title: Lignan dicarboxylates and terpenoids from the flower buds of Cananga odorata and their inhibitory effects on melanogenesis.
abstract: The methanolic extract from the flower buds of Cananga odorata showed an inhibitory effect on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extract, two new lignan dicarboxylates, canangalignans I and II, three new terpenoids, canangaterpenes I, II, and III, and eight known compounds were isolated. The structures of these compounds were elucidated on the basis of chemical/physicochemical evidence. Several mono- and sesquiterpene analogues significantly inhibited melanogenesis. In particular, canangaterpene I and (3R,3aR,8aS)-3-isopropyl-8a-methyl-8-oxo-1,2,3,3a,6,7,8,8a-octahydroazulene-5-carbaldehyde exhibited a potent inhibitory effect on melanogenesis [inhibition (%): 34.7±4.2 (p<0.01), 45.5±5.7 (p<0.01) at 1 μM, respectively] without inducing cytotoxicity. Moreover, the biological effect of these compounds was much stronger than that of the reference compound, arbutin. Thus, these isolated terpenoid derivatives may be promising therapeutic agents for the treatment of several skin disorders.
authors.affiliation: 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: Katsuyoshi
authors.initials: K
authors.lastname: Fujimoto
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
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
mesh_terms: D000465:Algorithms; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D054362:Cananga / Q000737:chemistry*; D003998:Dicarboxylic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D035264:Flowers / Q000737:chemistry; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008546:Melanoma, Experimental / Q000188:drug therapy; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013785:Thailand; D013806:Theophylline / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D003998:Dicarboxylic Acids; D017705:Lignans; D013729:Terpenes; C000589786:canangaterpene I; D013806:Theophylline