Sesquiterpene (C15)
Ring configuration
Germacrane
Sesquiterpenes
Biosynthesis
Overview
- References
Sesquiterpene Synthase
farnesyl diphosphate
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farnesyl cation
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| farnesane, acyclic ones
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cyclobutane, cyclopentane
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cyclofarnesane
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(E,E)-germacradienyl cation
- germacrane
- elemane
- lepidozane and bicyclogermacrane
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eudesmanyl cation
- cycloeudesmane
- emmotin ... 14(10→1) abeo form
- eudesmane (previously selinane)
 (selinene)
- 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
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vetispiradienyl_cation  → spirovetivane (= vetispirane)
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eremophilenyl cation (14(10→5) abeoeudesmane)
- eremophilane
- aristolane ... 6,11-cyclo form
- 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?
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guaiane
- xanthane, carabrane ... 4,5 seco form
- pseudoguaiane ... 15(4→5) abeo form
- valerenane ... 8(7→6) abeo form
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Cycloguaianes
- cubebane ... 1,6-cyclo form
- ivaxillarane ... 8,10-cyclo form
- aromadendrane ... 6,11- cyclo form
- rotundane ... 10,12-cyclo form
- bourbonane ... 6,10-cyclo form
- patchoulane ... 1,11-cyclo form
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(E,E)-humulyl cation
- humulane
- bicyclohumulane
- caryophyllane
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africanyl cation
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nerolidyl cation
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bisabolyl cation
- bisabolane
- thujopsane
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- bisabolane → 6,10-cyclization → acorane
- bisabolane → 7,11-cyclization → cuparane
- cuparane → methyl shift → herbertane liverwort,fungi
- cuparane → methyl shift → laurane Laurencia spp. (marine)
- cuparane → 2 methyl shifts →trichothecane [1]
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(Z,E)-germacradienyl cation
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| cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
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- cadinene
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(Z,E)-humulyl cation
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himachalane (lippifoliane, longipinane, longibornane, longifolane)
- longifolene
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| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane
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cycloheptenyl cation
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daucane (= carotane, isodaucane)
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| drimenyl cation
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drimane (iresin, seco, coloratane)
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| furodysyl cation
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furodysin (furodysinin)
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| chamigranyl cation
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chamigrane (secochamigrane)
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| Others
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| pinguisane, picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial
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Tricyclic
| Cedrane (isocedrane)
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| Prezizaane (zizaane)
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-Germacradienyl_cation.png)
→ spirovetivane (= vetispirane)
-Humulyl_cation.png)
-Germacradienyl_cation.png)
-Humulyl_cation.png)
-beta-Caryophyllene.png)
-Sesquithujene.png)
-delta-Cadinene.png)
-Longifolene.png)
