Enzymatic Hydrolysis of Rutin: Evaluation of Kinetic Parameters and Anti-Proliferative, Mutagenic and Anti-Mutagenic Effects.
Mariana Alves Sobreiro, Adriana Della Torre, Maria Elisa Melo Branco de Araújo, Paula Renata Bueno Campos Canella, João Ernesto de Carvalho, Patrícia de Oliveira Carvalho, Ana Lucia Tasca Gois Ruiz
Author Information
Mariana Alves Sobreiro: Health Sciences Postgraduate Program, Universidade São Francisco (USF), Bragança Paulista 12916-900, SP, Brazil.
Adriana Della Torre: Laboratory of Phytochemistry and Experimental Pharmacology and Toxicology (LAFTEX), Faculty of Pharmaceutical Sciences, University of Campinas, 200 Candido Portinari Street, Campinas 13083-871, SP, Brazil.
Maria Elisa Melo Branco de Araújo: Health Sciences Postgraduate Program, Universidade São Francisco (USF), Bragança Paulista 12916-900, SP, Brazil.
Paula Renata Bueno Campos Canella: Health Sciences Postgraduate Program, Universidade São Francisco (USF), Bragança Paulista 12916-900, SP, Brazil. ORCID
João Ernesto de Carvalho: Laboratory of Phytochemistry and Experimental Pharmacology and Toxicology (LAFTEX), Faculty of Pharmaceutical Sciences, University of Campinas, 200 Candido Portinari Street, Campinas 13083-871, SP, Brazil.
Patrícia de Oliveira Carvalho: Health Sciences Postgraduate Program, Universidade São Francisco (USF), Bragança Paulista 12916-900, SP, Brazil. ORCID
Ana Lucia Tasca Gois Ruiz: Laboratory of Phytochemistry and Experimental Pharmacology and Toxicology (LAFTEX), Faculty of Pharmaceutical Sciences, University of Campinas, 200 Candido Portinari Street, Campinas 13083-871, SP, Brazil. ORCID
The bioavailability of glucoside flavonoids is influenced by the nature of the sugar, glucosides being absorbed faster than rhamnoglucosides, for example. One strategy to enhance the bioavailability is enzymatic hydrolysis. In this study, some kinetic parameters of hesperidinase-mediated hydrolysis of rutin were evaluated using an UHPLC/QTOF-MS analysis of the products of a bioconversion reaction. The resulting hydrolyzed rutins (after 4, 8 and 12 h of reaction) were submitted to anti-proliferative and Cytokinesis-Block Micronucleus (CBMN) assays in CHO-K1 cells. In the hesperidinase-mediated hydrolysis, the final concentration of quercetin-3-O-glucoside (Q3G) was directly proportional to the rutin concentration and inversely proportional to the reaction time. At an anti-proliferative concentration (2.5 μg/mL), hydrolyzed rutin derivatives did not show a mutagenic effect, except for the sample with a higher content of Q3G (after 4 h of the enzymatic hydrolysis of rutin). Moreover, the higher Q3G content in hydrolyzed rutin protected the CHO-K1 cells 92% of the time against methyl methanesulfonate-induced mutagenic damage. These results suggested that the anti-mutagenic effect of hydrolyzed rutin might be related to antioxidant and cell death induction. Presenting a good lipophilicity/hydrophilicity ratio, together with antioxidant and anti-mutagenic activities, the hesperidinase-mediated hydrolyzed rutin seemed to be a promisor raw material for the development of food supplements.
