Diphenylemestrins A−E: diketopiperazine-diphenyl ether hybrids from Aspergillus nidulans

IF 4 2区医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE

Chinese Journal of Natural Medicines Pub Date : 2025-06-01 DOI:10.1016/S1875-5364(25)60891-0

Aimin Fu , Qin Li , Yang Xiao , Jiaxin Dong, Yuanyang Peng, Yu Chen, Qingyi Tong, Chunmei Chen, Yonghui Zhang, Hucheng Zhu

{"title":"Diphenylemestrins A−E: diketopiperazine-diphenyl ether hybrids from Aspergillus nidulans","authors":"Aimin Fu , Qin Li , Yang Xiao , Jiaxin Dong, Yuanyang Peng, Yu Chen, Qingyi Tong, Chunmei Chen, Yonghui Zhang, Hucheng Zhu","doi":"10.1016/S1875-5364(25)60891-0","DOIUrl":null,"url":null,"abstract":"<div><div>A chemical investigation of secondary metabolites (SMs) from <em>Aspergillus nidulans</em> resulted in the identification of five novel dioxopiperazine (DKP)-diphenyl ether hybrids, designated as diphenylemestrins A−E (<strong>1</strong>−<strong>5</strong>). These compounds <strong>1</strong>−<strong>5</strong> represent the first known dimers combining DKP and diphenyl ether structures, with compound <strong>4</strong> featuring an uncommon dibenzofuran as the diphenyl ether component. The structural elucidation and determination of absolute stereochemistry were accomplished through spectroscopic analysis and electronic circular dichroism (ECD) calculations. Notably, diphenylemestrin C (<strong>3</strong>) exhibited moderate cytostatic activity against NB4 cells, with a half maximal inhibitory concentration (IC<sub>50</sub>) value of 21.99 μmol·L<sup>−1</sup>, and induced apoptosis at higher concentrations.</div></div>","PeriodicalId":10002,"journal":{"name":"Chinese Journal of Natural Medicines","volume":"23 6","pages":"Pages 727-732"},"PeriodicalIF":4.0000,"publicationDate":"2025-06-01","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/S1875536425608910","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

A chemical investigation of secondary metabolites (SMs) from Aspergillus nidulans resulted in the identification of five novel dioxopiperazine (DKP)-diphenyl ether hybrids, designated as diphenylemestrins A−E (1−5). These compounds 1−5 represent the first known dimers combining DKP and diphenyl ether structures, with compound 4 featuring an uncommon dibenzofuran as the diphenyl ether component. The structural elucidation and determination of absolute stereochemistry were accomplished through spectroscopic analysis and electronic circular dichroism (ECD) calculations. Notably, diphenylemestrin C (3) exhibited moderate cytostatic activity against NB4 cells, with a half maximal inhibitory concentration (IC₅₀) value of 21.99 μmol·L⁻¹, and induced apoptosis at higher concentrations.

查看原文本刊更多论文

Diphenylemestrins A−E：双酮哌嗪-二苯醚杂交种

通过对尼杜曲霉次生代谢产物（SMs）的化学分析，鉴定出5个新的二氧哌嗪(DKP)-二苯基醚杂交种，命名为diphenylemestrins A−E（1−5）。这些化合物1 ~ 5是已知的第一个结合DKP和二苯基醚结构的二聚体，其中化合物4以一种罕见的二苯并呋喃作为二苯基醚组分。通过光谱分析和电子圆二色性（ECD）计算完成了结构解析和绝对立体化学的测定。值得注意的是，二苯甲素C(3)对NB4细胞表现出中等的细胞抑制活性，其半数最大抑制浓度（IC50）值为21.99 μmol·L−1，高浓度时可诱导细胞凋亡。

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.