Quinazolinone nitriles and related metabolites from the deep-sea-derived fungus Penicillium viridicatum MCCC 3A00265†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-12-17 Epub Date: 2024-12-24 DOI:10.1039/d4ob01795a
Meng Zhang , Tai-Zong Wu , Jia-Jian Wang , Hao-Yu Yu , Ji-Hong Zhang , Da-Li Meng , Xian-Wen Yang
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Abstract

Two new quinazolinone nitriles ( and ) and one new indole alkaloid (), 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 ( and ) are the sole representatives of quinazolinones featuring a nitrile group, while solitumidine F () incorporates a rare pyrrolidinedione unit as an indole terpenoid. In particular, compounds and exhibit significant activity in reactivating mutant p53 at 10 μM, indicating their potential for application in cancer therapy.

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深海来源真菌青霉菌mcc 3A00265的喹唑啉酮腈及其相关代谢物。
从深海来源的绿霉青霉MCCC 3A00265中分离到两个新的喹唑啉酮腈(1和2)和一个新的吲哚生物碱(3),并分离到13个已知化合物。通过广泛的光谱分析确定了它们的结构,并通过比较实验和计算的电子圆二色性(ECD)和旋光性(OR)数据以及生物遗传学因素确定了它们的绝对构型。viricyanoamide A和B(1和2)是具有腈基的喹唑啉酮的唯一代表,而solitumidine F(3)包含罕见的吡咯烷二酮单元作为吲哚萜类。特别是,化合物2和10在10 μM下对p53突变体的再激活表现出显著的活性,表明它们在癌症治疗中的应用潜力。
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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
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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