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Article

New Cytotoxic Cerebrosides from the Red Sea Cucumber Holothuria spinifera Supported by In-Silico Studies

1
Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Nahda University, Beni Suef 62513, Egypt
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Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, Riyadh 13414, Saudi Arabia
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Department of Pharmacognosy, Faculty of Pharmacy, Modern University for Technology and Information, Cairo 11566, Egypt
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Department of Pharmacognosy, Faculty of Pharmacy, Deraya University, New Minia 61111, Egypt
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Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut 71524, Egypt
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Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
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Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo 11566, Egypt
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Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt
*
Authors to whom correspondence should be addressed.
Equal contribution.
Mar. Drugs 2020, 18(8), 405; https://doi.org/10.3390/md18080405
Received: 30 June 2020 / Revised: 17 July 2020 / Accepted: 23 July 2020 / Published: 1 August 2020
(This article belongs to the Special Issue Nutraceuticals and Pharmaceuticals from Marine Fish and Invertebrates)
Bioactivity-guided fractionation of a methanolic extract of the Red Sea cucumber Holothuria spinifera and LC-HRESIMS-assisted dereplication resulted in the isolation of four compounds, three new cerebrosides, spiniferosides A (1), B (2), and C (3), and cholesterol sulfate (4). The chemical structures of the isolated compounds were established on the basis of their 1D NMR and HRMS spectral data. Metabolic profiling of the H. spinifera extract indicated the presence of diverse secondary metabolites, mostly hydroxy fatty acids, diterpenes, triterpenes, and cerebrosides. The isolated compounds were tested for their in vitro cytotoxicities against the breast adenocarcinoma MCF-7 cell line. Compounds 1, 2, 3, and 4 displayed promising cytotoxic activities against MCF-7 cells, with IC50 values of 13.83, 8.13, 8.27, and 35.56 µM, respectively, compared to that of the standard drug doxorubicin (IC50 8.64 µM). Additionally, docking studies were performed for compounds 1, 2, 3, and 4 to elucidate their binding interactions with the active site of the SET protein, an inhibitor of protein phosphatase 2A (PP2A), which could explain their cytotoxic activity. This study highlights the important role of these metabolites in the defense mechanism of the sea cucumber against fouling organisms and the potential uses of these active molecules in the design of new anticancer agents. View Full-Text
Keywords: LC-HRESIMS; Holothuria spinifera; cerebrosides; molecular docking; cytotoxicity LC-HRESIMS; Holothuria spinifera; cerebrosides; molecular docking; cytotoxicity
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MDPI and ACS Style

Abdelhameed, R.F.A.; Eltamany, E.E.; Hal, D.M.; Ibrahim, A.K.; AboulMagd, A.M.; Al-Warhi, T.; Youssif, K.A.; Abd El-kader, A.M.; Hassanean, H.A.; Fayez, S.; Bringmann, G.; Ahmed, S.A.; Abdelmohsen, U.R. New Cytotoxic Cerebrosides from the Red Sea Cucumber Holothuria spinifera Supported by In-Silico Studies. Mar. Drugs 2020, 18, 405. https://doi.org/10.3390/md18080405

AMA Style

Abdelhameed RFA, Eltamany EE, Hal DM, Ibrahim AK, AboulMagd AM, Al-Warhi T, Youssif KA, Abd El-kader AM, Hassanean HA, Fayez S, Bringmann G, Ahmed SA, Abdelmohsen UR. New Cytotoxic Cerebrosides from the Red Sea Cucumber Holothuria spinifera Supported by In-Silico Studies. Marine Drugs. 2020; 18(8):405. https://doi.org/10.3390/md18080405

Chicago/Turabian Style

Abdelhameed, Reda F.A., Enas E. Eltamany, Dina M. Hal, Amany K. Ibrahim, Asmaa M. AboulMagd, Tarfah Al-Warhi, Khayrya A. Youssif, Adel M. Abd El-kader, Hashim A. Hassanean, Shaimaa Fayez, Gerhard Bringmann, Safwat A. Ahmed, and Usama R. Abdelmohsen 2020. "New Cytotoxic Cerebrosides from the Red Sea Cucumber Holothuria spinifera Supported by In-Silico Studies" Marine Drugs 18, no. 8: 405. https://doi.org/10.3390/md18080405

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