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In the study of the synthesis of 14-epi-19-norprevitamin D(3), we found 14-epi-19-nortachysterol derivatives through C6,7-cis/trans isomerization. We also succeeded in their chemical synthesis and revealed their marked stability and potent VDR binding affinity. To the best of our knowledge, this is the first isolation of stable tachysterol analogues. Surprisingly, 14-epi-19-nortachysterol derivatives exhibited an unprecedented binding configurations for the ligand binding pocket in hVDR, C5,6-s-trans and C7,8-s-trans triene configurations, which were opposite the natural C7,8-ene-configuration of 1α,25(OH)(2)D(3).

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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 syn- The authors declare no conflict of interest.