New metabolic pathway of (24R)-24,25-dihydroxyvitamin D3: Epimerization of the 3-hydroxy group

Tatsuya Higashi, Ryuta Kikuchi, Kanako Miura, Kazutake Shimada, Hiroko Hiyamizu, Hidenori Ooi, Yoshiharu Iwabuchi, Susumi Hatakeyama, Noboru Kubodera

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

A new metabolic pathway of (24R)-24,25-dihydroxyvitamin D3 [24,25(OH)2D3] was clarified in the in vivo experiments. After the administration of 24,25(OH)2D3 to rats, a new monoglucuronide of a vitamin D metabolite was obtained from the bile together with 24,25(OH)2D3 3- and 24-glucuronides. The genin of the metabolite was identified as 3-epi- 24,25(OH)2D3 in comparison with the synthetic sample based on the data from 1HNMR, GC/MS, and LC/atmospheric pressure chemical ionization-MS. The conjugation position was determined to be the 24-hydroxy group by the LC/electrospray ionization-MS and MS/MS/MS combined with derivatization. To our knowledge, this is the first reported instance of the epimerization of the 3-hydroxy group of vitamin D compound with no hydroxy group at the 1 α- position.

Original languageEnglish
Pages (from-to)767-769
Number of pages3
JournalBiological and Pharmaceutical Bulletin
Volume22
Issue number7
DOIs
Publication statusPublished - 1999 Jul

Keywords

  • 3-epi-24,25-dihydroxyvitamin D
  • Glucuronide
  • In vivo metabolite
  • LC/MS
  • Synthesis

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

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