Bacterial metabolism of natural and synthetic sex hormones undergoing enterohepatic circulation
Abstract
Steroids undergoing enterohepatic circulation are exposed to bacterial metabolism particularly by obligate anaerobes which account for 99.99% of the fecal flora. The most common transformation is hydrolysis of conjugated steroids. The glucuronidases are synthesized by Escherichia coli and Bacteroides species. The bacterial catabolism of unconjugated steroids may be considered under several headings: 1. Reduction of ring-A due to clostridia species synthesizing specific enzymes; C. paraputrificum, 3 alpha,5 beta-reductase; C. innocuum, 3 beta,5 beta-reductase; and a new species C.J-1, 3 beta,5 alpha-reductase. 2. Reduction of the delta 5 bond by human fecal flora. The specific strain(s) synthesizing the enzyme have not yet been identified. 3. Reduction of 17-keto estrogens by the above mentioned ring-A reducing clostridia and by Eubacterium lentum. 4. Reduction of 17-keto androstenes by Bacteroides fragilis. 5. Desmolase mediated side chain cleavage at C17-C20 position of 17 alpha-hydroxysteroids by two new species Clostridium scindens and Eubacterium desmolans isolated from human and cat fecal flora respectively and by Clostridium cadavaris isolated from New York City sewage. 6. And 16 alpha- and 21-dehydroxylase by E. lentum a normal inhabitant of the human gut; it is the only organism known to synthesize 16 alpha- or 21-dehydroxylases. Due to the high specificity of the enzymes and the simplicity of extracting the metabolites, biosynthesis of reference compounds and radioimmunoassay reagents is practical and inexpensive. The enzymes can also be used for titration of specific bacterial strains in fecal flora and as markers for bacterial identification in particular for the strains difficult to be defined by regular biochemical reactions.
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Reactions catalyzed by different strains of gut bacteria include A-ring reduction, reduction of the Δ5-double bond, reduction of 17-keto estrogens and 17-keto androstenes, 17,20-cleavage of 17α-hydroxysteroids, and 16α- and 21-dehydroxylation.
“Reactions catalyzed by different strains of gut bacteria include (1) A-ring reduction, (2) reduction of the Δ5-double bond, (3) reduction of 17-keto estrogens and 17-keto androstenes, (4) 17,20-cleavage of 17α-hydroxysteroids, and (5) 16α- and 21-dehydroxylation”
From Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: a comprehensive review (2019) · cites this paper as [148]
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- Authors
- Winter, J., & Bokkenheuser, V. D.
- Affiliations
- St. Luke's-Roosevelt Hospital Center (US)
- Venue
- Journal of Steroid Biochemistry
- Publisher
- Elsevier BV
- Published
- 1987
- Volume
- 27
- Issue
- 4-6
- Pages
- 1145-1149
- ISSN
- 0022-4731 (ISSN-L)
- OpenAlex
- W2017969439
- Cited by
- 50
- References
- 21
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 3 · 2023: 1 · 2022: 2 · 2021: 3 · 2020: 2 · 2019: 1 · 2018: 1 · 2017: 2 · 2015: 4 · 2014: 1 · 2013: 1 · 2012: 3
- FWCI
- 0.00
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Steroid Biochemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Gut microbiota and health
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Keywords
- enterohepatic circulation, sex hormones, fecal microbiota, glucuronidase, Escherichia coli, Bacteroides, Clostridium
- MeSH terms
- Enterobacteriaceae, Enterohepatic Circulation, Humans, Lyases, Oxidation-Reduction, Oxidoreductases, Gonadal Steroid Hormones, 17-Ketosteroids
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