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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 1528 compounds in 448 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 = C(=O)Me
R4 = prenyl
R5 = H		 hypersampsonone I[d] H. sampsonii[a] +17.5 (1.0, m)[b] Y. Li 2023
11.14 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
11.15 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 sampsonione L H. sampsonii[a] +55 (0.06)[b] L.-H. Hu 2000
11.16 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
11.17 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
11.18 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
11.19 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
11.20 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
11.21 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
11.22 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
11.23 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
11.24 R1 = Ph
R2 = prenyl
(3S,6R)-R3 = hyperisampsinSideChain side-chain structure
R4 = prenyl
R5 = H
X = OH		 hyperisampsin M[d] H. sampsonii[a] +47 (0.1)[b] H. Zhu 2015b
11.25 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
11.26 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 = prenyl
R4 = prenyl		 hyperscabin H[d] H. scabrum[a] +21.5 (0.11, mc)[b] J. Ma 2021b
12.2 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = H		 hyperhimatin I[c] H. himalaicum[a] +40.2 (0.5, m)[b] H. Cheng 2022b
12.3 R1 = i-Pr
R2 = CH2CO2H
R3 = prenyl
R4 = H		 hyperhimatin D[c] H. himalaicum[a] +6.2 (0.5, m)[b] H. Cheng 2022b
12.4 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = 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 = prenyl
R4 = 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 = (R)-CH2CHOHCMe2OH
R4 = 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 = prenyl
R4 = H		 hyperhimatin E[c][e] H. himalaicum[a] +20.0 (0.5, m)[b] H. Cheng 2022b
12.8 R1 = Ph
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = 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: papuaforin A, papuaforin E, garcinielliptone F and others — A, bicyclononanes, exo
31
31.1 R1 = i-Pr
R2 = Me
R3 = H		 papuaforin A H. papuanum[a] +13 (0.1, m)[b] K. Winkelmann 2001a
31.2 R1 = i-Pr
R2 = Me
R3 = prenyl		 papuaforin E H. papuanum[a] +41 (0.1, m)[b] K. Winkelmann 2001a
31.3 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
31.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl		 pyrano[7,28-b]hyperforin H. perforatum[a] +83.5 (0.3)[b] M. D. Shan 2001
31.5 R1 = s-Bu
R2 = Me
R3 = H		 papuaforin C[e] H. papuanum[a] +23 (0.1, m)[b] K. Winkelmann 2001a
31.6 R1 = s-Bu
R2 = Me
R3 = prenyl		 papuaforin D[e] H. papuanum[a] +64 (0.1, m)[b] K. Winkelmann 2001a
31.7 R1 = s-Bu
R2 = prenyl
R3 = H		 garsubelone C[d][e] G. subelliptica[a] +6 (0.06, m)[b] Y.-G. Fu 2025
31.8 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hypercohin I[e] H. cohaerens[a] +60.0 (0.22, m)[b] X. Liu 2013a
31.9 R1 = Ph
R2 = prenyl
R3 = H		 scrobiculatone A C. scrobiculata[a] +44.7 (0.2)[b] A. L. M. Porto 2000, K. Winkelmann 2001a
31.10 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 32: hyperselancin B, hyperselancin A, androforin A and others — A, bicyclononanes, endo
32
32.1 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
32.2 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
32.3 R1 = s-Bu
R2 = prenyl
R3 = geranyl		 androforin A[e] H. androsaemum[a] −59.3 (0.23, MeOH)[b] K. Wang 2012
32.4 R1 = Ph
R2 = prenyl
R3 = prenyl		 plukenetione G C. plukenetii[a] NR G. E. Henry 1999
32.5 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 33: bellumone C, garcinielliptone B, hyperpatin F and others — A, bicyclononanes, exo
33
33.1 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
33.2 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
33.3 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
33.4 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
33.5 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
33.6 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
33.7 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
33.8 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
33.9 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
33.10 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
33.11 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 34: ochrocarpinone A — A, bicyclononanes, exo
34
34.1 ochrocarpinone A[e][o] Ochrocarpos punctatus +8.7 (0.15)[b] V. S. P. Chaturvedula 2002
Structure 35: hypersampsone K, garcimultiflorone L — A, bicyclononanes, endo
35
35.1 R = geranyl hypersampsone K H. sampsonii, H. attenuatum[a] +31.7 (0.376)[b] Y. H. Zeng 2012, D. Li 2015a
35.2 R = (R)-lavandulyl[f] garcimultiflorone L[c] G. multiflora[a] +65.4 (0.040, m)[b] Z.-Q. Wang 2018
Structure 36: hyperpatin H — A, bicyclononanes, exo
36
36.1 hyperpatin H[c] H. patulum[a] −105.0 (0.10, m)[b] J.-C. Huang 2025
Structure 37: garcimultinone D, garcimultinone E — A, bicyclononanes, exo
37
37.1 R = Ph garcimultinone D[d] G. multiflora[a] +186.27 (0.02, m)[b] H. Teng 2021
37.2 R = 3,4-dihydroxyphenyl garcimultinone E[d] G. multiflora[a] +11.22 (0.15, m)[b] H. Teng 2021
Structure 38: garcimultiflorone A — A, bicyclononanes, endo
38
38.1 garcimultiflorone A G. multiflora[a] −173 (0.12)[b] J.-J. Chen 2009
Structure 39: no name — A, bicyclononanes, endo
39
39.1 no common name C. obdeltifolia[a] +30.9 (0.3)[b] J. S. A. R. Teixeira 2005
Structure 40: hypersampsonone A — A, bicyclononanes, endo
40
40.1 hypersampsonone A[d] H. sampsonii[a] +46.1 (0.59)[b] J.-S. Zhang 2016
Structure 41: hypersampsone S — A, bicyclononanes, endo
41
41.1 hypersampsone S[d] (one of two by that name) H. sampsonii[a] +62.0 (0.50)[b] W.-J. Tian 2016
Structure 42: hypercohone D, ascynol P — A, bicyclononanes, exo
42
42.1 R1 = i-Pr
R2 = prenyl		 hypercohone D H. cohaerens[a] −97.0 (0.07, m)[b] J.-J. Zhang 2014a
42.2 R1 = i-Bu
R2 = Me		 ascynol P[c] H. ascyron[a] −130 (0.1, m)[b] Y.-L. Hu 2025
Structure 43: oxepahyperforin, uralione J, hyperforatone F and others — A, bicyclononanes, exo
43
43.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl		 oxepahyperforin H. perforatum[a] −73.7 (0.8)[b] L. Verotta 2000
43.2 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
43.3 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
43.4 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
43.5 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
43.6 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
43.7 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
43.8 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
43.9 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
43.10 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
43.11 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
43.12 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl		 hyperascyrin K[c] H. ascyron[a] −201 (0.2, m)[b] J.-W. Hu 2018
43.13 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
43.14 R1 = Ph
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl		 uralione I[c] H. uralum[a] −139 (0.1, m)[b] Z.-B. Zhou 2016b
43.15 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 44: hyperscabrone C, hypercohone E, ascynol Q and others — A, bicyclononanes, exo
44
44.1 R1 = i-Pr
R2 = Me		 hyperscabrone C[c] H. scabrum[a] −124 (0.1, m)[b] W. Gao 2016a
44.2 R1 = i-Pr
R2 = prenyl		 hypercohone E H. cohaerens[a] −42.8 (0.12, m)[b] J.-J. Zhang 2014a
44.3 R1 = i-Bu
R2 = Me		 ascynol Q[c] H. ascyron[a] −112 (0.1, m)[b] Y.-L. Hu 2025
44.4 R1 = (R)-s-Bu
R2 = Me		 hyperscabrone D[c] H. scabrum[a] −75 (0.1, m)[b] W. Gao 2016a
44.5 R1 = s-Bu
R2 = prenyl		 hyperibrin H[c][e] H. scabrum[a] NR W. Xu 2021
44.6 R1 = Ph
R2 = prenyl		 kiiacylphnol G[c] H. przewalskii[a] Maxim −125 (0.4, m)[b] Y. Duan 2022a
Structure 45: hyperkouytone A — A, bicyclononanes, caged
45
45.1 hyperkouytone A[d] H. kouytchense[a] −24.8 (0.21, m)[b] H.-Y. Lou 2024
Structure 46: hyperhookerione A — A, bicyclononanes, exo
46
46.1 hyperhookerione A[c] H. hookerianum[a] +127.8 (0.5, m)[b] Z. Guo 2025b
Structure 47: bellumone D, hyperibone J, subellinone and others — A, bicyclononanes, exo
47
47.1 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
47.2 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
47.3 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
47.4 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
47.5 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
47.6 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
47.7 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
47.8 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
47.9 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
47.10 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
47.11 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
47.12 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
47.13 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
47.14 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
47.15 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
47.16 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 48: hyperhookerione B, hyperhookerione C — A, bicyclononanes, exo
48
48.1 R = i-Pr hyperhookerione B[c] H. hookerianum[a] +221.6 (0.5, m)[b] Z. Guo 2025b
48.2 R = s-Bu hyperhookerione C[c][e] H. hookerianum[a] +33.3 (0.5, m)[b] Z. Guo 2025b
Structure 49: kiiacylphnol C, hyperhookerione D, hypseudohenrin I and others — A, bicyclononanes, exo
49
49.1 R = i-Pr
X = OH		 kiiacylphnol C[c] H. przewalskii[a] Maxim +61 (0.5, m)[b] Y. Duan 2022a
49.2 R = i-Pr
X = OMe		 hyperhookerione D[c] H. hookerianum[a] +77.8 (0.5, m)[b] Z. Guo 2025b
49.3 R = i-Pr
X = OEt		 hypseudohenrin I[c] H. pseudohenryi[a] +21.5 (20.6, m)[b] H.-R. Sun 2021a
49.4 R = s-Bu
X = OH		 hyperforcinol F[c][e] H. forrestii[a] +113 (0.2, m)[b] W.-J. Lu 2021
49.5 R = s-Bu
X = OEt		 hypseudohenrin J[c][e] H. pseudohenryi[a] +40.6 (0.71, m)[b] H.-R. Sun 2021a
Structure 50: przewalcyrone E, przewalcyrone F, hyphenrone T and others — A, bicyclononanes, exo
50
50.1 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
50.2 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
50.3 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
50.4 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
50.5 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
50.6 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
50.7 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
50.8 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
50.9 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
50.10 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
50.11 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
50.12 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
50.13 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
50.14 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
50.15 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
50.16 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
50.17 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
50.18 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
50.19 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
50.20 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 51: hyperhookerione H — A, bicyclononanes, exo
51
51.1 hyperhookerione H[c] H. hookerianum[a] −110 (0.5, m)[b] Z. Guo 2025b
Structure 52: hyperhookerione I — A, bicyclononanes, exo
52
52.1 hyperhookerione I[c] H. hookerianum[a] −163 (0.5, m)[b] Z. Guo 2025b
Structure 53: garcinielliptone H — A, bicyclononanes, exo
53
53.1 garcinielliptone H G. subelliptica[a] −14.3 (0.1)[b] J.-R. Weng 2003b
Structure 54: ascynol G — A, bicyclononanes, exo
54
54.1 ascynol G[c] H. ascyron[a] +78 (0.1, m)[b] Y.-L. Hu 2025
Structure 55: garcinielliptone G — A, bicyclononanes, exo
55
55.1 garcinielliptone G G. subelliptica[a] −53 (0.1)[b] J.-R. Weng 2003b, Y.-G. Fu 2025
Structure 56: hyperscabin D — A, bicyclononanes, exo
56
56.1 hyperscabin D[c] H. scabrum[a] +71.4 (0.08, mc)[b] J. Ma 2021b
Structure 57: hyperforone A — A, bicyclononanes, caged
57
57.1 hyperforone A[c] (one of two by that name) H. perforatum[a] −10.1 (0.1, m)[b] Y. Guo 2021b
Structure 58: hyperforone B — A, bicyclononanes, exo
58
58.1 hyperforone B[c] (one of two by that name) H. perforatum[a] −144.4 (0.5, m)[b] Y. Guo 2021b
Structure 59: hyperforone C — A, bicyclononanes, exo
59
59.1 hyperforone C[c] (one of two by that name) H. perforatum[a] −29.2 (0.3, m)[b] Y. Guo 2021b
Structure 60: hyperforone D — A, bicyclononanes, exo
60
60.1 hyperforone D[c] H. perforatum[a] +68.9 (0.9, m)[b] Y. Guo 2021b
Structure 61: hyperforone E — A, bicyclononanes, exo
61
61.1 hyperforone E[c] H. perforatum[a] −66.4 (0.3, m)[b] Y. Guo 2021b
Structure 62: hyperforone F — A, bicyclononanes, exo
62
62.1 hyperforone F[c] H. perforatum[a] −30.0 (0.8, m)[b] Y. Guo 2021b
Structure 63: hyperforone G — A, bicyclononanes, exo
63
63.1 hyperforone G[c] H. perforatum[a] −15.2 (0.4, m)[b] Y. Guo 2021b
Structure 64: hyperforone H — A, bicyclononanes, exo
64
64.1 hyperforone H[c] H. perforatum[a] −22.3 (0.9, m)[b] Y. Guo 2021b
Structure 65: hyperatin A — A, bicyclononanes, exo
65
65.1 hyperatin A[c] H. perforatum[a] +64.3 (0.1, m)[b] Y. Guo 2024
Structure 66: hyperatin D, hyperatin C, hyperatin B — A, bicyclononanes, exo
66
66.1 R = i-Pr
X = OH		 hyperatin D[c] H. perforatum[a] −24.5 (0.1, m)[b] Y. Guo 2024
66.2 R = i-PrO
X = OH		 hyperatin C[c] H. perforatum[a] −1.8 (0.2, m)[b] Y. Guo 2024
66.3 R = i-PrO
X = OMe		 hyperatin B[c] H. perforatum[a] −5.3 (0.2, m)[b] Y. Guo 2024
Structure 67: hyperacmose A, hyperacmose B — A, bicyclononanes, exo
67
67.1 R = i-Pr hyperacmose A[c] H. acmosepalum[a] +11.11 (2.8, m)[b] Z. Hu 2026
67.2 R = s-Bu hyperacmose B[c][e] H. acmosepalum[a] +8.63 (1.9, m)[b] Z. Hu 2026
Structure 68: hyperacmose C — A, bicyclononanes, exo
68
68.1 hyperacmose C[c] H. acmosepalum[a] +21.43 (0.56, m)[b] Z. Hu 2026
Structure 69: hypericumoxide N — A, bicyclononanes, exo
69
69.1 hypericumoxide N[d] H. scabrum[a] −24.2 (0.09, m)[b] R. Liu 2017
Structure 70: hyperpatone A — A, bicyclononanes, exo
70
70.1 hyperpatone A[c] H. patulum[a] −54.18 (0.3, m)[b] F. Zhang 2023
Structure 71: garcinielliptone J, norhyperpalum G, soulattrone A and others — A, bicyclononanes, exo
71
71.1 R1 = i-Pr
R2 = H		 garcinielliptone J G. subelliptica[a] −166 (0.2)[b] J.-R. Weng 2003b
71.2 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH		 norhyperpalum G[c] H. patulum[a] +107.6 (0.5, m)[b] Y. Duan 2021b
71.3 R1 = (S)-s-Bu
R2 = H		 soulattrone A Calophyllum soulattri +157.3 (0.19, e)[b] S. K. Nigam 1988
71.4 R1 = s-Bu
R2 = (E)-CH=CHCMe2OH		 norhyperpalum F[c][e] H. patulum[a] +92.0 (0.6, m)[b] Y. Duan 2021b
Structure 72: hyphenrone A, perforatumone, hyperuralone C and others — A, bicyclononanes, exo
72
72.1 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
72.2 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
72.3 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
72.4 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
72.5 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
72.6 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
72.7 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
72.8 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
72.9 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
72.10 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 73: hyperfol H — A, bicyclononanes, exo
73
73.1 hyperfol H[c][dd] H. perforatum[a] −203 (0.3, m)[b] H. Lou 2020b
Structure 74: hyperfol B — A, bicyclononanes, exo
74
74.1 hyperfol B[c] H. perforatum[a] −33.24 (0.09, m)[b] H.-Y. Lou 2020a
Structure 75: hyperkouytone N — A, bicyclononanes, exo
75
75.1 hyperkouytone N[c] H. kouytchense[a] −14.2 (0.24, m)[b] H.-Y. Lou 2024
Structure 76: hyperuralone G, hyperuralone H — A, bicyclononanes, endo
76
76.1 R = i-Pr hyperuralone G H. uralum[a] −37 (0.11, m)[b] J.-J. Zhang 2015
76.2 R = s-Bu hyperuralone H[e] H. uralum[a] −38 (0.3, m)[b] J.-J. Zhang 2015
Structure 77: hyphenrone C, hyphenrone I — A, bicyclononanes, exo
77
77.1 R = i-Pr hyphenrone C[c] H. henryi[a] −32.9 (0.10, m)[b] X.-W. Yang 2014, X.-W. Yang 2015
77.2 R = (S)-s-Bu hyphenrone I[c] H. henryi[a] +22 (0.1, m)[b] X.-W. Yang 2015
Structure 78: ascynol H — A, bicyclononanes, exo
78
78.1 ascynol H[c] H. ascyron[a] −22 (0.3, m)[b] Y.-L. Hu 2025
Structure 79: hyphenrone D — A, bicyclononanes, exo
79
79.1 hyphenrone D[c] H. henryi[a] −62.5 (0.10, m)[b] X.-W. Yang 2014
Structure 80: hyperlanin A — A, bicyclononanes, exo
80
80.1 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 81: hyperfol A — A, bicyclononanes, exo
81
81.1 hyperfol A[c] H. perforatum[a] −202.49 (0.3, m)[b] H.-Y. Lou 2020a
Structure 82: ascynol J, hyphenrone F, hyperpatuone M and others — A, bicyclononanes, exo
82
82.1 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
82.2 R1 = i-Pr
R2 = H
R3 = prenyl
R4 = prenyl		 hyphenrone F[c] H. henryi[a] −140 (0.10, m)[b] X.-W. Yang 2014
82.3 R1 = i-Pr
R2 = CO2Me
R3 = prenyl
R4 = prenyl		 hyperpatuone M[c] H. patulum[a] −52 (0.3, m)[b] F. Zhang 2026
82.4 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
82.5 R1 = Ph
R2 = H
R3 = Me
R4 = prenyl		 ascyronone C H. ascyron[a] −151 (0.30, m)[b] L.-M. Kong 2017
82.6 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 83: hyperforen A — A, bicyclononanes, exo
83
83.1 hyperforen A[c] H. perforatum[a] +9.53 (0.05, m)[b] H. Lou 2022
Structure 84: ascyronone A, hyperforcinol K, ascyronone B and others — A, bicyclononanes, exo
84
84.1 R1 = i-Pr
R2 = Me		 ascyronone A H. ascyron[a] +87 (0.04, m)[b] L.-M. Kong 2017
84.2 R1 = i-Pr
R2 = prenyl		 hyperforcinol K[c] H. forrestii[a] +57 (0.9, m)[b] W.-J. Lu 2021
84.3 R1 = s-Bu
R2 = Me		 ascyronone B[e] H. ascyron[a] +108 (0.11, m)[b] L.-M. Kong 2017
84.4 R1 = s-Bu
R2 = prenyl		 hyperforcinol E[c][e] H. forrestii[a] +70 (0.3, m)[b] W.-J. Lu 2021
Structure 85: uralin B — A, bicyclononanes, exo
85
85.1 uralin B[c] H. uralum[a] +63 (0.3, m)[b] Q.-Q. Fang 2021
Structure 86: hypsampsone A — B, bicyclononanes, endo
86
86.1 hypsampsone A[d] H. sampsonii[a] +71.49 (0.7, m)[b] Z.-Z. Zhang 2021
Structure 87: hypersampone A — A, bicyclononanes, exo
87
87.1 hypersampone A[d] H. sampsonii[a] −70.01 (1.7, m)[b] L. Huang 2022
Structure 88: hypersampone B, hypersampone C — A, bicyclononanes, exo
88
88.1 R = OBz hypersampone B[d] H. sampsonii[a] −67.93 (1.8, m)[b] L. Huang 2022
88.2 R = Bz hypersampone C[d] H. sampsonii[a] −21.54 (1.9, m)[b] L. Huang 2022
Structure 89: hyreptaone B, hyreptaone A, hyreptaone C — A, bicyclononanes, endo
89
89.1 R = i-Pr hyreptaone B[c] H. reptans[a] –75 (0.276, m)[b] Y. Zhou 2026
89.2 R = i-Bu hyreptaone A[c] H. reptans[a] –96 (0.046, m)[b] Y. Zhou 2026
89.3 R = (R)-s-Bu hyreptaone C[c] H. reptans[a] –78 (0.167, m)[b] Y. Zhou 2026
Structure 90: hyreptaone D, hyreptaone E — A, bicyclononanes, endo
90
90.1 R = i-Bu hyreptaone D[c] H. reptans[a] +46 (0.125, m)[b]  Y. Zhou 2026
90.2 R = (S)-s-Bu hyreptaone E[c] H. reptans[a] +61 (0.193, m)[b]  Y. Zhou 2026
Structure 91: hyperscabin A, norhyperpalum E — A, bicyclononanes, exo
91
91.1 R = i-Pr hyperscabin A[c] H. scabrum[a] +37.9 (0.05, mc)[b] J. Ma 2021a
91.2 R = s-Bu norhyperpalum E[c][e] H. patulum[a] +55.1 (0.3, m)[b] Y. Duan 2021b
Structure 92: hyperscabin B, hyperscabin C, norhyperpalum D — A, bicyclononanes, exo
92
92.1 R = i-Pr hyperscabin B[c] H. scabrum[a] +75.6 (0.18, mc)[b] J. Ma 2021a
92.2 R = s-Bu hyperscabin C[c][e] H. scabrum[a] +66.2 (0.08, mc)[b] J. Ma 2021a
92.3 R = Ph norhyperpalum D[c] H. patulum[a] −47.1 (0.2, m)[b] Y. Duan 2021b
Structure 93: hyperacmosin K, norhyperpalum B — A, bicyclononanes, exo
93
93.1 R = i-Pr hyperacmosin K[c] H. acmosepalum[a] +109.4 (0.1115, m)[b] M. Sun 2021a
93.2 R = Ph norhyperpalum B[c] H. patulum[a] −14.7 (0.6, m)[b] Y. Duan 2021b
Structure 94: hyperacmosin L, norhyperpalum C — A, bicyclononanes, exo
94
94.1 R = i-Pr hyperacmosin L[c] H. acmosepalum[a] +133.8 (0.068, m)[b] M. Sun 2021a
94.2 R = Ph norhyperpalum C[c] H. patulum[a] +3.3 (0.3, m)[b] Y. Duan 2021b
Structure 95: norhyperpalum A — A, bicyclononanes, endo
95
95.1 norhyperpalum A[d] H. patulum[a] −53.7 (0.3, m)[b] Y. Duan 2021b
Structure 96: hyperscabin E — A, bicyclononanes, endo
96
96.1 hyperscabin E[c] H. scabrum[a] +103.2 (0.14, mc)[b] J. Ma 2021b
Structure 97: hypertum A — A, bicyclononanes, exo
97
97.1 hypertum A[c] H. perforatum[a] −8.5 (0.05, m)[b] W.-Y. Liu 2025b
Structure 98: hyperhexanone F, hyperhexanone A, hyperacmosin M — A, bicyclononanes, endo
98
98.1 R1 = prenyl
R2 = Me		 hyperhexanone F[c] H. sampsonii[a] −40 (0.3, m)[b] Z.-Z. Zhang 2021
98.2 R1 = geranyl
R2 = Me		 hyperhexanone A[c] H. sampsonii[a] −13.3 (0.30)[b] H. Zhu 2016
98.3 R1 = geranyl
R2 = Et		 hyperacmosin M[c] H. acmosepalum[a] −54.5 (0.044, m)[b] M. Sun 2021a
Structure 99: hyperforcinol D — A, bicyclononanes, endo
99
99.1 hyperforcinol D[c] H. forrestii[a] +4 (0.7, m)[b] W.-J. Lu 2021
Structure 100: hyperacmosin D, hyperacmosin C — A, bicyclononanes, endo
100
100.1 R = i-Pr hyperacmosin D[c] H. acmosepalum[a] −25.45 (0.22, m)[b] X.-y. Suo 2021a
100.2 R = (S)-s-Bu hyperacmosin C[c] H. acmosepalum[a] −12.30 (0.26, m)[b] X.-y. Suo 2021a
Structure 101: hyperbenzone A — A, bicyclononanes, endo
101
101.1 hyperbenzone A[c] H. beanii[a] −4 (0.2, m)[b] W. Lu 2021
Structure 102: hyperbenzone B — A, bicyclononanes, endo
102
102.1 hyperbenzone B[c] H. beanii[a] +12 (0.1, m)[b] W. Lu 2021
Structure 103: spirohypolactone A — A, bicyclononanes, exo
103
103.1 spirohypolactone A[c] H. perforatum[a] +65.6 (0.6, m)[b] Y. Guo 2019a
Structure 104: spirohypolactone B, norhyperpalum H, hyperisenin B — A, bicyclononanes, exo
104
104.1 R1 = i-Pr
R2 = CH2CH2CH=CMe2		 spirohypolactone B[c] H. perforatum[a] +43.5 (0.6, m)[b] Y. Guo 2019a
104.2 R1 = s-Bu
R2 = CH2CH2CH=CMe2		 norhyperpalum H[c][e] H. patulum[a] +44.3 (0.5, m)[b] Y. Duan 2021b
104.3 R1 = Ph
R2 = (E)-CH=CHCH=CMe2		 hyperisenin B[c] H. seniawinii[a] +48.8 (0.3, m)[b] Y. Duan 2025
Structure 105: norhyperpalum I, hyperhexanone C, hyperhexanone D — A, bicyclononanes, exo
105
105.1 R = i-Pr
X = H		 norhyperpalum I[c] H. patulum[a] −9.6 (0.6, m)[b] Y. Duan 2021b
105.2 R = i-Pr
X = OH		 hyperhexanone C[c] H. perforatum[a] −17.8 (0.6, m)[b] Y. Guo 2019a
105.3 R = s-Bu
X = OH		 hyperhexanone D[c][e] H. perforatum[a] −30.3 (0.4, m)[b] Y. Guo 2019a
Structure 106: hyperhexanone E — A, bicyclononanes, endo
106
106.1 hyperhexanone E[c] H. perforatum[a] −139.0 (0.3, m)[b] Y. Guo 2019a
Structure 107: norsampsone A, norsampsone C, norgarmultinone A — A, bicyclononanes, endo
107
107.1 R = prenyl norsampsone A[c] H. sampsonii[a] +23.4 (0.50)[b] W.-J. Tian 2014a
107.2 R = geranyl norsampsone C[c] H. sampsonii[a] +26.0 (0.50)[b] W.-J. Tian 2014a
107.3 R = lavandulyl norgarmultinone A[c][e] G. multiflora[a] +77.78 (0.02, m)[b] H. Teng 2020
Structure 108: norsampsone B, norsampsone D — A, bicyclononanes, endo
108
108.1 R = prenyl norsampsone B[c] H. sampsonii[a] −28.6 (0.50)[b] W.-J. Tian 2014a
108.2 R = geranyl norsampsone D[c] H. sampsonii[a] −28.2 (0.50)[b] W.-J. Tian 2014a
Structure 109: norwilsonnol B — A, bicyclononanes, exo
109
109.1 norwilsonnol B[d] H. wilsonii[a] +111.0 (0.5, m)[b] S. Xie 2021
Structure 110: hyperisenin A — A, bicyclononanes, exo
110
110.1 hyperisenin A[d] H. seniawinii[a] +42.0 (0.1, m)[b] Y. Duan 2025
Structure 111: hypertum B — A, bicyclononanes, exo
111
111.1 hypertum B[c] H. perforatum[a] −9.5 (0.15, m)[b] W.-Y. Liu 2025b
Structure 112: norwilsonnol A — A, bicyclononanes, exo
112
112.1 norwilsonnol A[c] H. wilsonii[a] −174.0 (0.7, m)[b] S. Xie 2021
Structure 113: hyperwilsol A — A, bicyclononanes, exo
113
113.1 hyperwilsol A[c] H. wilsonii[a] −5.55 (0.08, m)[b] Z.-X. Wang 2025
Structure 114: hypseudohenrin H — A, bicyclononanes, exo
114
114.1 hypseudohenrin H[c] H. wilsonii[a] −8.56 (1.29, m)[b] M.-X. Sun 2024
Structure 115: hypertum C — A, bicyclononanes, exo
115
115.1 hypertum C[c] H. perforatum[a] −26.8 (0.05, m)[b] W.-Y. Liu 2025b
Structure 116: hypertum D, hypertum E — A, bicyclononanes, exo
116
116.1 X1 = OMe
X2 = H		 hypertum D[c] H. perforatum[a] mixture with hypertum E: −40.1 (0.1, m)[b] W.-Y. Liu 2025b
116.2 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 117: norgarmultinone B — A, bicyclononanes, exo
117
117.1 norgarmultinone B[c] G. multiflora[a] +43.37 (0.07, m)[b] H. Teng 2020
Structure 118: hypseudohenrin C — A, bicyclononanes, endo
118
118.1 hypseudohenrin C[c] H. pseudohenryi[a] +10.5 (1.14, m)[b] H. Sun 2021b
Structure 119: hyperwilsol D — A, bicyclononanes, exo
119
119.1 hyperwilsol D[c] H. wilsonii[a] −81.55 (0.04, m)[b] Z.-X. Wang 2025
Structure 120: hypseudohenrin D — A, bicyclononanes, endo
120
120.1 hypseudohenrin D[c] H. pseudohenryi[a] +10.9 (1.29, m)[b] H. Sun 2021b
Structure 121: garcinielliptone O, no name, hyperwilsol C and others — A, bicyclononanes, exo
121
121.1 R1 = i-Pr
R2 = H		 garcinielliptone O G. subelliptica[a] −277 (0.16)[b] J.-R. Weng 2004
121.2 R1 = i-Pr
R2 = prenyl		 no common name H. perforatum[a] +95.5 (1.1)[b] M. D. Shan 2001
121.3 R1 = (R)-s-Bu
R2 = prenyl		 hyperwilsol C[c] H. wilsonii[a] +93.99 (0.05, m)[b] Z.-X. Wang 2025
121.4 R1 = Ph
R2 = H		 hyperibrin G[d] H. scabrum[a] +80.2 (0.06, m)[b] J. Hu 2017
Structure 122: hypertum F, hypertum G — A, bicyclononanes, exo
122
122.1 R = i-Pr hypertum F[c] H. perforatum[a] +40.2 (0.02, m)[b] W.-Y. Liu 2025b
122.2 R = (S)-s-Bu hypertum G[c] H. perforatum[a] +49.5 (0.02, m)[b] W.-Y. Liu 2025b
Structure 123: spirohypertone B — A, bicyclononanes, exo
123
123.1 spirohypertone B[c] H. patulum[a] −15.2 (0.1, m)[b] Y. Duan 2024b
Structure 124: hypseudohenrin A, hypseudohenrin B — A, bicyclononanes, exo
124
124.1 R = CO2Me hypseudohenrin A[c] H. pseudohenryi[a] +9.8 (1.43, m)[b] H. Sun 2021b
124.2 R = H hypseudohenrin B[c] H. pseudohenryi[a] +12.9 (1.86, m)[b] H. Sun 2021b
Structure 125: hyperibrin A, hyperibrin B, hyperscabrone H and others — A, bicyclononanes, seco
125
125.1 R1 = i-Pr
R2 = Me
R3 = prenyl
X = H		 hyperibrin A[c] H. scabrum[a] +37.0 (0.05, m)[b] W. Gao 2016c
125.2 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
125.3 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
125.4 R1 = i-Pr
R2 = prenyl
R3 = H
X = H		 garcinielliptone N G. subelliptica[a] −42 (0.38)[b] J.-R. Weng 2004
125.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X = H		 no common name H. perforatum[a] +18.3 (1.8)[b] M. D. Shan 2001
125.6 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
125.7 R1 = s-Bu
R2 = Me
R3 = prenyl
X = H		 hypermonone H[c] H. monogynum[a] +7.88 0.24, m) Y.-R. Zeng 2021c
125.8 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
125.9 R1 = Ph
R2 = Me
R3 = prenyl
X = H		 norascyronone C H. ascyron[a] +15 (0.1, m)[b] Y.-L. Hu 2019
125.10 R1 = Ph
R2 = prenyl
R3 = prenyl
X = H		 hypseudohenrin E[c] H. pseudohenryi[a] +4.96 (3.43, m)[b] H. Sun 2021b
125.11 R1 = Ph
R2 = geranyl
R3 = H
X = H		 hyperhexanone B[c] H. sampsonii[a] −14.6 (0.15)[b] H. Zhu 2016
Structure 126: hyperscabrin A, hyperscabin K, hyperscabin L — A, bicyclononanes, seco
126
126.1 R1 = i-Pr
R2 = H		 hyperscabrin A[c] H. scabrum[a] −85.1 (0.06, mc)[b] J. Ma 2012
126.2 R1 = i-Pr
R2 = prenyl		 hyperscabin K[d] H. scabrum[a] −198.3 (0.17, mc)[b] J. Ma 2021b
126.3 R1 = s-Bu
R2 = prenyl		 hyperscabin L[d][e] H. scabrum[a] −178.4 (0.19, mc)[b] J. Ma 2021b
Structure 127: hyperscabin J — A, bicyclononanes, seco
127
127.1 hyperscabin J[c] H. scabrum[a] +36.6 (0.07, mc)[b] J. Ma 2021b
Structure 128: hyperscabrin B, hyperscabrin C — A, bicyclononanes, seco
128
128.1 R = i-Pr hyperscabrin B[c] H. scabrum[a] +27.6 (0.08, mc)[b] J. Ma 2012
128.2 R = s-Bu hyperscabrin C[c][e] H. scabrum[a] +22.4 (0.10, mc)[b] J. Ma 2012
Structure 129: norhypersampsone A — A, bicyclononanes, seco
129
129.1 norhypersampsone A H. sampsonii[a] −40.0 (0.5)[b] J.-S. Zhang 2017
Structure 130: yezo'otogirin C, yezo'otogirin A, ascynol E and others — A, bicyclononanes, caged
130
130.1 R1 = i-Pr
R2 = Me		 yezo'otogirin C[c] H. yezoense[a] −57.2 (0.05)[b] N. Tanaka 2009b
130.2 R1 = i-Pr
R2 = prenyl		 yezo'otogirin A[c] H. yezoense[a] −168.2 (0.25)[b] N. Tanaka 2009b
130.3 R1 = i-Bu
R2 = Me		 ascynol E[c] H. ascyron[a] −39 (0.2, m)[b] Y.-L. Hu 2025
130.4 R1 = (S)-s-Bu
R2 = Me		 hypermogin A[c] H. monogynum[a] −164.7 (0.2, m)[b] Y.-R. Zeng 2021a
130.5 R1 = (S)-s-Bu
R2 = prenyl		 yezo'otogirin B[c] H. yezoense[a] −165.7 (0.15)[b] N. Tanaka 2009b
Structure 131: hypermogin C, hypermogin B — A, bicyclononanes, caged
131
131.1 R = i-Pr hypermogin C[c] H. monogynum[a] −48.9 (0.12, m)[b] Y.-R. Zeng 2021a
131.2 R = (S)-s-Bu hypermogin B[c] H. monogynum[a] −38.0 (0.2, m)[b] Y.-R. Zeng 2021a
Structure 132: hypermogin D — A, bicyclononanes, caged
132
132.1 hypermogin D[c] H. monogynum[a] −32.0 (0.2, m)[b] Y.-R. Zeng 2021a
Structure 133: ascynol D — A, bicyclononanes, caged
133
133.1 ascynol D[c] H. ascyron[a] −31 (0.1, m)[b] Y.-L. Hu 2025
Structure 134: ascynol B — A, bicyclononanes, caged
134
134.1 ascynol B[c] H. ascyron[a] +17 (0.1, m)[b] Y.-L. Hu 2025
Structure 135: ascynol C — A, bicyclononanes, caged
135
135.1 ascynol C[c] H. ascyron[a] −82 (0.06, m)[b] Y.-L. Hu 2025
Structure 136: ascynol A — A, bicyclononanes, caged
136
136.1 ascynol A[c] H. ascyron[a] −42.6 (0.06, m)[b] Y.-L. Hu 2025
Structure 137: norascyronone A, norascyronone B — A, bicyclononanes, caged
137
137.1 X = H norascyronone A[c] H. ascyron[a] +68 (0.2, m)[b] Y.-L. Hu 2019
137.2 X = OH norascyronone B[c] H. ascyron[a] +22 (0.2, m)[b] Y.-L. Hu 2019
Structure 138: norprzewalsone A — A, bicyclononanes, caged
138
138.1 norprzewalsone A[c] H. przewalskii[a] +76.7 (0.4, m)[b] Y. Duan 2022b
Structure 139: hyperforatum A — A, bicyclononanes, exo
139
139.1 hyperforatum A[c] H. perforatum[a] +2 (0.1, m)[b] X. Wang 2024
Structure 140: hyperforatum B — A, bicyclononanes, endo
140
140.1 hyperforatum B[e] H. perforatum[a] +7.5 (1.00, m)[b] X. Wang 2024
Structure 141: hyperforatum C — A, bicyclononanes, seco
141
141.1 hyperforatum C[e] H. perforatum[a] +5.9 (0.35, m)[b] X. Wang 2024
Structure 142: hyperforone I, norprzewalsone B — A, bicyclononanes, exo
142
142.1 R = i-Pr hyperforone I[c] H. perforatum[a] +60.9 (0.6, m)[b] Y. Guo 2021b
142.2 R = s-Bu norprzewalsone B[c][e] H. przewalskii[a] +48.4 (0.3, m)[b] Y. Duan 2022b
Structure 143: hyperforone J — A, bicyclononanes, exo
143
143.1 hyperforone J[c] H. perforatum[a] −110.0 (0.3, m)[b] Y. Guo 2021b
Structure 144: hookerione C, hypersubone C, hookerione A and others — A, bicyclononanes, caged
144
144.1 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
144.2 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
144.3 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
144.4 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
144.5 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
144.6 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
144.7 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
144.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH=CMe2		 plukenetione A C. plukenetii[a] +1 (0.8)[b] G. E. Henry 1996
144.9 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
144.10 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
144.11 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
144.12 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
144.13 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
144.14 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
144.15 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
144.16 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
144.17 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
144.18 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
144.19 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
144.20 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
144.21 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
144.22 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
144.23 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 145: cumilcinol G, hyperattenin J — A, bicyclononanes, caged
145
145.1 R = prenyl cumilcinol G[d] H. wilsonii[a] +104.7 (0.2, m)[b] B. Tao 2024a
145.2 R = geranyl hyperattenin J[d] H. attenuatum[a] Choisy +23.8 (0.3, m)[b] D. Li 2015b
Structure 146: hyperadaman D — A, bicyclononanes, caged
146
146.1 hyperadaman D[d] H. wilsonii[a] +47.7 (0.2, m)[b] B. Tao 2024b
Structure 147: wilsonglucinol I — A, bicyclononanes, caged
147
147.1 wilsonglucinol I[d] H. wilsonii[a] +20.9 (0.25, m)[b] H. Cheng 2022a
Structure 148: garciyunnanone G — A, bicyclononanes, caged
148
148.1 garciyunnanone G[d] G. yunnan[a] Hu +4.4 (0.1, m)[b] M. Nan 2024
Structure 149: hyperadaman G, hyperadaman F — A, bicyclononanes, caged
149
149.1 R = i-Pr hyperadaman G[d] H. wilsonii[a] +43.2 (0.2, m)[b] B. Tao 2024b
149.2 R = Ph hyperadaman F[d] H. wilsonii[a] +87.7 (0.6, m)[b] B. Tao 2024b
Structure 150: hyperadaman B, hyperadaman A — A, bicyclononanes, caged
150
150.1 R = CH2COCHMe2 hyperadaman B[d] H. wilsonii[a] +5.7 (0.2, m)[b] B. Tao 2024b
150.2 R = CH2COC(Me)=CH2 hyperadaman A[d] H. wilsonii[a] +17.0 (0.1, m)[b] B. Tao 2024b
Structure 151: hyperadaman E — A, bicyclononanes, caged
151
151.1 hyperadaman E[d][z] H. wilsonii[a] +86.0 (0.2, m)[b] B. Tao 2024b
Structure 152: hyperisampsin B, hyperattenin L, garciyunnanone D — A, bicyclononanes, caged
152
152.1 R1 = geranyl
R2 = i-Pr
X = OH		 hyperisampsin B[d] H. sampsonii[a] +2.6 (0.08)[b] H. Zhu 2014
152.2 R1 = geranyl
R2 = i-Pr
X = OOH		 hyperattenin L[d] H. attenuatum[a] −1.7 (0.42)[b] D. Li 2018
152.3 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 153: hyperihirsolin A, hyperihirsolin B, hyperesternoid L and others — A, bicyclononanes, caged
153
153.1 R1 = i-Pr
R2 = prenyl
X = OH		 hyperihirsolin A H. hirsutum[a] −25.3 (0.62, m)[b] J. Max 2021
153.2 R1 = s-Bu
R2 = prenyl
X = OH		 hyperihirsolin B[e] H. hirsutum[a] −13.0 (0.90, m)[b] J. Max 2021
153.3 R1 = Ph
R2 = prenyl
X = OH		 hyperesternoid L[d] H. monogynum[a] −32.2 (0.2, m)[b] Z. Dong 2026a
153.4 R1 = Ph
R2 = geranyl
X = OH		 hyperisampsin A[d] H. sampsonii[a] −25.9 (0.16)[b] H. Zhu 2014
153.5 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
153.6 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 154: hypersampsonone M, hyperisampsin C, isohyperisampsin C and others — A, bicyclononanes, caged
154
154.1 R = prenyl hypersampsonone M[d] H. sampsonii[a] +10 (1.0, m)[b] Y. Li 2023
154.2 R = geranyl hyperisampsin C[d] H. sampsonii[a] −19.7 (0.30)[b] H. Zhu 2014
154.3 R = lavandulyl isohyperisampsin C[c][e] G. multiflora[a] +93.3 (0.02, m)[b] Y. Chen 2019a
154.4 R = (R)-lavandulyl[f] garciyunnanone E[d] G. yunnan[a] Hu +8.0 (0.2, m)[b] M. Nan 2024
Structure 155: hyperadaman C — A, bicyclononanes, caged
155
155.1 hyperadaman C[d] H. wilsonii[a] +36.2 (0.2, m)[b] B. Tao 2024b
Structure 156: hyperesternoid M, hyperisampsin D — A, bicyclononanes, caged
156
156.1 R = prenyl
X = OH		 hyperesternoid M[d] H. monogynum[a] −42.8 (0.1, m)[b] Z. Dong 2026a
156.2 R = geranyl
X = OOH		 hyperisampsin D[d] H. sampsonii[a] −25.1 (0.12)[b] H. Zhu 2014
Structure 157: hyperesternoid N, hypersubone B, garciyunnanone F — A, bicyclononanes, caged
157
157.1 R = prenyl
X = OOH		 hyperesternoid N[d] H. monogynum[a] −38.8 (0.2, m)[b] Z. Dong 2026a
157.2 R = geranyl
X = OH		 hypersubone B[d] H. subsessile[a] −52.2 (0.09, m)[b] Y. Liao 2015
157.3 R = lavandulyl
X = OOH		 garciyunnanone F[d] G. yunnan[a] Hu −63.2 (0.2, m)[b] M. Nan 2024
Structure 158: cumilcinol H, hyperisampsin E, no name and others — A, bicyclononanes, caged
158
158.1 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
158.2 R1 = Ph
R2 = prenyl
R3 = CMe=CH2
X = OH		 hyperisampsin E[d] H. sampsonii[a] +9.5 (0.23, m)[b] H. Zhu 2014
158.3 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
158.4 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperisampsin F[d] H. sampsonii[a] +2.0 (0.10, m)[b] H. Zhu 2014
158.5 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
158.6 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 159: garciyunnanone B — A, bicyclononanes, caged
159
159.1 garciyunnanone B[d][e] G. yunnan[a] Hu +27.5 (0.2, m)[b] M. Nan 2024
Structure 160: hyperesternoid I, hyperesternoid J, hyperesternoid K — A, bicyclononanes, caged
160
160.1 R = i-Pr hyperesternoid I[d] H. monogynum[a] −27.9 (0.2, m)[b] Z. Dong 2026a
160.2 R = i-Bu hyperesternoid J[d] H. monogynum[a] −31.7 (0.2, m)[b] Z. Dong 2026a
160.3 R = (R)-s-Bu hyperesternoid K[d] H. monogynum[a] −25.8 (0.2, m)[b] Z. Dong 2026a
Structure 161: hyperesternoid G — A, bicyclononanes, caged
161
161.1 hyperesternoid G[d] H. kouytchemse[a] −53.9 (0.3, m)[b] Z. Dong 2026a
Structure 162: hyperesternoid H — A, bicyclononanes, caged
162
162.1 hyperesternoid H[d] H. kouytchemse[a] −78.4 (0.2, m)[b] Z. Dong 2026a
Structure 163: hookerione G, hookerione H, hypersubone A and others — A, bicyclononanes, endo
163
163.1 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
163.2 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
163.3 R1 = geranyl
R2 = CO2Me
R3 = CH=CMe2		 hypersubone A[d] H. subsessile[a] −142.5 (0.09, m)[b] Y. Liao 2015
163.4 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
163.5 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 164: cumilcinol I — A, bicyclononanes, caged
164
164.1 cumilcinol I[d] H. wilsonii[a] +108.5 (0.2, m)[b] B. Tao 2024a
Structure 165: patumantane C, patumantane B — A, bicyclononanes, caged
165
165.1 R = H patumantane C[d] H. patulum[a] −190.7 (0.1, m)[b] Y. Duan 2024c
165.2 R = CO2Me patumantane B[d] H. patulum[a] −68.0 (0.1, acn)[b] Y. Duan 2024c
Structure 166: patumantane D — A, bicyclononanes, caged
166
166.1 patumantane D[d] H. patulum[a] −75.3 (0.1, m)[b] Y. Duan 2024c
Structure 167: hirsutofolin A, peroxyhirsutofolin A, hyperesternoid V and others — A, bicyclononanes, caged
167
167.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hirsutofolin A H. hirsutum[a] +5.8 (0.65, m)[b] J. Max 2021
167.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 peroxyhirsutofolin A H. hirsutum[a] +12.0 (0.79, m)[b] J. Max 2021
167.3 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
167.4 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 hyperacmosin F H. acmosepalum[a] −16.3 (0.10, m)[b] X. Wang 2020a
167.5 R1 = i-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hyperesternoid T[d] H. monogynum[a] −43.3 (0.2, m)[b] Z. Dong 2026a
167.6 R1 = i-Bu
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid U[d] H. monogynum[a] −45.2 (0.1, m)[b] Z. Dong 2026a
167.7 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
167.8 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
167.9 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
167.10 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
167.11 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
167.12 R1 = Ph
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid X[d] H. monogynum[a] −42.3 (0.1, m)[b] Z. Dong 2026a
167.13 R1 = Ph
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 otogirinin C H. erectum[a] Thunb. NR Y. Ishida 2010
167.14 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 168: pseudohenone F, pseudohenone G, garcimultiflorone P — A, bicyclononanes, caged
168
168.1 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
168.2 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
168.3 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
Structure 169: hypersampsone L — A, bicyclononanes, caged
169
169.1 hypersampsone L H. sampsonii[a] −67.4 (0.098)[b] Y. H. Zeng 2012
Structure 170: hypersampsone S — A, bicyclononanes, caged
170
170.1 hypersampsone S (one of two by that name) H. sampsonii[a] +33 (0.3)[b] J.-J. Chen 2014
Structure 171: hypseudohenone B, hypseudohenone C — A, bicyclononanes, caged
171
171.1 R = prenyl hypseudohenone B[d] H. pseudohenryi[a] +13.5 (0.147, m)[b] N.-N. Jiang 2023
171.2 R = geranyl hypseudohenone C[d] H. pseudohenryi[a] +13.1 (0.106, m)[b] N.-N. Jiang 2023
Structure 172: hypseudohenone A — A, bicyclononanes, caged
172
172.1 hypseudohenone A[d] H. pseudohenryi[a] +19.6 (0.222, m)[b] N.-N. Jiang 2023
Structure 173: patumantane A — A, bicyclononanes, caged
173
173.1 patumantane A[d] H. patulum[a] −56.9 (0.1, m)[b] Y. Duan 2024c
Structure 174: norsampsone E, hyperacmosin E, lathrophytoic acid A — A, bicyclononanes, caged
174
174.1 R1 = C(=O)i-Pr
R2 = geranyl		 norsampsone E[d] H. sampsonii[a] −63.0 (0.30)[b] W.-J. Tian 2017
174.2 R1 = C(=O)Ph
R2 = geranyl		 hyperacmosin E H. acmosepalum[a] −57.6 (0.175)[b] X. Wang 2020a
174.3 R1 = (R)-CHPhCH2CO2H
R2 = prenyl		 lathrophytoic acid A Kielmeyera lathrophyton +15 (0.23, m)[b] M. F. de Almeida 2011
Structure 175: hypersampsone N, hypersampsonone E — A, bicyclononanes, caged
175
175.1 R = prenyl hypersampsone N[d] H. sampsonii[a] +34.4 (0.50)[b] W.-J. Tian 2014b
175.2 R = geranyl hypersampsonone E[d] H. sampsonii[a] +3.21 (1.06)[b] J.-S. Zhang 2016
Structure 176: 3′-hydroxyisohirsutuman A, hyperwilsol B, hirsutuman B and others — A, bicyclononanes, caged
176
176.1 R1 = i-Pr
R2 = prenyl
R3 = E-CH=CHCMe2OH		 3′-hydroxyisohirsutuman A H. hirsutum[a] –35.2 (0.13, m)[b] J. Max 2021
176.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl		 hyperwilsol B[d] H. wilsonii[a] −72.34 (0.05, m)[b] Z.-X. Wang 2025
176.3 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hirsutuman B[e] H. hirsutum[a] −61.9 (0.68, m)[b] J. Max 2021
176.4 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
176.5 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
176.6 R1 = Ph
R2 = prenyl
R3 = CH2CH2CMe2OH		 no common name C. obdeltifolia[a] −5.1 (0.012)[b] F. G. Cruz 2004
176.7 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH		 hyphenrone M H. sampsonii[a] −82 (0.2, m)[b] X.-W. Yang 2015
176.8 R1 = Ph
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl		 wilsonglucinol J[c] H. wilsonii[a] +10.7 (0.5, m)[b] H. Cheng 2022a
176.9 R1 = Ph
R2 = geranyl
R3 = prenyl		 sampsonione A H. sampsonii[a] −49 (0.4)[b] L.-H. Hu 1998
176.10 R1 = Ph
R2 = geranyl
R3 = (E)-CH=CHCMe2OH		 hyphenrone N H. sampsonii[a] −89 (0.2, m)[b] X.-W. Yang 2015
176.11 R1 = Ph
R2 = geranyl
R3 = (E)-CH=CHCMe2OMe		 hypersampsonone D[d] H. sampsonii[a] −66.2 (0.52)[b] J.-S. Zhang 2016
Structure 177: hyperhomanoon A, hyperhomanoon B, hypersampsone O and others — A, bicyclononanes, caged
177
177.1 R1 = i-Pr
R2 = prenyl		 hyperhomanoon A[d] H. patulum[a] +6.2 (0.3, m)[b] B. Tao 2025
177.2 R1 = (S)-s-Bu
R2 = prenyl		 hyperhomanoon B[d] H. patulum[a] +45.0 (0.1, m)[b] B. Tao 2025
177.3 R1 = Ph
R2 = prenyl		 hypersampsone O[d] H. sampsonii[a] +15.2 (0.50)[b] W.-J. Tian 2014b
177.4 R1 = Ph
R2 = geranyl		 hyphenrone O H. sampsonii[a] −9 (0.1, m)[b] X.-W. Yang 2015
177.5 R1 = Ph
R2 = (R)-lavandulyl[f]		 garciyunnanone R[d] G. yunnan[a] Hu +9.2 (0.05, m)[b] M. Nan 2024
Structure 178: hyperhomanoon E — A, bicyclononanes, caged
178
178.1 hyperhomanoon E[d] H. patulum[a] −2.90 (0.5, m)[b] B. Tao 2025
Structure 179: hyperhomanoon D, hyperhomanoon C — A, bicyclononanes, caged
179
179.1 R = prenyl hyperhomanoon D[d] H. patulum[a] +95.3 (0.4, m)[b] B. Tao 2025
179.2 R = geranyl hyperhomanoon C[d] H. patulum[a] +26.2 (0.4, acn)[b] B. Tao 2025
Structure 180: hyperihirsan B, hypersubone G, hypersubone H and others — A, bicyclononanes, caged
180
180.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 hyperihirsan B H. hirsutum[a] +47.9 (0.18, m)[b] J. Max 2021
180.2 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH		 hypersubone G[d] H. subsessile[a] +37.5 (0.13, m)[b] T.-W. Cao 2020
180.3 R1 = i-Pr
R2 = geranyl
R3 = CMe2OOH		 hypersubone H[d] H. subsessile[a] +89.3 (0.08, m)[b] T.-W. Cao 2020
180.4 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
180.5 R1 = Ph
R2 = prenyl
R3 = CMe2OOH		 peroxysampsone A H. sampsonii[a] +17.0 (0.128)[b] Z. Y. Xiao 2010
180.6 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
180.7 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
180.8 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperisampsin O[d] H. sampsonii[a] +12 (0.2, m)[b] H.-C. Zhu 2017
180.9 R1 = Ph
R2 = lavandulyl
R3 = OH		 garcimultinone B[d][e] G. multiflora[a] +28.3 (0.04, m)[b] Y. Chen 2019a
180.10 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 garcimultiflorone G[e] G. multiflora[a] +5.6 (0.12)[b] C.-W. Ting 2014
180.11 R1 = Ph
R2 = lavandulyl
R3 = CMe2OOH		 isohyperisampsin O[d][e] G. multiflora[a] +22.4 (0.06, m)[b] Y. Chen 2019a
180.12 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 181: hypersubone F, hyperisampsin N, hyperbeanin G and others — A, bicyclononanes, caged
181
181.1 R = geranyl
X = H		 hypersubone F[d] H. subsessile[a] −73.4 (0.12, m)[b] T.-W. Cao 2020
181.2 R = geranyl
X = OH		 hyperisampsin N[d] H. sampsonii[a] −31 (0.1)[b] H.-C. Zhu 2017
181.3 R = geranyl
X = OOH		 hyperbeanin G[c] H. beanii[a] −40.0 (0.08, m)[b] Y. Ma 2022a
181.4 R = lavandulyl
X = OH		 garcimultinone N[d] G. multiflora[a] +12.59 (0.04, m)[b] H. Teng 2021
Structure 182: peroxysampsone B — A, bicyclononanes, caged
182
182.1 peroxysampsone B H. sampsonii, H. attenuatum[a] −41.2 (0.042)[b] Z. Y. Xiao 2010, D. Li 2015a
Structure 183: pyranohyperihirsan A, pyranohyperihirsan B — A, bicyclononanes, caged
183
183.1 R = i-Pr pyranohyperihirsan A H. hirsutum[a] −24.7, (0.29, m)[b] J. Max 2021
183.2 R = s-Bu pyranohyperihirsan B[e] H. hirsutum[a] −30.7 (0.25, m)[b] J. Max 2021
Structure 184: hyperattenin M — A, bicyclononanes, caged
184
184.1 hyperattenin M[d][s] H. attenuatum[a] −24.1 (0.19, m)[b] D. Li 2018
Structure 185: hypersampsonone B, isohypersampsonone B — A, bicyclononanes, caged
185
185.1 R = geranyl hypersampsonone B[d] H. sampsonii[a] +14.9 (0.35)[b] J.-S. Zhang 2016
185.2 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 186: hyperesternoid Y — A, bicyclononanes, caged
186
186.1 hyperesternoid Y[d] H. monogynum[a] −42.3 (0.1, m)[b] Z. Dong 2026a
Structure 187: hyperesternoid Z — A, bicyclononanes, caged
187
187.1 hyperesternoid Z[d] H. monogynum[a] −48.7 (0.1, m)[b] Z. Dong 2026a
Structure 188: wilsonglucinol A — A, bicyclononanes, caged
188
188.1 wilsonglucinol A[d] H. wilsonii[a] −14.4 (0.63, m)[b] Y. Zhang 2020
Structure 189: wilsonglucinol C, cumilcinol C, wilsonglucinol B and others — A, bicyclononanes, caged
189
189.1 R1 = i-Pr
R2 = prenyl		 wilsonglucinol C[d] H. wilsonii[a] −94.8 (0.84, m)[b] Y. Zhang 2020
189.2 R1 = s-Bu
R2 = prenyl		 cumilcinol C[d][e] H. wilsonii[a] −137.0 (0.1, m)[b] B. Tao 2024a
189.3 R1 = Ph
R2 = prenyl		 wilsonglucinol B[d] H. wilsonii[a] −51.2 (0.73, m)[b] Y. Zhang 2020
189.4 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 190: garcimultinone C — A, bicyclononanes, caged
190
190.1 garcimultinone C[d][e] G. multiflora[a] −59.4 (0.02, m)[b] H. Teng 2019
Structure 191: hyperesternoid D, hyperesternoid E — A, bicyclononanes, caged
191
191.1 R = i-Bu hyperesternoid D[d] H. monogynum[a] −69.8 (0.3, m)[b] Z. Dong 2026a
191.2 R = (R)-s-Bu hyperesternoid E[d] H. monogynum[a] −58.7 (0.3, m)[b] Z. Dong 2026a
Structure 192: hyperesternoid F — A, bicyclononanes, caged
192
192.1 hyperesternoid F[d] H. monogynum[a] −87.2 (0.3, m)[b] Z. Dong 2026a
Structure 193: cumilcinol A, dioxasampsone B, hypersampsonone C and others — A, bicyclononanes, caged
193
193.1 R1 = i-Pr
R2 = prenyl		 cumilcinol A[d] H. wilsonii[a] +170.8 (0.3, m)[b] B. Tao 2024a
193.2 R1 = Ph
R2 = prenyl		 dioxasampsone B[d] H. sampsonii[a] +77.0 (0.50)[b] W.-J. Tian 2014c
193.3 R1 = Ph
R2 = geranyl		 hypersampsonone C[d] H. sampsonii[a] +6.7 (0.15)[b] J.-S. Zhang 2016
193.4 R1 = Ph
R2 = lavandulyl		 isohypersampsonone C[d][e] G. multiflora[a] +81.7 (0.02, m)[b] Y. Chen 2019a
Structure 194: hookerione Q, hypersampsone M, pseudohenone C and others — A, bicyclononanes, caged
194
194.1 R1 = i-Pr
R2 = geranyl
X = H2		 hookerione Q H. hookerianum[a] +11.2 (0.12, m)[b] Y. Ye 2019
194.2 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
194.3 R1 = Ph
R2 = prenyl
X = O		 pseudohenone C H. pseudohenryi[a] N. Robson −5 (0.24, m)[b] X.-W. Yang 2017b
194.4 R1 = Ph
R2 = (E)-4-oxoprenyl
X = H2		 pseudohenone B H. pseudohenryi[a] N. Robson +7 (0.10, m)[b] X.-W. Yang 2017b
194.5 R1 = Ph
R2 = geranyl
X = H2		 hypersampsone I H. sampsonii[a] +18.6 (0.262)[b] Y. H. Zeng 2012
194.6 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
194.7 R1 = Ph
R2 = lavandulyl
X = O		 garciyunnanone I[d][e] G. yunnan[a] Hu +2 (0.1, m)[b] M. Nan 2024
Structure 195: hypersampsone C, hypersampsone P, hyperattenin F and others — A, bicyclononanes, caged
195
195.1 R1 = i-Pr
R2 = geranyl
X = H2		 hypersampsone C H. sampsonii[a] +14.3 (0.2)[b] Y.-L. Lin 2003
195.2 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
195.3 R1 = Ph
R2 = prenyl
X = O		 hyperattenin F[d] H. attenuatum[a] Choisy −2.9 (0.10, m)[b] D. Li 2015a
195.4 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
195.5 R1 = Ph
R2 = geranyl
X = H2		 sampsonione H H. sampsonii[a] +5.15 (0.07)[b] L.-H. Hu 1999b
195.6 R1 = Ph
R2 = geranyl
X = O		 hyperattenin G[d] H. attenuatum[a] Choisy −6.9 (0.16, m)[b] D. Li 2015a
195.7 R1 = Ph
R2 = lavandulyl
X = H2		 iso-sampsonione H[d][e] G. multiflora[a] +11.84 (0.08, m)[b] H. Teng 2019
195.8 R1 = Ph
R2 = lavandulyl
X = O		 garciyunnanone J[d][e] G. yunnan[a] Hu +5 (0.1, m)[b] M. Nan 2024
195.9 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 196: hookerione M, wilsonglucinol G, hyperesternoid Q and others — A, bicyclononanes, caged
196
196.1 R1 = i-Pr
R2 = prenyl
R3 = i-Pr
X = H		 hookerione M H. hookerianum[a] +68.1 (0.08, m)[b] Y. Ye 2019
196.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol G[d] H. wilsonii[a] +26.3 (0.27, m)[b] Y. Zhang 2020
196.3 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
X = H		 hyperesternoid Q[d] H. monogynum[a] −22.4 (0.1, m)[b] Z. Dong 2026a
196.4 R1 = i-Pr
R2 = geranyl
R3 = CMe=CH2
X = H		 hypersampsone A H. sampsonii[a] +21 (0.3)[b] Y.-L. Lin 2003
196.5 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
X = H		 hirsutusal C[e] H. hirsutum[a] N/A J. Max 2021
196.6 R1 = Ph
R2 = prenyl
R3 = i-Pr
X = H		 hookerione L H. hookerianum[a] +31.4 (0.10, m)[b] Y. Ye 2019
196.7 R1 = Ph
R2 = prenyl
R3 = CMe=CH2
X = H		 hypersampsone X[d] H. sampsonii[a] +27.1 (0.50)[b] W.-J. Tian 2017
196.8 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
196.9 R1 = Ph
R2 = prenyl
R3 = CMe2OOH
X = H		 hyperbeanin F[c] H. beanii[a] +10.0 (0.11, m)[b] Y. Ma 2022a
196.10 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperesternoid O[d] H. monogynum[a] −45.9 (0.3, m)[b] Z. Dong 2026a
196.11 R1 = Ph
R2 = prenyl
R3 = OH
X = H		 hypersampsonone L[d] H. sampsonii[a] +10 (1.0, m)[b] Y. Li 2023
196.12 R1 = Ph
R2 = geranyl
R3 = i-Pr
X = H		 hypersampsone D H. sampsonii[a] −35 (0.2)[b] Y.-L. Lin 2003
196.13 R1 = Ph
R2 = geranyl
R3 = CMe=CH2
X = H		 sampsonione D H. sampsonii[a] +12.27 (0.156)[b] L.-H. Hu 1999b
196.14 R1 = Ph
R2 = geranyl
R3 = CMe2OH
X = H		 sampsonione C H. sampsonii, H. attenuatum[a] +13.39 (0.174)[b] L.-H. Hu 1999b, D. Li 2015a
196.15 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
X = H		 hypersampsonone F[d] H. sampsonii[a] +6.73 (1.04)[b] J.-S. Zhang 2016
196.16 R1 = Ph
R2 = geranyl
R3 = OH
X = H		 cumilcinol D[d] H. wilsonii[a] −4.9 (0.3, m)[b] B. Tao 2024a
196.17 R1 = Ph
R2 = neryl
R3 = i-Pr
X = H		 hookerione I H. hookerianum[a] +24.2 (0.25, m)[b] Y. Ye 2019
196.18 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
196.19 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
196.20 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
196.21 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
196.22 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 197: wilsonglucinol F, hookerione O, cumilcinol F and others — A, bicyclononanes, caged
197
197.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 wilsonglucinol F[d] H. wilsonii[a] +29.2 (0.55, m)[b] Y. Zhang 2020
197.2 R1 = i-Pr
R2 = geranyl
R3 = CMe=CH2		 hookerione O H. hookerianum[a] +39.1 (0.25, m)[b] Y. Ye 2019
197.3 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH		 cumilcinol F[d][e] H. wilsonii[a] +104.7 (0.2, m)[b] B. Tao 2024a
197.4 R1 = Ph
R2 = prenyl
R3 = i-Pr		 hyperacmone F[d] H. maclarenii[a] +10.32 (0.126, m)[b] W.-L. Meng 2026
197.5 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 hypersampsone Q[d] H. sampsonii[a] +18.3 (0.4)[b] W.-J. Tian 2014b
197.6 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hypersampsone G H. sampsonii[a] +10.25 (0.401)[b] Y. H. Zeng 2009
197.7 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 hypersampsone J H. sampsonii[a] +11.4 (0.573)[b] Y. H. Zeng 2012
197.8 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 hypersampsonone G[d] H. sampsonii[a] +4.22 (0.9)[b] J.-S. Zhang 2016
197.9 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperattenin K[d] H. attenuatum[a] Choisy −11.5 (0.886, m)[b] D. Li 2015b
197.10 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 isohypersampsonone G[d][e] G. multiflora[a] +34.2 (0.01, m)[b] Y. Chen 2019a
Structure 198: wilsonglucinol D, hyperwilone C, wilsonglucinol E and others — A, bicyclononanes, caged
198
198.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol D[d] H. wilsonii[a] −17.7 (0.92, m)[b] Y. Zhang 2020
198.2 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
198.3 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
198.4 R1 = Ph
R2 = prenyl
R3 = OH
X = H		 no common name C. obdeltifolia, G. propinqua[a] NR F. G. Cruz 2004, T. Sriyatep 2017
198.5 R1 = Ph
R2 = prenyl
R3 = i-Pr
X = H		 hyphenrone Q H. sampsonii[a] −4 (0.2, m)[b] X.-W. Yang 2015
198.6 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
198.7 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperesternoid P[d] H. monogynum[a] −52.2 (0.2, m)[b] Z. Dong 2026a
198.8 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
198.9 R1 = Ph
R2 = geranyl
R3 = i-Pr
X = H		 hookerione K H. hookerianum[a] −33.1 (0.27, m)[b] Y. Ye 2019
198.10 R1 = Ph
R2 = geranyl
R3 = CMe2OH
X = H		 attenuatumione D H. attenuatum[a] −10.8 (0.15)[b] Z.-B. Zhou 2014
198.11 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
X = H		 hyperattenin I[d] H. attenuatum[a] Choisy −24.5 (0.23, m)[b] D. Li 2015a
198.12 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
198.13 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
198.14 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 199: hookerione N, hirsutusal A, cumilcinol E and others — A, bicyclononanes, caged
199
199.1 R1 = i-Pr
R2 = prenyl
R3 = i-Pr		 hookerione N H. hookerianum[a] −10.3 (0.13, m)[b] Y. Ye 2019
199.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 hirsutusal A[e] H. hirsutum[a] +36.7 (0.18, m)[b] J. Max 2021
199.3 R1 = i-Pr
R2 = prenyl
R3 = OH		 cumilcinol E[d] H. wilsonii[a] −2.0 (0.1, m)[b] B. Tao 2024a
199.4 R1 = i-Pr
R2 = geranyl
R3 = i-Pr		 hypersampsone B H. sampsonii[a] +12 (0.3)[b] Y.-L. Lin 2003
199.5 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH		 hookerione P H. hookerianum[a] −10.3 (0.13, m)[b] Y. Ye 2019
199.6 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH		 hirsutusal B[e] H. hirsutum[a] −6.9 (0.24, m)[b] J. Max 2021
199.7 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
199.8 R1 = Ph
R2 = prenyl
R3 = i-Pr		 hyphenrone P H. sampsonii[a] −83 (0.1, m)[b] X.-W. Yang 2015
199.9 R1 = Ph
R2 = prenyl
R3 = CMe=CH2		 hypercohone B H. cohaerens[a] −37.2 (0.11, m)[b] X. Liu 2013b
199.10 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 hyperacmosin G[c] H. acmosepalum[a] −8.3 (0.012)[b] X. Wang 2020a
199.11 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 sampsonione G[d] (prob. enantiomer) H. sampsonii[a] +10.0 (0.01)[b] L.-H. Hu 1999b
199.12 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
199.13 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
199.14 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hypersampsone E[c] H. sampsonii[a] +39 (0.2)[b] Y.-L. Lin 2003
199.15 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hyperichoisin B[d] (enantiomer) H. choisianum[a] −17.4 (0.285)[b] H.-B. Zhang 2021
199.16 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 hypercohone C H. cohaerens[a] −38.0 (0.09, m)[b] X. Liu 2013b
199.17 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 cowabenzophenone A (enantiomer) G. cowa[a] +137 (0.02)[b] T. Sriyatep 2014
199.18 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 sampsonione F[c] H. sampsonii[a] +14.5 (1.1)[b] L.-H. Hu 1999b
199.19 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 hyperichoisin C[d] (enantiomer) H. choisianum[a] −21.9 (0.31)[b] H.-B. Zhang 2021
199.20 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperberlone C[c] H. beanii[a] −0.34 (2, m)[b] Y.-W. Li 2022
199.21 R1 = Ph
R2 = neryl
R3 = i-Pr		 hookerione J H. hookerianum[a] −38.2 (0.12, m)[b] Y. Ye 2019
199.22 R1 = Ph
R2 = lavandulyl
R3 = CMeCH2		 garciyunnanone M[d][e] G. yunnan[a] Hu +4.3 (0.4, m)[b] M. Nan 2024
199.23 R1 = Ph
R2 = lavandulyl
R3 = i-Pr		 iso-hookerione J[d][e] G. multiflora[a] −4.70 (0.05, m)[b] H. Teng 2019
199.24 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 garciyunnanone P[d][e] G. yunnan[a] Hu −3.6 (0.1, m)[b] M. Nan 2024
199.25 R1 = Ph
R2 = lavandulyl
R3 = OH		 garciyunnanone H[d] G. yunnan[a] Hu +21.6 (0.1, m)[b] M. Nan 2024
Structure 200: hypertonii A — A, bicyclononanes, caged
200
200.1 hypertonii A[c] H. addingtonii[a] N. Robson +42.3 (0.1, acn)[b] Q. Feng 2025
Structure 201: dioxasampsone A — A, bicyclononanes, caged
201
201.1 dioxasampsone A[d] H. sampsonii[a] +16.8 (0.50)[b] W.-J. Tian 2014c
Structure 202: hyperesternoid R — A, bicyclononanes, caged
202
202.1 hyperesternoid R[d] H. monogynum[a] −32.7 (0.2, m)[b] Z. Dong 2026a
Structure 203: hyperesternoid S — A, bicyclononanes, caged
203
203.1 hyperesternoid S[d] H. monogynum[a] −24.8 (0.2, m)[b] Z. Dong 2026a
Structure 204: pseudohenone A — A, bicyclononanes, caged
204
204.1 pseudohenone A H. pseudohenryi[a] N. Robson +43 (0.20, m)[b] X.-W. Yang 2017b
Structure 205: cumilcinol B — A, bicyclononanes, caged
205
205.1 cumilcinol B[d] H. wilsonii[a] +98.0 (0.1, m)[b] B. Tao 2024a
Structure 206: hypercurpalone A — A, bicyclononanes, dimer
206
206.1 hypercurpalone A[d] H. curvisepalum[a] −17.9 (0.13, m)[b] Y. Ye 2022
Structure 207: hypseudone A — A, bicyclononanes, caged
207
207.1 hypseudone A[c] H. pseudohenryi[a] +38.2 (0.096, m)[b] N.-N. Jiang 2025
Structure 208: garsubelone A — A, bicyclononanes, dimer
208
208.1 garsubelone A[d] G. subelliptica[a] +103 (0.14, m)[b] Y.-L. Wang 2019
Structure 209: kielmeyeracin, hyperforatum D, spiranthenone B and others — B, bicyclononanes, exo
209
209.1 R1 = n-Pr
R2 = CHBuCO2Me
R3 = prenyl
R4 = prenyl
R5 = H		 kielmeyeracin[c][e] Kielmeyera variabilis −70 (0.1, m)[b] A. Coqueiro 2016
209.2 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
209.3 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
209.4 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
209.5 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
209.6 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
209.7 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
209.8 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
209.9 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
209.10 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
209.11 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
209.12 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
209.13 R1 = Ph
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 spiritone[e] C. spiritu-sanctensis[a] NR A. L. M. Porto 2000
209.14 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 18-hydroxyclusianone H. hypericoides[a] NR O. E. Christian 2008
209.15 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
209.16 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
209.17 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
209.18 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = prenyl		 garcicowin B G. cowa[a] −16.0 (0.21)[b] G. Xu 2010
209.19 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
209.20 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
209.21 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
209.22 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
209.23 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
209.24 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
209.25 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
209.26 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
209.27 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
209.28 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
209.29 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
209.30 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
209.31 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
209.32 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
209.33 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
209.34 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
209.35 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
209.36 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
209.37 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
209.38 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
209.39 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
209.40 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
209.41 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
209.42 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
209.43 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
209.44 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
209.45 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 210: hyperpapuanone, mesuaferroic acid M, laxifloranone and others — B, bicyclononanes, endo
210
210.1 R1 = i-Pr
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = H		 hyperpapuanone H. papuanum[a] +15 (0.1, m)[b] K. Winkelmann 2001a
210.2 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
210.3 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
210.4 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
210.5 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
210.6 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
210.7 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
210.8 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
210.9 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
210.10 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
210.11 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
210.12 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
210.13 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
210.14 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
210.15 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone Q G. cochinchinensis[a] −50 (0.21)[b] H. D. Nguyen 2011
210.16 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
210.17 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
210.18 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
210.19 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
210.20 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
210.21 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = H		 hyperibone L H. scabrum[a] +69.5 (0.2)[b] N. Tanaka 2004
210.22 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
210.23 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
210.24 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
210.25 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
210.26 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
210.27 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
210.28 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
210.29 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
210.30 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 14-deoxygarcinol[e] M. coccinea[a] −42 (0.3)[b] G. Marti 2009
210.31 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
210.32 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
210.33 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
210.34 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
210.35 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
210.36 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
210.37 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
210.38 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
210.39 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
210.40 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
210.41 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
210.42 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
210.43 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
210.44 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
210.45 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
210.46 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
210.47 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
210.48 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
210.49 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
210.50 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
210.51 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
210.52 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
210.53 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
210.54 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
210.55 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
210.56 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
210.57 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
210.58 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
210.59 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
210.60 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
210.61 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
210.62 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
210.63 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
210.64 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 211: garciyunnanimine A, garciyunnanimine C — B, bicyclononanes, enamine
211
211.1 R = prenyl garciyunnanimine A[c] G. yunnanensis[a] Hu +11.7 (0.03, m)[b] D. Zheng 2017, J.-Y. Xie 2024
211.2 R = geranyl garciyunnanimine C[c] G. yunnanensis[a] Hu +11.4 (0.041, m)[b] D. Zheng 2017, J.-Y. Xie 2024
Structure 212: hyperelamine A, hyperelanitrile C, hyperelanitrile A and others — B, bicyclononanes, enamine
212
212.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = H		 hyperelamine A[d] H. elatoides[a] +44.3 (0.11, m)[b] J.-Y. Xie 2024
212.2 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
212.3 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
212.4 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 213: hyperelanitrile D, hyperelanitrile B — B, bicyclononanes, enamine
213
213.1 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
213.2 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 214: oblongifolin M — B, bicyclononanes, exo
214
214.1 oblongifolin M[c][l][m] G. oblongifolia[a] −4.2 (0.05, m)[b] H. Zhang 2014a
Structure 215: enervosanone — B, bicyclononanes, exo
215
215.1 enervosanone Calophyllum enervosum +10 (0.2000, m)[b] M. Taher 2005
Structure 216: oxy-guttiferone K, oblongifolin G, oblongifolin I and others — B, bicyclononanes, exo
216
216.1 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
216.2 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
216.3 R1 = prenyl
R2 = geranyl
R3 = H
X1 = H
X2 = H
X3 = OH		 oblongifolin I G. oblongifolia[a] NR Y. Zhou 2010
216.4 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
216.5 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
216.6 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
216.7 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 217: garcimultiflorone I, 2,16-oxyguttiferone A, oblongifolin F and others — B, bicyclononanes, endo
217
217.1 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
217.2 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
217.3 R1 = prenyl
R2 = geranyl
R3 = H
X1 = OH
X2 = H		 oblongifolin F G. oblongifolia[a] −85.6 (0.41)[b] S.-X. Huang 2009
217.4 R1 = prenyl
R2 = geranyl
R3 = H
X1 = H
X2 = OH		 oblongifolin H G. oblongifolia[a] NR Y. Zhou 2010
217.5 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
217.6 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
217.7 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
217.8 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
217.9 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
217.10 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
217.11 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 218: garcinialone — B, bicyclononanes, exo
218
218.1 garcinialone[l][m] G. multiflora[a] −2.0 (0.02, m)[b] S.-C. Chien 2008
Structure 219: xanthochymusone N — B, bicyclononanes, endo
219
219.1 xanthochymusone N[d] G. xanthochymus[a] −16 (0.1, m)[b] Y.-G. Fu 2025
Structure 220: no name — B, bicyclononanes, exo
220
220.1 no common name G. indica[a] +18.9 (0.1, m)[b] R. Kaur 2012
Structure 221: symphonone I — B, bicyclononanes, exo
221
221.1 symphonone I S. globulifera[a] −22 (0.4)[b] G. Marti 2010
Structure 222: (+)-garciyunnanin L, (−)-garciyunnanin L, xanthochymusone O — B, bicyclononanes, endo
222
222.1 R = prenyl (+)-garciyunnanin L[c] G. yunnanensis[a] +28.5 (0.10, m)[b] D. Zheng 2021b
222.2 R = prenyl (−)-garciyunnanin L[d] G. xanthochymus[a] −21 (0.1, m)[b] Y.-G. Fu 2025
222.3 R = CH2CH2CMe=CH2 xanthochymusone O[d] G. xanthochymus[a] −21 (0.1, m)[b] Y.-G. Fu 2025
Structure 223: oxy-guttiferone K2, garcixanthochymone J — B, bicyclononanes, exo
223
223.1 R1 = prenyl
R2 = prenyl		 oxy-guttiferone K2 G. cambogia[a] +12.2 (0.1, m)[b] M. Masullo 2010
223.2 R1 = isolavandulyl[g]
R2 = H		 garcixanthochymone J[d][e] G. xanthochymus[a] +53.2 (0.73, m)[b] S. Jin 2021
Structure 224: 4,16-oxyguttiferone A, guttiferone O, garcim-2 and others — B, bicyclononanes, endo
224
224.1 R1 = prenyl
R2 = prenyl
R3 = prenyl		 4,16-oxyguttiferone A S. globulifera[a] +53 (1.0, m)[b] K. Cottet 2015
224.2 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
224.3 R1 = (S)-lavandulyl[f]
R2 = prenyl
R3 = H		 garcim-2[c] G. xanthochymus[a] N/A Z. Wu 2022
224.4 R1 = isolavandulyl[g]
R2 = prenyl
R3 = H		 nujiangefolin B[e] G. nujiangensis[a] +5 (0.10, m)[b] Z.-X. Xia 2012
Structure 225: garciyunnanensisin E — B, bicyclononanes, endo
225
225.1 garciyunnanensisin E[c][e] G. yunnanensis[a] −120.0 (0.1, m)[b] P.-X. Ji 2025
Structure 226: longistylione B, symphonone F, garcixanthochymone G — B, bicyclononanes, exo
226
226.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl		 longistylione B[c] H. longistylum[a] +0.8 (0.04, mc)[b] X. Cao 2017
226.2 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = prenyl
R4 = H		 symphonone F[e] S. globulifera[a] −9 (1.0)[b] G. Marti 2010
226.3 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 227: longistylione A, hyperscabrone F, hyperkouytone F and others — B, bicyclononanes, exo
227
227.1 R1 = Ph
R2 = Me
R3 = prenyl		 longistylione A[c] H. longistylum[a] −12.4 (0.4, mc)[b] X. Cao 2017
227.2 R1 = Ph
R2 = prenyl
R3 = H		 hyperscabrone F[c] H. scabrum[a] −18 (0.1, m)[b] W. Gao 2016a
227.3 R1 = Ph
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl		 hyperkouytone F[c] H. kouytchense[a] −46.5 (0.45, m)[b] H.-Y. Lou 2024
227.4 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = H		 symphonone G[e] S. globulifera[a] −4 (0.4)[b] G. Marti 2010
Structure 228: hyperascyrin N — B, bicyclononanes, exo
228
228.1 hyperascyrin N[d] H. ascyron[a] +40.0 (0.1, m)[b] B. Zhen 2019
Structure 229: no name — B, bicyclononanes, caged
229
229.1 no common name H. scabrum[a] +17.2 (1.0, m)[b] S. Soroury 2020
Structure 230: hyperbeanin Q, garcimultinone K, paucinochymol C and others — B, bicyclononanes, endo
230
230.1 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
230.2 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
230.3 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
230.4 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
230.5 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
230.6 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
230.7 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
230.8 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 231: hyperibone I, hyperibone H, garcimultinone L and others — B, bicyclononanes, endo
231
231.1 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
231.2 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
231.3 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
231.4 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
231.5 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 232: thorelione B — B, bicyclononanes, endo
232
232.1 thorelione B[e] Calophyllum thorelii +412.0 (0.14, e)[b] L.-T. T. Nguyen 2012
Structure 233: oblongifolin X, garcowacinol E, garcowacinol G — B, bicyclononanes, exo
233
233.1 R1 = CMe=CH2
R2 = H		 oblongifolin X[d] G. oblongifolia[a] −11.8 (0.03, m)[b] H. Zhang 2016
233.2 R1 = CMe=CH2
R2 = prenyl		 garcowacinol E[d] G. cowa[a] −36.0 (0.50, m)[b] S. Kaennakam 2022b
233.3 R1 = CMe2OH
R2 = prenyl		 garcowacinol G[d] G. cowa[a] −28.1 (0.30, m)[b] S. Kaennakam 2022b
Structure 234: garcowacinol H — B, bicyclononanes, exo
234
234.1 garcowacinol H[d] G. cowa[a] −21.2 (0.50, m)[b] S. Kaennakam 2022b
Structure 235: garcowacinol F, guttiferone R, oblongifolin R and others — B, bicyclononanes, exo
235
235.1 R1 = H
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl		 garcowacinol F[d] G. cowa[a] −25.0 (0.50, m)[b] S. Kaennakam 2022b
235.2 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
235.3 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
235.4 R1 = prenyl
R2 = CMe=CH2
R3 = prenyl
R4 = H		 hyperscabrone E[d] H. scabrum[a] −10 (0.1, m)[b] W. Gao 2016a
Structure 236: mesuaferroic acid C, mesuaferroic acid F, mesuaferroic acid A and others — B, bicyclononanes, endo
236
236.1 R1 = i-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid C[n] Mesua ferrea NR N. E. Rasol 2017
236.2 R1 = i-Bu
R2 = (S)-CHPhCH2CO2H
R3 = CH2CH(OH)CMe2OH		 mesuaferroic acid F[e][n] Mesua ferrea NR N. E. Rasol 2017
236.3 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid A[e] Mesua ferrea NR N. E. Rasol 2017
236.4 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = CH2CH(OH)CMe2OH		 mesuaferroic acid E[e][n] Mesua ferrea NR N. E. Rasol 2017
236.5 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
236.6 R1 = Ph
R2 = prenyl
R3 = (R)-CH2CH(OH)CMe2OH		 hypersampsone V[k] H. sampsonii[a] +13.0 (0.50)[b] W.-J. Tian 2016
236.7 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 237: mesuaferroic acid B, mesuaferroic acid J, hyperattenin E and others — B, bicyclononanes, endo
237
237.1 R1 = s-Bu
R2 = (S)-CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid B[e][n] Mesua ferrea NR N. E. Rasol 2017
237.2 R1 = CH2CMe2OH
R2 = CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid J[e] Mesua ferrea +4.25 (0.2, m)[b] X.-C. Zhang, 2020
237.3 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
237.4 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 238: paucinone A — B, bicyclononanes, endo
238
238.1 paucinone A G. paucinervis[a] −6.2 (0.05, m)[b] X.-M. Gao 2010
Structure 239: paucinone B — B, bicyclononanes, endo
239
239.1 paucinone B G. paucinervis[a] +58.7 (0.10, m)[b] X.-M. Gao 2010
Structure 240: paucinone C — B, bicyclononanes, endo
240
240.1 paucinone C G. paucinervis[a] +19.2 (0.17, m)[b] X.-M. Gao 2010
Structure 241: garcicowin A — B, bicyclononanes, noC3
241
241.1 garcicowin A G. cowa[a] −219.0 (0.09)[b] G. Xu 2010
Structure 242: garcowacinol D — B, bicyclononanes, noC3
242
242.1 garcowacinol D[d] G. cowa[a] +37.0 (0.50, m)[b] S. Kaennakam 2022b
Structure 243: garcowacinol C, oblongifolin S, xanthochymusone G — B, bicyclononanes, exo
243
243.1 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
243.2 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
243.3 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 244: oblongifolin W, 13,14-didehydroxy-7-epi-isogarcinol, 14-deoxy-7-epi-isogarcinol and others — B, bicyclononanes, exo
244
244.1 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
244.2 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
244.3 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl		 14-deoxy-7-epi-isogarcinol S. globulifera[a] −77 (0.9)[b] G. Marti 2010
244.4 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
244.5 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
244.6 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
244.7 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 symphonone C S. globulifera[a] −67 (1.0)[b] G. Marti 2010
244.8 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl		 symphonone B S. globulifera[a] −81 (1.0)[b] G. Marti 2010
244.9 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
244.10 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
244.11 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CHOHCMe2OH
R4 = prenyl		 symphonone D[e] S. globulifera[a] −41 (0.4)[b] G. Marti 2010
244.12 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 245: oblongifolin Y, hypersampsonone J, guttiferone T — B, bicyclononanes, endo
245
245.1 R1 = Ph
R2 = H
R3 = H
R4 = CH2CO2H		 oblongifolin Y[d] G. oblongifolia[a] +24.1 (0.06, m)[b] H. Zhang 2016
245.2 R1 = Ph
R2 = prenyl
R3 = OH
R4 = prenyl		 hypersampsonone J[d] H. sampsonii[a] +17.5 (1.0, m)[b] Y. Li 2023
245.3 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 246: 13,14-didehydroxyisoxanthochymol, garcimultinone M, 14-deoxyisogarcinol and others — B, bicyclononanes, endo
246
246.1 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
246.2 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
246.3 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
246.4 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
246.5 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
246.6 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
246.7 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
246.8 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
246.9 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
246.10 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
246.11 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
246.12 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
246.13 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe2OH
R4 = prenyl
R5 = prenyl		 coccinone C M. coccinea[a] −60 (0.2)[b] G. Marti 2009
246.14 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
246.15 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
246.16 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
246.17 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
246.18 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
246.19 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
246.20 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 247: garpedvinin E — B, bicyclononanes, endo
247
247.1 garpedvinin E[c] G. pedunculata[a] Roxb. −86.6 (0.30, m)[b] D.-L. Zou 2025
Structure 248: garpedvinin A — B, bicyclononanes, endo
248
248.1 garpedvinin A[c] G. pedunculata[a] Roxb. −86.6 (0.30, m)[b] D.-L. Zou 2025
Structure 249: garciesculentone A — B, bicyclononanes, endo
249
249.1 garciesculentone A[m] G. esculenta[a] −116.5 (0.06, m)[b] H. Zhang 2014b
Structure 250: garcinialiptone B — B, bicyclononanes, endo
250
250.1 garcinialiptone B G. subelliptica[a] +84.8 (5.40, m)[b] L.-J. Zhang 2010
Structure 251: garcicowin D — B, bicyclononanes, exo
251
251.1 garcicowin D G. cowa[a] +336.0 (0.12)[b] G. Xu 2010, Z.-H. Xu 2022
Structure 252: 13,14-didehydroxygarcicowin C, xanthochymusone H, garcicowin C and others — B, bicyclononanes, endo
252
252.1 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
252.2 R1 = 3-hydroxyphenyl
R2 = CH=CMe2		 xanthochymusone H[d] G. xanthochymus[a] +60 (0.1, m)[b] Z.-H. Xu 2022
252.3 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
252.4 R1 = 3,4-dihydroxyphenyl
R2 = CH=CMe2		 xanthochymusone I[d] (enantiomer) G. xanthochymus[a] +69 (0.1, m)[b] Z.-H. Xu 2022
252.5 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
252.6 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 253: garpedvinin D — B, bicyclononanes, endo
253
253.1 garpedvinin D[c] G. pedunculata[a] Roxb. −54.6 (0.1, m)[b] D.-L. Zou 2025
Structure 254: garcoblone E — B, bicyclononanes, endo
254
254.1 garcoblone E[c] G. oblongifolia, G. yunnanensis[a] −44.5 (1.0, m)[b] Z. Wu 2022, Z. Guo 2025a
Structure 255: coccinone A — B, bicyclononanes, endo
255
255.1 coccinone A M. coccinea[a] +28 (1.0)[b] G. Marti 2009
Structure 256: garpedvinin B — B, bicyclononanes, endo
256
256.1 garpedvinin B[c] G. pedunculata[a] Roxb. −65.5 (0.1, m)[b] D.-L. Zou 2025
Structure 257: garpedvinin C — B, bicyclononanes, endo
257
257.1 garpedvinin C[c] G. pedunculata[a] Roxb. −68.8 (0.1, m)[b] D.-L. Zou 2025
Structure 258: garcimultiflorone B, 13-hydroxygarcimultiflorone B — B, bicyclononanes, endo
258
258.1 R = Ph garcimultiflorone B G. multiflora[a] −132 (0.96)[b] J.-J. Chen 2009
258.2 R = 3-hydroxyphenyl 13-hydroxygarcimultiflorone B G. multiflora[a] −115 (0.13)[b] J.-J. Chen 2009
Structure 259: hyperascyrin M — B, bicyclononanes, endo
259
259.1 hyperascyrin M[d] H. ascyron[a] −57.2 (0.1, m)[b] B. Zhen 2019
Structure 260: garschomcinol E, garschomcinol D — B, bicyclononanes, endo
260
260.1 R = CH2CH2CHMeCO2H garschomcinol E[d][e] G. schomburgkiana[a] +12.5 (0.20, m)[b] S. Kaennakam 2022a
260.2 R = geranyl garschomcinol D[d] G. schomburgkiana[a] +13.1 (0.30, m)[b] S. Kaennakam 2022a
Structure 261: guttiferone S, longistylione D, ascyrone C and others — B, bicyclononanes, exo
261
261.1 R1 = H
R2 = prenyl
R3 = prenyl		 guttiferone S G. cochinchinensis[a] −10 (0.28, m)[b] H. D. Nguyen 2011, D. H. Le 2016
261.2 R1 = prenyl
R2 = Me
R3 = prenyl		 longistylione D[c] H. longistylum[a] +19.5 (0.13, mc)[b] X. Cao 2017
261.3 R1 = prenyl
R2 = Me
R3 = (E)-CH=CHCMe2OH		 ascyrone C[d] H. ascyron[a] +78 (0.06, m)[b] X. Deng 2022
261.4 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 262: garcowacinol J, garcowacinol I, longistylione C and others — B, bicyclononanes, exo
262
262.1 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
262.2 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
262.3 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
262.4 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
262.5 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
262.6 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
262.7 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 263: guttiferone H — B, bicyclononanes, exo
263
263.1 guttiferone H[e] G. xanthochymus[a] +94 (0.006)[b] S. Baggett 2005
Structure 264: garcixanthochymone K — B, bicyclononanes, exo
264
264.1 garcixanthochymone K[d] G. xanthochymus[a] −37.9 (0.20, m)[b] S. Jin 2021
Structure 265: burlemarxione E — B, bicyclononanes, caged
265
265.1 burlemarxione E C. burlemarxii[a] +11.0 (0.5)[b] C. G. Ferraz 2021
Structure 266: hyperprin A — B, bicyclononanes, caged
266
266.1 hyperprin A[d] H. przewalskii[a] −4.0 (0.10, m)[b] J.-F. Zong 2020
Structure 267: garciyunnanol D, garciyunnanol C, garciyunnanol B — B, bicyclononanes, exo
267
267.1 R = prenyl
X = OH		 garciyunnanol D[d] G. yunnanensis[a] +158 (0.64, m)[b] X.-Y. Hu 2024
267.2 R = geranyl
X = H		 garciyunnanol C[d] G. yunnanensis[a] +17 (0.18, m)[b] X.-Y. Hu 2024
267.3 R = geranyl
X = OH		 garciyunnanol B[d] G. yunnanensis[a] +115 (0.39, m)[b] X.-Y. Hu 2024
Structure 268: garciyunnanol A — B, bicyclononanes, exo
268
268.1 garciyunnanol A[d] G. yunnanensis[a] +14 (0.16, m)[b] X.-Y. Hu 2024
Structure 269: thoreliolide A — B, bicyclononanes, endo
269
269.1 thoreliolide A[d][e] Calophyllum thorelii +82.0 (0.45, e)[b] L.-T. T. Nguyen 2016
Structure 270: thoreliolide B — B, bicyclononanes, exo
270
270.1 thoreliolide B[d] Calophyllum thorelii −51.2 (0.75, e)[b] L.-T. T. Nguyen 2016
Structure 271: hyperibone K, hypersampsonone K, hyperibrin E and others — B, bicyclononanes, caged
271
271.1 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
271.2 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
271.3 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
271.4 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = CH=CMe2
R4 = prenyl		 18-hydroxyhyperibone K H. hypericoides[a] NR O. E. Christian 2008
271.5 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
271.6 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
271.7 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
271.8 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
271.9 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
271.10 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
271.11 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
271.12 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
271.13 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
271.14 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
271.15 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
271.16 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
271.17 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 272: garcixanthochymone C — B, bicyclononanes, caged
272
272.1 garcixanthochymone C G. xanthochymus[a] +51.0 (0.400, m)[b] Y. Chen 2017
Structure 273: oblongifolin J — B, bicyclononanes, caged
273
273.1 oblongifolin J[c] G. oblongifolia[a] +8.6 (0.03, m)[b] H. Zhang 2014a
Structure 274: hypersampsone R — B, bicyclononanes, endo
274
274.1 hypersampsone R (one of two by that name) H. sampsonii[a] +160 (0.1)[b] J.-J. Chen 2014
Structure 275: garcimultiflorone C — B, bicyclononanes, caged
275
275.1 garcimultiflorone C[e] G. multiflora[a] −25.3 (0.12)[b] J.-J. Chen 2009
Structure 276: garynthone B, garynthone C — B, bicyclononanes, caged
276
276.1 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
276.2 R = (S)-isolavandulyl[g] garynthone C[d] G. yunnanensis[a] +7.85 (0.1, m)[b] Z. Guo 2025a
Structure 277: soniiglucinol A — A, bicyclononanes, endo
277
277.1 soniiglucinol A[c] H. wilsonii[a] −74.0 (0.2, m)[b] S. Xie 2020a
Structure 278: soniiglucinol B — A, bicyclononanes, endo
278
278.1 soniiglucinol B[c][e] H. wilsonii[a] −139.4 (0.4, m)[b] S. Xie 2020a
Structure 279: hypersonin A, hypersonin C, hypersonin B — A, bicyclononanes, endo
279
279.1 R1 = i-Pr
R2 = prenyl		 hypersonin A[c] H. wilsonii[a] −13 (0.9, m)[b] S. Xie 2020b
279.2 R1 = i-Pr
R2 = geranyl		 hypersonin C[c] H. wilsonii[a] −2 (0.4, m)[b] S. Xie 2020b
279.3 R1 = s-Bu
R2 = prenyl		 hypersonin B[c][e] H. wilsonii[a] +3 (0.9, m)[b] S. Xie 2020b
Structure 280: hypersonin D — A, bicyclononanes, endo
280
280.1 hypersonin D[c][e] H. wilsonii[a] −1 (0.2, m)[b] S. Xie 2020b
Structure 281: soniiglucinol C — A, bicyclononanes, endo
281
281.1 soniiglucinol C[c] H. wilsonii[a] −151.3 (0.3, m)[b] S. Xie 2020a
Structure 282: soniiglucinol D — A, bicyclononanes, endo
282
282.1 soniiglucinol D[c] H. wilsonii[a] −24.9 (0.2, m)[b] S. Xie 2020a
Structure 283: enaimeone A — B, bicyclooctanes
283
283.1 enaimeone A H. papuanum[a] +27.8 (0.1, m)[b] K. Winkelmann 2001b, A. B. zur Bonsen 2023
Structure 284: enaimeone B, enaimeone C — B, bicyclooctanes
284
284.1 R = i-Pr enaimeone B H. papuanum[a] +29.4 (0.1, m)[b] K. Winkelmann 2001b, A. B. zur Bonsen 2023
284.2 R = s-Bu enaimeone C[e] H. papuanum[a] +32.9 (0.1, m)[b] K. Winkelmann 2001b, A. B. zur Bonsen 2023
Structure 285: hyperxylone B, hyperxylone A — B, bicyclooctanes
285
285.1 R1 = H
R2 = geranyl		 hyperxylone B[c] H. beanii[a] +41 (0.09, m)[b] X.-Y. Li 2022
285.2 R1 = prenyl
R2 = prenyl		 hyperxylone A[c] H. beanii[a] +38 (0.08, m)[b] X.-Y. Li 2022
Structure 286: ialibinone A, 1′-hydroxyialibinone A, yezo'otogirin E and others — B, bicyclooctanes
286
286.1 R1 = i-Pr
R2 = CMe=CH2		 ialibinone A H. papuanum[a] −22 (0.1)[b] K. Winkelmann 2000
286.2 R1 = i-Pr
R2 = CMe2OH		 1′-hydroxyialibinone A H. papuanum[a] +3.7 (0.1, m)[b] K. Winkelmann 2001b
286.3 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2		 yezo'otogirin E H. yezoense[a] +21.4 (1.7, m)[b] N. Tanaka 2016a
286.4 R1 = s-Bu
R2 = CMe=CH2		 ialibinone C[e] H. papuanum[a] −26 (0.1)[b] K. Winkelmann 2000
Structure 287: ialibinone E, ialibinone B, 1′-hydroxyialibinone B and others — B, bicyclooctanes
287
287.1 R1 = i-Pr
R2 = H		 ialibinone E H. papuanum[a] −33 (0.1)[b] K. Winkelmann 2000
287.2 R1 = i-Pr
R2 = CMe=CH2		 ialibinone B H. papuanum[a] −91 (0.1)[b] K. Winkelmann 2000
287.3 R1 = i-Pr
R2 = CMe2OH		 1′-hydroxyialibinone B H. papuanum[a] −35.7 (0.1, m)[b] K. Winkelmann 2001b
287.4 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2		 yezo'otogirin F H. yezoense[a] +75.9 (1.7, m)[b] N. Tanaka 2016a
287.5 R1 = s-Bu
R2 = CMe=CH2		 ialibinone D[e] H. papuanum[a] −72 (0.1)[b] K. Winkelmann 2000
287.6 R1 = s-Bu
R2 = CMe2OH		 1′-hydroxyialibinone D[e] H. papuanum[a] −30.3 (0.1, m)[b] K. Winkelmann 2001b
Structure 288: lancasternoid A — B, bicyclooctanes
288
288.1 lancasternoid A H. lancasteri[a] racemic J.-Q. You 2025
Structure 289: lancasternoid B — B, bicyclooctanes
289
289.1 lancasternoid B H. lancasteri[a] racemic J.-Q. You 2025
Structure 290: lancasternoid C — B, bicyclooctanes
290
290.1 lancasternoid C H. lancasteri[a] racemic J.-Q. You 2025
Structure 291: lancasternoid D — B, bicyclooctanes
291
291.1 lancasternoid D H. lancasteri[a] racemic J.-Q. You 2025
Structure 292: takaneone A — B, bicyclooctanes, twoC3
292
292.1 takaneone A H. sikokumontanum[a] +30.0 (0.2, m)[b] N. Tanaka 2008
Structure 293: takaneone B — B, bicyclooctanes, twoC3
293
293.1 takaneone B H. sikokumontanum[a] +24.0 (0.3, m)[b] N. Tanaka 2008
Structure 294: takaneone C, hyperelodione E — A, bicyclooctanes, twoC3
294
294.1 R = COCH3 takaneone C H. sikokumontanum[a] +61.9 (0.4, m)[b] N. Tanaka 2008
294.2 R = C(=CH2)CH2CH2CH=CMe2 hyperelodione E[d] H. elodeoides[a] +44.0 (0.24, m)[b] D.-R. Qiu 2021
Structure 295: hyperelodione F — A, bicyclooctanes, twoC3
295
295.1 hyperelodione F[d] H. elodeoides[a] +24.8 (0.33, m)[b] D.-R. Qiu 2021
Structure 296: garcibracgluinol A — bicyclooctanes, seco
296
296.1 garcibracgluinol A[c] G. bracteata[a] +141.4 (0.02, m)[b] J. Xu 2025
Structure 297: no name — B, bicyclooctanes, seco
297
297.1 no common name H. scabrum[a] +30.5 (1.0)[b] S. Soroury 2020
Structure 298: hyperireflexolide A — otherSpiro, seco
298
298.1 hyperireflexolide A[c] H. beanni[a] 0 (1.54)[b] L. Cardona 1993
Structure 299: hyperireflexolide B — otherSpiro, seco
299
299.1 hyperireflexolide B[c] H. beanni[a] 0 (0.74)[b] L. Cardona 1993, A. B. zur Bonsen 2023
Structure 300: hyperberlone A — otherBridgedBicycles, seco
300
300.1 hyperberlone A[c] H. beanni[a] 0 (0.74)[b] Y.-W. Li 2022
Structure 301: garcinielliptone HG, garcinielliptone HH — B, bicyclooctanes
301
301.1 garcinielliptone HG[c] G. subelliptica[a] −17 (0.02, m)[b] C.-C. Liaw 2019
301.2 garcinielliptone HH[d] (enantiomer) G. subelliptica[a] +16 (0.05, m)[b] C.-C. Liaw 2019
Structure 302: (−)-nemorosonol, (+)-nemorosonol, garmultinone D and others — caged, fourPlusTwo
302
302.1 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
302.2 R1 = prenyl
R2 = H
R3 = prenyl		 (+)-nemorosonol[d] (enantiomer) C. nemorosa[a] +203 (0.7)[b] F. delle Monache 1988, S. Cerrini 1993
302.3 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
302.4 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
302.5 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 303: trijapin A — caged, fourPlusTwo
303
303.1 trijapin A[c] T. japonicum[a] −25 (0.2, m)[b] A. Oya 2015
Structure 304: trijapin B, garcibracteamone J — caged, fourPlusTwo
304
304.1 R = prenyl trijapin B T. japonicum[a] −200 (0.1, m)[b] A. Oya 2015
304.2 R = CH2CH2CMe=CH2 garcibracteamone J[c] G. bracteata[a] −169 (0.02, m)[b] Q. Xue 2020
Structure 305: trijapin C — caged, fourPlusTwo
305
305.1 trijapin C T. japonicum[a] +38 (0.04, m)[b] A. Oya 2015
Structure 306: garmultinone A, garmultinone C — caged, fourPlusTwo
306
306.1 R = prenyl garmultinone A[d] G. multiflora[a] +176.4 (0.04, m)[b] Y. Chen 2019b
306.2 R = (E)-CH=CHCMe2OOH garmultinone C[d] G. multiflora[a] +207.2 (0.02, m)[b] Y. Chen 2019b
Structure 307: garmultinone B, 30-hydroxy-garmultinone B — caged, fourPlusTwo
307
307.1 R = Ph garmultinone B[d] G. multiflora[a] +173.9 (0.06, m)[b] Y. Chen 2019b
307.2 R = 3-hydroxyphenyl 30-hydroxy-garmultinone B[d] G. multiflora[a] +25.0 (0.1, m)[b] J. Cao 2024
Structure 308: garmultinone E — caged, fourPlusTwo
308
308.1 garmultinone E[d] (one of two by that name) G. multiflora[a] +85.0 (0.1, m)[b] J. Cao 2024
Structure 309: garmultinone F — caged, fourPlusTwo
309
309.1 garmultinone F[d] G. multiflora[a] +141.0 (0.1, m)[b] J. Cao 2024
Structure 310: (−)-garcimulin A, (+)-garcimulin A, garcimulin B and others — A, caged, exo
310
310.1 R1 = prenyl
R2 = prenyl		 (−)-garcimulin A[c] G. multiflora[a] −142.9 (0.11, m)[b] Y.-M. Fan 2015
310.2 R1 = prenyl
R2 = prenyl		 (+)-garcimulin A[d] (enantiomer) G. multiflora[a] +115.1 (0.11, m)[b] Y.-M. Fan 2015
310.3 R1 = CH2CH2CMe=CH2
R2 = prenyl		 garcimulin B[c] G. multiflora[a] −118.5 (0.21, m)[b] Y.-M. Fan 2015
310.4 R1 = CH2CH2CMe2OH
R2 = prenyl		 garcimulin C[d] G. multiflora[a] +67.0 (0.1, m)[b] J. Cao 2024
Structure 311: (−)-garmultin D, (+)-garmultin D, garmultin H and others — caged, fourPlusTwo
311
311.1 R1 = prenyl
R2 = prenyl		 (−)-garmultin D[c] G. multiflora[a] −166.7 (0.28, m)[b] D. S. Tian 2016
311.2 R1 = prenyl
R2 = prenyl		 (+)-garmultin D[d] (enantiomer) G. multiflora[a] +164.9 (0.30, m)[b] D. S. Tian 2016
311.3 R1 = prenyl
R2 = CH2CH2CMe2OH		 garmultin H[d] G. multiflora[a] +77.0 (0.1, m)[b] H. Luo 2025
311.4 R1 = CH2CH2CMe=CH2
R2 = prenyl		 garmultin E[d] G. multiflora[a] −79.2 (0.29, m)[b] D. S. Tian 2016
Structure 312: (−)-garmultin C, (+)-garmultin C — caged, fourPlusTwo
312
312.1 (−)-garmultin C[c] G. multiflora[a] −85.0 (0.20, m)[b] D. S. Tian 2016
312.2 (+)-garmultin C[d] (enantiomer) G. multiflora[a] +72.6 (0.23, m)[b] D. S. Tian 2016
Structure 313: (−)-garmultin A, (+)-garmultin A, garmultin B — caged, fourPlusTwo
313
313.1 R = prenyl (−)-garmultin A[c] G. multiflora[a] −112.8 (0.24, a)[b] D. S. Tian 2016
313.2 R = prenyl (+)-garmultin A[d] (enantiomer) G. multiflora[a] +110.2 (0.22, a)[b] D. S. Tian 2016
313.3 R = CH2CH2CMe=CH2 garmultin B[d] G. multiflora[a] −53.0 (0.37, m)[b] D. S. Tian 2016
Structure 314: (−)-garmultin F, (+)-garmultin F, garmultin G — caged, fourPlusTwo
314
314.1 R = prenyl (−)-garmultin F[c] G. multiflora[a] −39.0 (0.32, m)[b] D. S. Tian 2016
314.2 R = prenyl (+)-garmultin F[d] (enantiomer) G. multiflora[a] +30.2 (0.37, m)[b] D. S. Tian 2016
314.3 R = CH2CH2CMe=CH2 garmultin G[d] G. multiflora[a] −20.4 (0.25, m)[b] D. S. Tian 2016
Structure 315: hyperuralone A — caged, fourPlusTwo
315
315.1 hyperuralone A[d] H. uralum[a] +34.3 (0.2, m)[b] J.-J. Zhang 2014b
Structure 316: hyperforcinol B — caged, fourPlusTwo
316
316.1 hyperforcinol B[d] H. forrestii[a] +72 (0.2, m)[b] W.-J. Lu 2021
Structure 317: uralin A — caged, fourPlusTwo
317
317.1 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 318: burlemarxione A — caged, fourPlusTwo
318
318.1 burlemarxione A, and tautomer burlemarxione B C. burlemarxii[a] −113.0 (1.35)[b] C. G. Ferraz 2019
Structure 319: garcibractinone B, garcibractinone A — caged, fourPlusTwo, seco
319
319.1 R = prenyl garcibractinone B[c] G. bracteata[a] +20 (0.05, m)[b] Y. Chen 2020
319.2 R = CH2CH2CMe=CH2 garcibractinone A[c] G. bracteata[a] +72 (0.05, m)[b] Y. Chen 2020
Structure 320: hypatulin A — caged, fourPlusTwo, seco
320
320.1 hypatulin A[c] H. patulum[a] +40 (0.05, m)[b] N. Tanaka 2016b
Structure 321: hyperforcinol C — caged, fourPlusTwo, seco
321
321.1 hyperforcinol C[c] H. forrestii[a] +30 (0.2, m)[b] W.-J. Lu 2021
Structure 322: hypatulin B — fourPlusTwo, seco, uncaged
322
322.1 hypatulin B H. patulum[a] +27.0 (0.17, m)[b] N. Tanaka 2016b
Structure 323: garcimultiflin D, garcimultiflin A — caged, fourPlusTwo, seco
323
323.1 X1 = H
X2 = OH		 garcimultiflin D[d] G. multiflora[a] +10.0 (1.0, m)[b] H. Luo 2025
323.2 X1 = OH
X2 = H		 garcimultiflin A[d] G. multiflora[a] −15.0 (1.0, m)[b] J. Cao 2023
Structure 324: garcimultiflin B — caged, fourPlusTwo, seco
324
324.1 garcimultiflin B[d] G. multiflora[a] −10.0 (1.0, m)[b] J. Cao 2023
Structure 325: garcimultiflin C — caged, fourPlusTwo, seco
325
325.1 garcimultiflin C[d] G. multiflora[a] +11.0 (1.0, m)[b] J. Cao 2023
Structure 326: garcibracteatone, garcixanthochymone E, garcibracteatone D and others — A, caged, fourPlusTwo
326
326.1 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
326.2 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
326.3 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
326.4 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
326.5 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
326.6 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
326.7 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
326.8 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
326.9 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
326.10 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
326.11 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
326.12 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
326.13 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
326.14 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
326.15 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
326.16 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
326.17 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
326.18 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
326.19 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
326.20 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
326.21 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
326.22 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
326.23 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
326.24 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
326.25 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 327: garcibracteamone H, burlemarxione H, hyperforcinol A — caged, fourPlusTwo
327
327.1 R1 = CH2CH2CMe=CH2
R2 = H		 garcibracteamone H[c] G. bracteata[a] +40 (0.05, m)[b] Q. Xue 2020
327.2 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
327.3 R1 = prenyl
R2 = prenyl		 hyperforcinol A[d] H. forrestii[a] −39 (0.1, m)[b] W.-J. Lu 2021
Structure 328: hyperkouytone M — caged, fourPlusTwo
328
328.1 hyperkouytone M H. kouytchense[a] −24.8 (0.36, m)[b] H.-Y. Lou 2024
Structure 329: garcibracteamone I — caged, fourPlusTwo
329
329.1 garcibracteamone I[c] G. bracteata[a] −22 (0.05, m)[b] Q. Xue 2020
Structure 330: burlemarxione D — caged, fourPlusTwo
330
330.1 burlemarxione D C. burlemarxii[a] −8.0 (1.0)[b] C. G. Ferraz 2021
Structure 331: hyperlanin B — caged, fourPlusTwo
331
331.1 hyperlanin B[d] H. lancasteri[a] −32.1 (0.3, m)[b] J.-Q. You 2024
Structure 332: hyparillum B — caged, fourPlusTwo
332
332.1 hyparillum B[d] H. patulum[a] −51.5 (0.1)[b] Y. Duan 2024a
Structure 333: hyparillum A — caged, fourPlusTwo
333
333.1 hyparillum A[d] H. patulum[a] −26.1 (0.2)[b] Y. Duan 2024a
Structure 334: garcioblon D — caged, fourPlusTwo
334
334.1 garcioblon D[d] G. oblongifolia[a] −37.2 (0.3, m)[b] Q. Lin 2025
Structure 335: garcioblon A — caged, fourPlusTwo
335
335.1 garcioblon A[d] G. oblongifolia[a] −29.0 (0.4, m)[b] Q. Lin 2025
Structure 336: garcioblon B — caged, fourPlusTwo
336
336.1 garcioblon B[d] G. oblongifolia[a] −32.5 (0.4, m)[b] Q. Lin 2025
Structure 337: garcioblon C — caged, fourPlusTwo
337
337.1 garcioblon C[d] G. oblongifolia[a] −40.6 (0.5, m)[b] Q. Lin 2025
Structure 338: garcioblon E — caged, fourPlusTwo, seco
338
338.1 garcioblon E[d] G. oblongifolia[a] +16.7 (0.5, m)[b] Q. Lin 2025
Structure 339: garcioblon F — caged, fourPlusTwo, seco
339
339.1 garcioblon F[d] G. oblongifolia[a] +26.2 (0.3, m)[b] Q. Lin 2025
Structure 340: burlemarxione I — caged, fourPlusTwo
340
340.1 burlemarxione I[c] C. burle-marxii[a] NR M. do C. C. Silva 2024
Structure 341: garbractin A — caged, fourPlusTwo, seco
341
341.1 garbractin A[c] G. bracteata[a] −94.4 (0.05, m)[b] X.-N. Li 2023
Structure 342: garcibracgluinol B — fourPlusTwo, seco
342
342.1 garcibracgluinol B[c] G. bracteata[a] +248.1 (0.03, m)[b] J. Xu 2025
Structure 343: garcibracgluinol C — fourPlusTwo, seco
343
343.1 garcibracgluinol C[c] G. bracteata[a] +122.2 (0.07, m)[b] J. Xu 2025
Structure 344: xerophenone C, xerophenone A — B, otherBridgedBicycles
344
344.1 R = prenyl xerophenone C G. bracteata[a] +106 (1.0)[b] O. Thoison 2005
344.2 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 345: garcoblone B, garciyunnanin E, garciyunnanin F and others — B, otherBridgedBicycles
345
345.1 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
345.2 R1 = Ph
R2 = prenyl
R3 = CH2CO2H
R4 = H		 garciyunnanin E[c] G. yunnanensis[a] +103.1 (0.13, m)[b] D. Zheng 2021b
345.3 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
345.4 R1 = Ph
R2 = prenyl
R3 = CH2COCMe2OH
R4 = prenyl		 hyperberlone D[c] H. beanii[a] +1.6 (1.7, m)[b] Y.-W. Li 2022
345.5 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
345.6 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 346: garcoblone G, garcibractinol A, garcibractinol E — B, otherBridgedBicycles
346
346.1 R1 = prenyl
R2 = prenyl		 garcoblone G[c] G. oblongifolia[a] −24.1 (1.0, m)[b] S.-Y. Yang 2024
346.2 R1 = prenyl
R2 = CH2CH2CMe=CH2		 garcibractinol A[d] G. bracteata[a] −91.9 (0.04, m)[b] X. Li 2023
346.3 R1 = (E)-CH=CHCMe2OMe
R2 = CH2CH2CMe=CH2		 garcibractinol E[d] G. bracteata[a] −85.1 (0.06, m)[b] X. Li 2023
Structure 347: garcibractinol B, garcibractinol D, garcibractinol C and others — B, otherBridgedBicycles
347
347.1 R = prenyl garcibractinol B[d] G. bracteata[a] −13.3 (0.05, m)[b] X. Li 2023
347.2 R = (E)-CH=CHCMe2OH garcibractinol D[d] G. bracteata[a] −63.9 (0.05, m)[b] X. Li 2023
347.3 R = (E)-CH=CHCMe2OOH garcibractinol C[d] G. bracteata[a] −37.3 (0.05, m)[b] X. Li 2023
347.4 R = (R)-CH2CHOHCMe=CH2 garcibractinol F[d] G. bracteata[a] −5.1 (0.056, m)[b] X. Li 2023
Structure 348: garcoblone H — B, otherBridgedBicycles
348
348.1 garcoblone H[c] G. oblongifolia[a] −26.4 (1.0, m)[b] S.-Y. Yang 2024
Structure 349: garynthone A — B, caged, otherBridgedBicycles
349
349.1 garynthone A G. yunnanensis[a] racemic; +7.85 (0.1, m)[b] and −3.28 (0.1, m)[b] Z. Guo 2025a
Structure 350: garcibractinol G, garcibractinol H — B, otherBridgedBicycles
350
350.1 R = CMe2OH garcibractinol G[d] G. bracteata[a] +150.5 (0.05, m)[b] X. Li 2023
350.2 R = CMe=CH2 garcibractinol H[d] G. bracteata[a] +14.4 (0.04, m)[b] X. Li 2023
Structure 351: garciyunnanin D — B, otherBridgedBicycles
351
351.1 garciyunnanin D[c] G. yunnanensis[a] +23.1 (0.10, m)[b] D. Zheng 2021b
Structure 352: spirohypertone A — B, otherBridgedBicycles, seco
352
352.1 spirohypertone A[c] H. patulum[a] −10.2 (0.2, m)[b] Y. Duan 2024b
Structure 353: trijapin D — B, otherBridgedBicycles
353
353.1 trijapin D T. japonicum[a] −58 (0.6, m)[b] A. Oya 2015
Structure 354: xerophenone G — caged, otherBridgedBicycles
354
354.1 xerophenone G[c][e] G. multiflora[a] +103.0 (0.1, m)[b] J. Cao 2024
Structure 355: xerophenone F — caged, otherBridgedBicycles
355
355.1 xerophenone F[c][e] G. multiflora[a] +164.0 (0.1, m)[b] J. Cao 2024
Structure 356: xerophenone H — caged, otherBridgedBicycles
356
356.1 xerophenone H[e] G. multiflora[a] −15.0 (0.1, m)[b] W.-Y. Lyu 2025
Structure 357: xerophenone D — caged, otherBridgedBicycles
357
357.1 xerophenone D[c] G. multiflora[a] +116.0 (0.1, m)[b] J. Cao 2024
Structure 358: xerophenone E, xerophenone I — caged, otherBridgedBicycles
358
358.1 R = isolavandulyl[g] xerophenone E[c][e] G. multiflora[a] +23.0 (0.1, m)[b] J. Cao 2024
358.2 R = lavandulyl xerophenone I[c][e] G. multiflora[a] −18.0 (0.1, m)[b] H. Luo 2025
Structure 359: garcinielliptone HF — B, otherBridgedBicycles
359
359.1 garcinielliptone HF G. subelliptica[a] −16.7 (0.22, a)[b] C.-C. Wu 2008a
Structure 360: gambogenone — otherBridgedBicycles
360
360.1 gambogenone[e] G. xanthochymus[a] −5 (0.003, m)[b] S. Baggett 2005
Structure 361: garcibractinone C — otherBridgedBicycles
361
361.1 garcibractinone C[c] G. multiflora[a] +32.1 (0.02, m)[b] Q. Li 2022
Structure 362: hyperberin A, hyperberin B, hyperberin C — B, otherBridgedBicycles
362
362.1 R = (2R)-3,3-dimethyloxiran-2-yl hyperberin A[d] H. beanii[a] +69.1 (0.33, m)[b] W.-J. Xu 2019
362.2 R = (2S)-3,3-dimethyloxiran-2-yl hyperberin B[d] H. beanii[a] +95.8 (0.28, m)[b] W.-J. Xu 2019
362.3 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 363: hyperberlone E — B, otherBridgedBicycles
363
363.1 hyperberlone E[d] H. beanii[a] +5.7 (0.7, m)[b] Y.-W. Li 2022
Structure 364: hyperforone C, hyperforone B — B, otherBridgedBicycles, seco
364
364.1 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
364.2 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 365: hypercohin A, hypaluton B — A, otherBridgedBicycles
365
365.1 R = prenyl hypercohin A[c] H. cohaerens, H. forrestii[a] NR X.-W. Yang 2012, W.-J. Lu 2020
365.2 R = (E)-C=CCMe2OH hypaluton B[c] H. patulum[a] −108.7 (0.4, m)[b] Y. Duan 2021a
Structure 366: hyperforone A — A, otherBridgedBicycles, seco
366
366.1 hyperforone A[c] (one of two by that name) H. forrestii[a] −102 (0.1, m)[b] W.-J. Lu 2020
Structure 367: hypaluton A — A, otherBridgedBicycles, seco
367
367.1 hypaluton A[c] H. patulum[a] −64.2 (0.3, m)[b] Y. Duan 2021a
Structure 368: hyperbeanin P — A, otherBridgedBicycles
368
368.1 hyperbeanin P[c] H. beanii[a] −254 (0.2, m)[b] X.-Y. Suo 2021b
Structure 369: hyperprin B — A, otherBridgedBicycles
369
369.1 hyperprin B[c] H. przewalskii[a] −314.0 (0.10, m)[b] J.-F. Zong 2020
Structure 370: hyperacmosin R — A, exo, otherBridgedBicycles
370
370.1 hyperacmosin R[c] H. acmosepalum[a] −230.5 (0.14, m)[b] Y. Ma 2022b
Structure 371: hyperinoid A — otherBridgedBicycles, seco
371
371.1 hyperinoid A[c] H. patulum[a] +54.0 X. Jia 2020
Structure 372: hyperinoid B — otherBridgedBicycles, seco
372
372.1 hyperinoid B[c] H. patulum[a] +61.0 X. Jia 2020
Structure 373: (±)-hypandrone A — otherBridgedBicycles
373
373.1 (±)-hypandrone A H. androsaemum[a] 0 J. Wei 2024a
Structure 374: hypertaxoid B — B, otherBridgedBicycles
374
374.1 hypertaxoid B[d] H. elatoides[a] +13.1 (0.05, m)[b] J.-Y. Xie 2026
Structure 375: hypertaxoid A — B, otherBridgedBicycles
375
375.1 hypertaxoid A[d] H. elatoides[a] +76.1 (0.05, m)[b] J.-Y. Xie 2026
Structure 376: hypermonin A — B, otherBridgedBicycles, seco
376
376.1 hypermonin A[c] H. monogynum[a] +46.5 (0.20, m)[b] Y.-R. Zeng 2018
Structure 377: hypermonin B — B, otherBridgedBicycles, seco
377
377.1 hypermonin B[c] H. monogynum[a] +155.42 (0.24, m)[b] Y.-R. Zeng 2018
Structure 378: garciyunnanin G — B, otherBridgedBicycles, seco
378
378.1 garciyunnanin G[c] G. yunnanensis[a] +28.7 (0.10, m)[b] D. Zheng 2021b
Structure 379: hyperjaponiol B — spiroindanes
379
379.1 hyperjaponiol B[c] H. japonicum [a]Thunb. ex Murray +55.7 (0.1, m)[b] Y. Liu 2026
Structure 380: harrisotone A, harrisotone B, tomoeone B and others — spiroindanes, transHydrindane
380
380.1 R = Me
X = OH		 harrisotone A Harrisonia perforata +2.0 (0.27, m)[b] S. Yin 2009
380.2 R = Me
X = OOH		 harrisotone B Harrisonia perforata +25.4 (1.30, m)[b] S. Yin 2009
380.3 R = i-Pr
X = OH		 tomoeone B H. ascyron[a] +9.5 (1.1, m)[b] W. Hashida 2008
380.4 R = i-Pr
X = OOH		 tomoeone D H. ascyron[a] +10.4 (3.0, m)[b] W. Hashida 2008, H. Zhu 2015a
380.5 R = i-Bu
X = OH		 tomoeone F H. ascyron[a] +1.8 (1.8, m)[b] W. Hashida 2008
380.6 R = i-Bu
X = OOH		 tomoeone H H. ascyron[a] +5.2 (2.7, m)[b] W. Hashida 2008, H. Zhu 2015a
380.7 R = Ph
X = OH		 hyperbeanol A H. beanii[a] +2.74 (0.21)[b] X.-Q. Chen 2011
380.8 R = Ph
X = OOH		 hyperpatulol B[c] H. patulum[a] −35.2 (0.1, m)[b] Y.-Y. Liu 2019
Structure 381: hypulatone D, hyperascyrone D, hookerianone E and others — spiroindanes, transHydrindane
381
381.1 R1 = i-Pr
R2 = Me
X = H		 hypulatone D H. patulum[a] –12 (0.1, m)[b] Y.-F. Qiu 2026
381.2 R1 = i-Pr
R2 = prenyl
X = OH		 hyperascyrone D[c] H. ascyron[a] −7.8 (0.48, m)[b] H. Zhu 2015a
381.3 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
381.4 R1 = i-Bu
R2 = prenyl
X = OH		 hyperascyrone E[c] H. ascyron[a] −9.1 (0.68, m)[b] H. Zhu 2015a
381.5 R1 = Ph
R2 = prenyl
X = OH		 hyperpatulol A H. beanii[a] +14.27 (0.34)[b] X.-Q. Chen 2011, X. Liu 2026
Structure 382: harperoid B, harrisotone C, harrisotone E and others — spiroindanes, transHydrindane
382
382.1 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = H
X2 = H		 harperoid B Harrisonia perforata +15 (0.4, m)[b] P.-P. An 2026
382.2 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 harrisotone C Harrisonia perforata +11.1 (0.80, m)[b] S. Yin 2009
382.3 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 harrisotone E Harrisonia perforata +22.1 (0.09, m)[b] S. Yin 2009
382.4 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
382.5 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
382.6 R1 = i-Pr
R2 = Me
R3 = prenyl
X1 = OOH
X2 = H		 pyramidatone D H. pyramidatum[a] +20.0 (0.009)[b] R. Force 2014
382.7 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
382.8 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = OOH
X2 = H		 pyramidatone B H. pyramidatum[a] +15.5 (0.03)[b] R. Force 2014
382.9 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
382.10 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
382.11 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
382.12 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
382.13 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
382.14 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
382.15 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
382.16 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
382.17 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
382.18 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperbeanol C H. beanii[a] +31.21 (0.19)[b] X.-Q. Chen 2011
382.19 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 383: hyperpatulone D — spiroindanes, transHydrindane
383
383.1 hyperpatulone D[c] (one of two by that name) H. patulum[a] +83.6 (0.10, m)[b] Y.-x. Zhang 2021
Structure 384: harrisotone D, monosescinol C, hyperpatulol C and others — spiroindanes, transHydrindane
384
384.1 R1 = Me
R2 = prenyl
R3 = prenyl
X = OH		 harrisotone D Harrisonia perforata +4.1 (0.12, m)[b] S. Yin 2009
384.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = OH		 monosescinol C[c] H. longistylum[a] −30.0 (0.4, m)[b] Z. Shi 2024
384.3 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
384.4 R1 = i-Pr
R2 = prenyl
R3 = Me
X = OOH		 pyramidatone C H. pyramidatum[a] +17.3 (0.01)[b] R. Force 2014
384.5 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
384.6 R1 = (R)-s-Bu
R2 = prenyl
R3 = prenyl
X = OH		 hyperlagarol I[c] H. beanii[a] NR R.-D. Hu 2024
384.7 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
X = OH		 hyperlagarol H[c] H. beanii[a] NR R.-D. Hu 2024
384.8 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 385: hyperpatulol D, hyperpatulol E — spiroindanes, transHydrindane
385
385.1 R = i-Pr hyperpatulol D[c] H. patulum[a] +2.2 (0.1, m)[b] Y.-Y. Liu 2019
385.2 R = s-Bu hyperpatulol E[c][e] H. patulum[a] +10.6 (0.1, m)[b] Y.-Y. Liu 2019
Structure 386: hunascynol I — spiroindanes, transHydrindane
386
386.1 hunascynol I
(or its epimer, hunascynol J)		 H. ascyron[a] −0.7 (0.09, m)[b] Y.-L. Hu 2023
Structure 387: hunascynol J — spiroindanes, transHydrindane
387
387.1 hunascynol J
(or its epimer, hunascynol I)		 H. ascyron[a] −1.2 (0.11, m)[b] Y.-L. Hu 2023
Structure 388: kouytchin B, hyperascyrone B, hyperascyrone C and others — cisHydrindane, spiroindanes
388
388.1 R1 = i-Pr
R2 = Me
X = H		 kouytchin B[d][m] H. kouytchense[a] +27.1 (0.5, m)[b] C. Jing 2026
388.2 R1 = i-Pr
R2 = prenyl
X = OH		 hyperascyrone B[d] H. ascyron[a] −4.8 (0.24, m)[b] H. Zhu 2015a
388.3 R1 = i-Bu
R2 = prenyl
X = OH		 hyperascyrone C[d] H. ascyron[a] −3.8 (0.38, m)[b] H. Zhu 2015a
388.4 R1 = Ph
R2 = prenyl
X = OH		 hyperascyrone A[d] H. ascyron[a] −16.4 (0.33, m)[b] H. Zhu 2015a
Structure 389: hunascynol H, spirohypatone B, spihyperglucinol E and others — cisHydrindane, spiroindanes
389
389.1 R1 = i-Pr
R2 = prenyl
X = H		 hunascynol H H. ascyron[a] +50 (0.10, m)[b] Y.-L. Hu 2023
389.2 R1 = i-Pr
R2 = prenyl
X = OH		 spirohypatone B[c] H. patulum[a] +23.03 (0.101, m)[b] Y. Ye 2020
389.3 R1 = i-Bu
R2 = Me
X = OH		 spihyperglucinol E[c] H. longistylum[a] −18.3 (0.3, m)[b] Z. Shi 2022
389.4 R1 = i-Bu
R2 = prenyl
X = H		 hunascynol G H. ascyron[a] +53 (0.10, m)[b] Y.-L. Hu 2023
389.5 R1 = i-Bu
R2 = prenyl
X = OH		 hunascynol F[c] H. ascyron[a] −6.0 (0.10, m)[b] Y.-L. Hu 2023
389.6 R1 = (R)-s-Bu
R2 = Me
X = H		 hyperpatulone E[c] H. patulum[a] +44.3 (0.20, m)[b] Y.-x. Zhang 2021
389.7 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
389.8 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
389.9 R1 = (R)-s-Bu
R2 = prenyl
X = OH		 hunascynol D[c] H. ascyron[a] +5.0 (0.12, m)[b] Y.-L. Hu 2023
389.10 R1 = (S)-s-Bu
R2 = prenyl
X = OH		 hunascynol E[c] H. ascyron[a] +18 (0.15, m)[b] Y.-L. Hu 2023
389.11 R1 = Ph
R2 = prenyl
X = OH		 hyperbeanin C[c] H. beanii[a] +34.5 (0.12, m)[b] Y. Ma 2022a
Structure 390: chipericumin A, chipericumin B, sampsonol A — spiroindanes, transHydrindane
390
390.1 R1 = i-Pr
R2 = Me		 chipericumin A H. chinense[a] +84.3 (0.29, m)[b] S. Abe 2012
390.2 R1 = s-Bu
R2 = Me		 chipericumin B[e] H. chinense[a] +116.1 (0.46, m)[b] S. Abe 2012
390.3 R1 = Ph
R2 = prenyl		 sampsonol A H. sampsonii[a] −7.7 (0.5, mc)[b] W. Xin 2012
Structure 391: sampsonol B — spiroindanes, transHydrindane
391
391.1 sampsonol B H. sampsonii[a] +45.3 (0.5, mc)[b] W. Xin 2012
Structure 392: hyperhenone L — spiroindanes, transHydrindane
392
392.1 hyperhenone L H. henryi[a] −6 (0.08, m)[b] Y.-T. Duan 2018
Structure 393: lagarocladone B — spiroindanes, transHydrindane
393
393.1 lagarocladone B[c] H. lagarocladum[a] +63.8 (0.1, m)[b] L.-T. Lai 2026
Structure 394: hyperacmotone D — spiroindanes, transHydrindane
394
394.1 hyperacmotone D[c] H. acmosepalum[a] +20 (0.10, m)[b] A.-Z. Wang 2022
Structure 395: hyperacmotone E — spiroindanes, transHydrindane
395
395.1 hyperacmotone E[c] H. acmosepalum[a] –1 (0.10, m)[b] A.-Z. Wang 2022
Structure 396: hyperacmotone F — spiroindanes, transHydrindane
396
396.1 hyperacmotone F[c] H. acmosepalum[a] +60 (0.10, m)[b] A.-Z. Wang 2022
Structure 397: hypericumono A — seco, spiroindanes, transHydrindane
397
397.1 hypericumono A[c] H. monogynum[a] +24.443 (0.06, m)[b] Y.-R. Zeng 2026a
Structure 398: spiropatuol G, spiropatuol H — cisHydrindane, spiroindanes
398
398.1 R = i-Bu spiropatuol G[c] H. patulum[a] +3.0 (0.1, m)[b] Z. Shi 2026
398.2 R = s-Bu spiropatuol H[c][e] H. patulum[a] +11.6 (0.1, m)[b] Z. Shi 2026
Structure 399: harperoid C, sampsonol F, hyperhenone I and others — caged, spiroindanes, transHydrindane
399
399.1 R1 = Me
R2 = prenyl
R3 = prenyl
X = H		 harperoid C Harrisonia perforata +26 (0.4, m)[b] P.-P. An 2026
399.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = H		 sampsonol F H. sampsonii[a] +12.4 (0.5, mc)[b] W. Xin 2012
399.3 R1 = i-Pr
R2 = prenyl
R3 = Me
X = H		 hyperhenone I H. henryi[a] −516 (0.12, m)[b] Y.-T. Duan 2018
399.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X = H		 hyperlagarin A H. lagarocladum[a] −87.9 (0.29, m)[b] K. Wang 2019
399.5 R1 = i-Bu
R2 = Me
R3 = prenyl
X = H		 sampsonol E H. sampsonii[a] +25.8 (0.5, mc)[b] W. Xin 2012
399.6 R1 = s-Bu
R2 = Me
R3 = prenyl
X = H		 hyperhenone H[e] H. henryi[a] −71 (0.15, m)[b] Y.-T. Duan 2018
399.7 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
399.8 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
399.9 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X = H		 hyperlagarin B[e] H. lagarocladum[a] −87.9 (0.18, m)[b] K. Wang 2019
399.10 R1 = Ph
R2 = prenyl
R3 = Me
X = H		 sampsonol C H. sampsonii[a] +16.5 (0.5, mc)[b] W. Xin 2012
399.11 R1 = Ph
R2 = prenyl
R3 = prenyl
X = H		 hypercohone G H. cohaerens[a] −56.1 (0.16, m)[b] J.-J. Zhang 2014a
399.12 R1 = Ph
R2 = prenyl
R3 = prenyl
X = OH		 kouytchin A[c][m] H. kouytchense[a] −20.0 (0.5, m)[b] C. Jing 2026
399.13 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = Me
X = H		 sampsonol D H. sampsonii[a] +35.2 (0.5, mc)[b] W. Xin 2012
399.14 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 400: harperoid D, hyperhenone G, hyperpatulol I and others — caged, cisHydrindane, spiroindanes
400
400.1 R1 = Me
R2 = prenyl
R3 = prenyl		 harperoid D Harrisonia perforata −22 (0.4, m)[b] P.-P. An 2026
400.2 R1 = i-Pr
R2 = Me
R3 = prenyl		 hyperhenone G H. henryi[a] −99 (0.07, m)[b] Y.-T. Duan 2018
400.3 R1 = i-Pr
R2 = prenyl
R3 = Me		 hyperpatulol I[c] H. patulum[a] −9.4 (0.1, m)[b] Y.-Y. Liu 2019
400.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl		 hyperlagarin C H. lagarocladum[a] −89.7 (0.25, m)[b] K. Wang 2019
400.5 R1 = (S)-s-Bu
R2 = prenyl
R3 = Me		 hyperpatulol H[c] H. patulum[a] −31.2 (0.1, m)[b] Y.-Y. Liu 2019
400.6 R1 = Ph
R2 = prenyl
R3 = prenyl		 hyperbeanol F H. beanii[a] −46 (0.5, m)[b] Y.-R. Li 2019
Structure 401: hyperbeanol G — caged, cisHydrindane, spiroindanes
401
401.1 hyperbeanol G H. beanii[a] +15 (0.09, m)[b] Y.-R. Li 2019
Structure 402: hypehenol A — caged, OC3, spiroindanes
402
402.1 hypehenol A[c] H. henryi[a] +8.6 (0.23, m)[b] T. Yue 2026
Structure 403: hypehenol B, hypehenol C — caged, seco, spiroindanes
403
403.1 R = i-Pr hypehenol B[c] H. henryi[a] +6.2 (0.19, m)[b] T. Yue 2026
403.2 R = s-Bu hypehenol C[c][e] H. henryi[a] +10.8 (0.33, m)[b] T. Yue 2026
Structure 404: hunascynol A — caged, seco, spiroindanes
404
404.1 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 405: hunascynol B — caged, cisHydrindane, seco
405
405.1 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 406: hyperlagarol G — caged, spiroindanes
406
406.1 hyperlagarol G[c] H. beanii[a] NR R.-D. Hu 2024
Structure 407: hunascynol C — caged, cisHydrindane, spiroindanes
407
407.1 hunascynol C H. ascyron[a] +29 (0.14, m)[b] Y.-L. Hu 2023
Structure 408: hyperpatulone G — caged, cisHydrindane, spiroindanes
408
408.1 hyperpatulone G[c] H. patulum[a] +62.0 (0.10, m)[b] Y.-x. Zhang 2021
Structure 409: hyperbeanol H — caged, spiroindanes
409
409.1 hyperbeanol H H. beanii[a] +52 (0.7, m)[b] Y.-R. Li 2019
Structure 410: hypericumono D, spiropatuol E, spiropatuol F — caged, spiroindanes, transHydrindane
410
410.1 R = i-Pr hypericumono D[c] H. monogynum[a] −16.452 (0.24, m)[b] Y.-R. Zeng 2026a
410.2 R = i-Bu spiropatuol E[c] H. patulum[a] –45.5 (0.1, m)[b] Z. Shi 2026
410.3 R = s-Bu spiropatuol F[c][e] H. patulum[a] –56.6 (0.1, m)[b] Z. Shi 2026
Structure 411: hyperhenone K — caged, spiroindanes, transHydrindane
411
411.1 hyperhenone K H. henryi[a] −6 (0.07, m)[b] Y.-T. Duan 2018
Structure 412: spiropatuol D, spiropatuol B, spiropatuol C — caged, spiroindanes, transHydrindane
412
412.1 R = i-Pr spiropatuol D[c] H. patulum[a] +5.225 (0.4, m)[b] Z. Shi 2026
412.2 R = i-Bu spiropatuol B[c] H. patulum[a] +2.7 (0.5, m)[b] Z. Shi 2026
412.3 R = s-Bu spiropatuol C[c][e] H. patulum[a] –10.5 (0.3, m)[b] Z. Shi 2026
Structure 413: hyperispirone B — caged, spiroindanes, transHydrindane
413
413.1 hyperispirone B[c] H. beanii[a] −53 (0.18, m)[b] B. Yang 2022
Structure 414: hyperispirone A — caged, cisHydrindane, spiroindanes
414
414.1 hyperispirone A[c] H. beanii[a] +70 (0.15, m)[b] B. Yang 2022
Structure 415: hyperlagarol J — caged, cisHydrindane, spiroindanes
415
415.1 hyperlagarol J[c] H. beanii[a] NR R.-D. Hu 2024
Structure 416: hyperin C, hyperin D, hypatulone A — caged, spiroindanes, transHydrindane
416
416.1 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
416.2 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
416.3 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 417: hyperin A, hyperin B — caged, seco, spiroindanes
417
417.1 R = i-Pr hyperin A[c] H. monogynum[a] −78.50 (0.08, m)[b] Y.-R. Zeng 2021b, Y.-R. Zeng 2026b
417.2 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 418: hyperilongenol C, hyperilongenol B, hyperilongenol A — seco, spiroindanes
418
418.1 R = i-Pr hyperilongenol C[c] H. longistylum[a] +82.3 (0.5, m)[b] N. Zhang 2019a, N. Zhang 2019b
418.2 R = i-Bu hyperilongenol B[c] H. longistylum[a] +85.2 (0.3, m)[b] N. Zhang 2019a, N. Zhang 2019b
418.3 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 419: hyperlagarol C — caged, seco, spiroindanes
419
419.1 hyperlagarol C[c] H. beanii[a] NR R.-D. Hu 2024
Structure 420: hyperlagarol D — seco, spiroindanes
420
420.1 hyperlagarol D[c] H. beanii[a] NR R.-D. Hu 2024
Structure 421: spihyperglucinol A, spihyperglucinol B — caged, seco, spiroindanes
421
421.1 R = i-Bu spihyperglucinol A[c] H. longistylum[a] −130.0 (0.8, m)[b] Z. Shi 2022
421.2 R = s-Bu spihyperglucinol B[c][e] H. longistylum[a] −112.6 (0.1, m)[b] Z. Shi 2022
Structure 422: spihyperglucinol C, spihyperglucinol D — caged, seco, spiroindanes
422
422.1 R = i-Bu spihyperglucinol C[c] H. longistylum[a] −53.4 (0.4, m)[b] Z. Shi 2022
422.2 R = s-Bu spihyperglucinol D[c][e] H. longistylum[a] −61.6 (0.4, m)[b] Z. Shi 2022
Structure 423: hypericumono F — seco, spiroindanes, transHydrindane
423
423.1 hypericumono F[c] H. monogynum[a] −40.000 (0.10, m)[b] Y.-R. Zeng 2026a
Structure 424: biyouyanagiol, uralin D — seco, spiroindanes, transHydrindane
424
424.1 R = Me biyouyanagiol[y] H. chinense[a] +10.5 (0.5)[b] N. Tanaka 2009a
424.2 R = prenyl uralin D[c] H. uralum[a] +32 (0.1, m)[b] Q.-Q. Fang 2021
Structure 425: biyoulactone D, biyoulactone E — seco, spiroindanes, transHydrindane
425
425.1 R = i-Pr biyoulactone D H. chinense[a] −39.4 (0.1, m)[b] N. Tanaka 2012
425.2 R = s-Bu biyoulactone E[e] H. chinense[a] −14.4 (0.07, m)[b] N. Tanaka 2012
Structure 426: hyperbeanone A — seco, spiroindanes, transHydrindane
426
426.1 hyperbeanone A[c] H. beanii[a] −134 (0.15, m)[b] B. Yang 2021a
Structure 427: hypermonone B, hypermonone C, hypermonol J and others — seco, spiroindanes, transHydrindane
427
427.1 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
427.2 R = s-Bu hypermonone C[c][e] H. monogynum[a] −40.83 (0.07, m)[b] Y.-R. Zeng 2021c
427.3 R = (R)-s-Bu hypermonol J[c] H. monogynum[a] +42.5 (0.1, m)[b] Y. Li 2026
427.4 R = (S)-s-Bu hypermonol K[c] H. monogynum[a] +119.2 (0.1, m)[b] Y. Li 2026
Structure 428: hypermonol F — seco, spiroindanes, transHydrindane
428
428.1 hypermonol F[c] H. monogynum[a] –48.3 (m, 0.1)[b] Y. Li 2026
Structure 429: hypermonol G — seco, spiroindanes, transHydrindane
429
429.1 hypermonol G[c] H. monogynum[a] +41.5 (0.1, m)[b] Y. Li 2026
Structure 430: hypermonone D — seco, spiroindanes, transHydrindane
430
430.1 hypermonone D[c] H. monogynum[a] +47.26 (0.12, m)[b] Y.-R. Zeng 2021c
Structure 431: hypermonone A — cisHydrindane, seco, spiroindanes
431
431.1 hypermonone A[c] H. monogynum[a] +123.49 (0.09, m)[b] Y.-R. Zeng 2021c
Structure 432: hypermonol H, hypermonol L — cisHydrindane, seco, spiroindanes
432
432.1 R = i-Pr hypermonol H[c] H. monogynum[a] +124.7 (m, 0.1)[b] Y. Li 2026
432.2 R = (R)-s-Bu hypermonol L[c] H. monogynum[a] +6.4 (m, 0.1)[b] Y. Li 2026
Structure 433: hypermonane A — caged, seco, spiroindanes
433
433.1 hypermonane A[c][e] H. monogynum[a] +6.4 (0.1, m)[b] B. Geng 2026
Structure 434: hybeanone B, hybeanone A — seco, spiroindanes, transHydrindane
434
434.1 R = i-Pr hybeanone B[c] H. beanii[a] +72.3 (0.17, m)[b] B. Yang 2021b
434.2 R = (S)-s-Bu hybeanone A[c] H. beanii[a] +48.9 (0.09, m)[b] B. Yang 2021b
Structure 435: hypermonol A, hypermonol E — seco, spiroindanes, transHydrindane
435
435.1 R = i-Pr hypermonol A[c] H. monogynum[a] +25.8 (0.1, m)[b] J. Wei 2024b
435.2 R = (S)-s-Bu hypermonol E[c] H. monogynum[a] +18.8 (0.1, m)[b] J. Wei 2024b
Structure 436: hypermonol B, hypermonol C, hypermonol D — seco, spiroindanes, transHydrindane
436
436.1 R = i-Pr hypermonol B[c] H. monogynum[a] −64.6 (0.1, m)[b] J. Wei 2024b
436.2 R = (R)-s-Bu hypermonol C[c] H. monogynum[a] +10.4 (0.1, m)[b] J. Wei 2024b
436.3 R = (S)-s-Bu hypermonol D[c] H. monogynum[a] +5.4 (0.1, m)[b] J. Wei 2024b
Structure 437: biyoulactone A — seco, spiroindanes, transHydrindane
437
437.1 biyoulactone A[c] H. chinense[a] +8.1 (0.1, m)[b] N. Tanaka 2011
Structure 438: hypemoin A, biyoulactone B — seco, spiroindanes, transHydrindane
438
438.1 R = i-Pr hypemoin A[c] H. monogynum[a] +24 (0.2, m)[b] Y.-N. Li 2011
438.2 R = (S)-s-Bu biyoulactone B H. chinense[a] +9.7 (0.2, m)[b] N. Tanaka 2011
Structure 439: hypemoin B, biyoulactone C — cisHydrindane, seco, spiroindanes
439
439.1 R = i-Pr hypemoin B[c] H. monogynum[a] +48 (0.2, m)[b] Y.-N. Li 2011
439.2 R = (S)-s-Bu biyoulactone C H. chinense[a] +15.7 (0.09, m)[b] N. Tanaka 2011
Structure 440: furanmonogone B, hyperascone A, hyperascone B and others — seco, spiroindanes, transHydrindane
440
440.1 R1 = i-Pr
R2 = Me		 furanmonogone B[c][e] H. monogynum[a] −8 (0.1, m)[b] W.-J. Xu 2017
440.2 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH		 hyperascone A[c][aa] H. ascyron[a] Linn. +6.3 (0.03, m)[b] S. Wang 2024
440.3 R1 = i-Bu
R2 = (E)-CH=CHCMe2OH		 hyperascone B[c][aa] H. ascyron[a] Linn. +5.7 (0.03, m)[b] S. Wang 2024
440.4 R1 = s-Bu
R2 = Me		 furanmonogone A[c][e] H. monogynum[a] −12 (0.1, m)[b] W.-J. Xu 2017
440.5 R1 = Ph
R2 = (E)-CH=CHCMe2OH		 hyperhenone M[e] H. henryi[a] −31 (0.10, m)[b] Y.-T. Duan 2018
Structure 441: hypemoin E, hypemoin D, hypemoin C — seco, spiroindanes, transHydrindane
441
441.1 R = H hypemoin E[c] H. monogynum[a] −76 (0.1, m)[b] Y.-N. Li 2011
441.2 R = CO2Me hypemoin D[c] H. monogynum[a] +52 (0.1, m)[b] Y.-N. Li 2011
441.3 R = COCHMeCH2CH=CMe2 hypemoin C[c][e] H. monogynum[a] +48 (0.2, m)[b] Y.-N. Li 2011
Structure 442: longisglucinol A — seco, spiroindanes
442
442.1 longisglucinol A[c] H. longistylum[a] −31.2 (0.5, m)[b] N. Zhang 2020
Structure 443: hymoin B — seco, spiroindanes, transHydrindane
443
443.1 hymoin B[c] H. monogynum[a] +160.00 (0.10, m)[b] C. Yuan 2025
Structure 444: spirohypatone A, longisglucinol C, longisglucinol B and others — spiropentalanes
444
444.1 R1 = i-Pr
R2 = Me		 spirohypatone A[c] H. patulum[a] +105.54 (0.10, m)[b] Y. Ye 2020
444.2 R1 = i-Bu
R2 = Me		 longisglucinol C[c][ff] H. longistylum[a] +99.8 (0.5, m)[b] N. Zhang 2020
444.3 R1 = (S)-s-Bu
R2 = Me		 longisglucinol B[c][ff] H. longistylum[a] +106.9 (0.5, m)[b] N. Zhang 2020
444.4 R1 = Ph
R2 = prenyl		 hyperacmotone C[c] H. acmosepalum[a] +101 (0.20, m)[b] A.-Z. Wang 2022
Structure 445: harperoid A, spiropatuol A — spiropentalanes
445
445.1 R = Me harperoid A[c] Harrisonia perforata +12 (0.2, m)[b] P.-P. An 2026
445.2 R = i-Pr spiropatuol A[c] H. patulum[a] +60.625 (0.1, m)[b] Z. Shi 2026
Structure 446: hymoin A — caged, seco, spiropentalanes
446
446.1 hymoin A[c] H. monogynum[a] +77.92 (0.15, m)[b] C. Yuan 2025
Structure 447: hyperzrone A — spiropentalanes
447
447.1 hyperzrone A[c] H. beanii[a] +19.8 (0.1, m)[b] X.-Y. Li 2025
Structure 448: hyperzrone B — spiropentalanes
448
448.1 hyperzrone B[c] H. beanii[a] −1.7 (0.1, m)[b] X.-Y. Li 2025

Statistics

There are 1528 compounds listed.

FeatureNumber
bicyclo[3.3.1]nonanes1182
bicyclo[3.2.1]octanes28
bicyclo[2.2.2]octanes88
other bridged bicyclics53
spiroindanes166
spiropentalanes9
other spiro compounds2
exo at C(7)597
endo at C(7)554
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 A919
type B360
uncaged861
caged432
seco and nor280
enamine replacing carbonyl8
dimer2
trans-hydrindane119
cis-hydrindane34
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