Synthesis and Functional Characterization of Caffeic Acid Glucoside Using Leuconostoc mesenteroides Dextransucrase

• Published in: Journal of agricultural and food chemistry 2017-04, Vol.65 (13), p.2743-2750
• Main Authors: Nam, Seung-Hee, Kim, Young-Min, Walsh, Marie K, Wee, Young-Jung, Yang, Kwang-Yeol, Ko, Jin-A, Han, Songhee, Thanh Hanh Nguyen, Thi, Kim, Ji Young, Kim, Doman
• Format: Article
• Language: English
• Subjects: Bacterial Proteins - chemistry; Biocatalysis; Caffeic Acids - chemistry; Caffeic Acids - pharmacology; Cell Line; Cell Proliferation - drug effects; Glucosides - chemistry; Glucosides - pharmacology; Glucosyltransferases - chemistry; Humans; Leuconostoc mesenteroides - enzymology; Lipid Peroxidation - drug effects
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.7b00344

Caffeic acid was modified via transglucosylation using sucrose and dextransucrase from Leuconostoc mesenteroides B-512FMCM. Following enzymatic modification, a caffeic acid glucoside was isolated by butanol separation, silica gel chromatography, and preparative HPLC. The synthesized caffeic acid glucoside had a molecular mass-to-charge ratio of 365 m/z, and its structure was identified as caffeic acid-3-O-α-d-glucopyranoside. The production of this caffeic acid-3-O-α-d-glucopyranoside at a concentration of 153 mM was optimized using 325 mM caffeic acid, 355 mM sucrose, and 650 mU mL–1 dextransucrase in the synthesis reaction. In comparison with the caffeic acid, the caffeic acid-3-O-α-d-glucopyranoside displayed 3-fold higher water solubility, 1.66-fold higher antilipid peroxidation effect, 15% stronger inhibition of colon cancer cell growth, and 11.5-fold higher browning resistance. These results indicate that this caffeic acid-3-O-α-d-glucopyranoside may be a suitable functional component of food and pharmaceutical products.