Category:TP5

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==Sesquiterpene (C15)==
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=={{Bilingual|環の構造|Ring configuration}}==
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==={{Bilingual|ゲルマクレン|Germacrane}}===
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==={{Bilingual|セスキテルペン|Sesquiterpenes}}===
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=={{Bilingual|生合成|Biosynthesis}}==
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==={{Bilingual|概要|Overview}}===
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;References
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<references/>
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<br/>
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==={{Bilingual|セスキテルペン合成酵素|Sesquiterpene Synthase}}===
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{| class="wikitable"
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|-
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| farnesyl diphosphate<br/>[[Image:Farnesyl diphosphate.png|120px]]
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|-
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|align="center"| [[File:Arrow00d35.png]]
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<!---FARNESYL--->
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|-
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|rowspan="7" align="center"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]]
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|colspan="2"|
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{|
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| farnesane, acyclic ones
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| cyclobutane, cyclopentane
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| cyclofarnesane
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|}
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|-
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|rowspan="3"|(E,E)-germacradiene<br/>[[Image:(E,E)-Germacradienyl cation.png|100px]]
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* germacrane<br/>[[Image:Germacrene A.png|90px]]
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* lepidozane<br/>[[Image:Lepidozane.png|90px]]
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* bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]]
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| eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png|100px]]<!---[[Image:beta-Selinene.png|80px]]-->
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* cycloeudesmane
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* elemane ... 7,8 seco form
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* emmotin ... 14(10&rarr;1) abeo form
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* farfugin ... 14(10&rarr;9) abeo form
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* gorgonane 11(7&rarr;6) abeo form
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* oppositane ... 8(7&rarr;6) abeo form
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* valerane (= jatamansane) 15(4&rarr;5) abeo form
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|  vetispiradienyl cation<br/>[[Image:Vetispiradienyl_cation.png|90px]]
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* vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]]
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* spirovetivane (= vetispirane)<br/>[[Image:Spirovetivane.png|80px]]
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|-
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| eremophilane (= 14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
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* aristolochene<br/>[[Image:5-epi-Aristolochene.png|80px]]
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* aristolane ... 6,11-cyclo form<br/>[[Image:Aristolane.png|80px]]
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* chiloscyphane ...8(7&rarr;6) abeo form<br/>[[Image:Chiloscyphan.png|80px]]
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* nardosinane ... 11(7&rarr;6) abeo form<br/>[[Image:Nardosinane.png|80px]]
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* cacalol ... 14(5&rarr;6) abeo form<br/>[[Image:Cacalol.png|80px]]
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* fukinane ... 9(8&rarr;7) abeo form<br/>[[Image:Fukinane.png|80px]] [[Petasites japonicus]]
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* brasilane<br/>[[Image:Brasilane.png|80px]]
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* thapsane<br/>[[Image:Thapsane.png|80px]]
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* ishwarane<br/>[[Image:Ishwarane.png|80px]]
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|-
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| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane]
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* xanthane, carabrane ... 4,5 seco form
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* pseudoguaiane ... 15(4&rarr;5) abeo form
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* valerenane ... 8(7&rarr;6) abeo form
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|
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Cycloguaiane
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* cubebane ...  1,6-cyclo form<br/>[[Image:Cubebane.png|80px]]
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* ivaxillarane ... 8,10-cyclo form<br/>[[Image:Ivaxillarane.png|80px]]
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* aromadendrane ... 6,11- cyclo form<br/>[[Image:Aromadendrane.png|70px]]
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* rotundane ... 10,12-cyclo form<br/>[[Image:Rotundane.png|60px]]
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* patchoulane ... 1,11-cyclo form<br/>[[Image:Patchoulane.png|60px]]
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* bourbonane ... 6,10-cyclo form<br/>[[Image:Bourbonane.png|80px]]
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|-
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|rowspan="2"| (E,E)-humulane<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
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* bicyclohumulane<br/>[[Image:Bicyclohumulane.png|80px]]
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| [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane]<br/>[[Image:Africanane.png|90px]]
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|-
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| caryophyllane<br/>[[Image:(E)-beta-Caryophyllene.png|80px]]
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|-
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| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane]<br/>[[Image:Drimane.png|100px]]
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* iresin<br/>[[Image:Iresin.png|90px]]
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* coloratane<br/>[[Image:Coloratane.png|90px]]
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|
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<!---NEROLIDYL--->
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|-
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|rowspan="7"| nerolidyl cation<br/>[[Image:Nerolidyl cation.png|100px]]
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|rowspan="2"| bisabolane<br/>[[Image:Bisabolyl cation.png|100px]]
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* thujopsane<br/>[[Image:(-)-Sesquithujene.png|80px]]
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|  chamigrane ... 6,11-cyclobisabolane<br/>[[Image:Chamigrane|80px]]
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* acorane ... 6,10-cyclobisabolane<br/>[[Image:Acorane|60px]]
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* secochamigrane<br/>[[Image:Secochamigrane|60px]]
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|-
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| cuparane (= 7,11-cyclobisabolane)
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* herbertane [[liverwort,fungi]] ... 15(3&rarr;4) abeo form
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* laurane [[Laurencia spp. (marine)]] ... 13(11&rarr;10) abeo form
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| trichothecane <ref>Grove JF "Non-Macrocyclic Trichothecenes" Nat Prod Rep 5:187-209, 1988</ref>
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{|
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| gymnomitrane
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| widdrane
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|}
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|-
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| (Z,E)-germacradiene<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
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| cadinane<br/>[[Image:(+)-delta-Cadinene.png|80px]]
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* bulgarane, calamenene, muurolane, amorphane, cadalane
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* alliacane/primnatriene ... 2(3&rarr;4) abeo cadinane
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* oplopane ... 3(4&rarr;5) abeo cadinane
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* mutisianthol ... 6(7&rarr;8) abeo cadinane
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* copaane ... 5,10 cyclo cadinane
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|-
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|rowspan="2"| (Z,E)-humulane<br/>[[Image:(Z,E)-Humulyl cation.png|100px]]
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| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane]
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* lippifoliane
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* longipinane
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* longibornane
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* longifolane<br/>[[Image:(+)-Longifolene.png|80px]]
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|-
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| protoilludane
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* illudane
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* illudalane ... 4,6-secoilludane
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* sterpurane ... 5(6&rarr;7)-abeoilludane
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* lactarane, isolactarane, marasmane, merulane
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| hirsutane
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|-
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| cycloheptenyl cation<br/>[[Image:Cycloheptenyl cation.png|100px]]
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| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (= carotane)<br/>[[Image:Daucane.png|90px]]
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* isodaucane<br/>[[Image:Isodaucane.png|70px]]
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|-
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| furodysin<br/>[[Image:Furodysin.png|120px]]
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* furodysinin<br/>[[Image:Furodysinin.png|100px]]
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|-
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| others
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|
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{| class="wikitable"
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| [http://alamlearning.blogspot.com/2010/11/possible-biosynthetic-pathway-for.html pinguisane]<br/>[[Image:Pinguisane.png|100px]]
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|-
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| picrotoxane<br/>[[Image:Picrotoxane.png|100px]]
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|-
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| perforane<br/>[[Image:Perforane.png|90px]]
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|-
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| pacifigorgiane<br/>[[Image:Pacifigorgiane.png|90px]]
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|-
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| asteriscane<br/>[[Image:Asteriscane.png|80px]]
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|-
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| botrydial<br/>[[Image:Botrydial.png|100px]]
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|}
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{| class="wikitable"
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| tricyclic
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{|
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|-
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* cedrane<br/>[[Image:Cedrane.png|80px]]
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* isocedrane<br/>[[Image:Isocedrane.png|80px]]
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* zizaane<br/>[[Image:Zizaane.png|80px]]
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* prezizaane<br/>[[Image:Prezizaane.png|80px]]
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|-
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|}
  
 
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Revision as of 14:11, 14 December 2011

Contents

Sesquiterpene (C15)

Ring configuration

Germacrane

Sesquiterpene (C15)

Ring configuration

Germacrane

<p>



Sesquiterpenes

Biosynthesis

Overview

References


Sesquiterpene Synthase

{</p>


Sesquiterpenes

Biosynthesis

Overview

References


Sesquiterpene Synthase

farnesyl diphosphate
Farnesyl diphosphate.png
Arrow00d35.png
farnesyl cation
Farnesyl cation.png
farnesane, acyclic ones cyclobutane, cyclopentane cyclofarnesane
(E,E)-germacradiene
(E,E)-Germacradienyl cation.png
  • germacrane
    Germacrene A.png
  • lepidozane
    Lepidozane.png
  • bicyclogermacrane
    Bicyclogermacrane.png
eudesmane (= selinane)
Eudesmanyl cation.png
  • cycloeudesmane
  • elemane ... 7,8 seco form
  • emmotin ... 14(10→1) abeo form
  • farfugin ... 14(10→9) abeo form
  • gorgonane 11(7→6) abeo form
  • oppositane ... 8(7→6) abeo form
  • valerane (= jatamansane) 15(4→5) abeo form
vetispiradienyl cation
Vetispiradienyl cation.png
  • vetispiradiene
    Vetispiradiene.png
  • spirovetivane (= vetispirane)
    Spirovetivane.png
eremophilane (= 14(10→5) abeoeudesmane)
Eremophilenyl cation.png
  • aristolochene
    5-epi-Aristolochene.png
  • aristolane ... 6,11-cyclo form
    Aristolane.png
  • chiloscyphane ...8(7→6) abeo form
  • nardosinane ... 11(7→6) abeo form
  • brasilane?
  • cacalol ... 14(5→6) abeo form
  • fukinane ... 9(8→7) abeo form
    Petasites japonicus
  • ishwarane?
guaiane
  • xanthane, carabrane ... 4,5 seco form
  • pseudoguaiane ... 15(4→5) abeo form
  • valerenane ... 8(7→6) abeo form

Cycloguaiane

  • cubebane ... 1,6-cyclo form
    Cubebane.png
  • ivaxillarane ... 8,10-cyclo form
    Ivaxillarane.png
  • aromadendrane ... 6,11- cyclo form
    Aromadendrane.png
  • rotundane ... 10,12-cyclo form
    Rotundane.png
  • patchoulane ... 1,11-cyclo form
    Patchoulane.png
  • bourbonane ... 6,10-cyclo form
    Bourbonane.png
(E,E)-humulane
(E,E)-Humulyl cation.png
  • bicyclohumulane
    Bicyclohumulane.png
africanane
Africanane.png
caryophyllane
(E)-beta-Caryophyllene.png
drimane
Drimane.png
  • iresin
    Iresin.png
  • coloratane
    Coloratane.png
nerolidyl cation
Nerolidyl cation.png 		bisabolane
Bisabolyl cation.png
  • thujopsane
    (-)-Sesquithujene.png
chamigrane ... 6,11-cyclobisabolane
80px
  • acorane ... 6,10-cyclobisabolane
    60px
  • secochamigrane
    60px
cuparane (= 7,11-cyclobisabolane) trichothecane [1]
gymnomitrane widdrane
(Z,E)-germacradiene
(Z,E)-Germacradienyl cation.png 		cadinane
(+)-delta-Cadinene.png
  • bulgarane, calamenene, muurolane, amorphane, cadalane
  • alliacane/primnatriene ... 2(3→4) abeo cadinane
  • oplopane ... 3(4→5) abeo cadinane
  • mutisianthol ... 6(7→8) abeo cadinane
  • copaane ... 5,10 cyclo cadinane
(Z,E)-humulane
(Z,E)-Humulyl cation.png 		himachalane
  • lippifoliane
  • longipinane
  • longibornane
  • longifolane
    (+)-Longifolene.png
protoilludane
  • illudane
  • illudalane ... 4,6-secoilludane
  • sterpurane ... 5(6→7)-abeoilludane
  • lactarane, isolactarane, marasmane, merulane
hirsutane
cycloheptenyl cation
Cycloheptenyl cation.png 		daucane (= carotane)
Daucane.png
  • isodaucane
    Isodaucane.png
furodysin
Furodysin.png
  • furodysinin
    Furodysinin.png
others
pinguisane
Pinguisane.png
picrotoxane
Picrotoxane.png
perforane
Perforane.png
pacifigorgiane
Pacifigorgiane.png
asteriscane
Asteriscane.png
botrydial
Botrydial.png
tricyclic
  • cedrane
    Cedrane.png
  • isocedrane
    Isocedrane.png
  • zizaane
    Zizaane.png
  • prezizaane
    Prezizaane.png

Cite error: <ref> tags exist, but no <references/> tag was found

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