title: Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis.
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.
authors.affiliation: Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
authors.forename: Seikou
authors.initials: S
authors.lastname: Nakamura
authors.forename: Katsuyoshi
authors.initials: K
authors.lastname: Fujimoto
authors.forename: Takahiro
authors.initials: T
authors.lastname: Matsumoto
authors.forename: Souichi
authors.initials: S
authors.lastname: Nakashima
authors.forename: Tomoe
authors.initials: T
authors.lastname: Ohta
authors.forename: Keiko
authors.initials: K
authors.lastname: Ogawa
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
mesh_terms: D000215:Acylation; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D035264:Flowers / Q000737:chemistry*; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D008545:Melanoma / Q000139:chemically induced / Q000188:drug therapy* / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D027861:Prunus / Q000737:chemistry*; D011801:Quinic Acid / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013395:Sucrose / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013806:Theophylline; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D008543:Melanins; D011801:Quinic Acid; D013395:Sucrose; D013806:Theophylline