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DNA-protector and cytotoxic activity of secoisolariciresinol diglucoside derivatives

Stasevich, O. V., Shman, T. V., Mikhalenok, S. G., Kurchenko, V. P.
Chemistry of natural compounds 2010 v.46 no.5 pp. 704-709
Linum usitatissimum, acetylation, carbohydrates, chemical structure, cytotoxicity, free radicals, lignans, neoplasms, phenol, seeds
The relationship between the chemical structure and DNA-protector and cytotoxic activities of phenylpropane lignans was studied. Analogs were synthesized from the lignan secoisolariciresinol diglucoside (SDG) isolated from Linum usitatissimum seeds. It was shown that SDG derivatives secoisolariciresinol and secoisolariciresinol-4′,4″-diacetate, which were not glucosides, exhibited greater cytotoxic activity in vitro than the starting lignan. The cytotoxicity was slightly elevated upon acetylation of the aglycon phenol hydroxyls whereas the DNA-protector activity decreased substantially. The DNA-protector activity of the derivative without the carbohydrate was slightly greater than that of the starting SDG. This was explained by binding of free radicals by the butanediol hydroxyls. It was proposed that the activity of the cytotoxic derivatives was mediated by induction of apoptosis of the tumor cells.