{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T20:59:51Z","timestamp":1788469191489,"version":"build-2803163510"},"reference-count":18,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2023,6,28]],"date-time":"2023-06-28T00:00:00Z","timestamp":1687910400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Key Research and Development Project","award":["2022YFC2804500"],"award-info":[{"award-number":["2022YFC2804500"]}]},{"name":"National Key Research and Development Project","award":["2022YFC2804105"],"award-info":[{"award-number":["2022YFC2804105"]}]},{"name":"National Key Research and Development Project","award":["20ZR1470600"],"award-info":[{"award-number":["20ZR1470600"]}]},{"name":"National Key Research and Development Project","award":["2020PJD082"],"award-info":[{"award-number":["2020PJD082"]}]},{"name":"Natural Science Foundation of Shanghai","award":["2022YFC2804500"],"award-info":[{"award-number":["2022YFC2804500"]}]},{"name":"Natural Science Foundation of Shanghai","award":["2022YFC2804105"],"award-info":[{"award-number":["2022YFC2804105"]}]},{"name":"Natural Science Foundation of Shanghai","award":["20ZR1470600"],"award-info":[{"award-number":["20ZR1470600"]}]},{"name":"Natural Science Foundation of Shanghai","award":["2020PJD082"],"award-info":[{"award-number":["2020PJD082"]}]},{"name":"Shanghai Pujiang Program","award":["2022YFC2804500"],"award-info":[{"award-number":["2022YFC2804500"]}]},{"name":"Shanghai Pujiang Program","award":["2022YFC2804105"],"award-info":[{"award-number":["2022YFC2804105"]}]},{"name":"Shanghai Pujiang Program","award":["20ZR1470600"],"award-info":[{"award-number":["20ZR1470600"]}]},{"name":"Shanghai Pujiang Program","award":["2020PJD082"],"award-info":[{"award-number":["2020PJD082"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>A chemical investigation of the Arctic-derived fungus Eutypella sp. D-1 based on the OSMAC (one strain many compounds) approach resulted in the isolation of five cytosporin polyketides (compounds 1\u20133 and 11\u201312) from rice medium and eight cytosporins (compounds 2 and 4\u201311) from solid defined medium. The structures of the seven new compounds, eutypelleudesmane A (1), cytosporin Y (2), cytosporin Z (3), cytosporin Y1 (4), cytosporin Y2 (5), cytosporin Y3 (6), and cytosporin E1 (7), were elucidated by analyzing their detailed spectroscopic data. Structurally, cytosporin Y1 (4) may be a key intermediate in the biosynthesis of the isolated cytosporins, rather than an end product. Compound 1 contained a unique skeleton formed by the ester linkage of two moieties, cytosporin F (12) and the eudesmane-type sesquiterpene dihydroalanto glycol. Additionally, the occurrence of cyclic carbonate moieties in compounds 6 and 7 was found to be rare in nature. The antibacterial, immunosuppressive, and cytotoxic activities of all compounds derived from Eutypella sp. D-1 were evaluated. Unfortunately, only compounds 3, 6, 8, and 10\u201311 displayed immunosuppressive activity, with inhibitory rates of 62.9%, 59.5%, 67.8%, 55.8%, and 68.7%, respectively, at a concentration of 5 \u03bcg\/mL.<\/jats:p>","DOI":"10.3390\/md21070382","type":"journal-article","created":{"date-parts":[[2023,6,29]],"date-time":"2023-06-29T01:15:47Z","timestamp":1688001347000},"page":"382","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Cytosporin Derivatives from Arctic-Derived Fungus Eutypella sp. D-1 via the OSMAC Approach"],"prefix":"10.3390","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0516-4664","authenticated-orcid":false,"given":"Hao-Bing","family":"Yu","sequence":"first","affiliation":[{"name":"Naval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhe","family":"Ning","sequence":"additional","affiliation":[{"name":"Naval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo","family":"Hu","sequence":"additional","affiliation":[{"name":"Naval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu-Ping","family":"Zhu","sequence":"additional","affiliation":[{"name":"Basic Medical Experimental Teaching Center, College of Basic Medical Sciences, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiao-Ling","family":"Lu","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Molecular Biology, College of Basic Medical Sciences, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ying","family":"He","sequence":"additional","affiliation":[{"name":"Naval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bing-Hua","family":"Jiao","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Molecular Biology, College of Basic Medical Sciences, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3723-5711","authenticated-orcid":false,"given":"Xiao-Yu","family":"Liu","sequence":"additional","affiliation":[{"name":"Naval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,6,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Arrieche, D., Cabrera-Pardo, J.R., San-Martin, A., Carrasco, H., and Taborga, L. (2023). Natural Products from Chilean and Antarctic Marine Fungi and Their Biomedical Relevance. Mar. Drugs, 21.","DOI":"10.3390\/md21020098"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"119","DOI":"10.7164\/antibiotics.49.119","article-title":"Discovery of an angiotensin II binding inhibitor from a Cytospora sp. using semi-automated screening procedures","volume":"49","author":"Goetz","year":"1996","journal-title":"J. Antibiot."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"6751","DOI":"10.1016\/j.tetlet.2013.10.005","article-title":"Cytosporins F\u2013K, new epoxyquinols from the endophytic fungus Pestalotiopsis theae","volume":"54","author":"Akone","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5365","DOI":"10.1016\/j.tet.2008.03.016","article-title":"Cytosporin-related compounds from the marine-derived fungus Eutypella scoparia","volume":"64","author":"Ciavatta","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3089","DOI":"10.1021\/acs.jnatprod.9b00700","article-title":"Eutypellacytosporins A\u2013D, Meroterpenoids from the Arctic Fungus Eutypella sp. D-1","volume":"82","author":"Zhang","year":"2019","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"129","DOI":"10.3390\/md18020129","article-title":"Polyketide Derivatives from Mangrove Derived Endophytic Fungus Pseudopestalotiopsis theae","volume":"18","author":"Yu","year":"2020","journal-title":"Mar. Drugs"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1553","DOI":"10.1021\/acs.jnatprod.8b00039","article-title":"Libertellenones O\u2013S and Eutypellenones A and B, Pimarane Diterpene Derivatives from the Arctic Fungus Eutypella sp. D-1","volume":"81","author":"Yu","year":"2018","journal-title":"J. Nat. Prod."},{"key":"ref_8","first-page":"1181","article-title":"Secondary metabolites from Eutypella species and their bioactivities","volume":"36","author":"Tan","year":"2017","journal-title":"Mycosystema"},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Yu, H.-B., Wang, X.-L., Xu, W.-H., Zhang, Y.-X., Qian, Y.-S., Zhang, J.-P., Lu, X.-L., and Liu, X.-Y. (2018). Eutypellenoids A\u2013C, New Pimarane Diterpenes from the Arctic Fungus Eutypella sp. D-1. Mar. Drugs, 16.","DOI":"10.3390\/md16080284"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Romano, S., Jackson, S.A., Patry, S., and Dobson, A.D.W. (2018). Extending the \u201cOne Strain Many Compounds\u201d (OSMAC) Principle to Marine Microorganisms. Mar. Drugs, 16.","DOI":"10.3390\/md16070244"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"4821","DOI":"10.1016\/j.tet.2015.05.027","article-title":"Total synthesis of illicidione A and illihendione A","volume":"71","author":"Ren","year":"2015","journal-title":"Tetrahedron"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4001","DOI":"10.1016\/S0040-4039(01)00642-6","article-title":"Enantioselective syntheses of decursinol angelate and decursin","volume":"42","author":"Lim","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Zhang, Y.-H., Du, H.-F., Gao, W.-B., Li, W., Cao, F., and Wang, C.-Y. (2022). Anti-inflammatory Polyketides from the Marine-Derived Fungus Eutypella scoparia. Mar. Drugs, 20.","DOI":"10.3390\/md20080486"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1640","DOI":"10.1080\/14786419.2017.1285301","article-title":"A new hexahydrobenzopyran derivative from the gorgonian-derived Fungus Eutypella sp","volume":"31","author":"Liao","year":"2017","journal-title":"Nat. Prod. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1791","DOI":"10.1351\/pac200880081791","article-title":"Chemical wizardry? The generation of diversity in terpenoid biosynthesis","volume":"80","author":"Allemann","year":"2008","journal-title":"Pure Appl. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"961","DOI":"10.1080\/10286020.2018.1482880","article-title":"Bioactive metabolites from the Arctic fungus Nectria sp. B-13","volume":"21","author":"Yu","year":"2019","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Yu, H.-B., Gu, B.-B., Iwasaki, A., Jiang, W.-L., Ecker, A., Wang, S.-P., Yang, F., and Lin, H.-W. (2020). Dactylospenes A\u2013E, Sesterterpenes from the Marine Sponge Dactylospongia elegans. Mar. Drugs, 18.","DOI":"10.3390\/md18100491"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1579","DOI":"10.1021\/acs.jnatprod.1c00118","article-title":"Efophylins A and B, Two C2-Asymmetric Macrodiolide Immunosuppressants from Streptomyces malaysiensis","volume":"84","author":"Xu","year":"2021","journal-title":"J. Nat. 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