{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,30]],"date-time":"2026-04-30T03:06:48Z","timestamp":1777518408092,"version":"3.51.4"},"reference-count":29,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2016,10,18]],"date-time":"2016-10-18T00:00:00Z","timestamp":1476748800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Seventh Framework Programme","award":["312184"],"award-info":[{"award-number":["312184"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>A new napyradiomycin, MDN-0170 (1), was isolated from the culture broth of the marine-derived actinomycete strain CA-271078, together with three known related compounds identified as 4-dehydro-4a-dechloronapyradiomycin A1 (2), napyradiomycin A1 (3) and 3-chloro-6,8-dihydroxy-8-\u03b1-lapachone (4). The structure of the new compound was determined using a combination of spectroscopic techniques, including 1D and 2D NMR and electrospray-time of flight mass spectrometry (ESI-TOF MS). The relative configuration of compound 1, which contains two independent stereoclusters, has been established by molecular modelling in combination with nOe and coupling constant analyses. Biosynthetic arguments also allowed us to propose its absolute stereochemistry. The antimicrobial properties of the compounds isolated were evaluated against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, Aspergillus fumigatus, and Candida albicans. The potent bioactivity previously reported for compounds 2 and 3 against methicillin-sensitive S. aureus has been extended to methicillin-resistant strains in this report.<\/jats:p>","DOI":"10.3390\/md14100188","type":"journal-article","created":{"date-parts":[[2016,10,18]],"date-time":"2016-10-18T10:46:25Z","timestamp":1476787585000},"page":"188","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["MDN-0170, a New Napyradiomycin from Streptomyces sp. Strain CA-271078"],"prefix":"10.3390","volume":"14","author":[{"given":"Rodney","family":"Lacret","sequence":"first","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4556-688X","authenticated-orcid":false,"given":"Ignacio","family":"P\u00e9rez-Victoria","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Daniel","family":"Oves-Costales","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2389-8576","authenticated-orcid":false,"given":"Mercedes","family":"De la Cruz","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elizabeth","family":"Domingo","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jes\u00fas","family":"Mart\u00edn","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Caridad","family":"D\u00edaz","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Francisca","family":"Vicente","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4202-1219","authenticated-orcid":false,"given":"Olga","family":"Genilloud","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1607-5106","authenticated-orcid":false,"given":"Fernando","family":"Reyes","sequence":"additional","affiliation":[{"name":"Fundaci\u00f3n MEDINA, Centro de Excelencia en Investigaci\u00f3n de Medicamentos Innovadores en Andaluc\u00eda, Avda. del Conocimiento 34, 18016 Armilla (Granada), Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2016,10,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"494","DOI":"10.7164\/antibiotics.39.494","article-title":"Structures of new antibiotics napyradiomycins","volume":"39","author":"Shiomi","year":"1986","journal-title":"J. Antibiot."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1213","DOI":"10.7164\/antibiotics.40.1213","article-title":"New antibiotic napyradiomycins A2 and B4 and stereochemistry of napyradiomycins","volume":"40","author":"Shiomi","year":"1987","journal-title":"J. Antibiot."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/S0723-2020(86)80148-5","article-title":"Transfer of Chainia species to the genus Streptomyces with emended description of species","volume":"8","author":"Goodfellow","year":"1986","journal-title":"Syst. Appl. Microbiol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"623","DOI":"10.7164\/antibiotics.43.623","article-title":"A80915, A new antibiotic complex produced by Streptomyces aculeolatus. Discovery, taxonomy, fermentation, isolation, characterization, and antibacterial evaluation","volume":"43","author":"Fukuda","year":"1990","journal-title":"J. Antibiot."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"904","DOI":"10.1021\/np058011z","article-title":"Antibiotic terpenoid chloro-dihydroquinones from a new marine actinomycete","volume":"68","author":"Jensen","year":"2005","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1021\/np400466j","article-title":"Napyradiomycin derivatives, produced by a marine-derived actinomycete, illustrate cytotoxicity by induction of apoptosis","volume":"77","author":"Farnaes","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1021\/np070575a","article-title":"Terpenoids produced by actinomycetes: Napyradiomycins from Streptomyces antimycoticus NT17","volume":"71","author":"Motohashi","year":"2008","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Cheng, Y.B., Jensen, P.R., and Fenical, W. (2013). Cytotoxic and antimicrobial napyradiomycins from two marine-derived Streptomyces strains. Eur. J. Org. Chem., 3751\u20133757.","DOI":"10.1002\/ejoc.201300349"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"604","DOI":"10.7164\/antibiotics.48.604","article-title":"Isolation from Streptomyces of a novel naphthoquinone compound, naphthablin, that inhibits abl oncogene functions","volume":"48","author":"Umezawa","year":"1995","journal-title":"J. Antibiot."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2471","DOI":"10.1021\/ol060630r","article-title":"Azamerone, a terpenoid phthalazinone from a marine-derived bacterium related to the genus Streptomyces (Actinomycetales)","volume":"8","author":"Cho","year":"2006","journal-title":"Org. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1038\/ja.2008.113","article-title":"Studies on terpenoids produced by actinomycetes. 5-dimethylallylindole-3-carboxylic acid and A80915G-8\u2032\u2032-acid produced by marine-derived Streptomyces sp. MS239","volume":"61","author":"Motohashi","year":"2008","journal-title":"J. Antibiot."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2113","DOI":"10.3390\/md11062113","article-title":"Antibacterial and cytotoxic new napyradiomycins from the marine-derived Streptomyces sp. SCSIO 10428","volume":"11","author":"Wu","year":"2013","journal-title":"Mar. Drugs"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"680","DOI":"10.3390\/md9040680","article-title":"Bactericidal kinetics of marine-derived napyradiomycins against contemporary methicillin-resistant Staphylococcus aureus","volume":"9","author":"Haste","year":"2011","journal-title":"Mar. Drugs"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1038\/ja.2011.138","article-title":"Napyradiomycin A1, an inhibitor of mitochondrial complexes I and II","volume":"65","author":"Yamamoto","year":"2012","journal-title":"J. Antibiot."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"418","DOI":"10.1039\/C3OB41355A","article-title":"Napyradiomycins CNQ525.510B and A80915C target the hsp90 paralogue grp94","volume":"12","author":"Farnaes","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"128","DOI":"10.3390\/md13010128","article-title":"New ikarugamycin derivatives with antifungal and antibacterial properties from Streptomyces zhaozhouensis","volume":"13","author":"Lacret","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"716","DOI":"10.1099\/ijs.0.038075-0","article-title":"Introducing EzTaxon-e: A prokaryotic 16S rRNA gene sequence database with phylotypes that represent uncultured species","volume":"62","author":"Kim","year":"2012","journal-title":"Int. J. Syst. Evol. Microbiol."},{"key":"ref_18","first-page":"406","article-title":"The neighbor-joining method: A new method for reconstructing phylogenetic trees","volume":"4","author":"Saitou","year":"1987","journal-title":"Mol. Biol. Evol."},{"key":"ref_19","unstructured":"Munro, H.N. (1969). Mammalian Protein Metabolism, Academic Press."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1055\/s-0042-101763","article-title":"Combined LC\/UV\/MS and NMR strategies for the dereplication of marine natural products","volume":"82","author":"Reyes","year":"2016","journal-title":"Planta Med."},{"key":"ref_21","unstructured":"Dictionary of Natural Products (DPN 2016). Chapman & Hall\/CRC. Available online: http:\/\/dnp.Chemnetbase.Com\/intro\/index.jsp."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1069","DOI":"10.7164\/antibiotics.43.1069","article-title":"A novel series of milbemycin antibiotics from Streptomyces strain E225. II. Isolation, characterization, structure elucidation and solution conformations","volume":"43","author":"Baker","year":"1990","journal-title":"J. Antibiot."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"16362","DOI":"10.1074\/jbc.M611046200","article-title":"Molecular basis for chloronium-mediated meroterpene cyclization: Cloning, sequencing, and heterologous expression of the napyradiomycin biosynthetic gene cluster","volume":"282","author":"Winter","year":"2007","journal-title":"J. Biol. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"O1627","DOI":"10.1107\/S1600536804020094","article-title":"3,4a-Dichloro-10a-(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexylmethyl)-6,8-dihydroxy-2,2,7-trimethyl-3,4,4a,10a-tetrahydro-2h-benzo[g]chromene-5,10-dione","volume":"60","author":"Jensen","year":"2004","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2118","DOI":"10.1021\/np500577v","article-title":"MDN-0104, an antiplasmodial betaine lipid from Heterospora chenopodii","volume":"77","author":"Crespo","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"387","DOI":"10.3390\/md11020387","article-title":"Kocurin, the true structure of PM181104, an anti-methicillin-resistant Staphylococcus aureus (MRSA) thiazolyl peptide from the marine-derived bacterium Kocuria palustris","volume":"11","author":"Crespo","year":"2013","journal-title":"Mar. Drugs"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1177\/1087057111433459","article-title":"A new approach to drug discovery: High-throughput screening of microbial natural extracts against Aspergillus fumigatus using resazurin","volume":"17","author":"Monteiro","year":"2012","journal-title":"J. Biomol. Screen."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1016\/S1995-7645(13)60117-0","article-title":"Anti-fungal and anti-bacterial activities of ethanol extracts of selected traditional Chinese medicinal herbs","volume":"6","author":"Zhang","year":"2013","journal-title":"Asian Pac. J. Trop. Med."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1177\/108705719900400206","article-title":"A simple statistical parameter for use in evaluation and validation of high throughput screening assays","volume":"4","author":"Zhang","year":"1999","journal-title":"J. Biomol. Screen."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/14\/10\/188\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T19:33:17Z","timestamp":1760211197000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/14\/10\/188"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,10,18]]},"references-count":29,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2016,10]]}},"alternative-id":["md14100188"],"URL":"https:\/\/doi.org\/10.3390\/md14100188","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,10,18]]}}}