Category:LBSB

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Upper classes: LB LBS

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. When LCB is linked with a long-chain fatty acid via an amide bond, it is called a ceramide (Cer).[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、生体内ではスフィンゴ脂質の構成成分です。遊離のLCBは微量しか存在しません。長鎖塩基に長鎖脂肪酸がアミド結合したものを、セラミドと呼びます。

  1. Yamaji T, Hanada K "Sphingolipid metabolism and interorganellar localization of sphingolipid enzymes and lipid transfer proteins" Traffic 2015 16:101-122. PMID 25382749

Contents

Notation 表記法

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).

長鎖塩基 LCB は Sph と表します。 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)を意味し、18は炭素鎖長です。コロンの次にくる1は不飽和結合(二重結合)の数を表します。

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.
セラミドは Cer と表します。左側が長鎖塩基、スラッシュを挟んで右側は脂肪酸を表しています。このサイトでは上付き/下付きは使用せず(見づらいため)、 E (トランス), Z (シス)もイタリックにしていません。
Common Name sphingosine
(= (4E)-sphingenine)
スフィンゴシン
sphinganine
(= dihydrosphingosine)
スフィンガニン
phytosphingosine
(= 4-hydroxydihydrosphingosine)
フィトスフィンゴシン
6-hydroxysphingosine

6-ヒドロキシスフィンゴシン
Abbreviation d18:1 or So d18:0 or Sa (DHSo) t18:0 or Phyto t18:1 or 6-t18:1
Structure 構造
| OH
(C14-chain)OH
| NH2
| OH
(C14-chain)OH
| NH2
| OH
(C14-chain)OH
OH | | NH2
| OH
(C12-chain)
OH
| OH | NH2
Source 分布 Major in mammals Major in mammals Major in fungi and plant Found in skin

Long-chain base 長鎖塩基

The structural variation of LCB depends on biological species.[1]

生物種によってLCBの構造は大きく異なります。

Classification Long-chain base
Mammalia sphingosine (= (4E)-d18:1)
(4E)-d20:1 (nerve tissue), t18:0 (intestine)
Arthropoda short-chain sphingosine (d14:1, d16:1) [2]
Plantae (8E/Z)-d18:1, (8E/Z)-t18:1, (4E,8E/Z)-d18:2
Fungi 9-methyl (4E,8E)-d18:2, t18:0


Bioactivity

  • Free LCB induces apoptosis.[3]
  • Sphingosine 1-phosphate is a lipid mediator of cell proliferation and motility control.[4]

  • 遊離のLCBはアポトーシスを惹起します。
  • 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。

  1. Merrill AH "Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics" Chem. Rev. 2011 111:6387–6422. PMID 21942574
  2. 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 "Biochemical membrane lipidomics during Drosophila development" Dev Cell 2013 24:98-111. PMID 23260625
  3. Hung WC, Chang HC, Chuang LY "Activation of caspase-3-like proteases in apoptosis induced by sphingosine and other long-chain bases in Hep3B hepatoma cells" Biochem J. 1999 338:161-166. PMID 9931312
  4. Takabe K, Spiegel S."Export of sphingosine-1-phosphate and cancer progression"J Lipid Res. 2014 55:1839-46. PMID 24474820

Ceramide セラミド

The conjugated fatty acids are often length 16 to 26. In normal tissues, little ceramide exists as an intermediate of phospho- and glycosphingolipid, whereas in the skin (corneocyte), ceramides and fatty-acid conjugated acyl-ceramides dominates and exhibit the barrier function.

セラミドに結合する脂肪酸の炭素鎖長は16から26が多く、通常組織ではスフィンゴリン脂質やスフィンゴ糖脂質の中間体として少量存在します。皮膚の角質層にはセラミドに更に脂肪酸が結合したアシルセラミドがあり、皮膚のバリア機能を担います。

Composition

Species Glycosylceramide Glycosyl inositol phosphoceramide (GIPC)
Fatty acid Long chain base References Fatty acid Long chain base References
Plants 16:0 - 26:0
16:1 - 26:1
16:0
VLCFA
d18:2Δ4E8E/Z
d18:2Δ4E8E/Z
d18:1Δ8E/Z
t18:1Δ8E/Z
[1][2]
[1][2]
[1]
[1][2]
VLCFA
14:0 - 26:0
20:1 - 26:1
t18:1Δ8E/Z
t18:1Δ8E/Z, t18:0
t18:1Δ8E/Z, t18:0
[1]
[3]
[1][3]
Fungi 16:0 - 18:0
16:1 - 18:1
9-methyl d18:2Δ4E,8E
9-methyl d18:2Δ4E,8E
[4][2]
[4][2]
24:0 - 26:0
24:1 - 26:1
16:0 - 26:0
t18:0
t18:0
t18:0, t20:0
[4]
[2]
[2][3]

Bioactivity

  • Atopic dermatitis (and dry skin) is associated with a decrease and compositional change of ceramides.[5]
  • Ceramides involve in cell proliferation and autophagy, and ceramide 1-phosphate functions as a lipid mediator.[6]

  • アトピー性皮膚炎や乾燥肌ではセラミド量が減少し、組成も変化しています。
  • 通常細胞内ではLCBと同様に細胞増殖やオートファジーに関与し、セラミド末端にリン酸が結合した Cer-1-P も脂質メディエータとして働きます。


  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. PMID 23499054
  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.PMID 12827281
  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 406:995-1010 PMID 23887274
  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.PMID 22025918
  5. Macheleidt O, Kaiser HW, Sandhoff K "Deficiency of epidermal protein-bound omega-hydroxyceramides in atopic dermatitis" J Invest Dermatol. 2002 119:166-173. PMID 12164940
  6. Young MM, Kester M, Wang HG "Sphingolipids: regulators of crosstalk between apoptosis and autophagy" J Lipid Res.2013 54:5-19. PMID 23152582

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