title: Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa.
abstract: Microbial transformation of androst-4-en-3,17-dione (AD; I) using Neurospora crassa afforded six metabolites; 6beta,14alpha-dihydroxyandrost-4-en-3,17-dione (II), 6beta,9alpha-dihydroxyandrost-4-en-3,17-dione (III), 7alpha-hydroxyandrost-4-en-3,17-dione (IV), 9alpha-hydroxyandrost-4-en-3,17-dione (V), 14alpha-hydroxyandrost-4-en-3,17-dione (VI), and androst-4,6-dien-3,17-dione (VII). The steroid products were assigned by interpretation of their spectral data such as (1)H NMR, (13)C NMR, FTIR, and mass spectroscopy. The characteristic transformations observed were C-6beta, C-7alpha, C-9alpha, C-14alpha hydroxylations, and C6-C7 dehydrogenation. The best fermentation condition was found to be 6-day incubation at 25 degrees C and pH value of 5.0-6.5 according to TLC profiles. Time course study showed the accumulation of V and VI from the third day and IV from the fourth day of the fermentation. Optimum concentration of the substrate, which gave maximum bioconversion efficiency, was 3.5mM in one batch. Biotransformation was completely inhibited in a concentration above 7.0mM.
authors.affiliation: Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Medical Sciences/University of Tehran, Tehran 14174, Iran.
authors.forename: Mohammad Ali
authors.initials: MA
authors.lastname: Faramarzi
authors.forename: Maryam
authors.initials: M
authors.lastname: Aghelnejad
authors.forename: Mojtaba
authors.initials: M
authors.lastname: Tabatabaei Yazdi
authors.forename: Mohsen
authors.initials: M
authors.lastname: Amini
authors.forename: Naghmeh
authors.initials: N
authors.lastname: Hajarolasvadi
mesh_terms: D000735:Androstenedione / Q000737:chemistry / Q000378:metabolism*; D001711:Biotransformation; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D009492:Neurospora crassa / Q000378:metabolism*; D013696:Temperature
chemical_list: D000735:Androstenedione