Category:LBSP: Difference between revisions

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==Sphingomyelin and Phosphoethanolamine ceramide==
=={{Bilingual|スフィンゴミエリン|Sphingomyelin}}==


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;Mammalian SM synthase family
;Mammalian SM synthase family (SMS1 in golgi; SMS2 in plasma membrane)
: ceramide + phosphatidylcholine ←→ sphingomyelin + 1,2-diacylglycerol
: Phosphatidylcholine + Ceramide → Sphingomyelin + 1,2-Diacylglycerol
: ceramide + phosphatidylethanolamine ←→ PE-ceramide + 1,2-diacylglycerol
 
;Fruitfly CPE synthase
;SM degradation (Sphingomyelinase) SMase
: ceramide + CDP-ethanolamine ←→ PE-ceramide + CMP
: Sphingomyelin → Ceramide + Phosphocholine
 
=={{Bilingual|セラミドホスホエタノールアミン, セラミドアミノエチルホスホン酸|Ceramide phosphoethanolamine (CPE) and ceramide aminoethylphosphonate (CAEP)}}==
 
{{Twocolumn|
Ceramide phosphoethanolamine (CPE) is formed from a ceramide phosphate linked with ethanolamine. It is often found in insects, trace amount in many animals including bacteria, protozoa, and mammals, and absent in plants or fungi. Ceramide aminoethylphosphonate (CAEP) is similar to CPE but is formed by the C-P bonding. It is found in protozoa, cnidaria, mollusca, and echinodermata.
| セラミドホスホエタノールアミン(CPE)はセラミドにリン酸を介してエタノールアミンが結合したものです。昆虫に多く見出されますが、バクテリアから原生生物、哺乳動物まで多くの生物に微量ですが存在します。植物や菌類には見いだされていません。セラミドアミノエチルホスホン酸(CAEP)はCPEと似た構造ですがC-P結合を持ち、原生生物、刺胞動物、軟体動物、棘皮動物などに存在します。
}}
 
==={{Bilingual|生合成|Biosynthesis}}===
 
{{Twocolumn|
There exist three types of sphingomyelin synthase, two of which synthesize CPE. One is SM synthase 2 in cell- and golgi membranes and the other, SM synthase-like protein in the ER lumen (CPE synthase). <ref>Vacaru AM,  Tafesse FG, Ternes P et al. (2009) "Sphingomyelin synthase-related protein SMSr controls ceramide homeostasis in the ER" J Lipid Res 185(6):1013-1027. PMID 19506037</ref>
|スフィンゴミエリン (SM) 合成酵素には3タイプあり、そのうちの2種が CPE を合成します。一つはSM合成酵素SMS2で細胞膜やゴルジ体に存在し、他方は小胞体のスフィンゴミエリン1-関連酵素(SMSr/SAMD8)(CPE synthase)です。
}}
 
;SM synthase 2 family (SMS2)
: phosphatidylethanolamine + ceramide &rarr; CPE + 1,2-diacylglycerol
;CPE synthase (SMS1-related enzyme) SMSr/SAMD8
: CDP-ethanolamine + ceramide &rarr; CPE + CMP


==GIPC==
==GIPC==


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{{Twocolumn|
Glycosyl inositol phosphoceramides (GIPCs) were historically referred to as 'phytoglycolipids' (PGLs), although they are not plant-specific.<ref>Carter HE, Celmer WD, Galanos DS, Gigg RH, Lands EM, Law JH, Mueller KL, Nakayama T, Tomizawa HH, Weber E. 1958. Biochemistry of the sphingolipides. X. Phytoglycolipide, a complex phytosphingosine-containing lipide from plant seeds. Journal of the American Oil Chemists Society 35: 335–343</ref><ref>Carter HE, Brooks S, Gigg RH, Strobach DR, Suami T. 1964. Biochemistry of the sphingolipids. XVI. Structure of phytoglycolipid. Journal of Biological Chemistry 239: 743–746</ref>
Glycosyl inositol phosphoceramides (GIPCs) were historically referred to as 'phytoglycolipids' (PGLs) for their abundance in plants and fungi.<ref>Carter HE, Celmer WD, Galanos DS, Gigg RH, Lands EM, Law JH, Mueller KL, Nakayama T, Tomizawa HH, Weber E. 1958. Biochemistry of the sphingolipides. X. Phytoglycolipide, a complex phytosphingosine-containing lipide from plant seeds. Journal of the American Oil Chemists Society 35: 335–343</ref><ref>Carter HE, Brooks S, Gigg RH, Strobach DR, Suami T. 1964. Biochemistry of the sphingolipids. XVI. Structure of phytoglycolipid. Journal of Biological Chemistry 239: 743–746</ref>
PGL was defined as inositolceramide with hexosamine, and its head-group without hexosamine was called ceramide phosphate polysaccharide (CPPS). The term GIPC was later introduced to cover them.
Later found in bacteria, protozoa, and other animals (except chordata), PGLs are now called GIPCs. The structure is composed of ceramide with inositol phosphate (inositolphosphoceramide, IPC) and different sugars are attached.


In LipidBank, we classify GIPC into four types:
In LipidBank, we classify GIPC into four types:
# [[Volatile:ListMol/LBStitle?my_1=LBSP2|P2 series]]: Glucosamine next to inositol (Fungi and Protista)  
# [[Volatile:ListMol/LBStitle?my_1=LBSP2|P2 series]]: Glucosamine next to inositol (Fungi and Protista) <ref>Cerbón J, Falcon A, Hernández-Luna (2005) "Inositol phosphoceramide synthase is a regulator of intracellular levels of diacylglycerol and ceramide during the G1 to S transition in Saccharomyces cerevisiae" Biochem J. 2005 388(Pt 1):169-176. PMID 15560753</ref>
# [[Volatile:ListMol/LBStitle?my_1=LBSP3|P3 series]]: Glucuronic acid next to inositol (Plant)
# [[Volatile:ListMol/LBStitle?my_1=LBSP3|P3 series]]: Glucuronic acid next to inositol (Plant)<ref>Buré C, Cacas JL, Mongrand S, Schmitter JM (2014) "Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry" Anal Bioanal Chem. 406:995-1010. PMID 23887274</ref>
# [[Volatile:ListMol/LBStitle?my_1=LBSP4|P4 series]]: Mannose next to inositol (Fungi)  
# [[Volatile:ListMol/LBStitle?my_1=LBSP4|P4 series]]: Mannose next to inositol (Fungi)  
# [[Volatile:ListMol/LBStitle?my_1=LBSP5|P5 series]]: Others
# [[Volatile:ListMol/LBStitle?my_1=LBSP5|P5 series]]: Others
# (P1 series is sphingomyelin and phosphoethanolamine ceramide.)
# (P1 series is sphingomyelin and ceramide phosphoethanolamine.)
|
|
糖イノシトールセラミドリン酸 (GIPC) は歴史的にはフィト糖脂質 (PGL) として発見されたが、植物に特異な物質ではない。PGL はセラミドリン酸糖鎖 (CPPS) とよばれる構造の末端にヘキソサミンがつく構造とされ、後に GIPC と呼ばれるようになった。
グリコシルイノシトールホスホセラミド (GIPC) は植物に多く含まれるため、歴史的にフィト糖脂質 (phytoglycolipid, PGL) と呼ばれました。その後、菌類や植物だけでなく、バクテリア、原生生物、動物界(脊索動物は除く)での存在がわかり、現在はGIPCと呼ばれます。
構造はセラミドにイノシトールリン酸がついたイノシトールホスホセラミド(IPC)に、様々な糖がついて伸長します。


LipidBankではGIPCを4つに分類している。
LipidBankではGIPCを4つに分類しています。
# イノシトールの次がグルコサミン (原生動物と菌類)  
# イノシトールの次がグルコサミン (原生動物と菌類)  
# イノシトールの次がグルクロン酸 (植物)
# イノシトールの次がグルクロン酸 (植物)
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# その他
# その他
}}
}}


<references/>
<references/>

Revision as of 22:43, 15 March 2016


Upper classes: LB LBS


Sphingomyelin

In mammalian cells, the major headgroup of ceramides is phosphocholine (producing sphingomyelin), or complex polysaccharides (glycosphingolipids). There are three types of spingomyelin (SM) synthase (SMS1, SMS2, SMSr) and the latter produce ceramide phosphoethanolamine (CPE), whose biochemical function is yet unknown. In Drosophila (fruitfly), the headgroup of ceramides is either phosphoethanolamine or complex polysaccharides, and completely lacks sphingomyelin. It has its own CPE synthase, not homologous to SM synthases.

動物細胞ではセラミドの頭部にホスホコリン(スフィンゴミエリン SM ができる)、または複雑な糖鎖がつく。SM合成酵素には3種類あり、そのうちの2種はホスホエタノールアミンのついたセラミド CPE を合成する。 ショウジョウバエでは、セラミド頭部にホスホエタノールアミンか複雑な糖鎖がつき、スフィンゴミエリンは持たない。独自のCPE合成酵素があり、SM合成酵素とは相同性もない。

Mammalian SM synthase family (SMS1 in golgi; SMS2 in plasma membrane)
Phosphatidylcholine + Ceramide → Sphingomyelin + 1,2-Diacylglycerol
SM degradation (Sphingomyelinase) SMase
Sphingomyelin → Ceramide + Phosphocholine

Ceramide phosphoethanolamine (CPE) and ceramide aminoethylphosphonate (CAEP)

Ceramide phosphoethanolamine (CPE) is formed from a ceramide phosphate linked with ethanolamine. It is often found in insects, trace amount in many animals including bacteria, protozoa, and mammals, and absent in plants or fungi. Ceramide aminoethylphosphonate (CAEP) is similar to CPE but is formed by the C-P bonding. It is found in protozoa, cnidaria, mollusca, and echinodermata.

セラミドホスホエタノールアミン(CPE)はセラミドにリン酸を介してエタノールアミンが結合したものです。昆虫に多く見出されますが、バクテリアから原生生物、哺乳動物まで多くの生物に微量ですが存在します。植物や菌類には見いだされていません。セラミドアミノエチルホスホン酸(CAEP)はCPEと似た構造ですがC-P結合を持ち、原生生物、刺胞動物、軟体動物、棘皮動物などに存在します。

Biosynthesis

There exist three types of sphingomyelin synthase, two of which synthesize CPE. One is SM synthase 2 in cell- and golgi membranes and the other, SM synthase-like protein in the ER lumen (CPE synthase). [1]

スフィンゴミエリン (SM) 合成酵素には3タイプあり、そのうちの2種が CPE を合成します。一つはSM合成酵素SMS2で細胞膜やゴルジ体に存在し、他方は小胞体のスフィンゴミエリン1-関連酵素(SMSr/SAMD8)(CPE synthase)です。

SM synthase 2 family (SMS2)
phosphatidylethanolamine + ceramide → CPE + 1,2-diacylglycerol
CPE synthase (SMS1-related enzyme) SMSr/SAMD8
CDP-ethanolamine + ceramide → CPE + CMP

GIPC

Glycosyl inositol phosphoceramides (GIPCs) were historically referred to as 'phytoglycolipids' (PGLs) for their abundance in plants and fungi.[2][3] Later found in bacteria, protozoa, and other animals (except chordata), PGLs are now called GIPCs. The structure is composed of ceramide with inositol phosphate (inositolphosphoceramide, IPC) and different sugars are attached.

In LipidBank, we classify GIPC into four types:

  1. P2 series: Glucosamine next to inositol (Fungi and Protista) [4]
  2. P3 series: Glucuronic acid next to inositol (Plant)[5]
  3. P4 series: Mannose next to inositol (Fungi)
  4. P5 series: Others
  5. (P1 series is sphingomyelin and ceramide phosphoethanolamine.)

グリコシルイノシトールホスホセラミド (GIPC) は植物に多く含まれるため、歴史的にフィト糖脂質 (phytoglycolipid, PGL) と呼ばれました。その後、菌類や植物だけでなく、バクテリア、原生生物、動物界(脊索動物は除く)での存在がわかり、現在はGIPCと呼ばれます。 構造はセラミドにイノシトールリン酸がついたイノシトールホスホセラミド(IPC)に、様々な糖がついて伸長します。

LipidBankではGIPCを4つに分類しています。

  1. イノシトールの次がグルコサミン (原生動物と菌類)
  2. イノシトールの次がグルクロン酸 (植物)
  3. イノシトールの次がマンノース (菌類)
  4. その他



  1. Vacaru AM, Tafesse FG, Ternes P et al. (2009) "Sphingomyelin synthase-related protein SMSr controls ceramide homeostasis in the ER" J Lipid Res 185(6):1013-1027. PMID 19506037
  2. Carter HE, Celmer WD, Galanos DS, Gigg RH, Lands EM, Law JH, Mueller KL, Nakayama T, Tomizawa HH, Weber E. 1958. Biochemistry of the sphingolipides. X. Phytoglycolipide, a complex phytosphingosine-containing lipide from plant seeds. Journal of the American Oil Chemists Society 35: 335–343
  3. Carter HE, Brooks S, Gigg RH, Strobach DR, Suami T. 1964. Biochemistry of the sphingolipids. XVI. Structure of phytoglycolipid. Journal of Biological Chemistry 239: 743–746
  4. Cerbón J, Falcon A, Hernández-Luna (2005) "Inositol phosphoceramide synthase is a regulator of intracellular levels of diacylglycerol and ceramide during the G1 to S transition in Saccharomyces cerevisiae" Biochem J. 2005 388(Pt 1):169-176. PMID 15560753
  5. Buré C, Cacas JL, Mongrand S, Schmitter JM (2014) "Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry" Anal Bioanal Chem. 406:995-1010. PMID 23887274

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