Planta Medica International Open 2017; 4(S 01): S1-S202
DOI: 10.1055/s-0037-1608153
Poster Session
Georg Thieme Verlag KG Stuttgart · New York

Structure virtual screening of two cytotoxic compounds isolated from Papaver lacerum

O Bayazeid
1   Hacettepe University, Faculty of Pharmacy, Dept. of Pharmacognosy, ANKARA, Turkey
,
E Bedir
2   Izmir Institute of Technology, Faculty of Engineering, Dept. of Bioengineering, Izmir, Turkey
,
F Yalçın
1   Hacettepe University, Faculty of Pharmacy, Dept. of Pharmacognosy, ANKARA, Turkey
› Author Affiliations
Further Information

Publication History

Publication Date:
24 October 2017 (online)

 

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” (100µM) is cytotoxic to HeLa cells by more than 40% (p < 0.0001). As shown in Figure B “II” (100µM) 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 30µM was used as a positive control.

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Fig. 1

[1] Mukemre M, Behcet L, Cakilcioglu U. J Ethnopharmacol 2015; 166:361 – 74.

[2] Hawkins PC, Skillman AG, Nicholls A. J Med Chem. 2007; 50:74 – 82.

[3] Law V, Knox C, Djoumbou Y, Jewison T, Guo AC, Liu Y. Nucleic Acids Research. 2014; 42 (Database issue): D1091-D7.