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Biased distribution of the branched‐chain fatty acids in ceramides of vernix caseosa
Author(s) -
Oku Hirosuke,
Mimura Kunio,
Tokitsu Yumi,
Onaga Kyoko,
Iwasaki Hironori,
Chinen Isao
Publication year - 2000
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-000-534-x
Subject(s) - amide , chemistry , ceramide , fatty acid , long chain , organic chemistry , sphingosine , sphingolipid , stereochemistry , biochemistry , apoptosis , receptor , polymer science
The compositions of ester‐ and amide‐linked fatty acids from ceramides of human vernix caseosa were described with emphasis on the distribution of the branched‐chain fatty acid (BCFA). Two novel ceramides were isolated from vernix caseosa in the course of this study: the acylated type of esterified α‐OH‐hydroxyacid/sphingosine ceramide (Cer[EAS]) and nonacylated type of non‐OH fatty acid/hydroxysphingosine ceramide (Cer[NH]). Their chemical structures were identified by nuclear magnetic resonance and chemical procedure. The Cer[EAS] was an acylceramide and consisted of the highest concentrations of ester‐ and amide‐linked BCFA (62 and 67%, respectively). The iso‐ or anteiso‐branching structures of the aliphatic chains were confirmed by the mass spectra of their picolinyl or pyrrolidide derivatives. As a whole, amide‐linked fatty acids of ceramides 1–7 and Cer[NH] were normal types of straight‐chain fatty acids with or without α‐ or ω‐hydroxylation. The BCFA concentrations of amide‐linked fatty acids in these ceramides (ceramides 1–7 and Cer[NH]) were low and less than 10%. The BCFA thus occurred exclusively in a novel acylceramide of Cer[EAS] in the vernix caseosa.