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==Cerebrosides==
=={{Bilingual|セレブロシド|Cerebrosides}}==
{{Twocolumn|
{{Twocolumn|
Monoglycosylceramides (or cerebrosides) are glycosphingolipids where a single sugar is attached to the ceramide structure. Especially, glucopyranose-attached Glucosylceramide (GlcCer) and galactopyranose-attached Galactosylceramide (GalCer) are widely observed in all kingdoms, and therefore we do not register them in LipidBank <ref name="npr2003">Cerebrosides with 2-amino-2-deoxy or 2-O-isoprenyl glycosyl moieties are found in spongia. See RX Tan & JH Chen (2003) The cerebrosides. Nat Prod Rep 20:509-534</ref>. Instead, we summarize their distribution with bibliographic references for biological species<ref>Itonori S, Sugita M. Glycophylogenetic Aspects of Lower Animals. in Comprehensive Glycoscience Vol.3, Biochemistry of glycoconjugate glycans. (J.P. Kamerling, ed.) Elsevier, Oxford (UK). pp. 253-84 (2007)</ref><ref>Yamakawa T, Nishimura S. (1966) Cerebroside composition in animal brain. Jpn J Exp 36:101-102.</ref>.
Monoglycosylceramides (or cerebrosides) are glycosphingolipids where a single sugar is attached to the ceramide structure. Especially, glucopyranose-attached Glucosylceramide (GlcCer) and galactopyranose-attached Galactosylceramide (GalCer) are widely observed in all kingdoms, and therefore we do not register them in LipidBank <ref name="npr2003">Cerebrosides with 2-amino-2-deoxy or 2-O-isoprenyl glycosyl moieties are found in spongia. See RX Tan & JH Chen (2003) The cerebrosides. Nat Prod Rep 20:509-534</ref>. Instead, we summarize their distribution with bibliographic references for biological species<ref>Itonori S, Sugita M. Glycophylogenetic Aspects of Lower Animals. in Comprehensive Glycoscience Vol.3, Biochemistry of glycoconjugate glycans. (J.P. Kamerling, ed.) Elsevier, Oxford (UK). pp. 253-84 (2007)</ref>.


<big>GlcCer</big> is widely observed not only in Animal, Plant or Fungi kingdoms, but also in Protozoa Kingdom. Ceramides are formed from fatty acids and long-chain bases, and their structures (hydrocarbon chain length, the number and position of double bonds, existence of hydroxy and other modification groups) may vary, and become complex especially in Plant and Fungi Kingdoms, and Protostomia <ref>Sphingoid base chain may terminate with an isopropyl group in spongia, annelida, echinodermata, and bacteria. Terminal isobutyl or sec-pentyl group has been found only in echinodermata. Methylated or cyclopropane-containing sphingoid base is found in spongia, echinodermata, protochordata, and fungi.</ref>.
<big>GlcCer</big> is widely observed not only in Animal, Plant or Fungi kingdoms, but also in Protozoa Kingdom. Ceramides are formed from fatty acids and long-chain bases, and their structures (hydrocarbon chain length, the number and position of double bonds, existence of hydroxy and other modification groups) may vary, and become complex especially in Plant and Fungi Kingdoms, and Protostomia <ref>Sphingoid base chain may terminate with an isopropyl group in spongia, annelida, echinodermata, and bacteria. Terminal isobutyl or sec-pentyl group has been found only in echinodermata. Methylated or cyclopropane-containing sphingoid base is found in spongia, echinodermata, protochordata, and fungi.</ref>.
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<references/>
<references/>
=={{Bilingual|哺乳類のセレブロシド|Cerebrosides in Mammals}}==
{| class="wikitable"
|+ Lipids in Heart Muscle
|-
!
! Lipid (% wet weight)
! Phospholipid (% dry weight)
! Phosphatidylethanolamine<br/>PE (% dry weight)
! Phosphatidylcholine<br/>PC (% dry weight)
! Sphingomyelin (% dry weight)
! '''Cerebroside''' (% dry weight)
! Total cholesterol (% dry weight)
|-
! Human
| 8.3
| 6.3 - 7.5
| 1.4 - 2.8
| 3.3 - 5.7
| 0.2 - 0.5
| -
| -
|-
! Cow
| 3.1 - 19.5
| 7.4 - 11.8
| 5.3
| 4
| 0.5
| 2
| 0.4 (free)
|-
! Rat
| 0.4 - 2.4
| 5 - 8
| 0.84 (% wet)
| 2 (% wet)
| 0.14 (% wet)
| 1.4
| 0.4 - 0.6
|}
{| class="wikitable"
|+ Lipids in Rat Testis (TW Keenan et al. Biochim Biophys Acta 270:433, 1972; A Suzuki et al. J Biochem 82:461, 1977)
|-
! Fraction
! Total Lipid (mg/mg protein)
! Phosphate (ug/mg protein)
! Phospholipid<br/>(% total lipid)
! Neutral Lipid<br/>(% total lipid)
! '''Cerebroside''' (% total lipid)
! Sulfated glycolipid<br/>(nmol/g total weight)
|-
! Total testis
| 0.40
| 62.88
| 62.9
| 34.6
| 2.5
| 556 &plusmn; 34
|-
! Golgi
| 1.26
| 18.49
| 58.3
| 39.4
| 2.3
| -
|-
! Remnant granule
| 0.60
| 19.67
| 29.5
| 68.0
| 2.5
| -
|-
! Microsome
| 0.63
| 53.21
| 83.8
| 14.5
| 1.7
| -
|-
! Lipid corpuscle
| > 19
| 12
| 1.5
| 98.5
| -
| -
|}
{| class="wikitable sortable"
|+ '''Cerebroside''' and Sulfatide in Animal Brain (Yamakawa T, Nishimura S. Cerebroside composition in animal brain. Jpn J Exp 36:101, 1966)
|-
! Animal
! Kerasin<br/>(GalCer with straight chain)
! Phrenosin<br/>(GalCer with hydroxy chain)
! Sulfatide
|-
! Human cinerea (gray matter)
| 25
| 52
| 23
|-
! Human alba (white matter)
| 28
| 47
| 25
|-
! Cow cinerea
| 15
| 56
| 29
|-
! Cow alba
| 35
| 48
| 17
|-
! Dog
| 21
| 57
| 22
|-
! Cat
| 21
| 60
| 19
|-
! Mouse (4 weeks)
| 24
| 56
| 20
|-
! Rat (10 days)
| 35
| 42
| 23
|-
! Rat (35 days)
| 21
| 61
| 18
|-
! Rabbit
| 13
| 66
| 21
|-
! Guinea pig
| 28
| 54
| 18
|-
! Sheep
| 27
| 47
| 26
|-
! Chicken
| 44
| 37
| 19
|-
! Tuna
| 50
| 25
| 25
|-
! Shark
| 44
| 24
| 32
|}

Revision as of 06:24, 23 November 2015

Cerebrosides

Monoglycosylceramides (or cerebrosides) are glycosphingolipids where a single sugar is attached to the ceramide structure. Especially, glucopyranose-attached Glucosylceramide (GlcCer) and galactopyranose-attached Galactosylceramide (GalCer) are widely observed in all kingdoms, and therefore we do not register them in LipidBank [1]. Instead, we summarize their distribution with bibliographic references for biological species[2].

GlcCer is widely observed not only in Animal, Plant or Fungi kingdoms, but also in Protozoa Kingdom. Ceramides are formed from fatty acids and long-chain bases, and their structures (hydrocarbon chain length, the number and position of double bonds, existence of hydroxy and other modification groups) may vary, and become complex especially in Plant and Fungi Kingdoms, and Protostomia [3]. In Animal Kingdom, GlcCer is the basic structure for different derivative series such as Globo, Lacto, and Ganglio Series. In Protostomia, GlcCer is the major ceramide in its nerve tissue, e.g. shrimp brain [4], and the amide-linked fatty acids do not contain hydroxy groups. In Mammalia (of Deuterostomia), GlcCer is major in the spleen, blood, and skin. Gaucher's disease is an inborn metabolic disorder in which GlcCer accumulates in the liver and spleen because of the deficiency of the enzyme glucocerebrosidase to dissociate glucose from the ceramide structure.

モノグリコシルセラミド (またはセレブロシド) はセラミドに糖が1個エステル結合したスフィンゴ糖脂質である。特にグルコース(ピラノース型)が結合したグルコシルセラミド (GlcCer) とガラクトース(ピラノース型)が結合したガラクトシルセラミド (GalCer) は生物界に広く分布するのでデータベース中には掲載せず、ここに解説文と生物種ごとの報告例を掲載する。

GlcCerは系統発生的にみると動物の各組織に広く分布するだけでなく、植物界や菌界、原生生物界にも含まれる。セラミドは脂肪酸と長鎖塩基より構成される。脂肪酸と長鎖塩基の構造(炭化水素の鎖長、二重結合の数と位置、水酸基の有無、修飾基の有無など)の組み合わせは多岐にわたり、特に植物界や菌界、旧口動物のセラミドは複雑である。動物界において、GlcCerはさまざまな糖鎖を持つ糖脂質の基本構造になり、グロボ系列、ラクト系列、ガングリオ系列などが生成される。旧口(前口)動物の神経系にはGlcCerが多く含まれ(例えばエビ)、その脂肪酸にヒドロキシ酸は含まない特徴がある。後口動物の哺乳綱においては、脾臓、血液、皮膚などに多く含まれる。先天性代謝異常症であるゴーシェ (Gaucher) 病ではGlcCerを分解するグルコセレブロシダーゼが欠損しており、肝臓や脾臓にGlcCerが蓄積する。

GalCer has been observed in Eubacterial Domain, but not in Protozoa, Plant, or Fungi (except Ascomycota). It is widely observed in Animal Kingdom, but not in Ecdysozoa (cuticle-shedding animals) of Protostomia. Its ceramide structure differs widely as in GlcCer but not so complex as GlcCer in Plant and Fungi. GalCer is the basic structure for sulfatide (3-O-sulfogalactosylceramide or SM4) and Gala Series often found in Annelida (segmented worm). In Mammalia (of Deuterostomia), GalCer is major in the nerve tissue, especially myelin sheath, whose amido-linked fatty acids are hydroxylated at the C-2 position for more than 50%. Krabbe disease (globoid cell leukodystrophy) is an inborn metabolic disorder in which a small amount of psychosine (galactosylsphingosine, i.e., the lyso form of GalCer) induces demyelination because of the deficiency of the enzyme galactosylceramidase [5]. α-GalCer, found from Porifera (marine sponge), in which galactose is α-bonded to ceramide (not the usual β-bond), uniquely binds to human or mouse NKT cells and is considered a potent anti-tumor agent.

GalCerは真正細菌には存在するが、原生生物界、植物界、菌界(子嚢菌を除く)には報告がない。また動物界において広く分布するが旧口動物である脱皮動物には確認されていない。セラミドはGlcCerと同様にその構造は多岐にわたるが植物や菌類のGlcCerほど複雑ではない。GalCerはスルファチド (3-O-硫酸化ガラクトシルセラミドまたはSM4) や環形動物門に多く含まれるガラ系列の基本構造になる。新口動物である哺乳綱では神経系、特にミエリン鞘にGalCerが多く含まれ、その脂肪酸の50%以上は、C2位が水酸化されている。クラッベ病(グロボイド細胞ロイコジストロフィー; GLD)はガラクトシルセラミダーゼの欠損により微量のサイコシン(ガラクトシルスフィンゴシン、つまり GalCer のリゾ体)が蓄積して脱髄(ミエリンの破壊)を起こす遺伝性疾患である。また、海綿動物門に発見されたα-GalCerは、ガラクトースがセラミドに(通常のβでなく)α結合しており、ヒトやマウスのNKT細胞に特異的に結合することにより抗腫瘍効果を期待されている。

  1. Cerebrosides with 2-amino-2-deoxy or 2-O-isoprenyl glycosyl moieties are found in spongia. See RX Tan & JH Chen (2003) The cerebrosides. Nat Prod Rep 20:509-534
  2. Itonori S, Sugita M. Glycophylogenetic Aspects of Lower Animals. in Comprehensive Glycoscience Vol.3, Biochemistry of glycoconjugate glycans. (J.P. Kamerling, ed.) Elsevier, Oxford (UK). pp. 253-84 (2007)
  3. Sphingoid base chain may terminate with an isopropyl group in spongia, annelida, echinodermata, and bacteria. Terminal isobutyl or sec-pentyl group has been found only in echinodermata. Methylated or cyclopropane-containing sphingoid base is found in spongia, echinodermata, protochordata, and fungi.
  4. Okamura N, Stoskopf M, Hendricks F, Kishimoto Y. (1985) Phylogenetic dichotomy of nerve glycosphingolipids. Proc Natl Acad Sci, 82:6779-6782
  5. GalCer accumulates in the kidney and not in nerve tissues. See Igisu et al. (1983) Biochem Biophys Res Commun 110:940-944; Igisu et al. (1983) Brain 106:405-417;Igisu & Suzuki (1984) J Neuropath Exp Neurol 43:22-36.

Cerebrosides in Mammals

Lipids in Heart Muscle
Lipid (% wet weight) Phospholipid (% dry weight) Phosphatidylethanolamine
PE (% dry weight)
Phosphatidylcholine
PC (% dry weight)
Sphingomyelin (% dry weight) Cerebroside (% dry weight) Total cholesterol (% dry weight)
Human 8.3 6.3 - 7.5 1.4 - 2.8 3.3 - 5.7 0.2 - 0.5 - -
Cow 3.1 - 19.5 7.4 - 11.8 5.3 4 0.5 2 0.4 (free)
Rat 0.4 - 2.4 5 - 8 0.84 (% wet) 2 (% wet) 0.14 (% wet) 1.4 0.4 - 0.6
Lipids in Rat Testis (TW Keenan et al. Biochim Biophys Acta 270:433, 1972; A Suzuki et al. J Biochem 82:461, 1977)
Fraction Total Lipid (mg/mg protein) Phosphate (ug/mg protein) Phospholipid
(% total lipid)
Neutral Lipid
(% total lipid)
Cerebroside (% total lipid) Sulfated glycolipid
(nmol/g total weight)
Total testis 0.40 62.88 62.9 34.6 2.5 556 ± 34
Golgi 1.26 18.49 58.3 39.4 2.3 -
Remnant granule 0.60 19.67 29.5 68.0 2.5 -
Microsome 0.63 53.21 83.8 14.5 1.7 -
Lipid corpuscle > 19 12 1.5 98.5 - -
Cerebroside and Sulfatide in Animal Brain (Yamakawa T, Nishimura S. Cerebroside composition in animal brain. Jpn J Exp 36:101, 1966)
Animal Kerasin
(GalCer with straight chain)
Phrenosin
(GalCer with hydroxy chain)
Sulfatide
Human cinerea (gray matter) 25 52 23
Human alba (white matter) 28 47 25
Cow cinerea 15 56 29
Cow alba 35 48 17
Dog 21 57 22
Cat 21 60 19
Mouse (4 weeks) 24 56 20
Rat (10 days) 35 42 23
Rat (35 days) 21 61 18
Rabbit 13 66 21
Guinea pig 28 54 18
Sheep 27 47 26
Chicken 44 37 19
Tuna 50 25 25
Shark 44 24 32

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