Anoxic androgen degradation by the denitrifying bacterium Sterolibacterium denitrificans via the 2,3-seco pathway

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Title:	Anoxic androgen degradation by the denitrifying bacterium Sterolibacterium denitrificans via the 2,3-seco pathway
Authors:	王柏翔;Wang, Po-Hsiang;Yu, Chang-Ping;Lee, Tzong-Huei;Lin, Ching-Wen;Ismail, Wael;Wey, Shiaw-Pyng;Kuo, An-Ti;Chiang, Yin-Ru
Contributors:	工學院環境工程研究所
Keywords:	Anaerobiosis;Androgens;Androgens - metabolism;Anoxic conditions;Bacteria;Biodegradation;Biosensing Techniques - methods;Biotransformation;Carbon Isotopes - metabolism;Isotope Labeling;Metabolic Networks and Pathways;Metabolomics;Microbiology;Rhodocyclaceae - metabolism;Time Factors;Yeasts
Date:	2014-01-01
Issue Date:	2026-04-23 14:59:05 (UTC+8)
Publisher:	American Society for Microbiology;United States: American Society for Microbiology
Abstract:	摘要： The biodegradation of steroids is a crucial biochemical process mediated exclusively by bacteria. So far, information concerning the anoxic catabolic pathways of androgens is largely unknown, which has prevented many environmental investigations. In this work, we show that Sterolibacterium denitrificans DSMZ 13999 can anaerobically mineralize testosterone and some C 19 androgens. By using a 13 C-metabolomics approach and monitoring the sequential appearance of the intermediates, we demonstrated that S. denitrificans uses the 2,3- seco pathway to degrade testosterone under anoxic conditions. Furthermore, based on the identification of a C 17 intermediate, we propose that the A-ring cleavage may be followed by the removal of a C 2 side chain at C-5 of 17-hydroxy-1-oxo-2,3- seco -androstan-3-oic acid (the A-ring cleavage product) via retro-aldol reaction. The androgenic activities of the bacterial culture and the identified intermediates were assessed using the lacZ -based yeast androgen assay. The androgenic activity in the testosterone-grown S. denitrificans culture decreased significantly over time, indicating its ability to eliminate androgens. The A-ring cleavage intermediate (≤500 μM) did not exhibit androgenic activity, whereas the sterane-containing intermediates did. So far, only two androgen-degrading anaerobes ( Sterolibacterium denitrificans DSMZ 13999 [a betaproteobacterium] and Steroidobacter denitrificans DSMZ 18526 [a gammaproteobacterium]) have been isolated and characterized, and both of them use the 2,3- seco pathway to anaerobically degrade androgens. The key intermediate 2,3- seco -androstan-3-oic acid can be used as a signature intermediate for culture-independent environmental investigations of anaerobic degradation of C 19 androgens. 其他題名： Appl Environ Microbiol 出版者： United States: American Society for Microbiology 出版日期： 2014-06-01 出處： Applied and Environmental Microbiology, 2014-06, Vol.80 (11), p.3442-3452 版權： Copyright American Society for Microbiology Jun 2014 版權： Copyright © 2014, American Society for Microbiology. All Rights Reserved. 2014 American Society for Microbiology 識別號： ISSN: 0099-2240 識別號： ISSN: 1098-5336 識別號： ISSN: 1070-6291 識別號： EISSN: 1098-5336 識別號： EISSN: 1098-6596 識別號： DOI: 10.1128/AEM.03880-13 識別號： PMID: 24657867 識別號： CODEN: AEMIDF
Appears in Collections:	[Graduate Institute of Environmental Engineering ] journal & Dissertation

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