Category:TP3

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{{Twocolumn|
 
{{Twocolumn|
 
The starting point is squalene, which is formed by joining two FPPs tail-to-tail.
 
The starting point is squalene, which is formed by joining two FPPs tail-to-tail.
−
Bacterial cyclases use squalene directly, but those of the other species use  
+
Bacterial cyclases use squalene directly<ref>Bacterial squalene cyclases can accept oxidosqualene as their substrates, but oxidosqualene usually does not exist in bacteria</ref>, but those of the other species use  
 
2,3-oxidosqualene for cyclization.
 
2,3-oxidosqualene for cyclization.
  
−
* In bacteria, squalene is cyclized via the 17&alpha;-deoxydammarenyl cation to hopene and other triterpenes<ref>Bacterial squalene cyclases can accept oxidosqualene as their substrates, but oxidosqualene usually does not exist in bacteria</ref>.
+
* In bacteria, squalene is cyclized via the 17&alpha;-deoxydammarenyl cation to hopene and other triterpenes.
−
* In eukaryotes, 2,3-oxidosqualene is cyclized via the protosteryl cation to lanosterol (animals and fungi) or cycloartenol (plants) by a series of 1,2-hydride and methyl shifts (Wagner-Meerwein shifts).<ref>A trace amount of phytosterols comes from lanosterol. Ohyama K, Suzuki M, Kikuchi J, Saito K, Muranaka T (2009) Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis ''Proc Natl Acad Sci USA'' 106(3):725-730</ref>
+
* In eukaryotes, 2,3-oxidosqualene is cyclized via the protosteryl cation to lanosterol (animals and fungi) or cycloartenol (plants) by a series of 1,2-hydride and methyl shifts (Wagner-Meerwein shifts).<ref>In plants, a trace amount of phytosterols comes from lanosterol.<br/>''Ref.'' Ohyama K, Suzuki M, Kikuchi J, Saito K, Muranaka T (2009) Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis ''Proc Natl Acad Sci USA'' 106(3):725-730</ref>
−
* In plants, various triterpenes arise from the dammarenyl cation.
+
* In plants, various triterpenes arise from the 17&beta;-dammarenyl cation.
 
|
 
|
 
始まりとなる物質はスクアレンで、二分子のファルネシル二リン酸が末尾どうしで結合して作られます。バクテリアの環化酵素はスクアレンをそのまま利用しますが<ref>バクテリアのスクアレン環化酵素はオキシドスクアレンも基質として利用できますが、バクテリアはオキシドスクアレンを合成しません。</ref>、それ以外の生物種では2,3-オキシドスクアレンを利用します。
 
始まりとなる物質はスクアレンで、二分子のファルネシル二リン酸が末尾どうしで結合して作られます。バクテリアの環化酵素はスクアレンをそのまま利用しますが<ref>バクテリアのスクアレン環化酵素はオキシドスクアレンも基質として利用できますが、バクテリアはオキシドスクアレンを合成しません。</ref>、それ以外の生物種では2,3-オキシドスクアレンを利用します。
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* 更に植物の場合、17&beta;-ダンマラン型のカチオンから様々なトリテルペンが生成されます。
 
* 更に植物の場合、17&beta;-ダンマラン型のカチオンから様々なトリテルペンが生成されます。
 
}}
 
}}
 +
 +
===={{Bilingual|Eukaryotes|真核生物}}====
 +
{|
 +
|-
 +
! ({{Bilingual|Backbone Color Code: |骨格色分け: }}
 +
! style="background-color:#fdd"| Animals, fungi, and yeast
 +
! style="background-color:#dfd"| Plants only
 +
! )
 +
|}
  
 
<center>
 
<center>
 
{|style="text-align:center"
 
{|style="text-align:center"
−
|style="background-color:#fdd"| ANIMALS, FUNGI, and YEAST
 
−
|style="background-color:#dfd"| PLANTS
 
 
|-
 
|-
 
|colspan="7"| 2,3-oxidosqualene
 
|colspan="7"| 2,3-oxidosqualene
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|colspan="7"|[[Image:2,3-oxidosqualene.png]]
 
|colspan="7"|[[Image:2,3-oxidosqualene.png]]
 
|-
 
|-
−
|colspan="2" align="right"| lanosterol [[Image:Arrow00dl35.png]] synthase<ref>The most accessible enzyme among oxidosqualene cyclases.<br/>''Ref.'' Corey EJ, Russey WE, Ortiz-de-Montellano PR (1966) 2,3-Oxidosqualene, an intermediate in the biological synthesis of sterols from squalene ''J Am Chem Soc'' 88:4750-1</ref>
+
|colspan="2" align="right"|
 +
{|
 +
|lanosterol<br/>syntase<ref>Lanosterol synthase is the most accessible enzyme among oxidosqualene cyclases.<br/>''Ref.'' Corey EJ, Russey WE, Ortiz-de-Montellano PR (1966) 2,3-Oxidosqualene, an intermediate in the biological synthesis of sterols from squalene ''J Am Chem Soc'' 88:4750-1 </ref>
 +
|[[Image:Arrow00dl35.png]]
 +
|stepwise<br/>cyclization<ref>The cyclization process is stepwise, not concerted as previously thought. As one clue, squalene is not fully folded in the cyclase active site.<br/>''Ref.'' Reinert DJ, Balliano G, Schulz GE (2004) Conversion of squalene to the pentacarbocyclic hopene. ''Chem Biol'' 11:121-6</ref>
 +
|}
 
|colspan="2"|
 
|colspan="2"|
−
|align="left"| lupeol [[Image:Arrow00dr35.png]] synthase
+
|align="left"|
 +
{|
 +
|lupeol<br/>synthase
 +
|[[Image:Arrow00dr35.png]]
 +
|stepwise<br/>cyclization
 +
|}
 
|-
 
|-
−
| 17&beta;-protosteryl cation <small>(C-B-C)</small><ref>The rings of protosteryl cation are chair-boat-chair configuration. The C-17 chain is &beta;-configuration, not &alpha;.<br/>
+
| 17&beta;-protosteryl cation <small>(C-B-C)</small><ref>The C-17 chain of rotosteryl cation is &beta;-configuration, not &alpha;.<br/> ''Ref.'' Corey EJ, Virgil SC (1991) An experimental demonstration of the stereochemistry of enzymic cyclization of 2,3-oxidosqualene to the protosterol system, forerunner of lanosterol and cholesterol. [http://pubs.acs.org/doi/abs/10.1021/ja00010a073 ''J Am Chem Soc'' 113:4025-6]</ref> <br/>[[Image:Protosteryl cation.png]]
−
''Ref.'' Corey EJ, Virgil SC (1991) An experimental demonstration of the stereochemistry of enzymic cyclization of 2,3-oxidosqualene to the protosterol system, forerunner of lanosterol and cholesterol. [http://pubs.acs.org/doi/abs/10.1021/ja00010a073 ''J Am Chem Soc'' 113:4025-6]</ref>
+
| 1,2-shift<br/>[[Image:Arrow00r.png]]
−
<br/>[[Image:Protosteryl cation.png]]
+
−
| 1,2-shift<br/>[[Image:Arrow00r35.png]]
+
 
| colspan="2"|lanosteryl cation <small>(C-C-C)</small><br/>[[Image:Lanosteryl cation.png]]
 
| colspan="2"|lanosteryl cation <small>(C-C-C)</small><br/>[[Image:Lanosteryl cation.png]]
−
| 17&beta;-dammarenyl cation <small>(C-C-C)</small><ref>The rings of dammarenyl cation are all-chair configuration. The C-17 chain is &beta;-configuration.<br/>
+
| 17&beta;-dammarenyl cation <small>(C-C-C)</small><ref>The C-17 chain of dammarenyl cation is &beta;-configuration.<br/> ''Ref.'' Xiong Q, Rocco F, Wilson WK, Xu R, Ceruti M, Matsuda SPT (2005) Structure and reactivity of the dammarenyl cation: configuration transmission in triterpene synthesis. ''J Org. Chem. 70:5362-75</ref> <br/>[[Image:Dammarenyl cation.png]]
−
''Ref.'' Xiong Q, Rocco F, Wilson WK, Xu R, Ceruti M, Matsuda SPT (2005) Structure and reactivity of the dammarenyl cation: configuration transmission in triterpene synthesis. ''J Org. Chem. 70:5362-75</ref>
+
−
<br/>[[Image:Dammarenyl cation.png]]
+
 
|-
 
|-
 
|colspan="2"|
 
|colspan="2"|
 
{|
 
{|
 +
|
 +
{|
 +
|-
 
|D-ring<br/>expansion
 
|D-ring<br/>expansion
 
|[[Image:Arrow00d.png]]
 
|[[Image:Arrow00d.png]]
−
| &nbsp;&nbsp;&nbsp;&nbsp;
+
|}
−
| [[Image:Arrow00dr35.png]]protostane
+
|
 +
{|
 +
| [[Image:Arrow00dr35.png]]
 +
| fungus<br/>only<ref>Oxygenated protostane are known in ''Cephalosporium caerulens'', ''Fusidium coccineum'', and ''Aspergillus fumigatus'' (Ascomycota). <br/>''Ref.'' Hattori H, Igarashi H, Iwasaki S, Okuda S, (1969) Isolation of 3bhydroxy- 4b-methylfusida-17(20)[16,21-cis],24 diene (3b-hydroxyprotosta-
 +
17(20)[16,21-cis],24 diene) and a related triterpene alcohol ''Tetrahedron Lett'' 13, 1023–1026<br/>Tiwari KP, Choudhary RN (1981) Chemical examination of ''Wisteria sinensis'' ''Proc Natl Acad Sci India A'' 51, 263–271</ref>
 +
|-
 +
|
 +
|style="background-color:#fdd" align="right"| protostane
 +
|}
 
|}
 
|}
 
| colspan="2"|
 
| colspan="2"|
 
{|
 
{|
−
|[[Image:Arrow00d.png]] 1,2-shift
+
|1,2-shifts [[Image:Arrow00d.png]] all eukaryotes
 
|}
 
|}
 
|
 
|
 
{|
 
{|
 +
|-
 
| D-ring<br/>expansion
 
| D-ring<br/>expansion
 
|[[Image:Arrow00d.png]]
 
|[[Image:Arrow00d.png]]
 +
| [[Image:Arrow00dr35.png]]<br/><br/>
 +
|style="background-color:#dfd" align="center"| dammarane<br/>euphane<br/>tirucalane etc.<ref>Dammarane derivatives are unusually prevalent in the genus [[Species:Euphorbia|Euphorbia]].</ref>
 
|}
 
|}
 
|
 
|
 
|- valign="top"
 
|- valign="top"
−
| unknown cation<br/>[[Image:Lanosteryl cation.png]]
+
|colspan="2"| cation with the chain at C18 or C17 position<br/>[[Image:CBCC cation.png]]or [[Image:CBCC cation2.png]]
−
|
+
 
|
 
|
 
{|
 
{|
−
|style="background-color:#fdd"| lanostane<br/>cycloartane<br/>cucurbitane<br/>all steroids
+
|style="background-color:#fdd"| all steroids<br/>lanostane<br/>cycloartane<br/>cucurbitane<br/>ergostane etc.
 
|}
 
|}
 
|align="right"|
 
|align="right"|
 
{|
 
{|
−
| <br/><br/><br/>baccharane
+
|<br/><br/><br/>
−
| <br/><br/><br/>[[Image:Arrow00l35.png]]
+
|-
 +
|style="background-color:#dfd"| baccharane<br/>shionane
 +
| [[Image:Arrow00l35.png]]
 
|}
 
|}
 
| baccarenyl cation <small>(C-C-C-C)</small><br/>[[Image:Baccarenyl cation.png]]
 
| baccarenyl cation <small>(C-C-C-C)</small><br/>[[Image:Baccarenyl cation.png]]
 
|-
 
|-
−
|colspan="2"|
+
|
 +
{|
 +
| E-ring<br/>cyclization<br/>(from 17&beta;)
 +
| [[Image:Arrow00d.png]]
 +
|}
 +
|
 
{|
 
{|
 
| E-ring<br/>cyclization<br/>(from 18&alpha;)
 
| E-ring<br/>cyclization<br/>(from 18&alpha;)
 
| [[Image:Arrow00d.png]]
 
| [[Image:Arrow00d.png]]
−
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;
 
−
| E-ring<br/>cyclization<br/>(from 17&beta;)
 
−
| [[Image:Arrow00dr.png]]
 
 
|}
 
|}
 
|
 
|
 
|align="right"|
 
|align="right"|
 
{|
 
{|
−
| E-ring cyclization<br/>(from 18&alpha;)
+
| E-ring cyclization<br/>(from 17&alpha;/&beta;)
 
| [[Image:Arrow00dl.png]]
 
| [[Image:Arrow00dl.png]]
 
|}
 
|}
 
|colspan="2"|  
 
|colspan="2"|  
 
{|
 
{|
−
|E-ring<br/>&nbsp;
+
|E-ring cyclization<br/>(from 18&alpha;/&beta;)
 
|[[Image:Arrow00d.png]]
 
|[[Image:Arrow00d.png]]
−
|cyclization<br/>(from 18&beta;)
 
 
|}
 
|}
 
|- valign="top"
 
|- valign="top"
−
| hancolupyl cat. <small>(C-B-C-C)</small><br/>[[Image:Hancolupyl cation.png]]
+
| arborinyl cation <small>(C-B-C-C)</small><br/>[[Image:Arborinyl cation.png]]  
−
| colspan="2" align="left"| arborinyl cation <small>(C-B-C-C)</small><br/>[[Image:Arborinyl cation.png]]
+
| colspan="2" align="left"| unnamed cation <small>(C-B-C-C)</small><br/>[[Image:Hanco cation.png]]
−
| H18&beta;-lupyl cation <small>(C-C-C-B)</small><br/>[[Image:Lupyl cation2.png]]
+
| 21&alpha;-hopyl cation <small>(C-C-C-C)</small><br/>21&beta;-moretyl cation <small>(C-C-C-C)</small><ref>The 21''R'' stereocenter is usually lost in hydride shift.</ref><br/>[[Image:Hopyl cation.png]]
−
| H18&alpha;-lupyl cation <small>(C-C-C-C)</small><br/>[[Image:Lupyl cation.png]]
+
| H18&alpha;-lupyl cation <small>(C-C-C-C)</small><br/>H18&beta;-lupyl cation <small>(C-C-C-B)</small><br/>[[Image:Lupyl cation.png]]
 
|-
 
|-
−
|align="center"| 1,2-[[Image:Arrow00d35.png]] shift
+
|align="left"|
−
|align="center"| 1,2-[[Image:Arrow00d35.png]] shift
+
{|
 +
|1,2-shifts
 +
|[[Image:Arrow00d35.png]]
 +
|E-ring expansion
 +
|}
 
|
 
|
−
|align="center"| 1,2-[[Image:Arrow00d35.png]] shift
+
{|
−
|align="center"| 1,2-[[Image:Arrow00d35.png]] shift
+
|1,2-shifts
−
|-
+
|[[Image:Arrow00d35.png]]
−
|  
+
|E-ring expansion
 +
|}
 
|
 
|
 
|
 
|
 +
{|
 +
|1,2-shifts
 +
|[[Image:Arrow00d35.png]]
 +
|E-ring expansion
 +
|}
 
|
 
|
 +
{|
 +
|1,2-shifts
 +
|[[Image:Arrow00d35.png]]
 +
|E-ring expansion
 +
|}
 +
|-
 +
|style="background-color:#dfd"| arborinane (C-B-C-C)<br/>stictane (C-B-C-C-C)<ref>C-B-C-C-C rings are very rare and stictanediol from Ascomycota [[Species:Sticta|''Sticta'']] genus is the sole example.<br/>''Ref.'' Chin WJ, Corbett RE, Heng CK, Wilkins AL (1973) Lichens and fungi. XI. Isolation and structural elucidation of a new group of triterpenes from ''Sticta coronata, S. colensoi'', and ''S. flavicans''. ''J Chem Soc Perkin Trans'' 1:1437–46</ref>
 +
|style="background-color:#dfd"| hancokinane (C-B-C-C)
 
|
 
|
 +
|style="background-color:#dfd" align="left"| hopane (C-C-C-C)<br/> gammacerane (C-C-C-C-C)<br/> fernane (C-C-C-C)<br/> swertane (C-C-C-C-C)<br/>
 +
|style="background-color:#dfd" align="left"| oleanane (C-C-C-C-C)<br/> lupane (C-C-C-C)<br/> germanicane<br/> taraxastane (C-C-C-C-C)<br/> ursane (C-C-C-C-C/B)<br/> friedomadeirane (C-C-C-C)<ref>E-ring cyclization precedes D-ring expansion.</ref><br/>
 
|}
 
|}
  
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* Xu R, Fazio GC, Matsuda SPT (2004) On the origins of triterpenoid skeletal diversity. ''Phytochemstry'' 65:261-291 PMID 14751299
 
* Xu R, Fazio GC, Matsuda SPT (2004) On the origins of triterpenoid skeletal diversity. ''Phytochemstry'' 65:261-291 PMID 14751299
  
 +
===={{Bilingual|Bacteria|微生物}}====
 
{| style="text-align:center"
 
{| style="text-align:center"
 
|-
 
|-
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| [[Image:Arrow00r.png]]
 
| [[Image:Arrow00r.png]]
 
|-
 
|-
−
| squalene-hopene [[Image:Arrow00d35.png]] cyclase<ref>The most accessible enzyme among squalene cyclases. <br/>''Ref.'' Kannenberg EL, Poralla K (1999) Hopanoid biosyntehsis and function in bacteria. ''Naturwissenschaften'' 86:168-76.<br/>The cyclization process is stepwise, not concerted as previously thought. As one clue, squalene is not fully folded in the cyclase active site.<br/>''Ref.'' Reinert DJ, Balliano G, Schulz GE (2004) Conversion of squalene to the pentacarbocyclic hopene. ''Chem Biol'' 11:121-6</ref>
+
| squalene-hopene [[Image:Arrow00d35.png]] cyclase<ref>SH cyclase is the most accessible enzyme among squalene cyclases. <br/>''Ref.'' Kannenberg EL, Poralla K (1999) Hopanoid biosyntehsis and function in bacteria. ''Naturwissenschaften'' 86:168-76.</ref>
 
|
 
|
 
|-
 
|-

Revision as of 17:57, 9 August 2010

Contents

Triterpene (C30) Classes

Ring configuration

The basic structure is 4 carbon rings, cyclopenta[a]phenanthrene, gonane, or sterane. The rings B/C are always trans in all natural steroids. If the rings C/D are trans, it is called gonane. If its stereochemistry is unspecified, it is called sterane. Most steroids take gonane form, but in cardenolides and bufanolides, the rings C/D are cis.

Cyclopenta-a-phenanthrene.png Gonane.png
Cyclopenta[a]phenanthrene Gonane

The majority of steroids have methyl groups sticking out from the bridgehead positions C-10 and C-13. When these methyl groups (or hydrogens) stand above the plane, they are called β-configuration. Those below the plane are called α-configuration. If the configuration at any site is unknown, it is indicated as ξ (Greek Xi). By default, hydrogen atoms or substituents at the positions C-8, 9, 10, 13, and 14 are assumed to be 8β, 9α, 10β, 13β, and 14α configurations. C-5 is a special position, because there are as many 5α steroids as 5β are.

Cholestane.png 5alpha-steroid.png 5beta-steroid.png
cholestane backbone 5α-configuration 5β-configuration


Biosynthesis

The starting point is squalene, which is formed by joining two FPPs tail-to-tail. Bacterial cyclases use squalene directly[1], but those of the other species use 2,3-oxidosqualene for cyclization.

  • In bacteria, squalene is cyclized via the 17α-deoxydammarenyl cation to hopene and other triterpenes.
  • In eukaryotes, 2,3-oxidosqualene is cyclized via the protosteryl cation to lanosterol (animals and fungi) or cycloartenol (plants) by a series of 1,2-hydride and methyl shifts (Wagner-Meerwein shifts).[2]
  • In plants, various triterpenes arise from the 17β-dammarenyl cation.

真核生物

(骨格色分け: Animals, fungi, and yeast Plants only )
2,3-oxidosqualene
2,3-oxidosqualene.png
lanosterol
syntase[3] 		Arrow00dl35.png stepwise
cyclization[4]
lupeol
synthase 		Arrow00dr35.png stepwise
cyclization
17β-protosteryl cation (C-B-C)[5]
Protosteryl cation.png 		1,2-shift
Arrow00r.png 		lanosteryl cation (C-C-C)
Lanosteryl cation.png 		17β-dammarenyl cation (C-C-C)[6]
Dammarenyl cation.png
D-ring
expansion 		Arrow00d.png
Arrow00dr35.png fungus
only[7]
protostane
1,2-shifts Arrow00d.png all eukaryotes
D-ring
expansion 		Arrow00d.png Arrow00dr35.png

 dammarane
euphane
tirucalane etc.[8]
cation with the chain at C18 or C17 position
CBCC cation.pngor CBCC cation2.png
all steroids
lanostane
cycloartane
cucurbitane
ergostane etc.



baccharane
shionane 		Arrow00l35.png
baccarenyl cation (C-C-C-C)
Baccarenyl cation.png
E-ring
cyclization
(from 17β) 		Arrow00d.png
E-ring
cyclization
(from 18α) 		Arrow00d.png
E-ring cyclization
(from 17α/β) 		Arrow00dl.png
E-ring cyclization
(from 18α/β) 		Arrow00d.png
arborinyl cation (C-B-C-C)
Arborinyl cation.png 		unnamed cation (C-B-C-C)
Hanco cation.png 		21α-hopyl cation (C-C-C-C)
21β-moretyl cation (C-C-C-C)[9]
Hopyl cation.png 		H18α-lupyl cation (C-C-C-C)
H18β-lupyl cation (C-C-C-B)
Lupyl cation.png
1,2-shifts Arrow00d35.png E-ring expansion
1,2-shifts Arrow00d35.png E-ring expansion
1,2-shifts Arrow00d35.png E-ring expansion
1,2-shifts Arrow00d35.png E-ring expansion
arborinane (C-B-C-C)
stictane (C-B-C-C-C)[10] 		hancokinane (C-B-C-C) hopane (C-C-C-C)
gammacerane (C-C-C-C-C)
fernane (C-C-C-C)
swertane (C-C-C-C-C)
 oleanane (C-C-C-C-C)
lupane (C-C-C-C)
germanicane
taraxastane (C-C-C-C-C)
ursane (C-C-C-C-C/B)
friedomadeirane (C-C-C-C)[11]
  1. ↑ Bacterial squalene cyclases can accept oxidosqualene as their substrates, but oxidosqualene usually does not exist in bacteria
  2. ↑ In plants, a trace amount of phytosterols comes from lanosterol.
    Ref. Ohyama K, Suzuki M, Kikuchi J, Saito K, Muranaka T (2009) Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis Proc Natl Acad Sci USA 106(3):725-730
  3. ↑ Lanosterol synthase is the most accessible enzyme among oxidosqualene cyclases.
    Ref. Corey EJ, Russey WE, Ortiz-de-Montellano PR (1966) 2,3-Oxidosqualene, an intermediate in the biological synthesis of sterols from squalene J Am Chem Soc 88:4750-1
  4. ↑ The cyclization process is stepwise, not concerted as previously thought. As one clue, squalene is not fully folded in the cyclase active site.
    Ref. Reinert DJ, Balliano G, Schulz GE (2004) Conversion of squalene to the pentacarbocyclic hopene. Chem Biol 11:121-6
  5. ↑ The C-17 chain of rotosteryl cation is β-configuration, not α.
    Ref. Corey EJ, Virgil SC (1991) An experimental demonstration of the stereochemistry of enzymic cyclization of 2,3-oxidosqualene to the protosterol system, forerunner of lanosterol and cholesterol. J Am Chem Soc 113:4025-6
  6. ↑ The C-17 chain of dammarenyl cation is β-configuration.
    Ref. Xiong Q, Rocco F, Wilson WK, Xu R, Ceruti M, Matsuda SPT (2005) Structure and reactivity of the dammarenyl cation: configuration transmission in triterpene synthesis. J Org. Chem. 70:5362-75
  7. ↑ Oxygenated protostane are known in Cephalosporium caerulens, Fusidium coccineum, and Aspergillus fumigatus (Ascomycota).
    Ref. Hattori H, Igarashi H, Iwasaki S, Okuda S, (1969) Isolation of 3bhydroxy- 4b-methylfusida-17(20)[16,21-cis],24 diene (3b-hydroxyprotosta- 17(20)[16,21-cis],24 diene) and a related triterpene alcohol Tetrahedron Lett 13, 1023–1026
    Tiwari KP, Choudhary RN (1981) Chemical examination of Wisteria sinensis Proc Natl Acad Sci India A 51, 263–271
  8. ↑ Dammarane derivatives are unusually prevalent in the genus Euphorbia.
  9. ↑ The 21R stereocenter is usually lost in hydride shift.
  10. ↑ C-B-C-C-C rings are very rare and stictanediol from Ascomycota Sticta genus is the sole example.
    Ref. Chin WJ, Corbett RE, Heng CK, Wilkins AL (1973) Lichens and fungi. XI. Isolation and structural elucidation of a new group of triterpenes from Sticta coronata, S. colensoi, and S. flavicans. J Chem Soc Perkin Trans 1:1437–46
  11. ↑ E-ring cyclization precedes D-ring expansion.


Useful Reviews:

  • Xu R, Fazio GC, Matsuda SPT (2004) On the origins of triterpenoid skeletal diversity. Phytochemstry 65:261-291 PMID 14751299

微生物

BACTERIA
squalene
Squalene.png Arrow00r.png
squalene-hopene Arrow00d35.png cyclase[1]
17α-deoxydammarenyl cation[2]


Deoxydammarenyl cation.png

D-ring Arrow00d35.png expansion[3]
Hopyl cation.png
Arrow00d35.png
hopene
Hopene.png
Examples.

Design of Tri-terpene ID numbers ID番号の設計

12-DIGIT

T P 3 x y y r h g n c c
x ... species information
Symbol at x Kingdom Phyla Examples
I Animalia Arthropoda (Insects, crabs) ecdysteroids
V Chordate (Vertebrates) sex steroids, corticosteroids, anabolic steroids
O Others marine steroids
P Plantae Phytosterols lanosterols, cholesterols, brassinolides
S Saponins saponins
F Fungi ergosterols ergosterols
B Bacteria bacterial sterols hopanoids
y ... backbone structure (母核構造) 
Symbol at y Carbons Steroids Backbone Structure
GN C17 gonane Gonane.png
ES C18 estrane Estrane.png
AD C19 androstane Androstane.png
PG C21 pregnane Pregnane.png
CA C24 cholane Cholane.png
CL C27 cholestane Cholestane.png
CM C28 campestane Campestane.png
EG C28 ergostane Ergostane.png
SG C29 (4 rings) stigmastane Stigmastane.png
PR C29 (4 rings) poriferastane Poriferastane.png
Symbol at y Carbons Triterpenoids Backbone Structure
PS C30 protostane Protostane.png
EU C30 euphane Euphane.png
LN C30 lanostane Lanostane.png
CY C30 cycloartane Cycloartane.png
FS C29 fusidane Fusidane.png
HP C30 (5 rings) hopane Hopane.png
FN C30 (5 rings) fernane Fernane.png
CC C30 cucurbitane Cucurbitane.png
DM C30 dammarane Dammarane.png
BC C30 baccharane Baccharane.png
HL C30 holostane Holostane.png
PF C29 (5 rings) pfaffane Pfaffane.png
LP C30 (5 rings) lupane Lupane.png
OL C30 (5 rings) oleanane Oleanane.png
FD C30 (5 rings) friedelane Friedelane.png
TR C30 (5 rings) taraxastane Taraxastane.png
UR C30 (5 rings) ursane Ursane.png
SR C30 (5 rings) serratane Serratane.png


r ... number of major rings (環構造数) 

Click above categories to see details.

h ... hydroxylation pattern (水酸基数) 

Click above categories to see details.

g ... glycosylation pattern(糖修飾パターン) 

Click above categories to see details.

n ... number of sugars (修飾糖数) 

Click above categories to see details.

c ... serial number (通し番号)

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