Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives. (30th May 2019)

• Record Type: Journal Article
• Authors: Yang, Wei; Kortesniemi, Maaria; Ma, Xueying; Zheng, Jie; Yang, Baoru
• Is Part Of: Food chemistry. Volume 281(2019)
• Page Start: 189
• Page End: 196
• Publication Date: 2019-05-30
• Subjects: Anthocyanins -- Antioxidant capacity -- Blackcurrant -- Enzymatic acylation -- Lauric acid -- Lipophilicity -- Thermostability; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2018.12.111
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Enzymatic acylation occurred on glucoside and rutinoside of anthocyanins (ACNs). The relative proportions of ACNs did not affect the conversion yields of acylation. Acylation with lauric acid enhanced the lipophilicity and thermostability. Acylation improved the inhibition of lipid peroxidation in lipophilic environment. UV–vis absorbance property and the antioxidant activity were maintained. Abstract: 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.