title: Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis.
abstract: Transesterification of arbutin and undecylenic acid vinyl ester was catalyzed by alkaline protease, Bioprase, in dimethylformamide to get arbutin derivative having undecylenic acid at 6-position of glucose moiety, 6-O-undecylenoyl p-hydroxyphenyl beta-D-glucopyranoside. The reaction rate increased with increase of arbutin concentration, and when its concentration was 0.9 M, the conversion rate was more than 90% under addition of 2 M undecylenic acid vinyl ester. The obtained arbutin ester significantly suppressed melanin production in murine B16 melanoma cells.
authors.affiliation: National Institute of Advanced Industrial Science and Technology, Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan. y.tokiwa@aist.go.jp
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Tokiwa
authors.forename: Masaru
authors.initials: M
authors.lastname: Kitagawa
authors.forename: Takao
authors.initials: T
authors.lastname: Raku
authors.forename: Shusaku
authors.initials: S
authors.lastname: Yanagitani
authors.forename: Kenji
authors.initials: K
authors.lastname: Yoshino
mesh_terms: D000818:Animals; D001104:Arbutin / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000494:pharmacology; D001426:Bacterial Proteins / Q000737:chemistry; D045744:Cell Line, Tumor; D010450:Endopeptidases / Q000737:chemistry; D004952:Esters / Q000494:pharmacology*; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D008546:Melanoma, Experimental / Q000378:metabolism*; D051379:Mice; D012878:Skin Neoplasms / Q000378:metabolism*; D014476:Undecylenic Acids / Q000494:pharmacology*
chemical_list: D001426:Bacterial Proteins; D004952:Esters; D008543:Melanins; D014476:Undecylenic Acids; C521564:arbutin undecylenic acid ester; D001104:Arbutin; D010450:Endopeptidases; C087822:alkaline protease