Category:TP - Revision history

Adm: /* Biosynthesis Overview */

2012-07-05T13:41:46Z

‎Biosynthesis Overview

Adm: /* Biosynthesis Overview */

2012-07-05T07:06:05Z

‎Biosynthesis Overview

Adm: /* Biosynthesis Overview */

2012-07-05T05:38:45Z

‎Biosynthesis Overview

Adm: /* Classification */

2011-05-31T00:33:43Z

‎Classification

Adm: /* Biosynthesis */

2010-12-15T00:11:32Z

‎Biosynthesis

Adm: /* Overview */

2010-08-03T02:42:32Z

‎Overview

Adm: /* Overview */

2010-08-03T02:38:18Z

‎Overview

Adm: /* Biosynthesis Overview */

2010-07-31T09:32:42Z

‎Biosynthesis Overview

Adm: /* Methylerythritol-phosphate (MEP) Pathway */

2010-07-31T06:52:23Z

‎Methylerythritol-phosphate (MEP) Pathway

Adm: /* Terpene biosynthesis */

2010-07-31T06:23:19Z

‎Terpene biosynthesis

@@ Line 140: / Line 140: @@
 一方、MEP経路に関与する酵素群は色素体に存在し、そこでモノテルペン (C10)、ジテルペン (C20)、カロテン (C40)が合成されます。
 }}
+<center>
 <span style="background-color:#dfd">　　　　</span> ... reactions in plastids<br/>
 <span style="background-color:#ddf">　　　　</span> ... reactions in the cytosol & ER<br/>
 {| cellpadding="0" cellspacing="0"
 |-
+|
-|align="center"| C5
+|align="center"| '''C5'''<br/>hemiterpenes
 |align="center"| [[Image:Arrow00l.png]]
 |align="left" colspan="1"| IPP, DMAPP
 |-
-| ||
 |align="center"| +C5 [[Image:Arrow00d35.png]] (h-t)
 |-
 |-
+|
-|style="background-color:#dfd" align="center"| C10
+|style="background-color:#dfd" align="center"| '''C10'''<br/>monoterpenes
 |style="background-color:#dfd" align="center"| [[Image:Arrow00r.png]]
 |style="background-color:#dfd" align="center" colspan="4"| e.g. indole alkaloids, cannabinoids
 |-
-| ||
 |style="background-color:#dfd" align="center"| [[Image:Arrow00d35.png]]
 |style="background-color:#ddf" align="center"| [[Image:Arrow00dr35.png]] +C5 (h-t)
 |-
+|
 |style="background-color:#dfd" align="center"| +C5 [[Image:Arrow00d35.png]](h-t)
-|style="background-color:#ddf" align="center"| C15<br/>sesquiterpenes
+|style="background-color:#ddf" align="center"| '''C15'''<br/>sesquiterpenes
 |style="background-color:#ddf" align="center"| x2<br/>[[Image:Arrow00r.png]]<br/>(t-t)
-|style="background-color:#ddf" align="center"| C30
+|style="background-color:#ddf" align="center"| '''C30'''<br/>triterpenes
 |style="background-color:#ddf" align="center"| [[Image:Arrow00r35.png]]
 |style="background-color:#ddf" align="center"| steroids
 |-
-| ||
 |style="background-color:#dfd" align="center"| +C5 [[Image:Arrow00d35.png]](h-t)
+|
-|valign="top" align="center"| triterpenes
 |-
+|
-|style="background-color:#dfd" align="center"| C20
+|style="background-color:#dfd" align="center"| '''C20'''<br>diterpenes
 |style="background-color:#dfd" align="center"| x2<br/>[[Image:Arrow00r.png]]<br/>(t-t)
-|style="background-color:#dfd" align="center"| C40
+|style="background-color:#dfd" align="center"| '''C40'''<br/>tetraterpenes
 |style="background-color:#dfd" align="center"| [[Image:Arrow00r35.png]]
 |style="background-color:#dfd" align="center"| carotenoids
 |-
-| ||
 |style="background-color:#dfd" align="center"| +C5 [[Image:Arrow00d35.png]](h-t)
+|
-|valign="top" align="center"| tetraterpenes
 |-
+|
-|style="background-color:#dfd" align="center"| C25
+|style="background-color:#dfd" align="center"| '''C25'''<br/>sesterterpenes
 |-
-| ||
 |style="background-color:#dfd" align="center"| [[Image:Arrow00d35.png]]
 |-
+|
-|style="background-color:#dfd" align="center"| C5''n''
+|style="background-color:#dfd" align="center"| '''C5''' ''n'' <br>polyterpenes
 |style="background-color:#dfd" align="center"| [[Image:Arrow00r.png]]
 |style="background-color:#dfd" align="center"| polyprenols, quinones
 |}
-* (h-t) ... head-to-tail conjugation
+</center>
-* (t-t) ... tail-to-tail conjugation
 <references/>

@@ Line 143: / Line 143: @@
 <span style="background-color:#dfd">　　　　</span> ... reactions in plastids<br/>
 <span style="background-color:#ddf">　　　　</span> ... reactions in the cytosol & ER<br/>
-{| cellpadding="0"
+{| cellpadding="0" cellspacing="0"
 |-
 |align="right"| hemiterpenes
@@ Line 165: / Line 165: @@
 |style="background-color:#ddf" align="center"| [[Image:Arrow00dr35.png]] +C5 (h-t)
 |-
-|align="right"| sesquiterpenes
+|
 |style="background-color:#dfd" align="center"| +C5 [[Image:Arrow00d35.png]](h-t)

@@ Line 162: / Line 162: @@
 |-
 | ||
-|style="background-color:#ddf" align="center"| +C5 [[Image:Arrow00d35.png]](h-t)
+|style="background-color:#dfd" align="center"| [[Image:Arrow00d35.png]]
 |-
 |align="right"| sesquiterpenes
+|
-|style="background-color:#ddf" align="center"| C15
+|style="background-color:#dfd" align="center"| +C5 [[Image:Arrow00d35.png]](h-t)
 |style="background-color:#ddf" align="center"| x2<br/>[[Image:Arrow00r.png]]<br/>(t-t)
 |style="background-color:#ddf" align="center"| C30

@@ Line 39: / Line 39: @@
 {{Twocolumn|
 Depending on the number of isoprene units used, terpenoids are classified as follows.
-* hemi-terpenes (C5)
+* '''hemi'''-terpenes (C5)
-* mono- (C10)
+* '''mono'''-terpenes (C10) &sim; 1000
-* sesqui- (C15)
+** essential oils
-* di- (C20)
+* '''sesqui'''-terpenes (C15) &sim; 3000
-* sester- (C25)
+** mostly [[:Category:Asteraceae|Asteraceae]]
-* tri- (C30)
+* '''di'''-terpenes (C20) &sim; 2000
-* tetra- (C40)
+* '''sester'''-terpenes (C25)
-* poly- (C5)<sub>n</sub> (n > 8)
+* '''tri'''-terpenes (C30)
+|
 利用するイソプレン単位の数に応じて、以下のように分類されています。
 * ヘミテルペン　hemi-terpenes (C5)
-* モノ-　mono- (C10)
+* モノテルペン　mono- (C10)
-* セスキ-　sesqui- (C15)
+* セスキテルペン　sesqui- (C15)
-* ジ-　di- (C20)
+* ジテルペン　di- (C20)
-* セスタ-　sester- (C25)
+* セスタテルペン　sester- (C25)
-* トリ-　tri- (C30)
+* トリテルペン　tri- (C30)
-* テトラ-　tetra- (C40)
+* テトラテルペン　tetra- (C40)
-* ポリ-　poly- (C5)<sub>n</sub> (n > 8)
+* ポリテルペン　poly- (C5)<sub>n</sub> (n > 8)
 }}

@@ Line 75: / Line 75: @@
 |}
 </center>
 ===Mevalonate (MVA) Pathway===

@@ Line 17: / Line 17: @@
 </center>
 {{Twocolumn|
-Well known terpenes include myrrh from balm trees, fragrance or essential oils of herbs and roses.  Biologically, terpenes function as volatile expellant of herbivores and attractant of pollinators, or less volatile bitter antifeedants.  Many hormones, pheromones and signal compounds are also derived from terpenes.
+Well known terpenes include myrrh from balm trees, fragrance or essential oils of herbs and roses.  Biologically, terpenes function as volatile expellant of herbivores and attractant of pollinators, or less volatile bitter antifeedants.  Many hormones, pheromones, signal compounds, and rubbers are also derived from terpenes.
+|
 身近なテルペンの具体例として、香木から得られるミルラ（没薬）、ハーブやバラ等のエッセンシャルオイルや香り成分が挙げられます。
 生物学的な機能としては、草食動物の忌避物質、花粉を運ぶ昆虫の誘引物質、苦味成分による摂食阻害物質としても働きます。
-多くのホルモン、フェロモン、シグナル伝達物質がテルペン由来です。
+多くのホルモン、フェロモン、シグナル伝達物質、さらに（イソプレン）ゴムも、テルペン由来です。
 }}

@@ Line 3: / Line 3: @@
 {{Twocolumn|
 Terpenes are present in all living organisms.
-The word 'terpene' originates from turpentine, the distillation of resin from pine trees ([[:Category:Pinaceae|Pinaceae]]).  Chemically speaking, terpenes or terpenoids refer to all natural compounds build up from isoprene (C5, 2-methyl-1,3-butadiene) units.
+The word 'terpene' originates from turpentine, the distillation of resin from pine trees ([[:Category:Pinaceae|Pinaceae]]) whose main ingredients are &alpha;- and &beta;-pinene.  Chemically speaking, terpenes or terpenoids refer to all natural compounds build up from isoprene (C5, 2-methyl-1,3-butadiene) units.
 For this reason, terpenes are also called isoprenoids.
+|
-テルペンは全ての生物中に見出されます。
+テルペンという言葉は松の木の脂を蒸留して得られるテレビン油 (turpentine)に由来しますが （主成分は&alpha;- および &beta;-ピネン）、全ての生物中に見出されます。
-テルペンという言葉は松の木の脂を蒸留して得られるテレビン油 (turpentine)に由来しています。
 化学的には、C5ユニットのイソプレン (2-メチル 1,3-ブタジエン) から構成される天然化合物を全てテルペンまたはテルペノイドと呼びます。
 この理由で、テルペンのことをイソプレノイドとも呼びます。
-<br/>
+}}
-身近な具体例として、香木から得られるミルラ（没薬）、ハーブやバラ等のエッセンシャルオイルや香り成分が含まれます。
+<center>
-生物学的な機能としては、草食動物の忌避物質、花粉を運ぶ昆虫の誘引物質、苦味成分による摂食阻害物質として働きます。
+{|
-多くのホルモン、フェロモン、シグナル伝達物質もテルペン由来です。
+| [[Image:isoprene.png]]<br/>isoprene
 }}

@@ Line 113: / Line 113: @@
 ===Biosynthesis Overview===
 {{Twocolumn|
-Animals and fungi lack the MEP pathway and exclusively utilize the MVA pathway in cytosol <ref>Boucher Y, Doolittle WF “The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways” ''Mol Microbiol'' 37(4):703-716, 2000</ref>.  Plants use both pathways but selectively: IPP is turned into farnesyl diphosphate (C15) in the cytosol and the cytosol/endoplasmic reticulum boundary, and the MVA pathway is largely responsible for sesquiterpenoids (C15), steroids (C30), and triterpenoids (C30) <ref>McGarvey DJ, Croteau R “Terpenoid metabolism” ''Plant Cell'' 7:1015-1026, 1995</ref>.  On the other hands, enzymes related to the MEP pathway exist in plastids, and monoterpenoids (C10), diterpenoids (C20) and carotenoids (C40) are synthesized mainly there <ref>Lichtenthaler HK, Schwender J, Disch A, Rohmer M. “Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway” ''FEBS Lett'' 400(3):271-4, 1997</ref><ref>Turner G, Gershenzon J, Nielson EE, Froehlich JE, Croteau R “Limonene synthase, the enzyme responsible for monoterpene biosynthesis in peppermint, is localized to leucoplasts of oil gland secretory cells” ''Plant Physiol'' 120(3):879-886, 1999</ref>.
+Animals and fungi lack the MEP pathway and exclusively utilize the MVA pathway in cytosol <ref>Boucher Y, Doolittle WF “The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways” ''Mol Microbiol'' 37(4):703-716, 2000</ref>.  Bacteria and plants use both pathways but selectively: IPP is turned into farnesyl diphosphate (C15) in the cytosol and the cytosol/endoplasmic reticulum boundary, and the MVA pathway is largely responsible for sesquiterpenoids (C15), steroids (C30), and triterpenoids (C30) <ref>McGarvey DJ, Croteau R “Terpenoid metabolism” ''Plant Cell'' 7:1015-1026, 1995</ref>.  On the other hands, enzymes related to the MEP pathway exist in plastids, and monoterpenoids (C10), diterpenoids (C20) and carotenoids (C40) are synthesized mainly there <ref>Lichtenthaler HK, Schwender J, Disch A, Rohmer M. “Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway” ''FEBS Lett'' 400(3):271-4, 1997</ref><ref>Turner G, Gershenzon J, Nielson EE, Froehlich JE, Croteau R “Limonene synthase, the enzyme responsible for monoterpene biosynthesis in peppermint, is localized to leucoplasts of oil gland secretory cells” ''Plant Physiol'' 120(3):879-886, 1999</ref>.
+|
-動物と菌類にはMEP経路が無く、細胞質におけるMVA経路を用いてテルペンを合成します。
+動物と真菌類にはMEP経路が無く、細胞質におけるMVA経路を用いてテルペンを合成します。
-植物は両方の経路を持ち、役割分担させています。IPPは細胞質と小胞体との境界部分でファルネシル燐酸 (C15) になり、MVA経路によってセスキテルペン (C15)、ステロイド (C30)、トリテルペンが合成されます。
+バクテリアや植物は両方の経路を持ち、役割分担させています。IPPは細胞質と小胞体との境界部分でファルネシルリン酸 (C15) になり、MVA経路によってセスキテルペン (C15)、ステロイド (C30)、トリテルペンが合成されます。
 一方、MEP経路に関与する酵素群は色素体に存在し、そこでモノテルペン (C10)、ジテルペン (C20)、カロテン (C40)が合成されます。
 }}

@@ Line 98: / Line 98: @@
 ===Methylerythritol-phosphate (MEP) Pathway===
 {{Twocolumn|
-In plants, MVA is synthesized through the methylerythritol phosphate (MEP) pathway.
+In plants, terpenes are synthesized through the methylerythritol phosphate (MEP) pathway.
-This pathway is also referred to as deoxyxylulose phosphate (DXP) or MVA-independent pathway, but the name "MEP" is preferred to specify the isoprenoid biosynthesis, because DXP is also known as a precursor of pyridoxal, the major form of Vitamin B6 in animal tissues (Vitamin B6 includes pyridoxal, pyridoxamine, and pyridoxine and their phosphate forms) <ref>Tambasco-Studart M, Titiz O, Raschle T, Forster G, Amrhein N, Fitzpatrick TB “Vitamin B6 biosynthesis in higher plants” Proc Natl Acad Sci USA 102(38):13687-13692, 2005</ref>.
+This MVA-independent pathway is also referred to as deoxyxylulose phosphate (DXP) or , but the name "MEP" is preferred to specify the terpenoid biosynthesis, because DXP is also known as a precursor of pyridoxal, the major form of Vitamin B6 in animal tissues (Vitamin B6 includes pyridoxal, pyridoxamine, and pyridoxine and their phosphate forms) <ref>Tambasco-Studart M, Titiz O, Raschle T, Forster G, Amrhein N, Fitzpatrick TB “Vitamin B6 biosynthesis in higher plants” Proc Natl Acad Sci USA 102(38):13687-13692, 2005</ref>.
 <br/>
-Acetyl moiety from pyruvic acid is transferred onto D-glyceraldehyde 3-phosphate to form 1-deoxy-D-xylulose 5-phosphate.  Then it undergoes a reverse aldol rearrangement in an enzyme-bound manner to form a branched chain compound, 2-C-methyl-D-erythritol 4-phosphate (MEP).  MEP is attached by cytidine triphosphate (CTP) and its 2-hydroxyl position is phosphorylated, followed by a cyclization into 2-C-methyl-D-erythritol-2,4-cyclophosphate.  IPP and DMAPP are produced from the cyclic anhydride in still unidentified enzymatic steps.
+Acetyl moiety from pyruvic acid is transferred onto D-glyceraldehyde 3-phosphate using a reverse aldol mechanism　in an enzyme-bound fashion to form 1-deoxy-D-xylulose 5-phosphate.  Then it undergoes a Pinacol rearrangement to form a branched chain compound, 2-C-methyl-D-erythritol 4-phosphate (MEP).  MEP is cytidyl-diphosphorylated by CTP and its 2-hydroxyl position is phosphorylated by ATP.  Then cyclization occurs, producing 2-C-methyl-D-erythritol-2,4-cyclophosphate.  IPP and DMAPP are produced from the cyclic anhydride in still unidentified enzymatic steps using NADPH.
+|
+植物において、テルペンはメバロン酸を経由しないメチルエリスリトールリン酸 (MEP)　経路からも合成される。
 }}