Category:TP3 - Revision history

Adm: /* {{Bilingual|バクテリア・シダ類のスクアレン環化酵素|Squalene Cyclase in Bacteria and Ferns}} */

2012-12-08T02:55:31Z

‎{{Bilingual|バクテリア・シダ類のスクアレン環化酵素|Squalene Cyclase in Bacteria and Ferns}}

Adm: /* {{Bilingual|真核生物のオキシドスクアレン環化酵素|Oxidosqualene Cyclase in Eukaryotes}} */

2012-12-08T01:31:31Z

‎{{Bilingual|真核生物のオキシドスクアレン環化酵素|Oxidosqualene Cyclase in Eukaryotes}}

Adm: /* {{Bilingual|真核生物のオキシドスクアレン環化酵素|Oxidosqualene Cyclase in Eukaryotes}} */

2012-12-08T00:32:47Z

‎{{Bilingual|真核生物のオキシドスクアレン環化酵素|Oxidosqualene Cyclase in Eukaryotes}}

Adm: /* {{Bilingual|Squalene Cyclase in Bacteria and Ferns|バクテリア・シダ類のスクアレン環化酵素}} */

2011-12-07T12:07:53Z

‎{{Bilingual|Squalene Cyclase in Bacteria and Ferns|バクテリア・シダ類のスクアレン環化酵素}}

Adm: /* {{Bilingual|真核生物のオキシドスクアレン環化酵素|Oxidosqualene Cyclase in Eukaryotes}} */

2011-12-07T12:06:26Z

‎{{Bilingual|真核生物のオキシドスクアレン環化酵素|Oxidosqualene Cyclase in Eukaryotes}}

Adm at 12:01, 7 December 2011

2011-12-07T12:01:48Z

Adm: /* {{Bilingual|Overview|概要}} */

2011-01-07T08:24:02Z

‎{{Bilingual|Overview|概要}}

Adm at 08:23, 7 January 2011

2011-01-07T08:23:16Z

Adm: /* {{Bilingual|Oxidosqualene Cyclase in Eukaryotes|真核生物のオキシドスクアレン環化酵素}} */

2011-01-07T08:22:02Z

‎{{Bilingual|Oxidosqualene Cyclase in Eukaryotes|真核生物のオキシドスクアレン環化酵素}}

Adm at 17:14, 11 December 2010

2010-12-11T17:14:55Z

@@ Line 287: / Line 287: @@
 |style="background-color:#ddf"| hopene<br/>[[Image:Hopene.png|150px]]
 | [[Image:Arrow00l.png]]
-| hopyl cation <br/>[[Image:Hopyl cation.png|150px]]
+| hopyl cation (c-c-c-c)<br/>[[Image:Hopyl cation.png|150px]]
 |}
 {{Twocolumn|
-Hopanoids are widespread: they are found in bacteria, ferns, and geological sediments.
+Hopanoids are widespread: they are found in bacteria, ferns, and geological sediments. They are not found, however, in archaea or animals.
+|
-ホパノイドはバクテリアだけでなく、シダ類や地下堆積物からも見つかっています。
+ホパノイドはバクテリアだけでなく、シダ類や地下堆積物からも見つかっています。しかしアーキアや動物からは見つかっていません。
 }}

@@ Line 178: / Line 178: @@
 |style="background-color:#fdd"| all steroids<br/>lanostane<br/>cycloartane<br/>cucurbitane<br/>ergostane etc.
 |}
-|align="right"|
+|style="vertical-align:bottom"|
-{|
+{| style="margin-left:auto;margin-right:0;"
-|<br/><br/><br/>
-|-
 |style="background-color:#dfd"| baccharane<br/>shionane
 | [[Image:Arrow00l35.png]]
@@ Line 199: / Line 197: @@
 |}
+|
-|align="right"|
-{|
+{| style="margin-left:auto;margin-right:0;"
 | E-ring cyclization<br/>(from 17&alpha;/&beta;)
 | [[Image:Arrow00dl.png]]

@@ Line 139: / Line 139: @@
 | 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|150px]]
 | 1,2-shift<br/>[[Image:Arrow00r.png]]
-| colspan="2" align="left"|lanosteryl cation <small>(C-C-C)</small><br/>[[Image:Lanosteryl cation.png|150px]]
+| colspan="2" align="left"|lanosteryl cation <small>(C-B-C)</small><br/>[[Image:Lanosteryl cation.png|150px]]
 | 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|150px]]
 |-

@@ Line 262: / Line 262: @@
 |}
-==={{Bilingual|Squalene Cyclase in Bacteria and Ferns|バクテリア・シダ類のスクアレン環化酵素}}===
+==={{Bilingual|バクテリア・シダ類のスクアレン環化酵素|Squalene Cyclase in Bacteria and Ferns}}===
 {{Twocolumn|
@@ Line 273: / Line 273: @@
 {| style="text-align:center"
-| squalene<br/>[[Image:squalene.png]]
+| squalene<br/>[[Image:squalene.png|150px]]
 | [[Image:Arrow00r.png]]<br/>squalene-hopene cyclase<ref>SH cyclase is the most investigated enzyme among squalene cyclases. <br/>''Ref.'' Kannenberg EL, Poralla K (1999) Hopanoid biosyntehsis and function in bacteria. ''Naturwissenschaften'' 86:168-76.</ref>
 | 17&alpha;-deoxydammarenyl cation<ref>The C-17 chain of deoxydammarenyl cation is &alpha;-configuration, not &beta; as in eukaryotes.<br/>
-''Ref.'' Wendt KU, Schulz GE, Corey EJ, Liu DR (2000) Enzyme mechanisms for polycyclic triterpene formation. [http://www3.interscience.wiley.com/journal/72515653/abstract?CRETRY=1&SRETRY=0 ''Angew Chem, Int Ed'' 39:2812-33]</ref> <br/>[[Image:Deoxydammarenyl cation.png]]
+''Ref.'' Wendt KU, Schulz GE, Corey EJ, Liu DR (2000) Enzyme mechanisms for polycyclic triterpene formation. [http://www3.interscience.wiley.com/journal/72515653/abstract?CRETRY=1&SRETRY=0 ''Angew Chem, Int Ed'' 39:2812-33]</ref> <br/>[[Image:Deoxydammarenyl cation.png|150px]]
 |-
+|
@@ Line 287: / Line 287: @@
 |}
 |-
-|style="background-color:#ddf"| hopene<br/>[[Image:Hopene.png]]
+|style="background-color:#ddf"| hopene<br/>[[Image:Hopene.png|150px]]
 | [[Image:Arrow00l.png]]
-| hopyl cation <br/>[[Image:Hopyl cation.png]]
+| hopyl cation <br/>[[Image:Hopyl cation.png|150px]]
 |}

@@ Line 139: / Line 139: @@
 | 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|150px]]
 | 1,2-shift<br/>[[Image:Arrow00r.png]]
-| colspan="2"|lanosteryl cation <small>(C-C-C)</small><br/>[[Image:Lanosteryl cation.png|150px]]
+| colspan="2" align="left"|lanosteryl cation <small>(C-C-C)</small><br/>[[Image:Lanosteryl cation.png|150px]]
 | 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|150px]]
 |-

@@ Line 1: / Line 1: @@
 ==Triterpene (C30)==
-=={{Bilingual|Ring configuration|環の構造}}==
+=={{Bilingual|環の構造|Ring configuration}}==
-==={{Bilingual|Steroid|ステロイド}}===
+==={{Bilingual|ステロイド|Steroid}}===
 {{Twocolumn|
 The basic structure is 4 carbon rings, cyclopenta[a]phenanthrene, gonane, or sterane.
@@ Line 48: / Line 48: @@
 </center>
-==={{Bilingual|Triterpenes|トリテルペン}}===
+==={{Bilingual|トリテルペン|Triterpenes}}===
 {{Twocolumn|
@@ Line 56: / Line 56: @@
 }}
-=={{Bilingual|Biosynthesis|生合成}}==
+=={{Bilingual|生合成|Biosynthesis}}==
-==={{Bilingual|Overview|概要}}===
+==={{Bilingual|概要|Overview}}===
 {{Twocolumn|
 The starting point is squalene, which is formed by joining two FPPs tail-to-tail.
@@ Line 90: / Line 90: @@
 <br/>
-==={{Bilingual|Oxidosqualene Cyclase in Eukaryotes|真核生物のオキシドスクアレン環化酵素}}===
+==={{Bilingual|真核生物のオキシドスクアレン環化酵素|Oxidosqualene Cyclase in Eukaryotes}}===
 {{Twocolumn|
 Any path of reactions from the root (2,3-oxidosqualene) to any triterpene backbone with a colored background is catalyzed by a single enzyme called ''oxidosqualene cyclase'' (OSC) or ''terpene synthase h'' (tpsh).<ref>Terpene synthases a-f are responsible for mono-, sesquie- and diterpenes. Tps g is the squalene cyclase.</ref>
@@ Line 100: / Line 100: @@
 {|
 |-
-! {{Bilingual|Backbone Color Code: |骨格色分け: }}
+! {{Bilingual|骨格色分け:|Backbone Color Code:}}
 ! style="background-color:#fdd"| Animals, fungi, and yeast
 ! style="background-color:#dfd"| Plants only
+!
 |-
-! {{Bilingual|Six-membered rings: |6員環表記: }}
+! {{Bilingual|6員環表記:|Six-membered rings:}}
 ! colspan="2" | chair (C), or boat (B)
 |}
@@ Line 137: / Line 137: @@
 |}
 |-
-| 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]]
+| 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|150px]]
 | 1,2-shift<br/>[[Image:Arrow00r.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|150px]]
-| 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]]
+| 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|150px]]
 |-
 |colspan="2"|
@@ Line 173: / Line 173: @@
 |}
 |- valign="top"
-|colspan="2"| cation with the chain at C18 or C17 position<br/>[[Image:CBCC cation.png]]or [[Image:CBCC cation2.png]]
+|colspan="2"| cation with the chain at C18 or C17 position<br/>[[Image:CBCC cation.png|150px]]or [[Image:CBCC cation2.png|100px]]
+|
 {|
@@ Line 185: / Line 185: @@
 | [[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|150px]]
 |-
+|
@@ Line 210: / Line 210: @@
 |}
 |- valign="top"
-| arborinyl cation <small>(C-B-C-C)</small><br/>[[Image:Arborinyl cation.png]]
+| arborinyl cation <small>(C-B-C-C)</small><br/>[[Image:Arborinyl cation.png|150px]]
-| colspan="2" align="left"| unnamed cation <small>(C-B-C-C)</small><br/>[[Image:Hanco cation.png]]
+| colspan="2" align="left"| unnamed cation <small>(C-B-C-C)</small><br/>[[Image:Hanco cation.png|150px]]
-| 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]]
+| 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|150px]]
-| 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]]
+| 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|150px]]
 |-
 |align="left"|
@@ Line 308: / Line 308: @@
 <references/>
-==={{Bilingual|Bis-oxidosqualene Cyclase|ビスオキシドスクアレン環化酵素}}===
+==={{Bilingual|ビスオキシドスクアレン環化酵素|Bis-oxidosqualene Cyclase}}===
 {{Twocolumn|
 Squalene is oxidized by squalene oxidase to become 2,3-oxidosqualene.
@@ Line 331: / Line 331: @@
 <references/>
-=={{Bilingual|Design of Tri-terpene ID numbers|ID番号の設計}}==
+=={{Bilingual|ID番号の設計|Design of Tri-terpene ID numbers}}==
 <center>
 -DIGIT

@@ Line 82: / Line 82: @@
 * バクテリアでは、スクアレンが環化して17&alpha;-ダンマラン型カチオンとなり、最終的にホペン等のトリテルペンになります。
 * 真核生物では、2,3-オキシドスクアレンが環化してプロトステロール型カチオンを作り、プロトンとメチル基の転移 (Wagner-Meerweinシフト) を経て1,2-ラノステロール (動物や真菌類)、シクロアルテノール (植物)や、パルケオール（ナマコ） になります。
-* 植物ではラノステロールからも一部の植物ステロールが合成されます。シロイヌナズナの '''At3g45130''' はラノステロール合成遺伝子であり、オーソログが菊類の [[Species:Taraxacum|''Taraxacum officinale'']] や [[Species:Panax|''Panax ginseng]]、 真正バラ類の [[Species:Luffa|''Luffa cylindrica]] にあることから、真正双子葉類に幅広く見られると考えられます。パーケオールも幅広い植物に見られます。
+* 植物ではラノステロールからも一部の植物ステロールが合成されます。シロイヌナズナの '''At3g45130''' はラノステロール合成遺伝子であり、オーソログが菊類の [[Species:Taraxacum|''Taraxacum officinale'']] や [[Species:Panax|''Panax ginseng'']]、 真正バラ類の [[Species:Luffa|''Luffa cylindrica'']] にあることから、真正双子葉類に幅広く見られると考えられます。パーケオールも幅広い植物に見られます。
 * 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。
 }}

@@ Line 250: / Line 250: @@
 </center>
-{| class="wikitable collapsible collapsed"
+{| class="wikitable collapsible" style="width:100%"
 ! References
 |-

@@ Line 120: / Line 120: @@
 |colspan="2" align="right"|
 {|
-|lanosterol/<br/>cycloartenol<br/>syntase<ref>Lanosterol synthase is the most accessible enzyme among oxidosqualene cyclases, e.g. from mammalian liver or yeast. Cycloartenol synthase is the basic OSC in plants, although lanosterol synthase is also found. For the grouping of cyclases, check Xiong Q et al. (2005) in this page.<br/>''Ref.''
+|lanosterol/<br/>cycloartenol<br/>syntase<ref>Lanosterol synthase is the most accessible enzyme among oxidosqualene cyclases, e.g. from mammalian liver or yeast. Cycloartenol synthase is the basic OSC in plants, although lanosterol synthase is also found. For the grouping of cyclases, check the review by Xiong Q et al. (2005) in this page.<br/>''References.''
 * 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
-* Kolesnikova MD, Xiong Q, Lodeiro S, Hua L, Matsuda SPT (2006) Lanosterol biosynthesis in plants ''Arch Biochem Biophys'' 447:87-95</ref>
+* Kolesnikova MD, Xiong Q, Lodeiro S, Hua L, Matsuda SPT (2006) Lanosterol biosynthesis in plants ''Arch Biochem Biophys'' 447:87-95<br/>
 |[[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>
@@ Line 129: / Line 132: @@
 |align="left"|
 {|
-|lupeol<br/>synthase
+|lupeol/<br/>&beta;-amyrin<br/>synthase<ref>Lupeol synthases are found in [[Species:Glycyrrhiza|''Glycyrrhiza glabra'']], [[Species:Betula|''Betula'' platyphylla]], [[Species:Taraxacum|''Taraxacum officinale'']], and [[Species:Olea|''Olea europea'']]. They form a clade (74-81% identical) that is distinct from other OSCs. Lupeol synthase evolved before the divergence of asterids and eurosids. On the other hand, &beta;-amyrin synthases are considerably more distant (48-50% identical) than are the CAS enzymes (70-79% identical). &beta;-amyrin synthases in eudicotsa nd monocots may have independent origins.<ul><li>Haralampidis K, Bryan G, Qi X, Papadopoulou K, Bakht S, Melton R, Osbourn A (2001) A new class of oxidosqualene cyclases directs synthesis of antimicrobial phytoprotectants in monocots ''Proc Natl Acad Sci U S A'' 98(23):13431-6 <li>Qi X, Bakht S, Leggett M, Maxwell C, Melton R, Osbourn A (2004) A gene cluster for secondary metabolism in oat: implications for the evolution of metabolic diversity in plants ''Proc Natl Acad Sci U S A'' 101(21):8233-8</ul></ref>
 |[[Image:Arrow00dr35.png]]
 |stepwise<br/>cyclization
@@ Line 242: / Line 245: @@
+|
 |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/>
+|style="background-color:#dfd" align="left"| oleanane<ref>&beta;-amyrin has the oleanane skeleton</ref> (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/>
 |}