Amoenucles A−F, novel nucleoside derivatives with TNF-α inhibitory activities from Aspergillus amoenus TJ507

IF 4 2区医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE

Chinese Journal of Natural Medicines Pub Date : 2025-01-01 DOI:10.1016/S1875-5364(25)60805-3

Zhang Yeting , Shi Zhengyi , Zhao Chunhua , Li Lanqin , Chen Ming , Cao Yunfang , Wang Fengqing , Tao Bo , Huang Xinye , Guo Jieru , Qi Changxing , Sun Weiguang , Zhang Yonghui

{"title":"Amoenucles A−F, novel nucleoside derivatives with TNF-α inhibitory activities from Aspergillus amoenus TJ507","authors":"Zhang Yeting , Shi Zhengyi , Zhao Chunhua , Li Lanqin , Chen Ming , Cao Yunfang , Wang Fengqing , Tao Bo , Huang Xinye , Guo Jieru , Qi Changxing , Sun Weiguang , Zhang Yonghui","doi":"10.1016/S1875-5364(25)60805-3","DOIUrl":null,"url":null,"abstract":"<div><div>Amoenucles A−F (1−6), six previously undescribed nucleoside derivatives, and two known analogs (7 and 8) were isolated from the culture of Aspergillus amoenus TJ507. Their structures were elucidated through spectroscopic analysis, single-crystal X-ray crystallography, and chemical reactions. Notably, 3 and 4 represent the first reported instances of nucleosides with an attached pyrrole moiety. Of particular significance, the absolute configuration of the sugar moiety of 1−4 was determined using nuclear magnetic resonance (NMR), electric circular dichroism (ECD) calculations, and a hydrolysis reaction, presenting a potentially valuable method for confirming nucleoside structures. Furthermore, 1, 2, and 5−8 exhibited potential tumor necrosis factor α (TNF-α) inhibitory activities, which may provide a novel chemical template for the development of agents targeting autoimmune and inflammatory diseases.</div></div>","PeriodicalId":10002,"journal":{"name":"Chinese Journal of Natural Medicines","volume":"23 1","pages":"Pages 111-118"},"PeriodicalIF":4.0000,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Natural Medicines","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1875536425608053","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"INTEGRATIVE & COMPLEMENTARY MEDICINE","Score":null,"Total":0}

引用次数: 0

Abstract

Amoenucles A−F (1−6), six previously undescribed nucleoside derivatives, and two known analogs (7 and 8) were isolated from the culture of Aspergillus amoenus TJ507. Their structures were elucidated through spectroscopic analysis, single-crystal X-ray crystallography, and chemical reactions. Notably, 3 and 4 represent the first reported instances of nucleosides with an attached pyrrole moiety. Of particular significance, the absolute configuration of the sugar moiety of 1−4 was determined using nuclear magnetic resonance (NMR), electric circular dichroism (ECD) calculations, and a hydrolysis reaction, presenting a potentially valuable method for confirming nucleoside structures. Furthermore, 1, 2, and 5−8 exhibited potential tumor necrosis factor α (TNF-α) inhibitory activities, which may provide a novel chemical template for the development of agents targeting autoimmune and inflammatory diseases.

查看原文本刊更多论文

阿莫曲霉TJ507中具有TNF-α抑制活性的新型核苷衍生物阿莫曲霉A-F。

从阿莫纳曲霉TJ507培养物中分离出了阿莫纳曲霉A-F（1-6）、六种先前未描述的核苷衍生物和两种已知的类似物（7和8）。通过光谱分析、单晶x射线晶体学和化学反应对其结构进行了鉴定。值得注意的是，3和4代表了首次报道的具有附加吡咯片段的核苷的实例。特别重要的是，利用核磁共振（NMR）、电圆二色性（ECD）计算和水解反应确定了1-4的糖部分的绝对构型，为确定核苷结构提供了一种潜在的有价值的方法。此外，1、2和5-8表现出潜在的肿瘤坏死因子α (TNF-α)抑制活性，这可能为开发靶向自身免疫性和炎症性疾病的药物提供新的化学模板。

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

Chinese Journal of Natural Medicines INTEGRATIVE & COMPLEMENTARY MEDICINE-PHARMACOLOGY & PHARMACY

CiteScore

7.50

自引率

4.30%

发文量

2235

期刊介绍： The Chinese Journal of Natural Medicines (CJNM), founded and sponsored in May 2003 by China Pharmaceutical University and the Chinese Pharmaceutical Association, is devoted to communication among pharmaceutical and medical scientists interested in the advancement of Traditional Chinese Medicines (TCM). CJNM publishes articles relating to a broad spectrum of bioactive natural products, leading compounds and medicines derived from Traditional Chinese Medicines (TCM). Topics covered by the journal are: Resources of Traditional Chinese Medicines; Interaction and complexity of prescription; Natural Products Chemistry (including structure modification, semi-and total synthesis, bio-transformation); Pharmacology of natural products and prescription (including pharmacokinetics and toxicology); Pharmaceutics and Analytical Methods of natural products.