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

被引:26
|
作者
Matsumoto, Takahiro [1 ]
Nakamura, Seikou [1 ]
Nakashima, Souichi [1 ]
Yoshikawa, Masayuki [1 ]
Fujimoto, Katsuyoshi [1 ]
Ohta, Tomoe [1 ]
Morita, Azumi [1 ]
Yasui, Rie [1 ]
Kashiwazaki, Eri [1 ]
Matsuda, Hisashi [1 ]
机构
[1] Kyoto Pharmaceut Univ, Dept Pharmacognosy, Yamashina Ku, Kyoto 6078412, Japan
基金
日本学术振兴会;
关键词
Curcuma comosa; Diarylcomosol; Diarylheptanoid; Melanogenesis inhibitor; Thai traditional medicine; RADICAL SCAVENGING ACTIVITIES; CHINESE CAMELLIA-JAPONICA; FLOWER BUDS; OLEANANE-TYPE; TRITERPENE SAPONINS; ALPINIA-OFFICINARUM; PHENOLIC-COMPOUNDS; ACER-NIKOENSE; BARK; KWANGSIENSIS;
D O I
10.1016/j.bmcl.2013.07.010
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5178 / 5181
页数:4
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