Microbial Degradation of Sterols

Marsheck, William J.; Kraychy, Stephen; Muir, R. D.

doi:10.1128/aem.23.1.72-77.1972

Cited by 142 publications

(38 citation statements)

References 3 publications

(3 reference statements)

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“…The ability of phytosteroids, such as ␤-sitosterol from pine tree bark, to alter the reproductive endocrine status of goldfish [17] and data correlating the presence of androstenedione with abnormal masculinization of mosquitofish [7,9] were consistent with the hypothesis that phytosteroids serve as the primary precursors for microbes to produce progesterone and the biologically active androgens [9]. Figure 4 illustrates the bioconversion pathway of ␤-sitosterol in paper mill effluent to progesterone, androstenedione, and androstadienedione [18][19][20][21]. Paper mill effluent is rich in ␤-sitosterol, with concentrations ranging from 71 to 535 g/L of ␤-sitosterol among different Canadian paper mills (Cook DL et al, National Council for Air and Stream Improvement, Corrallis, OR, USA, unpublished data), compared with 49 g/L of progesterone measured in Fenholloway River sediment.…”

Section: Discussionsupporting

confidence: 56%

Naturally occurring progesterone in loblolly pine (Pinus taeda L.): A major steroid precursor of environmental androgens

Carson

Jenkins

Wilson

et al. 2008

Enviro Toxic and Chemistry

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Progesterone, androstenedione, and androstadienedione were previously identified in the water and sediment of the Fenholloway River (Taylor County, FL, USA), a river that contains populations of masculinized female mosquitofish downstream of a paper mill, at levels higher than those in the nearby Spring Creek. Plant sterols, such as beta-sitosterol in mill effluent derived from pine tree pulp, were suggested to be metabolized by bacteria to progesterone and androgens to account for the masculinization phenomenon. The current study made use of standard solid-phase methanol extraction procedures, high-performance liquid chromatography, liquid chromatography-mass spectrometry, and a cell-based, androgen-receptor transcription assay to determine naturally occurring progesterone levels in mature pine trees. Progesterone concentrations in the loblolly pine (Pinus taeda L.) were 49.34 +/- 4.1 nmol/g dry mature wood (15.5 +/- 1.29 microg/g), 12.26 +/- 1.78 nmol/g pine needles (3.85 +/- 0.56 microg/g), and 3.81 +/- 0.36 nmol/g pine bark (1.19 +/- 0.11 mug/g). The results suggest that naturally occurring progesterone from pine wood pulp contributes to increased progesterone levels downstream of paper mill effluent discharges and may serve as the natural steroid precursor for environmental androgen production that causes masculinization of female mosquitofish.

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Section: Discussionsupporting

confidence: 56%

Naturally occurring progesterone in loblolly pine (Pinus taeda L.): A major steroid precursor of environmental androgens

Carson

Jenkins

Wilson

et al. 2008

Enviro Toxic and Chemistry

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“…The abundant phytosterols found in pine-tree tall oils, such as ␤-sitosterol, campesterol, and stigmastanol [32], contain steroid rings and could potentially be modified into compounds with androgenic activity. For example, a common bacterium, Mycobacterium sp., has been shown to metabolize phytosterols and tall oils to androstadienedione and androstenedione [33,34]. Mycobacterium smegmatis has metabolized plant sterols to unidentified compounds that masculinized mosquitofish [35,36], and Escherichia coli has metabolized cholesterol to androstadienedione and androstenedione [37].…”

Section: Discussionmentioning

confidence: 99%

Identification of Androstenedione in a River Containing Paper Mill Effluent

Jenkins

Angus

McNatt

et al. 2001

Environ Toxicol Chem

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Effluent from a paper mill discharging into the Fenholloway River, Taylor County, Florida, USA, contains chemicals that masculinize females of the resident population of eastern mosquitofish (Gambusia holbrooki), as evidenced in females by elongated anal fins, which is normally a male-specific trait. To identify androgenic components in the effluent, water collected from the Fenholloway River and a control tributary was fractionated using solid-phase extraction and reverse-phase high-performance-liquid chromatography. Two Fenholloway River fractions induced androgen receptor-dependent transcriptional activity in transient transfection cell culture assays. Of these, androstenedione was confirmed by liquid chromatography-mass spectrometry with multiple reaction monitoring.

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“…Masculinization of wild female fish has been attributed to sterols that are found in many plants, especially in the resin fraction of conifers [32]. These plant sterols can be broken down by microorganisms to produce androgenic steroids [35], which can induce fish masculinization under laboratory conditions [32] and in the wild [36]. The SLR drains numerous rivers heavily polluted by pulp and paper mill effluents, which could be sources of plant sterols.…”

Section: Gonadal Lesionsmentioning

confidence: 99%

Health of Lake Whitefish (Coregonus Clupeaformis) With Elevated Tissue Levels of Environmental Contaminants

Mikaelian¹,

Lafontaine²,

Harshbarger³

et al. 2002

Environ Toxicol Chem

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Lake whitefish (Coregonus clupeaformis) were collected in 1996 from the St. Lawrence River, Quebec, Canada. Histologic examination was performed on major organs of 497 specimens and on the liver of 48 additional individuals. Preneoplastic and neoplastic hepatic changes consisted of vacuolated cell (n = 65), clear cell (n = 17), and acidophilic (n = 16) foci of altered hepatocyte, hepatocellular carcinoma (n = 12), cholangioma (n = 5), and cholangiocarcinoma (n = 28). Six fish were intersexes (1.2%), and 11.7% of the ovaries (26/223) had ducts containing spermatogonia or more differentiated cells of the male germ cell line. Asynchronous nodular maturation of the testes was present in 8.2% of the male fish (22/267). The mean hepatic concentrations of various contaminants, including polychlorinated biphenyls (PCBs), chlorobenzenes, pesticides, and trace metals, were 6 to 8 times higher in lake whitefish than in three other fish species (Ictalurus punctatus, Catostomus commersoni, and Stizostedion vitreum) collected at the same site. Condition factor of lake whitefish from this study was lower than that previously reported 40 to 50 years ago at this site and from contemporary pristine sites in the Great Lakes, USA. The presence of liver neoplasms, gonadal lesions, and a decreased condition factor in lake whitefish from the St. Lawrence River may be etiologically related to elevated tissue concentrations of toxic chemical contaminants.

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Microbial Degradation of Sterols

Cited by 142 publications

References 3 publications

Naturally occurring progesterone in loblolly pine (Pinus taeda L.): A major steroid precursor of environmental androgens

Naturally occurring progesterone in loblolly pine (Pinus taeda L.): A major steroid precursor of environmental androgens

Identification of Androstenedione in a River Containing Paper Mill Effluent

Health of Lake Whitefish (Coregonus Clupeaformis) With Elevated Tissue Levels of Environmental Contaminants

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