Category:TP5

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(Created page with "==Sesquiterpene (C15)== =={{Bilingual|環の構造|Ring configuration}}== ==={{Bilingual|ゲルマクレン|Germacrane}}=== {{Twocolumn| | }} ==={{Bilingual|セスキテ...")
 
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=={{Bilingual|生合成|Biosynthesis}}==
 
=={{Bilingual|生合成|Biosynthesis}}==
 
==={{Bilingual|概要|Overview}}===
 
==={{Bilingual|概要|Overview}}===
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The starting point is squalene, which is formed by joining two FPPs tail-to-tail.
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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
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2,3-oxidosqualene for cyclization.
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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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<center>
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{| style="text-align:center"
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| [[Image:squalene.png]]
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| [[Image:2,3-oxidosqualene.png]]
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|-
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| squalene
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| 2,3-oxidosqualene
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|}
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</center>
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{{Twocolumn|
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* In bacteria, squalene is cyclized via the 17&alpha;-deoxydammarenyl cation to hopene and other triterpenes.
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* In eukaryotes, 2,3-oxidosqualene is cyclized via the protosteryl cation to lanosterol (animals and fungi), cycloartenol (plants) or parkeol (sea cucumbers) by a series of 1,2-hydride and methyl shifts (Wagner-Meerwein shifts).
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* 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</ref> '''At3g45130''' is lanosterol synthase in ''Arabidopsis'' and its orthologs exist in asterids [[Species:Taraxacum|''Taraxacum officinale'']] and [[Species:Panax|''Panax ginseng]] and eurosid [[Species:Luffa|''Luffa cylindrica]].  Lanosterol synthase exists broadly among eudicots <ref>Kolesnikova MD, Xiong Q, Lodeiro S, Hua L, Matsuda SPT (2006) Lanosterol biosynthesis in plants ''Arch Biochem Biophys'' 447:87-95</ref>. Parkeol is also widespread in plants.
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* In plants, various triterpenes arise from the 17&beta;-dammarenyl cation.
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* 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。
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* 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。
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* 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。
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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。
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}}
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;References
 
;References
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|-
 
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| 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 (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
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|-
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| [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)
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 +
{| class="wikitable"
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| cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
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|}
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|-
 
|}
 
|}
  
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| nerolidyl cation
 
| nerolidyl cation
 
|-
 
|-
|rowspan="14"| &nbsp;
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|rowspan="6"| &nbsp;
 
|-
 
|-
 
| bisabolane
 
| bisabolane
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|-
 
|-
 
| cadinane (nor, seco, bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol)
 
| cadinane (nor, seco, bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol)
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| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane] (iresin, seco, coloratane)
 
|-
 
| [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)
 
 
{| class="wikitable"
 
| cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
 
|}
 
 
 
|-
 
|-
 
| [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)
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| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (isodaucane)
 
| [http://www.sciencedirect.com/science/article/pii/S0031942200903273 daucane] (isodaucane)
 
|-
 
|-
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| drimenyl cation
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| [http://www.sciencedirect.com/science/article/pii/S0040402099002562 drimane] (iresin, seco, coloratane)
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|-
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| illudyl cation
 
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane)
 
| (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane)
 
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|-
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| furodysyl cation
 
| furodysin (furodysinin)
 
| furodysin (furodysinin)
 
|-
 
|-
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| chamigranyl cation
 
| chamigrane (secochamigrane)
 
| chamigrane (secochamigrane)
 
|-
 
|-
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| [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]
 
| [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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|
 
{| class="wikitable"
 
{| class="wikitable"
 
| [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

Revision as of 12:53, 9 December 2011

Contents

Sesquiterpene (C15)

Ring configuration

Germacrane


Sesquiterpenes

Biosynthesis

Overview

References


Sesquiterpene Synthase

farnesyl diphosphate
Arrow00d.png
farnesyl cation
Arrow00d.png
farnesane, acyclic ones
cyclobutane, cyclopentane
cyclofarnesane
germacrane (elemane, 12-6/12-8 germacranolide, furano- nor- homo- seco-germacrane, bicyclogermacrane, lepidozane) [1]
eudesmane (emmotin, oppositane, farfugin, cycloeudesmane, gorgonane, valerane/Jatamansane, spirovetivane (= vetispirane), copaane, others)
eremophilane (furano-, seco-, abeo-, nor-, chiloscyphane, aristolane, nardosinane, brasilane (?), cacalol, page 133 fukinane Petasites japonicus, ishwarane
guaiane (guaianolide, dimer, seco, abeo, xanthane, carabrane, pseudoguaiane, cubebane, ivaxillarane, valerenane)
cycloguaiane (aromadendrane, patchoulane, rotundane, bourbonane)
humulane (caryyllophyllane, bicyclohumulane, africanane)
nerolidyl cation
 
bisabolane
cuparane (herbertane liverwort,fungi, laurane Laurencia spp. (marine), cyclolaurane, trichothecane (from scirpane), gymnomitrane)
cycloheptenyl cation
cadinane (nor, seco, bulgarane,calamenene, muurolane, amorphane, alliacane/primnatriene, oplopane, mutisianthol)
himachalane (lippifoliane, longipinane, longibornane, longifolane)
daucane (isodaucane)
drimenyl cation drimane (iresin, seco, coloratane)
illudyl cation (proto)illudane (illudane, sterpurane, illudalane, isolactarane, merulane, lactarane, marasmane)
furodysyl cation furodysin (furodysinin)
chamigranyl cation chamigrane (secochamigrane)
acorane
Others
pinguisane, picrotoxane, perforane, pacifigorgiane, asteriscane, botrydial


Tricyclic
Cedrane (isocedrane)
Prezizaane (zizaane)


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