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
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farnesyl cation
|
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(E,E)-germacradienyl cation-Germacradienyl_cation.png)
|
eudesmanyl cation 
|
vetispiradienyl_cation  → spirovetivane (= vetispirane)
| |||
eremophilenyl cation (14(10→5) abeoeudesmane)
| |||||
guaiane
|
Cycloguaianes
| ||||
(E,E)-humulyl cation-Humulyl_cation.png)
|
africanyl cation |
||||
nerolidyl cation
|
bisabolyl cation
|
| |||
(Z,E)-germacradienyl cation-Germacradienyl_cation.png)
|
| ||||
(Z,E)-humulyl cation-Humulyl_cation.png)
|
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 |
|
||||
-beta-Caryophyllene.png)
-Sesquithujene.png)
-delta-Cadinene.png)
-Longifolene.png)
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