{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T17:20:44Z","timestamp":1790011244432,"version":"4.0.1"},"reference-count":22,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2019,6,3]],"date-time":"2019-06-03T00:00:00Z","timestamp":1559520000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Three new butenolide derivatives, namely aspernolides N\u2013P (1\u20133), together with six known analogues (4\u20139), were isolated from the ethyl acetate (EtOAc) extract of the deep sea-derived fungus Aspergillus terreus YPGA10. The structures of compounds 1\u20133 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1 and 2 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compound 1 represents the rare example of Aspergillus-derived butenolide derivatives featured by a monosubstituted benzene ring. Compounds 6\u20139 exhibited remarkable inhibitory effects against \u03b1-glucosidase with IC50 values of 3.87, 1.37, 6.98, and 8.06 \u03bcM, respectively, being much more active than the positive control acarbose (190.2 \u03bcM).<\/jats:p>","DOI":"10.3390\/md17060332","type":"journal-article","created":{"date-parts":[[2019,6,3]],"date-time":"2019-06-03T11:31:01Z","timestamp":1559561461000},"page":"332","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Butenolide Derivatives with \u03b1-Glucosidase Inhibitions from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10"],"prefix":"10.3390","volume":"17","author":[{"given":"Zhongbin","family":"Cheng","sequence":"first","affiliation":[{"name":"Pharmaceutical College, Henan University, Kaifeng 475004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuanli","family":"Li","sequence":"additional","affiliation":[{"name":"Pharmaceutical College, Henan University, Kaifeng 475004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wan","family":"Liu","sequence":"additional","affiliation":[{"name":"Pharmaceutical College, Henan University, Kaifeng 475004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lijun","family":"Liu","sequence":"additional","affiliation":[{"name":"Pharmaceutical College, Henan University, Kaifeng 475004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jie","family":"Liu","sequence":"additional","affiliation":[{"name":"Pharmaceutical College, Henan University, Kaifeng 475004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wangjun","family":"Yuan","sequence":"additional","affiliation":[{"name":"Pharmaceutical College, Henan University, Kaifeng 475004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhuhua","family":"Luo","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Xu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qin","family":"Li","sequence":"additional","affiliation":[{"name":"Pharmaceutical College, Henan University, Kaifeng 475004, China"},{"name":"Eucommia Ulmoides Cultivation and Utilization of Henan Engineering Laboratory, Kaifeng 475004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,6,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1016\/j.phytochem.2008.10.017","article-title":"Aspernolides A and B, butenolides from a marine-derived fungus Aspergillus terreus","volume":"70","author":"Parvatkar","year":"2009","journal-title":"Phytochemistry"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1182","DOI":"10.1021\/np300897v","article-title":"Asperterrestide A, a cytotoxic cyclic tetrapeptide from the marine-derived fungus Aspergillus terreus SCSGAF0162","volume":"76","author":"He","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1007\/s11274-017-2228-3","article-title":"Bioactive compounds of Aspergillus terreus F7, an endophytic fungus from Hyptis suaveolens (L.) Poit","volume":"33","author":"Brissow","year":"2017","journal-title":"World J. Microb. Biot."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1221","DOI":"10.1248\/cpb.58.1221","article-title":"Butenolide and furandione from an endophytic Aspergillus terreus","volume":"58","author":"Nuclear","year":"2010","journal-title":"Chem. Pharm. Bull."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Zhang, Y.Y., Zhang, Y., Yao, Y.B., Lei, X.-L., and Qian, Z.J. (2018). Butyrolactone-I from coral-derived fungus Aspergillus terreus attenuates neuro-inflammatory response via suppression of NF-\u03baB pathway in BV-2 cells. Mar. Drugs, 16.","DOI":"10.3390\/md16060202"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1248\/cpb.48.559","article-title":"Butyrolactones from Aspergillus terreus","volume":"48","author":"Rao","year":"2000","journal-title":"Chem. Pharm. Bull."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1545","DOI":"10.1248\/cpb.58.1545","article-title":"Butyrolactones from the fungus Aspergillus terreus BCC 4651","volume":"58","author":"Haritakun","year":"2010","journal-title":"Chem. Pharm. Bull."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Yang, L.-H., Ou-Yang, H., Yan, X., Tang, B.W., Fang, M.J., Wu, Z., Chen, J.W., and Qiu, Y.-K. (2018). Open-ring butenolides from a marine-derived anti-neuroinflammatory fungus Aspergillus terreus Y10. Mar. Drugs, 16.","DOI":"10.3390\/md16110428"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1016\/j.bmcl.2017.12.049","article-title":"New butenolide derivatives from the marine sponge-derived fungus Aspergillus terreus","volume":"28","author":"Sun","year":"2018","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"422","DOI":"10.3389\/fchem.2018.00422","article-title":"\u03b1-Glucosidase inhibitors from the coral-associated fungus Aspergillus terreus","volume":"6","author":"Liu","year":"2018","journal-title":"Front. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"74","DOI":"10.14499\/indonesianjpharm29iss2pp74","article-title":"Isolation and identification of \u03b1-glucosidase inhibitor from Aspergillus terreus F38","volume":"29","author":"Munasaroh","year":"2018","journal-title":"Indones. J. Pharm."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"999","DOI":"10.1039\/C3NP70118B","article-title":"Recent advances in deep-sea natural products","volume":"31","author":"Skropeta","year":"2014","journal-title":"Nat. Prod. Rep."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.fitote.2018.12.022","article-title":"Two new meroterpenoids and two new monoterpenoids from the deep sea-derived fungus Penicillium sp. YPGA11","volume":"133","author":"Cheng","year":"2019","journal-title":"Fitoterapia"},{"key":"ref_14","first-page":"1","article-title":"Penicindopene A, a new indole diterpene from the deep-sea fungus Penicillium sp. YPCMAC1","volume":"Oct 1","author":"Liu","year":"2018","journal-title":"Nat. Prod. Res."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Cheng, Z., Xu, W., Liu, L., Li, S., Yuan, W., Luo, Z., Zhang, J., Cheng, Y., and Li, Q. (2018). Peniginsengins B\u2013E, new farnesylcyclohexenones from the deep sea-derived fungus Penicillium sp. YPGA11. Mar. Drugs, 16.","DOI":"10.3390\/md16100358"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1035","DOI":"10.1021\/acs.jnatprod.5b01103","article-title":"Eremophilane-type sesquiterpenoids from an Acremonium sp. fungus isolated from deep-sea sediments","volume":"79","author":"Cheng","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Li, Y., Liu, W., Xu, W., Zeng, X., Cheng, Z., and Li, Q. (2019). Aspterrics A and B, new sesquiterpenes from deep sea-derived fungus Aspergillus terreus YPGA10. Rec. Nat. Prod.","DOI":"10.25135\/rnp.131.19.04.1247"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1080\/14786410701852826","article-title":"Secondary metabolites of Aspergillus sp. F1, a commensal fungal strain of Trewia nudiflora","volume":"23","author":"Lin","year":"2009","journal-title":"Nat. Prod. Res."},{"key":"ref_19","unstructured":"(2013). Sybyl Software, Tripos Associates Inc.. version X 2.0."},{"key":"ref_20","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2009). Gaussian 09, Rev. C 01, Gaussian, Inc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5345","DOI":"10.1021\/acs.jafc.6b01909","article-title":"Antidiabetic potential of purple and red rice (Oryza sativa L.) bran extracts","volume":"64","author":"Boue","year":"2016","journal-title":"J. Agric. Food Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1505","DOI":"10.1021\/np300417q","article-title":"\u03b1-Glucosidase inhibitory hydrolyzable tannins from Eugenia jambolana seeds","volume":"75","author":"Omar","year":"2012","journal-title":"J. Nat. Prod."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/17\/6\/332\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:55:48Z","timestamp":1760187348000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/17\/6\/332"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,6,3]]},"references-count":22,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2019,6]]}},"alternative-id":["md17060332"],"URL":"https:\/\/doi.org\/10.3390\/md17060332","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,6,3]]}}}