title: Synthesis and Functional Characterization of Caffeic Acid Glucoside Using Leuconostoc mesenteroides Dextransucrase.
abstract: 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-1dextransucrase 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.
authors.forename: Seung-Hee
authors.identifier: http://orcid.org/0000-0001-5271-1275
authors.initials: SH
authors.lastname: Nam
authors.forename: Young-Min
authors.initials: YM
authors.lastname: Kim
authors.affiliation: Department of Nutrition, Dietetics, and Food Sciences, Utah State University , 8700 Old Main Hill, 750N 1200E, Logan, Utah 84322-8700, United States.
authors.forename: Marie K
authors.initials: MK
authors.lastname: Walsh
authors.affiliation: Department of Food Science and Technology, Yeungnam University , Gyeongbuk 38541, South Korea.
authors.forename: Young-Jung
authors.initials: YJ
authors.lastname: Wee
authors.forename: Kwang-Yeol
authors.initials: KY
authors.lastname: Yang
authors.forename: Jin-A
authors.initials: JA
authors.lastname: Ko
authors.forename: Songhee
authors.initials: S
authors.lastname: Han
authors.forename: Thi
authors.initials: T
authors.lastname: Thanh Hanh Nguyen
authors.forename: Ji Young
authors.initials: JY
authors.lastname: Kim
authors.forename: Doman
authors.identifier: http://orcid.org/0000-0003-0389-3441
authors.initials: D
authors.lastname: Kim
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry*; D055162:Biocatalysis; D002109:Caffeic Acids / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D005960:Glucosides / Q000737:chemistry* / Q000494:pharmacology; D005964:Glucosyltransferases / Q000737:chemistry*; D006801:Humans; D000070007:Leuconostoc mesenteroides / Q000201:enzymology*; D015227:Lipid Peroxidation / Q000187:drug effects
chemical_list: D001426:Bacterial Proteins; D002109:Caffeic Acids; D005960:Glucosides; D005964:Glucosyltransferases; C020025:dextransucrase; C040048:caffeic acid
keywords: Leuconostoc mesenteroides; caffeic acid; dextransucrase; transglucosylation