Novel synthesis of zerumbone-pendant derivatives and their biological activity |
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| Authors: | Takashi Kitayama Maki Nakahira Kae Yamasaki Hiromi Inoue Chika Imada Yuji Yonekura Masataka Awata Hikaru Takaya Yasushi Kawai Kohta Ohnishi Akira Murakami |
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| Institution: | 1. Department of Advanced Bioscience, Graduate School of Agriculture, Kinki University, Nara 631-8505, Japan;2. Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan;3. Nagahama Institute of Bio-Science and Technology, Nagahama, Shiga 526-0829, Japan;4. Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan |
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| Abstract: | Zerumbone 1, having powerful latent reactivity and containing two conjugated double bonds and a double conjugated carbonyl group is the major component of the essential oil of wild ginger, Zingiber zerumbet Smith. The conjugation system plays an important role in the expression of biological activity. N-Bromosuccinimide (NBS) reaction of 1 gave high reactive intermediate 2 with an exo-methylene group, which was obtained from 1 quantitatively. Treatment of 2 with nucleophiles gave various zerumbone-pendant derivatives, including C–H, C–O, C–N, and C–C bond formation, maintaining the conjugation system through SN2′-type reaction. Almost all zerumbone-pendant derivatives showed a good value of IC50 against the suppressive effect of NO generation. Among them, amine derivative 5, binding with 2 mol of zerumbone, showed the strongest activity (IC50: 0.24 μM). |
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