6-Hydroxy-4-sphingenine in human epidermal ceramides.
The solvent-extractable lipids of human epidermal stratum corneum consist predominantly of ceramides. In addition two non-extractable ceramides are chemically bound to the stratum corneum protein. One of the bound ceramides, constituting 50% of the bound lipids, was previously shown to consist of very long chan omega-hydroxyacids in amide linkage with sphingosine. The second bound caramide, which forms 25% of the bound lipids, was shown to contain the same hydroxyacids, but the sphingoid base was neither sphingosine nor phytosphingosine. In the present study, the undefined bound ceramide was shown by NMR and chemical procedures to be the omega-hydroxyacid derivative of a new base, 6-hydroxy-4-sphingenine. In addition, a ceramide previously known to constitute 25% of the extractable human stratum corneum ceramides has been found to contain the same novel sphingoid base, amide-linked to long-chain alpha-hydroxyacids. Finally, a new acylceramide has been isolated and identified that consists of very long chain omega-hydroxyacids in amide linkage with the novel sphingolipid, with fatty acids esterified wit the terminal hydroxyl group of the hydroxyacid.
Robson
K J
KJ
Marshall Dermatology Research Laboratories, Department of Dermatology, University of Iowa College of Medicine, Iowa City 52242.
Stewart
M E
ME
Michelsen
S
S
Lazo
N D
ND
Downing
D T
DT
D000328:Adult; D002518:Ceramides / Q000032:analysis* / Q000737:chemistry; D002855:Chromatography, Thin Layer; D004817:Epidermis / Q000737:chemistry*; D005233:Fatty Alcohols / Q000032:analysis* / Q000737:chemistry; D006801:Humans; D007231:Infant, Newborn; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives*
C092210:6-hydroxy-4-sphingenine; D002518:Ceramides; D005233:Fatty Alcohols; D013110:Sphingosine