Category:LBSB
Long-chain base
Long-chain base (LCB or sphingoid base) is a 2-aminoalkane (or alkene) 1,3-diol with 2R, 3R stereochemistry (D-erythro for dihydroxy LCB and D-ribo for trihydroxy LCB). Major types are listed in the following Table. Animals usually contain LCB of length 18 (d18:1) and a little amount of d20:1. In yeast (S. cerevisiae), the predominant LCB is 4-hydroxysphinganine (t18:0)[1]. In higher plants, six LCB are major( (8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2) with little d18:0, t18:0, and (4E)-d18:1. This means (4Z)-d18:1 is absent in plants. Insects contain LCB of shorter chains, e.g. d14:1 and d16:1. |
長鎖塩基（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-ジオールを指す（立体化学はジヒドロキシLCBがD-エリスロ、トリヒドロキシLCBがD-リボ型）。代表的なものは以下のとおり。動物は通常、鎖長18のLCBを持ち (d18:1)、少量の d20:1 がある。イースト（パン酵母）で主要なLCBは t18:0 になる。高等植物では 6 種の LCB、(8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2 が多く、少量の d18:0, t18:0, (4E)-d18:1、も見られる。(4Z)-d18:1 は見られない。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。 |
Notation
| Sph d18:1 |
Sph is an abbreviation of long-chain base. d or t stands for double, or triple hydroxy groups, respectively. (We count the terminal alcohol.) 18 is the carbon chain length. 1 is the number of unsaturated bonds (double bonds). |
Sphは長鎖塩基の略号。 d, t はそれぞれ 2, 3 個の水酸基を意味する （アルコールの水酸基含む）。18は炭素鎖の長さ。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 |
| 6-hydroxysphingosine (4E)-2-amino-octadec-4-ene-1,3,6-triol |
6-t18:1 | Found in skin |
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 |
[2][3] [2][3] [2] [2][3] |
hVLCFA h14:0 - h26:0 h20:1 - h26:1 |
t18:1Δ8E/Z t18:1Δ8E/Z, t18:0 t18:1Δ8E/Z, t18:0 |
[2] [4] [2][4] |
| Fungi | h16:0 - h18:0 h16:1 - h18:1 |
9-methyl d18:2Δ4E,8E 9-methyl d18:2Δ4E,8E |
[5][3] [5][3] |
h24:0 - h26:0 h24:1 - h26:1 h16:0 - h26:0 |
t18:0 t18:0 t18:0, t20:0 |
[5] [3] [3][4] |
- ↑ Yeast is an exceptional case. Many fungi contain a (4,8)-diunsaturated, 9-methyl-branched LCB.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 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.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 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.
- ↑ 4.0 4.1 4.2 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.
- ↑ 5.0 5.1 5.2 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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