Transformation of 25- and 1 Alpha-hydroxyvitamin D3 to 1 Alpha, 25-dihydroxyvitamin D3 by Using Streptomyces Sp. Strains

Overview

Journal Appl Environ Microbiol

Specialties Environmental Health
Microbiology

Date 1991 Oct 1

PMID 1746944

Citations 12

Authors

J Sasaki

A Mikami

K Mizoue

S Omura

Affiliations

Soon will be listed here.

Abstract

To enzymatically synthesize vitamin D derivatives, we screened about 300 Streptomyces sp. strains. Streptomyces sclerotialus FERM BP-1370 and Streptomyces roseoporus FERM BP-1574 were found to have the ability to convert 25-hydroxyvitamin D3 and 1 alpha-hydroxyvitamin D3, respectively, to 1 alpha, 25-dihydroxyvitamin D3. The average rates of 1 alpha hydroxylation of 25-hydroxyvitamin D3 were 6.9 micrograms liter-1 min-1 with FERM BP-1370 and 7.0 micrograms liter-1 min-1 with FERM BP-1574. The specific cytochrome P-450 inhibitors carbon monoxide, SKF-525-A, and metyrapone inhibited the hydroxylation of 1 alpha- and 25-hydroxyvitamin D3 to 1 alpha, 25-dihydroxyvitamin D3 by FERM BP-1370 and FERM BP-1574. The cytochromes P-450 of these strains were detected by reduced CO difference spectra in the whole-cell suspensions. The appearance of cytochrome P-450 suggests that the cytochromes P-450 of FERM BP-1370 and FERM BP-1574 carry out the hydroxylation of 25- and 1 alpha-hydroxyvitamin D3 to 1 alpha, 25-dihydroxyvitamin D3.

Citing Articles

Structural diversification of vitamin D using microbial biotransformations.

Garcia-Dominguez M, Gutierrez-Del-Rio I, Villar C, Perez-Gomez A, Sancho-Martinez I, Lombo F Appl Microbiol Biotechnol. 2024; 108(1):409.

PMID: 38970663 PMC: 11227467. DOI: 10.1007/s00253-024-13244-w.

Characterization of vitamin D3 biotransformation by the cell lysate of Actinomyces hyovaginalis CCASU-A11-2.

Abbas A, Elkhatib W, Aboulwafa M, Hassouna N, Aboshanab K AMB Express. 2024; 14(1):43.

PMID: 38658456 PMC: 11043238. DOI: 10.1186/s13568-024-01694-4.

Bioconversion of vitamin D into calcitriol by Actinomyces hyovaginalis isolate CCASU- A11-2.

Abbas A, Elkhatib W, Aboulwafa M, Hassouna N, Aboshanab K AMB Express. 2023; 13(1):73.

PMID: 37434090 PMC: 10335987. DOI: 10.1186/s13568-023-01574-3.

Vitamins as regulators of calcium-containing kidney stones - new perspectives on the role of the gut microbiome.

Chmiel J, Stuivenberg G, Al K, Akouris P, Razvi H, Burton J Nat Rev Urol. 2023; 20(10):615-637.

PMID: 37161031 PMC: 10169205. DOI: 10.1038/s41585-023-00768-5.

Bioconversion of vitamin D to bioactive calcifediol and calcitriol as high-value compounds.

Wang Z, Zeng Y, Jia H, Yang N, Liu M, Jiang M Biotechnol Biofuels Bioprod. 2022; 15(1):109.

PMID: 36229827 PMC: 9563128. DOI: 10.1186/s13068-022-02209-8.

References

Omura T, Sato R . THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. I. EVIDENCE FOR ITS HEMOPROTEIN NATURE. J Biol Chem. 1964; 239:2370-8. View

Lund J, DeLuca H . Biologically active metabolite of vitamin D3 from bone, liver, and blood serum. J Lipid Res. 1966; 7(6):739-44. View

Tanaka Y, Sicinski R, DeLuca H, Sai H, Ikekawa N . Unique rearrangement of ergocalciferol side chain in vitro: production of a biologically highly active homologue of 1,25-dihydroxyvitamin D3. Biochemistry. 1986; 25(19):5512-8. DOI: 10.1021/bi00367a025. View

Lu M, Wung W, Shih L, Callejas S, GEARIEN J, Thompson E . Molecular modification of anticholinergics as probes for muscarinic receptors. 1. Amino esters of alpha-substituted phenylacetic acid and related analogues. J Med Chem. 1987; 30(2):273-8. DOI: 10.1021/jm00385a008. View

Helmer B, Schnoes H, DeLuca H . 1H nuclear magnetic resonance studies of the conformations of vitamin D compounds in various solvents. Arch Biochem Biophys. 1985; 241(2):608-15. DOI: 10.1016/0003-9861(85)90587-9. View

Clements M, Johnson L, Fraser D . A new mechanism for induced vitamin D deficiency in calcium deprivation. Nature. 1987; 325(6099):62-5. DOI: 10.1038/325062a0. View

Kametani T, Furuyama H . Synthesis of vitamin D3 and related compounds. Med Res Rev. 1987; 7(2):147-71. DOI: 10.1002/med.2610070202. View

Ikekawa N . Structures and biological activities of vitamin D metabolites and their analogs. Med Res Rev. 1987; 7(3):333-66. DOI: 10.1002/med.2610070304. View

Seino Y, Tanaka H, Yamaoka K, Yabuuchi H . Circulating 1 alpha,25-dihydroxyvitamin D levels after a single dose of 1 alpha,25-dihydroxyvitamin D3 or 1 alpha-hydroxyvitamin D3 in normal men. Bone Miner. 1987; 2(6):479-85. View

10.

Mallon J, Hamilton J, Karol R, Ashley C, Matuszewski D, Tratnyek C . An improved competitive protein binding assay for 1,25-dihydroxyvitamin D. Arch Biochem Biophys. 1980; 201(1):277-85. DOI: 10.1016/0003-9861(80)90512-3. View

11.

DeLuca H, Schnoes H . Vitamin D: recent advances. Annu Rev Biochem. 1983; 52:411-39. DOI: 10.1146/annurev.bi.52.070183.002211. View

12.

Seino Y, Yamaoka K, Ishida M, Yabuuchi H, Ichikawa M, Ishige H . Biochemical characterization of 1,25(OH)2D3 receptors in chick embryonal duodenal cytosol. Calcif Tissue Int. 1982; 34(3):265-9. DOI: 10.1007/BF02411248. View

13.

Hansson R, Holmberg I, Wikvall K . 25-Hydroxylation vitamin D3 and side chain hydroxylations of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha-triol by purified rabbit and rat liver microsomal cytochromes P-450. J Biol Chem. 1981; 256(9):4345-9. View

14.

Bjorkhem I, Holmberg I, Oftebro H, Pedersen J . Properties of a reconstituted vitamin D3 25-hydroxylase from rat liver mitochondria. J Biol Chem. 1980; 255(11):5244-9. View

15.

Pike J, Haussler M . Characteristics and purification of the intstinal receptor for 1,25-dihydroxyvitamin D. Methods Enzymol. 1980; 67:508-22. DOI: 10.1016/s0076-6879(80)67064-5. View

16.

Hiwatashi A, Nishii Y, Ichikawa Y . Purification of cytochrome P-450D1 alpha (25-hydroxyvitamin D3-1 alpha-hydroxylase) of bovine kidney mitochondria. Biochem Biophys Res Commun. 1982; 105(1):320-7. DOI: 10.1016/s0006-291x(82)80047-8. View

17.

Hiwatashi A, Ichikawa Y . Purification and organ-specific properties of cholecalciferol 25-hydroxylase system: cytochrome P-450D25-linked mixed function oxidase system. Biochem Biophys Res Commun. 1980; 97(4):1443-9. DOI: 10.1016/s0006-291x(80)80027-1. View

18.

Chandler J, Pike J, Hagan L, Haussler M . A sensitive radioreceptor assay for 1 alpha, 25-dihydroxyvitamin D in biological fluids. Methods Enzymol. 1980; 67:522-8. DOI: 10.1016/s0076-6879(80)67065-7. View

19.

Tanaka Y, DeLuca H, Ikekawa N . High-pressure liquid chromatography of vitamin D metabolites and analogs. Methods Enzymol. 1980; 67:370-85. DOI: 10.1016/s0076-6879(80)67046-3. View

20.

Cerniglia C, Gibson D . Metabolism of naphthalene by cell extracts of Cunninghamella elegans. Arch Biochem Biophys. 1978; 186(1):121-7. DOI: 10.1016/0003-9861(78)90471-x. View