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. Issue 4 (2nd April 2016)

• Record Type: Journal Article
• Authors: Wukirsari, Tuti; Nishiwaki, Hisashi; Nishi, Kosuke; Sugahara, Takuya; Akiyama, Koichi; Kishida, Taro; Yamauchi, Satoshi
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 80:Issue 4(2016)
• Page Start: 669
• Page End: 675
• Publication Date: 2016-04-02
• Subjects: lignan -- epoxylignan -- cytotoxic activity -- verrucosin -- caspase; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1080/09168451.2015.1123603
• Languages: English
• ISSNs: 0916-8451

Abstract

Abstract: We compared the cytotoxic activities of dietary epoxylignans and their stereoisomers and found (−)-verrucosin, which is (7 S, 7′ R, 8 R, 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. Graphical abstract: : 3′, 4, 4′-Trimethoxy-7, 7′-epoxylignan showed highest IC50 value (2.4 μM) in this structure–cytotoxic activity relationship experiment of 7, 7′-epoxylignan. The IC50 value of natural (−)-verrucosin was 6.6 μM.