Secoisolariciresinol diglucoside (SDG) is isolated from Linum usitatissimum seeds. The antiproliferative effects of SDG (1) and its derivatives secoisolariciresinol (2) and secoisolariciresinol-4 ′, 4 ″-diacetate (3) have been evaluated on MCF-7 breast cancer cells and normal breast epithelial line MCF-10A. Lignan 1 has not shown cytotoxic effects on MCF-7 cells, while derivatives 2 and 3 have inhibited cell growth with IC 50 values of 25 and 11 µM, respectively. Estrogen receptor alpha is a key growth driver in MCF-7 cells. Compound 1 did not affect the activity of ERα, while derivatives 2 and 3 showed significant antiestrogenic effects.Compounds 2 and 3 caused apoptosis in the MCF-7 line, determined by the cleavage of PARP. SDG derivative 3 enhanced the effect of doxorubicin. SDG derivatives can be considered as promising agents that exhibit a combined antiestrogen and proapoptotic effect in hormonedependent breast cancer cells.
The optimum conditions for separating a lignan-containing extract from seeds of the oil flax (Linum usitatissimum) by thin-layer chromatography were identified. Elution using the method proposed here allowed identification of a brilliant blue fluorescent spot associated with the main lignan, which was secoisolariciresinol diglucoside (SDG), giving clear identification of this component in mixtures even without a standard. This method can be used for qualitative express analysis of phytopreparations based on lignans, with the aim of detecting adulterated phytopreparations and biologically active additives.
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-4c,4s-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.Lignans are natural biologically active compounds that consist of two phenylpropane units joined by a E-Ec-bond. Many representatives of this class exhibit antioxidant and antitumor properties [1]. Natural lignans are also interesting because of their ability to be used as templates for designing drugs with various biological activities (antitumor, antiviral, antifungal) [2]. Clear examples of medicines based on natural lignan are podophyllotoxin and its derivatives, the antitumor drugs etoposide and teniposide [2].Herein we report results from a study of the relationship between the chemical structure and biological activity of phenylpropane lignans that were synthesized from secoisolariciresinol diglucoside (SDG) isolated from seeds of Linum isutatissimum. We investigated the relationship of the DNA-protector and cytotoxic activity of the natural lignan SDG (1) and its derivatives to the chemical structure.
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