Chlorogenic acid, a major polyphenol in edible plants, possesses strong antioxidant activity, anti-lipid peroxidation and anticancer effects. It used for industrial applications; however, this is limited by its instability to heat or light. In this study, we, for the first time synthesized chlorogenic acid glucoside (CHG) via transglycosylation using dextransucrase from Leuconostoc mesenteroides and sucrose. CHG was purified and its structure determined by nuclear magnetic resonance and matrix-associated laser desorption ionization–time-of-flight mass spectroscopy. The production yield of CHG was 44.0% or 141 mM, as determined by response surface methodology. CHG possessed a 65% increase in water solubility and a 2-fold browning resistance and it displayed stronger inhibition of lipid peroxidation and of colon cancer cell growth by MTT assay, compared to chlorogenic acid. Therefore, this study may expand the industrial applications of chlorogenic acid as water-soluble or browning resistant compound (CHG) through enzymatic glycosylation.
Nam, Seung-Hee; Ko, Jin-A; Wee, Young-Jung; Walsh, Marie K.; Yang, Kwang-Yeol; Yim, Sun-Hee; Eun, Jon-Bang; Jun, Woojin; Park, Jang-Hyun; Kim, Young-Min; Han, Songhee; Nguyen, Thi Thanh Hanh; and Kim, Nahyun M., "Enzymatic synthesis of chlorogenic acid glucoside using dextransucrase and its physical and functional properties" (2017). Nutrition, Dietetics, and Food Sciences Faculty Publications. Paper 862.