1.Bioconversion of 3 beta-acetoxypregna-5,16-diene-20-one to androsta-1,4-diene-3,17-dione by mixed bacterial culture.
Patil S1, Shukla A, Shinde K, Banerjee T. Lett Appl Microbiol. 2002;35(2):95-7.
AIMS: To isolate a bacterium capable of degrading 3 beta-acetoxypregna-5,16-diene-20-one (16-DPA) to androsta-1,4-diene-3,17-dione (ADD) and to decipher the biodegradation pathway.
2.Inhibitory effect of 11 beta-hydroxypregna-1,4-diene-3,20-dione (delta HOP) on lymphocyte proliferation.
Rondinone CM1, Schillaci R, Castillo MB, Roldán A. Clin Exp Immunol. 1991 Nov;86(2):311-4.
We have compared the immunosuppressive effect of delta HOP and glucocorticoids on lymphocyte proliferation and IL-1 secretion. The new synthetic steroid only inhibited proliferation of phytohaemagglutinin (PHA)-stimulated human lymphocyte at high concentrations and the effect did not persist after washing out the steroid. In contrast, glucocorticoids produced the classical dose-response inhibition and the effect persisted when they were removed from the cultured medium. Although both steroids decreased IL-1 secretion from human monocytes stimulated with lipopolysaccharide (LPS), they exert the same effect through a different mechanism. The experiments we report suggest that the decrease of IL-1 synthesis produced by delta HOP could be caused by inhibition of LPS phagocytosis. These results support our hypothesis that delta HOP exerts its immunosuppressive and anti-inflammatory effect by a non-genomic mechanism.
Yousuf S1, Bibi M, Choudhary MI. Acta Crystallogr Sect E Struct Rep Online. 2011 Aug 1;67(Pt 8):o2122. doi: 10.1107/S1600536811028674. Epub 2011 Jul 23.
The title compound, C(21)H(28)O(3), is a fungal transformed metabolite of decoxycorticosterone acetate, consisting of four fused rings A, B, C and D. Ring A is nearly planar, with a maximum deviation of 0.010 (3) Å from the least-squares plane, while the trans-fused rings B and C adopt chair conformations. The five-membered ring D is in an envelope conformation. The orientation of the side chain is stabilized by an intramolecular O-H⋯O hydrogen bond. In the crystal, adjecent mol-ecules are linked by C-H⋯O hydrogen bonds into extended zigzag chains along the a axis.
4.Bioconversion of steroids by Cochliobolus lunatus--II. 11 beta-hydroxylation of 17 alpha, 21-dihydroxypregna-1,4-diene-3,20-dione 17-acetate in dependence of the inducer structure.
Undisz K1, Groh H, Stopsack H, Hörhold-Schubert C. J Steroid Biochem Mol Biol. 1992 Nov;43(6):543-7.
The 11 beta-hydroxylase of the filamentous fungus Cochliobolus lunatus m 118 was induced with the substrate 17 alpha, 21-dihydroxypregna-1,4-diene-3,20-dione 17-acetate (11 beta-deoxyprednisolone 17-acetate) itself, substrate analogues, different pregnane compounds, sterols, intermediates of microbial sterol side-chain degradation or bile acids, together with 24 different steroids in a standardized test system. The resulting 11 beta-hydroxylation rate, leading to prednisolone 17-acetate and prednisolone, respectively, was determined and compared with the hydroxylation rate of non-induced cultures. The transformation yield strongly depended on the inducer structure. The microbial sterol side-chain degradation intermediates (20S)-20-hydroxymethylpregn-4-en-3-one and the corresponding pregna-1,4-diene compound caused the highest induction effects (induction factors 5.1 and 4.9, respectively). The metabolism of (20S)-20-hydroxymethylpregna-1,4-dien-3-one during the cultivation was elucidated.