Naturally Occurring Progesterone in Loblolly Pine: 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.

Degradation of Bile Acids by Soil and Water Bacteria

“…Although only little information is available regarding the endocrine effects of hydroxylated ADDs and ADs, they might also have androgenic potential, since exogenous steroids with similar structures to testosterone affect the androgen signaling pathways in vertebrates [ 164 , 165 ]. Similarly, endocrine effects of bacterial sterol degradation on fish were suggested: masculinization of fish populations in rivers receiving paper-mill effluents [ 166 , 167 , 168 ] was traced back to the bacterial transformation of plant-derived sterols into androgenic steroids [ 169 , 170 , 171 ].…”

Exposure to Paper Mill Effluent at a Site in North Central Florida Elicits Molecular-Level Changes in Gene Expression Indicative of Progesterone and Androgen Exposure

“…The source of these progesterones is most likely the loblolly pine ( Pinus taeda L. ) which is highly prevalent along this entire area [38]. As anal fin elongation is found only at the Fenholloway River, this suggests that the causative chemical is specific to that site or may be related to a combined effect from both progesterone and androgen loads.…”

“…The presence of low levels of AR-active chemicals at both sites may be due to the breakdown of this chemical from high levels of progesterones in the sediments via microorganisms [37] . The source of these progesterones is most likely the loblolly pine ( Pinus taeda L. ) which is highly prevalent along this entire area [38] . As anal fin elongation is found only at the Fenholloway River, this suggests that the causative chemical is specific to that site or may be related to a combined effect from both progesterone and androgen loads.…”

Countercurrent separation assisted identification of two mammalian steroid hormones in Vitex negundo

“…In 1964, Leboeuf, Cavé, and Goutarel reported that progesterone was found in Holarrhena floribunda leaves [1]. Since then progesterone and its congeners were successively reported to be present in apple seeds [2], loblolly pine [3], common foxglove ( Digitalis purpurea L.), tobacco ( Nicotiana tabacum L.), elecampane ( Inula helenium L.) [4], Juglans regia [5] , Adonis aleppica [5], and wheat [6], mostly using chromatographic methods, but also via isolation [5]. Other mammalian steroid hormones have been reported in plants.…”