{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T20:16:39Z","timestamp":1784319399975,"version":"3.55.0"},"reference-count":26,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2016,4,26]],"date-time":"2016-04-26T00:00:00Z","timestamp":1461628800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Bioassay-guided fractionation of the organic extract of the Red Sea sponge Xestospongia testudinaria led to the isolation of 13 compounds including two new sterol esters, xestosterol palmitate (2) and xestosterol ester of l6\u2032-bromo-(7\u2032E,11\u2032E,l5\u2032E)-hexadeca-7\u2032,11\u2032,l5\u2032-triene-5\u2032,13\u2032-diynoic acid (4), together with eleven known compounds: xestosterol (1), xestosterol ester of 18\u2032-bromooctadeca-7\u2032E,9\u2032E-diene-7\u2032,15\u2032-diynoic acid (3), and the brominated acetylenic fatty acid derivatives, (5E,11E,15E,19E)-20-bromoeicosa-5,11,15,19-tetraene-9,17-diynoic acid (5), 18,18-dibromo-(9E)-octadeca-9,17-diene-5,7-diynoic acid (6), 18-bromooctadeca-(9E,17E)-diene-7,15-diynoic acid (7), 18-bromooctadeca-(9E,13E,17E)-triene-7,15-diynoic acid (8), l6-bromo (7E,11E,l5E)hexadeca-7,11,l5-triene-5,13-diynoic acid (9), 2-methylmaleimide-5-oxime (10), maleimide-5-oxime (11), tetillapyrone (12), and nortetillapyrone (13). The chemical structures of the isolated compounds were accomplished using one- and two-dimensional NMR, infrared and high-resolution electron impact mass spectroscopy (1D, 2D NMR, IR and HREIMS), and by comparison with the data of the known compounds. The total alcoholic and n-hexane extracts showed remarkable cytotoxic activity against human cervical cancer (HeLa), human hepatocellular carcinoma (HepG-2), and human medulloblastoma (Daoy) cancer cell lines. Interestingly, the dibrominated C18-acetylenic fatty acid (6) exhibited the most potent growth inhibitory activity against these cancer cell lines followed by Compounds 7 and 9. Apparently, the dibromination of the terminal olefinic moiety has an enhanced effect on the cytotoxic activity.<\/jats:p>","DOI":"10.3390\/md14050082","type":"journal-article","created":{"date-parts":[[2016,4,26]],"date-time":"2016-04-26T10:21:21Z","timestamp":1461666081000},"page":"82","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Cytotoxic Compounds from the Saudi Red Sea Sponge Xestospongia testudinaria"],"prefix":"10.3390","volume":"14","author":[{"given":"Ali","family":"El-Gamal","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"},{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, El-Mansoura 35516, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaza","family":"Al-Massarani","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1866-8258","authenticated-orcid":false,"given":"Lamiaa","family":"Shaala","sequence":"additional","affiliation":[{"name":"Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia"},{"name":"Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abdulrahman","family":"Alahdald","sequence":"additional","affiliation":[{"name":"Department of Clinical Pharmacy, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mansour","family":"Al-Said","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abdelkader","family":"Ashour","sequence":"additional","affiliation":[{"name":"Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2580-0253","authenticated-orcid":false,"given":"Ashok","family":"Kumar","sequence":"additional","affiliation":[{"name":"Vitiligo Research Chair, College of Medicine, King Saud University, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maged","family":"Abdel-Kader","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy, Sattam Bin Abdulaziz University, Al-kharj 11942, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wael","family":"Abdel-Mageed","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia"},{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2217-4039","authenticated-orcid":false,"given":"Diaa","family":"Youssef","sequence":"additional","affiliation":[{"name":"Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2016,4,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2619","DOI":"10.3390\/md8102619","article-title":"Antiviral lead compounds from marine sponges","volume":"8","author":"Sagar","year":"2010","journal-title":"Mar. Drugs"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"86","DOI":"10.2174\/138920109787048625","article-title":"Marine sponges: Potential sources of new antimicrobial drugs","volume":"10","author":"Laport","year":"2009","journal-title":"Curr. Pharm. Biotechnol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1216","DOI":"10.1021\/np040031y","article-title":"Marine natural products and related compounds in clinical and advanced preclinical trials","volume":"67","author":"Newman","year":"2004","journal-title":"J. Nat. Prod."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2201","DOI":"10.1002\/cbdv.201000024","article-title":"Chemical and biological aspects of marine sponges of the genus Xestospongia","volume":"7","author":"Zhou","year":"2010","journal-title":"Chem. Biodivers."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"El-Shitany, N.A., Shaala, L.A., Abbas, A.T., Abdel-dayem, U.A., Azhar, E.I., Ali, S.S., van Soest, R.W.M., and Youssef, D.T.A. (2015). Evaluation of the anti-inflammatory, antioxidant and immunomodulatory effects of the organic extract of the Red Sea marine sponge Xestospongia testudinaria against carrageenan induced rat paw inflammation. PLoS ONE, 10.","DOI":"10.1371\/journal.pone.0138917"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1055\/s-2003-37719","article-title":"Clionasterol: A potent inhibitor of complement component C1","volume":"69","author":"Cerqueira","year":"2003","journal-title":"Planta Medica"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1056","DOI":"10.1021\/np9604083","article-title":"Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica","volume":"59","author":"Edrada","year":"1996","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1749","DOI":"10.1271\/bbb.69.1749","article-title":"Novel relationship between the antifungal activity and cytotoxicity of marine-derived metabolite xestoquinone and its family","volume":"69","author":"Nakamura","year":"2005","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1170","DOI":"10.1021\/np50087a002","article-title":"Brominated polyacetylenic acids from the marine sponge Xestospongia muta: Inhibitors of HIV protease","volume":"55","author":"Patil","year":"1992","journal-title":"J. Nat. Prod."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1439","DOI":"10.1021\/np9901635","article-title":"Isolation of xestosterol esters of brominated acetylenic fatty acids from the marine sponge Xestospongia testudinaria","volume":"62","author":"Pham","year":"1999","journal-title":"J. Nat. Prod."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1248\/cpb.56.378","article-title":"Brominated unsaturated fatty acids from marine sponge collected in Papua New Guinea","volume":"56","author":"Taniguchi","year":"2008","journal-title":"Chem. Pharm. Bull. (Tokyo)"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"7837","DOI":"10.1016\/j.tet.2015.08.024","article-title":"Bioactive alkaloids from the Red Sea marine Verongid sponge Pseudoceratina arabica","volume":"71","author":"Shaala","year":"2015","journal-title":"Tetrahedron"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1621","DOI":"10.3390\/md13041621","article-title":"Bioactive secondary metabolites from a Red Sea marine Verongid sponge Suberea species","volume":"13","author":"Shaala","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1698","DOI":"10.3390\/md13041698","article-title":"Identification and bioactivity of compounds from the fungus Penicillium sp. CYE-87 isolated from a marine tunicate","volume":"13","author":"Shaala","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"6609","DOI":"10.3390\/md13116609","article-title":"Bioactive hydantoin alkaloids from the Red Sea marine sponge Hemimycale arabica","volume":"13","author":"Youssef","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3385","DOI":"10.1021\/jo01333a023","article-title":"Isolation, structure elucidation and partial synthesis of xestosterol, biosynthetically significant sterol from the sponge Xestospongia muta","volume":"44","author":"Kokke","year":"1979","journal-title":"J. Org. Chem."},{"key":"ref_17","first-page":"140","article-title":"Isolation and characterization of palmitic acid from ethyl acetate extract of root bark of Terminalia glaucescens","volume":"6","author":"Bulama","year":"2014","journal-title":"Chem. Mater. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1515\/znc-2015-5015","article-title":"Two new polyacetylene derivatives from the Red Sea sponge Xestospongia sp.","volume":"70","author":"Ayyad","year":"2015","journal-title":"Z. Naturforschung C"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"7667","DOI":"10.1016\/0040-4020(95)00405-W","article-title":"Brominated acetylenic fatty acids from Xestospongia sp., a marine spongebacteria association","volume":"51","author":"Brantley","year":"1995","journal-title":"Tetrahedron"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3257","DOI":"10.1016\/S0040-4020(01)90293-5","article-title":"Brominated unsaturated acids from the marine sponge Xestospongia sp.","volume":"43","author":"Hirsh","year":"1987","journal-title":"Tetrahedron"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1671","DOI":"10.1016\/S0040-4039(00)98581-2","article-title":"A brominated bisacetylenic acid from the marine sponge Xestospongia testudinaria","volume":"26","author":"Quinn","year":"1985","journal-title":"Tetrahedron Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"904","DOI":"10.1515\/znb-2005-0815","article-title":"Dibromotyrosine derivatives, a maleimide, aplysamine-2 and other constituents of the marine sponge Pseudoceratina purpurea","volume":"60b","author":"Kijjoa","year":"2005","journal-title":"Z. Naturforschung"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"40","DOI":"10.3390\/md502040","article-title":"Antifungal activity evaluation of the constituents of Haliclona baeri and Haliclona cymaeformis, collected from the Gulf of Thailand","volume":"5","author":"Wattanadilok","year":"2007","journal-title":"Mar. Drugs"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1056","DOI":"10.1021\/np0100690","article-title":"Tetillapyrone and nortetillapyrone, two unusual hydroxypyran-2-ones from the marine sponge Tetilla japonica","volume":"64","author":"Wattanadilok","year":"2001","journal-title":"J. Nat. Prod."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2173","DOI":"10.14233\/ajchem.2014.16849","article-title":"Antitumor activity of 1,2,4-triazolo[1,5-a]quinazolines","volume":"26","author":"Marzouk","year":"2014","journal-title":"Asian J. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"6658","DOI":"10.1021\/jm049486a","article-title":"Discovery of N-(2-chloro-6-methyl-phenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-1-yl)-2-methylpyrimidin-4-ylamino) thiazole-5-carboxamide (BMS-354825), a dual Src\/Abl kinase inhibitor with potent antitumor activity in preclinical assays","volume":"47","author":"Lombardo","year":"2004","journal-title":"J. Med. Chem."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/14\/5\/82\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T19:22:52Z","timestamp":1760210572000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/14\/5\/82"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,4,26]]},"references-count":26,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2016,5]]}},"alternative-id":["md14050082"],"URL":"https:\/\/doi.org\/10.3390\/md14050082","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,4,26]]}}}