title: Antioxidant and antiproliferative properties of methylated metabolites of anthocyanins.
abstract: Anthocyanins are major flavonoids in many plant foods and have been related to health promotion. In the human organism anthocyanins are metabolised to different metabolites. One of the most important phase II reactions of flavonoids is the methylation of the catechol group. This feature is expected to have an effect on the antioxidant and antiproliferative properties of flavonoids including anthocyanins. In this work, delphinidin-3-glucoside, cyanidin-3-glucoside and petunidin-3-glucoside methylated metabolites were obtained by enzymatic hemi-synthesis. The compounds were identified as monomethylated products by HPLC-MS and NMR. The methylated metabolites were found to still retain significant radical scavenging activity and reducing activity, suggesting that they could act as potential antioxidants in vivo. The antiproliferative activity of the metabolites in comparison with the parental anthocyanins was also evaluated in three cancer cell lines by sulforhodamine B assay. The conjugation with methyl groups decreased or did not alter the antiproliferative effect of the original anthocyanin.
authors.affiliation: Chemistry Investigation Centre (CIQ), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Portugal.
authors.forename: Iva
authors.initials: I
authors.lastname: Fernandes
authors.forename: Filipe
authors.initials: F
authors.lastname: Marques
authors.forename: Victor
authors.initials: V
authors.lastname: de Freitas
authors.forename: Nuno
authors.initials: N
authors.lastname: Mateus
mesh_terms: D000818:Animals; D000872:Anthocyanins / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005638:Fruit / Q000737:chemistry; D006131:Growth Inhibitors / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D008745:Methylation; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D051381:Rats; D027843:Vitis / Q000737:chemistry*
chemical_list: D000872:Anthocyanins; D000975:Antioxidants; D006131:Growth Inhibitors; D010936:Plant Extracts
keywords: Anthocyanins; Antioxidant; Antiproliferative; Metabolites; Methylation