Category:TP5

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|-
 
|-
 
| farnesyl diphosphate
 
| farnesyl diphosphate
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| cyclofarnesane
 
| cyclofarnesane
 
|-
 
|-
| germacrane (elemane, 12-6/12-8 germacranolide, furano- nor- homo- seco-germacrane, bicyclogermacrane, lepidozane) [http://www.pnas.org/content/95/5/2216/F1.expansion.html]
+
| germacrane (elemane, lepidozane, (bi)cyclogermacrane) [http://www.pnas.org/content/95/5/2216/F1.expansion.html]
  
 
{| class="wikitable"
 
{| class="wikitable"
| eudesmane (emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane, spirovetivane (= vetispirane), copaane, others)
+
| eudesmane (emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane, spirovetivane (= vetispirane))
 
|-
 
|-
| eremophilane (furano-, seco-, abeo-, nor-, 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
+
| 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
 
|-
 
|-
| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane] (guaianolide, dimer, seco, abeo, 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)
  
 
{| class="wikitable"
 
{| class="wikitable"
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| humulane (caryyllophyllane, bicyclohumulane, [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane])  
 
| humulane (caryyllophyllane, bicyclohumulane, [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane])  
 
|-
 
|-
| nerolidyl cation
+
| rowspan="2" | bisabolyl cation
|-
+
|rowspan="6"|  
+
|-
+
 
| 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)
+
| cuparane (herbertane [[liverwort,fungi]], laurane  [[Laurencia spp. (marine)]], cyclolaurane,  [http://www.springerlink.com/content/h40302g23g830241/ trichothecane] (from scirpane),  gymnomitrane, thujopsane, widdrane, )
|-
+
|
+
 
|}
 
|}
 
|-
 
|-
| cycloheptenyl cation
+
[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]
 
|-
 
|-
| cadinane (nor, seco, bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol)
+
| (Z,E)-germacradienyl cation
 +
| cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
 
|-
 
|-
 +
|rowspan="2"| (Z,E)-humulyl cation
 
| [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)
 
|-
 
|-
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (isodaucane)
+
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane
 +
|-
 +
| cycloheptenyl cation
 +
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (= carotane, isodaucane)
 
|-
 
|-
 
| drimenyl cation
 
| drimenyl cation
 
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane] (iresin, seco, coloratane)
 
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane] (iresin, seco, coloratane)
|-
 
| illudyl cation
 
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane)
 
 
|-
 
|-
 
| furodysyl cation
 
| furodysyl cation
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| chamigranyl cation
 
| chamigranyl cation
 
| chamigrane (secochamigrane)
 
| chamigrane (secochamigrane)
|-
 
|
 
| [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]
 
 
|-
 
|-
 
| Others
 
| Others
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| [http://alamlearning.blogspot.com/2010/11/possible-biosynthetic-pathway-for.html pinguisane], picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial
 
| [http://alamlearning.blogspot.com/2010/11/possible-biosynthetic-pathway-for.html pinguisane], picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial
 
|}
 
|}
 
  
 
{| class="wikitable"
 
{| class="wikitable"

Revision as of 18:48, 10 December 2011

Contents

Sesquiterpene (C15)

Ring configuration

Germacrane


Sesquiterpenes

Biosynthesis

Overview

References


Sesquiterpene Synthase

acorane
farnesyl diphosphate
Arrow00d.png
farnesyl cation
Arrow00d.png
farnesane, acyclic ones
cyclobutane, cyclopentane
cyclofarnesane
germacrane (elemane, lepidozane, (bi)cyclogermacrane) [1]
eudesmane (emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane, spirovetivane (= vetispirane))
eremophilane (chiloscyphane, aristolane, nardosinane, brasilane (?), cacalol, page 133 fukinane Petasites japonicus, ishwarane
guaiane (xanthane, carabrane, pseudoguaiane, cubebane, ivaxillarane, valerenane)
cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
humulane (caryyllophyllane, bicyclohumulane, africanane)
bisabolyl cation bisabolane
cuparane (herbertane liverwort,fungi, laurane Laurencia spp. (marine), cyclolaurane, trichothecane (from scirpane), gymnomitrane, thujopsane, widdrane, )
(Z,E)-germacradienyl cation cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
(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
pinguisane, picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial
Tricyclic
Cedrane (isocedrane)
Prezizaane (zizaane)


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