Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation.

Basic Information

ID: ALA4665747

Journal: J Nat Prod

Title: Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation.

Authors: Andreeva OV,Garifullin BF,Sharipova RR,Strobykina IY,Sapunova AS,Voloshina AD,Belenok MG,Dobrynin AB,Khabibulina LR,Kataev VE

Abstract: Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.

CiteXplore: 32786882

DOI: 10.1021/acs.jnatprod.0c00134

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