Category:TP5

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m (→‎{{Bilingual|セスキテルペン合成酵素|Sesquiterpene Synthase}})
m (→‎{{Bilingual|セスキテルペン合成酵素|Sesquiterpene Synthase}})
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<!---FARNESYL--->
 
<!---FARNESYL--->
 
|-
 
|-
−
|rowspan="6" align="center"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]]
+
|rowspan="7" align="center"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]]
 
|colspan="2"|
 
|colspan="2"|
 
{|
 
{|
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|}
 
|}
 
|-
 
|-
−
|rowspan="3"|(E,E)-germacradienyl cation<br/>[[Image:(E,E)-Germacradienyl cation.png|100px]]
+
|rowspan="3"|(E,E)-germacradiene<br/>[[Image:(E,E)-Germacradienyl cation.png|100px]] [[Image:Germacrene A.png|80px]]
−
* germacrane [[Image:Germacrene A.png|80px]]
+
* germacrane
−
* lepidozane and bicyclogermacrane
+
* lepidozane
−
| eudesmanyl cation <br/>[[Image:Eudesmanyl cation.png|100px]]
+
* bicyclogermacrane
 +
| eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png|100px]]  [[Image:beta-Selinene.png|80px]]
 
* cycloeudesmane
 
* cycloeudesmane
 
* elemane ... 7,8 seco form
 
* elemane ... 7,8 seco form
 
* emmotin ... 14(10&rarr;1) abeo form
 
* emmotin ... 14(10&rarr;1) abeo form
−
* eudesmane (previously selinane) [[Image:beta-Selinene.png|80px]] (selinene)
 
 
* farfugin ... 14(10&rarr;9) abeo form
 
* farfugin ... 14(10&rarr;9) abeo form
 
* gorgonane 11(7&rarr;6) abeo form
 
* gorgonane 11(7&rarr;6) abeo form
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|  vetispiradienyl_cation [[Image:Vetispiradienyl_cation.png|80px]] &rarr; spirovetivane (= vetispirane)
 
|  vetispiradienyl_cation [[Image:Vetispiradienyl_cation.png|80px]] &rarr; spirovetivane (= vetispirane)
 
|-
 
|-
−
| eremophilenyl cation (14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
+
| eremophilane (= 14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
 
    
 
    
−
* eremophilane
 
 
* aristolane ... 6,11-cyclo form [[Image:5-epi-Aristolochene.png|80px]]
 
* aristolane ... 6,11-cyclo form [[Image:5-epi-Aristolochene.png|80px]]
 
* chiloscyphane ...8(7&rarr;6) abeo form
 
* chiloscyphane ...8(7&rarr;6) abeo form
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* valerenane ... 8(7&rarr;6) abeo form
 
* valerenane ... 8(7&rarr;6) abeo form
 
|
 
|
−
Cycloguaianes
+
Cycloguaiane
 
* cubebane ...  1,6-cyclo form
 
* cubebane ...  1,6-cyclo form
 
* ivaxillarane ... 8,10-cyclo form
 
* ivaxillarane ... 8,10-cyclo form
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* patchoulane ... 1,11-cyclo form
 
* patchoulane ... 1,11-cyclo form
 
|-
 
|-
−
|rowspan="2"| (E,E)-humulyl cation<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
+
|rowspan="2"| (E,E)-humulane<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
−
* humulane
+
 
* bicyclohumulane
 
* bicyclohumulane
−
| africanyl cation<br/>  
+
| africanane<br/>  
 
* [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane])  
 
* [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane])  
 
|-
 
|-
−
| caryophyllenyl cation<br/>
+
| caryophyllane<br/> [[Image:(E)-beta-Caryophyllene.png|60px]]
−
* caryophyllane [[Image:(E)-beta-Caryophyllene.png|60px]]
+
 
|  
 
|  
 +
|-
 +
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane]
 +
* iresin
 +
* coloratane
 +
|
 
<!---NEROLIDYL--->
 
<!---NEROLIDYL--->
 
|-
 
|-
−
|rowspan="5"| nerolidyl cation<br/>[[Image:Nerolidyl cation.png|100px]]
+
|rowspan="7"| nerolidyl cation<br/>[[Image:Nerolidyl cation.png|100px]]
−
| bisabolyl cation<br/>[[Image:Bisabolyl cation.png|100px]]
+
|rowspan="2"| bisabolane<br/>[[Image:Bisabolyl cation.png|100px]]
−
* bisabolane
+
 
* thujopsane [[Image:(-)-Sesquithujene.png|80px]]
 
* thujopsane [[Image:(-)-Sesquithujene.png|80px]]
 
|  
 
|  
−
* <small>bisabolane &rarr; 6,10-cyclization &rarr;</small> acorane
+
* acorane ... 6,10-cyclobisabolane
−
* <small>bisabolane &rarr; 7,11-cyclization &rarr;</small> cuparane
+
* chamigrane ... 6,11-cyclobisabolane
−
* <small>cuparane &rarr; methyl shift &rarr;</small> herbertane [[liverwort,fungi]]
+
|-
−
* <small>cuparane &rarr; methyl shift &rarr;</small> laurane [[Laurencia spp. (marine)]]
+
| cuparane (= 7,11-cyclobisabolane)
−
* <small>cuparane &rarr; 2 methyl shifts &rarr;</small>trichothecane <ref>Grove JF "Non-Macrocyclic Trichothecenes" Nat Prod Rep 5:187-209, 1988</ref>
+
* herbertane [[liverwort,fungi]] ... 15(3&rarr;4) abeo form
 +
* laurane [[Laurencia spp. (marine)]] ... 13(11&rarr;10) abeo form
 +
| trichothecane <ref>Grove JF "Non-Macrocyclic Trichothecenes" Nat Prod Rep 5:187-209, 1988</ref>
 
{|
 
{|
 
| gymnomitrane
 
| gymnomitrane
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|}
 
|}
 
|-
 
|-
−
| (Z,E)-germacradienyl cation<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
+
| (Z,E)-germacradiene<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
−
|
+
| cadinane [[Image:(+)-delta-Cadinene.png|80px]]
−
{|
+
* bulgarane, calamenene, muurolane, amorphane, cadalane
−
| cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
+
* alliacane/primnatriene ... 2(3&rarr;4) abeo cadinane
−
|}
+
* oplopane ... 3(4&rarr;5) abeo cadinane
−
* cadinene [[Image:(+)-delta-Cadinene.png|80px]]
+
* mutisianthol ... 6(7&rarr;8) abeo cadinane
 +
* copaane ... 5,10 cyclo cadinane
 
|-
 
|-
−
|rowspan="2"| (Z,E)-humulyl cation<br/>[[Image:(Z,E)-Humulyl cation.png|100px]]
+
|rowspan="2"| (Z,E)-humulane<br/>[[Image:(Z,E)-Humulyl cation.png|100px]]
−
| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane] (lippifoliane, longipinane, longibornane, longifolane)
+
| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane]
−
* longifolene [[Image:(+)-Longifolene.png|80px]]
+
* lippifoliane
 +
* longipinane
 +
* longibornane
 +
* longifolane [[Image:(+)-Longifolene.png|80px]]
 
|-
 
|-
−
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane
+
| protoilludane
 +
* illudane
 +
* illudalane ... 4,6-secoilludane
 +
* sterpurane ... 5(6&rarr;7)-abeoilludane
 +
* lactarane, isolactarane, marasmane, merulane  
 +
| hirsutane
 
|-
 
|-
 
| cycloheptenyl cation<br/>[[Image:Cycloheptenyl cation.png|100px]]
 
| cycloheptenyl cation<br/>[[Image:Cycloheptenyl cation.png|100px]]
 
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (= carotane, isodaucane)
 
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (= carotane, isodaucane)
 
|-
 
|-
−
| drimenyl cation
+
| furodysin
−
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane] (iresin, seco, coloratane)
+
* furodysinin
−
|-
+
−
| furodysyl cation
+
−
| furodysin (furodysinin)
+
−
|-
+
−
| chamigranyl cation
+
−
| chamigrane (secochamigrane)
+
 
|-
 
|-
 
| Others
 
| Others

Revision as of 10:31, 13 December 2011

Contents

Sesquiterpene (C15)

Ring configuration

Germacrane


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 Germacrene A.png
  • germacrane
  • lepidozane
  • bicyclogermacrane
eudesmane (= selinane)
Eudesmanyl cation.png Beta-Selinene.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 → spirovetivane (= vetispirane)
eremophilane (= 14(10→5) abeoeudesmane)
Eremophilenyl cation.png
  • aristolane ... 6,11-cyclo form 5-epi-Aristolochene.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
  • 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)-humulane
(E,E)-Humulyl cation.png
  • bicyclohumulane
africanane
caryophyllane
(E)-beta-Caryophyllene.png
drimane
  • iresin
  • coloratane
nerolidyl cation
Nerolidyl cation.png 		bisabolane
Bisabolyl cation.png
  • thujopsane (-)-Sesquithujene.png
  • acorane ... 6,10-cyclobisabolane
  • chamigrane ... 6,11-cyclobisabolane
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, isodaucane)
furodysin
  • furodysinin
Others
pinguisane, picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial
Tricyclic
Cedrane (isocedrane)
Prezizaane (zizaane)



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

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