NDLI: Pathways and products for the metabolism of vitamin D3 by cytochrome P450scc.

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Pathways and products for the metabolism of vitamin D3 by cytochrome P450scc.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Tuckey, Robert C. Li, Wei Zjawiony, Jordan K. Zmijewski, Michal A. Nguyen, Minh N. Sweatman, Trevor Miller, Duane Slominski, Andrzej
Description	Country affiliation: Australia Author Affiliation: Tuckey RC ( School of Biomolecular, Biomedical and Chemical Sciences, The University of Western Australia, Crawley, WA, Australia. rtuckey@cyllene.uwa.edu.au)
Abstract	Cytochrome P450scc (CYP11A1) can hydroxylate vitamin D3 to produce 20-hydroxyvitamin D3 and other poorly characterized hydroxylated products. The present study aimed to identify all the products of vitamin D3 metabolism by P450scc, as well as the pathways leading to their formation. Besides 20-hydroxyvitamin D3, other major metabolites of vitamin D3 were a dihydroxyvitamin D3 and a trihydroxyvitamin D3 product. The dihydroxyvitamin D3 was clearly identified as 20,23-dihydroxyvitamin D3 by NMR, in contrast to previous reports that postulated hydroxyl groups in positions 20 and 22. NMR of the trihydroxy product identified it as 17alpha,20,23-trihydroxyvitamin D3. This product could be directly produced by P450scc acting on 20,23-dihydroxyvitamin D3, confirming that hydroxyl groups are present at positions 20 and 23. Three minor products of D3 metabolism by P450scc were identified by MS and by examining their subsequent metabolism by P450scc. These products were 23-hydroxyvitamin D3, 17alpha-hydroxyvitamin D3 and 17alpha,20-dihydroxyvitamin D3 and arise from the three P450scc-catalysed hydroxylations occurring in a different order. We conclude that the major pathway of vitamin D3 metabolism by P450scc is: vitamin D3 --> 20-hydroxyvitamin D3 --> 20,23-dihydroxyvitamin D3 --> 17alpha,20,23-trihydroxyvitamin D3. The major products dissociate from the P450scc active site and accumulate at a concentration well above the P450scc concentration. Our new identification of the major dihydroxyvitamin D3 product as 20,23-dihydroxyvitamin D3, rather than 20,22-dihydroxyvitamin D3, explains why there is no cleavage of the vitamin D3 side chain, unlike the metabolism of cholesterol by P450scc.
File Format	HTM / HTML
ISSN	1742464X
e-ISSN	17424658
DOI	10.1111/j.1742-4658.2008.06406.x
Journal	FEBS Journal
Issue Number	10
Volume Number	275
Language	English
Publisher	Wiley (on behalf of the Federation of European Biochemical Societies)
Publisher Date	2008-05-01
Publisher Place	Great Britain (UK)
Access Restriction	Open
Subject Keyword	Discipline Biochemistry Cholecalciferol Metabolism Cholesterol Side-chain Cleavage Enzyme Animals Chemistry Molecular Structure Nuclear Magnetic Resonance, Biomolecular Vitamin D Analogs & Derivatives Research Support, N.i.h., Extramural Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Cell Biology Biochemistry Molecular Biology

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