RRC ID 77887
Author Matsuda H, Nakashima S, Oda Y, Nakamura S, Yoshikawa M.
Title Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells.
Journal Bioorg Med Chem
Abstract The 80% aqueous acetone extract from the rhizomes of Alpinia officinarum, a Chinese medicinal herb, were found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Among the constituents isolated, four diarylheptanoids [5-hydroxy-1,7-diphenyl-3-heptanone, 7-(4('')-hydroxy-3('')-methoxyphenyl)-1-phenylhept-4-en-3-one, 5-hydroxy-7-(4('')-hydroxy-3('')-methoxyphenyl)-1-phenyl-3-heptanone, and 3,5-dihydroxy-1,7-diphenylheptane] and two flavonol constituents (kaempferide and galangin) inhibited melanogenesis with IC(50) values of 10-48microM, and several structural requirements of the active constituents for the inhibition were clarified. In addition, 7-(4('')-hydroxy-3('')-methoxyphenyl)-1-phenylhept-4-en-3-one, kaempferide, and galangin inhibited mRNA expression of tyrosinase and tyrosinase-related proteins-1 and -2, and the protein level of a microphthalmia-associated transcription factor.
Volume 17(16)
Pages 6048-53
Published 2009-8-15
DOI 10.1016/j.bmc.2009.06.057
PII S0968-0896(09)00616-6
PMID 19615910
MeSH Alpinia / chemistry* Animals Antineoplastic Agents / chemistry* Antineoplastic Agents / isolation & purification Antineoplastic Agents / pharmacology Enzyme Inhibitors / chemistry* Enzyme Inhibitors / isolation & purification Enzyme Inhibitors / pharmacology Flavonoids / chemistry Flavonoids / isolation & purification Flavonoids / pharmacology Kaempferols / chemistry Kaempferols / isolation & purification Kaempferols / pharmacology Melanoma, Experimental / drug therapy* Mice Monophenol Monooxygenase / antagonists & inhibitors* Monophenol Monooxygenase / metabolism Oxidoreductases / antagonists & inhibitors Oxidoreductases / metabolism Rhizome / chemistry
IF 3.073
Resource
Human and Animal Cells B16 melanoma 4A5(RCB0557)