دورية أكاديمية
Two C18 hydroxy-cyclohexenone fatty acids from mammalian epidermis: Potential relation to 12R-lipoxygenase and covalent binding of ceramides.
| العنوان: | Two C18 hydroxy-cyclohexenone fatty acids from mammalian epidermis: Potential relation to 12R-lipoxygenase and covalent binding of ceramides. |
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| المؤلفون: | Brash AR; Department of Pharmacology, Vanderbilt University School of Medicine, Nashville, Tennessee, USA. Electronic address: alan.brash@vanderbilt.edu., Noguchi S; Department of Pharmacology, Vanderbilt University School of Medicine, Nashville, Tennessee, USA., Boeglin WE; Department of Pharmacology, Vanderbilt University School of Medicine, Nashville, Tennessee, USA., Calcutt MW; Department of Biochemistry, Vanderbilt University School of Medicine, Nashville, Tennessee, USA., Stec DF; Department of Chemistry, Vanderbilt University, Nashville, Tennessee, USA., Schneider C; Department of Pharmacology, Vanderbilt University School of Medicine, Nashville, Tennessee, USA., Meyer JM; Department of Dermatology, Vanderbilt University Medical Center, and Dermatology Service, Department of Veterans Affairs, Tennessee Valley Healthcare System, Nashville, Tennessee, USA. |
| المصدر: | The Journal of biological chemistry [J Biol Chem] 2023 Jun; Vol. 299 (6), pp. 104739. Date of Electronic Publication: 2023 Apr 21. |
| نوع المنشور: | Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: Elsevier Inc. on behalf of American Society for Biochemistry and Molecular Biology Country of Publication: United States NLM ID: 2985121R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1083-351X (Electronic) Linking ISSN: 00219258 NLM ISO Abbreviation: J Biol Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: 2021- : [New York, NY] : Elsevier Inc. on behalf of American Society for Biochemistry and Molecular Biology Original Publication: Baltimore, MD : American Society for Biochemistry and Molecular Biology |
| مواضيع طبية MeSH: | Ceramides*/metabolism , Epidermis*/metabolism , Linoleic Acid*/metabolism , Lipoxygenase*, Animals ; Humans ; Mice ; Fatty Acids/metabolism ; Linoleic Acids ; Swine |
| مستخلص: | A key requirement in forming the water permeability barrier in the mammalian epidermis is the oxidation of linoleate esterified in a skin-specific acylceramide by the sequential actions of 12R-lipoxygenase, epidermal lipoxygenase-3, and the epoxyalcohol dehydrogenase SDR9C7 (short-chain dehydrogenase-reductase family 7 member 9). By mechanisms that remain unclear, this oxidation pathway promotes the covalent binding of ceramides to protein, forming a critical structure of the epidermal barrier, the corneocyte lipid envelope. Here, we detected, in porcine, mouse, and human epidermis, two novel fatty acid derivatives formed by KOH treatment from precursors covalently bound to protein: a "polar" lipid chromatographing on normal-phase HPLC just before omega-hydroxy ceramide and a "less polar" lipid nearer the solvent front. Approximately 100 μg of the novel lipids were isolated from porcine epidermis, and the structures were established by UV-spectroscopy, LC-MS, GC-MS, and NMR. Each is a C18 fatty acid and hydroxy-cyclohexenone with the ring on carbons C Competing Interests: Conflict of interest The authors declare that they have no conflicts of interest with the contents of this article. (Copyright © 2023 The Authors. Published by Elsevier Inc. All rights reserved.) |
| التعليقات: | Erratum in: J Biol Chem. 2024 Apr 4;300(4):107239. (PMID: 38579376) |
| معلومات مُعتمدة: | R01 GM134548 United States GM NIGMS NIH HHS; T32 GM007569 United States GM NIGMS NIH HHS |
| فهرسة مساهمة: | Keywords: NMR; ceramide; corneocyte; epidermis; essential fatty acid; linoleic acid; lipoxygenase; mass spectrometry |
| المشرفين على المادة: | 0 (Ceramides) 0 (Fatty Acids) 9KJL21T0QJ (Linoleic Acid) 0 (Linoleic Acids) EC 1.13.11.12 (Lipoxygenase) |
| تواريخ الأحداث: | Date Created: 20230422 Date Completed: 20230706 Latest Revision: 20240410 |
| رمز التحديث: | 20240410 |
| مُعرف محوري في PubMed: | PMC10209020 |
| DOI: | 10.1016/j.jbc.2023.104739 |
| PMID: | 37086788 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1083-351X |
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| DOI: | 10.1016/j.jbc.2023.104739 |