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Radical scavenging and antiproliferative effect of novel phenolic derivatives isolated from Nerium indicum against human breast cancer cell line (MCF-7)—an in silico and in vitro approach

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Abstract

Multiple drug resistance and increased side effects due to allopathic drugs has warned scientific community with a global alarm to identify molecules from natural sources to combat diseases with minimum or no side effects. The present investigation was aimed to identify and isolate secondary metabolites from traditionally used Nerium indicum using conventional column chromatography which led to the isolation of two compounds, C-I (fractions NB4f1) and C-II (fractions NC13b1). Further characterized, it is elucidated using spectral data and identified as N-(4-hydroxy-phenyl)-2-methoxy-2-phenyl-acetamide, molecular formula C15H15NO3, and molecular weight 257.3 (C-I) and N-(4-hydroxy-phenyl)-2-phenyl-N-phenylacetyl-acetamide, molecular formula C22H19NO3, and molecular weight 345.4 (C-II). Further, the isolated compounds were investigated using in silico approach by Autodock tool with four different proteins specific for cancer and in vitro assessed cell proliferation, and apoptosis against human breast cancer MCF 7 cell line. The results of the in silico model demonstrated potent binding affinity of both compounds with the proteins representing that the isolated molecules could be a drug of choice for cancer. Further, the isolated compounds revealed significant inhibition of cell proliferation (IC50 values 21 μg/mL for C-I, 19 μg/mL for C-II) with induced apoptosis with nuclear condensation effect on the MCF 7 cells in in vitro condition even at very low concentration. Compound treatment to MCF-7 cell line represented bright fetches indicating condensed chromatins and higher level of nuclear fragmentation with DAPI staining, indicating higher cell death due to induced apoptosis and confirmed using flow cytometry analysis representing inhibition of cell proliferation at S phase.

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  • 26 February 2020

    The correct presentation of the Author names are shown in this paper.

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Acknowledgments

Authors are thankful to the Management and Principal of K.S.Rangasamy College of Technology, Tiruchengode (DBT-FIST and DBT-STAR), for providing infrastructure and facilities to carry out this research work successfully. Moreover, we extend our heartfelt thanks to the management and Principal of C. Abdul Hakeem College for their support during the project.

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Authors and Affiliations

  1. Department of Chemistry, C. Abdul Hakeem College, Melvisharam, Vellore, Tamil Nadu, India

    Thangakumar Arunachalam, Syed Tajudeen Syed Ameen, Ibrahim Sheriff Ameer Khadharu & Dastageer M. Sabu

  2. Department of Biotechnology, K.S.Rangasamy College of Technology, Tiruchengode, Tamil Nadu, India

    Syed Zameer Ahmed Khader, Sidhra Syed Zameer Ahmed, Manimaran Vetrivel, Puniethaa Prabhu & Philp Robinson Jayachandran

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  1. Thangakumar Arunachalam
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  2. Syed Zameer Ahmed Khader
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  3. Sidhra Syed Zameer Ahmed
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  4. Manimaran Vetrivel
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Contributions

Mr. A. Thangakumar—purification of active principles from plant extract

Dr. K. Syed Zameer Ahmed—purification of active principles from plant extract and wrote the manuscript

Dr. S. Sidhra—purification of active principles from plant extract and corrected the manuscript

Dr. S. Syed Tajudeen—characterization of isolated compounds (IR, NMR)

Dr. A.K. Ibrahim Sheriff—characterization of isolated compound I and data writing

Dr. M.S.Dastageer—characterization of isolated compound II and data writing

Dr. P. Punitha, Dr. J. Philp Robinson, and Mr. V. Manimaran—performed Insilco work on Nerium indicum

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Correspondence to Syed Zameer Ahmed Khader.

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Arunachalam, T., Khader, S.Z.A., Syed Zameer Ahmed, S. et al. Radical scavenging and antiproliferative effect of novel phenolic derivatives isolated from Nerium indicum against human breast cancer cell line (MCF-7)—an in silico and in vitro approach. Environ Sci Pollut Res 27, 9038–9057 (2020). https://doi.org/10.1007/s11356-019-07252-x

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