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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 1467 compounds in 434 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 −0.58 (c 1.30, m) G. E. Henry 2006
1.2 R1 = i-Pr
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyperevolutin A H. revolutum Vahl +84.4 (0.5, m) L. A. Decosterd 1989
1.3 R1 = i-Pr
R2 = prenyl
R3 = H
R4 = prenyl
R5 = prenyl		 olympiforin B[c] H. olympicum L. +9.8 (0.116, m) 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 Crantz, H. perforatum, H. polyphyllum, H. triquetrifolium +7.2 (1, m), OMe: +7 (0.10, m) 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 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 +41 (5, e) 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 −33 (0.6) J.-R. Weng 2003a
1.8 R1 = i-Bu
R2 = H
R3 = geranyl
R4 = prenyl
R5 = H		 garcicosin G. verrucosa −10 (0.3) M. Rajaonarivelo 2016
1.9 R1 = s-Bu
R2 = H
R3 = H
R4 = prenyl
R5 = geranyl		 prolifenone A[e] H. prolificum +13.3 (0.145, m) G. E. Henry 2006
1.10 R1 = s-Bu
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyperevolutin B[e] H. revolutum 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 L. +20.97 (0.102, m) Y. Ilieva 2023
1.12 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 adsecohyperforin[e] H. perforatum NR A. Charchoglyan 2007
1.13 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 adhyperforin[e] H. perforatum NR P. Maisenbacher 1992
1.14 R1 = s-Bu
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H		 garcinielliptone D[e] G. subelliptica −22 (0.1) 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 +113 (0.1); OMe: +150 (0.8, m) and +49 (1.4) 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 −66 (0.2, m) W.-J. Lu 2020
1.17 R1 = Ph
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 chamone I[e] C. grandiflora NR J. Lokvam 2000
1.18 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 hydroxynemorosone C. nemorosa OMe: +143 (0.7, m) 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 −79.1 (7.83, m) 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 NR L. Ernst 2024
2.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl		 no common name H. sampsonii NR L. Ernst 2024
2.3 R1 = Ph
R2 = prenyl
R3 = prenyl		 plukenetione D, a.k.a. 7-epi-nemorosone[d] C. nemorosa, C. plukenetii, H. sampsonii OAc: +34.5 (0.03), −37.6 (0.1); OMe: +10.7 (3.1) 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 OMe: +92.7 (1.6) A. L. M. Porto 2000
2.5 R1 = Ph
R2 = geranyl
R3 = prenyl		 nemosampsone[d] H. sampsonii NR L. Ernst 2024
Structure 3: hyperfirin — A, bicyclononanes, noC7
3
3.1 hyperfirin H. perforatum 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 +13 (0.22, m) N.-N. Jiang 2019
4.2 R1 = i-Pr
R2 = (E)-CH2CH=CMeCHO
R3 = prenyl		 hypseudone C[c] H. pseudohenryi +25.5 (0.157, m) N.-N. Jiang 2025
4.3 R1 = i-Pr
R2 = (E)-CH2CH=CMeCH(OMe)2
R3 = prenyl		 hypseudone D[c] H. pseudohenryi +31.2 (0.078, m) N.-N. Jiang 2025
4.4 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH2CH=CMeCHO		 hyperkouytone B[c] H. kouytchense +41.2 (0.23, m) H.-Y. Lou 2024
4.5 R1 = s-Bu
R2 = (E)-CH2CH=CMeCHO
R3 = prenyl		 hypseudone B[c][e] H. pseudohenryi +34.9 (0.094, m) N.-N. Jiang 2025
Structure 5: hyperkouytone C — A, bicyclononanes, exo
5
5.1 hyperkouytone C[c] H. kouytchense −96.0 (0.5, m) H.-Y. Lou 2024
Structure 6: dorstenpictanone — A, bicyclononanes, exo
6
6.1 dorstenpictanone Dorstenia picta NR H. Hussain 2011
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 +42 (0.018, mc) V. Vajs 2003
7.2 R1 = i-Pr
R2 = prenyl
X1 = OH/H
X2 = H/OH		 furohyperforin A, mixture of epimers H. perforatum NR S. Trifunović 1998, V. Vajs 2003
7.3 R1 = i-Pr
R2 = prenyl
X1 = OMe
X2 = H		 hyperwilsone B[c] H. wilsonii +114.1 (0.2, acn) Y. Duan 2021c
7.4 R1 = i-Pr
R2 = prenyl
X1 = H
X2 = OMe		 hyperwilsone A[c] H. wilsonii +25.7 (0.2, acn) Y. Duan 2021c
7.5 R1 = (S)-s-Bu
R2 = prenyl
X1 = H
X2 = OMe		 lancasteroid F[c] H. lancasteri +5.8 (0.3, m) J.-Q. You 2025
7.6 R1 = (S)-s-Bu
R2 = prenyl
X1 = OMe
X2 = H		 lancasteroid E[c] H. lancasteri +115.7 (0.3, m) J.-Q. You 2025
7.7 R1 = Ph
R2 = H
X1 = H
X2 = H		 hyperscabrone B[c] H. scabrum −39 (0.1, m) W. Gao 2016a
7.8 R1 = Ph
R2 = H
X1 = H
X2 = OMe		 lancasteroid G[c] H. lancasteri −62.1 (0.3, m) J.-Q. You 2025
7.9 R1 = Ph
R2 = H
X1 = OMe
X2 = H		 lancasteroid H[c] H. lancasteri +1.7 (0.3, m) J.-Q. You 2025
7.10 R1 = Ph
R2 = prenyl
X1 = H
X2 = H		 hyphenrone X[c] H. henryi H. Lév & Vaniot −23 (0.18, m) Y. Liao 2016
7.11 R1 = Ph
R2 = prenyl
X1 = OMe
X2 = H		 hypseudohenrin F[c] H. pseudohenryi +22.2 (0.86, m) H. Sun 2021b
7.12 R1 = Ph
R2 = prenyl
X1 = H
X2 = OMe		 hypseudohenrin G[c] H. pseudohenryi −14.0 (0.57, m) 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 +52 (0.4, m) Y. Guo 2017
8.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 garsubellin A G. subelliptica −21 (e, 1.1) Y. Fukuyama 1997, Y. Fukuyama 1998
8.3 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = H
X = OH		 hyperhimatin G[c] H. himalaicum +48.4 (0.5, m) H. Cheng 2022b
8.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hypercohin G H. cohaerens +42.4 (0.20, m) X. Liu 2013a
8.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 furohyperforin H. perforatum, H. attenuatum +62.4 (0.9), +81.9 (0.9, m), +68 (0.2) 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 +75 (1.2) L. Verotta 2000
8.7 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = acetonyl		 hyperpatuone J[c] H. patulum −15.00 (0.3, m) 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 +38.7 (0.04, m), +7.2 (0.1, m) 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 +62.7 (0.3, m), +8.1 (0.1, m) 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 +33.92 (0.25, m) H.-Y. Lou 2024
8.11 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CHOHCMe=CH2
X = OH		 hyperforatin E[c] H. perforatum +66 (0.3, m) 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 +81 (0.3, m) Y. Guo 2017
8.13 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = CH2C(=O)CHMe2
X = OH		 hyperforatin G[c] H. perforatum +48 (0.6, m) Y. Guo 2017
8.14 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = CH2C(=O)CMe=CH2
X = OH		 hyperioxide D[c] H. perforatum +15.3 (0.1, m) 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 +26.6 (0.25, m) 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 +40.5 (0.19) 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 +117.0 (0.3, m) 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 +78.8 (0.17, m) Z.-B. Zhou 2022b
8.19 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OEt
X = OH		 hyperioxide C[c] H. perforatum +6.6 (0.1, m) X.-G. Pan 2025
8.20 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe=CH2
R4 = prenyl
X = OH		 hyperforatin Q[c] H. perforatum +87.7 (0.6, m) Y. Guo 2019b
8.21 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X = OH		 hyperformitin I[c] H. perforatum +59 (0.2, m) Y. Guo 2021a
8.22 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OOH
R4 = prenyl
X = OH		 hyperkouytone G H. kouytchense +47.38 (0.3, m) H.-Y. Lou 2024
8.23 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = prenyl
X = OH		 hyperioxide B[c] H. perforatum +60.0 (0.02, m) X.-G. Pan 2025
8.24 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl
X = OH		 no common name H. himalaicum +88.4 (0.2, m) 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 +140.2 (0.5, m) Z. Guo 2025
8.26 R1 = i-Pr
R2 = (R)-CH2CHOHCMe=CH2
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatin S[c] H. perforatum +62.2 (0.6, m) Y. Guo 2019b
8.27 R1 = i-Pr
R2 = (S)-CH2CHOHCMe=CH2
R3 = prenyl
R4 = prenyl
X = OH		 hypericumoxide J H. scabrum +3.4 (0.06, m) R. Liu 2017, Y. Guo 2019b
8.28 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
R4 = prenyl
X = OH		 hyperfol F[c] H. perforatum +31.35 (0.17, m) H. Lou 2020b
8.29 R1 = i-Pr
R2 = (E)-CH=CHCMe2OOH
R3 = prenyl
R4 = prenyl
X = OH		 hyperkouytone I H. kouytchense +28.38 (0.17, m) H.-Y. Lou 2024
8.30 R1 = i-Pr
(18R,39R)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatone B[c] H. perforatum +53.0 (0.5, m) Y. Guo 2018
8.31 R1 = i-Pr
(18R,39S)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin D H. cohaerens +81.5 (0.10, m) X. Liu 2013a
8.32 R1 = i-Pr
(18S,39R)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin B[c] H. cohaerens +30.8 (0.15, m) X. Liu 2013a
8.33 R1 = i-Pr
(18S,39S)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatone A[c] (one of two by that name) H. perforatum +31.8 (0.3, m) Y. Guo 2018, W.-Y. Liu 2025a
8.34 R1 = i-Pr
(18S,39R)-R2 =
R3 = prenyl
R4 = prenyl
X = OOH		 hyperforatone D[c] H. perforatum +26.1 (0.4, m) Y. Guo 2018
8.35 R1 = i-Pr
(27R,37R)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hypericumoxide K H. scabrum +65.2 (0.07, m) R. Liu 2017
8.36 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 garsubellin B[d][e] G. subelliptica −36 (0.6, e) Y. Fukuyama 1998, Y. Ma 2022b
8.37 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 hyperacmosin S[c][e] (enantiomer) G. acmosepalum +32.3 (0.52, e); +92.3 (0.05, m) Y. Ma 2022b
8.38 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hyperforcinol J, a.k.a. hyperiforin A[c][e] H. forrestii +70 (0.4, m), +77.3 (0.1, m) W.-J. Lu 2021, J.-F. Zong 2021
8.39 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 furoadhyperforin[e] H. perforatum NR S. Vugdelija 2000
8.40 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OOH		 hyperichoisin A[e] H. choisianum +45.78 (0.075, m) H.-B. Zhang 2021
8.41 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = acetonyl		 hyperpatuone K[c][e] H. patulum −35 (0.3, m) F. Zhang 2026
8.42 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CHOHCMe=CH2
X = OH		 hyperforatin T[c][e] H. perforatum +45.5 (c 0.2, m) Y. Guo 2019b
8.43 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe=CH2
X = OH		 hyperforatin U[c][e] H. perforatum +57.3 (0.3, m) Y. Guo 2019b
8.44 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OH
X = OH		 uralione P[c][e] H. uralum +27.2 (0.1, m) X. Li 2017
8.45 R1 = s-Bu
R2 = prenyl
R3 = (R)-CH2CHOHCMe=CH2
R4 = prenyl
X = OH		 hyperforatin R[c][e] H. perforatum +36.0 (0.3, m) Y. Guo 2019b
8.46 R1 = s-Bu
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = H
X = OH		 hyperhimatin H[c][e] H. himalaicum +44.0 (0.5, m) H. Cheng 2022b
8.47 R1 = s-Bu
R2 = CH(Pr)CH2CO2H
R3 = prenyl
R4 = H
X = OH		 sundaicumone B[e] Calophyllum sundaicum +48 (0.1, e) S. Cao 2006
8.48 R1 = s-Bu
R2 = CH(Pr)CH2CO2H
R3 = CH2CHOHCMe2OH
R4 = H
X = OH		 sundaicumone A[e] Calophyllum sundaicum +52 (0.2, e) S. Cao 2006
8.49 R1 = s-Bu
(18R,39S)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hypericumoxide L[e] H. scabrum +28.6 (0.02, m) R. Liu 2017
8.50 R1 = s-Bu
(18S,39R)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hyperforatone C[c][e] H. perforatum +21.5 (0.5, m) Y. Guo 2018
8.51 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 hyperibone G H. scabrum −29.3 (0.9) M. Matsuhisa 2002
8.52 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 propolone D (enantiomer) Cuban propolis +48.5 (0.7) I. M. Hernandez 2005
8.53 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hypercohin H H. cohaerens −19.0 (0.11, m) X. Liu 2013a
8.54 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 uraloidin A, a.k.a. uralodin A H. henryi subsp. uraloides −55.0 (0.10, m) N. Guo 2008, X.-Q. Chen 2010
8.55 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OOH		 hyperforcinol H, a.k.a. hyperiforin B[c] H. forrestii −20 (0.1, m), −7.3 (0.1, m) W.-J. Lu 2021, J.-F. Zong 2021
8.56 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe=CH2
X = OH		 hyperpatulone B[c] H. patulum +41.7 (1.0, m) Z.-N. Wu 2019
8.57 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe=CH2
X = OH		 hyperpatulone A[c] H. patulum +39.6 (1.0, m) Z.-N. Wu 2019
8.58 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe2OH
X = OH		 hyperpatulone D[c] (one of two by that name) H. patulum +51.8 (1.0, m) Z.-N. Wu 2019
8.59 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OH
X = OH		 hyperpatulone C[c] (one of two by that name) H. patulum +56.6 (1.0) Z.-N. Wu 2019
8.60 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCHO
X = OH		 hyperpatuone L[c] H. patulum +11.67 (0.3, m) F. Zhang 2026
8.61 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = (E)-CH=CHCMe2OH
X = OH		 kiiacylphnol F[c] H. przewalskii Maxim −12 (0.3, m) Y. Duan 2022a
8.62 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = geranyl
X = OH		 kiiacylphnol E[c] H. przewalskii Maxim +2 (0.2, m) Y. Duan 2022a
8.63 R1 = Ph
R2 = prenyl
R3 = geranyl
R4 = H
X = OOH		 trijapin E Triadenum japonicum −150 (0.2, m) A. Oya 2015
8.64 R1 = Ph
R2 = CH2CHOHCMe=CH2
R3 = prenyl
R4 = H
X = OH		 hyperibone D[e] H. scabrum −61.9 (0.7) M. Matsuhisa 2002
8.65 R1 = Ph
(18S,39R)-R2 =
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin C H. cohaerens −43.6 (0.10, m) X. Liu 2013a
8.66 R1 = Ph
R2 = CH2COCHMe2
R3 = prenyl
R4 = prenyl
X = OH		 kiiacylphnol D[c] H. przewalskii Maxim −9 (0.2, m) 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 +17.9 (0.10, m) X. Liu 2013a
9.2 R1 = i-Pr
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = H
X = OH		 garcinielliptone C G. subelliptica −40 (0.2) J.-R. Weng 2003a
9.3 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = H
X = OH		 hyperhimatin F[c] H. himalaicum −14.0 (0.5, m); H. Cheng 2022b
9.4 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 hypercohin F[e] H. cohaerens +18.6 (0.15, m) X. Liu 2013a
9.5 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OH		 hyperscabrone M[c] H. scabrum −29.0 (0.1, m) W. Gao 2016a
9.6 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OOH		 hyperscabrone A[c] H. scabrum −37 (0.1, m) W. Gao 2016a
9.7 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH		 uralione E H. uralum −30 (0.2) Z.-B. Zhou 2016b
9.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CHOHCMe2OH
X = OH		 uralione Q[c] H. uralum −23.4 (0.1, m) X. Li 2017
9.9 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OH
X = OH		 uralione R[c] H. uralum −32.0 (0.1, m) X. Li 2017
Structure 10: hypseudohenrin L — A, bicyclononanes, exo
10
10.1 hypseudohenrin L[c] H. pseudohenryi +22.4 (0.71, m) 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 −122 (0.18, m) X. Wang 2020b
11.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = H		 hyperhimatin J[c] H. himalaicum +116.7 (0.5, m) H. Cheng 2022b
11.3 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = prenyl		 hyperioxide A[c] H. perforatum +70.0 (0.02, m) 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 −128.8 (0.5, m) Z. Guo 2025
11.5 R1 = i-Pr
R2 = prenyl
R3 = (2S)-5-oxo-2-methyltetrahydrofuran-2-yl
R4 = prenyl
R5 = H		 hyperhookerione G[d] H. hookerianum −146.2 (0.5, m) Z. Guo 2025
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 −32.0 (0.1, m) G.-H. Liu 2025
11.7 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 hyperacmosin B[c] H. acmosepalum −53.0 (0.502, m) J. Wang 2019, J. Wang 2022
11.8 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = H		 hyperhimatin L[c] H. himalaicum +71.3 (0.5, m) H. Cheng 2022b
11.9 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 Choisy, H. sampsonii +22.0 (0.3), +43.9 (0.19) W.-J. Tian 2014c, D. Li 2015a
11.10 R1 = Ph
R2 = prenyl
R3 = OH
R4 = prenyl
R5 = H		 hyperattenin A[d] H. attenuatum Choisy +38.3 (0.92) D. Li 2015a
11.11 R1 = Ph
R2 = prenyl
R3 = C(=O)Me
R4 = prenyl
R5 = H		 hypersampsonone I[d] H. sampsonii +17.5 (1.0, m) Y. Li 2023
11.12 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
R5 = H		 sampsonione L H. sampsonii +55 (0.06) L.-H. Hu 2000
11.13 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = (E)-CH=CHCMe2OH
R5 = H		 hyperibone F H. scabrum −31.0 (0.2) M. Matsuhisa 2002, R. Ciochina 2006
11.14 R1 = Ph
R2 = prenyl
R3 = (S)-2-hydroxy-6-methyl-5-hepten-2-yl
R4 = prenyl
R5 = H		 sampsonione K H. sampsonii −5.6 (1.1) L.-H. Hu 2000, Z.-B. Zhou 2014
11.15 R1 = Ph
R2 = prenyl
R3 = (R)-2-hydroxy-6-methyl-5-hepten-2-yl
R4 = prenyl
R5 = H		 attenuatumione C H. attenuatum +20.9 (0.15) Z.-B. Zhou 2014
11.16 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 +37.3 (0.1, m) G.-H. Liu 2025
11.17 R1 = Ph
R2 = prenyl
R3 = (R)-5-oxo-2-methyltetrahydrofuran-2-yl
R4 = prenyl
R5 = H		 hyperisampsin I[d] H. sampsonii +42 (0.2) H. Zhu 2015b
11.18 R1 = Ph
R2 = prenyl
R3 = (S)-5-oxo-2-methyltetrahydrofuran-2-yl
R4 = prenyl
R5 = H		 hyperisampsin H[d] H. sampsonii +4 (0.2) H. Zhu 2015b
11.19 R1 = Ph
R2 = prenyl
(3R,6S)-R3 =
R4 = prenyl
R5 = H
X = OH		 hyperisampsin J[d] H. sampsonii +21 (0.3, m) H. Zhu 2015b
11.20 R1 = Ph
R2 = prenyl
(3R,6S)-R3 =
R4 = prenyl
R5 = H
X = OOH		 hyperisampsin K[d] H. sampsonii +12 (0.4) H. Zhu 2015b
11.21 R1 = Ph
R2 = prenyl
(3S,6R)-R3 =
R4 = prenyl
R5 = H
X = OH		 hyperisampsin M[d] H. sampsonii +47 (0.1) H. Zhu 2015b
11.22 R1 = Ph
R2 = prenyl
(3S,6R)-R3 =
R4 = prenyl
R5 = H
X = OOH		 hyperisampsin L[d] H. sampsonii +9 (0.1, m) H. Zhu 2015b
11.23 R1 = Ph
R2 = CH2CHOHCMe=CH2
R3 = CMe2OH
R4 = (E)-CH=CHCMe2OH
R5 = H		 hyperibone E[e] H. scabrum −56.0 (0.2) 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 +21.5 (0.11, mc) J. Ma 2021b
12.2 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = H		 hyperhimatin I[c] H. himalaicum +40.2 (0.5, m) H. Cheng 2022b
12.3 R1 = i-Pr
R2 = CH2CO2H
R3 = prenyl
R4 = H		 hyperhimatin D[c] H. himalaicum +6.2 (0.5, m) H. Cheng 2022b
12.4 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = H		 hyperacmosin A[c] H. acmosepalum +87.8 (0.337, m) J. Wang 2019, J. Wang 2022
12.5 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyperscabin I[d][e] H. scabrum +23.1 (0.10, mc) J. Ma 2021b
12.6 R1 = s-Bu
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = H		 hyperhimatin K[c][e] H. himalaicum +37.7 (0.5, m) H. Cheng 2022b
12.7 R1 = s-Bu
R2 = CH2CO2H
R3 = prenyl
R4 = H		 hyperhimatin E[c][e] H. himalaicum +20.0 (c 0.5, m) H. Cheng 2022b
Structure 13: otogirinin E — A, bicyclononanes, endo
13
13.1 otogirinin E[e] H. erectum 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 −44.8 (0.4, m) Y. Duan 2021c
14.2 R = s-Bu hyperwilsone K[c][e] H. wilsonii −6.96 (0.4, m) Y. Duan 2021c
Structure 15: kiiacylphnol A, kiiacylphnol B — A, bicyclononanes, exo
15
15.1 R = i-Pr kiiacylphnol A[c] H. przewalskii Maxim +13 (0.1, m) Y. Duan 2022a
15.2 R = s-Bu kiiacylphnol B[c][e] H. przewalskii Maxim +22 (0.6, m) 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 +69 (0.3, m) 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 −41 (0.3) 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 +60 (0.2, m) 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 +39.7 (0.13) 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 +85.7 (0.05, m) 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 +106 (0.3, m) 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 +63 (0.6, m), +61.5 (0.1, m) 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 +54 (0.6, m) 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 +78 (0.6, m) 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 +84 (0.5, m) 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 N. Robson +37.1 (0.1, m), +32.1 (0.5, m) 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 +36.7 (0.1, m) 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 +14.1 (0.10) 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 +20.9 (NR, m) 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 +162 (0.3, m), +147.6 (0.1, m) 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 +57.5 (0.3, m) 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 +14.2 (0.1, m) Y. Guo 2019b
16.18 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (R)-CH2CHOHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 uralione O[c] H. uralum +28.6 (0.1, m) X. Li 2017, Y.-F. Qiu 2023
16.19 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 +94 (0.5, m), +103.0 (0.1, m) Y. Guo 2021a, Z.-B. Zhou 2022a, Y.-F. Qiu 2023
16.20 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 +19.8 (0.10) J. Hu 2025
16.21 R1 = i-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 ascynol L[c] H. ascyron +20 (0.1, m) Y.-L. Hu 2025
16.22 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone B[c] H. ascyron, H. monogynum +80 (0.2, m) W.-J. Xu 2015, L.-M. Kong 2017
16.23 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer 2a[e] H. perforatum +66 (0.08, m) J.-B. Yang 2016
16.24 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperascyrin E[c] H. ascyron +16 (0.1, m) J.-W. Hu 2018
16.25 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = OH
X2 = H		 hyperascyrin H[c] H. ascyron +28 (0.2, m) J.-W. Hu 2018
16.26 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 hyperascyrin G[c] H. ascyron +12 (0.2, m) J.-W. Hu 2018
16.27 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperibrin F[c] H. scabrum −50.8 (0.07, m) J. Hu 2017
16.28 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 +35.7 (0.2), +27 (0.3) J.-R. Weng 2004, I. M. Hernandez 2005, X.-W. Yang 2017a
16.29 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 ascyronine A[c] H. ascyron −15.5 (0.1, m) E.-H. Zhang 2023
16.30 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 +36.5 (0.1, m), +17 (0.1) Z. P. Li 2019, Z.-B. Zhou 2016b, Y.-F. Qiu 2023
Structure 17: hypermongone C, garcinielliptone M, hyperformitin M and others — A, bicyclononanes, exo
17
17.1 R1 = i-Pr
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hypermongone C[c] H. monogynum −8 (0.2, m) W.-J. Xu 2015
17.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 garcinielliptone M[d] G. subelliptica +73 (0.2) J.-R. Weng 2004, X.-W. Yang 2017a, Y. Guo 2021a
17.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 hyperformitin M[c] (enantiomer) H. perforatum −48 (0.1, m) Y. Guo 2021a
17.4 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = H
X1 = H
X2 = H		 hyperhimatin P[c] H. himalaicum −44.7 (0.5, m) H. Cheng 2022b
17.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 attenuatumione F, a.k.a. hyperscabin G[c] H. attenuatum, H. scabrum +19.6 (0.18), +28.4 (0.1, mc) Z.-B. Zhou 2014, J. Ma 2021b, Y.-F. Qiu 2023
17.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = OH
X2 = H		 hyperforatin C[c] H. perforatum +12 (0.5, m) Y. Guo 2017
17.7 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = 2,3-epoxy-3-methylbutyl
X1 = H
X2 = H		 hypericumoxide A[e] H. scabrum +12.5 (0.06, m) R. Liu 2017, Y.-F. Qiu 2023
17.8 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hyperformitin F[c] H. perforatum +10 (0.1, m) Y. Guo 2021a
17.9 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OMe
X1 = H
X2 = H		 hyperforatin D[c] H. perforatum +12 (0.5, m) Y. Guo 2017
17.10 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 hyperforatin L[c] H. perforatum −7.5 (0.6, m) Y. Guo 2019b
17.11 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 hyperforatin M[c] H. perforatum +5.2 (0.3, m) Y. Guo 2019b
17.12 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hypericumoxide B[c] H. scabrum −12.5 (0.08, m) R. Liu 2017, Y.-F. Qiu 2023
17.13 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe=CH2
R4 = prenyl
X1 = H
X2 = H		 hyperforatin N[c] H. perforatum +35.0 (0.2, m) Y. Guo 2019b
17.14 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = H
X1 = H
X2 = H		 hyperhimatin O[c] H. himalaicum −6.2 (0.5, m) H. Cheng 2022b
17.15 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X1 = H
X2 = H		 hyperformitin B[c] H. perforatum +70 (0.3, mc) Y. Guo 2021a
17.16 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hypericumoxide C[c] H. scabrum +14.7 (0.03, m) R. Liu 2017, Y.-F. Qiu 2023
17.17 R1 = i-Pr
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 uralione K[c] H. uralum +6 (0.1) Z.-B. Zhou 2016b, Y.-F. Qiu 2023
17.18 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hyperformitin D, a.k.a. scabrumione B[c] H. perforatum, H. scabrum +31 (0.3, m), +61.5 (0.1, m) Z.-B. Zhou 2016b, Y. Guo 2021a, Y.-F. Qiu 2023
17.19 R1 = i-Bu
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 ascynol M[c] H. ascyron −15 (0.21, m) Y.-L. Hu 2025
17.20 R1 = (S)-s-Bu
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hypermongone A[c] H. monogynum +9 (0.2, m) W.-J. Xu 2015
17.21 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer 2b[c] H. scabrum, H. cohaerens +24 (0.06, m) J.-B. Yang 2016
17.22 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hyperascyrin F[c] H. ascyron −48 (0.4, m) J.-W. Hu 2018
17.23 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = OH		 hyperascyrin I[c] H. ascyron −35 (0.1, m) J.-W. Hu 2018
17.24 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 hyperibrin C[c] H. scabrum +92.5 (0.10, m) W. Gao 2016c
17.25 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 uralione F[c] H. uralum −32 (0.3) Z.-B. Zhou 2016b, Y.-F. Qiu 2023
17.26 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-isolavandulyl[g]
R4 = H
X1 = H
X2 = H		 garcinialiptone C G. subelliptica −94.0 (0.86, m) L.-J. Zhang 2010
Structure 18: sampsonione N, hyperacmosin O — A, bicyclononanes, endo
18
18.1 R = prenyl sampsonione N H. sampsonii +22.0 (0.090) Z. Y. Xiao 2007, Y.-F. Qiu 2023
18.2 R = geranyl hyperacmosin O, a.k.a. hypersampsonone H[d] H. acmosepalum, H. sampsonii −1.5 (0.1, m), + 7.5 (1.0, m) 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 +55 (0.04) L.-H. Hu 2000
19.2 R = (R)-lavandulyl[f]
X = OMe		 garcimultiflorone M[c][t][u][x] G. multiflora −32.8 (0.060, m) 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 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hypermongone H[c] H. monogynum +61 (0.2, m) W.-J. Xu 2015
21.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 garsubellin C[d] G. subelliptica +39 (0.4, e) Y. Fukuyama 1997, Y. Fukuyama 1998, Y. Guo 2021a
21.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 hyperformitin K[c] (enantiomer) H. perforatum −56 (0.4, e) Y. Guo 2021a
21.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 18-epi-furohyperforin isomer 1[r] H. perforatum +15 (0.3, m) C. Hashida 2008, X.-W. Yang 2018
21.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = OH
X2 = H		 hyperforatin K[c] H. perforatum −13 (0.5, m) Y. Guo 2017
21.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = OEt
X2 = H		 hyperacmosin P[c] H. acmosepalum −19.2 (0.1, m) M.-x. Sun 2021b
21.7 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 uralione L[c] H. uralum −29.0 (0.1, m) X. Li 2017
21.8 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (R)-CH2CH(OH)CMe=CH2
X1 = H
X2 = H		 15-epi-hyperforatin I[c] H. perforatum −28 (0.3, m) Y. Guo 2017
21.9 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OH
X1 = H
X2 = H		 hyperidione F[c] H. perforatum −30.0 (0.010, m) X.-G. Pan 2024
21.10 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CH(OH)CMe2OMe
X1 = H
X2 = H		 curvisepalumione D[c] H. curvisepalum N. Robson −23.3 (0.5, m) M.-M. Cao 2025
21.11 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hyperidione E[c] H. perforatum +1.5 (0.033, m) X.-G. Pan 2024
21.12 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CH(OH)CMe2OH
R4 = prenyl
X1 = H
X2 = H		 hyperidione C[c] H. perforatum +20.0 (0.020, m) X.-G. Pan 2024
21.13 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CH(OH)CMe2OH
R4 = prenyl
X1 = H
X2 = H		 no common name H. himalaicum +29.7 (0.1, m) G.-H. Liu 2025
21.14 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X1 = H
X2 = H		 hyperformitin H[c] H. perforatum +88 (0.3, m) Y. Guo 2021a
21.15 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hypericumoxide D H. scabrum +9.8 (0.07, m) R. Liu 2017
21.16 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
R4 = prenyl
X1 = H
X2 = OH		 ascyronine B[c] H. ascyron +13.9 (0.1, m) E.-H. Zhang 2023
21.17 R1 = i-Bu
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 ascynol N[c] H. ascyron +44 (0.2, m) Y.-L. Hu 2025
21.18 R1 = i-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hyperwilsone E[c] H. wilsonii −16.8 (0.6, m) Y. Duan 2021c
21.19 R1 = (S)-s-Bu
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hypermongone F[c] H. monogynum −44 (0.1, m) W.-J. Xu 2015
21.20 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer B[e][s] H. perforatum +14 (1.5) C. Hashida 2008, X.-W. Yang 2018
21.21 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 hyperascyrin A[c] H. ascyron −80 (0.1, m) J.-W. Hu 2018
21.22 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = OH		 hyperascyrin C[c] H. ascyron −67 (0.2, m) J.-W. Hu 2018
21.23 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 hyperibone A H. scabrum +57 (0.2), +63.7 (0.4) M. Matsuhisa 2002, I. M. Hernandez 2005
21.24 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 garcinielliptone I (enantiomer) G. subelliptica −37.7 (1.1) J.-R. Weng 2003b, R. Ciochina 2006
21.25 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 uralodin B H. henryi subsp. uraloides −24.6 (0.075, m) X. Q. Chen 2010
21.26 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = OH
X2 = H		 hypercohin J H. cohaerens −4.8 (0.09, m) X. Liu 2013a, X.-W. Yang 2018
21.27 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = OH		 hyperbeanin D[c] H. beanii +0.9 (0.11, m) Y. Ma 2022a
21.28 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H		 dihroxuralodin H. petiolulatum −27.9 (0.10, m) T. Rui 2017
Structure 22: hyperwilsone C — A, bicyclononanes, exo
22
22.1 hyperwilsone C[c] H. wilsonii −36.3 (0.3, m) 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 +34 (0.3, m) 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 +6 (0.1, m) 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 −12 (0.4, e) 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 +18 (0.4, e) Y. Guo 2021a
23.5 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = OH		 garcinielliptone P G. subelliptica −2 (1.6) 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 +50 (0.7) 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 +60.3 (0.04, m) 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 +44 (0.5, m) 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 +10.7 (0.09, m) R. Liu 2017
23.10 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CHOHCMe2OH
X1 = H
X2 = H		 uralione M[c] H. uralum +28.6 (0.1, m) X. Li 2017
23.11 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CHOHCMe2OH
X1 = H
X2 = H		 uralione N[c] H. uralum +38.8 (0.1, m) X. Li 2017
23.12 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = CH2C(=O)CHMe2
X1 = H
X2 = H		 hyperforatin H[c] H. perforatum +34 (0.5, m) Y. Guo 2017
23.13 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CHOHCMe=CH2
X1 = H
X2 = H		 hyperforatin I[c] H. perforatum +23 (0.4, m) Y. Guo 2017
23.14 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = H
X1 = H
X2 = H		 hyperhimatin M[c] H. himalaicum +37.8 (0.5, m) H. Cheng 2022b
23.15 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 hyperformitin G[c] H. perforatum +17 (0.3, m) Y. Guo 2021a
23.16 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OH
R5 = H
X1 = H
X2 = H		 hyperhimatin N[c] H. himalaicum +27.1 (0.5, m) H. Cheng 2022b
23.17 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (R)-CH2CHOHCMe2OH
R5 = prenyl
X1 = H
X2 = H		 hypericumoxide E[c] H. scabrum +9.8 (0.07, m) R. Liu 2017
23.18 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH
R5 = (S)-CH2CHOHCMe2OH
X1 = H
X2 = H		 hyperidione A[c] H. perforatum +20.0 (0.025, m) X.-G. Pan 2024
23.19 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 +11.9 (0.1, m) E.-H. Zhang 2023
23.20 R1 = i-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 ascynol O[c] H. ascyron −55 (0.1, m) Y.-L. Hu 2025
23.21 R1 = i-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperwilsone D[c] H. wilsonii +37.6 (0.4, m) Y. Duan 2021c
23.22 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hypermongone E[c] H. monogynum +9 (0.2, m) W.-J. Xu 2015
23.23 R1 = (S)-s-Bu
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = (R)-CH2CHOHCMe2OH
X1 = H
X2 = H		 hypermongone J[c] H. monogynum +6 (0.1, m) W.-J. Xu 2015
23.24 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 garsubellin E[e] G. subelliptica −7 (e, 0.4) Y. Fukuyama 1998
23.25 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 furoadhyperforin isomer A[e][s] H. perforatum +34 (0.9) C. Hashida 2008, X.-W. Yang 2018
23.26 R1 = (R)-s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CHOHCMe2OH
X1 = H
X2 = H		 hyperidione B[c] H. perforatum +120.0 (0.010, m) X.-G. Pan 2024
23.27 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 hyperascyrin B[c] H. ascyron −5 (0.2, m) J.-W. Hu 2018
23.28 R1 = Ph
R2 = CMe2OH
R3 = Me
R4 = prenyl
R5 = prenyl
X1 = H
X2 = OH		 hyperascyrin D[c] H. ascyron +3 (0.2, m) J.-W. Hu 2018
23.29 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
X1 = H
X2 = H		 hyperibone B H. scabrum, Cuban propolis −20.8 (0.5), −42.2 (0.1) M. Matsuhisa 2002, I. M. Hernandez 2005
23.30 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) V. S. P. Chaturvedula 2002
23.31 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
X1 = H
X2 = H		 uralodin C H. henryi subsp. uraloides −55.0 (0.010, m) X. Q. Chen 2010
23.32 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OH
X1 = H
X2 = H		 hypersampine B[c] H. sampsonii +13.9 (0.10, m) X.-P. Wang 2024
23.33 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = prenyl
R4 = (R)-lavandulyl[f]
R5 = H
X1 = H
X2 = H		 garcinielliptone FB G. subelliptica −66 (0.2) 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 +26.0 (0.050, m) X.-G. Pan 2024
24.2 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X = H		 scabrumione E H. scabrum +4.5 (0.04, m) Z.-B. Zhou 2022a
24.3 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = prenyl
X = H		 hyperwilone D[d] H. wilsonii +50.0 (0.74) J. Hao 2021
24.4 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = H		 hypersampsone U[d] H. sampsonii +28.2 (0.50) W.-J. Tian 2016
24.5 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OMe		 garcimultinone G[d] G. multiflora +159.26 (0.02, m) H. Teng 2021
24.6 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X = H		 hyperibone C H. scabrum −27.3 (0.3) M. Matsuhisa 2002, R. Ciochina 2006
24.7 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = prenyl
X = H		 hyperattenin C[d] H. attenuatum Choisy −8.4 (0.13, m) D. Li 2015a
24.8 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = prenyl
X = OEt		 hyperattenin D[d] H. attenuatum Choisy +100.4 (0.42, m) D. Li 2015a
24.9 R1 = Ph
R2 = (S)-lavandulyl[f]
R3 = prenyl
R4 = prenyl
X = H		 garcimultinone F[d] G. multiflora +186.27 (0.02, m) H. Teng 2021
24.10 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = prenyl
R4 = prenyl
X = H		 garcinielliptone GC[e] G. multiflora +159.4 (0.27, m) H. Yang 2020
Structure 25: sampsonione O, otogirinin D — A, bicyclononanes, endo
25
25.1 R = prenyl sampsonione O H. sampsonii +87.9 (0.073) Z. Y. Xiao 2007
25.2 R = geranyl otogirinin D H. erectum Thunb., H. attenuatum +160.0 (0.03, m) 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 NR K. Winkelmann 2001a
26.2 R1 = Ph
R2 = prenyl		 scrobiculatone B[c] C. scrobiculata +44.7 (0.2) A. L. M. Porto 2000
26.3 R1 = Ph
R2 = prenyl		 hyperscabrone K[d] (enantiomer) H. scabrum −57.2 (0.1, m) W. Gao 2016b, X.-W. Yang 2018
26.4 R1 = Ph
R2 = lavandulyl		 chamone II[e] C. grandiflora 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 −53.6 (0.03) G. E. Henry 1999
27.2 R1 = prenyl
R2 = prenyl		 hypersampsone F H. sampsonii +30 (0.2) Y.-L. Lin 2003, R. Ciochina 2006
27.3 R1 = lavandulyl
R2 = H		 garcimultine A[e]
(equilibrates rapidly with regioisomer garcimultine B)		 G. multiflora mixture with garcimultine B: +79.4 (0.336, m) H. Liu 2017
27.4 R1 = (S)-CH2CH(CMe2OH)CH2CH=CMe2
R2 = H		 garcimultinone H[d] G. multiflora +35.0 (0.02, m) 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 −1.1 (0.090, m) 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 +6 (0.05, m) 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 +66.4 (0.12, mc), +76.0 (0.10, m) 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 +49 (0.2) 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 −11.8 (0.5, m) 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 +19.8 (0.07, m) 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 +34.6 (0.1) 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 +10 (0.1, m) 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 −4.0 (0.5, m) 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 −6.7 (0.5, m) H. Cheng 2022b
28.10 R1 = Ph
R2 = Me
R3 = prenyl
R4 = CH2–prenyl
X1 = H
X2 = OH		 hyperacmosin I[c][ee] H. acmosepalum −122 (0.25, m) 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 −57.0 (0.38, m), −35.0 (0.10, m) 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 −28 (0.1) Z.-B. Zhou 2016b
28.13 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH2–prenyl
X1 = OH
X2 = H		 uralione C H. uralum −41 (0.1) 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 −58.5 (0.10, m) 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 −16.0 (0.10, m) 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) 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 −58.5 (0.1, m) 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 −49.3 (0.25, m) 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 −28 (0.1, m) 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 N. Robson +25.4 (0.1, acn) 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 N. Robson +18.6 (0.1, acn) 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 −62.8 (1.0) S. Chaturonrutsamee 2018
28.23 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = Me
X1 = H
X2 = H		 hyperscabrone N[c] G. multiflora −62.0 (0.1, m) 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 −5.07 (0.05, m) 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 −40.0 (0.1, m) 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 Roxb. +30.8 (0.10, m) D.-L. Zou 2025
Structure 29: hyperpatin D — A, bicyclononanes, exo
29
29.1 hyperpatin D[c] H. patulum −42.0 (0.10, m) 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 +62.8 (0.50) W.-J. Tian 2016
30.2 R = prenyl
X = OOH		 15,16-dihydro-16-hydroperoxyplukenetione F[e] C. havetiodes var. stenocarpa +24.7 (0.3) O. E. Christian 2001
30.3 R = geranyl
X = H		 hypersampsone H H. sampsonii +44.37 (0.222) 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 +73.90 (0.09, m) 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 +13 (0.1, m) K. Winkelmann 2001a
31.2 R1 = i-Pr
R2 = Me
R3 = prenyl		 papuaforin E H. papuanum +41 (0.1, m) K. Winkelmann 2001a
31.3 R1 = i-Pr
R2 = prenyl
R3 = H		 garcinielliptone F, a.k.a. garsubelone B[d] G. subelliptica −23 (0.09), −90.8 (0.08, m) 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 +83.5 (0.3) M. D. Shan 2001
31.5 R1 = s-Bu
R2 = Me
R3 = H		 papuaforin C[e] H. papuanum +23 (0.1, m) K. Winkelmann 2001a
31.6 R1 = s-Bu
R2 = Me
R3 = prenyl		 papuaforin D[e] H. papuanum +64 (0.1, m) K. Winkelmann 2001a
31.7 R1 = s-Bu
R2 = prenyl
R3 = H		 garsubelone C[d][e] G. subelliptica +6 (0.06, m) Y.-G. Fu 2025
31.8 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hypercohin I[e] H. cohaerens +60.0 (0.22, m) X. Liu 2013a
31.9 R1 = Ph
R2 = prenyl
R3 = H		 scrobiculatone A C. scrobiculata +44.7 (0.2) 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 −112.3 (0.33) 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 −9 (0.2) S. A. T. Fobofou 2016, Y.-G. Fu 2025
32.2 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hyperselancin A[c][e] H. lanceolatum −1 (0.3) S. A. T. Fobofou 2016, Y.-G. Fu 2025
32.3 R1 = s-Bu
R2 = prenyl
R3 = geranyl		 androforin A[e] H. androsaemum −59.3 (0.23, MeOH) K. Wang 2012
32.4 R1 = Ph
R2 = prenyl
R3 = prenyl		 plukenetione G C. plukenetii NR G. E. Henry 1999
32.5 R1 = Ph
R2 = lavandulyl
R3 = prenyl		 garcimultine B[e]
(equilibrates rapidly with regioisomer garcimultine A)		 G. multiflora mixture with garcimultine A: +79.4 (0.336, m) 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 +13 (0.1, m) X. Zhou 2021
33.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 garcinielliptone B G. subelliptica −23 (0.1) 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 +13.0 (0.10, m), +7.8 (0.1, m) 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 +13.6 (0.4, m) Y. Duan 2021c
33.5 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = OH
X2 = H		 hyperascyrin J[c] H. ascyron −68 (0.2, m) J.-W. Hu 2018
33.6 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
X1 = H
X2 = OH		 hyperacmosin H[c] H. acmosepalum −478 (0.25, m) X. Wang 2020b
33.7 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X1 = H
X2 = H		 propolone A Cuban propolis, H. attenuatum +40 (0.1) 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 −37 (0.1, m), −48.0 (0.10, m) 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 −30.0 (0.10, m) 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 −96.3 (0.30) 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 Roxb. +40.9 (0.10, m) D.-L. Zou 2025
Structure 34: ochrocarpinone A — A, bicyclononanes, exo
34
34.1 ochrocarpinone A[e][o] Ochrocarpos punctatus +8.7 (0.15) 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 +31.7 (0.376) Y. H. Zeng 2012, D. Li 2015a
35.2 R = (R)-lavandulyl[f] garcimultiflorone L[c] G. multiflora +65.4 (0.040, m) Z.-Q. Wang 2018
Structure 36: hyperpatin H — A, bicyclononanes, exo
36
36.1 hyperpatin H[c] H. patulum −105.0 (0.10, m) J.-C. Huang 2025
Structure 37: garcimultinone D, garcimultinone E — A, bicyclononanes, exo
37
37.1 R = Ph garcimultinone D[d] G. multiflora +186.27 (0.02, m) H. Teng 2021
37.2 R = 3,4-dihydroxyphenyl garcimultinone E[d] G. multiflora +11.22 (0.15, m) H. Teng 2021
Structure 38: garcimultiflorone A — A, bicyclononanes, endo
38
38.1 garcimultiflorone A G. multiflora −173 (0.12) J.-J. Chen 2009
Structure 39: no name — A, bicyclononanes, endo
39
39.1 no common name C. obdeltifolia +30.9 (0.3) J. S. A. R. Teixeira 2005
Structure 40: hypersampsonone A — A, bicyclononanes, endo
40
40.1 hypersampsonone A[d] H. sampsonii +46.1 (0.59) 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 +62.0 (0.50) 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 −97.0 (0.07, m) J.-J. Zhang 2014a
42.2 R1 = i-Bu
R2 = Me		 ascynol P[c] H. ascyron −130 (c 0.1, m) 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 −73.7 (0.8) L. Verotta 2000
43.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-CH2CHOHCMe2OH		 uralione J[c] H. uralum −48 (0.1, m) Z.-B. Zhou 2016b
43.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 hyperforatone F H. perforatum −70.0 (0.3, m) Y. Guo 2018
43.4 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH
R4 = prenyl		 hypericumoxide I[c] H. scabrum −67.3 (0.06, m) R. Liu 2017
43.5 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl		 hyperforatone G[c] H. perforatum −77.5 (0.3, m) Y. Guo 2018
43.6 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
R4 = prenyl		 hypericumoxide G[c] H. scabrum −60.3 (0.07, m) R. Liu 2017
43.7 R1 = i-Pr
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl
R4 = prenyl		 hypericumoxide H[c] H. scabrum −43.5 (0.06, m) R. Liu 2017
43.8 R1 = i-Pr
(18S,39R)-R2 =
R3 = prenyl
R4 = prenyl		 hyperforatone E H. perforatum −93.6 (0.9, m) Y. Guo 2018
43.9 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyphenrone E[c] H. henryi −117.6 (0.20, m) 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 −90.3 (0.9, m) Y. Guo 2018
43.11 R1 = s-Bu
R2 = (E)-CH=CHCH2OOH
R3 = prenyl
R4 = prenyl		 uralin C[c][e] H. uralum −82 (0.2, m) Q.-Q. Fang 2021
43.12 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl		 hyperascyrin K[c] H. ascyron −201 (0.2, m) 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 −240.8 (0.17, m), −210 (0.2) J.-J. Zhang 2014a, Z.-B. Zhou 2016b
43.14 R1 = Ph
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH
R4 = prenyl		 uralione I[c] H. uralum −139 (0.1, m) Z.-B. Zhou 2016b
43.15 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCH2OH
R4 = prenyl		 kiiacylphnol H[c] H. przewalskii Maxim −115 (0.4, m) 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 −124 (0.1, m) W. Gao 2016a
44.2 R1 = i-Pr
R2 = prenyl		 hypercohone E H. cohaerens −42.8 (0.12, m) J.-J. Zhang 2014a
44.3 R1 = i-Bu
R2 = Me		 ascynol Q[c] H. ascyron −112 (0.1, m) Y.-L. Hu 2025
44.4 R1 = (R)-s-Bu
R2 = Me		 hyperscabrone D[c] H. scabrum −75 (0.1, m) W. Gao 2016a
44.5 R1 = s-Bu
R2 = prenyl		 hyperibrin H[c][e] H. scabrum NR W. Xu 2021
44.6 R1 = Ph
R2 = prenyl		 kiiacylphnol G[c] H. przewalskii Maxim −125 (0.4, m) Y. Duan 2022a
Structure 45: hyperkouytone A — A, bicyclononanes, caged
45
45.1 hyperkouytone A[d] H. kouytchense −24.8 (0.21, m) H.-Y. Lou 2024
Structure 46: hyperhookerione A — A, bicyclononanes, exo
46
46.1 hyperhookerione A[c] H. hookerianum +127.8 (0.5, m) Z. Guo 2025
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 −11 (0.1, m) 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 L. +16.9 (0.3), +17 (1, m) 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 −2.8 (1.0, e); +1 (0.3) 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 +34 (1.0) L. Verotta 2000
47.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CHOHCMe2OH		 hyperfol C[c] H. perforatum −9.18 (0.05, m) H. Lou 2020b
47.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CHOHCMe2OH		 hyperfol D[c] H. perforatum −43.12 (0.12, m) H. Lou 2020b
47.7 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = (S)-CH2CHOHCMe2OMe		 hyperfol E[c] H. perforatum −27.09 (0.09, m) H. Lou 2020b
47.8 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl		 hyphenrone W H. henryi H. Lév & Vaniot +6 (0.08, m) Y. Liao 2016
47.9 R1 = i-Pr
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H		 garcinielliptone E G. subelliptica −51 (0.2) 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 −9 (0.1, m) X. Zhou 2021
47.11 R1 = i-Bu
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 ascyronone D H. ascyron −3 (0.18, m) 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) 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 +7 (0.1, m) 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 +32 (0.09, m) R. B. Grossman 2020
47.15 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyphenrone G[c] H. henryi +26 (0.4, m) 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 +54 (0.3, m) W.-J. Lu 2021
Structure 48: hyperhookerione B, hyperhookerione C — A, bicyclononanes, exo
48
48.1 R = i-Pr hyperhookerione B[c] H. hookerianum +221.6 (0.5, m) Z. Guo 2025
48.2 R = s-Bu hyperhookerione C[c][e] H. hookerianum +33.3 (0.5, m) Z. Guo 2025
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 Maxim +61 (0.5, m) Y. Duan 2022a
49.2 R = i-Pr
X = OMe		 hyperhookerione D[c] H. hookerianum +77.8 (0.5, m) Z. Guo 2025
49.3 R = i-Pr
X = OEt		 hypseudohenrin I[c] H. pseudohenryi +21.5 (20.6, m) H.-R. Sun 2021a
49.4 R = s-Bu
X = OH		 hyperforcinol F[c][e] H. forrestii +113 (0.2, m) W.-J. Lu 2021
49.5 R = s-Bu
X = OEt		 hypseudohenrin J[c][e] H. pseudohenryi +40.6 (0.71, m) 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 −88.18 (0.44, m) Y. Duan 2019
50.2 R1 = i-Pr
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 przewalcyrone F[c] H. przewalskii −47.25 (0.13, m) Y. Duan 2019
50.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = H
X2 = OH		 hyphenrone T[c] H. henryi H. Lév & Vaniot −118 (0.09, m) Y. Liao 2016
50.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyphenrone U H. henryi H. Lév & Vaniot −46 (0.16, m) Y. Liao 2016
50.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = O
X2 = O		 hypseudohenrin K[c] H. pseudohenryi −18.6 (1.13, m) H.-R. Sun 2021a
50.6 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe=CH2
X1 = H
X2 = OH		 hyperforatone J[c] H. perforatum −59.5 (0.2, m) Y. Guo 2018
50.7 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe=CH2
X1 = H
X2 = OH		 hyperforatone I[c] H. perforatum −40.0 (0.4, m) Y. Guo 2018
50.8 R1 = i-Pr
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OMe
X1 = H
X2 = OH		 hyperforatone O[c] H. perforatum −22.0 (0.3, m) Y. Guo 2018
50.9 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OMe
X1 = H
X2 = OH		 hyperforatone N[c] H. perforatum −52.7 (0.4, m) Y. Guo 2018
50.10 R1 = i-Pr
R2 = (R)-CH2CHOHCMe=CH2
R3 = prenyl
X1 = H
X2 = OH		 hyperforatone K[c] H. perforatum −35.4 (0.5, m) Y. Guo 2018
50.11 R1 = i-Pr
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl
X1 = H
X2 = OH		 hyperforatone L[c] H. perforatum −66.3 (0.3, m) Y. Guo 2018
50.12 R1 = i-Pr
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl
X1 = H
X2 = OH		 hyperforatone M[c] H. perforatum −10.4 (0.3, m) Y. Guo 2018
50.13 R1 = i-Bu
R2 = prenyl
R3 = H
X1 = H
X2 = OH		 przewalcyrone C[c] H. przewalskii −80.33 (0.3, m) Y. Duan 2019
50.14 R1 = i-Bu
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 przewalcyrone D[c] H. przewalskii −67.70 (0.18, m) Y. Duan 2019
50.15 R1 = (S)-s-Bu
R2 = prenyl
R3 = H
X1 = H
X2 = OH		 przewalcyrone A[c] H. przewalskii −109.29 (0.43, m) Y. Duan 2019
50.16 R1 = (S)-s-Bu
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 przewalcyrone B[c] H. przewalskii −132.38 (0.3, m) Y. Duan 2019
50.17 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperwilsone F[c] H. wilsonii −36.8 (0.4, m) Y. Duan 2021c
50.18 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X1 = H
X2 = OH		 hyphenrone V H. henryi H. Lév & Vaniot −38 (0.16, m) Y. Liao 2016
50.19 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperwilsone G[c] H. wilsonii −44.0 (0.3, m) Y. Duan 2021c
50.20 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = H
X2 = OH		 hyperwilsone H[c] H. wilsonii −60.6 (0.5, m) Y. Duan 2021c
Structure 51: hyperhookerione H — A, bicyclononanes, exo
51
51.1 hyperhookerione H[c] H. hookerianum −110 (0.5, m) Z. Guo 2025
Structure 52: hyperhookerione I — A, bicyclononanes, exo
52
52.1 hyperhookerione I[c] H. hookerianum −163 (0.5, m) Z. Guo 2025
Structure 53: garcinielliptone H — A, bicyclononanes, exo
53
53.1 garcinielliptone H G. subelliptica −14.3 (0.1) J.-R. Weng 2003b
Structure 54: ascynol G — A, bicyclononanes, exo
54
54.1 ascynol G[c] H. ascyron +78 (0.1, m) Y.-L. Hu 2025
Structure 55: garcinielliptone G — A, bicyclononanes, exo
55
55.1 garcinielliptone G G. subelliptica −53 (0.1) J.-R. Weng 2003b, Y.-G. Fu 2025
Structure 56: hyperscabin D — A, bicyclononanes, exo
56
56.1 hyperscabin D[c] H. scabrum +71.4 (0.08, mc) J. Ma 2021b
Structure 57: hyperforone A — A, bicyclononanes, caged
57
57.1 hyperforone A[c] (one of two by that name) H. perforatum −10.1 (0.1, m) Y. Guo 2021b
Structure 58: hyperforone B — A, bicyclononanes, exo
58
58.1 hyperforone B[c] (one of two by that name) H. perforatum −144.4 (0.5, m) Y. Guo 2021b
Structure 59: hyperforone C — A, bicyclononanes, exo
59
59.1 hyperforone C[c] (one of two by that name) H. perforatum −29.2 (0.3, m) Y. Guo 2021b
Structure 60: hyperforone D — A, bicyclononanes, exo
60
60.1 hyperforone D[c] H. perforatum +68.9 (0.9, m) Y. Guo 2021b
Structure 61: hyperforone E — A, bicyclononanes, exo
61
61.1 hyperforone E[c] H. perforatum −66.4 (0.3, m) Y. Guo 2021b
Structure 62: hyperforone F — A, bicyclononanes, exo
62
62.1 hyperforone F[c] H. perforatum −30.0 (0.8, m) Y. Guo 2021b
Structure 63: hyperforone G — A, bicyclononanes, exo
63
63.1 hyperforone G[c] H. perforatum −15.2 (0.4, m) Y. Guo 2021b
Structure 64: hyperforone H — A, bicyclononanes, exo
64
64.1 hyperforone H[c] H. perforatum −22.3 (0.9, m) Y. Guo 2021b
Structure 65: hyperatin A — A, bicyclononanes, exo
65
65.1 hyperatin A[c] H. perforatum +64.3 (0.1, m) 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 −24.5 (0.1, m) Y. Guo 2024
66.2 R = i-PrO
X = OH		 hyperatin C[c] H. perforatum −1.8 (0.2, m) Y. Guo 2024
66.3 R = i-PrO
X = OMe		 hyperatin B[c] H. perforatum −5.3 (0.2, m) Y. Guo 2024
Structure 67: hyperacmose A, hyperacmose B — A, bicyclononanes, exo
67
67.1 R = i-Pr hyperacmose A[c] H. acmosepalum +11.11 (2.8, m) Z. Hu 2026
67.2 R = s-Bu hyperacmose B[c][e] H. acmosepalum +8.63 (1.9, m) Z. Hu 2026
Structure 68: hyperacmose C — A, bicyclononanes, exo
68
68.1 hyperacmose C[c] H. acmosepalum +21.43 (0.56, m) Z. Hu 2026
Structure 69: hypericumoxide N — A, bicyclononanes, exo
69
69.1 hypericumoxide N[d] H. scabrum −24.2 (0.09, m) R. Liu 2017
Structure 70: hyperpatone A — A, bicyclononanes, exo
70
70.1 hyperpatone A[c] H. patulum −54.18 (0.3, m) 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 −166 (0.2) J.-R. Weng 2003b
71.2 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH		 norhyperpalum G[c] H. patulum +107.6 (c 0.5, m) Y. Duan 2021b
71.3 R1 = (S)-s-Bu
R2 = H		 soulattrone A Calophyllum soulattri +157.3 (c 0.19, e) S. K. Nigam 1988
71.4 R1 = s-Bu
R2 = (E)-CH=CHCMe2OH		 norhyperpalum F[c][e] H. patulum +92.0 (c 0.6, m) 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 −23.8 (0.25, m) X.-W. Yang 2014
72.2 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl		 perforatumone[d] (prob. enantiomer) H. perforatum +153 (2.9, a) J. Wu 2004, X.-W. Yang 2015
72.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 hyperuralone C H. uralum +3 (0.25, m) J.-J. Zhang 2015
72.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH		 hyperuralone E H. uralum +2 (0.11, m) J.-J. Zhang 2015
72.5 R1 = i-Pr
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl		 attenuatumione B H. attenuatum +4.8 (0.19) 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 +10 (0.2, m) F. Hu 2023
72.7 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyphenrone H[c] H. henryi −4 (0.1, m) X.-W. Yang 2015
72.8 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 hyperuralone D[e] H. uralum +4 (0.09, m) J.-J. Zhang 2015
72.9 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH		 hyperuralone F[e] H. uralum +2 (0.11, m) J.-J. Zhang 2015
72.10 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl		 hyphenrone B[c] H. henryi −39.8 (0.09, m) X.-W. Yang 2014
Structure 73: hyperfol H — A, bicyclononanes, exo
73
73.1 hyperfol H[c][dd] H. perforatum −203 (0.3, m) H. Lou 2020b
Structure 74: hyperfol B — A, bicyclononanes, exo
74
74.1 hyperfol B[c] H. perforatum −33.24 (0.09, m) H.-Y. Lou 2020a
Structure 75: hyperkouytone N — A, bicyclononanes, exo
75
75.1 hyperkouytone N[c] H. kouytchense −14.2 (0.24, m) H.-Y. Lou 2024
Structure 76: hyperuralone G, hyperuralone H — A, bicyclononanes, endo
76
76.1 R = i-Pr hyperuralone G H. uralum −37 (0.11, m) J.-J. Zhang 2015
76.2 R = s-Bu hyperuralone H[e] H. uralum −38 (0.3, m) J.-J. Zhang 2015
Structure 77: hyphenrone C, hyphenrone I — A, bicyclononanes, exo
77
77.1 R = i-Pr hyphenrone C[c] H. henryi −32.9 (0.10, m) X.-W. Yang 2014, X.-W. Yang 2015
77.2 R = (S)-s-Bu hyphenrone I[c] H. henryi +22 (c 0.1, m) X.-W. Yang 2015
Structure 78: ascynol H — A, bicyclononanes, exo
78
78.1 ascynol H[c] H. ascyron −22 (c 0.3, m) Y.-L. Hu 2025
Structure 79: hyphenrone D — A, bicyclononanes, exo
79
79.1 hyphenrone D[c] H. henryi −62.5 (0.10, m) 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 −18.0 (0.3, m) J.-Q. You 2024, W.-Y. Liu 2025a
Structure 81: hyperfol A — A, bicyclononanes, exo
81
81.1 hyperfol A[c] H. perforatum −202.49 (0.3, m) 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 −30 (0.1, m) Y.-L. Hu 2025
82.2 R1 = i-Pr
R2 = H
R3 = prenyl
R4 = prenyl		 hyphenrone F[c] H. henryi −140 (0.10, m) X.-W. Yang 2014
82.3 R1 = i-Pr
R2 = CO2Me
R3 = prenyl
R4 = prenyl		 hyperpatuone M[c] H. patulum −52 (0.3, m) F. Zhang 2026
82.4 R1 = s-Bu
R2 = H
R3 = Me
R4 = (E)-CH=CHCMe2OH		 ascynol K[c][e] H. ascyron −24 (0.1, m) Y.-L. Hu 2025
82.5 R1 = Ph
R2 = H
R3 = Me
R4 = prenyl		 ascyronone C H. ascyron −151 (0.30, m) L.-M. Kong 2017
82.6 R1 = Ph
R2 = H
R3 = Me
R4 = (E)-CH=CHCMe2OH		 ascynol I[c] H. ascyron −149 (0.1, m) Y.-L. Hu 2025
Structure 83: hyperforen A — A, bicyclononanes, exo
83
83.1 hyperforen A[c] H. perforatum +9.53 (0.05, m) 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 +87 (0.04, m) L.-M. Kong 2017
84.2 R1 = i-Pr
R2 = prenyl		 hyperforcinol K[c] H. forrestii +57 (0.9, m) W.-J. Lu 2021
84.3 R1 = s-Bu
R2 = Me		 ascyronone B[e] H. ascyron +108 (0.11, m) L.-M. Kong 2017
84.4 R1 = s-Bu
R2 = prenyl		 hyperforcinol E[c][e] H. forrestii +70 (0.3, m) W.-J. Lu 2021
Structure 85: uralin B — A, bicyclononanes, exo
85
85.1 uralin B[c] H. uralum +63 (0.3, m) Q.-Q. Fang 2021
Structure 86: hypsampsone A — B, bicyclononanes, endo
86
86.1 hypsampsone A[d] H. sampsonii +71.49 (0.7, m) Z.-Z. Zhang 2021
Structure 87: hypersampone A — A, bicyclononanes, exo
87
87.1 hypersampone A[d] H. sampsonii −70.01 (1.7, m) L. Huang 2022
Structure 88: hypersampone B, hypersampone C — A, bicyclononanes, exo
88
88.1 R = OBz hypersampone B[d] H. sampsonii −67.93 (1.8, m) L. Huang 2022
88.2 R = Bz hypersampone C[d] H. sampsonii −21.54 (1.9, m) L. Huang 2022
Structure 89: hyperscabin A, norhyperpalum E — A, bicyclononanes, exo
89
89.1 R = i-Pr hyperscabin A[c] H. scabrum +37.9 (0.05, mc) J. Ma 2021a
89.2 R = s-Bu norhyperpalum E[c][e] H. patulum +55.1 (0.3, m) Y. Duan 2021b
Structure 90: hyperscabin B, hyperscabin C, norhyperpalum D — A, bicyclononanes, exo
90
90.1 R = i-Pr hyperscabin B[c] H. scabrum +75.6 (0.18, mc) J. Ma 2021a
90.2 R = s-Bu hyperscabin C[c][e] H. scabrum +66.2 (0.08, mc) J. Ma 2021a
90.3 R = Ph norhyperpalum D[c] H. patulum −47.1 (0.2, m) Y. Duan 2021b
Structure 91: hyperacmosin K, norhyperpalum B — A, bicyclononanes, exo
91
91.1 R = i-Pr hyperacmosin K[c] H. acmosepalum +109.4 (0.1115, m) M. Sun 2021a
91.2 R = Ph norhyperpalum B[c] H. patulum −14.7 (0.6, m) Y. Duan 2021b
Structure 92: hyperacmosin L, norhyperpalum C — A, bicyclononanes, exo
92
92.1 R = i-Pr hyperacmosin L[c] H. acmosepalum +133.8 (0.068, m) M. Sun 2021a
92.2 R = Ph norhyperpalum C[c] H. patulum +3.3 (0.3, m) Y. Duan 2021b
Structure 93: norhyperpalum A — A, bicyclononanes, endo
93
93.1 norhyperpalum A[d] H. patulum −53.7 (c 0.3, m) Y. Duan 2021b
Structure 94: hyperscabin E — A, bicyclononanes, endo
94
94.1 hyperscabin E[c] H. scabrum +103.2 (0.14, mc) J. Ma 2021b
Structure 95: hypertum A — A, bicyclononanes, exo
95
95.1 hypertum A[c] H. perforatum −8.5 (0.05, m) W.-Y. Liu 2025b
Structure 96: hyperhexanone F, hyperhexanone A, hyperacmosin M — A, bicyclononanes, endo
96
96.1 R1 = prenyl
R2 = Me		 hyperhexanone F[c] H. sampsonii −40 (0.3, m) Z.-Z. Zhang 2021
96.2 R1 = geranyl
R2 = Me		 hyperhexanone A[c] H. sampsonii −13.3 (0.30) H. Zhu 2016
96.3 R1 = geranyl
R2 = Et		 hyperacmosin M[c] H. acmosepalum −54.5 (0.044, m) M. Sun 2021a
Structure 97: hyperforcinol D — A, bicyclononanes, endo
97
97.1 hyperforcinol D[c] H. forrestii +4 (0.7, m) W.-J. Lu 2021
Structure 98: hyperacmosin D, hyperacmosin C — A, bicyclononanes, endo
98
98.1 R = i-Pr hyperacmosin D[c] H. acmosepalum −25.45 (0.22, m) X.-y. Suo 2021a
98.2 R = (S)-s-Bu hyperacmosin C[c] H. acmosepalum −12.30 (0.26, m) X.-y. Suo 2021a
Structure 99: hyperbenzone A — A, bicyclononanes, endo
99
99.1 hyperbenzone A[c] H. beanii −4 (0.2, m) W. Lu 2021
Structure 100: hyperbenzone B — A, bicyclononanes, endo
100
100.1 hyperbenzone B[c] H. beanii +12 (0.1, m) W. Lu 2021
Structure 101: spirohypolactone A — A, bicyclononanes, exo
101
101.1 spirohypolactone A[c] H. perforatum +65.6 (0.6, m) Y. Guo 2019a
Structure 102: spirohypolactone B, norhyperpalum H, hyperisenin B — A, bicyclononanes, exo
102
102.1 R1 = i-Pr
R2 = CH2CH2CH=CMe2		 spirohypolactone B[c] H. perforatum +43.5 (0.6, m) Y. Guo 2019a
102.2 R1 = s-Bu
R2 = CH2CH2CH=CMe2		 norhyperpalum H[c][e] H. patulum +44.3 (0.5, m) Y. Duan 2021b
102.3 R1 = Ph
R2 = (E)-CH=CHCH=CMe2		 hyperisenin B[c] H. seniawinii +48.8 (0.3, m) Y. Duan 2025
Structure 103: norhyperpalum I, hyperhexanone C, hyperhexanone D — A, bicyclononanes, exo
103
103.1 R = i-Pr
X = H		 norhyperpalum I[c] H. patulum −9.6 (0.6, m) Y. Duan 2021b
103.2 R = i-Pr
X = OH		 hyperhexanone C[c] H. perforatum −17.8 (0.6, m) Y. Guo 2019a
103.3 R = s-Bu
X = OH		 hyperhexanone D[c][e] H. perforatum −30.3 (0.4, m) Y. Guo 2019a
Structure 104: hyperhexanone E — A, bicyclononanes, endo
104
104.1 hyperhexanone E[c] H. perforatum −139.0 (0.3, m) Y. Guo 2019a
Structure 105: norsampsone A, norsampsone C, norgarmultinone A — A, bicyclononanes, endo
105
105.1 R = prenyl norsampsone A[c] H. sampsonii +23.4 (0.50) W.-J. Tian 2014a
105.2 R = geranyl norsampsone C[c] H. sampsonii +26.0 (0.50) W.-J. Tian 2014a
105.3 R = lavandulyl norgarmultinone A[c][e] G. multiflora +77.78 (0.02, m) H. Teng 2020
Structure 106: norsampsone B, norsampsone D — A, bicyclononanes, endo
106
106.1 R = prenyl norsampsone B[c] H. sampsonii −28.6 (0.50) W.-J. Tian 2014a
106.2 R = geranyl norsampsone D[c] H. sampsonii −28.2 (0.50) W.-J. Tian 2014a
Structure 107: norwilsonnol B — A, bicyclononanes, exo
107
107.1 norwilsonnol B[d] H. wilsonii +111.0 (0.5, m) S. Xie 2021
Structure 108: hyperisenin A — A, bicyclononanes, exo
108
108.1 hyperisenin A[d] H. seniawinii +42.0 (0.1, m) Y. Duan 2025
Structure 109: hypertum B — A, bicyclononanes, exo
109
109.1 hypertum B[c] H. perforatum −9.5 (0.15, m) W.-Y. Liu 2025b
Structure 110: norwilsonnol A — A, bicyclononanes, exo
110
110.1 norwilsonnol A[c] H. wilsonii −174.0 (0.7, m) S. Xie 2021
Structure 111: hyperwilsol A — A, bicyclononanes, exo
111
111.1 hyperwilsol A[c] H. wilsonii −5.55 (0.08, m) Z.-X. Wang 2025
Structure 112: hypseudohenrin H — A, bicyclononanes, exo
112
112.1 hypseudohenrin H[c] H. wilsonii −8.56 (1.29, m) M.-X. Sun 2024
Structure 113: hypertum C — A, bicyclononanes, exo
113
113.1 hypertum C[c] H. perforatum −26.8 (0.05, m) W.-Y. Liu 2025b
Structure 114: hypertum D, hypertum E — A, bicyclononanes, exo
114
114.1 X1 = OMe
X2 = H		 hypertum D[c] H. perforatum mixture with hypertum E: −40.1 (0.1, m) W.-Y. Liu 2025b
114.2 X1 = H
X2 = OMe		 hypertum E[c] H. perforatum mixture with hypertum D: −40.1 (0.1, m) W.-Y. Liu 2025b
Structure 115: norgarmultinone B — A, bicyclononanes, exo
115
115.1 norgarmultinone B[c] G. multiflora +43.37 (0.07, m) H. Teng 2020
Structure 116: hypseudohenrin C — A, bicyclononanes, endo
116
116.1 hypseudohenrin C[c] H. pseudohenryi +10.5 (1.14, m) H. Sun 2021b
Structure 117: hyperwilsol D — A, bicyclononanes, exo
117
117.1 hyperwilsol D[c] H. wilsonii −81.55 (0.04, m) Z.-X. Wang 2025
Structure 118: hypseudohenrin D — A, bicyclononanes, endo
118
118.1 hypseudohenrin D[c] H. pseudohenryi +10.9 (1.29, m) H. Sun 2021b
Structure 119: garcinielliptone O, no name, hyperwilsol C and others — A, bicyclononanes, exo
119
119.1 R1 = i-Pr
R2 = H		 garcinielliptone O G. subelliptica −277 (0.16) J.-R. Weng 2004
119.2 R1 = i-Pr
R2 = prenyl		 no common name H. perforatum +95.5 (1.1) M. D. Shan 2001
119.3 R1 = (R)-s-Bu
R2 = prenyl		 hyperwilsol C[c] H. wilsonii +93.99 (0.05, m) Z.-X. Wang 2025
119.4 R1 = Ph
R2 = H		 hyperibrin G[d] H. scabrum +80.2 (0.06, m) J. Hu 2017
Structure 120: hypertum F, hypertum G — A, bicyclononanes, exo
120
120.1 R = i-Pr hypertum F[c] H. perforatum +40.2 (0.02, m) W.-Y. Liu 2025b
120.2 R = (S)-s-Bu hypertum G[c] H. perforatum +49.5 (0.02, m) W.-Y. Liu 2025b
Structure 121: spirohypertone B — A, bicyclononanes, exo
121
121.1 spirohypertone B[c] H. patulum −15.2 (0.1, m) Y. Duan 2024b
Structure 122: hypseudohenrin A, hypseudohenrin B — A, bicyclononanes, exo
122
122.1 R = CO2Me hypseudohenrin A[c] H. pseudohenryi +9.8 (1.43, m) H. Sun 2021b
122.2 R = H hypseudohenrin B[c] H. pseudohenryi +12.9 (1.86, m) H. Sun 2021b
Structure 123: hyperibrin A, hyperibrin B, hyperscabrone H and others — A, bicyclononanes, seco
123
123.1 R1 = i-Pr
R2 = Me
R3 = prenyl
X = H		 hyperibrin A[c] H. scabrum +37.0 (0.05, m) W. Gao 2016c
123.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = OH		 hyperibrin B, a.k.a. hypermonone I[c] H. monogynum, H. scabrum +53.2 (0.08, m), +46.03 (0.08, m) W. Gao 2016c, X. Wang 2021b, Y.-R. Zeng 2021c
123.3 R1 = i-Pr
R2 = Me
R3 = prenyl
X = OOH		 hyperscabrone H[c] H. scabrum +8.3 (0.1, m) W. Gao 2016a, X. Wang 2021b
123.4 R1 = i-Pr
R2 = prenyl
R3 = H
X = H		 garcinielliptone N G. subelliptica −42 (0.38) J.-R. Weng 2004
123.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X = H		 no common name H. perforatum +18.3 (1.8) M. D. Shan 2001
123.6 R1 = i-Bu
R2 = Me
R3 = (E)-CH=CHCMe2OH
X = H		 ascynol F[c] H. ascyron +22 (0.1, m) Y.-L. Hu 2025
123.7 R1 = s-Bu
R2 = Me
R3 = prenyl
X = H		 hypermonone H[c] H. monogynum +7.88 0.24, m) Y.-R. Zeng 2021c
123.8 R1 = s-Bu
R2 = Me
R3 = prenyl
X = OOH		 hyperscabrone I[c][e] H. scabrum +24 (0.1, m) W. Gao 2016a, X. Wang 2021b
123.9 R1 = Ph
R2 = Me
R3 = prenyl
X = H		 norascyronone C H. ascyron +15 (0.1, m) Y.-L. Hu 2019
123.10 R1 = Ph
R2 = prenyl
R3 = prenyl
X = H		 hypseudohenrin E[c] H. pseudohenryi +4.96 (3.43, m) H. Sun 2021b
123.11 R1 = Ph
R2 = geranyl
R3 = H
X = H		 hyperhexanone B[c] H. sampsonii −14.6 (0.15) H. Zhu 2016
Structure 124: hyperscabrin A, hyperscabin K, hyperscabin L — A, bicyclononanes, seco
124
124.1 R1 = i-Pr
R2 = H		 hyperscabrin A[c] H. scabrum −85.1 (0.06, mc) J. Ma 2012
124.2 R1 = i-Pr
R2 = prenyl		 hyperscabin K[d] H. scabrum −198.3 (0.17, mc) J. Ma 2021b
124.3 R1 = s-Bu
R2 = prenyl		 hyperscabin L[d][e] H. scabrum −178.4 (0.19, mc) J. Ma 2021b
Structure 125: hyperscabin J — A, bicyclononanes, seco
125
125.1 hyperscabin J[c] H. scabrum +36.6 (0.07, mc) J. Ma 2021b
Structure 126: hyperscabrin B, hyperscabrin C — A, bicyclononanes, seco
126
126.1 R = i-Pr hyperscabrin B[c] H. scabrum +27.6 (0.08, mc) J. Ma 2012
126.2 R = s-Bu hyperscabrin C[c][e] H. scabrum +22.4 (0.10, mc) J. Ma 2012
Structure 127: norhypersampsone A — A, bicyclononanes, seco
127
127.1 norhypersampsone A H. sampsonii −40.0 (0.5) J.-S. Zhang 2017
Structure 128: yezo'otogirin C, yezo'otogirin A, ascynol E and others — A, bicyclononanes, caged
128
128.1 R1 = i-Pr
R2 = Me		 yezo'otogirin C[c] H. yezoense −57.2 (0.05) N. Tanaka 2009b
128.2 R1 = i-Pr
R2 = prenyl		 yezo'otogirin A[c] H. yezoense −168.2 (0.25) N. Tanaka 2009b
128.3 R1 = i-Bu
R2 = Me		 ascynol E[c] H. ascyron −39 (0.2, m) Y.-L. Hu 2025
128.4 R1 = (S)-s-Bu
R2 = Me		 hypermogin A[c] H. monogynum −164.7 (0.2, m) Y.-R. Zeng 2021a
128.5 R1 = (S)-s-Bu
R2 = prenyl		 yezo'otogirin B[c] H. yezoense −165.7 (0.15) N. Tanaka 2009b
Structure 129: hypermogin C, hypermogin B — A, bicyclononanes, caged
129
129.1 R = i-Pr hypermogin C[c] H. monogynum −48.9 (0.12, m) Y.-R. Zeng 2021a
129.2 R = (S)-s-Bu hypermogin B[c] H. monogynum −38.0 (0.2, m) Y.-R. Zeng 2021a
Structure 130: hypermogin D — A, bicyclononanes, caged
130
130.1 hypermogin D[c] H. monogynum −32.0 (0.2, m) Y.-R. Zeng 2021a
Structure 131: ascynol D — A, bicyclononanes, caged
131
131.1 ascynol D[c] H. ascyron −31 (0.1, m) Y.-L. Hu 2025
Structure 132: ascynol B — A, bicyclononanes, caged
132
132.1 ascynol B[c] H. ascyron +17 (0.1, m) Y.-L. Hu 2025
Structure 133: ascynol C — A, bicyclononanes, caged
133
133.1 ascynol C[c] H. ascyron −82 (0.06, m) Y.-L. Hu 2025
Structure 134: ascynol A — A, bicyclononanes, caged
134
134.1 ascynol A[c] H. ascyron −42.6 (0.06, m) Y.-L. Hu 2025
Structure 135: norascyronone A, norascyronone B — A, bicyclononanes, caged
135
135.1 X = H norascyronone A[c] H. ascyron +68 (0.2, m) Y.-L. Hu 2019
135.2 X = OH norascyronone B[c] H. ascyron +22 (0.2, m) Y.-L. Hu 2019
Structure 136: norprzewalsone A — A, bicyclononanes, caged
136
136.1 norprzewalsone A[c] H. przewalskii +76.7 (0.4, m) Y. Duan 2022b
Structure 137: hyperforatum A — A, bicyclononanes, exo
137
137.1 hyperforatum A[c] H. perforatum +2 (0.1, m) X. Wang 2024
Structure 138: hyperforatum B — A, bicyclononanes, endo
138
138.1 hyperforatum B[e] H. perforatum +7.5 (1.00, m) X. Wang 2024
Structure 139: hyperforatum C — A, bicyclononanes, seco
139
139.1 hyperforatum C[e] H. perforatum +5.9 (0.35, m) X. Wang 2024
Structure 140: hyperforone I, norprzewalsone B — A, bicyclononanes, exo
140
140.1 R = i-Pr hyperforone I[c] H. perforatum +60.9 (0.6, m) Y. Guo 2021b
140.2 R = s-Bu norprzewalsone B[c][e] H. przewalskii +48.4 (0.3, m) Y. Duan 2022b
Structure 141: hyperforone J — A, bicyclononanes, exo
141
141.1 hyperforone J[c] H. perforatum −110.0 (0.3, m) Y. Guo 2021b
Structure 142: hookerione C, hypersubone C, hookerione A and others — A, bicyclononanes, caged
142
142.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hookerione C[d] H. hookerianum +2 (0.25, m) Y. Ye 2016
142.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = CH=CMe2		 hypersubone C[d] H. subsessile −13.3 (3.20, m) Y. Liao 2015
142.3 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hookerione A[d] H. hookerianum +5 (0.25, m) Y. Ye 2016
142.4 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hookerione B[d] H. hookerianum +32 (0.11, m) Y. Ye 2016
142.5 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hirsuton B[d] H. hirsutum +6.6 (0.30, m) J. Max 2021
142.6 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hirsuton A[d] H. hirsutum +3.7 (0.83, m) J. Max 2021
142.7 R1 = s-Bu
R2 = geranyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 hookerione D[d][e] H. hookerianum −27 (0.13, m) Y. Ye 2016
142.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH=CMe2		 plukenetione A C. plukenetii +1 (0.8) G. E. Henry 1996
142.9 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 (−)-28,29-epoxyplukenetione A[c] C. havetiodes var. stenocarpa, C. obdeltifolia −4.4 (1.0) O. E. Christian 2001, J. S. A. R. Teixeira 2005
142.10 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 (+)-28,29-epoxyplukenetione A[d] (enantiomer) H. sampsonii +8.8 (0.54) H. Zhu 2014
142.11 R1 = Ph
R2 = (Z)-CH=CHCMe2OH
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 wilsonglucinol H[d] H. wilsonii +2.4 (0.5, m) H. Cheng 2022a
142.12 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 sampsonione Q[d] H. sampsonii −9.65 (0.401) Z. Y. Xiao 2007
142.13 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = (S,S)-3-prenylmethyl-3-methyloxiran-2-yl		 hyperandrone A H. androsaemum +20.9 (0.25, m) K. Wang 2012, X.-W. Yang 2018
142.14 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 +39.3 (0.65) J. Hao 2021
142.15 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 +37.5 (0.17, mc) T. Řezanka 2007
142.16 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = CH=CMe2		 otogirinin A H. erectum Thunb., H. attenuatum − 8.1 (0.08, m) Y. Ishida 2010, D. Li 2015a
142.17 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = (S)-3,3-dimethyloxiran-2-yl		 sampsonione J[d] H. sampsonii +1.48 (0.2) L.-H. Hu 1999a, H. Zhu 2014
142.18 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 hyperisampsin G[d] H. sampsonii −8.7 (0.80) H. Zhu 2014
142.19 R1 = Ph
R2 = (R)-lavandulyl[f]
R3 = prenyl
R4 = CH=CMe2		 garcimultiflorone N[c][t][u][x] G. multiflora −28.9 (0.090, m) Z.-Q. Wang 2018
142.20 R1 = Ph
R2 = lavandulyl
R3 = prenyl
R4 = (R)-3,3-dimethyloxiran-2-yl		 epi-isosampsonione J[d][e] G. multiflora +55.0 (0.02, m) Y. Chen 2019a
142.21 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 +5.6 (0.12) C.-W. Ting 2012, Y. Chen 2019a
142.22 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 −32.8 (0.07, m) T.-W. Cao 2020
142.23 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 −12.7 (0.27, m) T.-W. Cao 2020
Structure 143: cumilcinol G, hyperattenin J — A, bicyclononanes, caged
143
143.1 R = prenyl cumilcinol G[d] H. wilsonii +104.7 (0.2, m) B. Tao 2024a
143.2 R = geranyl hyperattenin J[d] H. attenuatum Choisy +23.8 (0.3, m) D. Li 2015b
Structure 144: hyperadaman D — A, bicyclononanes, caged
144
144.1 hyperadaman D[d] H. wilsonii +47.7 (0.2, m) B. Tao 2024b
Structure 145: wilsonglucinol I — A, bicyclononanes, caged
145
145.1 wilsonglucinol I[d] H. wilsonii +20.9 (0.25, m) H. Cheng 2022a
Structure 146: garciyunnanone G — A, bicyclononanes, caged
146
146.1 garciyunnanone G[d] G. yunnan Hu +4.4 (0.1, m) M. Nan 2024
Structure 147: hyperadaman G, hyperadaman F — A, bicyclononanes, caged
147
147.1 R = i-Pr hyperadaman G[d] H. wilsonii +43.2 (0.2, m) B. Tao 2024b
147.2 R = Ph hyperadaman F[d] H. wilsonii +87.7 (0.6, m) B. Tao 2024b
Structure 148: hyperadaman B, hyperadaman A — A, bicyclononanes, caged
148
148.1 R = CH2COCHMe2 hyperadaman B[d] H. wilsonii +5.7 (0.2, m) B. Tao 2024b
148.2 R = CH2COC(Me)=CH2 hyperadaman A[d] H. wilsonii +17.0 (0.1, m) B. Tao 2024b
Structure 149: hyperadaman E — A, bicyclononanes, caged
149
149.1 hyperadaman E[d][z] H. wilsonii +86.0 (0.2, m) B. Tao 2024b
Structure 150: hyperisampsin B, hyperattenin L, garciyunnanone D — A, bicyclononanes, caged
150
150.1 R1 = geranyl
R2 = i-Pr
X = OH		 hyperisampsin B[d] H. sampsonii +2.6 (0.08) H. Zhu 2014
150.2 R1 = geranyl
R2 = i-Pr
X = OOH		 hyperattenin L[d] H. attenuatum −1.7 (0.42) D. Li 2018
150.3 R1 = lavandulyl[f]
R2 = H
X = OOH		 garciyunnanone D[d][e] G. yunnan Hu −5.4 (0.2, m) M. Nan 2024
Structure 151: hyperihirsolin A, hyperihirsolin B, hyperesternoid L and others — A, bicyclononanes, caged
151
151.1 R1 = i-Pr
R2 = prenyl
X = OH		 hyperihirsolin A H. hirsutum −25.3 (0.62, m) J. Max 2021
151.2 R1 = s-Bu
R2 = prenyl
X = OH		 hyperihirsolin B[e] H. hirsutum −13.0 (0.90, m) J. Max 2021
151.3 R1 = Ph
R2 = prenyl
X = OH		 hyperesternoid L[d] H. monogynum −32.2 (0.2, m) Z. Dong 2026
151.4 R1 = Ph
R2 = geranyl
X = OH		 hyperisampsin A[d] H. sampsonii −25.9 (0.16) H. Zhu 2014
151.5 R1 = Ph
R2 = (R)-lavandulyl[f]
X = OH		 garcimultiflorone O[c][t][v][x] G. multiflora +1.4 (0.73, m) Z.-Q. Wang 2018
151.6 R1 = Ph
R2 = lavandulyl[f]
X = OOH		 garciyunnanone C[d][e] G. yunnan Hu −5.4 (0.2, m) M. Nan 2024
Structure 152: hypersampsonone M, hyperisampsin C, isohyperisampsin C and others — A, bicyclononanes, caged
152
152.1 R = prenyl hypersampsonone M[d] H. sampsonii +10 (1.0, m) Y. Li 2023
152.2 R = geranyl hyperisampsin C[d] H. sampsonii −19.7 (0.30) H. Zhu 2014
152.3 R = lavandulyl isohyperisampsin C[c][e] G. multiflora +93.3 (0.02, m) Y. Chen 2019a
152.4 R = (R)-lavandulyl[f] garciyunnanone E[d] G. yunnan Hu +8.0 (0.2, m) M. Nan 2024
Structure 153: hyperadaman C — A, bicyclononanes, caged
153
153.1 hyperadaman C[d] H. wilsonii +36.2 (0.2, m) B. Tao 2024b
Structure 154: hyperesternoid M, hyperisampsin D — A, bicyclononanes, caged
154
154.1 R = prenyl
X = OH		 hyperesternoid M[d] H. monogynum −42.8 (0.1, m) Z. Dong 2026
154.2 R = geranyl
X = OOH		 hyperisampsin D[d] H. sampsonii −25.1 (0.12) H. Zhu 2014
Structure 155: hyperesternoid N, hypersubone B, garciyunnanone F — A, bicyclononanes, caged
155
155.1 R = prenyl
X = OOH		 hyperesternoid N[d] H. monogynum −38.8 (0.2, m) Z. Dong 2026
155.2 R = geranyl
X = OH		 hypersubone B[d] H. subsessile −52.2 (0.09, m) Y. Liao 2015
155.3 R = lavandulyl
X = OOH		 garciyunnanone F[d] G. yunnan Hu −63.2 (0.2, m) M. Nan 2024
Structure 156: cumilcinol H, hyperisampsin E, no name and others — A, bicyclononanes, caged
156
156.1 R1 = i-Pr
R2 = prenyl
R3 = CMe=CH2
X = OH		 cumilcinol H[d] H. wilsonii −6.6 (0.5, m) B. Tao 2024a
156.2 R1 = Ph
R2 = prenyl
R3 = CMe=CH2
X = OH		 hyperisampsin E[d] H. sampsonii +9.5 (0.23, m) H. Zhu 2014
156.3 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 no common name C. obdeltifolia +10.0 (0.4) J. S. A. R. Teixeira 2005
156.4 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperisampsin F[d] H. sampsonii +2.0 (0.10, m) H. Zhu 2014
156.5 R1 = Ph
R2 = geranyl
R3 = CMe=CH2
X = OH		 sampsonione I[d] H. sampsonii +16.88 (0.1) L.-H. Hu 1999a, H. Zhu 2014
156.6 R1 = Ph
R2 = (R)-lavandulyl[f]
R3 = CMe=CH2
X = OH		 garciyunnanone A[d] G. yunnan Hu +6.6 (0.1, m) M. Nan 2024
Structure 157: garciyunnanone B — A, bicyclononanes, caged
157
157.1 garciyunnanone B[d][e] G. yunnan Hu +27.5 (0.2, m) M. Nan 2024
Structure 158: hyperesternoid I, hyperesternoid J, hyperesternoid K — A, bicyclononanes, caged
158
158.1 R = i-Pr hyperesternoid I[d] H. monogynum −27.9 (0.2, m) Z. Dong 2026
158.2 R = i-Bu hyperesternoid J[d] H. monogynum −31.7 (0.2, m) Z. Dong 2026
158.3 R = (R)-s-Bu hyperesternoid K[d] H. monogynum −25.8 (0.2, m) Z. Dong 2026
Structure 159: hyperesternoid G — A, bicyclononanes, caged
159
159.1 hyperesternoid G[d] H. kouytchemse −53.9 (0.3, m) Z. Dong 2026
Structure 160: hyperesternoid H — A, bicyclononanes, caged
160
160.1 hyperesternoid H[d] H. kouytchemse −78.4 (0.2, m) Z. Dong 2026
Structure 161: hookerione G, hookerione H, hypersubone A and others — A, bicyclononanes, endo
161
161.1 R1 = prenyl
R2 = CO2Me
R3 = (S)-3,3-dimethyloxiran-2-yl		 hookerione G[d] H. hookerianum −213 (0.25, m) Y. Ye 2016
161.2 R1 = geranyl
R2 = H
R3 = (S)-3,3-dimethyloxiran-2-yl		 hookerione H[d] H. hookerianum −152 (0.14, m) Y. Ye 2016
161.3 R1 = geranyl
R2 = CO2Me
R3 = CH=CMe2		 hypersubone A[d] H. subsessile −142.5 (0.09, m) Y. Liao 2015
161.4 R1 = geranyl
R2 = CO2Me
R3 = (R)-3,3-dimethyloxiran-2-yl		 hookerione E[d] H. hookerianum −146 (0.16, m) Y. Ye 2016
161.5 R1 = geranyl
R2 = CO2Me
R3 = (S)-3,3-dimethyloxiran-2-yl		 hookerione F[d] H. hookerianum −198 (0.12, m) Y. Ye 2016
Structure 162: cumilcinol I — A, bicyclononanes, caged
162
162.1 cumilcinol I[d] H. wilsonii +108.5 (0.2, m) B. Tao 2024a
Structure 163: patumantane C, patumantane B — A, bicyclononanes, caged
163
163.1 R = H patumantane C[d] H. patulum −190.7 (0.1, m) Y. Duan 2024c
163.2 R = CO2Me patumantane B[d] H. patulum −68.0 (0.1, acn) Y. Duan 2024c
Structure 164: patumantane D — A, bicyclononanes, caged
164
164.1 patumantane D[d] H. patulum −75.3 (0.1, m) Y. Duan 2024c
Structure 165: hirsutofolin A, peroxyhirsutofolin A, hyperesternoid V and others — A, bicyclononanes, caged
165
165.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hirsutofolin A H. hirsutum +5.8 (0.65, m) J. Max 2021
165.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 peroxyhirsutofolin A H. hirsutum +12.0 (0.79, m) J. Max 2021
165.3 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid V[d] (prob. enantiomer) H. monogynum −35.2 (0.1, m) Z. Dong 2026
165.4 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 hyperacmosin F H. acmosepalum −16.3 (0.10, m) X. Wang 2020a
165.5 R1 = i-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hyperesternoid T[d] H. monogynum −43.3 (0.2, m) Z. Dong 2026
165.6 R1 = i-Bu
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid U[d] H. monogynum −45.2 (0.1, m) Z. Dong 2026
165.7 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hirsutofolin B[d][e] H. hirsutum −12.8 (1.15, m) J. Max 2021
165.8 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 hyperwilone B[c][e] (prob. enantiomer) H. wilsonii +51.1 (0.50) J. Hao 2021
165.9 R1 = (R)-s-Bu
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid W[d] H. monogynum −39.9 (0.1, m) Z. Dong 2026
165.10 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
R4 = E-CH=CHCMe2OOH		 3′-hydroperoxyisohirsutofolin B[e] H. hirsutum +20.1 (0.52, m) J. Max 2021
165.11 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = prenyl		 sampsonione R C. obdeltifolia, H. sampsonii, H. attenuatum +10.8 (0.011) F. G. Cruz 2004, Z. Y. Xiao 2007, D. Li 2015a
165.12 R1 = Ph
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl		 hyperesternoid X[d] H. monogynum −42.3 (0.1, m) Z. Dong 2026
165.13 R1 = Ph
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 otogirinin C H. erectum Thunb. NR Y. Ishida 2010
165.14 R1 = Ph
R2 = lavandulyl
R3 = CMe=CH2
R4 = OH		 epi-garcimultiflorone P[d][e] G. multiflora +5.32 (0.02, m) H. Teng 2019
Structure 166: pseudohenone F, pseudohenone G, garcimultiflorone P — A, bicyclononanes, caged
166
166.1 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 pseudohenone F H. pseudohenryi N. Robson −7 (0.10, m) X.-W. Yang 2017b
166.2 R1 = s-Bu
R2 = geranyl
R3 = CMe2OH
R4 = prenyl		 pseudohenone G[e] H. pseudohenryi N. Robson −8 (0.15, m) X.-W. Yang 2017b
166.3 R1 = Ph
R2 = (R)-lavandulyl[f]
R3 = CMe=CH2
R4 = OH		 garcimultiflorone P[c][t][u][x] G. multiflora −5.1 (0.19, m) Z.-Q. Wang 2018
Structure 167: hypersampsone L — A, bicyclononanes, caged
167
167.1 hypersampsone L H. sampsonii −67.4 (0.098) Y. H. Zeng 2012
Structure 168: hypersampsone S — A, bicyclononanes, caged
168
168.1 hypersampsone S (one of two by that name) H. sampsonii +33 (0.3) J.-J. Chen 2014
Structure 169: hypseudohenone B, hypseudohenone C — A, bicyclononanes, caged
169
169.1 R = prenyl hypseudohenone B[d] H. pseudohenryi +13.5 (0.147, m) N.-N. Jiang 2023
169.2 R = geranyl hypseudohenone C[d] H. pseudohenryi +13.1 (0.106, m) N.-N. Jiang 2023
Structure 170: hypseudohenone A — A, bicyclononanes, caged
170
170.1 hypseudohenone A[d] H. pseudohenryi +19.6 (0.222, m) N.-N. Jiang 2023
Structure 171: patumantane A — A, bicyclononanes, caged
171
171.1 patumantane A[d] H. patulum −56.9 (0.1, m) Y. Duan 2024c
Structure 172: norsampsone E, hyperacmosin E, lathrophytoic acid A — A, bicyclononanes, caged
172
172.1 R1 = C(=O)i-Pr
R2 = geranyl		 norsampsone E[d] H. sampsonii −63.0 (0.30) W.-J. Tian 2017
172.2 R1 = C(=O)Ph
R2 = geranyl		 hyperacmosin E H. acmosepalum −57.6 (0.175) X. Wang 2020a
172.3 R1 = (R)-CHPhCH2CO2H
R2 = prenyl		 lathrophytoic acid A Kielmeyera lathrophyton +15 (0.23, m) M. F. de Almeida 2011
Structure 173: hypersampsone N, hypersampsonone E — A, bicyclononanes, caged
173
173.1 R = prenyl hypersampsone N[d] H. sampsonii +34.4 (0.50) W.-J. Tian 2014b
173.2 R = geranyl hypersampsonone E[d] H. sampsonii +3.21 (1.06) J.-S. Zhang 2016
Structure 174: 3′-hydroxyisohirsutuman A, hyperwilsol B, hirsutuman B and others — A, bicyclononanes, caged
174
174.1 R1 = i-Pr
R2 = prenyl
R3 = E-CH=CHCMe2OH		 3′-hydroxyisohirsutuman A H. hirsutum &minus35.2 (0.13, m) J. Max 2021
174.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl		 hyperwilsol B[d] H. wilsonii −72.34 (0.05, m) Z.-X. Wang 2025
174.3 R1 = s-Bu
R2 = prenyl
R3 = prenyl		 hirsutuman B[e] H. hirsutum −61.9 (0.68, m) J. Max 2021
174.4 R1 = s-Bu
R2 = prenyl
R3 = E-CH=CHCMe2OH		 3′-hydroxyisohirsutuman B[e] H. hirsutum −69.5 (0.19, m) J. Max 2021
174.5 R1 = Ph
R2 = prenyl
R3 = prenyl		 sampsonione B C. obdeltifolia, G. propinqua, H. sampsonii +10.0 (0.018) L.-H. Hu 1998, F. G. Cruz 2004, T. Sriyatep 2017
174.6 R1 = Ph
R2 = prenyl
R3 = CH2CH2CMe2OH		 no common name C. obdeltifolia −5.1 (0.012) F. G. Cruz 2004
174.7 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH		 hyphenrone M H. sampsonii −82 (0.2, m) X.-W. Yang 2015
174.8 R1 = Ph
R2 = (R)-CH2CHOHCMe2OH
R3 = prenyl		 wilsonglucinol J[c] H. wilsonii +10.7 (0.5, m) H. Cheng 2022a
174.9 R1 = Ph
R2 = geranyl
R3 = prenyl		 sampsonione A H. sampsonii −49 (0.4) L.-H. Hu 1998
174.10 R1 = Ph
R2 = geranyl
R3 = (E)-CH=CHCMe2OH		 hyphenrone N H. sampsonii −89 (0.2, m) X.-W. Yang 2015
174.11 R1 = Ph
R2 = geranyl
R3 = (E)-CH=CHCMe2OMe		 hypersampsonone D[d] H. sampsonii −66.2 (0.52) J.-S. Zhang 2016
Structure 175: hyperhomanoon A, hyperhomanoon B, hypersampsone O and others — A, bicyclononanes, caged
175
175.1 R1 = i-Pr
R2 = prenyl		 hyperhomanoon A[d] H. patulum +6.2 (0.3, m) B. Tao 2025
175.2 R1 = (S)-s-Bu
R2 = prenyl		 hyperhomanoon B[d] H. patulum +45.0 (0.1, m) B. Tao 2025
175.3 R1 = Ph
R2 = prenyl		 hypersampsone O[d] H. sampsonii +15.2 (0.50) W.-J. Tian 2014b
175.4 R1 = Ph
R2 = geranyl		 hyphenrone O H. sampsonii −9 (0.1, m) X.-W. Yang 2015
175.5 R1 = Ph
R2 = (R)-lavandulyl[f]		 garciyunnanone R[d] G. yunnan Hu +9.2 (0.05, m) M. Nan 2024
Structure 176: hyperhomanoon E — A, bicyclononanes, caged
176
176.1 hyperhomanoon E[d] H. patulum −2.90 (0.5, m) B. Tao 2025
Structure 177: hyperhomanoon D, hyperhomanoon C — A, bicyclononanes, caged
177
177.1 R = prenyl hyperhomanoon D[d] H. patulum +95.3 (0.4, m) B. Tao 2025
177.2 R = geranyl hyperhomanoon C[d] H. patulum +26.2 (0.4, acn) B. Tao 2025
Structure 178: hyperihirsan B, hypersubone G, hypersubone H and others — A, bicyclononanes, caged
178
178.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 hyperihirsan B H. hirsutum +47.9 (0.18, m) J. Max 2021
178.2 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH		 hypersubone G[d] H. subsessile +37.5 (0.13, m) T.-W. Cao 2020
178.3 R1 = i-Pr
R2 = geranyl
R3 = CMe2OOH		 hypersubone H[d] H. subsessile +89.3 (0.08, m) T.-W. Cao 2020
178.4 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 plukenetione C C. plukenetii, H. sampsonii +65.9 (0.1) G. E. Henry 1999, O. E. Christian 2001, Z. Y. Xiao 2010
178.5 R1 = Ph
R2 = prenyl
R3 = CMe2OOH		 peroxysampsone A H. sampsonii +17.0 (0.128) Z. Y. Xiao 2010
178.6 R1 = Ph
R2 = (E)-CH=CHCMe2OOH
R3 = CMe2OH		 33-hydroperoxyisoplukenetione C C. havetiodes var. stenocarpa −3.9 (0.2) O. E. Christian 2001
178.7 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 otogirinin B H. erectum Thunb., H. attenuatum +12.0 (0.14, m) Y. Ishida 2010, D. Li 2015a
178.8 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperisampsin O[d] H. sampsonii +12 (0.2, m) H.-C. Zhu 2017
178.9 R1 = Ph
R2 = lavandulyl
R3 = OH		 garcimultinone B[d][e] G. multiflora +28.3 (0.04, m) Y. Chen 2019a
178.10 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 garcimultiflorone G[e] G. multiflora +5.6 (0.12) C.-W. Ting 2014
178.11 R1 = Ph
R2 = lavandulyl
R3 = CMe2OOH		 isohyperisampsin O[d][e] G. multiflora +22.4 (0.06, m) Y. Chen 2019a
178.12 R1 = Ph
R2 = (2S,3E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R3 = CMe2OH		 garcimultiflorone Q[c][t][u][x] G. multiflora −11.1 (0.21, m) Z.-Q. Wang 2018
Structure 179: hypersubone F, hyperisampsin N, hyperbeanin G and others — A, bicyclononanes, caged
179
179.1 R = geranyl
X = H		 hypersubone F[d] H. subsessile −73.4 (0.12, m) T.-W. Cao 2020
179.2 R = geranyl
X = OH		 hyperisampsin N[d] H. sampsonii −31 (0.1) H.-C. Zhu 2017
179.3 R = geranyl
X = OOH		 hyperbeanin G[c] H. beanii −40.0 (0.08, m) Y. Ma 2022a
179.4 R = lavandulyl
X = OH		 garcimultinone N[d] G. multiflora +12.59 (0.04, m) H. Teng 2021
Structure 180: peroxysampsone B — A, bicyclononanes, caged
180
180.1 peroxysampsone B H. sampsonii, H. attenuatum −41.2 (0.042) Z. Y. Xiao 2010, D. Li 2015a
Structure 181: pyranohyperihirsan A, pyranohyperihirsan B — A, bicyclononanes, caged
181
181.1 R = i-Pr pyranohyperihirsan A H. hirsutum −24.7, (0.29, m) J. Max 2021
181.2 R = s-Bu pyranohyperihirsan B[e] H. hirsutum −30.7 (0.25, m) J. Max 2021
Structure 182: hyperattenin M — A, bicyclononanes, caged
182
182.1 hyperattenin M[d][s] H. attenuatum −24.1 (0.19, m) D. Li 2018
Structure 183: hypersampsonone B, isohypersampsonone B — A, bicyclononanes, caged
183
183.1 R = geranyl hypersampsonone B[d] H. sampsonii +14.9 (0.35) J.-S. Zhang 2016
183.2 R = lavandulyl isohypersampsonone B[d][e] (inseparably mixed with epi-isohypersampsonone B, epimer at hemiacetal, in 5:1 ratio) G. multiflora +60.0 (0.01, m) Y. Chen 2019a
Structure 184: hyperesternoid Y — A, bicyclononanes, caged
184
184.1 hyperesternoid Y[d] H. monogynum −42.3 (0.1, m) Z. Dong 2026
Structure 185: hyperesternoid Z — A, bicyclononanes, caged
185
185.1 hyperesternoid Z[d] H. monogynum −48.7 (0.1, m) Z. Dong 2026
Structure 186: wilsonglucinol A — A, bicyclononanes, caged
186
186.1 wilsonglucinol A[d] H. wilsonii −14.4 (0.63, m) Y. Zhang 2020
Structure 187: wilsonglucinol C, cumilcinol C, wilsonglucinol B and others — A, bicyclononanes, caged
187
187.1 R1 = i-Pr
R2 = prenyl		 wilsonglucinol C[d] H. wilsonii −94.8 (0.84, m) Y. Zhang 2020
187.2 R1 = s-Bu
R2 = prenyl		 cumilcinol C[d][e] H. wilsonii −137.0 (0.1, m) B. Tao 2024a
187.3 R1 = Ph
R2 = prenyl		 wilsonglucinol B[d] H. wilsonii −51.2 (0.73, m) Y. Zhang 2020
187.4 R1 = Ph
R2 = (E)-CH=CHCMe2OH		 wilsonglucinol K, a.k.a. hypersampsone Y[d] H. wilsonii −4.0 (0.5, m), −74.0 (0.1, m) H. Cheng 2022a, J. Cao 2024
Structure 188: garcimultinone C — A, bicyclononanes, caged
188
188.1 garcimultinone C[d][e] G. multiflora −59.4 (0.02, m) H. Teng 2019
Structure 189: hyperesternoid D, hyperesternoid E — A, bicyclononanes, caged
189
189.1 R = i-Bu hyperesternoid D[d] H. monogynum −69.8 (0.3, m) Z. Dong 2026
189.2 R = (R)-s-Bu hyperesternoid E[d] H. monogynum −58.7 (0.3, m) Z. Dong 2026
Structure 190: hyperesternoid F — A, bicyclononanes, caged
190
190.1 hyperesternoid F[d] H. monogynum −87.2 (0.3, m) Z. Dong 2026
Structure 191: cumilcinol A, dioxasampsone B, hypersampsonone C and others — A, bicyclononanes, caged
191
191.1 R1 = i-Pr
R2 = prenyl		 cumilcinol A[d] H. wilsonii +170.8 (0.3, m) B. Tao 2024a
191.2 R1 = Ph
R2 = prenyl		 dioxasampsone B[d] H. sampsonii +77.0 (0.50) W.-J. Tian 2014c
191.3 R1 = Ph
R2 = geranyl		 hypersampsonone C[d] H. sampsonii +6.7 (0.15) J.-S. Zhang 2016
191.4 R1 = Ph
R2 = lavandulyl		 isohypersampsonone C[d][e] G. multiflora +81.7 (0.02, m) Y. Chen 2019a
Structure 192: hookerione Q, hypersampsone M, pseudohenone C and others — A, bicyclononanes, caged
192
192.1 R1 = i-Pr
R2 = geranyl
X = H2		 hookerione Q H. hookerianum +11.2 (0.12, m) Y. Ye 2019
192.2 R1 = Ph
R2 = prenyl
X = H2		 hypersampsone M[d] G. propinqua, H. sampsonii +56.6 (0.50) W.-J. Tian 2014a, T. Sriyatep 2017
192.3 R1 = Ph
R2 = prenyl
X = O		 pseudohenone C H. pseudohenryi N. Robson −5 (0.24, m) X.-W. Yang 2017b
192.4 R1 = Ph
R2 = (E)-4-oxoprenyl
X = H2		 pseudohenone B H. pseudohenryi N. Robson +7 (0.10, m) X.-W. Yang 2017b
192.5 R1 = Ph
R2 = geranyl
X = H2		 hypersampsone I H. sampsonii +18.6 (0.262) Y. H. Zeng 2012
192.6 R1 = Ph
R2 = geranyl
X = O		 sampsonione E H. sampsonii, H. attenuatum +57.7 (0.03) L.-H. Hu 1999b, D. Li 2015a
192.7 R1 = Ph
R2 = lavandulyl
X = O		 garciyunnanone I[d][e] G. yunnan Hu +2 (0.1, m) M. Nan 2024
Structure 193: hypersampsone C, hypersampsone P, hyperattenin F and others — A, bicyclononanes, caged
193
193.1 R1 = i-Pr
R2 = geranyl
X = H2		 hypersampsone C H. sampsonii +14.3 (0.2) Y.-L. Lin 2003
193.2 R1 = Ph
R2 = prenyl
X = H2		 hypersampsone P[d] H. sampsonii, H. subsessile +11.0 (0.3) W.-J. Tian 2014b, H.-M. Zhou 2020
193.3 R1 = Ph
R2 = prenyl
X = O		 hyperattenin F[d] H. attenuatum Choisy −2.9 (0.10, m) D. Li 2015a
193.4 R1 = Ph
R2 = CH2C(=O)CMe=CH2
X = H2		 pseudohenone D[d] H. pseudohenryi N. Robson +6 (0.28, m) X.-W. Yang 2017b
193.5 R1 = Ph
R2 = geranyl
X = H2		 sampsonione H H. sampsonii +5.15 (0.07) L.-H. Hu 1999b
193.6 R1 = Ph
R2 = geranyl
X = O		 hyperattenin G[d] H. attenuatum Choisy −6.9 (0.16, m) D. Li 2015a
193.7 R1 = Ph
R2 = lavandulyl
X = H2		 iso-sampsonione H[d][e] G. multiflora +11.84 (0.08, m) H. Teng 2019
193.8 R1 = Ph
R2 = lavandulyl
X = O		 garciyunnanone J[d][e] G. yunnan Hu +5 (0.1, m) M. Nan 2024
193.9 R1 = Ph
R2 = (E)-6,6-dimethoxy-3-methyl-2-hexenyl
X = H2		 hypercurpalone B[d] H. curvisepalum +1.94 (0.10, m) Y. Ye 2022
Structure 194: hookerione M, wilsonglucinol G, hyperesternoid Q and others — A, bicyclononanes, caged
194
194.1 R1 = i-Pr
R2 = prenyl
R3 = i-Pr
X = H		 hookerione M H. hookerianum +68.1 (0.08, m) Y. Ye 2019
194.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol G[d] H. wilsonii +26.3 (0.27, m) Y. Zhang 2020
194.3 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
X = H		 hyperesternoid Q[d] H. monogynum −22.4 (0.1, m) Z. Dong 2026
194.4 R1 = i-Pr
R2 = geranyl
R3 = CMe=CH2
X = H		 hypersampsone A H. sampsonii +21 (0.3) Y.-L. Lin 2003
194.5 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
X = H		 hirsutusal C[e] H. hirsutum N/A J. Max 2021
194.6 R1 = Ph
R2 = prenyl
R3 = i-Pr
X = H		 hookerione L H. hookerianum +31.4 (0.10, m) Y. Ye 2019
194.7 R1 = Ph
R2 = prenyl
R3 = CMe=CH2
X = H		 hypersampsone X[d] H. sampsonii +27.1 (0.50) W.-J. Tian 2017
194.8 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 plukenetione B C. plukenetii +17.2 (0.03) G. E. Henry 1999, R. B. Grossman 2000
194.9 R1 = Ph
R2 = prenyl
R3 = CMe2OOH
X = H		 hyperbeanin F[c] H. beanii +10.0 (0.11, m) Y. Ma 2022a
194.10 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperesternoid O[d] H. monogynum −45.9 (0.3, m) Z. Dong 2026
194.11 R1 = Ph
R2 = prenyl
R3 = OH
X = H		 hypersampsonone L[d] H. sampsonii +10 (1.0, m) Y. Li 2023
194.12 R1 = Ph
R2 = geranyl
R3 = i-Pr
X = H		 hypersampsone D H. sampsonii −35 (0.2) Y.-L. Lin 2003
194.13 R1 = Ph
R2 = geranyl
R3 = CMe=CH2
X = H		 sampsonione D H. sampsonii +12.27 (0.156) L.-H. Hu 1999b
194.14 R1 = Ph
R2 = geranyl
R3 = CMe2OH
X = H		 sampsonione C H. sampsonii, H. attenuatum +13.39 (0.174) L.-H. Hu 1999b, D. Li 2015a
194.15 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
X = H		 hypersampsonone F[d] H. sampsonii +6.73 (1.04) J.-S. Zhang 2016
194.16 R1 = Ph
R2 = geranyl
R3 = OH
X = H		 cumilcinol D[d] H. wilsonii −4.9 (0.3, m) B. Tao 2024a
194.17 R1 = Ph
R2 = neryl
R3 = i-Pr
X = H		 hookerione I H. hookerianum +24.2 (0.25, m) Y. Ye 2019
194.18 R1 = Ph
R2 = lavandulyl
R3 = CMe=CH2
X = H		 garciyunnanone K[d][e] G. yunnan Hu +12.9 (0.1, m) M. Nan 2024
194.19 R1 = Ph
R2 = lavandulyl
R3 = i-Pr
X = H		 garciyunnanone N[d][e] G. yunnan Hu +1.0 (0.2, m) M. Nan 2024
194.20 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH
X = H		 garciyunnanone Q[d][e] G. yunnan Hu +25.6 (0.2, m) M. Nan 2024
194.21 R1 = Ph
R2 = lavandulyl
R3 = CMe2OOH
X = H		 iso-hypersampsonone F[d][e] G. multiflora +5.60 (0.01, m) H. Teng 2019
194.22 R1 = Ph
R2 = lavandulyl
R3 = OH
X = H		 garcimultinone A[d][e] G. multiflora −25.6 (0.02, m) Y. Chen 2019a
Structure 195: wilsonglucinol F, hookerione O, cumilcinol F and others — A, bicyclononanes, caged
195
195.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 wilsonglucinol F[d] H. wilsonii +29.2 (0.55, m) Y. Zhang 2020
195.2 R1 = i-Pr
R2 = geranyl
R3 = CMe=CH2		 hookerione O H. hookerianum +39.1 (0.25, m) Y. Ye 2019
195.3 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH		 cumilcinol F[d][e] H. wilsonii +104.7 (0.2, m) B. Tao 2024a
195.4 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 hypersampsone Q[d] H. sampsonii +18.3 (0.4) W.-J. Tian 2014b
195.5 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hypersampsone G H. sampsonii +10.25 (0.401) Y. H. Zeng 2009
195.6 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 hypersampsone J H. sampsonii +11.4 (0.573) Y. H. Zeng 2012
195.7 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 hypersampsonone G[d] H. sampsonii +4.22 (0.9) J.-S. Zhang 2016
195.8 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperattenin K[d] H. attenuatum Choisy −11.5 (0.886, m) D. Li 2015b
195.9 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 isohypersampsonone G[d][e] G. multiflora +34.2 (0.01, m) Y. Chen 2019a
Structure 196: wilsonglucinol D, hyperwilone C, wilsonglucinol E and others — A, bicyclononanes, caged
196
196.1 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol D[d] H. wilsonii −17.7 (0.92, m) Y. Zhang 2020
196.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
X = H		 hyperwilone C[c] (enantiomer) H. wilsonii +47.3 (0.50, m) J. Hao 2021
196.3 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
X = H		 wilsonglucinol E, a.k.a. hirsutusal D[d][e] H. wilsonii −9.9 (0.34, m) Y. Zhang 2020, J. Max 2021
196.4 R1 = Ph
R2 = prenyl
R3 = OH
X = H		 no common name C. obdeltifolia, G. propinqua NR F. G. Cruz 2004, T. Sriyatep 2017
196.5 R1 = Ph
R2 = prenyl
R3 = i-Pr
X = H		 hyphenrone Q H. sampsonii −4 (0.2, m) X.-W. Yang 2015
196.6 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 attenuatumione A[c] H. attenuatum −19.3 (0.18) Z.-B. Zhou 2014, X.-W. Yang 2018
196.7 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH		 hyperesternoid P[d] H. monogynum −52.2 (0.2, m) Z. Dong 2026
196.8 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H		 hypercohone A[d] (prob. enantiomer) H. cohaerens +3.87 (0.21, m) X. Liu 2013b
196.9 R1 = Ph
R2 = geranyl
R3 = i-Pr
X = H		 hookerione K H. hookerianum −33.1 (0.27, m) Y. Ye 2019
196.10 R1 = Ph
R2 = geranyl
R3 = CMe2OH
X = H		 attenuatumione D H. attenuatum −10.8 (0.15) Z.-B. Zhou 2014
196.11 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
X = H		 hyperattenin I[d] H. attenuatum Choisy −24.5 (0.23, m) D. Li 2015a
196.12 R1 = Ph
R2 = lavandulyl
R3 = CMe=CH2
X = H		 garciyunnanone L[d][e] G. yunnan Hu −5.7 (0.2, m) M. Nan 2024
196.13 R1 = Ph
R2 = lavandulyl
R3 = i-Pr
X = H		 garciyunnanone O[d][e] G. yunnan Hu +2.0 (0.1, m) M. Nan 2024
Structure 197: hookerione N, hirsutusal A, cumilcinol E and others — A, bicyclononanes, caged
197
197.1 R1 = i-Pr
R2 = prenyl
R3 = i-Pr		 hookerione N H. hookerianum −10.3 (0.13, m) Y. Ye 2019
197.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH		 hirsutusal A[e] H. hirsutum +36.7 (0.18, m) J. Max 2021
197.3 R1 = i-Pr
R2 = prenyl
R3 = OH		 cumilcinol E[d] H. wilsonii −2.0 (0.1, m) B. Tao 2024a
197.4 R1 = i-Pr
R2 = geranyl
R3 = i-Pr		 hypersampsone B H. sampsonii +12 (0.3) Y.-L. Lin 2003
197.5 R1 = i-Pr
R2 = geranyl
R3 = CMe2OH		 hookerione P H. hookerianum −10.3 (0.13, m) Y. Ye 2019
197.6 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH		 hirsutusal B[e] H. hirsutum −6.9 (0.24, m) J. Max 2021
197.7 R1 = Ph
R2 = prenyl
R3 = OH		 pseudohenone E C. obdeltifolia, H. pseudohenryi N. Robson −27 (0.13, m) F. G. Cruz 2004, X.-W. Yang 2017b
197.8 R1 = Ph
R2 = prenyl
R3 = i-Pr		 hyphenrone P H. sampsonii −83 (0.1, m) X.-W. Yang 2015
197.9 R1 = Ph
R2 = prenyl
R3 = CMe=CH2		 hypercohone B H. cohaerens −37.2 (0.11, m) X. Liu 2013b
197.10 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 hyperacmosin G[c] H. acmosepalum −8.3 (0.012) X. Wang 2020a
197.11 R1 = Ph
R2 = prenyl
R3 = CMe2OH		 sampsonione G[d] (prob. enantiomer) C. obdeltifolia, H. sampsonii, H. attenuatum, H. wilsonii +10.0 (0.01) L.-H. Hu 1999b, F. G. Cruz 2004, D. Li 2015a, Y. Zhang 2020
197.12 R1 = Ph
R2 = geranyl
R3 = OH		 hyperattenin H[d] H. attenuatum Choisy −12.4 (0.26, m) D. Li 2015a, X.-W. Yang 2017b
197.13 R1 = Ph
R2 = geranyl
R3 = OH		 cowabenzophenone B[c] (prob. enantiomer) G. cowa +96 (0.048) T. Sriyatep 2014, X.-W. Yang 2017b
197.14 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hypersampsone E[c] H. sampsonii +39 (0.2) Y.-L. Lin 2003, H.-B. Zhang 2019
197.15 R1 = Ph
R2 = geranyl
R3 = i-Pr		 hyperichoisin B[d] (enantiomer) H. choisianum −17.4 (0.285) H.-B. Zhang 2021
197.16 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 hypercohone C H. cohaerens −38.0 (0.09, m) X. Liu 2013b
197.17 R1 = Ph
R2 = geranyl
R3 = CMe=CH2		 cowabenzophenone A (enantiomer) G. cowa +137 (0.02) T. Sriyatep 2014
197.18 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 sampsonione F[c] H. sampsonii, H. attenuatum, H. wilsonii +14.5 (1.1) L.-H. Hu 1999b, D. Li 2015a, H.-B. Zhang 2019, Y. Zhang 2020
197.19 R1 = Ph
R2 = geranyl
R3 = CMe2OH		 hyperichoisin C[d] (enantiomer) H. choisianum −21.9 (0.31) H.-B. Zhang 2021
197.20 R1 = Ph
R2 = geranyl
R3 = CMe2OOH		 hyperberlone C[c] H. beanii −0.34 (c 2, m) Y.-W. Li 2022
197.21 R1 = Ph
R2 = neryl
R3 = i-Pr		 hookerione J H. hookerianum −38.2 (0.12, m) Y. Ye 2019
197.22 R1 = Ph
R2 = lavandulyl
R3 = CMeCH2		 garciyunnanone M[d][e] G. yunnan Hu +4.3 (0.4, m) M. Nan 2024
197.23 R1 = Ph
R2 = lavandulyl
R3 = i-Pr		 iso-hookerione J[d][e] G. multiflora −4.70 (0.05, m) H. Teng 2019
197.24 R1 = Ph
R2 = lavandulyl
R3 = CMe2OH		 garciyunnanone P[d][e] G. yunnan Hu −3.6 (0.1, m) M. Nan 2024
197.25 R1 = Ph
R2 = lavandulyl
R3 = OH		 garciyunnanone H[d] G. yunnan Hu +21.6 (0.1, m) M. Nan 2024
Structure 198: hypertonii A — A, bicyclononanes, caged
198
198.1 hypertonii A[c] H. addingtonii N. Robson +42.3 (0.1, acn) Q. Feng 2025
Structure 199: dioxasampsone A — A, bicyclononanes, caged
199
199.1 dioxasampsone A[d] H. sampsonii +16.8 (0.50) W.-J. Tian 2014c
Structure 200: hyperesternoid R — A, bicyclononanes, caged
200
200.1 hyperesternoid R[d] H. monogynum −32.7 (0.2, m) Z. Dong 2026
Structure 201: hyperesternoid S — A, bicyclononanes, caged
201
201.1 hyperesternoid S[d] H. monogynum −24.8 (0.2, m) Z. Dong 2026
Structure 202: pseudohenone A — A, bicyclononanes, caged
202
202.1 pseudohenone A H. pseudohenryi N. Robson +43 (0.20, m) X.-W. Yang 2017b
Structure 203: cumilcinol B — A, bicyclononanes, caged
203
203.1 cumilcinol B[d] H. wilsonii +98.0 (0.1, m) B. Tao 2024a
Structure 204: hypercurpalone A — A, bicyclononanes, dimer
204
204.1 hypercurpalone A[d] H. curvisepalum −17.9 (0.13, m) Y. Ye 2022
Structure 205: hypseudone A — A, bicyclononanes, caged
205
205.1 hypseudone A[c] H. pseudohenryi +38.2 (0.096, m) N.-N. Jiang 2025
Structure 206: garsubelone A — A, bicyclononanes, dimer
206
206.1 garsubelone A[d] G. subelliptica +103 (0.14, m) Y.-L. Wang 2019
Structure 207: hyperforatum D, kielmeyeracin, spiranthenone B and others — B, bicyclononanes, exo
207
207.1 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 hyperforatum D H. perforatum +4.0 (1.00, m) X. Wang 2024
207.2 R1 = n-Pr
R2 = CHBuCO2Me
R3 = prenyl
R4 = prenyl
R5 = H		 kielmeyeracin[c][e] Kielmeyera variabilis −70 (0.1, m) A. Coqueiro 2016
207.3 R1 = i-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 spiranthenone B Spiranthera odoratissima −24 (0.10) L. C. Albernaz 2012, X.-W. Yang 2018
207.4 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe=O
R5 = H		 oblongifolin V[c] G. oblongifolia +4.3 (0.02, m) H. Zhang 2016
207.5 R1 = Ph
R2 = H
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin L[c] G. oblongifolia −15.1 (0.05, m) H. Zhang 2014a, X.-W. Yang 2018
207.6 R1 = Ph
R2 = H
R3 = prenyl
R4 = CH2C(=O)C(=CH2)CH2CH2CH=CMe2
R5 = H		 oblongifolin O[c][l][m] G. oblongifolia −20.8 (0.05, m) H. Zhang 2014a
207.7 R1 = Ph
R2 = H
R3 = prenyl
R4 = 6-oxo-ω-isogeranyl[h]
R5 = H		 oblongifolin N[c][l][m] G. oblongifolia −17.5 (0.04, m) H. Zhang 2014a
207.8 R1 = Ph
R2 = H
R3 = prenyl
R4 = (S)-6-hydroxy-ω-isogeranyl[h]
R5 = H		 oblongifolin Q[c][l][m] G. oblongifolia −222.2 (0.03, m) H. Zhang 2014a
207.9 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 hyperascyrin L[d] H. ascyron −58.5 (0.1, m) B. Zhen 2019
207.10 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 clusianone[c] C. congestiflora, C. spiritu-sanctensis, C. torresii, H. hypericoides +58.3 (0.7); OMe: +61 (1.4) C. M. A. de Oliveira 1996, A. L. Piccinelli 2005, V. Rodeschini 2007, G. E. Henry 2008, M. R. Garnsey 2010, F. Horeischi 2015
207.11 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 −14.3 (5.6, m) J. Merza 2006, M. Masullo 2008
207.12 R1 = Ph
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 spiritone[e] C. spiritu-sanctensis NR A. L. M. Porto 2000
207.13 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 18-hydroxyclusianone H. hypericoides NR O. E. Christian 2008
207.14 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone J, a.k.a. garciyunnanin A G. cambogia, G. gummi-gutta, G. virgata, G. yunnanensis −34.3 (1.75, m), −3.0 (0.11) J. Merza 2006, M. Masullo 2008, G. Xu 2008, P. Pandey 2024
207.15 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 ent-guttiferone J[l][m] (prob. enantiomer) R. edulis +10.8 (0.01, m) U. M. Acuña 2010
207.16 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin U[c] G. oblongifolia +48.2 (0.08, m) H. Zhang 2014a
207.17 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = prenyl		 garcicowin B G. cowa −16.0 (0.21) G. Xu 2010
207.18 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 aristophenone A[c] G. xanthochymus +58 (0.1); OAc: +53 (0.1), +54 (0.1) O. Cuesta-Rubio 2001b, S. Baggett 2005
207.19 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone K G. calcicola, G. cambogia, G. cowa, G. yunnanensis Hu −2 (0.35) S. Cao 2007, M. Masullo 2008, G. Xu 2010, D. Zheng 2017
207.20 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = CH2COCMe=CH2		 garciyunnanin J[c] G. yunnanensis +103.1 (0.13, m) D. Zheng 2021b
207.21 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = CH2CHOHCMe=CH2
R5 = prenyl		 schomburgkianone F[d][e] G. schomburgkiana −13 (0.4) D. H. Le 2016
207.22 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = CH2CHOHCMe=CH2
R5 = prenyl		 schomburgkianone G[d][e] (diastereomer) G. schomburgkiana +6 (c 0.3) D. H. Le 2016
207.23 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl		 garciyunnanol I[d] G. yunnanensis −58 (0.36, m) X.-Y. Hu 2024
207.24 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = CH2CO2H
R5 = prenyl		 garciyunnanol H[d] G. yunnanensis −12 (0.18, m) X.-Y. Hu 2024
207.25 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin B G. cowa, G. oblongifolia, G. yunnanensis Hu +17.6 (0.21) W. Hamed 2006, G. Xu 2010, D. Zheng 2017
207.26 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = prenyl		 guttiferone G G. humilis, G. macrophylla −25 (0.04), +8.7 (1.5) R. B. Williams 2003, K. Herath 2005, R. Ciochina 2006
207.27 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = prenyl		 oblongifolin C (prob. enantiomer) G. cowa, G. oblongifolia, G. yunnanensis Hu +14.5 (0.21) W. Hamed 2006, G. Xu 2010, D. Zheng 2017
207.28 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OH
R5 = prenyl		 garschomcinol A[d] G. schomburgkiana +12.5 (0.20, m) S. Kaennakam 2022a
207.29 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OMe
R5 = prenyl		 garschomcinol B[d] G. schomburgkiana +13.5 (0.28, m) S. Kaennakam 2022a
207.30 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OEt
R5 = prenyl		 garschomcinol C[d] G. schomburgkiana +14.7 (0.34, m) S. Kaennakam 2022a
207.31 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (R)-6-hydroxy-ω-isogeranyl[h]
R5 = prenyl		 schomburgkianone A[d] G. schomburgkiana +15 (0.7) D. H. Le 2016
207.32 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (S)-6-hydroxy-ω-isogeranyl[h]
R5 = prenyl		 schomburgkianone B[d] G. schomburgkiana +40 (1.0) D. H. Le 2016
207.33 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E,E)-CH2CH=CMeCH2CH=CHCMe2OH
R5 = prenyl		 schomburgkianone C[d] G. schomburgkiana +25 (0.8) D. H. Le 2016
207.34 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E,E)-CH2CH=CMeCH2CH=CHCMe2OMe
R5 = prenyl		 garciyunnanol E[d] G. yunnanensis +5 (0.36, m) X.-Y. Hu 2024
207.35 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone M[c] G. cambogia −29.8 (0.15, m) M. Masullo 2008, M. Masullo 2010
207.36 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = prenyl		 guttiferone P G. solomonensis +18.2 (0.33) A. R. Carroll 2009
207.37 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = geranyl
R5 = H		 guttiferone B G. cowa, S. globulifera −44 (0.5) K. R. Gustafson 1992, G. Xu 2010
207.38 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 7-epi-garcinol[e] M. coccinea −86 (0.8) G. Marti 2009
207.39 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-isolavandulyl[g]
R4 = prenyl
R5 = H		 xanthochymusone B[d] G. xanthochymus +137 (0.1, m) Z.-H. Xu 2022
207.40 R1 = 3,4-dihydroxyphenyl
R2 = (E)-CH2CH=CMeCH2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl		 garciyunnanol F[d] G. yunnanensis +7 (0.17, m) X.-Y. Hu 2024
207.41 R1 = 3,4-dihydroxyphenyl
R2 = (Z)-CH2CH=CMeCH2OH
R3 = prenyl
R4 = geranyl
R5 = prenyl		 garciyunnanol G[d] G. yunnanensis +11 (0.18, m) X.-Y. Hu 2024
207.42 R1 = 3,4-dihydroxyphenyl
R2 = geranyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone O (one of two by that name) G. solomonensis +30.7 (0.66) A. R. Carroll 2009
207.43 R1 = 3,4-dihydroxyphenyl
R2 = ω-isogeranyl[h]
R3 = prenyl
R4 = geranyl
R5 = H		 semsinone A[n] G. semseii +52 (0.1) J. J. Magadula 2008
207.44 R1 = 2,4,5-trihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone L G. calcicola −8 (0.06) S. Cao 2007
Structure 208: hyperpapuanone, laxifloranone, mesuaferroic acid H and others — B, bicyclononanes, endo
208
208.1 R1 = i-Pr
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = H		 hyperpapuanone H. papuanum +15 (0.1, m) K. Winkelmann 2001a
208.2 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = prenyl
R4 = prenyl
R5 = H		 laxifloranone[e] Marila laxiflora +23.6 (0.8, m) H. R. Bokesch 1999
208.3 R1 = i-Bu
R2 = CHPhCH2CO2Me
R3 = prenyl
R4 = prenyl
R5 = H		 mesuaferroic acid H[e] Mesua ferrea +15.9 (0.2, m) X.-C. Zhang, 2020
208.4 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = H		 mesuaferroic acid I[e] Mesua ferrea +2.15 (0.2, m) X.-C. Zhang, 2020
208.5 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) X.-C. Zhang, 2020
208.6 R1 = CH(OH)CMe2OH
R2 = CHPhCH2CO2H
R3 = prenyl
R4 = prenyl
R5 = H		 mesuaferroic acid K[e] Mesua ferrea +3.25 (0.2, m) X.-C. Zhang, 2020
208.7 R1 = Ph
R2 = H
R3 = prenyl
R4 = Me
R5 = H		 oblongifolin P[c] G. oblongifolia −56.3 (0.05, m) H. Zhang 2014a
208.8 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = H		 garciniaphenone[m] G. brasiliensis −52.8 (0.1) P. B. M. C. Derogis 2008
208.9 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone Q G. cochinchinensis −50 (0.21) H. D. Nguyen 2011
208.10 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl		 cowanone, a.k.a. chamuangone (prob. enantiomer) G. cowa +5 (1.0) K. Trisuwan 2012, A. Sakunpak 2012
208.11 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = prenyl		 garcowacinol A[d] G. cowa −35.0 (0.50, m) S. Kaennakam 2022b
208.12 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe2OMe
R5 = prenyl		 garcowacinol B[d] G. cowa −46.5 (0.50, m) S. Kaennakam 2022b
208.13 R1 = Ph
R2 = H
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin AA[c] G. oblongifolia −36.2 (0.05, m) H. Zhang 2016, X.-W. Yang 2018
208.14 R1 = Ph
R2 = H
R3 = prenyl
R4 = (E)-CH2CH=CMeCH2CH2CH2CMe2OH
R5 = H		 oblongifolin Z[c][m] G. oblongifolia −23.5 (0.03, m) H. Zhang 2016
208.15 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = H		 hyperibone L H. scabrum +69.5 (0.2) N. Tanaka 2004
208.16 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl		 hyperelatone A[d] H. elatoides +189.3 (0.1) X.-T. Yan 2019
208.17 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 7-epi-clusianone[d] C. sandinensis, C. torresii, H. elegans, H. hypericoides +62.3 (1.1) F. Delle Monache 1991, M. H. Santos 1998, T. M. de Almeida Alves 1999, K. Winkelmann 2001a, A. L. Piccinelli 2005, P. T. Nedialkov 2016, L. Wang 2021
208.18 R1 = Ph
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 garcimultiflorone K[c] (one of two by that name) G. multiflora −92.4 (0.41, m) L.-Y. Cheng 2018a
208.19 R1 = Ph
R2 = prenyl
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone C[d] G. picrorhiza +15 (0.10, m) E. R. Sukandar 2020
208.20 R1 = Ph
R2 = geranyl
R3 = prenyl
R4 = prenyl
R5 = H		 hyperbeone A[c] H. beanii −4.7 (0.08, m) W.-X. Li 2021
208.21 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 18-hydroxy-7-epi-clusianone H. hypericoides +64 (0.29) O. E. Christian 2008
208.22 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin E G. oblongifolia +65.1 (0.40) S.-X. Huang 2009
208.23 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone N G. cambogia −34.5 (0.07, m) M. Masullo 2008
208.24 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H		 14-deoxygarcinol[e] M. coccinea −42 (0.3) G. Marti 2009
208.25 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = (S)-isolavandulyl[g]
R4 = prenyl
R5 = H		 xanthochymusone A[d] G. xanthochymus +137 (0.1, m) Z.-H. Xu 2022
208.26 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone B[d] G. picrorhiza +12 (0.10, m) E. R. Sukandar 2020
208.27 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 garcimultiflorone H[d] G. multiflora +29.8 (0.62, m) W. Fu 2015
208.28 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl		 guttiferone A S. globulifera, G. livingstonei, G. humilis +34 (1.7) K. R. Gustafson 1992, R. B. Williams 2003
208.29 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H		 oblongifolin A G. cowa, G. oblongifolia, G. yunnanesis Hu +23 (0.35) W. Hamed 2006, G. Xu 2010, D. Zheng 2017
208.30 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (R)-6-hydroxy-ω-isogeranyl[h]
R5 = H		 oblongifolin T[c] G. oblongifolia +10.8 (0.05, m) H. Zhang 2014a, X.-W. Yang 2018
208.31 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 −271.4 (0.17, m), +28 (0.10, m) A. Soemiati 2006, S. Hartati 2008, E. R. Sukandar 2020
208.32 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = H		 guttiferone I[i] (one of two by that name) G. griffithii −68 (1.2) R. W. Fuller 1999
208.33 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R4 = prenyl
R5 = H		 nujiangefolin E[d][e] G. nujiangensis −22.48 (0.11, m) X.-J. Liu 2023
208.34 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = 2,2-dimethyl-5-isopropenyl-3-tetrahydrofurylmethyl
R4 = prenyl
R5 = H		 paucinochymol A[d][e] G. paucinervis −38.8 (0.01, m) X. Tan 2020
208.35 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = geranyl
R5 = H		 oblongifolin D G. cowa, G. oblongifolia +44.6 (0.21) W. Hamed 2006, G. Xu 2010
208.36 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 Hu, M. coccinea, Allanblackia stuhlmannii −138 (0.1), −293 (0.4) 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
208.37 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 Hu +101 (0.5) 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
208.38 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = prenyl		 guttiferone D[e] S. globulifera +92 (0.9) as mix with guttiferone C K. R. Gustafson 1992
208.39 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = CH2CHOHCMe2OH
R5 = H		 garcimultiflorone F[e] G. multiflora −68.7 (0.49, m) X. Liu 2010, X. Wang 2021a
208.40 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-lavandulyl[f]
R4 = CH2CHOHCMe2OH
R5 = H		 isogarcimultiflorone F[e] (diastereomer) G. multiflora −46.0 (c 0.50, m) X. Liu 2010, X. Wang 2021a
208.41 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = (S)-CH2CHOHCMe2OMe
R5 = H		 garciesculentone C[e] G. esculenta −24.9 (0.08, m) H. Zhang 2014b
208.42 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 +138 (0.1), +12.6 (1.0) C. G. Karanjgoakar 1973, D. L. Dreyer. <i>Phytochemistry</i> <b>1974</b> 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
208.43 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = isolavandulyl[g]
R4 = prenyl
R5 = prenyl		 guttiferone C[e] S. globulifera +92 (0.9) as mix with guttiferone D K. R. Gustafson 1992
208.44 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 +10 (0.1, m) U. M. Acuña 2010
208.45 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (2R)-4-hydroxyisolavandulyl[g]
R4 = prenyl
R5 = H		 garcimultiflorone E[e] G. multiflora −43.6 (0.41, m) X. Liu 2010, X. Wang 2021a
208.46 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (4R)-4-hydroxyisolavandulyl[g]
R4 = prenyl
R5 = H		 garciesculentone E[e] G. esculenta −14.3 (0.03, m) H. Zhang 2014b
208.47 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (4S)-4-hydroxyisolavandulyl[g]
R4 = prenyl
R5 = H		 garciesculentone D[e] G. esculenta −15.9 (0.05, m) H. Zhang 2014b
208.48 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = (1S)-2-methylene-4,4-dimethylcyclohexylmethyl
R4 = prenyl
R5 = H		 acuminophenone A R. acuminata +208 (0.01) G. R. Almanza 2011
208.49 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) L.-T. T. Nguyen 2012
208.50 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (2,4,4-trimethyl-2-cyclohexenyl)methyl
R4 = prenyl
R5 = H		 coccinone F M. coccinea −32 (0.7) G. Marti 2009
208.51 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = (1S,3R)-3-(2-hydroxyisopropyl)-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone D[d] G. picrorhiza +34 (0.10, m) E. R. Sukandar 2020
208.52 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = (1S,3S)-3-acetyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone E[d] G. picrorhiza +5 (0.10, m) E. R. Sukandar 2020
208.53 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 +170.0 (0.1, m) P.-X. Ji 2025
208.54 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 +27 (0.10, m) E. R. Sukandar 2020
208.55 R1 = 3,4-dihydroxyphenyl
R2 = CH2CH2CMe2OH
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 garcimultiflorone D (one of two by that name) G. multiflora −53.6 (0.48, m) X. Liu 2010, X. Wang 2021a
208.56 R1 = 3,4-dihydroxyphenyl
R2 = CH2CHOHCMe2OH
R3 = (S)-lavandulyl[f]
R4 = prenyl
R5 = H		 18-hydroxygarcimultiflorone D[e] G. multiflora −33.3 (0.12, m) X. Liu 2010, X. Wang 2021a
208.57 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = prenyl
R4 = prenyl
R5 = H		 coccinone G[e] M. coccinea −16 (1.0) G. Marti 2009
208.58 R1 = 3,4-dihydroxyphenyl
R2 = (2,4,4-trimethyl-1-cyclohexenyl)methyl
R3 = prenyl
R4 = prenyl
R5 = H		 coccinone H M. coccinea −16 (1.0) G. Marti 2009
Structure 209: garciyunnanimine A, garciyunnanimine C — B, bicyclononanes, enamine
209
209.1 R = prenyl garciyunnanimine A[c] G. yunnanensis Hu +11.7 (0.03, m) D. Zheng 2017, J.-Y. Xie 2024
209.2 R = geranyl garciyunnanimine C[c] G. yunnanensis Hu +11.4 (0.041, m) D. Zheng 2017, J.-Y. Xie 2024
Structure 210: hyperelamine A, hyperelanitrile C, hyperelanitrile A and others — B, bicyclononanes, enamine
210
210.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = H		 hyperelamine A[d] H. elatoides +44.3 (0.11, m) J.-Y. Xie 2024
210.2 R1 = Ph
R2 = Me
R3 = prenyl
R4 = (R)-CH(CH3)C≡N		 hyperelanitrile C[d] H. elatoides +28.3 (0.10, m) J.-Y. Xie 2024
210.3 R1 = Ph
R2 = Me
R3 = prenyl
R4 = (S)-CH(CH3)C≡N		 hyperelanitrile A[d] H. elatoides +91.1 (0.05, m) J.-Y. Xie 2024
210.4 R1 = 3,4-dihydroxyphenyl
R2 = (S)-lavandulyl[f]
R3 = H
R4 = H		 garciyunnanimine B[c] G. yunnanensis Hu −69.0 (0.035, m) D. Zheng 2017, J.-Y. Xie 2024
Structure 211: hyperelanitrile D, hyperelanitrile B — B, bicyclononanes, enamine
211
211.1 R = (R)-CH(CH3)C≡N hyperelanitrile D[d] (inseparable E/Z mixture with hyperelanitrile C at exocyclic double bond) H. elatoides N/D J.-Y. Xie 2024
211.2 R = (S)-CH(CH3)C≡N hyperelanitrile B[d] (inseparable E/Z mixture with hyperelanitrile A at exocyclic double bond) H. elatoides N/D J.-Y. Xie 2024
Structure 212: oblongifolin M — B, bicyclononanes, exo
212
212.1 oblongifolin M[c][l][m] G. oblongifolia −4.2 (0.05, m) H. Zhang 2014a
Structure 213: enervosanone — B, bicyclononanes, exo
213
213.1 enervosanone Calophyllum enervosum +10 (0.2000, m) M. Taher 2005
Structure 214: oxy-guttiferone K, oblongifolin G, oblongifolin I and others — B, bicyclononanes, exo
214
214.1 R1 = prenyl
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = OH
X3 = H		 oxy-guttiferone K[d] G. cambogia +20.9 (0.1) M. Masullo 2008, M. Masullo 2010
214.2 R1 = prenyl
R2 = geranyl
R3 = H
X1 = OH
X2 = OH
X3 = H		 oblongifolin G G. oblongifolia +5.9 (0.41) S.-X. Huang 2009
214.3 R1 = prenyl
R2 = geranyl
R3 = H
X1 = H
X2 = H
X3 = OH		 oblongifolin I G. oblongifolia NR Y. Zhou 2010
214.4 R1 = prenyl
R2 = geranyl
R3 = prenyl
X1 = OH
X2 = OH
X3 = H		 garciyunnanin B G. yunnanensis +18.1 (0.12) G. Xu 2008
214.5 R1 = prenyl
R2 = geranyl
R3 = prenyl
X1 = H
X2 = OH
X3 = OH		 garciyunnanin K[d] G. yunnanensis +2.2 (0.10, m) D. Zheng 2021b
214.6 R1 = geranyl
R2 = prenyl
R3 = H
X1 = OH
X2 = OH
X3 = H		 oxy-guttiferone M G. cambogia −96.2 (0.1, m) M. Masullo 2010
214.7 R1 = lavandulyl
R2 = prenyl
R3 = H
X1 = OH
X2 = OH
X3 = H		 symphonone H[e] S. globulifera −37 (0.2) G. Marti 2010
Structure 215: garcimultiflorone I, 2,16-oxyguttiferone A, oblongifolin F and others — B, bicyclononanes, endo
215
215.1 R1 = prenyl
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 garcimultiflorone I[d] G. multiflora −42.1 (0.36, m) W. Fu 2015
215.2 R1 = prenyl
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 2,16-oxyguttiferone A[d] S. globulifera +48 (1.0, m) K. Cottet 2015
215.3 R1 = prenyl
R2 = geranyl
R3 = H
X1 = OH
X2 = H		 oblongifolin F G. oblongifolia −85.6 (0.41) S.-X. Huang 2009
215.4 R1 = prenyl
R2 = geranyl
R3 = H
X1 = H
X2 = OH		 oblongifolin H G. oblongifolia NR Y. Zhou 2010
215.5 R1 = geranyl
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 oxy-guttiferone I G. cambogia +23.8 (0.1, m) M. Masullo 2010
215.6 R1 = (S)-lavandulyl[f]
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 garcimultiflorone J[c] G. multiflora +11.11 (0.44, m) W. Fu 2015, X. Wang 2021a
215.7 R1 = isolavandulyl[g]
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 nujiangefolin A[e] G. nujiangensis −2 (0.10, m) Z.-X. Xia 2012
215.8 R1 = (R)-isolavandulyl[g]
R2 = (E)-CH=CHCMe2OH
R3 = H
X1 = OH
X2 = H		 nujiangefolin D[d] G. nujiangensis −12 (0.10, m) Z. Tang 2019
215.9 R1 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 picrorhizone H[d] G. picrorhiza −7 (0.10, m) E. R. Sukandar 2020
215.10 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) L.-T. T. Nguyen 2012
215.11 R1 = (2S)-4-hydroxyisolavandulyl[g]
R2 = prenyl
R3 = H
X1 = OH
X2 = H		 garciesculentone B[e] G. esculenta +18.4 (0.04, m) H. Zhang 2014b
Structure 216: garcinialone — B, bicyclononanes, exo
216
216.1 garcinialone[l][m] G. multiflora −2.0 (0.02, m) S.-C. Chien 2008
Structure 217: xanthochymusone N — B, bicyclononanes, endo
217
217.1 xanthochymusone N[d] G. xanthochymus −16 (0.1, m) Y.-G. Fu 2025
Structure 218: no name — B, bicyclononanes, exo
218
218.1 no common name G. indica +18.9 (0.1, m) R. Kaur 2012
Structure 219: symphonone I — B, bicyclononanes, exo
219
219.1 symphonone I S. globulifera −22 (0.4) G. Marti 2010
Structure 220: (+)-garciyunnanin L, (−)-garciyunnanin L, xanthochymusone O — B, bicyclononanes, endo
220
220.1 R = prenyl (+)-garciyunnanin L[c] G. yunnanensis +28.5 (0.10, m) D. Zheng 2021b
220.2 R = prenyl (−)-garciyunnanin L[d] G. xanthochymus −21 (0.1, m) Y.-G. Fu 2025
220.3 R = CH2CH2CMe=CH2 xanthochymusone O[d] G. xanthochymus −21 (0.1, m) Y.-G. Fu 2025
Structure 221: oxy-guttiferone K2, garcixanthochymone J — B, bicyclononanes, exo
221
221.1 R1 = prenyl
R2 = prenyl		 oxy-guttiferone K2 G. cambogia +12.2 (0.1, m) M. Masullo 2010
221.2 R1 = isolavandulyl[g]
R2 = H		 garcixanthochymone J[d][e] G. xanthochymus +53.2 (0.73, m) S. Jin 2021
Structure 222: 4,16-oxyguttiferone A, guttiferone O, garcim-2 and others — B, bicyclononanes, endo
222
222.1 R1 = prenyl
R2 = prenyl
R3 = prenyl		 4,16-oxyguttiferone A S. globulifera +53 (1.0, m) K. Cottet 2015
222.2 R1 = prenyl
R2 = geranyl
R3 = H		 guttiferone O, a.k.a. oxy-oblongifolin A (one of two by that first name) G. afzelii +45 (0.2, a) A. M. Lannang 2010
222.3 R1 = (S)-lavandulyl[f]
R2 = prenyl
R3 = H		 garcim-2[c] G. xanthochymus N/A Z. Wu 2022
222.4 R1 = isolavandulyl[g]
R2 = prenyl
R3 = H		 nujiangefolin B[e] G. nujiangensis +5 (0.10, m) Z.-X. Xia 2012
Structure 223: garciyunnanensisin E — B, bicyclononanes, endo
223
223.1 garciyunnanensisin E[c][e] G. yunnanensis −120.0 (0.1, m) P.-X. Ji 2025
Structure 224: longistylione B, symphonone F, garcixanthochymone G — B, bicyclononanes, exo
224
224.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl		 longistylione B[c] H. longistylum +0.8 (0.04, mc) X. Cao 2017
224.2 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = prenyl
R4 = H		 symphonone F[e] S. globulifera −9 (1.0) G. Marti 2010
224.3 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = prenyl
R4 = H		 garcixanthochymone G[d][e] G. xanthochymus +28.5 (0.87, m) S. Jin 2021
Structure 225: longistylione A, hyperscabrone F, hyperkouytone F and others — B, bicyclononanes, exo
225
225.1 R1 = Ph
R2 = Me
R3 = prenyl		 longistylione A[c] H. longistylum −12.4 (0.4, mc) X. Cao 2017
225.2 R1 = Ph
R2 = prenyl
R3 = H		 hyperscabrone F[c] H. scabrum −18 (0.1, m) W. Gao 2016a
225.3 R1 = Ph
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl		 hyperkouytone F[c] H. kouytchense −46.5 (0.45, m) H.-Y. Lou 2024
225.4 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = H		 symphonone G[e] S. globulifera −4 (0.4) G. Marti 2010
Structure 226: hyperascyrin N — B, bicyclononanes, exo
226
226.1 hyperascyrin N[d] H. ascyron +40.0 (0.1, m) B. Zhen 2019
Structure 227: no name — B, bicyclononanes, caged
227
227.1 no common name H. scabrum +17.2 (1.0, m) S. Soroury 2020
Structure 228: hyperbeanin Q, garcimultinone K, paucinochymol C and others — B, bicyclononanes, endo
228
228.1 R1 = i-Pr
R2 = CMe2OH
R3 = geranyl
R4 = prenyl
R5 = H		 hyperbeanin Q[c] H. beanii −19.5 (0.4, m) X.-Y. Suo 2021b
228.2 R1 = Ph
R2 = CMe2OH
R3 = (2R,3E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R4 = prenyl
R5 = H		 garcimultinone K[d] G. multiflora −12.00 (0.05, m) H. Teng 2021
228.3 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = geranyl
R4 = prenyl
R5 = H		 paucinochymol C[d] G. paucinervis +17.2 (0.02, m) X. Tan 2020
228.4 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = lavandulyl
R4 = prenyl
R5 = H		 paucinochymol B[d][e] G. paucinervis −46.6 (0.02, m) X. Tan 2020
228.5 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = isolavandulyl[g]
R4 = prenyl
R5 = H		 nujiangefolin C[e] G. nujiangensis +20 (0.05, m) Z.-X. Xia 2012
228.6 R1 = 3,4-dihydroxyphenyl
R2 = CMe2OH
R3 = (E)-CH2CH(CMe=CH2)CH=CHCMe2OH
R4 = prenyl
R5 = H		 garciyunnanensisin D[d][e] G. yunnanensis +112.0 (0.1, m) P.-X. Ji 2025
228.7 R1 = 3,4-hydroxyphenyl
R2 = CMe2OH
R3 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R4 = prenyl
R5 = H		 picrorhizone F[d] G. picrorhiza +11 (0.10, m) E. R. Sukandar 2020
228.8 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 +11 (0.10, m) E. R. Sukandar 2020
Structure 229: hyperibone I, hyperibone H, garcimultinone L and others — B, bicyclononanes, endo
229
229.1 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H		 hyperibone I H. scabrum +13.3 (0.3) M. Matsuhisa 2002, R. Ciochina 2006, K. Lindermayr 2013
229.2 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = H		 hyperibone H H. scabrum +12.4 (0.4) M. Matsuhisa 2002, R. Ciochina 2006
229.3 R1 = Ph
R2 = (S)-lavandulyl[f]
R3 = prenyl
R4 = H		 garcimultinone L[d] G. multiflora +110.00 (0.04, m) H. Teng 2021
229.4 R1 = 3,4-dihydroxyphenyl
R2 = (S)-lavandulyl
R3 = prenyl
R4 = H		 garynthone D G. yunnanensis racemic; +21.52 (0.1, m) and −18.83 (0.1, m) Z. Guo 2025
229.5 R1 = 3,4-dihydroxyphenyl
R2 = (S)-isolavandulyl[g]
R3 = prenyl
R4 = H		 garynthone E[d] G. yunnanensis −31.07 (0.1, m) Z. Guo 2025
Structure 230: thorelione B — B, bicyclononanes, endo
230
230.1 thorelione B[e] Calophyllum thorelii +412.0 (0.14, e) L.-T. T. Nguyen 2012
Structure 231: oblongifolin X, garcowacinol E, garcowacinol G — B, bicyclononanes, exo
231
231.1 R1 = CMe=CH2
R2 = H		 oblongifolin X[d] G. oblongifolia −11.8 (0.03, m) H. Zhang 2016
231.2 R1 = CMe=CH2
R2 = prenyl		 garcowacinol E[d] G. cowa −36.0 (0.50, m) S. Kaennakam 2022b
231.3 R1 = CMe2OH
R2 = prenyl		 garcowacinol G[d] G. cowa −28.1 (0.30, m) S. Kaennakam 2022b
Structure 232: garcowacinol H — B, bicyclononanes, exo
232
232.1 garcowacinol H[d] G. cowa −21.2 (0.50, m) S. Kaennakam 2022b
Structure 233: garcowacinol F, guttiferone R, oblongifolin R and others — B, bicyclononanes, exo
233
233.1 R1 = H
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl		 garcowacinol F[d] G. cowa −25.0 (0.50, m) S. Kaennakam 2022b
233.2 R1 = H
R2 = CMe2OH
R3 = prenyl
R4 = prenyl		 guttiferone R[d] G. cochinchinensis −57.5 (0.33, m) H. D. Nguyen 2011, S. Kaennakam 2022b
233.3 R1 = H
R2 = CMe2OH
R3 = geranyl
R4 = H		 oblongifolin R[d][l][m] G. oblongifolia −54.5 (0.03, m) H. Zhang 2014a
233.4 R1 = prenyl
R2 = CMe=CH2
R3 = prenyl
R4 = H		 hyperscabrone E[d] H. scabrum −10 (0.1, m) W. Gao 2016a
Structure 234: mesuaferroic acid A, mesuaferroic acid E, mesuaferroic acid C and others — B, bicyclononanes, endo
234
234.1 R1 = s-Bu
R2 = CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid A[e][m] Mesua ferrea NR N. E. Rasol 2017
234.2 R1 = s-Bu
R2 = CHPhCH2CO2H
R3 = CH2CHOHCMe2OH		 mesuaferroic acid E[e][m] Mesua ferrea NR N. E. Rasol 2017
234.3 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid C[e][m] Mesua ferrea NR N. E. Rasol 2017
234.4 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = CH2CHOHCMe2OH		 mesuaferroic acid F[e][m] Mesua ferrea NR N. E. Rasol 2017
234.5 R1 = Ph
R2 = prenyl
R3 = prenyl		 sampsonione P, a.k.a. hyperscabrone L H. sampsonii, H. scabrum +18.6 (0.022), +40.0 (0.1, m) W. Gao 2016b, Z. Y. Xiao 2007
234.6 R1 = Ph
R2 = prenyl
R3 = (R)-CH2CHOHCMe2OH		 hypersampsone V[k] H. sampsonii +13.0 (0.50) W.-J. Tian 2016
234.7 R1 = Ph
R2 = prenyl
R3 = (S)-CH2CHOHCMe2OH		 hypersampsone W[k] H. sampsonii +0.60 (0.50) W.-J. Tian 2016
Structure 235: mesuaferroic acid B, mesuaferroic acid J, hyperattenin E and others — B, bicyclononanes, endo
235
235.1 R1 = s-Bu
R2 = CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid B[e][m] Mesua ferrea NR N. E. Rasol 2017
235.2 R1 = CH2CMe2OH
R2 = CHPhCH2CO2H
R3 = prenyl		 mesuaferroic acid J[e] Mesua ferrea +4.25 (0.2, m) X.-C. Zhang, 2020
235.3 R1 = Ph
R2 = prenyl
R3 = prenyl		 hyperattenin E, a.k.a. hyperibrin D[d] H. scabrum −13.0 (0.19, m) D. Li 2015a, W. Gao 2016c, X.-W. Yang 2018
235.4 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-6,6-dimethyl-2-methylenecyclohexylmethyl		 paucinone D G. paucinervis +41.6 (0.11, m) X.-M. Gao 2010
Structure 236: paucinone A — B, bicyclononanes, endo
236
236.1 paucinone A G. paucinervis −6.2 (0.05, m) X.-M. Gao 2010
Structure 237: paucinone B — B, bicyclononanes, endo
237
237.1 paucinone B G. paucinervis +58.7 (0.10, m) X.-M. Gao 2010
Structure 238: paucinone C — B, bicyclononanes, endo
238
238.1 paucinone C G. paucinervis +19.2 (0.17, m) X.-M. Gao 2010
Structure 239: garcicowin A — B, bicyclononanes, noC3
239
239.1 garcicowin A G. cowa −219.0 (0.09) G. Xu 2010
Structure 240: garcowacinol D — B, bicyclononanes, noC3
240
240.1 garcowacinol D[d] G. cowa +37.0 (0.50, m) S. Kaennakam 2022b
Structure 241: garcowacinol C, oblongifolin S, xanthochymusone G — B, bicyclononanes, exo
241
241.1 R1 = Ph
R2 = H
R3 = H
R4 = prenyl
R5 = prenyl		 garcowacinol C[d] G. cowa +28.5 (0.50, m) S. Kaennakam 2022b
241.2 R1 = Ph
R2 = H
R3 = OH
R4 = geranyl
R5 = H		 oblongifolin S[d][l][m] G. oblongifolia −37.8 (0.04, m) H. Zhang 2014a
241.3 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H		 xanthochymusone G[d] G. xanthochymus −141 (0.1, m) Z.-H. Xu 2022
Structure 242: oblongifolin W, 13,14-didehydroxy-7-epi-isogarcinol, 14-deoxy-7-epi-isogarcinol and others — B, bicyclononanes, exo
242
242.1 R1 = Ph
R2 = H
R3 = H
R4 = (E)-CH=CHCMe=O		 oblongifolin W[d] G. oblongifolia +20.0 (0.03, m) H. Zhang 2016
242.2 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl		 13,14-didehydroxy-7-epi-isogarcinol G. multiflora −185 (0.13) J.-J. Chen 2009, X. Wang 2021a
242.3 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl		 14-deoxy-7-epi-isogarcinol S. globulifera −77 (0.9) G. Marti 2010
242.4 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl		 7-epi-isogarcinol M. coccinea, S. globulifera −158 (1.0) G. Marti 2009, G. Marti 2010
242.5 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = 3-methylbutyl		 epunctanone G. epunctata Stapf +24.9 (0.00985, a) G. Y. T. Fotso 2014
242.6 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe=CH2		 symphonone A S. globulifera −37 (0.7) G. Marti 2010
242.7 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH		 symphonone C S. globulifera −67 (1.0) G. Marti 2010
242.8 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl		 symphonone B S. globulifera −81 (1.0) G. Marti 2010
242.9 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl		 7-epi-coccinone B S. globulifera −50 (0.9) G. Marti 2010
242.10 R1 = 3,4-hydroxyphenyl
R2 = prenyl
R3 = CH2CH2CMe=CH2
R4 = prenyl		 xanthochymusone F[d] G. xanthochymus +141 (0.1, m) Z.-H. Xu 2022
242.11 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CHOHCMe2OH
R4 = prenyl		 symphonone D[e] S. globulifera −41 (0.4) G. Marti 2010
242.12 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CHOHCMe2OH
R4 = prenyl		 symphonone E[e] (diastereomer) S. globulifera −50 (0.4) G. Marti 2010
Structure 243: oblongifolin Y, hypersampsonone J, guttiferone T — B, bicyclononanes, endo
243
243.1 R1 = Ph
R2 = H
R3 = H
R4 = CH2CO2H		 oblongifolin Y[d] G. oblongifolia +24.1 (0.06, m) H. Zhang 2016
243.2 R1 = Ph
R2 = prenyl
R3 = OH
R4 = prenyl		 hypersampsonone J[d] H. sampsonii +17.5 (1.0, m) Y. Li 2023
243.3 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CH2CMe=CH2
R4 = CH2CHOHCMe=CH2		 guttiferone T[e] G. cochinchinensis −14 (0.3) B. T. D. Trinh 2013
Structure 244: 13,14-didehydroxyisoxanthochymol, garcimultinone M, 14-deoxyisogarcinol and others — B, bicyclononanes, endo
244
244.1 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 13,14-didehydroxyisoxanthochymol[d] G. multiflora +205.7 (0.15) L.-Y. Cheng 2018b
244.2 R1 = Ph
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 garcimultinone M[c] (enantiomer) G. multiflora −114.44 (0.02, m) H. Teng 2021
244.3 R1 = 3-hydroxyphenyl
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 14-deoxyisogarcinol G. indica −178.0 (0.1, m) R. Kaur 2012
244.4 R1 = 3-hydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 xanthochymusone C[d] G. xanthochymus +132 (0.1, m) Z.-H. Xu 2022
244.5 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl		 isoxanthochymol[d] G. pyrifera, G. subelliptica, G. xanthochymus, G. ovafolia +181 (0.6, e) C. G. Karanjgoakar 1973, K. R. Gustafson 1992, M. Iinuma 1996, D. Roux 2000, S. Baggett 2005, C. Socolsky 2015
244.6 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 −224 (0.1, m) 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
244.7 R1 = 3,4-hydroxyphenyl
R2 = Me
R3 = prenyl
R4 = CH2CH2CMe2OH
R5 = prenyl		 xanthochymusone D[d] G. xanthochymus +186 (0.1, m) Z.-H. Xu 2022
244.8 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 (+)-cycloxanthochymol G. pyrifera, G. subelliptica, M. coccinea +112 (1) M. Iinuma 1996, D. Roux 2000, G. Marti 2009
244.9 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 (−)-cycloxanthochymol[j] (enantiomer) G. subelliptica −80.9 (2.20, m) L.-J. Zhang 2010
244.10 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = prenyl
R4 = CH2CHOHCMe2OH
R5 = prenyl		 coccinone D[e] M. coccinea −76 (0.4) G. Marti 2009
244.11 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = prenyl
R4 = CH2CHOHCMe2OH
R5 = prenyl		 coccinone E[e] (diastereomer) M. coccinea −70 (0.3) G. Marti 2009
244.12 R1 = 3,4-hydroxyphenyl
R2 = Me
R3 = CH2CH2CMe=CH2
R4 = CH2CH2CMe2OH
R5 = prenyl		 xanthochymusone E[d] G. xanthochymus +117 (0.1, m) Z.-H. Xu 2022
244.13 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe2OH
R4 = prenyl
R5 = prenyl		 coccinone C M. coccinea −60 (0.2) G. Marti 2009
244.14 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = (S)-CH2CH(OH)CMe=CH2
R4 = prenyl
R5 = prenyl		 garpedvinin F[c] G. pedunculata Roxb. −118.3 (0.1, m) D.-L. Zou 2025
244.15 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe2OH
R4 = (S)-CH2CHOHCMe2OH
R5 = CH2CH2CMe2OH		 garcixanthochymone H[d] G. xanthochymus +31.6 (0.25, m) S. Jin 2021
244.16 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2CH2CMe2OH
R4 = (R)-CH2CHOHCMe2OH
R5 = CH2CH2CMe2OH		 garcixanthochymone I[d] G. xanthochymus +17.8 (0.33, m) S. Jin 2021
244.17 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = CH2COCMe=CH2
R4 = prenyl
R5 = prenyl		 garcixanthochymone F[d] G. xanthochymus +55.3 (0.21, m) S. Jin 2021
244.18 R1 = 3,4-dihydroxyphenyl
R2 = Me
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl		 coccinone B M. coccinea −55 (0.3) G. Marti 2009
244.19 R1 = 3,4-dihydroxyphenyl
R2 = CH2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl		 garynthone H G. yunnanensis racemic; +160.00 (0.1, m) and −182.25 (0.1, m) Z. Guo 2025
244.20 R1 = 3,4-dihydroxyphenyl
R2 = CH2OH
R3 = CH2CH2CMe=CH2
R4 = prenyl
R5 = prenyl		 garynthone I[d] G. yunnanensis +96.5 (0.1, m) Z. Guo 2025
Structure 245: garpedvinin E — B, bicyclononanes, endo
245
245.1 garpedvinin E[c] G. pedunculata Roxb. −86.6 (0.30, m) D.-L. Zou 2025
Structure 246: garpedvinin A — B, bicyclononanes, endo
246
246.1 garpedvinin A[c] G. pedunculata Roxb. −86.6 (0.30, m) D.-L. Zou 2025
Structure 247: garciesculentone A — B, bicyclononanes, endo
247
247.1 garciesculentone A[m] G. esculenta −116.5 (0.06, m) H. Zhang 2014b
Structure 248: garcinialiptone B — B, bicyclononanes, endo
248
248.1 garcinialiptone B G. subelliptica +84.8 (5.40, m) L.-J. Zhang 2010
Structure 249: garcicowin D — B, bicyclononanes, exo
249
249.1 garcicowin D G. cowa +336.0 (0.12) G. Xu 2010, Z.-H. Xu 2022
Structure 250: 13,14-didehydroxygarcicowin C, xanthochymusone H, garcicowin C and others — B, bicyclononanes, endo
250
250.1 R1 = Ph
R2 = CH=CMe2		 13,14-didehydroxygarcicowin C[c] G. multiflora −68.6 (0.18) L.-Y. Cheng 2018b, Y.-G. Fu 2025
250.2 R1 = 3-hydroxyphenyl
R2 = CH=CMe2		 xanthochymusone H[d] G. xanthochymus +60 (0.1, m) Z.-H. Xu 2022
250.3 R1 = 3,4-dihydroxyphenyl
R2 = CH=CMe2		 garcicowin C[c] G. cowa −72.1 (0.10) G. Xu 2010, Z.-H. Xu 2022
250.4 R1 = 3,4-dihydroxyphenyl
R2 = CH=CMe2		 xanthochymusone I[d] (enantiomer) G. xanthochymus +69 (0.1, m) Z.-H. Xu 2022
250.5 R1 = 3,4-dihydroxyphenyl
R2 = (R)-CH(OH)CMe2OH		 garynthone G G. yunnanensis racemic; +160 (0.1, m) and −76.85 (0.1, m) Z. Guo 2025
250.6 R1 = 3,4-dihydroxyphenyl
R2 = (R)-CH(OH)CMe2OMe		 garynthone F G. yunnanensis racemic; +114.47 (0.1, m) and −135.64 (0.1, m) Z. Guo 2025
Structure 251: garpedvinin D — B, bicyclononanes, endo
251
251.1 garpedvinin D[c] G. pedunculata Roxb. −54.6 (0.1, m) D.-L. Zou 2025
Structure 252: garcoblone E — B, bicyclononanes, endo
252
252.1 garcoblone E[c] G. oblongifolia, G. yunnanensis −44.5 (1.0, m) Z. Wu 2022, Z. Guo 2025
Structure 253: coccinone A — B, bicyclononanes, endo
253
253.1 coccinone A M. coccinea +28 (1.0) G. Marti 2009
Structure 254: garpedvinin B — B, bicyclononanes, endo
254
254.1 garpedvinin B[c] G. pedunculata Roxb. −65.5 (0.1, m) D.-L. Zou 2025
Structure 255: garpedvinin C — B, bicyclononanes, endo
255
255.1 garpedvinin C[c] G. pedunculata Roxb. −68.8 (0.1, m) D.-L. Zou 2025
Structure 256: garcimultiflorone B, 13-hydroxygarcimultiflorone B — B, bicyclononanes, endo
256
256.1 R = Ph garcimultiflorone B G. multiflora −132 (0.96) J.-J. Chen 2009
256.2 R = 3-hydroxyphenyl 13-hydroxygarcimultiflorone B G. multiflora −115 (0.13) J.-J. Chen 2009
Structure 257: hyperascyrin M — B, bicyclononanes, endo
257
257.1 hyperascyrin M[d] H. ascyron −57.2 (0.1, m) B. Zhen 2019
Structure 258: garschomcinol E, garschomcinol D — B, bicyclononanes, endo
258
258.1 R = CH2CH2CHMeCO2H garschomcinol E[d][e] G. schomburgkiana +12.5 (0.20, m) S. Kaennakam 2022a
258.2 R = geranyl garschomcinol D[d] G. schomburgkiana +13.1 (0.30, m) S. Kaennakam 2022a
Structure 259: guttiferone S, longistylione D, ascyrone C and others — B, bicyclononanes, exo
259
259.1 R1 = H
R2 = prenyl
R3 = prenyl		 guttiferone S G. cochinchinensis −10 (0.28, m) H. D. Nguyen 2011, D. H. Le 2016
259.2 R1 = prenyl
R2 = Me
R3 = prenyl		 longistylione D[c] H. longistylum +19.5 (0.13, mc) X. Cao 2017
259.3 R1 = prenyl
R2 = Me
R3 = (E)-CH=CHCMe2OH		 ascyrone C[d] H. ascyron +78 (0.06, m) X. Deng 2022
259.4 R1 = prenyl
R2 = Me
R3 = (E)-CH=CHC(Me)=CH2		 ascyrone E[d] H. ascyron +3 (0.09, MeOH) X. Deng 2022
Structure 260: garcowacinol J, garcowacinol I, longistylione C and others — B, bicyclononanes, exo
260
260.1 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = CMe=CH2		 garcowacinol J[d] G. cowa +18.0 (0.10, m) S. Kaennakam 2022b
260.2 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = CMe2OH		 garcowacinol I[d] G. cowa +13.5 (0.10, m) S. Kaennakam 2022b
260.3 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = CMe2OH		 longistylione C[c] H. longistylum +154.3 (0.33, mc) X. Cao 2017
260.4 R1 = Ph
R2 = prenyl
R3 = Me
R4 = (E)-CH=CHCMe2OH
R5 = CMe2OH		 ascyrone D[d] H. ascyron +11 (0.11, m) X. Deng 2022
260.5 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = Me
R4 = prenyl
R5 = CMe2OH		 ascyrone A[d] H. ascyron +6 (0.05, m) X. Deng 2022
260.6 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = Me
R4 = (E)-CH=CHCMe2OH
R5 = CMe2OH		 ascyrone B[d] H. ascyron +34 (0.16, m) X. Deng 2022
260.7 R1 = 3,4-dihydroxyphenyl
R2 = H
R3 = prenyl
R4 = geranyl
R5 = CMe2OH		 schomburgkianone E[d] G. schomburgkiana +104 (0.4) D. H. Le 2016
Structure 261: guttiferone H — B, bicyclononanes, exo
261
261.1 guttiferone H[e] G. xanthochymus +94 (0.006) S. Baggett 2005
Structure 262: garcixanthochymone K — B, bicyclononanes, exo
262
262.1 garcixanthochymone K[d] G. xanthochymus −37.9 (0.20, m) S. Jin 2021
Structure 263: burlemarxione E — B, bicyclononanes, caged
263
263.1 burlemarxione E C. burlemarxii +11.0 (0.5) C. G. Ferraz 2021
Structure 264: hyperprin A — B, bicyclononanes, caged
264
264.1 hyperprin A[d] H. przewalskii −4.0 (0.10, m) J.-F. Zong 2020
Structure 265: garciyunnanol D, garciyunnanol C, garciyunnanol B — B, bicyclononanes, exo
265
265.1 R = prenyl
X = OH		 garciyunnanol D[d] G. yunnanensis +158 (0.64, m) X.-Y. Hu 2024
265.2 R = geranyl
X = H		 garciyunnanol C[d] G. yunnanensis +17 (0.18, m) X.-Y. Hu 2024
265.3 R = geranyl
X = OH		 garciyunnanol B[d] G. yunnanensis +115 (0.39, m) X.-Y. Hu 2024
Structure 266: garciyunnanol A — B, bicyclononanes, exo
266
266.1 garciyunnanol A[d] G. yunnanensis +14 (0.16, m) X.-Y. Hu 2024
Structure 267: thoreliolide A — B, bicyclononanes, endo
267
267.1 thoreliolide A[d][e] Calophyllum thorelii +82.0 (0.45, e) L.-T. T. Nguyen 2016
Structure 268: thoreliolide B — B, bicyclononanes, exo
268
268.1 thoreliolide B[d] Calophyllum thorelii −51.2 (0.75, e) L.-T. Nguyen 2016
Structure 269: hyperibone K, hypersampsonone K, hyperibrin E and others — B, bicyclononanes, caged
269
269.1 R1 = Ph
R2 = prenyl
R3 = CH=CMe2
R4 = prenyl		 hyperibone K[d] H. scabrum +22.3 (0.3) N. Tanaka 2004, J. Qi 2010
269.2 R1 = Ph
R2 = prenyl
R3 = CH=CMe2
R4 = (E)-4-oxo-3-methyl-2-buten-1-yl		 hypersampsonone K[d] H. sampsonii −7.5 (1.0, m) Y. Li 2023
269.3 R1 = Ph
R2 = prenyl
R3 = CH2C(=O)CH3
R4 = prenyl		 hyperibrin E[d] H. scabrum +47.3 ( 0.06, m) J. Hu 2017
269.4 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = CH=CMe2
R4 = prenyl		 18-hydroxyhyperibone K H. hypericoides NR O. E. Christian 2008
269.5 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2C(=O)CH3
R4 = prenyl		 oblongifolin K[c] G. oblongifolia +55.4 (0.07, m) H. Zhang 2014a
269.6 R1 = 3,4-dihydroxyphenyl
R2 = lavandulyl
R3 = CH=CMe2
R4 = prenyl		 garciniagifolone A[e] G. oblongifolia +7.0 (0.09, m) W.-G. Shan 2012
269.7 R1 = 3,4-dihydroxyphenyl
R2 = 2,4,4-trimethyl-1-cyclohexen-1-ylmethyl
R3 = CH=CMe2
R4 = prenyl		 garpauvinin A[d] G. paucinervis −49.86 (c 0.91, m) C.-C. Jia 2023
269.8 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = CH=CMe2
R4 = prenyl		 (+)-garcinialiptone A[e][j] G. subelliptica +12.1 (3.40, m) L.-J. Zhang 2010
269.9 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = CH=CMe2
R4 = prenyl		 (−)-garcinialiptone A[e][j] (enantiomer) G. subelliptica, G. yunnanensis −17.3 (3.36, m) L.-J. Zhang 2010
269.10 R1 = 3,4-dihydroxyphenyl
R2 = CH2CH(CMe=CH2)CH2CH2CMe2OH
R3 = CH=CMe2
R4 = prenyl		 garcixanthochymone A[e] G. xanthochymus −13.8 (0.660, m) Y. Chen 2017
269.11 R1 = 3,4-dihydroxyphenyl
R2 = (E)-CH2CH(CMe=CH2)CH=CHCMe2OH
R3 = CH=CMe2
R4 = prenyl		 garciyunnanensisin B[d][e] G. yunnanensis −130.8 (0.1, m) P.-X. Ji 2025
269.12 R1 = 3,4-dihydroxyphenyl
R2 = (S)-lavandulyl
R3 = (R)-3,3-dimethyloxiran-2-yl
R4 = prenyl		 garpedvinin I[d] G. pedunculata Roxb. −54.7 (0.1, m) D.-L. Zou 2025
269.13 R1 = 3,4-dihydroxyphenyl
R2 = (2R,4S)-CH2CH(CMe=CH2)CH2CH(OOH)CMe=CH2
R3 = CH=CMe2
R4 = prenyl		 garpedvinin J[d] G. pedunculata Roxb. −79.0 (0.1, m) D.-L. Zou 2025
269.14 R1 = 3,4-dihydroxyphenyl
R2 = (S,E)-CH2CH(CMe=CH2)CH=CHCMe2OH
R3 = CH=CMe2
R4 = prenyl		 garpedvinin H[d] G. pedunculata Roxb. −79.0 (0.1, m) D.-L. Zou 2025
269.15 R1 = 3,4-dihydroxyphenyl
R2 = (S,E)-CH2CH(CMe=CH2)CH=CHCMe2OOH
R3 = CH=CMe2
R4 = prenyl		 garpedvinin G[d] G. pedunculata Roxb. −118.3 (0.1, m) D.-L. Zou 2025
269.16 R1 = 3,4-dihydroxyphenyl
R2 = 4-hydroxyisolavandulyl[g]
R3 = CH=CMe2
R4 = prenyl		 garcixanthochymone B[e] G. xanthochymus −0.81 (0.410, m) Y. Chen 2017
269.17 R1 = 3,4-dihydroxyphenyl
R2 = isolavandulyl[g]
R3 = OH
R4 = prenyl		 garciyunnanensisin A[d][e] G. yunnanensis −150.2 (0.1, m) P.-X. Ji 2025
Structure 270: garcixanthochymone C — B, bicyclononanes, caged
270
270.1 garcixanthochymone C G. xanthochymus +51.0 (0.400, m) Y. Chen 2017
Structure 271: oblongifolin J — B, bicyclononanes, caged
271
271.1 oblongifolin J[c] G. oblongifolia +8.6 (0.03, m) H. Zhang 2014a
Structure 272: hypersampsone R — B, bicyclononanes, endo
272
272.1 hypersampsone R (one of two by that name) H. sampsonii +160 (0.1) J.-J. Chen 2014
Structure 273: garcimultiflorone C — B, bicyclononanes, caged
273
273.1 garcimultiflorone C[e] G. multiflora −25.3 (0.12) J.-J. Chen 2009
Structure 274: garynthone B, garynthone C — B, bicyclononanes, caged
274
274.1 R = (S)-lavandulyl garynthone B G. yunnanensis racemic; +28.70 (0.1, m) and −30.33 (0.1, m) Z. Guo 2025
274.2 R = (S)-isolavandulyl[g] garynthone C[d] G. yunnanensis +7.85 (0.1, m) Z. Guo 2025
Structure 275: soniiglucinol A — A, bicyclononanes, endo
275
275.1 soniiglucinol A[c] H. wilsonii −74.0 (0.2, m) S. Xie 2020a
Structure 276: soniiglucinol B — A, bicyclononanes, endo
276
276.1 soniiglucinol B[c][e] H. wilsonii −139.4 (0.4, m) S. Xie 2020a
Structure 277: hypersonin A, hypersonin C, hypersonin B — A, bicyclononanes, endo
277
277.1 R1 = i-Pr
R2 = prenyl		 hypersonin A[c] H. wilsonii −13 (0.9, m) S. Xie 2020b
277.2 R1 = i-Pr
R2 = geranyl		 hypersonin C[c] H. wilsonii −2 (0.4, m) S. Xie 2020b
277.3 R1 = s-Bu
R2 = prenyl		 hypersonin B[c][e] H. wilsonii +3 (0.9, m) S. Xie 2020b
Structure 278: hypersonin D — A, bicyclononanes, endo
278
278.1 hypersonin D[c][e] H. wilsonii −1 (0.2, m) S. Xie 2020b
Structure 279: soniiglucinol C — A, bicyclononanes, endo
279
279.1 soniiglucinol C[c] H. wilsonii −151.3 (0.3, m) S. Xie 2020a
Structure 280: soniiglucinol D — A, bicyclononanes, endo
280
280.1 soniiglucinol D[c] H. wilsonii −24.9 (0.2, m) S. Xie 2020a
Structure 281: enaimeone A — B, bicyclooctanes
281
281.1 enaimeone A H. papuanum +27.8 (0.1, m) K. Winkelmann 2001b, A. B. zur Bonsen 2023
Structure 282: enaimeone B, enaimeone C — B, bicyclooctanes
282
282.1 R = i-Pr enaimeone B H. papuanum +29.4 (0.1, m) K. Winkelmann 2001b, A. B. zur Bonsen 2023
282.2 R = s-Bu enaimeone C[e] H. papuanum +32.9 (0.1, m) K. Winkelmann 2001b, A. B. zur Bonsen 2023
Structure 283: hyperxylone B, hyperxylone A — B, bicyclooctanes
283
283.1 R1 = H
R2 = geranyl		 hyperxylone B[c] H. beanii +41 (0.09, m) X.-Y. Li 2022
283.2 R1 = prenyl
R2 = prenyl		 hyperxylone A[c] H. beanii +38 (0.08, m) X.-Y. Li 2022
Structure 284: ialibinone A, 1′-hydroxyialibinone A, yezo'otogirin E and others — B, bicyclooctanes
284
284.1 R1 = i-Pr
R2 = CMe=CH2		 ialibinone A H. papuanum −22 (0.1) K. Winkelmann 2000
284.2 R1 = i-Pr
R2 = CMe2OH		 1′-hydroxyialibinone A H. papuanum +3.7 (0.1, m) K. Winkelmann 2001b
284.3 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2		 yezo'otogirin E H. yezoense +21.4 (1.7, m) N. Tanaka 2016a
284.4 R1 = s-Bu
R2 = CMe=CH2		 ialibinone C[e] H. papuanum −26 (0.1) K. Winkelmann 2000
Structure 285: ialibinone E, ialibinone B, 1′-hydroxyialibinone B and others — B, bicyclooctanes
285
285.1 R1 = i-Pr
R2 = H		 ialibinone E H. papuanum −33 (0.1) K. Winkelmann 2000
285.2 R1 = i-Pr
R2 = CMe=CH2		 ialibinone B H. papuanum −91 (0.1) K. Winkelmann 2000
285.3 R1 = i-Pr
R2 = CMe2OH		 1′-hydroxyialibinone B H. papuanum −35.7 (0.1, m) K. Winkelmann 2001b
285.4 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2		 yezo'otogirin F H. yezoense +75.9 (1.7, m) N. Tanaka 2016a
285.5 R1 = s-Bu
R2 = CMe=CH2		 ialibinone D[e] H. papuanum −72 (0.1) K. Winkelmann 2000
285.6 R1 = s-Bu
R2 = CMe2OH		 1′-hydroxyialibinone D[e] H. papuanum −30.3 (0.1, m) K. Winkelmann 2001b
Structure 286: lancasternoid A — B, bicyclooctanes
286
286.1 lancasternoid A H. lancasteri racemic J.-Q. You 2025
Structure 287: lancasternoid B — B, bicyclooctanes
287
287.1 lancasternoid B H. lancasteri racemic J.-Q. You 2025
Structure 288: lancasternoid C — B, bicyclooctanes
288
288.1 lancasternoid C H. lancasteri racemic J.-Q. You 2025
Structure 289: lancasternoid D — B, bicyclooctanes
289
289.1 lancasternoid D H. lancasteri racemic J.-Q. You 2025
Structure 290: takaneone A — B, bicyclooctanes, twoC3
290
290.1 takaneone A H. sikokumontanum +30.0 (0.2, m) N. Tanaka 2008
Structure 291: takaneone B — B, bicyclooctanes, twoC3
291
291.1 takaneone B H. sikokumontanum +24.0 (0.3, m) N. Tanaka 2008
Structure 292: takaneone C, hyperelodione E — A, bicyclooctanes, twoC3
292
292.1 R = COCH3 takaneone C H. sikokumontanum +61.9 (0.4, m) N. Tanaka 2008
292.2 R = C(=CH2)CH2CH2CH=CMe2 hyperelodione E[d] H. elodeoides +44.0 (0.24, m) D.-R. Qiu 2021
Structure 293: hyperelodione F — A, bicyclooctanes, twoC3
293
293.1 hyperelodione F[d] H. elodeoides +24.8 (0.33, m) D.-R. Qiu 2021
Structure 294: garcibracgluinol A — bicyclooctanes, seco
294
294.1 garcibracgluinol A[c] G. bracteata +141.4 (0.02, m) J. Xu 2025
Structure 295: no name — B, bicyclooctanes, seco
295
295.1 no common name H. scabrum +30.5 (1.0) S. Soroury 2020
Structure 296: hyperireflexolide A — otherSpiro, seco
296
296.1 hyperireflexolide A[c] H. beanni 0 (1.54) L. Cardona 1993
Structure 297: hyperireflexolide B — otherSpiro, seco
297
297.1 hyperireflexolide B[c] H. beanni 0 (0.74) L. Cardona 1993, A. B. zur Bonsen 2023
Structure 298: hyperberlone A — otherBridgedBicycles, seco
298
298.1 hyperberlone A[c] H. beanni 0 (0.74) Y.-W. Li 2022
Structure 299: garcinielliptone HG, garcinielliptone HH — B, bicyclooctanes
299
299.1 garcinielliptone HG[c] G. subelliptica −17 (0.02, m) C.-C. Liaw 2019
299.2 garcinielliptone HH[d] (enantiomer) G. subelliptica +16 (0.05, m) C.-C. Liaw 2019
Structure 300: (−)-nemorosonol, (+)-nemorosonol, garmultinone D and others — caged, fourPlusTwo
300
300.1 R1 = prenyl
R2 = H
R3 = prenyl		 (−)-nemorosonol, a.k.a. burlemarxione C[c] C. burle-marxii, T. japonicum −207 (0.7), −48 (1.35) A. Oya 2015, C. G. Ferraz 2019, M. do C. C. Silva 2024
300.2 R1 = prenyl
R2 = H
R3 = prenyl		 (+)-nemorosonol[d] (enantiomer) C. nemorosa +203 (0.7) F. Delle Monache 1988, S. Cerrini 1993
300.3 R1 = prenyl
R2 = H
R3 = cis-3-isopropenyl-2,2-dimethylcyclopentyl		 garmultinone D[d][e] G. multiflora +172.5 (0.04, m) Y. Chen 2019b
300.4 R1 = CH2CH2CMe=CH2
R2 = H
R3 = prenyl		 doitunggarcinone B, a.k.a. burlemarxione G C burle-marxii, G. propinqua −129 (0.054), −14.0 (0.5) C. Tantapakul 2012, H. P. Pepper 2012, C. G. Ferraz 2021, M. do C. C. Silva 2024
300.5 R1 = prenyl
R2 = prenyl
R3 = prenyl		 ascyronone E, a.k.a. hypatulin C[d][w] H. ascyron, H. patulum −86.8 (0.1, m), +102.5 (0.3, m) Z. P. Li 2019, N. Tanaka 2019
Structure 301: trijapin A — caged, fourPlusTwo
301
301.1 trijapin A[c] T. japonicum −25 (0.2, m) A. Oya 2015
Structure 302: trijapin B, garcibracteamone J — caged, fourPlusTwo
302
302.1 R = prenyl trijapin B T. japonicum −200 (0.1, m) A. Oya 2015
302.2 R = CH2CH2CMe=CH2 garcibracteamone J[c] G. bracteata −169 (0.02, m) Q. Xue 2020
Structure 303: trijapin C — caged, fourPlusTwo
303
303.1 trijapin C T. japonicum +38 (0.04, m) A. Oya 2015
Structure 304: garmultinone A, garmultinone C — caged, fourPlusTwo
304
304.1 R = prenyl garmultinone A[d] G. multiflora +176.4 (0.04, m) Y. Chen 2019b
304.2 R = (E)-CH=CHCMe2OOH garmultinone C[d] G. multiflora +207.2 (0.02, m) Y. Chen 2019b
Structure 305: garmultinone B, 30-hydroxy-garmultinone B — caged, fourPlusTwo
305
305.1 R = Ph garmultinone B[d] G. multiflora +173.9 (0.06, m) Y. Chen 2019b
305.2 R = 3-hydroxyphenyl 30-hydroxy-garmultinone B[d] G. multiflora +25.0 (0.1, m) J. Cao 2024
Structure 306: garmultinone E — caged, fourPlusTwo
306
306.1 garmultinone E[d] (one of two by that name) G. multiflora +85.0 (0.1, m) J. Cao 2024
Structure 307: garmultinone F — caged, fourPlusTwo
307
307.1 garmultinone F[d] G. multiflora +141.0 (0.1, m) J. Cao 2024
Structure 308: (−)-garcimulin A, (+)-garcimulin A, garcimulin B and others — A, bicyclononanes, caged
308
308.1 R1 = prenyl
R2 = prenyl		 (−)-garcimulin A[c] G. multiflora −142.9 (0.11, m) Y.-M. Fan 2015
308.2 R1 = prenyl
R2 = prenyl		 (+)-garcimulin A[d] (enantiomer) G. multiflora +115.1 (0.11, m) Y.-M. Fan 2015
308.3 R1 = CH2CH2CMe=CH2
R2 = prenyl		 garcimulin B[c] G. multiflora −118.5 (0.21, m) Y.-M. Fan 2015
308.4 R1 = CH2CH2CMe2OH
R2 = prenyl		 garcimulin C[d] G. multiflora +67.0 (0.1, m) J. Cao 2024
Structure 309: (−)-garmultin D, (+)-garmultin D, garmultin H and others — caged, fourPlusTwo
309
309.1 R1 = prenyl
R2 = prenyl		 (−)-garmultin D[c] G. multiflora −166.7 (0.28, m) D. S. Tian 2016
309.2 R1 = prenyl
R2 = prenyl		 (+)-garmultin D[d] (enantiomer) G. multiflora +164.9 (0.30, m) D. S. Tian 2016
309.3 R1 = prenyl
R2 = CH2CH2CMe2OH		 garmultin H[d] G. multiflora +77.0 (0.1, m) H. Luo 2025
309.4 R1 = CH2CH2CMe=CH2
R2 = prenyl		 garmultin E[d] G. multiflora −79.2 (0.29, m) D. S. Tian 2016
Structure 310: (−)-garmultin C, (+)-garmultin C — caged, fourPlusTwo
310
310.1 (−)-garmultin C[c] G. multiflora −85.0 (0.20, m) D. S. Tian 2016
310.2 (+)-garmultin C[d] (enantiomer) G. multiflora +72.6 (0.23, m) D. S. Tian 2016
Structure 311: (−)-garmultin A, (+)-garmultin A, garmultin B — caged, fourPlusTwo
311
311.1 R = prenyl (−)-garmultin A[c] G. multiflora −112.8 (0.24, a) D. S. Tian 2016
311.2 R = prenyl (+)-garmultin A[d] (enantiomer) G. multiflora +110.2 (0.22, a) D. S. Tian 2016
311.3 R = CH2CH2CMe=CH2 garmultin B[d] G. multiflora −53.0 (0.37, m) D. S. Tian 2016
Structure 312: (−)-garmultin F, (+)-garmultin F, garmultin G — caged, fourPlusTwo
312
312.1 R = prenyl (−)-garmultin F[c] G. multiflora −39.0 (0.32, m) D. S. Tian 2016
312.2 R = prenyl (+)-garmultin F[d] (enantiomer) G. multiflora +30.2 (0.37, m) D. S. Tian 2016
312.3 R = CH2CH2CMe=CH2 garmultin G[d] G. multiflora −20.4 (0.25, m) D. S. Tian 2016
Structure 313: hyperuralone A — caged, fourPlusTwo
313
313.1 hyperuralone A[d] H. uralum +34.3 (0.2, m) J.-J. Zhang 2014b
Structure 314: hyperforcinol B — caged, fourPlusTwo
314
314.1 hyperforcinol B[d] H. forrestii +72 (0.2, m) W.-J. Lu 2021
Structure 315: uralin A — caged, fourPlusTwo
315
315.1 uralin A, a.k.a. hyperacmosin N[d] H. acmosepalum, H. uralum +71 (0.2, m), +47.3 (0.1, m) Q.-Q. Fang 2021, M.-x. Sun 2021b
Structure 316: burlemarxione A — caged, fourPlusTwo
316
316.1 burlemarxione A C. burlemarxii −113.0 (1.35) C. G. Ferraz 2019
Structure 317: garcibractinone B, garcibractinone A — caged, fourPlusTwo, seco
317
317.1 R = prenyl garcibractinone B[c] G. bracteata +20 (0.05, m) Y. Chen 2020
317.2 R = CH2CH2CMe=CH2 garcibractinone A[c] G. bracteata +72 (0.05, m) Y. Chen 2020
Structure 318: hypatulin A — caged, fourPlusTwo, seco
318
318.1 hypatulin A[c] H. patulum +40 (0.05, m) N. Tanaka 2016b
Structure 319: hyperforcinol C — caged, fourPlusTwo, seco
319
319.1 hyperforcinol C[c] H. forrestii +30 (0.2, m) W.-J. Lu 2021
Structure 320: hypatulin B — fourPlusTwo, seco, uncaged
320
320.1 hypatulin B H. patulum +27.0 (0.17, m) N. Tanaka 2016b
Structure 321: garcimultiflin D, garcimultiflin A — caged, fourPlusTwo, seco
321
321.1 X1 = H
X2 = OH		 garcimultiflin D[d] G. multiflora +10.0 (1.0, m) H. Luo 2025
321.2 X1 = OH
X2 = H		 garcimultiflin A[d] G. multiflora −15.0 (1.0, m) J. Cao 2023
Structure 322: garcimultiflin B — caged, fourPlusTwo, seco
322
322.1 garcimultiflin B[d] G. multiflora −10.0 (1.0, m) J. Cao 2023
Structure 323: garcimultiflin C — caged, fourPlusTwo, seco
323
323.1 garcimultiflin C[d] G. multiflora +11.0 (1.0, m) J. Cao 2023
Structure 324: garcibracteatone, garcixanthochymone E, garcibracteatone D and others — A, caged, fourPlusTwo
324
324.1 R1 = prenyl
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone G. bracteata −1 (1.00) O. Thoison 2005
324.2 R1 = prenyl
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = OH
X3 = OH		 garcixanthochymone E G. xanthochymus +9.49 (0.604, m) Y. Chen 2017
324.3 R1 = prenyl
R2 = H
R3 = H
R4 = (E)-CH=CHCMe2OH
X1 = H
X2 = H
X3 = H		 garcibracteatone D[c] G. bracteata −74.4 (0.01, m) X.-N. Li 2023
324.4 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 −6.5 (2.9, m), −12 (0.1, m) C. Hashida 2014, X.-W. Yang 2015, N. Tanaka 2019
324.5 R1 = prenyl
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH
X1 = H
X2 = H
X3 = H		 hyperkouytone K[d] H. kouytchense −20.0 (0.27, m) H.-Y. Lou 2024
324.6 R1 = prenyl
R2 = (E)-CH=CHCMe2OH
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperuralone B[d] H. uralum −14.6 (0.14, m) J.-J. Zhang 2014b
324.7 R1 = prenyl
R2 = (E)-CH=CHCMe2OOH
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperberlone B[d] H. beanii −8.9 (0.4, m) Y.-W. Li 2022
324.8 R1 = CH2CH2CMe=CH2
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 doitunggarcinone A G. propinqua −133.3 (0.015) C. Tantapakul 2012, H. P. Pepper 2012
324.9 R1 = CH2CH2CMe=CH2
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = OH
X3 = OH		 garcixanthochymone D G. xanthochymus +22.7 (0.577, m) Y. Chen 2017
324.10 R1 = CH2CH2CMe=CH2
R2 = H
R3 = H
R4 = (E)-CH=CHCMe2OH
X1 = H
X2 = H
X3 = H		 garcibracteatone E[c] G. bracteata +3.63 (0.05, m) X.-N. Li 2023
324.11 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 −31.0 (0.1, m) J. Cao 2024
324.12 R1 = (R)-CH2CH(OH)CMe=CH2
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone A[c] G. bracteata +34.8 (0.25, m) X.-N. Li 2023
324.13 R1 = (R)-CH2CH(OH)CMe2OH
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone B[c] G. bracteata +8.08 (0.06, m) X.-N. Li 2023
324.14 R1 = (S)-CH2CH(OH)CMe2OH
R2 = H
R3 = H
R4 = prenyl
X1 = H
X2 = H
X3 = H		 garcibracteatone C[c] G. bracteata +46.18 (0.05, m) X.-N. Li 2023
324.15 R1 = (R)-CH2CH(OH)CMe2OH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone B[d] H. patulum −18.2 (0.3, m) F. Zhang 2026
324.16 R1 = (S)-CH2CH(OH)CMe2OH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone A[d] H. patulum −22.5 (0.3, m) F. Zhang 2026
324.17 R1 = (R)-CH2CH(OH)CMe2OMe
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone D[d] H. patulum −26.1 (0.3, m) F. Zhang 2026
324.18 R1 = (S)-CH2CH(OH)CMe2OMe
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone C[d] H. patulum −23.6 (0.3, m) F. Zhang 2026
324.19 R1 = (R)-CH2CH(OH)CMe=CH2
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone F[d] H. patulum −15.2 (0.3, m) F. Zhang 2026
324.20 R1 = (S)-CH2CH(OH)CMe=CH2
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone E[d] H. patulum −17.95 (0.3, m) F. Zhang 2026
324.21 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 −42.6 (0.33, m), −19.8 (0.3, m) H.-Y. Lou 2024, F. Zhang 2026
324.22 R1 = (S)-2,3-epoxy-3-methylbutyl
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone G[d] H. patulum −15.2 (0.3, m) F. Zhang 2026
324.23 R1 = (E)-CH=CHCMe2OH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyphenrone R H. henryi H. Lév & Vaniot −15 (0.15, m) Y. Liao 2016
324.24 R1 = (E)-CH=CHCMe2OOH
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyphenrone S H. henryi H. Lév & Vaniot −14 (0.12, m) Y. Liao 2016
324.25 R1 = (E)-CH=CHCMe2OMe
R2 = H
R3 = prenyl
R4 = prenyl
X1 = H
X2 = H
X3 = H		 hyperpatuone I[d] H. patulum −52 (0.3, m) F. Zhang 2026
Structure 325: garcibracteamone H, burlemarxione H, hyperforcinol A — caged, fourPlusTwo
325
325.1 R1 = CH2CH2CMe=CH2
R2 = H		 garcibracteamone H[c] G. bracteata +40 (0.05, m) Q. Xue 2020
325.2 R1 = CH2CH2CMe=CH2
R2 = H		 burlemarxione H[d] (enantiomer) C. burle-marxii −40.0 (0.5) M. do C. C. Silva 2024, Q. Xue 2020
325.3 R1 = prenyl
R2 = prenyl		 hyperforcinol A[d] H. forrestii −39 (0.1, m) W.-J. Lu 2021
Structure 326: hyperkouytone M — caged, fourPlusTwo
326
326.1 hyperkouytone M H. kouytchense −24.8 (0.36, m) H.-Y. Lou 2024
Structure 327: garcibracteamone I — caged, fourPlusTwo
327
327.1 garcibracteamone I[c] G. bracteata −22 (0.05, m) Q. Xue 2020
Structure 328: burlemarxione D — caged, fourPlusTwo
328
328.1 burlemarxione D C. burlemarxii −8.0 (1.0) C. G. Ferraz 2021
Structure 329: hyperlanin B — caged, fourPlusTwo
329
329.1 hyperlanin B[d] H. lancasteri −32.1 (0.3, m) J.-Q. You 2024
Structure 330: hyparillum B — caged, fourPlusTwo
330
330.1 hyparillum B[d] H. patulum −51.5 (0.1) Y. Duan 2024a
Structure 331: hyparillum A — caged, fourPlusTwo
331
331.1 hyparillum A[d] H. patulum −26.1 (0.2) Y. Duan 2024a
Structure 332: garcioblon D — caged, fourPlusTwo
332
332.1 garcioblon D[d] G. oblongifolia −37.2 (0.3, m) Q. Lin 2025
Structure 333: garcioblon A — caged, fourPlusTwo
333
333.1 garcioblon A[d] G. oblongifolia −29.0 (0.4, m) Q. Lin 2025
Structure 334: garcioblon B — caged, fourPlusTwo
334
334.1 garcioblon B[d] G. oblongifolia −32.5 (0.4, m) Q. Lin 2025
Structure 335: garcioblon C — caged, fourPlusTwo
335
335.1 garcioblon C[d] G. oblongifolia −40.6 (0.5, m) Q. Lin 2025
Structure 336: garcioblon E — caged, fourPlusTwo, seco
336
336.1 garcioblon E[d] G. oblongifolia +16.7 (0.5, m) Q. Lin 2025
Structure 337: garcioblon F — caged, fourPlusTwo, seco
337
337.1 garcioblon F[d] G. oblongifolia +26.2 (0.3, m) Q. Lin 2025
Structure 338: burlemarxione I — caged, fourPlusTwo
338
338.1 burlemarxione I[c] C. burle-marxii NR M. do C. C. Silva 2024
Structure 339: garbractin A — caged, fourPlusTwo, seco
339
339.1 garbractin A[c] G. bracteata −94.4 (0.05, m) X.-N. Li 2023
Structure 340: garcibracgluinol B — fourPlusTwo, seco
340
340.1 garcibracgluinol B[c] G. bracteata +248.1 (0.03, m) J. Xu 2025
Structure 341: garcibracgluinol C — fourPlusTwo, seco
341
341.1 garcibracgluinol C[c] G. bracteata +122.2 (0.07, m) J. Xu 2025
Structure 342: xerophenone C, xerophenone A — B, otherBridgedBicycles
342
342.1 R = prenyl xerophenone C G. bracteata +106 (1.0) O. Thoison 2005
342.2 R = CH2CH2CMe=CH2 xerophenone A[d] C. portlandiana, G. propinqua −36.4 (0.055, a) G. E. Henry 1995, T. Sriyatep 2017
Structure 343: garcoblone B, garciyunnanin E, garciyunnanin F and others — B, otherBridgedBicycles
343
343.1 R1 = Ph
R2 = prenyl
R3 = CH2CH(OMe)2
R4 = H		 garcoblone B[c] G. oblongifolia +21.5 (1.0, m) Z. Wu 2022
343.2 R1 = Ph
R2 = prenyl
R3 = CH2CO2H
R4 = H		 garciyunnanin E[c] G. yunnanensis +103.1 (0.13, m) D. Zheng 2021b
343.3 R1 = Ph
R2 = prenyl
R3 = CH2COCMe2OH
R4 = H		 garciyunnanin F, a.k.a. garcoblone A[c] G. oblongifolia, G. yunnanensis +137.6, +21.5 (0.10, m) D. Zheng 2021b, Z. Wu 2022
343.4 R1 = Ph
R2 = prenyl
R3 = CH2COCMe2OH
R4 = prenyl		 hyperberlone D[c] H. beanii +1.6 (1.7, m) Y.-W. Li 2022
343.5 R1 = Ph
R2 = (S)-lavandulyl
R3 = CH2COCMe2OH
R4 = H		 garcoblone D[c][f] G. oblongifolia +27.2 (1.0, m) Z. Wu 2022
343.6 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = CH2COCMe2OH
R4 = H		 garcoblone C[c] G. oblongifolia +41.2 (1.0, m) Z. Wu 2022
Structure 344: garcoblone G, garcibractinol A, garcibractinol E — B, otherBridgedBicycles
344
344.1 R1 = prenyl
R2 = prenyl		 garcoblone G[c] G. oblongifolia −24.1 (1.0, m) S.-Y. Yang 2024
344.2 R1 = prenyl
R2 = CH2CH2CMe=CH2		 garcibractinol A[d] G. bracteata −91.9 (0.04, m) X. Li 2023
344.3 R1 = (E)-CH=CHCMe2OMe
R2 = CH2CH2CMe=CH2		 garcibractinol E[d] G. bracteata −85.1 (0.06, m) X. Li 2023
Structure 345: garcibractinol B, garcibractinol D, garcibractinol C and others — B, otherBridgedBicycles
345
345.1 R = prenyl garcibractinol B[d] G. bracteata −13.3 (0.05, m) X. Li 2023
345.2 R = (E)-CH=CHCMe2OH garcibractinol D[d] G. bracteata −63.9 (0.05, m) X. Li 2023
345.3 R = (E)-CH=CHCMe2OOH garcibractinol C[d] G. bracteata −37.3 (0.05, m) X. Li 2023
345.4 R = (R)-CH2CHOHCMe=CH2 garcibractinol F[d] G. bracteata −5.1 (0.056, m) X. Li 2023
Structure 346: garcoblone H — B, otherBridgedBicycles
346
346.1 garcoblone H[c] G. oblongifolia −26.4 (1.0, m) S.-Y. Yang 2024
Structure 347: garynthone A — B, caged, otherBridgedBicycles
347
347.1 garynthone A G. yunnanensis racemic; +7.85 (0.1, m) and −3.28 (0.1, m) Z. Guo 2025
Structure 348: garcibractinol G, garcibractinol H — B, otherBridgedBicycles
348
348.1 R = CMe2OH garcibractinol G[d] G. bracteata +150.5 (0.05, m) X. Li 2023
348.2 R = CMe=CH2 garcibractinol H[d] G. bracteata +14.4 (0.04, m) X. Li 2023
Structure 349: garciyunnanin D — B, otherBridgedBicycles
349
349.1 garciyunnanin D[c] G. yunnanensis +23.1 (0.10, m) D. Zheng 2021b
Structure 350: spirohypertone A — B, otherBridgedBicycles, seco
350
350.1 spirohypertone A[c] H. patulum −10.2 (0.2, m) Y. Duan 2024b
Structure 351: trijapin D — B, otherBridgedBicycles
351
351.1 trijapin D T. japonicum −58 (0.6, m) A. Oya 2015
Structure 352: xerophenone G — caged, otherBridgedBicycles
352
352.1 xerophenone G[c][e] G. multiflora +103.0 (0.1, m) J. Cao 2024
Structure 353: xerophenone F — caged, otherBridgedBicycles
353
353.1 xerophenone F[c][e] G. multiflora +164.0 (0.1, m) J. Cao 2024
Structure 354: xerophenone H — caged, otherBridgedBicycles
354
354.1 xerophenone H[e] G. multiflora −15.0 (0.1, m) W.-Y. Lyu 2025
Structure 355: xerophenone D — caged, otherBridgedBicycles
355
355.1 xerophenone D[c] G. multiflora +116.0 (0.1, m) J. Cao 2024
Structure 356: xerophenone E, xerophenone I — caged, otherBridgedBicycles
356
356.1 R = isolavandulyl[g] xerophenone E[c][e] G. multiflora +23.0 (0.1, m) J. Cao 2024
356.2 R = lavandulyl xerophenone I[c][e] G. multiflora −18.0 (0.1, m) H. Luo 2025
Structure 357: garcinielliptone HF — B, otherBridgedBicycles
357
357.1 garcinielliptone HF G. subelliptica −16.7 (0.22, a) C.-C. Wu 2008a
Structure 358: gambogenone — otherBridgedBicycles
358
358.1 gambogenone[e] G. xanthochymus −5 (0.003, m) S. Baggett 2005
Structure 359: garcibractinone C — otherBridgedBicycles
359
359.1 garcibractinone C[c] G. multiflora +32.1 (0.02, m) Q. Li 2022
Structure 360: hyperberin A, hyperberin B, hyperberin C — B, otherBridgedBicycles
360
360.1 R = (2R)-3,3-dimethyloxiran-2-yl hyperberin A[d] H. beanii +69.1 (0.33, m) W.-J. Xu 2019
360.2 R = (2S)-3,3-dimethyloxiran-2-yl hyperberin B[d] H. beanii +95.8 (0.28, m) W.-J. Xu 2019
360.3 R = (1S)-1,2-dihydroxy-2-methyl-1-propyl hyperberin C[d] H. beanii +144.5 (0.19, m) W.-X. Li 2021
Structure 361: hyperberlone E — B, otherBridgedBicycles
361
361.1 hyperberlone E[d] H. beanii +5.7 (0.7, m) Y.-W. Li 2022
Structure 362: hyperforone C, hyperforone B — B, otherBridgedBicycles, seco
362
362.1 R1 = H
R2 = benzoyl		 hyperforone C[c] (one of two by that name) H. forrestii −115 (0.1, m) W.-J. Lu 2020
362.2 R1 = benzoyl
R2 = H		 hyperforone B[c] (one of two by that name) H. forrestii −70 (0.1, m) W.-J. Lu 2020
Structure 363: hypercohin A, hypaluton B — A, otherBridgedBicycles
363
363.1 R = prenyl hypercohin A[c] H. cohaerens, H. forrestii NR X.-W. Yang 2012, W.-J. Lu 2020
363.2 R = (E)-C=CCMe2OH hypaluton B[c] H. patulum −108.7 (0.4, m) Y. Duan 2021a
Structure 364: hyperforone A — A, otherBridgedBicycles, seco
364
364.1 hyperforone A[c] (one of two by that name) H. forrestii −102 (0.1, m) W.-J. Lu 2020
Structure 365: hypaluton A — A, otherBridgedBicycles, seco
365
365.1 hypaluton A[c] H. patulum −64.2 (0.3, m) Y. Duan 2021a
Structure 366: hyperbeanin P — A, otherBridgedBicycles
366
366.1 hyperbeanin P[c] H. beanii −254 (0.2, m) X.-Y. Suo 2021b
Structure 367: hyperprin B — A, otherBridgedBicycles
367
367.1 hyperprin B[c] H. przewalskii −314.0 (0.10, m) J.-F. Zong 2020
Structure 368: hyperacmosin R — A, exo, otherBridgedBicycles
368
368.1 hyperacmosin R[c] H. acmosepalum −230.5 (0.14, m) Y. Ma 2022b
Structure 369: hyperinoid A — otherBridgedBicycles, seco
369
369.1 hyperinoid A[c] H. patulum +54.0 X. Jia 2020
Structure 370: hyperinoid B — otherBridgedBicycles, seco
370
370.1 hyperinoid B[c] H. patulum +61.0 X. Jia 2020
Structure 371: (±)-hypandrone A — otherBridgedBicycles
371
371.1 (±)-hypandrone A H. androsaemum 0 J. Wei 2024a
Structure 372: hypertaxoid B — B, otherBridgedBicycles
372
372.1 hypertaxoid B[d] H. elatoides +13.1 (0.05, m) J.-Y. Xie 2026
Structure 373: hypertaxoid A — B, otherBridgedBicycles
373
373.1 hypertaxoid A[d] H. elatoides +76.1 (0.05, m) J.-Y. Xie 2026
Structure 374: hypermonin A — B, otherBridgedBicycles, seco
374
374.1 hypermonin A[c] H. monogynum +46.5 (0.20, m) Y.-R. Zeng 2018
Structure 375: hypermonin B — B, otherBridgedBicycles, seco
375
375.1 hypermonin B[c] H. monogynum +155.42 (0.24, m) Y.-R. Zeng 2018
Structure 376: garciyunnanin G — B, otherBridgedBicycles, seco
376
376.1 garciyunnanin G[c] G. yunnanensis +28.7 (0.10, m) D. Zheng 2021b
Structure 377: harrisotone A, harrisotone B, tomoeone B and others — spiroindanes
377
377.1 R = Me
X = OH		 harrisotone A Harrisonia perforata +2.0 (0.27, m) S. Yin 2009
377.2 R = Me
X = OOH		 harrisotone B Harrisonia perforata +25.4 (1.30, m) S. Yin 2009
377.3 R = i-Pr
X = OH		 tomoeone B H. ascyron +9.5 (1.1, m) W. Hashida 2008
377.4 R = i-Pr
X = OOH		 tomoeone D H. ascyron +10.4 (3.0, m) W. Hashida 2008, H. Zhu 2015a
377.5 R = i-Bu
X = OH		 tomoeone F H. ascyron +1.8 (1.8, m) W. Hashida 2008
377.6 R = i-Bu
X = OOH		 tomoeone H H. ascyron +5.2 (2.7, m) W. Hashida 2008, H. Zhu 2015a
377.7 R = Ph
X = OH		 hyperbeanol A H. beanii +2.74 (0.21) X.-Q. Chen 2011
377.8 R = Ph
X = OOH		 hyperpatulol B[c] H. patulum −35.2 (0.1, m) Y.-Y. Liu 2019
Structure 378: hyperascyrone D, hookerianone E, hyperascyrone E and others — spiroindanes
378
378.1 R = i-Pr
X = OH		 hyperascyrone D[c] H. ascyron −7.8 (0.48, m) H. Zhu 2015a
378.2 R = i-Pr
X = OOH		 hookerianone E, a.k.a. hyperiforin C[c] H. hookerianum, H. forrestii +30 (0.1, m), +53.0 (c 0.1, m) Q.-Q. Wang 2020, J.-F. Zong 2021
378.3 R = i-Bu
X = OH		 hyperascyrone E[c] H. ascyron −9.1 (0.68, m) H. Zhu 2015a
378.4 R = Ph
X = OH		 hyperbeanol B H. beanii +14.27 (0.34) X.-Q. Chen 2011
Structure 379: harperoid B, harrisotone C, harrisotone E and others — spiroindanes
379
379.1 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = H
X2 = H		 harperoid B Harrisonia perforata +15 (0.4, m) P.-P. An 2026
379.2 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 harrisotone C Harrisonia perforata +11.1 (0.80, m) S. Yin 2009
379.3 R1 = Me
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 harrisotone E Harrisonia perforata +22.1 (0.09, m) S. Yin 2009
379.4 R1 = Et
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 hyperpatulone F[c] one of two by that name H. patulum +22.8 (1.0, m) Z.-N. Wu 2019
379.5 R1 = i-Pr
R2 = Me
R3 = prenyl
X1 = OH
X2 = H		 chipericumin C H. chinense, H. pyramidatum +35.1 (0.33, m) S. Abe 2012, R. Force 2014
379.6 R1 = i-Pr
R2 = Me
R3 = prenyl
X1 = OOH
X2 = H		 pyramidatone D H. pyramidatum +20.0 (0.009) R. Force 2014
379.7 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 pyramidatone A, a.k.a. chipericumin E H. pyramidatum, H. riparium +12.5 (0.005), +12.0 (0.5, m) R. Force 2014, M. F. Tala 2015
379.8 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = OOH
X2 = H		 pyramidatone B H. pyramidatum +15.5 (0.03) R. Force 2014
379.9 R1 = i-Pr
R2 = prenyl
R3 = Me
X1 = OH
X2 = OH		 hyperpatulol F[c] H. patulum +14.0 (0.1, m) Y.-Y. Liu 2019
379.10 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 tomoeone A[c] H. ascyron +33.2 (2.9, m) W. Hashida 2008, Y.-L. Hu 2023
379.11 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 tomoeone C H. ascyron +17.4 (4.9, m) W. Hashida 2008, H. Zhu 2015a, Y.-L. Hu 2023
379.12 R1 = s-Bu
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 chipericumin D[e] H. chinense +67.4 (0.33, m) S. Abe 2012
379.13 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperascyrone F[c][e] H. ascyron +41.1 (0.13, m) H. Zhu 2015a
379.14 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 hookerianone D[c][e] H. hookerianum +14 (0.1, m) Q.-Q. Wang 2020
379.15 R1 = i-Bu
R2 = prenyl
R3 = Me
X1 = OH
X2 = H		 hyperpatulone C[c] (one of two by that name) H. patulum +81.8 (0.10, m) Y.-x. Zhang 2021
379.16 R1 = i-Bu
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 tomoeone E H. ascyron, H. cohaerens +40.3 (1.0, m) W. Hashida 2008, J.-J. Zhang 2014a
379.17 R1 = i-Bu
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 tomoeone G H. ascyron +25.4 (1.7, m) W. Hashida 2008, H. Zhu 2015a
379.18 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = OH
X2 = H		 hyperbeanol C H. beanii +31.21 (0.19) X.-Q. Chen 2011
379.19 R1 = Ph
R2 = prenyl
R3 = prenyl
X1 = OOH
X2 = H		 hyperbeanol D H. beanii +42.73 (0.42) X.-Q. Chen 2011
Structure 380: hyperpatulone D — spiroindanes
380
380.1 hyperpatulone D[c] (one of two by that name) H. patulum +83.6 (0.10, m) Y.-x. Zhang 2021
Structure 381: harrisotone D, monosescinol C, hyperpatulol C and others — spiroindanes
381
381.1 R1 = Me
R2 = prenyl
R3 = prenyl
X = OH		 harrisotone D Harrisonia perforata +4.1 (0.12, m) S. Yin 2009
381.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = OH		 monosescinol C[c] H. longistylum −30.0 (0.4, m) Z. Shi 2024
381.3 R1 = i-Pr
R2 = prenyl
R3 = Me
X = OH		 hyperpatulol C[c] H. patulum +18.8 (0.1, m) Y.-Y. Liu 2019
381.4 R1 = i-Pr
R2 = prenyl
R3 = Me
X = OOH		 pyramidatone C H. pyramidatum +17.3 (0.01) R. Force 2014
381.5 R1 = (R)-s-Bu
R2 = Me
R3 = prenyl
X = OH		 monosescinol B[c] H. longistylum −37.3 (0.5, m) Z. Shi 2024
381.6 R1 = (R)-s-Bu
R2 = prenyl
R3 = prenyl
X = OH		 hyperlagarol I[c] H. beanii NR R.-D. Hu 2024
381.7 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
X = OH		 hyperlagarol H[c] H. beanii NR R.-D. Hu 2024
381.8 R1 = Ph
R2 = prenyl
R3 = prenyl
X = OH		 hyperpatulol A H. patulum +34.2 (0.1, m) Y.-Y. Liu 2019
Structure 382: hyperpatulol D, hyperpatulol E — spiroindanes
382
382.1 R = i-Pr hyperpatulol D[c] H. patulum +2.2 (0.1, m) Y.-Y. Liu 2019
382.2 R = s-Bu hyperpatulol E[c][e] H. patulum +10.6 (0.1, m) Y.-Y. Liu 2019
Structure 383: hunascynol I — spiroindanes
383
383.1 hunascynol I
(or its epimer, hunascynol J)		 H. ascyron −0.7 (0.09, m) Y.-L. Hu 2023
Structure 384: hunascynol J — spiroindanes
384
384.1 hunascynol J
(or its epimer, hunascynol I)		 H. ascyron −1.2 (0.11, m) Y.-L. Hu 2023
Structure 385: kouytchin B, hyperascyrone B, hyperascyrone C and others — spiroindanes
385
385.1 R1 = i-Pr
R2 = Me
X = H		 kouytchin B[d][m] H. kouytchense +27.1 (0.5, m) C. Jing 2026
385.2 R1 = i-Pr
R2 = prenyl
X = OH		 hyperascyrone B[d] H. ascyron −4.8 (0.24, m) H. Zhu 2015a
385.3 R1 = i-Bu
R2 = prenyl
X = OH		 hyperascyrone C[d] H. ascyron −3.8 (0.38, m) H. Zhu 2015a
385.4 R1 = Ph
R2 = prenyl
X = OH		 hyperascyrone A[d] H. ascyron −16.4 (0.33, m) H. Zhu 2015a
Structure 386: hunascynol H, spirohypatone B, spihyperglucinol E and others — spiroindanes
386
386.1 R1 = i-Pr
R2 = prenyl
X = H		 hunascynol H H. ascyron +50 (0.10, m) Y.-L. Hu 2023
386.2 R1 = i-Pr
R2 = prenyl
X = OH		 spirohypatone B[c] H. patulum +23.03 (0.101, m) Y. Ye 2020
386.3 R1 = i-Bu
R2 = Me
X = OH		 spihyperglucinol E[c] H. longistylum −18.3 (0.3, m) Z. Shi 2022
386.4 R1 = i-Bu
R2 = prenyl
X = H		 hunascynol G H. ascyron +53 (0.10, m) Y.-L. Hu 2023
386.5 R1 = i-Bu
R2 = prenyl
X = OH		 hunascynol F[c] H. ascyron −6.0 (0.10, m) Y.-L. Hu 2023
386.6 R1 = (R)-s-Bu
R2 = Me
X = H		 hyperpatulone E[c] H. patulum +44.3 (0.20, m) Y.-x. Zhang 2021
386.7 R1 = (S)-s-Bu
R2 = Me
X = H		 hyperpatulone F[c] (one of two by that name) H. patulum +12.4 (0.10, m) Y.-x. Zhang 2021
386.8 R1 = s-Bu
R2 = Me
X = OH		 hyperielliptone HB[c][e] H. geminiflorum +1.0 (1) C.-C. Wu 2008b, Z. Shi 2022
386.9 R1 = (R)-s-Bu
R2 = prenyl
X = OH		 hunascynol D[c] H. ascyron +5.0 (0.12, m) Y.-L. Hu 2023
386.10 R1 = (S)-s-Bu
R2 = prenyl
X = OH		 hunascynol E[c] H. ascyron +18 (0.15, m) Y.-L. Hu 2023
386.11 R1 = Ph
R2 = prenyl
X = OH		 hyperbeanin C[c] H. beanii +34.5 (0.12, m) Y. Ma 2022a
Structure 387: chipericumin A, chipericumin B, sampsonol A — spiroindanes
387
387.1 R1 = i-Pr
R2 = Me		 chipericumin A H. chinense +84.3 (0.29, m) S. Abe 2012
387.2 R1 = s-Bu
R2 = Me		 chipericumin B[e] H. chinense +116.1 (0.46, m) S. Abe 2012
387.3 R1 = Ph
R2 = prenyl		 sampsonol A H. sampsonii −7.7 (0.5, mc) W. Xin 2012
Structure 388: sampsonol B — spiroindanes
388
388.1 sampsonol B H. sampsonii +45.3 (0.5, mc) W. Xin 2012
Structure 389: hyperhenone L — spiroindanes
389
389.1 hyperhenone L H. henryi −6 (0.08, m) Y.-T. Duan 2018
Structure 390: hyperacmotone D — spiroindanes
390
390.1 hyperacmotone D[c] H. acmosepalum +20 (0.10, m) A.-Z. Wang 2022
Structure 391: hyperacmotone E — spiroindanes
391
391.1 hyperacmotone E[c] H. acmosepalum –1 (0.10, m) A.-Z. Wang 2022
Structure 392: hyperacmotone F — spiroindanes
392
392.1 hyperacmotone F[c] H. acmosepalum +60 (0.10, m) A.-Z. Wang 2022
Structure 393: hyperacmotone B — spiroindanes
393
393.1 hyperacmotone B[c] H. acmosepalum –92 (0.05, m) A.-Z. Wang 2022
Structure 394: harperoid C, sampsonol F, hyperhenone I and others — spiroindanes
394
394.1 R1 = Me
R2 = prenyl
R3 = prenyl
X = H		 harperoid C Harrisonia perforata +26 (0.4, m) P.-P. An 2026
394.2 R1 = i-Pr
R2 = Me
R3 = prenyl
X = H		 sampsonol F H. sampsonii +12.4 (0.5, mc) W. Xin 2012
394.3 R1 = i-Pr
R2 = prenyl
R3 = Me
X = H		 hyperhenone I H. henryi −516 (0.12, m) Y.-T. Duan 2018
394.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
X = H		 hyperlagarin A H. lagarocladum −87.9 (0.29, m) K. Wang 2019
394.5 R1 = i-Bu
R2 = Me
R3 = prenyl
X = H		 sampsonol E H. sampsonii +25.8 (0.5, mc) W. Xin 2012
394.6 R1 = s-Bu
R2 = Me
R3 = prenyl
X = H		 hyperhenone H[e] H. henryi −71 (0.15, m) Y.-T. Duan 2018
394.7 R1 = (S)-s-Bu
R2 = Me
R3 = prenyl
X = H		 hyperpatulol G[cc] H. patulum −40.6 (0.1, m) Y.-Y. Liu 2019
394.8 R1 = s-Bu
R2 = prenyl
R3 = prenyl
X = H		 hyperlagarin B[e] H. lagarocladum −87.9 (0.18, m) K. Wang 2019
394.9 R1 = Ph
R2 = prenyl
R3 = Me
X = H		 sampsonol C H. sampsonii +16.5 (0.5, mc) W. Xin 2012
394.10 R1 = Ph
R2 = prenyl
R3 = prenyl
X = H		 hypercohone G H. cohaerens −56.1 (0.16, m) J.-J. Zhang 2014a
394.11 R1 = Ph
R2 = prenyl
R3 = prenyl
X = OH		 kouytchin A[c][m] H. kouytchense −20.0 (0.5, m) C. Jing 2026
394.12 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = Me
X = H		 sampsonol D H. sampsonii +35.2 (0.5, mc) W. Xin 2012
394.13 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
X = H		 hyperhenone J H. henryi −15 (0.22, m) Y.-T. Duan 2018
Structure 395: harperoid D, hyperhenone G, hyperpatulol I and others — spiroindanes
395
395.1 R1 = Me
R2 = prenyl
R3 = prenyl		 harperoid D Harrisonia perforata −22 (0.4, m) P.-P. An 2026
395.2 R1 = i-Pr
R2 = Me
R3 = prenyl		 hyperhenone G H. henryi −99 (0.07, m) Y.-T. Duan 2018
395.3 R1 = i-Pr
R2 = prenyl
R3 = Me		 hyperpatulol I[c] H. patulum −9.4 (0.1, m) Y.-Y. Liu 2019
395.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl		 hyperlagarin C H. lagarocladum −89.7 (0.25, m) K. Wang 2019
395.5 R1 = (S)-s-Bu
R2 = prenyl
R3 = Me		 hyperpatulol H[c] H. patulum −31.2 (0.1, m) Y.-Y. Liu 2019
395.6 R1 = Ph
R2 = prenyl
R3 = prenyl		 hyperbeanol F H. beanii −46 (0.5, m) Y.-R. Li 2019
Structure 396: hyperbeanol G — spiroindanes
396
396.1 hyperbeanol G H. beanii +15 (0.09, m) Y.-R. Li 2019
Structure 397: hunascynol A — spiroindanes
397
397.1 hunascynol A, a.k.a. hyperlagarol A H. ascyron, H. beanii +15 (0.5, m) Y.-L. Hu 2023, R.-D. Hu 2024
Structure 398: hunascynol B — spiroindanes
398
398.1 hunascynol B, a.k.a. hyperlagarol B H. ascyron, H. beanii +57 (0.14, m) Y.-L. Hu 2023, R.-D. Hu 2024
Structure 399: hyperlagarol G — caged, spiroindanes
399
399.1 hyperlagarol G[c] H. beanii NR R.-D. Hu 2024
Structure 400: hunascynol C — spiroindanes
400
400.1 hunascynol C H. ascyron +29 (0.14, m) Y.-L. Hu 2023
Structure 401: hyperpatulone G — spiroindanes
401
401.1 hyperpatulone G[c] H. patulum +62.0 (0.10, m) Y.-x. Zhang 2021
Structure 402: hyperbeanol H — spiroindanes
402
402.1 hyperbeanol H H. beanii +52 (0.7, m) Y.-R. Li 2019
Structure 403: hyperhenone K — spiroindanes
403
403.1 hyperhenone K H. henryi −6 (0.07, m) Y.-T. Duan 2018
Structure 404: hyperispirone B — caged, spiroindanes
404
404.1 hyperispirone B[c] H. beanii −53 (0.18, m) B. Yang 2022
Structure 405: hyperispirone A — caged, spiroindanes
405
405.1 hyperispirone A[c] H. beanii +70 (0.15, m) B. Yang 2022
Structure 406: hyperlagarol J — caged, spiroindanes
406
406.1 hyperlagarol J[c] H. beanii NR R.-D. Hu 2024
Structure 407: hymoin C, hymoin D, hypatulone A — caged, spiroindanes
407
407.1 R1 = i-Pr
R2 = Me		 hymoin C[c] H. monogynum −76.00 (0.11, m) Y.-R. Zeng 2021b
407.2 R1 = s-Bu
R2 = Me		 hymoin D[c][e] H. monogynum −30.22 (0.13, m) Y.-R. Zeng 2021b
407.3 R1 = Ph
R2 = prenyl		 hypatulone A[c] H. patulum +11.2 (0.10, m) Y.-Y. Liu 2018, X.-W. Yang 2020
Structure 408: hymoin A, hymoin B — caged, seco, spiroindanes
408
408.1 R = i-Pr hymoin A[c] (one of two by that name) H. monogynum −78.50 (0.08, m) Y.-R. Zeng 2021b
408.2 R = s-Bu hymoin B[c][e] (one of two by that name) H. monogynum −64.29 (0.13, m) Y.-R. Zeng 2021b
Structure 409: hyperilongenol C, hyperilongenol B, hyperilongenol A — seco, spiroindanes
409
409.1 R = i-Pr hyperilongenol C[c] H. longistylum +82.3 (0.5, m) N. Zhang 2019a, N. Zhang 2019b
409.2 R = i-Bu hyperilongenol B[c] H. longistylum +85.2 (0.3, m) N. Zhang 2019a, N. Zhang 2019b
409.3 R1 = s-Bu
R2 = (mixture of s-Bu epimers)		 hyperilongenol A[c] H. longistylum +89.4 (0.6, m) N. Zhang 2019a, N. Zhang 2019b
Structure 410: hyperlagarol C — caged, seco, spiroindanes
410
410.1 hyperlagarol C[c] H. beanii NR R.-D. Hu 2024
Structure 411: hyperlagarol D — seco, spiroindanes
411
411.1 hyperlagarol D[c] H. beanii NR R.-D. Hu 2024
Structure 412: spihyperglucinol A, spihyperglucinol B — caged, seco, spiroindanes
412
412.1 R = i-Bu spihyperglucinol A[c] H. longistylum −130.0 (0.8, m) Z. Shi 2022
412.2 R = s-Bu spihyperglucinol B[c][e] H. longistylum −112.6 (0.1, m) Z. Shi 2022
Structure 413: spihyperglucinol C, spihyperglucinol D — caged, seco, spiroindanes
413
413.1 R = i-Bu spihyperglucinol C[c] H. longistylum −53.4 (0.4, m) Z. Shi 2022
413.2 R = s-Bu spihyperglucinol D[c][e] H. longistylum −61.6 (0.4, m) Z. Shi 2022
Structure 414: biyouyanagiol, uralin D — seco, spiroindanes
414
414.1 R = Me biyouyanagiol[y] H. chinense +10.5 (0.5) N. Tanaka 2009a
414.2 R = prenyl uralin D[c] H. uralum +32 (0.1, m) Q.-Q. Fang 2021
Structure 415: biyoulactone D, biyoulactone E — seco, spiroindanes
415
415.1 R = i-Pr biyoulactone D H. chinense −39.4 (0.1, m) N. Tanaka 2012
415.2 R = s-Bu biyoulactone E[e] H. chinense −14.4 (0.07, m) N. Tanaka 2012
Structure 416: hyperbeanone A — seco, spiroindanes
416
416.1 hyperbeanone A[c] H. beanii −134 (0.15, m) B. Yang 2021a
Structure 417: hypermonone B, hypermonone C — seco, spiroindanes
417
417.1 R = i-Pr hypermonone B[c] H. monogynum +56.31 (0.07, m) Y.-R. Zeng 2021c
417.2 R = s-Bu hypermonone C[c][e] H. monogynum −40.83 (0.07, m) Y.-R. Zeng 2021c
Structure 418: hypermonone D — seco, spiroindanes
418
418.1 hypermonone D[c] H. monogynum +47.26 (0.12, m) Y.-R. Zeng 2021c
Structure 419: hypermonone A — seco, spiroindanes
419
419.1 hypermonone A[c] H. monogynum +123.49 (0.09, m) Y.-R. Zeng 2021c
Structure 420: hybeanone B, hybeanone A — seco, spiroindanes
420
420.1 R = i-Pr hybeanone B[c] H. beanii +72.3 (0.17, m) B. Yang 2021b
420.2 R = (S)-s-Bu hybeanone A[c] H. beanii +48.9 (0.09, m) B. Yang 2021b
Structure 421: hypermonol A, hypermonol E — seco, spiroindanes
421
421.1 R = i-Pr hypermonol A[c] H. monogynum +25.8 (0.1, m) J. Wei 2024b
421.2 R = (S)-s-Bu hypermonol E[c] H. monogynum +18.8 (0.1, m) J. Wei 2024b
Structure 422: hypermonol B, hypermonol C, hypermonol D — seco, spiroindanes
422
422.1 R = i-Pr hypermonol B[c] H. monogynum −64.6 (0.1, m) J. Wei 2024b
422.2 R = (R)-s-Bu hypermonol C[c] H. monogynum +10.4 (0.1, m) J. Wei 2024b
422.3 R = (S)-s-Bu hypermonol D[c] H. monogynum +5.4 (0.1, m) J. Wei 2024b
Structure 423: biyoulactone A — seco, spiroindanes
423
423.1 biyoulactone A[c] H. chinense +8.1 (0.1, m) N. Tanaka 2011
Structure 424: hypemoin A, biyoulactone B — seco, spiroindanes
424
424.1 R = i-Pr hypemoin A[c] H. monogynum +24 (0.2, m) Y.-N. Li 2011
424.2 R = (S)-s-Bu biyoulactone B H. chinense +9.7 (0.2, m) N. Tanaka 2011
Structure 425: hypemoin B, biyoulactone C — seco, spiroindanes
425
425.1 R = i-Pr hypemoin B[c] H. monogynum +48 (0.2, m) Y.-N. Li 2011
425.2 R = (S)-s-Bu biyoulactone C H. chinense +15.7 (0.09, m) N. Tanaka 2011
Structure 426: furanmonogone B, hyperascone A, hyperascone B and others — seco, spiroindanes
426
426.1 R1 = i-Pr
R2 = Me		 furanmonogone B[c][e] H. monogynum −8 (0.1, m) W.-J. Xu 2017
426.2 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH		 hyperascone A[c][aa] H. ascyron Linn. +6.3 (0.03, m) S. Wang 2024
426.3 R1 = i-Bu
R2 = (E)-CH=CHCMe2OH		 hyperascone B[c][aa] H. ascyron Linn. +5.7 (0.03, m) S. Wang 2024
426.4 R1 = s-Bu
R2 = Me		 furanmonogone A[c][e] H. monogynum −12 (0.1, m) W.-J. Xu 2017
426.5 R1 = Ph
R2 = (E)-CH=CHCMe2OH		 hyperhenone M[e] H. henryi −31 (0.10, m) Y.-T. Duan 2018
Structure 427: hypemoin E, hypemoin D, hypemoin C — seco, spiroindanes
427
427.1 R = H hypemoin E[c] H. monogynum −76 (0.1, m) Y.-N. Li 2011
427.2 R = CO2Me hypemoin D[c] H. monogynum +52 (0.1, m) Y.-N. Li 2011
427.3 R = COCHMeCH2CH=CMe2 hypemoin C[c][e] H. monogynum +48 (0.2, m) Y.-N. Li 2011
Structure 428: longisglucinol A — seco, spiroindanes
428
428.1 longisglucinol A[c] H. longistylum −31.2 (0.5, m) N. Zhang 2020
Structure 429: hymoin B — seco, spiroindanes
429
429.1 hymoin B[c] (one of two by that name) H. monogynum +160.00 (0.10, m) C. Yuan 2025
Structure 430: spirohypatone A, longisglucinol C, longisglucinol B and others — spiropentalanes
430
430.1 R1 = i-Pr
R2 = Me		 spirohypatone A[c] H. patulum +105.54 (0.10, m) Y. Ye 2020
430.2 R1 = i-Bu
R2 = Me		 longisglucinol C[c][ff] H. longistylum +99.8 (0.5, m) N. Zhang 2020
430.3 R1 = (S)-s-Bu
R2 = Me		 longisglucinol B[c][ff] H. longistylum +106.9 (0.5, m) N. Zhang 2020
430.4 R1 = Ph
R2 = prenyl		 hyperacmotone C[c] H. acmosepalum +101 (0.20, m) A.-Z. Wang 2022
Structure 431: harperoid A — caged, seco, spiropentalanes
431
431.1 harperoid A[c] Harrisonia perforata +12 (0.2, m) P.-P. An 2026
Structure 432: hymoin A — caged, seco, spiropentalanes
432
432.1 hymoin A[c] (one of two by that name) H. monogynum +77.92 (0.15, m) C. Yuan 2025
Structure 433: hyperzrone A — spiropentalanes
433
433.1 hyperzrone A[c] H. beanii +19.8 (0.1, m) X.-Y. Li 2025
Structure 434: hyperzrone B — spiropentalanes
434
434.1 hyperzrone B[c] H. beanii −1.7 (0.1, m) X.-Y. Li 2025

Statistics

There are 1467 compounds listed.

FeatureNumber
bicyclo[3.3.1]nonanes1149
bicyclo[3.2.1]octanes28
bicyclo[2.2.2]octanes88
other bridged bicyclics53
spiroindanes143
spiropentalanes8
other spiro compounds2
exo at C(7)579
endo at C(7)535
two substituents at C(3) (not caged)98
no substituent at C(7)2
no substituent at C(3)5
acyloxy substituent at C(3)8
type A889
type B353
uncaged831
caged394
seco and nor263
enamine replacing carbonyl8
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