title: An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity.
abstract: An efficient process for the purification of anthocyanin monomeric isomers from wild blueberries of Lake Saint-Jean region (Quebec, Canada) was developed and easy scalable at industrial purpose. The blueberries were soaked in acidified ethanol, filtered, and the filtrate was cleaned by solid phase extraction using silica gel C-18 and DSC-SCX cation-exchange resin. Anthocyanin-enriched elutes (87 wt.%) were successfully fractionated by preparative liquid chromatography. The major anthocyanins mono-galactoside, -glucoside and -arabinoside isomers of delphinidin, cyanidin, petunidin, peonidin and malvidin were isolated with a purity up to 100% according to their LC-MS and (1)H NMR spectra. The oxygen radical absorbance capacity (ORAC) of the obtained pure anthocyanins was evaluated. Delphinidin-3-galactoside has the highest capacity (13.062 ± 2.729 μmol TE/μmol), and malvidin-3-glucoside the lowest (0.851 ± 0.032 μmol TE/μmol). A mechanistic pathway preview is suggested for the anthocyanins scavenging free radical activity by hydrogen transfer.
authors.affiliation: Laval University, Department of Soil Sciences and Agri-Food Engineering, Building Paul-Comtois, Quebec G1V 0A6, Canada. Electronic address: nasima.chorfa.1@ulaval.ca.
authors.forename: Nasima
authors.initials: N
authors.lastname: Chorfa
authors.affiliation: Centre de Recherche Industrielle du Quebec, 333, rue Franquet, Quebec G1P 4C7, Canada. Electronic address: Sylvain.Savard@criq.qc.ca.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Savard
authors.affiliation: Laval University, Department of Soil Sciences and Agri-Food Engineering, Building Paul-Comtois, Quebec G1V 0A6, Canada. Electronic address: khaled.belkacemi@sga.ulaval.ca.
authors.forename: Khaled
authors.initials: K
authors.lastname: Belkacemi
mesh_terms: D000872:Anthocyanins / Q000032:analysis* / Q000302:isolation & purification; D029798:Blueberry Plants / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D016166:Free Radical Scavengers / Q000494:pharmacology*; D010936:Plant Extracts / Q000494:pharmacology*
chemical_list: D000872:Anthocyanins; D016166:Free Radical Scavengers; D010936:Plant Extracts
keywords: AAPH (2,2’-azobis[2-methylpropionamidine] dihydrochloride) (2-[(1-amino-1-imino-2-methylpropan-2-yl)diazenyl]-2methylpropanimidamide] dihydrochloride) PubChem CID: 76344); Anthocyanins; Ascorbic acid ((2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one) (PubChem CID: 54670067); Blueberries; Cyanidin-3,5-di-glucoside chloride (2-(3,4-dihydroxyphenyl)-3-(|A-d-glucopyranosyloxy)-7-hydroxychromenium-5-yl A-d-glucopyranoside chloride) (PubChem CID: 164999); Cyanidin-3-glucoside (kuromanin) ((2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol) (PubChem CID: 441667); Delphinidin-3-glucoside (myrtillin) ((2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(3,4,5trihydroxyphenyl)chromenylium-3-yl] oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride) (PubChem CID: 165558); Dibasic potassium phosphate (dipotassium;hydrogen phosphate) (PubChem CID: 24450); Fluorescein sodium salt (disodium;2-(3-oxido-6-oxoxanthen-9-yl) benzoate) (PubChem CID: 10608); Formic acid (PubChem CID: 284); Malvidin-3,5-di-glucoside chloride (2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3,5,7-triol;chloride) (PubChem CID: 69512); Malvidin-3-glucoside (oenin) chloride (2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride) (PubChem CID: 12313693); Methanol (PubChem CID: 887); Monobasic potassium phosphate (potassium;dihydrogen phosphate) (PubChem CID: 516951); ORAC; Potassium hydroxide (potassium;hydroxide) (PubChem CID: 14797); Preparative-HPLC; Silica (dioxosilane) (PubChem CID:24261); Trolox (6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid) (PubChem CID:40634); Vaccinium angustifolium Aiton and Vaccinium myrtilloides Michaux