title: Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of Curcuma comosa in B16 melanoma cells.
abstract: The methanolic extract from the dried rhizomes of Curcuma comosa cultivated in Thailand was found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extract, three new diarylheptanoids, diarylcomosols I-III, were isolated together with 12 known diarylheptanoids. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The diarylheptanoids inhibited melanogenesis, and several structural requirements of the active constituents for the inhibition were clarified. In particular, (3R)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol exhibited stronger inhibitory effect [IC50=0.36 μM] without inducing cytotoxicity. The biological effect was much stronger than that of a reference compound, arbutin [IC50=174 μM]. We conclude that diarylheptanoid analogs are promising therapeutic agents for the treatment of skin disorders.
authors.affiliation: Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Matsumoto
authors.forename: Seikou
authors.initials: S
authors.lastname: Nakamura
authors.forename: Souichi
authors.initials: S
authors.lastname: Nakashima
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
authors.forename: Katsuyoshi
authors.initials: K
authors.lastname: Fujimoto
authors.forename: Tomoe
authors.initials: T
authors.lastname: Ohta
authors.forename: Azumi
authors.initials: A
authors.lastname: Morita
authors.forename: Rie
authors.initials: R
authors.lastname: Yasui
authors.forename: Eri
authors.initials: E
authors.lastname: Kashiwazaki
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D030024:Curcuma / Q000737:chemistry*; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D008544:Melanocytes / Q000187:drug effects* / Q000378:metabolism; D008546:Melanoma, Experimental / Q000188:drug therapy* / Q000473:pathology; D051379:Mice; D015394:Molecular Structure; D027343:Rhizome / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D036381:Diarylheptanoids
keywords: Curcuma comosa; Diarylcomosol; Diarylheptanoid; Melanogenesis inhibitor; Thai traditional medicine