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| − | ==Sesquiterpene (C15)==
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| − | =={{Bilingual|環の構造|Ring configuration}}==
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| − |
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| − | ==={{Bilingual|ゲルマクレン|Germacrane}}===
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| − | {{Twocolumn|
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| − |
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| | ==Sesquiterpene (C15)== | | ==Sesquiterpene (C15)== |
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| | * aristolochene<br/>[[Image:5-epi-Aristolochene.png|80px]] | | * aristolochene<br/>[[Image:5-epi-Aristolochene.png|80px]] |
| | * aristolane ... 6,11-cyclo form<br/>[[Image:Aristolane.png|80px]] | | * aristolane ... 6,11-cyclo form<br/>[[Image:Aristolane.png|80px]] |
| − | * chiloscyphane ...8(7→6) abeo form<br/>[[Image:Chiloscyphan.png|80px]] | + | * chiloscyphane ...8(7→6) abeo form<br/>[[Image:Chiloscyphane.png|80px]] |
| | * nardosinane ... 11(7→6) abeo form<br/>[[Image:Nardosinane.png|80px]] | | * nardosinane ... 11(7→6) abeo form<br/>[[Image:Nardosinane.png|80px]] |
| | * cacalol ... 14(5→6) abeo form<br/>[[Image:Cacalol.png|80px]] | | * cacalol ... 14(5→6) abeo form<br/>[[Image:Cacalol.png|80px]] |
| Line 85: |
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| | * thapsane<br/>[[Image:Thapsane.png|80px]] | | * thapsane<br/>[[Image:Thapsane.png|80px]] |
| | * ishwarane<br/>[[Image:Ishwarane.png|80px]] | | * ishwarane<br/>[[Image:Ishwarane.png|80px]] |
| − | |-
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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→5) abeo form
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| − | * valerenane ... 8(7→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→4) abeo form
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| − | * laurane [[Laurencia spp. (marine)]] ... 13(11→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→4) abeo cadinane
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| − | * oplopane ... 3(4→5) abeo cadinane
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| − | * mutisianthol ... 6(7→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→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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| − |
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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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| − |
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| − | |
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| − |
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| − |
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| − | }}
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| − |
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| − |
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| − | ==={{Bilingual|セスキテルペン|Sesquiterpenes}}===
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| − |
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| − | {{Twocolumn|
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| − | |
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| − | }}
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| − |
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| − | =={{Bilingual|生合成|Biosynthesis}}==
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| − | ==={{Bilingual|概要|Overview}}===
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| − |
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| − |
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| − | ;References
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| − | <references/>
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| − | <br/>
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| − |
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| − | ==={{Bilingual|セスキテルペン合成酵素|Sesquiterpene Synthase}}===
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| − | {{Twocolumn|
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| − |
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| − |
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| − | |
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| − |
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| − |
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| − | }}
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| − |
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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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| − |
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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→1) abeo form
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| − | * farfugin ... 14(10→9) abeo form
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| − | * gorgonane 11(7→6) abeo form
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| − | * oppositane ... 8(7→6) abeo form
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| − | * valerane (= jatamansane) 15(4→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→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→6) abeo form
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| − | * nardosinane ... 11(7→6) abeo form
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| − | * brasilane?
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| − | * cacalol ... 14(5→6) abeo form
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| − | * fukinane ... 9(8→7) abeo form<br/>[[Petasites japonicus]]
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| − | * ishwarane?
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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] | | | [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane] |
farnesyl diphosphate
|
|
farnesyl cation
|
| farnesane, acyclic ones
|
cyclobutane, cyclopentane
|
cyclofarnesane
|
|
(E,E)-germacradiene
- germacrane
- lepidozane
- bicyclogermacrane
|
eudesmane (= selinane)
- 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
- vetispiradiene
- spirovetivane (= vetispirane)
|
eremophilane (= 14(10→5) abeoeudesmane)
- aristolochene
- aristolane ... 6,11-cyclo form
- chiloscyphane ...8(7→6) abeo form
- nardosinane ... 11(7→6) abeo form
- cacalol ... 14(5→6) abeo form
- fukinane ... 9(8→7) abeo form
 Petasites japonicus
- brasilane
- thapsane
- 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
- ivaxillarane ... 8,10-cyclo form
- aromadendrane ... 6,11- cyclo form
- rotundane ... 10,12-cyclo form
- patchoulane ... 1,11-cyclo form
- bourbonane ... 6,10-cyclo form
|
(E,E)-humulane
- bicyclohumulane
|
africanane
|
caryophyllane
|
drimane
- iresin
- coloratane
|
|
nerolidyl cation
|
bisabolane
- thujopsane
|
chamigrane ... 6,11-cyclobisabolane
80px
- acorane ... 6,10-cyclobisabolane
60px
- secochamigrane
60px
|
| cuparane (= 7,11-cyclobisabolane)
|
trichothecane [1]
|
(Z,E)-germacradiene
|
cadinane
- 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
|
himachalane
- lippifoliane
- longipinane
- longibornane
- longifolane
|
protoilludane
- illudane
- illudalane ... 4,6-secoilludane
- sterpurane ... 5(6→7)-abeoilludane
- lactarane, isolactarane, marasmane, merulane
|
hirsutane
|
cycloheptenyl cation
|
daucane (= carotane)
- isodaucane
|
furodysin
- furodysinin
|
| others
|
pinguisane
|
picrotoxane
|
perforane
|
pacifigorgiane
|
asteriscane
|
botrydial
|
tricyclic
- cedrane
- isocedrane
- zizaane
- prezizaane
|
|
-Germacradienyl_cation.png)
-Humulyl_cation.png)
-beta-Caryophyllene.png)
-Germacradienyl_cation.png)
-delta-Cadinene.png)
-Humulyl_cation.png)
-Sesquithujene.png)
-Longifolene.png)
