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A previous report has demonstrated the existence of a C4-hydroxylated vitamin D(2) metabolite in serum of rats treated with pharmacological doses of vitamin D(2). However, the biological significance and metabolic fate of this metabolite have not been described. To explore its potential biological activities, we therefore synthesized 1α,4α,25-trihydroxyvitamin D(3) and its diastereoisomer, 1α,4β,25-trihydroxyvitamin D(3), using Trost Pd-mediated coupling reaction, and studied their vitamin D receptor (VDR) binding affinity, osteocalcin promoter transactivation activity, and their further metabolism by human CYP24A1 as well as by human liver microsomal fraction based on CYP- and UDP-glucuronosyltransferases (UGTs)-reactions.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Synthesis and Biological Activities of 1α,4α,25- and 1α,4β,25-Trihydroxyvitamin D&lt;sub&gt;3&lt;/sub&gt; and Their Metabolism by Human CYP24A1 and UDP-Glucuronosyltransferase