{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,23]],"date-time":"2025-11-23T15:12:10Z","timestamp":1763910730191,"version":"3.45.0"},"reference-count":33,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T00:00:00Z","timestamp":1762128000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001322","name":"South African Medical Research Council","doi-asserted-by":"publisher","award":["AMR DD96815"],"award-info":[{"award-number":["AMR DD96815"]}],"id":[{"id":"10.13039\/501100001322","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100017177","name":"German Academic Exchange Service France","doi-asserted-by":"publisher","award":["91758998"],"award-info":[{"award-number":["91758998"]}],"id":[{"id":"10.13039\/100017177","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100021828","name":"DAAD","doi-asserted-by":"publisher","award":["91700877"],"award-info":[{"award-number":["91700877"]}],"id":[{"id":"10.13039\/100021828","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2025,11,18]]},"abstract":"\n Marine sponges of the genus\n Oceanapia<\/jats:italic>\n are prolific producers of bioactive secondary metabolites. Four known bifunctional sphingolipids are isolated: isorhizochalin (\n 1<\/jats:bold>\n ), rhizochalin (\n 2<\/jats:bold>\n ), rhizochalin C (\n 3<\/jats:bold>\n ), and oceanapiside (\n 4<\/jats:bold>\n ) from\n Oceanapia ramsayi<\/jats:italic>\n sponges. These compounds are derivatized to form aglycones (\n 1b\u20104b<\/jats:bold>\n ), perbenzoates (\n 1c\u20134c<\/jats:bold>\n ), and\n bis<\/jats:italic>\n \u2010oxazoline (\n 2e<\/jats:bold>\n ). The compounds and their derivatives are investigated for their cytotoxicity against three breast cancer cell lines (HCC70, MDA\u2010MB\u2010231, MCF7). All four sphingolipids are cytotoxic with significant selectivity indices (SI) for the three breast cancer cells. Compound\n 1<\/jats:bold>\n has high selectivity against the HCC70 cell line,\n 4<\/jats:bold>\n against the MDA\u2010MB\u2010231 cells, and aglycon\n 4b<\/jats:bold>\n against both the MDA\u2010MB\u2010231 and MCF7 cell lines, respectively, demonstrating the functional importance of the sugar units and terminal amino\u2010alcohol stereochemistry. Compounds\n 1<\/jats:bold>\n \u2013\n 4<\/jats:bold>\n also show promising antibacterial activity against\n Staphylococcus aureus, Acinetobacter baumannii<\/jats:italic>\n ,\n Pseudomonas aeruginosa<\/jats:italic>\n ,\n Escherichia coli<\/jats:italic>\n , and the multiple antibiotic\u2010resistant\n Klebsiella pneumoniae<\/jats:italic>\n test strains, with compound\n 2<\/jats:bold>\n exhibiting the greatest activity. Derivatization diminished potency, indicating that the sugar moiety and stereochemistry are functionally important for antibacterial activity.\n <\/jats:p>","DOI":"10.1002\/cmdc.202500392","type":"journal-article","created":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T21:16:08Z","timestamp":1762204568000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Dual Biological Potential: Anticancer and Antibacterial Activities of\n Bis\u2010<\/i>\n \u03b1, \u03c9\u2010Bifunctional Sphingolipids from the Marine Sponge\n Oceanapia ramsayi<\/i>"],"prefix":"10.1002","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7610-4178","authenticated-orcid":false,"given":"Dele Abdissa","family":"Keneni","sequence":"first","affiliation":[{"name":"Department of Chemistry Rhodes University Makhanda 6140 South Africa"},{"name":"Department of Chemistry College of Natural Sciences Jimma University Jimma P.O. Box 378 Ethiopia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8754-4566","authenticated-orcid":false,"given":"Idris","family":"Njanje","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Microbiology and Bioinformatics Rhodes University Makhanda 6140 South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9641-2912","authenticated-orcid":false,"given":"Jarmo\u2010Charles Julian","family":"Kalinski","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Microbiology and Bioinformatics Rhodes University Makhanda 6140 South Africa"},{"name":"Department of Biochemistry University of California Riverside Riverside CA 92521 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0694-7487","authenticated-orcid":false,"given":"Michelle","family":"Isaacs","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Microbiology and Bioinformatics Rhodes University Makhanda 6140 South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8519-681X","authenticated-orcid":false,"given":"Tarryn","family":"Swart","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Microbiology and Bioinformatics Rhodes University Makhanda 6140 South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8288-9290","authenticated-orcid":false,"given":"Candace","family":"Davison","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Microbiology and Bioinformatics Rhodes University Makhanda 6140 South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jo\u2010Anne","family":"de la Mare","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Microbiology and Bioinformatics Rhodes University Makhanda 6140 South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8694-367X","authenticated-orcid":false,"given":"Rosemary Ann","family":"Dorrington","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Microbiology and Bioinformatics Rhodes University Makhanda 6140 South Africa"},{"name":"South African Institute for Aquatic Biodiversity Makhanda 6140 South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,11,3]]},"reference":[{"doi-asserted-by":"publisher","key":"e_1_2_9_2_1","DOI":"10.3390\/md15090272"},{"doi-asserted-by":"publisher","key":"e_1_2_9_3_1","DOI":"10.3390\/md20080528"},{"doi-asserted-by":"publisher","key":"e_1_2_9_4_1","DOI":"10.1021\/acs.jnatprod.9b01285"},{"doi-asserted-by":"publisher","key":"e_1_2_9_5_1","DOI":"10.1186\/s43141-021-00290-4"},{"doi-asserted-by":"publisher","key":"e_1_2_9_6_1","DOI":"10.3390\/md20020144"},{"doi-asserted-by":"publisher","key":"e_1_2_9_7_1","DOI":"10.1007\/s10600-007-0164-4"},{"doi-asserted-by":"publisher","key":"e_1_2_9_8_1","DOI":"10.1248\/bpb.34.1553"},{"doi-asserted-by":"publisher","key":"e_1_2_9_9_1","DOI":"10.1248\/bpb.32.955"},{"doi-asserted-by":"publisher","key":"e_1_2_9_10_1","DOI":"10.1007\/s11745-009-3322-6"},{"doi-asserted-by":"publisher","key":"e_1_2_9_11_1","DOI":"10.3390\/molecules13040772"},{"doi-asserted-by":"publisher","key":"e_1_2_9_12_1","DOI":"10.1016\/S0040-4039(01)89027-4"},{"doi-asserted-by":"publisher","key":"e_1_2_9_13_1","DOI":"10.1021\/np990190v"},{"doi-asserted-by":"publisher","key":"e_1_2_9_14_1","DOI":"10.1021\/np049710z"},{"doi-asserted-by":"publisher","key":"e_1_2_9_15_1","DOI":"10.1016\/j.plipres.2010.10.003"},{"doi-asserted-by":"publisher","key":"e_1_2_9_16_1","DOI":"10.3390\/ijms15034356"},{"doi-asserted-by":"publisher","key":"e_1_2_9_17_1","DOI":"10.1016\/j.neuron.2008.12.023"},{"doi-asserted-by":"publisher","key":"e_1_2_9_18_1","DOI":"10.1007\/s11745-009-3360-0"},{"doi-asserted-by":"publisher","key":"e_1_2_9_19_1","DOI":"10.18632\/oncotarget.24764"},{"doi-asserted-by":"publisher","key":"e_1_2_9_20_1","DOI":"10.1002\/1521-3773(20001117)39:22<4076::AID-ANIE4076>3.0.CO;2-D"},{"doi-asserted-by":"publisher","key":"e_1_2_9_21_1","DOI":"10.1021\/np0704811"},{"doi-asserted-by":"publisher","key":"e_1_2_9_22_1","DOI":"10.1016\/S0960-894X(02)00367-0"},{"doi-asserted-by":"publisher","key":"e_1_2_9_23_1","DOI":"10.1021\/jacs.8b07319"},{"doi-asserted-by":"publisher","key":"e_1_2_9_24_1","DOI":"10.1517\/13543784.13.8.1045"},{"key":"e_1_2_9_25_1","first-page":"e01312","volume":"10","author":"Kong D.","year":"2022","journal-title":"Microbiol. Spectr."},{"doi-asserted-by":"publisher","key":"e_1_2_9_26_1","DOI":"10.1128\/iai.26.3.1202-1210.1979"},{"doi-asserted-by":"publisher","key":"e_1_2_9_27_1","DOI":"10.1128\/AAC.8.3.251"},{"doi-asserted-by":"publisher","key":"e_1_2_9_28_1","DOI":"10.1002\/jps.2600621018"},{"doi-asserted-by":"publisher","key":"e_1_2_9_29_1","DOI":"10.1021\/acsinfecdis.1c00318"},{"key":"e_1_2_9_30_1","first-page":"539","volume":"100","author":"Davies\u2010Coleman M. T.","year":"2004","journal-title":"S. Afr. J. Sci."},{"doi-asserted-by":"publisher","key":"e_1_2_9_31_1","DOI":"10.37275\/ehi.v2i1.15"},{"key":"e_1_2_9_32_1","doi-asserted-by":"crossref","first-page":"e0271389","DOI":"10.1371\/journal.pone.0271389","volume":"8","author":"Kemboi D.","year":"2022","journal-title":"PLoS One"},{"volume-title":"Assay Guidance Manual","year":"2016","author":"Riss T. L.","key":"e_1_2_9_33_1"},{"doi-asserted-by":"publisher","key":"e_1_2_9_34_1","DOI":"10.1371\/journal.pone.0155139"}],"container-title":["ChemMedChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cmdc.202500392","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,23]],"date-time":"2025-11-23T15:08:02Z","timestamp":1763910482000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cmdc.202500392"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,11,3]]},"references-count":33,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2025,11,18]]}},"alternative-id":["10.1002\/cmdc.202500392"],"URL":"https:\/\/doi.org\/10.1002\/cmdc.202500392","archive":["Portico"],"relation":{},"ISSN":["1860-7179","1860-7187"],"issn-type":[{"type":"print","value":"1860-7179"},{"type":"electronic","value":"1860-7187"}],"subject":[],"published":{"date-parts":[[2025,11,3]]},"assertion":[{"value":"2025-05-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-03","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202500392"}}