期刊
MOLECULAR NUTRITION & FOOD RESEARCH
卷 61, 期 12, 页码 -出版社
WILEY
DOI: 10.1002/mnfr.201700562
关键词
alpha-13 '-OH; alpha-13 '-hydroxychromanol; alpha-13 '-COOH; alpha-13 '-carboxy-chromanol; long-chain metabolites of vitamin E
资金
- Federal Ministry of Education and Research [01EA1411A]
- Deutsche Forschungsgemeinschaft (DFG) [RTG 1715, SFB1127, FOR1406]
- German Ministry of Economics and Technology Energy via AiF (German Federation of Industrial Research Associations) [AiF 16642 BR]
- FEI (Research Association of the German Food Industry)
- Free State of Thuringia
- European Social Fund [2016 FGR 0045]
- DFG [Wa 3836/1-1]
Scope: Cytochrome-dependent metabolism of vitamin E initially forms the long-chain metabolites (LCM) 13'-hydroxychromanols (13'-OH) and 13'-carboxychromanols (13'-COOH), which occur in human blood. Little is known about their biological functions. Material and results: A structure-activity relationship study using alpha- and delta-tocopherol (TOH), their LCM (alpha-13'-OH, delta-13'-OH, alpha-13'-COOH, and delta-13'-COOH) and representatives of their substructures (alpha-carboxyethylhydroxychromanol and pristanic acid) is performed to unravel critical structural elements of the LCM for biological activity. Prominent effects are mediated by alpha- and delta-LCM, as scavenger receptor cluster of differentiation 36 (CD36) expression is induced in human THP-1 macrophages and lipopolysaccharide-stimulated inducible nitric oxide synthase (iNos) expression is inhibited in murine RAW264.7 macrophages, while the other molecules are less or not effective. Conclusion: The LCM effects depend on the presence of the chromanol ring system and on the modification of the side-chain but not on the substitution pattern of the chromanol ring. Therefore, it can be concluded that for mediation of effects by LCM the entire molecule is needed and that the effects are specific. We propose the LCM of the micronutrient vitamin E as a new class of regulatory metabolites, but further studies are needed to corroborate this hypothesis.
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