Category:TP5

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Line 57: Line 57:
 
* bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]]
 
* bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]]
 
| eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png|100px]]<!---[[Image:beta-Selinene.png|80px]]-->
 
| eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png|100px]]<!---[[Image:beta-Selinene.png|80px]]-->
 +
 +
{| class="wikitable"
 +
|align="top"|
 
* cycloeudesmane<br/>[[Image:Cycloeudesmane.png|85px]]
 
* cycloeudesmane<br/>[[Image:Cycloeudesmane.png|85px]]
 
* elemane ... 7,8 seco form<br/>[[Image:Elemene.png|85px]]
 
* elemane ... 7,8 seco form<br/>[[Image:Elemene.png|85px]]
 
* emmotin ... 14(10&rarr;1) abeo form<br/>[[Image:Emmotin.png|85px]]
 
* emmotin ... 14(10&rarr;1) abeo form<br/>[[Image:Emmotin.png|85px]]
 
* farfugin ... 14(10&rarr;9) abeo form<br/>[[Image:Farfugin.png|85px]]
 
* farfugin ... 14(10&rarr;9) abeo form<br/>[[Image:Farfugin.png|85px]]
 +
|align="top"|
 
* gorgonane 11(7&rarr;6) abeo form<br/>[[Image:Gorgonane.png|70px]]
 
* gorgonane 11(7&rarr;6) abeo form<br/>[[Image:Gorgonane.png|70px]]
 
* oppositane ... 8(7&rarr;6) abeo form<br/>[[Image:Oppositane.png|85px]]
 
* oppositane ... 8(7&rarr;6) abeo form<br/>[[Image:Oppositane.png|85px]]
 
* valerane (= jatamansane) 15(4&rarr;5) abeo form<br/>[[Image:Valerane.png|85px]]
 
* valerane (= jatamansane) 15(4&rarr;5) abeo form<br/>[[Image:Valerane.png|85px]]
 +
|}
 
|  vetispiradienyl cation<br/>[[Image:Vetispiradienyl_cation.png|90px]]
 
|  vetispiradienyl cation<br/>[[Image:Vetispiradienyl_cation.png|90px]]
 
* vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]]
 
* vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]]
Line 69: Line 74:
 
|-
 
|-
 
| eremophilane (= 14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
 
| eremophilane (= 14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
 +
{| class="wikitable"
 +
|align="top"|
 
* aristolochene<br/>[[Image:5-epi-Aristolochene.png|85px]]
 
* aristolochene<br/>[[Image:5-epi-Aristolochene.png|85px]]
 
* aristolane ... 6,11-cyclo form<br/>[[Image:Aristolane.png|80px]]
 
* aristolane ... 6,11-cyclo form<br/>[[Image:Aristolane.png|80px]]
Line 74: Line 81:
 
* nardosinane ... 11(7&rarr;6) abeo form<br/>[[Image:Nardosinane.png|70px]]
 
* nardosinane ... 11(7&rarr;6) abeo form<br/>[[Image:Nardosinane.png|70px]]
 
* cacalol ... 14(5&rarr;6) abeo form<br/>[[Image:Cacalol.png|85px]]
 
* cacalol ... 14(5&rarr;6) abeo form<br/>[[Image:Cacalol.png|85px]]
 +
|align="top"|
 
* fukinane ... 9(8&rarr;7) abeo form<br/>[[Image:Fukinane.png|85px]] [[Petasites japonicus]]
 
* fukinane ... 9(8&rarr;7) abeo form<br/>[[Image:Fukinane.png|85px]] [[Petasites japonicus]]
 
* brasilane<br/>[[Image:Brasilane.png|75px]]
 
* brasilane<br/>[[Image:Brasilane.png|75px]]
−
* thapsane<br/>[[Image:Thapsane.png|85px]]
+
|}
−
* ishwarane<br/>[[Image:Ishwarane.png|60px]]
+
| ishwarane ... 10,12-cycloeremophilane<br/>[[Image:Ishwarane.png|60px]]
 
|-
 
|-
 
| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane]<br/>[[Image:Guaiane.png|85px]]
 
| [http://www.orc.wur.nl/UK/Research/Bio-catalyzed+and+bio-based+synthesis+(dr.+M.C.R.+Franssen)/Sesquiterpene+biosynthesis guaiane]<br/>[[Image:Guaiane.png|85px]]
 +
{| class="wikitable"
 +
|valign="top"|
 
* xanthane ... 4,5 seco form<br/>[[Image:Xanthane.png|70px]]
 
* xanthane ... 4,5 seco form<br/>[[Image:Xanthane.png|70px]]
 
* carabrane ... 4,5 seco form<br/>[[Image:Carabrane.png|70px]]
 
* carabrane ... 4,5 seco form<br/>[[Image:Carabrane.png|70px]]
 +
|valign="top"|
 
* pseudoguaiane ... 15(4&rarr;5) abeo form<br/>[[Image:Pseudoguaiane.png|70px]]
 
* pseudoguaiane ... 15(4&rarr;5) abeo form<br/>[[Image:Pseudoguaiane.png|70px]]
 
* valerenane ... 8(7&rarr;6) abeo form<br/>[[Image:Valerenane.png|75px]]
 
* valerenane ... 8(7&rarr;6) abeo form<br/>[[Image:Valerenane.png|75px]]
 +
|}
 
|
 
|
 
cycloguaiane
 
cycloguaiane
 +
{| class="wikitable"
 +
|valign="top"|
 
* cubebane ...  1,6-cyclo form<br/>[[Image:Cubebane.png|80px]]
 
* cubebane ...  1,6-cyclo form<br/>[[Image:Cubebane.png|80px]]
 
* ivaxillarane ... 8,10-cyclo form<br/>[[Image:Ivaxillarane.png|80px]]
 
* ivaxillarane ... 8,10-cyclo form<br/>[[Image:Ivaxillarane.png|80px]]
 
* aromadendrane ... 6,11- cyclo form<br/>[[Image:Aromadendrane.png|70px]]
 
* aromadendrane ... 6,11- cyclo form<br/>[[Image:Aromadendrane.png|70px]]
 +
|valign="top"|
 
* rotundane ... 10,12-cyclo form<br/>[[Image:Rotundane.png|60px]]
 
* rotundane ... 10,12-cyclo form<br/>[[Image:Rotundane.png|60px]]
 
* patchoulane ... 1,11-cyclo form<br/>[[Image:Patchoulane.png|60px]]
 
* patchoulane ... 1,11-cyclo form<br/>[[Image:Patchoulane.png|60px]]
 
* bourbonane ... 6,10-cyclo form<br/>[[Image:Bourbonane.png|80px]]
 
* bourbonane ... 6,10-cyclo form<br/>[[Image:Bourbonane.png|80px]]
 +
|}
 
|-
 
|-
 
|rowspan="2"| (E,E)-humulane<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
 
|rowspan="2"| (E,E)-humulane<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
 
* bicyclohumulane<br/>[[Image:Bicyclohumulane.png|80px]]
 
* bicyclohumulane<br/>[[Image:Bicyclohumulane.png|80px]]
 
| caryophyllane<br/>[[Image:(E)-beta-Caryophyllene.png|80px]]
 
| caryophyllane<br/>[[Image:(E)-beta-Caryophyllene.png|80px]]
 +
|
 +
* pentalenane
 +
* panasinsane
 +
* [http://www.ism2.univ-cezanne.fr/fichiers_pdf/1034.pdf silphinane]
 +
{| class="wikitable"
 +
|valign="top"|
 +
* silphiperfoliane
 +
* presilphiperforliane
 +
|valign="top"|
 +
* [http://pubs.acs.org/doi/abs/10.1021/jo00075a004 isocomane]
 +
* modhephane
 +
* quadrane
 +
|}
 
|-
 
|-
 
| [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane]<br/>[[Image:Africanane.png|80px]]
 
| [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane]<br/>[[Image:Africanane.png|80px]]
 +
| precapnellane
 +
{|
 +
| * capnellane
 +
|}
 
|-
 
|-
 
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane]<br/>[[Image:Drimane.png|100px]]
 
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane]<br/>[[Image:Drimane.png|100px]]
Line 110: Line 143:
 
| chamigrane ... 6,11-cyclobisabolane<br/>[[Image:Chamigrane.png|90px]]
 
| chamigrane ... 6,11-cyclobisabolane<br/>[[Image:Chamigrane.png|90px]]
 
* acorane ... 6,10-cyclobisabolane<br/>[[Image:Acorane.png|80px]]
 
* acorane ... 6,10-cyclobisabolane<br/>[[Image:Acorane.png|80px]]
 +
| cedrane ... 6,10- 2,11-bicyclobisabolane
 +
{| class="wikitable"
 +
|-
 +
cedrane<br/>[[Image:Cedrane.png|80px]]
 +
* isocedrane<br/>[[Image:Isocedrane.png|80px]]
 +
 +
campherenane
 +
* &alpha; &beta;-santalane
 +
 +
prezizaane ??<br/>[[Image:Prezizaane.png|80px]]
 +
* zizaane ??<br/>[[Image:Zizaane.png|80px]]
 +
|}
 
|-
 
|-
 
| cuparane (= 7,11-cyclobisabolane)<br/>[[Image:Cuparane.png|95px]]
 
| cuparane (= 7,11-cyclobisabolane)<br/>[[Image:Cuparane.png|95px]]
Line 123: Line 168:
 
| (Z,E)-germacradiene<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
 
| (Z,E)-germacradiene<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
 
| cadinane<br/>[[Image:Cadinane.png|90px]]
 
| cadinane<br/>[[Image:Cadinane.png|90px]]
 +
{| class="wikitable"
 +
|valign="top"|
 
* muurolane<br/>[[Image:Muurolane.png|80px]]
 
* muurolane<br/>[[Image:Muurolane.png|80px]]
 
* bulgarane<br/>[[Image:Bulgarane.png|80px]]
 
* bulgarane<br/>[[Image:Bulgarane.png|80px]]
Line 128: Line 175:
 
* calamenene<br/>[[Image:Calamenene.png|80px]]
 
* calamenene<br/>[[Image:Calamenene.png|80px]]
 
* cadalane<br/>[[Image:Cadalane.png|80px]]
 
* cadalane<br/>[[Image:Cadalane.png|80px]]
 +
|valign="top"|
 
* alliacane ... 2(3&rarr;4) abeo cadinane<br/>[[Image:Alliacane.png|80px]]
 
* alliacane ... 2(3&rarr;4) abeo cadinane<br/>[[Image:Alliacane.png|80px]]
 
* primnatriene ... 2(3&rarr;4) abeo cadinane<br/>[[Image:Primnatriene.png|80px]]
 
* primnatriene ... 2(3&rarr;4) abeo cadinane<br/>[[Image:Primnatriene.png|80px]]
Line 133: Line 181:
 
* mutisianthol ... 6(7&rarr;8) abeo cadinane<br/>[[Image:Mutisianthol.png|90px]]
 
* mutisianthol ... 6(7&rarr;8) abeo cadinane<br/>[[Image:Mutisianthol.png|90px]]
 
* copaane ... 5,10 cyclo cadinane<br/>[[Image:Copaane.png|80px]]
 
* copaane ... 5,10 cyclo cadinane<br/>[[Image:Copaane.png|80px]]
 +
|}
 +
| copacamphane ... 3,7-cyclocadinane
 +
* cyclocopacamphane
 +
* sinularane
 +
* cyclosinularane
 
|-
 
|-
 
|rowspan="2"| (Z,E)-humulane<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]<br/>[[Image:Himachalane.png|85px]]
 
| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane]<br/>[[Image:Himachalane.png|85px]]
−
* lippifoliane<br/>[[Image:Lippifoliane.png|80px]]
+
{| class="wikitable"
−
* longipinane<br/>[[Image:Longipinane.png|75px]]
+
|valign="top"|
−
* longibornane<br/>[[Image:Longibornane.png|75px]]
+
* lippifoliane ... 7,9-cyclo form<br/>[[Image:Lippifoliane.png|80px]]
−
* longifolane<br/>[[Image:Longifolane.png|70px]]<!--[[Image:(+)-Longifolene.png|60px]]-->
+
* longipinane ... 2,7-cyclo form<br/>[[Image:Longipinane.png|75px]]
 +
|valign="top"|
 +
* longibornane ... 3,7-cyclo form<br/>[[Image:Longibornane.png|75px]]
 +
* longifolane ... ?<br/>[[Image:Longifolane.png|70px]]<!--[[Image:(+)-Longifolene.png|60px]]-->
 +
|}
 
|-
 
|-
 
| protoilludane<br/>[[Image:Protoilludane.png|95px]]
 
| protoilludane<br/>[[Image:Protoilludane.png|95px]]
 +
{| class="wikitable"
 +
|align="top"|
 
* illudane<br/>[[Image:Illudane.png|85px]]
 
* illudane<br/>[[Image:Illudane.png|85px]]
 
* illudalane ... 4,6-secoilludane<br/>[[Image:Illudalane.png|85px]]
 
* illudalane ... 4,6-secoilludane<br/>[[Image:Illudalane.png|85px]]
 
* sterpurane ... 5(6&rarr;7)-abeoilludane<br/>[[Image:Sterpurane.png|85px]]
 
* sterpurane ... 5(6&rarr;7)-abeoilludane<br/>[[Image:Sterpurane.png|85px]]
 
* isolactarane<br/>[[Image:Isolactarane.png|85px]]
 
* isolactarane<br/>[[Image:Isolactarane.png|85px]]
 +
|align="top"|
 
* merulane<br/>[[Image:Merulane.png|85px]]
 
* merulane<br/>[[Image:Merulane.png|85px]]
 
* lactarane<br/>[[Image:Lactarane.png|85px]]
 
* lactarane<br/>[[Image:Lactarane.png|85px]]
 
* marasmane<br/>[[Image:Marasmane.png|75px]]
 
* marasmane<br/>[[Image:Marasmane.png|75px]]
−
| hirsutane<br/>[[Image:Hirsutane.png|90px]]
+
|}
 +
| [http://books.google.co.jp/books?id=NVhl4oZ9gssC&pg=PA112&lpg=PA112&dq=hirsutane+biosynthesis&source=bl&ots=FkU-OMSTG4&sig=cU9UurL1lEat_nG8PSxgOSUHZJo&hl=en&ei=UercTtLeHs7prQfh86meCQ&sa=X&oi=book_result&ct=result&resnum=1&ved=0CBoQ6AEwAA#v=onepage&q=hirsutane%20biosynthesis&f=false hirsutane]<br/>[[Image:Hirsutane.png|90px]]
 
|-
 
|-
 
| 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)<br/>[[Image:Daucane.png|90px]]
 
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (= carotane)<br/>[[Image:Daucane.png|90px]]
 
* isodaucane<br/>[[Image:Isodaucane.png|70px]]
 
* isodaucane<br/>[[Image:Isodaucane.png|70px]]
 +
| sativane
 +
* helminthosporane ... 13,14-seco sativane
 
|-
 
|-
 
| furodysin<br/>[[Image:Furodysin.png|120px]]
 
| furodysin<br/>[[Image:Furodysin.png|120px]]
Line 172: Line 235:
 
|-
 
|-
 
| botrydial<br/>[[Image:Botrydial.png|100px]]
 
| botrydial<br/>[[Image:Botrydial.png|100px]]
−
|}
 
−
 
−
{| class="wikitable"
 
−
| tricyclic
 
−
{|
 
−
|-
 
−
* cedrane<br/>[[Image:Cedrane.png|80px]]
 
−
* isocedrane<br/>[[Image:Isocedrane.png|80px]]
 
−
* zizaane<br/>[[Image:Zizaane.png|80px]]
 
−
* prezizaane<br/>[[Image:Prezizaane.png|80px]]
 
 
|-
 
|-
 +
| [http://ddr.nal.usda.gov/bitstream/10113/45147/1/IND44408488.pdf thapsane] (head-to-head)<br/>[[Image:Thapsane.png|85px]]
 
|}
 
|}

Revision as of 01:10, 20 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 cyclofarnesan
(E,E)-germacradiene
(E,E)-Germacradienyl cation.png
  • germacrane
    Germacrene A.png
  • lepidozane
    Lepidozane.png
  • bicyclogermacrane
    Bicyclogermacrane.png
eudesmane (= selinane)
Eudesmanyl cation.png
  • cycloeudesmane
    Cycloeudesmane.png
  • elemane ... 7,8 seco form
    Elemene.png
  • emmotin ... 14(10→1) abeo form
    Emmotin.png
  • farfugin ... 14(10→9) abeo form
    Farfugin.png
  • gorgonane 11(7→6) abeo form
    Gorgonane.png
  • oppositane ... 8(7→6) abeo form
    Oppositane.png
  • valerane (= jatamansane) 15(4→5) abeo form
    Valerane.png
vetispiradienyl cation
Vetispiradienyl cation.png
  • vetispiradiene
    Vetispiradiene.png
  • spirovetivane (= vetispirane)
    Spirovetivane.png
eremophilane (= 14(10→5) abeoeudesmane)
Eremophilenyl cation.png
  • aristolochene
    5-epi-Aristolochene.png
  • aristolane ... 6,11-cyclo form
    Aristolane.png
  • chiloscyphane ...8(7→6) abeo form
    Chiloscyphane.png
  • nardosinane ... 11(7→6) abeo form
    Nardosinane.png
  • cacalol ... 14(5→6) abeo form
    Cacalol.png
ishwarane ... 10,12-cycloeremophilane
Ishwarane.png
guaiane
Guaiane.png
  • xanthane ... 4,5 seco form
    Xanthane.png
  • carabrane ... 4,5 seco form
    Carabrane.png
  • pseudoguaiane ... 15(4→5) abeo form
    Pseudoguaiane.png
  • valerenane ... 8(7→6) abeo form
    Valerenane.png

cycloguaiane

  • cubebane ... 1,6-cyclo form
    Cubebane.png
  • ivaxillarane ... 8,10-cyclo form
    Ivaxillarane.png
  • aromadendrane ... 6,11- cyclo form
    Aromadendrane.png
  • rotundane ... 10,12-cyclo form
    Rotundane.png
  • patchoulane ... 1,11-cyclo form
    Patchoulane.png
  • bourbonane ... 6,10-cyclo form
    Bourbonane.png
(E,E)-humulane
(E,E)-Humulyl cation.png
  • bicyclohumulane
    Bicyclohumulane.png
caryophyllane
(E)-beta-Caryophyllene.png
  • silphiperfoliane
  • presilphiperforliane
africanane
Africanane.png 		precapnellane
* capnellane
drimane
Drimane.png
  • iresin
    Iresin.png
  • coloratane
    Coloratane.png
nerolidyl cation
Nerolidyl cation.png 		bisabolane
Bisabolyl cation.png
  • thujopsane
    (-)-Sesquithujene.png
chamigrane ... 6,11-cyclobisabolane
Chamigrane.png
  • acorane ... 6,10-cyclobisabolane
    Acorane.png
cedrane ... 6,10- 2,11-bicyclobisabolane cedrane
Cedrane.png
  • isocedrane
    Isocedrane.png
campherenane
  • α β-santalane
prezizaane ??
Prezizaane.png
  • zizaane ??
    Zizaane.png
cuparane (= 7,11-cyclobisabolane)
Cuparane.png 		trichothecane [1]
Trichothecane.png
  • gymnomitrane
    Gymnomitrane.png
widdrane
(Z,E)-germacradiene
(Z,E)-Germacradienyl cation.png 		cadinane
Cadinane.png
  • muurolane
    Muurolane.png
  • bulgarane
    Bulgarane.png
  • amorphane
    Amorphane.png
  • calamenene
    Calamenene.png
  • cadalane
    Cadalane.png
  • alliacane ... 2(3→4) abeo cadinane
    Alliacane.png
  • primnatriene ... 2(3→4) abeo cadinane
    Primnatriene.png
  • oplopane ... 3(4→5) abeo cadinane
    Oplopane.png
  • mutisianthol ... 6(7→8) abeo cadinane
    Mutisianthol.png
  • copaane ... 5,10 cyclo cadinane
    Copaane.png
copacamphane ... 3,7-cyclocadinane
  • cyclocopacamphane
  • sinularane
  • cyclosinularane
(Z,E)-humulane
(Z,E)-Humulyl cation.png 		himachalane
Himachalane.png
  • lippifoliane ... 7,9-cyclo form
    Lippifoliane.png
  • longipinane ... 2,7-cyclo form
    Longipinane.png
  • longibornane ... 3,7-cyclo form
    Longibornane.png
  • longifolane ... ?
    Longifolane.png
protoilludane
Protoilludane.png
  • illudane
    Illudane.png
  • illudalane ... 4,6-secoilludane
    Illudalane.png
  • sterpurane ... 5(6→7)-abeoilludane
    Sterpurane.png
  • isolactarane
    Isolactarane.png
  • merulane
    Merulane.png
  • lactarane
    Lactarane.png
  • marasmane
    Marasmane.png
hirsutane
Hirsutane.png
cycloheptenyl cation
Cycloheptenyl cation.png 		daucane (= carotane)
Daucane.png
  • isodaucane
    Isodaucane.png
sativane
  • helminthosporane ... 13,14-seco sativane
furodysin
Furodysin.png
  • furodysinin
    Furodysinin.png
others
pinguisane
Pinguisane.png
picrotoxane
Picrotoxane.png
perforane
Perforane.png
pacifigorgiane
Pacifigorgiane.png
asteriscane
Asteriscane.png
botrydial
Botrydial.png
thapsane (head-to-head)
Thapsane.png

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