Microbiological hydroxylation of androst-1,4-dien-3,17-dione by Neurospora crassa

Faramarzi, Mohammad Ali, Hajarolasvadi, Naghmeh, Yazdi, Mojtaba Tabatabaei, Amini, Mohsen and Aghelnejad, Maryam (2007) Microbiological hydroxylation of androst-1,4-dien-3,17-dione by Neurospora crassa. Biocatalysis and Biotransformation, 25 1: 72-78. doi:10.1080/10242420600893850


Author Faramarzi, Mohammad Ali
Hajarolasvadi, Naghmeh
Yazdi, Mojtaba Tabatabaei
Amini, Mohsen
Aghelnejad, Maryam
Title Microbiological hydroxylation of androst-1,4-dien-3,17-dione by Neurospora crassa
Formatted title
Microbiological hydroxylation of androst-1,4-dien-3,17-dione by Neurospora crassa
Journal name Biocatalysis and Biotransformation   Check publisher's open access policy
ISSN 1024-2422
1029-2446
Publication date 2007-01
Sub-type Article (original research)
DOI 10.1080/10242420600893850
Volume 25
Issue 1
Start page 72
End page 78
Total pages 7
Place of publication London, United Kingdom
Publisher Informa Healthcare
Language eng
Formatted abstract
Nine hydroxy-derived androstadiene compounds were isolated from the fermentation broth of Neurospora crassa when incubated in the presence of androst-1,4-dien-3,17-dione (ADD; I) for 7 days. Hydroxylations at 6β, 7β, 11α, 14α- positions and 17-carbonyl reduction of the substrate were the characteristics observed in this biotransformation. Their structures were determined by spectroscopic methods as 17β-hydroxyandrost-1,4-dien-3-one (II), 14α-hydroxyandrost-1,4-dien-3,17-dione (III), 6β-hydroxyandrost-1,4-dien-3,17-dione (IV), 11α-hydroxyandrost-1,4-dien-3,17-dione (V), 6β,17β-dihydroxyandrost-1,4-dien-3-one (VI), 7β-hydroxyandrost-1,4-dien-3,17-dione (VII), 14α,17β-dihydroxyandrost-1,4-dien-3-one (VIII), 6β,14α-dihydroxyandrost-1,4-dien-3,17-dione (IX), and 11α,17β-dihydroxyandrost-1,4-dien-3-one (X). A new steroid substance, 6β,14α-dihydroxyandrost-1,4-dien-3,17-dione (IX), was also characterized during this study. The best fermentation condition was found to be 7-day incubation at 25°C and pH values of 5.0–6.0 in the presence of 0.05 g 100 mL−1 of the substrate. At a concentration above 0.075 g 100 mL−1, the biotransformation was completely inhibited.

Keyword Androst-1,4-dien-3,17-dione
Biotransformation
Microbial hydroxylation
Neurospora crassa
Steroid
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ
Additional Notes Published January-February 2007.

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Pharmacy Publications
 
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