Skip to main content
NCBI home page
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1981 Aug;78(8):4805–4808. doi: 10.1073/pnas.78.8.4805

23,25-Dihydroxyvitamin D3: a natural precursor in the biosynthesis of 25-hydroxyvitamin D3-26,23-lactone.

Y Tanaka, H F DeLuca, H K Schnoes, N Ikekawa, T Eguchi
PMCID: PMC320253  PMID: 6975475

Abstract

To elucidate the biosynthesis of 25-hydroxyvitamin D3-26,23-lactone, two known metabolites of 25-hydroxyvitamin D3--23,25-dihydroxyvitamin D3 and 25,26-dihydroxyvitamin D3--were incubated individually with kidney homogenate prepared from vitamin D-supplemented chickens, a preparation known to produce the lactone from 25-hydroxyvitamin D3. The 25-hydroxyvitamin D3-26,23-lactone produced in vitro was then separated, purified, identified, and quantitated by consecutive straight-phase and reverse-phase high-performance liquid chromatography. 23,25-Dihydroxyvitamin D3 is a far better substrate for production of 25-hydroxyvitamin D3-26,23-lactone than is 25,26-dihydroxyvitamin D3. Production of lactone is highly selective for the natural 23(S)-hydroxy-23,25-dihydroxyvitamin D3 while both epimers of 25,26-dihydroxyvitamin D3 resulted in small amounts of product comigrating with natural lactone. It appears that 23(S),25-dihydroxyvitamin D3, but not 25,26-dihydroxyvitamin D3, is a natural precursor in the synthesis of 25-hydroxyvitamin D3-26,23-lactone; this result also implies that the configuration of the lactone at C-23 is S.

Full text

PDF
4805

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. DeLuca H. F., Suda T., Schnoes H. K., Tanaka Y., Holick M. F. 25,26-dihydroxycholecalciferol, a metabolite of vitamin D3 with intestinal calcium transport activity. Biochemistry. 1970 Nov 24;9(24):4776–4780. doi: 10.1021/bi00826a022. [DOI] [PubMed] [Google Scholar]
  2. Eisman J. A., Hamstra A. J., Kream B. E., DeLuca H. F. 1,25-Dihydroxyvitamin D in biological fluids: a simplified and sensitive assay. Science. 1976 Sep 10;193(4257):1021–1023. doi: 10.1126/science.1085035. [DOI] [PubMed] [Google Scholar]
  3. Holick M. F., DeLuca H. F. A new chromatographic system for vitamin D3 and its metabolites: resoluation of a new vitamin D3 metabolite. J Lipid Res. 1971 Jul;12(4):460–465. [PubMed] [Google Scholar]
  4. Hollis B. W., Roos B. A., Lambert P. W. 25,26-Dihydroxycholecalciferol: a precursor in the renal synthesis of 25-hydroxycholecalciferol-26,23-lactone. Biochem Biophys Res Commun. 1980 Jul 31;95(2):520–528. doi: 10.1016/0006-291x(80)90815-3. [DOI] [PubMed] [Google Scholar]
  5. Horst R. L., Shepard R. M., Jorgensen N. A., DeLuca H. F. The determination of 24,25-dihydroxyvitamin D and 25,26-dihydroxyvitamin D in plasma from normal and nephrectomized man. J Lab Clin Med. 1979 Feb;93(2):277–285. [PubMed] [Google Scholar]
  6. Omdahl J., Holick M., Suda T., Tanaka Y., DeLuca H. F. Biological activity of 1,25-dihydroxycholecalciferol. Biochemistry. 1971 Jul 20;10(15):2935–2940. doi: 10.1021/bi00791a022. [DOI] [PubMed] [Google Scholar]
  7. Shephard R. M., Deluca H. F. Plasma concentrations of vitamin D3 and its metabolites in the rat as influenced by vitamin D3 or 25-hydroxyvitamin D3 intakes. Arch Biochem Biophys. 1980 Jun;202(1):43–53. doi: 10.1016/0003-9861(80)90404-x. [DOI] [PubMed] [Google Scholar]
  8. Tanaka Y., Halloran B., Schnoes H. K., DeLuca H. F. In vitro production of 1,25-dihydroxyvitamin D3 by rat placental tissue. Proc Natl Acad Sci U S A. 1979 Oct;76(10):5033–5035. doi: 10.1073/pnas.76.10.5033. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Tanaka Y., Shepard R. A., DeLuca H. F., Schnoes H. K. The 26-hydroxylation of 25-hydroxyvitamin D3 in vitro by chick renal homogenates. Biochem Biophys Res Commun. 1978 Jul 14;83(1):7–13. doi: 10.1016/0006-291x(78)90390-x. [DOI] [PubMed] [Google Scholar]
  10. Tanaka Y., Wichmann J. K., Paaren H. E., Schnoes H. K., DeLuca H. F. Role of kidney tissue in the production of 25-hydroxyvitamin D3-26,23-lactone and 1 alpha, 25-dihydroxyvitamin D3-26,23-lactone. Proc Natl Acad Sci U S A. 1980 Nov;77(11):6411–6414. doi: 10.1073/pnas.77.11.6411. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Tanaka Y., Wichmann J. K., Schnoes H. K., DeLuca H. F. Isolation and identification of 23,25-dihydroxyvitamin D3, an in vivo metabolite of vitamin D3. Biochemistry. 1981 Jun 23;20(13):3875–3879. doi: 10.1021/bi00516a032. [DOI] [PubMed] [Google Scholar]
  12. Wichmann J. K., DeLuca H. F., Schnoes H. K., Horst R. L., Shepard R. M., Jorgensen N. A. 25-Hydroxyvitamin D3 26,23-lactone: a new in vivo metabolite of vitamin D. Biochemistry. 1979 Oct 30;18(22):4775–4780. doi: 10.1021/bi00589a002. [DOI] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES