Retroconversion of estrogens into androgens by bacteria via a cobalamin-mediated methylation

Wang, Po Hsiang; Chen, Yi Lung; Wei, Sean Ting Shyang; Wu, Kan; Lee, Tzong‐Huei; Wu, Tien Yu; Chiang, Yin-Ru

doi:10.1073/pnas.1914380117

Cited by 49 publications

(43 citation statements)

References 63 publications

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“…Moreover, recent discoveries of steroid degraders in eukaryotic hosts (Ding et al , ; Holert et al , ) suggest a bidirectional interaction between steroid degraders and their eukaryotic hosts. The discovery of cobalamin auxotrophy in many steroid‐degrading anaerobes (Wei et al , ; Wang et al , ) indicates cobalamin cross‐feedings within microbial communities. These findings may also offer another avenue for future studies.…”

Section: Challenges and Future Perspectivesmentioning

confidence: 99%

Microbial degradation of steroid sex hormones: implications for environmental and ecological studies

Chiang

Wei

Wang

et al. 2019

Microbial Biotechnology

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Steroid hormones modulate development, reproduction and communication in eukaryotes. The widespread occurrence and persistence of steroid hormones have attracted public attention due to their endocrine-disrupting effects on both wildlife and human beings. Bacteria are responsible for mineralizing steroids from the biosphere. Aerobic degradation of steroid hormones relies on O 2 as a co-substrate of oxygenases to activate and to cleave the recalcitrant steroidal core ring. To date, two oxygen-dependent degradation pathwaysthe 9,10-seco pathway for androgens and the 4,5-seco pathways for oestrogens have been characterized. Under anaerobic conditions, denitrifying bacteria adopt the 2,3-seco pathway to degrade different steroid structures. Recent meta-omics revealed that microorganisms able to degrade steroids are highly diverse and ubiquitous in different ecosystems. This review also summarizes culture-independent approaches using the characteristic metabolites and catabolic genes to monitor steroid biodegradation in various ecosystems.

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Section: Challenges and Future Perspectivesmentioning

confidence: 99%

Microbial degradation of steroid sex hormones: implications for environmental and ecological studies

Chiang

Wei

Wang

et al. 2019

Microbial Biotechnology

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“…Wang et al [ 51 ] described the estradiol degradation strategy that is based on the conversion of estrogens to androgens and the subsequent degradation by the anaerobic 2,3-seco pathway. Denitratisoma sp.…”

Section: Microbiological Degradation Of Edcsmentioning

confidence: 99%

“…strain DHT3 converts estrogens into androgens through the cobalamin-dependent methylation of estrogen, including the formation of a nucleophilic carboanion at C-10 on the phenolic A-ring. Androgenic intermediates are catabolized to 9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid (HIP) [ 51 , 52 ].…”

Section: Microbiological Degradation Of Edcsmentioning

confidence: 99%

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Suitability of Immobilized Systems for Microbiological Degradation of Endocrine Disrupting Compounds

Wojcieszyńska

Marchlewicz

2020

Molecules

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The rising pollution of the environment with endocrine disrupting compounds has increased interest in searching for new, effective bioremediation methods. Particular attention is paid to the search for microorganisms with high degradation potential and the possibility of their use in the degradation of endocrine disrupting compounds. Increasingly, immobilized microorganisms or enzymes are used in biodegradation systems. This review presents the main sources of endocrine disrupting compounds and identifies the risks associated with their presence in the environment. The main pathways of degradation of these compounds by microorganisms are also presented. The last part is devoted to an overview of the immobilization methods used for the purposes of enabling the use of biocatalysts in environmental bioremediation.

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“…Mineralization of natural estrogens is only accomplished by microorganisms (Thayanukul et al, 2010;Chen et al, 2017 andWang et al, 2020;Chiang et al, 2020). Complete estrogen mineralization by bacteria was first described by Coombe et al (1966) in actinobacterium Nocardia sp.…”

Section: Introductionmentioning

confidence: 99%

Genetic and metabolite biomarkers reveal actinobacteria-mediated estrogen biodegradation in urban estuarine sediment

Hsiao

Chen

Meng

et al. 2020

Preprint

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Steroidal estrogens are often accumulated in urban estuarine sediments worldwide at microgram per gram levels. These aromatic steroids have been classified as endocrine disruptors with an EC50 at sub-nanomolar concentrations and classified as Group 1 carcinogens by the World Health Organization. Microbial degradation is a naturally occurring mechanism that mineralizes estrogens in the biosphere; however, the corresponding genes in estrogen-degrading actinobacteria remain unidentified. In this study, we identified a gene cluster encoding several putative estrogen-degrading genes in actinobacterium Rhodococcus sp. strain B50. Among them, the oecB and oecC genes involved in estrogenic A-ring cleavage were identified through gene-disruption experiments. We also detected the accumulation of two extracellular estrogenic metabolites, including pyridinestrone acid (PEA) and 3aα-H-4α(3’-propanoate)-7aβ-methylhexahydro-1,5-indanedione (HIP), in the estrone-fed strain B50 cultures. Since actinobacterial oecC and proteobacterial oecC shared less than 40% sequence identity, oecC could serve as a specific biomarker to differentiate the contribution of actinobacteria and proteobacteria in environmental estrogen degradation. Therefore, oecC and the extracellular metabolites PEA and HIP were used as biomarkers to investigate estrogen biodegradation in an urban estuarine sediment. Interestingly, our data suggested that actinobacteria, rather than alpha-proteobacteria function in sewage treatment plants, are actively degrading estrogens in the urban estuarine sediment.Graphical AbstractHighlightsIsolation of an estrogen-degrading actinobacterium Rhodococcus sp. strain B50 and establishment of a strain B50 genetic manipulation system.Strain B50 exhibits a two-fold estrogen degradation rate of that of estrogen-degrading alpha-proteobacteria under the same cultivation conditions.Functional characterization of two oxygenase genes, oecB and oecC, involved in estrogenic A-ring cleavage in actinobacteria.Identification of two extracellular estrogenic metabolites, PEA and HIP, in the estrone-fed strain B50 cultures.Detection of actinobacterial oecC sequences as well as PEA and HIP in the estrone-spiked urban estuarine sediments.

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Retroconversion of estrogens into androgens by bacteria via a cobalamin-mediated methylation

Cited by 49 publications

References 63 publications

Microbial degradation of steroid sex hormones: implications for environmental and ecological studies

Microbial degradation of steroid sex hormones: implications for environmental and ecological studies

Suitability of Immobilized Systems for Microbiological Degradation of Endocrine Disrupting Compounds

Genetic and metabolite biomarkers reveal actinobacteria-mediated estrogen biodegradation in urban estuarine sediment

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