lipidbank_wiki - User contributions [en]

Category:LBSB

2022-08-16T01:11:24Z

Yasugi: /* Biosynthesis */

{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}

{{Twocolumn|
Long-chain base (LCB or sphingoid base) is a 2-aminoalkane (or alkene) 1,3-diol. In cells, it constitutes sphingolipids and little exists as a free form.
When LCB is linked with a long-chain fatty acid via an amide bond, it is called a ceramide (Cer).<ref>Yamaji T, Hanada K "Sphingolipid metabolism and interorganellar localization of sphingolipid enzymes and lipid transfer proteins" Traffic 2015 16:101-122. PMID 25382749</ref>
|
長鎖塩基 LCB（またはスフィンゴイド塩基）は 2-アミノアルカン（またはアルケン） 1,3-ジオールを指し、生体内ではスフィンゴ脂質の構成成分です。遊離のLCBは微量しか存在しません。長鎖塩基に長鎖脂肪酸がアミド結合したものを、セラミドと呼びます。
}}
<references/>

==Notation 表記法 ==
{|
|style="background:lightgray" width="200px"| Sph d18:1 
|Sph is an abbreviation of LCB. ''d'' or ''t'' stands for double or triple hydroxy groups, respectively. (We count the terminal alcohol.) 18 is the carbon chain length. 1 after the colon is the number of unsaturated bonds (double bonds).
|width="30%"|
長鎖塩基 LCB は Sph と表します。 ''d'', ''t'' はそれぞれ 2, 3 個の水酸基（アルコールの水酸基含む）を意味し、18は炭素鎖長です。コロンの次にくる1は不飽和結合（二重結合）の数を表します。
|}

{|
|style="background:lightgray" width="200px"| Cer  d18:1Δ8E/20:0 
| Cer is an abbreviations of ceramide. The first part indicates the sphingoid base and the second, after the slash, fatty acid. In this website we do not use superscripts or subscripts for readability. Also we do not italicize E (or trans) and Z (or cis) for the same reason.
|width="30%"| セラミドは　Cer　と表します。左側が長鎖塩基、スラッシュを挟んで右側は脂肪酸を表しています。このサイトでは上付き／下付きは使用せず（見づらいため）、 E (トランス）, Z (シス）もイタリックにしていません。
|}

{| style="border-spacing: 20px;"
|-
! '''Common Name'''
| sphingosine (= (4E)-sphingenine) スフィンゴシン
| sphinganine (= dihydrosphingosine) スフィンガニン
| phytosphingosine (= 4-hydroxydihydrosphingosine) フィトスフィンゴシン
| 6-hydroxysphingosine 6-ヒドロキシスフィンゴシン
|-
! '''Abbreviation'''
| d18:1 or So
| d18:0 or Sa (DHSo)
| t18:0 or Phyto
| t18:1 or 6-t18:1
|-
! '''Structure 構造'''
| {{LBS/Sph|OH}}
| {{LBS/DHSph|OH}}
| {{LBS/PhytoSph|OH}}
| {{LBS/6HSph|OH}}
|-
! '''Source 分布'''
| Major in mammals
| Major in mammals
| Major in fungi and plant
| Found in skin
|}

==Long-chain base 長鎖塩基==

{{Twocolumn|
The structural variation of LCB depends on biological species.<ref>Merrill AH "Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics" Chem. Rev. 2011 111:6387–6422. PMID 21942574</ref>
|生物種によってLCBの構造は大きく異なります。
}}

{| class="wikitable"
! Classification || Long-chain base
|-
| Mammalia || sphingosine (= (4E)-d18:1) (4E)-d20:1 (nerve tissue), t18:0 (intestine)
|-
| Arthropoda || short-chain sphingosine (d14:1, d16:1) <ref>Guan XL, Cestra G, Shui G, Kuhrs A, Schittenhelm RB, Hafen E, van der Goot FG, Robinett CC, Gatti M, Gonzalez-Gaitan M, Wenk MR "Biochemical membrane lipidomics during Drosophila development" Dev Cell 2013 24:98-111. PMID 23260625</ref>
|-
| Plantae || (8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2
|-
| Fungi || 9-methyl (4E,8E)-d18:2, t18:0
|}

===Bioactivity===
{{Twocolumn|
* Free LCB induces apoptosis.<ref>Hung WC, Chang HC, Chuang LY "Activation of caspase-3-like proteases in apoptosis induced by sphingosine and other long-chain bases in Hep3B hepatoma cells" Biochem J. 1999 338:161-166. PMID 9931312</ref>
* Sphingosine 1-phosphate is a lipid mediator of cell proliferation and motility control.<ref>Takabe K, Spiegel S."Export of sphingosine-1-phosphate and cancer progression"J Lipid Res. 2014 55:1839-46. PMID 24474820</ref>
|
* 遊離のLCBはアポトーシスを惹起します。
* スフィンゴシン 1リン酸 (Sph-1-P) は脂質メディエータとして細胞増殖や運動制御に働きます。
}}

<references/>

==Ceramide セラミド==

{{Twocolumn|
The conjugated fatty acids are often length 16 to 26. In normal tissues, little ceramide exists as an intermediate of phospho- and glycosphingolipid, whereas in the skin (corneocyte), ceramides and fatty-acid conjugated acyl-ceramides dominates and exhibit the barrier function.
| セラミドに結合する脂肪酸の炭素鎖長は16から26が多く、通常組織ではスフィンゴリン脂質やスフィンゴ糖脂質の中間体として少量存在します。皮膚の角質層にはセラミドに更に脂肪酸が結合したアシルセラミドがあり、皮膚のバリア機能を担います。
}}

===Composition===
{| class="wikitable"
|-
!rowspan="2"| Species
!colspan="3"| Glycosylceramide
!colspan="3"| Glycosyl inositol phosphoceramide (GIPC)
|-
! Fatty acid
! Long chain base
! References
! Fatty acid
! Long chain base
! References
|-
!Plants
| 16:0 - 26:0 16:1 - 26:1 16:0 VLCFA
| d18:2Δ4E8E/Z d18:2Δ4E8E/Z d18:1Δ8E/Z t18:1Δ8E/Z
| <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. PMID 23499054</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.PMID 12827281</ref> <ref name="Mark"/><ref name="War"/> <ref name="Mark"/> <ref name="Mark"/><ref name="War"/>
| VLCFA 14:0 - 26:0 20:1 - 26:1
| t18:1Δ8E/Z t18:1Δ8E/Z, t18:0 t18:1Δ8E/Z, t18:0
| <ref name="Mark"/> <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 406:995-1010 PMID 23887274</ref> <ref name="Mark"/><ref name="Bure"/>
|-
!Fungi
| 16:0 - 18:0 16:1 - 18:1
| 9-methyl d18:2Δ4E,8E 9-methyl d18:2Δ4E,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.PMID 22025918</ref><ref name="War"/> <ref name="Nim"/><ref name="War"/>
| 24:0 - 26:0 24:1 - 26:1 16:0 - 26:0
| t18:0 t18:0 t18:0, t20:0
| <ref name="Nim"/> <ref name="War"/> <ref name="War"/><ref name="Bure"/>
|}

===Bioactivity===

{{Twocolumn|
* Atopic dermatitis (and dry skin) is associated with a decrease and compositional change of ceramides.<ref>Macheleidt O, Kaiser HW, Sandhoff K "Deficiency of epidermal protein-bound omega-hydroxyceramides in atopic dermatitis" J Invest Dermatol. 2002 119:166-173. PMID 12164940</ref>
* Ceramides involve in cell proliferation and autophagy, and ceramide 1-phosphate functions as a lipid mediator.<ref>Young MM, Kester M, Wang HG "Sphingolipids: regulators of crosstalk between apoptosis and autophagy" J Lipid Res.2013 54:5-19. PMID 23152582</ref>
|
* アトピー性皮膚炎や乾燥肌ではセラミド量が減少し、組成も変化しています。
* 通常細胞内ではLCBと同様に細胞増殖やオートファジーに関与し、セラミド末端にリン酸が結合した Cer-1-P も脂質メディエータとして働きます。
}}

<references/>

===Metabolism===

[[:Category:LBS/Biosynthesis|Metabolism, Glycosphingolipid in Plant and Fungi]]

Category:LBSB

2022-08-16T00:59:54Z

Yasugi: /* Biosynthesis */

{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}

{{Twocolumn|
Long-chain base (LCB or sphingoid base) is a 2-aminoalkane (or alkene) 1,3-diol. In cells, it constitutes sphingolipids and little exists as a free form.
When LCB is linked with a long-chain fatty acid via an amide bond, it is called a ceramide (Cer).<ref>Yamaji T, Hanada K "Sphingolipid metabolism and interorganellar localization of sphingolipid enzymes and lipid transfer proteins" Traffic 2015 16:101-122. PMID 25382749</ref>
|
長鎖塩基 LCB（またはスフィンゴイド塩基）は 2-アミノアルカン（またはアルケン） 1,3-ジオールを指し、生体内ではスフィンゴ脂質の構成成分です。遊離のLCBは微量しか存在しません。長鎖塩基に長鎖脂肪酸がアミド結合したものを、セラミドと呼びます。
}}
<references/>

==Notation 表記法 ==
{|
|style="background:lightgray" width="200px"| Sph d18:1 
|Sph is an abbreviation of LCB. ''d'' or ''t'' stands for double or triple hydroxy groups, respectively. (We count the terminal alcohol.) 18 is the carbon chain length. 1 after the colon is the number of unsaturated bonds (double bonds).
|width="30%"|
長鎖塩基 LCB は Sph と表します。 ''d'', ''t'' はそれぞれ 2, 3 個の水酸基（アルコールの水酸基含む）を意味し、18は炭素鎖長です。コロンの次にくる1は不飽和結合（二重結合）の数を表します。
|}

{|
|style="background:lightgray" width="200px"| Cer  d18:1Δ8E/20:0 
| Cer is an abbreviations of ceramide. The first part indicates the sphingoid base and the second, after the slash, fatty acid. In this website we do not use superscripts or subscripts for readability. Also we do not italicize E (or trans) and Z (or cis) for the same reason.
|width="30%"| セラミドは　Cer　と表します。左側が長鎖塩基、スラッシュを挟んで右側は脂肪酸を表しています。このサイトでは上付き／下付きは使用せず（見づらいため）、 E (トランス）, Z (シス）もイタリックにしていません。
|}

{| style="border-spacing: 20px;"
|-
! '''Common Name'''
| sphingosine (= (4E)-sphingenine) スフィンゴシン
| sphinganine (= dihydrosphingosine) スフィンガニン
| phytosphingosine (= 4-hydroxydihydrosphingosine) フィトスフィンゴシン
| 6-hydroxysphingosine 6-ヒドロキシスフィンゴシン
|-
! '''Abbreviation'''
| d18:1 or So
| d18:0 or Sa (DHSo)
| t18:0 or Phyto
| t18:1 or 6-t18:1
|-
! '''Structure 構造'''
| {{LBS/Sph|OH}}
| {{LBS/DHSph|OH}}
| {{LBS/PhytoSph|OH}}
| {{LBS/6HSph|OH}}
|-
! '''Source 分布'''
| Major in mammals
| Major in mammals
| Major in fungi and plant
| Found in skin
|}

==Long-chain base 長鎖塩基==

{{Twocolumn|
The structural variation of LCB depends on biological species.<ref>Merrill AH "Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics" Chem. Rev. 2011 111:6387–6422. PMID 21942574</ref>
|生物種によってLCBの構造は大きく異なります。
}}

{| class="wikitable"
! Classification || Long-chain base
|-
| Mammalia || sphingosine (= (4E)-d18:1) (4E)-d20:1 (nerve tissue), t18:0 (intestine)
|-
| Arthropoda || short-chain sphingosine (d14:1, d16:1) <ref>Guan XL, Cestra G, Shui G, Kuhrs A, Schittenhelm RB, Hafen E, van der Goot FG, Robinett CC, Gatti M, Gonzalez-Gaitan M, Wenk MR "Biochemical membrane lipidomics during Drosophila development" Dev Cell 2013 24:98-111. PMID 23260625</ref>
|-
| Plantae || (8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2
|-
| Fungi || 9-methyl (4E,8E)-d18:2, t18:0
|}

===Bioactivity===
{{Twocolumn|
* Free LCB induces apoptosis.<ref>Hung WC, Chang HC, Chuang LY "Activation of caspase-3-like proteases in apoptosis induced by sphingosine and other long-chain bases in Hep3B hepatoma cells" Biochem J. 1999 338:161-166. PMID 9931312</ref>
* Sphingosine 1-phosphate is a lipid mediator of cell proliferation and motility control.<ref>Takabe K, Spiegel S."Export of sphingosine-1-phosphate and cancer progression"J Lipid Res. 2014 55:1839-46. PMID 24474820</ref>
|
* 遊離のLCBはアポトーシスを惹起します。
* スフィンゴシン 1リン酸 (Sph-1-P) は脂質メディエータとして細胞増殖や運動制御に働きます。
}}

<references/>

==Ceramide セラミド==

{{Twocolumn|
The conjugated fatty acids are often length 16 to 26. In normal tissues, little ceramide exists as an intermediate of phospho- and glycosphingolipid, whereas in the skin (corneocyte), ceramides and fatty-acid conjugated acyl-ceramides dominates and exhibit the barrier function.
| セラミドに結合する脂肪酸の炭素鎖長は16から26が多く、通常組織ではスフィンゴリン脂質やスフィンゴ糖脂質の中間体として少量存在します。皮膚の角質層にはセラミドに更に脂肪酸が結合したアシルセラミドがあり、皮膚のバリア機能を担います。
}}

===Composition===
{| class="wikitable"
|-
!rowspan="2"| Species
!colspan="3"| Glycosylceramide
!colspan="3"| Glycosyl inositol phosphoceramide (GIPC)
|-
! Fatty acid
! Long chain base
! References
! Fatty acid
! Long chain base
! References
|-
!Plants
| 16:0 - 26:0 16:1 - 26:1 16:0 VLCFA
| d18:2Δ4E8E/Z d18:2Δ4E8E/Z d18:1Δ8E/Z t18:1Δ8E/Z
| <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. PMID 23499054</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.PMID 12827281</ref> <ref name="Mark"/><ref name="War"/> <ref name="Mark"/> <ref name="Mark"/><ref name="War"/>
| VLCFA 14:0 - 26:0 20:1 - 26:1
| t18:1Δ8E/Z t18:1Δ8E/Z, t18:0 t18:1Δ8E/Z, t18:0
| <ref name="Mark"/> <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 406:995-1010 PMID 23887274</ref> <ref name="Mark"/><ref name="Bure"/>
|-
!Fungi
| 16:0 - 18:0 16:1 - 18:1
| 9-methyl d18:2Δ4E,8E 9-methyl d18:2Δ4E,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.PMID 22025918</ref><ref name="War"/> <ref name="Nim"/><ref name="War"/>
| 24:0 - 26:0 24:1 - 26:1 16:0 - 26:0
| t18:0 t18:0 t18:0, t20:0
| <ref name="Nim"/> <ref name="War"/> <ref name="War"/><ref name="Bure"/>
|}

===Bioactivity===

{{Twocolumn|
* Atopic dermatitis (and dry skin) is associated with a decrease and compositional change of ceramides.<ref>Macheleidt O, Kaiser HW, Sandhoff K "Deficiency of epidermal protein-bound omega-hydroxyceramides in atopic dermatitis" J Invest Dermatol. 2002 119:166-173. PMID 12164940</ref>
* Ceramides involve in cell proliferation and autophagy, and ceramide 1-phosphate functions as a lipid mediator.<ref>Young MM, Kester M, Wang HG "Sphingolipids: regulators of crosstalk between apoptosis and autophagy" J Lipid Res.2013 54:5-19. PMID 23152582</ref>
|
* アトピー性皮膚炎や乾燥肌ではセラミド量が減少し、組成も変化しています。
* 通常細胞内ではLCBと同様に細胞増殖やオートファジーに関与し、セラミド末端にリン酸が結合した Cer-1-P も脂質メディエータとして働きます。
}}

<references/>

===Biosynthesis===

[[:Category:LBS/Biosynthesis|Biosynthesis生合成]]

Category:LBSB

2022-08-16T00:53:29Z

Yasugi: /* Ceramide セラミド */

Category:LBSP

2022-08-15T05:59:22Z

Yasugi:

{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
__TOC__

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

{{Twocolumn|
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>
|
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。
}}

<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);">(C14-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;">OCH2CH2N+(CH3)3</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 → Sphingomyelin + 1,2-Diacylglycerol
:
;SM degradation (Sphingomyelinase) SMase
: Sphingomyelin → 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>
|
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。
}}

<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);">(C14-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;">OCH2CH2NH2</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 → CPE + 1,2-diacylglycerol
;CPE synthase (SMS1-related enzyme) SMSr/SAMD8
: CDP-ethanolamine + ceramide → CPE + CMP

<references/>

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

{{Twocolumn|
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.)
|
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
}}

<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);">(C14-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>
</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===
;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>
:Phosphatidylinositol + Ceramide → Inositol phosphoceramide + Diacylglycerol

<references/>

==Sphingolipids in All Kingdoms==

{{:Category:ScientificClassification/LBSC}}

Category:LBSC

2022-08-15T05:50:30Z

Yasugi: /* Cerebrosides in All Kingdoms */

Cerebroside
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
{|
|{{LBS/Cer|O-Glucose}} GlcCer
|{{LBS/Cer|O-Galactose}} GalCer
|-
|colspan=2|
{{Twocolumn|
Monoglycosylceramides (or cerebrosides) are glycosphingolipids where a single sugar is attached to the ceramide structure. Especially, glucopyranose-attached Glucosylceramide (GlcCer) and galactopyranose-attached Galactosylceramide (GalCer) are widely observed in all kingdoms. These ubiquitous molecules are not registered in LipidBank. Instead, we summarize their distribution with bibliographic references with species information.
|
モノグリコシルセラミド (またはセレブロシド) はセラミドに糖が1個エステル結合したスフィンゴ糖脂質です。特にグルコース（ピラノース型）が結合したグルコシルセラミド (GlcCer) とガラクトース（ピラノース型）が結合したガラクトシルセラミド (GalCer) は生物界に広く分布するので、データベース中には掲載せず、ここに解説と生物種ごとの報告例を掲載します。
}}
|}

==Glucosylceramide (GlcCer)==

{{Twocolumn|
GlcCer is widely observed not only in Animal, Plant or Fungi kingdoms, but also in Protozoa Kingdom<ref>Tan RX, Chen JH. "The cerebrosides" Nat Prod Rep. 2003;20:509-34.PMID 14620845, Yu R.K. Yanagisawa M. Ariga T. Glycosphingolipid Structures,in Comprehensive Glycoscience Vol.1,pp. 73-122,doi 10.1016/B978-044451967-2/00003-9, Itonori S, Sugita M. Glycophylogenetic Aspects of Lower Animals. in Comprehensive Glycoscience Vol.3, pp. 253-84, doi 10.1016/B978-044451967-2/00050-7 (J.P. Kamerling, ed.) Elsevier, Oxford (UK). (2007)</ref>. Ceramide structures (hydrocarbon chain length, the number and position of double bonds, existence of hydroxy and other modification groups) may vary, and become complex especially in Plant and Fungi Kingdoms, and Protostomia <ref>Sphingoid base chain may terminate with an isopropyl group in spongia, annelida, echinodermata, and bacteria. Terminal isobutyl or sec-pentyl group has been found only in echinodermata. Methylated or cyclopropane-containing sphingoid base is found in spongia, echinodermata, protochordata, and fungi.</ref>.
In Animal Kingdom, GlcCer is the basic structure for different derivative series such as Globo, Lacto, and Ganglio Series. In Protostomia, GlcCer is the major ceramide in its nerve tissue, e.g. shrimp brain <ref>Okamura N, Stoskopf M, Hendricks F, Kishimoto Y. "Phylogenetic dichotomy of nerve glycosphingolipids" Proc Natl Acad Sci, 1985 82:6779-6782 PMID 3863128 </ref>, and its amide-linked fatty acids do not contain hydroxy groups. GlcCer in plants contains many α-hydroxy fatty acids. In some cold-resistant plants ω9-unsaturated fatty acids are detected. In Mammalia (of Deuterostomia), GlcCer is major in the spleen, blood, and skin.

Gaucher's disease is an inborn metabolic disorder in which GlcCer accumulates in the liver and spleen because of the deficiency of the enzyme glucocerebrosidase to dissociate glucose from the ceramide structure <ref> Brady RO, Kanfer JN, Shapiro D. "Metabolism of glucocerebrosides. II. Evidence of an enzymatic deficiency in Gaucher's desease" Biochem Biophys Res Commun. 1965;18:221-5 PMID 14282020 </ref>.
|
'''GlcCer'''は系統発生的にみると動物の各組織に広く分布するだけでなく、植物界や菌界、原生生物界にも含まれます。セラミド構造（炭化水素の鎖長、二重結合の数と位置、水酸基の有無、修飾基の有無など）の組み合わせは多岐にわたり、特に植物界や菌界、旧口動物のセラミドは複雑です。動物界において、GlcCerはさまざまな糖鎖を持つ糖脂質の基本構造になり、グロボ系列、ラクト系列、ガングリオ系列などが生成されます。旧口（前口）動物の神経系にはGlcCerが多く含まれ（例えばエビ）、セラミド骨格の脂肪酸に水酸基を含みません。対して、植物は α-水酸化の脂肪酸が多く、耐冷性植物の一部からは ω9-不飽和の脂肪酸も見だされています。後口動物の哺乳綱において、GlcCerは、脾臓、血液、皮膚などに多く含まれます。

先天性代謝異常症であるゴーシェ (Gaucher) 病は、GlcCerを分解するグルコセレブロシダーゼが欠損し、肝臓や脾臓にGlcCerが蓄積して発症します。
}}

==Galactosylceramide (GalCer)==
{{Twocolumn|
GalCer has been observed in Eubacterial Domain, but not in Protozoa, Plant, or Fungi (except Ascomycota). It is widely observed in Animal Kingdom, but not in Ecdysozoa (cuticle-shedding animals) of Protostomia. Its ceramide structure differs widely as in GlcCer but not so complex as GlcCer in Plant and Fungi. GalCer is the basic structure for sulfatide (3-O-sulfogalactosylceramide or SM4) and Gala Series often found in Annelida (segmented worm). In Mammalia (of Deuterostomia), GalCer is major in the nerve tissue, especially myelin sheath, whose amido-linked fatty acids are hydroxylated at the C-2 position for more than 50%.

Krabbe disease (globoid cell leukodystrophy) is an inborn metabolic disorder in which a small amount of psychosine (galactosylsphingosine, i.e., the lyso form of GalCer) induces demyelination because of the deficiency of the enzyme galactosylceramidase <ref>Suzuki K. "Globoid cell leukodystrophy (Krabbe's disease): update" J Child Neurol. 2003;18:595-603.PMID 14572137, Suzuki K. "Evolving concept of the pathogenesis of globoid cell leukodystrophy (Krabbe disease)" Proc Jpn Acad Ser B Phys Biol Sci 2003; 79:1-8</ref>. α-GalCer, found from Porifera (marine sponge), in which galactose is α-bonded to ceramide (not the usual β-bond), uniquely binds to human or mouse NKT cells and is considered a potent anti-tumor agent.<ref>Kitamura H, Iwakabe K, Yahata T, Nishimura S, Ohta A, Ohmi Y, Sato M, Takeda K, Okumura K, Van Kaer L, Kawano T, Taniguchi M, Nishimura T. "The natural killer T (NKT) cell ligand alpha-galactosylceramide demonstrates its immunopotentiating effect by inducing interleukin (IL)-12 production by dendritic cells and IL-12 receptor expression on NKT cells" J Exp Med. 1999; 5;189(7):1121-8. PMID 10190903 </ref>
|
'''GalCer'''は真正細菌に存在しますが、原生生物界、植物界、菌界（子嚢菌を除く）では報告がありません。動物界に広く分布しますが旧口動物である脱皮動物には確認されていません。セラミド構造は、GlcCerと同様に多様ですが、植物や菌類のGlcCerほど複雑ではありません。GalCerはスルファチド (3-O-硫酸化ガラクトシルセラミドまたはSM4) や環形動物門に多く含まれるガラ系列の基本構造です。
後口動物である哺乳綱では神経系、特にミエリン鞘にGalCerが多く含まれ、その脂肪酸の50%以上は、C2位が水酸化されています。

クラッベ病（グロボイド細胞ロイコジストロフィー; GLD）はガラクトシルセラミダーゼの欠損により微量のサイコシン（ガラクトシルスフィンゴシン、つまり GalCer のリゾ体）が蓄積して脱髄（ミエリンの破壊）を起こす遺伝性疾患です。また、海綿動物門に発見されたα-GalCerは、ガラクトースがセラミドに（通常のβでなく）α結合しており、ヒトやマウスのNKT細胞に特異的に結合し抗腫瘍効果がみられます。
}}

<references/>

==Cerebrosides in Mammals==

====Lipids in Heart Muscle====

{| class="wikitable collapsible collapsed"
|-
!
! Lipid (% wet weight)
! Phospholipid (% dry weight)
! Phosphatidylethanolamine PE (% dry weight)
! Phosphatidylcholine PC (% dry weight)
! Sphingomyelin (% dry weight)
! '''Cerebroside''' (% dry weight)
! Total cholesterol (% dry weight)
|-
! Human
| 8.3
| 6.3 - 7.5
| 1.4 - 2.8
| 3.3 - 5.7
| 0.2 - 0.5
| -
| -
|-
! Cow
| 3.1 - 19.5
| 7.4 - 11.8
| 5.3
| 4
| 0.5
| 2
| 0.4 (free)
|-
! Rat
| 0.4 - 2.4
| 5 - 8
| 0.84 (% wet)
| 2 (% wet)
| 0.14 (% wet)
| 1.4
| 0.4 - 0.6
|-
|colspan="8"|生化学データブック[I] 14. 臓器・組織の成分、心臓　脂質 p1636 1981 日本生化学会編　東京化学同人　ISBN 978-4-807901-74-6
|}

====Lipids in Rat Testis====
{| class="wikitable collapsible collapsed"
|-
! Fraction
! Total Lipid (mg/mg protein)
! Phosphate (ug/mg protein)
! Phospholipid (% total lipid)
! Neutral Lipid (% total lipid)
! '''Cerebroside''' (% total lipid)
! Sulfated glycolipid (nmol/g total weight)
|-
! Total testis
| 0.40
| 62.88
| 62.9
| 34.6
| 2.5
| 556 ± 34
|-
! Golgi
| 1.26
| 18.49
| 58.3
| 39.4
| 2.3
| -
|-
! Remnant granule
| 0.60
| 19.67
| 29.5
| 68.0
| 2.5
| -
|-
! Microsome
| 0.63
| 53.21
| 83.8
| 14.5
| 1.7
| -
|-
! Lipid corpuscle
| > 19
| 12
| 1.5
| 98.5
| -
| -
|-
|colspan="7"| Keenan TW et al. "Lipid composition of subcellular fractions from rat testis"Biochim Biophys Acta 1972; 270:433-443, PMID 4340988 Suzuki A et al. "Decrease of seminolipid content in the testes of rats with vitamin A deficiency determined by high performance liquid chromatography"J Biochem 1977; 82:461-7 PMID 91479
|}

====Cerebroside and Sulfatide Ratio in Animal Brain ====

{| class="wikitable sortable collapsible collapsed"
|-
! Animal
! Kerasin (GalCer with straight fatty-acyl chain)
! Phrenosin (GalCer with hydroxy fatty-acyl chain)
! Sulfatide
|-
! Human cinerea (gray matter)
| 25
| 52
| 23
|-
! Human alba (white matter)
| 28
| 47
| 25
|-
! Cow cinerea
| 15
| 56
| 29
|-
! Cow alba
| 35
| 48
| 17
|-
! Dog
| 21
| 57
| 22
|-
! Cat
| 21
| 60
| 19
|-
! Mouse (4 weeks)
| 24
| 56
| 20
|-
! Rat (10 days)
| 35
| 42
| 23
|-
! Rat (35 days)
| 21
| 61
| 18
|-
! Rabbit
| 13
| 66
| 21
|-
! Guinea pig
| 28
| 54
| 18
|-
! Sheep
| 27
| 47
| 26
|-
! Chicken
| 44
| 37
| 19
|-
! Tuna
| 50
| 25
| 25
|-
! Shark
| 44
| 24
| 32
|-
| colspan="4" | (weight %) From: Yamakawa T, Nishimura S. "Cerebroside composition in animal brain" Jpn J Exp 1966; 36:101-2 PMID 5297247
|}

====Fatty acid composition of bovine brains====

{| class="wikitable sortable collapsible collapsed"
|-
!colspan="5"| Nonhydroxy fatty acid (adjusted GC peak %)
!colspan="3"| Hydroxy fatty acid
|-
! fatty acid || Ceramide || Sphingomyelin || Cerebroside || Sulfatide || fatty acid || Cerebroside || Sulfatide
|-
|12:0
|colspan="4"| - || 12h:0 || 0.4 || 0.3
|-
|13:0
|colspan="4"| - || 13h:0 || 0.2 || 0.2
|-
| 14:0 || 0.6 || 0.3 || 0.2 || 0.8 || 14h:0 || 0.8 || 3.9
|-
| 15:0 || 0.2 || 0.1 || tr. || 0.3 || 15h:0 || tr. || 0.3
|-
| 16:0 || 4.5 || 5.9 || 3.5 || 4.1 || 16h:0 || 0.1 || 0.7
|-
| 16:1 || 0.4 || tr. || 0.1 || 0.7 || 16h:1 || tr. || 1.7
|-
| 17:0 || tr. || 0.3 || tr. || tr. || 17h:0 || 0.2 || 0.9
|-
| 18:0 || 35.2 || 40.1 || 5.8 || 3.3 || 18h:0 || 16.2 || 12.3
|-
| 18:1 || 2.1 || 0.7 || 2.7 || 5.2 || 18h:1 || - || -
|-
| 19:0 || 0.1 || 0.1 || 0.2 || 0.3 || 19h:0 || 0.4 || 0.3
|-
| 20:0 || 1.0 || 0.4 || 0.6 || 0.3 || 20h:0 || 0.5 || 0.7
|-
| 20:1 || 0.5 || tr. || 0.3 || 0.4 || 20h:1 || - || -
|-
| 21:0 || tr. || tr. || - || - || 21h:1 || - || -
|-
| 22:0 || 3.3 || 3.5 || 3.6 || 3.5 || 22h:0 || 5.8 || 7.7
|-
| 22:1 || 0.5 || 0.6 || 0.6 || 0.6 || 22h:1 || - || -
|-
| 23:0 || 3.7 || 2.8 || 5.2 || 3.1 || 23h:0 || 8.9 || 6.5
|-
| 23:1 || 1.0 || 1.0 || 1.2 || 0.8 || 23h:1 || - || -
|-
| 24:0 || 9.8 || 10.7 || 17.4 || 17.8 || 24h:0 || 30.1 || 26.0
|-
| 24:1 || 18.4 || 24.6 || 39.3 || 39.5 || 24h:1 || 14.6 || 16.7
|-
| 25:0 || 1.4 || 1.5 || 3.6 || 2.2 || 25h:0 || 7.0 || 4.5
|-
| 25:1 || 3.0 || 3.3 || 6.2 || 5.2 || 25h:1 || 3.0 || 2.8
|-
| 26:0 || 2.3 || 0.6 || 1.7 || 2.3 || 26h:0 || 3.9 || 3.8
|-
| 26:1 || 3.6 || 2.6 || 7.6 || 8.5 || 26h:1 || 6.3 || 6.5
|-
| 27:0 || 2.9 || - || - || - || 27h:0 || - || -
|-
| 27:1 || 1.8 || - || tr. || - || 27h:1 || - || -
|-
|colspan="8"| From: O'Brien JS, Rouser G "The fatty acid composition of brain sphingolipids: sphingomyelin, ceramide, cerebroside, and cerebroside sulfate"J Lipid Res1964; 5:339-342.PMID 5873370 Per cent of FA of each column. No PUFA, trace amount of hydroxy FA in ceramide, no hydroxy FA in sphingomyelin. The total ratio of nonhydroxy to hydroxy acids in cerebroside and sulfatide were 42:58 and 77:23, respectively (77:13 in the original paper). Human brain has a similar composition.
|}

==Sphingolipids in All Kingdoms==

{{:Category:ScientificClassification/LBSC}}

==Biosynthesis==

{{Twocolumn|
In Mammalia, GlcCer is synthesized by ceramide glucosyltransferase (CGlcT) at the cytosolic membrane of the Golgi apparatus, and GalCer is synthesized by ceramide galactosyltransferase (CGalT) at the lumen of the endoplasmic reticulum (ER). These enzymes do not share any sequence similarity and CGlcT possesses its transmembrane region at the N-terminal (type III) whereas CGalT possesses it at the C-terminal (type I).<ref>Sprong H, Degroote S, Nilsson T, Kawakita M, Ishida N, van der Sluijs P, van Meer G "Association of the Golgi UDP-galactose transporter with UDP-galactose:ceramide galactosyltransferase allows UDP-galactose import in the endoplasmic reticulum" Mol Biol Cell. 2003;4:3482-93　PMID 12925779</ref>
|
哺乳動物では、ゴルジ装置の細胞質側に局在するグルコシルセラミド合成酵素（CGlcT）によって GlcCer が、小胞体の内腔側に局在するガラクトシルセラミド合成酵素（CGalT）によって GalCer が作られます。これらの酵素は配列相同性が無く、CGlcT は膜貫通領域が N 末端側（III型酵素）、CGalT は C 末端側（I型酵素）です。
}}

{| class="wikitable" style="text-align:center"
|-
!
! GlcCer || GalCer
|-
! Enzyme
| CGlcT (EC 2.4.1.80)
| CGalT (EC 2.4.1.45)
|-
! Reaction
| Ceramide + UDP-glucose → GlcCer + UDP
| Ceramide + UDP-galactose → GalCer + UDP
|-
! Location
| '''Golgi (outside)''' → flipflop → Golgi (inside)
| '''ER lumen'''
|}

{{Twocolumn|
Since all glycolipid synthesizing enzymes (except for CGlcT and CGalT) reside at the lumen of the Golgi apparatus, GlcCer must be flip-flopped from the cytosolic side to the lumen by an eyzyme called flippase.
To synthesize GalCer, UDP-galactose and ceramide must transport the ER membrane. UDP-galactose transporter 2 (UGT2) is considered to be responsible.

GalT can also work on glycerolipid, and synthsizes sulfated glyceroglycolipid in mammalian testis, called seminolipid.
|
CGlcT, CGalT 以外の糖脂質合成酵素はゴルジ装置の内腔側にあり、GlcCer はゴルジ膜の細胞質側から内腔側にフリッパーゼと呼ばれる酵素で移動（フリップフロップ）します。GalCer の場合は、UDPガラクトースとセラミドが小胞体膜を通過します。UDPガラクトーストランスポータ2 (UGT2) が関与するようです。

CGalTはグリセロ脂質にも作用し、精巣の硫酸化グリセロ糖脂質であるセミノリピドも合成します。
}}

<references/>

Category:LBS

2022-08-13T06:00:23Z

Yasugi: /* {{Bilingual|概要|Class Overview}} */

{{Huge|{{Bilingual|スフィンゴ脂質|Sphingolipid}}}}
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
{| style="float:left"
| __TOC__
|}
=={{Bilingual|概要|Class Overview}}==

{{Twocolumn|
Three Sphingolipid categories (LBS) exist in this database.
|このデータベースではスフィンゴ脂質を以下に分けています。
}}

<center>
{|
|-
| style="vertical-align:top" width="33%"|
[[:Category:LBSB| '''Ceramide''']] {{LBS/Cer|OH}} セラミド
| style="vertical-align:top" width="33%"|
'''Glycosphingolipid''' {{LBS/Cer|O-(sugar)}} スフィンゴ糖脂質
| style="vertical-align:top" width="33%"|
[[:Category:LBSP| '''Phosphosphingolipid''']] {{LBS/Cer|O-(phosphate)}} スフィンゴリン脂質
|-
|
*[[:Category:LBSB|Long-chain base and ceramide]]
|
*[[:Category:LBSC|Cerebroside (monohexosyl ceramides)]]
*[[:Category:LBSG|Acidic glycosphingolipid]]
|
*[[:Category:LBSP|Sphingomyelin, CPE, CAEP and GIPC]]
|}
</center>

<center>
{| class="wikitable"
|<big>
[[:Category:LBS/Search|{{Bilingual|スフィンゴ脂質検索画面にいく|Go to Sphingolipid search.}}]]
</big>
|}
</center>

==={{Bilingual|スフィンゴ脂質の歴史|History of Sphingolipids}}===
{{Twocolumn|
Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure.<ref>Thudichum J.L.W. "A Treatise on the Chemical Constitution of the Balliere" Tindall and Cox, London, 1884</ref> The basic structure is a long-chain base (long-chain amino-alcohol) whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides.
Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (oligo)saccharides, respectively. Phosphosphingolipid includes sphingomyelin, and glycosphingolipid, cerebrosides and gangliosides. Both are abundant in neural tissues.<ref>Gault CR, Obeid LM, Hannun YA "An overview of sphingolipid synthesis to breakdown" Adv Exp Med Biol. 2010;688:1-23. PMID 20919643</ref>
|
スフィンゴ脂質は J.L.W. Thudichum (1829-1901) により機能や構造未知の脂質として脳から見いだされました。基本骨格は長鎖塩基 (長鎖アミノアルコール) のアミノ基が長鎖脂肪酸とアミド結合したもので、セラミドと呼ばれます。
スフィンゴ脂質はセラミドにリン酸が結合したスフィンゴリン脂質と糖が結合したスフィンゴ糖脂質に分けられます。スフィンゴリン脂質にはスフィンゴミエリンが、スフィンゴ糖脂質にはセレブロシドやガングリオシドなどが含まれ、いずれも神経系に多く存在します。
}}

<references/>

=={{Bilingual|スフィンゴ脂質|Sphingolipid}}==

==={{Bilingual|表記法|Notation}}===
{| class="wikitable collapsible collapsed" style="width:80%"
!colspan="4" align="center" style="background:lightgray"| Symbol Abbreviations (e.g. Glc = glucose)
|-
!colspan="4" align="center" style="background:lightgray"| Backbones
{{#repeatnum:LBS/AbbrevRow|1|
Cer && ceramide && セラミド &&
Sph && sphingosine && スフィンゴシン &&
}}
|-
!colspan="4" align="center" style="background:lightgray"| Sugars
{{#repeatnum:LBS/AbbrevRow|1|
Glc && glucose && グルコース && C6H12O6 &&
Gal && galactose && ガラクトース && C6H12O6 &&
GlcNAc && ''N''-acetyl-glucosamine && ''N''-アセチルグルコサミン && C8H15NO6
GalNAc && ''N''-acetyl-galactosamine && ''N''-アセチルガラクトサミン && C8H15NO6
GlcN && glucosamine && グルコサミン && C6H13NO5
GalN && galactosamine && ガラクトサミン && C6H13NO5
GlcA && glucuronic acid && グルクロン酸 && C6H10O7
GalA && galacturonic acid && ガラクツロン酸 && C6H10O7 &&
Man && mannose && マンノース && C6H12O6 && 18950
Rha && rhamnose (= 6-deoxy-mannose) && ラムノース (6-デオキシマンノース) && C6H12O5 && 19233
Ins && inositol && イノシトール && C6H12O6 && 892
Fuc && fucose (= 6-deoxy-galactose) && フコース (6-デオキシガラクトース) && C6H12O5 && 17106
Ara && arabinose && アラビノース && C5H10O5 && 5460291
Xyl && xylose && キシロース && C5H10O5 && 135191
NeuNH && (deacetyl) neuraminic acid (pyruvate + mannosamine) && ノイラミン酸 (ピルビン酸＋マンノサミン) && C9H17N1O8 && 513472
NeuAc && ''N''-acetyl-neuraminic acid && ''N''-アセチルノイラミン酸 && C11H19NO9 && 439197
NeuGc && ''N''-glycolyl-neuraminic acid && ''N''-グリコリルノイラミン酸 && C11H19NO10 && 123802
Kdn && 2-keto-3-deoxy-D-glycero- D-galacto-nononic acid && デアミノノイラミン酸 && C9H16O9 && 13991616
}}
|-
!colspan="4" align="center" style="background:lightgray"| Modifiers
{{#repeatnum:LBS/AbbrevRow|1|
AEPn && aminoethylphosphonic acid, or (2-aminoethyl)hydroxyphosphoryl- && アミノエチルホスホン酸（C-P結合）
MAEPn && ''N''-methyl aminoethylphosphonic acid, or (''N''-methyl-2-aminoethyl) hydroxyphosphoryl- && AEPnの''N''-メチル体（C-P結合）
EtnP && phosphoethanolamine (PEA), or 2-aminoethanolphospho- && ホスホエタノールアミン
PC && Phosphocholine && ホスホコリン
Butenyl && Butenyl && ブテニル基
Me && Methyl && メチル基
Et && Ethyl && エチル基
}}
|}

==={{Bilingual|分類体系|Page/ID-Code Design}}===
{{Twocolumn|
Major series of phosphosphingolipids are determined by molecules bound to their phosphates, and the series of glycosphingolipids are determined by oligosaccharides bound to their ceramides. The IUPAC series of glycosphingolipids (1977) were based on the order and bonding patterns of four sugars rooting at the long-chain base. Our series, however, are based on three sugars. Two original series, Echino and Schisto, are also added.
|スフィンゴリン脂質はリン酸に結合する分子や糖の種類、スフィンゴ糖脂質はセラミドに結合する糖鎖により系列を作成しています。1977年にIUPACが提唱したスフィンゴ糖脂質の系列は、長鎖塩基に結合する四糖の並びと結合を基準にしています。ここではより広い糖鎖の系列を検索できるよう、三糖を基準に分類しています。また新たにEchinoとSchistoの系列を加えています。
}}

{|
|
<table border=1>
<tr>
<td style="background-color:yellowgreen;" width=20px align="center"><big>L</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>B</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>S</big>
<td style="background-color:green;" width=20px align="center"><big>''G/P''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s1''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s2''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n1''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n2''</big>
<td style="background-color:firebrick; color:white" width=20px align="center"><big>''y''</big>
<td style="background-color:white;" width=20px align="center"><big>''c1''</big>
<td style="background-color:white;" width=20px align="center"><big>''c2''</big>
</tr>
</table>
|  
|
{| class="wikitable"
! '''G/P''' || '''G''' (glyco) || '''P''' (phospho)
|-
! '''s1, s2'''
|colspan="3"| structure code as explained below
|-
! '''n1, n2'''
|colspan="2"| number of sugars (2 digits)
|-
! '''y'''
|colspan="2"| number of sialic acids (1 digit)
|-
! '''c1, c2'''
|colspan="2"| serial numbers
|}
|}

==={{Bilingual|スフィンゴ糖脂質１文字目|First (s1) Digit for Glycosphingolipid}}===

{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
! colspan=2 | Major Series
|-
! Cerebroside
| colspan="3" style="text-align:left" | '''For GalCer and GlcCer, visit [[:Category:LBSC|this page]].'''
|-
! starting with <big>Galactose</big>
| [[Volatile:ListMol/LBStitle|LBSG1|'''G1''']] ([[Volatile:ClassMatrix|LBSG1.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG1}} items]])
|style="text-align:right"| '''Gal'''-Cer
|
{| style="width:100%;"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4?6?Galb1-Cer|Gala / Neogala]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4/6Galb1-Cer}}
|-
|style="border:0;text-align:left"|[[Volatile:ListMol/LBS|Mainchain.*Galb1-4Glcb1-3Galb1-Cer|Spirometo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Glcb1-3Galb1-Cer}}
|}
|-
! rowspan="8" | starting with <big>Glucose</big>
|-
| [[Volatile:ListMol/LBStitle|LBSG2|'''G2''']] ([[Volatile:ClassMatrix|LBSG2.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG2}} items]])
|style="text-align:right"| '''GalNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-4Galb1-4Glcb1-Cer|Ganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio]]<ref name="iso">In IUPAC, "iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*GlcNAcb1-3$.*GalNAcb1-4$Galb1-4Glcb1-Cer|Lactoganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3(GalNAcb1-4)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-3$?Galb1-4Glcb1-Cer|a-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|b-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|c-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|α-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|β-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG3|'''G3''']] ([[Volatile:ClassMatrix|LBSG3.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG3}} items]])
|style="text-align:right"| '''GlcNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer|Lacto]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto]]<ref name="neo">In IUPAC, "neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG4|'''G4''']] ([[Volatile:ClassMatrix|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG4}} items]])
|style="text-align:right"| '''Galα'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4Galb1-4Glcb1-Cer|Globo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-3Galb1-4Glcb1-Cer|Isoglobo]]<ref name="iso"/>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG5|'''G5''']] ([[Volatile:ClassMatrix|LBSG5.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG5}} items]])
|style="text-align:right"| Gal-Glc-Cer (Other than G2&sim;G4)
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-4Galb1-4Glcb1-Cer|Muco]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG6|'''G6''']] ([[Volatile:ClassMatrix|LBSG6.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG6}} items]])
|style="text-align:right"| '''Man'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcNAcb1-3Manb1-4Glcb1-Cer|Arthro]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3Manb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Mana1-3Manb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG7|'''G7''']] ([[Volatile:ClassMatrix|LBSG7.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG7}} items]])
|style="text-align:right"| '''NeuAc'''/'''NeuGc'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Neu(A~G)c.2-6Glcb1-Cer|Echino]]
|style="border:0;text-align:right"| '''NeuGc''' or {{LBS/FormatSugar|NeuAca2-6Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG8|'''G8''']] ([[Volatile:ClassMatrix|LBSG8.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG8}} items]])
|style="text-align:right"| '''GalNAc'''-Glc-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAc.1-4Glc.1-Cer|Schisto]]<ref>Makaaru CK, Damian RT, Smith DF, Cummings RD. "The human blood fluke Schistosoma mansoni synthesizes a novel type of glycosphingolipid" J Biol Chem 1992 267:2251-2257 PMID 1733932</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Glcb1-Cer}}
|}
|-
! starting with <big>Other Sugars</big>
| [[Volatile:ListMol/LBStitle|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|'''G'''('''A'''&sim;'''R''')]]
|colspan="2"| Symbols follow the Sugar-digit table.
|}
<references/>

==={{Bilingual|スフィンゴリン脂質１文字目|First (s1) Digit for Phosphosphingolipid}}===
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
!colspan="2"| Major Series
|-
! No Sugar Attached
| '''P1''' ([[:Category:LBSP|LBSP]])
| R-P-Cer
| Sphingomyelin and Ceramide phosphoetanolamine (Visit [[:Category:LBSP|this page]].)
|-
! rowspan="4" | starting with <big>Inositol</big>
| [[Volatile:ListMol/LBStitle|LBSP2|'''P2''']] ({{#countTitle:LBSP2}} items)
| style="text-align:right"| '''GlcN'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcN.1-.Ins-P-Cer|Protozoa & Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP3|'''P3''']] ({{#countTitle:LBSP3}} items)
|style="text-align:right"| '''GlcA'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcA.1-.Ins-P-Cer|Plant-specific]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcAa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP4|'''P4''']] ({{#countTitle:LBSP4}} items)
| style="text-align:right"| '''Man'''α/β1−2/6Ins1-P-Cer
|
{| style="width:100%"
| style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Man.1-.Ins-P-Cer|Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|Mana/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP5|'''P5''']] ({{#countTitle:LBSP5}} items)
| style="text-align:right"| Others
| style="text-align:right"| {{LBS/FormatSugar|Ins1-P-Cer}}
|}

==={{Bilingual|コード２文字目|Second (s2) Digit}}===

{{Bilingual|クリックすると一覧が出ます。記号の略称については|Click to see the full list. For abbreviations, see}} [[#Notation]].

{|
|-
| valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''A'''
| Glc [[File:LBS-Monomer-Glc.png]]
|-
! '''B'''
| Gal [[File:LBS-Monomer-Gal.png]]
|-
! '''C'''
| GlcNAc [[File:LBS-Monomer-GlcNAc.png]]
|-
! '''D'''
| GalNAc [[File:LBS-Monomer-GalNAc.png]]
|-
! '''E'''
| GlcN [[File:LBS-Monomer-GlcN.png]]
|-
! '''F'''
| GalN [[File:LBS-Monomer-GalN.png]]
|-
! '''G'''
| GlcA [[File:LBS-Monomer-GlcA.png]]
|-
! '''H'''
| GalA [[File:LBS-Monomer-GalA.png]]
|-
! '''I'''
| not used
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''J'''
| [[Volatile:ListMol/LBS|Structure.*Man|Mannose]] [[File:LBS-Monomer-Man.png]]
|-
! '''K'''
| [[Volatile:ListMol/LBS|Structure.*Rha|Rhamnose]] [[File:LBS-Monomer-Rha.png]]
|-
! '''L'''
| [[Volatile:ListMol/LBS|{{#encode:Structure.*Ins(Me)?-P-[^Cer]}}|Inositol]]
|-
! '''M'''
| Fucose ([[Volatile:ListMol/LBS|{{#encode:Structure[^F]+Fuc[^F]+$}}| 1]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){2}[^F]+$}}|2]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){3}}}|>3]]) [[File:LBS-Monomer-Fuc.png]]
|-
! '''N'''
| [[Volatile:ListMol/LBS|Structure.*Ara|Arabinose]] [[File:LBS-Monomer-Ara.png]]
|-
! '''O'''
| [[Volatile:ListMol/LBS|Structure.*Xyl|Xylose]] [[File:LBS-Monomer-Xyl.png]]
|-
! '''P'''
| [[Volatile:ListMol/LBS|Structure.*(NeuAc~NeuNH)|NeuAc / NeuNH]] [[File:LBS-Monomer-NeuAc.png]]
|-
! '''Q'''
| [[Volatile:ListMol/LBS|Structure.*(NeuGc)|NeuGc]] [[File:LBS-Monomer-NeuGc.png]]
|-
! '''R'''
| [[Volatile:ListMol/LBS|Structure.*(KDN)|Kdn]] [[File:LBS-Monomer-KDN.png]]
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''S'''
| [[Volatile:ListMol/LBS|Structure.*(Phospho)|Phosphate (except GIPC)]] [[File:LBS-Monomer-P.png]]
|-
! '''T'''
| [[Volatile:ListMol/LBS|Structure.*(AEPn)|(M)AEPn]], [[Volatile:ListMol/LBS|Structure.*(EtnP)|EtnP]], [[Volatile:ListMol/LBS|Structure.*(PC)|PC]] [[File:LBS-Monomer-AEPn.png]]
|-
! '''U'''
| [[Volatile:ListMol/LBS|Structure.*Sulfo|Sulfate]] [[File:LBS-Monomer-S.png]]
|-
! '''V'''
| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
|}

=={{Bilingual|生合成|Biosynthesis}}==
{{Twocolumn|
Sphingosine is synthesized from decarboxylating condensation of palmitoyl CoA with serine on the ER membrane. It is a 18-carbon amino alcohol (16 carbons from palmitic acid and 2 from serine) with one unsaturated bond (trans-form) at the C-4 position (2-amino-4-octadecene-1,3-diol). ([[:Category:LBS/Biosynthesis|more details]])
|
スフィンゴシンはパルミトイルCoAがアミノ酸セリンと脱炭酸縮合して生成します。炭素を18個含むアミノアルコール(16個がパルミチン酸、2個がセリン由来)でトランス型の不飽和結合をC-4に1つ含みます。（[[:Category:LBS/Biosynthesis|詳細はこちら]]）
}}

Category:LB

2022-08-13T05:52:58Z

Yasugi: /* Class Overview */

{{Huge|LipidBank}}
{{LB/Header}}
==Class Overview==

{{Twocolumn|
Biogenic substances insoluble to water are collectively called as '''lipid'''. Lipid is generally classified into the following three types.
* '''Simple lipid''' ... fatty acid esters of alchohol such as glycerol and sphingoid base.
* '''Complex lipid''' ... glycosylated or phosphorylated version of the simple lipid.
* '''Derived lipid''' ... alcohols and fatty acids derived by hydrolyzing the simple lipid. Also includes sterols and polyketides.
|
水に溶けない生体成分を一般に脂質と呼び、以下の3つに分けられます。
* '''単純脂質''' ... アルコールと脂肪酸のエステルで、スフィンゴ骨格とグリセロ骨格のものに大別されます。
* '''複合脂質''' ... 単純脂質にリン酸や糖がついたものです。
* '''誘導脂質''' ... 単純脂質を分解して得られるアルコール、脂肪酸。ステロールやポリケチドもここに含めます。
}}
<center>
{| class="wikitable"
|-
! colspan="3" | Lipid Overview
|-
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBF|LBF: Fatty acyls 脂肪酸アシル]]
 [[Image:LBF.png|100px]] 
Includes:
* fatty acids and acyl derivatives of length more than 7
| align="left" style="vertical-align:top" width=33%|
Glycerolipids グリセロ脂質
 [[Image:LBG.png|100px]] Includes:
* mono, di, triacyl glycerol
* glycoglycerolipid (mainly plants)
* phosphoglycerolipid
* [[:Category:LBGA|LBGA: Archaeal Lipid (Ether-type) 古細菌の脂質]]
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBS|LBS: Sphingolipids スフィンゴ脂質]]
 [[Image:LBS.png|110px]] Includes:
* [[:Category:LBSB|LBSB: long-chain base and ceramide]]
* [[:Category:LBSC|LBSC: cerebroside]]
* [[:Category:LBSG|LBSG: acidic glycosphingolipid]]
* [[:Category:LBSP|LBSP: phosphosphingolipid]]
|-
| style="vertical-align:top"|
| style="vertical-align:top"| Polyketides (not ready)
| style="vertical-align:top"| Sterols (not ready)
|}
</center>

; Related projects
* [[Lipoquality:Database|LipoQuality Database]]

Category:LB

2022-08-13T05:51:06Z

Yasugi: /* Class Overview */

{{Huge|LipidBank}}
{{LB/Header}}
==Class Overview==

{{Twocolumn|
Biogenic substances insoluble to water are collectively called as '''lipid'''. Lipid is generally classified into the following three types.
* '''Simple lipid''' ... fatty acid esters of alchohol such as glycerol and sphingoid base.
* '''Complex lipid''' ... glycosylated or phosphorylated version of the simple lipid.
* '''Derived lipid''' ... alcohols and fatty acids derived by hydrolyzing the simple lipid. Also includes sterols and polyketides.
|
水に溶けない生体成分を一般に脂質と呼び、以下の3つに分けられます。
* '''単純脂質''' ... アルコールと脂肪酸のエステルで、スフィンゴ骨格とグリセロ骨格のものに大別されます。
* '''複合脂質''' ... 単純脂質にリン酸や糖がついたものです。
* '''誘導脂質''' ... 単純脂質を分解して得られるアルコール、脂肪酸。ステロールやポリケチドもここに含めます。
}}
<center>
{| class="wikitable"
|-
! colspan="3" | Lipid Overview
|-
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBF|LBF: Fatty acyls 脂肪酸アシル]]
 [[Image:LBF.png|100px]] 
Includes:
* fatty acids and acyl derivatives of length more than 7
| align="left" style="vertical-align:top" width=33%|
Glycerolipids グリセロ脂質
 [[Image:LBG.png|100px]] Includes:
* mono, di, triacyl glycerol
* glycoglycerolipid (mainly plants)
* phosphoglycerolipid
* [[:Category:LBGA|LBGA: Archaeal Lipid (Ether-type) 古細菌の脂質]]
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBF|LBF: Sphingolipids スフィンゴ脂質]]
 [[Image:LBS.png|110px]] Includes:
* [[:Category:LBSB|LBSB: long-chain base and ceramide]]
* [[:Category:LBSC|LBSC: cerebroside]]
* [[:Category:LBSG|LBSG: acidic glycosphingolipid]]
* [[:Category:LBSP|LBSP: phosphosphingolipid]]
|-
| style="vertical-align:top"|
| style="vertical-align:top"| Polyketides (not ready)
| style="vertical-align:top"| Sterols (not ready)
|}
</center>

; Related projects
* [[Lipoquality:Database|LipoQuality Database]]

Category:LBS

2022-08-12T05:20:35Z

Yasugi: /* {{Bilingual|概要|Class Overview}} */

{{Huge|{{Bilingual|スフィンゴ脂質|Sphingolipid}}}}
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
{| style="float:left"
| __TOC__
|}
=={{Bilingual|概要|Class Overview}}==

{{Twocolumn|
Three Sphingolipid categories (LBS) exist in this database.
|このデータベースではスフィンゴ脂質を以下に分けています。
}}

<center>
{|
|-
| style="vertical-align:top" width="33%"|
[[:Category:LBSB| '''Ceramide''']] {{LBS/Cer|OH}} セラミド
| style="vertical-align:top" width="33%"|
[[:Category:LBSG| '''Glycosphingolipid''']] {{LBS/Cer|O-(sugar)}} スフィンゴ糖脂質
| style="vertical-align:top" width="33%"|
[[:Category:LBSP| '''Phosphosphingolipid''']] {{LBS/Cer|O-(phosphate)}} スフィンゴリン脂質
|-
|
*[[:Category:LBSB|Long-chain base and ceramide]]
|
*[[:Category:LBSC|Cerebroside (monohexosyl ceramides)]]
*[[:Category:LBSG|Acidic glycosphingolipid]]
|
*[[:Category:LBSP|Sphingomyelin, CPE, CAEP and GIPC]]
|}
</center>

<center>
{| class="wikitable"
|<big>
[[:Category:LBS/Search|{{Bilingual|スフィンゴ脂質検索画面にいく|Go to Sphingolipid search.}}]]
</big>
|}
</center>

==={{Bilingual|スフィンゴ脂質の歴史|History of Sphingolipids}}===
{{Twocolumn|
Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure.<ref>Thudichum J.L.W. "A Treatise on the Chemical Constitution of the Balliere" Tindall and Cox, London, 1884</ref> The basic structure is a long-chain base (long-chain amino-alcohol) whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides.
Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (oligo)saccharides, respectively. Phosphosphingolipid includes sphingomyelin, and glycosphingolipid, cerebrosides and gangliosides. Both are abundant in neural tissues.<ref>Gault CR, Obeid LM, Hannun YA "An overview of sphingolipid synthesis to breakdown" Adv Exp Med Biol. 2010;688:1-23. PMID 20919643</ref>
|
スフィンゴ脂質は J.L.W. Thudichum (1829-1901) により機能や構造未知の脂質として脳から見いだされました。基本骨格は長鎖塩基 (長鎖アミノアルコール) のアミノ基が長鎖脂肪酸とアミド結合したもので、セラミドと呼ばれます。
スフィンゴ脂質はセラミドにリン酸が結合したスフィンゴリン脂質と糖が結合したスフィンゴ糖脂質に分けられます。スフィンゴリン脂質にはスフィンゴミエリンが、スフィンゴ糖脂質にはセレブロシドやガングリオシドなどが含まれ、いずれも神経系に多く存在します。
}}

<references/>

=={{Bilingual|スフィンゴ脂質|Sphingolipid}}==

==={{Bilingual|表記法|Notation}}===
{| class="wikitable collapsible collapsed" style="width:80%"
!colspan="4" align="center" style="background:lightgray"| Symbol Abbreviations (e.g. Glc = glucose)
|-
!colspan="4" align="center" style="background:lightgray"| Backbones
{{#repeatnum:LBS/AbbrevRow|1|
Cer && ceramide && セラミド &&
Sph && sphingosine && スフィンゴシン &&
}}
|-
!colspan="4" align="center" style="background:lightgray"| Sugars
{{#repeatnum:LBS/AbbrevRow|1|
Glc && glucose && グルコース && C6H12O6 &&
Gal && galactose && ガラクトース && C6H12O6 &&
GlcNAc && ''N''-acetyl-glucosamine && ''N''-アセチルグルコサミン && C8H15NO6
GalNAc && ''N''-acetyl-galactosamine && ''N''-アセチルガラクトサミン && C8H15NO6
GlcN && glucosamine && グルコサミン && C6H13NO5
GalN && galactosamine && ガラクトサミン && C6H13NO5
GlcA && glucuronic acid && グルクロン酸 && C6H10O7
GalA && galacturonic acid && ガラクツロン酸 && C6H10O7 &&
Man && mannose && マンノース && C6H12O6 && 18950
Rha && rhamnose (= 6-deoxy-mannose) && ラムノース (6-デオキシマンノース) && C6H12O5 && 19233
Ins && inositol && イノシトール && C6H12O6 && 892
Fuc && fucose (= 6-deoxy-galactose) && フコース (6-デオキシガラクトース) && C6H12O5 && 17106
Ara && arabinose && アラビノース && C5H10O5 && 5460291
Xyl && xylose && キシロース && C5H10O5 && 135191
NeuNH && (deacetyl) neuraminic acid (pyruvate + mannosamine) && ノイラミン酸 (ピルビン酸＋マンノサミン) && C9H17N1O8 && 513472
NeuAc && ''N''-acetyl-neuraminic acid && ''N''-アセチルノイラミン酸 && C11H19NO9 && 439197
NeuGc && ''N''-glycolyl-neuraminic acid && ''N''-グリコリルノイラミン酸 && C11H19NO10 && 123802
Kdn && 2-keto-3-deoxy-D-glycero- D-galacto-nononic acid && デアミノノイラミン酸 && C9H16O9 && 13991616
}}
|-
!colspan="4" align="center" style="background:lightgray"| Modifiers
{{#repeatnum:LBS/AbbrevRow|1|
AEPn && aminoethylphosphonic acid, or (2-aminoethyl)hydroxyphosphoryl- && アミノエチルホスホン酸（C-P結合）
MAEPn && ''N''-methyl aminoethylphosphonic acid, or (''N''-methyl-2-aminoethyl) hydroxyphosphoryl- && AEPnの''N''-メチル体（C-P結合）
EtnP && phosphoethanolamine (PEA), or 2-aminoethanolphospho- && ホスホエタノールアミン
PC && Phosphocholine && ホスホコリン
Butenyl && Butenyl && ブテニル基
Me && Methyl && メチル基
Et && Ethyl && エチル基
}}
|}

==={{Bilingual|分類体系|Page/ID-Code Design}}===
{{Twocolumn|
Major series of phosphosphingolipids are determined by molecules bound to their phosphates, and the series of glycosphingolipids are determined by oligosaccharides bound to their ceramides. The IUPAC series of glycosphingolipids (1977) were based on the order and bonding patterns of four sugars rooting at the long-chain base. Our series, however, are based on three sugars. Two original series, Echino and Schisto, are also added.
|スフィンゴリン脂質はリン酸に結合する分子や糖の種類、スフィンゴ糖脂質はセラミドに結合する糖鎖により系列を作成しています。1977年にIUPACが提唱したスフィンゴ糖脂質の系列は、長鎖塩基に結合する四糖の並びと結合を基準にしています。ここではより広い糖鎖の系列を検索できるよう、三糖を基準に分類しています。また新たにEchinoとSchistoの系列を加えています。
}}

{|
|
<table border=1>
<tr>
<td style="background-color:yellowgreen;" width=20px align="center"><big>L</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>B</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>S</big>
<td style="background-color:green;" width=20px align="center"><big>''G/P''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s1''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s2''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n1''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n2''</big>
<td style="background-color:firebrick; color:white" width=20px align="center"><big>''y''</big>
<td style="background-color:white;" width=20px align="center"><big>''c1''</big>
<td style="background-color:white;" width=20px align="center"><big>''c2''</big>
</tr>
</table>
|  
|
{| class="wikitable"
! '''G/P''' || '''G''' (glyco) || '''P''' (phospho)
|-
! '''s1, s2'''
|colspan="3"| structure code as explained below
|-
! '''n1, n2'''
|colspan="2"| number of sugars (2 digits)
|-
! '''y'''
|colspan="2"| number of sialic acids (1 digit)
|-
! '''c1, c2'''
|colspan="2"| serial numbers
|}
|}

==={{Bilingual|スフィンゴ糖脂質１文字目|First (s1) Digit for Glycosphingolipid}}===

{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
! colspan=2 | Major Series
|-
! Cerebroside
| colspan="3" style="text-align:left" | '''For GalCer and GlcCer, visit [[:Category:LBSC|this page]].'''
|-
! starting with <big>Galactose</big>
| [[Volatile:ListMol/LBStitle|LBSG1|'''G1''']] ([[Volatile:ClassMatrix|LBSG1.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG1}} items]])
|style="text-align:right"| '''Gal'''-Cer
|
{| style="width:100%;"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4?6?Galb1-Cer|Gala / Neogala]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4/6Galb1-Cer}}
|-
|style="border:0;text-align:left"|[[Volatile:ListMol/LBS|Mainchain.*Galb1-4Glcb1-3Galb1-Cer|Spirometo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Glcb1-3Galb1-Cer}}
|}
|-
! rowspan="8" | starting with <big>Glucose</big>
|-
| [[Volatile:ListMol/LBStitle|LBSG2|'''G2''']] ([[Volatile:ClassMatrix|LBSG2.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG2}} items]])
|style="text-align:right"| '''GalNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-4Galb1-4Glcb1-Cer|Ganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio]]<ref name="iso">In IUPAC, "iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*GlcNAcb1-3$.*GalNAcb1-4$Galb1-4Glcb1-Cer|Lactoganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3(GalNAcb1-4)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-3$?Galb1-4Glcb1-Cer|a-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|b-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|c-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|α-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|β-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG3|'''G3''']] ([[Volatile:ClassMatrix|LBSG3.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG3}} items]])
|style="text-align:right"| '''GlcNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer|Lacto]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto]]<ref name="neo">In IUPAC, "neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG4|'''G4''']] ([[Volatile:ClassMatrix|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG4}} items]])
|style="text-align:right"| '''Galα'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4Galb1-4Glcb1-Cer|Globo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-3Galb1-4Glcb1-Cer|Isoglobo]]<ref name="iso"/>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG5|'''G5''']] ([[Volatile:ClassMatrix|LBSG5.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG5}} items]])
|style="text-align:right"| Gal-Glc-Cer (Other than G2&sim;G4)
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-4Galb1-4Glcb1-Cer|Muco]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG6|'''G6''']] ([[Volatile:ClassMatrix|LBSG6.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG6}} items]])
|style="text-align:right"| '''Man'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcNAcb1-3Manb1-4Glcb1-Cer|Arthro]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3Manb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Mana1-3Manb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG7|'''G7''']] ([[Volatile:ClassMatrix|LBSG7.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG7}} items]])
|style="text-align:right"| '''NeuAc'''/'''NeuGc'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Neu(A~G)c.2-6Glcb1-Cer|Echino]]
|style="border:0;text-align:right"| '''NeuGc''' or {{LBS/FormatSugar|NeuAca2-6Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG8|'''G8''']] ([[Volatile:ClassMatrix|LBSG8.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG8}} items]])
|style="text-align:right"| '''GalNAc'''-Glc-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAc.1-4Glc.1-Cer|Schisto]]<ref>Makaaru CK, Damian RT, Smith DF, Cummings RD. "The human blood fluke Schistosoma mansoni synthesizes a novel type of glycosphingolipid" J Biol Chem 1992 267:2251-2257 PMID 1733932</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Glcb1-Cer}}
|}
|-
! starting with <big>Other Sugars</big>
| [[Volatile:ListMol/LBStitle|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|'''G'''('''A'''&sim;'''R''')]]
|colspan="2"| Symbols follow the Sugar-digit table.
|}
<references/>

==={{Bilingual|スフィンゴリン脂質１文字目|First (s1) Digit for Phosphosphingolipid}}===
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
!colspan="2"| Major Series
|-
! No Sugar Attached
| '''P1''' ([[:Category:LBSP|LBSP]])
| R-P-Cer
| Sphingomyelin and Ceramide phosphoetanolamine (Visit [[:Category:LBSP|this page]].)
|-
! rowspan="4" | starting with <big>Inositol</big>
| [[Volatile:ListMol/LBStitle|LBSP2|'''P2''']] ({{#countTitle:LBSP2}} items)
| style="text-align:right"| '''GlcN'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcN.1-.Ins-P-Cer|Protozoa & Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP3|'''P3''']] ({{#countTitle:LBSP3}} items)
|style="text-align:right"| '''GlcA'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcA.1-.Ins-P-Cer|Plant-specific]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcAa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP4|'''P4''']] ({{#countTitle:LBSP4}} items)
| style="text-align:right"| '''Man'''α/β1−2/6Ins1-P-Cer
|
{| style="width:100%"
| style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Man.1-.Ins-P-Cer|Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|Mana/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP5|'''P5''']] ({{#countTitle:LBSP5}} items)
| style="text-align:right"| Others
| style="text-align:right"| {{LBS/FormatSugar|Ins1-P-Cer}}
|}

==={{Bilingual|コード２文字目|Second (s2) Digit}}===

{{Bilingual|クリックすると一覧が出ます。記号の略称については|Click to see the full list. For abbreviations, see}} [[#Notation]].

{|
|-
| valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''A'''
| Glc [[File:LBS-Monomer-Glc.png]]
|-
! '''B'''
| Gal [[File:LBS-Monomer-Gal.png]]
|-
! '''C'''
| GlcNAc [[File:LBS-Monomer-GlcNAc.png]]
|-
! '''D'''
| GalNAc [[File:LBS-Monomer-GalNAc.png]]
|-
! '''E'''
| GlcN [[File:LBS-Monomer-GlcN.png]]
|-
! '''F'''
| GalN [[File:LBS-Monomer-GalN.png]]
|-
! '''G'''
| GlcA [[File:LBS-Monomer-GlcA.png]]
|-
! '''H'''
| GalA [[File:LBS-Monomer-GalA.png]]
|-
! '''I'''
| not used
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''J'''
| [[Volatile:ListMol/LBS|Structure.*Man|Mannose]] [[File:LBS-Monomer-Man.png]]
|-
! '''K'''
| [[Volatile:ListMol/LBS|Structure.*Rha|Rhamnose]] [[File:LBS-Monomer-Rha.png]]
|-
! '''L'''
| [[Volatile:ListMol/LBS|{{#encode:Structure.*Ins(Me)?-P-[^Cer]}}|Inositol]]
|-
! '''M'''
| Fucose ([[Volatile:ListMol/LBS|{{#encode:Structure[^F]+Fuc[^F]+$}}| 1]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){2}[^F]+$}}|2]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){3}}}|>3]]) [[File:LBS-Monomer-Fuc.png]]
|-
! '''N'''
| [[Volatile:ListMol/LBS|Structure.*Ara|Arabinose]] [[File:LBS-Monomer-Ara.png]]
|-
! '''O'''
| [[Volatile:ListMol/LBS|Structure.*Xyl|Xylose]] [[File:LBS-Monomer-Xyl.png]]
|-
! '''P'''
| [[Volatile:ListMol/LBS|Structure.*(NeuAc~NeuNH)|NeuAc / NeuNH]] [[File:LBS-Monomer-NeuAc.png]]
|-
! '''Q'''
| [[Volatile:ListMol/LBS|Structure.*(NeuGc)|NeuGc]] [[File:LBS-Monomer-NeuGc.png]]
|-
! '''R'''
| [[Volatile:ListMol/LBS|Structure.*(KDN)|Kdn]] [[File:LBS-Monomer-KDN.png]]
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''S'''
| [[Volatile:ListMol/LBS|Structure.*(Phospho)|Phosphate (except GIPC)]] [[File:LBS-Monomer-P.png]]
|-
! '''T'''
| [[Volatile:ListMol/LBS|Structure.*(AEPn)|(M)AEPn]], [[Volatile:ListMol/LBS|Structure.*(EtnP)|EtnP]], [[Volatile:ListMol/LBS|Structure.*(PC)|PC]] [[File:LBS-Monomer-AEPn.png]]
|-
! '''U'''
| [[Volatile:ListMol/LBS|Structure.*Sulfo|Sulfate]] [[File:LBS-Monomer-S.png]]
|-
! '''V'''
| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
|}

=={{Bilingual|生合成|Biosynthesis}}==
{{Twocolumn|
Sphingosine is synthesized from decarboxylating condensation of palmitoyl CoA with serine on the ER membrane. It is a 18-carbon amino alcohol (16 carbons from palmitic acid and 2 from serine) with one unsaturated bond (trans-form) at the C-4 position (2-amino-4-octadecene-1,3-diol). ([[:Category:LBS/Biosynthesis|more details]])
|
スフィンゴシンはパルミトイルCoAがアミノ酸セリンと脱炭酸縮合して生成します。炭素を18個含むアミノアルコール(16個がパルミチン酸、2個がセリン由来)でトランス型の不飽和結合をC-4に1つ含みます。（[[:Category:LBS/Biosynthesis|詳細はこちら]]）
}}

Category:LBSP

2022-08-11T02:17:59Z

Yasugi: Undo revision 116964 by Yasugi (talk)

Category:LBSP

2022-08-11T02:07:19Z

Yasugi:

{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
__TOC__

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

{{Twocolumn|
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>
|
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。
}}

<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);">(C14-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;">OCH2CH2N+(CH3)3</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 → Sphingomyelin + 1,2-Diacylglycerol
:
;SM degradation (Sphingomyelinase) SMase
: Sphingomyelin → 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>
|
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。
}}

<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);">(C14-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;">OCH2CH2NH2</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 → CPE + 1,2-diacylglycerol
;CPE synthase (SMS1-related enzyme) SMSr/SAMD8
: CDP-ethanolamine + ceramide → CPE + CMP

<references/>

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

{{Twocolumn|
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.)
|
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
}}

<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);">(C14-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>
</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===
;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>
:Phosphatidylinositol + Ceramide → Inositol phosphoceramide + Diacylglycerol

==Phosphosphingolipids in All Kingdoms==

{{:Category:ScientificClassification/LBSC}}

<references/>

Category:LBS

2022-08-10T05:47:45Z

Yasugi: /* {{Bilingual|概要|Class Overview}} */

{{Huge|{{Bilingual|スフィンゴ脂質|Sphingolipid}}}}
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
{| style="float:left"
| __TOC__
|}
=={{Bilingual|概要|Class Overview}}==

{{Twocolumn|
Three Sphingolipid categories (LBS) exist in this database.
|このデータベースではスフィンゴ脂質を以下に分けています。
}}

<center>
{|
|-
| style="vertical-align:top" width="33%"|
[[:Category:LBSB| '''Ceramide''']] {{LBS/Cer|OH}} セラミド
| style="vertical-align:top" width="33%"|
[[:Category:LBSG| '''Glycosphingolipid''']] {{LBS/Cer|O-(sugar)}} スフィンゴ糖脂質
| style="vertical-align:top" width="33%"|
[[:Category:LBSP| '''Phosphosphingolipid''']] {{LBS/Cer|O-(phosphate)}} スフィンゴリン脂質
|-
|
*[[:Category:LBSB|Long-chain base and ceramide]]
|
*[[:Category:LBSC|Cerebroside (monohexosyl ceramides)]]
*[[:Category:LBSG|Acidic glycosylceramide ]]
|
*[[:Category:LBSP|Sphingomyelin, CPE, CAEP and GIPC]]
|}
</center>

<center>
{| class="wikitable"
|<big>
[[:Category:LBS/Search|{{Bilingual|スフィンゴ脂質検索画面にいく|Go to Sphingolipid search.}}]]
</big>
|}
</center>

==={{Bilingual|スフィンゴ脂質の歴史|History of Sphingolipids}}===
{{Twocolumn|
Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure.<ref>Thudichum J.L.W. "A Treatise on the Chemical Constitution of the Balliere" Tindall and Cox, London, 1884</ref> The basic structure is a long-chain base (long-chain amino-alcohol) whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides.
Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (oligo)saccharides, respectively. Phosphosphingolipid includes sphingomyelin, and glycosphingolipid, cerebrosides and gangliosides. Both are abundant in neural tissues.<ref>Gault CR, Obeid LM, Hannun YA "An overview of sphingolipid synthesis to breakdown" Adv Exp Med Biol. 2010;688:1-23. PMID 20919643</ref>
|
スフィンゴ脂質は J.L.W. Thudichum (1829-1901) により機能や構造未知の脂質として脳から見いだされました。基本骨格は長鎖塩基 (長鎖アミノアルコール) のアミノ基が長鎖脂肪酸とアミド結合したもので、セラミドと呼ばれます。
スフィンゴ脂質はセラミドにリン酸が結合したスフィンゴリン脂質と糖が結合したスフィンゴ糖脂質に分けられます。スフィンゴリン脂質にはスフィンゴミエリンが、スフィンゴ糖脂質にはセレブロシドやガングリオシドなどが含まれ、いずれも神経系に多く存在します。
}}

<references/>

=={{Bilingual|スフィンゴ脂質|Sphingolipid}}==

==={{Bilingual|表記法|Notation}}===
{| class="wikitable collapsible collapsed" style="width:80%"
!colspan="4" align="center" style="background:lightgray"| Symbol Abbreviations (e.g. Glc = glucose)
|-
!colspan="4" align="center" style="background:lightgray"| Backbones
{{#repeatnum:LBS/AbbrevRow|1|
Cer && ceramide && セラミド &&
Sph && sphingosine && スフィンゴシン &&
}}
|-
!colspan="4" align="center" style="background:lightgray"| Sugars
{{#repeatnum:LBS/AbbrevRow|1|
Glc && glucose && グルコース && C6H12O6 &&
Gal && galactose && ガラクトース && C6H12O6 &&
GlcNAc && ''N''-acetyl-glucosamine && ''N''-アセチルグルコサミン && C8H15NO6
GalNAc && ''N''-acetyl-galactosamine && ''N''-アセチルガラクトサミン && C8H15NO6
GlcN && glucosamine && グルコサミン && C6H13NO5
GalN && galactosamine && ガラクトサミン && C6H13NO5
GlcA && glucuronic acid && グルクロン酸 && C6H10O7
GalA && galacturonic acid && ガラクツロン酸 && C6H10O7 &&
Man && mannose && マンノース && C6H12O6 && 18950
Rha && rhamnose (= 6-deoxy-mannose) && ラムノース (6-デオキシマンノース) && C6H12O5 && 19233
Ins && inositol && イノシトール && C6H12O6 && 892
Fuc && fucose (= 6-deoxy-galactose) && フコース (6-デオキシガラクトース) && C6H12O5 && 17106
Ara && arabinose && アラビノース && C5H10O5 && 5460291
Xyl && xylose && キシロース && C5H10O5 && 135191
NeuNH && (deacetyl) neuraminic acid (pyruvate + mannosamine) && ノイラミン酸 (ピルビン酸＋マンノサミン) && C9H17N1O8 && 513472
NeuAc && ''N''-acetyl-neuraminic acid && ''N''-アセチルノイラミン酸 && C11H19NO9 && 439197
NeuGc && ''N''-glycolyl-neuraminic acid && ''N''-グリコリルノイラミン酸 && C11H19NO10 && 123802
Kdn && 2-keto-3-deoxy-D-glycero- D-galacto-nononic acid && デアミノノイラミン酸 && C9H16O9 && 13991616
}}
|-
!colspan="4" align="center" style="background:lightgray"| Modifiers
{{#repeatnum:LBS/AbbrevRow|1|
AEPn && aminoethylphosphonic acid, or (2-aminoethyl)hydroxyphosphoryl- && アミノエチルホスホン酸（C-P結合）
MAEPn && ''N''-methyl aminoethylphosphonic acid, or (''N''-methyl-2-aminoethyl) hydroxyphosphoryl- && AEPnの''N''-メチル体（C-P結合）
EtnP && phosphoethanolamine (PEA), or 2-aminoethanolphospho- && ホスホエタノールアミン
PC && Phosphocholine && ホスホコリン
Butenyl && Butenyl && ブテニル基
Me && Methyl && メチル基
Et && Ethyl && エチル基
}}
|}

==={{Bilingual|分類体系|Page/ID-Code Design}}===
{{Twocolumn|
Major series of phosphosphingolipids are determined by molecules bound to their phosphates, and the series of glycosphingolipids are determined by oligosaccharides bound to their ceramides. The IUPAC series of glycosphingolipids (1977) were based on the order and bonding patterns of four sugars rooting at the long-chain base. Our series, however, are based on three sugars. Two original series, Echino and Schisto, are also added.
|スフィンゴリン脂質はリン酸に結合する分子や糖の種類、スフィンゴ糖脂質はセラミドに結合する糖鎖により系列を作成しています。1977年にIUPACが提唱したスフィンゴ糖脂質の系列は、長鎖塩基に結合する四糖の並びと結合を基準にしています。ここではより広い糖鎖の系列を検索できるよう、三糖を基準に分類しています。また新たにEchinoとSchistoの系列を加えています。
}}

{|
|
<table border=1>
<tr>
<td style="background-color:yellowgreen;" width=20px align="center"><big>L</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>B</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>S</big>
<td style="background-color:green;" width=20px align="center"><big>''G/P''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s1''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s2''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n1''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n2''</big>
<td style="background-color:firebrick; color:white" width=20px align="center"><big>''y''</big>
<td style="background-color:white;" width=20px align="center"><big>''c1''</big>
<td style="background-color:white;" width=20px align="center"><big>''c2''</big>
</tr>
</table>
|  
|
{| class="wikitable"
! '''G/P''' || '''G''' (glyco) || '''P''' (phospho)
|-
! '''s1, s2'''
|colspan="3"| structure code as explained below
|-
! '''n1, n2'''
|colspan="2"| number of sugars (2 digits)
|-
! '''y'''
|colspan="2"| number of sialic acids (1 digit)
|-
! '''c1, c2'''
|colspan="2"| serial numbers
|}
|}

==={{Bilingual|スフィンゴ糖脂質１文字目|First (s1) Digit for Glycosphingolipid}}===

{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
! colspan=2 | Major Series
|-
! Cerebroside
| colspan="3" style="text-align:left" | '''For GalCer and GlcCer, visit [[:Category:LBSC|this page]].'''
|-
! starting with <big>Galactose</big>
| [[Volatile:ListMol/LBStitle|LBSG1|'''G1''']] ([[Volatile:ClassMatrix|LBSG1.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG1}} items]])
|style="text-align:right"| '''Gal'''-Cer
|
{| style="width:100%;"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4?6?Galb1-Cer|Gala / Neogala]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4/6Galb1-Cer}}
|-
|style="border:0;text-align:left"|[[Volatile:ListMol/LBS|Mainchain.*Galb1-4Glcb1-3Galb1-Cer|Spirometo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Glcb1-3Galb1-Cer}}
|}
|-
! rowspan="8" | starting with <big>Glucose</big>
|-
| [[Volatile:ListMol/LBStitle|LBSG2|'''G2''']] ([[Volatile:ClassMatrix|LBSG2.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG2}} items]])
|style="text-align:right"| '''GalNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-4Galb1-4Glcb1-Cer|Ganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio]]<ref name="iso">In IUPAC, "iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*GlcNAcb1-3$.*GalNAcb1-4$Galb1-4Glcb1-Cer|Lactoganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3(GalNAcb1-4)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-3$?Galb1-4Glcb1-Cer|a-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|b-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|c-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|α-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|β-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG3|'''G3''']] ([[Volatile:ClassMatrix|LBSG3.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG3}} items]])
|style="text-align:right"| '''GlcNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer|Lacto]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto]]<ref name="neo">In IUPAC, "neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG4|'''G4''']] ([[Volatile:ClassMatrix|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG4}} items]])
|style="text-align:right"| '''Galα'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4Galb1-4Glcb1-Cer|Globo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-3Galb1-4Glcb1-Cer|Isoglobo]]<ref name="iso"/>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG5|'''G5''']] ([[Volatile:ClassMatrix|LBSG5.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG5}} items]])
|style="text-align:right"| Gal-Glc-Cer (Other than G2&sim;G4)
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-4Galb1-4Glcb1-Cer|Muco]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG6|'''G6''']] ([[Volatile:ClassMatrix|LBSG6.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG6}} items]])
|style="text-align:right"| '''Man'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcNAcb1-3Manb1-4Glcb1-Cer|Arthro]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3Manb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Mana1-3Manb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG7|'''G7''']] ([[Volatile:ClassMatrix|LBSG7.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG7}} items]])
|style="text-align:right"| '''NeuAc'''/'''NeuGc'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Neu(A~G)c.2-6Glcb1-Cer|Echino]]
|style="border:0;text-align:right"| '''NeuGc''' or {{LBS/FormatSugar|NeuAca2-6Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG8|'''G8''']] ([[Volatile:ClassMatrix|LBSG8.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG8}} items]])
|style="text-align:right"| '''GalNAc'''-Glc-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAc.1-4Glc.1-Cer|Schisto]]<ref>Makaaru CK, Damian RT, Smith DF, Cummings RD. "The human blood fluke Schistosoma mansoni synthesizes a novel type of glycosphingolipid" J Biol Chem 1992 267:2251-2257 PMID 1733932</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Glcb1-Cer}}
|}
|-
! starting with <big>Other Sugars</big>
| [[Volatile:ListMol/LBStitle|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|'''G'''('''A'''&sim;'''R''')]]
|colspan="2"| Symbols follow the Sugar-digit table.
|}
<references/>

==={{Bilingual|スフィンゴリン脂質１文字目|First (s1) Digit for Phosphosphingolipid}}===
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
!colspan="2"| Major Series
|-
! No Sugar Attached
| '''P1''' ([[:Category:LBSP|LBSP]])
| R-P-Cer
| Sphingomyelin and Ceramide phosphoetanolamine (Visit [[:Category:LBSP|this page]].)
|-
! rowspan="4" | starting with <big>Inositol</big>
| [[Volatile:ListMol/LBStitle|LBSP2|'''P2''']] ({{#countTitle:LBSP2}} items)
| style="text-align:right"| '''GlcN'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcN.1-.Ins-P-Cer|Protozoa & Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP3|'''P3''']] ({{#countTitle:LBSP3}} items)
|style="text-align:right"| '''GlcA'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcA.1-.Ins-P-Cer|Plant-specific]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcAa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP4|'''P4''']] ({{#countTitle:LBSP4}} items)
| style="text-align:right"| '''Man'''α/β1−2/6Ins1-P-Cer
|
{| style="width:100%"
| style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Man.1-.Ins-P-Cer|Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|Mana/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP5|'''P5''']] ({{#countTitle:LBSP5}} items)
| style="text-align:right"| Others
| style="text-align:right"| {{LBS/FormatSugar|Ins1-P-Cer}}
|}

==={{Bilingual|コード２文字目|Second (s2) Digit}}===

{{Bilingual|クリックすると一覧が出ます。記号の略称については|Click to see the full list. For abbreviations, see}} [[#Notation]].

{|
|-
| valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''A'''
| Glc [[File:LBS-Monomer-Glc.png]]
|-
! '''B'''
| Gal [[File:LBS-Monomer-Gal.png]]
|-
! '''C'''
| GlcNAc [[File:LBS-Monomer-GlcNAc.png]]
|-
! '''D'''
| GalNAc [[File:LBS-Monomer-GalNAc.png]]
|-
! '''E'''
| GlcN [[File:LBS-Monomer-GlcN.png]]
|-
! '''F'''
| GalN [[File:LBS-Monomer-GalN.png]]
|-
! '''G'''
| GlcA [[File:LBS-Monomer-GlcA.png]]
|-
! '''H'''
| GalA [[File:LBS-Monomer-GalA.png]]
|-
! '''I'''
| not used
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''J'''
| [[Volatile:ListMol/LBS|Structure.*Man|Mannose]] [[File:LBS-Monomer-Man.png]]
|-
! '''K'''
| [[Volatile:ListMol/LBS|Structure.*Rha|Rhamnose]] [[File:LBS-Monomer-Rha.png]]
|-
! '''L'''
| [[Volatile:ListMol/LBS|{{#encode:Structure.*Ins(Me)?-P-[^Cer]}}|Inositol]]
|-
! '''M'''
| Fucose ([[Volatile:ListMol/LBS|{{#encode:Structure[^F]+Fuc[^F]+$}}| 1]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){2}[^F]+$}}|2]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){3}}}|>3]]) [[File:LBS-Monomer-Fuc.png]]
|-
! '''N'''
| [[Volatile:ListMol/LBS|Structure.*Ara|Arabinose]] [[File:LBS-Monomer-Ara.png]]
|-
! '''O'''
| [[Volatile:ListMol/LBS|Structure.*Xyl|Xylose]] [[File:LBS-Monomer-Xyl.png]]
|-
! '''P'''
| [[Volatile:ListMol/LBS|Structure.*(NeuAc~NeuNH)|NeuAc / NeuNH]] [[File:LBS-Monomer-NeuAc.png]]
|-
! '''Q'''
| [[Volatile:ListMol/LBS|Structure.*(NeuGc)|NeuGc]] [[File:LBS-Monomer-NeuGc.png]]
|-
! '''R'''
| [[Volatile:ListMol/LBS|Structure.*(KDN)|Kdn]] [[File:LBS-Monomer-KDN.png]]
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''S'''
| [[Volatile:ListMol/LBS|Structure.*(Phospho)|Phosphate (except GIPC)]] [[File:LBS-Monomer-P.png]]
|-
! '''T'''
| [[Volatile:ListMol/LBS|Structure.*(AEPn)|(M)AEPn]], [[Volatile:ListMol/LBS|Structure.*(EtnP)|EtnP]], [[Volatile:ListMol/LBS|Structure.*(PC)|PC]] [[File:LBS-Monomer-AEPn.png]]
|-
! '''U'''
| [[Volatile:ListMol/LBS|Structure.*Sulfo|Sulfate]] [[File:LBS-Monomer-S.png]]
|-
! '''V'''
| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
|}

=={{Bilingual|生合成|Biosynthesis}}==
{{Twocolumn|
Sphingosine is synthesized from decarboxylating condensation of palmitoyl CoA with serine on the ER membrane. It is a 18-carbon amino alcohol (16 carbons from palmitic acid and 2 from serine) with one unsaturated bond (trans-form) at the C-4 position (2-amino-4-octadecene-1,3-diol). ([[:Category:LBS/Biosynthesis|more details]])
|
スフィンゴシンはパルミトイルCoAがアミノ酸セリンと脱炭酸縮合して生成します。炭素を18個含むアミノアルコール(16個がパルミチン酸、2個がセリン由来)でトランス型の不飽和結合をC-4に1つ含みます。（[[:Category:LBS/Biosynthesis|詳細はこちら]]）
}}

Category:LB

2022-08-10T05:24:57Z

Yasugi: /* Class Overview */

{{Huge|LipidBank}}
{{LB/Header}}
==Class Overview==

{{Twocolumn|
Biogenic substances insoluble to water are collectively called as '''lipid'''. Lipid is generally classified into the following three types.
* '''Simple lipid''' ... fatty acid esters of alchohol such as glycerol and sphingoid base.
* '''Complex lipid''' ... glycosylated or phosphorylated version of the simple lipid.
* '''Derived lipid''' ... alcohols and fatty acids derived by hydrolyzing the simple lipid. Also includes sterols and polyketides.
|
水に溶けない生体成分を一般に脂質と呼び、以下の3つに分けられます。
* '''単純脂質''' ... アルコールと脂肪酸のエステルで、スフィンゴ骨格とグリセロ骨格のものに大別されます。
* '''複合脂質''' ... 単純脂質にリン酸や糖がついたものです。
* '''誘導脂質''' ... 単純脂質を分解して得られるアルコール、脂肪酸。ステロールやポリケチドもここに含めます。
}}
<center>
{| class="wikitable"
|-
! colspan="3" | Lipid Overview
|-
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBF|LBF: Fatty acyls 脂肪酸アシル]]
 [[Image:LBF.png|100px]] 
Includes:
* fatty acids and acyl derivatives of length more than 7
| align="left" style="vertical-align:top" width=33%|
Glycerolipids グリセロ脂質
 [[Image:LBG.png|100px]] Includes:
* mono, di, triacyl glycerol
* glycoglycerolipid (mainly plants)
* phosphoglycerolipid
* [[:Category:LBGA|LBGA: Archaeal Lipid (Ether-type) 古細菌の脂質]]
| align="left" style="vertical-align:top" width=33%|
Sphingolipids スフィンゴ脂質
 [[Image:LBS.png|110px]] Includes:
* [[:Category:LBSB|LBSB: long-chain base and ceramide]]
* [[:Category:LBSC|LBSC: cerebroside]]
* [[:Category:LBSG|LBSG: acidic glycosphingolipid]]
* [[:Category:LBSP|LBSP: phosphosphingolipid]]
|-
| style="vertical-align:top"|
| style="vertical-align:top"| Polyketides (not ready)
| style="vertical-align:top"| Sterols (not ready)
|}
</center>

; Related projects
* [[Lipoquality:Database|LipoQuality Database]]

Category:LBS

2022-08-10T01:55:25Z

Yasugi: /* {{Bilingual|概要|Class Overview}} */

{{Huge|{{Bilingual|スフィンゴ脂質|Sphingolipid}}}}
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
{| style="float:left"
| __TOC__
|}
=={{Bilingual|概要|Class Overview}}==

{{Twocolumn|
Three Sphingolipid categories (LBS) exist in this database.
|このデータベースではスフィンゴ脂質を以下に分けています。
}}

<center>
{|
|-
| style="vertical-align:top" width="33%"|
[[:Category:LBSB| '''Ceramide''']] {{LBS/Cer|OH}} セラミド
| style="vertical-align:top" width="33%"|
[[:Category:LBSG| '''Glycosphingolipid''']] {{LBS/Cer|O-(sugar)}} スフィンゴ糖脂質
| style="vertical-align:top" width="33%"|
[[:Category:LBSP| '''Phosphosphingolipid''']] {{LBS/Cer|O-(phosphate)}} スフィンゴリン脂質
|-
|
*[[:Category:LBSB|Long-chain base and ceramide]]
|
*[[:Category:LBSC|Cerebroside (monohexosyl ceramides)]]
*[[:Category:LBSG|Acidic glycosylceramide ]]
|
*[[:Category:LBSP|Sphingomyelins and GIPC]]
|}
</center>

<center>
{| class="wikitable"
|<big>
[[:Category:LBS/Search|{{Bilingual|スフィンゴ脂質検索画面にいく|Go to Sphingolipid search.}}]]
</big>
|}
</center>

==={{Bilingual|スフィンゴ脂質の歴史|History of Sphingolipids}}===
{{Twocolumn|
Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure.<ref>Thudichum J.L.W. "A Treatise on the Chemical Constitution of the Balliere" Tindall and Cox, London, 1884</ref> The basic structure is a long-chain base (long-chain amino-alcohol) whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides.
Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (oligo)saccharides, respectively. Phosphosphingolipid includes sphingomyelin, and glycosphingolipid, cerebrosides and gangliosides. Both are abundant in neural tissues.<ref>Gault CR, Obeid LM, Hannun YA "An overview of sphingolipid synthesis to breakdown" Adv Exp Med Biol. 2010;688:1-23. PMID 20919643</ref>
|
スフィンゴ脂質は J.L.W. Thudichum (1829-1901) により機能や構造未知の脂質として脳から見いだされました。基本骨格は長鎖塩基 (長鎖アミノアルコール) のアミノ基が長鎖脂肪酸とアミド結合したもので、セラミドと呼ばれます。
スフィンゴ脂質はセラミドにリン酸が結合したスフィンゴリン脂質と糖が結合したスフィンゴ糖脂質に分けられます。スフィンゴリン脂質にはスフィンゴミエリンが、スフィンゴ糖脂質にはセレブロシドやガングリオシドなどが含まれ、いずれも神経系に多く存在します。
}}

<references/>

=={{Bilingual|スフィンゴ脂質|Sphingolipid}}==

==={{Bilingual|表記法|Notation}}===
{| class="wikitable collapsible collapsed" style="width:80%"
!colspan="4" align="center" style="background:lightgray"| Symbol Abbreviations (e.g. Glc = glucose)
|-
!colspan="4" align="center" style="background:lightgray"| Backbones
{{#repeatnum:LBS/AbbrevRow|1|
Cer && ceramide && セラミド &&
Sph && sphingosine && スフィンゴシン &&
}}
|-
!colspan="4" align="center" style="background:lightgray"| Sugars
{{#repeatnum:LBS/AbbrevRow|1|
Glc && glucose && グルコース && C6H12O6 &&
Gal && galactose && ガラクトース && C6H12O6 &&
GlcNAc && ''N''-acetyl-glucosamine && ''N''-アセチルグルコサミン && C8H15NO6
GalNAc && ''N''-acetyl-galactosamine && ''N''-アセチルガラクトサミン && C8H15NO6
GlcN && glucosamine && グルコサミン && C6H13NO5
GalN && galactosamine && ガラクトサミン && C6H13NO5
GlcA && glucuronic acid && グルクロン酸 && C6H10O7
GalA && galacturonic acid && ガラクツロン酸 && C6H10O7 &&
Man && mannose && マンノース && C6H12O6 && 18950
Rha && rhamnose (= 6-deoxy-mannose) && ラムノース (6-デオキシマンノース) && C6H12O5 && 19233
Ins && inositol && イノシトール && C6H12O6 && 892
Fuc && fucose (= 6-deoxy-galactose) && フコース (6-デオキシガラクトース) && C6H12O5 && 17106
Ara && arabinose && アラビノース && C5H10O5 && 5460291
Xyl && xylose && キシロース && C5H10O5 && 135191
NeuNH && (deacetyl) neuraminic acid (pyruvate + mannosamine) && ノイラミン酸 (ピルビン酸＋マンノサミン) && C9H17N1O8 && 513472
NeuAc && ''N''-acetyl-neuraminic acid && ''N''-アセチルノイラミン酸 && C11H19NO9 && 439197
NeuGc && ''N''-glycolyl-neuraminic acid && ''N''-グリコリルノイラミン酸 && C11H19NO10 && 123802
Kdn && 2-keto-3-deoxy-D-glycero- D-galacto-nononic acid && デアミノノイラミン酸 && C9H16O9 && 13991616
}}
|-
!colspan="4" align="center" style="background:lightgray"| Modifiers
{{#repeatnum:LBS/AbbrevRow|1|
AEPn && aminoethylphosphonic acid, or (2-aminoethyl)hydroxyphosphoryl- && アミノエチルホスホン酸（C-P結合）
MAEPn && ''N''-methyl aminoethylphosphonic acid, or (''N''-methyl-2-aminoethyl) hydroxyphosphoryl- && AEPnの''N''-メチル体（C-P結合）
EtnP && phosphoethanolamine (PEA), or 2-aminoethanolphospho- && ホスホエタノールアミン
PC && Phosphocholine && ホスホコリン
Butenyl && Butenyl && ブテニル基
Me && Methyl && メチル基
Et && Ethyl && エチル基
}}
|}

==={{Bilingual|分類体系|Page/ID-Code Design}}===
{{Twocolumn|
Major series of phosphosphingolipids are determined by molecules bound to their phosphates, and the series of glycosphingolipids are determined by oligosaccharides bound to their ceramides. The IUPAC series of glycosphingolipids (1977) were based on the order and bonding patterns of four sugars rooting at the long-chain base. Our series, however, are based on three sugars. Two original series, Echino and Schisto, are also added.
|スフィンゴリン脂質はリン酸に結合する分子や糖の種類、スフィンゴ糖脂質はセラミドに結合する糖鎖により系列を作成しています。1977年にIUPACが提唱したスフィンゴ糖脂質の系列は、長鎖塩基に結合する四糖の並びと結合を基準にしています。ここではより広い糖鎖の系列を検索できるよう、三糖を基準に分類しています。また新たにEchinoとSchistoの系列を加えています。
}}

{|
|
<table border=1>
<tr>
<td style="background-color:yellowgreen;" width=20px align="center"><big>L</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>B</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>S</big>
<td style="background-color:green;" width=20px align="center"><big>''G/P''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s1''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s2''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n1''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n2''</big>
<td style="background-color:firebrick; color:white" width=20px align="center"><big>''y''</big>
<td style="background-color:white;" width=20px align="center"><big>''c1''</big>
<td style="background-color:white;" width=20px align="center"><big>''c2''</big>
</tr>
</table>
|  
|
{| class="wikitable"
! '''G/P''' || '''G''' (glyco) || '''P''' (phospho)
|-
! '''s1, s2'''
|colspan="3"| structure code as explained below
|-
! '''n1, n2'''
|colspan="2"| number of sugars (2 digits)
|-
! '''y'''
|colspan="2"| number of sialic acids (1 digit)
|-
! '''c1, c2'''
|colspan="2"| serial numbers
|}
|}

==={{Bilingual|スフィンゴ糖脂質１文字目|First (s1) Digit for Glycosphingolipid}}===

{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
! colspan=2 | Major Series
|-
! Cerebroside
| colspan="3" style="text-align:left" | '''For GalCer and GlcCer, visit [[:Category:LBSC|this page]].'''
|-
! starting with <big>Galactose</big>
| [[Volatile:ListMol/LBStitle|LBSG1|'''G1''']] ([[Volatile:ClassMatrix|LBSG1.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG1}} items]])
|style="text-align:right"| '''Gal'''-Cer
|
{| style="width:100%;"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4?6?Galb1-Cer|Gala / Neogala]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4/6Galb1-Cer}}
|-
|style="border:0;text-align:left"|[[Volatile:ListMol/LBS|Mainchain.*Galb1-4Glcb1-3Galb1-Cer|Spirometo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Glcb1-3Galb1-Cer}}
|}
|-
! rowspan="8" | starting with <big>Glucose</big>
|-
| [[Volatile:ListMol/LBStitle|LBSG2|'''G2''']] ([[Volatile:ClassMatrix|LBSG2.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG2}} items]])
|style="text-align:right"| '''GalNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-4Galb1-4Glcb1-Cer|Ganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio]]<ref name="iso">In IUPAC, "iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*GlcNAcb1-3$.*GalNAcb1-4$Galb1-4Glcb1-Cer|Lactoganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3(GalNAcb1-4)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-3$?Galb1-4Glcb1-Cer|a-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|b-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|c-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|α-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|β-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG3|'''G3''']] ([[Volatile:ClassMatrix|LBSG3.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG3}} items]])
|style="text-align:right"| '''GlcNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer|Lacto]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto]]<ref name="neo">In IUPAC, "neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG4|'''G4''']] ([[Volatile:ClassMatrix|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG4}} items]])
|style="text-align:right"| '''Galα'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4Galb1-4Glcb1-Cer|Globo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-3Galb1-4Glcb1-Cer|Isoglobo]]<ref name="iso"/>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG5|'''G5''']] ([[Volatile:ClassMatrix|LBSG5.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG5}} items]])
|style="text-align:right"| Gal-Glc-Cer (Other than G2&sim;G4)
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-4Galb1-4Glcb1-Cer|Muco]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG6|'''G6''']] ([[Volatile:ClassMatrix|LBSG6.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG6}} items]])
|style="text-align:right"| '''Man'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcNAcb1-3Manb1-4Glcb1-Cer|Arthro]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3Manb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Mana1-3Manb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG7|'''G7''']] ([[Volatile:ClassMatrix|LBSG7.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG7}} items]])
|style="text-align:right"| '''NeuAc'''/'''NeuGc'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Neu(A~G)c.2-6Glcb1-Cer|Echino]]
|style="border:0;text-align:right"| '''NeuGc''' or {{LBS/FormatSugar|NeuAca2-6Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG8|'''G8''']] ([[Volatile:ClassMatrix|LBSG8.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG8}} items]])
|style="text-align:right"| '''GalNAc'''-Glc-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAc.1-4Glc.1-Cer|Schisto]]<ref>Makaaru CK, Damian RT, Smith DF, Cummings RD. "The human blood fluke Schistosoma mansoni synthesizes a novel type of glycosphingolipid" J Biol Chem 1992 267:2251-2257 PMID 1733932</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Glcb1-Cer}}
|}
|-
! starting with <big>Other Sugars</big>
| [[Volatile:ListMol/LBStitle|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|'''G'''('''A'''&sim;'''R''')]]
|colspan="2"| Symbols follow the Sugar-digit table.
|}
<references/>

==={{Bilingual|スフィンゴリン脂質１文字目|First (s1) Digit for Phosphosphingolipid}}===
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
!colspan="2"| Major Series
|-
! No Sugar Attached
| '''P1''' ([[:Category:LBSP|LBSP]])
| R-P-Cer
| Sphingomyelin and Ceramide phosphoetanolamine (Visit [[:Category:LBSP|this page]].)
|-
! rowspan="4" | starting with <big>Inositol</big>
| [[Volatile:ListMol/LBStitle|LBSP2|'''P2''']] ({{#countTitle:LBSP2}} items)
| style="text-align:right"| '''GlcN'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcN.1-.Ins-P-Cer|Protozoa & Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP3|'''P3''']] ({{#countTitle:LBSP3}} items)
|style="text-align:right"| '''GlcA'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcA.1-.Ins-P-Cer|Plant-specific]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcAa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP4|'''P4''']] ({{#countTitle:LBSP4}} items)
| style="text-align:right"| '''Man'''α/β1−2/6Ins1-P-Cer
|
{| style="width:100%"
| style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Man.1-.Ins-P-Cer|Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|Mana/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP5|'''P5''']] ({{#countTitle:LBSP5}} items)
| style="text-align:right"| Others
| style="text-align:right"| {{LBS/FormatSugar|Ins1-P-Cer}}
|}

==={{Bilingual|コード２文字目|Second (s2) Digit}}===

{{Bilingual|クリックすると一覧が出ます。記号の略称については|Click to see the full list. For abbreviations, see}} [[#Notation]].

{|
|-
| valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''A'''
| Glc [[File:LBS-Monomer-Glc.png]]
|-
! '''B'''
| Gal [[File:LBS-Monomer-Gal.png]]
|-
! '''C'''
| GlcNAc [[File:LBS-Monomer-GlcNAc.png]]
|-
! '''D'''
| GalNAc [[File:LBS-Monomer-GalNAc.png]]
|-
! '''E'''
| GlcN [[File:LBS-Monomer-GlcN.png]]
|-
! '''F'''
| GalN [[File:LBS-Monomer-GalN.png]]
|-
! '''G'''
| GlcA [[File:LBS-Monomer-GlcA.png]]
|-
! '''H'''
| GalA [[File:LBS-Monomer-GalA.png]]
|-
! '''I'''
| not used
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''J'''
| [[Volatile:ListMol/LBS|Structure.*Man|Mannose]] [[File:LBS-Monomer-Man.png]]
|-
! '''K'''
| [[Volatile:ListMol/LBS|Structure.*Rha|Rhamnose]] [[File:LBS-Monomer-Rha.png]]
|-
! '''L'''
| [[Volatile:ListMol/LBS|{{#encode:Structure.*Ins(Me)?-P-[^Cer]}}|Inositol]]
|-
! '''M'''
| Fucose ([[Volatile:ListMol/LBS|{{#encode:Structure[^F]+Fuc[^F]+$}}| 1]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){2}[^F]+$}}|2]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){3}}}|>3]]) [[File:LBS-Monomer-Fuc.png]]
|-
! '''N'''
| [[Volatile:ListMol/LBS|Structure.*Ara|Arabinose]] [[File:LBS-Monomer-Ara.png]]
|-
! '''O'''
| [[Volatile:ListMol/LBS|Structure.*Xyl|Xylose]] [[File:LBS-Monomer-Xyl.png]]
|-
! '''P'''
| [[Volatile:ListMol/LBS|Structure.*(NeuAc~NeuNH)|NeuAc / NeuNH]] [[File:LBS-Monomer-NeuAc.png]]
|-
! '''Q'''
| [[Volatile:ListMol/LBS|Structure.*(NeuGc)|NeuGc]] [[File:LBS-Monomer-NeuGc.png]]
|-
! '''R'''
| [[Volatile:ListMol/LBS|Structure.*(KDN)|Kdn]] [[File:LBS-Monomer-KDN.png]]
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''S'''
| [[Volatile:ListMol/LBS|Structure.*(Phospho)|Phosphate (except GIPC)]] [[File:LBS-Monomer-P.png]]
|-
! '''T'''
| [[Volatile:ListMol/LBS|Structure.*(AEPn)|(M)AEPn]], [[Volatile:ListMol/LBS|Structure.*(EtnP)|EtnP]], [[Volatile:ListMol/LBS|Structure.*(PC)|PC]] [[File:LBS-Monomer-AEPn.png]]
|-
! '''U'''
| [[Volatile:ListMol/LBS|Structure.*Sulfo|Sulfate]] [[File:LBS-Monomer-S.png]]
|-
! '''V'''
| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
|}

=={{Bilingual|生合成|Biosynthesis}}==
{{Twocolumn|
Sphingosine is synthesized from decarboxylating condensation of palmitoyl CoA with serine on the ER membrane. It is a 18-carbon amino alcohol (16 carbons from palmitic acid and 2 from serine) with one unsaturated bond (trans-form) at the C-4 position (2-amino-4-octadecene-1,3-diol). ([[:Category:LBS/Biosynthesis|more details]])
|
スフィンゴシンはパルミトイルCoAがアミノ酸セリンと脱炭酸縮合して生成します。炭素を18個含むアミノアルコール(16個がパルミチン酸、2個がセリン由来)でトランス型の不飽和結合をC-4に1つ含みます。（[[:Category:LBS/Biosynthesis|詳細はこちら]]）
}}

Category:LB

2022-08-10T01:52:50Z

Yasugi: /* Class Overview */

{{Huge|LipidBank}}
{{LB/Header}}
==Class Overview==

{{Twocolumn|
Biogenic substances insoluble to water are collectively called as '''lipid'''. Lipid is generally classified into the following three types.
* '''Simple lipid''' ... fatty acid esters of alchohol such as glycerol and sphingoid base.
* '''Complex lipid''' ... glycosylated or phosphorylated version of the simple lipid.
* '''Derived lipid''' ... alcohols and fatty acids derived by hydrolyzing the simple lipid. Also includes sterols and polyketides.
|
水に溶けない生体成分を一般に脂質と呼び、以下の3つに分けられます。
* '''単純脂質''' ... アルコールと脂肪酸のエステルで、スフィンゴ骨格とグリセロ骨格のものに大別されます。
* '''複合脂質''' ... 単純脂質にリン酸や糖がついたものです。
* '''誘導脂質''' ... 単純脂質を分解して得られるアルコール、脂肪酸。ステロールやポリケチドもここに含めます。
}}
<center>
{| class="wikitable"
|-
! colspan="3" | Lipid Overview
|-
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBF|LBF: Fatty acyls 脂肪酸アシル]]
 [[Image:LBF.png|100px]] 
Includes:
* fatty acids and acyl derivatives of length more than 7
| align="left" style="vertical-align:top" width=33%|
Glycerolipids グリセロ脂質
 [[Image:LBG.png|100px]] Includes:
* mono, di, triacyl glycerol
* glycoglycerolipid (mainly plants)
* phosphoglycerolipid
* [[:Category:LBGA|LBGA: Archaeal Lipid (Ether-type) 古細菌の脂質]]
| align="left" style="vertical-align:top" width=33%|
Sphingolipids スフィンゴ脂質
 [[Image:LBS.png|110px]] Includes:
* [[:Category:LBSB|LBSB: long-chain base and ceramide]]
* [[:Category:LBSG|LBSG: acidic glycosphingolipid]]
* [[:Category:LBSP|LBSP: phosphosphingolipid]]
|-
| style="vertical-align:top"|
| style="vertical-align:top"| Polyketides (not ready)
| style="vertical-align:top"| Sterols (not ready)
|}
</center>

; Related projects
* [[Lipoquality:Database|LipoQuality Database]]

Category:LBS

2022-08-10T01:46:55Z

Yasugi: /* {{Bilingual|概要|Class Overview}} */

{{Huge|{{Bilingual|スフィンゴ脂質|Sphingolipid}}}}
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
{| style="float:left"
| __TOC__
|}
=={{Bilingual|概要|Class Overview}}==

{{Twocolumn|
Three Sphingolipid categories (LBS) exist in this database.
|このデータベースではスフィンゴ脂質を以下に分けています。
}}

<center>
{|
|-
| style="vertical-align:top" width="33%"|
[[:Category:LBSB| '''Ceramide''']] {{LBS/Cer|OH}} セラミド
| style="vertical-align:top" width="33%"|
[[:Category:LBSG| '''Glycosphingolipid''']] {{LBS/Cer|O-(sugar)}} スフィンゴ糖脂質
| style="vertical-align:top" width="33%"|
[[:Category:LBSP| '''Phosphosphingolipid''']] {{LBS/Cer|O-(phosphate)}} スフィンゴリン脂質
|-
|
*[[:Category:LBSB|Long-chain base and ceramide]]
|
*[[:Category:LBSC|Cerebroside (monohexosyl ceramides)]]
*[[:Category:LBSG|Glycosylceramide ]]
|
*[[:Category:LBSP|Sphingomyelins and GIPC]]
|}
</center>

<center>
{| class="wikitable"
|<big>
[[:Category:LBS/Search|{{Bilingual|スフィンゴ脂質検索画面にいく|Go to Sphingolipid search.}}]]
</big>
|}
</center>

==={{Bilingual|スフィンゴ脂質の歴史|History of Sphingolipids}}===
{{Twocolumn|
Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure.<ref>Thudichum J.L.W. "A Treatise on the Chemical Constitution of the Balliere" Tindall and Cox, London, 1884</ref> The basic structure is a long-chain base (long-chain amino-alcohol) whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides.
Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (oligo)saccharides, respectively. Phosphosphingolipid includes sphingomyelin, and glycosphingolipid, cerebrosides and gangliosides. Both are abundant in neural tissues.<ref>Gault CR, Obeid LM, Hannun YA "An overview of sphingolipid synthesis to breakdown" Adv Exp Med Biol. 2010;688:1-23. PMID 20919643</ref>
|
スフィンゴ脂質は J.L.W. Thudichum (1829-1901) により機能や構造未知の脂質として脳から見いだされました。基本骨格は長鎖塩基 (長鎖アミノアルコール) のアミノ基が長鎖脂肪酸とアミド結合したもので、セラミドと呼ばれます。
スフィンゴ脂質はセラミドにリン酸が結合したスフィンゴリン脂質と糖が結合したスフィンゴ糖脂質に分けられます。スフィンゴリン脂質にはスフィンゴミエリンが、スフィンゴ糖脂質にはセレブロシドやガングリオシドなどが含まれ、いずれも神経系に多く存在します。
}}

<references/>

=={{Bilingual|スフィンゴ脂質|Sphingolipid}}==

==={{Bilingual|表記法|Notation}}===
{| class="wikitable collapsible collapsed" style="width:80%"
!colspan="4" align="center" style="background:lightgray"| Symbol Abbreviations (e.g. Glc = glucose)
|-
!colspan="4" align="center" style="background:lightgray"| Backbones
{{#repeatnum:LBS/AbbrevRow|1|
Cer && ceramide && セラミド &&
Sph && sphingosine && スフィンゴシン &&
}}
|-
!colspan="4" align="center" style="background:lightgray"| Sugars
{{#repeatnum:LBS/AbbrevRow|1|
Glc && glucose && グルコース && C6H12O6 &&
Gal && galactose && ガラクトース && C6H12O6 &&
GlcNAc && ''N''-acetyl-glucosamine && ''N''-アセチルグルコサミン && C8H15NO6
GalNAc && ''N''-acetyl-galactosamine && ''N''-アセチルガラクトサミン && C8H15NO6
GlcN && glucosamine && グルコサミン && C6H13NO5
GalN && galactosamine && ガラクトサミン && C6H13NO5
GlcA && glucuronic acid && グルクロン酸 && C6H10O7
GalA && galacturonic acid && ガラクツロン酸 && C6H10O7 &&
Man && mannose && マンノース && C6H12O6 && 18950
Rha && rhamnose (= 6-deoxy-mannose) && ラムノース (6-デオキシマンノース) && C6H12O5 && 19233
Ins && inositol && イノシトール && C6H12O6 && 892
Fuc && fucose (= 6-deoxy-galactose) && フコース (6-デオキシガラクトース) && C6H12O5 && 17106
Ara && arabinose && アラビノース && C5H10O5 && 5460291
Xyl && xylose && キシロース && C5H10O5 && 135191
NeuNH && (deacetyl) neuraminic acid (pyruvate + mannosamine) && ノイラミン酸 (ピルビン酸＋マンノサミン) && C9H17N1O8 && 513472
NeuAc && ''N''-acetyl-neuraminic acid && ''N''-アセチルノイラミン酸 && C11H19NO9 && 439197
NeuGc && ''N''-glycolyl-neuraminic acid && ''N''-グリコリルノイラミン酸 && C11H19NO10 && 123802
Kdn && 2-keto-3-deoxy-D-glycero- D-galacto-nononic acid && デアミノノイラミン酸 && C9H16O9 && 13991616
}}
|-
!colspan="4" align="center" style="background:lightgray"| Modifiers
{{#repeatnum:LBS/AbbrevRow|1|
AEPn && aminoethylphosphonic acid, or (2-aminoethyl)hydroxyphosphoryl- && アミノエチルホスホン酸（C-P結合）
MAEPn && ''N''-methyl aminoethylphosphonic acid, or (''N''-methyl-2-aminoethyl) hydroxyphosphoryl- && AEPnの''N''-メチル体（C-P結合）
EtnP && phosphoethanolamine (PEA), or 2-aminoethanolphospho- && ホスホエタノールアミン
PC && Phosphocholine && ホスホコリン
Butenyl && Butenyl && ブテニル基
Me && Methyl && メチル基
Et && Ethyl && エチル基
}}
|}

==={{Bilingual|分類体系|Page/ID-Code Design}}===
{{Twocolumn|
Major series of phosphosphingolipids are determined by molecules bound to their phosphates, and the series of glycosphingolipids are determined by oligosaccharides bound to their ceramides. The IUPAC series of glycosphingolipids (1977) were based on the order and bonding patterns of four sugars rooting at the long-chain base. Our series, however, are based on three sugars. Two original series, Echino and Schisto, are also added.
|スフィンゴリン脂質はリン酸に結合する分子や糖の種類、スフィンゴ糖脂質はセラミドに結合する糖鎖により系列を作成しています。1977年にIUPACが提唱したスフィンゴ糖脂質の系列は、長鎖塩基に結合する四糖の並びと結合を基準にしています。ここではより広い糖鎖の系列を検索できるよう、三糖を基準に分類しています。また新たにEchinoとSchistoの系列を加えています。
}}

{|
|
<table border=1>
<tr>
<td style="background-color:yellowgreen;" width=20px align="center"><big>L</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>B</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>S</big>
<td style="background-color:green;" width=20px align="center"><big>''G/P''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s1''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s2''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n1''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n2''</big>
<td style="background-color:firebrick; color:white" width=20px align="center"><big>''y''</big>
<td style="background-color:white;" width=20px align="center"><big>''c1''</big>
<td style="background-color:white;" width=20px align="center"><big>''c2''</big>
</tr>
</table>
|  
|
{| class="wikitable"
! '''G/P''' || '''G''' (glyco) || '''P''' (phospho)
|-
! '''s1, s2'''
|colspan="3"| structure code as explained below
|-
! '''n1, n2'''
|colspan="2"| number of sugars (2 digits)
|-
! '''y'''
|colspan="2"| number of sialic acids (1 digit)
|-
! '''c1, c2'''
|colspan="2"| serial numbers
|}
|}

==={{Bilingual|スフィンゴ糖脂質１文字目|First (s1) Digit for Glycosphingolipid}}===

{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
! colspan=2 | Major Series
|-
! Cerebroside
| colspan="3" style="text-align:left" | '''For GalCer and GlcCer, visit [[:Category:LBSC|this page]].'''
|-
! starting with <big>Galactose</big>
| [[Volatile:ListMol/LBStitle|LBSG1|'''G1''']] ([[Volatile:ClassMatrix|LBSG1.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG1}} items]])
|style="text-align:right"| '''Gal'''-Cer
|
{| style="width:100%;"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4?6?Galb1-Cer|Gala / Neogala]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4/6Galb1-Cer}}
|-
|style="border:0;text-align:left"|[[Volatile:ListMol/LBS|Mainchain.*Galb1-4Glcb1-3Galb1-Cer|Spirometo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Glcb1-3Galb1-Cer}}
|}
|-
! rowspan="8" | starting with <big>Glucose</big>
|-
| [[Volatile:ListMol/LBStitle|LBSG2|'''G2''']] ([[Volatile:ClassMatrix|LBSG2.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG2}} items]])
|style="text-align:right"| '''GalNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-4Galb1-4Glcb1-Cer|Ganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio]]<ref name="iso">In IUPAC, "iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*GlcNAcb1-3$.*GalNAcb1-4$Galb1-4Glcb1-Cer|Lactoganglio]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3(GalNAcb1-4)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-3$?Galb1-4Glcb1-Cer|a-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|b-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-8NeuAca2-3$?Galb1-4Glcb1-Cer|c-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|α-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*$?NeuAca2-8NeuAca2-6$?GalNAcb1-4Galb1-4Glcb1-Cer|β-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG3|'''G3''']] ([[Volatile:ClassMatrix|LBSG3.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG3}} items]])
|style="text-align:right"| '''GlcNAcβ'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer|Lacto]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto]]<ref name="neo">In IUPAC, "neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG4|'''G4''']] ([[Volatile:ClassMatrix|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG4}} items]])
|style="text-align:right"| '''Galα'''-Galβ-Glcβ-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4Galb1-4Glcb1-Cer|Globo]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-3Galb1-4Glcb1-Cer|Isoglobo]]<ref name="iso"/>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-3Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG5|'''G5''']] ([[Volatile:ClassMatrix|LBSG5.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG5}} items]])
|style="text-align:right"| Gal-Glc-Cer (Other than G2&sim;G4)
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Galb1-4Galb1-4Glcb1-Cer|Muco]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4Galb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG6|'''G6''']] ([[Volatile:ClassMatrix|LBSG6.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG6}} items]])
|style="text-align:right"| '''Man'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcNAcb1-3Manb1-4Glcb1-Cer|Arthro]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNAcb1-3Manb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Mana1-3Manb1-4Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG7|'''G7''']] ([[Volatile:ClassMatrix|LBSG7.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG7}} items]])
|style="text-align:right"| '''NeuAc'''/'''NeuGc'''-Glcβ-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Neu(A~G)c.2-6Glcb1-Cer|Echino]]
|style="border:0;text-align:right"| '''NeuGc''' or {{LBS/FormatSugar|NeuAca2-6Glcb1-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSG8|'''G8''']] ([[Volatile:ClassMatrix|LBSG8.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG8}} items]])
|style="text-align:right"| '''GalNAc'''-Glc-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAc.1-4Glc.1-Cer|Schisto]]<ref>Makaaru CK, Damian RT, Smith DF, Cummings RD. "The human blood fluke Schistosoma mansoni synthesizes a novel type of glycosphingolipid" J Biol Chem 1992 267:2251-2257 PMID 1733932</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Glcb1-Cer}}
|}
|-
! starting with <big>Other Sugars</big>
| [[Volatile:ListMol/LBStitle|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|'''G'''('''A'''&sim;'''R''')]]
|colspan="2"| Symbols follow the Sugar-digit table.
|}
<references/>

==={{Bilingual|スフィンゴリン脂質１文字目|First (s1) Digit for Phosphosphingolipid}}===
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
!colspan="2"| Major Series
|-
! No Sugar Attached
| '''P1''' ([[:Category:LBSP|LBSP]])
| R-P-Cer
| Sphingomyelin and Ceramide phosphoetanolamine (Visit [[:Category:LBSP|this page]].)
|-
! rowspan="4" | starting with <big>Inositol</big>
| [[Volatile:ListMol/LBStitle|LBSP2|'''P2''']] ({{#countTitle:LBSP2}} items)
| style="text-align:right"| '''GlcN'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcN.1-.Ins-P-Cer|Protozoa & Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|GlcNa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP3|'''P3''']] ({{#countTitle:LBSP3}} items)
|style="text-align:right"| '''GlcA'''α/β1−2/6Ins1-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GlcA.1-.Ins-P-Cer|Plant-specific]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|GlcAa/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP4|'''P4''']] ({{#countTitle:LBSP4}} items)
| style="text-align:right"| '''Man'''α/β1−2/6Ins1-P-Cer
|
{| style="width:100%"
| style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Man.1-.Ins-P-Cer|Fungi-specific]]
| style="border:0;text-align:right"| {{LBS/FormatSugar|Mana/b1-2/6Ins1-P-Cer}}
|}
|-
| [[Volatile:ListMol/LBStitle|LBSP5|'''P5''']] ({{#countTitle:LBSP5}} items)
| style="text-align:right"| Others
| style="text-align:right"| {{LBS/FormatSugar|Ins1-P-Cer}}
|}

==={{Bilingual|コード２文字目|Second (s2) Digit}}===

{{Bilingual|クリックすると一覧が出ます。記号の略称については|Click to see the full list. For abbreviations, see}} [[#Notation]].

{|
|-
| valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''A'''
| Glc [[File:LBS-Monomer-Glc.png]]
|-
! '''B'''
| Gal [[File:LBS-Monomer-Gal.png]]
|-
! '''C'''
| GlcNAc [[File:LBS-Monomer-GlcNAc.png]]
|-
! '''D'''
| GalNAc [[File:LBS-Monomer-GalNAc.png]]
|-
! '''E'''
| GlcN [[File:LBS-Monomer-GlcN.png]]
|-
! '''F'''
| GalN [[File:LBS-Monomer-GalN.png]]
|-
! '''G'''
| GlcA [[File:LBS-Monomer-GlcA.png]]
|-
! '''H'''
| GalA [[File:LBS-Monomer-GalA.png]]
|-
! '''I'''
| not used
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''J'''
| [[Volatile:ListMol/LBS|Structure.*Man|Mannose]] [[File:LBS-Monomer-Man.png]]
|-
! '''K'''
| [[Volatile:ListMol/LBS|Structure.*Rha|Rhamnose]] [[File:LBS-Monomer-Rha.png]]
|-
! '''L'''
| [[Volatile:ListMol/LBS|{{#encode:Structure.*Ins(Me)?-P-[^Cer]}}|Inositol]]
|-
! '''M'''
| Fucose ([[Volatile:ListMol/LBS|{{#encode:Structure[^F]+Fuc[^F]+$}}| 1]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){2}[^F]+$}}|2]], [[Volatile:ListMol/LBS|{{#encode:Structure([^F]+Fuc){3}}}|>3]]) [[File:LBS-Monomer-Fuc.png]]
|-
! '''N'''
| [[Volatile:ListMol/LBS|Structure.*Ara|Arabinose]] [[File:LBS-Monomer-Ara.png]]
|-
! '''O'''
| [[Volatile:ListMol/LBS|Structure.*Xyl|Xylose]] [[File:LBS-Monomer-Xyl.png]]
|-
! '''P'''
| [[Volatile:ListMol/LBS|Structure.*(NeuAc~NeuNH)|NeuAc / NeuNH]] [[File:LBS-Monomer-NeuAc.png]]
|-
! '''Q'''
| [[Volatile:ListMol/LBS|Structure.*(NeuGc)|NeuGc]] [[File:LBS-Monomer-NeuGc.png]]
|-
! '''R'''
| [[Volatile:ListMol/LBS|Structure.*(KDN)|Kdn]] [[File:LBS-Monomer-KDN.png]]
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''S'''
| [[Volatile:ListMol/LBS|Structure.*(Phospho)|Phosphate (except GIPC)]] [[File:LBS-Monomer-P.png]]
|-
! '''T'''
| [[Volatile:ListMol/LBS|Structure.*(AEPn)|(M)AEPn]], [[Volatile:ListMol/LBS|Structure.*(EtnP)|EtnP]], [[Volatile:ListMol/LBS|Structure.*(PC)|PC]] [[File:LBS-Monomer-AEPn.png]]
|-
! '''U'''
| [[Volatile:ListMol/LBS|Structure.*Sulfo|Sulfate]] [[File:LBS-Monomer-S.png]]
|-
! '''V'''
| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
|}

=={{Bilingual|生合成|Biosynthesis}}==
{{Twocolumn|
Sphingosine is synthesized from decarboxylating condensation of palmitoyl CoA with serine on the ER membrane. It is a 18-carbon amino alcohol (16 carbons from palmitic acid and 2 from serine) with one unsaturated bond (trans-form) at the C-4 position (2-amino-4-octadecene-1,3-diol). ([[:Category:LBS/Biosynthesis|more details]])
|
スフィンゴシンはパルミトイルCoAがアミノ酸セリンと脱炭酸縮合して生成します。炭素を18個含むアミノアルコール(16個がパルミチン酸、2個がセリン由来)でトランス型の不飽和結合をC-4に1つ含みます。（[[:Category:LBS/Biosynthesis|詳細はこちら]]）
}}

Category:LB

2022-08-10T01:38:06Z

Yasugi: /* Class Overview */

{{Huge|LipidBank}}
{{LB/Header}}
==Class Overview==

{{Twocolumn|
Biogenic substances insoluble to water are collectively called as '''lipid'''. Lipid is generally classified into the following three types.
* '''Simple lipid''' ... fatty acid esters of alchohol such as glycerol and sphingoid base.
* '''Complex lipid''' ... glycosylated or phosphorylated version of the simple lipid.
* '''Derived lipid''' ... alcohols and fatty acids derived by hydrolyzing the simple lipid. Also includes sterols and polyketides.
|
水に溶けない生体成分を一般に脂質と呼び、以下の3つに分けられます。
* '''単純脂質''' ... アルコールと脂肪酸のエステルで、スフィンゴ骨格とグリセロ骨格のものに大別されます。
* '''複合脂質''' ... 単純脂質にリン酸や糖がついたものです。
* '''誘導脂質''' ... 単純脂質を分解して得られるアルコール、脂肪酸。ステロールやポリケチドもここに含めます。
}}
<center>
{| class="wikitable"
|-
! colspan="3" | Lipid Overview
|-
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBF|LBF: Fatty acyls 脂肪酸アシル]]
 [[Image:LBF.png|100px]] 
Includes:
* fatty acids and acyl derivatives of length more than 7
| align="left" style="vertical-align:top" width=33%|
Glycerolipids グリセロ脂質
 [[Image:LBG.png|100px]] Includes:
* mono, di, triacyl glycerol
* glycoglycerolipid (mainly plants)
* phosphoglycerolipid
* [[:Category:LBGA|LBGA: Archaeal Lipid (Ether-type) 古細菌の脂質]]
| align="left" style="vertical-align:top" width=33%|
Sphingolipids スフィンゴ脂質
 [[Image:LBS.png|110px]] Includes:
* [[:Category:LBSB|LBSB: long-chain base and ceramide]]
* [[:Category:LBSG|LBSG: glycosphingolipid]]
* [[:Category:LBSP|LBSP: phosphosphingolipid]]
|-
| style="vertical-align:top"|
| style="vertical-align:top"| Polyketides (not ready)
| style="vertical-align:top"| Sterols (not ready)
|}
</center>

; Related projects
* [[Lipoquality:Database|LipoQuality Database]]

Category:LB

2022-08-09T14:23:33Z

Yasugi: /* Class Overview */

{{Huge|LipidBank}}
{{LB/Header}}
==Class Overview==

{{Twocolumn|
Biogenic substances insoluble to water are collectively called as '''lipid'''. Lipid is generally classified into the following three types.
* '''Simple lipid''' ... fatty acid esters of alchohol such as glycerol and sphingoid base.
* '''Complex lipid''' ... glycosylated or phosphorylated version of the simple lipid.
* '''Derived lipid''' ... alcohols and fatty acids derived by hydrolyzing the simple lipid. Also includes sterols and polyketides.
|
水に溶けない生体成分を一般に脂質と呼び、以下の3つに分けられます。
* '''単純脂質''' ... アルコールと脂肪酸のエステルで、スフィンゴ骨格とグリセロ骨格のものに大別されます。
* '''複合脂質''' ... 単純脂質にリン酸や糖がついたものです。
* '''誘導脂質''' ... 単純脂質を分解して得られるアルコール、脂肪酸。ステロールやポリケチドもここに含めます。
}}
<center>
{| class="wikitable"
|-
! colspan="3" | Lipid Overview
|-
| align="left" style="vertical-align:top" width=33%|
[[:Category:LBF|LBF: Fatty acyls 脂肪酸アシル]]
 [[Image:LBF.png|100px]] 
Includes:
* fatty acids and acyl derivatives of length more than 7
| align="left" style="vertical-align:top" width=33%|
Glycerolipids グリセロ脂質
 [[Image:LBG.png|100px]] Includes:
* mono, di, triacyl glycerol
* glycoglycerolipid (mainly plants)
* phosphoglycerolipid
* [[:Category:LBGA|LBGA: Archaeal Lipid (Ether-type) 古細菌の脂質]]
| align="left" style="vertical-align:top" width=33%|
Sphingolipids スフィンゴ脂質
 [[Image:LBS.png|110px]] Includes:
* [[:Category:LBSB|LBSB: ceramide and long-chain base]]
* [[:Category:LBSG|LBSG: glycosphingolipid]]
* [[:Category:LBSP|LBSP: phosphosphingolipid]]
|-
| style="vertical-align:top"|
| style="vertical-align:top"| Polyketides (not ready)
| style="vertical-align:top"| Sterols (not ready)
|}
</center>

; Related projects
* [[Lipoquality:Database|LipoQuality Database]]

Sandbox1

2010-10-18T04:25:44Z

Yasugi:

--d100 10 --

a