 2009b
135.3 R1 = i-Bu
R2 = Me		 ascynol E[c] H. ascyron[a] −39 (0.2, m)[b] Y.-L. Hu 2025
135.4 R1 = (S)-s-Bu
R2 = Me		 hypermogin A[c] H. monogynum[a] −164.7 (0.2, m)[b] Y.-R. Zeng 2021a
135.5 R1 = (S)-s-Bu
R2 = prenyl		 yezo'otogirin B[c] H. yezoense[a] −165.7 (0.15)[b] N. Tanaka 2009b
Structure 136: hypermogin C, hypermogin B — A, bicyclononanes, caged
136
136.1 R = i-Pr hypermogin C[c] H. monogynum[a] −48.9 (0.12, m)[b] Y.-R. Zeng 2021a
136.2 R = (S)-s-Bu hypermogin B[c] H. monogynum[a] −38.0 (0.2, m)[b] Y.-R. Zeng 2021a
Structure 137: hypermogin D — A, bicyclononanes, caged
137
137.1 hypermogin D[c] H. monogynum[a] −32.0 (0.2, m)[b] Y.-R. Zeng 2021a
Structure 138: ascynol D — A, bicyclononanes, caged
138
138.1 ascynol D[c] H. ascyron[a] −31 (0.1, m)[b] Y.-L. Hu 2025
Structure 139: ascynol B — A, bicyclononanes, caged
139
139.1 ascynol B[c] H. ascyron[a] +17 (0.1, m)[b] Y.-L. Hu 2025
Structure 140: ascynol C — A, bicyclononanes, caged
140
140.1 ascynol C[c] H. ascyron[a] −82 (0.06, m)[b] Y.-L. Hu 2025
Structure 141: ascynol A — A, bicyclononanes, caged
141
141.1 ascynol A[c] H. ascyron[a] −42.6 (0.06, m)[b] Y.-L. Hu 2025
Structure 142: norascyronone A, norascyronone B — A, bicyclononanes, caged
142
142.1 X = H norascyronone A[c] H. ascyron[a] +68 (0.2, m)[b] Y.-L. Hu 2019
142.2 X = OH norascyronone B[c] H. ascyron[a] +22 (0.2, m)[b] Y.-L. Hu 2019
Structure 143: norprzewalsone A — A, bicyclononanes, caged
143
143.1 norprzewalsone A[c] H. przewalskii[a] +76.7 (0.4, m)[b] Y. Duan 2022b
Structure 144: hyperforatum A — A, bicyclononanes, exo
144
144.1 hyperforatum A[c] H. perforatum[a] +2 (0.1, m)[b] X. Wang 2024
Structure 145: hyperforatum B — A, bicyclononanes, endo
145
145.1 hyperforatum B[e] H. perforatum[a] +7.5 (1.00, m)[b] X. Wang 2024
Structure 146: hyperforatum C — A, bicyclononanes, seco
146
146.1 hyperforatum C[e] H. perforatum[a] +5.9 (0.35, m)[b] X. Wang 2024
Structure 147: hyperforone I, norprzewalsone B — A, bicyclononanes, exo
147
147.1 R = i-Pr hyperforone I[c] H. perforatum[a] +60.9 (0.6, m)[b] Y. Guo 2021b
147.2 R = s-Bu norprzewalsone B[c][e] H. przewalskii[a] +48.4 (0.3, m)[b] Y. Duan 2022b
Structure 148: hyperforone J — A, bicyclononanes, exo
148
148.1 hyperforone J[c] H. perforatum[a] −110.0 (0.3, m)[b] Y. Guo 2021b
Structure 149: hookerione C, hypersubone C, hookerione A and others — A, bicyclononanes, caged
149
149.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hookerione C[d] H. hookerianum[a] +2 (0.25, m)[b] Y. Ye 2016
149.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = CH=CMe2		 hypersubone C[d] H. subsessile[a] −13.3 (3.20, m)[b] Y. Liao 2015
149.3 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hookerione A[d] H. hookerianum[a] +5 (0.25, m)[b] Y. Ye 2016
149.4 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hookerione B[d] H. hookerianum[a] +32 (0.11, m)[b] Y. Ye 2016
149.5 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hirsuton B[d] H. hirsutum[a] +6.6 (0.30, m)[b] J. Max 2021
149.6 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hirsuton A[d] H. hirsutum[a] +3.7 (0.83, m)[b] J. Max 2021
149.7 R1 = s-Bu
R2 = geranyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hookerione D[d][e] H. hookerianum[a] −27 (0.13, m)[b] Y. Ye 2016
149.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH=CMe2		 plukenetione A C. plukenetii[a] +1 (0.8)[b] G. E. Henry 1996
149.9 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 (−)-28,29-epoxyplukenetione A[c] C. havetiodes[a] var. stenocarpa, C. obdeltifolia[a] −4.4 (1.0)[b] O. E. Christian 2001, J. S. A. R. Teixeira 2005
149.10 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 (+)-28,29-epoxyplukenetione A[d] (enantiomer) H. sampsonii[a] +8.8 (0.54)[b] H. Zhu 2014
149.11 R1 = Ph
R2 = (Z)-CH=CHCMe2OH
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 wilsonglucinol H[d] H. wilsonii[a] +2.4 (0.5, m)[b] H. Cheng 2022a
149.12 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 sampsonione Q[d] H. sampsonii[a] −9.65 (0.401)[b] Z. Y. Xiao 2007
149.13 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S,S)-3-prenylmethyl-3-methyloxiran-2-yl		 hyperandrone A H. androsaemum[a] +20.9 (0.25, m)[b] K. Wang 2012, X.-W. Yang 2018
149.14 R1 = Ph
R2 = prenyl
R3 = (E)-4-oxo-3-methyl-2-buten-1-yl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hyperwilone A[d] H. wilsonii[a] +39.3 (0.65)[b] J. Hao 2021
149.15 R1 = Ph
R2 = (E,R,R)-3,5-dimethyl-1-hepten-1-yl
R3 = (E,E)-6-oxo-3,4-dimethyl-2,4-hexadien-1-yl
R4 = CH=CMe2		 sinaicinone H. sinaicum[a] +37.5 (0.17, mc)[b] T. Řezanka 2007
149.16 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = CH=CMe2		 otogirinin A H. erectum[a] Thunb., H. attenuatum[a] − 8.1 (0.08, m)[b] Y. Ishida 2010, D. Li 2015a
149.17 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 sampsonione J[d] H. sampsonii[a] +1.48 (0.2)[b] L.-H. Hu 1999a, H. Zhu 2014
149.18 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hyperisampsin G[d] H. sampsonii[a] −8.7 (0.80)[b] H. Zhu 2014
149.19 R1 = Ph
R2 = (R)-lavandulyl[f]
R3 = prenyl
R4 = CH=CMe2		 garcimultiflorone N[c][t][u][x] G. multiflora[a] −28.9 (0.090, m)[b] Z.-Q. Wang 2018
149.20 R1 = Ph
R2 = lavandulyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 epi-isosampsonione J[d][e] G. multiflora[a] +55.0 (0.02, m)[b] Y. Chen 2019a
149.21 R1 = Ph
R2 = lavandulyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 garcimultiflorone D, a.k.a. isosampsonione J[e] (one of two by the first name) G. multiflora[a] +5.6 (0.12)[b] C.-W. Ting 2012, Y. Chen 2019a
149.22 R1 = Ph
R2 = (E,E)-7-hydroxy-3,7-dimethyl-2,5-octadienyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hypersubone D[d] H. subsessile[a] −32.8 (0.07, m)[b] T.-W. Cao 2020
149.23 R1 = Ph
R2 = (E)-5-(3,3-dimethyloxiran-2-yl)-3-methyl-2-penten-1-yl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hypersubone E[d][e] H. subsessile[a] −12.7 (0.27, m)[b] T.-W. Cao 2020
Structure 150: cumilcinol G, hyperattenin J — A, bicyclononanes, caged
150
150.1 R = prenyl cumilcinol G[d] H. wilsonii[a] +104.7 (0.2, m)[b] B. Tao 2024a
150.2 R = geranyl hyperattenin J[d] H. attenuatum[a] Choisy +23.8 (0.3, m)[b] D. Li 2015b
Structure 151: hyperadaman D — A, bicyclononanes, caged
151
151.1 hyperadaman D[d] H. wilsonii[a] +47.7 (0.2, m)[b] B. Tao 2024b
Structure 152: wilsonglucinol I — A, bicyclononanes, caged
152
152.1 wilsonglucinol I[d] H. wilsonii[a] +20.9 (0.25, m)[b] H. Cheng 2022a
Structure 153: garciyunnanone G — A, bicyclononanes, caged
153
153.1 garciyunnanone G[d] G. yunnan[a] Hu +4.4 (0.1, m)[b] M. Nan 2024
Structure 154: hyperadaman G, hyperadaman F — A, bicyclononanes, caged
154
154.1 R = i-Pr hyperadaman G[d] H. wilsonii[a] +43.2 (0.2, m)[b] B. Tao 2024b
154.2 R = Ph hyperadaman F[d] H. wilsonii[a] +87.7 (0.6, m)[b] B. Tao 2024b
Structure 155: hyperadaman B, hyperadaman A — A, bicyclononanes, caged
155
155.1 R = CH2COCHMe2 hyperadaman B[d] H. wilsonii[a] +5.7 (0.2, m)[b] B. Tao 2024b
155.2 R = CH2COC(Me)=CH2 hyperadaman A[d] H. wilsonii[a] +17.0 (0.1, m)[b] B. Tao 2024b
Structure 156: hyperadaman E — A, bicyclononanes, caged
156
156.1 hyperadaman E[d][z] H. wilsonii[a] +86.0 (0.2, m)[b] B. Tao 2024b
Structure 157: hyperisampsin B, hyperattenin L, garciyunnanone D — A, bicyclononanes, caged
157
157.1 R1 = geranyl
R2 = i-Pr
X = OH		 hyperisampsin B[d] H. sampsonii[a] +2.6 (0.08)[b] H. Zhu 2014
157.2 R1 = geranyl
R2 = i-Pr
X = OOH		 hyperattenin L[d] H. attenuatum[a] −1.7 (0.42)[b] D. Li 2018
157.3 R1 = lavandulyl[f]
R2 = H
X = OOH		 garciyunnanone D[d][e] G. yunnan[a] Hu −5.4 (0.2, m)[b] M. Nan 2024
Structure 158: hyperihirsolin A, hyperihirsolin B, hyperesternoid L and others — A, bicyclononanes, caged
158
158.1 R1 = i-Pr
R2 = prenyl
X = OH		 hyperihirsolin A H. hirsutum[a] −25.3 (0.62, m)[b] J. Max 2021
158.2 R1 = s-Bu
R2 = prenyl
X = OH		 hyperihirsolin B[e] H. hirsutum[a] −13.0 (0.90, m)[b] J. Max 2021
158.3 R1 = Ph
R2 = prenyl
X = OH		 hyperesternoid L[d] H. monogynum[a] −32.2 (0.2, m)[b] Z. Dong 2026a
158.4 R1 = Ph
R2 = geranyl
X = OH		 hyperisampsin A[d] H. sampsonii[a] −25.9 (0.16)[b] H. Zhu 2014
158.5 R1 = Ph
R2 = (R)-lavandulyl[f]
X = OH		 garcimultiflorone O[c][t][v][x] G. multiflora[a] +1.4 (0.73, m)[b] Z.-Q. Wang 2018
158.6 R1 = Ph
R2 = lavandulyl[f]
X = OOH		 garciyunnanone C[d][e] G. yunnan[a] Hu −5.4 (0.2, m)[b] M. Nan 2024
Structure 159: hypersampsonone M, hyperisampsin C, isohyperisampsin C and others — A, bicyclononanes, caged
159
159.1 R = prenyl hypersampsonone M[d] H. sampsonii[a] +10 (1.0, m)[b] Y. Li 2023
159.2 R = geranyl hyperisampsin C[d] H. sampsonii[a] −19.7 (0.30)[b] H. Zhu 2014
159.3 R = lavandulyl isohyperisampsin C[c][e] G. multiflora[a] +93.3 (0.02, m)[b] Y. Chen 2019a
159.4 R = (R)-lavandulyl[f] garciyunnanone E[d] G. yunnan[a] Hu +8.0 (0.2, m)[b] M. Nan 2024
Structure 160: hyperadaman C — A, bicyclononanes, caged
160
160.1 hyperadaman C[d] H. wilsonii[a] +36.2 (0.2, m)[b] B. Tao 2024b
Structure 161: hyperesternoid M, hyperisampsin D — A, bicyclononanes, caged
161
161.1 R = prenyl
X = OH		 hyperesternoid M[d] H. monogynum[a] −42.8 (0.1, m)[b] Z. Dong 2026a
161.2 R = geranyl
X = OOH		 hyperisampsin D[d] H. sampsonii[a] −25.1 (0.12)[b] H. Zhu 2014
Structure 162: hyperesternoid N, hypersubone B, hyperadditionciol D and others — A, bicyclononanes, caged
162
162.1 R = prenyl
X = OOH		 hyperesternoid N[d] H. monogynum[a] −38.8 (0.2, m)[b] Z. Dong 2026a
162.2 R = geranyl
X = OH		 hypersubone B[d] H. subsessile[a] −52.2 (0.09, m)[b] Y. Liao 2015
162.3 R = geranyl
X = OOH		 hyperadditionciol D[d] H. addingtonii[a] −40 (0.05, m)[b] J. Chen 2026
162.4 R = lavandulyl
X = OOH		 garciyunnanone F[d] G. yunnan[a] Hu −63.2 (0.2, m)[b] M. Nan 2024
Structure 163: cumilcinol H, hyperisampsin E, no name and others — A, bicyclononanes, caged
163
163.1 R1 = i-Pr
R2 = prenyl
R3 = CMe=CH2
X = OH		 cumilcinol H[d] H. wilsonii[a] −6.6 (0.5, m)[b] B. Tao 2024a
163.2 R1 = Ph
R2 = prenyl
R3 = CMe=CH2
X = OH		 hyperisampsin E[d] H. sampsonii[a] +9.5 (0.23, m)[b] H. Zhu 2014
163.3 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 no common name C. obdeltifolia[a] +10.0 (0.4)[b] J. S. A. R. Teixeira 2005
163.4 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperisampsin F[d] H. sampsonii[a] +2.0 (0.10, m)[b] H. Zhu 2014
163.5 R1 = Ph
R2 = geranyl
R3 = CMe=CH2
X = OH		 sampsonione I[d] H. sampsonii[a] +16.88 (0.1)[b] L.-H. Hu 1999a, H. Zhu 2014
163.6 R1 = Ph
R2 = (R)-lavandulyl[f]
R3 = CMe=CH2
X = OH		 garciyunnanone A[d] G. yunnan[a] Hu +6.6 (0.1, m)[b] M. Nan 2024
Structure 164: garciyunnanone B — A, bicyclononanes, caged
164
164.1 garciyunnanone B[d][e] G. yunnan[a] Hu +27.5 (0.2, m)[b] M. Nan 2024
Structure 165: hyperesternoid I, hyperesternoid J, hyperesternoid K — A, bicyclononanes, caged
165
165.1 R = i-Pr hyperesternoid I[d] H. monogynum[a] −27.9 (0.2, m)[b] Z. Dong 2026a
165.2 R = i-Bu hyperesternoid J[d] H. monogynum[a] −31.7 (0.2, m)[b] Z. Dong 2026a
165.3 R = (R)-s-Bu hyperesternoid K[d] H. monogynum[a] −25.8 (0.2, m)[b] Z. Dong 2026a
Structure 166: hyperesternoid G — A, bicyclononanes, caged
166
166.1 hyperesternoid G[d] H. kouytchemse[a] −53.9 (0.3, m)[b] Z. Dong 2026a
Structure 167: hyperesternoid H — A, bicyclononanes, caged
167
167.1 hyperesternoid H[d] H. kouytchemse[a] −78.4 (0.2, m)[b] Z. Dong 2026a
Structure 168: hookerione G, hookerione H, hypersubone A and others — A, bicyclononanes, endo
168
168.1 R1 = prenyl
R2 = CO2Me
R3 = (S)-3,3-dimethyloxiran-2-yl		 hookerione G[d] H. hookerianum[a] −213 (0.25, m)[b] Y. Ye 2016
168.2 R1 = geranyl
R2 = H
R3 = (S)-3,3-dimethyloxiran-2-yl		 hookerione H[d] H. hookerianum[a] −152 (0.14, m)[b] Y. Ye 2016
168.3 R1 = geranyl
R2 = CO2Me
R3 = CH=CMe2		 hypersubone A[d] H. subsessile[a] −142.5 (0.09, m)[b] Y. Liao 2015
168.4 R1 = geranyl
R2 = CO2Me
R3 = (R)-3,3-dimethyloxiran-2-yl		 hookerione E[d] H. hookerianum[a] −146 (0.16, m)[b] Y. Ye 2016
168.5 R1 = geranyl
R2 = CO2Me
R3 = (S)-3,3-dimethyloxiran-2-yl		 hookerione F[d] H. hookerianum[a] −198 (0.12, m)[b] Y. Ye 2016
Structure 169: cumilcinol I — A, bicyclononanes, caged
169
169.1 cumilcinol I[d] H. wilsonii[a] +108.5 (0.2, m)[b] B. Tao 2024a
Structure 170: patumantane C, patumantane B — A, bicyclononanes, caged
170
170.1 R = H patumantane C[d] H. patulum[a] −190.7 (0.1, m)[b] Y. Duan 2024c
170.2 R = CO2Me patumantane B[d] H. patulum[a] −68.0 (0.1, acn)[b] Y. Duan 2024c
Structure 171: patumantane D — A, bicyclononanes, caged
171
171.1 patumantane D[d] H. patulum[a] −75.3 (0.1, m)[b] Y. Duan 2024c
Structure 172: hirsutofolin A, peroxyhirsutofolin A, hyperesternoid V and others — A, bicyclononanes, caged
172
172.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hirsutofolin A H. hirsutum[a] +5.8 (0.65, m)[b] J. Max 2021
172.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 peroxyhirsutofolin A H. hirsutum[a] +12.0 (0.79, m)[b] J. Max 2021
172.3 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid V[d] (prob. enantiomer) H. monogynum[a] −35.2 (0.1, m)[b] Z. Dong 2026a
172.4 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 hyperacmosin F H. acmosepalum[a] −16.3 (0.10, m)[b] X. Wang 2020a
172.5 R1 = i-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hyperesternoid T[d] H. monogynum[a] −43.3 (0.2, m)[b] Z. Dong 2026a
172.6 R1 = i-Bu
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid U[d] H. monogynum[a] −45.2 (0.1, m)[b] Z. Dong 2026a
172.7 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hirsutofolin B[d][e] H. hirsutum[a] −12.8 (1.15, m)[b] J. Max 2021
172.8 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hyperwilone B[c][e] (prob. enantiomer) H. wilsonii[a] +51.1 (0.50)[b] J. Hao 2021
172.9 R1 = (R)-s-Bu
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid W[d] H. monogynum[a] −39.9 (0.1, m)[b] Z. Dong 2026a
172.10 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = E-CH=CHCMe2OOH		 3′-hydroperoxyisohirsutofolin B[e] H. hirsutum[a] +20.1 (0.52, m)[b] J. Max 2021
172.11 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 sampsonione R C. obdeltifolia, H. sampsonii, H. attenuatum[a] +10.8 (0.011)[b] F. G. Cruz 2004, Z. Y. Xiao 2007, D. Li 2015a
172.12 R1 = Ph
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid X[d] H. monogynum[a] −42.3 (0.1, m)[b] Z. Dong 2026a
172.13 R1 = Ph
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 otogirinin C H. erectum[a] Thunb. NR Y. Ishida 2010
172.14 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = H		 hypersampsone L H. sampsonii[a] −67.4 (0.098)[b] Y. H. Zeng 2012
172.15 R1 = Ph
R2 = lavandulyl
R3 = CMe=CH2
R4 = OH		 epi-garcimultiflorone P[d][e] G. multiflora[a] +5.32 (0.02, m)[b] H. Teng 2019
Structure 173: pseudohenone F, pseudohenone G, garcimultiflorone P and others — A, bicyclononanes, caged
173
173.1 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 pseudohenone F H. pseudohenryi[a] N. Robson −7 (0.10, m)[b] X.-W. Yang 2017b
173.2 R1 = s-Bu
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 pseudohenone G[e] H. pseudohenryi[a] N. Robson −8 (0.15, m)[b] X.-W. Yang 2017b
173.3 R1 = Ph
R2 = (R)-lavandulyl[f]
R3 = CMe=CH2
R4 = OH		 garcimultiflorone P[c][t][u][x] G. multiflora[a] −5.1 (0.19, m)[b] Z.-Q. Wang 2018
173.4 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
R4 = prenyl		 hyperadditionciol E[d] H. addingtonii[a] −14 (0.05, m)[b] J. Chen 2026
173.5 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = H		 hypersampsone S (one of two by that name) H. sampsonii[a] +33 (0.3)[b] J.-J. Chen 2014
Structure 174: hypseudohenone B, hypseudohenone C — A, bicyclononanes, caged
174
174.1 R = prenyl hypseudohenone B[d] H. pseudohenryi[a] +13.5 (0.147, m)[b] N.-N. Jiang 2023
174.2 R = geranyl hypseudohenone C[d] H. pseudohenryi[a] +13.1 (0.106, m)[b] N.-N. Jiang 2023
Structure 175: hypseudohenone A — A, bicyclononanes, caged
175
175.1 hypseudohenone A[d] H. pseudohenryi[a] +19.6 (0.222, m)[b] N.-N. Jiang 2023
Structure 176: patumantane A — A, bicyclononanes, caged
176
176.1 patumantane A[d] H. patulum[a] −56.9 (0.1, m)[b] Y. Duan 2024c
Structure 177: hypersamponol C, norsampsone E, hyperacmosin E and others — A, bicyclononanes, caged
177
177.1 R1 = prenyl
R2 = prenyl		 hypersamponol C[d] H. sampsonii[a] –81.30 (0.049, m)[b] U. Kim 2026
177.2 R1 = C(=O)i-Pr
R2 = geranyl		 norsampsone E[d] H. sampsonii[a] −63.0 (0.30)[b] W.-J. Tian 2017
177.3 R1 = C(=O)Ph
R2 = geranyl		 hyperacmosin E H. acmosepalum[a] −57.6 (0.175)[b] X. Wang 2020a
177.4 R1 = (R)-CHPhCH2CO2H
R2 = prenyl		 lathrophytoic acid A Kielmeyera lathrophyton +15 (0.23, m)[b] M. F. de Almeida 2011
Structure 178: hypersampsone N, hypersampsonone E — A, bicyclononanes, caged
178
178.1 R = prenyl hypersampsone N[d] H. sampsonii[a] +34.4 (0.50)[b] W.-J. Tian 2014b
178.2 R = geranyl hypersampsonone E[d] H. sampsonii[a] +3.21 (1.06)[b] J.-S. Zhang 2016
Structure 179: 3′-hydroxyisohirsutuman A, hyperwilsol B, hirsutuman B and others — A, bicyclononanes, caged
179
179.1 R1 = i-Pr
R2 = prenyl
R3 = E-CH=CHCMe2OH		 3′-hydroxyisohirsutuman A H. hirsutum[a] –35.2 (0.13, m)[b] J. Max 2021
179.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl		 hyperwilsol B[d] H. wilsonii[a] −72.34 (0.05, m)[b] Z.-X. Wang 2025
179.3 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hirsutuman B[e] H. hirsutum[a] −61.9 (0.68, m)[b] J. Max 2021
179.4 R1 = s-Bu
R2 = prenyl
R3 = E-CH=CHCMe2OH		 3′-hydroxyisohirsutuman B[e] H. hirsutum[a] −69.5 (0.19, m)[b] J. Max 2021
179.5 R1 = Ph
R2 = prenyl
R3 = prenyl		 sampsonione B C. obdeltifolia, G. propinqua, H. sampsonii[a] +10.0 (0.018)[b] L.-H. Hu 1998, F. G. Cruz 2004, T. Sriyatep 2017
179.6 R1 = Ph
R2 = prenyl
R3 = CH2CH2CMe2OH		 no common name C. obdeltifolia[a] −5.1 (0.012)[b] F. G. Cruz 2004
179.7 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH		 hyphenrone M H. sampsonii[a] −82 (0.2, m)[b] X.-W. Yang 2015
179.8 R1 = Ph
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl		 wilsonglucinol J[c] H. wilsonii[a] +10.7 (0.5, m)[b] H. Cheng 2022a
179.9 R1 = Ph
R2 = geranyl
R3 = prenyl		 sampsonione A H. sampsonii[a] −49 (0.4)[b] L.-H. Hu 1998
179.10 R1 = Ph
R2 = geranyl
R3 = (E)-CH=CHCMe2OH		 hyphenrone N H. sampsonii[a] −89 (0.2, m)[b] X.-W. Yang 2015
179.11 R1 = Ph
R2 = geranyl
R3 = (E)-CH=CHCMe2OMe		 hypersampsonone D[d] H. sampsonii[a] −66.2 (0.52)[b] J.-S. Zhang 2016
Structure 180: hyperhomanoon A, hyperhomanoon B, hypersampsone O and others — A, bicyclononanes, caged
180
180.1 R1 = i-Pr
R2 = prenyl		 hyperhomanoon A[d] H. patulum[a] +6.2 (0.3, m)[b] B. Tao 2025
180.2 R1 = (S)-s-Bu
R2 = prenyl		 hyperhomanoon B[d] H. patulum[a] +45.0 (0.1, m)[b] B. Tao 2025
180.3 R1 = Ph
R2 = prenyl		 hypersampsone O[d] H. sampsonii[a] +15.2 (0.50)[b] W.-J. Tian 2014b
180.4 R1 = Ph
R2 = geranyl		 hyphenrone O H. sampsonii[a] −9 (0.1, m)[b] X.-W. Yang 2015
180.5 R1 = Ph
R2 = (R)-lavandulyl[f]		 garciyunnanone R[d] G. yunnan[a] Hu +9.2 (0.05, m)[b] M. Nan 2024
Structure 181: hyperhomanoon E — A, bicyclononanes, caged
181
181.1 hyperhomanoon E[d] H. patulum[a] −2.90 (0.5, m)[b] B. Tao 2025
Structure 182: hyperhomanoon D, hyperhomanoon C — A, bicyclononanes, caged
182
182.1 R = prenyl hyperhomanoon D[d] H. patulum[a] +95.3 (0.4, m)[b] B. Tao 2025
182.2 R = geranyl hyperhomanoon C[d] H. patulum[a] +26.2 (0.4, acn)[b] B. Tao 2025
Structure 183: hyperihirsan B, hypersubone G, hypersubone H and others — A, bicyclononanes, caged
183
183.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 hyperihirsan B H. hirsutum[a] +47.9 (0.18, m)[b] J. Max 2021
183.2 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH		 hypersubone G[d] H. subsessile[a] +37.5 (0.13, m)[b] T.-W. Cao 2020
183.3 R1 = i-Pr
R2 = geranyl
R3 = CMe2OOH		 hypersubone H[d] H. subsessile[a] +89.3 (0.08, m)[b] T.-W. Cao 2020
183.4 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 plukenetione C C. plukenetii, H. sampsonii[a] +65.9 (0.1)[b] G. E. Henry 1999, O. E. Christian 2001, Z. Y. Xiao 2010
183.5 R1 = Ph
R2 = prenyl
R3 = CMe2OOH		 peroxysampsone A H. sampsonii[a] +17.0 (0.128)[b] Z. Y. Xiao 2010
183.6 R1 = Ph
R2 = (E)-CH=CHCMe2OOH
R3 = CMe2OH		 33-hydroperoxyisoplukenetione C C. havetiodes[a] var. stenocarpa −3.9 (0.2)[b] O. E. Christian 2001
183.7 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 otogirinin B H. erectum[a] Thunb., H. attenuatum[a] +12.0 (0.14, m)[b] Y. Ishida 2010, D. Li 2015a
183.8 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperisampsin O[d] H. sampsonii[a] +12 (0.2, m)[b] H.-C. Zhu 2017
183.9 R1 = Ph
R2 = lavandulyl
R3 = OH		 garcimultinone B[d][e] G. multiflora[a] +28.3 (0.04, m)[b] Y. Chen 2019a
183.10 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 garcimultiflorone G[e] G. multiflora[a] +5.6 (0.12)[b] C.-W. Ting 2014
183.11 R1 = Ph
R2 = lavandulyl
R3 = CMe2OOH		 isohyperisampsin O[d][e] G. multiflora[a] +22.4 (0.06, m)[b] Y. Chen 2019a
183.12 R1 = Ph
R2 = (2S,3E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R3 = CMe2OH		 garcimultiflorone Q[c][t][u][x] G. multiflora[a] −11.1 (0.21, m)[b] Z.-Q. Wang 2018
Structure 184: hypersubone F, hyperisampsin N, hyperbeanin G and others — A, bicyclononanes, caged
184
184.1 R = geranyl
X = H		 hypersubone F[d] H. subsessile[a] −73.4 (0.12, m)[b] T.-W. Cao 2020
184.2 R = geranyl
X = OH		 hyperisampsin N[d] H. sampsonii[a] −31 (0.1)[b] H.-C. Zhu 2017
184.3 R = geranyl
X = OOH		 hyperbeanin G[c] H. beanii[a] −40.0 (0.08, m)[b] Y. Ma 2022a
184.4 R = lavandulyl
X = OH		 garcimultinone N[d] G. multiflora[a] +12.59 (0.04, m)[b] H. Teng 2021
Structure 185: peroxysampsone B — A, bicyclononanes, caged
185
185.1 peroxysampsone B H. sampsonii, H. attenuatum[a] −41.2 (0.042)[b] Z. Y. Xiao 2010, D. Li 2015a
Structure 186: pyranohyperihirsan A, pyranohyperihirsan B — A, bicyclononanes, caged
186
186.1 R = i-Pr pyranohyperihirsan A H. hirsutum[a] −24.7, (0.29, m)[b] J. Max 2021
186.2 R = s-Bu pyranohyperihirsan B[e] H. hirsutum[a] −30.7 (0.25, m)[b] J. Max 2021
Structure 187: hyperattenin M — A, bicyclononanes, caged
187
187.1 hyperattenin M[d][s] H. attenuatum[a] −24.1 (0.19, m)[b] D. Li 2018
Structure 188: hypersampsonone B, isohypersampsonone B — A, bicyclononanes, caged
188
188.1 R = geranyl hypersampsonone B[d] H. sampsonii[a] +14.9 (0.35)[b] J.-S. Zhang 2016
188.2 R = lavandulyl isohypersampsonone B[d][e] (inseparably mixed with epi-isohypersampsonone B, epimer at hemiacetal, in 5:1 ratio) G. multiflora[a] +60.0 (0.01, m)[b] Y. Chen 2019a
Structure 189: hyperesternoid Y — A, bicyclononanes, caged
189
189.1 hyperesternoid Y[d] H. monogynum[a] −42.3 (0.1, m)[b] Z. Dong 2026a
Structure 190: hyperesternoid Z — A, bicyclononanes, caged
190
190.1 hyperesternoid Z[d] H. monogynum[a] −48.7 (0.1, m)[b] Z. Dong 2026a
Structure 191: wilsonglucinol A — A, bicyclononanes, caged
191
191.1 wilsonglucinol A[d] H. wilsonii[a] −14.4 (0.63, m)[b] Y. Zhang 2020
Structure 192: wilsonglucinol C, cumilcinol C, wilsonglucinol B and others — A, bicyclononanes, caged
192
192.1 R1 = i-Pr
R2 = prenyl		 wilsonglucinol C[d] H. wilsonii[a] −94.8 (0.84, m)[b] Y. Zhang 2020
192.2 R1 = s-Bu
R2 = prenyl		 cumilcinol C[d][e] H. wilsonii[a] −137.0 (0.1, m)[b] B. Tao 2024a
192.3 R1 = Ph
R2 = prenyl		 wilsonglucinol B[d] H. wilsonii[a] −51.2 (0.73, m)[b] Y. Zhang 2020
192.4 R1 = Ph
R2 = (E)-CH=CHCMe2OH		 wilsonglucinol K, a.k.a. hypersampsone Y[d] H. wilsonii[a] −4.0 (0.5, m)[b], −74.0 (0.1, m)[b] H. Cheng 2022a, J. Cao 2024
Structure 193: garcimultinone C — A, bicyclononanes, caged
193
193.1 garcimultinone C[d][e] G. multiflora[a] −59.4 (0.02, m)[b] H. Teng 2019
Structure 194: hyperesternoid D, hyperesternoid E — A, bicyclononanes, caged
194
194.1 R = i-Bu hyperesternoid D[d] H. monogynum[a] −69.8 (0.3, m)[b] Z. Dong 2026a
194.2 R = (R)-s-Bu hyperesternoid E[d] H. monogynum[a] −58.7 (0.3, m)[b] Z. Dong 2026a
Structure 195: hyperesternoid F — A, bicyclononanes, caged
195
195.1 hyperesternoid F[d] H. monogynum[a] −87.2 (0.3, m)[b] Z. Dong 2026a
Structure 196: cumilcinol A, dioxasampsone B, hypersampsonone C and others — A, bicyclononanes, caged
196
196.1 R1 = i-Pr
R2 = prenyl		 cumilcinol A[d] H. wilsonii[a] +170.8 (0.3, m)[b] B. Tao 2024a
196.2 R1 = Ph
R2 = prenyl		 dioxasampsone B[d] H. sampsonii[a] +77.0 (0.50)[b] W.-J. Tian 2014c
196.3 R1 = Ph
R2 = geranyl		 hypersampsonone C[d] H. sampsonii[a] +6.7 (0.15)[b] J.-S. Zhang 2016
196.4 R1 = Ph
R2 = lavandulyl		 isohypersampsonone C[d][e] G. multiflora[a] +81.7 (0.02, m)[b] Y. Chen 2019a
Structure 197: hookerione Q, hypersampsone M, pseudohenone C and others — A, bicyclononanes, caged
197
197.1 R1 = i-Pr
R2 = geranyl
X = H2		 hookerione Q H. hookerianum[a] +11.2 (0.12, m)[b] Y. Ye 2019
197.2 R1 = Ph
R2 = prenyl
X = H2		 hypersampsone M[d] G. propinqua, H. sampsonii[a] +56.6 (0.50)[b] W.-J. Tian 2014a, T. Sriyatep 2017
197.3 R1 = Ph
R2 = prenyl
X = O		 pseudohenone C H. pseudohenryi[a] N. Robson −5 (0.24, m)[b] X.-W. Yang 2017b
197.4 R1 = Ph
R2 = (E)-4-oxoprenyl
X = H2		 pseudohenone B H. pseudohenryi[a] N. Robson +7 (0.10, m)[b] X.-W. Yang 2017b
197.5 R1 = Ph
R2 = geranyl
X = H2		 hypersampsone I H. sampsonii[a] +18.6 (0.262)[b] Y. H. Zeng 2012
197.6 R1 = Ph
R2 = geranyl
X = O		 sampsonione E H. sampsonii, H. attenuatum[a] +57.7 (0.03)[b] L.-H. Hu 1999b, D. Li 2015a
197.7 R1 = Ph
R2 = lavandulyl
X = O		 garciyunnanone I[d][e] G. yunnan[a] Hu +2 (0.1, m)[b] M. Nan 2024
Structure 198: hypersampsone C, hypersampsone P, hyperattenin F and others — A, bicyclononanes, caged
198
198.1 R1 = i-Pr
R2 = geranyl
X = H2		 hypersampsone C H. sampsonii[a] +14.3 (0.2)[b] Y.-L. Lin 2003
198.2 R1 = Ph
R2 = prenyl
X = H2		 hypersampsone P[d] H. sampsonii, H. subsessile[a] +11.0 (0.3)[b] W.-J. Tian 2014b, H.-M. Zhou 2020
198.3 R1 = Ph
R2 = prenyl
X = O		 hyperattenin F[d] H. attenuatum[a] Choisy −2.9 (0.10, m)[b] D. Li 2015a
198.4 R1 = Ph
R2 = CH2C(=O)CMe=CH2
X = H2		 pseudohenone D[d] H. pseudohenryi[a] N. Robson +6 (0.28, m)[b] X.-W. Yang 2017b
198.5 R1 = Ph
R2 = geranyl
X = H2		 sampsonione H H. sampsonii[a] +5.15 (0.07)[b] L.-H. Hu 1999b
198.6 R1 = Ph
R2 = geranyl
X = O		 hyperattenin G[d] H. attenuatum[a] Choisy −6.9 (0.16, m)[b] D. Li 2015a
198.7 R1 = Ph
R2 = lavandulyl
X = H2		 iso-sampsonione H[d][e] G. multiflora[a] +11.84 (0.08, m)[b] H. Teng 2019
198.8 R1 = Ph
R2 = lavandulyl
X = O		 garciyunnanone J[d][e] G. yunnan[a] Hu +5 (0.1, m)[b] M. Nan 2024
198.9 R1 = Ph
R2 = (E)-6,6-dimethoxy-3-methyl-2-hexenyl
X = H2		 hypercurpalone B[d] H. curvisepalum[a] +1.94 (0.10, m)[b] Y. Ye 2022
Structure 199: hookerione M, wilsonglucinol G, hyperesternoid Q and others — A, bicyclononanes, caged
199
199.1 R1 = i-Pr
R2 = prenyl
R3 = i-Pr
X = H		 hookerione M H. hookerianum[a] +68.1 (0.08, m)[b] Y. Ye 2019
199.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol G[d] H. wilsonii[a] +26.3 (0.27, m)[b] Y. Zhang 2020
199.3 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
X = H		 hyperesternoid Q[d] H. monogynum[a] −22.4 (0.1, m)[b] Z. Dong 2026a
199.4 R1 = i-Pr
R2 = geranyl
R3 = CMe=CH2
X = H		 hypersampsone A H. sampsonii[a] +21 (0.3)[b] Y.-L. Lin 2003
199.5 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
X = H		 hirsutusal C[e] H. hirsutum[a] N/A J. Max 2021
199.6 R1 = Ph
R2 = prenyl
R3 = i-Pr
X = H		 hookerione L H. hookerianum[a] +31.4 (0.10, m)[b] Y. Ye 2019
199.7 R1 = Ph
R2 = prenyl
R3 = CMe=CH2
X = H		 hypersampsone X[d] H. sampsonii[a] +27.1 (0.50)[b] W.-J. Tian 2017
199.8 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 plukenetione B C. plukenetii[a] +17.2 (0.03)[b] G. E. Henry 1999, R. B. Grossman 2000
199.9 R1 = Ph
R2 = prenyl
R3 = CMe2OOH
X = H		 hyperbeanin F[c] H. beanii[a] +10.0 (0.11, m)[b] Y. Ma 2022a
199.10 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperesternoid O[d] H. monogynum[a] −45.9 (0.3, m)[b] Z. Dong 2026a
199.11 R1 = Ph
R2 = prenyl
R3 = OH
X = H		 hypersampsonone L[d] H. sampsonii[a] +10 (1.0, m)[b] Y. Li 2023
199.12 R1 = Ph
R2 = geranyl
R3 = i-Pr
X = H		 hypersampsone D H. sampsonii[a] −35 (0.2)[b] Y.-L. Lin 2003
199.13 R1 = Ph
R2 = geranyl
R3 = CMe=CH2
X = H		 sampsonione D H. sampsonii[a] +12.27 (0.156)[b] L.-H. Hu 1999b
199.14 R1 = Ph
R2 = geranyl
R3 = CMe2OH
X = H		 sampsonione C H. sampsonii, H. attenuatum[a] +13.39 (0.174)[b] D. Li 2015a
199.15 R1 = Ph
R2 = geranyl
R3 = CMe2OH
X = OH		 hyperadditionciol F H. addingtonii[a] +6 (0.05, m)[b] J. Chen 2026
199.16 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
X = H		 hypersampsonone F[d] H. sampsonii[a] +6.73 (1.04)[b] J.-S. Zhang 2016
199.17 R1 = Ph
R2 = geranyl
R3 = OH
X = H		 cumilcinol D[d] H. wilsonii[a] −4.9 (0.3, m)[b] B. Tao 2024a
199.18 R1 = Ph
R2 = geranyl
R3 = OH
X = H		 hypersamponol A[c] (enantiomer) H. sampsonii[a] –6.22 (0.064, m)[b] U. Kim 2026
199.19 R1 = Ph
R2 = neryl
R3 = i-Pr
X = H		 hookerione I H. hookerianum[a] +24.2 (0.25, m)[b] Y. Ye 2019
199.20 R1 = Ph
R2 = lavandulyl
R3 = CMe=CH2
X = H		 garciyunnanone K[d][e] G. yunnan[a] Hu +12.9 (0.1, m)[b] M. Nan 2024
199.21 R1 = Ph
R2 = lavandulyl
R3 = i-Pr
X = H		 garciyunnanone N[d][e] G. yunnan[a] Hu +1.0 (0.2, m)[b] M. Nan 2024
199.22 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH
X = H		 garciyunnanone Q[d][e] G. yunnan[a] Hu +25.6 (0.2, m)[b] M. Nan 2024
199.23 R1 = Ph
R2 = lavandulyl
R3 = CMe2OOH
X = H		 iso-hypersampsonone F[d][e] G. multiflora[a] +5.60 (0.01, m)[b] H. Teng 2019
199.24 R1 = Ph
R2 = lavandulyl
R3 = OH
X = H		 garcimultinone A[d][e] G. multiflora[a] −25.6 (0.02, m)[b] Y. Chen 2019a
Structure 200: wilsonglucinol F, hookerione O, cumilcinol F and others — A, bicyclononanes, caged
200
200.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 wilsonglucinol F[d] H. wilsonii[a] +29.2 (0.55, m)[b] Y. Zhang 2020
200.2 R1 = i-Pr
R2 = geranyl
R3 = CMe=CH2		 hookerione O H. hookerianum[a] +39.1 (0.25, m)[b] Y. Ye 2019
200.3 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH		 cumilcinol F[d][e] H. wilsonii[a] +104.7 (0.2, m)[b] B. Tao 2024a
200.4 R1 = Ph
R2 = prenyl
R3 = i-Pr		 hyperacmone F[d] H. maclarenii[a] +10.32 (0.126, m)[b] W.-L. Meng 2026
200.5 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 hypersampsone Q[d] H. sampsonii[a] +18.3 (0.4)[b] W.-J. Tian 2014b
200.6 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hypersampsone G H. sampsonii[a] +10.25 (0.401)[b] Y. H. Zeng 2009
200.7 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 hypersampsone J H. sampsonii[a] +11.4 (0.573)[b] Y. H. Zeng 2012
200.8 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 hypersampsonone G[d] H. sampsonii[a] +4.22 (0.9)[b] J.-S. Zhang 2016
200.9 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperattenin K[d] H. attenuatum[a] Choisy −11.5 (0.886, m)[b] D. Li 2015b
200.10 R1 = Ph
R2 = geranyl
R3 = OH		 hypersamponol B[c] H. sampsonii[a] –17.50 (0.023, m)[b] U. Kim 2026
200.11 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 isohypersampsonone G[d][e] G. multiflora[a] +34.2 (0.01, m)[b] Y. Chen 2019a
Structure 201: wilsonglucinol D, hyperwilone C, wilsonglucinol E and others — A, bicyclononanes, caged
201
201.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol D[d] H. wilsonii[a] −17.7 (0.92, m)[b] Y. Zhang 2020
201.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 hyperwilone C[c] (enantiomer) H. wilsonii[a] +47.3 (0.50, m)[b] J. Hao 2021
201.3 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol E, a.k.a. hirsutusal D[d][e] H. wilsonii[a] −9.9 (0.34, m)[b] Y. Zhang 2020, J. Max 2021
201.4 R1 = Ph
R2 = prenyl
R3 = OH
X = H		 no common name C. obdeltifolia, G. propinqua[a] NR F. G. Cruz 2004, T. Sriyatep 2017
201.5 R1 = Ph
R2 = prenyl
R3 = i-Pr
X = H		 hyphenrone Q H. sampsonii[a] −4 (0.2, m)[b] X.-W. Yang 2015
201.6 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 attenuatumione A[c] H. attenuatum[a] −19.3 (0.18)[b] Z.-B. Zhou 2014, X.-W. Yang 2018
201.7 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperesternoid P[d] H. monogynum[a] −52.2 (0.2, m)[b] Z. Dong 2026a
201.8 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 hypercohone A[d] (prob. enantiomer) H. cohaerens[a] +3.87 (0.21, m)[b] X. Liu 2013b
201.9 R1 = Ph
R2 = geranyl
R3 = i-Pr
X = H		 hookerione K H. hookerianum[a] −33.1 (0.27, m)[b] Y. Ye 2019
201.10 R1 = Ph
R2 = geranyl
R3 = CMe2OH
X = H		 attenuatumione D H. attenuatum[a] −10.8 (0.15)[b] Z.-B. Zhou 2014
201.11 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
X = H		 hyperattenin I[d] H. attenuatum[a] Choisy −24.5 (0.23, m)[b] D. Li 2015a
201.12 R1 = Ph
R2 = (Z)-geranyl
R3 = CMe2OH
X = H		 hyperacmone G[d] H. maclarenii[a] –30.52 (0.057, m)[b] W.-L. Meng 2026
201.13 R1 = Ph
R2 = lavandulyl
R3 = CMe=CH2
X = H		 garciyunnanone L[d][e] G. yunnan[a] Hu −5.7 (0.2, m)[b] M. Nan 2024
201.14 R1 = Ph
R2 = lavandulyl
R3 = i-Pr
X = H		 garciyunnanone O[d][e] G. yunnan[a] Hu +2.0 (0.1, m)[b] M. Nan 2024
Structure 202: hookerione N, hirsutusal A, cumilcinol E and others — A, bicyclononanes, caged
202
202.1 R1 = i-Pr
R2 = prenyl
R3 = i-Pr		 hookerione N H. hookerianum[a] −10.3 (0.13, m)[b] Y. Ye 2019
202.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 hirsutusal A[e] H. hirsutum[a] +36.7 (0.18, m)[b] J. Max 2021
202.3 R1 = i-Pr
R2 = prenyl
R3 = OH		 cumilcinol E[d] H. wilsonii[a] −2.0 (0.1, m)[b] B. Tao 2024a
202.4 R1 = i-Pr
R2 = geranyl
R3 = i-Pr		 hypersampsone B H. sampsonii[a] +12 (0.3)[b] Y.-L. Lin 2003
202.5 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH		 hookerione P H. hookerianum[a] −10.3 (0.13, m)[b] Y. Ye 2019
202.6 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH		 hirsutusal B[e] H. hirsutum[a] −6.9 (0.24, m)[b] J. Max 2021
202.7 R1 = Ph
R2 = prenyl
R3 = OH		 pseudohenone E C. obdeltifolia, H. pseudohenryi[a] N. Robson −27 (0.13, m)[b] F. G. Cruz 2004, X.-W. Yang 2017b
202.8 R1 = Ph
R2 = prenyl
R3 = i-Pr		 hyphenrone P H. sampsonii[a] −83 (0.1, m)[b] X.-W. Yang 2015
202.9 R1 = Ph
R2 = prenyl
R3 = CMe=CH2		 hypercohone B H. cohaerens[a] −37.2 (0.11, m)[b] X. Liu 2013b
202.10 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 hyperacmosin G[c] H. acmosepalum[a] −8.3 (0.012)[b] X. Wang 2020a
202.11 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 sampsonione G[d] (prob. enantiomer) H. sampsonii[a] +10.0 (0.01)[b] L.-H. Hu 1999b
202.12 R1 = Ph
R2 = geranyl
R3 = OH		 hyperattenin H[d] H. attenuatum[a] Choisy −12.4 (0.26, m)[b] D. Li 2015a, X.-W. Yang 2017b
202.13 R1 = Ph
R2 = geranyl
R3 = OH		 cowabenzophenone B[c] (prob. enantiomer) G. cowa[a] +96 (0.048)[b] T. Sriyatep 2014, X.-W. Yang 2017b
202.14 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hypersampsone E[c] H. sampsonii[a] +39 (0.2)[b] Y.-L. Lin 2003
202.15 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hyperichoisin B[d] (enantiomer) H. choisianum[a] −17.4 (0.285)[b] H.-B. Zhang 2021
202.16 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 hypercohone C H. cohaerens[a] −38.0 (0.09, m)[b] X. Liu 2013b
202.17 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 cowabenzophenone A (enantiomer) G. cowa[a] +137 (0.02)[b] T. Sriyatep 2014
202.18 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 sampsonione F[c] H. sampsonii[a] +14.5 (1.1)[b] L.-H. Hu 1999b
202.19 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 hyperichoisin C[d] (enantiomer) H. choisianum[a] −21.9 (0.31)[b] H.-B. Zhang 2021
202.20 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperberlone C[c] H. beanii[a] −0.34 (2, m)[b] Y.-W. Li 2022
202.21 R1 = Ph
R2 = neryl
R3 = i-Pr		 hookerione J H. hookerianum[a] −38.2 (0.12, m)[b] Y. Ye 2019
202.22 R1 = Ph
R2 = lavandulyl
R3 = CMeCH2		 garciyunnanone M[d][e] G. yunnan[a] Hu +4.3 (0.4, m)[b] M. Nan 2024
202.23 R1 = Ph
R2 = lavandulyl
R3 = i-Pr		 iso-hookerione J[d][e] G. multiflora[a] −4.70 (0.05, m)[b] H. Teng 2019
202.24 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 garciyunnanone P[d][e] G. yunnan[a] Hu −3.6 (0.1, m)[b] M. Nan 2024
202.25 R1 = Ph
R2 = lavandulyl
R3 = OH		 garciyunnanone H[d] G. yunnan[a] Hu +21.6 (0.1, m)[b] M. Nan 2024
Structure 203: hypertonii A — A, bicyclononanes, caged
203
203.1 hypertonii A[c] H. addingtonii[a] N. Robson +42.3 (0.1, acn)[b] Q. Feng 2025
Structure 204: dioxasampsone A — A, bicyclononanes, caged
204
204.1 dioxasampsone A[d] H. sampsonii[a] +16.8 (0.50)[b] W.-J. Tian 2014c
Structure 205: hyperesternoid R — A, bicyclononanes, caged
205
205.1 hyperesternoid R[d] H. monogynum[a] −32.7 (0.2, m)[b] Z. Dong 2026a
Structure 206: hyperesternoid S — A, bicyclononanes, caged
206
206.1 hyperesternoid S[d] H. monogynum[a] −24.8 (0.2, m)[b] Z. Dong 2026a
Structure 207: pseudohenone A — A, bicyclononanes, caged
207
207.1 pseudohenone A H. pseudohenryi[a] N. Robson +43 (0.20, m)[b] X.-W. Yang 2017b
Structure 208: cumilcinol B — A, bicyclononanes, caged
208
208.1 cumilcinol B[d] H. wilsonii[a] +98.0 (0.1, m)[b] B. Tao 2024a
Structure 209: hypercurpalone A — A, bicyclononanes, dimer
209
209.1 hypercurpalone A[d] H. curvisepalum[a] −17.9 (0.13, m)[b] Y. Ye 2022
Structure 210: hypseudone A — A, bicyclononanes, caged
210
210.1 hypseudone A[c] H. pseudohenryi[a] +38.2 (0.096, m)[b] N.-N. Jiang 2025
Structure 211: garsubelone A — A, bicyclononanes, dimer
211
211.1 garsubelone A[d] G. subelliptica[a] +103 (0.14, m)[b] Y.-L. Wang 2019
Structure 212: kielmeyeracin, hyperforatum D, spiranthenone B and others — B, bicyclononanes, exo
212
212.1 R1 = n-Pr
R2 = CHBuCO2Me
R3 = prenyl
R4 = prenyl
R5 = H		 kielmeyeracin[c][e] Kielmeyera variabilis −70 (0.1, m)[b] A. Coqueiro 2016
212.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyperforatum D H. perforatum[a] +4.0 (1.00, m)[b] X. Wang 2024
212.3 R1 = i-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 spiranthenone B Spiranthera odoratissima −24 (0.10)[b] L. C. Albernaz 2012, X.-W. Yang 2018
212.4 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl
R4 = CH2CH(OH)CMe2OH
R5 = H		 mesuaferroic acid S[c][e] Mesua ferrea L. +5.10 (0.1, m)[b] Q. Zhang 2026
212.5 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe=O
R5 = H		 oblongifolin V[c] G. oblongifolia[a] +4.3 (0.02, m)[b] H. Zhang 2016
212.6 R1 = Ph
R2 = H
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin L[c] G. oblongifolia[a] −15.1 (0.05, m)[b] H. Zhang 2014a, X.-W. Yang 2018
212.7 R1 = Ph
R2 = H
R3 = prenyl
R4 = CH2C(=O)C(=CH2)CH2CH2CH=CMe2
R5 = H		 oblongifolin O[c][l][m] G. oblongifolia[a] −20.8 (0.05, m)[b] H. Zhang 2014a
212.8 R1 = Ph
R2 = H
R3 = prenyl
R4 = 6-oxo-ω-isogeranyl[h]
R5 = H		 oblongifolin N[c][l][m] G. oblongifolia[a] −17.5 (0.04, m)[b] H. Zhang 2014a
212.9 R1 = Ph
R2 = H
R3 = prenyl
R4 = (S)-6-hydroxy-ω-isogeranyl[h]
R5 = H		 oblongifolin Q[c][l][m] G. oblongifolia[a] −222.2 (0.03, m)[b] H. Zhang 2014a
212.10 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 hyperascyrin L[d] H. ascyron[a] −58.5 (0.1, m)[b] B. Zhen 2019
212.11 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 clusianone[c] C. congestiflora, C. spiritu-sanctensis, C. torresii, H. hypericoides[a] +58.3 (0.7)[b]; OMe: +61 (1.4)[b] C. M. A. de Oliveira 1996, A. L. Piccinelli 2005, V. Rodeschini 2007, M. R. Garnsey 2010, F. Horeischi 2015
212.12 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone I, a.k.a. 13-deoxyguttiferone J[i] (one of two by the first name) G. cambogia, G. virgata[a] −14.3 (5.6, m)[b] J. Merza 2006, M. Masullo 2008
212.13 R1 = Ph
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 spiritone[e] C. spiritu-sanctensis[a] NR A. L. M. Porto 2000
212.14 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 18-hydroxyclusianone H. hypericoides[a] NR O. E. Christian 2008
212.15 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone J, a.k.a. garciyunnanin A, and tautomer iso-guttiferone J G. cambogia, G. gummi-gutta, G. virgata, G. yunnanensis[a] −34.3 (1.75, m)[b], −3.0 (0.11)[b] J. Merza 2006, M. Masullo 2008, G. Xu 2008, P. Pandey 2024
212.16 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 ent-guttiferone J[l][m] (prob. enantiomer) R. edulis[a] +10.8 (0.01, m)[b] U. M. Acuña 2010
212.17 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin U[c] G. oblongifolia[a] +48.2 (0.08, m)[b] H. Zhang 2014a
212.18 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = prenyl		 garcicowin B G. cowa[a] −16.0 (0.21)[b] G. Xu 2010
212.19 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 aristophenone A, and tautomer aristophenone B[c] G. xanthochymus[a] +58 (0.1)[b]; OAc: +53 (0.1)[b], +54 (0.1)[b] O. Cuesta-Rubio 2001b, S. Baggett 2005
212.20 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone K G. calcicola, G. cambogia, G. cowa, G. yunnanensis[a] Hu −2 (0.35)[b] S. Cao 2007, M. Masullo 2008, G. Xu 2010, D. Zheng 2017
212.21 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = CH2COCMe=CH2		 garciyunnanin J[c] G. yunnanensis[a] +103.1 (0.13, m)[b] D. Zheng 2021b
212.22 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = CH2CHOHCMe=CH2
R5 = prenyl		 schomburgkianone F[d][e] G. schomburgkiana[a] −13 (0.4)[b] D. H. Le 2016
212.23 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = CH2CHOHCMe=CH2
R5 = prenyl		 schomburgkianone G[d][e] (diastereomer) G. schomburgkiana[a] +6 (0.3)[b] D. H. Le 2016
212.24 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl		 garciyunnanol I[d] G. yunnanensis[a] −58 (0.36, m)[b] X.-Y. Hu 2024
212.25 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = CH2CO2H
R5 = prenyl		 garciyunnanol H[d] G. yunnanensis[a] −12 (0.18, m)[b] X.-Y. Hu 2024
212.26 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin B G. cowa, G. oblongifolia, G. yunnanensis[a] Hu +17.6 (0.21)[b] W. Hamed 2006, G. Xu 2010, D. Zheng 2017
212.27 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = prenyl		 guttiferone G G. humilis, G. macrophylla[a] −25 (0.04)[b], +8.7 (1.5)[b] R. B. Williams 2003, K. Herath 2005, R. Ciochina 2006
212.28 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = prenyl		 oblongifolin C (prob. enantiomer) G. cowa, G. oblongifolia, G. yunnanensis[a] Hu +14.5 (0.21)[b] W. Hamed 2006, G. Xu 2010, D. Zheng 2017
212.29 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OH
R5 = prenyl		 garschomcinol A[d] G. schomburgkiana[a] +12.5 (0.20, m)[b] S. Kaennakam 2022a
212.30 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OMe
R5 = prenyl		 garschomcinol B[d] G. schomburgkiana[a] +13.5 (0.28, m)[b] S. Kaennakam 2022a
212.31 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OEt
R5 = prenyl		 garschomcinol C[d] G. schomburgkiana[a] +14.7 (0.34, m)[b] S. Kaennakam 2022a
212.32 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (R)-6-hydroxy-ω-isogeranyl[h]
R5 = prenyl		 schomburgkianone A[d] G. schomburgkiana[a] +15 (0.7)[b] D. H. Le 2016
212.33 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (S)-6-hydroxy-ω-isogeranyl[h]
R5 = prenyl		 schomburgkianone B[d] G. schomburgkiana[a] +40 (1.0)[b] D. H. Le 2016
212.34 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E,E)-CH2CH=CMeCH2CH=CHCMe2OH
R5 = prenyl		 schomburgkianone C[d] G. schomburgkiana[a] +25 (0.8)[b] D. H. Le 2016
212.35 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E,E)-CH2CH=CMeCH2CH=CHCMe2OMe
R5 = prenyl		 garciyunnanol E[d] G. yunnanensis[a] +5 (0.36, m)[b] X.-Y. Hu 2024
212.36 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone M[c] G. cambogia[a] −29.8 (0.15, m)[b] M. Masullo 2008, M. Masullo 2010
212.37 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = prenyl		 guttiferone P G. solomonensis[a] +18.2 (0.33)[b] A. R. Carroll 2009
212.38 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = geranyl
R5 = H		 guttiferone B G. cowa, S. globulifera[a] −44 (0.5)[b] K. R. Gustafson 1992, G. Xu 2010
212.39 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 7-epi-garcinol[e] M. coccinea[a] −86 (0.8)[b] G. Marti 2009
212.40 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-isolavandulyl[g]
R4 = prenyl
R5 = H		 xanthochymusone B[d] G. xanthochymus[a] +137 (0.1, m)[b] Z.-H. Xu 2022
212.41 R1 = 3,4-dihydroxyphenyl
R2 = (E)-CH2CH=CMeCH2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl		 garciyunnanol F[d] G. yunnanensis[a] +7 (0.17, m)[b] X.-Y. Hu 2024
212.42 R1 = 3,4-dihydroxyphenyl
R2 = (Z)-CH2CH=CMeCH2OH
R3 = prenyl
R4 = geranyl
R5 = prenyl		 garciyunnanol G[d] G. yunnanensis[a] +11 (0.18, m)[b] X.-Y. Hu 2024
212.43 R1 = 3,4-dihydroxyphenyl
R2 = geranyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone O (one of two by that name) G. solomonensis[a] +30.7 (0.66)[b] A. R. Carroll 2009
212.44 R1 = 3,4-dihydroxyphenyl
R2 = ω-isogeranyl[h]
R3 = prenyl
R4 = geranyl
R5 = H		 semsinone A[n] G. semseii[a] +52 (0.1)[b] J. J. Magadula 2008
212.45 R1 = 2,4,5-trihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone L G. calcicola[a] −8 (0.06)[b] S. Cao 2007
Structure 213: hyperpapuanone, mesuaferroic acid M, laxifloranone and others — B, bicyclononanes, endo
213
213.1 R1 = i-Pr
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = H		 hyperpapuanone H. papuanum[a] +15 (0.1, m)[b] K. Winkelmann 2001a
213.2 R1 = i-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl
R4 = (R)-CH(NH2)CH=CMe2
R5 = H		 mesuaferroic acid M[c] Mesua ferrea L. +53.22 (0.1, m)[b] Q. Zhang 2026
213.3 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = prenyl
R4 = prenyl
R5 = H		 laxifloranone[e] Marila laxiflora +23.6 (0.8, m)[b] H. R. Bokesch 1999
213.4 R1 = i-Bu
R2 = CHPhCH2CO2Me
R3 = prenyl
R4 = prenyl
R5 = H		 mesuaferroic acid H[e] Mesua ferrea +15.9 (0.2, m)[b] X.-C. Zhang, 2020
213.5 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = H		 mesuaferroic acid I[e] Mesua ferrea +2.15 (0.2, m)[b] X.-C. Zhang, 2020
213.6 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = prenyl
R4 = CH2CH(OH)CMe=CH2
R5 = H		 mesuaferroic acid L[e] Mesua ferrea +8.5 (0.2, m)[b] X.-C. Zhang, 2020
213.7 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl
R4 = prenyl
R5 = H		 mesuaferroic acid O[c][e] Mesua ferrea L. +12.73 (0.1, m)[b] Q. Zhang 2026
213.8 R1 = s-Bu
R2 = (S)-CHPhCH2CO2Et
R3 = prenyl
R4 = prenyl
R5 = H		 mesuaferroic acid P[c][e] Mesua ferrea L. +91.22 (0.16, m)[b] Q. Zhang 2026
213.9 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl
R4 = (R)-CH(NH2)CH=CMe2
R5 = H		 mesuaferroic acid N[c][e] Mesua ferrea L. +22.74 (0.73, m)[b] Q. Zhang 2026
213.10 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = H		 mesuaferroic acid Q[c][e] Mesua ferrea L. +3.40 (0.1, m)[b] Q. Zhang 2026
213.11 R1 = s-Bu
R2 = (S)-CHPhCH2CO2Me
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = H		 mesuaferroic acid R[c][e] Mesua ferrea L. +10.23 (1.33, m)[b] Q. Zhang 2026
213.12 R1 = CH(OH)CMe2OH
R2 = CHPhCH2CO2H
R3 = prenyl
R4 = prenyl
R5 = H		 mesuaferroic acid K[e] Mesua ferrea +3.25 (0.2, m)[b] X.-C. Zhang, 2020
213.13 R1 = Ph
R2 = H
R3 = prenyl
R4 = Me
R5 = H		 oblongifolin P[c] G. oblongifolia[a] −56.3 (0.05, m)[b] H. Zhang 2014a
213.14 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = H		 garciniaphenone[m] G. brasiliensis[a] −52.8 (0.1)[b] P. B. M. C. Derogis 2008
213.15 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone Q G. cochinchinensis[a] −50 (0.21)[b] H. D. Nguyen 2011
213.16 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 cowanone, a.k.a. chamuangone (prob. enantiomer) G. cowa[a] +5 (1.0)[b] K. Trisuwan 2012, A. Sakunpak 2012
213.17 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl		 garcowacinol A[d] G. cowa[a] −35.0 (0.50, m)[b] S. Kaennakam 2022b
213.18 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe2OMe
R5 = prenyl		 garcowacinol B[d] G. cowa[a] −46.5 (0.50, m)[b] S. Kaennakam 2022b
213.19 R1 = Ph
R2 = H
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin AA[c] G. oblongifolia[a] −36.2 (0.05, m)[b] H. Zhang 2016, X.-W. Yang 2018
213.20 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OH
R5 = H		 oblongifolin Z[c][m] G. oblongifolia[a] −23.5 (0.03, m)[b] H. Zhang 2016
213.21 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = H		 hyperibone L H. scabrum[a] +69.5 (0.2)[b] N. Tanaka 2004
213.22 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 hyperelatone A[d] H. elatoides[a] +189.3 (0.1)[b] X.-T. Yan 2019
213.23 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 7-epi-clusianone[d] C. sandinensis, C. torresii, H. elegans, H. hypericoides[a] +62.3 (1.1)[b] F. delle Monache 1991, M. H. Santos 1998, T. M. de Almeida Alves 1999, K. Winkelmann 2001a, A. L. Piccinelli 2005, P. T. Nedialkov 2011, L. Wang 2021
213.24 R1 = Ph
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 garcimultiflorone K[c] (one of two by that name) G. multiflora[a] −92.4 (0.41, m)[b] L.-Y. Cheng 2018
213.25 R1 = Ph
R2 = prenyl
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone C[d] G. picrorhiza[a] +15 (0.10, m)[b] E. R. Sukandar 2020
213.26 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = prenyl
R5 = H		 hyperbeone A[c] H. beanii[a] −4.7 (0.08, m)[b] W.-X. Li 2021
213.27 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 18-hydroxy-7-epi-clusianone H. hypericoides[a] +64 (0.29)[b] O. E. Christian 2008
213.28 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin E G. oblongifolia[a] +65.1 (0.40)[b] S.-X. Huang 2009
213.29 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone N G. cambogia[a] −34.5 (0.07, m)[b] M. Masullo 2008
213.30 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 14-deoxygarcinol[e] M. coccinea[a] −42 (0.3)[b] G. Marti 2009
213.31 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = (S)-isolavandulyl[g]
R4 = prenyl
R5 = H		 xanthochymusone A[d] G. xanthochymus[a] +137 (0.1, m)[b] Z.-H. Xu 2022
213.32 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone B[d] G. picrorhiza[a] +12 (0.10, m)[b] E. R. Sukandar 2020
213.33 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 garcimultiflorone H[d] G. multiflora[a] +29.8 (0.62, m)[b] W. Fu 2015
213.34 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone A S. globulifera, G. livingstonei, G. humilis[a] +34 (1.7)[b] K. R. Gustafson 1992, R. B. Williams 2003
213.35 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin A G. cowa, G. oblongifolia, G. yunnanesis[a] Hu +23 (0.35)[b] W. Hamed 2006, G. Xu 2010, D. Zheng 2017
213.36 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (R)-6-hydroxy-ω-isogeranyl[h]
R5 = H		 oblongifolin T[c] G. oblongifolia[a] +10.8 (0.05, m)[b] H. Zhang 2014a, X.-W. Yang 2018
213.37 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = (1R,3S)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 garcinopicrobenzophenone, a.k.a. eugeniaphenone[d] G. eugeniaefolia, G. picrorhiza[a] −271.4 (0.17, m)[b], +28 (0.10, m)[b] A. Soemiati 2006, S. Hartati 2008, E. R. Sukandar 2020
213.38 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone I[i] (one of two by that name) G. griffithii[a] −68 (1.2)[b] R. W. Fuller 1999
213.39 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R4 = prenyl
R5 = H		 nujiangefolin E[d][e] G. nujiangensis[a] −22.48 (0.11, m)[b] X.-J. Liu 2023
213.40 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = 2,2-dimethyl-5-isopropenyl-3-tetrahydrofurylmethyl
R4 = prenyl
R5 = H		 paucinochymol A[d][e] G. paucinervis[a] −38.8 (0.01, m)[b] X. Tan 2020
213.41 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = geranyl
R5 = H		 oblongifolin D G. cowa, G. oblongifolia[a] +44.6 (0.21)[b] W. Hamed 2006, G. Xu 2010
213.42 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 garcinol, a.k.a. (−)-camboginol, a.k.a. guttiferone F[c] G. cambogia, G. cowa, G. indica, G. pedunculata, G. yunnanensis [a] Hu, M. coccinea, Allanblackia stuhlmannii[a] −138 (0.1)[b], −293 (0.4)[b] A. V. Rama Rao 1980, N. Krishnamurthy 1981, A. Sahu 1989, R. W. Fuller 1999, G. Marti 2009, G. Xu 2010, C. Socolsky 2015, D. Zheng 2017, D. Zheng 2021a, X. Wang 2021a
213.43 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 guttiferone E, a.k.a. (+)-camboginol[d] (enantiomer) Cuban propolis, C. rosea, G. ovafolia, G. virgata, G. yunnanensis[a] Hu +101 (0.5)[b] K. R. Gustafson 1992, R. W. Fuller 1999, O. Cuesta Rubio 1999, O. Cuesta-Rubio 2002, J. Merza 2006, C. Socolsky 2015, D. Zheng 2021a
213.44 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = prenyl		 guttiferone D[e] S. globulifera[a] +92 (0.9)[b] as mix with guttiferone C K. R. Gustafson 1992
213.45 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = CH2CHOHCMe2OH
R5 = H		 garcimultiflorone F[e] G. multiflora[a] −68.7 (0.49, m)[b] X. Liu 2010, X. Wang 2021a
213.46 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = CH2CHOHCMe2OH
R5 = H		 isogarcimultiflorone F[e] (diastereomer) G. multiflora[a] −46.0 (0.50, m)[b] X. Liu 2010, X. Wang 2021a
213.47 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = (S)-CH2CHOHCMe2OMe
R5 = H		 garciesculentone C[e] G. esculenta[a] −24.9 (0.08, m)[b] H. Zhang 2014b
213.48 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-isolavandulyl[g]
R4 = prenyl
R5 = H		 xanthochymol, a.k.a. garcinielliptone FC[d] Cuban propolis, G. mannii, G. staudtii, G. subelliptica, G. virgata, G. xanthochymus, G. madrunno, Platonia insignis[a] +138 (0.1)[b], +12.6 (1.0)[b] C. G. Karanjgoakar 1973, D. L. Dreyer 1974, G. Venkatswamy 1975, J. F. Blount 1976, O. Cuesta Rubio 1999, D. Roux 2000, O. Cuesta-Rubio 2002, S. Baggett 2005, J. Merza 2006, C.-C. Wu 2008a, J. S. Costa 2013, Y. Luo 2023
213.49 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = isolavandulyl[g]
R4 = prenyl
R5 = prenyl		 guttiferone C[e] S. globulifera[a] +92 (0.9)[b] as mix with guttiferone D K. R. Gustafson 1992
213.50 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (4R)-4-hydroxygeranyl
R4 = prenyl
R5 = H		 32-hydroxy-7-epi-guttiferone M[d][l][m] R. edulis[a] +10 (0.1, m)[b] U. M. Acuña 2010
213.51 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (2R)-4-hydroxyisolavandulyl[g]
R4 = prenyl
R5 = H		 garcimultiflorone E[e] G. multiflora[a] −43.6 (0.41, m)[b] X. Liu 2010, X. Wang 2021a
213.52 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (4R)-4-hydroxyisolavandulyl[g]
R4 = prenyl
R5 = H		 garciesculentone E[e] G. esculenta[a] −14.3 (0.03, m)[b] H. Zhang 2014b
213.53 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (4S)-4-hydroxyisolavandulyl[g]
R4 = prenyl
R5 = H		 garciesculentone D[e] G. esculenta[a] −15.9 (0.05, m)[b] H. Zhang 2014b
213.54 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = (1S)-2-methylene-4,4-dimethylcyclohexylmethyl
R4 = prenyl
R5 = H		 acuminophenone A R. acuminata[a] +208 (0.01)[b] G. R. Almanza 2011
213.55 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = 3-isopropenyl-2,2-dimethylcyclopentyl
R4 = prenyl
R5 = H		 thorelione A[e] Calophyllum thorelii +91.9 (1.0, m)[b] L.-T. T. Nguyen 2012
213.56 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (2,4,4-trimethyl-2-cyclohexenyl)methyl
R4 = prenyl
R5 = H		 coccinone F M. coccinea[a] −32 (0.7)[b] G. Marti 2009
213.57 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = (1S,3R)-3-(2-hydroxyisopropyl)-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone D[d] G. picrorhiza[a] +34 (0.10, m)[b] E. R. Sukandar 2020
213.58 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = (1S,3S)-3-acetyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone E[d] G. picrorhiza[a] +5 (0.10, m)[b] E. R. Sukandar 2020
213.59 R1 = 3,4-dihydroxyphenyl
R2 = (E)-CH=CHCMe2OH
R3 = (E)-CH2CH(CMe=CH2)CH(OH)CH=CMe2
R4 = prenyl
R5 = H		 garciyunnanensisin C[c][e] G. yunnanensis[a] +170.0 (0.1, m)[b] P.-X. Ji 2025
213.60 R1 = 3,4-hydroxyphenyl
R2 = (E)-CH2CH=C(Me)CH2OH
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone A[d] G. picrorhiza[a] +27 (0.10, m)[b] E. R. Sukandar 2020
213.61 R1 = 3,4-dihydroxyphenyl
R2 = CH2CH2CMe2OH
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 garcimultiflorone D (one of two by that name) G. multiflora[a] −53.6 (0.48, m)[b] X. Liu 2010, X. Wang 2021a
213.62 R1 = 3,4-dihydroxyphenyl
R2 = CH2CHOHCMe2OH
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 18-hydroxygarcimultiflorone D[e] G. multiflora[a] −33.3 (0.12, m)[b] X. Liu 2010, X. Wang 2021a
213.63 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = prenyl
R4 = prenyl
R5 = H		 coccinone G[e] M. coccinea[a] −16 (1.0)[b] G. Marti 2009
213.64 R1 = 3,4-dihydroxyphenyl
R2 = (2,4,4-trimethyl-1-cyclohexenyl)methyl
R3 = prenyl
R4 = prenyl
R5 = H		 coccinone H M. coccinea[a] −16 (1.0)[b] G. Marti 2009
Structure 214: garciyunnanimine A, garciyunnanimine C — B, bicyclononanes, enamine
214
214.1 R = prenyl garciyunnanimine A[c] G. yunnanensis[a] Hu +11.7 (0.03, m)[b] D. Zheng 2017, J.-Y. Xie 2024
214.2 R = geranyl garciyunnanimine C[c] G. yunnanensis[a] Hu +11.4 (0.041, m)[b] D. Zheng 2017, J.-Y. Xie 2024
Structure 215: hyperelamine A, hyperelanitrile C, hyperelanitrile A and others — B, bicyclononanes, enamine
215
215.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = H		 hyperelamine A[d] H. elatoides[a] +44.3 (0.11, m)[b] J.-Y. Xie 2024
215.2 R1 = Ph
R2 = Me
R3 = prenyl
R4 = (R)-CH(CH3)C≡N		 hyperelanitrile C[d] H. elatoides[a] +28.3 (0.10, m)[b] J.-Y. Xie 2024
215.3 R1 = Ph
R2 = Me
R3 = prenyl
R4 = (S)-CH(CH3)C≡N		 hyperelanitrile A[d] H. elatoides[a] +91.1 (0.05, m)[b] J.-Y. Xie 2024
215.4 R1 = 3,4-dihydroxyphenyl
R2 = (S)-lavandulyl[f]
R3 = H
R4 = H		 garciyunnanimine B[c] G. yunnanensis[a] Hu −69.0 (0.035, m)[b] D. Zheng 2017, J.-Y. Xie 2024
Structure 216: hyperelanitrile D, hyperelanitrile B — B, bicyclononanes, enamine
216
216.1 R = (R)-CH(CH3)C≡N hyperelanitrile D[d] (inseparable E/Z mixture with hyperelanitrile C at exocyclic double bond) H. elatoides[a] N/D J.-Y. Xie 2024
216.2 R = (S)-CH(CH3)C≡N hyperelanitrile B[d] (inseparable E/Z mixture with hyperelanitrile A at exocyclic double bond) H. elatoides[a] N/D J.-Y. Xie 2024
Structure 217: oblongifolin M — B, bicyclononanes, exo
217
217.1 oblongifolin M[c][l][m] G. oblongifolia[a] −4.2 (0.05, m)[b] H. Zhang 2014a
Structure 218: enervosanone — B, bicyclononanes, exo
218
218.1 enervosanone Calophyllum enervosum +10 (0.2000, m)[b] M. Taher 2005
Structure 219: oxy-guttiferone K, oblongifolin G, oblongifolin I and others — B, bicyclononanes, exo
219
219.1 R1 = prenyl
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = OH
X3 = H		 oxy-guttiferone K[d] G. cambogia[a] +20.9 (0.1)[b] M. Masullo 2008, M. Masullo 2010
219.2 R1 = prenyl
R2 = geranyl
R3 = H
X1 = OH
X2 = OH
X3 = H		 oblongifolin G G. oblongifolia[a] +5.9 (0.41)[b] S.-X. Huang 2009
219.3 R1 = prenyl
R2 = geranyl
R3 = H
X1 = H
X2 = H
X3 = OH		 oblongifolin I G. oblongifolia[a] NR Y. Zhou 2010
219.4 R1 = prenyl
R2 = geranyl
R3 = prenyl
X1 = OH
X2 = OH
X3 = H		 garciyunnanin B G. yunnanensis[a] +18.1 (0.12)[b] G. Xu 2008
219.5 R1 = prenyl
R2 = geranyl
R3 = prenyl
X1 = H
X2 = OH
X3 = OH		 garciyunnanin K[d] G. yunnanensis[a] +2.2 (0.10, m)[b] D. Zheng 2021b
219.6 R1 = geranyl
R2 = prenyl
R3 = H
X1 = OH
X2 = OH
X3 = H		 oxy-guttiferone M G. cambogia[a] −96.2 (0.1, m)[b] M. Masullo 2010
219.7 R1 = lavandulyl
R2 = prenyl
R3 = H
X1 = OH
X2 = OH
X3 = H		 symphonone H[e] S. globulifera[a] −37 (0.2)[b] G. Marti 2010
Structure 220: garcimultiflorone I, 2,16-oxyguttiferone A, oblongifolin F and others — B, bicyclononanes, endo
220
220.1 R1 = prenyl
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 garcimultiflorone I[d] G. multiflora[a] −42.1 (0.36, m)[b] W. Fu 2015
220.2 R1 = prenyl
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 2,16-oxyguttiferone A[d] S. globulifera[a] +48 (1.0, m)[b] K. Cottet 2015
220.3 R1 = prenyl
R2 = geranyl
R3 = H
X1 = OH
X2 = H		 oblongifolin F G. oblongifolia[a] −85.6 (0.41)[b] S.-X. Huang 2009
220.4 R1 = prenyl
R2 = geranyl
R3 = H
X1 = H
X2 = OH		 oblongifolin H G. oblongifolia[a] NR Y. Zhou 2010
220.5 R1 = geranyl
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 oxy-guttiferone I G. cambogia[a] +23.8 (0.1, m)[b] M. Masullo 2010
220.6 R1 = (S)-lavandulyl[f]
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 garcimultiflorone J[c] G. multiflora[a] +11.11 (0.44, m)[b] W. Fu 2015, X. Wang 2021a
220.7 R1 = isolavandulyl[g]
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 nujiangefolin A[e] G. nujiangensis[a] −2 (0.10, m)[b] Z.-X. Xia 2012
220.8 R1 = (R)-isolavandulyl[g]
R2 = (E)-CH=CHCMe2OH
R3 = H
X1 = OH
X2 = H		 nujiangefolin D[d] G. nujiangensis[a] −12 (0.10, m)[b] Z. Tang 2019
220.9 R1 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 picrorhizone H[d] G. picrorhiza[a] −7 (0.10, m)[b] E. R. Sukandar 2020
220.10 R1 = 3-isopropenyl-2,2-dimethylcyclopentyl
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 oxy-thorelione A[e] Calophyllum thorelii +91.9 (1.0, m)[b] L.-T. T. Nguyen 2012
220.11 R1 = (2S)-4-hydroxyisolavandulyl[g]
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 garciesculentone B[e] G. esculenta[a] +18.4 (0.04, m)[b] H. Zhang 2014b
Structure 221: garcinialone — B, bicyclononanes, exo
221
221.1 garcinialone[l][m] G. multiflora[a] −2.0 (0.02, m)[b] S.-C. Chien 2008
Structure 222: xanthochymusone N — B, bicyclononanes, endo
222
222.1 xanthochymusone N[d] G. xanthochymus[a] −16 (0.1, m)[b] Y.-G. Fu 2025
Structure 223: no name — B, bicyclononanes, exo
223
223.1 no common name G. indica[a] +18.9 (0.1, m)[b] R. Kaur 2012
Structure 224: symphonone I — B, bicyclononanes, exo
224
224.1 symphonone I S. globulifera[a] −22 (0.4)[b] G. Marti 2010
Structure 225: (+)-garciyunnanin L, (−)-garciyunnanin L, xanthochymusone O — B, bicyclononanes, endo
225
225.1 R = prenyl (+)-garciyunnanin L[c] G. yunnanensis[a] +28.5 (0.10, m)[b] D. Zheng 2021b
225.2 R = prenyl (−)-garciyunnanin L[d] G. xanthochymus[a] −21 (0.1, m)[b] Y.-G. Fu 2025
225.3 R = CH2CH2CMe=CH2 xanthochymusone O[d] G. xanthochymus[a] −21 (0.1, m)[b] Y.-G. Fu 2025
Structure 226: oxy-guttiferone K2, garcixanthochymone J — B, bicyclononanes, exo
226
226.1 R1 = prenyl
R2 = prenyl		 oxy-guttiferone K2 G. cambogia[a] +12.2 (0.1, m)[b] M. Masullo 2010
226.2 R1 = isolavandulyl[g]
R2 = H		 garcixanthochymone J[d][e] G. xanthochymus[a] +53.2 (0.73, m)[b] S. Jin 2021
Structure 227: 4,16-oxyguttiferone A, guttiferone O, garcim-2 and others — B, bicyclononanes, endo
227
227.1 R1 = prenyl
R2 = prenyl
R3 = prenyl		 4,16-oxyguttiferone A S. globulifera[a] +53 (1.0, m)[b] K. Cottet 2015
227.2 R1 = prenyl
R2 = geranyl
R3 = H		 guttiferone O, a.k.a. oxy-oblongifolin A (one of two by that first name) G. afzelii[a] +45 (0.2, a)[b] A. M. Lannang 2010
227.3 R1 = (S)-lavandulyl[f]
R2 = prenyl
R3 = H		 garcim-2[c] G. xanthochymus[a] N/A Z. Wu 2022
227.4 R1 = isolavandulyl[g]
R2 = prenyl
R3 = H		 nujiangefolin B[e] G. nujiangensis[a] +5 (0.10, m)[b] Z.-X. Xia 2012
Structure 228: garciyunnanensisin E — B, bicyclononanes, endo
228
228.1 garciyunnanensisin E[c][e] G. yunnanensis[a] −120.0 (0.1, m)[b] P.-X. Ji 2025
Structure 229: longistylione B, symphonone F, garcixanthochymone G — B, bicyclononanes, exo
229
229.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl		 longistylione B[c] H. longistylum[a] +0.8 (0.04, mc)[b] X. Cao 2017
229.2 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = prenyl
R4 = H		 symphonone F[e] S. globulifera[a] −9 (1.0)[b] G. Marti 2010
229.3 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = prenyl
R4 = H		 garcixanthochymone G[d][e] G. xanthochymus[a] +28.5 (0.87, m)[b] S. Jin 2021
Structure 230: longistylione A, hyperscabrone F, hyperkouytone F and others — B, bicyclononanes, exo
230
230.1 R1 = Ph
R2 = Me
R3 = prenyl		 longistylione A[c] H. longistylum[a] −12.4 (0.4, mc)[b] X. Cao 2017
230.2 R1 = Ph
R2 = prenyl
R3 = H		 hyperscabrone F[c] H. scabrum[a] −18 (0.1, m)[b] W. Gao 2016a
230.3 R1 = Ph
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl		 hyperkouytone F[c] H. kouytchense[a] −46.5 (0.45, m)[b] H.-Y. Lou 2024
230.4 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = H		 symphonone G[e] S. globulifera[a] −4 (0.4)[b] G. Marti 2010
Structure 231: hyperascyrin N — B, bicyclononanes, exo
231
231.1 hyperascyrin N[d] H. ascyron[a] +40.0 (0.1, m)[b] B. Zhen 2019
Structure 232: hyperbeanin Q, garcimultinone K, paucinochymol C and others — B, bicyclononanes, endo
232
232.1 R1 = i-Pr
R2 = CMe2OH
R3 = geranyl
R4 = prenyl
R5 = H		 hyperbeanin Q[c] H. beanii[a] −19.5 (0.4, m)[b] X.-Y. Suo 2021b
232.2 R1 = Ph
R2 = CMe2OH
R3 = (2R,3E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R4 = prenyl
R5 = H		 garcimultinone K[d] G. multiflora[a] −12.00 (0.05, m)[b] H. Teng 2021
232.3 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = geranyl
R4 = prenyl
R5 = H		 paucinochymol C[d] G. paucinervis[a] +17.2 (0.02, m)[b] X. Tan 2020
232.4 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = lavandulyl
R4 = prenyl
R5 = H		 paucinochymol B[d][e] G. paucinervis[a] −46.6 (0.02, m)[b] X. Tan 2020
232.5 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = isolavandulyl[g]
R4 = prenyl
R5 = H		 nujiangefolin C[e] G. nujiangensis[a] +20 (0.05, m)[b] Z.-X. Xia 2012
232.6 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = (E)-CH2CH(CMe=CH2)CH=CHCMe2OH
R4 = prenyl
R5 = H		 garciyunnanensisin D[d][e] G. yunnanensis[a] +112.0 (0.1, m)[b] P.-X. Ji 2025
232.7 R1 = 3,4-hydroxyphenyl
R2 = CMe2OH
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone F[d] G. picrorhiza[a] +11 (0.10, m)[b] E. R. Sukandar 2020
232.8 R1 = 3,4-hydroxyphenyl
R2 = CH(Me)CO2H
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone G[d][e] G. picrorhiza[a] +11 (0.10, m)[b] E. R. Sukandar 2020
Structure 233: hyperibone I, hyperibone H, garcimultinone L and others — B, bicyclononanes, endo
233
233.1 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H		 hyperibone I H. scabrum[a] +13.3 (0.3)[b] M. Matsuhisa 2002, R. Ciochina 2006, K. Lindermayr 2013
233.2 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = H		 hyperibone H H. scabrum[a] +12.4 (0.4)[b] M. Matsuhisa 2002, R. Ciochina 2006
233.3 R1 = Ph
R2 = (S)-lavandulyl[f]
R3 = prenyl
R4 = H		 garcimultinone L[d] G. multiflora[a] +110.00 (0.04, m)[b] H. Teng 2021
233.4 R1 = 3,4-dihydroxyphenyl
R2 = (S)-lavandulyl
R3 = prenyl
R4 = H		 garynthone D G. yunnanensis[a] racemic; +21.52 (0.1, m)[b] and −18.83 (0.1, m)[b] Z. Guo 2025a
233.5 R1 = 3,4-dihydroxyphenyl
R2 = (S)-isolavandulyl[g]
R3 = prenyl
R4 = H		 garynthone E[d] G. yunnanensis[a] −31.07 (0.1, m)[b] Z. Guo 2025a
Structure 234: thorelione B — B, bicyclononanes, endo
234
234.1 thorelione B[e] Calophyllum thorelii +412.0 (0.14, e)[b] L.-T. T. Nguyen 2012
Structure 235: oblongifolin X, garcowacinol E, garcowacinol G — B, bicyclononanes, exo
235
235.1 R1 = CMe=CH2
R2 = H		 oblongifolin X[d] G. oblongifolia[a] −11.8 (0.03, m)[b] H. Zhang 2016
235.2 R1 = CMe=CH2
R2 = prenyl		 garcowacinol E[d] G. cowa[a] −36.0 (0.50, m)[b] S. Kaennakam 2022b
235.3 R1 = CMe2OH
R2 = prenyl		 garcowacinol G[d] G. cowa[a] −28.1 (0.30, m)[b] S. Kaennakam 2022b
Structure 236: garcowacinol H — B, bicyclononanes, exo
236
236.1 garcowacinol H[d] G. cowa[a] −21.2 (0.50, m)[b] S. Kaennakam 2022b
Structure 237: garcowacinol F, guttiferone R, oblongifolin R and others — B, bicyclononanes, exo
237
237.1 R1 = H
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl		 garcowacinol F[d] G. cowa[a] −25.0 (0.50, m)[b] S. Kaennakam 2022b
237.2 R1 = H
R2 = CMe2OH
R3 = prenyl
R4 = prenyl		 guttiferone R[d] G. cochinchinensis[a] −57.5 (0.33, m)[b] H. D. Nguyen 2011, S. Kaennakam 2022b
237.3 R1 = H
R2 = CMe2OH
R3 = geranyl
R4 = H		 oblongifolin R[d][l][m] G. oblongifolia[a] −54.5 (0.03, m)[b] H. Zhang 2014a
237.4 R1 = prenyl
R2 = CMe=CH2
R3 = prenyl
R4 = H		 hyperscabrone E[d] H. scabrum[a] −10 (0.1, m)[b] W. Gao 2016a
Structure 238: mesuaferroic acid C, mesuaferroic acid F, mesuaferroic acid A and others — B, bicyclononanes, endo
238
238.1 R1 = i-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid C[n] Mesua ferrea NR N. E. Rasol 2017
238.2 R1 = i-Bu
R2 = (S)-CHPhCH2CO2H
R3 = CH2CH(OH)CMe2OH		 mesuaferroic acid F[e][n] Mesua ferrea NR N. E. Rasol 2017
238.3 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid A[e] Mesua ferrea NR N. E. Rasol 2017
238.4 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = CH2CH(OH)CMe2OH		 mesuaferroic acid E[e][n] Mesua ferrea NR N. E. Rasol 2017
238.5 R1 = Ph
R2 = prenyl
R3 = prenyl		 sampsonione P, a.k.a. hyperscabrone L H. sampsonii, H. scabrum[a] +18.6 (0.022)[b], +40.0 (0.1, m)[b] W. Gao 2016b, Z. Y. Xiao 2007
238.6 R1 = Ph
R2 = prenyl
R3 = (R)-CH2CH(OH)CMe2OH		 hypersampsone V[k] H. sampsonii[a] +13.0 (0.50)[b] W.-J. Tian 2016
238.7 R1 = Ph
R2 = prenyl
R3 = (S)-CH2CH(OH)CMe2OH		 hypersampsone W[k] H. sampsonii[a] +0.60 (0.50)[b] W.-J. Tian 2016
Structure 239: mesuaferroic acid B, mesuaferroic acid J, hyperattenin E and others — B, bicyclononanes, endo
239
239.1 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid B[e][n] Mesua ferrea NR N. E. Rasol 2017
239.2 R1 = CH2CMe2OH
R2 = CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid J[e] Mesua ferrea +4.25 (0.2, m)[b] X.-C. Zhang, 2020
239.3 R1 = Ph
R2 = prenyl
R3 = prenyl		 hyperattenin E, a.k.a. hyperibrin D[d] H. scabrum[a] −13.0 (0.19, m)[b] D. Li 2015a, W. Gao 2016c, X.-W. Yang 2018
239.4 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-6,6-dimethyl-2-methylenecyclohexylmethyl		 paucinone D G. paucinervis[a] +41.6 (0.11, m)[b] X.-M. Gao 2010
Structure 240: paucinone A — B, bicyclononanes, endo
240
240.1 paucinone A G. paucinervis[a] −6.2 (0.05, m)[b] X.-M. Gao 2010
Structure 241: paucinone B — B, bicyclononanes, endo
241
241.1 paucinone B G. paucinervis[a] +58.7 (0.10, m)[b] X.-M. Gao 2010
Structure 242: paucinone C — B, bicyclononanes, endo
242
242.1 paucinone C G. paucinervis[a] +19.2 (0.17, m)[b] X.-M. Gao 2010
Structure 243: garcicowin A — B, bicyclononanes, noC3
243
243.1 garcicowin A G. cowa[a] −219.0 (0.09)[b] G. Xu 2010
Structure 244: garcowacinol D — B, bicyclononanes, noC3
244
244.1 garcowacinol D[d] G. cowa[a] +37.0 (0.50, m)[b] S. Kaennakam 2022b
Structure 245: garcowacinol C, oblongifolin S, xanthochymusone G — B, bicyclononanes, exo
245
245.1 R1 = Ph
R2 = H
R3 = H
R4 = prenyl
R5 = prenyl		 garcowacinol C[d] G. cowa[a] +28.5 (0.50, m)[b] S. Kaennakam 2022b
245.2 R1 = Ph
R2 = H
R3 = OH
R4 = geranyl
R5 = H		 oblongifolin S[d][l][m] G. oblongifolia[a] −37.8 (0.04, m)[b] H. Zhang 2014a
245.3 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 xanthochymusone G[d] G. xanthochymus[a] −141 (0.1, m)[b] Z.-H. Xu 2022
Structure 246: oblongifolin W, 13,14-didehydroxy-7-epi-isogarcinol, 14-deoxy-7-epi-isogarcinol and others — B, bicyclononanes, exo
246
246.1 R1 = Ph
R2 = H
R3 = H
R4 = (E)-CH=CHCMe=O		 oblongifolin W[d] G. oblongifolia[a] +20.0 (0.03, m)[b] H. Zhang 2016
246.2 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl		 13,14-didehydroxy-7-epi-isogarcinol G. multiflora[a] −185 (0.13)[b] J.-J. Chen 2009, X. Wang 2021a
246.3 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl		 14-deoxy-7-epi-isogarcinol S. globulifera[a] −77 (0.9)[b] G. Marti 2010
246.4 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl		 7-epi-isogarcinol M. coccinea, S. globulifera[a] −158 (1.0)[b] G. Marti 2009, G. Marti 2010
246.5 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = 3-methylbutyl		 epunctanone G. epunctata[a] Stapf +24.9 (0.00985, a)[b] G. Y. T. Fotso 2014
246.6 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe=CH2		 symphonone A S. globulifera[a] −37 (0.7)[b] G. Marti 2010
246.7 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 symphonone C S. globulifera[a] −67 (1.0)[b] G. Marti 2010
246.8 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl		 symphonone B S. globulifera[a] −81 (1.0)[b] G. Marti 2010
246.9 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl		 7-epi-coccinone B S. globulifera[a] −50 (0.9)[b] G. Marti 2010
246.10 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = CH2CH2CMe=CH2
R4 = prenyl		 xanthochymusone F[d] G. xanthochymus[a] +141 (0.1, m)[b] Z.-H. Xu 2022
246.11 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CHOHCMe2OH
R4 = prenyl		 symphonone D[e] S. globulifera[a] −41 (0.4)[b] G. Marti 2010
246.12 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CHOHCMe2OH
R4 = prenyl		 symphonone E[e] (diastereomer) S. globulifera[a] −50 (0.4)[b] G. Marti 2010
Structure 247: oblongifolin Y, hypersampsonone J, guttiferone T — B, bicyclononanes, endo
247
247.1 R1 = Ph
R2 = H
R3 = H
R4 = CH2CO2H		 oblongifolin Y[d] G. oblongifolia[a] +24.1 (0.06, m)[b] H. Zhang 2016
247.2 R1 = Ph
R2 = prenyl
R3 = OH
R4 = prenyl		 hypersampsonone J[d] H. sampsonii[a] +17.5 (1.0, m)[b] Y. Li 2023
247.3 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CH2CMe=CH2
R4 = CH2CHOHCMe=CH2		 guttiferone T[e] G. cochinchinensis[a] −14 (0.3)[b] B. T. D. Trinh 2013
Structure 248: 13,14-didehydroxyisoxanthochymol, garcimultinone M, 14-deoxyisogarcinol and others — B, bicyclononanes, endo
248
248.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 13,14-didehydroxyisoxanthochymol[d] G. multiflora[a] +205.7 (0.15)[b] G. Xu 2010
248.2 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 garcimultinone M[c] (enantiomer) G. multiflora[a] −114.44 (0.02, m)[b] H. Teng 2021
248.3 R1 = 3-hydroxyphenyl
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 14-deoxyisogarcinol G. indica[a] −178.0 (0.1, m)[b] R. Kaur 2012
248.4 R1 = 3-hydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 xanthochymusone C[d] G. xanthochymus[a] +132 (0.1, m)[b] Z.-H. Xu 2022
248.5 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 isoxanthochymol[d] G. pyrifera, G. subelliptica, G. xanthochymus, G. ovafolia[a] +181 (0.6, e)[b] C. G. Karanjgoakar 1973, K. R. Gustafson 1992, M. Iinuma 1996, D. Roux 2000, S. Baggett 2005, C. Socolsky 2015
248.6 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 isogarcinol, a.k.a. cambogin, a.k.a. 30-epi-cambogin[c] (enantiomer) G. indica, G. cambogia, G. cochinchinensis, G. cowa, G. pedunculata[a] −224 (0.1, m)[b] A. V. Rama Rao 1980, N. Krishnamurthy 1981, N. Krishnamurthy 1982, A. Sahu 1989, R. W. Fuller 1999, G. Xu 2010, B. T. D. Trinh 2013, C. Socolsky 2015, D. Zheng 2021a, X. Wang 2021a
248.7 R1 = 3,4-hydroxyphenyl
R2 = Me
R3 = prenyl
R4 = CH2CH2CMe2OH
R5 = prenyl		 xanthochymusone D[d] G. xanthochymus[a] +186 (0.1, m)[b] Z.-H. Xu 2022
248.8 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 (+)-cycloxanthochymol G. pyrifera, G. subelliptica, M. coccinea[a] +112 (1)[b] M. Iinuma 1996, D. Roux 2000, G. Marti 2009
248.9 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 (−)-cycloxanthochymol[j] (enantiomer) G. subelliptica[a] −80.9 (2.20, m)[b] L.-J. Zhang 2010
248.10 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = prenyl
R4 = CH2CHOHCMe2OH
R5 = prenyl		 coccinone D[e] M. coccinea[a] −76 (0.4)[b] G. Marti 2009
248.11 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = prenyl
R4 = CH2CHOHCMe2OH
R5 = prenyl		 coccinone E[e] (diastereomer) M. coccinea[a] −70 (0.3)[b] G. Marti 2009
248.12 R1 = 3,4-hydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = CH2CH2CMe2OH
R5 = prenyl		 xanthochymusone E[d] G. xanthochymus[a] +117 (0.1, m)[b] Z.-H. Xu 2022
248.13 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe2OH
R4 = prenyl
R5 = prenyl		 coccinone C M. coccinea[a] −60 (0.2)[b] G. Marti 2009
248.14 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = (S)-CH2CH(OH)CMe=CH2
R4 = prenyl
R5 = prenyl		 garpedvinin F[c] G. pedunculata[a] Roxb. −118.3 (0.1, m)[b] D.-L. Zou 2025
248.15 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe2OH
R4 = (S)-CH2CHOHCMe2OH
R5 = CH2CH2CMe2OH		 garcixanthochymone H[d] G. xanthochymus[a] +31.6 (0.25, m)[b] S. Jin 2021
248.16 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = CH2CH2CMe2OH		 garcixanthochymone I[d] G. xanthochymus[a] +17.8 (0.33, m)[b] S. Jin 2021
248.17 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2COCMe=CH2
R4 = prenyl
R5 = prenyl		 garcixanthochymone F[d] G. xanthochymus[a] +55.3 (0.21, m)[b] S. Jin 2021
248.18 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl		 coccinone B M. coccinea[a] −55 (0.3)[b] G. Marti 2009
248.19 R1 = 3,4-dihydroxyphenyl
R2 = CH2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl		 garynthone H G. yunnanensis[a] racemic; +160.00 (0.1, m)[b] and −182.25 (0.1, m)[b] Z. Guo 2025a
248.20 R1 = 3,4-dihydroxyphenyl
R2 = CH2OH
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 garynthone I[d] G. yunnanensis[a] +96.5 (0.1, m)[b] Z. Guo 2025a
Structure 249: garpedvinin E — B, bicyclononanes, endo
249
249.1 garpedvinin E[c] G. pedunculata[a] Roxb. −86.6 (0.30, m)[b] D.-L. Zou 2025
Structure 250: garpedvinin A — B, bicyclononanes, endo
250
250.1 garpedvinin A[c] G. pedunculata[a] Roxb. −86.6 (0.30, m)[b] D.-L. Zou 2025
Structure 251: garciesculentone A — B, bicyclononanes, endo
251
251.1 garciesculentone A[m] G. esculenta[a] −116.5 (0.06, m)[b] H. Zhang 2014b
Structure 252: garcinialiptone B — B, bicyclononanes, endo
252
252.1 garcinialiptone B G. subelliptica[a] +84.8 (5.40, m)[b] L.-J. Zhang 2010
Structure 253: garcicowin D — B, bicyclononanes, exo
253
253.1 garcicowin D G. cowa[a] +336.0 (0.12)[b] G. Xu 2010, Z.-H. Xu 2022
Structure 254: 13,14-didehydroxygarcicowin C, xanthochymusone H, garcicowin C and others — B, bicyclononanes, endo
254
254.1 R1 = Ph
R2 = CH=CMe2		 13,14-didehydroxygarcicowin C[c] G. multiflora[a] −68.6 (0.18)[b] G. Xu 2010, Y.-G. Fu 2025
254.2 R1 = 3-hydroxyphenyl
R2 = CH=CMe2		 xanthochymusone H[d] G. xanthochymus[a] +60 (0.1, m)[b] Z.-H. Xu 2022
254.3 R1 = 3,4-dihydroxyphenyl
R2 = CH=CMe2		 garcicowin C[c] G. cowa[a] −72.1 (0.10)[b] G. Xu 2010, Z.-H. Xu 2022
254.4 R1 = 3,4-dihydroxyphenyl
R2 = CH=CMe2		 xanthochymusone I[d] (enantiomer) G. xanthochymus[a] +69 (0.1, m)[b] Z.-H. Xu 2022
254.5 R1 = 3,4-dihydroxyphenyl
R2 = (R)-CH(OH)CMe2OH		 garynthone G G. yunnanensis[a] racemic; +160 (0.1, m)[b] and −76.85 (0.1, m)[b] Z. Guo 2025a
254.6 R1 = 3,4-dihydroxyphenyl
R2 = (R)-CH(OH)CMe2OMe		 garynthone F G. yunnanensis[a] racemic; +114.47 (0.1, m)[b] and −135.64 (0.1, m)[b] Z. Guo 2025a
Structure 255: garpedvinin D — B, bicyclononanes, endo
255
255.1 garpedvinin D[c] G. pedunculata[a] Roxb. −54.6 (0.1, m)[b] D.-L. Zou 2025
Structure 256: garcoblone E — B, bicyclononanes, endo
256
256.1 garcoblone E[c] G. oblongifolia, G. yunnanensis[a] −44.5 (1.0, m)[b] Z. Wu 2022, Z. Guo 2025a
Structure 257: coccinone A — B, bicyclononanes, endo
257
257.1 coccinone A M. coccinea[a] +28 (1.0)[b] G. Marti 2009
Structure 258: garpedvinin B — B, bicyclononanes, endo
258
258.1 garpedvinin B[c] G. pedunculata[a] Roxb. −65.5 (0.1, m)[b] D.-L. Zou 2025
Structure 259: garpedvinin C — B, bicyclononanes, endo
259
259.1 garpedvinin C[c] G. pedunculata[a] Roxb. −68.8 (0.1, m)[b] D.-L. Zou 2025
Structure 260: garcimultiflorone B, 13-hydroxygarcimultiflorone B — B, bicyclononanes, endo
260
260.1 R = Ph garcimultiflorone B G. multiflora[a] −132 (0.96)[b] J.-J. Chen 2009
260.2 R = 3-hydroxyphenyl 13-hydroxygarcimultiflorone B G. multiflora[a] −115 (0.13)[b] J.-J. Chen 2009
Structure 261: hyperascyrin M — B, bicyclononanes, endo
261
261.1 hyperascyrin M[d] H. ascyron[a] −57.2 (0.1, m)[b] B. Zhen 2019
Structure 262: garschomcinol E, garschomcinol D — B, bicyclononanes, endo
262
262.1 R = CH2CH2CHMeCO2H garschomcinol E[d][e] G. schomburgkiana[a] +12.5 (0.20, m)[b] S. Kaennakam 2022a
262.2 R = geranyl garschomcinol D[d] G. schomburgkiana[a] +13.1 (0.30, m)[b] S. Kaennakam 2022a
Structure 263: guttiferone S, longistylione D, ascyrone C and others — B, bicyclononanes, exo
263
263.1 R1 = H
R2 = prenyl
R3 = prenyl		 guttiferone S G. cochinchinensis[a] −10 (0.28, m)[b] H. D. Nguyen 2011, D. H. Le 2016
263.2 R1 = prenyl
R2 = Me
R3 = prenyl		 longistylione D[c] H. longistylum[a] +19.5 (0.13, mc)[b] X. Cao 2017
263.3 R1 = prenyl
R2 = Me
R3 = (E)-CH=CHCMe2OH		 ascyrone C[d] H. ascyron[a] +78 (0.06, m)[b] X. Deng 2022
263.4 R1 = prenyl
R2 = Me
R3 = (E)-CH=CHC(Me)=CH2		 ascyrone E[d] H. ascyron[a] +3 (0.09, MeOH)[b] X. Deng 2022
Structure 264: garcowacinol J, garcowacinol I, longistylione C and others — B, bicyclononanes, exo
264
264.1 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = CMe=CH2		 garcowacinol J[d] G. cowa[a] +18.0 (0.10, m)[b] S. Kaennakam 2022b
264.2 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = CMe2OH		 garcowacinol I[d] G. cowa[a] +13.5 (0.10, m)[b] S. Kaennakam 2022b
264.3 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = CMe2OH		 longistylione C[c] H. longistylum[a] +154.3 (0.33, mc)[b] X. Cao 2017
264.4 R1 = Ph
R2 = prenyl
R3 = Me
R4 = (E)-CH=CHCMe2OH
R5 = CMe2OH		 ascyrone D[d] H. ascyron[a] +11 (0.11, m)[b] X. Deng 2022
264.5 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = Me
R4 = prenyl
R5 = CMe2OH		 ascyrone A[d] H. ascyron[a] +6 (0.05, m)[b] X. Deng 2022
264.6 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = Me
R4 = (E)-CH=CHCMe2OH
R5 = CMe2OH		 ascyrone B[d] H. ascyron[a] +34 (0.16, m)[b] X. Deng 2022
264.7 R1 = 3,4-dihydroxyphenyl
R2 = H
R3 = prenyl
R4 = geranyl
R5 = CMe2OH		 schomburgkianone E[d] G. schomburgkiana[a] +104 (0.4)[b] D. H. Le 2016
Structure 265: guttiferone H — B, bicyclononanes, exo
265
265.1 guttiferone H[e] G. xanthochymus[a] +94 (0.006)[b] S. Baggett 2005
Structure 266: garcixanthochymone K — B, bicyclononanes, exo
266
266.1 garcixanthochymone K[d] G. xanthochymus[a] −37.9 (0.20, m)[b] S. Jin 2021
Structure 267: burlemarxione E — B, bicyclononanes, caged
267
267.1 burlemarxione E C. burlemarxii[a] +11.0 (0.5)[b] C. G. Ferraz 2021
Structure 268: hyperprin A — B, bicyclononanes, caged
268
268.1 hyperprin A[d] H. przewalskii[a] −4.0 (0.10, m)[b] J.-F. Zong 2020
Structure 269: garciyunnanol D, garciyunnanol C, garciyunnanol B — B, bicyclononanes, exo
269
269.1 R = prenyl
X = OH		 garciyunnanol D[d] G. yunnanensis[a] +158 (0.64, m)[b] X.-Y. Hu 2024
269.2 R = geranyl
X = H		 garciyunnanol C[d] G. yunnanensis[a] +17 (0.18, m)[b] X.-Y. Hu 2024
269.3 R = geranyl
X = OH		 garciyunnanol B[d] G. yunnanensis[a] +115 (0.39, m)[b] X.-Y. Hu 2024
Structure 270: garciyunnanol A — B, bicyclononanes, exo
270
270.1 garciyunnanol A[d] G. yunnanensis[a] +14 (0.16, m)[b] X.-Y. Hu 2024
Structure 271: thoreliolide A — B, bicyclononanes, endo
271
271.1 thoreliolide A[d][e] Calophyllum thorelii +82.0 (0.45, e)[b] L.-T. T. Nguyen 2016
Structure 272: thoreliolide B — B, bicyclononanes, exo
272
272.1 thoreliolide B[d] Calophyllum thorelii −51.2 (0.75, e)[b] L.-T. T. Nguyen 2016
Structure 273: hyperibone K, hypersampsonone K, hyperibrin E and others — B, bicyclononanes, caged
273
273.1 R1 = Ph
R2 = prenyl
R3 = CH=CMe2
R4 = prenyl		 hyperibone K[d] H. scabrum[a] +22.3 (0.3)[b] N. Tanaka 2004, J. Qi 2010
273.2 R1 = Ph
R2 = prenyl
R3 = CH=CMe2
R4 = (E)-4-oxo-3-methyl-2-buten-1-yl		 hypersampsonone K[d] H. sampsonii[a] −7.5 (1.0, m)[b] Y. Li 2023
273.3 R1 = Ph
R2 = prenyl
R3 = CH2C(=O)CH3
R4 = prenyl		 hyperibrin E[d] H. scabrum[a] +47.3 (0.06, m)[b] J. Hu 2017
273.4 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = CH=CMe2
R4 = prenyl		 18-hydroxyhyperibone K H. hypericoides[a] NR O. E. Christian 2008
273.5 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2C(=O)CH3
R4 = prenyl		 oblongifolin K[c] G. oblongifolia[a] +55.4 (0.07, m)[b] H. Zhang 2014a
273.6 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = CH=CMe2
R4 = prenyl		 garciniagifolone A[e] G. oblongifolia[a] +7.0 (0.09, m)[b] W.-G. Shan 2012
273.7 R1 = 3,4-dihydroxyphenyl
R2 = 2,4,4-trimethyl-1-cyclohexen-1-ylmethyl
R3 = CH=CMe2
R4 = prenyl		 garpauvinin A[d] G. paucinervis[a] −49.86 (0.91, m)[b] C.-C. Jia 2023
273.8 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = CH=CMe2
R4 = prenyl		 (+)-garcinialiptone A[e][j] G. subelliptica[a] +12.1 (3.40, m)[b] L.-J. Zhang 2010
273.9 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = CH=CMe2
R4 = prenyl		 (−)-garcinialiptone A[e][j] (enantiomer) G. subelliptica, G. yunnanensis[a] −17.3 (3.36, m)[b] L.-J. Zhang 2010
273.10 R1 = 3,4-dihydroxyphenyl
R2 = CH2CH(CMe=CH2)CH2CH2CMe2OH
R3 = CH=CMe2
R4 = prenyl		 garcixanthochymone A[e] G. xanthochymus[a] −13.8 (0.660, m)[b] Y. Chen 2017
273.11 R1 = 3,4-dihydroxyphenyl
R2 = (E)-CH2CH(CMe=CH2)CH=CHCMe2OH
R3 = CH=CMe2
R4 = prenyl		 garciyunnanensisin B[d][e] G. yunnanensis[a] −130.8 (0.1, m)[b] P.-X. Ji 2025
273.12 R1 = 3,4-dihydroxyphenyl
R2 = (S)-lavandulyl
R3 = (R)-3,3-dimethyloxiran-2-yl
R4 = prenyl		 garpedvinin I[d] G. pedunculata[a] Roxb. −54.7 (0.1, m)[b] D.-L. Zou 2025
273.13 R1 = 3,4-dihydroxyphenyl
R2 = (2R,4S)-CH2CH(CMe=CH2)CH2CH(OOH)CMe=CH2
R3 = CH=CMe2
R4 = prenyl		 garpedvinin J[d] G. pedunculata[a] Roxb. −79.0 (0.1, m)[b] D.-L. Zou 2025
273.14 R1 = 3,4-dihydroxyphenyl
R2 = (S,E)-CH2CH(CMe=CH2)CH=CHCMe2OH
R3 = CH=CMe2
R4 = prenyl		 garpedvinin H[d] G. pedunculata[a] Roxb. −79.0 (0.1, m)[b] D.-L. Zou 2025
273.15 R1 = 3,4-dihydroxyphenyl
R2 = (S,E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R3 = CH=CMe2
R4 = prenyl		 garpedvinin G[d] G. pedunculata[a] Roxb. −118.3 (0.1, m)[b] D.-L. Zou 2025
273.16 R1 = 3,4-dihydroxyphenyl
R2 = 4-hydroxyisolavandulyl[g]
R3 = CH=CMe2
R4 = prenyl		 garcixanthochymone B[e] G. xanthochymus[a] −0.81 (0.410, m)[b] Y. Chen 2017
273.17 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = OH
R4 = prenyl		 garciyunnanensisin A[d][e] G. yunnanensis[a] −150.2 (0.1, m)[b] P.-X. Ji 2025
Structure 274: garcixanthochymone C — B, bicyclononanes, caged
274
274.1 garcixanthochymone C G. xanthochymus[a] +51.0 (0.400, m)[b] Y. Chen 2017
Structure 275: oblongifolin J — B, bicyclononanes, caged
275
275.1 oblongifolin J[c] G. oblongifolia[a] +8.6 (0.03, m)[b] H. Zhang 2014a
Structure 276: hypersampsone R — B, bicyclononanes, endo
276
276.1 hypersampsone R (one of two by that name) H. sampsonii[a] +160 (0.1)[b] J.-J. Chen 2014
Structure 277: garcimultiflorone C — B, bicyclononanes, caged
277
277.1 garcimultiflorone C[e] G. multiflora[a] −25.3 (0.12)[b] J.-J. Chen 2009
Structure 278: hypersamponol D — B, bicyclononanes, caged
278
278.1 hypersamponol D[d] H. scabrum, H. sampsonii[a]  +17.2 (1.0, m)[b], +25.46 (0.016, m)[b] U. Kim 2026, S. Soroury 2020
Structure 279: garynthone B, garynthone C — B, bicyclononanes, caged
279
279.1 R = (S)-lavandulyl garynthone B G. yunnanensis[a] racemic; +28.70 (0.1, m)[b] and −30.33 (0.1, m)[b] Z. Guo 2025a
279.2 R = (S)-isolavandulyl[g] garynthone C[d] G. yunnanensis[a] +7.85 (0.1, m)[b] Z. Guo 2025a
Structure 280: soniiglucinol A — A, bicyclononanes, endo
280
280.1 soniiglucinol A[c] H. wilsonii[a] −74.0 (0.2, m)[b] S. Xie 2020a
Structure 281: soniiglucinol B — A, bicyclononanes, endo
281
281.1 soniiglucinol B[c][e] H. wilsonii[a] −139.4 (0.4, m)[b] S. Xie 2020a
Structure 282: hypersonin A, hypersonin C, hypersonin B — A, bicyclononanes, endo
282
282.1 R1 = i-Pr
R2 = prenyl		 hypersonin A[c] H. wilsonii[a] −13 (0.9, m)[b] S. Xie 2020b
282.2 R1 = i-Pr
R2 = geranyl		 hypersonin C[c] H. wilsonii[a] −2 (0.4, m)[b] S. Xie 2020b
282.3 R1 = s-Bu
R2 = prenyl		 hypersonin B[c][e] H. wilsonii[a] +3 (0.9, m)[b] S. Xie 2020b
Structure 283: hypersonin D — A, bicyclononanes, endo
283
283.1 hypersonin D[c][e] H. wilsonii[a] −1 (0.2, m)[b] S. Xie 2020b
Structure 284: soniiglucinol C — A, bicyclononanes, endo
284
284.1 soniiglucinol C[c] H. wilsonii[a] −151.3 (0.3, m)[b] S. Xie 2020a
Structure 285: soniiglucinol D — A, bicyclononanes, endo
285
285.1 soniiglucinol D[c] H. wilsonii[a] −24.9 (0.2, m)[b] S. Xie 2020a
Structure 286: enaimeone A — B, bicyclooctanes
286
286.1 enaimeone A H. papuanum[a] +27.8 (0.1, m)[b] K. Winkelmann 2001b, A. B. zur Bonsen 2023
Structure 287: enaimeone B, enaimeone C — B, bicyclooctanes
287
287.1 R = i-Pr enaimeone B H. papuanum[a] +29.4 (0.1, m)[b] K. Winkelmann 2001b, A. B. zur Bonsen 2023
287.2 R = s-Bu enaimeone C[e] H. papuanum[a] +32.9 (0.1, m)[b] K. Winkelmann 2001b, A. B. zur Bonsen 2023
Structure 288: hyperxylone B, hyperxylone A — B, bicyclooctanes
288
288.1 R1 = H
R2 = geranyl		 hyperxylone B[c] H. beanii[a] +41 (0.09, m)[b] X.-Y. Li 2022
288.2 R1 = prenyl
R2 = prenyl		 hyperxylone A[c] H. beanii[a] +38 (0.08, m)[b] X.-Y. Li 2022
Structure 289: ialibinone A, 1′-hydroxyialibinone A, yezo'otogirin E and others — B, bicyclooctanes
289
289.1 R1 = i-Pr
R2 = CMe=CH2		 ialibinone A H. papuanum[a] −22 (0.1)[b] K. Winkelmann 2000
289.2 R1 = i-Pr
R2 = CMe2OH		 1′-hydroxyialibinone A H. papuanum[a] +3.7 (0.1, m)[b] K. Winkelmann 2001b
289.3 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2		 yezo'otogirin E H. yezoense[a] +21.4 (1.7, m)[b] N. Tanaka 2016a
289.4 R1 = s-Bu
R2 = CMe=CH2		 ialibinone C[e] H. papuanum[a] −26 (0.1)[b] K. Winkelmann 2000
Structure 290: ialibinone E, ialibinone B, 1′-hydroxyialibinone B and others — B, bicyclooctanes
290
290.1 R1 = i-Pr
R2 = H		 ialibinone E H. papuanum[a] −33 (0.1)[b] K. Winkelmann 2000
290.2 R1 = i-Pr
R2 = CMe=CH2		 ialibinone B H. papuanum[a] −91 (0.1)[b] K. Winkelmann 2000
290.3 R1 = i-Pr
R2 = CMe2OH		 1′-hydroxyialibinone B H. papuanum[a] −35.7 (0.1, m)[b] K. Winkelmann 2001b
290.4 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2		 yezo'otogirin F H. yezoense[a] +75.9 (1.7, m)[b] N. Tanaka 2016a
290.5 R1 = s-Bu
R2 = CMe=CH2		 ialibinone D[e] H. papuanum[a] −72 (0.1)[b] K. Winkelmann 2000
290.6 R1 = s-Bu
R2 = CMe2OH		 1′-hydroxyialibinone D[e] H. papuanum[a] −30.3 (0.1, m)[b] K. Winkelmann 2001b
Structure 291: lancasternoid A — B, bicyclooctanes
291
291.1 lancasternoid A H. lancasteri[a] racemic J.-Q. You 2025
Structure 292: lancasternoid B — B, bicyclooctanes
292
292.1 lancasternoid B H. lancasteri[a] racemic J.-Q. You 2025
Structure 293: lancasternoid C — B, bicyclooctanes
293
293.1 lancasternoid C H. lancasteri[a] racemic J.-Q. You 2025
Structure 294: lancasternoid D — B, bicyclooctanes
294
294.1 lancasternoid D H. lancasteri[a] racemic J.-Q. You 2025
Structure 295: takaneone A — B, bicyclooctanes, twoC3
295
295.1 takaneone A H. sikokumontanum[a] +30.0 (0.2, m)[b] N. Tanaka 2008
Structure 296: takaneone B — B, bicyclooctanes, twoC3
296
296.1 takaneone B H. sikokumontanum[a] +24.0 (0.3, m)[b] N. Tanaka 2008
Structure 297: takaneone C, hyperelodione E — A, bicyclooctanes, twoC3
297
297.1 R = COCH3 takaneone C H. sikokumontanum[a] +61.9 (0.4, m)[b] N. Tanaka 2008
297.2 R = C(=CH2)CH2CH2CH=CMe2 hyperelodione E[d] H. elodeoides[a] +44.0 (0.24, m)[b] D.-R. Qiu 2021
Structure 298: hyperelodione F — A, bicyclooctanes, twoC3
298
298.1 hyperelodione F[d] H. elodeoides[a] +24.8 (0.33, m)[b] D.-R. Qiu 2021
Structure 299: garcibracgluinol A — bicyclooctanes, seco
299
299.1 garcibracgluinol A[c] G. bracteata[a] +141.4 (0.02, m)[b] J. Xu 2025
Structure 300: no name — B, bicyclooctanes, seco
300
300.1 no common name H. scabrum[a] +30.5 (1.0)[b] S. Soroury 2020
Structure 301: hyperireflexolide A — otherSpiro, seco
301
301.1 hyperireflexolide A[c] H. beanni[a] 0 (1.54)[b] L. Cardona 1993
Structure 302: hyperireflexolide B — otherSpiro, seco
302
302.1 hyperireflexolide B[c] H. beanni[a] 0 (0.74)[b] L. Cardona 1993, A. B. zur Bonsen 2023
Structure 303: hyperberlone A — otherBridgedBicycles, seco
303
303.1 hyperberlone A[c] H. beanni[a] 0 (0.74)[b] Y.-W. Li 2022
Structure 304: garcinielliptone HG, garcinielliptone HH — B, bicyclooctanes
304
304.1 garcinielliptone HG[c] G. subelliptica[a] −17 (0.02, m)[b] C.-C. Liaw 2019
304.2 garcinielliptone HH[d] (enantiomer) G. subelliptica[a] +16 (0.05, m)[b] C.-C. Liaw 2019
Structure 305: (−)-nemorosonol, (+)-nemorosonol, garmultinone D and others — caged, fourPlusTwo
305
305.1 R1 = prenyl
R2 = H
R3 = prenyl		 (−)-nemorosonol, a.k.a. burlemarxione C, and tautomer isonemorosonol[c] C. burle-marxii, T. japonicum[a] −207 (0.7)[b], −48 (1.35)[b] A. Oya 2015, C. G. Ferraz 2019, M. do C. C. Silva 2024
305.2 R1 = prenyl
R2 = H
R3 = prenyl		 (+)-nemorosonol[d] (enantiomer) C. nemorosa[a] +203 (0.7)[b] F. delle Monache 1988, S. Cerrini 1993
305.3 R1 = prenyl
R2 = H
R3 = cis-3-isopropenyl-2,2-dimethylcyclopentyl		 garmultinone D[d][e] G. multiflora[a] +172.5 (0.04, m)[b] Y. Chen 2019b
305.4 R1 = CH2CH2CMe=CH2
R2 = H
R3 = prenyl		 doitunggarcinone B, a.k.a. burlemarxione G, and tautomer burlemarxione F C burle-marxii, G. propinqua[a] −129 (0.054)[b], −14.0 (0.5)[b] C. Tantapakul 2012, H. P. Pepper 2012, C. G. Ferraz 2021, M. do C. C. Silva 2024
305.5 R1 = prenyl
R2 = prenyl
R3 = prenyl		 ascyronone E, a.k.a. hypatulin C[d][w] H. ascyron, H. patulum[a] −86.8 (0.1, m)[b], +102.5 (0.3, m)[b] Z. P. Li 2019, N. Tanaka 2020
Structure 306: trijapin A — caged, fourPlusTwo
306
306.1 trijapin A[c] T. japonicum[a] −25 (0.2, m)[b] A. Oya 2015
Structure 307: trijapin B, garcibracteamone J — caged, fourPlusTwo
307
307.1 R = prenyl trijapin B T. japonicum[a] −200 (0.1, m)[b] A. Oya 2015
307.2 R = CH2CH2CMe=CH2 garcibracteamone J[c] G. bracteata[a] −169 (0.02, m)[b] Q. Xue 2020
Structure 308: trijapin C — caged, fourPlusTwo
308
308.1 trijapin C T. japonicum[a] +38 (0.04, m)[b] A. Oya 2015
Structure 309: garmultinone A, garmultinone C — caged, fourPlusTwo
309
309.1 R = prenyl garmultinone A[d] G. multiflora[a] +176.4 (0.04, m)[b] Y. Chen 2019b
309.2 R = (E)-CH=CHCMe2OOH garmultinone C[d] G. multiflora[a] +207.2 (0.02, m)[b] Y. Chen 2019b
Structure 310: garmultinone B, 30-hydroxy-garmultinone B — caged, fourPlusTwo
310
310.1 R = Ph garmultinone B[d] G. multiflora[a] +173.9 (0.06, m)[b] Y. Chen 2019b
310.2 R = 3-hydroxyphenyl 30-hydroxy-garmultinone B[d] G. multiflora[a] +25.0 (0.1, m)[b] J. Cao 2024
Structure 311: garmultinone E — caged, fourPlusTwo
311
311.1 garmultinone E[d] (one of two by that name) G. multiflora[a] +85.0 (0.1, m)[b] J. Cao 2024
Structure 312: garmultinone F — caged, fourPlusTwo
312
312.1 garmultinone F[d] G. multiflora[a] +141.0 (0.1, m)[b] J. Cao 2024
Structure 313: (−)-garcimulin A, (+)-garcimulin A, garcimulin B and others — A, caged, exo
313
313.1 R1 = prenyl
R2 = prenyl		 (−)-garcimulin A[c] G. multiflora[a] −142.9 (0.11, m)[b] Y.-M. Fan 2015
313.2 R1 = prenyl
R2 = prenyl		 (+)-garcimulin A[d] (enantiomer) G. multiflora[a] +115.1 (0.11, m)[b] Y.-M. Fan 2015
313.3 R1 = CH2CH2CMe=CH2
R2 = prenyl		 garcimulin B[c] G. multiflora[a] −118.5 (0.21, m)[b] Y.-M. Fan 2015
313.4 R1 = CH2CH2CMe2OH
R2 = prenyl		 garcimulin C[d] G. multiflora[a] +67.0 (0.1, m)[b] J. Cao 2024
Structure 314: (−)-garmultin D, (+)-garmultin D, garmultin H and others — caged, fourPlusTwo
314
314.1 R1 = prenyl
R2 = prenyl		 (−)-garmultin D[c] G. multiflora[a] −166.7 (0.28, m)[b] D. S. Tian 2016
314.2 R1 = prenyl
R2 = prenyl		 (+)-garmultin D[d] (enantiomer) G. multiflora[a] +164.9 (0.30, m)[b] D. S. Tian 2016
314.3 R1 = prenyl
R2 = CH2CH2CMe2OH		 garmultin H[d] G. multiflora[a] +77.0 (0.1, m)[b] H. Luo 2025
314.4 R1 = CH2CH2CMe=CH2
R2 = prenyl		 garmultin E[d] G. multiflora[a] −79.2 (0.29, m)[b] D. S. Tian 2016
Structure 315: (−)-garmultin C, (+)-garmultin C — caged, fourPlusTwo
315
315.1 (−)-garmultin C[c] G. multiflora[a] −85.0 (0.20, m)[b] D. S. Tian 2016
315.2 (+)-garmultin C[d] (enantiomer) G. multiflora[a] +72.6 (0.23, m)[b] D. S. Tian 2016
Structure 316: (−)-garmultin A, (+)-garmultin A, garmultin B — caged, fourPlusTwo
316
316.1 R = prenyl (−)-garmultin A[c] G. multiflora[a] −112.8 (0.24, a)[b] D. S. Tian 2016
316.2 R = prenyl (+)-garmultin A[d] (enantiomer) G. multiflora[a] +110.2 (0.22, a)[b] D. S. Tian 2016
316.3 R = CH2CH2CMe=CH2 garmultin B[d] G. multiflora[a] −53.0 (0.37, m)[b] D. S. Tian 2016
Structure 317: (−)-garmultin F, (+)-garmultin F, garmultin G — caged, fourPlusTwo
317
317.1 R = prenyl (−)-garmultin F[c] G. multiflora[a] −39.0 (0.32, m)[b] D. S. Tian 2016
317.2 R = prenyl (+)-garmultin F[d] (enantiomer) G. multiflora[a] +30.2 (0.37, m)[b] D. S. Tian 2016
317.3 R = CH2CH2CMe=CH2 garmultin G[d] G. multiflora[a] −20.4 (0.25, m)[b] D. S. Tian 2016
Structure 318: hyperuralone A — caged, fourPlusTwo
318
318.1 hyperuralone A[d] H. uralum[a] +34.3 (0.2, m)[b] J.-J. Zhang 2014b
Structure 319: hyperforcinol B — caged, fourPlusTwo
319
319.1 hyperforcinol B[d] H. forrestii[a] +72 (0.2, m)[b] W.-J. Lu 2021
Structure 320: uralin A — caged, fourPlusTwo
320
320.1 uralin A, a.k.a. hyperacmosin N[d] H. acmosepalum, H. uralum[a] +71 (0.2, m)[b], +47.3 (0.1, m)[b] Q.-Q. Fang 2021, M.-x. Sun 2021b
Structure 321: burlemarxione A — caged, fourPlusTwo
321
321.1 burlemarxione A, and tautomer burlemarxione B C. burlemarxii[a] −113.0 (1.35)[b] C. G. Ferraz 2019
Structure 322: garcibractinone B, garcibractinone A — caged, fourPlusTwo, seco
322
322.1 R = prenyl garcibractinone B[c] G. bracteata[a] +20 (0.05, m)[b] Y. Chen 2020
322.2 R = CH2CH2CMe=CH2 garcibractinone A[c] G. bracteata[a] +72 (0.05, m)[b] Y. Chen 2020
Structure 323: hypatulin A — caged, fourPlusTwo, seco
323
323.1 hypatulin A[c] H. patulum[a] +40 (0.05, m)[b] N. Tanaka 2016b
Structure 324: hyperforcinol C — caged, fourPlusTwo, seco
324
324.1 hyperforcinol C[c] H. forrestii[a] +30 (0.2, m)[b] W.-J. Lu 2021
Structure 325: hypatulin B — caged, fourPlusTwo, seco
325
325.1 hypatulin B H. patulum[a] +27.0 (0.17, m)[b] N. Tanaka 2016b
Structure 326: hyperadditionciol K — caged, otherBridgedBicycles, seco
326
326.1 hyperadditionciol K[c] H. addingtonii[a] +14 (0.05, m)[b] J. Chen 2026
Structure 327: garcimultiflin D, garcimultiflin A — caged, fourPlusTwo, seco
327
327.1 X1 = H
X2 = OH		 garcimultiflin D[d] G. multiflora[a] +10.0 (1.0, m)[b] H. Luo 2025
327.2 X1 = OH
X2 = H		 garcimultiflin A[d] G. multiflora[a] −15.0 (1.0, m)[b] J. Cao 2023
Structure 328: garcimultiflin B — caged, fourPlusTwo, seco
328
328.1 garcimultiflin B[d] G. multiflora[a] −10.0 (1.0, m)[b] J. Cao 2023
Structure 329: garcimultiflin C — caged, fourPlusTwo, seco
329
329.1 garcimultiflin C[d] G. multiflora[a] +11.0 (1.0, m)[b] J. Cao 2023
Structure 330: garcibracteatone, garcixanthochymone E, garcibracteatone D and others — A, caged, fourPlusTwo
330
330.1 R1 = prenyl
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone G. bracteata[a] −1 (1.00)[b] O. Thoison 2005
330.2 R1 = prenyl
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = OH
X3 = OH		 garcixanthochymone E G. xanthochymus[a] +9.49 (0.604, m)[b] Y. Chen 2017
330.3 R1 = prenyl
R2 = H
R3 = H
R4 = (E)-CH=CHCMe2OH
X1 = H
X2 = H
X3 = H		 garcibracteatone D[c] G. bracteata[a] −74.4 (0.01, m)[b] X.-N. Li 2023
330.4 R1 = prenyl
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyphenrone L, a.k.a. hypelodin B[d] H. elodeoides, H. henryi, H. sampsonii[a] −6.5 (2.9, m)[b], −12 (0.1, m)[b] C. Hashida 2014, X.-W. Yang 2015, N. Tanaka 2020
330.5 R1 = prenyl
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH
X1 = H
X2 = H
X3 = H		 hyperkouytone K[d] H. kouytchense[a] −20.0 (0.27, m)[b] H.-Y. Lou 2024
330.6 R1 = prenyl
R2 = (E)-CH=CHCMe2OH
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperuralone B[d] H. uralum[a] −14.6 (0.14, m)[b] J.-J. Zhang 2014b
330.7 R1 = prenyl
R2 = (E)-CH=CHCMe2OOH
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperberlone B[d] H. beanii[a] −8.9 (0.4, m)[b] Y.-W. Li 2022
330.8 R1 = CH2CH2CMe=CH2
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 doitunggarcinone A G. propinqua[a] −133.3 (0.015)[b] C. Tantapakul 2012, H. P. Pepper 2012
330.9 R1 = CH2CH2CMe=CH2
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = OH
X3 = OH		 garcixanthochymone D G. xanthochymus[a] +22.7 (0.577, m)[b] Y. Chen 2017
330.10 R1 = CH2CH2CMe=CH2
R2 = H
R3 = H
R4 = (E)-CH=CHCMe2OH
X1 = H
X2 = H
X3 = H		 garcibracteatone E[c] G. bracteata[a] +3.63 (0.05, m)[b] X.-N. Li 2023
330.11 R1 = CH2CH2CMe2OH
R2 = H
R3 = H
R4 = CH2CH2CMe2OH
X1 = OH
X2 = OH
X3 = H		 hyphenrone Y[d] (one of two by that name) G. multiflora[a] −31.0 (0.1, m)[b] J. Cao 2024
330.12 R1 = (R)-CH2CH(OH)CMe=CH2
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone A[c] G. bracteata[a] +34.8 (0.25, m)[b] X.-N. Li 2023
330.13 R1 = (R)-CH2CH(OH)CMe2OH
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone B[c] G. bracteata[a] +8.08 (0.06, m)[b] X.-N. Li 2023
330.14 R1 = (S)-CH2CH(OH)CMe2OH
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone C[c] G. bracteata[a] +46.18 (0.05, m)[b] X.-N. Li 2023
330.15 R1 = (R)-CH2CH(OH)CMe2OH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone B[d] H. patulum[a] −18.2 (0.3, m)[b] F. Zhang 2026
330.16 R1 = (S)-CH2CH(OH)CMe2OH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone A[d] H. patulum[a] −22.5 (0.3, m)[b] F. Zhang 2026
330.17 R1 = (R)-CH2CH(OH)CMe2OMe
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone D[d] H. patulum[a] −26.1 (0.3, m)[b] F. Zhang 2026
330.18 R1 = (S)-CH2CH(OH)CMe2OMe
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone C[d] H. patulum[a] −23.6 (0.3, m)[b] F. Zhang 2026
330.19 R1 = (R)-CH2CH(OH)CMe=CH2
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone F[d] H. patulum[a] −15.2 (0.3, m)[b] F. Zhang 2026
330.20 R1 = (S)-CH2CH(OH)CMe=CH2
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone E[d] H. patulum[a] −17.95 (0.3, m)[b] F. Zhang 2026
330.21 R1 = (R)-2,3-epoxy-3-methylbutyl
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperkouytone L, a.k.a. hyperpatuone H[d] H. kouytchense, H. patulum[a] −42.6 (0.33, m)[b], −19.8 (0.3, m)[b] H.-Y. Lou 2024, F. Zhang 2026
330.22 R1 = (S)-2,3-epoxy-3-methylbutyl
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone G[d] H. patulum[a] −15.2 (0.3, m)[b] F. Zhang 2026
330.23 R1 = (E)-CH=CHCMe2OH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyphenrone R H. henryi[a] H. Lév & Vaniot −15 (0.15, m)[b] Y. Liao 2016
330.24 R1 = (E)-CH=CHCMe2OOH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyphenrone S H. henryi[a] H. Lév & Vaniot −14 (0.12, m)[b] Y. Liao 2016
330.25 R1 = (E)-CH=CHCMe2OMe
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone I[d] H. patulum[a] −52 (0.3, m)[b] F. Zhang 2026
Structure 331: garcibracteamone H, burlemarxione H, hyperforcinol A — caged, fourPlusTwo
331
331.1 R1 = CH2CH2CMe=CH2
R2 = H		 garcibracteamone H[c] G. bracteata[a] +40 (0.05, m)[b] Q. Xue 2020
331.2 R1 = CH2CH2CMe=CH2
R2 = H		 burlemarxione H[d] (enantiomer) C. burle-marxii[a] −40.0 (0.5)[b] M. do C. C. Silva 2024, Q. Xue 2020
331.3 R1 = prenyl
R2 = prenyl		 hyperforcinol A[d] H. forrestii[a] −39 (0.1, m)[b] W.-J. Lu 2021
Structure 332: hyperkouytone M — caged, fourPlusTwo
332
332.1 hyperkouytone M H. kouytchense[a] −24.8 (0.36, m)[b] H.-Y. Lou 2024
Structure 333: garcibracteamone I — caged, fourPlusTwo
333
333.1 garcibracteamone I[c] G. bracteata[a] −22 (0.05, m)[b] Q. Xue 2020
Structure 334: burlemarxione D — caged, fourPlusTwo
334
334.1 burlemarxione D C. burlemarxii[a] −8.0 (1.0)[b] C. G. Ferraz 2021
Structure 335: hyperlanin B — caged, fourPlusTwo
335
335.1 hyperlanin B[d] H. lancasteri[a] −32.1 (0.3, m)[b] J.-Q. You 2024
Structure 336: hyparillum B — caged, fourPlusTwo
336
336.1 hyparillum B[d] H. patulum[a] −51.5 (0.1)[b] Y. Duan 2024a
Structure 337: hyparillum A — caged, fourPlusTwo
337
337.1 hyparillum A[d] H. patulum[a] −26.1 (0.2)[b] Y. Duan 2024a
Structure 338: garcioblon D — caged, fourPlusTwo
338
338.1 garcioblon D[d] G. oblongifolia[a] −37.2 (0.3, m)[b] Q. Lin 2025
Structure 339: garcioblon A — caged, fourPlusTwo
339
339.1 garcioblon A[d] G. oblongifolia[a] −29.0 (0.4, m)[b] Q. Lin 2025
Structure 340: garcioblon B — caged, fourPlusTwo
340
340.1 garcioblon B[d] G. oblongifolia[a] −32.5 (0.4, m)[b] Q. Lin 2025
Structure 341: garcioblon C — caged, fourPlusTwo
341
341.1 garcioblon C[d] G. oblongifolia[a] −40.6 (0.5, m)[b] Q. Lin 2025
Structure 342: garcioblon E — caged, fourPlusTwo, seco
342
342.1 garcioblon E[d] G. oblongifolia[a] +16.7 (0.5, m)[b] Q. Lin 2025
Structure 343: garcioblon F — caged, fourPlusTwo, seco
343
343.1 garcioblon F[d] G. oblongifolia[a] +26.2 (0.3, m)[b] Q. Lin 2025
Structure 344: burlemarxione I — caged, fourPlusTwo
344
344.1 burlemarxione I[c] C. burle-marxii[a] NR M. do C. C. Silva 2024
Structure 345: garbractin A — caged, fourPlusTwo, seco
345
345.1 garbractin A[c] G. bracteata[a] −94.4 (0.05, m)[b] X.-N. Li 2023
Structure 346: garcibracgluinol B — fourPlusTwo, seco
346
346.1 garcibracgluinol B[c] G. bracteata[a] +248.1 (0.03, m)[b] J. Xu 2025
Structure 347: garcibracgluinol C — fourPlusTwo, seco
347
347.1 garcibracgluinol C[c] G. bracteata[a] +122.2 (0.07, m)[b] J. Xu 2025
Structure 348: xerophenone C, xerophenone A — B, otherBridgedBicycles
348
348.1 R = prenyl xerophenone C G. bracteata[a] +106 (1.0)[b] O. Thoison 2005
348.2 R = CH2CH2CMe=CH2 xerophenone A, and tautomer xerophenone B[d] C. portlandiana, G. propinqua[a] −36.4 (0.055, a)[b] G. E. Henry 1995, T. Sriyatep 2017
Structure 349: garcoblone B, garciyunnanin E, garciyunnanin F and others — B, otherBridgedBicycles
349
349.1 R1 = Ph
R2 = prenyl
R3 = CH2CH(OMe)2
R4 = H		 garcoblone B[c] G. oblongifolia[a] +21.5 (1.0, m)[b] Z. Wu 2022
349.2 R1 = Ph
R2 = prenyl
R3 = CH2CO2H
R4 = H		 garciyunnanin E[c] G. yunnanensis[a] +103.1 (0.13, m)[b] D. Zheng 2021b
349.3 R1 = Ph
R2 = prenyl
R3 = CH2COCMe2OH
R4 = H		 garciyunnanin F, a.k.a. garcoblone A[c] G. oblongifolia, G. yunnanensis[a] +137.6, +21.5 (0.10, m)[b] D. Zheng 2021b, Z. Wu 2022
349.4 R1 = Ph
R2 = prenyl
R3 = CH2COCMe2OH
R4 = prenyl		 hyperberlone D[c] H. beanii[a] +1.6 (1.7, m)[b] Y.-W. Li 2022
349.5 R1 = Ph
R2 = (S)-lavandulyl
R3 = CH2COCMe2OH
R4 = H		 garcoblone D[c][f] G. oblongifolia[a] +27.2 (1.0, m)[b] Z. Wu 2022
349.6 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = CH2COCMe2OH
R4 = H		 garcoblone C[c] G. oblongifolia[a] +41.2 (1.0, m)[b] Z. Wu 2022
Structure 350: garcoblone G, garcibractinol A, garcibractinol E — B, otherBridgedBicycles
350
350.1 R1 = prenyl
R2 = prenyl		 garcoblone G[c] G. oblongifolia[a] −24.1 (1.0, m)[b] S.-Y. Yang 2024
350.2 R1 = prenyl
R2 = CH2CH2CMe=CH2		 garcibractinol A[d] G. bracteata[a] −91.9 (0.04, m)[b] X. Li 2023
350.3 R1 = (E)-CH=CHCMe2OMe
R2 = CH2CH2CMe=CH2		 garcibractinol E[d] G. bracteata[a] −85.1 (0.06, m)[b] X. Li 2023
Structure 351: garcibractinol B, garcibractinol D, garcibractinol C and others — B, otherBridgedBicycles
351
351.1 R = prenyl garcibractinol B[d] G. bracteata[a] −13.3 (0.05, m)[b] X. Li 2023
351.2 R = (E)-CH=CHCMe2OH garcibractinol D[d] G. bracteata[a] −63.9 (0.05, m)[b] X. Li 2023
351.3 R = (E)-CH=CHCMe2OOH garcibractinol C[d] G. bracteata[a] −37.3 (0.05, m)[b] X. Li 2023
351.4 R = (R)-CH2CHOHCMe=CH2 garcibractinol F[d] G. bracteata[a] −5.1 (0.056, m)[b] X. Li 2023
Structure 352: garcoblone H — B, otherBridgedBicycles
352
352.1 garcoblone H[c] G. oblongifolia[a] −26.4 (1.0, m)[b] S.-Y. Yang 2024
Structure 353: garynthone A — B, caged, otherBridgedBicycles
353
353.1 garynthone A G. yunnanensis[a] racemic; +7.85 (0.1, m)[b] and −3.28 (0.1, m)[b] Z. Guo 2025a
Structure 354: garcibractinol G, garcibractinol H — B, otherBridgedBicycles
354
354.1 R = CMe2OH garcibractinol G[d] G. bracteata[a] +150.5 (0.05, m)[b] X. Li 2023
354.2 R = CMe=CH2 garcibractinol H[d] G. bracteata[a] +14.4 (0.04, m)[b] X. Li 2023
Structure 355: garciyunnanin D — B, otherBridgedBicycles
355
355.1 garciyunnanin D[c] G. yunnanensis[a] +23.1 (0.10, m)[b] D. Zheng 2021b
Structure 356: spirohypertone A — B, otherBridgedBicycles, seco
356
356.1 spirohypertone A[c] H. patulum[a] −10.2 (0.2, m)[b] Y. Duan 2024b
Structure 357: trijapin D — B, otherBridgedBicycles
357
357.1 trijapin D T. japonicum[a] −58 (0.6, m)[b] A. Oya 2015
Structure 358: xerophenone G — caged, otherBridgedBicycles
358
358.1 xerophenone G[c][e] G. multiflora[a] +103.0 (0.1, m)[b] J. Cao 2024
Structure 359: xerophenone F — caged, otherBridgedBicycles
359
359.1 xerophenone F[c][e] G. multiflora[a] +164.0 (0.1, m)[b] J. Cao 2024
Structure 360: xerophenone H — caged, otherBridgedBicycles
360
360.1 xerophenone H[e] G. multiflora[a] −15.0 (0.1, m)[b] W.-Y. Lyu 2025
Structure 361: xerophenone D — caged, otherBridgedBicycles
361
361.1 xerophenone D[c] G. multiflora[a] +116.0 (0.1, m)[b] J. Cao 2024
Structure 362: xerophenone E, xerophenone I — caged, otherBridgedBicycles
362
362.1 R = isolavandulyl[g] xerophenone E[c][e] G. multiflora[a] +23.0 (0.1, m)[b] J. Cao 2024
362.2 R = lavandulyl xerophenone I[c][e] G. multiflora[a] −18.0 (0.1, m)[b] H. Luo 2025
Structure 363: garcinielliptone HF — B, otherBridgedBicycles
363
363.1 garcinielliptone HF G. subelliptica[a] −16.7 (0.22, a)[b] C.-C. Wu 2008a
Structure 364: gambogenone — otherBridgedBicycles
364
364.1 gambogenone[e] G. xanthochymus[a] −5 (0.003, m)[b] S. Baggett 2005
Structure 365: garcibractinone C — otherBridgedBicycles
365
365.1 garcibractinone C[c] G. multiflora[a] +32.1 (0.02, m)[b] Q. Li 2022
Structure 366: hyperberin A, hyperberin B, hyperberin C — B, otherBridgedBicycles
366
366.1 R = (2R)-3,3-dimethyloxiran-2-yl hyperberin A[d] H. beanii[a] +69.1 (0.33, m)[b] W.-J. Xu 2019
366.2 R = (2S)-3,3-dimethyloxiran-2-yl hyperberin B[d] H. beanii[a] +95.8 (0.28, m)[b] W.-J. Xu 2019
366.3 R = (1S)-1,2-dihydroxy-2-methyl-1-propyl hyperberin C[d] H. beanii[a] +144.5 (0.19, m)[b] W.-X. Li 2021
Structure 367: hyperberlone E — B, otherBridgedBicycles
367
367.1 hyperberlone E[d] H. beanii[a] +5.7 (0.7, m)[b] Y.-W. Li 2022
Structure 368: hyperforone C, hyperforone B — B, otherBridgedBicycles, seco
368
368.1 R1 = H
R2 = benzoyl		 hyperforone C[c] (one of two by that name) H. forrestii[a] −115 (0.1, m)[b] W.-J. Lu 2020
368.2 R1 = benzoyl
R2 = H		 hyperforone B[c] (one of two by that name) H. forrestii[a] −70 (0.1, m)[b] W.-J. Lu 2020
Structure 369: hypercohin A, hypaluton B — A, otherBridgedBicycles
369
369.1 R = prenyl hypercohin A[c] H. cohaerens, H. forrestii[a] NR X.-W. Yang 2012, W.-J. Lu 2020
369.2 R = (E)-C=CCMe2OH hypaluton B[c] H. patulum[a] −108.7 (0.4, m)[b] Y. Duan 2021a
Structure 370: hyperforone A — A, otherBridgedBicycles, seco
370
370.1 hyperforone A[c] (one of two by that name) H. forrestii[a] −102 (0.1, m)[b] W.-J. Lu 2020
Structure 371: hypaluton A — A, otherBridgedBicycles, seco
371
371.1 hypaluton A[c] H. patulum[a] −64.2 (0.3, m)[b] Y. Duan 2021a
Structure 372: hyperbeanin P — A, otherBridgedBicycles
372
372.1 hyperbeanin P[c] H. beanii[a] −254 (0.2, m)[b] X.-Y. Suo 2021b
Structure 373: hyperprin B — A, otherBridgedBicycles
373
373.1 hyperprin B[c] H. przewalskii[a] −314.0 (0.10, m)[b] J.-F. Zong 2020
Structure 374: hyperacmosin R — A, exo, otherBridgedBicycles
374
374.1 hyperacmosin R[c] H. acmosepalum[a] −230.5 (0.14, m)[b] Y. Ma 2022b
Structure 375: hyperinoid A — otherBridgedBicycles, seco
375
375.1 hyperinoid A[c] H. patulum[a] +54.0 X. Jia 2020
Structure 376: hyperinoid B — otherBridgedBicycles, seco
376
376.1 hyperinoid B[c] H. patulum[a] +61.0 X. Jia 2020
Structure 377: (±)-hypandrone A — otherBridgedBicycles
377
377.1 (±)-hypandrone A H. androsaemum[a] 0 J. Wei 2024a
Structure 378: hypertaxoid B — B, otherBridgedBicycles
378
378.1 hypertaxoid B[d] H. elatoides[a] +13.1 (0.05, m)[b] J.-Y. Xie 2026
Structure 379: hypertaxoid A — B, otherBridgedBicycles
379
379.1 hypertaxoid A[d] H. elatoides[a] +76.1 (0.05, m)[b] J.-Y. Xie 2026
Structure 380: hypermonin A — B, otherBridgedBicycles, seco
380
380.1 hypermonin A[c] H. monogynum[a] +46.5 (0.20, m)[b] Y.-R. Zeng 2018
Structure 381: hypermonin B — B, otherBridgedBicycles, seco
381
381.1 hypermonin B[c] H. monogynum[a] +155.42 (0.24, m)[b] Y.-R. Zeng 2018
Structure 382: garciyunnanin G — B, otherBridgedBicycles, seco
382
382.1 garciyunnanin G[c] G. yunnanensis[a] +28.7 (0.10, m)[b] D. Zheng 2021b
Structure 383: harrisotone A, harrisotone B, tomoeone B and others — spiroindanes, transHydrindane
383
383.1 R = Me
X = OH		 harrisotone A Harrisonia perforata +2.0 (0.27, m)[b] S. Yin 2009
383.2 R = Me
X = OOH		 harrisotone B Harrisonia perforata +25.4 (1.30, m)[b] S. Yin 2009
383.3 R = i-Pr
X = OH		 tomoeone B H. ascyron[a] +9.5 (1.1, m)[b] W. Hashida 2008
383.4 R = i-Pr
X = OOH		 tomoeone D H. ascyron[a] +10.4 (3.0, m)[b] W. Hashida 2008, H. Zhu 2015a
383.5 R = i-Bu
X = OH		 tomoeone F H. ascyron[a] +1.8 (1.8, m)[b] W. Hashida 2008
383.6 R = i-Bu
X = OOH		 tomoeone H H. ascyron[a] +5.2 (2.7, m)[b] W. Hashida 2008, H. Zhu 2015a
383.7 R = Ph
X = OH		 hyperbeanol A H. beanii[a] +2.74 (0.21)[b] X.-Q. Chen 2011
383.8 R = Ph
X = OOH		 hyperpatulol B[c] H. patulum[a] −35.2 (0.1, m)[b] Y.-Y. Liu 2019
Structure 384: hypulatone D, hypermone C, hyperascyrone D and others — spiroindanes, transHydrindane
384
384.1 R1 = i-Pr
R2 = Me
X = H		 hypulatone D H. patulum[a] –12 (0.1, m)[b] Y.-F. Qiu 2026
384.2 R1 = i-Pr
R2 = Me
X = OH		 hypermone C[c] H. monogynum −15.6 (0.1, m)[b] W. Tian 2026
384.3 R1 = i-Pr
R2 = prenyl
X = OH		 hyperascyrone D[c] H. ascyron[a] −7.8 (0.48, m)[b] H. Zhu 2015a
384.4 R1 = i-Pr
R2 = prenyl
X = OOH		 hookerianone E, a.k.a. hyperiforin C[c] H. hookerianum, H. forrestii[a] +30 (0.1, m)[b], +53.0 (0.1, m)[b] Q.-Q. Wang 2020, J.-F. Zong 2021
384.5 R1 = i-Bu
R2 = prenyl
X = OH		 hyperascyrone E[c] H. ascyron[a] −9.1 (0.68, m)[b] H. Zhu 2015a
384.6 R1 = (R)-s-Bu
R2 = Me
X = OH		 hypermone A[c] H. monogynum −10.0 (0.1, m)[b] W. Tian 2026
384.7 R1 = (S)-s-Bu
R2 = Me
X = OH		 hypermone B[c] H. monogynum −39.6 (0.1, m)[b] W. Tian 2026
384.8 R1 = Ph
R2 = prenyl
X = OH		 hyperpatulol A H. beanii[a] +14.27 (0.34)[b] X.-Q. Chen 2011, X. Liu 2026
Structure 385: harperoid B, harrisotone C, harrisotone E and others — spiroindanes, transHydrindane
385
385.1 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = H
X2 = H		 harperoid B Harrisonia perforata +15 (0.4, m)[b] P.-P. An 2026
385.2 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 harrisotone C Harrisonia perforata +11.1 (0.80, m)[b] S. Yin 2009
385.3 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 harrisotone E Harrisonia perforata +22.1 (0.09, m)[b] S. Yin 2009
385.4 R1 = Et
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 hyperpatulone F[c] one of two by that name H. patulum[a] +22.8 (1.0, m)[b] Z.-N. Wu 2019
385.5 R1 = i-Pr
R2 = Me
R3 = prenyl
X1 = OH
X2 = H		 chipericumin C H. chinense, H. pyramidatum[a] +35.1 (0.33, m)[b] S. Abe 2012, R. Force 2014
385.6 R1 = i-Pr
R2 = Me
R3 = prenyl
X1 = OOH
X2 = H		 pyramidatone D H. pyramidatum[a] +20.0 (0.009)[b] R. Force 2014
385.7 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = H
X2 = H		 hypermone E[c] H. monogynum[a] +12 (0.1, m)[b] W. Tian 2026
385.8 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 pyramidatone A, a.k.a. chipericumin E H. pyramidatum, H. riparium[a] +12.5 (0.005)[b], +12.0 (0.5, m)[b] R. Force 2014, M. F. Tala 2015
385.9 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = OOH
X2 = H		 pyramidatone B H. pyramidatum[a] +15.5 (0.03)[b] R. Force 2014
385.10 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = OH
X2 = OH		 hyperpatulol F[c] H. patulum[a] +14.0 (0.1, m)[b] Y.-Y. Liu 2019
385.11 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 tomoeone A[c] H. ascyron[a] +33.2 (2.9, m)[b] W. Hashida 2008, Y.-L. Hu 2023
385.12 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 tomoeone C H. ascyron[a] +17.4 (4.9, m)[b] W. Hashida 2008, H. Zhu 2015a, Y.-L. Hu 2023
385.13 R1 = s-Bu
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 chipericumin D[e] H. chinense[a] +67.4 (0.33, m)[b] S. Abe 2012
385.14 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperascyrone F[c][e] H. ascyron[a] +41.1 (0.13, m)[b] H. Zhu 2015a
385.15 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 hookerianone D[c][e] H. hookerianum[a] +14 (0.1, m)[b] Q.-Q. Wang 2020
385.16 R1 = (R)-s-Bu
R2 = prenyl
R3 = Me
X1 = H
X2 = H		 hyperpatulone E[c] H. patulum[a] +44.3 (0.20, m)[b] Y.-x. Zhang 2021, W. Tian 2026
385.17 R1 = i-Bu
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 hyperpatulone C[c] (one of two by that name) H. patulum[a] +81.8 (0.10, m)[b] Y.-x. Zhang 2021
385.18 R1 = i-Bu
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 tomoeone E H. ascyron, H. cohaerens[a] +40.3 (1.0, m)[b] W. Hashida 2008, J.-J. Zhang 2014a
385.19 R1 = i-Bu
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 tomoeone G H. ascyron[a] +25.4 (1.7, m)[b] W. Hashida 2008, H. Zhu 2015a
385.20 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperbeanol C H. beanii[a] +31.21 (0.19)[b] X.-Q. Chen 2011
385.21 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 hyperbeanol D H. beanii[a] +42.73 (0.42)[b] X.-Q. Chen 2011
Structure 386: hyperpatulone D — spiroindanes, transHydrindane
386
386.1 hyperpatulone D[c] (one of two by that name) H. patulum[a] +83.6 (0.10, m)[b] Y.-x. Zhang 2021
Structure 387: harrisotone D, monosescinol C, hyperpatulol C and others — spiroindanes, transHydrindane
387
387.1 R1 = Me
R2 = prenyl
R3 = prenyl
X = OH		 harrisotone D Harrisonia perforata +4.1 (0.12, m)[b] S. Yin 2009
387.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = OH		 monosescinol C[c] H. longistylum[a] −30.0 (0.4, m)[b] Z. Shi 2024
387.3 R1 = i-Pr
R2 = prenyl
R3 = Me
X = OH		 hyperpatulol C, and tautomer hypericumono C[c] H. monogynum, H. patulum[a] +18.8 (0.1, m)[b];  −135.323 (0.15, m)[b] Y.-Y. Liu 2019
387.4 R1 = i-Pr
R2 = prenyl
R3 = Me
X = OOH		 pyramidatone C H. pyramidatum[a] +17.3 (0.01)[b] R. Force 2014
387.5 R1 = s-Bu
R2 = prenyl
R3 = Me
X = OH		 hypermone D[c][e] H. monogynum +5.2 (0.1, m)[b] W. Tian 2026
387.6 R1 = (R)-s-Bu
R2 = Me
R3 = prenyl
X = OH		 monosescinol B[c] H. longistylum[a] −37.3 (0.5, m)[b] Z. Shi 2024
387.7 R1 = (R)-s-Bu
R2 = prenyl
R3 = prenyl
X = OH		 hyperlagarol I[c] H. beanii[a] NR R.-D. Hu 2024
387.8 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
X = OH		 hyperlagarol H[c] H. beanii[a] NR R.-D. Hu 2024
387.9 R1 = Ph
R2 = prenyl
R3 = prenyl
X = OH		 hyperbeanol B H. patulum[a] +34.2 (0.1, m)[b] Y.-Y. Liu 2019, X. Liu 2026
Structure 388: hyperpatulol D, hyperpatulol E — spiroindanes, transHydrindane
388
388.1 R = i-Pr hyperpatulol D[c] H. patulum[a] +2.2 (0.1, m)[b] Y.-Y. Liu 2019
388.2 R = s-Bu hyperpatulol E[c][e] H. patulum[a] +10.6 (0.1, m)[b] Y.-Y. Liu 2019
Structure 389: hunascynol I — spiroindanes, transHydrindane
389
389.1 hunascynol I
(or its epimer, hunascynol J)		 H. ascyron[a] −0.7 (0.09, m)[b] Y.-L. Hu 2023
Structure 390: hunascynol J — spiroindanes, transHydrindane
390
390.1 hunascynol J
(or its epimer, hunascynol I)		 H. ascyron[a] −1.2 (0.11, m)[b] Y.-L. Hu 2023
Structure 391: kouytchin B, hyperascyrone B, hyperascyrone C and others — cisHydrindane, spiroindanes
391
391.1 R1 = i-Pr
R2 = Me
X = H		 kouytchin B[d][m] H. kouytchense[a] +27.1 (0.5, m)[b] C. Jing 2026
391.2 R1 = i-Pr
R2 = prenyl
X = OH		 hyperascyrone B[d] H. ascyron[a] −4.8 (0.24, m)[b] H. Zhu 2015a
391.3 R1 = i-Bu
R2 = prenyl
X = OH		 hyperascyrone C[d] H. ascyron[a] −3.8 (0.38, m)[b] H. Zhu 2015a
391.4 R1 = Ph
R2 = prenyl
X = OH		 hyperascyrone A[d] H. ascyron[a] −16.4 (0.33, m)[b] H. Zhu 2015a
Structure 392: hunascynol H, spirohypatone B, spihyperglucinol E and others — cisHydrindane, spiroindanes
392
392.1 R1 = i-Pr
R2 = prenyl
X = H		 hunascynol H H. ascyron[a] +50 (0.10, m)[b] Y.-L. Hu 2023
392.2 R1 = i-Pr
R2 = prenyl
X = OH		 spirohypatone B[c] H. patulum[a] +23.03 (0.101, m)[b] Y. Ye 2020
392.3 R1 = i-Bu
R2 = Me
X = OH		 spihyperglucinol E[c] H. longistylum[a] −18.3 (0.3, m)[b] Z. Shi 2022
392.4 R1 = i-Bu
R2 = prenyl
X = H		 hunascynol G H. ascyron[a] +53 (0.10, m)[b] Y.-L. Hu 2023
392.5 R1 = i-Bu
R2 = prenyl
X = OH		 hunascynol F[c] H. ascyron[a] −6.0 (0.10, m)[b] Y.-L. Hu 2023
392.6 R1 = (S)-s-Bu
R2 = Me
X = H		 hyperpatulone F[c] (one of two by that name) H. patulum[a] +12.4 (0.10, m)[b] Y.-x. Zhang 2021
392.7 R1 = s-Bu
R2 = Me
X = OH		 hyperielliptone HB[c][e] H. geminiflorum[a] +1.0 (1)[b] C.-C. Wu 2008b, Z. Shi 2022
392.8 R1 = (R)-s-Bu
R2 = prenyl
X = OH		 hunascynol D[c] H. ascyron[a] +5.0 (0.12, m)[b] Y.-L. Hu 2023
392.9 R1 = (S)-s-Bu
R2 = prenyl
X = OH		 hunascynol E[c] H. ascyron[a] +18 (0.15, m)[b] Y.-L. Hu 2023
392.10 R1 = Ph
R2 = prenyl
X = OH		 hyperbeanin C[c] H. beanii[a] +34.5 (0.12, m)[b] Y. Ma 2022a
Structure 393: hyperjaponiol B — spiroindanes
393
393.1 hyperjaponiol B[c] H. japonicum [a]Thunb. ex Murray +55.7 (0.1, m)[b] Y. Liu 2026
Structure 394: chipericumin A, chipericumin B, sampsonol A — spiroindanes, transHydrindane
394
394.1 R1 = i-Pr
R2 = Me		 chipericumin A H. chinense[a] +84.3 (0.29, m)[b] S. Abe 2012
394.2 R1 = s-Bu
R2 = Me		 chipericumin B[e] H. chinense[a] +116.1 (0.46, m)[b] S. Abe 2012
394.3 R1 = Ph
R2 = prenyl		 sampsonol A H. sampsonii[a] −7.7 (0.5, mc)[b] W. Xin 2012
Structure 395: sampsonol B — spiroindanes, transHydrindane
395
395.1 sampsonol B H. sampsonii[a] +45.3 (0.5, mc)[b] W. Xin 2012
Structure 396: hyperhenone L — spiroindanes, transHydrindane
396
396.1 hyperhenone L H. henryi[a] −6 (0.08, m)[b] Y.-T. Duan 2018
Structure 397: lagarocladone B — spiroindanes, transHydrindane
397
397.1 lagarocladone B[c] H. lagarocladum[a] +63.8 (0.1, m)[b] L.-T. Lai 2026
Structure 398: hyperacmotone D — spiroindanes, transHydrindane
398
398.1 hyperacmotone D[c] H. acmosepalum[a] +20 (0.10, m)[b] A.-Z. Wang 2022
Structure 399: hyperacmotone E — spiroindanes, transHydrindane
399
399.1 hyperacmotone E[c] H. acmosepalum[a] –1 (0.10, m)[b] A.-Z. Wang 2022
Structure 400: hyperacmotone F — spiroindanes, transHydrindane
400
400.1 hyperacmotone F[c] H. acmosepalum[a] +60 (0.10, m)[b] A.-Z. Wang 2022
Structure 401: hypericumono A — seco, spiroindanes, transHydrindane
401
401.1 hypericumono A[c] H. monogynum[a] +24.443 (0.06, m)[b] Y.-R. Zeng 2026a
Structure 402: spiropatuol G, spiropatuol H — cisHydrindane, spiroindanes
402
402.1 R = i-Bu spiropatuol G[c] H. patulum[a] +3.0 (0.1, m)[b] Z. Shi 2026
402.2 R = s-Bu spiropatuol H[c][e] H. patulum[a] +11.6 (0.1, m)[b] Z. Shi 2026
Structure 403: harperoid C, sampsonol F, hyperhenone I and others — caged, spiroindanes, transHydrindane
403
403.1 R1 = Me
R2 = prenyl
R3 = prenyl
X = H		 harperoid C Harrisonia perforata +26 (0.4, m)[b] P.-P. An 2026
403.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = H		 sampsonol F H. sampsonii[a] +12.4 (0.5, mc)[b] W. Xin 2012
403.3 R1 = i-Pr
R2 = prenyl
R3 = Me
X = H		 hyperhenone I H. henryi[a] −516 (0.12, m)[b] Y.-T. Duan 2018
403.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X = H		 hyperlagarin A H. lagarocladum[a] −87.9 (0.29, m)[b] K. Wang 2019
403.5 R1 = i-Bu
R2 = Me
R3 = prenyl
X = H		 sampsonol E H. sampsonii[a] +25.8 (0.5, mc)[b] W. Xin 2012
403.6 R1 = s-Bu
R2 = Me
R3 = prenyl
X = H		 hyperhenone H[e] H. henryi[a] −71 (0.15, m)[b] Y.-T. Duan 2018
403.7 R1 = (S)-s-Bu
R2 = Me
R3 = prenyl
X = H		 hyperpatulol G[cc] H. patulum[a] −40.6 (0.1, m)[b] Y.-Y. Liu 2019
403.8 R1 = s-Bu
R2 = prenyl
R3 = Me
X = H		 hypericumono E[c][e] H. monogynum[a] +48.000 (0.10, m)[b] Y.-T. Duan 2018
403.9 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X = H		 hyperlagarin B[e] H. lagarocladum[a] −87.9 (0.18, m)[b] K. Wang 2019
403.10 R1 = Ph
R2 = prenyl
R3 = Me
X = H		 sampsonol C H. sampsonii[a] +16.5 (0.5, mc)[b] W. Xin 2012
403.11 R1 = Ph
R2 = prenyl
R3 = prenyl
X = H		 hypercohone G H. cohaerens[a] −56.1 (0.16, m)[b] J.-J. Zhang 2014a
403.12 R1 = Ph
R2 = prenyl
R3 = prenyl
X = OH		 kouytchin A[c][m] H. kouytchense[a] −20.0 (0.5, m)[b] C. Jing 2026
403.13 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = Me
X = H		 sampsonol D H. sampsonii[a] +35.2 (0.5, mc)[b] W. Xin 2012
403.14 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
X = H		 hyperhenone J H. henryi[a] −15 (0.22, m)[b] Y.-T. Duan 2018
Structure 404: harperoid D, hyperhenone G, hyperpatulol I and others — caged, cisHydrindane, spiroindanes
404
404.1 R1 = Me
R2 = prenyl
R3 = prenyl		 harperoid D Harrisonia perforata −22 (0.4, m)[b] P.-P. An 2026
404.2 R1 = i-Pr
R2 = Me
R3 = prenyl		 hyperhenone G H. henryi[a] −99 (0.07, m)[b] Y.-T. Duan 2018
404.3 R1 = i-Pr
R2 = prenyl
R3 = Me		 hyperpatulol I[c] H. patulum[a] −9.4 (0.1, m)[b] Y.-Y. Liu 2019
404.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl		 hyperlagarin C H. lagarocladum[a] −89.7 (0.25, m)[b] K. Wang 2019
404.5 R1 = (S)-s-Bu
R2 = prenyl
R3 = Me		 hyperpatulol H[c] H. patulum[a] −31.2 (0.1, m)[b] Y.-Y. Liu 2019
404.6 R1 = Ph
R2 = prenyl
R3 = prenyl		 hyperbeanol F H. beanii[a] −46 (0.5, m)[b] Y.-R. Li 2019
Structure 405: hyperbeanol G — caged, cisHydrindane, spiroindanes
405
405.1 hyperbeanol G H. beanii[a] +15 (0.09, m)[b] Y.-R. Li 2019
Structure 406: hypehenol A — caged, OC3, spiroindanes
406
406.1 hypehenol A[c] H. henryi[a] +8.6 (0.23, m)[b] T. Yue 2026
Structure 407: hypehenol B, hypehenol C — caged, seco, spiroindanes
407
407.1 R = i-Pr hypehenol B[c] H. henryi[a] +6.2 (0.19, m)[b] T. Yue 2026
407.2 R = s-Bu hypehenol C[c][e] H. henryi[a] +10.8 (0.33, m)[b] T. Yue 2026
Structure 408: hunascynol A — caged, seco, spiroindanes
408
408.1 hunascynol A, a.k.a. hyperlagarol A H. ascyron, H. beanii[a] +15 (0.5, m)[b] Y.-L. Hu 2023, R.-D. Hu 2024
Structure 409: hunascynol B — caged, cisHydrindane, seco
409
409.1 hunascynol B, a.k.a. hyperlagarol B H. ascyron, H. beanii[a] +57 (0.14, m)[b] Y.-L. Hu 2023, R.-D. Hu 2024
Structure 410: hyperlagarol G — caged, spiroindanes
410
410.1 hyperlagarol G[c] H. beanii[a] NR R.-D. Hu 2024
Structure 411: hunascynol C — caged, cisHydrindane, spiroindanes
411
411.1 hunascynol C H. ascyron[a] +29 (0.14, m)[b] Y.-L. Hu 2023
Structure 412: hyperpatulone G — caged, cisHydrindane, spiroindanes
412
412.1 hyperpatulone G[c] H. patulum[a] +62.0 (0.10, m)[b] Y.-x. Zhang 2021
Structure 413: hyperbeanol H — caged, spiroindanes
413
413.1 hyperbeanol H H. beanii[a] +52 (0.7, m)[b] Y.-R. Li 2019
Structure 414: hypericumono D, spiropatuol E, spiropatuol F — caged, spiroindanes, transHydrindane
414
414.1 R = i-Pr hypericumono D[c] H. monogynum[a] −16.452 (0.24, m)[b] Y.-R. Zeng 2026a
414.2 R = i-Bu spiropatuol E[c] H. patulum[a] –45.5 (0.1, m)[b] Z. Shi 2026
414.3 R = s-Bu spiropatuol F[c][e] H. patulum[a] –56.6 (0.1, m)[b] Z. Shi 2026
Structure 415: hyperhenone K — caged, spiroindanes, transHydrindane
415
415.1 hyperhenone K H. henryi[a] −6 (0.07, m)[b] Y.-T. Duan 2018
Structure 416: spiropatuol D, spiropatuol B, spiropatuol C — caged, spiroindanes, transHydrindane
416
416.1 R = i-Pr spiropatuol D[c] H. patulum[a] +5.225 (0.4, m)[b] Z. Shi 2026
416.2 R = i-Bu spiropatuol B[c] H. patulum[a] +2.7 (0.5, m)[b] Z. Shi 2026
416.3 R = s-Bu spiropatuol C[c][e] H. patulum[a] –10.5 (0.3, m)[b] Z. Shi 2026
Structure 417: hyperispirone B — caged, spiroindanes, transHydrindane
417
417.1 hyperispirone B[c] H. beanii[a] −53 (0.18, m)[b] B. Yang 2022
Structure 418: hyperispirone A — caged, cisHydrindane, spiroindanes
418
418.1 hyperispirone A[c] H. beanii[a] +70 (0.15, m)[b] B. Yang 2022
Structure 419: hyperlagarol J — caged, cisHydrindane, spiroindanes
419
419.1 hyperlagarol J[c] H. beanii[a] NR R.-D. Hu 2024
Structure 420: hyperin C, hyperin D, hypatulone A — caged, spiroindanes, transHydrindane
420
420.1 R1 = i-Pr
R2 = Me		 hyperin C[c] H. monogynum[a] −76.00 (0.11, m)[b] Y.-R. Zeng 2021b, Y.-R. Zeng 2026b
420.2 R1 = s-Bu
R2 = Me		 hyperin D[c][e] H. monogynum[a] −30.22 (0.13, m)[b] Y.-R. Zeng 2021b, Y.-R. Zeng 2026b
420.3 R1 = Ph
R2 = prenyl		 hypatulone A[c] H. patulum[a] +11.2 (0.10, m)[b] Y.-Y. Liu 2018, X.-W. Yang 2020
Structure 421: hyperin A, hyperin B — caged, seco, spiroindanes
421
421.1 R = i-Pr hyperin A[c] H. monogynum[a] −78.50 (0.08, m)[b] Y.-R. Zeng 2021b, Y.-R. Zeng 2026b
421.2 R = s-Bu hyperin B[c][e] H. monogynum[a] −64.29 (0.13, m)[b] Y.-R. Zeng 2021b, Y.-R. Zeng 2026b
Structure 422: hyperilongenol C, hyperilongenol B, hyperilongenol A — seco, spiroindanes
422
422.1 R = i-Pr hyperilongenol C[c] H. longistylum[a] +82.3 (0.5, m)[b] N. Zhang 2019a, N. Zhang 2019b
422.2 R = i-Bu hyperilongenol B[c] H. longistylum[a] +85.2 (0.3, m)[b] N. Zhang 2019a, N. Zhang 2019b
422.3 R = s-Bu hyperilongenol A[c] (mixture of s-Bu epimers) H. longistylum[a] +89.4 (0.6, m)[b] N. Zhang 2019a, N. Zhang 2019b
Structure 423: hyperlagarol C — caged, seco, spiroindanes
423
423.1 hyperlagarol C[c] H. beanii[a] NR R.-D. Hu 2024
Structure 424: hyperlagarol D — seco, spiroindanes
424
424.1 hyperlagarol D[c] H. beanii[a] NR R.-D. Hu 2024
Structure 425: spihyperglucinol A, spihyperglucinol B — caged, seco, spiroindanes
425
425.1 R = i-Bu spihyperglucinol A[c] H. longistylum[a] −130.0 (0.8, m)[b] Z. Shi 2022
425.2 R = s-Bu spihyperglucinol B[c][e] H. longistylum[a] −112.6 (0.1, m)[b] Z. Shi 2022
Structure 426: spihyperglucinol C, spihyperglucinol D — caged, seco, spiroindanes
426
426.1 R = i-Bu spihyperglucinol C[c] H. longistylum[a] −53.4 (0.4, m)[b] Z. Shi 2022
426.2 R = s-Bu spihyperglucinol D[c][e] H. longistylum[a] −61.6 (0.4, m)[b] Z. Shi 2022
Structure 427: hypericumono F — seco, spiroindanes, transHydrindane
427
427.1 hypericumono F[c] H. monogynum[a] −40.000 (0.10, m)[b] Y.-R. Zeng 2026a
Structure 428: biyouyanagiol, uralin D — seco, spiroindanes, transHydrindane
428
428.1 R = Me biyouyanagiol[y] H. chinense[a] +10.5 (0.5)[b] N. Tanaka 2009a
428.2 R = prenyl uralin D[c] H. uralum[a] +32 (0.1, m)[b] Q.-Q. Fang 2021
Structure 429: biyoulactone D, biyoulactone E — seco, spiroindanes, transHydrindane
429
429.1 R = i-Pr biyoulactone D H. chinense[a] −39.4 (0.1, m)[b] N. Tanaka 2012
429.2 R = s-Bu biyoulactone E[e] H. chinense[a] −14.4 (0.07, m)[b] N. Tanaka 2012
Structure 430: hyperbeanone A — seco, spiroindanes, transHydrindane
430
430.1 hyperbeanone A[c] H. beanii[a] −134 (0.15, m)[b] B. Yang 2021a
Structure 431: hypermonone B, hypermonone C, hypermonol J and others — seco, spiroindanes, transHydrindane
431
431.1 R = i-Pr hypermonone B, a.k.a. hypermonol I[c] H. monogynum[a] +56.31 (0.07, m)[b] Y.-R. Zeng 2021c, Y. Li 2026
431.2 R = s-Bu hypermonone C[c][e] H. monogynum[a] −40.83 (0.07, m)[b] Y.-R. Zeng 2021c
431.3 R = (R)-s-Bu hypermonol J[c] H. monogynum[a] +42.5 (0.1, m)[b] Y. Li 2026
431.4 R = (S)-s-Bu hypermonol K[c] H. monogynum[a] +119.2 (0.1, m)[b] Y. Li 2026
Structure 432: hypermonol F — seco, spiroindanes, transHydrindane
432
432.1 hypermonol F[c] H. monogynum[a] –48.3 (m, 0.1)[b] Y. Li 2026
Structure 433: hypermonol G — seco, spiroindanes, transHydrindane
433
433.1 hypermonol G[c] H. monogynum[a] +41.5 (0.1, m)[b] Y. Li 2026
Structure 434: hypermonone D — seco, spiroindanes, transHydrindane
434
434.1 hypermonone D[c] H. monogynum[a] +47.26 (0.12, m)[b] Y.-R. Zeng 2021c
Structure 435: hypermonone A — cisHydrindane, seco, spiroindanes
435
435.1 hypermonone A[c] H. monogynum[a] +123.49 (0.09, m)[b] Y.-R. Zeng 2021c
Structure 436: hypermonol H, hypermonol L — cisHydrindane, seco, spiroindanes
436
436.1 R = i-Pr hypermonol H[c] H. monogynum[a] +124.7 (m, 0.1)[b] Y. Li 2026
436.2 R = (R)-s-Bu hypermonol L[c] H. monogynum[a] +6.4 (m, 0.1)[b] Y. Li 2026
Structure 437: hypermonane A — caged, seco, spiroindanes
437
437.1 hypermonane A[c][e] H. monogynum[a] +6.4 (0.1, m)[b] B. Geng 2026
Structure 438: hybeanone B, hybeanone A — seco, spiroindanes, transHydrindane
438
438.1 R = i-Pr hybeanone B[c] H. beanii[a] +72.3 (0.17, m)[b] B. Yang 2021b
438.2 R = (S)-s-Bu hybeanone A[c] H. beanii[a] +48.9 (0.09, m)[b] B. Yang 2021b
Structure 439: hypermonol A, hypermonol E — seco, spiroindanes, transHydrindane
439
439.1 R = i-Pr hypermonol A[c] H. monogynum[a] +25.8 (0.1, m)[b] J. Wei 2024b
439.2 R = (S)-s-Bu hypermonol E[c] H. monogynum[a] +18.8 (0.1, m)[b] J. Wei 2024b
Structure 440: hypermonol B, hypermonol C, hypermonol D — seco, spiroindanes, transHydrindane
440
440.1 R = i-Pr hypermonol B[c] H. monogynum[a] −64.6 (0.1, m)[b] J. Wei 2024b
440.2 R = (R)-s-Bu hypermonol C[c] H. monogynum[a] +10.4 (0.1, m)[b] J. Wei 2024b
440.3 R = (S)-s-Bu hypermonol D[c] H. monogynum[a] +5.4 (0.1, m)[b] J. Wei 2024b
Structure 441: biyoulactone A — seco, spiroindanes, transHydrindane
441
441.1 biyoulactone A[c] H. chinense[a] +8.1 (0.1, m)[b] N. Tanaka 2011
Structure 442: hypemoin A, biyoulactone B — seco, spiroindanes, transHydrindane
442
442.1 R = i-Pr hypemoin A[c] H. monogynum[a] +24 (0.2, m)[b] Y.-N. Li 2011
442.2 R = (S)-s-Bu biyoulactone B H. chinense[a] +9.7 (0.2, m)[b] N. Tanaka 2011
Structure 443: hypemoin B, biyoulactone C — cisHydrindane, seco, spiroindanes
443
443.1 R = i-Pr hypemoin B[c] H. monogynum[a] +48 (0.2, m)[b] Y.-N. Li 2011
443.2 R = (S)-s-Bu biyoulactone C H. chinense[a] +15.7 (0.09, m)[b] N. Tanaka 2011
Structure 444: furanmonogone B, hyperascone A, hyperascone B and others — seco, spiroindanes, transHydrindane
444
444.1 R1 = i-Pr
R2 = Me		 furanmonogone B[c][e] H. monogynum[a] −8 (0.1, m)[b] W.-J. Xu 2017
444.2 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH		 hyperascone A[c][aa] H. ascyron[a] Linn. +6.3 (0.03, m)[b] S. Wang 2024
444.3 R1 = i-Bu
R2 = (E)-CH=CHCMe2OH		 hyperascone B[c][aa] H. ascyron[a] Linn. +5.7 (0.03, m)[b] S. Wang 2024
444.4 R1 = s-Bu
R2 = Me		 furanmonogone A[c][e] H. monogynum[a] −12 (0.1, m)[b] W.-J. Xu 2017
444.5 R1 = Ph
R2 = (E)-CH=CHCMe2OH		 hyperhenone M[e] H. henryi[a] −31 (0.10, m)[b] Y.-T. Duan 2018
Structure 445: hypemoin E, hypemoin D, hypemoin C — seco, spiroindanes, transHydrindane
445
445.1 R = H hypemoin E[c] H. monogynum[a] −76 (0.1, m)[b] Y.-N. Li 2011
445.2 R = CO2Me hypemoin D[c] H. monogynum[a] +52 (0.1, m)[b] Y.-N. Li 2011
445.3 R = COCHMeCH2CH=CMe2 hypemoin C[c][e] H. monogynum[a] +48 (0.2, m)[b] Y.-N. Li 2011
Structure 446: longisglucinol A — seco, spiroindanes
446
446.1 longisglucinol A[c] H. longistylum[a] −31.2 (0.5, m)[b] N. Zhang 2020
Structure 447: hymoin B — seco, spiroindanes, transHydrindane
447
447.1 hymoin B[c] H. monogynum[a] +160.00 (0.10, m)[b] C. Yuan 2025
Structure 448: spirohypatone A, hypermone F, longisglucinol C and others — spiropentalanes
448
448.1 R1 = i-Pr
R2 = Me
R3 = prenyl		 spirohypatone A[c] H. patulum[a] +105.54 (0.10, m)[b] Y. Ye 2020
448.2 R1 = i-Pr
R2 = prenyl
R3 = Me		 hypermone F[c] H. monogynum[a] +67.2 (0.1, m)[b] W. Tian 2026
448.3 R1 = i-Bu
R2 = Me
R3 = prenyl		 longisglucinol C[c][ff] H. longistylum[a] +99.8 (0.5, m)[b] N. Zhang 2020
448.4 R1 = (S)-s-Bu
R2 = Me
R3 = prenyl		 longisglucinol B[c][ff] a.k.a. either hypermone G or hypermone H H. longistylum[a] +106.9 (0.5, m)[b] N. Zhang 2020
448.5 R1 = (R)- or (S)-s-Bu
R2 = Me
R3 = prenyl		 hypermone G[c] (may be identical to longisglucinol B) H. monogynum[a] +74 (0.1, m)[b] W. Tian 2026
448.6 R1 = (R)- or (S)-s-Bu
R2 = Me
R3 = prenyl		 hypermone H[c][e] (may be identical to longisglucinol B) H. monogynum[a] +46 (0.5, m)[b] W. Tian 2026
448.7 R1 = Ph
R2 = prenyl
R3 = prenyl		 hyperacmotone C[c] H. acmosepalum[a] +101 (0.20, m)[b] A.-Z. Wang 2022
Structure 449: harperoid A, spiropatuol A — spiropentalanes
449
449.1 R = Me harperoid A[c] Harrisonia perforata +12 (0.2, m)[b] P.-P. An 2026
449.2 R = i-Pr spiropatuol A[c] H. patulum[a] +60.625 (0.1, m)[b] Z. Shi 2026
Structure 450: hymoin A — caged, seco, spiropentalanes
450
450.1 hymoin A[c] H. monogynum[a] +77.92 (0.15, m)[b] C. Yuan 2025
Structure 451: hyperzrone A — spiropentalanes
451
451.1 hyperzrone A[c] H. beanii[a] +19.8 (0.1, m)[b] X.-Y. Li 2025
Structure 452: hyperzrone B — spiropentalanes
452
452.1 hyperzrone B[c] H. beanii[a] −1.7 (0.1, m)[b] X.-Y. Li 2025

Statistics

There are 1554 compounds listed.

FeatureNumber
bicyclo[3.3.1]nonanes1199
bicyclo[3.2.1]octanes28
bicyclo[2.2.2]octanes88
other bridged bicyclics54
spiroindanes171
spiropentalanes12
other spiro compounds2
exo at C(7)597
endo at C(7)571
two substituents at C(3) (not caged)103
no substituent at C(7)2
no substituent at C(3)5
acyloxy substituent at C(3)9
type A936
type B360
uncaged867
caged440
seco and nor286
enamine replacing carbonyl8
dimer2
trans-hydrindane125
cis-hydrindane33
enantiomeric pairs (including probable ones) 0

The Grossman–Jacobs and Rastrelli rules are:

C(7) orientation ΔδH(6) δC(7) JH(6ax)–H(7)
exo 0.3–1.2 ppm 41–44 ppm 10–13 Hz
endo either 0.0–0.2 ppm or 45–49 ppm 6–8 Hz