Microbial transformation of oral contraceptive ethisterone by Aspergillus niger and Cunninghamella blakesleeana.
Aspergillus niger
Biotransformation
Cunninghamella blakesleeana
Estrogen
Ethisterone
Oral contraceptive
Journal
Steroids
ISSN: 1878-5867
Titre abrégé: Steroids
Pays: United States
ID NLM: 0404536
Informations de publication
Date de publication:
02 2020
02 2020
Historique:
received:
13
04
2019
revised:
20
07
2019
accepted:
01
08
2019
pubmed:
11
8
2019
medline:
12
1
2021
entrez:
11
8
2019
Statut:
ppublish
Résumé
Ethisterone (17α-ethynyl-17β-hydroxyandrost-4-en-3-one) (1) is a synthetic steroidal estrogen. It is extensively used as an oral contraceptive. The current study involves the structural transformation of ethisterone (1) by Aspergillus niger, and Cunninghamella blakesleeana. Fermentation of 1 with C. blakesleeana afforded two new polar metabolites, 17α-ethynyl-6β,15β,17β-trihydroxyandrost-4-en-3-one, and 17α-ethynyl-7β,15β,17β-trihydroxyandrost-4-en-3-one, while transformation of ethisterone with A. niger yielded a new metabolite, 17α-ethynyl-6α,17β-dihydroxyandrost-4-en-3-one, along with a known metabolite, 17α-ethynyl-11α,17β-dihydroxyandrost-4-en-3-one. Modern spectroscopic techniques were used to characterize the structures of all transformed products.
Identifiants
pubmed: 31400394
pii: S0039-128X(19)30157-6
doi: 10.1016/j.steroids.2019.108467
pii:
doi:
Substances chimiques
Contraceptives, Oral
0
Ethisterone
P201BVY1MJ
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
108467Informations de copyright
Copyright © 2019 Elsevier Inc. All rights reserved.