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 v...

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Published inJournal of lipid research Vol. 35; no. 11; pp. 2060 - 2068
Main Authors ROBSON, KJ, STEWART, ME, MICHELSEN, S, LAZO, ND, DOWNING, DT
Format Journal Article
LanguageEnglish
Published BETHESDA LIPID RESEARCH INC 01.11.1994
Elsevier
Subjects
Adult
Biochemistry & Molecular Biology
Ceramides - analysis
Ceramides - chemistry
Chromatography, Thin Layer
Epidermis - chemistry
Fatty Alcohols - analysis
Fatty Alcohols - chemistry
Humans
Infant, Newborn
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Male
Molecular Structure
Science & Technology
Sphingosine - analogs & derivatives
GLUCOSYLCERAMIDES
CORNEOCYTE ENVELOPE
NMR
HUMAN STRATUM-CORNEUM
ACYLCERAMIDES
KERATINOCYTES
PHYTOSPHINGOSINE
PIG EPIDERMIS
STRATUM CORNEUM
PERMEABILITY BARRIER
MAMMALIAN EPIDERMIS
LIPIDS
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Summary: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 chain omega-hydroxyacids in amide linkage with sphingosine. The second bound ceramide, 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 with the terminal hydroxyl group of the hydroxyacid.
Bibliography:Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-2275
1539-7262
DOI:10.1016/S0022-2275(20)39952-1