Biotransformations of Steroids

Abstract

Different types of microbiological transformation of steroids are reviewed, with special attention given to bioconversions applied in the manufacturing of steroid hormones, i.e., 11 alpha- 11 beta-, 16 alpha-, 17 alpha-hydroxylations and 1-dehydrogenation. Availability and utilization of raw materials for industrial production of steroids of the estrane, androstane, and pregnane series are discussed. Among the current trends in steroid research of a practical nature, immobilization of enzymes and living cells and the spore process are emphasized as alternative techniques of steroid transformation of possible future importance. Efforts to recognize, in cell-free preparations, the components of steroid-transforming enzyme systems as well as the cellular mechanisms of control of their biosynthesis and activity are described in order to illustrate the main subjects of current basic investigation in steroid bioconversion.

Identification and targeted disruption of the gene encoding the main 3-ketosteroid dehydrogenase in Mycobacterium smegmatis

“…The resulting constructs carrying putative M. smegmatis ksdD-1 and ksdD-2 genes were named pTS1 and pAB42, respectively. The putative ksdD genes of M. tuberculosis were PCR-amplified using TbD1s (Martin, 1977;Sedlaczek, 1988). KSTH, Steroid 9a-hydroxylase; KSDD, 3-ketosteroid dehydrogenase; 9OHADD, 9a-hydroxy-1,4-androstadiene-3,17-dione.…”

“…A number of Mycobacterium strains treated with mutagens have been reported to accumulate sterol biodegradation intermediates such as 4-androstene-3,17-dione (AD) and 1,4-androstadiene-3,17-dione (ADD) (Mahato & Garai, 1997;Martin, 1977;Szentirmai, 1990). These intermediates may be used as precursors for the production of steroid drugs and hormones (Sedlaczek, 1988). Two enzymes, 3-ketosteroid D 1 -dehydrogenase (KsdD) and 3-ketosteroid 9a-hydroxylase (KsdH) are essential to initiate steroid ring degradation (Fig.…”

Transformations of testosterone and related steroids in Absidia glauca culture

“…For many years fungi have been used for the hydroxylation of steroids (SEDLACZEK 1988, HOLLAND 1999 since their enzyme systems catalyse reactions with high regio-and stereospecifity. Microbial transformations can be carried out giving higher yields at lower costs than chemical methods (SEDLACZEK 1988).…”

Purification, crystallization and preliminary X-ray crystallographic analysis of 3-ketosteroid Δ1-dehydrogenase fromRhodococcus erythropolisSQ1

“…Through their biotransformation, a large variety of physiologically active steroid intermediates are produced (Horinouchi et al, 2003;Sedlaczek, 1988). These intermediates and their derivatives are utilized extensively as drugs and hormones because of their anti-inflammatory, diuretic, anabolic, contraceptive, anti-androgenic, progestational and anticancer properties (Donova, 2007;Mahato & Garai, 1997).…”