RRC ID 44009
Author Kikuchi T, Watanabe K, Tochigi Y, Yamamoto A, Fukatsu M, Ezaki Y, Tanaka R, Akihisa T.
Title Melanogenesis inhibitory activity of sesquiterpenes from Canarium ovatum resin in mouse B16 melanoma cells.
Journal Chem Biodivers
Abstract Four known sesquiterpene alcohols, i.e., 1-4, ten triterpene alcohols, i.e., 5-14, and four triterpene acids, i.e., 15-18, were isolated from the MeOH extract of Canarium ovatum resin (elemi resin). Upon evaluation of the previously described compounds 1-18 on the melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three sesquiterpene alcohols, i.e., cryptomeridiol (1), 4-epicryptomeridiol (2), and cadin-1(14)-ene-7α,11-diol (4), exhibited inhibitory effects with 27.4-34.1 and 39.0-56.9% reduction of melanin content at 50 and 100 μM, respectively, with no or very low toxicity to the cells (80.9-103.9% of cell viability at 100 μM). Western-blot analysis revealed that compounds 1 and 2 reduced the protein levels of MITF (=microphtalmia-associated transcription factor), tyrosinase, and TRP-2 (=tyrosine-related protein 2), mostly in a concentration-dependent manner, suggesting that these compounds exhibit melanogenesis inhibitory activity on α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of tyrosinase and TRP-2. Three sesquiterpene alcohols, i.e., 1, 2, and 4, are, therefore, considered to be valuable as potential skin-whitening agents.
Volume 9(8)
Pages 1500-7
Published 2012-8-1
DOI 10.1002/cbdv.201200111
PMID 22899610
MeSH Animals Burseraceae / chemistry* Cell Line, Tumor Cell Survival / drug effects Melanins / antagonists & inhibitors* Melanins / metabolism Melanoma, Experimental / metabolism* Mice Microphthalmia-Associated Transcription Factor / antagonists & inhibitors Microphthalmia-Associated Transcription Factor / metabolism Monophenol Monooxygenase / antagonists & inhibitors Monophenol Monooxygenase / metabolism Resins, Plant / chemistry* Resins, Plant / isolation & purification Resins, Plant / pharmacology* Sesquiterpenes / chemistry* Sesquiterpenes / isolation & purification Sesquiterpenes / pharmacology* alpha-MSH / antagonists & inhibitors alpha-MSH / metabolism
IF 2.039
Times Cited 10
WOS Category CHEMISTRY, MULTIDISCIPLINARY BIOCHEMISTRY & MOLECULAR BIOLOGY
Resource
Human and Animal Cells B16 melanoma 4A5(RCB0557)