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 as follows. 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. | Sphingoid base is a 2-aminoalkane (or alkene) 1,3-diol with 2R, 3R stereochemistry. Major types are listed as follows. 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. | ||
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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。 | 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。 | ||
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{| class="wikitable" | {| class="wikitable" | ||
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| d18:0 | | d18:0 | ||
| Sa or DHSo | | Sa or DHSo | ||
| | | Lacking the trans-double bond of sphingosine | ||
|- | |- | ||
| 4-hydroxysphinganine = phytosphingosine | | 4-hydroxysphinganine = phytosphingosine | ||
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| | | | ||
| Found in skin | | Found in skin | ||
|} | |||
====Notation==== | |||
{| | |||
|style="background:lightgray"| <font size="+2">d18:1</font> | |||
| ''h'', ''d'' or ''t'' stands for single, double, or triple hydroxy groups, respectively.<br/>18 is the carbon chain length.<br/>1 is the number of unsaturated bonds (double bonds). | |||
|} | |} | ||
| Line 44: | Line 49: | ||
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。 | 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。 | ||
}} | }} | ||
{| 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 | |||
| h16:0 - h26:0<br/>h16:1 - h26:1<br/>h16:0<br/>VLCFA | |||
| d18:2Δ4E8E/Z<br/>d18:2Δ4E8E/Z<br/>d18:1Δ8E/Z<br/>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. doi: 10.1016/j.pbi.2013.02.009.</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.doi: 10.1007/s00018-003-2243-4.</ref><br/><ref name="Mark"/><ref name="War"/><br/><ref name="Mark"/><br/><ref name="Mark"/><ref name="War"/> | |||
| hVLCFA<br/>h14:0 - h26:0<br/>h20:1 - h26:1 | |||
| t18:1Δ8E/Z<br/>t18:1Δ8E/Z, t18:0<br/>t18:1Δ8E/Z, t18:0 | |||
| <ref name="Mark"/><br/><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 doi: 10.1007/s00216-013-7130-8.</ref><br/><ref name="Mark"/><ref name="Bure"/> | |||
|- | |||
|Fungi | |||
| h16:0 - h18:0<br/>h16:1 - h18:1 | |||
| 9-mehtyl d18:2Δ4E,8E<br/>9-mehtyl 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. doi: 10.3389/fmicb.2011.00212.</ref><ref name="War"/><br/><ref name="Nim"/><ref name="War"/> | |||
| h24:0 - h26:0<br/>h24:1 - h26:1<br/>h16:0 - h26:0 | |||
| t18:0<br/>t18:0<br/>t18:0, t20:0 | |||
| <ref name="Nim"/><br/><ref name="War"/><br/><ref name="War"/><ref name="Bure"/> | |||
|} | |||
<references/> | |||
Revision as of 03:20, 25 November 2015
Sphingoid bases
Sphingoid base is a 2-aminoalkane (or alkene) 1,3-diol with 2R, 3R stereochemistry. Major types are listed as follows. 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. |
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。 |
| Name | Symbol | Abbreviation | Note |
|---|---|---|---|
| sphingosine | 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-mehtyl d18:2Δ4E,8E 9-mehtyl 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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