{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,26]],"date-time":"2026-06-26T14:52:41Z","timestamp":1782485561381,"version":"3.54.5"},"reference-count":33,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2021,9,27]],"date-time":"2021-09-27T00:00:00Z","timestamp":1632700800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Microbiol."],"abstract":"<jats:p>Three new tetramic acid derivatives (<jats:bold>1<\/jats:bold>\u2013<jats:bold>3<\/jats:bold>) and a new polyketide (<jats:bold>4<\/jats:bold>) along with eight known compounds (<jats:bold>5<\/jats:bold>\u2013<jats:bold>12<\/jats:bold>) were isolated from cultures of the deep-sea-derived fungus <jats:italic>Penicillium<\/jats:italic> sp. SCSIO06868. Four new structures were elucidated by analysis of one-dimensional\/two-dimensional nuclear magnetic resonance (NMR) data and high-resolution electrospray ionization mass spectrometry. Their absolute configurations were established by X-ray crystallography analysis and comparison of the experimental and reported electronic circular dichroism (ECD) values or specific optical rotation. Compound <jats:bold>3<\/jats:bold> exhibited potent, selective inhibitory activities against <jats:italic>Staphylococcus aureus<\/jats:italic> and methicillin-resistant <jats:italic>S. aureus<\/jats:italic> with minimum inhibitory concentration values of both 2.5 \u03bcg\/ml. Also, compound <jats:bold>3<\/jats:bold> showed weak antiviral activity against severe acute respiratory syndrome coronavirus 2 main protease, which was responsible for the coronavirus disease 2019 pandemic.<\/jats:p>","DOI":"10.3389\/fmicb.2021.730807","type":"journal-article","created":{"date-parts":[[2021,9,27]],"date-time":"2021-09-27T18:22:21Z","timestamp":1632766941000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":11,"title":["New Tetramic Acid Derivatives From the Deep-Sea-Derived Fungus Penicillium sp. SCSIO06868 With SARS-CoV-2 Mpro Inhibitory Activity Evaluation"],"prefix":"10.3389","volume":"12","author":[{"given":"Xiaoyan","family":"Pang","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weihao","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xuefeng","family":"Zhou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bin","family":"Yang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinpeng","family":"Tian","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junfeng","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shihai","family":"Xu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yonghong","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2021,9,27]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"1833","DOI":"10.1016\/S0040-4020(00)00092-2","article-title":"Melophlins A and B, novel tetramic acids reversing the phenotype of ras-transformed cells, from the marine sponge melophlus sarassinorum.","volume":"56","author":"Aoki","year":"2000","journal-title":"Tetrahedron"},{"key":"B2","doi-asserted-by":"publisher","first-page":"3650","DOI":"10.1021\/acs.orglett.6b01699","article-title":"Chrysamides A-C, three dimeric nitrophenyl trans-epoxyamides produced by the deep-sea-derived fungus Penicillium chrysogenum SCSIO41001.","volume":"18","author":"Chen","year":"2016","journal-title":"Org. Lett."},{"key":"B3","doi-asserted-by":"publisher","DOI":"10.3390\/md18010047","article-title":"Pyrenosetins A-C, new decalinoylspirotetramic acid derivatives isolated by bioactivity-based molecular networking from the seaweed-derived fungus Pyrenochaetopsis sp. FVE-001.","volume":"18","author":"Fan","year":"2020","journal-title":"Mar. Drugs"},{"key":"B4","doi-asserted-by":"publisher","first-page":"1197","DOI":"10.1080\/14786419.2018.1553880","article-title":"Two new aromatic polyketides from a deep-sea fungus Penicillium sp. SCSIO 06720.","volume":"34","author":"Guo","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"B5","doi-asserted-by":"publisher","DOI":"10.3390\/md18020114","article-title":"The biological and chemical diversity of tetramic acid compounds from marine-derived microorganisms.","volume":"18","author":"Jiang","year":"2020","journal-title":"Mar. Drugs"},{"key":"B6","doi-asserted-by":"publisher","DOI":"10.3390\/md14040076","article-title":"Potential pharmacological resources: natural bioactive compounds from marine-derived fungi.","volume":"14","author":"Jin","year":"2016","journal-title":"Mar. Drugs"},{"key":"B7","doi-asserted-by":"publisher","first-page":"289","DOI":"10.1038\/s41586-020-2223-y","article-title":"Structure of Mpro from SARS-CoV-2 and discovery of its inhibitors.","volume":"582","author":"Jin","year":"2020","journal-title":"Nature"},{"key":"B8","doi-asserted-by":"publisher","first-page":"2455","DOI":"10.1021\/jo3026737","article-title":"Synthesis of penicillenol C1 and of a bis-azide analogue for photoaffinity labeling.","volume":"78","author":"Kempf","year":"2013","journal-title":"J. Org. Chem."},{"key":"B9","doi-asserted-by":"publisher","first-page":"100","DOI":"10.1016\/j.fitote.2013.08.017","article-title":"Bioactive polyketides and alkaloids from Penicillium citrinum, a fungal endophyte isolated from Ocimum tenuiflorum.","volume":"91","author":"Lai","year":"2013","journal-title":"Fitoterapia"},{"key":"B10","doi-asserted-by":"publisher","first-page":"1051","DOI":"10.1007\/BF02980236","article-title":"Two new metabolites with cytotoxicities from deep-sea fungus, Aspergillus sydowi YHll-2.","volume":"33","author":"Li","year":"2007","journal-title":"Arch. Pharm. Res."},{"key":"B11","doi-asserted-by":"publisher","first-page":"27381","DOI":"10.1073\/pnas.2010470117","article-title":"Identify potent SARS-CoV-2 main protease inhibitors via accelerated free energy perturbation-based virtual screening of existing drugs.","volume":"117","author":"Li","year":"2020","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"key":"B12","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1248\/cpb.56.217","article-title":"Penicillenols from Penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum.","volume":"56","author":"Lin","year":"2008","journal-title":"Chem. Pharm. Bull."},{"key":"B13","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25010114","article-title":"Hyalodendrins A and B, new decalin-type tetramic acid larvicides from the endophytic fungus Hyalodendriella sp. Ponipodef12.","volume":"25","author":"Mao","year":"2019","journal-title":"Molecules"},{"key":"B14","doi-asserted-by":"publisher","first-page":"50566","DOI":"10.1039\/c4ra09047k","article-title":"Naturally occurring tetramic acid products: isolation, structure elucidation and biological activity.","volume":"4","author":"Mo","year":"2014","journal-title":"RSC Adv."},{"key":"B15","doi-asserted-by":"publisher","first-page":"8","DOI":"10.1002\/0471250953.bi0814s24","article-title":"Using AutoDock for ligand-receptor docking.","volume":"24","author":"Morris","year":"2008","journal-title":"Curr. Protoc. Bioinformatics"},{"key":"B16","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2020.1855643","article-title":"Tetramic acid based alkaloids from Aspergillus amoenus Roberg strain UP197-antibiotic properties and new pyranterreones.","author":"Nord","year":"2020","journal-title":"Nat. Prod. Res."},{"key":"B17","doi-asserted-by":"publisher","first-page":"1860","DOI":"10.1021\/acs.jnatprod.8b00345","article-title":"Spiro-phthalides and isocoumarins isolated from the marine-sponge-derived fungus Setosphaeria sp. SCSIO41009.","volume":"81","author":"Pang","year":"2018","journal-title":"J. Nat. Prod."},{"key":"B18","doi-asserted-by":"publisher","DOI":"10.1016\/j.fitote.2019.104406","article-title":"New quinoline alkaloid and bisabolane-type sesquiterpenoid derivatives from the deep-sea-derived fungus Aspergillus sp. SCSIO06786.","volume":"140","author":"Pang","year":"2020","journal-title":"Fitoterapia"},{"key":"B19","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.104600","article-title":"Structurally various sorbicillinoids from the deep-sea sediment derived fungus Penicillium sp. SCSIO06871.","volume":"107","author":"Pang","year":"2021","journal-title":"Bioorg. Chem."},{"key":"B20","doi-asserted-by":"publisher","first-page":"442","DOI":"10.2174\/1568026620666201207095117","article-title":"An updated review on SARS-CoV-2 main proteinase (MPro): protein structure and small-molecule inhibitors.","volume":"21","author":"Sabbah","year":"2021","journal-title":"Curr. Top. Med. Chem."},{"key":"B21","doi-asserted-by":"publisher","first-page":"4203","DOI":"10.1016\/j.bmc.2008.02.069","article-title":"Tetramic and tetronic acids: an update on new derivatives and biological aspects.","volume":"16","author":"Schobert","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"B22","doi-asserted-by":"publisher","first-page":"10333","DOI":"10.1002\/chem.201901405","article-title":"Aminotenuazonic acid: isolation, structure elucidation, total synthesis and herbicidal activity of a new tetramic acid from fruiting bodies of Laccaria species.","volume":"25","author":"Schrey","year":"2019","journal-title":"Chemistry"},{"key":"B23","doi-asserted-by":"publisher","first-page":"4391","DOI":"10.1021\/jo300527f","article-title":"A synthetic approach to diverse 3-acyltetramic acids via O- to C-acyl rearrangement and application to the total synthesis of penicillenol series.","volume":"77","author":"Sengoku","year":"2012","journal-title":"J. Org. Chem."},{"key":"B24","doi-asserted-by":"publisher","first-page":"1698","DOI":"10.3390\/md13041698","article-title":"Identification and bioactivity of compounds from the fungus Penicillium sp. CYE-87 isolated from a marine tunicate.","volume":"13","author":"Shaala","year":"2015","journal-title":"Mar. Drugs"},{"key":"B25","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.ijbiomac.2021.02.071","article-title":"Potential drug targets of SARS-CoV-2: from genomics to therapeutics.","volume":"177","author":"Shamsi","year":"2021","journal-title":"Int. J. Biol. Macromol."},{"key":"B26","doi-asserted-by":"publisher","first-page":"9328","DOI":"10.1016\/j.tet.2015.10.010","article-title":"Cytotoxic and antiviral tetramic acid derivatives from the deep-sea-derived fungus Trichobotrys effuse DFFSCS021.","volume":"71","author":"Sun","year":"2015","journal-title":"Tetrahedron"},{"key":"B27","doi-asserted-by":"publisher","first-page":"273","DOI":"10.1021\/np049661q","article-title":"Scalusamides A-C, new pyrrolidine alkaloids from the marine-derived fungus Penicillium citrinum.","volume":"68","author":"Tsuda","year":"2005","journal-title":"J. Nat. Prod."},{"key":"B28","doi-asserted-by":"publisher","first-page":"2910","DOI":"10.1021\/acs.jafc.6b00527","article-title":"Antifungal new oxepine-containing alkaloids and xanthones from the deep-sea-derived fungus Aspergillus versicolor SCSIO 05879.","volume":"64","author":"Wang","year":"2016","journal-title":"J. Agric. Food Chem."},{"key":"B29","doi-asserted-by":"publisher","first-page":"1390","DOI":"10.1002\/cmdc.202000241","article-title":"Synthesis of tetramic acid fragments derived from Vancoresmycin showing inhibitory effects towards S. aureus.","volume":"15","author":"Wingen","year":"2020","journal-title":"Chem. Med. Chem."},{"key":"B30","doi-asserted-by":"publisher","first-page":"3242","DOI":"10.1021\/acs.jnatprod.9b00206","article-title":"Melongenaterpenes A-L, vetispirane-type sesquiterpenoids from the roots of Solanum melongena.","volume":"82","author":"Yin","year":"2019","journal-title":"J. Nat. Prod."},{"key":"B31","doi-asserted-by":"publisher","first-page":"2944","DOI":"10.1055\/s-0030-1259045","article-title":"First stereoselective synthesis of penicillenol A1 via novel O- to C-acyl rearrangement of O-acyltetramic acid.","volume":"2010","author":"Yoda","year":"2010","journal-title":"Synlett"},{"key":"B32","doi-asserted-by":"publisher","first-page":"271","DOI":"10.1016\/j.ijbiomac.2020.06.007","article-title":"Corona virus versus existence of human on the earth: a computational and biophysical approach.","volume":"161","author":"Zehra","year":"2020","journal-title":"Int. J. Biol. Macromol."},{"key":"B33","doi-asserted-by":"publisher","first-page":"947","DOI":"10.1021\/acs.jnatprod.8b01029","article-title":"Anti-inflammatory mono- and dimeric sorbicillinoids from the marine-derived fungus Trichoderma reesei 4670.","volume":"82","author":"Zhang","year":"2019","journal-title":"J. Nat. Prod."}],"container-title":["Frontiers in Microbiology"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fmicb.2021.730807\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,9,27]],"date-time":"2021-09-27T18:22:23Z","timestamp":1632766943000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fmicb.2021.730807\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,9,27]]},"references-count":33,"alternative-id":["10.3389\/fmicb.2021.730807"],"URL":"https:\/\/doi.org\/10.3389\/fmicb.2021.730807","relation":{},"ISSN":["1664-302X"],"issn-type":[{"value":"1664-302X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,9,27]]},"article-number":"730807"}}