Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings |
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Authors: | Satoshi Yamauchi Tuti Wukirsari Yoshiaki Ochi Hisashi Nishiwaki Kosuke Nishi Takuya Sugahara Koichi Akiyama Taro Kishida |
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Institution: | 1. Graduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan;2. South Ehime Fisheries Research Center, 1289-1 Funakoshi, Ainan, Ehime 798-4292, Japan;3. Advanced Research Support Center (ADRES), Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan |
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Abstract: | The new lignano-9,9′-lactones (α,β-dibenzyl-γ-butyrolactone lignans), which showed the higher cytotoxicity than arctigenin, were synthesized. The well-known cytotoxic arctigenin showed activity against HL-60 cells (EC50 = 12 μM), however, it was inactive against HeLa cells (EC50 > 100 μM). The synthesized (3,4-dichloro, 2′-butoxy)-derivative 55 and (3,4-dichloro, 4′-butyl)-derivative 66 bearing the lignano-9,9′-lactone structures showed the EC50 values of 10 μM and 9.4 μM against HL-60 cells, respectively. Against HeLa cells, the EC50 value of the derivative 66 was 27 μM. By comparing the activities with the corresponding 9,9′-epoxy structure (tetrahydrofuran compounds), the importance of the lactone structure of 55 and 66 for the higher activities was shown. The substituents on the aromatic ring of the lignano-9,9′-lactones affected the cytotoxicity level, observing more than 10-fold difference. |
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Keywords: | Lignan Arctigenin Matairesinol γ-Butyrolactone Lignano-9 9′-lactone α β-Dibenzyl-γ-butyrolactone |
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