Studies on the microbial transformation of androst-1,4-dien-3,17-dione with Acremonium strictum

Abstract

The strain of Acremonium strictum PTCC 5282 was applied to investigate the biotransformation of androst-1,4-dien-3,17-dione (I; ADD). Microbial products obtained were purified by preparative TLC and the pure metabolites were characterized on the basis of their spectroscopic features (13C NMR, 1H NMR, FTIR, MS) and physical constants (melting points and optical rotations). The 15 alpha-Hydroxyandrost-1,4-dien-3,17-dione (II), 17 beta-hydroxyandrost-1,4-dien-3-one (III), androst-4-en-3,17-dione (IV; AD), 15 alpha-hydroxyandrost-4-en-3,17-dione (V), 15 alpha,17 beta-dihydroxyandrost-1,4-dien-3-one (VI) and testosterone (VII) were produced during this fermentation. Formation of the 15 alpha,17 beta-dihydroxy derivative of ADD is reported for the first time during steroid biotransformation. The bioconversion reactions observed were 1,2-hydrogenation, 15 alpha-hydroxylation and 17-ketone reduction. From the time course profile of this biotransformation, ketone reduction and 1,2-hydrogenation were observed from the first day of fermentation while 15 alpha-hydroxylation occurred from the third day. Optimum concentration of the substrate, which gave the maximum bioconversion efficiency, was 0.5 mg ml(-1) in one batch. The highest yield of the microbial products recorded in this work was achieved within the pH range 6.5-7.3 and at the temperature of 27 degrees C.

Efficient biotransformation of cholesterol to androsta-1,4-diene-3,17-dione by a newly isolated actinomycete Gordonia neofelifaecis

“…13 C NMR signals are shown inTable 1. These data, in addition to the reported values(Faramarzi et al 2006;Al-Aboudi et al 2008), confirmed the proposed structure of androsta-1, 4-diene-3 17-dione.Androst-4-ene-3,17-dione (VI) Colorless crystals (crystallized from ethyl acetate); mp 176-178°C, [a] D ? 183°( CHCl 3 , c = 1.0), lit(Johnson et al 1960); mp 171.5-172.5°C, [a] D ?…”

“…117°(CHCl 3 , c = 1.0), lit (Faramarzi et al 2006 Table 1. The same NMR data were also reported earlier (Nagasawa et al 1969;Lin et al 2009).…”

Fungal transformation of androsta-1,4-diene-3,17-dione by Aspergillus brasiliensis

“…Reduction of 17-carbonyl group of ADD has been reported previously by Mucor racemosus and Acremonium strictum and Cephalosporium aphidicola fermention [11,12]. 11α-hydroxyandrost-1,4-diene-3,17-dione (III) which is used in the preparation of anti-osteoporosis active compounds, has been previously obtained by ADD biotransformation in Cephalosporium aphidicola, Rhizopus arrhizus and Aspergillus ochraceus culture media [13,20,22].…”

Steroid dan Lignan dari Kayu Batang Durio oxleyanus (Malvaceae)

“…Androst-1,4-dien-3,7-dion (1), diperoleh berupa padatan putih dengan nilai [ ] 23 D +106,4 o (CHCl 3 ); literatur (Faramarzi, 2006)…”

“…Jenis senyawa steroid yang juga pernah diisolasi adalah β-sitosterol dan 3-β-hidroksi-21normetil-19-vinilidenilursan (Venkatesh et al, 2010) dari buah tumbuhan D. zibethinus. Senyawa 1 juga telah ditemukan dari beberapa tumbuhan seperti pada Scenedesmus quadricauda dan Acremonium strictum (DellaGreca, 1996;Faramarzi, 2006 (DellaGreca, 1996) c senyawa boldion dari Acremonium strictum (Faramarzi, M. A., 2006) 2) pada C 169,2 ppm (C-9"'), C 168,7 ppm (C-9), dan empat gugus metoksi pada C 56,7, 56,6, 56,5 dan 56,4 ppm. Berdasarkan data 1 H-NMR dan 13 C-NMR di atas dapat diketahui bahwa senyawa 2 adalah golongan lignan dengan nama boehmenan.…”