Synthesis and determination of configuration of natural 25-hydroxyvitamin D3 26,23-lactone*

AUTOR(ES)

Eguchi, Tadashi

RESUMO

The four stereoisomers of 25-hydroxyvitamin D3 26,23-lactone were synthesized by a stereoselective lactonization method. Natural 25-hydroxyvitamin D3 26,23-lactone was produced from 25-hydroxy-[3α-3H]vitamin D3 by in vitro incubation of kidney homogenate prepared from vitamin D-supplemented chickens or was isolated from the serum of rats given 1,25-dihydroxyvitamin D3 and 25-hydroxy-[3α-3H]vitamin D3. The four synthetic isomers and the naturally produced 25-hydroxyvitamin D3 26,23-lactone were subjected to high-performance liquid chromatography in a system capable of separating the four isomers. The natural lactone comigrated with synthetic (23S,25R)-25-hydroxyvitamin D3 26,23-lactone, establishing it as the natural vitamin D3 metabolite.

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