{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T07:19:20Z","timestamp":1791875960150,"version":"4.3.4"},"reference-count":21,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2018,7,9]],"date-time":"2018-07-09T00:00:00Z","timestamp":1531094400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["41506156"],"award-info":[{"award-number":["41506156"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Natural Science Fundation of Guangdong Province","award":["2016A030310095"],"award-info":[{"award-number":["2016A030310095"]}]},{"name":"Natural Science Fundation of Jiangxi Province","award":["20171BCB24011"],"award-info":[{"award-number":["20171BCB24011"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Four new structurally related metabolites, one \u03b3-lactone named gliomasolide F (1), one \u03b4-lactone named gliomasolide G (2), and two medium-chain fatty acids named gliomacids A\u2013B (3\u20134), each containing nine carbons in total, were identified from the sponge-associated fungus Gliomastix sp. ZSDS1-F7-2. The planar chemical structures of these novel C9 metabolites were elucidated by nuclear magnetic resonance (NMR) spectroscopic methods, in connection with the analysis of high-resolution mass spectrometry (HRMS) and infrared (IR) data. The absolute configuration of 1, was determined by comparisons of experimental circular dichroism (CD) and optical rotation (OR) value with corresponding ones computed by quantum chemistry. The relative configuration of 2 was determined by the Nuclear Overhauser effect spectroscopy (NOESY) spectrum, while its absolute configuration was tentatively determined in view of the biogenetic and biosynthetic relationships between 1 and 2. Compounds 3\u20134, originally as an inseparable mixture, were successfully isolated after chemical modifications. The stereo-chemistries of compounds 3\u20134 were assumed by comparison of 13C NMR with those of the similar moiety reported in literature, in addition to the biogenetic and biosynthetic relationships with 1. The plausible biosynthetic relationships among these four C9 metabolites were supposed. Biologically, compounds 1\u20134 showed no cytotoxic effect against HeLa cell line at concentrations up to 25 \u03bcg\/mL, while 1 exhibited moderate antifouling activity against the settlement of Balanus amphitrite larvae with IC50 being 12.8 \u03bcg\/mL and LC50 &gt; 25 \u03bcg\/mL. The co-occurrence of macrolides gliomasolides A\u2014E and four C9 metabolites in the same fermentation culture made us assume that these C9 metabolites might be biosynthetic building blocks toward the construction of more complex macrolides such as gliomasolides A\u2014E or other unidentified polyketides.<\/jats:p>","DOI":"10.3390\/md16070231","type":"journal-article","created":{"date-parts":[[2018,7,9]],"date-time":"2018-07-09T11:18:53Z","timestamp":1531135133000},"page":"231","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Four New C9 Metabolites from the Sponge-Associated Fungus Gliomastix sp. ZSDS1-F7-2"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5002-9827","authenticated-orcid":false,"given":"Jun","family":"Zhang","sequence":"first","affiliation":[{"name":"National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, China"},{"name":"Department of Chemistry, Jinan University, Guangzhou 510000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhiqiang","family":"Yang","sequence":"additional","affiliation":[{"name":"National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan","family":"Liang","sequence":"additional","affiliation":[{"name":"National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liping","family":"Zhong","sequence":"additional","affiliation":[{"name":"National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huiting","family":"Lin","sequence":"additional","affiliation":[{"name":"National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Balian","family":"Zhong","sequence":"additional","affiliation":[{"name":"National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou 341000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liangchun","family":"Li","sequence":"additional","affiliation":[{"name":"School of Life Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shihai","family":"Xu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Jinan University, Guangzhou 510000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yonghong","family":"Liu","sequence":"additional","affiliation":[{"name":"Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,7,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2789","DOI":"10.1016\/j.tetlet.2014.02.062","article-title":"Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp.","volume":"55","author":"Zhou","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1021\/np060516h","article-title":"Aurantiomides A\u2013C, quinazoline alkaloids from the sponge-derived fungus Penicillium aurantiogriseum SP0-19","volume":"70","author":"Xin","year":"2007","journal-title":"J. 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