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==Sphingoid bases==
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
__TOC__
 
 
 
=={{Bilingual|スフィンゴミエリン|Sphingomyelin}}==


{{Twocolumn|
{{Twocolumn|
Sphingoid base is a 2-aminoalkane (or alkene) 1,3-diol with 2R, 3R stereochemistry. Major types are listed as follows. Plants contain desaturated sphingosines, i.g. 4,8-sphingediene (d18:2), and insects contain sphingoid bases of shorter chains, e.g. d14:1 and d16:1.  
Sphingomyelin (SM) is a ceramide linked with phosphocholine, and is found in nerves of vertebrate, especially myelin sheath. The long-chain base of SM is mostly d18:1 and some d18:0, just like glycosphingolipid. Fatty acid components are length 16-24 and hydroxy fatty acids are not included.<ref>Merrill, A.H. "Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics" Chem. Rev. 2011, 111, 6387–6422. PMID 21942574</ref>
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スフィンゴイド塩基は 2-アミノアルカン（アルケン） 1,3-ジオールを指す。代表的なものは以下のとおり。植物は不飽和のスフィンゴシン、例えば　4,8-スフィンゲジエン (d18:2)をもち、昆虫は短い炭素鎖のスフィンゴイド塩基、例えば d14:1, d16:1 を持つ。
スフィンゴミエリン (SM) はセラミドにホスホコリンが結合した構造で、脊椎動物の神経系、特にミエリン鞘に多くあります。SMの長鎖塩基はスフィンゴ糖脂質と同様に d18:1 が多く、 d18:0 も含まれます。脂肪酸は鎖長 16-24 で構成され、ヒドロキシ酸は通常含まれません。
}}
}}


{| class="wikitable"
<table style="border-spacing: 1;">
|-
<tr>
! Name
<td colspan="2"></td>
! Symbol
<td style="transform:scaleY(0.5) translateX(0.9em) translateY(2em);">|</td>
! Abbreviation
<td colspan="2" style="transform: translateX(-0.5em);">OH</td>
! Note
<td></td>
|-
<td style="transform:  translateY(1.5em) translateX(1.2em) rotate(90deg);">=</td>
| sphingosine
<td>O</td>
| d18:1
</tr>
| So
<tr>
<td style="transform:translateY(-0.3em);">(C<sub>14</sub>-chain)</td><td style="transform: rotate(45deg) scaleX(2)">＝</td><td style="transform:scaleX(1.5)">／</td><td style="transform:scaleX(1.5)">＼</td><td style="transform:scaleX(1.5)">／</td><td style="transform:rotate(30deg) translateY(-0.1em) translateX(-0.3em)">ー </td><td>Oー</td><td>Pー</td><td style="color: red;">OCH<sub>2</sub>CH<sub>2</sub><b>N<sup>+</sup>(CH<sub>3</sub>)<sub>3</sub></b></td>
</tr>
<tr><td colspan="3" style="text-align:right; transform:translateX(0.5em);">(fatty acid) ー</td>
<td style="transform: scaleY(0.5) translateX(0.9em) translateY(-2.5em);">|</td>
<td colspan="2" style="transform: translateX(-0.5em);">NH</td>
<td style="transform:scaleY(0.5) translateY(-2em) translateX(2em);">|</td>
<td colspan="2">OH</td>
</tr>
</table>
 
 
===Biosynthesis===
{{Twocolumn|
Sphingomyelin synthase is classified into three groups  (SMS1, SMS2, SMSr), and two of them synthesize SM at Golgi (SMS1) and plasma membrane (SMS2). In mammals, a protein called CERT transports ceramide from ER to Golgi to synthesize SM.
For degradation of SM, many enzymes are known that function in acidic, neutral, or alkaline conditions.<ref>Gault CR, Obeid LM, Hannun YA. "An overview of sphingolipid metabolism: from synthesis to breakdown" Adv Exp Med Biol. 2010;688:1-23. PMID 20919643, Yamaji T, Hanada K. "Sphingolipid metabolism and interorganellar transport: localization of sphingolipid enzymes and lipid transfer proteins" Traffic 2015 16:101-22.PMID 25382749 Zhang Y, Cheng Y, Hansen GH, Niels-Christiansen LL, Koentgen F, Ohlsson L, Nilsson A, Duan RD. "Crucial role of alkaline sphingomyelinase in sphingomyelin digestion: a study on enzymeknockout mice" J Lipid Res. 2011 52:771-81 PMID 21177474</ref>
| SM合成酵素には3種類あり (SMS1, SMS2, SMSr)、そのうちの2種がゴルジ体 (SMS1) と細胞膜 (SMS2) でSMを合成します。哺乳動物ではSM合成時にセラミドを小胞体からゴルジ体に運ぶタンパク質CERTが知られています。SM分解酵素 (SMase) は種類が多く、酸性、中性、アルカリ性で働く酵素があります。
}}
 
;Mammalian SM synthase family (SMS1 in golgi; SMS2 in plasma membrane)
: Phosphatidylcholine + Ceramide &rarr; Sphingomyelin + 1,2-Diacylglycerol
:
;SM degradation (Sphingomyelinase) SMase
: Sphingomyelin &rarr; Ceramide + Phosphocholine
 
===Bioactivity===
{{Twocolumn|
SM involves in cellular absorption of transferrin, cancer, and arterial sclerosis. Niemann-Pick disease type A / B, an inborn metabolic disease, is caused by accumulation of SM through the shortage of acid sphingomyelinase.<ref>Slotte JP. "Biological functions of sphingomyelins" Prog Lipid Res. 2013; 52:424-37.PMID 23684760, Horinouchi K, Erlich S, Perl DP, Ferlinz K, Bisgaier CL, Sandhoff K, Desnick RJ, Stewart CL, Schuchman EH.  "Acid sphingomyelinase deficient mice: a model of types A and B Niemann−Pick disease" Nat Genet. 1995;10:288-93. PMID 7670466</ref>
| SMはトランスフェリンの細胞内吸収、がん、動脈硬化に関係します。先天性代謝異常症のニーマンピック病A型、B型は酸性SMaseの不足によりSMが蓄積する疾患です。
}}
 
<references/>
 
=={{Bilingual|セラミドホスホエタノールアミン|CPE and 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.<ref>Bhat HB, Ishitsuka R, Inaba T, Murate M, Abe M, Makino A, Kohyama-Koganeya A, Kurahashi A, Kishimoto T, Tahara M, Yamamo A, Nagamune K, Hirabayashi Y, Juni N, Umeda M, Fujimori F, Nishibori K, Yamaji A, Greimel P, Kobayashi T,  Evaluation of aegerolysins as novel tools to detect and visualize ceramide phosphoethanolamine, a major sphingolipid in invertebrates, FASEB J. 2015 29:3920-34.PMID 26060215 Hannich JT, Umebayashi K, Riezman H. Distribution and functions of sterols and sphingolipids. Cold Spring Harb Perspect Biol. 2011 3. pii: a004762.PMID 21454248</ref>
 
Ceramide aminoethylphosphonate (CAEP) is similar to CPE but is formed by the C-P bonding. It is found in protozoa, cnidaria, mollusca, and echinodermata.<ref>Hori T, Itasaka O, Inoue H. Biochemistry of shellfish lipid. 3. Purification and elemental analysis of ceramide aminoethylphosphonate from Corbicula complex lipid mixtures. J Biochem. 1966 59:570-3. PMID 5962677</ref>
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|-
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。
| sphinganine = dihydrosphingosine
| d18:0
| Sa or DHSo
| Lacking the trans-double bond of sphingosine
|-
|  4-hydroxysphinganine = phytosphingosine
| t18:0
| Phyto
| Originally found in plants but also in animals
|-
| 6-hydroxysphingosine
| 6-t18:1
|
| Found in skin
|}


====Notation====
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。
{|
}}
|style="background:lightgray"| <font size="+2">d18:1</font>&nbsp;
 
| ''h'', ''d''  or ''t'' stands for single, double, or triple hydroxy groups, respectively.<br/>18 is the carbon chain length.<br/>1 is the number of unsaturated bonds (double bonds).
<table style="border-spacing: 1;">
|}
<tr>
<td colspan="2"></td>
<td style="transform:scaleY(0.5) translateX(0.9em) translateY(2em);">|</td>
<td colspan="2" style="transform: translateX(-0.5em);">OH</td>
<td></td>
<td style="transform:  translateY(1.5em) translateX(1.2em) rotate(90deg);">=</td>
<td>O</td>
</tr>
<tr>
<td style="transform:translateY(-0.3em);">(C<sub>14</sub>-chain)</td><td style="transform: rotate(45deg) scaleX(2)">＝</td><td style="transform:scaleX(1.5)">／</td><td style="transform:scaleX(1.5)">＼</td><td style="transform:scaleX(1.5)">／</td><td style="transform:rotate(30deg) translateY(-0.1em) translateX(-0.3em)">ー </td><td>Oー</td><td>Pー</td><td style="color: red;">OCH<sub>2</sub>CH<sub>2</sub><b>NH<sub>2</sub></b></td>
</tr>
<tr><td colspan="3" style="text-align:right; transform:translateX(0.5em);">(fatty acid) ー</td>
<td style="transform: scaleY(0.5) translateX(0.9em) translateY(-2.5em);">|</td>
<td colspan="2" style="transform: translateX(-0.5em);">NH</td>
<td style="transform:scaleY(0.5) translateY(-2em) translateX(2em);">|</td>
<td colspan="2">OH</td>
</tr>
</table>
 
===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>Ternes P, Brouwers JF, van den Dikkenberg J, Holthuis JC. “Sphingomyelin synthase SMS2 displays dual activity as ceramide phosphoethanolaminesynthase”J Lipid Res. 2009; 50:2270-7. PMID 19454763</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


<references/>


==Ceramides==
=={{bilingual|グリコシルイノシトールホスホセラミド|GIPC}}==


{{Twocolumn|
{{Twocolumn|
The word ceramide (Cer) basically refers to all N-acyl-sphingoid bases, but most representative one is N-acylsphingosines. The conjugated fatty acids are often 16 to 26 carbon chains, but ceramides in skin may contain >30 carbon chains.  
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.  Biochemistry of the sphingolipides. X. Phytoglycolipide, a complex phytosphingosine-containing lipide from plant seeds. Journal of the American Oil Chemists Society 1958 35: 335–343　DOI 10.1007/BF02640547</ref><ref>Carter HE, Kisic A. “Countercurrent distribution of inosol lipids of plant seeds” J Lipid Res. 1969; 10:356-62. PMID 4307829</ref>
Later found in bacteria, protista, 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.<ref>Buré C, Cacas JL, Mongrand S, Schmitter JM  "Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry" Anal Bioanal Chem. 2014 406:995-1010. PMID 23887274</ref><ref>Gronnier J, Germain V, Gouguet P, Cacas JL, Mongrand S. ”GIPC: Glycosyl Inositol Phospho Ceramides, the major sphingolipids on earth”Plant Signal Behav. 2016 2;11(4):e1152438 PMID 27074617</ref>
 
===Classification===
 
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=LBSP3|P3 series]]: Glucuronic acid next to inositol (Plant)
# [[Volatile:ListMol/LBStitle?my_1=LBSP4|P4 series]]: Mannose next to inositol (Fungi)
# [[Volatile:ListMol/LBStitle?my_1=LBSP5|P5 series]]: Others
# (P1 series is sphingomyelin and ceramide phosphoethanolamine.)
|
|
セラミドという言葉は基本的に N-アシルスフィンゴイド塩基を指すが、最も代表的なものは N-アシルスフィンゴシンである。結合する脂肪酸の炭素長は16から26だが、皮膚のセラミドには長さが30以上の場合もある。
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、以前はフィト糖脂質 (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）に存在することがわかり、現在はGIPCと呼ばれます。
セラミドにイノシトールリン酸が結合し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。
 
# イノシトールの次がグルコサミン (原生生物と菌類)
# 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マンノース (菌類)
# その他
}}
}}


{| class="wikitable"
<table style="border-spacing: 1;">
|-
<tr>
!rowspan="2"| Species
<td colspan="2"></td>
!colspan="3"| Glycosylceramide
<td style="transform:scaleY(0.5) translateX(0.9em) translateY(2em);">|</td>
!colspan="3"| Glycosyl inositol phosphoceramide (GIPC)
<td colspan="2" style="transform: translateX(-0.5em);">OH</td>
|-
<td></td>
! Fatty acid
<td style="transform: translateY(1.5em) translateX(1.2em) rotate(90deg);">=</td>
! Long chain base
<td>O</td>
! References
</tr>
! Fatty acid
<tr>
! Long chain base
<td style="transform:translateY(-0.3em);">(C<sub>14</sub>-chain)</td><td style="transform: rotate(45deg) scaleX(2)">＝</td><td style="transform:scaleX(1.5)">／</td><td style="transform:scaleX(1.5)">＼</td><td style="transform:scaleX(1.5)">／</td><td style="transform:rotate(30deg) translateY(-0.1em) translateX(-0.3em)">ー </td><td>Oー</td><td>Pー</td><td style="color: red;">O-Inositol-(sugar chain)</td>
! References
</tr>
|-
<tr><td colspan="3" style="text-align:right; transform:translateX(0.5em);">(fatty acid) ー</td>
|Plants
<td style="transform: scaleY(0.5) translateX(0.9em) translateY(-2.5em);">|</td>
| h16:0 - h26:0<br/>h16:1 - h26:1<br/>h16:0<br/>VLCFA
<td colspan="2" style="transform: translateX(-0.5em);">NH</td>
| d18:2&Delta;4E8E/Z<br/>d18:2&Delta;4E8E/Z<br/>d18:1&Delta;8E/Z<br/>t18:1&Delta;8E/Z
<td style="transform:scaleY(0.5) translateY(-2em) translateX(2em);">|</td>
| <ref name=Mark>Markham JE, Lynch DV, Napier JA, Dunn TM, Cahoon EB. Plant sphingolipids: function follows form. Curr Opin Plant Biol. 2013 16: 350-7. doi: 10.1016/j.pbi.2013.02.009.</ref><ref name="War">Warnecke D, Heinz E..Recently discovered functions of glucosylceramides in plants and fungi. Cell Mol Life Sci. 2003 60:919-41.doi: 10.1007/s00018-003-2243-4.</ref><br/><ref name="Mark"/><ref name="War"/><br/><ref name="Mark"/><br/><ref name="Mark"/><ref name="War"/>
<td colspan="2">OH</td>
| hVLCFA<br/>h14:0 - h26:0<br/>h20:1 - h26:1
</tr>
| t18:1&Delta;8E/Z<br/>t18:1&Delta;8E/Z, t18:0<br/>t18:1&Delta;8E/Z, t18:0
</table>
| <ref name="Mark"/><br/><ref name="Bure">Buré C, Cacas JL, Mongrand S, Schmitter JM. Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry. Anal Bioanal Chem. 2013 doi: 10.1007/s00216-013-7130-8.</ref><br/><ref name="Mark"/><ref name="Bure"/>
 
|-
===Biosynthesis===
|Fungi
;Inositol phosphoceramide synthase (IPCS)<ref>Zhong W, Murphy DJ, Georgopapadakou NH. “Inhibition of yeast inositol phosphorylceramide synthase by aureobasidin A measured by afluorometric assay” FEBS Lett. 1999; 17;463:241-4. PMID 10606729</ref>
| h16:0 - h18:0<br/>h16:1 - h18:1
:Phosphatidylinositol + Ceramide &rarr; Inositol phosphoceramide + Diacylglycerol
| 9-methyl d18:2&Delta;4E,8E<br/>9-methyl d18:2&Delta;4E,8E
 
| <ref name="Nim">Nimrichter L, Rodrigues ML. Fungal glucosylceramides: from structural components to biologically active targets of new antimicrobials. Front Microbiol. 2011 2:212. doi: 10.3389/fmicb.2011.00212.</ref><ref name="War"/><br/><ref name="Nim"/><ref name="War"/>
| h24:0 - h26:0<br/>h24:1 - h26:1<br/>h16:0 - h26:0
| t18:0<br/>t18:0<br/>t18:0, t20:0
| <ref name="Nim"/><br/><ref name="War"/><br/><ref name="War"/><ref name="Bure"/>
|}


<references/>
<references/>
==Sphingolipids in All Kingdoms==
{{:Category:ScientificClassification/LBSC}}

Latest revision as of 05:59, 15 August 2022


Upper classes: LB LBS


Sphingomyelin

Sphingomyelin (SM) is a ceramide linked with phosphocholine, and is found in nerves of vertebrate, especially myelin sheath. The long-chain base of SM is mostly d18:1 and some d18:0, just like glycosphingolipid. Fatty acid components are length 16-24 and hydroxy fatty acids are not included.[1]

スフィンゴミエリン (SM) はセラミドにホスホコリンが結合した構造で、脊椎動物の神経系、特にミエリン鞘に多くあります。SMの長鎖塩基はスフィンゴ糖脂質と同様に d18:1 が多く、 d18:0 も含まれます。脂肪酸は鎖長 16-24 で構成され、ヒドロキシ酸は通常含まれません。

| OH = O
(C14-chain)＝／＼／ー OーPーOCH2CH2N+(CH3)3
(fatty acid) ー | NH | OH


Biosynthesis

Sphingomyelin synthase is classified into three groups (SMS1, SMS2, SMSr), and two of them synthesize SM at Golgi (SMS1) and plasma membrane (SMS2). In mammals, a protein called CERT transports ceramide from ER to Golgi to synthesize SM. For degradation of SM, many enzymes are known that function in acidic, neutral, or alkaline conditions.[2]

SM合成酵素には3種類あり (SMS1, SMS2, SMSr)、そのうちの2種がゴルジ体 (SMS1) と細胞膜 (SMS2) でSMを合成します。哺乳動物ではSM合成時にセラミドを小胞体からゴルジ体に運ぶタンパク質CERTが知られています。SM分解酵素 (SMase) は種類が多く、酸性、中性、アルカリ性で働く酵素があります。

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

Bioactivity

SM involves in cellular absorption of transferrin, cancer, and arterial sclerosis. Niemann-Pick disease type A / B, an inborn metabolic disease, is caused by accumulation of SM through the shortage of acid sphingomyelinase.[3]

SMはトランスフェリンの細胞内吸収、がん、動脈硬化に関係します。先天性代謝異常症のニーマンピック病A型、B型は酸性SMaseの不足によりSMが蓄積する疾患です。

  1. ↑ Merrill, A.H. "Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics" Chem. Rev. 2011, 111, 6387–6422. PMID 21942574
  2. ↑ Gault CR, Obeid LM, Hannun YA. "An overview of sphingolipid metabolism: from synthesis to breakdown" Adv Exp Med Biol. 2010;688:1-23. PMID 20919643, Yamaji T, Hanada K. "Sphingolipid metabolism and interorganellar transport: localization of sphingolipid enzymes and lipid transfer proteins" Traffic 2015 16:101-22.PMID 25382749 Zhang Y, Cheng Y, Hansen GH, Niels-Christiansen LL, Koentgen F, Ohlsson L, Nilsson A, Duan RD. "Crucial role of alkaline sphingomyelinase in sphingomyelin digestion: a study on enzymeknockout mice" J Lipid Res. 2011 52:771-81 PMID 21177474
  3. ↑ Slotte JP. "Biological functions of sphingomyelins" Prog Lipid Res. 2013; 52:424-37.PMID 23684760, Horinouchi K, Erlich S, Perl DP, Ferlinz K, Bisgaier CL, Sandhoff K, Desnick RJ, Stewart CL, Schuchman EH. "Acid sphingomyelinase deficient mice: a model of types A and B Niemann−Pick disease" Nat Genet. 1995;10:288-93. PMID 7670466

CPE and 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.[1]

Ceramide aminoethylphosphonate (CAEP) is similar to CPE but is formed by the C-P bonding. It is found in protozoa, cnidaria, mollusca, and echinodermata.[2]

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。

| OH = O
(C14-chain)＝／＼／ー OーPーOCH2CH2NH2
(fatty acid) ー | NH | OH

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). [3]

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
  1. ↑ Bhat HB, Ishitsuka R, Inaba T, Murate M, Abe M, Makino A, Kohyama-Koganeya A, Kurahashi A, Kishimoto T, Tahara M, Yamamo A, Nagamune K, Hirabayashi Y, Juni N, Umeda M, Fujimori F, Nishibori K, Yamaji A, Greimel P, Kobayashi T, Evaluation of aegerolysins as novel tools to detect and visualize ceramide phosphoethanolamine, a major sphingolipid in invertebrates, FASEB J. 2015 29:3920-34.PMID 26060215 Hannich JT, Umebayashi K, Riezman H. Distribution and functions of sterols and sphingolipids. Cold Spring Harb Perspect Biol. 2011 3. pii: a004762.PMID 21454248
  2. ↑ Hori T, Itasaka O, Inoue H. Biochemistry of shellfish lipid. 3. Purification and elemental analysis of ceramide aminoethylphosphonate from Corbicula complex lipid mixtures. J Biochem. 1966 59:570-3. PMID 5962677
  3. ↑ Ternes P, Brouwers JF, van den Dikkenberg J, Holthuis JC. “Sphingomyelin synthase SMS2 displays dual activity as ceramide phosphoethanolaminesynthase”J Lipid Res. 2009; 50:2270-7. PMID 19454763

GIPC

Glycosyl inositol phosphoceramides (GIPCs) were historically referred to as 'phytoglycolipids' (PGLs) for their abundance in plants and fungi.[1][2] Later found in bacteria, protista, 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.[3][4]

Classification

In LipidBank, we classify GIPC into four types:

  1. P2 series: Glucosamine next to inositol (Fungi and Protista)
  2. P3 series: Glucuronic acid next to inositol (Plant)
  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、以前はフィト糖脂質 (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）に存在することがわかり、現在はGIPCと呼ばれます。 セラミドにイノシトールリン酸が結合し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 (原生生物と菌類)
  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

| OH = O
(C14-chain)＝／＼／ー OーPーO-Inositol-(sugar chain)
(fatty acid) ー | NH | OH

Biosynthesis

Inositol phosphoceramide synthase (IPCS)[5]
Phosphatidylinositol + Ceramide → Inositol phosphoceramide + Diacylglycerol


  1. ↑ Carter HE, Celmer WD, Galanos DS, Gigg RH, Lands EM, Law JH, Mueller KL, Nakayama T, Tomizawa HH, Weber E. Biochemistry of the sphingolipides. X. Phytoglycolipide, a complex phytosphingosine-containing lipide from plant seeds. Journal of the American Oil Chemists Society 1958 35: 335–343　DOI 10.1007/BF02640547
  2. ↑ Carter HE, Kisic A. “Countercurrent distribution of inosol lipids of plant seeds” J Lipid Res. 1969; 10:356-62. PMID 4307829
  3. ↑ Buré C, Cacas JL, Mongrand S, Schmitter JM "Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry" Anal Bioanal Chem. 2014 406:995-1010. PMID 23887274
  4. ↑ Gronnier J, Germain V, Gouguet P, Cacas JL, Mongrand S. ”GIPC: Glycosyl Inositol Phospho Ceramides, the major sphingolipids on earth”Plant Signal Behav. 2016 2;11(4):e1152438 PMID 27074617
  5. ↑ Zhong W, Murphy DJ, Georgopapadakou NH. “Inhibition of yeast inositol phosphorylceramide synthase by aureobasidin A measured by afluorometric assay” FEBS Lett. 1999; 17;463:241-4. PMID 10606729

Sphingolipids in All Kingdoms

The table lists biological species from which sphingolipids were identified. Icons indicate representative species. The icons are used in sphingolipid references together with Synthesis.png for chemical synthesis.

ここに示す分類表にはスフィンゴ脂質が報告された生物が記載されており、アイコンは代表種を表します。スフィンゴ脂質関連の文献にはこれらのアイコンの他、化学合成を表すSynthesis.pngも使われます。

Domain Kingdom Phylum Class Order Model organism Icon Galactosylceramides (GalCer)
(*β configuration unless otherwise state) 		Glucosylceramides (GlcCer)
(*β configuration unless otherwise state) 		Glycosphingolipids
(GSL) 		Ceramide phosphoethanolamine
(CPE) 		Sphingomyelin
(SM) 		Ceramide aminoethylphosphonate
(CAEP) 		Ceramide methylaminoethylphosphonate
(CMAEP) 		Glycosyl inositol phosphoceramides
(GIPC)
ドメイン 界 門 綱 目 モデル生物 Species
(Structure) 		FA, LCB References Species
(Structure) 		FA, LCB References Species
(Structure) 		FA, LCB References Major series Species
(Structure) 		FA, LCB References Species
(Structure) 		FA, LCB References Species
(Structure) 		FA, LCB References Species
(Structure) 		FA, LCB References Species
(Structure) 		FA, LCB References
真正細菌
Bacteria 		バクテロイデス門
Bacteroidetes 		腸内細菌 Bacteria.png Bacteroides
fragilis
(α-GalCer) 		br-h17:0,
br-d17:0 		PubMed Bacteroides
fragilis 		br-h17:0,
br-d17:0 		PubMed Sphingobacterium
spiritivorum
/ATCC33861
(Ins-P-Cer) 		br-15:0,
br-h15:0,
br-d17:0 		PubMed
シアノバクテリア門
Cyanobacteria 		藍色細菌 Scytonema
julianum
(Acetyl-
sphingomyelin) 		15:1,d18:1 PubMed
プロテオバクテリア門
Proteobacteria 		大腸菌 Cystobacter
fuscus
(β-GalCer) 		br-h17:0,
br-d19:2 		DOI Sphingomonas
paucimobilis
(GlcAα-Cer) 		h14:0,d18:0 PubMed Sorangium
cellulosum 		h16:1,
br-h17:1,
h18:1,
br-d21:3,
br-d21:2 		PubMed Bacteriovorax
stolpii 		br-h15:0,
br-15:0,
br-t17:0,
br-d17:0 		PubMed
真核生物
Eukaryota 		原生生物界
Protista 		メタモナーダ門 Metamonada 鞭毛虫 Protista.png Giardia
lamblia 		undescribed PubMed Trichomonas
vaginalis 		16:0,d18:1 PubMed Giardia
lamblia 		16:0,d18:1 DOI
ユーグレノゾア門
Euglenozoa 		Leishmania
amazonensis

Plasmodium
falciparum 		undescribed

h10:0,h120,
d18:0,d20:0 		PubMed

PubMed 		Leishmania
amazonensis
(Galβ1-3Galα1
-4Galβ1
-4Glcβ1-Cer)

Plasmodium
falciparum
(trihexosyl-
ceramide)

Trypanosoma
brucei
(GM3,GM1,
GD1a,GD1b) 		undescribed

h12:0,h14:0,
d18:0,d20:0

undescribed 		PubMed

PubMed

PubMed 		Globo,
a-series,
b-series 		Leishmania
major 		18:0,d16:1 PubMed Plasmodium
falciparum 		undescribed PubMed Trypanosoma
brucei
(Ins-P-Cer) 		16:0,17:0,
18:0 d16:0,
d17:0,d18:1,
d18:0,d19:0,
d20:0,d20:1 		PubMed
(*Procyclic
formのみ)
繊毛虫門
Ciliophora 		繊毛虫 Entodinium
caudatum 		undescribed PubMed Tetrahymena
pyriformis
/WH-14 		16:0,
br-17:0,
br-18:0,
br-h17:0,
h18:0,
br-d17:1,
br-d18:1 		PubMed Tetrahymena
pyriformis
/WH-14 		16:0,
br-18:0,
br-h17:0,
d18:1 		PubMed
植物界
Plantae 		緑藻植物門
Chlorophyta 		クロレラ Plantae.png Pseudococcomyxa
chodatii 		h16:0,h18:0,h20:0,
h22:0,h24:0
d18:2,t18:0,t18:1 		DOI Chlorella
kessleri
(Galα1-4Galβ1
-4Glcβ1-Cer) 		undescribed PubMed Globo Chlorella
variabilis
(Hex(2)-Ins
-P-Cer) 		h24:1, t18:0 Nebraska
Univ.,2015
(*学位論文。
ESI-MS分析,
糖の種類は
Hexとしか
判別できない)
ストレプト植物門
Streptophyta
(*被子植物門を除く) (except Angiosperm) 		緑色植物 Ginkgo
biloba

Stenochlaena
palustris 		h16:0,d18:2

h24:0,d18:2 		DOI

DOI 		Pteridum
aquilinum
(HexNAc-HexA
-(Hex-)Ins
-P-Cer) 		h24:0,t18:0 PubMed
(*MALDI-MS分析,
糖の種類は
Hexとしか
判別できない)
被子植物門
Angiosperm 		シロイヌナズナ Arabidopsis
thaliana 		16:0,h24:1,
d18:1,t18:1 		PubMed Prunus
armeniaca
/kernel 		undescribed J.Chromatogra.,
294,519-524,
1984 		Arabidopsis
thaliana
/leaves
(Glc-GlcA
-Ins-P-Cer) 		h24:0,t18:1 PubMed
菌界
Fungi 		接合菌門
Zygomycota 		ケカビ、クモノスカビ Fungi.png Mucor
hiemalis 		h14:0,h16:0,
br-d19:2,d20:1 		PubMed Mucor
hiemalis
(Galβ1-6Galβ1
-Cer) 		h24:0,h25:0,
h26:0,t18:0 		PubMed Gala PubMed
(*接合菌門に
はGIPC
は含まれ
ない。)
子嚢菌門
Ascomycota 		酵母、コウジカビ Aspergillus
oryzae 		h18:0,br-d19:2 PubMed Aspergillus
oryzae 		h18:0,br-d19:2 PubMed Neurospora
crassa
(Glcα1-2Galβ1-
6Galβ1-6Galβ1-Cer) 		h24:0,t18:0 PubMed Gala Aspergillus
nidulans
(Manα1-3Manα
-2Ins-P-Cer) 		h24:0,t18:0 PubMed
担子菌門
Basidiomycota 		キノコ Cryptococcus
neoformans 		h18:0,br-d19:2 PubMed Cryptococcus
neoformans
(Ins-P-6Manα1
-2Ins-P-Cer) 		undescribed PubMed
動物界
Animalia 		海綿動物門
Porifera 		カイメン Porifera.png Agelas
mauritianus
(α-GalCer)


Chondropsis sp.
(β-GalCer)

h24:0,br-t18:0


h24:0,br-d18:1

DOI


DOI

Haliclona sp. h22:0,t18:1 DOI Amphimedon
viridis
(GlcNAcα1-Cer,
GlcNAcβ1-Cer) 		h22:0,br-t20:1,
h22:0,br-t20:1,
br-t19:0 		DOI Svenzea
zeai
(Arapβ1
-6Ins-P-Cer) 		16:0,
br-16:0,
br-17:0,
d26:1,d26:0 		PubMed
刺胞動物門
Cnidaria 		クラゲ Cnidaria.png Metridium
senile

Sarcophyton ehrenbergi
(α-GlcCer) 		h16:0,h20:0,
br-d19:2

h18:0,br-d19:3 		PubMed

PubMed 		PubMed
(*刺胞動物門はCPEをもたない。) 		PubMed
(*刺胞動物門はSMをもたない。) 		Aurelia
aurita 		14:0,16:0,
d18:1,t18:0 		PubMed Aurelia
aurita 		14:0,16:0,
d18:1,t18:0 		PubMed
    (旧口動物、冠輪)
(Protostomia, Lophotrochozoa) 		扁形動物門
Platyhelminthes 		吸虫綱
Trematoda 		ジストマ Platyhelminthes.png Fasciola
hepatica 		18:0,h18:0,
t18:0,t20:0 		PubMed Fasciola
hepatica

Schistosoma mansoni 		18:0,h18:0,
t18:0,t20:0

h16:0,t18:0,
t20:0 		PubMed

PubMed 		Fasciola
hepatica
(Galα1-4Galβ1
-4-Glcβ1-Cer)

Schistosoma
mansoni
(GalNAcβ1
-4Glcβ1-Cer)

Schistosoma
mansoni
(GM1,GD1a,
GD1b,GT1b) 		undescribed

h16:0,26:0

undescribed 		PubMed

PubMed

DOI 		Globo,
Schisto,
Ganglio,
a-series 		Paramphistomum
cervi 		16:0,18:1 PubMed
渦虫綱
Tubellaria 		プラナリア Dugesia
dorotocephala 		undescribed PubMed
条虫綱
Cestoda 		サナダムシ Diphyllobothrium
hottai 		16:0,18:0,26:0,
28:0,d18:0,
d20:0,t18:0,
t20:0 		PubMed Diphyllobothrium
hottai 		16:0,18:0,
26:0,28:0,
d18:0,d20:0,
t18:0,t20:0 		PubMed Diphyllobothrium
hottai
(Galβ1-4(Fucα1-3)Glcβ1-3Galβ1-Cer)

Spirometra
erinacei
(Galβ1-4(Fucα1-3)Glcβ1-3Galβ1-Cer)

Echinococcus
multilocularis
(GM1,GM3,
GD1a,GM2) 		16:0,18:0,
26:0,28:0,
d18:0,d20:0,
t18:0

18:0,18:1,
d18:0,t18:0

16:0,24:0,
24:1,d18:1 		PubMed

PubMed

PubMed 		Spirometo,
a-series 		Hymenolepis
diminuta 		undescribed PubMed
外肛動物門
Bryozoa 		コケムシ Pectinatella
magnifica 		undescribed DOI Pectinatella
magnifica
(GlcNAcβ1
-4Glcβ1-Cer) 		undescribed DOI
腕足動物門
Brachiopoda 		シャミセンガイ Brachiopoda.png Lingula
unguis 		h16:0,h17:0,
h18:0,d18:1,
d18:3 		DOI Lingula
unguis
(Manα1-3Manβ1
-4Glcβ1-Cer) 		16:0,18:0,
d18:3 		DOI Mollu Lingula
unguis 		16:0,18:0,
h16:0,h18:0,
d18:1,d18:3 		滋賀大学教育学部紀要,自然科学・教育科学,45,31-42,1995
環形動物門
Annelida 		貧毛綱
Oligochaeta 		ミミズ Annelida.png Pheretima
aspergillum 		22:0,24:0,
h22:0,h23:0,
h24:0,br-d18:1,
d18:1,t18:0 		DOI Pheretima
aspergillum 		22:0,24:0,
br-d18:1,
d18:1,
br-d19:1 		DOI Pheretima
aspergillum
(Galβ1-6Galβ1-Cer)

Pheretima
hilgendorfi
(PC-6Galβ1
-6Galβ1-Cer) 		22:0,24:0,
h24:0,
br-d18:1,
d18:1,t18:0

22:0,24:0,
br-d18:1,
br-d19:1 		DOI

PubMed 		Neogala (*環形動物門では
SMは見つからない。)
PubMed
(*SM-Binding Protein, Lyseninはミミズから抽出。)
ヒル綱
Hirudinea 		ヒル Hirudo
nipponica
(β-GalCer) 		16:0,22:0,
24:0,d18:1,
br-d19:1,
d22:3 		DOI Hirudo
nipponica
(Galα1-6Galβ1-Cer,
PC-6Galβ1
-6Galβ1-Cer) 		16:0,22:0,
24:0,d18:1,
br-d19:1,
16:0,22:0,
24:0,t18:0,
br-t19:0,
d22:3 		DOI Isoneogala (*環形動物門ではSMは見つからない。)
多毛綱
Polychaeta 		サシバゴカイ目
Phyllodocida 		イトメ Tylorrhynchus
heterochaetus 		16:0,17:0,
18:0,h16:0,
h17:0 d18:1,
d18:2 		DOI Tylorrhynchus
heterochaetus 		16:0,17:0,
18:0,h16:0,
h17:0 		DOI Tylorrhynchus
heterochaetus
(PC-6Galβ1-Cer) 		16:0,d18:1,
d18:2 		DOI (*環形動物門ではSMは見つからない。) Tylorrhynchus
heterochaetus
(InsMe-P-Cer) 		h16:0,h18:0,
t18:0 		DOI
ケヤリ目
Sabellida 		エラコ Pseudopotamilla
occelata 		16:0,18:0,
h16:0,h18:0,
d18:1 		DOI Pseudopotamilla
occelata 		16:0,18:0,
h16:0,h18:0,
d18:1 		DOI Pseudopotamilla
occelata
(Galα1-4Galβ1-Cer,
Galβ1-4Glcβ1-Cer) 		16:0,18:0,
d18:1,
20:1,22:1,
d18:1 		DOI Gala (*環形動物門ではSMは見つからない。) Pseudopotamilla
occelata
(Ins-P-Cer) 		undescribed DOI
軟体動物門
Mollusca 		二枚貝綱
Bivalvia 		二枚貝 Mollusca.png Hyriopsis
schlegelii
/egg 		14:0,16:0,
h16:0,d18:1,
br-d19:1 		PubMed Hyriopsis
schlegelii
/egg 		14:0,16:0,
h16:0,d18:1,
br-d19:1 		PubMed Hyriopsis
schlegelii
/sperm
(Manα1-3Manβ1
-4Glcβ1-Cer) 		16:0,18:0,
20:0,d18:1,
br-d18:1 		PubMed
PubMed 		Mollu Pinctada
martensii 		h16:0,h18:0,
d18:1,d18:0 		PubMed Pinctada
martensii 		16:0,17:0,
18:0,d16:1,
d18:1,d18:2 		滋賀大学教育学部紀要,自然科学,54,41-48,2004 Hyriopsis
schlegelii
/egg 		15:0,16:0,
d18:1 		DOI Mytilus
galloprovincialis 		16:0,h16:0,
d18:1,t18:0 		PubMed
腹足綱
Gastropoda 		巻貝 Chlorostoma
argyrostoma
turbinatum 		16:0,h16:0,
h18:0,d18:1,
d18:2 		PubMed Euhadra
hickonis 		16:0,h16:0,
br-d19:1,
d18:1 		DOI Chlorostoma
argyrostoma
turbinatum
(Galβ1-6Galβ1-Cer) 		16:0,17:0,
h16:0,h18:0,
d18:1,
br-d18:1,
d18:2,d19:1 		PubMed Neogala Heterogen
longispira 		undescribed PubMed Sinotaia
historica 		undescribed PubMed Monodonta
labio 		undescribed PubMed Monodonta
labio 		undescribed PubMed
頭足綱
Cephalopoda 		イカ、タコ Ommastrephes
sloani pacificus
/sperm 		16:0,18:0,
22:0,22:1,
d16:1 		滋賀大学教育学部紀要,自然科学・教育科学,44,17-23,1994 Ommastrephes
sloani pacificus
/sperm 		16:0,18:0,
22:0,22:1,
d16:1 		滋賀大学教育学部紀要,自然科学・教育科学,44,17-23,1994 Ommastrephes
sloani pacificus
/sperm
(Manβ1-4Manβ1
-4Glcβ1-Cer)

Todarodes
pacificus
(GT3,GQ1c) 		16:0,18:1,
22:1,24:1,
d16:1

undescribed 		滋賀大学教育学部紀要,自然科学・教育科学,44,17-23,1994

PubMed 		c-series Todarodes
pacificu
/viscera 		16:0,18:0,
24:1,d16:1 		滋賀大学教育学部紀要,自然科学,59,29-37,2009 Todarodes
pacificus
/viscera 		16:0,22:1,
24:1,d16:1 		滋賀大学教育学部紀要,自然科学,59,29-37,2009
(旧口動物、脱皮)
(Protostomia, Ecdysozoa) 		線形動物門
Nematoda 		クロマドラ綱
Chromadorea 		回虫 Nematoda.png Ascaris
suum
/adult

Ascaris
suum 		h24:0,br-d17:1,
br-d17:0,
br-t17:0,t18:0 		PubMed

DOI 		Ascaris
suum
(HSO3-3Galβ1-Cer)

Ascaris
suum
/adult
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer)

Ascaris
suum
(PC-6GlcNAcβ1-3Manβ1-4Glcβ1-Cer) 		24:0,h24:0,br-d17:1,
br-d17:0,
br-t18:0

h24:0,br-d17:1,
br-d17:0

h22:0,h24:0,
br-d17:1,
br-d17:0 		PubMed

PubMed

DOI 		Arthro Ascaris
suum 		24:0,h24:0,
br-d17:1,
br-d17:0,
br-t17:0 		DOI Ascaris
suum
(Galα1-
2Ins-P-Cer) 		24:0,h24:0,
br-d17:0,
d18:0 		PubMed
節足動物門 Arthropoda 昆虫綱 Insecta　 ハエ Arthropoda.png Lucilia
caesar
/larvae 		16:0,18:0,
20:0,22:0,
d14:1,d16:1 		PubMed Lucilia
caesar
/larvae
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer) 		16:0,18:0,
20:0,22:0,
d14:1,d16:1 		PubMed Arthro Lucilia
caesar
/pupae 		20:0,22:0 PubMed
(*昆虫綱ではショウジョウバエなど少数の種のみCPEを多くもつ。) 		Aedes
aegypti
/cells 		18:0,20:0,
22:0 		PubMed
(*昆虫綱では多くの種がSMをもつ。)
甲殻亜門
軟甲綱
Crustacea
Malacostraca 		エビ、カニ Penaeus
duorarum
/ventral nerve 		undescribed PubMed Euphausia
superba
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer)

Euphausia
superba
(MAEPn-6Glcβ1-Cer) 		22:1,24:1,
d14:1

22:1,h22:1,
h24:1,d14:1,
br-d18:3,
d18:3 		DOI

PubMed 		Arthro Erimacrus
isenbeckii 		18:0,20:0,
22:0,22:1,
d14:1,d14:0 		滋賀大学教育学部紀要,自然科学,52,9-16,2002
甲殻亜門
鰓脚綱
Crustacea　Branchiopoda 		カブトエビ、ミジンコ Artemia
franciscana 		18:0,22:0,
h18:0,d16:1,
d17:1 		PubMed Artemia
franciscana
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer) 		22:0,d16:1,
d17:1 		PubMed Arthro Artemia
franciscana 		18:0,22:0,
d16:1,d17:1 		PubMed
多足亜門
ヤスデ綱
Myriapoda Diplopoda 		ヤスデ Parafontaria
laminata 		h(2- or 3-hydroxy)23:0,
h(2- or 3-hydroxy)24:0,
d17:1,br-d18:1,
d18:1 		PubMed Parafontaria
laminata
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer) 		22:0,23:0,
24:0,d17:1,
br-d18:1 		PubMed Arthro Parafontaria
laminata 		16:0,17:0,
18:0,22:0,
d17:1,d18:1 		滋賀文化短期大学紀要,3,71-78,1993 Spirostreptus
asthene s
/oocytes 		undescribed DOI
(新口動物)
(Deuterostomia) 		棘皮動物門
Echinodermata 		ウミユリ綱
Crinoidea 		　 ウミユリ Echinodermata.png Comanthus
japonica 		24:0,h18:0,
h22:1,h24:0,
d16:1,d18:2,
t16:0 		PubMed Comanthus
japonica
(Ins-P-Cer) 		22:0,24:0,
d16:1 		DOI
DOI
(*9-O-MeNeuGc
が結合したGIPC
がある。)
DOI
(*9-O-MeNeuAc
が結合したGIPC
がある。)
ヒトデ綱
Asteroidea 		ヒトデ Culcita
novaeguineae 		h22:0,br-t16:0 PubMed Asterias
rubens 		d18:2,d22:1,
d22:2 		PubMed Luidia
maculata
(Galβ1-4Glcβ1-Cer)

Luidia
maculata
((3-sulfo)Galβ1
-4Galβ1
-4Glcβ1-Cer)

Luidia
maculata
(GM3)

Luidia
maculata
(GD3) 		h16:0,h22:0,
h24:0,
br-d19:1,
t16:0,
br-t17:0,
t22:1

h22:0,
br-t19:0

h22:0,t19:0

h22:0,t17:0 		DOI

DOI

DOI

PubMed 		a-series,
b-series 		Distolasterias
nipon 		undescribed DOI
クモヒトデ綱
Ophiuroidea 		クモヒトデ Ophiocoma
scolopendrina
(NeuGcα2
-6Glcβ1-Cer,
GM5,
HSO3-8NeuAcα2
-6Glcβ1-Cer) 		18:0,t18:0,
br-t18:0,
h22:0,t18:0,
br-t18:0 		PubMed Echino
ウニ綱
Echinoidea 		ウニ Anthocidaris
crassispina
/egg 		22:1,24:1,
h22:1,h24:1,
t18:0 		PubMed Anthocidaris
crassispina
/egg
(Galα1-6Glcβ1Cer)

Anthocidaris
crassispina
/egg
(NeuGcα2
-6Glcβ1-Cer,
GM5,
HSO3-8NeuGcα2
-6Glcβ1-Cer) 		22:1,24:1,
h22:1,h24:1,
t18:0

h22:1,h23:1,
h24:1,t18:0 		PubMed

PubMed 		Echino Strongylocentrotus
intermedius 		undescribed DOI
ナマコ綱
Holothuroidea 		ナマコ Bohadschia
argus 		h24:1,d17:1,
br-d17:1 		PubMed Cucumaria
echinata 		h22:0,h23:0,
h24:0,
br-d17:1 		DOI Holothuria
leucospilota
(NeuGcα2
-6Glcβ1-Cer,
GM5) 		h22:0,h23:0,
h24:0,h24:1,
br-t17:0,br-t18:0,
br-t19:0 		DOI Echino
脊索動物門
Chordata 		ホヤ綱
Ascidiacea 		ホヤ Ascidia.png Aplidium
nordmani,
Styela
partita,
Botryllus
leachii 		h24:0,t18:0,
br-t19:0 		DOI Microcosmus
sulcatus
(Galβ1-4(Fucα1
-3)Glcβ1-Cer) 		h22:0,h23:0,
t19:0 		DOI Ciona
intestinalis 		16:0,18:0,
18:1,d16:1,
d18:2 		PubMed
軟骨魚綱
Chondrichthyes 		エイ Chondrichthyes.png Carcharhinus
plumbeus
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		undescribed PubMed Squalus
acanthias
/rectal gland 		undescribed PubMed Bathyraja
smirnovi
(GM2,GD2) 		undescribed PubMed a-series,
b-series 		Torpedo
marmorata
/electric organ 		16:0,24:1,
d18:1 		PubMed
条鰭綱
Actinopterygii 		硬骨魚 Actinopterygii.png Cyprinus
carpio
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		24:1,h24:0 PubMed Theragra
chalcogramm
/brain 		24:1 PubMed Latimeria
chalumnae
(GM3,GD3)

Theragra
chalcogramma
(9-O-Ac-GT3) 		16:0,18:0,
24:1,d18:1

undescribed 		DOI

PubMed 		a-series,
b-series,
c-series 		Latimeria
chalumnae
/brain 		undescribed DOI
両生綱
Amphibia 		カエル Amphibia.png Rana
catesbeiana
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		18:0,24:1,
h24:1,d18:0,
d18:1 		PubMed Bufo
japonicus
/skin 		22:0,24:0,
h22:0,h24:0,
t18:0 		PubMed Rana
pipiens
(GD1b,GT1b) 		undescribed DOI b-series Rana
pipiens
/spinal cord 		undescribed J.Exp.Biol. 29, 203-210, 1952
爬虫綱
Reptilias 		ワニ Reptilia.png Iguana spp.
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		nonhydroxy FA,hydoroxy FA PubMed Anolis
carolinensis
/kidney 		h23:0,h24:0,
h24:1,d18:1 		PubMed Pseudemys
scripta elegans
/brain
(GM1,GD1a,GD1b,
GT1b,GQ1b) 		undescribed PubMed a-series,
b-series 		Tropidurus
torquatus 		undescribed PubMed
鳥綱
Aves 		トリ Aves.png Gallus
gallus domesticus
/sciatic nerve
(Gal-Cer,SO3-3Galβ1-Cer) 		22:0,24:0,
h22:0,h24:0 		PubMed Gallus
gallus
domesticus
/lens 		undescribed PubMed Anser
anser
/brain
(GM1,GD1a,GD1b,
GT1b,GQ1b) 		undescribed PubMed a-series,
b-series 		Colurnba
livia domestica
/liver 		16:0,18:0,
20:4 		PubMed
哺乳綱
Mammalia 		無盲腸目
Eulipotyphla 		モグラ Mammalia.png Suncus
murinus
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		24:0,h24:0,
d18:1 		PubMed Suncus
murinus
/brain 		24:0,h24:0,
d18:1 		PubMed Suncus
murinus
/brain
(GalNAcβ1-4Galβ1
-4Glcβ1-Cer,
GM1,GD1a,GD1b,
GT1b) 		24:0,d18:1 PubMed Ganglio,
a-series,
b-series 		Suncus
murinus
/liver 		undescribed PubMed
食肉目
Carnivora 		ネコ、イヌ Felis
silvestris catus
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		undescribed PubMed Canis
lupus familiaris
/intestine 		20:0,22:0,
24:0,hFA 		PubMed Felis
silvestris catus
/brain
(GM1,GD1a,GD1b,
GT1b,GQ1b) 		undescribed PubMed a-series,
b-series 		Canis lupus
familiaris
/brain 		undescribed PubMed
奇蹄目
Perissodactyla 		ウマ Equus
caballus
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		22:0,24:0,
24:1,h22:0,
h24:0,h24:1,
d18:1 		PubMed Equus
caballus
/spleen 		16:0,22:0,
24:0 		PubMed Equus
caballus
/brain
(GM4,GM3,GM2,
GM1,GD1a,GD1b,
GT1b) 		18:0,20:0,
24:0,h24:0,
h24:1,d18:1,
d20:1 		PubMed a-series,
b-series 		Equus
caballus
/spinal cord 		16:0,18:0,
22:0,24:1 		DOI
鯨偶蹄目
Cetartiodactyla 		ウシ、ブタ Bos
taurus
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		18:0,24:0,
24:1,h18:0,
h24:0,h24:1,
d18:1 		PubMed Bos
taurus
/spleen 		22:0,23:0,
24:0 		PubMed Bos
taurus
/brain
(GM2,GM1,GD3,
GD1a,GD1b) 		undescribed PubMed a-series,
b-series 		Bos
taurus
/brain 		18:0,24:0,24:1,
d18:1 		PubMed Ovis
aries
/brain,
Capra
linnaeus
/brain 		undescribed PubMed
兎目
Lagomorpha 		ウサギ Oryctolagus
cuniculus
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		undescribed PubMed Oryctolagus
cuniculus
/skin fibroblasts 		undescribed PubMed Oryctolagus
cuniculus
/brain
(GM1,GD1a,GD1b,
GT1) 		undescribed PubMed a-series,
b-series 		Oryctolagus
cuniculus
/brain 		undescribed PubMed
齧歯目
Rodentia 		ラット、マウス Rattus
norvegicus
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		undescribed PubMed Mus
musculus
/erythrocytes 		16:0,18:1,
22:0,24:1,
d18:1 		PubMed Rattus
norvegicus
/brain
(GM1,GD1a,GD1b,
GT) 		undescribed PubMed a-series,
b-series 		Rattus
norvegicus
/brain 		undescribed PubMed
霊長目
Primates 		ヒト Primates.png Homo
sapiens
/brain
(Gal-Cer,SO3-3Galβ1-Cer) 		18:0,24:1,
24:0,25:1,
25:0,26:1,
h16:0,h22:0,
h23:0,h24:1,
h24:0 		PubMed Homo
sapiens
/spleen of
Gaucher's
disease

Homo
sapiens
/blood 		22:0,d18:1

undescribed 		PubMed

PubMed 		Homo
sapiens
/brain
(GM1,GD1a,GD1b,
GT1b) 		undescribed PubMed a-series,
b-series 		Homo
sapiens
/brain 		18:0,24:1 PubMed

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