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

Abstract

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.

Activation of the Androgen Receptor by Intratumoral Bioconversion of Androstanediol to Dihydrotestosterone in Prostate Cancer

“…De novo synthesis of DHT from progesterone is an alternative pathway involved in environmental androgen production (44) and in castration-recurrent prostate cancer (10). During androgen deprivation therapy, androstenedione is a major circulating adrenal androgen converted to DHT through testosterone.…”

Effects of model aromatizable (17α-methyltestosterone) and non-aromatizable (5α-dihydrotestosterone) androgens on the adult mummichog (Fundulus heteroclitus) in a short-term reproductive endocrine bioassay

“…Androgen activity was not linked to effluent treatment type, mill location or mill process (Milestone et al, 2012). The presence of androgens in pulp mill effluent (PME) may be due to bacterial metabolism of plant sterols and other steroids commonly found in PME (Jenkins et al, 2001;Parks et al, 2001;Carson et al, 2008). Antiandrogenic responses to sewage can occur due to the ability of presumed estrogenic substances to also act as androgen receptor (AR) antagonists to disrupt endocrine function (Gray et al, 1997;Batty and Lim, 1999).…”

Identification of a thiolase gene essential for β-oxidation of the acyl side chain of the steroid compound cholate in Pseudomonas sp. strain Chol1

“…As steroids are ubiquitous and abundant in the environment, bacterial steroid degradation is an important part of the CO 2 ‐releasing site of the global carbon cycle. Bacterial degradation is particularly important for the degradation of natural and synthetic steroid hormones, which can influence the fertility of animals as endocrine disruptors (Carson et al , 2008; Combalbert & Hernandez‐Raquet, 2010). Furthermore, bacterial transformation of steroids is an essential part of the production of steroid drugs in biotechnology (Bortolini et al , 1997; Mahato & Garai, 1997).…”