Papaver species have been used to treat several diseases in Anatolia [1]. Chromatographic investigations on the P. lacerum methanolic extract (MeOH) resulted in isolation of a phenolic compound (I) and a new mevalonic acid derivative (II). Structures of the compounds were elucidated as tyrosol-1-O-β-D-xylopyranosyl-(1→6)-O-β-D-glucopyranoside and 5-O-(6-O-a-L-rhamnopyranosyl-β-D-glucopyranosyl mevalonic acid by spectroscopic analysis. A ligand based virtual screening technique (Rocs & EON) was used to screen I and II in drug like libraries, which provided similar structures [2]. For compound I, the most similar active ligand was EPIRUBICIN which is used to treat breast cancers [3]. ROCS TanimotoCombo was 0.665. EON ET combo was 0.911. For compound II, the most similar active ligand was VISMODEGIB, which is used to treat basal-cell carcinoma [3]. ROCS TanimotoCombo was 0.794. EON ET combo was 0.85. MTT cytotoxicity assay was carried out to assess cytotoxicity of I and II on HeLa cell line, which revealed moderate activity. In Figure A “I” (100 µM) is cytotoxic to HeLa cells by more than 40% (p < 0.0001). As shown in Figure B “II” (100 µM) is cytotoxic to HeLa cells by 65% (p< 0.0001), whereas P. lacerum MeOH extract exhibited more cytotoxicity with 17% cell viability at 100 µg/mL (p< 0.0001). Cisplatin 30 µM was used as a positive control.
References:
[1] Mukemre M, Behcet L, Cakilcioglu U. J Ethnopharmacol 2015; 166:361-74.
[2] Hawkins PC, Skillman AG, Nicholls A. J Med Chem. 2007; 50(1):74-82.
[3] Law V, Knox C, Djoumbou Y, Jewison T, Guo AC, Liu Y. DrugBank 4.0: shedding new light on drug metabolism. Nucleic Acids Research. 2014; 42 (Database issue): D1091-D7.