Characterization of oxyphytosterols generated by beta-sitosterol ozonization

Autor(es)

Martins, Igor Rodrigues ^[1] ; Onuki, Janice ^[2] ; Miyamoto, Sayuri ^[3] ; Uemi, Miriam ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Paulo, Inst Environm Chem & Pharmaceut Sci, Dept Chem, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP - Brazil

^[2] Butantan Inst, Lab Dev & Innovat, Sao Paulo - Brazil

^[3] Univ Sao Paulo, Inst Chem, Dept Biochem, Sao Paulo - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Archives of Biochemistry and Biophysics; v. 689, AUG 15 2020.
• Citações Web of Science: 0

Resumo

beta-Sitosterol (beta Sito) 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. beta Sito 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-dimethy l-1,2,3,3a,4,5,6,7- octahydroinden-4-yl] acetaldehyde (beta Sec), (2-{[}(7aR)-5-{[}(2R,5S)-5-hydroxy-2-methyl-7-oxo-oxepan-2-yl]-1,7a-dime thyl-1,2,3,3a,4,5,6,7octahydroinden-4-yl] acetaldehyde (beta Lac) and 2-((7aR)-5-((1R,4S)-4-hydroxy-1-methyl-2-oxocyclohexyl)1,7a-dimethylocta hydro-1Hinden-4-yl) acetic acid (beta COOH) generated by ozonization of beta Sito, through their synthesis and molecular characterization. The cytotoxic effect of beta Sito and its main oxyphytosterol beta Sec was evaluated and both reduced the HepG2 cell viability. (AU)

• Processo FAPESP: 13/07937-8 - Redoxoma
• Beneficiário: Ohara Augusto
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 14/14801-8 - Oxisteróis são capazes de modificar a ubiquitina e comprometer o processo proteolítico ubiquitina proteassoma?
• Beneficiário: Miriam Uemi
• Modalidade de apoio: Auxílio à Pesquisa - Regular