Isaria fumosorosea KCh J2 entomopathogenic strain as an effective biocatalyst for steroid compound transformations
Ewa Kozłowska , Monika Dymarska , Edyta Kostrzewa-Susłow , Tomasz Janeczko
The catalytic activity of enzymes produced by an entomopathogenic filamentous fungus (Isaria fumosorosea KCh J2) towards selected steroid compounds (androstenedione, adrenosterone, progesterone, 17α-methyltestosterone and dehydroepiandrosterone) was investigated. All tested substrates were efficiently transformed. The structure of the substrate has a crucial impact on regio- and stereoselectivity of hydroxylation since it affects binding to the active site of the enzyme. Androstenedione was hydroxylated in the 7α-position to give a key intermediate in the synthesis of the diuretic-7α-hydroxyandrost-4-ene-3,17-dione with 82% conversion. Adrenosterone and 17α-methyltestosterone were hydroxylated in the 6β-position. Hydroxylated derivatives such as 15β-hydroxy-17α-methyltestosterone and 6β,12β-dihydroxy-17α-methyltestosterone were also observed. In the culture of Isaria fumosorosea KCh J2, DHEA was effectively hydroxylated in the C-7 position and then oxidized to give 7-oxo-DHEA, 3β,7α- and 3β,7β-dihydroxy-17a-oxa-D-homo-androst-5-ene-17-one. We obtained 7β-OH-DHEA lactone with 82% yield during 3 days transformation of highly concentrated (5 g/L) DHEA.
|Journal series||Molecules, ISSN 1420-3049, (A 30 pkt)|
|Publication size in sheets||0.65|
|Keywords in English||Biotransformation, Dehydroepiandrosterone, DHEA, Isaria fumosorosea, Steroid lactones|
|Internal identifier||64659; PX-5a5f2520d5defae3633fbc5e|
|License||Journal (articles only); author's final; ; with publication|
|Score||= 30.0, 09-09-2020, ArticleFromJournal|
|Publication indicators||= 10; = 8; : 2017 = 1.146; : 2017 = 3.098 (2) - 2017=3.268 (5)|
|Citation count*||12 (2020-07-08)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.