title: Synthesis of acyl arbutin by an immobilized lipase and its suppressive ability against lipid oxidation in a bulk system and O/W emulsion.
abstract: Acyl arbutin was synthesized through the condensation of arbutin with a saturated fatty acid (C6-18) by the immobilized lipase in a batch reaction. The conversion at 10 and 20 g/l-solvent of immobilized lipase reached 45% over 2 d, but the initial reaction rate per amount of immobilized lipase decreased at 20 g/l-solvent. The radical scavenging activity of acyl arbutin in an ethanol solution was independent of the acyl chain length, although the rate constant, k, estimated for the oxidation of methyl linoleate in a bulk system with acyl arbutin by using the Weibull equation, decreased as the acyl chain length increased. This indicates the antioxidative ability of acyl arbutin with a long acyl chain to be due to its lipophilicity. Furthermore, it is suggested that dodecanoyl arbutin mainly acted on the interface between the oil and water phases in an O/W emulsion, and effectively suppressed the oxidation induced at the interface.
authors.affiliation: Department of Biotechnology and Chemistry, School of Engineering, Kinki University, Takaya, Higashi-Hiroshima, Japan.
authors.forename: Mizuka
authors.initials: M
authors.lastname: Nagai
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Watanabe
authors.forename: Masato
authors.initials: M
authors.lastname: Nomura
mesh_terms: D001104:Arbutin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002175:Candida / Q000201:enzymology; D004655:Emulsions; D004800:Enzymes, Immobilized / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D057927:Hydrophobic and Hydrophilic Interactions; D007700:Kinetics; D008041:Linoleic Acids / Q000737:chemistry; D008049:Lipase / Q000378:metabolism*; D050356:Lipid Metabolism / Q000187:drug effects*; D009821:Oils / Q000737:chemistry; D010084:Oxidation-Reduction / Q000187:drug effects; D014867:Water / Q000737:chemistry
chemical_list: D004655:Emulsions; D004800:Enzymes, Immobilized; D016166:Free Radical Scavengers; D008041:Linoleic Acids; D009821:Oils; C547202:dodecanoylarbutin; D014867:Water; C005575:methyl linoleate; D001104:Arbutin; D008049:Lipase