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Wong Education Foundation","doi-asserted-by":"publisher","award":["GJTD-2020-12"],"award-info":[{"award-number":["GJTD-2020-12"]}],"id":[{"id":"10.13039\/501100012692","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Marine sponge-derived fungi have been proven to be a prolific source of bioactive natural products. Two new alkaloids, polonimides E (1) and D (2), and a new butenolide derivative, eutypoid F (11), were isolated from the Beibu Gulf sponge-derived fungus, Penicillium sp. SCSIO 41413, together with thirteen known compounds (3\u201310, 12\u201316). Their structures were determined by detailed NMR, MS spectroscopic analyses, and electronic circular dichroism (ECD) analyses. Butenolide derivatives 11 and 12 exhibited inhibitory effect against the enzyme PI3K with IC50 values of 1.7 \u03bcM and 9.8 \u03bcM, respectively. The molecular docking was also performed to understand the inhibitory activity, while 11 and 12 showed obvious protein\/ligand-binding effects to the PI3K protein. Moreover, 4 and 15 displayed obvious inhibitory activity against LPS-induced NF-\u03baB activation in RAW264.7 cells at 10 \u00b5M.<\/jats:p>","DOI":"10.3390\/md21010027","type":"journal-article","created":{"date-parts":[[2022,12,29]],"date-time":"2022-12-29T02:54:42Z","timestamp":1672282482000},"page":"27","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Two New Alkaloids and a New Butenolide Derivative from the Beibu Gulf Sponge-Derived Fungus Penicillium sp. SCSIO 41413"],"prefix":"10.3390","volume":"21","author":[{"given":"Yuxiu","family":"Ye","sequence":"first","affiliation":[{"name":"Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiaqi","family":"Liang","sequence":"additional","affiliation":[{"name":"CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology\/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianglian","family":"She","sequence":"additional","affiliation":[{"name":"CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology\/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiuping","family":"Lin","sequence":"additional","affiliation":[{"name":"CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology\/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6702-5366","authenticated-orcid":false,"given":"Junfeng","family":"Wang","sequence":"additional","affiliation":[{"name":"CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology\/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8327-3108","authenticated-orcid":false,"given":"Yonghong","family":"Liu","sequence":"additional","affiliation":[{"name":"Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China"},{"name":"CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology\/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dehua","family":"Yang","sequence":"additional","affiliation":[{"name":"The National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanhui","family":"Tan","sequence":"additional","affiliation":[{"name":"State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541001, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2114-1609","authenticated-orcid":false,"given":"Xiaowei","family":"Luo","sequence":"additional","affiliation":[{"name":"Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9601-4869","authenticated-orcid":false,"given":"Xuefeng","family":"Zhou","sequence":"additional","affiliation":[{"name":"Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China"},{"name":"CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology\/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"fiz089","DOI":"10.1093\/femsec\/fiz089","article-title":"Diversity and antimicrobial potential of Actinobacteria isolated from diverse marine sponges along the Beibu Gulf of the South China Sea","volume":"95","author":"Liu","year":"2019","journal-title":"FEMS Microbiol. 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Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1007\/978-3-642-55519-0_5","article-title":"Bioactive natural products from marine invertebrates and associated fungi","volume":"37","author":"Proksch","year":"2003","journal-title":"Prog. Mol. Subcell. Biol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1021\/acs.jmedchem.0c02026","article-title":"Marine natural products: A potential source of anti-hepatocellular carcinoma drugs","volume":"64","author":"Ren","year":"2021","journal-title":"J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Guo, X.C., Zhang, Y.H., Gao, W.B., Pan, L., Zhu, H.J., and Cao, F. (2020). Absolute configurations and chitinase inhibitions of quinazoline-containing diketopiperazines from the marine-derived fungus Penicillium polonicum. Mar. Drugs., 18.","DOI":"10.3390\/md18090479"},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Peng, Q., Chen, W., Lin, X., Xiao, J., Liu, Y., and Zhou, X. (2022). Butenolides from the coral-derived fungus Aspergillius terreus SCSIO41404. Mar. Drugs, 20.","DOI":"10.3390\/md20030212"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1248\/cpb.47.1491","article-title":"New quinazoline alkaloids from Glycosmis cochinchinensis","volume":"47","author":"Ito","year":"1999","journal-title":"Chem. Pharm. Bull."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Xing, C.P., Chen, D., Xie, C.L., Liu, Q., Zhong, T.H., Shao, Z., Liu, G., Luo, L.Z., and Yang, X.W. (2021). Anti-food allergic compounds from Penicillium griseofulvum MCCC 3A00225, a deep-sea-derived fungus. Mar. Drugs, 19.","DOI":"10.3390\/md19040224"},{"key":"ref_11","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. Nat. Prod."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"559","DOI":"10.3390\/md10030559","article-title":"Activation of the dormant secondary metabolite production by introducing gentamicin-resistance in a marine-derived Penicillium purpurogenum G59","volume":"10","author":"Chai","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1085","DOI":"10.1007\/s00044-017-2130-4","article-title":"Bioactive secondary metabolites from new terrestrial Streptomyces sp. TN82 strain: Isolation, structure elucidation and biological activity","volume":"27","author":"El","year":"2018","journal-title":"Med. Chem. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"322","DOI":"10.1007\/s10600-011-9922-4","article-title":"Isolation, structure elucidation, crystal structure, and biological activity of a marine natural alkaloid, viridicatol","volume":"47","author":"Wei","year":"2011","journal-title":"Chem. Nat. Compd."},{"key":"ref_15","first-page":"16","article-title":"Study on the alkaloiods from two great white shark\u2019s gill-derived Penicillium strains and their bioactivity","volume":"35","author":"Feng","year":"2016","journal-title":"Chin. J. Mar. Drugs."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"622","DOI":"10.1038\/s41429-020-0302-9","article-title":"Inhibition of cellular inflammatory mediator production and amelioration of learning deficit in flies by deep sea Aspergillus-derived cyclopenin","volume":"73","author":"Wang","year":"2020","journal-title":"J. Antibiot."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2744","DOI":"10.3390\/md8112744","article-title":"Verrucisidinol and verrucosidinol acetate, two pyrone-type polyketides isolated from a marine derived fungus, Penicillium aurantiogriseum","volume":"8","author":"Yu","year":"2010","journal-title":"Mar. Drugs."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1038\/ja.2005.26","article-title":"Deoxyverrucosidin, a novel GRP78\/BiP down-regulator, produced by Penicillium sp.","volume":"58","author":"Choo","year":"2005","journal-title":"J. Antibiot."},{"key":"ref_19","first-page":"1329","article-title":"New verrucosidin derivatives from the marine-derived fungus Penicillium sp. XL-01","volume":"13","author":"Xu","year":"2018","journal-title":"Nat. Prod. Commun."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"857041","DOI":"10.3389\/fmicb.2022.857041","article-title":"Thiodiketopiperazines and alkane derivatives produced by the mangrove sediment\u2013derived fungus Penicillium ludwigii SCSIO 41408","volume":"13","author":"Cai","year":"2022","journal-title":"Front. Microbiol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3611","DOI":"10.1021\/acs.jmedchem.5b00352","article-title":"Structure-based design of potent and selective inhibitors of the metabolic kinase PFKFB3","volume":"58","author":"Boyd","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4242","DOI":"10.1111\/bph.15179","article-title":"A marine fungus-derived nitrobenzoyl sesquiterpenoid suppresses receptor activator of NF-kB ligand-induced osteoclastogenesis and inflammatory bone destruction","volume":"177","author":"Tan","year":"2020","journal-title":"Brit. J. Pharmacol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1021\/acs.jnatprod.7b00698","article-title":"Nitrobenzoyl sesquiterpenoids with cytotoxic activities from a marinederived Aspergillus ochraceus fungus","volume":"81","author":"Tan","year":"2018","journal-title":"J. Nat. Prod."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1371","DOI":"10.1021\/acs.orglett.8b00142","article-title":"Soliseptide A, a cyclic hexapeptide possessing piperazic acid groups from Streptomyces solisilvae HNM30702","volume":"20","author":"Wang","year":"2018","journal-title":"Org. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"128271","DOI":"10.1016\/j.bmcl.2021.128271","article-title":"Discovery of cinnoline derivatives as potent PI3K inhibitors with antiproliferative activity","volume":"48","author":"Tian","year":"2021","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. 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