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    Article

    Studies on the Red Sea Sponge Haliclona sp. for its Chemical and Cytotoxic Properties

    Shaza Mohamed Al-Massarani1★, Ali Ali El-Gamal1,2, Mansour Sulaiman Al-Said1, Maged S. Abdel-Kader3,4, Abdelkader E. Ashour5, Ashok Kumar6, Wael M. Abdel-Mageed1,7, Adnan Jathlan Al-Rehaily1, Hazem A. Ghabbour8, Hoong-Kun Fun8★ Corresponding author

    1. 1Departments of Pharmacognosy, Pharmacology and Toxicology and Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
    2. 2Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, El-Mansoura 35516, Egypt.
    3. 3Department of Pharmacognosy, College of Pharmacy, Alexandria University, Alexandria 21215, Egypt.
    4. 4Department of Pharmacognosy, College of Pharmacy, Sattam Bin Abdulaziz University, Al-kharj 11942, Saudi Arabia.
    5. 5Departments of Pharmacology and Toxicology, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
    6. 6Vitiligo Research Chair, College of Medicine, King Saud University, Riyadh, Saudi Arabia.
    7. 7Department of Pharmacognosy, Faculty of Pharmacy, Assiut University 71526, Assiut, Egypt.
    8. 8Departments of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

    CORRESPONDENCE

    Shaza Mohamed Al-Massarani

    Departments of Pharmacognosy, Pharmacology and Toxicology and Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

    shazams@yahoo.com

    Received: 01-07-2015; Revised: 22-07-2015; Accepted: 03-02-2016.

    Volume 12, Issue 46 · pp. 114–9 · PUBLISHED 2 March 2016 · DOI: 10.4103/0973-1296.177906

    View on Pharmacogn. Mag. original site ↗

    ABSTRACT

    Background: A great number of novel compounds with rich chemical diversity and significant bioactivity have been reported from Red Sea sponges. Objective: To isolate, identify, and evaluate the cytotoxic activity of the chemical constituents of a sponge belonging to genus Haliclona collected from the Eastern coast of the Red Sea. Materials and Methods: The total ethanolic extract of the titled sponge was subjected to intensive chromatographic fractionation and purification guided by cytotoxic bioassay toward various cancer cell lines. The structures of the isolated compounds were elucidated using spectroscopic techniques including one‑dimension and two‑dimension nuclear magnetic resonance, mass spectrometry, ultraviolet, and infrared data, as well as comparison with the reported spectral data for the known compounds. X‑ray single‑crystal structure determination was performed to determine the absolute configuration of compound 4. The screening of antiproliferative activity of the compounds was carried on three tumor cell lines, namely the human cervical cancer (HeLa), human hepatocellular carcinoma (HepG2), and human medulloblastoma (Daoy) cells using MTT assay. Results: This investigation resulted in the isolation of a new indole alkaloid, 1‑(1H‑indol‑3‑yloxy) propan‑2‑ol (1), with the previously synthesized pyrrolidine alkaloid, (2R, 3S, 4R, 5R) pyrrolidine‑(1‑hydroxyethyl)‑3,4‑diol hydrochloride (4), isolated here from a natural source for the first time. In addition, six known compounds tetillapyrone (2), nortetillapyrone (3), 2‑methyl maleimide‑5‑oxime (5), maleimide‑5‑oxime (6), 5‑(hydroxymethyl) dihydrofuran‑2 (3H)‑one (7), and ergosta‑5,24 (28)‑dien‑3‑ol (8) were also identified. Most of the isolated compounds exhibited weak cytotoxic activity against HepG‑2, Daoy, and HeLa cancer cell lines. Conclusion: This is the first report of the occurrence of the indole and pyrrolidine alkaloids, 1‑(1H‑indol‑2‑yloxy) propan‑2‑ol (1), and the ‑ (1‑hydroxyethyl)‑3,4‑diol hydrochloride (4), in the Red Sea Haliclona sp.

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      Al-Massarani, S. M., El-Gamal, A. A., Al-Said, M. S., Abdel-Kader, M. S., Ashour, A. E., Kumar, A., Abdel-Mageed, W. M., Al-Rehaily, A. J., Ghabbour, H. A., & Fun, H. (2016). Studies on the Red Sea Sponge Haliclona sp. for its Chemical and Cytotoxic Properties. Pharmacognosy Magazine, 12(46), 114–9. https://doi.org/10.4103/0973-1296.177906