<i>Fusarium lini</i> Potential for the Biotransformation of Norandrostenedione and Evaluation of Urease and Chymotrypsin Properties of the Transformed Products

Several androgenic steroids have been biotransformed\r\nby fungi into metabolites with numerous biological properties. Incubation of\r\nnorandrostenedione (1) with Fusarium lini NRRL 2204 was carried out for the first time, yielding two new\r\nmetabolites, 3,7β-dihydroxy-19-norandrost-1,3,5-trien-17-one (3) and 6α,10β,17β-trihydroxy-19-nor-4-androsten-3-one (4), along with three known compounds, 3-hydroxy-19-norandrost-1,3,5-trien-17-one\r\n(2), 10β, 17β-dihydroxy-19-nor-4-androsten-3-one (5) and 10β-hydroxy-19-nor-4- androsten-3,17-dione (6). Their structures were elucidated by extensive\r\nspectroscopic analyses, including 1D-, 2D-NMR, and HR-MS experiments. Substrate 1 and its derivatives 2-6 were evaluated in vitro for their urease and chymotrypsin inhibitory properties.\r\nCompounds 2 and 3 were found to have strong urease activity with\r\nIC50 = 23.7 ± 0.17 and 10.2 ± 0.28 μm, respectively, as compared\r\nto the standard drug thiourea (IC50 = 21.6 ± 0.12 μm). Compounds 4, 5 and 6 showed good chymotrypsin activity with IC50 values of\r\n6.4 ± 0.19, 15.6 ± 0.46 and 18.4 ± 0.65 μm, respectively, as compared to standard chymostatin\r\nwith IC50 = 5.7 ± 0.14 μm. These transformed metabolites may form the basis for the future\r\ndevelopment of new drugs against ulcer, inflammation, bacterial and viral\r\ndiseases.