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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) 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) 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) 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) Tatsis 2007, Porzel 2014, Mitsopoulou 2015, Nedialkov 2015
1.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H
secohyperforin H. perforatum NR Charchoglyan 2007, Sparling 2015
1.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl
hyperforin[c] H. perforatum, H. attenuatum +41 (5, e) Gurevich 1971 (includes translation), Bystrov 1975, Bystrov 1978, 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) Weng 2003a
1.8 R1 = i-Bu
R2 = H
R3 = geranyl
R4 = prenyl
R5 = H
garcicosin G. verrucosa −10 (0.3) 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) Henry 2006
1.10 R1 = s-Bu
R2 = H
R3 = prenyl
R4 = prenyl
R5 = prenyl
hyperevolutin B[e] H. revolutum Vahl NR 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) Ilieva 2023
1.12 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H
adsecohyperforin[e] H. perforatum NR Charchoglyan 2007
1.13 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl
adhyperforin[e] H. perforatum NR Maisenbacher 1992
1.14 R1 = s-Bu
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
garcinielliptone D[e] G. subelliptica −22 (0.1) 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) de Oliveira 1996, de Oliveira 1999, Lokvam 2000, Cuesta-Rubio 2001a, 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 Lokvam 2000
1.18 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H
hydroxynemorosone C. nemorosa OMe: +143 (0.7, m) de Oliveira 1996, 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 Ernst 2024
2.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl
no common name H. sampsonii NR 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) Henry 1999, de Oliveira 1999, Grossman 2000, X.-W. Yang 2017a, Ernst 2024
2.4 R1 = Ph
R2 = prenyl
R3 = (E)-4-acetoxyprenyl
insignone C. insignis OMe: +92.7 (1.6) Porto 2000
2.5 R1 = Ph
R2 = geranyl
R3 = prenyl
nemosampsone[d] H. sampsonii NR Ernst 2024
Structure 3: hyperfirin — A, bicyclononanes, noC7
3
hyperfirin H. perforatum NR 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) Jiang 2019
4.2 R1 = i-Pr
R2 = (E)-CH2CH=CMeCHO
R3 = prenyl
hypseudone C[c] H. pseudohenryi +25.5 (0.157, m) 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) 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) Jiang 2025
Structure 5: hyperkouytone C — A, bicyclononanes, exo
5
hyperkouytone C[c] H. kouytchense −96.0 (0.5, m) H.-Y. Lou 2024
Structure 6: dorstenpictanone — A, bicyclononanes, exo
6
dorstenpictanone Dorstenia picta NR 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
R3 = X1 = H
R4 = X2 = H
deoxyfurohyperforin A H. perforatum +42 (0.018, mc) Vajs 2003
7.2 R1 = i-Pr
R2 = prenyl
R3 = X1 = OH/H
R4 = X2 = H/OH
furohyperforin A, mixture of epimers H. perforatum NR Trifunovi&#263 1998, Vajs 2003
7.3 R1 = i-Pr
R2 = prenyl
R3 = X1 = OMe
R4 = X2 = H
hyperwilsone B[c] H. wilsonii +114.1 (0.2, acn) Y. Duan 2021c
7.4 R1 = i-Pr
R2 = prenyl
R3 = X1 = H
R4 = X2 = OMe
hyperwilsone A[c] H. wilsonii +25.7 (0.2, acn) Y. Duan 2021c
7.5 R1 = (S)-s-Bu
R2 = prenyl
R3 = X1 = H
R4 = X2 = OMe
lancasteroid F[c] H. lancasteri +5.8 (0.3, m) J.-Q. You 2025
7.6 R1 = (S)-s-Bu
R2 = prenyl
R3 = X1 = OMe
R4 = X2 = H
lancasteroid E[c] H. lancasteri +115.7 (0.3, m) J.-Q. You 2025
7.7 R1 = Ph
R2 = H
R3 = X1 = H
R4 = X2 = H
hyperscabrone B[c] H. scabrum −39 (0.1, m) W. Gao 2016a
7.8 R1 = Ph
R2 = H
R3 = X1 = H
R4 = X2 = OMe
lancasteroid G[c] H. lancasteri −62.1 (0.3, m) J.-Q. You 2025
7.9 R1 = Ph
R2 = H
R3 = X1 = OMe
R4 = X2 = H
lancasteroid H[c] H. lancasteri +1.7 (0.3, m) J.-Q. You 2025
7.10 R1 = Ph
R2 = prenyl
R3 = X1 = H
R4 = X2 = H
hyphenrone X[c] H. henryi H. Lév & Vaniot −23 (0.18, m) Liao 2016
7.11 R1 = Ph
R2 = prenyl
R3 = X1 = OMe
R4 = X2 = H
hypseudohenrin F[c] H. pseudohenryi +22.2 (0.86, m) H. Sun 2021b
7.12 R1 = Ph
R2 = prenyl
R3 = X1 = H
R4 = 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) Fukuyama 1997, 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) Trifunovi&#263 1998, 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) 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, Bridi 2018, 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) 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) 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) 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, Zong 2021
8.39 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
X = OH
furoadhyperforin[e] H. perforatum NR 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) Matsuhisa 2002
8.52 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
X = OH
propolone D (enantiomer) Cuban propolis +48.5 (0.7) 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, 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) Oya 2015
8.64 R1 = Ph
R2 = CH2CHOHCMe=CH2
R3 = prenyl
R4 = H
X = OH
hyperibone D[e] H. scabrum −61.9 (0.7) 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) 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
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) Matsuhisa 2002, 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) 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) 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) 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) 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) 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) 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) Matsuhisa 2002, 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
otogirinin E[e] H. erectum Thunb. NR 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
garcinielliptone L[d] G. subelliptica −41 (0.3) Weng 2004, X.-W. Yang 2017a, Y. Guo 2021a
16.3 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
furohyperforin isomer 2, a.k.a. attenuatumione E[c] H. attenuatum, H. perforatum +39.7 (0.13) Lee 2006, C. Hashida 2008, Z.-B. Zhou 2014, X.-W. Yang 2018, Qiu 2023
16.5 R1 = i-Pr
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl
R5 = prenyl
R6 = X1 = H
R7 = 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
R6 = X1 = OH
R7 = 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
R6 = X1 = H
R7 = 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, Qiu 2023
16.8 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (E)-CH=CHCMe2OMe
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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, Qiu 2023
16.16 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = (R)-CH2CHOHCMe=CH2
R5 = prenyl
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
uralione O[c] H. uralum +28.6 (0.1, m) X. Li 2017, Qiu 2023
16.19 R1 = i-Pr
R2 = CMe2OH
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
R5 = prenyl
R6 = X1 = H
R7 = 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, Qiu 2023
16.20 R1 = i-Pr
R2 = CMe2OH
R3 = CH2CH(OH)CMe2OH
R4 = prenyl
R5 = (R)-2,3-epoxy-3-methylbutyl
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
hypermongone B[c] H. ascyron, H. monogynum +80 (0.2, m) W.-J. Xu 2015, Kong 2017
16.23 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = OH
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
propolone C, a.k.a. garcinielliptone K[d] (enantiomer) Cuban propolis, G. subelliptica +35.7 (0.2), +27 (0.3) Weng 2004, Hernandez 2005, X.-W. Yang 2017a
16.29 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = (R)-CH2CH(OH)CMe2OH
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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, 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
garcinielliptone M[d] G. subelliptica +73 (0.2) Weng 2004, X.-W. Yang 2017a, Y. Guo 2021a
17.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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, Qiu 2023
17.6 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = X2 = H
hypericumoxide A[e] H. scabrum +12.5 (0.06, m) R. Liu 2017, Qiu 2023
17.8 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
hypericumoxide B[c] H. scabrum −12.5 (0.08, m) R. Liu 2017, Qiu 2023
17.13 R1 = i-Pr
R2 = prenyl
R3 = (S)-CH2CHOHCMe=CH2
R4 = prenyl
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
hypericumoxide C[c] H. scabrum +14.7 (0.03, m) R. Liu 2017, Qiu 2023
17.17 R1 = i-Pr
R2 = (S)-CH2CHOHCMe2OH
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = X2 = H
uralione K[c] H. uralum +6 (0.1) Z.-B. Zhou 2016b, Qiu 2023
17.18 R1 = i-Pr
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = 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, Qiu 2023
17.19 R1 = i-Bu
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
uralione F[c] H. uralum −32 (0.3) Z.-B. Zhou 2016b, Qiu 2023
17.26 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = (S)-isolavandulyl[g]
R4 = H
R5 = X1 = H
R6 = 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) Xiao 2007, 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
lathrophytoic acid B Kielmeyera lathrophyton NR 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
garsubellin C[d] G. subelliptica +39 (0.4, e) Fukuyama 1997, Fukuyama 1998, Y. Guo 2021a
21.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = H
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = OEt
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
hyperibone A H. scabrum +57 (0.2), +63.7 (0.4) Matsuhisa 2002, Hernandez 2005
21.24 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
R5 = X1 = H
R6 = X2 = H
garcinielliptone I (enantiomer) G. subelliptica −37.7 (1.1) Weng 2003b, Ciochina 2006
21.25 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
dihroxuralodin H. petiolulatum −27.9 (0.10, m) Rui 2017
Structure 22: hyperwilsone C — A, bicyclononanes, exo
22
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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
garsubellin D[d] G. subelliptica −12 (0.4, e) Fukuyama 1998, Y. Guo 2021a
23.4 R1 = i-Pr
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
furohyperforin isomer 1[r] H. perforatum +50 (0.7) Lee 2006, C. Hashida 2008, X.-W. Yang 2018
23.7 R1 = i-Pr
R2 = CMe=CH2
R3 = prenyl
R4 = prenyl
R5 = prenyl
R6 = X1 = H
R7 = 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
R6 = X1 = OH
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
garsubellin E[e] G. subelliptica −7 (e, 0.4) Fukuyama 1998
23.25 R1 = s-Bu
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = X2 = H
hyperibone B H. scabrum, Cuban propolis −20.8 (0.5), −42.2 (0.1) Matsuhisa 2002, Hernandez 2005
23.30 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
R6 = X1 = H
R7 = X2 = H
ochrocarpinone C[o][p] (perhaps enantiomer) Ochrocarpos punctatus +0.21 (0.38) Chaturvedula 2002
23.31 R1 = Ph
R2 = CMe2OH
R3 = prenyl
R4 = prenyl
R5 = prenyl
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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
R6 = X1 = H
R7 = 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) 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) Teng 2021
24.6 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = prenyl
X = H
hyperibone C H. scabrum −27.3 (0.3) Matsuhisa 2002, 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) 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) Xiao 2007
25.2 R = geranyl otogirinin D H. erectum Thunb., H. attenuatum +160.0 (0.03, m) 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 Winkelmann 2001a
26.2 R1 = Ph
R2 = prenyl
scrobiculatone B[c] C. scrobiculata +44.7 (0.2) 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 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) Henry 1999
27.2 R1 = prenyl
R2 = prenyl
hypersampsone F H. sampsonii +30 (0.2) Y.-L. Lin 2003, 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) 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = OH
uralione B H. uralum −28 (0.1) Z.-B. Zhou 2016b
28.13 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH2–prenyl
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = OH
R6 = X2 = H
propolone B Cuban propolis +38.2 (0.6) Hernandez 2005, W. Gao 2016b
28.17 R1 = Ph
R2 = (S)-CH2CH(OH)CMe2OH
R3 = prenyl
R4 = Me
R5 = X1 = OH
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
garcinuntin B[c] G. nuntasaenii −62.8 (1.0) Chaturonrutsamee 2018
28.23 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = Me
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
garcimultinone J[d] G. multiflora −5.07 (0.05, m) Teng 2021
28.25 R1 = 3,4-dihydroxyphenyl
R2 = 2,2,6,6-tetramethyl-3-oxanylmethyl
R3 = prenyl
R4 = Me
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = 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
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) 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) 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) Winkelmann 2001a
31.2 R1 = i-Pr
R2 = Me
R3 = prenyl
papuaforin E H. papuanum +41 (0.1, m) 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) 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) Winkelmann 2001a
31.6 R1 = s-Bu
R2 = Me
R3 = prenyl
papuaforin D[e] H. papuanum +64 (0.1, m) 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) Porto 2000, 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) 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) Fobofou 2016, Y.-G. Fu 2025
32.2 R1 = s-Bu
R2 = prenyl
R3 = prenyl
hyperselancin A[c][e] H. lanceolatum −1 (0.3) 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 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
R5 = X1 = H
R6 = 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
R5 = X1 = H
R6 = X2 = H
garcinielliptone B G. subelliptica −23 (0.1) Weng 2003a
33.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = X2 = OH
hyperacmosin H[c] H. acmosepalum −478 (0.25, m) X. Wang 2020b
33.7 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = H
R5 = X1 = H
R6 = X2 = H
propolone A Cuban propolis, H. attenuatum +40 (0.1) Cuesta Rubio 1999, D. Li 2015a
33.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = 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
R5 = X1 = OH
R6 = 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
R5 = X1 = H
R6 = X2 = H
garcinuntin A[c] G. nuntasaenii −96.3 (0.30) Chaturonrutsamee 2018
33.11 R1 = 3,4-dihydroxyphenyl
R2 = (S)-2,2,6,6-tetramethyl-3-oxanylmethyl
R3 = CH2CH2CMe2OH
R4 = H
R5 = X1 = H
R6 = 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
ochrocarpinone A[e][o] Ochrocarpos punctatus +8.7 (0.15) 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
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) Teng 2021
37.2 R = 3,4-dihydroxyphenyl garcimultinone E[d] G. multiflora +11.22 (0.15, m) Teng 2021
Structure 38: garcimultiflorone A — A, bicyclononanes, endo
38
garcimultiflorone A G. multiflora −173 (0.12) J.-J. Chen 2009
Structure 39: no    name — A, bicyclononanes, endo
39
no common name C. obdeltifolia +30.9 (0.3) Teixeira 2005
Structure 40: hypersampsonone A — A, bicyclononanes, endo
40
hypersampsonone A[d] H. sampsonii +46.1 (0.59) J.-S. Zhang 2016
Structure 41: hypersampsone S — A, bicyclononanes, endo
41
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) 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
hyperkouytone A[d] H. kouytchense −24.8 (0.21, m) H.-Y. Lou 2024
Structure 46: hyperhookerione A — A, bicyclononanes, exo
46
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) Tanaka 2004, Benkiki 2014, 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) Fukuyama 1993, C.-N. Lin 1996, 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) 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) 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) 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) 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) Liao 2016
47.9 R1 = i-Pr
R2 = CH2CH2CMe2OH
R3 = prenyl
R4 = prenyl
R5 = H
garcinielliptone E G. subelliptica −51 (0.2) Weng 2003a, 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) Kong 2017
47.12 R1 = i-Bu
R2 = prenyl
R3 = prenyl
R4 = (E)-4-oxoprenyl
R5 = H
spiranthenone A Spiranthera odoratissima +11 (0.19) 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, Kong 2017
47.14 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H
garcinielliptone T[e] G. subelliptica +32 (0.09, m) 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
R4 = X1 = H
R5 = X2 = OH
przewalcyrone E[c] H. przewalskii −88.18 (0.44, m) Duan 2019
50.2 R1 = i-Pr
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
przewalcyrone F[c] H. przewalskii −47.25 (0.13, m) Duan 2019
50.3 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = X1 = H
R5 = X2 = OH
hyphenrone T[c] H. henryi H. Lév & Vaniot −118 (0.09, m) Liao 2016
50.4 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = H
hyphenrone U H. henryi H. Lév & Vaniot −46 (0.16, m) Liao 2016
50.5 R1 = i-Pr
R2 = prenyl
R3 = prenyl
R4 = X1, 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
R4 = X1 = H
R5 = 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
R4 = X1 = H
R5 = 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
R4 = X1 = H
R5 = 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
R4 = X1 = H
R5 = 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
R4 = X1 = H
R5 = 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
R4 = X1 = H
R5 = 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
R4 = X1 = H
R5 = X2 = OH
hyperforatone M[c] H. perforatum −10.4 (0.3, m) Y. Guo 2018
50.13 R1 = i-Bu
R2 = prenyl
R3 = H
R4 = X1 = H
R5 = X2 = OH
przewalcyrone C[c] H. przewalskii −80.33 (0.3, m) Duan 2019
50.14 R1 = i-Bu
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
przewalcyrone D[c] H. przewalskii −67.70 (0.18, m) Duan 2019
50.15 R1 = (S)-s-Bu
R2 = prenyl
R3 = H
R4 = X1 = H
R5 = X2 = OH
przewalcyrone A[c] H. przewalskii −109.29 (0.43, m) Duan 2019
50.16 R1 = (S)-s-Bu
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
przewalcyrone B[c] H. przewalskii −132.38 (0.3, m) Duan 2019
50.17 R1 = (S)-s-Bu
R2 = prenyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = H
hyperwilsone F[c] H. wilsonii −36.8 (0.4, m) Y. Duan 2021c
50.18 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = X1 = H
R5 = X2 = OH
hyphenrone V H. henryi H. Lév & Vaniot −38 (0.16, m) Liao 2016
50.19 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = H
hyperwilsone G[c] H. wilsonii −44.0 (0.3, m) Y. Duan 2021c
50.20 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = X1 = H
R5 = X2 = OH
hyperwilsone H[c] H. wilsonii −60.6 (0.5, m) Y. Duan 2021c
Structure 51: hyperhookerione H — A, bicyclononanes, exo
51
hyperhookerione H[c] H. hookerianum −110 (0.5, m) Z. Guo 2025
Structure 52: hyperhookerione I — A, bicyclononanes, exo
52
hyperhookerione I[c] H. hookerianum −163 (0.5, m) Z. Guo 2025
Structure 53: garcinielliptone H — A, bicyclononanes, exo
53
garcinielliptone H G. subelliptica −14.3 (0.1) Weng 2003b
Structure 54: ascynol G — A, bicyclononanes, exo
54
ascynol G[c] H. ascyron +78 (0.1, m) Y.-L. Hu 2025
Structure 55: garcinielliptone G — A, bicyclononanes, exo
55
garcinielliptone G G. subelliptica −53 (0.1) Weng 2003b, Y.-G. Fu 2025
Structure 56: hyperscabin D — A, bicyclononanes, exo
56
hyperscabin D[c] H. scabrum +71.4 (0.08, mc) J. Ma 2021b
Structure 57: hyperforone  A — A, bicyclononanes, caged
57
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
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
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
hyperforone D[c] H. perforatum +68.9 (0.9, m) Y. Guo 2021b
Structure 61: hyperforone E — A, bicyclononanes, exo
61
hyperforone E[c] H. perforatum −66.4 (0.3, m) Y. Guo 2021b
Structure 62: hyperforone F — A, bicyclononanes, exo
62
hyperforone F[c] H. perforatum −30.0 (0.8, m) Y. Guo 2021b
Structure 63: hyperforone G — A, bicyclononanes, exo
63
hyperforone G[c] H. perforatum −15.2 (0.4, m) Y. Guo 2021b
Structure 64: hyperforone H — A, bicyclononanes, exo
64
hyperforone H[c] H. perforatum −22.3 (0.9, m) Y. Guo 2021b
Structure 65: hyperatin A — A, bicyclononanes, exo
65
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
hyperacmose C[c] H. acmosepalum +21.43 (0.56, m) Z. Hu 2026
Structure 69: hypericumoxide N — A, bicyclononanes, exo
69
hypericumoxide N[d] H. scabrum −24.2 (0.09, m) R. Liu 2017
Structure 70: hyperpatone A — A, bicyclononanes, exo
70
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) 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) 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
hyperfol H[c][dd] H. perforatum −203 (0.3, m) Lou 2020b
Structure 74: hyperfol B — A, bicyclononanes, exo
74
hyperfol B[c] H. perforatum −33.24 (0.09, m) Lou 2020a
Structure 75: hyperkouytone N — A, bicyclononanes, exo
75
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
ascynol H[c] H. ascyron −22 (c 0.3, m) Y.-L. Hu 2025
Structure 79: hyphenrone D — A, bicyclononanes, exo
79
hyphenrone D[c] H. henryi −62.5 (0.10, m) X.-W. Yang 2014
Structure 80: hyperlanin A — A, bicyclononanes, exo
80
hyperlanin A, a.k.a. hyperforatone A[c] (one of two by the second name) H. lancasteri −18.0 (0.3, m) You 2024, W.-Y. Liu 2025a
Structure 81: hyperfol A — A, bicyclononanes, exo
81
hyperfol A[c] H. perforatum −202.49 (0.3, m) 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) 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
hyperforen A[c] H. perforatum +9.53 (0.05, m) 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) 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) 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
uralin B[c] H. uralum +63 (0.3, m) Q.-Q. Fang 2021
Structure 86: hypsampsone A — B, bicyclononanes, endo
86
hypsampsone A[d] H. sampsonii +71.49 (0.7, m) Z.-Z. Zhang 2021
Structure 87: hypersampone A — A, bicyclononanes, exo
87
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
norhyperpalum A[d] H. patulum −53.7 (c 0.3, m) Y. Duan 2021b
Structure 94: hyperscabin E — A, bicyclononanes, endo
94
hyperscabin E[c] H. scabrum +103.2 (0.14, mc) J. Ma 2021b
Structure 95: hypertum A — A, bicyclononanes, exo
95
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) 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
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) Suo 2021a
98.2 R = (S)-s-Bu hyperacmosin C[c] H. acmosepalum −12.30 (0.26, m) Suo 2021a
Structure 99: hyperbenzone A — A, bicyclononanes, endo
99
hyperbenzone A[c] H. beanii −4 (0.2, m) Lu 2021
Structure 100: hyperbenzone B — A, bicyclononanes, endo
100
hyperbenzone B[c] H. beanii +12 (0.1, m) Lu 2021
Structure 101: spirohypolactone A — A, bicyclononanes, exo
101
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
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) 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
norwilsonnol B[d] H. wilsonii +111.0 (0.5, m) Xie 2021
Structure 108: hyperisenin A — A, bicyclononanes, exo
108
hyperisenin A[d] H. seniawinii +42.0 (0.1, m) Y. Duan 2025
Structure 109: hypertum B — A, bicyclononanes, exo
109
hypertum B[c] H. perforatum −9.5 (0.15, m) W.-Y. Liu 2025b
Structure 110: norwilsonnol A — A, bicyclononanes, exo
110
norwilsonnol A[c] H. wilsonii −174.0 (0.7, m) Xie 2021
Structure 111: hyperwilsol A — A, bicyclononanes, exo
111
hyperwilsol A[c] H. wilsonii −5.55 (0.08, m) Z.-X. Wang 2025
Structure 112: hypseudohenrin H — A, bicyclononanes, exo
112
hypseudohenrin H[c] H. wilsonii −8.56 (1.29, m) M.-X. Sun 2024
Structure 113: hypertum C — A, bicyclononanes, exo
113
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 R1 = X1 = OMe
R2 = X2 = H
hypertum D[c] H. perforatum mixture with hypertum E: −40.1 (0.1, m) W.-Y. Liu 2025b
114.2 R1 = X1 = H
R2 = 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
norgarmultinone B[c] G. multiflora +43.37 (0.07, m) Teng 2020
Structure 116: hypseudohenrin C — A, bicyclononanes, endo
116
hypseudohenrin C[c] H. pseudohenryi +10.5 (1.14, m) H. Sun 2021b
Structure 117: hyperwilsol D — A, bicyclononanes, exo
117
hyperwilsol D[c] H. wilsonii −81.55 (0.04, m) Z.-X. Wang 2025
Structure 118: hypseudohenrin D — A, bicyclononanes, endo
118
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) 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
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) 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) 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
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
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) Tanaka 2009b
128.2 R1 = i-Pr
R2 = prenyl
yezo'otogirin A[c] H. yezoense −168.2 (0.25) 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) 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
hypermogin D[c] H. monogynum −32.0 (0.2, m) Y.-R. Zeng 2021a
Structure 131: ascynol D — A, bicyclononanes, caged
131
ascynol D[c] H. ascyron −31 (0.1, m) Y.-L. Hu 2025
Structure 132: ascynol B — A, bicyclononanes, caged
132
ascynol B[c] H. ascyron +17 (0.1, m) Y.-L. Hu 2025
Structure 133: ascynol C — A, bicyclononanes, caged
133
ascynol C[c] H. ascyron −82 (0.06, m) Y.-L. Hu 2025
Structure 134: ascynol A — A, bicyclononanes, caged
134
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
norprzewalsone A[c] H. przewalskii +76.7 (0.4, m) Y. Duan 2022b
Structure 137: hyperforatum A — A, bicyclononanes, exo
137
hyperforatum A[c] H. perforatum +2 (0.1, m) X. Wang 2024
Structure 138: hyperforatum B — A, bicyclononanes, endo
138
hyperforatum B[e] H. perforatum +7.5 (1.00, m) X. Wang 2024
Structure 139: hyperforatum C — A, bicyclononanes, seco
139
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
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) Ye 2016
142.2 R1 = i-Pr
R2 = geranyl
R3 = prenyl
R4 = CH=CMe2
hypersubone C[d] H. subsessile −13.3 (3.20, m) 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) 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) 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) 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) 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) Ye 2016
142.8 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = CH=CMe2
plukenetione A C. plukenetii +1 (0.8) 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) Christian 2001, 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) 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) 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) 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) 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) 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, 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) 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) 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
hyperadaman D[d] H. wilsonii +47.7 (0.2, m) B. Tao 2024b
Structure 145: wilsonglucinol I — A, bicyclononanes, caged
145
wilsonglucinol I[d] H. wilsonii +20.9 (0.25, m) H. Cheng 2022a
Structure 146: garciyunnanone G — A, bicyclononanes, caged
146
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
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) 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) Max 2021
151.2 R1 = s-Bu
R2 = prenyl
X = OH
hyperihirsolin B[e] H. hirsutum −13.0 (0.90, m) 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) 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) 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
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) 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) 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) Zhu 2014
156.3 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H
no common name C. obdeltifolia +10.0 (0.4) Teixeira 2005
156.4 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = OH
hyperisampsin F[d] H. sampsonii +2.0 (0.10, m) 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, 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
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
hyperesternoid G[d] H. kouytchemse −53.9 (0.3, m) Z. Dong 2026
Structure 160: hyperesternoid H — A, bicyclononanes, caged
160
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) Ye 2016
161.2 R1 = geranyl
R2 = H
R3 = (S)-3,3-dimethyloxiran-2-yl
hookerione H[d] H. hookerianum −152 (0.14, m) Ye 2016
161.3 R1 = geranyl
R2 = CO2Me
R3 = CH=CMe2
hypersubone A[d] H. subsessile −142.5 (0.09, m) Liao 2015
161.4 R1 = geranyl
R2 = CO2Me
R3 = (R)-3,3-dimethyloxiran-2-yl
hookerione E[d] H. hookerianum −146 (0.16, m) Ye 2016
161.5 R1 = geranyl
R2 = CO2Me
R3 = (S)-3,3-dimethyloxiran-2-yl
hookerione F[d] H. hookerianum −198 (0.12, m) Ye 2016
Structure 162: cumilcinol I — A, bicyclononanes, caged
162
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
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) Max 2021
165.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OOH
R4 = prenyl
peroxyhirsutofolin A H. hirsutum +12.0 (0.79, m) 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) 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) 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) Max 2021
165.11 R1 = Ph
R2 = prenyl
R3 = CMe2OH
R4 = prenyl
sampsonione R C. obdeltifolia, H. sampsonii, H. attenuatum +10.8 (0.011) Cruz 2004, 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 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) 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
hypersampsone L H. sampsonii −67.4 (0.098) Y. H. Zeng 2012
Structure 168: hypersampsone  S — A, bicyclononanes, caged
168
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
hypseudohenone A[d] H. pseudohenryi +19.6 (0.222, m) N.-N. Jiang 2023
Structure 171: patumantane A — A, bicyclononanes, caged
171
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) 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) 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) Max 2021
174.4 R1 = s-Bu
R2 = prenyl
R3 = E-CH=CHCMe2OH
3‴-hydroxyisohirsutuman B[e] H. hirsutum −69.5 (0.19, m) 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, Cruz 2004, Sriyatep 2017
174.6 R1 = Ph
R2 = prenyl
R3 = CH2CH2CMe2OH
no common name C. obdeltifolia −5.1 (0.012) 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
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) 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) Henry 1999, Christian 2001, Xiao 2010
178.5 R1 = Ph
R2 = prenyl
R3 = CMe2OOH
peroxysampsone A H. sampsonii +17.0 (0.128) Xiao 2010
178.6 R1 = Ph
R2 = (E)-CH=CHCMe2OOH
R3 = CMe2OH
33-hydroperoxyisoplukenetione C C. havetiodes var. stenocarpa −3.9 (0.2) Christian 2001
178.7 R1 = Ph
R2 = geranyl
R3 = CMe2OH
otogirinin B H. erectum Thunb., H. attenuatum +12.0 (0.14, m) Ishida 2010, D. Li 2015a
178.8 R1 = Ph
R2 = geranyl
R3 = CMe2OOH
hyperisampsin O[d] H. sampsonii +12 (0.2, m) 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) 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) 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) Teng 2021
Structure 180: peroxysampsone B — A, bicyclononanes, caged
180
peroxysampsone B H. sampsonii, H. attenuatum −41.2 (0.042) 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) Max 2021
181.2 R = s-Bu pyranohyperihirsan B[e] H. hirsutum −30.7 (0.25, m) Max 2021
Structure 182: hyperattenin M — A, bicyclononanes, caged
182
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
hyperesternoid Y[d] H. monogynum −42.3 (0.1, m) Z. Dong 2026
Structure 185: hyperesternoid Z — A, bicyclononanes, caged
185
hyperesternoid Z[d] H. monogynum −48.7 (0.1, m) Z. Dong 2026
Structure 186: wilsonglucinol A — A, bicyclononanes, caged
186
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
garcimultinone C[d][e] G. multiflora −59.4 (0.02, m) 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
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) 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, 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) 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) 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 Max 2021
194.6 R1 = Ph
R2 = prenyl
R3 = i-Pr
X = H
hookerione L H. hookerianum +31.4 (0.10, m) Ye 2019
194.7 R1 = Ph
R2 = prenyl
R3 = CMe=CH2
X = H
hypersampsone X[d] H. sampsonii +27.1 (0.50) Tian, 2017
194.8 R1 = Ph
R2 = prenyl
R3 = CMe2OH
X = H
plukenetione B C. plukenetii +17.2 (0.03) Henry 1999, 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) 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) 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) 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) 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, Max 2021
196.4 R1 = Ph
R2 = prenyl
R3 = OH
X = H
no common name C. obdeltifolia, G. propinqua NR Cruz 2004, 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) 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) Ye 2019
197.2 R1 = i-Pr
R2 = prenyl
R3 = CMe2OH
hirsutusal A[e] H. hirsutum +36.7 (0.18, m) 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) Ye 2019
197.6 R1 = s-Bu
R2 = prenyl
R3 = CMe2OH
hirsutusal B[e] H. hirsutum −6.9 (0.24, m) Max 2021
197.7 R1 = Ph
R2 = prenyl
R3 = OH
pseudohenone E C. obdeltifolia, H. pseudohenryi N. Robson −27 (0.13, m) 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, 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) 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) 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) 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) 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
hypertonii A[c] H. addingtonii N. Robson +42.3 (0.1, acn) Q. Feng 2025
Structure 199: dioxasampsone A — A, bicyclononanes, caged
199
dioxasampsone A[d] H. sampsonii +16.8 (0.50) W.-J. Tian 2014c
Structure 200: hyperesternoid R — A, bicyclononanes, caged
200
hyperesternoid R[d] H. monogynum −32.7 (0.2, m) Z. Dong 2026
Structure 201: hyperesternoid S — A, bicyclononanes, caged
201
hyperesternoid S[d] H. monogynum −24.8 (0.2, m) Z. Dong 2026
Structure 202: pseudohenone A — A, bicyclononanes, caged
202
pseudohenone A H. pseudohenryi N. Robson +43 (0.20, m) X.-W. Yang 2017b
Structure 203: cumilcinol B — A, bicyclononanes, caged
203
cumilcinol B[d] H. wilsonii +98.0 (0.1, m) B. Tao 2024a
Structure 204: hypercurpalone A — A, bicyclononanes, dimer
204
hypercurpalone A[d] H. curvisepalum −17.9 (0.13, m) Y. Ye 2022
Structure 205: hypseudone A — A, bicyclononanes, caged
205
hypseudone A[c] H. pseudohenryi +38.2 (0.096, m) Jiang 2025
Structure 206: garsubelone A — A, bicyclononanes, dimer
206
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) Coqueiro 2016
207.3 R1 = i-Bu
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H
spiranthenone B Spiranthera odoratissima −24 (0.10) 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) de Oliveira 1996, Piccinelli 2005, Rodeschini 2007, Henry 2008, Garnsey 2010, 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) Merza 2006, Masullo 2008
207.12 R1 = Ph
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H
spiritone[e] C. spiritu-sanctensis NR Porto 2000
207.13 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = H
18-hydroxyclusianone H. hypericoides NR Christian 2008
207.14 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
R5 = prenyl
guttiferone J, a.k.a. garciyunnanin A and tautomer iso-guttiferone J G. cambogia, G. gummi-gutta, G. virgata, G. yunnanensis −34.3 (1.75, m), −3.0 (0.11) Merza 2006, Masullo 2008, G. Xu 2008, 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) 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) Cuesta-Rubio 2001b, 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, Masullo 2008, G. Xu 2010, 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) 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) 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) 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) Hamed 2006, G. Xu 2010, 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) Williams 2003, Herath 2005, 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) Hamed 2006, G. Xu 2010, 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) 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) 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) 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) 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) 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) 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) Masullo 2008, Masullo 2010
207.36 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = prenyl
guttiferone P G. solomonensis +18.2 (0.33) 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) 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) 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) 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) 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) Winkelmann 2001a
208.2 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = prenyl
R4 = prenyl
R5 = H
laxifloranone[e] Marila laxiflora +23.6 (0.8, m) 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) 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) Trisuwan 2012, 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) 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) 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) Tanaka 2004
208.16 R1 = Ph
R2 = prenyl
R3 = Me
R4 = prenyl
R5 = prenyl
hyperelatone A[d] H. elatoides +189.3 (0.1) 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) Delle Monache 1991, Santos 1998, de Almeida Alves 1999, Winkelmann 2001a, Piccinelli 2005, 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) 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) Christian 2008
208.22 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
R5 = H
oblongifolin E G. oblongifolia +65.1 (0.40) Huang 2009
208.23 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = geranyl
R4 = prenyl
R5 = H
guttiferone N G. cambogia −34.5 (0.07, m) Masullo 2008
208.24 R1 = 3-hydroxyphenyl
R2 = prenyl
R3 = lavandulyl
R4 = prenyl
R5 = H
14-deoxygarcinol[e] M. coccinea −42 (0.3) 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) 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) 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) Gustafson 1992, 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) Hamed 2006, G. Xu 2010, 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) Soemiati 2006, Hartati 2008, 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) 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) 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) 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) Rama Rao 1980, Krishnamurthy 1981, Sahu 1989, Fuller 1999, Marti 2009, G. Xu 2010, Socolsky 2015, Zheng 2017, 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) Gustafson 1992, Fuller 1999, Cuesta Rubio 1999, Cuesta Rubio 2002, Merza 2006, Socolsky 2015, 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 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) Karanjgoakar 1973, Dreyer 1974, Venkatswamy 1975, Blount 1976, Cuesta Rubio 1999, Roux 2000, Cuesta Rubio 2002, Baggett 2005, Merza 2006, C.-C. Wu 2008a, 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 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) 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) 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) 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) 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) 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) 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) 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) 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) Zheng 2017, J.-Y. Xie 2024
209.2 R = geranyl garciyunnanimine C[c] G. yunnanensis Hu +11.4 (0.041, m) 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) 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
oblongifolin M[c][l][m] G. oblongifolia −4.2 (0.05, m) H. Zhang 2014a
Structure 213: enervosanone — B, bicyclononanes, exo
213
enervosanone Calophyllum enervosum +10 (0.2000, 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
R4 = X1 = OH
R5 = X2 = OH
R6 = X3 = H
oxy-guttiferone K[d] G. cambogia +20.9 (0.1) Masullo 2008, Masullo 2010
214.2 R1 = prenyl
R2 = geranyl
R3 = H
R4 = X1 = OH
R5 = X2 = OH
R6 = X3 = H
oblongifolin G G. oblongifolia +5.9 (0.41) Huang 2009
214.3 R1 = prenyl
R2 = geranyl
R3 = H
R4 = X1 = H
R5 = X2 = H
R6 = X3 = OH
oblongifolin I G. oblongifolia NR Y. Zhou 2010
214.4 R1 = prenyl
R2 = geranyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = OH
R6 = X3 = H
garciyunnanin B G. yunnanensis +18.1 (0.12) G. Xu 2008
214.5 R1 = prenyl
R2 = geranyl
R3 = prenyl
R4 = X1 = H
R5 = X2 = OH
R6 = X3 = OH
garciyunnanin K[d] G. yunnanensis +2.2 (0.10, m) Zheng 2021b
214.6 R1 = geranyl
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = OH
R6 = X3 = H
oxy-guttiferone M G. cambogia −96.2 (0.1, m) Masullo 2010
214.7 R1 = lavandulyl
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = OH
R6 = X3 = H
symphonone H[e] S. globulifera −37 (0.2) 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
R4 = X1 = OH
R5 = X2 = H
garcimultiflorone I[d] G. multiflora −42.1 (0.36, m) Fu 2015
215.2 R1 = prenyl
R2 = prenyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = H
2,16-oxyguttiferone A[d] S. globulifera +48 (1.0, m) Cottet 2015
215.3 R1 = prenyl
R2 = geranyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
oblongifolin F G. oblongifolia −85.6 (0.41) Huang 2009
215.4 R1 = prenyl
R2 = geranyl
R3 = H
R4 = X1 = H
R5 = X2 = OH
oblongifolin H G. oblongifolia NR Y. Zhou 2010
215.5 R1 = geranyl
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
oxy-guttiferone I G. cambogia +23.8 (0.1, m) Masullo 2010
215.6 R1 = (S)-lavandulyl[f]
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
garcimultiflorone J[c] G. multiflora +11.11 (0.44, m) Fu 2015, X. Wang 2021a
215.7 R1 = isolavandulyl[g]
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
nujiangefolin A[e] G. nujiangensis −2 (0.10, m) Xia 2012
215.8 R1 = (R)-isolavandulyl[g]
R2 = (E)-CH=CHCMe2OH
R3 = H
R4 = X1 = OH
R5 = X2 = H
nujiangefolin D[d] G. nujiangensis −12 (0.10, m) Tang 2019
215.9 R1 = (1S,3R)-3-isopropenyl-2,2-dimethylcyclobutylmethyl
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = X2 = H
picrorhizone H[d] G. picrorhiza −7 (0.10, m) Sukandar 2020
215.10 R1 = 3-isopropenyl-2,2-dimethylcyclopentyl
R2 = prenyl
R3 = H
R4 = X1 = OH
R5 = 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
R4 = X1 = OH
R5 = X2 = H
garciesculentone B[e] G. esculenta +18.4 (0.04, m) H. Zhang 2014b
Structure 216: garcinialone — B, bicyclononanes, exo
216
garcinialone[l][m] G. multiflora −2.0 (0.02, m) Chien 2008
Structure 217: xanthochymusone N — B, bicyclononanes, endo
217
xanthochymusone N[d] G. xanthochymus −16 (0.1, m) Y.-G. Fu 2025
Structure 218: no      name — B, bicyclononanes, exo
218
no common name G. indica +18.9 (0.1, m) Kaur 2012
Structure 219: symphonone I — B, bicyclononanes, exo
219
symphonone I S. globulifera −22 (0.4) 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) 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) Masullo 2010
221.2 R1 = isolavandulyl[g]
R2 = H
garcixanthochymone J[d][e] G. xanthochymus +53.2 (0.73, m) 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) 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) 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) Xia 2012
Structure 223: garciyunnanensisin E — B, bicyclononanes, endo
223
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) 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) 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) Marti 2010
Structure 226: hyperascyrin N — B, bicyclononanes, exo
226
hyperascyrin N[d] H. ascyron +40.0 (0.1, m) B. Zhen 2019
Structure 227: no         name — B, bicyclononanes, caged
227
no common name H. scabrum +17.2 (1.0, m) 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) 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) 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) 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) 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) 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) 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) Matsuhisa 2002, Ciochina 2006, Lindermayr 2013
229.2 R1 = Ph
R2 = prenyl
R3 = (E)-CH=CHCMe2OH
R4 = H
hyperibone H H. scabrum +12.4 (0.4) Matsuhisa 2002, Ciochina 2006
229.3 R1 = Ph
R2 = (S)-lavandulyl[f]
R3 = prenyl
R4 = H
garcimultinone L[d] G. multiflora +110.00 (0.04, m) 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
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) Kaennakam 2022b
231.3 R1 = CMe2OH
R2 = prenyl
garcowacinol G[d] G. cowa −28.1 (0.30, m) Kaennakam 2022b
Structure 232: garcowacinol H — B, bicyclononanes, exo
232
garcowacinol H[d] G. cowa −21.2 (0.50, m) 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) 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, 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 Rasol 2017
234.2 R1 = s-Bu
R2 = CHPhCH2CO2H
R3 = CH2CHOHCMe2OH
mesuaferroic acid E[e][m] Mesua ferrea NR Rasol 2017
234.3 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = prenyl
mesuaferroic acid C[e][m] Mesua ferrea NR Rasol 2017
234.4 R1 = i-Bu
R2 = CHPhCH2CO2H
R3 = CH2CHOHCMe2OH
mesuaferroic acid F[e][m] Mesua ferrea NR 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, 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 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
paucinone A G. paucinervis −6.2 (0.05, m) X.-M. Gao 2010
Structure 237: paucinone B — B, bicyclononanes, endo
237
paucinone B G. paucinervis +58.7 (0.10, m) X.-M. Gao 2010
Structure 238: paucinone C — B, bicyclononanes, endo
238
paucinone C G. paucinervis +19.2 (0.17, m) X.-M. Gao 2010
Structure 239: garcicowin A — B, bicyclononanes, noC3
239
garcicowin A G. cowa −219.0 (0.09) G. Xu 2010
Structure 240: garcowacinol D — B, bicyclononanes, noC3
240
garcowacinol D[d] G. cowa +37.0 (0.50, m) 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) 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) Marti 2010
242.4 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = prenyl
7-epi-isogarcinol M. coccinea, S. globulifera −158 (1.0) Marti 2009, Marti 2010
242.5 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = 3-methylbutyl
epunctanone G. epunctata Stapf +24.9 (0.00985, a) Fotso 2014
242.6 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe=CH2
symphonone A S. globulifera −37 (0.7) Marti 2010
242.7 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = (E)-CH=CHCMe2OH
symphonone C S. globulifera −67 (1.0) Marti 2010
242.8 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = prenyl
R4 = geranyl
symphonone B S. globulifera −81 (1.0) 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) 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) Marti 2010
242.12 R1 = 3,4-dihydroxyphenyl
R2 = prenyl
R3 = CH2CHOHCMe2OH
R4 = prenyl
symphonone E[e] (diastereomer) S. globulifera −50 (0.4) 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) 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) Teng 2021
244.3 R1 = 3-hydroxyphenyl
R2 = Me
R3 = prenyl
R4 = prenyl
R5 = prenyl
14-deoxyisogarcinol G. indica −178.0 (0.1, m) 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) Karanjgoakar 1973, Gustafson 1992, Iinuma 1996, Roux 2000, Baggett 2005, 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) Rama Rao 1980, Krishnamurthy 1981, Krishnamurthy 1982, Sahu 1989, Fuller 1999, G. Xu 2010, Trinh 2013, Socolsky 2015, 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) Iinuma 1996, Roux 2000, 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) 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) 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) 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) 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) 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) 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) 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
garpedvinin E[c] G. pedunculata Roxb. −86.6 (0.30, m) D.-L. Zou 2025
Structure 246: garpedvinin A — B, bicyclononanes, endo
246
garpedvinin A[c] G. pedunculata Roxb. −86.6 (0.30, m) D.-L. Zou 2025
Structure 247: garciesculentone A — B, bicyclononanes, endo
247
garciesculentone A[m] G. esculenta −116.5 (0.06, m) H. Zhang 2014b
Structure 248: garcinialiptone B — B, bicyclononanes, endo
248
garcinialiptone B G. subelliptica +84.8 (5.40, m) L.-J. Zhang 2010
Structure 249: garcicowin D — B, bicyclononanes, exo
249
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
garpedvinin D[c] G. pedunculata Roxb. −54.6 (0.1, m) D.-L. Zou 2025
Structure 252: garcoblone E — B, bicyclononanes, endo
252
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
coccinone A M. coccinea +28 (1.0) Marti 2009
Structure 254: garpedvinin B — B, bicyclononanes, endo
254
garpedvinin B[c] G. pedunculata Roxb. −65.5 (0.1, m) D.-L. Zou 2025
Structure 255: garpedvinin C — B, bicyclononanes, endo
255
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
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) Kaennakam 2022a
258.2 R = geranyl garschomcinol D[d] G. schomburgkiana +13.1 (0.30, m) 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, 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) Deng 2022
259.4 R1 = prenyl
R2 = Me
R3 = (E)-CH=CHC(Me)=CH2
ascyrone E[d] H. ascyron +3 (0.09, MeOH) 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) Kaennakam 2022b
260.2 R1 = Ph
R2 = H
R3 = prenyl
R4 = prenyl
R5 = CMe2OH
garcowacinol I[d] G. cowa +13.5 (0.10, m) 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) 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) 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) Deng 2022
260.7 R1 = 3,4-dihydroxyphenyl
R2 = H
R3 = prenyl
R4 = geranyl
R5 = CMe2OH
schomburgkianone E[d] G. schomburgkiana +104 (0.4) Le 2016
Structure 261: guttiferone H — B, bicyclononanes, exo
261
guttiferone H[e] G. xanthochymus +94 (0.006) Baggett 2005
Structure 262: garcixanthochymone K — B, bicyclononanes, exo
262
garcixanthochymone K[d] G. xanthochymus −37.9 (0.20, m) Jin 2021
Structure 263: burlemarxione E — B, bicyclononanes, caged
263
burlemarxione E C. burlemarxii +11.0 (0.5) Ferraz 2021
Structure 264: hyperprin A — B, bicyclononanes, caged
264
hyperprin A[d] H. przewalskii −4.0 (0.10, m) 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
garciyunnanol A[d] G. yunnanensis +14 (0.16, m) X.-Y. Hu 2024
Structure 267: thoreliolide A — B, bicyclononanes, endo
267
thoreliolide A[d][e] Calophyllum thorelii +82.0 (0.45, e) L.-T. T. Nguyen 2016
Structure 268: thoreliolide B — B, bicyclononanes, exo
268
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) Tanaka 2004, 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 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
garcixanthochymone C G. xanthochymus +51.0 (0.400, m) Y. Chen 2017
Structure 271: oblongifolin J — B, bicyclononanes, caged
271
oblongifolin J[c] G. oblongifolia +8.6 (0.03, m) H. Zhang 2014a
Structure 272: hypersampsone  R — B, bicyclononanes, endo
272
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
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
soniiglucinol A[c] H. wilsonii −74.0 (0.2, m) Xie 2020a
Structure 276: soniiglucinol B — A, bicyclononanes, endo
276
soniiglucinol B[c][e] H. wilsonii −139.4 (0.4, m) 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) Xie 2020b
277.2 R1 = i-Pr
R2 = geranyl
hypersonin C[c] H. wilsonii −2 (0.4, m) Xie 2020b
277.3 R1 = s-Bu
R2 = prenyl
hypersonin B[c][e] H. wilsonii +3 (0.9, m) Xie 2020b
Structure 278: hypersonin D — A, bicyclononanes, endo
278
hypersonin D[c][e] H. wilsonii −1 (0.2, m) Xie 2020b
Structure 279: soniiglucinol C — A, bicyclononanes, endo
279
soniiglucinol C[c] H. wilsonii −151.3 (0.3, m) Xie 2020a
Structure 280: soniiglucinol D — A, bicyclononanes, endo
280
soniiglucinol D[c] H. wilsonii −24.9 (0.2, m) Xie 2020a
Structure 281: enaimeone A — B, bicyclooctanes
281
enaimeone A H. papuanum +27.8 (0.1, m) Winkelmann 2001b, 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) Winkelmann 2001b, zur Bonsen 2023
282.2 R = s-Bu enaimeone C[e] H. papuanum +32.9 (0.1, m) Winkelmann 2001b, 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) Winkelmann 2000
284.2 R1 = i-Pr
R2 = CMe2OH
1′-hydroxyialibinone A H. papuanum +3.7 (0.1, m) Winkelmann 2001b
284.3 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2
yezo'otogirin E H. yezoense +21.4 (1.7, m) Tanaka 2016a
284.4 R1 = s-Bu
R2 = CMe=CH2
ialibinone C[e] H. papuanum −26 (0.1) 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) Winkelmann 2000
285.2 R1 = i-Pr
R2 = CMe=CH2
ialibinone B H. papuanum −91 (0.1) Winkelmann 2000
285.3 R1 = i-Pr
R2 = CMe2OH
1′-hydroxyialibinone B H. papuanum −35.7 (0.1, m) Winkelmann 2001b
285.4 R1 = i-Pr
R2 = C(=CH2)CH2CH2CH=CMe2
yezo'otogirin F H. yezoense +75.9 (1.7, m) Tanaka 2016a
285.5 R1 = s-Bu
R2 = CMe=CH2
ialibinone D[e] H. papuanum −72 (0.1) Winkelmann 2000
285.6 R1 = s-Bu
R2 = CMe2OH
1′-hydroxyialibinone D[e] H. papuanum −30.3 (0.1, m) Winkelmann 2001b
Structure 286: lancasternoid A — B, bicyclooctanes
286
lancasternoid A H. lancasteri racemic J.-Q. You 2025
Structure 287: lancasternoid B — B, bicyclooctanes
287
lancasternoid B H. lancasteri racemic J.-Q. You 2025
Structure 288: lancasternoid C — B, bicyclooctanes
288
lancasternoid C H. lancasteri racemic J.-Q. You 2025
Structure 289: lancasternoid D — B, bicyclooctanes
289
lancasternoid D H. lancasteri racemic J.-Q. You 2025
Structure 290: takaneone A — B, bicyclooctanes, twoC3
290
takaneone A H. sikokumontanum +30.0 (0.2, m) Tanaka 2008
Structure 291: takaneone B — B, bicyclooctanes, twoC3
291
takaneone B H. sikokumontanum +24.0 (0.3, m) 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) 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
hyperelodione F[d] H. elodeoides +24.8 (0.33, m) D.-R. Qiu 2021
Structure 294: garcibracgluinol A — bicyclooctanes, seco
294
garcibracgluinol A[c] G. bracteata +141.4 (0.02, m) J. Xu 2025
Structure 295: no          name — B, bicyclooctanes, seco
295
no common name H. scabrum +30.5 (1.0) Soroury 2020
Structure 296: hyperireflexolide A — otherSpiro, seco
296
hyperireflexolide A[c] H. beanni 0 (1.54) Cardona 1993
Structure 297: hyperireflexolide B — otherSpiro, seco
297
hyperireflexolide B[c] H. beanni 0 (0.74) Cardona 1993, zur Bonsen 2023
Structure 298: hyperberlone A — otherBridgedBicycles, seco
298
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) Liaw 2019
299.2 garcinielliptone HH[d] (enantiomer) G. subelliptica +16 (0.05, m) 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) Oya 2015, Ferraz 2019, M. do C. C. Silva 2024
300.2 R1 = prenyl
R2 = H
R3 = prenyl
(+)-nemorosonol[d] (enantiomer) C. nemorosa +203 (0.7) Delle Monache 1988, 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) Tantapakul 2012, Pepper 2012, 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, Tanaka 2019
Structure 301: trijapin A — caged, fourPlusTwo
301
trijapin A[c] T. japonicum −25 (0.2, m) Oya 2015
Structure 302: trijapin B, garcibracteamone J — caged, fourPlusTwo
302
302.1 R = prenyl trijapin B T. japonicum −200 (0.1, m) 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
trijapin C T. japonicum +38 (0.04, m) 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
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
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) Fan 2015
308.2 R1 = prenyl
R2 = prenyl
(+)-garcimulin A[d] (enantiomer) G. multiflora +115.1 (0.11, m) Fan 2015
308.3 R1 = CH2CH2CMe=CH2
R2 = prenyl
garcimulin B[c] G. multiflora −118.5 (0.21, 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
hyperuralone A[d] H. uralum +34.3 (0.2, m) J.-J. Zhang 2014b
Structure 314: hyperforcinol B — caged, fourPlusTwo
314
hyperforcinol B[d] H. forrestii +72 (0.2, m) W.-J. Lu 2021
Structure 315: uralin A — caged, fourPlusTwo
315
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
burlemarxione A C. burlemarxii −113.0 (1.35) 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
hypatulin A[c] H. patulum +40 (0.05, m) Tanaka 2016b
Structure 319: hyperforcinol C — caged, fourPlusTwo, seco
319
hyperforcinol C[c] H. forrestii +30 (0.2, m) W.-J. Lu 2021
Structure 320: hypatulin B — fourPlusTwo, seco, uncaged
320
hypatulin B H. patulum +27.0 (0.17, m) Tanaka 2016b
Structure 321: garcimultiflin D, garcimultiflin A — caged, fourPlusTwo, seco
321
321.1 R1 = X1 = H
R2 = X2 = OH
garcimultiflin D[d] G. multiflora +10.0 (1.0, m) H. Luo 2025
321.2 R1 = X1 = OH
R2 = X2 = H
garcimultiflin A[d] G. multiflora −15.0 (1.0, m) J. Cao 2023
Structure 322: garcimultiflin B — caged, fourPlusTwo, seco
322
garcimultiflin B[d] G. multiflora −10.0 (1.0, m) J. Cao 2023
Structure 323: garcimultiflin C — caged, fourPlusTwo, seco
323
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
R5 = X1 = H
R6 = X2 = H
R7 = X3 = H
garcibracteatone G. bracteata −1 (1.00) Thoison 2005
324.2 R1 = prenyl
R2 = H
R3 = H
R4 = prenyl
R5 = X1 = H
R6 = X2 = OH
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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, Tanaka 2019
324.5 R1 = prenyl
R2 = H
R3 = prenyl
R4 = (E)-CH=CHCMe2OOH
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = X3 = H
doitunggarcinone A G. propinqua −133.3 (0.015) Tantapakul 2012, Pepper 2012
324.9 R1 = CH2CH2CMe=CH2
R2 = H
R3 = H
R4 = prenyl
R5 = X1 = H
R6 = X2 = OH
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = OH
R6 = X2 = OH
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = 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
R5 = X1 = H
R6 = X2 = H
R7 = X3 = H
hyphenrone R H. henryi H. Lév & Vaniot −15 (0.15, m) Liao 2016
324.24 R1 = (E)-CH=CHCMe2OOH
R2 = H
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = X2 = H
R7 = X3 = H
hyphenrone S H. henryi H. Lév & Vaniot −14 (0.12, m) Liao 2016
324.25 R1 = (E)-CH=CHCMe2OMe
R2 = H
R3 = prenyl
R4 = prenyl
R5 = X1 = H
R6 = X2 = H
R7 = 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
hyperkouytone M H. kouytchense −24.8 (0.36, m) H.-Y. Lou 2024
Structure 327: garcibracteamone I — caged, fourPlusTwo
327
garcibracteamone I[c] G. bracteata −22 (0.05, m) Q. Xue 2020
Structure 328: burlemarxione D — caged, fourPlusTwo
328
burlemarxione D C. burlemarxii −8.0 (1.0) Ferraz 2021
Structure 329: hyperlanin B — caged, fourPlusTwo
329
hyperlanin B[d] H. lancasteri −32.1 (0.3, m) You 2024
Structure 330: hyparillum B — caged, fourPlusTwo
330
hyparillum B[d] H. patulum −51.5 (0.1) Y. Duan 2024a
Structure 331: hyparillum A — caged, fourPlusTwo
331
hyparillum A[d] H. patulum −26.1 (0.2) Y. Duan 2024a
Structure 332: garcioblon D — caged, fourPlusTwo
332
garcioblon D[d] G. oblongifolia −37.2 (0.3, m) Q. Lin 2025
Structure 333: garcioblon A — caged, fourPlusTwo
333
garcioblon A[d] G. oblongifolia −29.0 (0.4, m) Q. Lin 2025
Structure 334: garcioblon B — caged, fourPlusTwo
334
garcioblon B[d] G. oblongifolia −32.5 (0.4, m) Q. Lin 2025
Structure 335: garcioblon C — caged, fourPlusTwo
335
garcioblon C[d] G. oblongifolia −40.6 (0.5, m) Q. Lin 2025
Structure 336: garcioblon E — caged, fourPlusTwo, seco
336
garcioblon E[d] G. oblongifolia +16.7 (0.5, m) Q. Lin 2025
Structure 337: garcioblon F — caged, fourPlusTwo, seco
337
garcioblon F[d] G. oblongifolia +26.2 (0.3, m) Q. Lin 2025
Structure 338: burlemarxione I — caged, fourPlusTwo
338
burlemarxione I[c] C. burle-marxii NR M. do C. C. Silva 2024
Structure 339: garbractin A — caged, fourPlusTwo, seco
339
garbractin A[c] G. bracteata −94.4 (0.05, m) X.-N. Li 2023
Structure 340: garcibracgluinol B — fourPlusTwo, seco
340
garcibracgluinol B[c] G. bracteata +248.1 (0.03, m) J. Xu 2025
Structure 341: garcibracgluinol C — fourPlusTwo, seco
341
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) Thoison 2005
342.2 R = CH2CH2CMe=CH2 xerophenone A[d] C. portlandiana, G. propinqua −36.4 (0.055, a) Henry 1995, 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) 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) 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
garcoblone H[c] G. oblongifolia −26.4 (1.0, m) S.-Y. Yang 2024
Structure 347: garynthone A — B, caged, otherBridgedBicycles
347
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
garciyunnanin D[c] G. yunnanensis +23.1 (0.10, m) Zheng 2021b
Structure 350: spirohypertone A — B, otherBridgedBicycles, seco
350
spirohypertone A[c] H. patulum −10.2 (0.2, m) Y. Duan 2024b
Structure 351: trijapin D — B, otherBridgedBicycles
351
trijapin D T. japonicum −58 (0.6, m) Oya 2015
Structure 352: xerophenone G — caged, otherBridgedBicycles
352
xerophenone G[c][e] G. multiflora +103.0 (0.1, m) J. Cao 2024
Structure 353: xerophenone F — caged, otherBridgedBicycles
353
xerophenone F[c][e] G. multiflora +164.0 (0.1, m) J. Cao 2024
Structure 354: xerophenone H — caged, otherBridgedBicycles
354
xerophenone H[e] G. multiflora −15.0 (0.1, m) W.-Y. Lyu 2025
Structure 355: xerophenone D — caged, otherBridgedBicycles
355
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
garcinielliptone HF G. subelliptica −16.7 (0.22, a) C.-C. Wu 2008a
Structure 358: gambogenone — otherBridgedBicycles
358
gambogenone[e] G. xanthochymus −5 (0.003, m) Baggett 2005
Structure 359: garcibractinone C — otherBridgedBicycles
359
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
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
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
hypaluton A[c] H. patulum −64.2 (0.3, m) Y. Duan 2021a
Structure 366: hyperbeanin P — A, otherBridgedBicycles
366
hyperbeanin P[c] H. beanii −254 (0.2, m) X.-Y. Suo 2021b
Structure 367: hyperprin B — A, otherBridgedBicycles
367
hyperprin B[c] H. przewalskii −314.0 (0.10, m) Zong 2020
Structure 368: hyperacmosin R — A, exo, otherBridgedBicycles
368
hyperacmosin R[c] H. acmosepalum −230.5 (0.14, m) Y. Ma 2022b
Structure 369: hyperinoid A — otherBridgedBicycles, seco
369
hyperinoid A[c] H. patulum +54.0 X. Jia 2020
Structure 370: hyperinoid B — otherBridgedBicycles, seco
370
hyperinoid B[c] H. patulum +61.0 X. Jia 2020
Structure 371: (±)-hypandrone A — otherBridgedBicycles
371
(±)-hypandrone A H. androsaemum 0 J. Wei 2024a
Structure 372: hypertaxoid B — B, otherBridgedBicycles
372
hypertaxoid B[d] H. elatoides +13.1 (0.05, m) J.-Y. Xie 2026
Structure 373: hypertaxoid A — B, otherBridgedBicycles
373
hypertaxoid A[d] H. elatoides +76.1 (0.05, m) J.-Y. Xie 2026
Structure 374: hypermonin A — B, otherBridgedBicycles, seco
374
hypermonin A[c] H. monogynum +46.5 (0.20, m) Y.-R. Zeng 2018
Structure 375: hypermonin B — B, otherBridgedBicycles, seco
375
hypermonin B[c] H. monogynum +155.42 (0.24, m) Y.-R. Zeng 2018
Structure 376: garciyunnanin G — B, otherBridgedBicycles, seco
376
garciyunnanin G[c] G. yunnanensis +28.7 (0.10, m) 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) Yin 2009
377.2 R = Me
X = OOH
harrisotone B Harrisonia perforata +25.4 (1.30, m) 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, 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, 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) 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, Zong 2021
378.3 R = i-Bu
X = OH
hyperascyrone E[c] H. ascyron −9.1 (0.68, m) 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
R4 = X1 = H
R5 = X2 = H
harperoid B Harrisonia perforata +15 (0.4, m) P.-P. An 2026
379.2 R1 = Me
R2 = prenyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = H
harrisotone C Harrisonia perforata +11.1 (0.80, m) Yin 2009
379.3 R1 = Me
R2 = prenyl
R3 = prenyl
R4 = X1 = OOH
R5 = X2 = H
harrisotone E Harrisonia perforata +22.1 (0.09, m) Yin 2009
379.4 R1 = Et
R2 = prenyl
R3 = Me
R4 = X1 = OH
R5 = 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
R4 = X1 = OH
R5 = X2 = H
chipericumin C H. chinense, H. pyramidatum +35.1 (0.33, m) Abe 2012, Force 2014
379.6 R1 = i-Pr
R2 = Me
R3 = prenyl
R4 = X1 = OOH
R5 = X2 = H
pyramidatone D H. pyramidatum +20.0 (0.009) Force 2014
379.7 R1 = i-Pr
R2 = prenyl
R3 = Me
R4 = X1 = OH
R5 = X2 = H
pyramidatone A, a.k.a. chipericumin E H. pyramidatum, H. riparium +12.5 (0.005), +12.0 (0.5, m) Force 2014, Tala 2015
379.8 R1 = i-Pr
R2 = prenyl
R3 = Me
R4 = X1 = OOH
R5 = X2 = H
pyramidatone B H. pyramidatum +15.5 (0.03) Force 2014
379.9 R1 = i-Pr
R2 = prenyl
R3 = Me
R4 = X1 = OH
R5 = 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
R4 = X1 = OH
R5 = 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
R4 = X1 = OOH
R5 = X2 = H
tomoeone C H. ascyron +17.4 (4.9, m) W. Hashida 2008, Zhu 2015a, Y.-L. Hu 2023
379.12 R1 = s-Bu
R2 = prenyl
R3 = Me
R4 = X1 = OH
R5 = X2 = H
chipericumin D[e] H. chinense +67.4 (0.33, m) Abe 2012
379.13 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = H
hyperascyrone F[c][e] H. ascyron +41.1 (0.13, m) Zhu 2015a
379.14 R1 = s-Bu
R2 = prenyl
R3 = prenyl
R4 = X1 = OOH
R5 = 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
R4 = X1 = OH
R5 = 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
R4 = X1 = OH
R5 = 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
R4 = X1 = OOH
R5 = X2 = H
tomoeone G H. ascyron +25.4 (1.7, m) W. Hashida 2008, Zhu 2015a
379.18 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = X1 = OH
R5 = X2 = H
hyperbeanol C H. beanii +31.21 (0.19) X.-Q. Chen 2011
379.19 R1 = Ph
R2 = prenyl
R3 = prenyl
R4 = X1 = OOH
R5 = X2 = H
hyperbeanol D H. beanii +42.73 (0.42) X.-Q. Chen 2011
Structure 380: hyperpatulone  D — spiroindanes
380
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) 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) 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
hunascynol I
(or its epimer, hunascynol J)
H. ascyron −0.7 (0.09, m) Y.-L. Hu 2023
Structure 384: hunascynol J — spiroindanes
384
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) Zhu 2015a
385.3 R1 = i-Bu
R2 = prenyl
X = OH
hyperascyrone C[d] H. ascyron −3.8 (0.38, m) Zhu 2015a
385.4 R1 = Ph
R2 = prenyl
X = OH
hyperascyrone A[d] H. ascyron −16.4 (0.33, m) 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) Abe 2012
387.2 R1 = s-Bu
R2 = Me
chipericumin B[e] H. chinense +116.1 (0.46, m) Abe 2012
387.3 R1 = Ph
R2 = prenyl
sampsonol A H. sampsonii −7.7 (0.5, mc) Xin 2012
Structure 388: sampsonol B — spiroindanes
388
sampsonol B H. sampsonii +45.3 (0.5, mc) Xin 2012
Structure 389: hyperhenone L — spiroindanes
389
hyperhenone L H. henryi −6 (0.08, m) Duan 2018
Structure 390: hyperacmotone D — spiroindanes
390
hyperacmotone D[c] H. acmosepalum +20 (0.10, m) A.-Z. Wang 2022
Structure 391: hyperacmotone E — spiroindanes
391
hyperacmotone E[c] H. acmosepalum –1 (0.10, m) A.-Z. Wang 2022
Structure 392: hyperacmotone F — spiroindanes
392
hyperacmotone F[c] H. acmosepalum +60 (0.10, m) A.-Z. Wang 2022
Structure 393: hyperacmotone B — spiroindanes
393
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) Xin 2012
394.3 R1 = i-Pr
R2 = prenyl
R3 = Me
X = H
hyperhenone I H. henryi −516 (0.12, m) 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) Xin 2012
394.6 R1 = s-Bu
R2 = Me
R3 = prenyl
X = H
hyperhenone H[e] H. henryi −71 (0.15, m) 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) 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) Xin 2012
394.13 R1 = Ph
R2 = (E)-CH=CHCMe2OH
R3 = prenyl
X = H
hyperhenone J H. henryi −15 (0.22, m) 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) 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
hyperbeanol G H. beanii +15 (0.09, m) Y.-R. Li 2019
Structure 397: hunascynol A — spiroindanes
397
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
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
hyperlagarol G[c] H. beanii NR R.-D. Hu 2024
Structure 400: hunascynol C — spiroindanes
400
hunascynol C H. ascyron +29 (0.14, m) Y.-L. Hu 2023
Structure 401: hyperpatulone G — spiroindanes
401
hyperpatulone G[c] H. patulum +62.0 (0.10, m) Y.-x. Zhang 2021
Structure 402: hyperbeanol H — spiroindanes
402
hyperbeanol H H. beanii +52 (0.7, m) Y.-R. Li 2019
Structure 403: hyperhenone K — spiroindanes
403
hyperhenone K H. henryi −6 (0.07, m) Duan 2018
Structure 404: hyperispirone B — caged, spiroindanes
404
hyperispirone B[c] H. beanii −53 (0.18, m) B. Yang 2022
Structure 405: hyperispirone A — caged, spiroindanes
405
hyperispirone A[c] H. beanii +70 (0.15, m) B. Yang 2022
Structure 406: hyperlagarol J — caged, spiroindanes
406
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
hyperlagarol C[c] H. beanii NR R.-D. Hu 2024
Structure 411: hyperlagarol D — seco, spiroindanes
411
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) 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) Tanaka 2012
415.2 R = s-Bu biyoulactone E[e] H. chinense −14.4 (0.07, m) Tanaka 2012
Structure 416: hyperbeanone A — seco, spiroindanes
416
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
hypermonone D[c] H. monogynum +47.26 (0.12, m) Y.-R. Zeng 2021c
Structure 419: hypermonone A — seco, spiroindanes
419
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
biyoulactone A[c] H. chinense +8.1 (0.1, m) 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) 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) 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) 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
longisglucinol A[c] H. longistylum −31.2 (0.5, m) N. Zhang 2020
Structure 429: hymoin  B — seco, spiroindanes
429
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
harperoid A[c] Harrisonia perforata +12 (0.2, m) P.-P. An 2026
Structure 432: hymoin  A — caged, seco, spiropentalanes
432
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
hyperzrone A[c] H. beanii +19.8 (0.1, m) X.-Y. Li 2025
Structure 434: hyperzrone B — spiropentalanes
434
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