Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C, Tehran, Iran.
Department of Chemistry, Ilam Branch, Islamic Azad University, Ilam, Iran.
Biotechnol Lett. 2020 Sep;42(9):1767-1775. doi: 10.1007/s10529-020-02902-4. Epub 2020 May 2.
The ability of five fungal species belonging to two genera of Aspergillus and Fusarium has been examined in the microbial transformation of androst-4-ene-3, 17-dione (AD). Furthermore, the biotransformation of nandrolone decanoate (2) by F. fujikuroi has been studied. AD (1) was converted by cultures of Aspergillus sp. PTCC 5266 to form 11α-hydroxy-AD (3) as the only product, with a yield of 86% in 3 days. Moreover, two hydroxylated metabolites 11α-hydroxy-AD (3, 65%) and 7β-hydroxy-AD (4; 18%) were isolated in biotransformation of AD by A. nidulans. On the other hand, it was metabolized by F. oxysporum to produce 14α-hydroxy-AD (5; 38%) and testosterone (6; 12%). Microbial transformation of AD by F. solani led to the production of 11α-hydroxy-AD (3; 54%) and testosterone (6; 14%). AD was reduced at the 17-position by F. fujikuroi to produce testosterone in the yield of 42%. Finally, nandrolone decanoate was transformed by F. fujikuroi via hydrolysis and oxidation at the 17-position to produce two metabolites namely 17β-hydroxyestr-4-en-3-one (7, 25.4%) and estr-4-en-3,17-dione (8, 33%), respectively. The all metabolites were purified and subsequently identified based on their spectra data analysis and comparing them to the literature data.
五种真菌物种的能力属于两个属的曲霉和镰刀菌已检查在微生物转化和雄甾-4-烯-3,17-二酮（广告）。此外，癸酸诺龙（2）的生物转化由藤仓镰刀菌进行了研究。广告（1）被培养物转化为曲霉菌 PTCC 5266形成 11α-羟基-广告（3）作为唯一的产物，在 3 天内产率为 86%。此外，两个羟化代谢物 11α-羟基-广告（3,65%）和 7β-羟基-广告（4;18%）在生物转化中分离出的广告由 A. nidulans。另一方面，它被 F. oxysporum代谢生成 14α-羟基-广告（5;38%）和睾丸激素（6;12%）。广告的微生物转化由 F. solani导致产生 11α-羟基-广告（3;54%）和睾丸激素（6;14%）。广告在 17-位置由 F. fujikuroi还原生成睾丸激素，产率为 42%。最后，癸酸诺龙被藤仓镰刀菌通过水解和氧化在 17-位置转化为两种代谢物，即 17β-羟基雌甾-4-烯-3-酮（7,25.4%）和雌甾-4-烯-3,17-二酮（8,33%）。所有代谢物均经纯化，并根据其谱数据分析进行鉴定，并与文献数据进行比较。
