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Article

Holospiniferoside: A New Antitumor Cerebroside from The Red Sea Cucumber Holothuria spinifera: In Vitro and In Silico Studies

1
Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt
2
Department of Pharmacognosy, Faculty of Pharmacy, Deraya University, New Minia 61111, Egypt
3
Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt
4
Department of Marine Science, Faculty of Science, Suez Canal University, Ismailia 41522, Egypt
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Department of Biochemistry, Collage of Science, University of Jeddah, Jeddah 80203, Saudi Arabia
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Department of Chemistry of Pharmacology, Faculty of Pharmacy, Jouf University, Skaka 2014, Saudi Arabia
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Department of Clinical Pharmacology, Faculty of Medicine, Beni Suef University, Beni-Suef 62513, Egypt
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Pharmaceutical Chemistry Department, Faculty of Pharmacy, Nahda University, Beni Suef 62513, Egypt
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Department of Pharmacognosy, Faculty of Pharmacy, Modern University for Technology and Information, Cairo 12585, Egypt
10
Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editors: Shugeng Cao, Mostafa Rateb and Jianguang Luo
Molecules 2021, 26(6), 1555; https://doi.org/10.3390/molecules26061555
Received: 19 February 2021 / Revised: 7 March 2021 / Accepted: 9 March 2021 / Published: 12 March 2021
Chemical investigation of the methanolic extract of the Red Sea cucumber Holothuria spinifera led to the isolation of a new cerebroside, holospiniferoside (1), together with thymidine (2), methyl-α-d-glucopyranoside (3), a new triacylglycerol (4), and cholesterol (5). Their chemical structures were established by NMR and mass spectrometric analysis, including gas chromatography–mass spectrometry (GC–MS) and high-resolution mass spectrometry (HRMS). All the isolated compounds are reported in this species for the first time. Moreover, compound 1 exhibited promising in vitro antiproliferative effect on the human breast cancer cell line (MCF-7) with IC50 of 20.6 µM compared to the IC50 of 15.3 µM for the drug cisplatin. To predict the possible mechanism underlying the cytotoxicity of compound 1, a docking study was performed to elucidate its binding interactions with the active site of the protein Mdm2–p53. Compound 1 displayed an apoptotic activity via strong interaction with the active site of the target protein. This study highlights the importance of marine natural products in the design of new anticancer agents. View Full-Text
Keywords: Holothuria spinifera; HRMS; cerebrosides; molecular docking; cytotoxicity Holothuria spinifera; HRMS; cerebrosides; molecular docking; cytotoxicity
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MDPI and ACS Style

Eltamany, E.E.; Abdelmohsen, U.R.; Hal, D.M.; Ibrahim, A.K.; Hassanean, H.A.; Abdelhameed, R.F.A.; Temraz, T.A.; Hajjar, D.; Makki, A.A.; Hendawy, O.M.; AboulMagd, A.M.; Youssif, K.A.; Bringmann, G.; Ahmed, S.A. Holospiniferoside: A New Antitumor Cerebroside from The Red Sea Cucumber Holothuria spinifera: In Vitro and In Silico Studies. Molecules 2021, 26, 1555. https://doi.org/10.3390/molecules26061555

AMA Style

Eltamany EE, Abdelmohsen UR, Hal DM, Ibrahim AK, Hassanean HA, Abdelhameed RFA, Temraz TA, Hajjar D, Makki AA, Hendawy OM, AboulMagd AM, Youssif KA, Bringmann G, Ahmed SA. Holospiniferoside: A New Antitumor Cerebroside from The Red Sea Cucumber Holothuria spinifera: In Vitro and In Silico Studies. Molecules. 2021; 26(6):1555. https://doi.org/10.3390/molecules26061555

Chicago/Turabian Style

Eltamany, Enas E., Usama R. Abdelmohsen, Dina M. Hal, Amany K. Ibrahim, Hashim A. Hassanean, Reda F.A. Abdelhameed, Tarek A. Temraz, Dina Hajjar, Arwa A. Makki, Omnia M. Hendawy, Asmaa M. AboulMagd, Khayrya A. Youssif, Gerhard Bringmann, and Safwat A. Ahmed 2021. "Holospiniferoside: A New Antitumor Cerebroside from The Red Sea Cucumber Holothuria spinifera: In Vitro and In Silico Studies" Molecules 26, no. 6: 1555. https://doi.org/10.3390/molecules26061555

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