Category:LBSB: Difference between revisions
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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. The structural variation depends on biological species. | 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. The structural variation depends on biological species.<ref>Merrill AH (2011) "Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics" Chem. Rev. 111, 6387–6422. PMID 21942574</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-ジオールを指します。生体内ではスフィンゴ脂質の構成成分で、遊離のLCBは微量しか存在しません。生物種によってLCBの構造は大きく異なります。 | |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-ジオールを指します。生体内ではスフィンゴ脂質の構成成分で、遊離のLCBは微量しか存在しません。生物種によってLCBの構造は大きく異なります。 | ||
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| Higher animals || sphingosine (= (4E)-d18:1) [general] <br/> (4E)-d20:1 [nerve tissue], t18:0 [intestine] | | Higher animals || sphingosine (= (4E)-d18:1) [general] <br/> (4E)-d20:1 [nerve tissue], t18:0 [intestine] | ||
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| Insects || short-chain sphingosine (d14:1, d16:1) [general] | | Insects || short-chain sphingosine (d14:1, d16:1) [general]<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 (2013) "Biochemical membrane lipidomics during Drosophila development" Dev Cell 24, 98-111. PMID 23260625</ref> | ||
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| Plants || (8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2 [general] | | Plants || (8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2 [general] | ||
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| Fungi || 9-methyl (4E,8E)-d18:2, t18:0 [general] | | Fungi || 9-methyl (4E,8E)-d18:2, t18:0 [general] | ||
|} | |} | ||
===Notation=== | ===Notation=== | ||
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* Sphingosine 1-phosphate is a lipid mediator of cell proliferation and motility control. | * Sphingosine 1-phosphate is a lipid mediator of cell proliferation and motility control. | ||
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* 遊離のLCBはアポトーシスを惹起します。 | * 遊離のLCBはアポトーシスを惹起します。<ref>Hung WC, Chang HC, Chuang LY (1999) "Activation of caspase-3-like proteases in apoptosis induced by sphingosine and other long-chain bases in Hep3B hepatoma cells" Biochem J. 338:161-166. PMID 9931312</ref> | ||
* 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。 | * 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。 | ||
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<references/> | |||
==Ceramides== | ==Ceramides== | ||
Revision as of 18:24, 15 March 2016
Long-chain base
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. The structural variation depends on biological species.[1] |
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-ジオールを指します。生体内ではスフィンゴ脂質の構成成分で、遊離のLCBは微量しか存在しません。生物種によってLCBの構造は大きく異なります。 |
| Species | |
|---|---|
| Higher animals | sphingosine (= (4E)-d18:1) [general] (4E)-d20:1 [nerve tissue], t18:0 [intestine] |
| Insects | short-chain sphingosine (d14:1, d16:1) [general][2] |
| Plants | (8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2 [general] |
| Fungi | 9-methyl (4E,8E)-d18:2, t18:0 [general] |
Notation
| 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). |
Sphは長鎖塩基 LCB の略号。 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）。18は炭素鎖長。コロンの次にくる1は不飽和結合（二重結合）の数。 |
Major Sphingoid
| Name | Symbol | Abbreviation | Note |
|---|---|---|---|
| sphingosine = (4E)-sphingenine (4E)-2-amino-octadec-4-ene-1,3-diol |
d18:1 | So | Major in mammals |
| sphinganine = dihydrosphingosine 2-amino-octadecane-1,3-diol |
d18:0 | Sa or DHSo | Lacking the trans-double bond of sphingosine |
| 4-hydroxysphinganine = phytosphingosine 2-amino-octadecane-1,3,4-triol |
t18:0 | Phyto | Major in fungi and plant |
| 6-hydroxysphingosine (4E)-2-amino-octadec-4-ene-1,3,6-triol |
6-t18:1 | Found in skin |
Bioactivity
|
|
- ↑ Merrill AH (2011) "Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics" Chem. Rev. 111, 6387–6422. PMID 21942574
- ↑ 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 (2013) "Biochemical membrane lipidomics during Drosophila development" Dev Cell 24, 98-111. PMID 23260625
- ↑ Hung WC, Chang HC, Chuang LY (1999) "Activation of caspase-3-like proteases in apoptosis induced by sphingosine and other long-chain bases in Hep3B hepatoma cells" Biochem J. 338:161-166. PMID 9931312
Ceramides
The word ceramide (Cer) basically refers to all N-acyl-sphingoid bases, but most representative one is N-acylsphingosines. The conjugated fatty acids are often 16 to 26 carbon chains. In mammalian skin, free ceramides comprise 55% of the intercellular lipid layer and exhibit barrier function. The ceramides may contain >30 carbon chains. Atopic dermatitis (and dry skin) is associated with a decrease and compositional change of such ceramides. In industry, ceramides are extracted from vegetable-oil cakes from corn, rice, wheat, soybean, and others. |
セラミドという言葉は基本的に N-アシルスフィンゴイド塩基を指すが、最も代表的なものは N-アシルスフィンゴシンである。結合する脂肪酸の炭素長は16から26である。 動物の皮膚における角質細胞間脂質では遊離のセラミドが55S%を占め、バリア機能を持つ。セラミドの長さも30以上に及ぶ。アトピー性皮膚炎や乾燥肌ではセラミド量が減少し、組成も変化していることが知られる。 工業的には、セラミドはトウモロコシ、コメ、コムギ、ダイズ等からの植物油滓から精製する。 |
Notation
| 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. |
Cerはセラミドの略号。左側が長鎖塩基、スラッシュを挟んで右側に脂肪酸。このサイトでは上付き／下付きは使用しない（見づらいため）。また E (トランス）, Z (シス）もイタリックにしていない。 |
Composition
| Species | Glycosylceramide | Glycosyl inositol phosphoceramide (GIPC) | ||||
|---|---|---|---|---|---|---|
| Fatty acid | Long chain base | References | Fatty acid | Long chain base | References | |
| Plants | h16:0 - h26:0 h16:1 - h26:1 h16:0 VLCFA |
d18:2Δ4E8E/Z d18:2Δ4E8E/Z d18:1Δ8E/Z t18:1Δ8E/Z |
[1][2] [1][2] [1] [1][2] |
hVLCFA h14:0 - h26:0 h20:1 - h26:1 |
t18:1Δ8E/Z t18:1Δ8E/Z, t18:0 t18:1Δ8E/Z, t18:0 |
[1] [3] [1][3] |
| Fungi | h16:0 - h18:0 h16:1 - h18:1 |
9-methyl d18:2Δ4E,8E 9-methyl d18:2Δ4E,8E |
[4][2] [4][2] |
h24:0 - h26:0 h24:1 - h26:1 h16:0 - h26:0 |
t18:0 t18:0 t18:0, t20:0 |
[4] [2] [2][3] |
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Markham JE, Lynch DV, Napier JA, Dunn TM, Cahoon EB. Plant sphingolipids: function follows form. Curr Opin Plant Biol. 2013 16: 350-7. doi: 10.1016/j.pbi.2013.02.009.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 Warnecke D, Heinz E..Recently discovered functions of glucosylceramides in plants and fungi. Cell Mol Life Sci. 2003 60:919-41.doi: 10.1007/s00018-003-2243-4.
- ↑ 3.0 3.1 3.2 Buré C, Cacas JL, Mongrand S, Schmitter JM. Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry. Anal Bioanal Chem. 2013 doi: 10.1007/s00216-013-7130-8.
- ↑ 4.0 4.1 4.2 Nimrichter L, Rodrigues ML. Fungal glucosylceramides: from structural components to biologically active targets of new antimicrobials. Front Microbiol. 2011 2:212. doi: 10.3389/fmicb.2011.00212.
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