Synthesis of acyl arbutin by an immobilized lipase and its suppressive ability against lipid oxidation in a bulk system and O/W emulsion.
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.
Nagai
Mizuka
M
Department of Biotechnology and Chemistry, School of Engineering, Kinki University, Takaya, Higashi-Hiroshima, Japan.
Watanabe
Yoshiyuki
Y
Nomura
Masato
M
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
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