Characterization of oxyphytosterols generated by β-sitosterol ozonization.

Characterization of oxyphytosterols generated by β-sitosterol ozonization. Arch Biochem Biophys. 2020 Jun 23;:108472 Authors: Martins IR, Onuki J, Miyamoto S, Uemi M Abstract β-Sitosterol (βSito) is the most abundant phytosterol found in elevated concentrations in vegetable oils, nuts, seeds, cereals, fruits, and in many phytosterol-enriched foods. Although the benefits, there is a concern in terms of food quality and health due to the increasing consumption of phytosterols and the possible adverse side effects of their oxidation products, oxyphytosterols. βSito has a similar structure to cholesterol, with an unsaturated double bond at C5-C6, which is susceptible to oxidation by reactive oxygen species like ozone, generating oxyphytosterols. In this work we propose a mechanism of formation of three oxyphytosterols 2-[(7aR)-5-[(1R,4S)-4-hydroxy-1-methyl-2-oxocyclohexyl]-1,7a-dimethyl-1,2,3,3a,4,5,6,7- octahydroinden-4-yl]acetaldehyde (βSec), (2-[(7aR)-5-[(2R,5S)-5-hydroxy-2-methyl-7-oxo-oxepan- 2-yl]-1,7a-dimethyl-1,2,3,3a,4,5,6,7-octahydroinden-4- yl] acetaldehyde (βLac) and 2-((7aR)-5-((1R,4S)-4-hydroxy-1-methyl-2- oxocyclohexyl)-1,7a-dimethyloctahydro-1Hinden-4-yl) (βCOOH) generated by ozonization of βSito, through their synthesis and molecular characterization. The cytotoxic effect of βSito and its main oxyphytosterol βSec was evaluated and both reduced the HepG2 cell viability. PMID: 32590065 [PubMed - as suppli...
Source: Archives of Biochemistry and Biophysics - Category: Biochemistry Authors: Tags: Arch Biochem Biophys Source Type: research