Production of Androgens by Microbial Transformation of Progesterone
            <i>in Vitro</i>
            : A Model for Androgen Production in Rivers Receiving Paper Mill Effluent

Jenkins, Ronald L.; Wilson, Elizabeth M.; Angus, Robert A.; Howell, W. Mike; Kirk, Marion; Moore, Ray; Nance, Marione; Brown, Amber N.

doi:10.1289/ehp.7161

Cited by 88 publications

(55 citation statements)

References 23 publications

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“…The biotransformation of the first two pathways happened at 17β position at ring-D. Progesterone was transformed via the first pathway into 17α-hydroxyproges- terone (17α-OHP), and subsequently into AED and ADD. This could be supported by the previous study of Jenkins et al, 38 who found the same transformation by bacteria. Based on previous studies about steroids biodegradation, 21,25,27,38,39 progesterone could be transformed into testosterone acetate (TAC) and four identified products (1−4) T, 17β-BOL, AED, and ADD via the second pathway, where these products could be converted to one another (Figure 4).…”

Section: ■ Results and Discussionsupporting

confidence: 83%

“…This could be supported by the previous study of Jenkins et al, 38 who found the same transformation by bacteria. Based on previous studies about steroids biodegradation, 21,25,27,38,39 progesterone could be transformed into testosterone acetate (TAC) and four identified products (1−4) T, 17β-BOL, AED, and ADD via the second pathway, where these products could be converted to one another (Figure 4). Compared with the residual progesterone in the media, the concentrations of these four detected steroids (products 1−4) by LC-MS/MS, 16 were very low (below 14 μg/L), reaching a peak at 5.7 h, then decreasing gradually (SI Figure S6), indicating that only a relatively low percentage of progesterone was degraded into these androgens, where they were also easily degraded under aerobic conditions.…”

Section: ■ Results and Discussionsupporting

confidence: 83%

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Degradation of Norgestrel by Bacteria from Activated Sludge: Comparison to Progesterone

Liu¹,

Ying²,

Yousheng³

et al. 2013

Environ. Sci. Technol.

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Natural and synthetic progestagens in the environment have become a concern due to their adverse effects on aquatic organisms. Laboratory studies were performed to investigate aerobic biodegradation of norgestrel by bacteria from activated sludge in comparison with progesterone, and to identify their degradation products and biotransformation pathways. The degradation of norgestrel followed first order reaction kinetics (T 1/2 = 12.5 d), while progesterone followed zero order reaction kinetics (T 1/2 = 4.3 h). Four and eight degradation products were identified for norgestrel and progesterone, respectively. Six norgestrel-degrading bacterial strains (Enterobacter ludwigii, Aeromonas hydrophila subsp. dhakensis, Pseudomonas monteilii, Comamonas testosteroni, Exiguobacterium acetylicum, and Chryseobacterium indologenes) and one progesterone-degrading bacterial strain (Comamonas testosteroni) were successfully isolated from the enrichment culture inoculated with aerobic activated sludge. To our best knowledge, this is the first report on the biodegradation products and degrading bacteria for norgestrel under aerobic conditions.

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Section: ■ Results and Discussionsupporting

confidence: 83%

Section: ■ Results and Discussionsupporting

confidence: 83%

Degradation of Norgestrel by Bacteria from Activated Sludge: Comparison to Progesterone

Liu¹,

Ying²,

Yousheng³

et al. 2013

Environ. Sci. Technol.

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“…Surface water and sediment samples were collected from the Liuxi, Shijing, and Zhujiang rivers of the Pearl River system in the dry season (December [17][18]2007) and the wet season (September [10][11][12]2008). In total, 15 sampling sites along the three rivers were selected (Fig.…”

Section: Sample Collection and Extractionmentioning

confidence: 99%

“…Male fish feminization in receiving waters has been related to residual natural and synthetic estrogens from municipal STP effluents [8,9]. Effluents from pulp and paper mills displayed androgenic activity in female fish, leading to masculinization or sex reversal of female fish [10,11]. Very recently, screening assays revealed that androgenic activity also exists widely in industrial and hospital wastewaters, municipal STP effluents, and even in surface water in association with estrogen, progesterone, and glucocorticoid receptor activities [12,13].…”

Section: Introductionmentioning

confidence: 99%

Screening of multiple hormonal activities in surface water and sediment from the Pearl River system, South China, using effect‐directed in vitro bioassays

Zhao

Ying

Yang

et al. 2011

Enviro Toxic and Chemistry

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Abstract-This paper reports screening of multiple hormonal activities (estrogenic and androgenic activities, antiestrogenic and antiandrogenic activities) for surface water and sediment from the Pearl River system (Liuxi, Zhujiang, and Shijing rivers) in South China, using in vitro recombinant yeast bioassays. The detection frequencies for estrogenic and antiandrogenic activities were both 100% in surface water and 81 and 93% in sediment, respectively. The levels of estrogenic activity were 0.23 to 324 ng 17b-estradiol equivalent concentration (EEQ)/L in surface water and 0 to 101 ng EEQ/g in sediment. Antiandrogenic activities were in the range of 20.4 to 935 Â 10 3 ng flutamide equivalent concentration (FEQ)/L in surface water and 0 to 154 Â 10 3 ng FEQ/g in sediment. Moreover, estrogenic activity and antiandrogenic activity in sediment showed good correlation (R 2 ¼ 0.7187), suggesting that the agonists of estrogen receptor and the antagonists of androgen receptor co-occurred in sediment. The detection frequencies for androgenic and antiestrogenic activities were 41 and 29% in surface water and 61 and 4% in sediment, respectively. The levels of androgenic activities were 0 to 45.4 ng dihydrotestosterone equivalent concentration (DEQ)/L in surface water, and the potency was very weak in the only detected sediment site. The levels of antiestrogenic activity were 0 to 1,296 Â 10 3 ng tamoxifen equivalent concentration (TEQ)/L in surface water and 0 to 89.5 Â 10 3 ng TEQ/g in sediment. The Shijing River displayed higher levels of hormonal activities than the Zhujiang and Liuxi rivers, indicating that the Shijing River had been suffering from heavy contamination with endocrine-disrupting chemicals. The equivalent concentrations of hormonal activities in some sites were greater than the lowest-observed-effect concentrations reported in the literature, suggesting potential adverse effects on aquatic organisms. Environ.

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“…More recently, the androgenic and antiandrogenic activities of chemicals have been described in association with paper and pulp mill effluents (Svenson and Allard, 2004), rivers (Thomas et al, 2002), and effluents from wastewater treatment plants (Blankvoort et al, 2005). While androgenic activity in rivers may be a partial result of microbial degradation of phytosterols to progesterone and then to androgens (Jenkins et al, 2004), anti-androgenic activity is derived from anthropogenic chemicals (Sumpter, 2005). Naturally occurring reproductive hormones such as 17b-estradiol, testosterone, and their metabolites are commonly detected in sewage treatment works (STW) effluents (Desbrow et al, 1998).…”

Section: Introductionmentioning

confidence: 99%

Acute and chronic effects of testosterone and 4-hydroxyandrostenedione to the crustacean Daphnia magna

Barbosa

Nogueira

Soares

2008

Ecotoxicology and Environmental Safety

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a b s t r a c tSteroid compounds have been globally detected in surface waters. The ecological impacts of these biologically active chemicals are largely unknown. Toxicity of testosterone and 4-hydroxyandrostenedione was assessed for the freshwater cladoceran Daphnia magna. Acute toxicity tests showed that 6.20 mg L À1 of testosterone, the highest concentration tested, did not have effect on the daphnids, whereas 4-hydroxyandrostenedione had an EC 50 of 4.26 mg L À1 . Chronic toxicity tests were carried out using survival, body length, fecundity, and fertility as endpoints. Long-term testosterone exposure reduced D. magna fecundity and fertility at concentrations ranging from 0.31 to 2.48 mg L À1 . The significant decrease in fecundity was associated with an increase in aborted eggs. Long-term 4-hydroxyandrostenedione exposure at 0.84 mg L À1 increased the mortality of the neonates. The chronic toxicity effects were observed at concentrations higher than the measured environmental concentrations of these compounds. Nevertheless, the reproductive impairment of the daphnids is likely to occur at environmental levels as an ultimate response to long-term exposure.

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Production of Androgens by Microbial Transformation of Progesterone in Vitro : A Model for Androgen Production in Rivers Receiving Paper Mill Effluent

Cited by 88 publications

References 23 publications

Degradation of Norgestrel by Bacteria from Activated Sludge: Comparison to Progesterone

Degradation of Norgestrel by Bacteria from Activated Sludge: Comparison to Progesterone

Screening of multiple hormonal activities in surface water and sediment from the Pearl River system, South China, using effect‐directed in vitro bioassays

Acute and chronic effects of testosterone and 4-hydroxyandrostenedione to the crustacean Daphnia magna

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