title: Enzymatic de-glycosylation of rutin improves its antioxidant and antiproliferative activities.
abstract: Bioavailability and biological properties of flavonoid glycosides can be improved after the enzymatic hydrolysis of specific glycosyl groups. In this study, we evaluate the antioxidant and antiproliferative potential of rutin after enzymatic hydrolysis performed by α-l-rhamnosidases (hesperidinase from Penicillium sp. and naringinase from Penicillium decumbens) previously heated at 70°C for 30 min to inactivate the undesirable β-d-glucosidase activity. The highest in vitro antioxidant activity determined by DPPH radical scavenging was achieved with rutin hydrolyzed by hesperidinase. Rutin was predominantly bioconverted into quercetin-3-glucoside. There was no statistical difference between xanthine oxidase inhibition by rutin before and after hydrolysis. However, in vitro inhibitory activity against ten human tumor cell lines showed that hydrolyzed rutin exerted a more potent antiproliferative effect than quercetin and rutin on various cancer cell lines, specially glioma, and ovarian and breast adenocarcinomas. These results indicate that quercetin-3-glucoside could be a promising functional derivative obtained by rutin hydrolysis.
authors.affiliation: Laboratory of Multidisciplinary Research, São Francisco University, USF, São Francisco de Assis Avenue, 218, 12916-900 Bragança Paulista, SP, Brazil.
authors.forename: Maria Elisa Melo Branco
authors.initials: ME
authors.lastname: de Araújo
authors.forename: Yollanda E
authors.initials: YE
authors.lastname: Moreira Franco
authors.forename: Thiago Grando
authors.initials: TG
authors.lastname: Alberto
authors.forename: Mariana Alves
authors.initials: MA
authors.lastname: Sobreiro
authors.forename: Marco Aurélio
authors.initials: MA
authors.lastname: Conrado
authors.forename: Denise Gonçalves
authors.initials: DG
authors.lastname: Priolli
authors.forename: Alexandra C H
authors.initials: AC
authors.lastname: Frankland Sawaya
authors.forename: Ana Lucia T G
authors.initials: AL
authors.lastname: Ruiz
authors.forename: João Ernesto
authors.initials: JE
authors.lastname: de Carvalho
authors.forename: Patrícia
authors.initials: P
authors.lastname: de Oliveira Carvalho
mesh_terms: D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D005656:Fungal Proteins / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D006868:Hydrolysis; D015394:Molecular Structure; D009097:Multienzyme Complexes / Q000737:chemistry*; D010407:Penicillium / Q000201:enzymology*; D012431:Rutin / Q000737:chemistry* / Q000494:pharmacology*; D001617:beta-Glucosidase / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D005656:Fungal Proteins; D009097:Multienzyme Complexes; D012431:Rutin; D006026:Glycoside Hydrolases; C023307:hesperidinase; C039827:naringinase; D001617:beta-Glucosidase