RRC ID 69817
Author Nakamura S, Fujimoto K, Matsumoto T, Nakashima S, Ohta T, Ogawa K, Matsuda H, Yoshikawa M.
Title Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis.
Journal Phytochemistry
Abstract The methanolic extract from the flower buds of Prunus mume, cultivated in Zhejiang Province, China, showed an inhibitory effect on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the methanolic extract, five acylated sucroses, mumeoses A-E, and three acylated quinic acid analogs, 5-O-(E)-p-coumaroylquinic acid ethyl ester, and mumeic acid-A and its methyl ester, were isolated together with 13 known compounds. The chemical structures of the compounds were elucidated on the basis of chemical and physicochemical evidence. Inhibitory effects of the isolated compounds on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were also investigated. Acylated quinic acid analogs substantially inhibited melanogenesis. In particular, 5-O-(E)-feruloylquinic acid methyl ester exhibited a potent inhibitory effect [inhibition (%): 21.5±1.0 (P<0.01) at 0.1 μM]. Moreover, its biological effect was much stronger than that of the reference compound, arbutin [inhibition (%): 10.6±0.6 (P<0.01) at 10 μM]. Interestingly, the obtained acylated quinic acid analogs displaying melanogenesis inhibitory activity showed no cytotoxicity [cell viability >97% at 10 μM]. It is concluded that acylated quinic acid analogs are promising therapeutic agents for the treatment of skin disorders.
Volume 92
Pages 128-36
Published 2013-8-1
DOI 10.1016/j.phytochem.2013.04.012
PII S0031-9422(13)00153-2
PMID 23693120
MeSH Acylation Animals Antineoplastic Agents, Phytogenic / chemistry Antineoplastic Agents, Phytogenic / isolation & purification Antineoplastic Agents, Phytogenic / pharmacology* Cell Survival / drug effects Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Flowers / chemistry* Melanins / antagonists & inhibitors* Melanins / biosynthesis Melanoma / chemically induced Melanoma / drug therapy* Melanoma / metabolism Mice Molecular Structure Prunus / chemistry* Quinic Acid / chemistry Quinic Acid / isolation & purification Quinic Acid / pharmacology* Structure-Activity Relationship Sucrose / chemistry Sucrose / isolation & purification Sucrose / pharmacology* Theophylline Tumor Cells, Cultured
IF 3.044
Human and Animal Cells B16 melanoma 4A5(RCB0557)