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

Po Hsiang Wang, Chang Ping Yu, Zong-Huei Li, Ching Wen Lin, Wael Ismail, Shiaw Pyng Wey, An Ti Kuo, Yin Ru Chiang

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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 C19 androgens. By using a 13C-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 C17 intermediate, we propose that the A-ring cleavage may be followed by the removal of a C2 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 C19 androgens.

Original languageEnglish
Pages (from-to)3442-3452
Number of pages11
JournalApplied and Environmental Microbiology
Volume80
Issue number11
DOIs
Publication statusPublished - 2014

Fingerprint

Sterolibacterium denitrificans
denitrifying bacteria
androgen
androgens
Androgens
Bacteria
degradation
bacterium
testosterone
cleavage
Testosterone
Biochemical Phenomena
Betaproteobacteria
Gammaproteobacteria
beta-Proteobacteria
Acids
Metabolomics
anaerobes
acids
acid

ASJC Scopus subject areas

  • Applied Microbiology and Biotechnology
  • Food Science
  • Biotechnology
  • Ecology

Cite this

Anoxic androgen degradation by the denitrifying bacterium Sterolibacterium denitrificans via the 2,3-seco pathway. / Wang, Po Hsiang; Yu, Chang Ping; Li, Zong-Huei; Lin, Ching Wen; Ismail, Wael; Wey, Shiaw Pyng; Kuo, An Ti; Chiang, Yin Ru.

In: Applied and Environmental Microbiology, Vol. 80, No. 11, 2014, p. 3442-3452.

Research output: Contribution to journalArticle

Wang, Po Hsiang ; Yu, Chang Ping ; Li, Zong-Huei ; Lin, Ching Wen ; Ismail, Wael ; Wey, Shiaw Pyng ; Kuo, An Ti ; Chiang, Yin Ru. / Anoxic androgen degradation by the denitrifying bacterium Sterolibacterium denitrificans via the 2,3-seco pathway. In: Applied and Environmental Microbiology. 2014 ; Vol. 80, No. 11. pp. 3442-3452.
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