Category:LBSP: Difference between revisions

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Sphingoid base is a 2-aminoalkane (or alkene) 1,3-diol with 2R, 3R stereochemistry. Major types are listed in the following Table. Plants contain desaturated sphingosines, i.g. 4,8-sphingediene (d18:2), and insects contain sphingoid bases of shorter chains, e.g. d14:1 and d16:1. Animals usually contain sphingoid bases of length 18 and a little amount of 20.
Sphingoid base is a 2-aminoalkane (or alkene) 1,3-diol with 2R, 3R stereochemistry. Major types are listed in the following Table. Plants contain desaturated sphingosines, i.g. 4,8-sphingediene (d18:2), and insects contain sphingoid bases of shorter chains, e.g. d14:1 and d16:1. Animals usually contain sphingoid bases of length 18 and a little amount of 20.
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スフィンゴイド塩基は 2-アミノアルカン(アルケン) 1,3-ジオールを指す。代表的なものは以下のとおり。植物は不飽和のスフィンゴシン、例えば 4,8-スフィンゲジエン (d18:2)をもち、昆虫は短い炭素鎖のスフィンゴイド塩基、例えば d14:1, d16:1 を持つ。動物の場合、通常の鎖長は18で20のものが少量存在する。
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-ジオールを指す。代表的なものは以下のとおり。植物は不飽和のスフィンゴシン、例えば 4,8-スフィンゲジエン (d18:2)をもち、昆虫は短い炭素鎖のスフィンゴイド塩基、例えば d14:1, d16:1 を持つ。動物の場合、通常の鎖長は18で20のものが少量存在する。
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Revision as of 04:44, 25 November 2015

Sphingoid bases

Sphingoid base is a 2-aminoalkane (or alkene) 1,3-diol with 2R, 3R stereochemistry. Major types are listed in the following Table. Plants contain desaturated sphingosines, i.g. 4,8-sphingediene (d18:2), and insects contain sphingoid bases of shorter chains, e.g. d14:1 and d16:1. Animals usually contain sphingoid bases of length 18 and a little amount of 20.

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-ジオールを指す。代表的なものは以下のとおり。植物は不飽和のスフィンゴシン、例えば 4,8-スフィンゲジエン (d18:2)をもち、昆虫は短い炭素鎖のスフィンゴイド塩基、例えば d14:1, d16:1 を持つ。動物の場合、通常の鎖長は18で20のものが少量存在する。

Name Symbol Abbreviation Note
sphingosine
(2-amino-4-octadecene-1,3-diol)
d18:1 So
sphinganine = dihydrosphingosine d18:0 Sa or DHSo Lacking the trans-double bond of sphingosine
4-hydroxysphinganine = phytosphingosine t18:0 Phyto Originally found in plants but also in animals
6-hydroxysphingosine 6-t18:1 Found in skin

Notation

d18:1  h, d or t stands for single, double, or triple hydroxy groups, respectively.
18 is the carbon chain length.
1 is the number of unsaturated bonds (double bonds).

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, but ceramides in skin may contain >30 carbon chains.

セラミドという言葉は基本的に N-アシルスフィンゴイド塩基を指すが、最も代表的なものは N-アシルスフィンゴシンである。結合する脂肪酸の炭素長は16から26だが、皮膚のセラミドには長さが30以上の場合もある。

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. 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. 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. 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. 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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