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Lignan Dicarboxylates and Terpenoids from the Flower Buds of Cananga odorata and Their Inhibitory Effects on Melanogenesis

2014; American Chemical Society; Volume: 77; Issue: 4 Linguagem: Inglês

10.1021/np401091f

1520-6025

Takahiro Μatsumoto, Seikou Nakamura, Souichi Nakashima, Katsuyoshi Fujimoto, Masayuki Yoshikawa, Tomoe Ohta, K. Ogawa, Hisashi Matsuda,

Phytochemical compounds biological activities

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.