Novel pathway for bacterial metabolism of bisphenol A. Rearrangements and stilbene cleavage in bisphenol A metabolism.
نویسندگان
چکیده
Bisphenol A (BPA) is metabolized by a Gram-negative aerobic bacterium via a novel pathway involving oxidative skeletal rearrangement of the BPA. Oxidation of the aliphatic methyl group of BPA leads to coproduction of the methyl-hyroxylated 2,2-bis(4-hydroxyphenyl)-1-propanol and a skeletally rearranged triol 1,2-bis(4-hydroxyphenyl)-2-propanol. The major route of metabolism (> 80%) is through the rearrangement. The 1,2-bis(4-hydroxyphenyl)-2-propanol is dehydrated to 4,4'-dihydroxy-alpha-methylstilbene, which is rapidly cleaved by oxidation to 4-hydroxybenzaldehyde and 4-hydroxyacetophenone. 4-Hydroxybenzaldehyde is oxidized to 4-hydroxybenzoic acid. Both 4-hydroxybenzoic acid and 4-hydroxyacetophenone are mineralized. The minor product of BPA hydroxylation, 2,2-bis(4-hydroxyphenyl)-1-propanol, is further oxidized to form both 2,2-bis(4-hydroxyphenyl)propanoic acid and a skeletally rearranged tetraol, 2,3-bis(4-hydroxyphenyl)-1,2-propanediol. As is the case in the hydroxylation of BPA, the major product is skeletally rearranged. 2,3-Bis(4-hydroxyphenyl)-1,2-propanediol is slowly transformed to 4-hydroxyphenacyl alcohol.
منابع مشابه
Bisphenol-A analogue (bisphenol-S) exposure alters female reproductive tract and apoptosis/oxidative gene expression in blastocyst-derived cells
Objective(s): One of the major endocrine-disrupting chemicals, Bisphenol-S (BPS) has replaced bisphenol-A due to public health anxiety. The present study evaluated low dosage BPS effect on female reproductive potential, hormonal disruption, and gene expression pathways of blastocyst-derived cells.Materials and Methods: NMRI female mice (...
متن کاملA Review of Driver Genetic Alterations in Thyroid Cancers
Thyroid cancer is a frequent endocrine related malignancy with continuous increasing incidence. There has been moving development in understanding its molecular pathogenesis recently mainly through the explanation of the original role of several key signaling pathways and related molecular distributors. Central to these mechanisms are the genetic and epigenetic alterations in these pathways, su...
متن کاملNovel pathway of metabolic activation of bisphenol A-related compounds for estrogenic activity.
We previously demonstrated that estrogenic activity of bisphenol A (BPA) in the yeast estrogen screening assay was increased severalfold after incubation with rat liver S9 fraction in the presence of a NADPH-generating system. In this study, we investigated whether eight BPA-related compounds are similarly activated metabolically by rat liver S9 fraction. Three of the analogs exhibited an incre...
متن کاملBisphenol a glucuronide, a major metabolite in rat bile after liver perfusion.
The environmental estrogen bisphenol A, orally introduced into the body, passes through the liver and modulates the endocrine system to elicit irreversible changes in the functioning of reproduction. To elucidate the actual and dynamic metabolism of bisphenol A in the liver before its arrival at target organs, this study evaluated the metabolism and disposition of the compound within the passag...
متن کاملComparative modelling of 3D-structure of Geobacter sp. M21 (a metal reducing bacteria) Mn-Fe superoxide dismutase and its binding properties with bisphenol-A, aminotriazole and ethylene-diurea
Superoxide dismutase play important roles in iron-respiratory bacteria such as Geobacteraceae as an antioxidant defense, and probably an effective enzyme of electron transfer network. Regarding the application of iron-respiratory bacteria in environmental biotechnology particularly biodegradation and bioremediation, understanding the mechanism of inhibition/induction of superoxide dismutase by ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- The Journal of biological chemistry
دوره 269 10 شماره
صفحات -
تاریخ انتشار 1994