Category:LBSC

From lipidbank_wiki

Cerebroside


Upper classes: LB LBS

| OH
(C14-chain)O-Glucose
(fatty acid) ー | NH
GlcCer
| OH
(C14-chain)O-Galactose
(fatty acid) ー | NH
GalCer

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. These ubiquitous molecules are not registered in LipidBank. Instead, we summarize their distribution with bibliographic references with species information.

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す。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、ここに解説と生物種ごとの報告例を掲載します。

Glucosylceramide (GlcCer)

GlcCer is widely observed not only in Animal, Plant or Fungi kingdoms, but also in Protozoa Kingdom[1]. Ceramide 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 [2]. 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 [3], and its amide-linked fatty acids do not contain hydroxy groups. GlcCer in plants contains many α-hydroxy fatty acids. In some cold-resistant plants ω9-unsaturated fatty acids are detected. 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 [4].

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ます。セラミド構造(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す。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ます。旧口(前口)動物の神経系にはGlcCerが多く含まれ(例えばエビ)、セラミド骨格の脂肪酸に水酸基を含みません。対して、植物は α-水酸化の脂肪酸が多く、耐冷性植物の一部からは ω9-不飽和の脂肪酸も見だされています。後口動物の哺乳綱において、GlcCerは、脾臓、血液、皮膚などに多く含まれます。

先天性代謝異常症であるゴーシェ (Gaucher) 病は、GlcCerを分解するグルコセレブロシダーゼが欠損し、肝臓や脾臓にGlcCerが蓄積して発症します。

Galactosylceramide (GalCer)

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.[6]

GalCerは真正細菌に存在しますが、原生生物界、植物界、菌界(子嚢菌を除く)では報告がありません。動物界に広く分布しますが旧口動物である脱皮動物には確認されていません。セラミド構造は、GlcCerと同様に多様ですが、植物や菌類のGlcCerほど複雑ではありません。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です。 後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ます。

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す。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し抗腫瘍効果がみられます。

  1. Tan RX, Chen JH. "The cerebrosides" Nat Prod Rep. 2003;20:509-34.PMID 14620845, Yu R.K. Yanagisawa M. Ariga T. Glycosphingolipid Structures,in Comprehensive Glycoscience Vol.1,pp. 73-122,doi 10.1016/B978-044451967-2/00003-9, Itonori S, Sugita M. Glycophylogenetic Aspects of Lower Animals. in Comprehensive Glycoscience Vol.3, pp. 253-84, doi 10.1016/B978-044451967-2/00050-7 (J.P. Kamerling, ed.) Elsevier, Oxford (UK). (2007)
  2. 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.
  3. Okamura N, Stoskopf M, Hendricks F, Kishimoto Y. "Phylogenetic dichotomy of nerve glycosphingolipids" Proc Natl Acad Sci, 1985 82:6779-6782 PMID 3863128
  4. Brady RO, Kanfer JN, Shapiro D. "Metabolism of glucocerebrosides. II. Evidence of an enzymatic deficiency in Gaucher's desease" Biochem Biophys Res Commun. 1965;18:221-5 PMID 14282020
  5. Suzuki K. "Globoid cell leukodystrophy (Krabbe's disease): update" J Child Neurol. 2003;18:595-603.PMID 14572137, Suzuki K. "Evolving concept of the pathogenesis of globoid cell leukodystrophy (Krabbe disease)" Proc Jpn Acad Ser B Phys Biol Sci 2003; 79:1-8
  6. Kitamura H, Iwakabe K, Yahata T, Nishimura S, Ohta A, Ohmi Y, Sato M, Takeda K, Okumura K, Van Kaer L, Kawano T, Taniguchi M, Nishimura T. "The natural killer T (NKT) cell ligand alpha-galactosylceramide demonstrates its immunopotentiating effect by inducing interleukin (IL)-12 production by dendritic cells and IL-12 receptor expression on NKT cells" J Exp Med. 1999; 5;189(7):1121-8. PMID 10190903

Cerebrosides in Mammals

Lipids in Heart Muscle

Lipids in Rat Testis

Cerebroside and Sulfatide Ratio in Animal Brain

Fatty acid composition of bovine brains

Sphingolipids in All Kingdoms

The table lists biological species from which sphingolipids were identified. Icons indicate representative species. The icons are used in sphingolipid references together with Synthesis.png for chemical synthesis.

ここに示す分類表にはスフィンゴ脂質が報告された生物が記載されており、アイコンは代表種を表します。スフィンゴ脂質関連の文献にはこれらのアイコンの他、化学合成を表すSynthesis.pngも使われます。

Domain Kingdom Phylum Class Order Model organism Icon Galactosylceramides (GalCer)
(*β configuration unless otherwise state)
Glucosylceramides (GlcCer)
(*β configuration unless otherwise state)
Glycosphingolipids
(GSL)
Ceramide phosphoethanolamine
(CPE)
Sphingomyelin
(SM)
Ceramide aminoethylphosphonate
(CAEP)
Ceramide methylaminoethylphosphonate
(CMAEP)
Glycosyl inositol phosphoceramides
(GIPC)
ドメイン モデル生物 Species
(Structure)
FA, LCB References Species
(Structure)
FA, LCB References Species
(Structure)
FA, LCB References Major series Species
(Structure)
FA, LCB References Species
(Structure)
FA, LCB References Species
(Structure)
FA, LCB References Species
(Structure)
FA, LCB References Species
(Structure)
FA, LCB References
真正細菌
Bacteria
バクテロイデス門
Bacteroidetes
腸内細菌 Bacteria.png Bacteroides
fragilis
(α-GalCer)
br-h17:0,
br-d17:0
PubMed Bacteroides
fragilis
br-h17:0,
br-d17:0
PubMed Sphingobacterium
spiritivorum
/ATCC33861
(Ins-P-Cer)
br-15:0,
br-h15:0,
br-d17:0
PubMed
シアノバクテリア門
Cyanobacteria
藍色細菌 Scytonema
julianum
(Acetyl-
sphingomyelin)
15:1,d18:1 PubMed
プロテオバクテリア門
Proteobacteria
大腸菌 Cystobacter
fuscus
(β-GalCer)
br-h17:0,
br-d19:2
DOI Sphingomonas
paucimobilis
(GlcAα-Cer)
h14:0,d18:0 PubMed Sorangium
cellulosum
h16:1,
br-h17:1,
h18:1,
br-d21:3,
br-d21:2
PubMed Bacteriovorax
stolpii
br-h15:0,
br-15:0,
br-t17:0,
br-d17:0
PubMed
真核生物
Eukaryota
原生生物界
Protista
メタモナーダ門 Metamonada 鞭毛虫 Protista.png Giardia
lamblia
undescribed PubMed Trichomonas
vaginalis
16:0,d18:1 PubMed Giardia
lamblia
16:0,d18:1 DOI
ユーグレノゾア門
Euglenozoa
Leishmania
amazonensis

Plasmodium
falciparum
undescribed

h10:0,h120,
d18:0,d20:0
PubMed

PubMed
Leishmania
amazonensis
(Galβ1-3Galα1
-4Galβ1
-4Glcβ1-Cer)

Plasmodium
falciparum
(trihexosyl-
ceramide)

Trypanosoma
brucei
(GM3,GM1,
GD1a,GD1b)
undescribed

h12:0,h14:0,
d18:0,d20:0

undescribed
PubMed

PubMed

PubMed
Globo,
a-series,
b-series
Leishmania
major
18:0,d16:1 PubMed Plasmodium
falciparum
undescribed PubMed Trypanosoma
brucei
(Ins-P-Cer)
16:0,17:0,
18:0 d16:0,
d17:0,d18:1,
d18:0,d19:0,
d20:0,d20:1
PubMed
(*Procyclic
formのみ)
繊毛虫門
Ciliophora
繊毛虫 Entodinium
caudatum
undescribed PubMed Tetrahymena
pyriformis
/WH-14
16:0,
br-17:0,
br-18:0,
br-h17:0,
h18:0,
br-d17:1,
br-d18:1
PubMed Tetrahymena
pyriformis
/WH-14
16:0,
br-18:0,
br-h17:0,
d18:1
PubMed
植物界
Plantae
緑藻植物門
Chlorophyta
クロレラ Plantae.png Pseudococcomyxa
chodatii
h16:0,h18:0,h20:0,
h22:0,h24:0
d18:2,t18:0,t18:1
DOI Chlorella
kessleri
(Galα1-4Galβ1
-4Glcβ1-Cer)
undescribed PubMed Globo Chlorella
variabilis
(Hex(2)-Ins
-P-Cer)
h24:1, t18:0 Nebraska
Univ.,2015

(*学位論文。
ESI-MS分析,
糖の種類は
Hexとしか
判別できない)
ストレプト植物門
Streptophyta
(*被子植物門を除く) (except Angiosperm)
緑色植物 Ginkgo
biloba

Stenochlaena
palustris
h16:0,d18:2

h24:0,d18:2
DOI

DOI
Pteridum
aquilinum
(HexNAc-HexA
-(Hex-)Ins
-P-Cer)
h24:0,t18:0 PubMed
(*MALDI-MS分析,
糖の種類は
Hexとしか
判別できない)
被子植物門
Angiosperm
シロイヌナズナ Arabidopsis
thaliana
16:0,h24:1,
d18:1,t18:1
PubMed Prunus
armeniaca
/kernel
undescribed J.Chromatogra.,
294,519-524,
1984
Arabidopsis
thaliana
/leaves
(Glc-GlcA
-Ins-P-Cer)
h24:0,t18:1 PubMed
菌界
Fungi
接合菌門
Zygomycota
ケカビ、クモノスカビ Fungi.png Mucor
hiemalis
h14:0,h16:0,
br-d19:2,d20:1
PubMed Mucor
hiemalis
(Galβ1-6Galβ1
-Cer)
h24:0,h25:0,
h26:0,t18:0
PubMed Gala PubMed
(*接合菌門に
はGIPC
は含まれ
ない。)
子嚢菌門
Ascomycota
酵母、コウジカビ Aspergillus
oryzae
h18:0,br-d19:2 PubMed Aspergillus
oryzae
h18:0,br-d19:2 PubMed Neurospora
crassa
(Glcα1-2Galβ1-
6Galβ1-6Galβ1-Cer)
h24:0,t18:0 PubMed Gala Aspergillus
nidulans
(Manα1-3Manα
-2Ins-P-Cer)
h24:0,t18:0 PubMed
担子菌門
Basidiomycota
キノコ Cryptococcus
neoformans
h18:0,br-d19:2 PubMed Cryptococcus
neoformans
(Ins-P-6Manα1
-2Ins-P-Cer)
undescribed PubMed
動物界
Animalia
海綿動物門
Porifera
カイメン Porifera.png Agelas
mauritianus
(α-GalCer)


Chondropsis sp.
(β-GalCer)

h24:0,br-t18:0


h24:0,br-d18:1

DOI


DOI

Haliclona sp. h22:0,t18:1 DOI Amphimedon
viridis
(GlcNAcα1-Cer,
GlcNAcβ1-Cer)
h22:0,br-t20:1,
h22:0,br-t20:1,
br-t19:0
DOI Svenzea
zeai
(Arapβ1
-6Ins-P-Cer)
16:0,
br-16:0,
br-17:0,
d26:1,d26:0
PubMed
刺胞動物門
Cnidaria
クラゲ Cnidaria.png Metridium
senile

Sarcophyton ehrenbergi
(α-GlcCer)
h16:0,h20:0,
br-d19:2

h18:0,br-d19:3
PubMed

PubMed
PubMed
(*刺胞動物門はCPEをもたない。)
PubMed
(*刺胞動物門はSMをもたない。)
Aurelia
aurita
14:0,16:0,
d18:1,t18:0
PubMed Aurelia
aurita
14:0,16:0,
d18:1,t18:0
PubMed
    (旧口動物、冠輪)
(Protostomia, Lophotrochozoa)
扁形動物門
Platyhelminthes
吸虫綱
Trematoda
ジストマ Platyhelminthes.png Fasciola
hepatica
18:0,h18:0,
t18:0,t20:0
PubMed Fasciola
hepatica

Schistosoma mansoni
18:0,h18:0,
t18:0,t20:0

h16:0,t18:0,
t20:0
PubMed

PubMed
Fasciola
hepatica
(Galα1-4Galβ1
-4-Glcβ1-Cer)

Schistosoma
mansoni
(GalNAcβ1
-4Glcβ1-Cer)

Schistosoma
mansoni
(GM1,GD1a,
GD1b,GT1b)
undescribed

h16:0,26:0

undescribed
PubMed

PubMed

DOI
Globo,
Schisto,
Ganglio,
a-series
Paramphistomum
cervi
16:0,18:1 PubMed
渦虫綱
Tubellaria
プラナリア Dugesia
dorotocephala
undescribed PubMed
条虫綱
Cestoda
サナダムシ Diphyllobothrium
hottai
16:0,18:0,26:0,
28:0,d18:0,
d20:0,t18:0,
t20:0
PubMed Diphyllobothrium
hottai
16:0,18:0,
26:0,28:0,
d18:0,d20:0,
t18:0,t20:0
PubMed Diphyllobothrium
hottai
(Galβ1-4(Fucα1-3)Glcβ1-3Galβ1-Cer)

Spirometra
erinacei
(Galβ1-4(Fucα1-3)Glcβ1-3Galβ1-Cer)

Echinococcus
multilocularis
(GM1,GM3,
GD1a,GM2)
16:0,18:0,
26:0,28:0,
d18:0,d20:0,
t18:0

18:0,18:1,
d18:0,t18:0

16:0,24:0,
24:1,d18:1
PubMed

PubMed

PubMed
Spirometo,
a-series
Hymenolepis
diminuta
undescribed PubMed
外肛動物門
Bryozoa
コケムシ Pectinatella
magnifica
undescribed DOI Pectinatella
magnifica
(GlcNAcβ1
-4Glcβ1-Cer)
undescribed DOI
腕足動物門
Brachiopoda
シャミセンガイ Brachiopoda.png Lingula
unguis
h16:0,h17:0,
h18:0,d18:1,
d18:3
DOI Lingula
unguis
(Manα1-3Manβ1
-4Glcβ1-Cer)
16:0,18:0,
d18:3
DOI Mollu Lingula
unguis
16:0,18:0,
h16:0,h18:0,
d18:1,d18:3
滋賀大学教育学部紀要,自然科学・教育科学,45,31-42,1995
環形動物門
Annelida
貧毛綱
Oligochaeta
ミミズ Annelida.png Pheretima
aspergillum
22:0,24:0,
h22:0,h23:0,
h24:0,br-d18:1,
d18:1,t18:0
DOI Pheretima
aspergillum
22:0,24:0,
br-d18:1,
d18:1,
br-d19:1
DOI Pheretima
aspergillum
(Galβ1-6Galβ1-Cer)

Pheretima
hilgendorfi
(PC-6Galβ1
-6Galβ1-Cer)
22:0,24:0,
h24:0,
br-d18:1,
d18:1,t18:0

22:0,24:0,
br-d18:1,
br-d19:1
DOI

PubMed
Neogala (*環形動物門では
SMは見つからない。)
PubMed
(*SM-Binding Protein, Lyseninはミミズから抽出。)
ヒル綱
Hirudinea
ヒル Hirudo
nipponica
(β-GalCer)
16:0,22:0,
24:0,d18:1,
br-d19:1,
d22:3
DOI Hirudo
nipponica
(Galα1-6Galβ1-Cer,
PC-6Galβ1
-6Galβ1-Cer)
16:0,22:0,
24:0,d18:1,
br-d19:1,
16:0,22:0,
24:0,t18:0,
br-t19:0,
d22:3
DOI Isoneogala (*環形動物門ではSMは見つからない。)
多毛綱
Polychaeta
サシバゴカイ目
Phyllodocida
イトメ Tylorrhynchus
heterochaetus
16:0,17:0,
18:0,h16:0,
h17:0 d18:1,
d18:2
DOI Tylorrhynchus
heterochaetus
16:0,17:0,
18:0,h16:0,
h17:0
DOI Tylorrhynchus
heterochaetus
(PC-6Galβ1-Cer)
16:0,d18:1,
d18:2
DOI (*環形動物門ではSMは見つからない。) Tylorrhynchus
heterochaetus
(InsMe-P-Cer)
h16:0,h18:0,
t18:0
DOI
ケヤリ目
Sabellida
エラコ Pseudopotamilla
occelata
16:0,18:0,
h16:0,h18:0,
d18:1
DOI Pseudopotamilla
occelata
16:0,18:0,
h16:0,h18:0,
d18:1
DOI Pseudopotamilla
occelata
(Galα1-4Galβ1-Cer,
Galβ1-4Glcβ1-Cer)
16:0,18:0,
d18:1,
20:1,22:1,
d18:1
DOI Gala (*環形動物門ではSMは見つからない。) Pseudopotamilla
occelata
(Ins-P-Cer)
undescribed DOI
軟体動物門
Mollusca
二枚貝綱
Bivalvia
二枚貝 Mollusca.png Hyriopsis
schlegelii
/egg
14:0,16:0,
h16:0,d18:1,
br-d19:1
PubMed Hyriopsis
schlegelii
/egg
14:0,16:0,
h16:0,d18:1,
br-d19:1
PubMed Hyriopsis
schlegelii
/sperm
(Manα1-3Manβ1
-4Glcβ1-Cer)
16:0,18:0,
20:0,d18:1,
br-d18:1
PubMed
PubMed
Mollu Pinctada
martensii
h16:0,h18:0,
d18:1,d18:0
PubMed Pinctada
martensii
16:0,17:0,
18:0,d16:1,
d18:1,d18:2
滋賀大学教育学部紀要,自然科学,54,41-48,2004 Hyriopsis
schlegelii
/egg
15:0,16:0,
d18:1
DOI Mytilus
galloprovincialis
16:0,h16:0,
d18:1,t18:0
PubMed
腹足綱
Gastropoda
巻貝 Chlorostoma
argyrostoma
turbinatum
16:0,h16:0,
h18:0,d18:1,
d18:2
PubMed Euhadra
hickonis
16:0,h16:0,
br-d19:1,
d18:1
DOI Chlorostoma
argyrostoma
turbinatum
(Galβ1-6Galβ1-Cer)
16:0,17:0,
h16:0,h18:0,
d18:1,
br-d18:1,
d18:2,d19:1
PubMed Neogala Heterogen
longispira
undescribed PubMed Sinotaia
historica
undescribed PubMed Monodonta
labio
undescribed PubMed Monodonta
labio
undescribed PubMed
頭足綱
Cephalopoda
イカ、タコ Ommastrephes
sloani pacificus
/sperm
16:0,18:0,
22:0,22:1,
d16:1
滋賀大学教育学部紀要,自然科学・教育科学,44,17-23,1994 Ommastrephes
sloani pacificus
/sperm
16:0,18:0,
22:0,22:1,
d16:1
滋賀大学教育学部紀要,自然科学・教育科学,44,17-23,1994 Ommastrephes
sloani pacificus
/sperm
(Manβ1-4Manβ1
-4Glcβ1-Cer)

Todarodes
pacificus
(GT3,GQ1c)
16:0,18:1,
22:1,24:1,
d16:1

undescribed
滋賀大学教育学部紀要,自然科学・教育科学,44,17-23,1994

PubMed
c-series Todarodes
pacificu
/viscera
16:0,18:0,
24:1,d16:1
滋賀大学教育学部紀要,自然科学,59,29-37,2009 Todarodes
pacificus
/viscera
16:0,22:1,
24:1,d16:1
滋賀大学教育学部紀要,自然科学,59,29-37,2009
(旧口動物、脱皮)
(Protostomia, Ecdysozoa)
線形動物門
Nematoda
クロマドラ綱
Chromadorea
回虫 Nematoda.png Ascaris
suum
/adult

Ascaris
suum
h24:0,br-d17:1,
br-d17:0,
br-t17:0,t18:0
PubMed

DOI
Ascaris
suum
(HSO3-3Galβ1-Cer)

Ascaris
suum
/adult
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer)

Ascaris
suum
(PC-6GlcNAcβ1-3Manβ1-4Glcβ1-Cer)
24:0,h24:0,br-d17:1,
br-d17:0,
br-t18:0

h24:0,br-d17:1,
br-d17:0

h22:0,h24:0,
br-d17:1,
br-d17:0
PubMed

PubMed

DOI
Arthro Ascaris
suum
24:0,h24:0,
br-d17:1,
br-d17:0,
br-t17:0
DOI Ascaris
suum
(Galα1-
2Ins-P-Cer)
24:0,h24:0,
br-d17:0,
d18:0
PubMed
節足動物門 Arthropoda 昆虫綱 Insecta  ハエ Arthropoda.png Lucilia
caesar
/larvae
16:0,18:0,
20:0,22:0,
d14:1,d16:1
PubMed Lucilia
caesar
/larvae
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer)
16:0,18:0,
20:0,22:0,
d14:1,d16:1
PubMed Arthro Lucilia
caesar
/pupae
20:0,22:0 PubMed
(*昆虫綱ではショウジョウバエなど少数の種のみCPEを多くもつ。)
Aedes
aegypti
/cells
18:0,20:0,
22:0
PubMed
(*昆虫綱では多くの種がSMをもつ。)
甲殻亜門
軟甲綱
Crustacea
Malacostraca
エビ、カニ Penaeus
duorarum
/ventral nerve
undescribed PubMed Euphausia
superba
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer)

Euphausia
superba
(MAEPn-6Glcβ1-Cer)
22:1,24:1,
d14:1

22:1,h22:1,
h24:1,d14:1,
br-d18:3,
d18:3
DOI

PubMed
Arthro Erimacrus
isenbeckii
18:0,20:0,
22:0,22:1,
d14:1,d14:0
滋賀大学教育学部紀要,自然科学,52,9-16,2002
甲殻亜門
鰓脚綱
Crustacea Branchiopoda
カブトエビ、ミジンコ Artemia
franciscana
18:0,22:0,
h18:0,d16:1,
d17:1
PubMed Artemia
franciscana
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer)
22:0,d16:1,
d17:1
PubMed Arthro Artemia
franciscana
18:0,22:0,
d16:1,d17:1
PubMed
多足亜門
ヤスデ綱
Myriapoda Diplopoda
ヤスデ Parafontaria
laminata
h(2- or 3-hydroxy)23:0,
h(2- or 3-hydroxy)24:0,
d17:1,br-d18:1,
d18:1
PubMed Parafontaria
laminata
(GlcNAcβ1-3Manβ1
-4Glcβ1-Cer)
22:0,23:0,
24:0,d17:1,
br-d18:1
PubMed Arthro Parafontaria
laminata
16:0,17:0,
18:0,22:0,
d17:1,d18:1
滋賀文化短期大学紀要,3,71-78,1993 Spirostreptus
asthene s
/oocytes
undescribed DOI
(新口動物)
(Deuterostomia)
棘皮動物門
Echinodermata
ウミユリ綱
Crinoidea
  ウミユリ Echinodermata.png Comanthus
japonica
24:0,h18:0,
h22:1,h24:0,
d16:1,d18:2,
t16:0
PubMed Comanthus
japonica
(Ins-P-Cer)
22:0,24:0,
d16:1
DOI
DOI
(*9-O-MeNeuGc
が結合したGIPC
がある。)
DOI
(*9-O-MeNeuAc
が結合したGIPC
がある。)
ヒトデ綱
Asteroidea
ヒトデ Culcita
novaeguineae
h22:0,br-t16:0 PubMed Asterias
rubens
d18:2,d22:1,
d22:2
PubMed Luidia
maculata
(Galβ1-4Glcβ1-Cer)

Luidia
maculata
((3-sulfo)Galβ1
-4Galβ1
-4Glcβ1-Cer)

Luidia
maculata
(GM3)

Luidia
maculata
(GD3)
h16:0,h22:0,
h24:0,
br-d19:1,
t16:0,
br-t17:0,
t22:1

h22:0,
br-t19:0

h22:0,t19:0

h22:0,t17:0
DOI

DOI

DOI

PubMed
a-series,
b-series
Distolasterias
nipon
undescribed DOI
クモヒトデ綱
Ophiuroidea
クモヒトデ Ophiocoma
scolopendrina
(NeuGcα2
-6Glcβ1-Cer,
GM5,
HSO3-8NeuAcα2
-6Glcβ1-Cer)
18:0,t18:0,
br-t18:0,
h22:0,t18:0,
br-t18:0
PubMed Echino
ウニ綱
Echinoidea
ウニ Anthocidaris
crassispina
/egg
22:1,24:1,
h22:1,h24:1,
t18:0
PubMed Anthocidaris
crassispina
/egg
(Galα1-6Glcβ1Cer)

Anthocidaris
crassispina
/egg
(NeuGcα2
-6Glcβ1-Cer,
GM5,
HSO3-8NeuGcα2
-6Glcβ1-Cer)
22:1,24:1,
h22:1,h24:1,
t18:0

h22:1,h23:1,
h24:1,t18:0
PubMed

PubMed
Echino Strongylocentrotus
intermedius
undescribed DOI
ナマコ綱
Holothuroidea
ナマコ Bohadschia
argus
h24:1,d17:1,
br-d17:1
PubMed Cucumaria
echinata
h22:0,h23:0,
h24:0,
br-d17:1
DOI Holothuria
leucospilota
(NeuGcα2
-6Glcβ1-Cer,
GM5)
h22:0,h23:0,
h24:0,h24:1,
br-t17:0,br-t18:0,
br-t19:0
DOI Echino
脊索動物門
Chordata
ホヤ綱
Ascidiacea
ホヤ Ascidia.png Aplidium
nordmani,
Styela
partita,
Botryllus
leachii
h24:0,t18:0,
br-t19:0
DOI Microcosmus
sulcatus
(Galβ1-4(Fucα1
-3)Glcβ1-Cer)
h22:0,h23:0,
t19:0
DOI Ciona
intestinalis
16:0,18:0,
18:1,d16:1,
d18:2
PubMed
軟骨魚綱
Chondrichthyes
エイ Chondrichthyes.png Carcharhinus
plumbeus
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
undescribed PubMed Squalus
acanthias
/rectal gland
undescribed PubMed Bathyraja
smirnovi
(GM2,GD2)
undescribed PubMed a-series,
b-series
Torpedo
marmorata
/electric organ
16:0,24:1,
d18:1
PubMed
条鰭綱
Actinopterygii
硬骨魚 Actinopterygii.png Cyprinus
carpio
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
24:1,h24:0 PubMed Theragra
chalcogramm
/brain
24:1 PubMed Latimeria
chalumnae
(GM3,GD3)

Theragra
chalcogramma
(9-O-Ac-GT3)
16:0,18:0,
24:1,d18:1

undescribed
DOI

PubMed
a-series,
b-series,
c-series
Latimeria
chalumnae
/brain
undescribed DOI
両生綱
Amphibia
カエル Amphibia.png Rana
catesbeiana
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
18:0,24:1,
h24:1,d18:0,
d18:1
PubMed Bufo
japonicus
/skin
22:0,24:0,
h22:0,h24:0,
t18:0
PubMed Rana
pipiens
(GD1b,GT1b)
undescribed DOI b-series Rana
pipiens
/spinal cord
undescribed J.Exp.Biol. 29, 203-210, 1952
爬虫綱
Reptilias
ワニ Reptilia.png Iguana spp.
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
nonhydroxy FA,hydoroxy FA PubMed Anolis
carolinensis
/kidney
h23:0,h24:0,
h24:1,d18:1
PubMed Pseudemys
scripta elegans
/brain
(GM1,GD1a,GD1b,
GT1b,GQ1b)
undescribed PubMed a-series,
b-series
Tropidurus
torquatus
undescribed PubMed
鳥綱
Aves
トリ Aves.png Gallus
gallus domesticus
/sciatic nerve
(Gal-Cer,SO3-3Galβ1-Cer)
22:0,24:0,
h22:0,h24:0
PubMed Gallus
gallus
domesticus
/lens
undescribed PubMed Anser
anser
/brain
(GM1,GD1a,GD1b,
GT1b,GQ1b)
undescribed PubMed a-series,
b-series
Colurnba
livia domestica
/liver
16:0,18:0,
20:4
PubMed
哺乳綱
Mammalia
無盲腸目
Eulipotyphla
モグラ Mammalia.png Suncus
murinus
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
24:0,h24:0,
d18:1
PubMed Suncus
murinus
/brain
24:0,h24:0,
d18:1
PubMed Suncus
murinus
/brain
(GalNAcβ1-4Galβ1
-4Glcβ1-Cer,
GM1,GD1a,GD1b,
GT1b)
24:0,d18:1 PubMed Ganglio,
a-series,
b-series
Suncus
murinus
/liver
undescribed PubMed
食肉目
Carnivora
ネコ、イヌ Felis
silvestris catus
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
undescribed PubMed Canis
lupus familiaris
/intestine
20:0,22:0,
24:0,hFA
PubMed Felis
silvestris catus
/brain
(GM1,GD1a,GD1b,
GT1b,GQ1b)
undescribed PubMed a-series,
b-series
Canis lupus
familiaris
/brain
undescribed PubMed
奇蹄目
Perissodactyla
ウマ Equus
caballus
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
22:0,24:0,
24:1,h22:0,
h24:0,h24:1,
d18:1
PubMed Equus
caballus
/spleen
16:0,22:0,
24:0
PubMed Equus
caballus
/brain
(GM4,GM3,GM2,
GM1,GD1a,GD1b,
GT1b)
18:0,20:0,
24:0,h24:0,
h24:1,d18:1,
d20:1
PubMed a-series,
b-series
Equus
caballus
/spinal cord
16:0,18:0,
22:0,24:1
DOI
鯨偶蹄目
Cetartiodactyla
ウシ、ブタ Bos
taurus
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
18:0,24:0,
24:1,h18:0,
h24:0,h24:1,
d18:1
PubMed Bos
taurus
/spleen
22:0,23:0,
24:0
PubMed Bos
taurus
/brain
(GM2,GM1,GD3,
GD1a,GD1b)
undescribed PubMed a-series,
b-series
Bos
taurus
/brain
18:0,24:0,24:1,
d18:1
PubMed Ovis
aries
/brain,
Capra
linnaeus
/brain
undescribed PubMed
兎目
Lagomorpha
ウサギ Oryctolagus
cuniculus
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
undescribed PubMed Oryctolagus
cuniculus
/skin fibroblasts
undescribed PubMed Oryctolagus
cuniculus
/brain
(GM1,GD1a,GD1b,
GT1)
undescribed PubMed a-series,
b-series
Oryctolagus
cuniculus
/brain
undescribed PubMed
齧歯目
Rodentia
ラット、マウス Rattus
norvegicus
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
undescribed PubMed Mus
musculus
/erythrocytes
16:0,18:1,
22:0,24:1,
d18:1
PubMed Rattus
norvegicus
/brain
(GM1,GD1a,GD1b,
GT)
undescribed PubMed a-series,
b-series
Rattus
norvegicus
/brain
undescribed PubMed
霊長目
Primates
ヒト Primates.png Homo
sapiens
/brain
(Gal-Cer,SO3-3Galβ1-Cer)
18:0,24:1,
24:0,25:1,
25:0,26:1,
h16:0,h22:0,
h23:0,h24:1,
h24:0
PubMed Homo
sapiens
/spleen of
Gaucher's
disease

Homo
sapiens
/blood
22:0,d18:1

undescribed
PubMed

PubMed
Homo
sapiens
/brain
(GM1,GD1a,GD1b,
GT1b)
undescribed PubMed a-series,
b-series
Homo
sapiens
/brain
18:0,24:1 PubMed

Biosynthesis

In Mammalia, GlcCer is synthesized by ceramide glucosyltransferase (CGlcT) at the cytosolic membrane of the Golgi apparatus, and GalCer is synthesized by ceramide galactosyltransferase (CGalT) at the lumen of the endoplasmic reticulum (ER). These enzymes do not share any sequence similarity and CGlcT possesses its transmembrane region at the N-terminal (type III) whereas CGalT possesses it at the C-terminal (type I).[1]

哺乳動物では、ゴルジ装置の細胞質側に局在するグルコシルセラミド合成酵素(CGlcT)によって GlcCer が、小胞体の内腔側に局在するガラクトシルセラミド合成酵素(CGalT)によって GalCer が作られます。これらの酵素は配列相同性が無く、CGlcT は膜貫通領域が N 末端側(III型酵素)、CGalT は C 末端側(I型酵素)です。

GlcCer GalCer
Enzyme CGlcT (EC 2.4.1.80) CGalT (EC 2.4.1.45)
Reaction Ceramide + UDP-glucose → GlcCer + UDP Ceramide + UDP-galactose → GalCer + UDP
Location Golgi (outside) → flipflop → Golgi (inside) ER lumen

Since all glycolipid synthesizing enzymes (except for CGlcT and CGalT) reside at the lumen of the Golgi apparatus, GlcCer must be flip-flopped from the cytosolic side to the lumen by an eyzyme called flippase. To synthesize GalCer, UDP-galactose and ceramide must transport the ER membrane. UDP-galactose transporter 2 (UGT2) is considered to be responsible.

GalT can also work on glycerolipid, and synthsizes sulfated glyceroglycolipid in mammalian testis, called seminolipid.

CGlcT, CGalT 以外の糖脂質合成酵素はゴルジ装置の内腔側にあり、GlcCer はゴルジ膜の細胞質側から内腔側にフリッパーゼと呼ばれる酵素で移動(フリップフロップ)します。GalCer の場合は、UDPガラクトースとセラミドが小胞体膜を通過します。UDPガラクトーストランスポータ2 (UGT2) が関与するようです。

CGalTはグリセロ脂質にも作用し、精巣の硫酸化グリセロ糖脂質であるセミノリピドも合成します。

  1. Sprong H, Degroote S, Nilsson T, Kawakita M, Ishida N, van der Sluijs P, van Meer G "Association of the Golgi UDP-galactose transporter with UDP-galactose:ceramide galactosyltransferase allows UDP-galactose import in the endoplasmic reticulum" Mol Biol Cell. 2003;4:3482-93 PMID 12925779

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