Giang Nam Pham, Béatrice Josselin, Arnaud Cousseau, Blandine Baratte, Marie Dayras, Christophe Le Meur, Stella Debaets, Amélie Weill, Thomas Robert, Gaëtan Burgaud, Ian Probert, Fatouma Mohamed Abdoul-Latif, Laurent Boyer, Stéphane Bach, Mohamed Mehiri
{"title":"来自海洋真菌 Fusarium equiseti UBOCC-A-117302 的新 Fusarochromanone 衍生物。","authors":"Giang Nam Pham, Béatrice Josselin, Arnaud Cousseau, Blandine Baratte, Marie Dayras, Christophe Le Meur, Stella Debaets, Amélie Weill, Thomas Robert, Gaëtan Burgaud, Ian Probert, Fatouma Mohamed Abdoul-Latif, Laurent Boyer, Stéphane Bach, Mohamed Mehiri","doi":"10.3390/md22100444","DOIUrl":null,"url":null,"abstract":"<p><p>Two new fusarochromanone derivatives, deacetylfusarochromene (<b>1</b>) and deacetamidofusarochrom-2',3-diene (<b>2</b>), along with the previously reported metabolites fusarochromanone TDP-2 (<b>3</b>), fusarochromene (<b>4</b>), 2,2-dimethyl-5-amino-6-(2'<i>E</i>-ene-4'-hydroxylbutyryl)-4-chromone (<b>5</b>), fusarochromanone (<b>6</b>), (-)-chrysogine (<b>7</b>), and equisetin (<b>8</b>), were isolated from the marine fungus <i>Fusarium equiseti</i> UBOCC-A-117302. The structures of the compounds were determined by extensive spectrometric (HRMS) and spectroscopic (1D and 2D NMR) analyses, as well as specific rotation. Among them, <b>2</b> and <b>5</b> showed inhibition of three protein kinases with IC<sub>50</sub> values ranging from 1.42 to 25.48 μM. Cytotoxicity and antimicrobial activity of all isolated compounds were also evaluated. Six fusarochromanone derivatives (<b>1</b>-<b>6</b>) exhibited diverse activities against three cell lines, RPE-1, HCT-116, and U2OS (IC<sub>50</sub> values ranging from 0.058 to 84.380 μM). Equisetin (<b>8</b>) showed bactericidal activities against <i>Bacillus cereus</i> and <i>Listeria monocytogenes</i> (MBC values of 7.8 and 31.25 µM, respectively), and bacteriostatic activity against <i>Enterococcus faecalis</i> (MIC value of 31.25 µM). Compounds <b>2</b> and <b>4</b> showed bacteriostatic activities against <i>Listeria monocytogenes</i> (MIC of 125 µM).</p>","PeriodicalId":18222,"journal":{"name":"Marine Drugs","volume":"22 10","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11509758/pdf/","citationCount":"0","resultStr":"{\"title\":\"New Fusarochromanone Derivatives from the Marine Fungus <i>Fusarium equiseti</i> UBOCC-A-117302.\",\"authors\":\"Giang Nam Pham, Béatrice Josselin, Arnaud Cousseau, Blandine Baratte, Marie Dayras, Christophe Le Meur, Stella Debaets, Amélie Weill, Thomas Robert, Gaëtan Burgaud, Ian Probert, Fatouma Mohamed Abdoul-Latif, Laurent Boyer, Stéphane Bach, Mohamed Mehiri\",\"doi\":\"10.3390/md22100444\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Two new fusarochromanone derivatives, deacetylfusarochromene (<b>1</b>) and deacetamidofusarochrom-2',3-diene (<b>2</b>), along with the previously reported metabolites fusarochromanone TDP-2 (<b>3</b>), fusarochromene (<b>4</b>), 2,2-dimethyl-5-amino-6-(2'<i>E</i>-ene-4'-hydroxylbutyryl)-4-chromone (<b>5</b>), fusarochromanone (<b>6</b>), (-)-chrysogine (<b>7</b>), and equisetin (<b>8</b>), were isolated from the marine fungus <i>Fusarium equiseti</i> UBOCC-A-117302. The structures of the compounds were determined by extensive spectrometric (HRMS) and spectroscopic (1D and 2D NMR) analyses, as well as specific rotation. Among them, <b>2</b> and <b>5</b> showed inhibition of three protein kinases with IC<sub>50</sub> values ranging from 1.42 to 25.48 μM. Cytotoxicity and antimicrobial activity of all isolated compounds were also evaluated. Six fusarochromanone derivatives (<b>1</b>-<b>6</b>) exhibited diverse activities against three cell lines, RPE-1, HCT-116, and U2OS (IC<sub>50</sub> values ranging from 0.058 to 84.380 μM). Equisetin (<b>8</b>) showed bactericidal activities against <i>Bacillus cereus</i> and <i>Listeria monocytogenes</i> (MBC values of 7.8 and 31.25 µM, respectively), and bacteriostatic activity against <i>Enterococcus faecalis</i> (MIC value of 31.25 µM). Compounds <b>2</b> and <b>4</b> showed bacteriostatic activities against <i>Listeria monocytogenes</i> (MIC of 125 µM).</p>\",\"PeriodicalId\":18222,\"journal\":{\"name\":\"Marine Drugs\",\"volume\":\"22 10\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-09-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11509758/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Marine Drugs\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://doi.org/10.3390/md22100444\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Marine Drugs","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.3390/md22100444","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
New Fusarochromanone Derivatives from the Marine Fungus Fusarium equiseti UBOCC-A-117302.
Two new fusarochromanone derivatives, deacetylfusarochromene (1) and deacetamidofusarochrom-2',3-diene (2), along with the previously reported metabolites fusarochromanone TDP-2 (3), fusarochromene (4), 2,2-dimethyl-5-amino-6-(2'E-ene-4'-hydroxylbutyryl)-4-chromone (5), fusarochromanone (6), (-)-chrysogine (7), and equisetin (8), were isolated from the marine fungus Fusarium equiseti UBOCC-A-117302. The structures of the compounds were determined by extensive spectrometric (HRMS) and spectroscopic (1D and 2D NMR) analyses, as well as specific rotation. Among them, 2 and 5 showed inhibition of three protein kinases with IC50 values ranging from 1.42 to 25.48 μM. Cytotoxicity and antimicrobial activity of all isolated compounds were also evaluated. Six fusarochromanone derivatives (1-6) exhibited diverse activities against three cell lines, RPE-1, HCT-116, and U2OS (IC50 values ranging from 0.058 to 84.380 μM). Equisetin (8) showed bactericidal activities against Bacillus cereus and Listeria monocytogenes (MBC values of 7.8 and 31.25 µM, respectively), and bacteriostatic activity against Enterococcus faecalis (MIC value of 31.25 µM). Compounds 2 and 4 showed bacteriostatic activities against Listeria monocytogenes (MIC of 125 µM).
期刊介绍:
Marine Drugs (ISSN 1660-3397) publishes reviews, regular research papers and short notes on the research, development and production of drugs from the sea. Our aim is to encourage scientists to publish their experimental and theoretical research in as much detail as possible, particularly synthetic procedures and characterization information for bioactive compounds. There is no restriction on the length of the experimental section.