Isolation, identification, and metabolism of (23S,25R)-25-hydroxyvitamin D3 26,23-lactol. A biosynthetic precursor of (23S,25R)-25-hydroxyvitamin D3 26,23-lactone

• Published in: The Journal of biological chemistry Vol. 259; no. 2; pp. 884 - 889
• Main Authors: Yamada, S, Nakayama, K, Takayama, H, Shinki, T, Takasaki, Y, Suda, T
• Format: Journal Article
• Language: English
• Published: Bethesda, MD Elsevier Inc 25.01.1984; American Society for Biochemistry and Molecular Biology
• Subjects: Analytical, structural and metabolic biochemistry; Animals; Biological and medical sciences; Calcifediol - analogs & derivatives; Calcifediol - isolation & purification; Calcifediol - metabolism; Chickens; Chromatography, High Pressure Liquid; Coenzymes, vitamins; Fundamental and applied biological sciences. Psychology; Hydroxycholecalciferols - metabolism; Kidney - metabolism; Mass Spectrometry; Other biological molecules; Stereoisomerism; Vertebrata; Homogenate; Vitamin; Biosynthesis; Chicken; Aves; Metabolism; Chemical synthesis; Kidney
• ISSN: 0021-9258; 1083-351X
• DOI: 10.1016/S0021-9258(17)43539-3

23S,25R,26-Trihydroxyvitamin D3 and (23S,25R)-25-hydroxyvitamin D3 26,23-lactol were chemically synthesized, and the metabolism of the two compounds to (23S,25R)-25-hydroxyvitamin D3 26,23-lactone in chick kidney homogenates was studied. 23S,25R,26-trihydroxyvitamin D3 was efficiently metabolized to the lactone in kidney homogenates from vitamin D-supplemented chicks, but not from vitamin D-deficient chicks. In contrast, the (23S,25R)-25-hydroxyvitamin D3 26,23-lactol was converted to the lactone in kidney homogenates regardless of the vitamin D status of the animals used. A new metabolite was isolated in pure form from the incubation mixture of 23S,25R,26-trihydroxyvitamin D3 with kidney homogenates prepared from vitamin D-supplemented chicks. The metabolite was identified as (23S,25R)-25-hydroxyvitamin D3 26,23-lactol by its ultraviolet and mass spectra and by derivatization. The structure was confirmed by direct comparison with an authentic sample on high pressure liquid chromatography. The evidence suggests that the stereochemistries of the isolated lactol at the 23- and 25-positions are S and R, respectively.