Microbial hydroxylation of 13-ethyl-17β-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one

Degradation of Norgestrel by Bacteria from Activated Sludge: Comparison to Progesterone

“…To the best of our knowledge, only two previous studies reported that norgestrel could be transformed by microorganism via hydroxylation reactions at different positions. 36,37 This is the first report on the biodegradation products of norgestrel by bacteria from aerobic activated sludge.…”

Biotransformation of progesterone and norgestrel by two freshwater microalgae (Scenedesmus obliquus and Chlorella pyrenoidosa): Transformation kinetics and products identification

“…This is the first report on algal transformation of norgestrel and the formation of the two transformation products. However, hydroxyl derivatives have been observed in the degradation of norgestrel by some industrial fungi including Rhizopus nigricans, R. arrhizus and Aspergillus niger (Hu et al, 1996).…”

“…Recent laboratory studies showed that progesterone and norgestrel could affect fish reproduction and hormone receptor gene expressions at ng L À1 levels (Zeilinger et al, 2009;DeQuattro et al, 2012;Zucchi et al, 2012). Some investigations from pharmaceutical industry indicate that steroids including progesterone and norgestrel could be transformed by algae, bacteria and fungi (Hu et al, 1996;Pollio et al, 1996;Huszcza et al, 2005;Eshrat and Aroona, 2011). However, in-depth studies are needed to understand the role of various microbes like algae in the fate of progesterone and norgestrel in the aquatic environment, including their transformation mechanisms and transformation products.…”

Oxidation of lynestrenol by the fungusCunninghamella elegans

“…The location of the hydroxyl group at C-10 was deduced on the basis of the heteronuclear multiple bond connectivity (HMBC) interaction of H-4 ( 5.76) with C-10 ( 68.2). The orientation of the OH-group at C-10 was deduced from the downfield chemical shifts of C-1 and C-9, and by the upfield shifts of C-6, C-8, and C-11 (À4.2, À6.1 and À2.9 ppm, respectively) as compared to the substrate 1, as well as a chemical shift comparison with the reported data of a closely related compound, 13-ethyl-10,17-dihydroxy-18, 19-dinor-17-pregn-4-en-20-yn-3-one (Hu, Tian, Sun, & Han, 1996). Compound 2 was therefore identified as 19-nor-17-pregn-4-en-20-yn-3-one-10,17-diol (ZakeljMavric et al, 1986).…”