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    Article

    Ingenine F: A New Cytotoxic Tetrahydro Carboline Alkaloid from the Indonesian Marine Sponge Acanthostrongylophora ingens

    Sabrin Ibrahim2,3★, Gamal Mohamed4,5, Rwaida Al Haidari2, Amal El‑Kholy6,7, Mohamed Zayed2,8★ Corresponding author

    1. 1Department of Pharmacognosy and Pharmaceutical Chemistry, College of Pharmacy, Taibah University, Al Madinah Al Munawwarah 41477, Saudi Arabia.
    2. 2Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.
    3. 3Department of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah, 21589, Saudi Arabia.
    4. 4Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524, Egypt.
    5. 5Department of Clinical and Hospital Pharmacy, College of Pharmacy, Taibah University, Al Madinah Al Munawwarah 30078, Saudi Arabia.
    6. 6Department of Clinical Pharmacy, Faculty of Pharmacy, Ain-Shams University, Cairo 11566.
    7. 7Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.

    CORRESPONDENCE

    Sabrin Ibrahim

    Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.

    sribrahim@taibahu.edu.sa

    Received: 23-10-2017; Revised: 23-11-2017.

    Volume 14, Issue 54 · pp. 231–234 · PUBLISHED 10 April 2018 · DOI: 10.4103/pm.pm_489_17

    View on Pharmacogn. Mag. original site ↗

    ABSTRACT

    Background: Marine organisms are established to be a wealthy source of bioactive compounds with diverse chemical structures and bioactivities. Acanthostrongylophora ingens is known to be rich with pyrimidine b-carboline and manzamine-type alkaloids. The goal of the present work is to isolate and identify new alkaloids from A. ingens as well as to assess the cytotoxic potential of these metabolites towards various cancer cell lines. Methods: The crude MeOH extract of the sponge was separated by vacuum liquid chromatography (VLC), using n-hexane, EtOAc, and MeOH. The EtOAc fraction was chromatographed on VLC, SiO2, sephadex LH-20, and RP18 columns, affording four metabolites. Their structures were identified using infrared, ultraviolet, high‑resolution mass spectrometry, and nuclear magnetic resonance spectroscopic techniques, as well as comparison with the published data. Results: A new 1,2,3,4‑tetrahydro‑β‑carboline (THβCs) alkaloid, ingenine F (4) and three known compounds: Annomontine (1), acanthomine A (2), and 1‑oxo‑1,2,3,4‑THβCs (3) were isolated and identified. Ingenine F (4) exhibited cytotoxic activity toward hormone‑dependent breast carcinoma (MCF7), colon carcinoma (HCT116), and lung carcinoma (A549) cell lines with IC50 values of 2.82, 1.00, and 2.37 μM, respectively, compared to doxorubicin (IC50 0.012, 0.036, and 0.102 μM, respectively). Conclusion: It is the first report for the isolation of THβCs alkaloids from A. ingens. The THβCs alkaloid with N‑methylbutyramide unit as found in ingenine F is very rarely encountered in nature. Ingenine F may provide new promising candidates for potential cytotoxic agent.

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      Ibrahim, S., Mohamed, G., Haidari, R. A., El‑Kholy, A., & Zayed, M. (2018). Ingenine F: A New Cytotoxic Tetrahydro Carboline Alkaloid from the Indonesian Marine Sponge Acanthostrongylophora ingens. Pharmacognosy Magazine, 14(54), 231–234. https://doi.org/10.4103/pm.pm_489_17