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
| 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). |
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 yeast (S. cerevisiae) |
| 6-hydroxysphingosine (4E)-2-amino-octadec-4-ene-1,3,6-triol |
6-t18:1 | Found in skin |
- ↑ Yeast is an exceptional case. Many fungi contain a (4,8)-diunsaturated, 9-methyl-branched LCB.
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 | The first part indicates the LCB part and the second, fatty acid. In this page 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. |
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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