{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,20]],"date-time":"2026-03-20T02:55:10Z","timestamp":1773975310997,"version":"3.50.1"},"reference-count":31,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2023,6,2]],"date-time":"2023-06-02T00:00:00Z","timestamp":1685664000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"national infrastructure PT-OPENSCREEN","award":["NORTE-01-0145-FEDER-085468"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-085468"]}]},{"name":"national infrastructure PT-OPENSCREEN","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"national infrastructure PT-OPENSCREEN","award":["UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDP\/04423\/2020"]}]},{"name":"national funds through the FCT\u2014Foundation for Science and Technology","award":["NORTE-01-0145-FEDER-085468"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-085468"]}]},{"name":"national funds through the FCT\u2014Foundation for Science and Technology","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"national funds through the FCT\u2014Foundation for Science and Technology","award":["UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDP\/04423\/2020"]}]},{"name":"Office of the Ministry of Higher Education, Science, Research and Innovation","award":["NORTE-01-0145-FEDER-085468"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-085468"]}]},{"name":"Office of the Ministry of Higher Education, Science, Research and Innovation","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"Office of the Ministry of Higher Education, Science, Research and Innovation","award":["UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDP\/04423\/2020"]}]},{"name":"Thailand Science Research and Innovation","award":["NORTE-01-0145-FEDER-085468"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-085468"]}]},{"name":"Thailand Science Research and Innovation","award":["UIDB\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020"]}]},{"name":"Thailand Science Research and Innovation","award":["UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDP\/04423\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Five undescribed pentaketide derivatives, (R)-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1H-2-benzopyran-1-one (1), [(3S,4R)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1H-isochromen-3-yl]methyl acetate (2), (R)-5, 7-dimethoxy-3-((S)-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3H)-one (4b), (S)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3H)-one (5), and a p-hydroxyphenyl-2-pyridone derivative, avellaneanone (6), were isolated together with the previously reported (R)-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (3), (R)-7-hydroxy-3-((S)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (4a) and isosclerone (7), from the ethyl acetate extract of a culture of a marine sponge-derived fungus, Hamigera avellanea KUFA0732. The structures of the undescribed compounds were elucidated using 1D and 2D NMR, as well as high-resolution mass spectral analyses. The absolute configurations of the stereogenic carbons in 1, 4b, 5, and 6 were established by X-ray crystallographic analysis. The absolute configurations of C-3 and C-4 in 2 were determined by ROESY correlations and on the basis of their common biosynthetic origin with 1. The crude fungal extract and the isolated compounds 1, 3, 4b, 5, 6, and 7 were assayed for their growth inhibitory activity against various plant pathogenic fungi viz. Alternaria brassicicola, Bipolaris oryzae, Colletotrichum capsici, C. gloeosporiodes, Curvularia oryzae, Fusarium semitectum, Lasiodiplodia theobromae, Phytophthora palmivora, Pyricularia oryzae, Rhizoctonia oryzae and Sclerotium rolfsii.<\/jats:p>","DOI":"10.3390\/md21060344","type":"journal-article","created":{"date-parts":[[2023,6,5]],"date-time":"2023-06-05T02:18:29Z","timestamp":1685931509000},"page":"344","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Pentaketides and 5-p-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus Hamigera avellanea KUFA0732"],"prefix":"10.3390","volume":"21","author":[{"given":"Rotchana","family":"Klaram","sequence":"first","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9079-3010","authenticated-orcid":false,"given":"Tida","family":"Dethoup","sequence":"additional","affiliation":[{"name":"Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2257-8941","authenticated-orcid":false,"given":"F\u00e1tima P.","family":"Machado","sequence":"additional","affiliation":[{"name":"Interdisciplinary Centre of Marine Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix\u00f5es, Av. General Norton de Matos s\/n, 4450-208 Matosinhos, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8352-6539","authenticated-orcid":false,"given":"Lu\u00eds","family":"Gales","sequence":"additional","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"},{"name":"Instituto de Biologia Molecular e Celular (i3S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1434-3958","authenticated-orcid":false,"given":"Decha","family":"Kumla","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences, Burapha University, 169 Long Had Bangsaen Rd, Chonburi 20131, Thailand"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5495-5556","authenticated-orcid":false,"given":"Salar","family":"Hafez Ghoran","sequence":"additional","affiliation":[{"name":"HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5397-4672","authenticated-orcid":false,"given":"Em\u00edlia","family":"Sousa","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica e Farmac\u00eautica, Departamento de Ci\u00eancias Qu\u00edmicas, Faculdade de Farm\u00e1cia, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal"}]},{"given":"Sharad","family":"Mistry","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur M. 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