title: Effect of the structure of dietary epoxylignan on its cytotoxic activity: relationship between the structure and the activity of 7,7'-epoxylignan and the introduction of apoptosis by caspase 3/7.
abstract: We compared the cytotoxic activities of dietary epoxylignans and their stereoisomers and found (-)-verrucosin, which is (7S,7'R,8R,8'R)-7,7'-epoxylignan, to be the most cytotoxic epoxylignan against HeLa cells (IC50 = 6.6 μM). On the other hand, the activity was about a factor of 10 less against HL-60. In this research on the relationship between the structure and cytotoxic activity of (-)-verrucosin 13, the 7-(4-methoxyphenyl)-7'-(3,4-dimethoxyphenyl) derivative 60, for which the activity (IC50 = 2.4 μM) is three times greater than (-)-verrucosin 13, was discovered. The induction of apoptosis by caspase 3/7 was observed upon treatment with the (-)-verrucosin derivative.
authors.affiliation: a Faculty of Agriculture , Ehime University , Matsuyama , Japan.
authors.forename: Tuti
authors.initials: T
authors.lastname: Wukirsari
authors.affiliation: a Faculty of Agriculture , Ehime University , Matsuyama , Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Nishiwaki
authors.affiliation: a Faculty of Agriculture , Ehime University , Matsuyama , Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Nishi
authors.affiliation: a Faculty of Agriculture , Ehime University , Matsuyama , Japan.|b South Ehime Fisheries Research Center , Ainan , Japan.
authors.forename: Takuya
authors.initials: T
authors.lastname: Sugahara
authors.affiliation: c Advanced Research Support Center (ADRES) , Ehime University , Matsuyama , Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Akiyama
authors.affiliation: a Faculty of Agriculture , Ehime University , Matsuyama , Japan.|b South Ehime Fisheries Research Center , Ainan , Japan.
authors.forename: Taro
authors.initials: T
authors.lastname: Kishida
authors.affiliation: a Faculty of Agriculture , Ehime University , Matsuyama , Japan.|b South Ehime Fisheries Research Center , Ainan , Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
mesh_terms: D017209:Apoptosis / Q000187:drug effects*; D053148:Caspase 3 / Q000378:metabolism*; D053179:Caspase 7 / Q000378:metabolism*; D004032:Diet; D004852:Epoxy Compounds / Q000737:chemistry* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D017705:Lignans / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D004852:Epoxy Compounds; D017705:Lignans; D053148:Caspase 3; D053179:Caspase 7
keywords: caspase; cytotoxic activity; epoxylignan; lignan; verrucosin