{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,24]],"date-time":"2026-06-24T12:49:57Z","timestamp":1782305397514,"version":"3.54.5"},"reference-count":21,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2023,1,3]],"date-time":"2023-01-03T00:00:00Z","timestamp":1672704000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Australian Research Council (ARC)","award":["FT200100243"],"award-info":[{"award-number":["FT200100243"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Two novel free porphyrins, isabellins A and B, as well as the known compounds corallistin D and deuteroporphyrin IX were isolated from a marine sponge Isabela sp. LC-MS analysis of the crude extract revealed that the natural products were present both as free porphyrins and iron(III) coordinated hemins, designated isabellihemin A, isabellihemin B, corallistihemin D and deuterohemin IX, respectively. Structures were determined via high-resolution mass spectrometry, UV-Vis spectroscopy and extensive NOESY NMR spectroscopic experiments. The type-I alkyl substitution pattern of isabellin A and isabellihemin A was assigned unambiguously by single crystal X-ray diffraction. Biological evaluation of the metabolites revealed potent cytotoxicity for isabellin A against the NS-1 murine myeloma cell line.<\/jats:p>","DOI":"10.3390\/md21010041","type":"journal-article","created":{"date-parts":[[2023,1,4]],"date-time":"2023-01-04T02:54:55Z","timestamp":1672800895000},"page":"41","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Type-I Hemins and Free Porphyrins from a Western Australian Sponge Isabela sp."],"prefix":"10.3390","volume":"21","author":[{"given":"Samuele","family":"Sala","sequence":"first","affiliation":[{"name":"School of Molecular Sciences, The University of Western Australia, Crawley, WA 6009, Australia"},{"name":"Australian National Phenome Centre and Centre for Computational and Systems Medicine, Health Futures Institute, Murdoch University, Harry Perkins Building, Perth, WA 6150, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen","family":"Moggach","sequence":"additional","affiliation":[{"name":"School of Molecular Sciences, The University of Western Australia, Crawley, WA 6009, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7037-7135","authenticated-orcid":false,"given":"Gareth","family":"Nealon","sequence":"additional","affiliation":[{"name":"School of Molecular Sciences, The University of Western Australia, Crawley, WA 6009, Australia"},{"name":"Centre for Microscopy, Characterisation and Analysis, The University of Western Australia, Crawley, WA 6009, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jane","family":"Fromont","sequence":"additional","affiliation":[{"name":"Collection and Research, Western Australian Museum, Welshpool, WA 6106, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oliver","family":"Gomez","sequence":"additional","affiliation":[{"name":"Collection and Research, Western Australian Museum, Welshpool, WA 6106, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2451-3148","authenticated-orcid":false,"given":"Daniel","family":"Vuong","sequence":"additional","affiliation":[{"name":"Microbial Screening Technologies Pty. Ltd., Smithfield, NSW 2164, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ernest","family":"Lacey","sequence":"additional","affiliation":[{"name":"Microbial Screening Technologies Pty. Ltd., Smithfield, NSW 2164, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2545-6939","authenticated-orcid":false,"given":"Gavin","family":"Flematti","sequence":"additional","affiliation":[{"name":"School of Molecular Sciences, The University of Western Australia, Crawley, WA 6009, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Paterson, I., Britton, R., Delgado, O., and Wright, A.E. (2004). Stereochemical determination of dictyostatin, a novel microtubule-stabilising macrolide from the marine sponge Corallistidae sp. Chem. Commun., 632\u2013633.","DOI":"10.1002\/chin.200431189"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1534","DOI":"10.1016\/S0040-4039(00)99512-1","article-title":"Corallistine, a new polynitrogen compound from the sponge Corallistes fulvodesmus L. & L.","volume":"30","author":"Debitus","year":"1989","journal-title":"Tetrahedron Lett."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1451","DOI":"10.1002\/hlca.19890720704","article-title":"Corallistin A, a second example of a free porphyrin from a living organism. Isolation from the demosponge Corallistes sp. of the coral see and inhibition of abnormal cells","volume":"72","author":"Guerriero","year":"1989","journal-title":"Helv. Chim. Acta"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1489","DOI":"10.1002\/hlca.19930760410","article-title":"On the Novel Free Porphyrins Corallistin B, C, D, and E: Isolation from the demosponge Corallistes sp. of the Coral Sea and Reactivity of Their Nickel 55 (II) Complexes toward Formylating Reagents","volume":"76","author":"Guerriero","year":"1993","journal-title":"Helv. Chim. Acta"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"8093","DOI":"10.1016\/0040-4039(94)88251-7","article-title":"Total synthesis of new porphyrins isolated from the coral sea demosponge Corallistes sp.","volume":"35","author":"Pandey","year":"1994","journal-title":"Tetrahedron Lett."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4231","DOI":"10.1016\/S0040-4039(00)92135-X","article-title":"Total synthesis of corallistin A","volume":"32","author":"Scott","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"ref_7","unstructured":"Pisera, A. Personal communication."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/S1572-1000(04)00007-9","article-title":"Photosensitizers in clinical PDT","volume":"1","author":"Allison","year":"2004","journal-title":"Photodiagnosis Photodyn. Ther."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1038\/285017a0","article-title":"Biosynthesis of the pigments of life: Formation of the macrocycle","volume":"285","author":"Battersby","year":"1980","journal-title":"Nature"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1137","DOI":"10.1002\/pro.405","article-title":"Structure and function of enzymes in heme biosynthesis","volume":"19","author":"Layer","year":"2010","journal-title":"Protein Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1039\/np9850200019","article-title":"The biosynthesis of porphyrins, chlorophylls, and vitamin B12","volume":"2","author":"Leeper","year":"1985","journal-title":"Nat. Prod. Rep."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Shrestha, S., Sorolla, A., Fromont, J., Blancafort, P., and Flematti, G.R. (2018). Aurantoside C Targets and Induces Apoptosis in Triple Negative Breast Cancer Cells. Mar Drugs, 16.","DOI":"10.3390\/md16100361"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Shrestha, S., Sorolla, A., Fromont, J., Blancafort, P., and Flematti, G.R. (2018). Crambescidin 800, Isolated from the Marine Sponge Monanchora viridis, Induces Cell Cycle Arrest and Apoptosis in Triple-Negative Breast Cancer Cells. Mar Drugs, 16.","DOI":"10.3390\/md16020053"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1007\/s10750-011-0845-7","article-title":"Living on the edge: The sponge fauna of Australia\u2019s southwestern and northwestern deep continental margin","volume":"687","author":"Fromont","year":"2012","journal-title":"Hydrobiologia"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1627\/jpi.57.18","article-title":"Removal of Nickel and Vanadium from Heavy Oils Using Supercritical Water","volume":"57","author":"Mandal","year":"2014","journal-title":"J. Jpn. Pet. Inst."},{"key":"ref_16","unstructured":"White, W.M. (2018). Porphyrins. Encyclopedia of Geochemistry: A Comprehensive Reference Source on the Chemistry of the Earth, Springer International Publishing."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"7512","DOI":"10.1021\/jo971176v","article-title":"NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities","volume":"62","author":"Gottlieb","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. C"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Crystallogr."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/j.ijpddr.2021.01.001","article-title":"TriTOX: A novel Trichomonas vaginalis assay platform for high-throughput screening of compound libraries","volume":"15","author":"Lam","year":"2021","journal-title":"Int. J. Parasitol. Drugs Drug Resist."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/21\/1\/41\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T17:58:00Z","timestamp":1760119080000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/21\/1\/41"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,3]]},"references-count":21,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2023,1]]}},"alternative-id":["md21010041"],"URL":"https:\/\/doi.org\/10.3390\/md21010041","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,3]]}}}