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

IF 4.9 2区 医学 Q1 CHEMISTRY, MEDICINAL Marine Drugs Pub Date : 2024-09-28 DOI:10.3390/md22100444
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":"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}
引用次数: 0

Abstract

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).

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
来自海洋真菌 Fusarium equiseti UBOCC-A-117302 的新 Fusarochromanone 衍生物。
两种新的扶桑色酮衍生物,脱乙酰基扶桑色烯(1)和脱乙酰氨基扶桑色-2',3-二烯(2),以及之前报道的代谢物扶桑色酮 TDP-2 (3)、扶桑色烯(4)、从海洋真菌 Fusarium equiseti UBOCC-A-117302 中分离出了 2,2-二甲基-5-氨基-6-(2'E-烯-4'-羟基丁酰)-4-色酮 (5)、fusarochromanone (6)、(-)-chrysogine (7) 和 equisetin (8)。这些化合物的结构是通过广泛的光谱(HRMS)和光谱(一维和二维 NMR)分析以及特定旋转测定的。其中,2 和 5 对三种蛋白激酶有抑制作用,IC50 值在 1.42 至 25.48 μM 之间。此外,还对所有分离化合物的细胞毒性和抗菌活性进行了评估。六种扶桑色原酮衍生物(1-6)对 RPE-1、HCT-116 和 U2OS 三种细胞系表现出不同的活性(IC50 值从 0.058 到 84.380 μM)。赤黄素(8)对蜡样芽孢杆菌和李斯特菌具有杀菌活性(MBC 值分别为 7.8 和 31.25 µM),对粪肠球菌具有抑菌活性(MIC 值为 31.25 µM)。化合物 2 和 4 对单核细胞增生李斯特菌具有抑菌活性(MIC 值为 125 µM)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Marine Drugs
Marine Drugs 医学-医药化学
CiteScore
9.60
自引率
14.80%
发文量
671
审稿时长
1 months
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.
期刊最新文献
Antioxidative and Anti-Atopic Dermatitis Effects of Peptides Derived from Hydrolyzed Sebastes schlegelii Tail By-Products. Metabolite Profiling of Macroalgae: Biosynthesis and Beneficial Biological Properties of Active Compounds. Characterization of Phytoplankton-Derived Amino Acids and Tracing the Source of Organic Carbon Using Stable Isotopes in the Amundsen Sea. Discovery of Anti-Inflammatory Alkaloids from Sponge Stylissa massa Suggests New Biosynthetic Pathways for Pyrrole-Imidazole Alkaloids. Talaroterpenoids A-F: Six New Seco-Terpenoids from the Marine-Derived Fungus Talaromyces aurantiacus.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1