Production of malodorous steroids from androsta-5,16-dienes and androsta-4,16-dienes by Corynebacteria and other human axillary bacteria

• Published in: The Journal of steroid biochemistry and molecular biology 2003-12, Vol.87 (4), p.327-336
• Main Authors: Decréau, Richard A, Marson, Charles M, Smith, Kelvin E, Behan, John M
• Format: Article
• Language: English
• Subjects: Actinomycetales - genetics; Actinomycetales - isolation & purification; Actinomycetales - metabolism; Anaerobiosis; Androstadienes - chemistry; Androstadienes - metabolism; Androstadienones; Androstenols - chemistry; Androstenols - metabolism; Axilla - microbiology; Biological and medical sciences; Biotransformation; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Corynebacteria; Corynebacterium; Culture Media; Fundamental and applied biological sciences. Psychology; Humans; Micrococcus; Odorants; Oxidation-Reduction; Species Specificity; Stereoisomerism; Steroids; Steroids - biosynthesis; Steroids - chemistry; Time Factors; Vertebrates: endocrinology
• ISSN: 0960-0760; 1879-1220
• DOI: 10.1016/j.jsbmb.2003.09.005

The biotransformations of a number of steroids, chiefly 5,6,16,17-tetradehydro-androstanes, are reported. The strains investigated were Corynebacteria sp. G38, G40, G41, B, Brevis sp. CW5 and Micrococcus sp. M-DH2. Corynebacterium sp. G41 proved remarkably efficient in effecting oxidative isomerisation of 5-ene-3-sterols into the corresponding 4-en-3-ones. The main biochemical reactions involved were oxidation at C-3; no reduction processes were observed. Conversions of 3β-sterols into the C-3 oxo-steroids were high, but were correspondingly low for the 3α-sterol epimers. Androsta-4,16-dien-3-one and 5β-androsta-16-en-3-one are crucial to the formation of malodour. The rate of formation of these compounds was measured over 72 h incubation periods using three substrates: androsta-5,16-dien-3β-ol, androsta-4,16-dien-3β-ol and androsta-5,16-dien-3-one. Induction studies of the transformation of the androsta-5,16-dien-3β-ol into the very odorous compound androsta-4,16-dien-3-one showed that cells incubated with a mixture of antibiotics displayed the same extent of biotransformation as normal cells if the concentration of antibiotic was low (1, 3, 5 and 7 μg/ml), although at concentrations higher than 10 μg/ml, biotransformation yields were reduced. Pre-incubation with a 3β-fluoro-steroid inhibited the formation of the odorous androsta-4,16-dien-3-one.