Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis

• Published in: Bioorganic & medicinal chemistry letters Vol. 17; no. 11; pp. 3105 - 3108
• Main Authors: Tokiwa, Yutaka, Kitagawa, Masaru, Raku, Takao, Yanagitani, Shusaku, Yoshino, Kenji
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.06.2007; Elsevier
• Subjects: Animals; Arbutin; Arbutin - analogs & derivatives; Arbutin - biosynthesis; Arbutin - pharmacology; Bacterial Proteins - chemistry; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Cell Line, Tumor; Endopeptidases - chemistry; Esters - pharmacology; Fundamental and applied biological sciences. Psychology; Medical sciences; Melanin; Melanins - antagonists & inhibitors; Melanins - biosynthesis; Melanoma, Experimental - metabolism; Methods. Procedures. Technologies; Mice; Pharmacology. Drug treatments; Skin Neoplasms - metabolism; Skin, nail, hair, dermoskeleton; Tyrosinase; Tyrosinase inhibitor; Undecylenic acid; Undecylenic Acids - pharmacology; Tyrosinase inhibitor; Arbutin; Tyrosinase; Melanin; Undecylenic acid; Spontaneous; Glucose; Ester; B16-Melanoma; Glycoside; Tumor cell; Enzymatic synthesis; Catalytic reaction; Aldose; Enzyme; Rodentia; Enzyme inhibitor; Malignant tumor; Monophenol monooxygenase; Melanogenesis; Transesterification; Peptidases; Vertebrata; Mammalia; Mouse; Animal; Phenols; Hydrolases; Oxidoreductases
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2007.03.039

Transesterification of arbutin and undecylenic acid vinyl ester was catalyzed by protease to get arbutin derivative having undecylenic acid ester. The arbutin ester significantly suppressed melanin production in murine B16 melanoma cells. 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 β- 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.