Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of Curcuma comosa in B16 melanoma cells

作者：Matsumoto Takahiro; Nakamura Seikou; Nakashima Souichi; Yoshikawa Masayuki; Fujimoto Katsuyoshi; Ohta Tomoe; Morita Azumi; Yasui Rie; Kashiwazaki Eri; Matsuda Hisashi^*

来源：Bioorganic & Medicinal Chemistry Letters, 2013, 23(18): 5178-5181.

DOI：10.1016/j.bmcl.2013.07.010

• Curcuma comosa
• Diarylcomosol
• Diarylheptanoid
• Melanogenesis inhibitor
• Thai traditional medicine

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 mu M] without inducing cytotoxicity. The biological effect was much stronger than that of a reference compound, arbutin [IC50 = 174 mu M]. We conclude that diarylheptanoid analogs are promising therapeutic agents for the treatment of skin disorders.

• 出版日期2013-9-15