Isolation and Characterization of the Anticancer Compound Piceatannol from Sophora Interrupta Bedd

• Published in: International journal of preventive medicine Vol. 6; no. 1; p. 101
• Main Authors: Mathi, Pardhasaradhi, Das, Snehasish, Nikhil, Kumar, Roy, Partha, Yerra, Srikanth, Ravada, Suryachandra Rao, Bokka, Venkata Raman, Botlagunta, Mahendran
• Format: Journal Article
• Language: English
• Published: Iran Medknow Publications and Media Pvt. Ltd 2015; Medknow Publications & Media Pvt. Ltd; Medknow Publications & Media Pvt Ltd; Wolters Kluwer Medknow Publications
• Subjects: Active fraction; Angiogenesis; Breast cancer; Cancer; cancer cell lines; Cell cycle; characterization; Chromatography; Flavonoids; Fourier transforms; High performance liquid chromatography; Hydrocarbons; Legumes; Metabolism; Metabolites; NMR; Nuclear magnetic resonance; Nuclear magnetic resonance spectroscopy; Original; phenol; piceatannol; Prevention; Sophora interrupta roots; India; phenol; Active fraction; cancer cell lines; Sophora interrupta roots; piceatannol; characterization
• ISSN: 2008-7802; 2008-8213
• DOI: 10.4103/2008-7802.167181

Sophora belongs to the family of Fabaceae and the species in this genus are currently used as a folklore medicine for preventing a variety of ailments including cancer. Our aim was to identify and validate an anticancer compound from Sophora interrupta using multi-spectroscopic, anticancer screening, and molecular docking approach. The cytotoxicity of the various solvent extracts, petroleum ether, n-butanol, and ethyl acetate (EtOAc) of the S. interrupta root powder was evaluated in a breast cancer cell lines (MCF-7). The extract that had anticancer activity was subjected to column chromatography based on the polarity of the solvents. The anticancer activity of the elution fractions was validated using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The isolated metabolite fraction with anticancer activity was run through a C18 column isocratic and gradient high-performance liquid chromatography (HPLC). The structure of the isolated compound was characterized using (1)H nuclear magnetic resonance (NMR), (13)C-NMR, Fourier transform infrared spectroscopy, and liquid chromatography-mass spectrometer methods. The crude EtAOc extract effectively inhibited the proliferation of MCF-7 cells. The column eluted chloroform and EtOAc (4:6) fraction of the EtOAc extract showed significant anticancer activity in the MCF-7 cells compared with normal mesenchymal stem cells. This fraction showed three major peaks in the HPLC chromatogram and the first major peak with a retention time (RT) of 7.153 was purified using preparative-HPLC. The structure of the compound is a piceatannol, which is a metabolic product of resveratrol. Piceatannol formed direct two hydrogen bond interactions between Cys912 (2H), and Glu878 of vascular endothelial growth factor receptor 1 (VEGFR1) with a glide-score (G-score) of -10.193, and two hydrogen bond interactions between Cys919, and Asp1046 of VEGFR2, with a G-score of -8.359. The structure is similar to that of the crystallized protein for VEGFR1 and R2. Piceatannol is a secondary metabolite of S. interrupta that has anticancer activity. Moreover, piceatannol has been isolated for the first time from S. interrupta.