New Metabolic Pathway of (24R)-24, 25-Dihydroxyvitamin D3 : Epimerization of the 3-Hydroxy Group

A new metabolic pathway of (24R)-24, 25-dihydroxyvitamin D3 [24, 25(OH)2D3] was clarified in the 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 gen...

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Published in:Biological & pharmaceutical bulletin 1999/07/15, Vol.22(7), pp.767-769
Main Authors: HIGASHI, Tatsuya, KIKUCHI, Ryuta, MIURA, Kanako, SHIMADA, Kazutake, HIYAMIZU, Hiroko, OOI, Hidenori, IWABUCHI, Yoshiharu, HATAKEYAMA, Susumi, KUBODERA, Noboru
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Language:English
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24,25-Dihydroxyvitamin D 3 - metabolism
3-epi-24, 25-dihydroxyvitamin D3
Animals
Biological and medical sciences
Gas Chromatography-Mass Spectrometry
General and cellular metabolism. Vitamins
glucuronide
in vivo metabolite
LC/MS
Magnetic Resonance Spectroscopy
Medical sciences
Pharmacology. Drug treatments
Rats
synthesis
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container_issue 7
container_start_page 767
container_title Biological & pharmaceutical bulletin
container_volume 22
creator HIGASHI, Tatsuya
KIKUCHI, Ryuta
MIURA, Kanako
SHIMADA, Kazutake
HIYAMIZU, Hiroko
OOI, Hidenori
IWABUCHI, Yoshiharu
HATAKEYAMA, Susumi
KUBODERA, Noboru
description A new metabolic pathway of (24R)-24, 25-dihydroxyvitamin D3 [24, 25(OH)2D3] was clarified in the 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 1H-NMR, 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 1α-position.
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source Free Full-Text Journals in Chemistry
subjects 24,25-Dihydroxyvitamin D 3 - metabolism
3-epi-24, 25-dihydroxyvitamin D3
Animals
Biological and medical sciences
Gas Chromatography-Mass Spectrometry
General and cellular metabolism. Vitamins
glucuronide
in vivo metabolite
LC/MS
Magnetic Resonance Spectroscopy
Medical sciences
Pharmacology. Drug treatments
Rats
synthesis
title New Metabolic Pathway of (24R)-24, 25-Dihydroxyvitamin D3 : Epimerization of the 3-Hydroxy Group
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