Category:TP5

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=={{Bilingual|生合成|Biosynthesis}}==
 
=={{Bilingual|生合成|Biosynthesis}}==
 
==={{Bilingual|概要|Overview}}===
 
==={{Bilingual|概要|Overview}}===
 +
Two major classes of terpene synthases exist: "transoid" and "cisoid" synthase.
 +
Transoid synthase directly ionizes ('trans','trans')-farnesyl diphosphate, whereas
 +
Cisoid synthase first isomerizes C2-C3 double bond to produce the neutral (3'R')- or (3'S')-nerolidyl diphosphate (enzyme-bound) and then ionizes it.
 +
 +
{| class="wikitable" style="text-align:right"
 +
! Substrate || Type || Intermediate
 +
|-
 +
| rowspan="2"| Farnesyl diphosphate (FPP)<br/>[[Image:Farnesyl_diphosphate.png]]
 +
| Transoid synthase on (2-''trans'',6-''trans'')-FPP<br/>
 +
| [[Image:Farnesyl_cation.png]]
 +
|-
 +
| Cisoid synthase on (2-''cis'',6-''trans'')-FPP<br/>
 +
| (nerolidyl cation)<br/>[[Image:Nerolidyl_cation.png]]
 +
|}
  
  
Line 38: Line 52:
 
{| class="wikitable"
 
{| class="wikitable"
 
|-
 
|-
−
| farnesyl diphosphate
+
| farnesyl diphosphate<br/>[[Image:Farnesyl diphosphate.png|120px]]
 
|-
 
|-
−
| [[File:Arrow00d.png]]
+
|align="center"| [[File:Arrow00d35.png]]
 +
 
 +
<!---FARNESYL--->
 
|-
 
|-
−
| farnesyl cation
+
|rowspan="7" align="center" valign="top"| farnesyl cation<br/>[[Image:Farnesyl cation.png|100px]]
 +
|colspan="2"|
 +
{|
 +
| farnesane, acyclic ones
 +
| cyclobutane, cyclopentane
 +
| cyclofarnesan
 +
|}
 
|-
 
|-
−
|rowspan="6"| [[File:Arrow00d.png]]
+
|rowspan="3" valign="top"|(E,E)-germacradiene<br/>[[Image:(E,E)-Germacradienyl cation.png]]
 +
<hr style="border:dashed"/>
 +
* germacrane<br/>[[Image:Germacrene A.png|90px]]
 +
* lepidozane<br/>[[Image:Lepidozane.png|90px]]
 +
* bicyclogermacrane<br/>[[Image:Bicyclogermacrane.png|90px]]
 +
| eudesmane (= selinane)<br/>[[Image:Eudesmanyl cation.png]]<!---[[Image:beta-Selinene.png|80px]]-->
 +
<hr style="border:dashed"/>
 +
* cycloeudesmane<br/>[[Image:Cycloeudesmane.png|85px]]
 +
* elemane ... 7,8 seco form<br/>[[Image:Elemene.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]]
 +
* gorgonane 11(7&rarr;6) abeo form<br/>[[Image:Gorgonane.png|70px]]
 +
* 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]]
 +
|valign="top"|vetispiradienyl cation<br/>[[Image:Vetispiradienyl_cation.png|90px]]
 +
<hr style="border:dashed"/>
 +
* vetispiradiene<br/>[[Image:Vetispiradiene.png|80px]]
 +
* spirovetivane (= vetispirane)<br/>[[Image:Spirovetivane.png|80px]]
 
|-
 
|-
−
| farnesane, acyclic ones
+
| eremophilane (= 14(10&rarr;5) abeoeudesmane)<br/>[[Image:Eremophilenyl cation.png|100px]]
 +
* aristolochene<br/>[[Image:5-epi-Aristolochene.png|85px]]
 +
* aristolane ... 6,11-cyclo form<br/>[[Image:Aristolane.png|80px]]
 +
* chiloscyphane ...8(7&rarr;6) abeo form<br/>[[Image:Chiloscyphane.png|80px]]
 +
* nardosinane ... 11(7&rarr;6) abeo form<br/>[[Image:Nardosinane.png|70px]]
 +
* cacalol ... 14(5&rarr;6) abeo form<br/>[[Image:Cacalol.png|85px]]
 +
* fukinane ... 9(8&rarr;7) abeo form<br/>[[Image:Fukinane.png|85px]] [[Petasites japonicus]]
 +
* brasilane<br/>[[Image:Brasilane.png|75px]]
 +
* thapsane<br/>[[Image:Thapsane.png|85px]]
 +
* ishwarane<br/>[[Image:Ishwarane.png|60px]]
 
|-
 
|-
−
| cyclobutane, cyclopentane
+
| [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]]
 +
* xanthane ... 4,5 seco form<br/>[[Image:Xanthane.png|70px]]
 +
* carabrane ... 4,5 seco form<br/>[[Image:Carabrane.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]]
 +
|
 +
cycloguaiane
 +
* cubebane ...  1,6-cyclo form<br/>[[Image:Cubebane.png|80px]]
 +
* ivaxillarane ... 8,10-cyclo form<br/>[[Image:Ivaxillarane.png|80px]]
 +
* aromadendrane ... 6,11- cyclo form<br/>[[Image:Aromadendrane.png|70px]]
 +
* rotundane ... 10,12-cyclo form<br/>[[Image:Rotundane.png|60px]]
 +
* patchoulane ... 1,11-cyclo form<br/>[[Image:Patchoulane.png|60px]]
 +
* bourbonane ... 6,10-cyclo form<br/>[[Image:Bourbonane.png|80px]]
 
|-
 
|-
−
| cyclofarnesane
+
|rowspan="2"| (E,E)-humulane<br/>[[Image:(E,E)-Humulyl cation.png|100px]]
 +
* bicyclohumulane<br/>[[Image:Bicyclohumulane.png|80px]]
 +
| caryophyllane<br/>[[Image:(E)-beta-Caryophyllene.png|80px]]
 
|-
 
|-
−
| germacrane (elemane, lepidozane, (bi)cyclogermacrane) [http://www.pnas.org/content/95/5/2216/F1.expansion.html]
+
| [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane]<br/>[[Image:Africanane.png|80px]]
−
 
+
−
{| class="wikitable"
+
−
| eudesmane (emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane, spirovetivane (= vetispirane))
+
 
|-
 
|-
−
| 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.sciencedirect.com/science/article/pii/S0040402099002562 drimane]<br/>[[Image:Drimane.png|100px]]
 +
* iresin<br/>[[Image:Iresin.png|90px]]
 +
* coloratane<br/>[[Image:Coloratane.png|90px]]
 +
|
 +
<!---NEROLIDYL--->
 
|-
 
|-
−
| [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)
+
|rowspan="7"| nerolidyl cation<br/>[[Image:Nerolidyl cation.png|100px]]
−
 
+
|rowspan="2"| bisabolane<br/>[[Image:Bisabolyl cation.png|100px]]
−
{| class="wikitable"
+
* thujopsane<br/>[[Image:(-)-Sesquithujene.png|80px]]
−
| cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
+
| chamigrane ... 6,11-cyclobisabolane<br/>[[Image:Chamigrane.png|90px]]
−
|}
+
* acorane ... 6,10-cyclobisabolane<br/>[[Image:Acorane.png|80px]]
 
|-
 
|-
 +
| cuparane (= 7,11-cyclobisabolane)<br/>[[Image:Cuparane.png|95px]]
 +
* herbertane [[liverwort,fungi]] ... 15(3&rarr;4) abeo form<br/>[[Image:Herbertane.png|80px]]
 +
* laurane [[Laurencia spp. (marine)]] ... 13(11&rarr;10) abeo form<br/>[[Image:Laurane.png|90px]]
 +
* cyclolaurane <br/>[[Image:Cyclolaurane.png|85px]]
 +
| trichothecane <ref>Grove JF "Non-Macrocyclic Trichothecenes" Nat Prod Rep 5:187-209, 1988</ref><br/>[[Image:Trichothecane.png|50px]]
 +
* gymnomitrane<br/>[[Image:Gymnomitrane.png|70px]]
 +
{|
 +
| widdrane<!--structure not shown<br/>[[Image:Widdrane.png|70px]]-->
 
|}
 
|}
−
 
 
|-
 
|-
−
| humulane (caryyllophyllane, bicyclohumulane, [http://stoltz.caltech.edu/seminars/2009_Henry.pdf africanane])  
+
| (Z,E)-germacradiene<br/>[[Image:(Z,E)-Germacradienyl cation.png|100px]]
 +
| cadinane<br/>[[Image:Cadinane.png|90px]]
 +
* muurolane<br/>[[Image:Muurolane.png|80px]]
 +
* bulgarane<br/>[[Image:Bulgarane.png|80px]]
 +
* amorphane<br/>[[Image:Amorphane.png|80px]]
 +
* calamenene<br/>[[Image:Calamenene.png|80px]]
 +
* cadalane<br/>[[Image:Cadalane.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]]
 +
* oplopane ... 3(4&rarr;5) abeo cadinane<br/>[[Image:Oplopane.png|80px]]
 +
* mutisianthol ... 6(7&rarr;8) abeo cadinane<br/>[[Image:Mutisianthol.png|90px]]
 +
* copaane ... 5,10 cyclo cadinane<br/>[[Image:Copaane.png|80px]]
 
|-
 
|-
−
| rowspan="2" | bisabolyl cation
+
|rowspan="2"| (Z,E)-humulane<br/>[[Image:(Z,E)-Humulyl cation.png|100px]]
−
| bisabolane
+
| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane]<br/>[[Image:Himachalane.png|85px]]
−
{| class="wikitable"
+
* lippifoliane<br/>[[Image:Lippifoliane.png|80px]]
−
| cuparane (herbertane [[liverwort,fungi]], laurane  [[Laurencia spp. (marine)]], cyclolaurane,  [http://www.springerlink.com/content/h40302g23g830241/ trichothecane] (from scirpane),  gymnomitrane, thujopsane, widdrane, )
+
* longipinane<br/>[[Image:Longipinane.png|75px]]
−
|}
+
* longibornane<br/>[[Image:Longibornane.png|75px]]
 +
* longifolane<br/>[[Image:Longifolane.png|70px]]<!--[[Image:(+)-Longifolene.png|60px]]-->
 
|-
 
|-
−
[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]
+
| protoilludane<br/>[[Image:Protoilludane.png|95px]]
 +
* illudane<br/>[[Image:Illudane.png|85px]]
 +
* illudalane ... 4,6-secoilludane<br/>[[Image:Illudalane.png|85px]]
 +
* sterpurane ... 5(6&rarr;7)-abeoilludane<br/>[[Image:Sterpurane.png|85px]]
 +
* isolactarane<br/>[[Image:Isolactarane.png|85px]]
 +
* merulane<br/>[[Image:Merulane.png|85px]]
 +
* lactarane<br/>[[Image:Lactarane.png|85px]]
 +
* marasmane<br/>[[Image:Marasmane.png|75px]]
 +
| hirsutane<br/>[[Image:Hirsutane.png|90px]]
 
|-
 
|-
−
| (Z,E)-germacradienyl cation
+
| cycloheptenyl cation<br/>[[Image:Cycloheptenyl cation.png|100px]]
−
| cadinane (bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol, cadalane, copaane)
+
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (= carotane)<br/>[[Image:Daucane.png|90px]]
 +
* isodaucane<br/>[[Image:Isodaucane.png|70px]]
 
|-
 
|-
−
|rowspan="2"| (Z,E)-humulyl cation
+
| furodysin<br/>[[Image:Furodysin.png|120px]]
−
| [http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200300812/pdf himachalane] (lippifoliane, longipinane, longibornane, longifolane)
+
* furodysinin<br/>[[Image:Furodysinin.png|100px]]
 
|-
 
|-
−
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane) --> hirsutane
+
| others
 +
|
 +
{| class="wikitable"
 +
| [http://alamlearning.blogspot.com/2010/11/possible-biosynthetic-pathway-for.html pinguisane]<br/>[[Image:Pinguisane.png|100px]]
 
|-
 
|-
−
| cycloheptenyl cation
+
| picrotoxane<br/>[[Image:Picrotoxane.png|100px]]
−
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (= carotane, isodaucane)
+
 
|-
 
|-
−
| drimenyl cation
+
| perforane<br/>[[Image:Perforane.png|90px]]
−
| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane] (iresin, seco, coloratane)
+
 
|-
 
|-
−
| furodysyl cation
+
| pacifigorgiane<br/>[[Image:Pacifigorgiane.png|90px]]
−
| furodysin (furodysinin)
+
 
|-
 
|-
−
| chamigranyl cation
+
| asteriscane<br/>[[Image:Asteriscane.png|80px]]
−
| chamigrane (secochamigrane)
+
 
|-
 
|-
−
| Others
+
| botrydial<br/>[[Image:Botrydial.png|100px]]
−
|
+
−
{| class="wikitable"
+
−
| [http://alamlearning.blogspot.com/2010/11/possible-biosynthetic-pathway-for.html pinguisane], picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial
+
 
|}
 
|}
  
 
{| class="wikitable"
 
{| class="wikitable"
−
| Tricyclic
+
| tricyclic
 
{|
 
{|
−
| Cedrane (isocedrane)
 
 
|-
 
|-
−
| Prezizaane (zizaane)
+
* cedrane<br/>[[Image:Cedrane.png|80px]]
−
|}
+
* isocedrane<br/>[[Image:Isocedrane.png|80px]]
−
 
+
* zizaane<br/>[[Image:Zizaane.png|80px]]
−
 
+
* prezizaane<br/>[[Image:Prezizaane.png|80px]]
 +
* clovane<br/>[[Image:Clovane.png|80px]]
 +
* precapnellane<br/>[[Image:Precapnellane.png|80px]]
 +
* capnellane<br/>[[Image:Capnellane.png|80px]]
 +
* pentalenane<br/>[[Image:Pentalenane.png|80px]]
 +
* silphinane<br/>[[Image:Silphinane.png|80px]]
 +
* silphiperfoliane<br/>[[Image:Silphiperfoliane.png|80px]]
 +
* presilphiperfolane<br/>[[Image:Presilphiperfolane.png|80px]]
 +
* isocomane<br/>[[Image:Isocomane.png|80px]]
 +
* panasinsane<br/>[[Image:Panasinsane.png|80px]]
 +
* modhephane<br/>[[Image:Modhephane.png|80px]]
 +
* quadrane<br/>[[Image:Quadrane.png|80px]]
 +
* campherenane<br/>[[Image:Campherenane.png|80px]]
 +
* alpha-santalane<br/>[[Image:alpha-Santalane.png|80px]]
 +
* beta-santalane<br/>[[Image:beta-Santalane.png|80px]]
 +
* sativane<br/>[[Image:Sativane.png|80px]]
 +
* helminthosporane<br/>[[Image:Helminthosporane.png|80px]]
 +
* copacamphane<br/>[[Image:Copacamphane.png|80px]]
 +
* cyclocopacamphane<br/>[[Image:Cyclocopacamphane.png|80px]]
 +
* sinularane<br/>[[Image:Sinularane.png|80px]]
 +
* cyclosinularane<br/>[[Image:Cyclosinularane.png|80px]]
 +
|-
 
|}
 
|}

Latest revision as of 13:17, 22 July 2014

Contents

[edit] Sesquiterpene (C15)

[edit] Ring configuration

[edit] Germacrane


[edit] Sesquiterpenes

[edit] Biosynthesis

[edit] Overview

Two major classes of terpene synthases exist: "transoid" and "cisoid" synthase. Transoid synthase directly ionizes ('trans','trans')-farnesyl diphosphate, whereas Cisoid synthase first isomerizes C2-C3 double bond to produce the neutral (3'R')- or (3'S')-nerolidyl diphosphate (enzyme-bound) and then ionizes it.

Substrate Type Intermediate
Farnesyl diphosphate (FPP)
Farnesyl diphosphate.png 		Transoid synthase on (2-trans,6-trans)-FPP
 Farnesyl cation.png
Cisoid synthase on (2-cis,6-trans)-FPP
 (nerolidyl cation)
Nerolidyl cation.png


References


[edit] 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
  • fukinane ... 9(8→7) abeo form
    Fukinane.png Petasites japonicus
  • brasilane
    Brasilane.png
  • thapsane
    Thapsane.png
  • ishwarane
    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
africanane
Africanane.png
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
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
(Z,E)-humulane
(Z,E)-Humulyl cation.png 		himachalane
Himachalane.png
  • lippifoliane
    Lippifoliane.png
  • longipinane
    Longipinane.png
  • longibornane
    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
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
tricyclic
  • cedrane
    Cedrane.png
  • isocedrane
    Isocedrane.png
  • zizaane
    Zizaane.png
  • prezizaane
    Prezizaane.png
  • clovane
    Clovane.png
  • precapnellane
    Precapnellane.png
  • capnellane
    Capnellane.png
  • pentalenane
    Pentalenane.png
  • silphinane
    Silphinane.png
  • silphiperfoliane
    Silphiperfoliane.png
  • presilphiperfolane
    Presilphiperfolane.png
  • isocomane
    Isocomane.png
  • panasinsane
    Panasinsane.png
  • modhephane
    Modhephane.png
  • quadrane
    Quadrane.png
  • campherenane
    Campherenane.png
  • alpha-santalane
    Alpha-Santalane.png
  • beta-santalane
    Beta-Santalane.png
  • sativane
    Sativane.png
  • helminthosporane
    Helminthosporane.png
  • copacamphane
    Copacamphane.png
  • cyclocopacamphane
    Cyclocopacamphane.png
  • sinularane
    Sinularane.png
  • cyclosinularane
    Cyclosinularane.png

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