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| 1 |  |
4,8-sphingadienine |
DLB0001 | Akira Hayashi |
d18:2 (4,8) |
C18H35O2N1 | 297.476 | |
Glycolipids of oyster (Ostrea gigas) (Ref. 0001/0002); N-methyl aminoethyl phosphonyl trigalactoside obtained from the shellfish, Turbo cornutus (15.6%) (Ref. 0009); Five sphingoglycolipids obtained from the Shellfish, Turbo Cornutus (8.8-16.9%) (Ref. 0010); Ceramide aminoethyl phosphonate of Sea star, Metridium senile (Ref. 0003); Cerebroside of dimorphic human pathogen, Candida albicans(Ref. 0004); Ceramide aminoethylphosphonateof oyster (adductor muscle 19.3%, gills 30.7%, mantle 29.0%,viscera 52.3%) (Ref. 0005);Sphingophosphonolipids in 8 kinds of shellfish (11.7-52.3%) (Ref. 0006); Aminoalkylphosphonylcerebroside isolated from the muscle part (11.3%) (Ref. 0007) and the visceral part (15.6%) (Ref. 0009) of Turbo cornutus; Five kinds of Gala-6 series sphingoglycolipids of marine snail, Chlorostoma argyrostoma turbinatum (16.9-32.7%) (Ref. 0011). |
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| 2 |  |
Docosa-4,15-sphingadienine/ 1,3-Dihydroxy-2-amino-4,15-docosadiene (Ref. 0012) |
DLB0002 | Akira Hayashi |
d22:2 (4,15 ) |
C22H43O2N1 | 353.582 | |
EI/MS of N-acetyl-O-TMS deriv. of polyhydroxy deriv. obtained by osmium oxidation of the LCB(Ref. 0012) |
Ceramide N-methylaminoethyl phosphonate in the shellfish, Turbo cornutus (Ref. 0012). |
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| 3 |  |
4-Hydroxy-docosa-15-sphingenine/ 1,3,4-Trihydroxy-2-amino-15-docosene (Ref. 0012) |
DLB0003 | Akira Hayashi |
t22:1 (15) |
C22H45O3N1 | 371.598 | |
N-Methylaminoethyl phosphonate containing the LCB is oxidized with periodate. Obtained aldehyde is reduced with NaBH4 to alcohol, which is oxidized with osmium to polyhydroxy alcohol. MS of TMS deriv. of the polyhydroxy alcohol(Ref. 0012). |
Ceramide aminoethylphosphonate obtained from the shellfish, Turbo Cornutus (Ref. 0012). |
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| 4 |  |
DLB0004 | Akira Hayashi |
d18:2 (4,14) |
C18H35O2N1 | 297.476 | |
GC data of N-acetyl-O-TMS-LCB (column: 3% SE-30/3%XE-60/3%OV-17(Ref. 0014) |
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| 5 |  |
Dodecasphinganine/ 1,3-Dihydroxy-2-aminododecane (Ref. 0016) |
DLB0005 | Akira Hayashi |
d12:0 |
C12H27O2N1 | 217.348 | |
ECL value of aldehyde obtained by periodate oxidation of the LCB/GC-MS of alcohol obtained by reduction of the aldehyde (no data) (Ref. 0016) |
Sphingomyelin obtained from spray-dried buttermilk powder (Ref. 0016) |
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| 6 |  |
DLB0006 | Akira Hayashi |
d14:0 |
C14H31O2N1 | 245.401 | |
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| 7 |  |
DLB0007 | Akira Hayashi |
d15:0 |
C14H29O2N1 | 243.386 | |
Identification with ECL values of aldehydes obtained by periodate oxidation of the LCB and GC-MS of alcohols obtained from the aldehydes (no MS data) (Ref. 0016) |
Sphingomyelin obtained from spray-dried buttermilk powder (Ref. 0016) |
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| 8 |  |
Hexadecasphinganine/ 1,3-Dihydroxy-2-aminohexadecane |
DLB0008 | Akira Hayashi |
d16:0 |
C16H35O2N1 | 273.455 | |
Sphingomyelin obtained from spray-dried butternilk powder (Ref. 0016); Sphingomyelin obtained from atherosclerotic human aorta (0.6  0.1%) (Ref. 0017); Cerebroside (2.7%) and Sphingomyelin (4.8%) of beef kidney (Ref. 0018>; Sphingolipid of house fly larva (trace) (Ref. 0019); human plasna sphingomyelin (Ref. 0013); Weak alkali stable lipids of yeast, Hansenula ciferrii (0.5%) (Ref. 0021). |
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| 9 |  |
Heptadecasphinganine/ 1,3-Dihydroxy-2-amino-heptadecane(Ref. 0016) |
DLB0009 | Akira Hayashi |
d17:0 |
C17H37O2N1 | 287.481 | |
Identified with ECL values of aldehydes obtained from the LCB and GC-MS of alcohols obtained by reduction of the aldehydes. |
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| 10 |  |
D(+)-Sphinganine/D(+)- Erythro-1,3-dihydroxy-2-aminooctadecane/D(+)-2S, 3R-1, 3-dihydroxy-2-aminooctadecane |
DLB0010 | Akira Hayashi |
d18:0 |
C18H39O2N1 | 301.508 | |
Effect on phorbol-dependent differentiation of HL-60 cell(Ref. 0037) |
[a]22D=+19.2 (Erythro-triacetyl) (Ref. 0023) |
1H-NMR (Ref. 0260) |
EI-MS of N-acetyl-O-TMS-LCB shows no molecular ion, but shows [M-15 ] ion (m/z 472) and [M-103] ion. (Ref. 0025) |
GC data (column: 2% OV-1) of N-Acetyl-O-TMS-LCB (Ref. 0025) |
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| 11 |  |
Nonadecasphinganine/1,3-dihydroxy-2-aminononadecane (Ref. 0016) |
DLB0011 | Akira Hayashi |
d19:0 |
C19H41O2N1 | 315.534 | |
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| 12 |  |
DLB0012 | Akira Hayashi |
d20:0 |
C20H43O2N1 | 329.561 | |
IR of DNP-derivative shows the same spectrum as that of DNP-C18-dihydrosphingosine. |
Milk sphingomyelin (0.6mole%) (Ref. 0016)/Mild alkali stable lipids obtained from yeast, Hansenula (0.4%)(Ref. 0021)/Human brain gangliosides(Ref. 0026)/Ox brain gangliosides (Ref. 0026)/Hair gangliosides (Ref. 0026) / Human brain gray-white matter gangliosides(1-2%) (Ref. 0027) / 18% in long chain bases of mucolipids obtained from ox brain (Ref. 0028). |
Element analyisis of DNP-derivative (Ref. 0026). |
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| 13 |  |
2X,3X-Dodeca-X-4-sphingenine / 1,3-Dihydroxy-2-amino-4-dodecene (Ref. 0016) |
DLB0013 | Akira Hayashi |
d12:1(4) |
C12H25O2N1 | 215.332 | |
Milk sphingomyelin (0.5mole% ) (Ref. 0016) |
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| 14 |  |
2X,3X-Trideca-X-4-sphingenine / 1,3-Dihydroxy-2-amino-4-tridecene (Ref. 0016) |
DLB0014 | Akira Hayashi |
d13:1 (4) |
C13H27O2N1 | 229.359 | |
Milk sphingomyelin (0.4 mole% ) (Ref. 0016) |
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| 15 |  |
DLB0015 | Akira Hayashi |
d14:1(4t) |
C14H29O2N1 | 243.386 | |
EI-MS (a part) (Ref. 0029) |
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| 16 |  |
2X,3X-Pentadeca-X-4-sphingenine / 1,3-Dihyhydroxy-2-amino-4-pentadecene (Ref. 0016) |
DLB0016 | Akira Hayashi |
d15:1(4 ) |
C15H31O2N1 | 257.412 | |
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| 17 |  |
Hexadeca-X-4-sphingenine/ D-Erythro-1,3-dihydroxy-2-amino-trans-4-hexadecene (Ref. 0016) |
DLB0017 | Akira Hayashi |
d16:1(4) |
C16H33O2N1 | 271.439 | |
Sphingomyelin of cow milk(21.0 mole%) (Ref. 0016); Sphingomyelin fo human serum (Ref. 0022); Mild alkali stable lipids of larvae of house fly, Musca domestica (23%) (Ref. 0019); Sphingolipids of atherosclerotic human aorta (Ref. 0017); Sphingomyelin of human plasma(Ref. 0014/0020); Vental cord of Procambarus clark II (crawfish) ; Ceramide aminoethylphosphonate isolated from the oyster(adductor muscle 75.9%, gills 18.4%, mantle 20.4%, viscera 10.8%)(Ref. 0005); Five kinds of glycolipids from Turbo cornutus (9.7-23.2%) (Ref. 0010); Aminoalkylphosphonyl cerebroside isolated from the viscera of Turbo cornutus (2.7%) (Ref. 0008); Aminoalkylphosphonyl cerebroside of the muscle of Turbo cornutus (5.3%) (Ref. 0007); Sphingophosphonolipid obtained from 8 kinds of shellfish (Ref. 0006); Sphingolipids of Barnea dilatata (cerebroside 20.7%, ceramide aminoethylphosphonate 5.1%) (Ref. 0003); five kinds of Gala-6 series sphingoglycolipids (1.9-5.0%) (Ref. 0011); N-methylaminoethyl trigalactosylceramide of Turbo cornutus (6.0%) (Ref. 0009). |
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| 18 |  |
2X,3X-Heptadeca-X-4-sphingenine/ 1,3-Dihydroxy-2-amino-4-heptadecene (Ref. 0032) |
DLB0018 | Akira Hayashi |
d17:1 (4) |
C17H35O2N1 | 285.465 | |
EI/MS of N-acetyl-O-TMS derivative (Ref. 0014) |
Sphingomyelin obtained from cow milk (Ref. 0032); Sphingomyelin of human serum (Ref. 0022); Sphingomyelin isolated from atherosclerotic human aorta (Ref. 0017); Mild alkali stable lipids obtained from house fly, Musca domestica (Ref. 0019); Sphingomyelin from human plasma (Ref. 0014/0020); Ceramide aminoethylphosphonate from Ostrea gigas ( gills 4.1%, mantle 5.4%, viscera 4.2%) (Ref. 0005); Ceramide 2-N-aminoethylphosphonate of Turbo cornutus (Ref. 0033); Sphingophosphonolipids of 8 kinds of shellfishes (4.0-17.1%) (Ref. 0006); Aminoalkylphosphonyl cerebroside of muscle part of Turbo cornutus (8.0%) (Ref. 0007); Aminoalkylphosphonyl cerebroside of visceral part of Turbo cornutus (5.7%) (Ref. 0008); N-Methylaminoethylphosphonyl trigalactosylceramide from Turbo cornutus (Ref. 0009); Five kinds of sphingoglycolipids from Turbo cornutus (9.3-21.6%) (Ref. 0010); Five kinds of Gala-6 series sphingoglycolipids from Chlorostoma argyrostoma turbinatum (3.7-5.7%) (Ref. 0011). |
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| 19 |  |
Sphingosine |
DLB0019 | Akira Hayashi |
d18:1 (4) |
C18H37O2N1 | 299.492 | |
Inhibitor for protein kinase C (Ref. 0036/0037/0038); Inhibition of protein kinase C, sec-kinase, calmodulin-dependent enzymes, insulin receptor tyrosine kinase, CTP:phosphocholine cytidyltransferase, phosphatidic acid phosphohydrase, 150 kDa diacylglycerol kinase, and thyrotropin-releasing hormone binding (Ref. 5017); Inhibition of RNA primase (Ref. 5018) ; Inhibition of monoacylglycerol acyltransferase (Ref. 0519); Activation of casein kinase, EGF-receptor tyrosine kinase, phospholipase D, and 80 kDa |
[a]D =+3.25  (Ref. 5012) |
Insol. in water. Soluble in CHCl3, EtOH and MeOH (Ref. 5012) |
trans double bond (980cm-1, 10.3nm) |
Sphingomyelin of human plasma (Ref. 0014); Sphingoglycolipids from Ostrea gigas (Ref. 0002); Ceramide aminoethylphosphonate from Ostrea gigas (adductor muscle 4.7%, gills 25.3%, mantle 23.0%, viscera 17.9%) (Ref. 0008); Sphingophosphonolipids obtained from eight kinds of shellfish (10.2-41.5%) (Ref. 0006); Aminoalkylphosphonyl cerebroside from Turbo cornutus (muscle part 14.6% (Ref. 0007), visceral part 18.0% (Ref. 0008) ); N-Methylaminoethylphosphonyl trigalactosyl ceramide from Turbo cornutus (Ref. 0009); Five kinds of sphingoglycolipids obtained from Turbo cornutus (26.6-43.5%) (Ref. 0010); Five kinds of Gala-6 series glycolipids from Chlorostoma argyrostoma turbinatum (16.6-30.6%) (Ref. 0011); Barnea dilatata japonica (cerebroside 11.5%, ceramide aminoethylphosphonate 13.5%) (Ref. 0031); Ubiquitous in eukaryotes, limited types of prokaryotes (Ref. 5001) |
Sphingosine is not a direct precursor for ceramide synthesis in the de novo synthetic pathway, although exogenous sphingosine is converted to ceramide probably by the same enzyme as dihydrosphingosine-N-acyltransferase in cells. Thus, cellular sphingosine is mainly produced by hydrolysis of ceramide. Sphingosine is converted to Sphingossine-7-phosphate in the degradation pathway. (Ref. 5002) |
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| 20 |  |
2X, 3X-8-sphingenine / 1,3-Dihydroxy-2-amino-trans-8-octadecene (Ref. 0039) |
DLB0020 | Akira Hayashi |
d18:1 (8) |
C18H37O2N1 | 299.492 | |
970cm-1 (Ref. 0039) |
Cerebroside obtained from flour (Ref. 0039) |
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| 21 |  |
DLB0021 | Akira Hayashi |
d19:1 (4) |
C19H39O2N1 | 313.519 | |
Sphingomyelin obtained from cow milk (0.8 mole%) (Ref. 0016); Human and rat brain (Ref. 0040); Human kidney (Ref. 0040); Ceramide aminoethylphosphonate from Ostrea gigas (adductor muscle 0, gills 12.9%, mantle 13.1%, viscera 6.4%) (Ref. 0005); Sphingophosphonolipids obtained from 8 kinds of shellfish (2.7-21.9%) (Ref. 0006); Aminoalkylphosphonyl cerebroside from Turbo cornutus (muscle 1.7%, (Ref. 0007), viscera 1.3% (Ref. 0008)); N-methylaminoethylphosphonyl trigalactosyl ceramide from Turbo cornutus (3.4%) (Ref. 0009); Five kinds of Gala-6 series sphingoglycolipids from Chlorostoma argyrostoma turbinatum (16.0, 20.3, 15.7, 16.0, 16.6%) (Ref. 0011); Barnea dilatata japonica (cerebroside 12.4%, ceramide aminoethylphosphonate 5.0%) (Ref. 0031). |
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| 22 |  |
DLB0022 | Akira Hayashi |
d20:1 (4) |
C20H41O2N1 | 327.545 | |
106-107 C (triacetyl derivative) (Ref. 0041) |
[a]21D = -22.89 (triacetyl derivative) (Ref. 0041) |
IR spectrum of triacetyl derivative (Ref. 0041) |
Total ganglioside fraction obtained from human and cow brains (Ref. 0026); Brain gangliosides of human (43%) , calf (34%), rabbit, dog, rat, and cow (Ref. 0027); Sphingophosphonolipids of 8 kinds of shellfish ( chiton 4.9%, others 0) (Ref. 0006); Aminoalkylphosphonyl cerebroside from Tirbo cornutus (muscle part 2.5%, (Ref. 0007), visceral part 1.3% (Ref. 0008); Mucolipids of ox brain (33-46%) (Ref. 0028). |
Isolated (Ref. 0041) |
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| 23 |  |
2X, 3X-Eicosa-X-11-sphingenine / 1,3-Dihydroxy-2-amino-11-eicosene (Ref. 0042) |
DLB0023 | Akira Hayashi |
d20:1 (11) |
C20H41O2N1 | 327.545 | |
Phosphosphingolipid of scorpion, Centruroides sculpturatus (8%) (Ref. 0042) |
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| 24 |  |
2X, 3X-Docosa-X-4-sphingenine / 1,3-Dihydroxy-2-amino-4-docosene (Ref. 0041) |
DLB0024 | Akira Hayashi |
d22:1 (4) |
C22H45O2N1 | 355.598 | |
Human brain ganglioside (trace) (Ref. 0041) |
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| 25 |  |
Erythro-docosa-cis-9-sphingenine / Erythro-1,3-dihydroxy-2-amino-cis-9-docosene (Ref. 0003) |
DLB0025 | Akira Hayashi |
d22:1 (9) |
C22H45O2N1 | 355.598 | |
Ei-MS of N-DNP-O-TMS-derivative (Ref. 0003) |
Cerebroside of sea star, Asterias rubens (Ref. 0003) |
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| 26 |  |
Erythro-docosa-cis-13-sphingenine / Erythro-1,3-dihydroxy-2-amino-cis-13-docosene (Ref. 0003) |
DLB0026 | Akira Hayashi |
d22:1 (13) |
C22H45O2N1 | 355.598 | |
EI-MS of N-DNP-O-TMS derivative (Ref. 0003) |
Cerebroside of a sea star, Asterias rubens (Ref. 0003) |
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| 27 |  |
2X,3X-Hexadecasphingadienine / 1,3-Dihydroxy-2-amino-hexadecadiene (Ref. 0040) |
DLB0027 | Akira Hayashi |
d16:2 |
C16H31O2N1 | 269.423 | |
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| 28 |  |
2X,3X-Heptadecasphingadienine / 1,3-Dihydroxy-2-aminoheptadecadiene (Ref. 0040) |
DLB0028 | Akira Hayashi |
d17:2 |
C17H33O2N1 | 283.449 | |
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| 29 |  |
2X,3X-X-4,X-13-sphingadienine / 1,3-Dihydroxy-2-amino-4,13-octadecadiene (Ref. 0032) |
DLB0029 | Akira Hayashi |
d18:2 (4,13) |
C18H35O2N1 | 297.476 | |
cow heart (Ref. 0032) |
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| 30 |  |
2X, 3X-X-4, X-12-sphingadienine / 1,3-Dihydroxy-2-amino-4,12-octadecadiene (Ref. 0020) |
DLB0030 | Akira Hayashi |
d18:2 (4,12) |
C18H35O2N1 | 297.476 | |
Sphingomyelin obtained from human plasma (Ref. 0020) |
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| 31 |  |
2X, 3X-sphingadienine / 1,3-Dihydroxy-2-aminooctadecadiene (Ref. 0017) |
DLB0031 | Akira Hayashi |
d18:2 |
C18H35O2N1 | 297.476 | |
Sphingomyelin obtained from atherosclerotic human aorta (Ref. 0017) |
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| 32 |  |
2X, 3X-eicosa-X-4, X-11-sphingadienine / 1,3-Dihydroxy-2-amino-4, 11-icosadienine (Ref. 0042) |
DLB0032 | Akira Hayashi |
d20:2 (4,11) |
C20H39O2N1 | 325.529 | |
Phosphosphingolipid of a scorpion, Centruroides scalpturatus (35%) (Ref. 0042) |
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| 33 |  |
2X, 3X-eicosasphingadienine / 1, 3-Dihydroxy-2-aminoicosadienine (Ref. 0032) |
DLB0033 | Akira Hayashi |
d20:2 |
C20H39O2N1 | 325.529 | |
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| 34 |  |
Erythro-docosa-trans-4-cis-9-sphingadienine / Erythro-1, 3-dihydroxy-2-amino-trans-4, cis-9-docosadiene (Ref. 0003) |
DLB0034 | Akira Hayashi |
d22:2 (4,9) |
C22H43O2N1 | 353.582 | |
EI-MS of N-DNP-O-TMS derivative (Ref. 0003) |
Cerebroside of a sea star, Asterias rubens (Ref. 0003) |
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| 35 |  |
Erythro-docosa-4-13-sphingadienine / Erythro-1, 3-dihydroxy-2-amino-trans-4, cis-13-docosadiene (Ref. 0003) |
DLB0035 | Akira Hayashi |
d22:2 (4,13) |
C22H43O2N1 | 353.582 | |
EI-MS of N-DNP-O-TMS derivative (Ref. 0003) |
Cerebroside of a sea star, Asteria rubens (Ref. 0003) |
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| 36 |  |
DLB0036 | Akira Hayashi |
9-Me-d18:2 (4, 8) |
C19H37O2N1 | 311.503 | |
A fruiting-inducing activity |
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| 37 |  |
2X, 3X-octadecasphingadienine / 1, 3-Dihydroxy-2-amino-docosadienine (Ref. 0033) |
DLB0037 | Akira Hayashi |
d22:2 |
C22H43O2N1 | 353.582 | |
Ceramide-2-aminoethylphosphonate from Turbo cornutus (Ref. 0033); Sphingophosphonolipids from 8 kinds of shellfish (muscle of Turbo cornutus 25.3%, viscera of Turbo cornutus 8.2%, Monodonta labio 5.2%) (Ref. 0006); Aminoalkylphosphonyl cerebroside from Turbo cornutus (muscle part 36.6% (Ref. 0007), visceral part 23.5% (Ref. 0008); N-Methylaminoethylphosphonyl trigalactosyl ceramide (20.6% (Ref. 0009); Five kinds of sphingophosphonoglycolipids from Turbo cornutus ( 8.9, 11.0, 8.4, 6.9, 5.0%) (Ref. 0010) |
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| 38 |  |
DLB0038 | Akira Hayashi |
t17:0 |
C17H37O3N1 | 303.481 | |
Sphingolipids of human and ox stomach (Ref. 0056); Cerebroside of sea cucumber (Ref. 0051); Ceramide N-methylaminoethylphosphonate of snail, Turbo cornutus (Ref. 0050); Phosphonocerebroside of snail, Turbo cornutus (Ref. 0007/0008); Cerebroside of ox kidney (Ref. 0018); Sphingomyelin in medulla and cortex of ox kidney (Ref. 0049); Sphingomyelin of ox kidney (Ref. 0003); Sulfatide of rectal gland of spiny dogfish (Ref. 0003); Mild a;kali stable lipids from yeast, Hansenula ciferrii (Ref. 0021) |
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| 39 |  |
phytosphingosine |
D-ribo-1, 3, 4-trihydroxy-2-aminooctadecane / 4D-hydroxysphinganine (Ref. 0052) |
DLB0039 | Akira Hayashi |
t18:0 |
C18H39O3N1 | 317.507 | |
EI-MS of TMS-derivative (Ref. 0021) |
Main component of sphingomyelin from ox kidney (Ref. 0003); ox kidney cerebroside (53%) (Ref. 0018); Cerebroside of a sea cucumber (Ref. 0051); N-Methylaminoethylphosphonyl trigalactosyl ceramide (7.1%) (Ref. 0009); Sphingomyelin of medulla and cortex of ox kidney (Ref. 0049); Ceramide 2-N-methylaminoethylphosphonate of Turbo cornutus (Ref. 0050); Aminoalkylphosphonyl cerebroside of muscle part of Turbo cornutus (Ref. 0007); N-methylaminoethylphosphonyl galactosyl ceramide (Ref. 0008); Mild alkali stable lipids of yeast, Hansenula ciferrii (8%) (Ref. 0021); Human and ox sphingolipids (Ref. 0056); Ceramide of human and animal hair and Cerebroside of human kidney (Ref. 0054) |
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| 40 |  |
1, 3, 4-Trihydroxy-2-aminononadecane / 4X-Hydroxy-2X, 3X-nonadecasphinganine |
DLB0040 | Akira Hayashi |
t19:0 |
C19H41O3N1 | 331.534 | |
Mild alkali stable lipids of Hansenula ciferrii (Ref. 0021); Cerebrin of corn (Ref. 0040); Sphingomyelin of ox kidney (Ref. 0003); Sphingolipids of human and ox (Ref. 0056); Cerebroside of human kidney and ceramide of hair of human and animals (Ref. 0054); Sphingomyelin of medulla and cortex of ox kidney (Ref. 0049); Phosphonocerebroside of viscera of snail, Turbo cornutus (Ref. 0008). |
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| 41 |  |
DLB0041 | Akira Hayashi |
t20:0 |
C20H43O3N1 | 345.560 | |
Mild alkali stable lipids of yeast, Hansenula ciferrii (Ref. 0021); Ceramide in hair of human and animals (Ref. 0054); Sphingomyelin of medulla and cortex in ox kidney (Ref. 0049) ; Sphingomyelin of ox kidney (Ref. 0003); Ceramide 2-N-methylaminoethylphosphonate of a snail, Turbo cornutus (Ref. 0056); Phosphonocerebroside of a snail, Turbo cornutus (Ref. 0008); Human and ox sphingolipids (Ref. 0056). |
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| 42 |  |
D-ribo-1, 3, 4-trihydroxy-2-amino-trans-8-octadecane / 4D-Hydroxy-trans-8-sphingenine (Ref. 0051) (2S, 3S, 4R, 8E)-form |
DLB0042 | Akira Hayashi |
t18:1 (8t)/8E-DPS |
C18H37O3N1 | 315.491 | |
Insol. in water. Soluble in CHCl3 and EtOH. |
8E-DPS is probably formed by desaturation of phytosphingosine. Alternatively, phytoceramide may be desaturated to form dehydrophytoceramide having an 8E-DPS backbone (Ref. 5031) |
Sphingosine D8-desaturase (plants) (Ref. 5031) |
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| 43 |  |
D-Ribo-1, 3, 4-trihydroxy-2-amino-cis-8-octadecene / 4D-Hydroxy-cis-8-sphingenine (2S, 3S, 4R, 8Z)-form |
DLB0043 | Akira Hayashi |
t18:1 ( 8c )/ 8Z-DPS |
C18H37O3N1 | 315.491 | |
Insol. in water. So;b;e in CHCl3 and EtOH. |
8Z-DPS is probably formed by desaturation of phytosphingosine. Alternatively phytoceramide may be desaturated to form dehydrophytoceramide having a 8Z-DPS backbone. A sphingolipid D8-desaturase seems to catalyze both 8E and 8Z unsaturation (Ref. 5031) |
Sphingolipid D8-desaturase (plants) (Ref. 5031) |
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| 44 |  |
1, 3-Dihydroxy-2-amino-16-methylheptadecane / 16-Methyl-2X, 3X-heptadecasphinganine |
DLB0044 | Akira Hayashi |
iso-d18:0 |
C18H39O2N1 | 301.508 | |
||||||||||||||||||||
| 45 |  |
DLB0045 | Akira Hayashi |
d18:3 (4, 8, 10) |
C18H33O2N1 | 295.460 | |
1H-NMR of aldehyde derived from this base (Ref. 0058) |
||||||||||||||||||||
| 46 |  |
1, 3-Dihydroxy-2-amino-9-methyl-trans-4, trans 8, trans-10-octatri ene / (4E, 8E, 10E)-2-amino-9-methyl-4, 8. 10-octade3catriene-1, 3diol (Ref. 0058) |
DLB0046 | Akira Hayashi |
9-Me-d18:3 (4, 8, 10) |
|
Glucosyl ceramide obtained from a sea star, Asterias amurensis (7.7%) (Ref. 0058) |
|||||||||||||||||||||
| 47 |  |
L(-)-Erythro-Dihydrosphingosine/L(-)-2R, 3S-1, 3-Dihydoxy-2-amino-octadecane/L(-)-Sphinganine |
DLB0047 | Akira Hayashi |
L-erythro-d18:0 |
C18H39O2N1 | 301.508 | |
||||||||||||||||||||
| 48 |  |
D(+)-Threo-Dihydrosphingosine/D(+)-2R, 3R-1, 3-Dihydroxy-2-Amino-octadecane/D(+)-Sphinganine |
DLB0048 | Akira Hayashi |
D-threo-d18:0 |
C18H39O2N1 | 301.508 | |
||||||||||||||||||||
| 49 |  |
L(-)-Threo-Dihydrosphingosine/ L(-)-2S, 3S-1,3-Dihydroxy-2-amino-octadecane/L(-)-Sphinganine |
DLB0049 | Akira Hayashi |
L-threo-d18:0 |
C18H39O2N1 | 301.508 | |
||||||||||||||||||||
| 50 |  |
DLB0101 | Akira Hayashi |
15-Me-d16:0 / iso-d17:0 |
C17H37O2N1 | 287.481 | |
Animals, Protozoa |
||||||||||||||||||||
| 51 |  |
DLB0102 | Akira Hayashi |
16-Me-d17:0 / iso-d18:0 |
C18H39O2N1 | 301.508 | |
Animals |
||||||||||||||||||||
| 52 |  |
DLB0103 | Akira Hayashi |
17-Me-d18:0 / iso d19:0 |
C19H41O2N1 | 315.534 | |
Animals |
||||||||||||||||||||
| 53 |  |
2-Amino-18-methylnonadecane-1, 3-diol (Ref. 0101) |
DLB0104 | Akira Hayashi |
18-Me-d19:0/ iso-d20:0 |
C20H43O2M1 | |
Animals |
||||||||||||||||||||
| 54 |  |
2-Amino-14-methylhexadecane-1, 3-diol (Ref. 0101) |
DLB0105 | Akira Hayashi |
14-Me-d16:0/ anteiso-d17:0 |
|
Animals. |
|||||||||||||||||||||
| 55 |  |
DLB0106 | Akira Hayashi |
16-Me-d18:0 / anteiso-d19:0 |
C19H41O2N1 | 315.534 | |
Animals; Harderian gland of a guinea pig. |
||||||||||||||||||||
| 56 |  |
2-Amino-12-methyl-4-tridecene-1, 3-diol (Ref. 0101) |
DLB0107 | Akira Hayashi |
12-Me-d13:1 (4) / iso-d14:1(4) |
C14H29O2N1 | 243.386 | |
Animals. |
|||||||||||||||||||
| 57 |  |
2-Amino-13-methyl-4-tetradecene-1, 3-diol (Ref. 0101) |
DLB0108 | Akira Hayashi |
13-Me-d14:1 (4) / iso-d15:1 (4) |
C15H31O2N1 | 257.412 | |
Animals. |
|||||||||||||||||||
| 58 |  |
DLB0109 | Akira Hayashi |
15-Me-d16:1 (4) / iso-d17:1 (4) |
C17H35O2N1 | 285.465 | |
Animals. |
||||||||||||||||||||
| 59 |  |
DLB0110 | Akira Hayashi |
16-Me-d17:1 (4) / iso-d18:1 (4) |
C18H37N2O1 | 297.499 | |
Animals. |
||||||||||||||||||||
| 60 |  |
DLB0111 | Akira Hayashi |
17-Me-d18:1 (4)/ iso-d18:1 (4) |
C19H39O2N1 | 313.519 | |
Animals. |
||||||||||||||||||||
| 61 |  |
2-Amino-18-methyl-4-nonadecane-1, 3-diol (Ref. 0106) |
DLB0112 | Akira Hayashi |
18-Me-d19:0 / iso-d-20:0 |
C20H41O2N1 | 327.545 | |
Animals. |
|||||||||||||||||||
| 62 |  |
2-Amino-12-methyl-4-tetradecene-1, 3-diol (Ref. 0101) |
DLB0113 | Akira Hayashi |
12-Me-d14:0 / anteiso-d15:0 |
C15H31O2N1 | 257.412 | |
Animals. |
|||||||||||||||||||
| 63 |  |
DLB0114 | Akira Hayashi |
14-Me-d16:1 (4) / anteiso-d17:1 (4) |
C17H35O2N1 | 285.465 | |
Animals. |
||||||||||||||||||||
| 64 |  |
DLB0115 | Akira Hayashi |
16-Me-d18:1 (4)/ anteiso-d 19:1 (4) |
C19H39O2N1 | 313.519 | |
Animals. |
||||||||||||||||||||
| 65 |  |
DLB0116 | Akira Hayashi |
17-Me-d19:1 (4) / anteiso-d20:1 (4) |
C20H41O2N1 | 327.545 | |
Animals. |
||||||||||||||||||||
| 66 |  |
2-Amino-14-methylpentadecane-1, 3, 4-triol (Ref. 0107) |
DLB0117 | Akira Hayashi |
14-Me-t15:0 / iso-t16:0 |
C16H35O3N1 | 289.454 | |
Animals. |
|||||||||||||||||||
| 67 |  |
DLB0118 | Akira Hayashi |
15-Me-t16:0 / iso-t17:0 |
C17H37O3N1 | 303.481 | |
Animals. |
||||||||||||||||||||
| 68 |  |
iso-phytosphingosine |
DLB0119 | Akira Hayashi |
16-Me-t17:0 / iso-t18:0 |
C18H39O3N1 | 317.507 | |
Animals; Fungi. |
|||||||||||||||||||
| 69 |  |
DLB0120 | Akira Hayashi |
17-Me-t18:0 / iso-t19:0 |
C19H41O3N1 | 331.534 | |
Animals; fungi. |
||||||||||||||||||||
| 70 |  |
2-Amino-18-methylnonadecane-1, 3, 4-triol (Ref. 0104) |
DLB0121 | Akira Hayashi |
18-Me-t19:0 |
C20H43O3N1 | 345.560 | |
Fungi. |
|||||||||||||||||||
| 71 |  |
DLB0122 | Akira Hayashi |
19-Me-t20:0 /iso-t21:0 |
C21H45O3N1 | 359.587 | |
Animals; Fungi. |
||||||||||||||||||||
| 72 |  |
2-Amino-20-methylhenicosane-1, 3, 4-triol (Ref. 0104) |
DLB0123 | Akira Hayashi |
20-Me-t21:0 / iso-t22:0 |
C22H47O3N1 | 373.614 | |
Fungi. |
|||||||||||||||||||
| 73 |  |
2-Amino-14-methylhexadecane-1, 3, 4-triol (Ref. 0107) |
DLB0124 | Akira Hayashi |
14-Me-t16:0 / anteiso-t17:0 |
C17H37O3N1 | 303.481 | |
||||||||||||||||||||
| 74 |  |
2-Amino-15-methylheptadecane-1, 3, 4-triol (Ref. 0107) |
DLB0125 | Akira Hayashi |
15-Me-t17:0 / anteiso-t18:0 |
C18H39O3N1 | 317.507 | |
Animals. |
|||||||||||||||||||
| 75 |  |
DLB0126 | Akira Hayashi |
16-Me-t18:0 / anteiso-t19:0 |
C19H37O3N1 | 327.502 | |
Animals. |
||||||||||||||||||||
| 76 |  |
2-Amino-20-methyl-X-henicosene-1, 3, 4-triol (Ref. 0104) |
DLB0127 | Akira Hayashi |
20-Me-t21:1 (X) / iso-t22:1 (X) |
C22H45O3N1 | 371.598 | |
Fungi. |
|||||||||||||||||||
| 77 |  |
2-Amino-9-methyl-4, 8-octadecadiene-1, 3-diol (Ref. 010801090110>> |
DLB0128 | Akira Hayashi |
9-Me-d18:2 (4, 8) |
C19H37O2N1 | 311.503 | |
Fungi; Animals. |
|||||||||||||||||||
| 78 |  |
DLB0129 | Akira Hayashi |
10-Me-d16:0 |
C17H37O2N1 | 287.481 | |
Harderian gland of a guinea pig. |
||||||||||||||||||||
| 79 |  |
DLB0130 | Akira Hayashi |
9-Me-d16:0 |
C17H37O2N1 | 287.481 | |
Harderian gland of a guinea pig. |
||||||||||||||||||||
| 80 |  |
DLB0131 | Akira Hayashi |
8-Me-d16:0 |
C17H37O2N1 | 287.481 | |
Harderian gland of a guinea pig. |
||||||||||||||||||||
| 81 |  |
DLB0132 | Akira Hayashi |
10-Me-d17:0 |
C18H39O2N1 | 301.508 | |
Harderian gland of a guinea pig |
||||||||||||||||||||
| 82 |  |
DLB0133 | Akira Hayashi |
9-Me-d17:0 |
C18H39O2N1 | 301.508 | |
Hardeian gland of a guinea pig. |
||||||||||||||||||||
| 83 |  |
DLB0134 | Akira Hayashi |
8-Me-d17:0 |
C18H39O2N1 | 301.508 | |
Harderian gland of a guines pig. |
||||||||||||||||||||
| 84 |  |
DLB0135 | Akira Hayashi |
10-Me-d18:0 |
C19H41O2N1 | 315.534 | |
Harderian gland of a guinea pig. |
||||||||||||||||||||
| 85 |  |
4-Hydroxyeicosasphinganine |
DLB0201 | Akira Hayashi |
2S, 3S, 4R-t20:0 |
C20H43O3N1 | 345.560 | |
97-99 C (Ref. 0218) |
[a]17D==8.1 (C, 0.34 in CHCl3) (Ref. 0218) |
||||||||||||||||||
| 86 |  |
DLB0202 | Akira Hayashi |
C27H47O4N1 | 449.666 | |
136-137 C (Ref. 0214) |
[a]D=+3.6 (C, 1 in pyr) (Ref. 0214) |
||||||||||||||||||||
| 87 |  |
DLB0203 | Akira Hayashi |
C33H53O3N1 | 511.779 | |
||||||||||||||||||||||
| 88 |  |
DLB0204 | Akira Hayashi |
Tri-Ac-d18:1 (4) |
C24H43O5N1 | 425.602 | |
103.5-104 (Ref. 0250) |
||||||||||||||||||||
| 89 |  |
DLB0205 | Akira Hayashi |
Tri-benzoyl-d18:1 (4) |
C39H49O3N1 | 579.811 | |
121.5-123.5 (Ref. 0250) |
[a]27D = -11.2 (Ref. 0250) |
Crist. (EtOH) |
||||||||||||||||||
| 90 |  |
DLB0206 | Akira Hayashi |
2S, 3S, 4R-t16:0 |
C16H35O3N1 | 289.454 | |
Acanthacerebroside of total sea star. |
CAS registry nymber: 114379-45-2 (Ref. 0250) |
|||||||||||||||||||
| 91 |  |
DLB0207 | Akira Hayashi |
C24H43O7N1 | 457.601 | |
[a]25D=+27.9 (C, 1.5 in CHCl3) (Ref. 0203) |
Neat 3280cm-1 (NH), 1745cm-1 (OAc), 1660cm-1 (NAc) (Ref. 0203) |
1H-NMR (270MHz) d=6.09 (d, J=9.4Hz, 1H, NH), 5.11 (dd, J=8.3, 3.1Hz, 1H, 3-H), 2.08 (s, 3H, NAc), 2.05 (s, 6H, 2OAc), 2.03 (s, 3H, OAc) 13C-NMR (25.02MHz) d=171.2, 170.9, 170.1, 169.8 (s, C=O), 23.3 (q, COCH3), 22.8 (t)< 22.1 (q, COCH2) (Ref. 0203) |
EI-MS, M+ 457.3037 (Ref. 0203) |
||||||||||||||||||
| 92 |  |
DLB0208 | Akira Hayashi |
2S, 3R, 4R-t16:0 |
C16H35O3N1 | 289.454 | |
Cas registry number:127061-67-0 (Ref. 0250) |
||||||||||||||||||||
| 93 |  |
DLB0209 | Akira Hayashi |
C24H43O3N1 | 393.603 | |
[a]27D=+6.13 (C, 0.56 in CHCl3) (Ref. 0203) |
CAS registry number:128898-88-4 (Ref. 0250) |
||||||||||||||||||||
| 94 |  |
DLB0210 | Akira Hayashi |
2S, 3R, 4S-t16:0 |
C16H35O3N1 | 289.454 | |
|||||||||||||||||||||
| 95 |  |
DLB0211 | Akira Hayashi |
C24H43O7N1 | 457.601 | |
||||||||||||||||||||||
| 96 |  |
DLB0212 | Akira Hayashi |
2S, 3S, 4S-t16:0 |
C16H35O3N1 | 289.454 | |
|||||||||||||||||||||
| 97 |  |
DLB0213 | Akira Hayashi |
C24H43O3N1 | 393.603 | |
[a]28D=3.3 (C, 0.46 in CHCl3) (Ref. 0214) |
|||||||||||||||||||||
| 98 |  |
DLB0214 | Akira Hayashi |
C18H37O4N1S1 | 363.557 | |
||||||||||||||||||||||
| 99 |  |
DLB0215 | Akira Hayashi |
N-Bz-t18:1 (8) |
C25H37O5N1 | 431.565 | |
128-129 (Ref. 0250) |
Cryst. (Me2CO) (Ref. 0250) |
|||||||||||||||||||
| 100 |  |
Octadecasphingosine, cerebrin base, Dihydrosphingosine |
DLB0216 | Akira Hayashi |
2R, 3R-d18:0 |
C18H39O2N1 | 301.508 | |
108 C (Ref. 0245) |
[a]28546=+13 (10:1CHCl3/MeOH) (Ref. 0245) |
GC-MS of N-acetyl-bis-O-trimethylsilyl derivatives : 472 [M-15], 384 [M-103] (Ref. 0245) |
RADIO THIN-LAYER CHROMATOGRAMS(045) |
Rat plasma membrane (Ref. 0245) |
Radio thin-layer chromatogram (Ref. 0245) |
||||||||||||||
| 101 |  |
DLB0217 | Akira Hayashi |
C20H41O3N1 | 343.544 | |
96-97 C (Ref. 0241) |
[a]28546=+6.2 (10:1 hexane/EtOH) (Ref. 0241) |
||||||||||||||||||||
| 102 |  |
DLB0218 | Akira Hayashi |
C24H45O5N1 |
|
46 C (Ref. 0241) |
[a28546=+8.0 (pentane) (Ref. 0241) |
|||||||||||||||||||||
| 103 |  |
DLB0219 | Akira Hayashi |
C18H39O2N1 | 301.508 | |
108 C (Ref. 0245) |
[a]28D=-14.1 (CHCl3) (Ref. 0245) |
GC-MS of N-Acetyl-bis-O-trimethyksilyl derivatives : 472 [M-15 ], 384 [M-103 ] (Ref. 0245) |
Radio thin-layer chromatograms (Ref. 0245) |
Radio thin-layer chromatogram (Ref. 0245) |
|||||||||||||||||
| 104 |  |
DLB0220 | Akira Hayashi |
N, O-Ac-d18:0 |
C24H45O5N1 | 427.618 | |
46 C (Ref. 0241) |
[a]28546=-8.0 (pentane) (Ref. 0241) |
|||||||||||||||||||
| 105 |  |
Octadecasphinganine, cerebrin base, dihydrosphingosine |
DLB0221 | Akira Hayashi |
2R, 3S-d18:0 |
C18H39O2N1 | 301.508 | |
79 C (Ref. 0245) |
[a28546=-6.5 (10:1 hexane/EtOH) (Ref. 0045) |
GC-MS of N-Acetyl-bis-O-trimethylsilyl derivatives : 472 [M-15 ], 384 [ M-103 ] (Ref. 0245) |
RADIO THIN-LAYER CHROMATOGRAMS(045) |
Radio thin-layer chromatogram (Ref. 0245) |
|||||||||||||||
| 106 |  |
DLB0222 | Akira Hayashi |
N-Ac-d18:0 |
C20H41O3N1 | 343.544 | |
124-125 C (Ref. 0241) |
[a]28546=-8 (10:1 hexane/EtOH (Ref. 0241) |
|||||||||||||||||||
| 107 |  |
DLB0223 | Akira Hayashi |
C24H45O5N1 | 427.618 | |
96-97 C (Ref. 0241) |
[ a]28546=-21 (10:1 hexane/EtOH) (Ref. 0241) |
||||||||||||||||||||
| 108 |  |
Octadecasphinganine, Cerebrin base, Dihydrosphingosine |
DLB0224 | Akira Hayashi |
2S. 3R-d18:0 |
C18H39O2N1 | 301.508 | |
Inhibition of protein kinase C activity (Ref. 5013) |
Insol in water, soluble in CHCl3and hot EtOH (Ref. 5012) |
13C-NMR: 63ppm -CH2OH, 69.4ppm -CH- (Ref. 0244) |
GC-MS of N-Acetyl-bis-O-trimethylsilyl derivative (Ref. 0245) |
RADIO THIN-LAYER CHROMATOGRAMS (045) |
Sphinganine is formed by reduction of 3-ketosphingosine. Sphinganine is anabolized to dihydroceramide by dihydrosphingosine-N-acyltransferase, or catabolized to dihydrosphingosine-1-phosphate by the same enzyme as sphingosine kinase (Ref. 5002) |
Radio thin-layer chromatogram (Ref. 0245) |
|||||||||||||
| 109 |  |
DLB0225 | Akira Hayashi |
C24H45O5N1 | 427.618 | |
||||||||||||||||||||||
| 110 |  |
DLB0226 | Akira Hayashi |
2S, 3R-N-Ac-d18:0 |
C20H41O3N1 | 343.544 | |
124-125 C (Ref. 0241) |
[a]28546=+7.7 (10:1 hexane/EtOH) (Ref. 0241) |
|||||||||||||||||||
| 111 |  |
DLB0227 | Akira Hayashi |
C26H37O7N1 | 475.575 | |
49-50 C (Ref. 0247) |
[a]25D =+5 (C, 4.8 in DMF) (Ref. 0247) |
Yeast, Hansenula ciferrii (Ref. 0247) |
Crist. (Petr. ether) (Ref. 0247) |
||||||||||||||||||
| 112 |  |
4-Hydroxysphinganine / phytosphingosine |
DLB0228 | Akira Hayashi |
2S, 3S, 4R-t18:0 |
C18H39O3N1 | 317.507 | |
Insol. in water. Soluble in CHCl3 and EtOH |
Phytosph. is probably formed by hydroxylation of dihydrosphingosine. Alternatively dihydroceramide may be hydroxylated to form phytoceramide having a Phytosph. backbone. Phytosph. is converted to phytosphingosine-1-phosphate in the degradation pathway by the same enzyme as sphingosine kinase. (Ref. 5027) |
||||||||||||||||||
| 113 |  |
DLB0229 | Akira Hayashi |
N-Bz-t18:0 |
C25H43O4N1 | 421.613 | |
137.8-138.8 C (Ref. 0247) |
[a]D = +5 (C, 5.2 in pyridine) (Ref. 0247) |
Yeast, Hansenula ciferrii (Ref. 0247) |
Crist.(EtOAc) (Ref. 0247) |
|||||||||||||||||
| 114 |  |
DLB0230 | Akira Hayashi |
C31H49O7N1 | 547.723 | |
78-80 C (Ref. 0247) |
[a]D = +22 (C, 0.5 in CHCl3) (Ref. 0247) |
Yeast, Hansenula cifrrii (Ref. 0247) |
Crist. (Petr. ether) (Ref. 0247) |
||||||||||||||||||
| 115 |  |
DLB0231 | Akira Hayashi |
N-Bz-O-Ac-t18:1 (8) |
|
77-78 (Ref. 0250) |
[a]25D = +10 (c, 0.76 in CHCl3) (Ref. 0250) |
|||||||||||||||||||||
| 116 |  |
2-Amino-16-methyl-octadecane-1, 3-diol / 16-Methylsphinganine (Ref. 0253) |
DLB0232 | Akira Hayashi |
16-Me-d18:0 / anteiso-d19:0 |
C19H41O2N1 | 315.534 | |
GC-MS of alcohol methyl ether obtained from LCB via aldehyde; m/z 224 [M-32], 195 [M-32-29], 167 [M-32-57], 70 (specific ion for anteiso branching) . (Ref. 0253) |
Calculation of DHf of alkyl fragment ion produced in EI-MS of alcohol methyl ether / Presumption of space filling minimum-energy structure of the hydrocarbon chain. (Ref. 0253) |
||||||||||||||||||
| 117 |  |
2-Amino-4, 11-octadecadiene-1, 3-diol / Sphinga-4, 11-dienine (Ref. 0254) |
DLB0233 | Akira Hayashi |
d18:2 (4, 11) |
C18H35O2N1 | 297.476 | |
GC-MS of polyhydroxyalcohol obtained from the base / GC-MS of aldehyde obtained by periodate oxidation of the base (Ref. 0254) |
|||||||||||||||||||
| 118 |  |
2-Aminononadecatrienine-1, 3-diol (Ref. 0255) |
DLB0234 | Akira Hayashi |
d19:3 |
C19H35O2N1 | 309.487 | |
GC-MS of N-Ac-LCB ; m/z 495 [M+], 480 [M-15], 436 [M-59], 405 [M-90], 390 [M-105], 321 [M-174]. (Ref. 0254) |
|||||||||||||||||||
| 119 |  |
2-Amino-16-methyl-octadecane-1, 3, 4-triol / 4-Hydroxy-16-methylsphinganine (Ref. 0256) |
DLB0235 | Akira Hayashi |
16-Me-t18:0 /anteiso-t19:0 |
C19H41O3N1 | 331.534 | |
||||||||||||||||||||
| 120 |  |
DLB0236 | Akira Hayashi |
15-Me-t16:0 / iso-t17:0 |
C17H39O3N1 | 305.496 | |
Ei-Ms of aldehyde derived from the base (Ref. 0259) |
||||||||||||||||||||
| 121 |  |
DLB0237 | Akira Hayashi |
16-Me-t17:0 / iso-t18:0 |
C18H39O3N1 | 317.507 | |
Sphingoglycolipids of marine sponge (45.9%) (Ref. 0259); Ceramide dihexoside of marine sponge (as TMS-LCB 43.9%, as aldehyde 31.4%) (Ref. 0258); Ceramide monohexoside (as TMS-LCB 39.1%) (Ref. 0258>; Ceramide II of Euhadea hickonis (1.4%) (Ref. 0256); Sphingoglycolipids of Euhadra hickonis (Ceramide monohexoside 1.3%, Ceramide dihexoside 13.7%) (Ref. 0253). |
||||||||||||||||||||
| 122 |  |
2-Amino-17-methyl-octadecane-1, 3, 4-triol / 4-Hydroxy-17-methylsphinganine (Ref. 0259) |
DLB0238 | Akira Hayashi |
17-Me-t18:0 / iso-t19:0 |
C19H41O3N1 | 331.534 | |
Sphingolipids of Euhadra hickonis (SPnL 1.5%, Gal-cer 2.1%, Glc-cer 5.2%, total CMH 5.5%, CDH 2.9%) (Ref. 0253) |
GC of aldehyde obtained fromceramide dihexoside of marine sponge using polar liquid phase (ECL 15.60, tr.) (Ref. 0259) |
||||||||||||||||||
| 123 |  |
DLB0239 | Akira Hayashi |
16-Me-t18:0 / anteiso-t19:0 |
C19H41O3N1 | 331.534 | |
Ceramide dihexoside of marine sponge, Halichondria japonica (as TMS-LCB 17.5%, as aldehyde 19.6%)(Ref. 0258); Ceramide monohexoside of marine sponge ( as TMS-LCB 16.9%) (Ref. 0258); Sphingoglycolipids of marine sponge (20.1% ) (Ref. 0259); Sphingolipids of Euhadra hickonis (SPnL 4.1%, Gal-cer 2.4%, Glc-cer 2.6%, total CMH 15.0%, CDH 20.6% ) (Ref. 0253). |
||||||||||||||||||||
| 124 |  |
2-Amino-17-methylnonadecane-1, 3, 4-triol / 4-Hydroxy-17-methylnonadecasphingosine (Ref. 0259) |
DLB0240 | Akira Hayashi |
17-Me-t19:0 / anteiso-t20:0 |
C20H43O3N1 | 345.560 | |
Sphingoglycolipids of marine sponge (4.0%) (Ref. 0259) |
|||||||||||||||||||
| 125 |  |
3-Ketodihydrosphingosine / 3-Ketosphinganine |
2S-1-Hydroxy-2-amino-octadecane-3-one |
DLB0241 | Akira Hayashi |
KDS |
C18H37O2N1 | 299.492 | |
Insol. in water, soluble in CHCl3 and hot EtOH |
Ubiquitous in eukaryotes (and also inlimited types of prokaryotes ) as a metabolically transient intermediate (Ref. 5001) |
|||||||||||||||||
| 126 |  |
N-Acyl-(2S, 3R)-dihydrosphingosine / N-Acyl-(2S, 3R)-sphinganine / (2S, 3R)-2-(N-Acylamino)-octadecane-1, 3-diol |
DLB5001 | Akira Hayashi |
DCer |
|
An inactive control of biological activity of ceramide (Ref. 5032) |
Insol. in water. Sol. in CHCl3 and ether. |
Ubiquitous in eukaryotes (Ref. 5001) |
|||||||||||||||||||
| 127 |  |
N-Acyl-(2S, 3R, 4E)-sphingosine / (2S, 3R, 4E)-2-(N-acylamino)-4-octadecene-1, 3-diol |
DLB5002 | Akira Hayashi |
Cer |
|
Inhibitions of diacylglycerol kinase, and phospholipase D (Ref. 5017/5035) ; Activation of protein kinase Czeta, a ceramide-activated protein kinase, protein phosphatase (heterotrimeric 2A group), c-Raf, Vav, and phospholipase A2 (Ref. 5017/5035) ; Induction of differentiation, cell-cycle arrest, and apoptosis (Ref. 5017/5031/5036) |
Insol. in water, soluble in CHCl3, EtOH. (Ref. 5012) |
Ubiquitous in eukaryotes (Ref. 5001) |
Cer is synthesized by desaturation of dihydroceramide (Ref. 5002/5033/5034); Cer is anabolized to various complex sphingolipids including sphingomyelin, glucosylceramide, galactosylceramide, and so on. Cer is formed by degradation of complex sphingolipids. Cer is hydrolyzed to sphingosine and fatyy acid by ceramidase in the degradation pathway (Ref. 5002) |
||||||||||||||||||
| 128 |  |
N-Acyl-(2S,3S, 4R)-phytosphingosine / (2S, 3S, 4R)-2-(N-acylamino)-octadecane-1, 3, 4-triol |
DLB5003 | Akira Hayashi |
PhytoCer |
|
Insol. in water. Sol. in CHCl3 and ether |
|||||||||||||||||||||
| 129 |  |
N-Acyl-(2S, 3S, 4R, 8E)-8-dehydrophytosphingosine / (2S, 3S, 4S)-2-(N-acylamino)-8E-octadecene-1, 3, 4-triol |
DLB5004 | Akira Hayashi |
8E-DPSCer |
|
Insol. in water. Soluble in CHCl3 and EtOH. |
Plants (Ref. 5030) |
8E-DPSCer is probably formed by D8-trans-desaturation of phytoceramide, or by N-acylation of 8E-dehydrophytosphingosine (Ref. 5031) |
Sphingolipid D8-desaturase (plants) (Ref. 5031) |
||||||||||||||||||
| 130 |  |
N-Acyl-(2S, 3S, 4R, 8Z)-8-dehydrophytosphingosine / (2S, 3S, 4R)-2-(N-acylamino)-8Z-octadecene-1, 3, 4-triol |
DLB5005 | Akira Hayashi |
8Z-DPSCer |
|
Possible involvement in cold-resistance (Ref. 5030) |
Insol. in water, Sol. in CHCl3 and EtOH. |
Plants (Ref. 5030) |
6Z-DPSCer is probably formrf by D8-cis-desaturation pf phytoceramide, or by N-acylation of 8Z-dehydrophytosphingosine(Ref. 5031) |
Sphingolipid D8-desaturase (plants) (Ref. 5031) |
|||||||||||||||||
| 131 |  |
2-Tetradecanoylamino-4-octadecene-1, 3-diol / N-Tetradecanoyl-4-sphingenine (Ref. 5037) |
DLB5006 | Akira Hayashi |
d18:1-n14:0 |
C32H63O3N1 | 509.848 | |
Present in blood plasma lipids (Ref. 5037) |
nC14:0 |
||||||||||||||||||
| 132 |  |
2-Hexadecanoylamino-4-octadecene-1, 3-diol / N-Hexadecanoyl-4-sphingenine (Ref. 5037) |
DLB5007 | Akira Hayashi |
d18:1-n16:0 |
C34H67O3N1 | 537.901 | |
Present in blood and brain lipids (Ref. 5037) |
nC16:0 |
||||||||||||||||||
| 133 |  |
0-Octadec-9-enoylamino-4-octadecene-1, 3diol / N-Octadec-9-enoyl-4-sphingenine / N-Oleoyl-4-sphingenine (Ref. 5037) |
DLB5008 | Akira Hayashi |
d18:1-n18:1 |
C36H69O3N1 | 563.938 | |
Present in blood and brain lipids (Ref. 5037) |
nC18:1 (9) |
||||||||||||||||||
| 134 |  |
N-Octadecanoylamino-4-octadecene-1, 3-diol / N-Octadecanoyl-4-sphingenine (Ref. 5037) |
DLB5009 | Akira Hayashi |
d18:1-n18:0 |
C36H71O3N1 | 565.954 | |
Present in blood and brain lipids (Ref. 5037) |
nC18:0 |
||||||||||||||||||
| 135 |  |
2-Eicosanoylamino-4-octadecene-1, 3-diol / N-Eicosanoyl-4-sphingenine / N-Icosanoyl-4-sphingenine (Ref. 5037) |
DLB5010 | Akira Hayashi |
d18:0-n20:0 |
C38H75O3N1 | 594.007 | |
Present in blood and brain lipids (Ref. 5037) |
nC20:0 |
||||||||||||||||||
| 136 |  |
2-Docosanoylamino-4-octadecene-1, 3-diol / N-Docosanoyl-4-sphingenine (Ref. 5037) |
DLB5011 | Akira Hayashi |
d18:1-n22:0 |
C40H79O3N1 | 622.060 | |
Present in brain and blood lipids (Ref. 5037) |
nC22:0 |
||||||||||||||||||
| 137 |  |
N-13-Docosenoylamino--4-octadecene-1, 3-diol / N-13-Docosenoyl-4-sphingenine (Ref. 5037) |
DLB5012 | Akira Hayashi |
d18:1-n22:1 |
C40H77O3N1 | 620.044 | |
Present in blood lipids (Ref. 5037) |
nC22:1 (13) |
||||||||||||||||||
| 138 |  |
2-Tetracosanoylamino-4-octadecene-1, 3-diol / N-Tetracosanoyl-4-sphingenine (Ref. 5037) |
DLB5013 | Akira Hayashi |
d18:1-n24:0 |
C42H83O3N1 | 650.113 | |
93-96 C (Ref. 0251) |
Present in blood and brain lipids (Ref. 5037) |
||||||||||||||||||
| 139 |  |
C(2)-ceramide |
N-methylamino-4-octadecene-1, 3-diol/N-methyl-4-sphingenine/D-erythro-N-acetylsphingosine |
DLB8001 | Takehiko Yokomizo |
C(2)-Cer |
C20H39NO3 | 341.529 | |
Soluble in chloroform, ethanol,methanol, and DMSO (up to 5 mg/ml). |
Produced by the action of a PAF:sphingosine CoA-independent transacetylase. |
nC2:0 |
||||||||||||||||
| 140 |  |
C(8)-ceramide |
N-octanoylamino-4-octadecene-1, 3-diol/N-octanoyl-4-sphingenine/D-erythro-N-octanoylsphingosine |
DLB8002 | Takehiko Yokomizo |
C(8)-Cer |
C26H51NO3 | 425.688 | |
Soluble in ethanol, methanol, chloroform, and DMSO (up to 5 mg/ml). |
nC8:0 |
|||||||||||||||||
| 141 |  |
C(16)-ceramide |
N-octanoylamino-4-octadecene-1, 3-diol/N-octanoyl-4-sphingenine/D-erythro-N-palmitoylsphingosine |
DLB8003 | Takehiko Yokomizo |
C(16)-Cer |
C34H67NO3 | 537.901 | |
Soluble in chloroform (up to 5 mg/ml). |
nC16:0 |
|||||||||||||||||
| 142 |  |
C(2)-dihydroceramide/C(2)-dihydrosphingosine/C(2)-sphinganine |
N-methylamino-4-octadecene-1, 3-diol/N-methyl-4-sphinganine/D-erythro-N-acetylsphinganine |
DLB8004 | Takehiko Yokomizo |
DHC(2)-Cer |
C20H41NO3 | 343.544 | |
C2 Dihydroceramide is inactive and may be used as a negative control for C2 ceramide (Ref. 8008). |
Soluble in chloroform, ethanol, and methanol. |
nC2:0 |
||||||||||||||||
| 143 |  |
C(8)-dihydroceramide/C(8)-dihydrosphingosine/C(8)-sphinganine |
N-octanoylamino-4-octadecene-1, 3-diol/N-octanoyl-4-sphinganine/D-erythro-N-octanoylsphinganine |
DLB8005 | Takehiko Yokomizo |
DHC(8)-Cer |
C26H53NO3 | 427.704 | |
C8 Dihydroceramide is inactive and may be used as a negative control for C8 ceramide (Ref. 8008). |
Soluble in ethanol, DMSO, and chloroform. |
nC8:0 |
||||||||||||||||
| 144 | No image | N,N-dimethylsphingosine |
N,N-dimethylamino-4-octadecene-1, 3-diol/N,N-dimethyl-4-sphingenine/D-erythro-N,N-dimethylsphingosine |
DLB8006 | Takehiko Yokomizo |
DMS |
C20H41NO2 | 327.545 | Soluble in ethanol, isopropanol, chloroform, and methanol. |
Produced endogenously via ceramide catabolism. |
bnC2:0 |
|||||||||||||||||
| 145 |  |
C(8)-Ceramine |
N-octylamino-4-octadecene-1, 3-diol/N-octyl-4-sphingenine/N-octyl-D-erythro-sphingosine |
DLB8007 | Takehiko Yokomizo |
C(8)-Ceramine |
C26H53NO2 | 411.705 | |
An analog of ceramide inert to ceramidases. Rapidly induces apoptosis (Ref. 8013). |
Soluble in ethanol and DMSO. |
nC8:0 |
||||||||||||||||
| AUTHOR | : | Hayashi, A. and Matsubara, T. |
| TITLE | : | On the occurrence of sphinga-4,8-dienine in oyster glycolipid. PubMed ID:4313695 |
| JOURNAL | : | Biochim. Biophys. Acta |
| VOL | : | 202 PAGE : 228-230 (1970) |
| AUTHOR | : | Hayashi, A. and Matsubara. T. |
| TITLE | : | Determination of the structure of sphinga-4,8-dienine from oyster glycolipids by gas chromatography and mass spectrometry. PubMed ID:4331787 |
| JOURNAL | : | Biochim. Biophys. Acta |
| VOL | : | 248 PAGE : 306-314 (1971) |
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| TITLE | : | On the chemistry and occurrence of sphingolipid long-chain bases. PubMed ID:4394487 |
| JOURNAL | : | Chem. Phys. Lipids |
| VOL | : | 5 PAGE : 6-43 (1970) |
| AUTHOR | : | Matsubara, T., Hayashi, A., Banno, Y., Morita, T., and Nozawa, Y. |
| TITLE | : | Cerebroside of the dimorphic human pathogen, Candida albicans PubMed ID:3555875 |
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| VOL | : | 43 PAGE : 1-12 (1987) |
| AUTHOR | : | Matsubara, T. |
| TITLE | : | The structure and distribution of ceramide aminoethylphosphonates in the oyster (Ostrea gigas). PubMed ID:1137715 |
| JOURNAL | : | Biochim. Biophys. Acta |
| VOL | : | 388 PAGE : 353-360 (1975) |
| AUTHOR | : | Matsubara, T. |
| TITLE | : | Distribution of the dienic long chain bases in shellfish sphingophosphonolipids. |
| JOURNAL | : | Chem. Phys. Lipids |
| VOL | : | 14 PAGE : 247-259 (1975) |
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| TITLE | : | Characterization of aminoalkylphophonyl cerebrosides in muscle tissue of Turbo cornutus. PubMed ID:699219 |
| JOURNAL | : | Chem. Phys. Lipids |
| VOL | : | 22 PAGE : 9-23 (1978) |
| AUTHOR | : | Matsuura, F. |
| TITLE | : | Phosphonosphingoglycolipid, a novel sphingolipid from the viscera of Turbo cornutus. PubMed ID:890866 |
| JOURNAL | : | Chem. Phys. Lipids |
| VOL | : | 19 PAGE : 223-242 (1977) |
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| TITLE | : | A new homologue of phosphonosphingolipid, N-methylaminoethyl-phosphonyltrigalactosylceramide. |
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| VOL | : | 1006 PAGE : 89-96 (1989) |
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| TITLE | : | Structural studies on glycolipid of shellfish. III. Novel glycolipids from Turbo cornutus PubMed ID:6263873 |
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| TITLE | : | Structural studies on glycolipids of shellfish. V. Gala-6 series glycosphingolipids of the marine snail, Chlorostoma argyrostoma turbinatum PubMed ID:3011773 |
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| TITLE | : | Characterization of docosa-4,15-sphingadienine and 4-hydroxy-docosa-15-sphingenine in sphingophosphonolipids from Turbo cornutus by gas chromatography-mass spectrometry PubMed ID:1122564 |
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| VOL | : | 14 PAGE : 102-105 (1975) |
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| TITLE | : | Gas chromatography and mass spectrometry of sphingolipid bases. Characterization of sphinga-4,14-dienine from plasma sphingomyelin PubMed ID:5660077 |
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| VOL | : | 7 PAGE : 2609-2614 (1968) |
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| VOL | : | 10 PAGE : 687-693 (1969) |
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| TITLE | : | Polar lipids in bovine milk. I. Long-chain bases in sphingomyelin PubMed ID:5816447 |
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| VOL | : | 176 PAGE : 537-546 (1969) |
| AUTHOR | : | Panganamala, R. V., Geer, J. C., and Cornwell, D. G. |
| TITLE | : | Long-chain bases in the sphingolipids of atherosclerotic human aorta PubMed ID:4307832 |
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| AUTHOR | : | Carter, H. E., and Hirschberg, C. B. |
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| AUTHOR | : | Stanacev, N.Z. and Chargaff, E. |
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| JOURNAL | : | Japan. Oil Chem. Soc. (Yukagaku ) |
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| TITLE | : | Identification of molecular species of ceramide 2-N-methyl-aminoethylphosphates containing normal fatty acids and dihydroxy long-chain bases from Turbo cornutus. PubMed ID:4733854 |
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| TITLE | : | Biochemistry of the sphingosine III. Structure of sphingosine |
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| AUTHOR | : | Carter, H. E., and Humiston, C. G. |
| TITLE | : | Biochemistry of the sphingolipides. V. The structure of sphingine PubMed ID:14861218 |
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| VOL | : | 191 PAGE : 727-733 (1951) |
| AUTHOR | : | Hannun, Y. A., Loomis, C. R., Merrill, A. H., Jr., and Bell, R. M. |
| TITLE | : | Sphingosine inhibition of protein kinase C activity and of phorbol dibutyrate binding in vitro and in human platelets PubMed ID:3462188 |
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| TITLE | : | Biochemistry of the sphingolipids. XIII. Determination of the structure of cerebrosides from wheat flour PubMed ID:13691142 |
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| VOL | : | 236 PAGE : 1912-1916 (1961) |
| AUTHOR | : | Karlsson, K. A., and Holm, G. A. |
| TITLE | : | Studies on sphingosines. 9. C19-sphingosines, hitherto unknown sphingosines PubMed ID:5859480 |
| JOURNAL | : | Acta Chem Scand. |
| VOL | : | 19 PAGE : 2423-2425 (1965) |
| AUTHOR | : | Klenk, E., and Huang, R. T. |
| TITLE | : | [A method for the preparation of ceramide from brain gangliosides and the nature of their sphingosine bases] PubMed ID:4310673 |
| JOURNAL | : | Hoppe Seylers Z Physiol Chem. |
| VOL | : | 350 PAGE : 1081-1087 (1969) |
| AUTHOR | : | O'Connor, J. D., Polito, A. J., Monroe, R. E., Sweeley, C. C., and Bieber, L. L. |
| TITLE | : | Characterization of invertebrate sphingolipid bases: occurrence of eicosasphinga-4, 11-dienine and eicosasphing-11-enine in scorpion PubMed ID:5417188 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 202 PAGE : 195-197 (1970) |
| AUTHOR | : | Ballio, A., Casinovi, C. G., Framondino, M., Marino, G., Nota, G., and Santurbano, B. |
| TITLE | : | A new cerebroside from Fusicoccum amygdali Del PubMed ID:454639 |
| JOURNAL | : | Biochim Biophys Acta. |
| VOL | : | 573 PAGE : 51-60 (1979) |
| AUTHOR | : | Karlsson, K.-A., Leffler, H., and Samuelsson, B.O. |
| TITLE | : | Characterization of cerebroside (monoglycosyl ceramide) from the sea anemone, Metridium senile. Identification of the major long-chain base as an unusual dienic base with a methyl branch at a double bond. PubMed ID:38852 |
| JOURNAL | : | Biochim. Biophys. Acta |
| VOL | : | 574 PAGE : 79-92 (1979) |
| AUTHOR | : | Ohnishi, M., Kawase, S., Ito, S., and Fujino, Y. |
| TITLE | : | On sphingolipids of Basidiomycota, Grifola frondosa (in Japanese) |
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