Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives.

Acylation Anthocyanins / analysis Antioxidants / analysis Glucosides / analysis Lipid Peroxidation Magnetic Resonance Spectroscopy Ribes / chemistry Tandem Mass Spectrometry
Anthocyanins Antioxidant capacity Blackcurrant Enzymatic acylation Lauric acid Lipophilicity Thermostability

Journal

Food chemistry
ISSN: 1873-7072
Titre abrégé: Food Chem
Pays: England
ID NLM: 7702639

Informations de publication

Date de publication:
30 May 2019
Historique:
received: 03 10 2018
revised: 28 12 2018
accepted: 29 12 2018
entrez: 20 1 2019
pubmed: 20 1 2019
medline: 14 3 2019
Statut: ppublish

Résumé

Anthocyanin-rich fractions isolated from blackcurrant (Ribes nigrum L.) including delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were enzymatically acylated with lauric acid. All the four anthocyanins were successfully monoacylated, and their relative proportions did not affect the conversion yield. The acylation occurred at the 6″-OH position of the glucosides and at the rhamnose 4‴-OH of the rutinosides. The rutinoside moieties of the anthocyanins were successfully acylated for the first time, and the corresponding acylation sites were verified by NMR analysis. The acylation enhanced the lipophilicity. The hydrophilic anthocyanin rutinosides were more lipophilic after acylation. Introducing lauric acid into the anthocyanins significantly improved the thermostability and capacity to inhibit lipid peroxidation and maintained UV-vis absorbance and antioxidant activity. This research provides important insights into acylation of mixed anthocyanins with different glycosyl moieties.

Identifiants

DOI: 10.1016/j.foodchem.2018.12.111 PMID: 30658747
pubmed: 30658747
pii: S0308-8146(19)30020-2
doi: 10.1016/j.foodchem.2018.12.111
pii:
doi:

Substances chimiques

Anthocyanins 0
Antioxidants 0
Glucosides 0
cyanidin-3-O-beta-glucopyranoside 0
delphinidin-3-rutinoside 15674-58-5
delphinidin 3-O-glucopyranoside 474A9U89JS
cyanidin 3-rutinoside OR49FC491X

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

189-196

Informations de copyright

Copyright © 2019. Published by Elsevier Ltd.

Auteurs

Wei Yang (W)

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland. Electronic address: wei.yang@utu.fi.

Maaria Kortesniemi (M)

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland. Electronic address: mkkort@utu.fi.

Xueying Ma (X)

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland. Electronic address: xueying.ma@utu.fi.

Jie Zheng (J)

Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China; Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland. Electronic address: zhengjie@jnu.edu.cn.

Baoru Yang (B)

Food Chemistry and Food Development, Department of Biochemistry, University of Turku, FI-20014 Turku, Finland. Electronic address: baoru.yang@utu.fi.

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Classifications MeSH

questionsmedicales.fr › Métabolisme › Acylation › Enzymatic acylation of blackcurrant (Ribes...
questionsmedicales.fr › Facteurs biologiques › Pigments biologiques › Anthocyanes › Enzymatic acylation of blackcurrant (Ribes...
questionsmedicales.fr › Actions chimiques et utilisations › Utilisations spécialisées de produits chimiques › Agents protecteurs › Antioxydants › Enzymatic acylation of blackcurrant (Ribes...
questionsmedicales.fr › Glucides › Hétérosides › Glucosides › Enzymatic acylation of blackcurrant (Ribes...
questionsmedicales.fr › Métabolisme › Métabolisme énergétique › Oxydoréduction › Peroxydation lipidique › Enzymatic acylation of blackcurrant (Ribes...
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Analyse spectrale › Spectroscopie par résonance magnétique › Enzymatic acylation of blackcurrant (Ribes...
questionsmedicales.fr › Eucaryotes › Viridiplantae › Streptophyta › Embryophyta › Tracheobionta › Magnoliopsida › Rosanae › Rosales › Grossulariaceae › Ribes › Enzymatic acylation of blackcurrant (Ribes...
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Spectrométrie de masse › Spectrométrie de masse en tandem › Enzymatic acylation of blackcurrant (Ribes...