Formation of 5α steroids by biotranformation involving the 5α-reductase activity of Penicillium decumbens

Steroid-transforming enzymes in fungi

“…Several Penicillium spp. (Penicillium decumbens, P. chrysogenum, Penicillium crustosum) can reduce double bonds in testosterone, to form 5␣-DHT [84,109], and a 5␣-reductase from P. crustosum has been characterised. The K M and V max values for reduction of testosterone were determined as 0.22 ± 0.07 M and 0.83 ± 0.05 pmol 5␣-DHT/mg mycelium/day, respectively [110].…”

“…11␤-hydroxlase, 11␣-hydroxylase, 5␣-reductase) [82][83][84]94,95]. These enzymes can be applicable for the production of bile acids (7␣-hydroxylase), neurosteroids (5␣-reductase), cardioactive steroids (14␣-hydroxylase) [103], androgens (3␤-HSD, 17␤-HSD, 5␣-reductase, 1 -dehydrogenase) [106], and progestins ( 1 -dehydrogenase, 11␣-hydroxylase, 11␤-hydroxylase) [5].…”

Biotransformation of testosterone by the filamentous fungus Penicillium pinophilum

“…The 1 H NMR spectrum revealed a new signal as a triplet of doublet at 4.04 ppm (J = 10.3 Hz and J = 4.6 Hz) and a mild down eld shift for H-19 signal (Δ 0.12 ppm). As well, the13 C NMR spectrum exhibited a signi cant shift for C-11 signal from 20.67 to 69.07 (Δ 48.40 ppm) along with down eld shifts for C-12 (Δ 12.26 ppm) and C-9 (Δ 5.38) ppm. These data supported the presence of a hydroxyl group at the C-11 position.…”

“…The 1 H and 13 C NMR spectra were acquired using Bruker Avance 500 and 300 (Bruker BioSpin GmbH, Rheinstetten, Germany) at 500 and 300 MHz, 125 and 75 MHz, respectively in CDCl 3 . The ESI-MS spectra were recorded on an Agilent 6410 Triple Quad mass spectrometer in positive ion mode (Agilent Technologies, Inc., Wilmington, DE, USA).…”

“…17β-Hydroxyandrost-4-en-3-one (Testosterone) (substrate I): White solid; R f in Chloroform-Methanol (8.8- 13 C NMR (CDCl 3 , 75 MHz) spectrum have been presented in Table 1.…”