Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732
Five undescribed pentaketide derivatives, (<i>R</i>)-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1<i>H</i>-2-benzopyran-1-one (<b>1</b>), [(3<i>S</i>,4<i>R</i>)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1<i>H<...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-06-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/21/6/344 |
| _version_ | 1827736666945617920 |
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| author | Rotchana Klaram Tida Dethoup Fátima P. Machado Luís Gales Decha Kumla Salar Hafez Ghoran Emília Sousa Sharad Mistry Artur M. S. Silva Anake Kijjoa |
| author_facet | Rotchana Klaram Tida Dethoup Fátima P. Machado Luís Gales Decha Kumla Salar Hafez Ghoran Emília Sousa Sharad Mistry Artur M. S. Silva Anake Kijjoa |
| author_sort | Rotchana Klaram |
| collection | DOAJ |
| description | Five undescribed pentaketide derivatives, (<i>R</i>)-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1<i>H</i>-2-benzopyran-1-one (<b>1</b>), [(3<i>S</i>,4<i>R</i>)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1<i>H</i>-isochromen-3-yl]methyl acetate (<b>2</b>), (<i>R</i>)-5, 7-dimethoxy-3-((<i>S)</i>-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3<i>H</i>)-one (<b>4b</b>), (<i>S</i>)-7-hydroxy-3-((<i>S</i>)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3<i>H</i>)-one (<b>5</b>), and a <i>p</i>-hydroxyphenyl-2-pyridone derivative, avellaneanone (<b>6</b>), were isolated together with the previously reported (<i>R</i>)-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3<i>H</i>)-one (<b>3</b>), (<i>R</i>)-7-hydroxy-3-((<i>S</i>)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3<i>H</i>)-one (<b>4a</b>) and isosclerone (<b>7</b>), from the ethyl acetate extract of a culture of a marine sponge-derived fungus, <i>Hamigera avellanea</i> 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 <b>1</b>, <b>4b</b>, <b>5</b>, and <b>6</b> were established by X-ray crystallographic analysis. The absolute configurations of C-3 and C-4 in <b>2</b> were determined by ROESY correlations and on the basis of their common biosynthetic origin with <b>1</b>. The crude fungal extract and the isolated compounds <b>1</b>, <b>3</b>, <b>4b</b>, <b>5</b>, <b>6,</b> and <b>7</b> were assayed for their growth inhibitory activity against various plant pathogenic fungi viz. <i>Alternaria brassicicola</i>, <i>Bipolaris oryzae</i>, <i>Colletotrichum capsici, C. gloeosporiodes</i>, <i>Curvularia oryzae</i>, <i>Fusarium semitectum</i>, <i>Lasiodiplodia theobromae</i>, <i>Phytophthora palmivora</i>, <i>Pyricularia oryzae</i>, <i>Rhizoctonia oryzae</i> and <i>Sclerotium rolfsii</i>. |
| first_indexed | 2024-03-11T02:13:37Z |
| format | Article |
| id | doaj.art-8e5702be233e4e7abb2aa356c247399c |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T02:13:37Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-8e5702be233e4e7abb2aa356c247399c2023-11-18T11:22:35ZengMDPI AGMarine Drugs1660-33972023-06-0121634410.3390/md21060344Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732Rotchana Klaram0Tida Dethoup1Fátima P. Machado2Luís Gales3Decha Kumla4Salar Hafez Ghoran5Emília Sousa6Sharad Mistry7Artur M. S. Silva8Anake Kijjoa9ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, PortugalDepartment of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok 10240, ThailandInterdisciplinary Centre of Marine Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n, 4450-208 Matosinhos, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, PortugalFaculty of Pharmaceutical Sciences, Burapha University, 169 Long Had Bangsaen Rd, Chonburi 20131, ThailandHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, PakistanLaboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, PortugalDepartment of Chemistry, University of Leicester, University Road, Leicester LE 7 RH, UKDepartamento de Química & QOPNA, Universidade de Aveiro, 3810-193 Aveiro, PortugalICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, PortugalFive undescribed pentaketide derivatives, (<i>R</i>)-6,8-dihydroxy-4,5-dimethyl-3-methylidene-3,4-dihydro-1<i>H</i>-2-benzopyran-1-one (<b>1</b>), [(3<i>S</i>,4<i>R</i>)-3,8-dihydroxy-6-methoxy-4,5-dimethyl-1-oxo-3,4-dihydro-1<i>H</i>-isochromen-3-yl]methyl acetate (<b>2</b>), (<i>R</i>)-5, 7-dimethoxy-3-((<i>S)</i>-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3<i>H</i>)-one (<b>4b</b>), (<i>S</i>)-7-hydroxy-3-((<i>S</i>)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran 1(3<i>H</i>)-one (<b>5</b>), and a <i>p</i>-hydroxyphenyl-2-pyridone derivative, avellaneanone (<b>6</b>), were isolated together with the previously reported (<i>R</i>)-3-acetyl-7-hydroxy-5-methoxy-3,4-dimethylisobenzofuran-1(3<i>H</i>)-one (<b>3</b>), (<i>R</i>)-7-hydroxy-3-((<i>S</i>)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3<i>H</i>)-one (<b>4a</b>) and isosclerone (<b>7</b>), from the ethyl acetate extract of a culture of a marine sponge-derived fungus, <i>Hamigera avellanea</i> 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 <b>1</b>, <b>4b</b>, <b>5</b>, and <b>6</b> were established by X-ray crystallographic analysis. The absolute configurations of C-3 and C-4 in <b>2</b> were determined by ROESY correlations and on the basis of their common biosynthetic origin with <b>1</b>. The crude fungal extract and the isolated compounds <b>1</b>, <b>3</b>, <b>4b</b>, <b>5</b>, <b>6,</b> and <b>7</b> were assayed for their growth inhibitory activity against various plant pathogenic fungi viz. <i>Alternaria brassicicola</i>, <i>Bipolaris oryzae</i>, <i>Colletotrichum capsici, C. gloeosporiodes</i>, <i>Curvularia oryzae</i>, <i>Fusarium semitectum</i>, <i>Lasiodiplodia theobromae</i>, <i>Phytophthora palmivora</i>, <i>Pyricularia oryzae</i>, <i>Rhizoctonia oryzae</i> and <i>Sclerotium rolfsii</i>.https://www.mdpi.com/1660-3397/21/6/344<i>Hamigera avellanea</i>Aspergillaceaemarine sponge-associated funguspentaketidesdihydrochromone5-<i>p</i>-hydroxy-2-pyridone |
| spellingShingle | Rotchana Klaram Tida Dethoup Fátima P. Machado Luís Gales Decha Kumla Salar Hafez Ghoran Emília Sousa Sharad Mistry Artur M. S. Silva Anake Kijjoa Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732 Marine Drugs <i>Hamigera avellanea</i> Aspergillaceae marine sponge-associated fungus pentaketides dihydrochromone 5-<i>p</i>-hydroxy-2-pyridone |
| title | Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732 |
| title_full | Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732 |
| title_fullStr | Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732 |
| title_full_unstemmed | Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732 |
| title_short | Pentaketides and 5-<i>p</i>-Hydroxyphenyl-2-pyridone Derivative from the Culture Extract of a Marine Sponge-Associated Fungus <i>Hamigera avellanea</i> KUFA0732 |
| title_sort | pentaketides and 5 i p i hydroxyphenyl 2 pyridone derivative from the culture extract of a marine sponge associated fungus i hamigera avellanea i kufa0732 |
| topic | <i>Hamigera avellanea</i> Aspergillaceae marine sponge-associated fungus pentaketides dihydrochromone 5-<i>p</i>-hydroxy-2-pyridone |
| url | https://www.mdpi.com/1660-3397/21/6/344 |
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