Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis.
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.
Tokiwa
Yutaka
Y
National Institute of Advanced Industrial Science and Technology, Central 6, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8566, Japan. y.tokiwa@aist.go.jp
Kitagawa
Masaru
M
Raku
Takao
T
Yanagitani
Shusaku
S
Yoshino
Kenji
K
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*
D001426:Bacterial Proteins; D004952:Esters; D008543:Melanins; D014476:Undecylenic Acids; C521564:arbutin undecylenic acid ester; D001104:Arbutin; D010450:Endopeptidases; C087822:alkaline protease