New Fusarochromanone Derivatives from the Marine Fungus Fusarium equiseti UBOCC-A-117302

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).

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Publication Details

Journal
Marine Drugs
Published
2024-09-28
DOI
https://doi.org/10.3390/md22100444
Citations
5
Primary Topic
Microbial Natural Products and Biosynthesis
Type
article
Field-Weighted Citation Impact
2.24

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article

New Fusarochromanone Derivatives from the Marine Fungus Fusarium equiseti UBOCC-A-117302

Amélie Weill, Giang Nam Pham, Arnaud Cousseau, Stéphane Bach et al.
5 citations
Marine Drugs
Microbial Natural Products and Biosynthesis
2.24
article

New Fusarochromanone Derivatives from the Marine Fungus Fusarium equiseti UBOCC-A-117302

Amélie Weill, Giang Nam Pham, Arnaud Cousseau, Stéphane Bach, Ian Probert, Béatrice Josselin, Thomas Robert, Mohamed Mehiri, Stella Debaets, Marie Dayras, Gaëtan Burgaud, Christophe Le Meur, Fatouma Mohamed Abdoul‐Latif, Laurent Boyer, Blandine Baratte
article en
5 citations

Abstract

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).

Marine DrugsVol. 22(10)
Centre National de la Recherche Scientifique (FR), Inserm (FR), Université de Bretagne Occidentale (FR), Université Côte d'Azur (FR), Station Biologique de Roscoff (FR), Sorbonne Université (FR), Institut de Chimie de Nice (FR), Laboratoire de Biologie Intégrative des Modèles Marins (FR), Institut National de Recherche pour l'Agriculture, l'Alimentation et l'Environnement (FR), Centre Méditerranéen de Médecine Moléculaire (FR), Laboratoire de Biodiversité et Biotechnologies Microbiennes (FR), Centre d'Étude et de Recherche de Djibouti (DJ)
Infrastructures en Biologie Santé et Agronomie, Conseil Régional de Bretagne, Cancéropôle Grand Ouest
Life below water
Openalex Percentile: Top 12%
Microbial Natural Products and Biosynthesis
2.24
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