A1 Refereed original research article in a scientific journal
Enzymatic Acylation of Anthocyanins Isolated from Alpine Bearberry (Arctostaphylos alpina) and Lipophilic Properties, Thermostability, and Antioxidant Capacity of the Derivatives
Authors: Wei Yang, Maaria Kortesniemi, Baoru Yang, Jie Zheng
Publisher: AMER CHEMICAL SOC
Publication year: 2018
Journal: Journal of Agricultural and Food Chemistry
Journal name in source: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Journal acronym: J AGR FOOD CHEM
Volume: 66
Issue: 11
First page : 2909
Last page: 2916
Number of pages: 8
ISSN: 0021-8561
DOI: https://doi.org/10.1021/acs.jafc.7b05924
Abstract
Cyanidin-3-O-galactoside (cy-gal) isolated from alpine bearberry (Arctostaphylos alpine L.) was enzymatically acylated with saturated fatty acids of different chain lengths with Candida antarctica lipase immobilized on acrylic resin (Novozyme 435). The acylation reaction was optimized by considering the reaction medium, acyl donor, substrate molar ratio, reaction temperature, and reaction time. The highest conversion yield of 73% was obtained by reacting cy-gal with lauric acid (molar ratio of 1:10) in tert-butanol at 60 degrees C for 72 h. A novel compound was synthesized, which was identified as cyanidin-3-O-(6 ''-dodecanoyl)galactoside by mass spectrometry and nuclear magnetic resonance. Introducing lauric acid into cy-gal significantly improved both the lipophilicity and thermostability and substantially preserved the ultraviolet visible absorbance and antioxidant properties. The research provides important insight in expanding the application of natural anthocyanins in the cosmetic and food industries.
Cyanidin-3-O-galactoside (cy-gal) isolated from alpine bearberry (Arctostaphylos alpine L.) was enzymatically acylated with saturated fatty acids of different chain lengths with Candida antarctica lipase immobilized on acrylic resin (Novozyme 435). The acylation reaction was optimized by considering the reaction medium, acyl donor, substrate molar ratio, reaction temperature, and reaction time. The highest conversion yield of 73% was obtained by reacting cy-gal with lauric acid (molar ratio of 1:10) in tert-butanol at 60 degrees C for 72 h. A novel compound was synthesized, which was identified as cyanidin-3-O-(6 ''-dodecanoyl)galactoside by mass spectrometry and nuclear magnetic resonance. Introducing lauric acid into cy-gal significantly improved both the lipophilicity and thermostability and substantially preserved the ultraviolet visible absorbance and antioxidant properties. The research provides important insight in expanding the application of natural anthocyanins in the cosmetic and food industries.
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