Category:TP5
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|rowspan="3"|(E,E)-germacradienyl cation<br/>[[Image:(E,E)-Germacradienyl cation.png|100px]] | |rowspan="3"|(E,E)-germacradienyl cation<br/>[[Image:(E,E)-Germacradienyl cation.png|100px]] | ||
− | * | + | * germacrane [[Image:Germacrene A.png|80px]] |
− | * | + | * elemane |
− | * | + | * lepidozane and bicyclogermacrane |
− | + | ||
| eudesmanyl cation <br/>[[Image:Eudesmanyl cation.png|100px]] | | eudesmanyl cation <br/>[[Image:Eudesmanyl cation.png|100px]] | ||
− | + | * cycloeudesmane | |
− | * | + | * emmotin ... 14(10→1) abeo form |
− | + | * eudesmane (previously selinane) [[Image:beta-Selinene.png|80px]] (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 | ||
+ | | vetispiradienyl_cation [[Image:Vetispiradienyl_cation.png|80px]] → spirovetivane (= vetispirane) | ||
|- | |- | ||
− | | | + | | eremophilenyl cation (14(10→5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]] |
− | | | + | |
− | + | * eremophilane | |
+ | * aristolane ... 6,11-cyclo form [[Image:5-epi-Aristolochene.png|80px]] | ||
+ | * 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? | ||
|- | |- | ||
− | | | + | | [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane] |
− | + | * xanthane, carabrane ... 4,5 seco form | |
− | * | + | * pseudoguaiane ... 15(4→5) abeo form |
− | * | + | * valerenane ... 8(7→6) abeo form |
+ | | | ||
+ | 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 | ||
|- | |- | ||
− | | [ | + | | (E,E)-humulyl cation<br/>[[Image:(E,E)-Humulyl cation.png|100px]] |
+ | * humulane | ||
+ | * bicyclohumulane | ||
+ | * caryophyllane [[Image:(E)-beta-Caryophyllene.png|60px]] | ||
+ | | africanyl cation<br/> | ||
+ | * [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane]) | ||
− | + | | | |
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
<!---NEROLIDYL---> | <!---NEROLIDYL---> | ||
|- | |- | ||
|rowspan="5"| nerolidyl cation<br/>[[Image:Nerolidyl cation.png|100px]] | |rowspan="5"| nerolidyl cation<br/>[[Image:Nerolidyl cation.png|100px]] | ||
| bisabolyl cation<br/>[[Image:Bisabolyl cation.png|100px]] | | bisabolyl cation<br/>[[Image:Bisabolyl cation.png|100px]] | ||
− | + | * bisabolane | |
− | + | * thujopsane [[Image:(-)-Sesquithujene.png|80px]] | |
− | | cuparane | + | | |
− | | | + | * <small>bisabolane → 6,10-cyclization →</small> acorane |
− | |widdrane | + | * <small>bisabolane → 7,11-cyclization →</small> cuparane |
+ | * <small>cuparane → methyl shift →</small> herbertane [[liverwort,fungi]] | ||
+ | * <small>cuparane → methyl shift →</small> laurane [[Laurencia spp. (marine)]] | ||
+ | * <small>cuparane → 2 methyl shifts →</small>trichothecane <ref>Grove JF "Non-Macrocyclic Trichothecenes" Nat Prod Rep 5:187-209, 1988</ref> | ||
+ | {| | ||
+ | | gymnomitrane | ||
+ | | widdrane | ||
|} | |} | ||
− | |||
− | |||
− | |||
|- | |- | ||
| (Z,E)-germacradienyl cation<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]] | | (Z,E)-germacradienyl cation<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]] |
Revision as of 15:29, 12 December 2011
Contents |
Sesquiterpene (C15)
Ring configuration
Germacrane
Sesquiterpenes
Biosynthesis
Overview
- References
Sesquiterpene Synthase
farnesyl diphosphate | |||||
farnesyl cation |
| ||||
(E,E)-germacradienyl cation |
eudesmanyl cation |
vetispiradienyl_cation → spirovetivane (= vetispirane) | |||
eremophilenyl cation (14(10→5) abeoeudesmane)
| |||||
guaiane
|
Cycloguaianes
| ||||
(E,E)-humulyl cation |
africanyl cation |
||||
nerolidyl cation |
bisabolyl cation |
| |||
(Z,E)-germacradienyl cation |
| ||||
(Z,E)-humulyl cation |
himachalane (lippifoliane, longipinane, longibornane, longifolane) | ||||
(proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane | |||||
cycloheptenyl cation |
daucane (= carotane, isodaucane) | ||||
drimenyl cation | drimane (iresin, seco, coloratane) | ||||
furodysyl cation | furodysin (furodysinin) | ||||
chamigranyl cation | chamigrane (secochamigrane) | ||||
Others |
|
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