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Biased distribution of the branched-chain fatty acids in ceramides of vernix caseosa

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Lipids

Abstract

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.

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Abbreviations

BCFA:

branched-chain fatty acid

Cer[EAS]:

esterified α-OH-hydroxyacid/sphingosine ceramide

Cer[NH]:

non-OH fatty acid/hydroxysphingosine ceramide

GC-MS:

gas chromatography-mass spectrometry

HPTLC:

high-performance thin-layer chromatography

NMR:

nuclear magnetic resonance

TLC:

thin-layer chromatography

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Author information

Authors and Affiliations

  1. Cosmetic Laboratory, Kanebo Ltd., 250-0002, Kanagawa-Ken, Japan

    Kunio Mimura & Yumi Tokitsu

  2. Laboratory of Applied Biochemistry, Faculty of Agriculture, University of the Ryukyus, Nishihara-Cho, 903-0213, Okinawa-Ken, Japan

    Hirosuke Oku, Kyoko Onaga, Hironori Iwasaki & Isao Chinen

Authors
  1. Hirosuke Oku
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  2. Kunio Mimura
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  3. Yumi Tokitsu
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  4. Kyoko Onaga
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  5. Hironori Iwasaki
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  6. Isao Chinen
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Correspondence to Hirosuke Oku.

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Oku, H., Mimura, K., Tokitsu, Y. et al. Biased distribution of the branched-chain fatty acids in ceramides of vernix caseosa. Lipids 35, 373–381 (2000). https://doi.org/10.1007/s11745-000-534-x

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  • DOI: https://doi.org/10.1007/s11745-000-534-x

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