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: Takahiro Matsumoto, Seikou Nakamura, Souichi Nakashima, Katsuyoshi Fujimoto, Masayuki Yoshikawa, Tomoe Ohta, Keiko Ogawa, Hisashi Matsuda
• Journal: Journal of natural products (J Nat Prod) Vol. 77 Issue 4 Pg. 990-9 (Apr 25 2014) ISSN: 1520-6025 [Electronic] United States
• PMID: 24601675 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Dicarboxylic Acids
• Lignans
• Terpenes
• canangaterpene I
• Theophylline

Topics

• Algorithms
• Animals
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Cananga (chemistry)
• Dicarboxylic Acids (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Flowers (chemistry)
• Lignans (chemistry, isolation & purification, pharmacology)
• Melanoma, Experimental (drug therapy)
• Mice
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Stereoisomerism
• Terpenes (chemistry, isolation & purification, pharmacology)
• Thailand
• Theophylline (pharmacology)