Inhibitory effects of arbutin-beta-glycosides synthesized from enzymatic transglycosylation for melanogenesis.
To develop a new skin whitening agent, arbutin-beta-glycosides were synthesized and evaluated for their melanogenesis inhibitory activities. Three active compounds were synthesized via the transglycosylation reaction of Thermotoga neapolitana beta-glucosidase and purified by recycling preparative HPLC. As compared with arbutin (IC(50 )= 6 mM), the IC(50 )values of these compounds were 8, 10, and 5 mM for beta-D -glucopyranosyl-(1-->6)-arbutin, beta-D: -glucopyranosyl-(1-->4)-arbutin, and beta-D -glucopyranosyl-(1-->3)-arbutin, respectively. beta-D: -Glucosyl-(1-->3)-arbutin also exerted the most profound inhibitory effects on melanin synthesis in B16F10 melanoma cells. Melanin synthesis was inhibited to a significant degree at 5 mM, at which concentration the melanin content was reduced to below 70% of that observed in the untreated cells. Consequently, beta-D: -glucopyranosyl-(1-->3)-arbutin is a more effective depigmentation agent and is also less cytotoxic than the known melanogenesis inhibitor, arbutin.
Jun
So-Young
SY
Department of Biological Sciences, College of Natural Sciences, Pusan National University, Busan 609-735, Republic of Korea.
Park
Kyung-Min
KM
Choi
Ki-Won
KW
Jang
Min Kyung
MK
Kang
Hwan Yul
HY
Lee
Sang-Hyeon
SH
Park
Kwan-Hwa
KH
Cha
Jaeho
J
D000818:Animals; D001104:Arbutin / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D006031:Glycosylation; D008543:Melanins / Q000378:metabolism; D008545:Melanoma / Q000378:metabolism / Q000473:pathology; D051379:Mice; D015394:Molecular Structure; D046949:Thermotoga neapolitana / Q000201:enzymology / Q000378:metabolism; D001617:beta-Glucosidase / Q000378:metabolism
D006027:Glycosides; D008543:Melanins; D001104:Arbutin; D001617:beta-Glucosidase