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Long chain base and Ceramide

(total 145)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
4,8-sphingadienine
Erythro-octadeca-4E,8E-sphingadienine/ D-Erythro-1.3-dihydroxy-2-amino-trans-4-trans-8-octadecadiene (Ref. 0001/0002/0003)
 DLB0001
Akira Hayashi
d18:2 (4,8)
 C18H35O2N1 297.476 Download ChemDraw structure file


MS of aldehyde obtained by periodate oxidation of the LCB(Ref. 0002); MS of N-acetyl-di-O-TMS LC(Ref. 0002); MS of TMS-polyhydroxy compound obtained by osmium oxidation of N-acetyl-LCB(Ref. 0002/0005); MS of TMS deriv. of methylated, hydroxylated DNP-LCB(Ref. 0003).


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).




[0001] / [0002] / [0003] / [0004] / [0005] / [0006] / [0007] / [0009] / [0010] / [0011]
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 Download ChemDraw structure file


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).




[0012]
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 Download ChemDraw structure file


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).




[0012]
4
Octadeca-4,14-sphingadienine/ Erythro-1,3-dihyfroxy-2-amino-trans-4,cis-14-octadecadiene (Ref. 0013/0014/0015)
 DLB0004
Akira Hayashi
d18:2 (4,14)
 C18H35O2N1 297.476 Download ChemDraw structure file


EI/MS of N-acetyl-O-TMS-LCB(Ref. 0014); EI/MS of TMS deriv. of polyhydroxy compd. obtained by methylation and hydroxylation of DNP-LCB(Ref. 0003)


Sphingomyelin obtained from human blood plasma (Ref. 0003/0013/0014/0015)



GC data of N-acetyl-O-TMS-LCB (column: 3% SE-30/3%XE-60/3%OV-17(Ref. 0014)
[0003] / [0013] / [0014] / [0015]
5
Dodecasphinganine/ 1,3-Dihydroxy-2-aminododecane (Ref. 0016)
 DLB0005
Akira Hayashi
d12:0
 C12H27O2N1 217.348 Download ChemDraw structure file


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)




[0016]
6
Tetradecasphinganine/ 1,3-Dihydroxy-2-aminotetradecane (Ref. 0016/0017)
 DLB0006
Akira Hayashi
d14:0
 C14H31O2N1 245.401 Download ChemDraw structure file


ECL Value of aldehyde obtained by periodate oxidation of the LCB/ GC-MS of alcohol obtained by reduction of the alcohol ( no data)(Ref. 0016)/GLC of 1,3-dioxylane deriv. of aldehyde which is obtained from the LCB (Ref. 0017)


Sphingomyelin obtained from Spray- dried buttermilk powder(Ref. 0016)/sphingomyelin of human aorta (Ref. 0017)




[0016] / [0017]
7
Pentadecasphinganine/ 1,3-Dihydroxy-2-aminopentadecane (Ref. 0016/0017/0019)
 DLB0007
Akira Hayashi
d15:0
 C14H29O2N1 243.386 Download ChemDraw structure file


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)




[0016] / [0017] / [0019]
8
Hexadecasphinganine/ 1,3-Dihydroxy-2-aminohexadecane
 DLB0008
Akira Hayashi
d16:0
 C16H35O2N1 273.455 Download ChemDraw structure file


ECL value of aldehyde obtained by periodate oxidation of the LCB/GC-MS of alcohol oatained by reduction of the alcohol (no data) (Ref. 0016)/ GLC of 1,3-dioxylane deriv. of aldehyde obtained from the LCB (Ref. 0017)/ GC-MS of N-acetyl-O-TMS-LCB (Ref. 0019)


Sphingomyelin obtained from spray-dried butternilk powder (Ref. 0016); Sphingomyelin obtained from atherosclerotic human aorta (0.6pm0.1%) (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).




[0013] / [0016] / [0017] / [0018] / [0019] / [0021]
9
Heptadecasphinganine/ 1,3-Dihydroxy-2-amino-heptadecane(Ref. 0016)
 DLB0009
Akira Hayashi
d17:0
 C17H37O2N1 287.481 Download ChemDraw structure file


Identified with ECL values of aldehydes obtained from the LCB and GC-MS of alcohols obtained by reduction of the aldehydes.


Milk sphingomyelin (1.1 mole%)/human blood serum sphingomyelin (Ref. 0022)/human blood plasma sphingomyelin(Ref. 0020)/human blood plasma sphingomyelin (0.3 %) (Ref. 0013)/mild alkali stable lipids of yeast, Hansenula ciferrii (0.1 %) (Ref. 0021).




[0013] / [0016] / [0020] / [0021] / [0022]
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 Download ChemDraw structure file
Effect on phorbol-dependent differentiation of HL-60 cell(Ref. 0037)
143-145degC(tribenzoyldihydrosphingosine) (Ref. 0034)/122-123 degC/79degC (Ref. 0261)/124-125degC (N-acetyl-D(+)-sphinganine) (Ref. 0261)/ 96-97degC (Triacetyl deriv.) (Ref. 0261)
[a]22D=+19.2 (Erythro-triacetyl) (Ref. 0023)
[a]28546 = +6.0deg (in CHCl3-MeOH, 10:1) (Ref. 0261)/[a]28546 = +7.7deg (in Hexeane-EtOH, 10:1) (N-acetyl deriv.) (Ref. 0261) [a]28546 =+21deg in hexane-EtOH(10:1) (Triacetyl deriv.) (Ref. 0261)
Racem. Threo-triacetyl-dihydrosphingosine (Ref. 0024)/Optically active triacetyldihydrosphingosine (Ref. 0024)/Raswm. Erythro-triacetyl-dihydrosphingosine(Ref. 0024)
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)


Ceramide phospholipid obtained from CR2A strain of anaerobic bacteria, Bacteroides melaninogenicus (Ref. 0025)/Milk sphingomyelin (5.9 mole %) (Ref. 0016)



GC data (column: 2% OV-1) of N-Acetyl-O-TMS-LCB (Ref. 0025)
[0016] / [0023] / [0024] / [0025] / [0034] / [0037] / [0260] / [0261]
11
Nonadecasphinganine/1,3-dihydroxy-2-aminononadecane (Ref. 0016)
 DLB0011
Akira Hayashi
d19:0
 C19H41O2N1 315.534 Download ChemDraw structure file





Milk Sphingomyelin (0.2 mole%) (Ref. 0016)/Mild alkali-stable lipids obtained from yeast, Hansenula ciferrii (Ref. 0021)




[0016] / [0021]
12
Eicosasphinganine/ 1,3-Dihydroxy-2-aminoeicosane (Ref. 0016/0026/0028)
 DLB0012
Akira Hayashi
d20:0
 C20H43O2N1 329.561 Download ChemDraw structure file

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).
[0016] / [0021] / [0026] / [0027] / [0028]
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 Download ChemDraw structure file





Milk sphingomyelin (0.5mole% ) (Ref. 0016)




[0016]
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 Download ChemDraw structure file





Milk sphingomyelin (0.4 mole% ) (Ref. 0016)




[0016]
15
Tetradeca-4-sphingenine / D-erythro-1,3-dihydroxy-2-amino-trans-4-tetradecene (Ref. 0016/0017/0019)
 DLB0015
Akira Hayashi
d14:1(4t)
 C14H29O2N1 243.386 Download ChemDraw structure file


EI-MS (a part) (Ref. 0029)


Milk sphingomyelin (1.3 mole%) (Ref. 0016) / Atherosclerotic human aorta sphingomyelin (Ref. 0017) / Mild alkali-stable lipids obtained from larvae of house fly, Musca domestica (54 %) (Ref. 0019) / Total polar lipids obtained from vental cord of cray fish, Procambrus clarkii (Ref. 0029)




[0016] / [0017] / [0019] / [0029]
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 Download ChemDraw structure file





Milk sphingomyelin (0.5 mole%) (Ref. 0016)/ Mild alkali-stable lipids obtained fron larvae of house fly, Mucosa domestica (Ref. 0019)




[0016] / [0019]
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 Download ChemDraw structure file


Ei/MS of N-acetyl-O-TMS derivative (Ref. 0031); EI/MS of O-TMS derivative (Ref. 0030).


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).




[0003] / [0005] / [0006] / [0007] / [0008] / [0009] / [0010] / [0011] / [0014] / [0016] / [0017] / [0019] / [0020] / [0022] / [0030] / [0031]
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 Download ChemDraw structure file


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).




[0005] / [0006] / [0007] / [0008] / [0009] / [0010] / [0011] / [0014] / [0017] / [0019] / [0020] / [0022] / [0032] / [0033]
19
Sphingosine
4-Sphingenine / D-Erytjro-1,3-dihydroxy-2-amino-trans-4-octadecene , 2S, 3R, 4E-form (Ref. 0032/0034)
 DLB0019
Akira Hayashi
d18:1 (4)
 C18H37O2N1 299.492 Download ChemDraw structure file
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
80-84deg/79-81deg; 82.5-83degC (Ref. 5012)
[a]D =+3.25deg (Ref. 5012)
Insol. in water. Soluble in CHCl3, EtOH and MeOH (Ref. 5012)
trans double bond (980cm-1, 10.3nm)
1H-NMR (Ref. 0260)/ 220MHz-1H-NMR (Ref. 0262)
EI/MS of N-acetyl-O-TMS derivative (Ref. 0002/0014)


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)
(Ref. 5024/5025/5026)
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)
Sphingosine kinase (yeast and mouse) (Ref. 5014/5015); Acid ceramidase (mouse and human) (Ref. 5022/5023)

[0002] / [0006] / [0007] / [0008] / [0009] / [0010] / [0011] / [0014] / [0031] / [0032] / [0034] / [0036] / [0037] / [0038] / [0260] / [0262] / [5001] / [5002] / [5012] / [5014] / [5015] / [5017] / [5018] / [5021] / [5022] / [5023] / [5024] / [5025] / [5026]
20
2X, 3X-8-sphingenine / 1,3-Dihydroxy-2-amino-trans-8-octadecene (Ref. 0039)
 DLB0020
Akira Hayashi
d18:1 (8)
 C18H37O2N1 299.492 Download ChemDraw structure file

970cm-1 (Ref. 0039)




Cerebroside obtained from flour (Ref. 0039)




[0039]
21
2X, 3X-nonadeca-X-4-sphingenine / 1,3-Dihydroxy-2-amino-4-nonadecene (Ref. 0016/0040)
 DLB0021
Akira Hayashi
d19:1 (4)
 C19H39O2N1 313.519 Download ChemDraw structure file





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).




[0005] / [0006] / [0007] / [0008] / [0009] / [0011] / [0016] / [0031] / [0040]
22
Eicosa-4-sphingenine / D-Erythro-1,3-dihydroxy-2-amino-trans-4-eicosene (Ref. 0026/0027/0028/0006/0041)
 DLB0022
Akira Hayashi
d20:1 (4)
 C20H41O2N1 327.545 Download ChemDraw structure file

106-107degC (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)
[0006] / [0007] / [0008] / [0026] / [0027] / [0028] / [0041]
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 Download ChemDraw structure file





Phosphosphingolipid of scorpion, Centruroides sculpturatus (8%) (Ref. 0042)




[0042]
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 Download ChemDraw structure file





Human brain ganglioside (trace) (Ref. 0041)




[0041]
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 Download ChemDraw structure file


Ei-MS of N-DNP-O-TMS-derivative (Ref. 0003)


Cerebroside of sea star, Asterias rubens (Ref. 0003)




[0003]
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 Download ChemDraw structure file


EI-MS of N-DNP-O-TMS derivative (Ref. 0003)


Cerebroside of a sea star, Asterias rubens (Ref. 0003)




[0003]
27
2X,3X-Hexadecasphingadienine / 1,3-Dihydroxy-2-amino-hexadecadiene (Ref. 0040)
 DLB0027
Akira Hayashi
d16:2
 C16H31O2N1 269.423 Download ChemDraw structure file










[0040]
28
2X,3X-Heptadecasphingadienine / 1,3-Dihydroxy-2-aminoheptadecadiene (Ref. 0040)
 DLB0028
Akira Hayashi
d17:2
 C17H33O2N1 283.449 Download ChemDraw structure file










[0040]
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 Download ChemDraw structure file





cow heart (Ref. 0032)




[0032]
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 Download ChemDraw structure file





Sphingomyelin obtained from human plasma (Ref. 0020)




[0020]
31
2X, 3X-sphingadienine / 1,3-Dihydroxy-2-aminooctadecadiene (Ref. 0017)
 DLB0031
Akira Hayashi
d18:2
 C18H35O2N1 297.476 Download ChemDraw structure file





Sphingomyelin obtained from atherosclerotic human aorta (Ref. 0017)




[0017]
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 Download ChemDraw structure file





Phosphosphingolipid of a scorpion, Centruroides scalpturatus (35%) (Ref. 0042)




[0042]
33
2X, 3X-eicosasphingadienine / 1, 3-Dihydroxy-2-aminoicosadienine (Ref. 0032)
 DLB0033
Akira Hayashi
d20:2
 C20H39O2N1 325.529 Download ChemDraw structure file





Ceramide aminoethylphosphonate obtained from oyster, Ostrea gigas (adductor muscle 0, gills 7.6%, mantle 8.5%, viscera 8.1%) (Ref. 0005); Sphingophosphonolipids obtained from 8 kinds of shellfish (chiton 29.8%, Tegula lishkei 12.6%, Cellana eucosmia 47.1%) (Ref. 0006)




[0005] / [0006] / [0032]
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 Download ChemDraw structure file


EI-MS of N-DNP-O-TMS derivative (Ref. 0003)


Cerebroside of a sea star, Asterias rubens (Ref. 0003)




[0003]
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 Download ChemDraw structure file


EI-MS of N-DNP-O-TMS derivative (Ref. 0003)


Cerebroside of a sea star, Asteria rubens (Ref. 0003)




[0003]
36
9-Methyl-2X, 3X-octadeca-4E, 8E-sphingadienine / 9- Methyl-1, 3-dihydroxy-2-amino-trans-4, trans-8-octadecadiene (Ref. 0004/0043/0044/0052)
 DLB0036
Akira Hayashi
9-Me-d18:2 (4, 8)
 C19H37O2N1 311.503 Download ChemDraw structure file
A fruiting-inducing activity
1H-NMR of cerebroside containing this base (Ref. 0043/0044/0046)
EI-MS of O-TMS derivative (Ref. 0004); EI-MS of DNP derivative (Ref. 0044); EI-MS of N-DNP-O-TMS derivative (Ref. 0044)


Cerebroside of dimorphic human pathogen, Candida albicans (Ref. 0004); Cerebroside of imperfect fungus, Fusicoccum amygdali (Ref. 0043); Cerebroside of a sea star, Metridium senile (Ref. 0044); Cerebroside of Glitora frondosa (Ref. 0045); Cerebroside of Schizophylum commune (Ref. 0046).




[0004] / [0043] / [0044] / [0045] / [0046] / [0047] / [0052]
37
2X, 3X-octadecasphingadienine / 1, 3-Dihydroxy-2-amino-docosadienine (Ref. 0033)
 DLB0037
Akira Hayashi
d22:2
 C22H43O2N1 353.582 Download ChemDraw structure file





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)




[0006] / [0007] / [0008] / [0009] / [0010] / [0033]
38
1, 3, 4-Trihydroxy-2-aminoheptadecane / 4X-Hydroxy-2X, 3X-heptadecasphinganine (Ref. 0003/0032)
 DLB0038
Akira Hayashi
t17:0
 C17H37O3N1 303.481 Download ChemDraw structure file





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)




[0003] / [0007] / [0008] / [0018] / [0021] / [0032] / [0049] / [0050] / [0051] / [0056]
39
phytosphingosine
D-ribo-1, 3, 4-trihydroxy-2-aminooctadecane / 4D-hydroxysphinganine (Ref. 0052)
 DLB0039
Akira Hayashi
t18:0
 C18H39O3N1 317.507 Download ChemDraw structure file


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)
(Ref. 0053)



[0003] / [0007] / [0008] / [0009] / [0018] / [0021] / [0049] / [0050] / [0051] / [0052] / [0053] / [0054] / [0056]
40
1, 3, 4-Trihydroxy-2-aminononadecane / 4X-Hydroxy-2X, 3X-nonadecasphinganine
 DLB0040
Akira Hayashi
t19:0
 C19H41O3N1 331.534 Download ChemDraw structure file





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).




[0003] / [0008] / [0021] / [0040] / [0049] / [0054] / [0056]
41
DLB0041
Akira Hayashi
t20:0
 C20H43O3N1 345.560 Download ChemDraw structure file





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).
(Ref. 0053)



[0003] / [0008] / [0021] / [0049] / [0053] / [0054] / [0056]
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 Download ChemDraw structure file

Insol. in water. Soluble in CHCl3 and EtOH.




Cerebroside of hay and concentrate (22.9 % and 22.7%, respectively) (Ref. 0055); Phosphonocerebroside of muscle part of Turbo cornutus (Ref. 0007); Phosphonocerebroside in visceral part of Turbo cornutus (Ref. 0008); Plants (Ref. 5030)

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)

[0007] / [0008] / [0051] / [0055] / [5030] / [5031]
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 Download ChemDraw structure file

Insol. in water. So;b;e in CHCl3 and EtOH.




Cerebroside in hay (74.4%) and concentrate (58.2%) (Ref. 0055); Plants (Ref. 5030)

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)

[0055] / [5030] / [5031]
44
1, 3-Dihydroxy-2-amino-16-methylheptadecane / 16-Methyl-2X, 3X-heptadecasphinganine
 DLB0044
Akira Hayashi
iso-d18:0
 C18H39O2N1 301.508 Download ChemDraw structure file





Sphingomyelin of coe milk (Ref. 0016); Sphingomyelin of medulla and cortex of oxkidney (Ref. 0049); Ceramide phospholipids of anaerobic bacteria, Bacteroides melaninogenicus (4%) (Ref. 0025)Sphingolipids of human and ox (Ref. 0056); Sphingomyelin of oxkidney (Ref. 0003)




[0003] / [0016] / [0025] / [0049] / [0056]
45
1, 3-Dihydroxy-2-amino-trans-4, trans-8, trans-10-octadecatriene / Octadeca-trans4, trans-8, trans-10-sphingatriene (Ref. 0057/0058)
 DLB0045
Akira Hayashi
d18:3 (4, 8, 10)
 C18H33O2N1 295.460 Download ChemDraw structure file

1H-NMR of aldehyde derived from this base (Ref. 0058)
EI-MS of O-TMS derivative (Ref. 0057); EI-MS of TMS-polyhydroxy-N-acetyl derivative (Ref. 0057); EI-MS of TMS-polyhydroxy-alcohol (C16:3) derived from this base (Ref. 0057);


Major component of ceramide mohexoside obtained from Lingula unguis (Ref. 0057) ; Glucosyl ceramide obtained from a sea star, Asterias amurensis (17.4%) (Ref. 0058); Phosphonocerebroside Antarctic , Euphausia superba (48.2%)




[0057] / [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)
 Download ChemDraw structure file





Glucosyl ceramide obtained from a sea star, Asterias amurensis (7.7%) (Ref. 0058)




[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 Download ChemDraw structure file

79degC (Ref. 0261)/124-125degC (N-acetyl deriv.) (Ref. 0261)/ 96-97degC (Triacetyl deriv.) (Ref. 0261)
[a]28546 = -6.0deg (in CHCl3-MeOH, 10:1) (Ref. 0261)/ [a]28546 =-8.0deg (in hexane-EtOH 10:1) (N-acetyl deriv.) (Ref. 0261)/[a]28546=-21deg (in hexane-EtOH 10:1) (Triacetyl deriv.) (Ref. 0261)









[0261]
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 Download ChemDraw structure file

108degC (Ref. 0261)/96-97degC (N-acetyl deric.) (Ref. 0261) 46degC (triacetyl deriv.) (Ref. 0261)
[a]28546 =+13deg (Ref. 0261)/ {a]28546 = +6.2deg in hexane-EtOH (10:1) (N-acetyl deriv.) (Ref. 0261)/ [a]28546 = +8.0deg in pentane (triacetyl deriv.) (Ref. 0261)









[0261]
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 Download ChemDraw structure file

108degC (Ref. 0261)/ 96-97degC (N-acetyl deriv.) (Ref. 0261) / 46degC (Triacetyl deriv.) (Ref. 0261)
[a]28546 = -13deg (Ref. 0261)/ [a]28546 = -6.5deg in hexane-EtOH (10:1) (N-acetyl deriv.) (Ref. 0261) / [a]28546 =-8.0deg in pentane (Triacetyl deriv.) (Ref. 0261)









[0261]
50
2-Amino-15-methyl hexadecane-1, 3-diol (Ref. 0101/0103)
 DLB0101
Akira Hayashi
15-Me-d16:0 / iso-d17:0
 C17H37O2N1 287.481 Download ChemDraw structure file





Animals, Protozoa




[0101] / [0103]
51
2-Amino-16-methylheptadecane-1, 3-diol (Ref. 0101/0103)
 DLB0102
Akira Hayashi
16-Me-d17:0 / iso-d18:0
 C18H39O2N1 301.508 Download ChemDraw structure file





Animals




[0101] / [0103]
52
2-Amino-17-methyloctacecane-1, 3-diol (Ref. 0101/0103)
 DLB0103
Akira Hayashi
17-Me-d18:0 / iso d19:0
 C19H41O2N1 315.534 Download ChemDraw structure file





Animals




[0101] / [0103]
53
2-Amino-18-methylnonadecane-1, 3-diol (Ref. 0101)
 DLB0104
Akira Hayashi
18-Me-d19:0/ iso-d20:0
 C20H43O2M1 Download ChemDraw structure file





Animals




[0101]
54
2-Amino-14-methylhexadecane-1, 3-diol (Ref. 0101)
 DLB0105
Akira Hayashi
14-Me-d16:0/ anteiso-d17:0
 Download ChemDraw structure file





Animals.




[0101]
55
2-Amino-16-methyloctadecane-1, 3-diol (Ref. 0101/0103/0111/0112)
 DLB0106
Akira Hayashi
16-Me-d18:0 / anteiso-d19:0
 C19H41O2N1 315.534 Download ChemDraw structure file





Animals; Harderian gland of a guinea pig.




[0101] / [0103] / [0111] / [0112]
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 Download ChemDraw structure file





Animals.




[0101]
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 Download ChemDraw structure file





Animals.




[0101]
58
2-Amino-15-methyl-4-hexadecene-1, 3-diol (Ref. 0101/0103)
 DLB0109
Akira Hayashi
15-Me-d16:1 (4) / iso-d17:1 (4)
 C17H35O2N1 285.465 Download ChemDraw structure file





Animals.




[0101] / [0103]
59
2-Amino-16-methyl-4-heptadecene-1, 3-diol (Ref. 0101/0103/0102)
 DLB0110
Akira Hayashi
16-Me-d17:1 (4) / iso-d18:1 (4)
 C18H37N2O1 297.499 Download ChemDraw structure file





Animals.




[0101] / [0102] / [0103]
60
2-Amino-17-methyl-4-octadecene-1, 3-diol (Ref. 0101/0102/0103/0106)
 DLB0111
Akira Hayashi
17-Me-d18:1 (4)/ iso-d18:1 (4)
 C19H39O2N1 313.519 Download ChemDraw structure file





Animals.




[0101] / [0102] / [0103] / [0106]
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 Download ChemDraw structure file





Animals.




[0106]
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 Download ChemDraw structure file





Animals.




[0101]
63
2-Amino-14-methyl-4-hexadecene-1, 3-diol (Ref. 0101/0112)
 DLB0114
Akira Hayashi
14-Me-d16:1 (4) / anteiso-d17:1 (4)
 C17H35O2N1 285.465 Download ChemDraw structure file





Animals.




[0101] / [0112]
64
2-Amino-16-methyl-4-octadecene-1, 3-diol (Ref. 0101/0102/0103/0105/0112)
 DLB0115
Akira Hayashi
16-Me-d18:1 (4)/ anteiso-d 19:1 (4)
 C19H39O2N1 313.519 Download ChemDraw structure file





Animals.




[0101] / [0102] / [0103] / [0105] / [0112]
65
2-Amino-17-methyl-4-nonadecene-1, 3-diol (Ref. 0101/0106)
 DLB0116
Akira Hayashi
17-Me-d19:1 (4) / anteiso-d20:1 (4)
 C20H41O2N1 327.545 Download ChemDraw structure file





Animals.




[0101] / [0106]
66
2-Amino-14-methylpentadecane-1, 3, 4-triol (Ref. 0107)
 DLB0117
Akira Hayashi
14-Me-t15:0 / iso-t16:0
 C16H35O3N1 289.454 Download ChemDraw structure file





Animals.




[0107]
67
2-Amino-15-methylhexadecane-1, 3, 4-triol (Ref. 0101/0103/0107)
 DLB0118
Akira Hayashi
15-Me-t16:0 / iso-t17:0
 C17H37O3N1 303.481 Download ChemDraw structure file





Animals.




[0101] / [0103] / [0107]
68
iso-phytosphingosine
2-Amino-16-methylheptadecane-1, 3, 4-triol (Ref. 0101/0102/0103/0104/0107)
 DLB0119
Akira Hayashi
16-Me-t17:0 / iso-t18:0
 C18H39O3N1 317.507 Download ChemDraw structure file





Animals; Fungi.




[0101] / [0102] / [0103] / [0104] / [0107]
69
2-Amino-17-methyl-octadecane-1, 3, 4-triol (Ref. 0101/0102/0103/0104)
 DLB0120
Akira Hayashi
17-Me-t18:0 / iso-t19:0
 C19H41O3N1 331.534 Download ChemDraw structure file





Animals; fungi.




[0101] / [0102] / [0103] / [0104]
70
2-Amino-18-methylnonadecane-1, 3, 4-triol (Ref. 0104)
 DLB0121
Akira Hayashi
18-Me-t19:0
 C20H43O3N1 345.560 Download ChemDraw structure file





Fungi.




[0104]
71
2-Amino-19-methylicosane-1, 3, 4-triol (Ref. 0101/0104)
 DLB0122
Akira Hayashi
19-Me-t20:0 /iso-t21:0
 C21H45O3N1 359.587 Download ChemDraw structure file





Animals; Fungi.




[0101] / [0104]
72
2-Amino-20-methylhenicosane-1, 3, 4-triol (Ref. 0104)
 DLB0123
Akira Hayashi
20-Me-t21:0 / iso-t22:0
 C22H47O3N1 373.614 Download ChemDraw structure file





Fungi.




[0104]
73
2-Amino-14-methylhexadecane-1, 3, 4-triol (Ref. 0107)
 DLB0124
Akira Hayashi
14-Me-t16:0 / anteiso-t17:0
 C17H37O3N1 303.481 Download ChemDraw structure file










[0107]
74
2-Amino-15-methylheptadecane-1, 3, 4-triol (Ref. 0107)
 DLB0125
Akira Hayashi
15-Me-t17:0 / anteiso-t18:0
 C18H39O3N1 317.507 Download ChemDraw structure file





Animals.




[0107]
75
2-Amino-16-methyloctadecane-1, 3, 4-triol (Ref. 0101/0102/0103/0105)
 DLB0126
Akira Hayashi
16-Me-t18:0 / anteiso-t19:0
 C19H37O3N1 327.502 Download ChemDraw structure file





Animals.




[0101] / [0102] / [0103] / [0105]
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 Download ChemDraw structure file





Fungi.




[0104]
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 Download ChemDraw structure file





Fungi; Animals.




[0108]
78
2-Amino-10-methylhexadecane-1, 3-diol (Ref. 0111/0112)
 DLB0129
Akira Hayashi
10-Me-d16:0
 C17H37O2N1 287.481 Download ChemDraw structure file





Harderian gland of a guinea pig.




[0111] / [0112]
79
2-Amino-9-methylhexadecane-1, 3-diol (Ref. 0111/0112)
 DLB0130
Akira Hayashi
9-Me-d16:0
 C17H37O2N1 287.481 Download ChemDraw structure file





Harderian gland of a guinea pig.




[0111] / [0112]
80
2-Amino-8-methylhexadecane-1, 3-diol (Ref. 0111/0112)
 DLB0131
Akira Hayashi
8-Me-d16:0
 C17H37O2N1 287.481 Download ChemDraw structure file





Harderian gland of a guinea pig.




[0111] / [0112]
81
2-Amino-10-methylheptadecane-1, 3-diol (Ref. 0111/0112)
 DLB0132
Akira Hayashi
10-Me-d17:0
 C18H39O2N1 301.508 Download ChemDraw structure file





Harderian gland of a guinea pig




[0111] / [0112]
82
2-Amino-9-methylheptadecane-1, 3-diol (Ref. 0111/0112)
 DLB0133
Akira Hayashi
9-Me-d17:0
 C18H39O2N1 301.508 Download ChemDraw structure file





Hardeian gland of a guinea pig.




[0111] / [0112]
83
2-Amino-8-methylheptadecane-1, 3-diol (Ref. 0111/0112)
 DLB0134
Akira Hayashi
8-Me-d17:0
 C18H39O2N1 301.508 Download ChemDraw structure file





Harderian gland of a guines pig.




[0111] / [0112]
84
2-Amino-10-methyloctadecane-1, 3-diol (Ref. 0111/0112)
 DLB0135
Akira Hayashi
10-Me-d18:0
 C19H41O2N1 315.534 Download ChemDraw structure file





Harderian gland of a guinea pig.




[0111] / [0112]
85
4-Hydroxyeicosasphinganine
2-Amino-1, 3, 4-icosanetriol, (2S, 3S, 4R)-Form / D(+)-ribo-2-amino-1, 3, 4-trihydroxyicosane (Ref. 0201/0218/0249)
 DLB0201
Akira Hayashi
2S, 3S, 4R-t20:0
 C20H43O3N1 345.560 Download ChemDraw structure file

97-99degC (Ref. 0218)
[a]17D==8.1deg(C, 0.34 in CHCl3) (Ref. 0218)








(Ref. 0232/0233/0234)
[0201] / [0218] / [0232] / [0233] / [0234] / [0249]
86
2-(N-benzoyl)-amino-1, 3, 4-icosanetriol (Ref. 0202/0214/0249)
 DLB0202
Akira Hayashi
C27H47O4N1 449.666 Download ChemDraw structure file

136-137degC (Ref. 0214)
[a]D=+3.6deg(C, 1 in pyr) (Ref. 0214)








(Ref. 0232/0233/0234)
[0202] / [0214] / [0232] / [0233] / [0234] / [0249]
87
2-(N-Benzoyl)-amino-1, 3, 4-icosanetri-O-acetate (Ref. 0203/0214/0249)
 DLB0203
Akira Hayashi
C33H53O3N1 511.779 Download ChemDraw structure file









(Ref. 0232/0233/0234)
[0203] / [0214] / [0232] / [0233] / [0234] / [0249]
88
2-(N-acetylamino)-1.3-(O-diacetylhydroxy)-4-octadecene, (2s, 3R, 4E)-form (Ref. 0204/0251)
 DLB0204
Akira Hayashi
Tri-Ac-d18:1 (4)
 C24H43O5N1 425.602 Download ChemDraw structure file

103.5-104deg(Ref. 0250)
[a]19D = -24.1deg/ [a]D = -13deg (c, 0.5 in CHCl3) (Ref. 0250)









[0204] / [0250] / [0251]
89
2-(N-benzoylamino)-1, 3-(O-diacetylhydroxy)-4-octadecene, (2S, 3R, 4E)-form. (Ref. 0205/0252)
 DLB0205
Akira Hayashi
Tri-benzoyl-d18:1 (4)
 C39H49O3N1 579.811 Download ChemDraw structure file

121.5-123.5deg (Ref. 0250)
[a]27D = -11.2deg (Ref. 0250)








Crist. (EtOH)
[0205] / [0250] / [0252]
90
2-Amino-1, 3, 4-hexadecanetriol, (2S, 3S, 4R)-form (Ref. 0206/0203/0205/0249)
 DLB0206
Akira Hayashi
2S, 3S, 4R-t16:0
 C16H35O3N1 289.454 Download ChemDraw structure file





Acanthacerebroside of total sea star.



CAS registry nymber: 114379-45-2 (Ref. 0250)
[0203] / [0205] / [0206] / [0249] / [0250]
91
(2S, 3S, 4R)-2-Acetamide-1, 3, 4-triacetoxyhexadecane (Ref. 0203/0205/0207/0249)
 DLB0207
Akira Hayashi
C24H43O7N1 457.601 Download ChemDraw structure file

[a]25D=+27.9deg (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)







[0203] / [0205] / [0207] / [0249]
92
2-Amino-1, 3, 4-hexadecanetriol, (2S, 3R, 4R)-form (Ref. 0203/0205/0208/0249)
 DLB0208
Akira Hayashi
2S, 3R, 4R-t16:0
 C16H35O3N1 289.454 Download ChemDraw structure file









Cas registry number:127061-67-0 (Ref. 0250)
[0203] / [0205] / [0208] / [0249] / [0250]
93
(2S, 3R, 4R)-2-Acetamido-1, 3, 4-triacetoxyhexadecane (Ref. 0203/0205/02090249>>
 DLB0209
Akira Hayashi
C24H43O3N1 393.603 Download ChemDraw structure file

[a]27D=+6.13deg (C, 0.56 in CHCl3) (Ref. 0203)








CAS registry number:128898-88-4 (Ref. 0250)
[0203] / [0205] / [0209] / [0250]
94
2-Amino-1, 3, 4-hexadecanetriol, (2S, 3R, 4S)-form (Ref. 0203/0205/0210/0249)
 DLB0210
Akira Hayashi
2S, 3R, 4S-t16:0
 C16H35O3N1 289.454 Download ChemDraw structure file










[0203] / [0205] / [0210] / [0249]
95
2-(N-Acetyl)-amino-1, 3, 4-hexadecane-O, O, O-triacetate, (2S, 3R, 4S)-form (Ref. 0203/0205/0211/0249)
 DLB0211
Akira Hayashi
C24H43O7N1 457.601 Download ChemDraw structure file










[0203] / [0205] / [0211] / [0249]
96
2-Amino-1, 3, 4-hexadecanetriol, (2S, 3S, 4S)-form (Ref. 0203/0205/0212/0249)
 DLB0212
Akira Hayashi
2S, 3S, 4S-t16:0
 C16H35O3N1 289.454 Download ChemDraw structure file










[0203] / [0205] / [0212] / [0249]
97
2-(N-Acetyl)-amino-1, 3, 4 -hexadecane-O, O, O-triacetate, (2S, 3S, 4S)-form / (2S, 3S, 4S)-2-Acetamido-1, 3, 4-triacetoxyhexadecane (Ref. 0203/0205/0213/0249)
 DLB0213
Akira Hayashi
C24H43O3N1 393.603 Download ChemDraw structure file

[a]28D=3.3deg (C, 0.46 in CHCl3) (Ref. 0214)









[0203] / [0205] / [0213] / [0214] / [0249]
98
2-Amino-3-hydroxy-4-octadecene-1-sulfonic acid, (2S, 3R)-form (Ref. 0221/0214/0249)
 DLB0214
Akira Hayashi
C18H37O4N1S1 363.557 Download ChemDraw structure file










[0214] / [0221] / [0249]
99
2-(N-benzoylamino)-8-octadecene-1, 3, 4-triol, (2S, 3S, 4R, 8E)-form. (Ref. 0215/0252)
 DLB0215
Akira Hayashi
N-Bz-t18:1 (8)
 C25H37O5N1 431.565 Download ChemDraw structure file

128-129deg (Ref. 0250)








Cryst. (Me2CO) (Ref. 0250)
[0215] / [0250] / [0252]
100
Octadecasphingosine, cerebrin base, Dihydrosphingosine
2-Amino-1, 3-octadecandiol, (2R, 3R)-from (Ref. 0216/0241/0245/0250)
 DLB0216
Akira Hayashi
2R, 3R-d18:0
 C18H39O2N1 301.508 Download ChemDraw structure file

108degC (Ref. 0245)
[a]28546=+13deg (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)
[0216] / [0250]
101
2-(N-Acetyl)-amino-1, 3-octadecanediol, (2R, 3R)-form (Ref. 0217/0241/0242/0243/0250)
 DLB0217
Akira Hayashi
C20H41O3N1 343.544 Download ChemDraw structure file

96-97degC (Ref. 0241)
[a]28546=+6.2deg (10:1 hexane/EtOH) (Ref. 0241)









[0217] / [0250]
102
2-(N-Acetyl)-amino-1, 3-(O-diacetyl)-octadecanediol , (2R, 3R)-form (Ref. 0218/0241/0242/0243/0250>
 DLB0218
Akira Hayashi
C24H45O5N1
 Download ChemDraw structure file

46degC (Ref. 0241)
[a28546=+8.0deg (pentane) (Ref. 0241)









[0218] / [0250]
103
2-Amino-1, 3-octadeanediol, (2S, 3S)-form (Ref. 0219/0241/0245/0250)
 DLB0219
Akira Hayashi
C18H39O2N1 301.508 Download ChemDraw structure file

108degC (Ref. 0245)
[a]28D=-14.1deg (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)

Cerebroside (Ref. 0241); Rat plasma membrane (Ref. 0245)



Radio thin-layer chromatogram (Ref. 0245)
[0219] / [0250]
104
2-(N-Acetyl)-1, 3-(O-diacetyl)-octadecanediol, (2S, 3S)-form (Ref. 0220/0241/0242/0243/0250)
 DLB0220
Akira Hayashi
N, O-Ac-d18:0
 C24H45O5N1 427.618 Download ChemDraw structure file

46degC (Ref. 0241)
[a]28546=-8.0deg (pentane) (Ref. 0241)









[0220] / [0250]
105
Octadecasphinganine, cerebrin base, dihydrosphingosine
2-Amino-1, 3-octadecanediol , (2R,3S)-form (Ref. 0221/0241/0245/0250)
 DLB0221
Akira Hayashi
2R, 3S-d18:0
 C18H39O2N1 301.508 Download ChemDraw structure file

79degC (Ref. 0245)
[a28546=-6.5deg (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)

Cerebroside (Ref. 0241); Rat plasma membrane (Ref. 0245)



Radio thin-layer chromatogram (Ref. 0245)
[0045] / [0221] / [0250]
106
2-(N-Acetyl)-1, 3-octadecanediol, (2R, 3S)-form (Ref. 0222/0241/0245/0250)
 DLB0222
Akira Hayashi
N-Ac-d18:0
 C20H41O3N1 343.544 Download ChemDraw structure file

124-125degC (Ref. 0241)
[a]28546=-8deg (10:1 hexane/EtOH (Ref. 0241)









[0222] / [0250]
107
2-(N-Acetyl)-amino-1,3-(O-diacetyl)-octadecanediol, (2R, 3S)-form (Ref. 0223/0241/0242/0243/0250)
 DLB0223
Akira Hayashi
C24H45O5N1 427.618 Download ChemDraw structure file

96-97degC (Ref. 0241)
[ a]28546=-21deg (10:1 hexane/EtOH) (Ref. 0241)









[0223] / [0250]
108
Octadecasphinganine, Cerebrin base, Dihydrosphingosine
2-Amino-1, 3-Octadecanediol, (2S, 3R)-form (Ref. 0224/0241/0244/0245/0250)
 DLB0224
Akira Hayashi
2S. 3R-d18:0
 C18H39O2N1 301.508 Download ChemDraw structure file
Inhibition of protein kinase C activity (Ref. 5013)
79degC, 108-109degC, Sulfate: Mp. 150degC (AcOH) (Ref. 0245) ; 85-87degC (Ref. 5012)
[a]18546=+6.5deg (10:1 CHCl3), [a]28D=+13.5deg (C, 0.75 in CHCl3) (Ref. 0245)
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)

Cerebroside (Ref. 0244); Rat plasma membrane (Ref. 0245); Ubiquitous in eukaryotes (mainly as a metabolic intermediate) (Ref. 5001)
(Ref. 5016)
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)
3-Ketodihydrosphingosine reductase (yeast ) (Ref. 5010) ; Sphingosine kinase (yeast and mouse) (Ref. 5014/5015)
Radio thin-layer chromatogram (Ref. 0245)
[0224] / [0250] / [5001] / [5002] / [5010] / [5012] / [5013] / [5014] / [5015] / [5016]
109
2-(N-Acetyl)-amino-1, 3-(di-O-acetyl)-octadecanediol, (2S, 3R)-form (Ref. 0225/0241/0242/0243/0250)
 DLB0225
Akira Hayashi
C24H45O5N1 427.618 Download ChemDraw structure file

96-97degC (90-93degC) (Ref. 0241)
[a]19_D=+16deg (C, 0.5 in CHCl3), +21deg (10:1 hexane /EtOH) (Ref. 0241)









[0225] / [0250]
110
2-(N-Acetyl)-1,3-octadecanadiol, (2S, 3R)-form (Ref. 0226/0241/0242/0243/0250)
 DLB0226
Akira Hayashi
2S, 3R-N-Ac-d18:0
 C20H41O3N1 343.544 Download ChemDraw structure file

124-125degC (Ref. 0241)
[a]28546=+7.7deg (10:1 hexane/EtOH) (Ref. 0241)









[0226] / [0250]
111
2-(N-Acetyl)-1, 3, 4-(O-triacetyl)-octadecanetriol, (2S, 3S, 4R )-form (Ref. 0227/0250)
 DLB0227
Akira Hayashi
C26H37O7N1 475.575 Download ChemDraw structure file

49-50degC (Ref. 0247)
[a]25D =+5deg (C, 4.8 in DMF) (Ref. 0247)




Yeast, Hansenula ciferrii (Ref. 0247)



Crist. (Petr. ether) (Ref. 0247)
[0227] / [0250]
112
4-Hydroxysphinganine / phytosphingosine
2-Amino-1, 3, 4-octadecanetriol, (2S, 3S, 4R)-form (Ref. 0228/0232/0233/0234/0250)
 DLB0228
Akira Hayashi
2S, 3S, 4R-t18:0
 C18H39O3N1 317.507 Download ChemDraw structure file

Insol. in water. Soluble in CHCl3 and EtOH




Sphingolipids in cerebroside or ganglioside (Ref. 0248/0249); Yeast, Hansenula cifferrii (Ref. 0247); Ubiquitous un eukaryotes ( especially abundant in plants, yeast and fungi) (Ref. 5001/5027)
(Ref. 0232/0233/0234/5026)
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)
Sphingolipid 4-hydroxylase (yeast) (Ref. 5028/5029); Sphigosine kinase ( yeast and mouse) (Ref. 5014/5015)

[0228] / [0232] / [0233] / [0234] / [0249] / [0250] / [5001] / [5014] / [5015] / [5026] / [5027] / [5028] / [5029]
113
2-(N-Benzoylamino)-1, 3, 4-octadecanetriol, (2S, 3S, 4R)-form (Ref. 0229/0250)
 DLB0229
Akira Hayashi
N-Bz-t18:0
 C25H43O4N1 421.613 Download ChemDraw structure file

137.8-138.8degC (Ref. 0247)
[a]D = +5deg (C, 5.2 in pyridine) (Ref. 0247)




Yeast, Hansenula ciferrii (Ref. 0247)



Crist.(EtOAc) (Ref. 0247)
[0229] / [0250]
114
2-N-benzoylamino)-1, 3, 4-(O-triacetyl)-octadecanetriol, (2S, 3S, 4R)-form, (Ref. 0230/0250)
 DLB0230
Akira Hayashi
C31H49O7N1 547.723 Download ChemDraw structure file

78-80degC (Ref. 0247)
[a]D = +22deg (C, 0.5 in CHCl3) (Ref. 0247)




Yeast, Hansenula cifrrii (Ref. 0247)



Crist. (Petr. ether) (Ref. 0247)
[0230] / [0250]
115
2-(N-benzoylamino)-1, 3, 4-(O-triacetylhydroxy)-8-octadecene, (2S, 3S, 4R, 8E)-form. (Ref. 0231/0252)
 DLB0231
Akira Hayashi
N-Bz-O-Ac-t18:1 (8)
 Download ChemDraw structure file

77-78deg (Ref. 0250)
[a]25D = +10deg (c, 0.76 in CHCl3) (Ref. 0250)








Cryst. (hexane); Cas registry number: 25277-37-6/51153-53-8 (Ref. 0250)
[0231] / [0250] / [0252]
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 Download ChemDraw structure file


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)
[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 Download ChemDraw structure file


GC-MS of polyhydroxyalcohol obtained from the base / GC-MS of aldehyde obtained by periodate oxidation of the base (Ref. 0254)


Ceramide aminoethylphosphonate of Hemifusus ternatanus (Ref. 0254)/ Sphingolipids of Barnea dilatata japonica (Ref. 0255)




[0254] / [0255]
118
2-Aminononadecatrienine-1, 3-diol (Ref. 0255)
 DLB0234
Akira Hayashi
d19:3
 C19H35O2N1 309.487 Download ChemDraw structure file


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)







[0254] / [0255]
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 Download ChemDraw structure file





Ceramides in Euhadra hickonis (Ceramide I 3.1%, Ceramide II 47.2%) (Ref. 0256)/ Sphingolipisa of Euhadra hickonis (Gal-cer 2.4%, Glc-cer 2.6%, sphingophosphonolipids 4.1%) (Ref. 0257)Ceramide dihexoside of marine sponge (20.1%) (Ref. 0259)




[0256] / [0257] / [0259]
120
2-Amino-15-methyl-hexadecane-1, 3, 4-triol / 4-Hydroxy-15-methylhexadecasphinganine (Ref. 0258/0259)
 DLB0236
Akira Hayashi
15-Me-t16:0 / iso-t17:0
 C17H39O3N1 305.496 Download ChemDraw structure file


Ei-Ms of aldehyde derived from the base (Ref. 0259)


Sphingoglycolipids of marine sponge (5.8%) (Ref. 0259); Ceramide dihexoside of marine sponge (as TMS-L CB 0.5%) (Ref. 0258);




[0258] / [0259]
121
2-Amino-16-methyl-heptadecane-1, 3, 4-triol / 4-Hydroxy-16-Methylheptadecasphinganine (Ref. 0256/0259)
 DLB0237
Akira Hayashi
16-Me-t17:0 / iso-t18:0
 C18H39O3N1 317.507 Download ChemDraw structure file


Ei-MS of aldehyde derived from the LCB (Ref. 0259); CI-MS(methane) of aldehyde derived from the LCB (Ref. 0259); CI-MS (isobutane) of aldehyde derived from the base (Ref. 0259)


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).




[0253] / [0256] / [0258] / [0259]
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 Download ChemDraw structure file





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)
[0253] / [0259]
123
2-Amino-16-Methyl-octadecane-1, 3, 4-triol / 4-Hydroxy-16-methylsphinganine (Ref. 02568/0259)
 DLB0239
Akira Hayashi
16-Me-t18:0 / anteiso-t19:0
 C19H41O3N1 331.534 Download ChemDraw structure file


Ei-MS of aldehyde derived from the base of sphingoglycolipids in sponge (Ref. 0259); CI-MS (methane)of aldehyde derived from the base (Ref. 0259); CI-MS (isobutane) of aldehyde derived from the base (Ref. 0259)


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).




[0253] / [0256] / [0258] / [0259]
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 Download ChemDraw structure file





Sphingoglycolipids of marine sponge (4.0%) (Ref. 0259)




[0259]
125
3-Ketodihydrosphingosine / 3-Ketosphinganine
2S-1-Hydroxy-2-amino-octadecane-3-one
 DLB0241
Akira Hayashi
KDS
 C18H37O2N1 299.492 Download ChemDraw structure file

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)
(Ref. 5011)
3KDS is formed by condensation of L-serine with palmitoyl CoA, the reaction catalyzed by serine palmitoyltransferase (SPT) (Ref. 5002/5003); 3KDS is converted to dihydrosphingosine by 3-ketodihydrosphingosine reductase (Ref. 5002)
LCB1 and LCB2 subunits of SPT (yeast, mouse, human) (Ref. 5004/5005/5006/5007/5008/5009); 3-ketodihydrosphingosine reductase (yeast) (Ref. 5010)

[5001] / [5002] / [5003] / [5004] / [5005] / [5006] / [5007] / [5008] / [5009] / [5010] / [5011]
126
N-Acyl-(2S, 3R)-dihydrosphingosine / N-Acyl-(2S, 3R)-sphinganine / (2S, 3R)-2-(N-Acylamino)-octadecane-1, 3-diol
 DLB5001
Akira Hayashi
DCer
 Download ChemDraw structure file
An inactive control of biological activity of ceramide (Ref. 5032)
Insol. in water. Sol. in CHCl3 and ether.




Ubiquitous in eukaryotes (Ref. 5001)

DCer is formed by N-acylation of dihydrosphingosine (Ref. 5002); DCer is desaturated to be converted to Cer (Ref. 5033/5034)


[5001] / [5002] / [5032] / [5033] / [5034]
127
N-Acyl-(2S, 3R, 4E)-sphingosine / (2S, 3R, 4E)-2-(N-acylamino)-4-octadecene-1, 3-diol
 DLB5002
Akira Hayashi
Cer
 Download ChemDraw structure file
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)
(Ref. 5024)
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)
Acid ceramidase (mouse and human) (Ref. 5022/5023); Genetic defacts in acidic ceramidase cause Farber disease (Ref. 5022/5023)

[5001] / [5002] / [5012] / [5017] / [5022] / [5023] / [5024] / [5031] / [5033] / [5034] / [5035] / [5036]
128
N-Acyl-(2S,3S, 4R)-phytosphingosine / (2S, 3S, 4R)-2-(N-acylamino)-octadecane-1, 3, 4-triol
 DLB5003
Akira Hayashi
PhytoCer
 Download ChemDraw structure file

Insol. in water. Sol. in CHCl3 and ether




Ubiquitous in eukaryotes (especially abundant in Plants, yeast, and fungi) (Ref. 5001/5027)

PhytoCer is probably synthesized by 4-hydroxylation of dihydroceramide. lternatively, PhytoCer may be synthesized by N-acylation of phytosphingosine (Ref. 5028/5029); In fungi and yeast, PhytoCer is anabolyzed to complex sphingolipids with inositolphosphate containing head groups (Ref. 5027)
Sphingolipid 4-hydroxylase ( yeast) (Ref. 5028/5029)

[5001] / [5027] / [5028] / [5029]
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
 Download ChemDraw structure file

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)

[5030] / [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
 Download ChemDraw structure file
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)

[5030] / [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 Download ChemDraw structure file





Present in blood plasma lipids (Ref. 5037)



nC14:0
[5037]
132
2-Hexadecanoylamino-4-octadecene-1, 3-diol / N-Hexadecanoyl-4-sphingenine (Ref. 5037)
 DLB5007
Akira Hayashi
d18:1-n16:0
 C34H67O3N1 537.901 Download ChemDraw structure file





Present in blood and brain lipids (Ref. 5037)



nC16:0
[5037]
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 Download ChemDraw structure file





Present in blood and brain lipids (Ref. 5037)



nC18:1 (9)
[5037]
134
N-Octadecanoylamino-4-octadecene-1, 3-diol / N-Octadecanoyl-4-sphingenine (Ref. 5037)
 DLB5009
Akira Hayashi
d18:1-n18:0
 C36H71O3N1 565.954 Download ChemDraw structure file

97-98degC / 91-93degC (Ref. 0251)




Present in blood and brain lipids (Ref. 5037)



nC18:0
[0251] / [5037]
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 Download ChemDraw structure file





Present in blood and brain lipids (Ref. 5037)



nC20:0
[5037]
136
2-Docosanoylamino-4-octadecene-1, 3-diol / N-Docosanoyl-4-sphingenine (Ref. 5037)
 DLB5011
Akira Hayashi
d18:1-n22:0
 C40H79O3N1 622.060 Download ChemDraw structure file





Present in brain and blood lipids (Ref. 5037)



nC22:0
[5037]
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 Download ChemDraw structure file





Present in blood lipids (Ref. 5037)



nC22:1 (13)
[5037]
138
2-Tetracosanoylamino-4-octadecene-1, 3-diol / N-Tetracosanoyl-4-sphingenine (Ref. 5037)
 DLB5013
Akira Hayashi
d18:1-n24:0
 C42H83O3N1 650.113 Download ChemDraw structure file

93-96degC (Ref. 0251)




Present in blood and brain lipids (Ref. 5037)



Cryst. (MeOH) (Ref. 0251)
nC24:0
[0251] / [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 Download ChemDraw structure file
Inhibits cell proliferation and induces monocytic differentiation of HL-60 cells (Ref. 8001)and induces apoptosis (Ref. 8002). It stimulates protein phosphatase 2A, activates MAP kinase and SAP kinase and induces PKCd and e translocation.
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
[8001] / [8002]
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 Download ChemDraw structure file
Induces monocytic differentiation (Ref. 8001). Stimulates IL-2 secretion and induces apoptosis (Ref. 8002/8003/8004).
Soluble in ethanol, methanol, chloroform, and DMSO (up to 5 mg/ml).








nC8:0
[8001] / [8002] / [8003] / [8004]
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 Download ChemDraw structure file
Induces monocytic differentiation (Ref. 8001) and apoptosis (Ref. 8002). Activates PKCz (Ref. 8005). Activates a cytosolic serine/threonine protein phosphatase (Ref. 8007). Stimulates ceramide-activated protein kinase (Ref. 8006).
Soluble in chloroform (up to 5 mg/ml).








nC16:0
[8001] / [8002] / [8005] / [8006] / [8007]
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 Download ChemDraw structure file
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
[8008]
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 Download ChemDraw structure file
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
[8008]
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
Blocks the conversion of sphingosine to sphingosine-1-phosphate by inhibiting sphingosine kinase (Ref. 8012). Induces EGF receptor autophosphorylation (Ref. 8010). Inhibits cell growth (Ref. 8011) and promotes apoptosis. Inhibits protein kinase C and enhance src-kinase activity (Ref. 8009).
Soluble in ethanol, isopropanol, chloroform, and methanol.






Produced endogenously via ceramide catabolism.

bnC2:0
[8009] / [8010] / [8011] / [8012]
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 Download ChemDraw structure file
An analog of ceramide inert to ceramidases. Rapidly induces apoptosis (Ref. 8013).
Soluble in ethanol and DMSO.








nC8:0
[8013]
Reference
[0001]
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)
[TOP]
[0002]
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)
[TOP]
[0003]
AUTHOR:Karlsson, K.-A.
TITLE:On the chemistry and occurrence of sphingolipid long-chain bases. PubMed ID:4394487
JOURNAL:Chem. Phys. Lipids
VOL:5 PAGE : 6-43 (1970)
[TOP]
[0004]
AUTHOR:Matsubara, T., Hayashi, A., Banno, Y., Morita, T., and Nozawa, Y.
TITLE:Cerebroside of the dimorphic human pathogen, Candida albicans PubMed ID:3555875
JOURNAL:Chem Phys Lipids.
VOL:43 PAGE : 1-12 (1987)
[TOP]
[0005]
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)
[TOP]
[0006]
AUTHOR:Matsubara, T.
TITLE:Distribution of the dienic long chain bases in shellfish sphingophosphonolipids.
JOURNAL:Chem. Phys. Lipids
VOL:14 PAGE : 247-259 (1975)
[TOP]
[0007]
AUTHOR:Hayashi, A. and Matsuura, F.
TITLE:Characterization of aminoalkylphophonyl cerebrosides in muscle tissue of Turbo cornutus. PubMed ID:699219
JOURNAL:Chem. Phys. Lipids
VOL:22 PAGE : 9-23 (1978)
[TOP]
[0008]
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)
[TOP]
[0009]
AUTHOR:Hayashi, A. and Matsubara, T.
TITLE:A new homologue of phosphonosphingolipid, N-methylaminoethyl-phosphonyltrigalactosylceramide.
JOURNAL:Biochim. Biophys. Acta
VOL:1006 PAGE : 89-96 (1989)
[TOP]
[0010]
AUTHOR:Matsubara, T., and Hayashi, A.
TITLE:Structural studies on glycolipid of shellfish. III. Novel glycolipids from Turbo cornutus PubMed ID:6263873
JOURNAL:J Biochem (Tokyo).
VOL:89 PAGE : 645-650 (1981)
[TOP]
[0011]
AUTHOR:Matsubara, T., and Hayashi, A.
TITLE:Structural studies on glycolipids of shellfish. V. Gala-6 series glycosphingolipids of the marine snail, Chlorostoma argyrostoma turbinatum PubMed ID:3011773
JOURNAL:J Biochem (Tokyo).
VOL:99 PAGE : 1401-1408 (1986)
[TOP]
[0012]
AUTHOR:Hayashk, A., Matsubara, T., and Matsuura, F.
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
JOURNAL:Chem Phys Lipids.
VOL:14 PAGE : 102-105 (1975)
[TOP]
[0013]
AUTHOR:Karlsson, K. A.
TITLE:Studies on sphingosines. 16. The chemical structure of a dienic long chain base of human blood plasma sphingomyelins PubMed ID:5585679
JOURNAL:Acta Chem Scand.
VOL:21 PAGE : 2577-2578 (1967)
[TOP]
[0014]
AUTHOR:Polito, A. J., Akita, T., and Sweeley, C. C.
TITLE:Gas chromatography and mass spectrometry of sphingolipid bases. Characterization of sphinga-4,14-dienine from plasma sphingomyelin PubMed ID:5660077
JOURNAL:Biochemistry.
VOL:7 PAGE : 2609-2614 (1968)
[TOP]
[0015]
AUTHOR:Renknen, O. and Hirvisalo, E. L.
TITLE:Structure of plasma sphingadienine. PubMed ID:5356753
JOURNAL:J. Lipid Res.
VOL:10 PAGE : 687-693 (1969)
[TOP]
[0016]
AUTHOR:Morrison, W. R.
TITLE:Polar lipids in bovine milk. I. Long-chain bases in sphingomyelin PubMed ID:5816447
JOURNAL:Biochim Biophys Acta.
VOL:176 PAGE : 537-546 (1969)
[TOP]
[0017]
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
JOURNAL:J Lipid Res.
VOL:10 PAGE : 445-455 (1969)
[TOP]
[0018]
AUTHOR:Carter, H. E., and Hirschberg, C. B.
TITLE:Phytosphingosines and branched sphingosines in kidney PubMed ID:5660054
JOURNAL:Biochemistry.
VOL:7 PAGE : 2296-2300 (1968)
[TOP]
[0019]
AUTHOR:Bieber, L. L., O'Connor, J. D., and Sweeley, C. C.
TITLE:The occurrence of tetradecasphing-4-enine and hexadecasphing-4-enine as the principal sphingosines of Musca domestica larvae and adults PubMed ID:5811205
JOURNAL:Biochim Biophys Acta.
VOL:187 PAGE : 157-159 (1969)
[TOP]
[0020]
AUTHOR:Karlsson, K.-A.
TITLE:Studies on sphingosines. 6. C16- and C17-sphingosines, hitherto unknown sphingosines.
JOURNAL:Acta Chem. Scand.
VOL:18 PAGE : 2395-2396 (1964)
[TOP]
[0021]
AUTHOR:Karlsson, K.-A.
TITLE:Studies on sphingosines. II. The chemical structure of phytosphingosine of human origin and a note on the lipid composition of the yeast Hansenula ciferrii. PubMed ID:5964492
JOURNAL:Acta Chem. Scand.
VOL:20 PAGE : 2884-2885 (1966)
[TOP]
[0022]
AUTHOR:Hirvisalo, E. L., and Renkonen, O.
TITLE:Composition of human serum sphingomyelins PubMed ID:4312626
JOURNAL:J Lipid Res.
VOL:11 PAGE : 54-59 (1970)
[TOP]
[0023]
AUTHOR:Carter, H.E. and Shapiro, D.
TITLE:Configuration of dihydrosphingosine.
JOURNAL:J. Amer. Chem. Soc.
VOL:75 PAGE : 5131-5132 (1953)
[TOP]
[0024]
AUTHOR:Jenny, E.F. and Grob, C.A.
TITLE:Die Synthese von Erythro-Dihydrosphingosin aus Trans-2-Octadecene-1-asure
JOURNAL:Helv. Chim. Acta
VOL:36 PAGE : 1936-1944 (1953)
[TOP]
[0025]
AUTHOR:White, D. C., Tucker, A. N., and Sweeley, C. C.
TITLE:Characterization of the iso-branched sphinganines from the ceramide phospholipids of Bacteroides melaninogenicus PubMed ID:5364262
JOURNAL:Biochim Biophys Acta.
VOL:187 PAGE : 527-532 (1969)
[TOP]
[0026]
AUTHOR:Karlsson, K.-A.
TITLE:Studies on sphingosines. III. C20-dihydrosphingosine, a hitherto unknown sphingosine.
JOURNAL:Acta Chem. Scand.
VOL:18 PAGE : 565-566 (1964)
[TOP]
[0027]
AUTHOR:Sambasivarao, K. and McCluer, R.H.
TITLE:Lipid components of gangliosides.
JOURNAL:J. Lipid Res.
VOL:5 PAGE : 103-108 (1964)
[TOP]
[0028]
AUTHOR:Stanacev, N.Z. and Chargaff, E.
TITLE:Studies on the chemistry of mucolipids: Occurrence of the long-chain base icosasphingosine, composition of fatty acids, fractionation attempts.
JOURNAL:Biochim. Biophys. Acta
VOL:98 PAGE : 168-181 (1965)
[TOP]
[0029]
AUTHOR:Moscatelli, E.A. and Gilliland, K.E.
TITLE:14:Sphingosine, a novel sphingosine base from Procambarus clarkii. PubMed ID:5785694
JOURNAL:Lipids
VOL:4 PAGE : 244-245 (1969)
[TOP]
[0030]
AUTHOR:Matsubara, T. and Hayashi, A.
TITLE:Identification of molecular species of ceramide aminoethyl phosphonate from oyster adductor by gas-liquid chromatography-mass spectrometry. PubMed ID:4693503
JOURNAL:Biochim. Biophys. Acta
VOL:296 PAGE : 171-178 (1973)
[TOP]
[0031]
AUTHOR:Mishima, Y. and Hayashi, A.
TITLE:Studies on sphingolipids of Barnea (Umitakea) dilatata japonica I. Cerebroside and Ceramide aminoethylphosphonate (in Japanene )
JOURNAL:Japan. Oil Chem. Soc. (Yukagaku )
VOL:27 PAGE : 92-97 (1978)
[TOP]
[0032]
AUTHOR:Karlsson, K.-A.
TITLE:Sphingolipid long chain bases. PubMed ID:4921900
JOURNAL:Lipids
VOL:5 PAGE : 878-891 (1970)
[TOP]
[0033]
AUTHOR:Matsuura, F., Matsubara, T., and Hayashi, A.
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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VOL:74 PAGE : 49-57 (1973)
[TOP]
[0034]
AUTHOR:Carter, H.E., Glick, F.J., Norris, W.P., and Phillips, G.E.
TITLE:Biochemistry of the sphingosine III. Structure of sphingosine
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VOL:170 PAGE : 285-294 (1947)
[TOP]
[0035]
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)
[TOP]
[0036]
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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VOL:261 PAGE : 12604-12609 (1986)
[TOP]
[0037]
AUTHOR:Merrill, A. H., Jr., Sereni, A. M., Stevens, V. L., Hannun, Y. A., Bell, R. M., and Kinkade, J. M., Jr.
TITLE:Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases PubMed ID:3462189
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[TOP]
[0038]
AUTHOR:Hall, F. L., Fernyhough, P., Ishii, D. N., and Vulliet, P. R.
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[TOP]
[0039]
AUTHOR:Carter, H. E., Hendry, R. A., Nojima, S., Stanacev, N. Z., and Ohno, K.
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)
[TOP]
[0040]
AUTHOR:Karlsson, K. A., and Holm, G. A.
TITLE:Studies on sphingosines. 9. C19-sphingosines, hitherto unknown sphingosines PubMed ID:5859480
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VOL:19 PAGE : 2423-2425 (1965)
[TOP]
[0041]
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
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VOL:350 PAGE : 1081-1087 (1969)
[TOP]
[0042]
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
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VOL:202 PAGE : 195-197 (1970)
[TOP]
[0043]
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
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VOL:573 PAGE : 51-60 (1979)
[TOP]
[0044]
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
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VOL:574 PAGE : 79-92 (1979)
[TOP]
[0045]
AUTHOR:Ohnishi, M., Kawase, S., Ito, S., and Fujino, Y.
TITLE:On sphingolipids of Basidiomycota, Grifola frondosa (in Japanese)
JOURNAL:Proc. Jpn. Conf. Biochem. Lipids
VOL:26 PAGE : 112-115 (1984)
[TOP]
[0046]
AUTHOR:Kawai, G., and Ikeda, Y.
TITLE:Structure of biologically active and inactive cerebroside prepared from Schizophyllum commune. PubMed ID:4039347
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VOL:26 PAGE : 338-343 (1985)
[TOP]
[0047]
AUTHOR:Kawai, G., and Ikeda, Y.
TITLE:Chemistry and functional moiety of a fruiting-inducing cerebroside in Schizophyllum commune
JOURNAL:Biochem. Biophys. Acta
VOL:754 PAGE : 243-248 (1983)
[TOP]
[0048]
AUTHOR:Popvic, M.
TITLE:Dienic sphingosine bases
JOURNAL:Bull. Soc. Conseil. Acad. RSF Yogoslavie
VOL:11 PAGE : 98-100 (1966)
[TOP]
[0049]
AUTHOR:Morrison, W. R.
TITLE:Long-chain bases in the sphingolipids of bovine milk and kidney, rumen bacteria, rumen protozoa, hay and concentrate PubMed ID:4737329
JOURNAL:Biochim Biophys Acta.
VOL:316 PAGE : 98-107 (1973)
[TOP]
[0050]
AUTHOR:Hayashi, A. and Matsuura, F.
TITLE:2-Hydroxy fatty acid and phytosphingosine-containing ceramide 2-N-methyl-aminoethylphosphonate from Turbo cornutus
JOURNAL:Chem. Phys. Lipids
VOL:10 PAGE : 51-65 (1973)
[TOP]
[0051]
AUTHOR:Hayashi, A., Chen, H.-C., and Shiono, H.
TITLE:Studies on sterol sulfate, sterol glycoside and cerebroside of sea-cucumber , Stichopus japonicus ( in Japanese)
JOURNAL:J. Fac. Sci. Tech., Kinki Univ.
VOL:26 PAGE : 73-85 (1990)
[TOP]
[0052]
AUTHOR:Carter, H. E., and Hendrickson, H. S.
TITLE:Biochemistry of the sphingolipids. XV. Structure of phytosphingosine and dehydrophytospingosine PubMed ID:14018956
JOURNAL:Biochemistry.
VOL:2 PAGE : 389-393 (1963)
[TOP]
[0053]
AUTHOR:Gigg, J., and Gigg, R.
TITLE:A synthesis of phytosphingosines from D-galactose
JOURNAL:J. Chem. Soc. (C)
VOL: PAGE : 1876-1879 (1966)
[TOP]
[0054]
AUTHOR:Karlsson, K.-A
TITLE:Studies on sphingosines 7. The existence of C18- and C20-phytosphingosine in animal tissues
JOURNAL:Acta Chem. Scand.
VOL:18 PAGE : 2397-2398 (1964)
[TOP]
[0055]
AUTHOR:Morrison, W.R.
TITLE:Cis and trans isomers of 4-hydroxy-8-sphingenine in plant cerebrosides
JOURNAL:Chem. Phys. Lipids
VOL:11 PAGE : 99-102 (1973)
[TOP]
[0056]
AUTHOR:Karlsson, K.-A., Samuelsson, B.E., and Steen, G.O.
TITLE:Structure and function of sphingolipids 1. Differences in sphingolipid long-chain base pattern between kidney cortex, medulla and papillae. PubMed ID:5727637
JOURNAL:Acta Chem. Scand.
VOL:22 PAGE : 1361-1363 (1968)
[TOP]
[0057]
AUTHOR:Hayashi, A., Mishima, Y., and Matsubara, T.
TITLE:Occurrence and structural determination of octadecasphinga-4, 8, 10-trienine
JOURNAL:Chem. Phys. Lipids
VOL:52 PAGE : 171-178 (1990)
[TOP]
[0058]
AUTHOR:Irie, A., Kubo, H., and Hoshi, M.
TITLE:Glucosylceramide having a novel triunsaturated long-chain base from the spermatozoa of the starfish, Asteras amurensis. PubMed ID:2358431
JOURNAL:J. Biochem.
VOL:107 PAGE : 578-586 (1990)
[TOP]
[0059]
AUTHOR:Itonori, S., Kamemura, K., Narushima, K., Sonku, N., Itasaka, O., Hori, T., and Sugita, M.
TITLE:Characterization of a new phosphonocerebroside, N-methyl-2-aminoethyl-phosphonylglucosylceramide from the antarctic krill, Euphausia Superba. PubMed ID:1998750
JOURNAL:Biochim. Biophys. Acta
VOL:1081 PAGE : 321-327 (1991)
[TOP]
[0101]
AUTHOR:Karlsson, K.-A.
TITLE:Sphingolipid long chain bases. PubMed ID:4921900
JOURNAL:Lipids
VOL:5 PAGE : 878-891 (1970)
[TOP]
[0102]
AUTHOR:Karlsson, K. A., Samuelsson, B. E., and Steen, G. O.
TITLE:Identification of hitherto unknown branched-chain bases in sulphatides of the salt (rectal) gland of spiny dogfish PubMed ID:4713159
JOURNAL:Biochim Biophys Acta.
VOL:306 PAGE : 307-316 (1973)
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