Meng Zhang, Tai-Zong Wu, Jia-Jian Wang, Hao-Yu Yu, Ji-Hong Zhang, Da-Li Meng and Xian-Wen Yang
{"title":"Quinazolinone nitriles and related metabolites from the deep-sea-derived fungus Penicillium viridicatum MCCC 3A00265†","authors":"Meng Zhang, Tai-Zong Wu, Jia-Jian Wang, Hao-Yu Yu, Ji-Hong Zhang, Da-Li Meng and Xian-Wen Yang","doi":"10.1039/D4OB01795A","DOIUrl":null,"url":null,"abstract":"<p >Two new quinazolinone nitriles (<strong>1</strong> and <strong>2</strong>) and one new indole alkaloid (<strong>3</strong>), together with 13 known compounds, were isolated from the deep-sea-derived <em>Penicillium viridicatum</em> MCCC 3A00265. Their structures were determined by extensive spectroscopic analysis, with the absolute configurations established by comparing experimental and calculated electronic circular dichroism (ECD) and optical rotation (OR) data as well as biogenetic considerations. Viricyanoamides A and B (<strong>1</strong> and <strong>2</strong>) are the sole representatives of quinazolinones featuring a nitrile group, while solitumidine F (<strong>3</strong>) incorporates a rare pyrrolidinedione unit as an indole terpenoid. In particular, compounds <strong>2</strong> and <strong>10</strong> exhibit significant activity in reactivating mutant p53 at 10 μM, indicating their potential for application in cancer therapy.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" 6","pages":" 1380-1385"},"PeriodicalIF":2.7000,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/ob/d4ob01795a","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Two new quinazolinone nitriles (1 and 2) and one new indole alkaloid (3), together with 13 known compounds, were isolated from the deep-sea-derived Penicillium viridicatum MCCC 3A00265. Their structures were determined by extensive spectroscopic analysis, with the absolute configurations established by comparing experimental and calculated electronic circular dichroism (ECD) and optical rotation (OR) data as well as biogenetic considerations. Viricyanoamides A and B (1 and 2) are the sole representatives of quinazolinones featuring a nitrile group, while solitumidine F (3) incorporates a rare pyrrolidinedione unit as an indole terpenoid. In particular, compounds 2 and 10 exhibit significant activity in reactivating mutant p53 at 10 μM, indicating their potential for application in cancer therapy.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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