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.

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.

Key words:

• lignan
• epoxylignan
• cytotoxic activity
• verrucosin
• caspase

Acknowledgment

Part of this study was performed at ADRES (Johoku station) of Ehime University. We are grateful to Marutomo Co. for financial support.

Disclosure statement

No potential conflict of interest was reported by the authors.