Cladoic Acid, an Anti-Trypanosoma cruzi Polyketide from Cladosporium sp. TP-F2020.

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL
Journal of Natural Products Pub Date : 2024-08-23 Epub Date: 2024-08-05 DOI:10.1021/acs.jnatprod.4c00567
Md Masud Rana, Shiyang Lu, Tatiana Ascencio Menjívar, Keisuke Fukaya, Junko Nakajima-Shimada, Daisuke Urabe, Yasuhiro Igarashi
{"title":"Cladoic Acid, an Anti-<i>Trypanosoma cruzi</i> Polyketide from <i>Cladosporium</i> sp. TP-F2020.","authors":"Md Masud Rana, Shiyang Lu, Tatiana Ascencio Menjívar, Keisuke Fukaya, Junko Nakajima-Shimada, Daisuke Urabe, Yasuhiro Igarashi","doi":"10.1021/acs.jnatprod.4c00567","DOIUrl":null,"url":null,"abstract":"<p><p>A new polyketide, cladoic acid, was isolated from a fungus of the genus <i>Cladosporium</i>. The structure of the highly oxygenated <i>trans</i>-decalin ring with an all-<i>E</i> triene side chain was elucidated by extensive spectroscopic analysis. The unique chair/twist-boat conformation of the <i>trans</i>-decalin core and the flexibility of the B-ring were demonstrated by computer-aided conformational analysis. Cladoic acid was active against <i>Trypanosoma cruzi</i> and inhibited the proliferation of amastigotes and epimastigotes with IC<sub>50</sub> values of 27 and 46 μM, respectively, but it did not show any appreciable activity against P388 murine leukemia cells, bacteria, or fungi, indicating it is a potential candidate for drug development against Chagas disease.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2126-2131"},"PeriodicalIF":3.3000,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c00567","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/8/5 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

Abstract

A new polyketide, cladoic acid, was isolated from a fungus of the genus Cladosporium. The structure of the highly oxygenated trans-decalin ring with an all-E triene side chain was elucidated by extensive spectroscopic analysis. The unique chair/twist-boat conformation of the trans-decalin core and the flexibility of the B-ring were demonstrated by computer-aided conformational analysis. Cladoic acid was active against Trypanosoma cruzi and inhibited the proliferation of amastigotes and epimastigotes with IC50 values of 27 and 46 μM, respectively, but it did not show any appreciable activity against P388 murine leukemia cells, bacteria, or fungi, indicating it is a potential candidate for drug development against Chagas disease.

Abstract Image

克拉多酸--一种来自克拉多孢菌 TP-F2020 的抗克鲁斯锥虫多酮。
一种新的多酮类化合物克拉多酸是从一种克拉多孢属真菌中分离出来的。通过大量光谱分析,阐明了带有全 E 三烯侧链的高含氧反式萘环的结构。计算机辅助构象分析证明了反式萘烷核心独特的椅子/扭船构象和 B 环的灵活性。克拉多酸对克鲁斯锥虫有活性,能抑制非原虫和表原虫的增殖,IC50 值分别为 27 和 46 μM,但对 P388 小鼠白血病细胞、细菌或真菌没有显示出明显的活性,这表明克拉多酸是开发抗南美锥虫病药物的潜在候选物质。
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 求助全文
来源期刊
CiteScore
9.10
自引率
5.90%
发文量
294
审稿时长
2.3 months
期刊介绍: The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
×
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
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
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 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信