Abstract
The microbial degradation of cholic acid by Pseudomonas sp. N.C.I.B. 10590 was studied, and two major products were isolated and identified as 7 alpha, 12 beta-dihydroxyandrosta-1,4-diene-3,17-dione and 7 alpha, 12 alpha-dihydroxy-3-oxopregna-1,4-diene-20-carboxylic acid. Four minor products were isolated and evidence is given for the following structures: 7 alpha, 12 alpha-dihydroxyandrosta-1,4-diene-3,17-dione, 12 beta-hydroxyandrosta-1,4,6-triene-3,17-dione, 7 alpha, 12 beta, 17 beta-trihydroxyandrosta-1,4-dien-3-one and 7 alpha, 12 alpha-dihydroxy-3-oxopregn-4-ene-20-carboxylic acid. The significance of the production of the steroid products is discussed, along with the possible enzymic mechanisms responsible for their production.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Bridgeman J. E., Cherry P. C., Clegg A. S., Evans J. M., Jones E. R., Kasal A., Kumar V., Meakins G. D., Morisawa Y., Richards E. E. Microbiological hydroxylation of steroids. 1. Proton magnetic resonance spectra of ketones, alcohols, and acetates in the androstane, pregnane, and oestrane series. J Chem Soc Perkin 1. 1970;2:250–257. doi: 10.1039/j39700000250. [DOI] [PubMed] [Google Scholar]
- Hayakawa S. Microbiological transformation of bile acids. Adv Lipid Res. 1973;11:143–192. doi: 10.1016/b978-0-12-024911-4.50011-8. [DOI] [PubMed] [Google Scholar]
- Hill M. J. The role of colon anaerobes in the metabolism of bile acids and steroids, and its relation to colon cancer. Cancer. 1975 Dec;36(6 Suppl):2387–2400. doi: 10.1002/1097-0142(197512)36:6<2387::aid-cncr2820360618>3.0.co;2-4. [DOI] [PubMed] [Google Scholar]
- Midtvedt T. Microbial bile acid transformation. Am J Clin Nutr. 1974 Nov;27(11):1341–1347. doi: 10.1093/ajcn/27.11.1341. [DOI] [PubMed] [Google Scholar]
- Owen R. W., Bilton R. F., Tenneson M. E. The degradation of cholic acid and deoxycholic acid by Bacteroides species under strict anaerobic conditions. Biochem Soc Trans. 1977;5(6):1711–1713. doi: 10.1042/bst0051711. [DOI] [PubMed] [Google Scholar]
- Severina L. O., Torgov I. V., Skrjabin G. K., Wulfson N. S., Zaretskii V. I., Papernaja I. B. The enzymatic transformation of cholic acid by the culture Mycobacterium mucosum 1210. Tetrahedron. 1969 Feb;25(3):485–491. doi: 10.1016/s0040-4020(01)83260-9. [DOI] [PubMed] [Google Scholar]
- Severina L. O., Torgov I. V., Skrjabin G. K., Wulfson N. S., Zaretskii V. I., Papernaja I. B. Transformation of cholic acid by the culture Mycobacterium N 1210. Tetrahedron. 1968 Mar;24(5):2145–2153. doi: 10.1016/0040-4020(68)88116-5. [DOI] [PubMed] [Google Scholar]
- Sih C. J., Whitlock H. W., Jr Biochemistry of steroids. Annu Rev Biochem. 1968;37:661–694. doi: 10.1146/annurev.bi.37.070168.003305. [DOI] [PubMed] [Google Scholar]
- Tenneson M. E., Baty J. D., Bilton R. F., Mason A. N. The degradation of chenodeoxycholic acid by Pseudomonas Spp. N.C.I.B. 10590. J Steroid Biochem. 1979 Mar;10(3):311–316. doi: 10.1016/0022-4731(79)90258-9. [DOI] [PubMed] [Google Scholar]
- Tenneson M. E., Bilton R. F., Mason A. N. The degradation of lithocholic acid by Pseudomonas Spp NCIB 10590. FEBS Lett. 1978 Jul 1;91(1):140–143. doi: 10.1016/0014-5793(78)80035-0. [DOI] [PubMed] [Google Scholar]
- Tenneson M. E., Bilton R. F., Mason A. N. The degradation of taurocholic acid and glycocholic acid by Pseudomonas spp. N.C.I.B. 10590. Biochem Soc Trans. 1978;6(5):975–979. doi: 10.1042/bst0060975. [DOI] [PubMed] [Google Scholar]
- Tenneson M. E., Owen R. W., Mason A. N. The anaerobic side-chain cleavage of bile acids by Escherichia coli isolated from human faeces [proceedings]. Biochem Soc Trans. 1977;5(6):1758–1760. doi: 10.1042/bst0051758. [DOI] [PubMed] [Google Scholar]