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Cytotoxic activity evaluation and molecular docking study of phenolic derivatives from Achillea fragrantissima (Forssk.) growing in Egypt

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Abstract

Achillea fragrantissima (Forssk) Sch. Bip. (Asteraceae) is one of the most important medicinal plant species in Egypt. Phytochemical investigation of the methanolic extract of A. fragrantissima led to the isolation of two phenolic compounds Piceol (1) and Veratric acid (2), which are reported for the first time from this plant. In addition, four known flavonoid compounds; Eupatilin 7-methyl ether (3), Chrysosplenol D (4), Cirsiliol (5), and Cirsimaritin (6) were isolated. Structure elucidation was achieved using spectroscopic techniques, including one-dimensional and two-dimensional nuclear magnetic resonance. Potential cytotoxic activities of the isolated compounds were measured by the sulphorhodamine B assay. Compounds 1, 2, 3, 4, 5, and 6 displayed cytotoxic activity against (MCF7) with IC50 values of 18.2, 15.7, 9.5, 8.33, 3.23, and 3.83 µg/ml, respectively, and against (HepG2) with IC50 values of 19.4, 41.2, 28.3, 20.8, 23.8, and 23.8 µg/ml, respectively. Also there was moderate cytotoxic activity against (A549) with IC50 values of 17.8, 13.6, 3.98, and 10.3 µg/ml for the compounds 1, 2, 4 and 5, respectively, and against (HeLa) with IC50 values of 10.1, 10.4, 4.88, and 3.98 µg/ml for the compounds 3, 4, 5, and 6, respectively. In addition, compounds 4 and 5 showed cytotoxic activity against (PC3) with IC50 values of 3.83 and 3.98 µg/ml, respectively. An in silico study was performed, where cirsiliol (5) and piceol (1) were docked into the active sites of the crystal structures of PI3K and Akt, two protein kinases which are involved in prostate and breast cancer proliferation and survival.

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Acknowledgements

We are grateful to pro. Abd-Elraouf M., Faculty of Science, Sues Canal University, Ismailia, Egypt, for taxonomic identification of the plant.

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Authors and Affiliations

  1. Department of Pharmacognosy, Faculty of Pharmacy and Pharmaceutical Industries, Sinai University, North Sinai, Egypt

    Basma M. Awad

  2. Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, 41522, Egypt

    Eman S. Habib, Amany K. Ibrahim & Safwat A. Ahmed

  3. National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Oxford, MS, 38677, USA

    Amira S. Wanas, Mohamed M. Radwan & Mahmoud A. ElSohly

  4. Faculty of Pharmacy, Pharmacognosy, Minia University, Minia, Egypt

    Amira S. Wanas

  5. Faculty of Pharmacy, Pharmacognosy Department, Alexandria University, Alexandria, Egypt

    Mohamed M. Radwan

  6. Department of Medicinal Chemistry, Faculty of Pharmacy, Suez Canal University, Ismailia, 41522, Egypt

    Mohamed A. Helal & Mahmoud A. ElSohly

  7. Department of Pharmaceutics, School of Pharmacy, The University of Mississippi, University, Oxford, MS, 38677, USA

    Mahmoud A. ElSohly

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  1. Basma M. Awad
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Correspondence to Safwat A. Ahmed.

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Awad, B.M., Habib, E.S., Ibrahim, A.K. et al. Cytotoxic activity evaluation and molecular docking study of phenolic derivatives from Achillea fragrantissima (Forssk.) growing in Egypt. Med Chem Res 26, 2065–2073 (2017). https://doi.org/10.1007/s00044-017-1918-6

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