Category:TP5

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(→‎{{Bilingual|セスキテルペン合成酵素|Sesquiterpene Synthase}})
(→‎{{Bilingual|セスキテルペン合成酵素|Sesquiterpene Synthase}})
Line 38: Line 38:
 
{| class="wikitable"
 
{| class="wikitable"
 
|-
 
|-
−
| farnesyl diphosphate
+
| farnesyl diphosphate<br/>[[Image:Farnesyl diphosphate.png|100px]]
 
|-
 
|-
−
| [[File:Arrow00d.png]]
+
|align="center"| [[File:Arrow00d35.png]]
−
|-
+
 
−
| farnesyl cation
+
<!---FARNESYL--->
−
|-
+
−
|rowspan="6"| [[File:Arrow00d.png]]
+
 
|-
 
|-
 +
|rowspan="5" align="center"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]]
 +
|colspan="2"|
 +
{|
 
| farnesane, acyclic ones
 
| farnesane, acyclic ones
−
|-
 
 
| cyclobutane, cyclopentane
 
| cyclobutane, cyclopentane
−
|-
 
 
| cyclofarnesane
 
| cyclofarnesane
 +
|}
 
|-
 
|-
−
| germacrane (elemane, lepidozane, (bi)cyclogermacrane) [http://www.pnas.org/content/95/5/2216/F1.expansion.html]
+
|rowspan="3"|(E,E)-germacradienyl cation<br/>[[Image:(E,E)-Germacradienyl cation.png|100px]]
 +
* germacrene [[Image:Germacrene A.png|80px]]
 +
* elemene
 +
* lepidozene
 +
* bicyclogermacrene
 +
| eudesmanyl cation <br/>[[Image:Eudesmanyl cation.png|100px]]
  
−
{| class="wikitable"
+
* selinene [[Image:beta-Selinene.png|80px]]
−
| eudesmane (emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane, spirovetivane (= vetispirane))
+
 
 +
{|
 +
| emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane
 
|-
 
|-
−
| eremophilane (chiloscyphane, aristolane, nardosinane, brasilane (?), cacalol, [http://books.google.co.jp/books?id=5BAPWB67TKUC&pg=PA107&lpg=PA107&dq=%22fukinane+biosynthesis%22&source=bl&ots=3rsiXnan_y&sig=HZGm1AsNYp7JZqtjqkf5iuY59Cg&hl=en&ei=Vs7cTs6UI8LJrAfEpvTvDA&sa=X&oi=book_result&ct=result&resnum=2&ved=0CCMQ6AEwAQ#v=onepage&q&f=false) page 133 fukinane] [[Petasites japonicus]], ishwarane
+
| vetispiradienyl_cation [[Image:Vetispiradienyl_cation.png|80px]]
 +
| spirovetivane (= vetispirane)
 +
|}
 +
|-
 +
| eremophilenyl cation<br/>(1,2-CH<sub>3</sub> shift from eudesmanyl cation)<br/>[[Image:Eremophilenyl cation.png|100px]]
 +
eremophilane (chiloscyphane, nardosinane, brasilane (?), cacalol, [http://books.google.co.jp/books?id=5BAPWB67TKUC&pg=PA107&lpg=PA107&dq=%22fukinane+biosynthesis%22&source=bl&ots=3rsiXnan_y&sig=HZGm1AsNYp7JZqtjqkf5iuY59Cg&hl=en&ei=Vs7cTs6UI8LJrAfEpvTvDA&sa=X&oi=book_result&ct=result&resnum=2&ved=0CCMQ6AEwAQ#v=onepage&q&f=false) page 133 fukinane] [[Petasites japonicus]], ishwarane
 +
* eremophilene
 +
* aristolochene [[Image:5-epi-Aristolochene.png|80px]]
 
|-
 
|-
 
| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane] (xanthane, carabrane, pseudoguaiane, cubebane, ivaxillarane, valerenane)
 
| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane] (xanthane, carabrane, pseudoguaiane, cubebane, ivaxillarane, valerenane)
Line 63: Line 77:
 
{| class="wikitable"
 
{| class="wikitable"
 
| cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
 
| cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
−
|}
 
−
|-
 
 
|}
 
|}
  
 
|-
 
|-
 +
| (E,E)-humulyl cation<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
 
| humulane (caryyllophyllane, bicyclohumulane, [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane])  
 
| humulane (caryyllophyllane, bicyclohumulane, [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane])  
 +
* caryophyllene [[Image:(E)-beta-Caryophyllene.png|60px]]
 +
<!---NEROLIDYL--->
 
|-
 
|-
−
| bisabolyl cation
+
|rowspan="5"| nerolidyl cation<br/>[[Image:Nerolidyl cation.png|100px]]
 +
| bisabolyl cation<br/>[[Image:Bisabolyl cation.png|100px]]
 
| bisabolane
 
| bisabolane
 
{| class="wikitable"
 
{| class="wikitable"
−
| cuparane (herbertane [[liverwort,fungi]], laurane  [[Laurencia spp. (marine)]], cyclolaurane,  [http://www.springerlink.com/content/h40302g23g830241/ trichothecane] (from scirpane),  gymnomitrane, thujopsane, widdrane, )
+
| cuparane (herbertane [[liverwort,fungi]], laurane  [[Laurencia spp. (marine)]], cyclolaurane,  [http://www.springerlink.com/content/h40302g23g830241/ trichothecane] (from scirpane),  gymnomitrane
 +
| thujopsane [[Image:(-)-Sesquithujene.png|80px]]
 +
|widdrane
 
|}
 
|}
 +
 
|-
 
|-
 
  [http://books.google.co.jp/books?id=rIoXXL7OGCoC&pg=PA126&lpg=PA126&dq=acorane+biosynthesis&source=bl&ots=j7EPQ5aaAk&sig=m5dMiXfi-aaPjlY1OhSuYcU4oGY&hl=en&ei=veTcTpiaJYPLrQe5yMirCw&sa=X&oi=book_result&ct=result&resnum=7&ved=0CE4Q6AEwBg#v=onepage&q=acorane%20biosynthesis&f=false acorane]
 
  [http://books.google.co.jp/books?id=rIoXXL7OGCoC&pg=PA126&lpg=PA126&dq=acorane+biosynthesis&source=bl&ots=j7EPQ5aaAk&sig=m5dMiXfi-aaPjlY1OhSuYcU4oGY&hl=en&ei=veTcTpiaJYPLrQe5yMirCw&sa=X&oi=book_result&ct=result&resnum=7&ved=0CE4Q6AEwBg#v=onepage&q=acorane%20biosynthesis&f=false acorane]
 
|-
 
|-
−
| (Z,E)-germacradienyl cation
+
| (Z,E)-germacradienyl cation<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
 +
|
 +
{|
 
| cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
 
| cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
 +
|}
 +
* cadinene [[Image:(+)-delta-Cadinene.png|80px]]
 
|-
 
|-
−
|rowspan="2"| (Z,E)-humulyl cation
+
|rowspan="2"| (Z,E)-humulyl cation<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] (lippifoliane, longipinane, longibornane, longifolane)
 +
* longifolene [[Image:(+)-Longifolene.png|80px]]
 
|-
 
|-
 
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane
 
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane
 
|-
 
|-
−
| cycloheptenyl cation
+
| 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)
 
|-
 
|-

Revision as of 11:36, 12 December 2011

Contents

Sesquiterpene (C15)

Ring configuration

Germacrane


Sesquiterpenes

Biosynthesis

Overview

References


Sesquiterpene Synthase

acorane
farnesyl diphosphate
Farnesyl diphosphate.png
Arrow00d35.png
farnesyl cation
Farnesyl cation.png
farnesane, acyclic ones cyclobutane, cyclopentane cyclofarnesane
(E,E)-germacradienyl cation
(E,E)-Germacradienyl cation.png
  • germacrene Germacrene A.png
  • elemene
  • lepidozene
  • bicyclogermacrene
eudesmanyl cation
Eudesmanyl cation.png
  • selinene Beta-Selinene.png
emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane
vetispiradienyl_cation Vetispiradienyl cation.png spirovetivane (= vetispirane)
eremophilenyl cation
(1,2-CH3 shift from eudesmanyl cation)
Eremophilenyl cation.png

eremophilane (chiloscyphane, nardosinane, brasilane (?), cacalol, page 133 fukinane Petasites japonicus, ishwarane

  • eremophilene
  • aristolochene 5-epi-Aristolochene.png
guaiane (xanthane, carabrane, pseudoguaiane, cubebane, ivaxillarane, valerenane)
cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
(E,E)-humulyl cation
(E,E)-Humulyl cation.png 		humulane (caryyllophyllane, bicyclohumulane, africanane)
  • caryophyllene (E)-beta-Caryophyllene.png
nerolidyl cation
Nerolidyl cation.png 		bisabolyl cation
Bisabolyl cation.png 		bisabolane
cuparane (herbertane liverwort,fungi, laurane Laurencia spp. (marine), cyclolaurane, trichothecane (from scirpane), gymnomitrane thujopsane (-)-Sesquithujene.png widdrane
(Z,E)-germacradienyl cation
(Z,E)-Germacradienyl cation.png
cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
  • cadinene (+)-delta-Cadinene.png
(Z,E)-humulyl cation
(Z,E)-Humulyl cation.png 		himachalane (lippifoliane, longipinane, longibornane, longifolane)
  • longifolene (+)-Longifolene.png
(proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane
cycloheptenyl cation
Cycloheptenyl cation.png 		daucane (= carotane, isodaucane)
drimenyl cation drimane (iresin, seco, coloratane)
furodysyl cation furodysin (furodysinin)
chamigranyl cation chamigrane (secochamigrane)
Others
pinguisane, picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial
Tricyclic
Cedrane (isocedrane)
Prezizaane (zizaane)


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