Jialin Li , Hao Jia , Chen Chen , Shu An , Jianchen Yu , Jie Yuan , Yuhua Long , Mengfeng Li
{"title":"红树林内生真菌Talaromyces amestolkiae scu - f0041中具有抗sars - cov -2和抗炎活性的七环巯基萜类化合物。","authors":"Jialin Li , Hao Jia , Chen Chen , Shu An , Jianchen Yu , Jie Yuan , Yuhua Long , Mengfeng Li","doi":"10.1016/j.phytochem.2024.114344","DOIUrl":null,"url":null,"abstract":"<div><div>Under the guidance of LC‒MS/MS-based molecular networking, three previously undescribed berkeleyacetal type meroterpenoids, amestolknoids A-C (<strong>1</strong>–<strong>3</strong>), together with ten known analogues (<strong>4</strong>–<strong>13</strong>) were isolated and identified from the mangrove endophytic fungus <em>Talaromyces amestolkiae</em> SCNU–F0041. Amestolknoids A (<strong>1</strong>) and B (<strong>2</strong>) are unprecedentedly congested 6/7/6/5/5/5/5 heptacyclic scaffolds characterized by two chiral spiroketal centers. Amestolknoids A (<strong>1</strong>) and C (<strong>3</strong>) represent the first examples of chlorinated berkeleyacetal type meroterpenoids. Their structures were established by extensive spectroscopic analyses and single crystal X-ray diffraction. Bioassays revealed that amestolknoid C (<strong>3</strong>) exhibited excellent antiviral activity against SARS-CoV-2 with an EC<sub>50</sub> value of 2.50 μM and strong inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells with an IC<sub>50</sub> value of 4.10 μM. Compounds <strong>2</strong>, <strong>4</strong>, <strong>6</strong>, <strong>9</strong> and <strong>11</strong> showed moderate to good anti-inflammatory activities with IC<sub>50</sub> values of 41.78, 3.91, 43.52, 20.79, and 33.26 μM, respectively.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"231 ","pages":"Article 114344"},"PeriodicalIF":3.2000,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Congested heptacyclic meroterpenoids with anti-SARS-CoV-2 and anti-inflammatory activities from mangrove endophytic fungus Talaromyces amestolkiae SCNU–F0041\",\"authors\":\"Jialin Li , Hao Jia , Chen Chen , Shu An , Jianchen Yu , Jie Yuan , Yuhua Long , Mengfeng Li\",\"doi\":\"10.1016/j.phytochem.2024.114344\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Under the guidance of LC‒MS/MS-based molecular networking, three previously undescribed berkeleyacetal type meroterpenoids, amestolknoids A-C (<strong>1</strong>–<strong>3</strong>), together with ten known analogues (<strong>4</strong>–<strong>13</strong>) were isolated and identified from the mangrove endophytic fungus <em>Talaromyces amestolkiae</em> SCNU–F0041. Amestolknoids A (<strong>1</strong>) and B (<strong>2</strong>) are unprecedentedly congested 6/7/6/5/5/5/5 heptacyclic scaffolds characterized by two chiral spiroketal centers. Amestolknoids A (<strong>1</strong>) and C (<strong>3</strong>) represent the first examples of chlorinated berkeleyacetal type meroterpenoids. Their structures were established by extensive spectroscopic analyses and single crystal X-ray diffraction. Bioassays revealed that amestolknoid C (<strong>3</strong>) exhibited excellent antiviral activity against SARS-CoV-2 with an EC<sub>50</sub> value of 2.50 μM and strong inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells with an IC<sub>50</sub> value of 4.10 μM. Compounds <strong>2</strong>, <strong>4</strong>, <strong>6</strong>, <strong>9</strong> and <strong>11</strong> showed moderate to good anti-inflammatory activities with IC<sub>50</sub> values of 41.78, 3.91, 43.52, 20.79, and 33.26 μM, respectively.</div></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":\"231 \",\"pages\":\"Article 114344\"},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-11-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0031942224003819\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224003819","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Congested heptacyclic meroterpenoids with anti-SARS-CoV-2 and anti-inflammatory activities from mangrove endophytic fungus Talaromyces amestolkiae SCNU–F0041
Under the guidance of LC‒MS/MS-based molecular networking, three previously undescribed berkeleyacetal type meroterpenoids, amestolknoids A-C (1–3), together with ten known analogues (4–13) were isolated and identified from the mangrove endophytic fungus Talaromyces amestolkiae SCNU–F0041. Amestolknoids A (1) and B (2) are unprecedentedly congested 6/7/6/5/5/5/5 heptacyclic scaffolds characterized by two chiral spiroketal centers. Amestolknoids A (1) and C (3) represent the first examples of chlorinated berkeleyacetal type meroterpenoids. Their structures were established by extensive spectroscopic analyses and single crystal X-ray diffraction. Bioassays revealed that amestolknoid C (3) exhibited excellent antiviral activity against SARS-CoV-2 with an EC50 value of 2.50 μM and strong inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells with an IC50 value of 4.10 μM. Compounds 2, 4, 6, 9 and 11 showed moderate to good anti-inflammatory activities with IC50 values of 41.78, 3.91, 43.52, 20.79, and 33.26 μM, respectively.
期刊介绍：
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.
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