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An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity.
Food Chem. 2016 Apr 15; 197 Pt B:1226-34.FC

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+Show Affiliations

Laval University, Department of Soil Sciences and Agri-Food Engineering, Building Paul-Comtois, Quebec G1V 0A6, Canada. Electronic address: nasima.chorfa.1@ulaval.ca.Centre de Recherche Industrielle du Quebec, 333, rue Franquet, Quebec G1P 4C7, Canada. Electronic address: Sylvain.Savard@criq.qc.ca.Laval University, Department of Soil Sciences and Agri-Food Engineering, Building Paul-Comtois, Quebec G1V 0A6, Canada. Electronic address: khaled.belkacemi@sga.ulaval.ca.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26675861

Citation

Chorfa, Nasima, et al. "An Efficient Method for High-purity Anthocyanin Isomers Isolation From Wild Blueberries and Their Radical Scavenging Activity." Food Chemistry, vol. 197 Pt B, 2016, pp. 1226-34.
Chorfa N, Savard S, Belkacemi K. An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity. Food Chem. 2016;197 Pt B:1226-34.
Chorfa, N., Savard, S., & Belkacemi, K. (2016). An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity. Food Chemistry, 197 Pt B, 1226-34. https://doi.org/10.1016/j.foodchem.2015.11.076
Chorfa N, Savard S, Belkacemi K. An Efficient Method for High-purity Anthocyanin Isomers Isolation From Wild Blueberries and Their Radical Scavenging Activity. Food Chem. 2016 Apr 15;197 Pt B:1226-34. PubMed PMID: 26675861.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity. AU - Chorfa,Nasima, AU - Savard,Sylvain, AU - Belkacemi,Khaled, Y1 - 2015/11/21/ PY - 2015/06/26/received PY - 2015/11/06/revised PY - 2015/11/14/accepted PY - 2015/12/18/entrez PY - 2015/12/18/pubmed PY - 2016/9/10/medline KW - AAPH (2,2’-azobis[2-methylpropionamidine] dihydrochloride) (2-[(1-amino-1-imino-2-methylpropan-2-yl)diazenyl]-2methylpropanimidamide] dihydrochloride) PubChem CID: 76344) KW - Anthocyanins KW - Ascorbic acid ((2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one) (PubChem CID: 54670067) KW - Blueberries KW - 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) KW - 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) KW - 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) KW - Dibasic potassium phosphate (dipotassium;hydrogen phosphate) (PubChem CID: 24450) KW - Fluorescein sodium salt (disodium;2-(3-oxido-6-oxoxanthen-9-yl) benzoate) (PubChem CID: 10608) KW - Formic acid (PubChem CID: 284) KW - Malvidin-3,5-di-glucoside chloride (2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3,5,7-triol;chloride) (PubChem CID: 69512) KW - 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) KW - Methanol (PubChem CID: 887) KW - Monobasic potassium phosphate (potassium;dihydrogen phosphate) (PubChem CID: 516951) KW - ORAC KW - Potassium hydroxide (potassium;hydroxide) (PubChem CID: 14797) KW - Preparative-HPLC KW - Silica (dioxosilane) (PubChem CID:24261) KW - Trolox (6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid) (PubChem CID:40634) KW - Vaccinium angustifolium Aiton and Vaccinium myrtilloides Michaux SP - 1226 EP - 34 JF - Food chemistry JO - Food Chem VL - 197 Pt B N2 - 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. SN - 1873-7072 UR - https://www.unboundmedicine.com/medline/citation/26675861/An_efficient_method_for_high_purity_anthocyanin_isomers_isolation_from_wild_blueberries_and_their_radical_scavenging_activity_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0308-8146(15)30221-1 DB - PRIME DP - Unbound Medicine ER -