Xi-Hong Liu , Yu-Nan Qian , Zhi-Xiang Xie , Peng-Hai Tian , Zheng-Hui Huang , Bin Zhou , Jian-Min Yue
{"title":"Stereochemical insights into enantioselective antiplasmodial lignanamides from the twigs and leaves of Solanum erianthum","authors":"Xi-Hong Liu , Yu-Nan Qian , Zhi-Xiang Xie , Peng-Hai Tian , Zheng-Hui Huang , Bin Zhou , Jian-Min Yue","doi":"10.1016/j.phytochem.2024.114163","DOIUrl":null,"url":null,"abstract":"<div><p>Stereochemical investigations on the twigs and leaves of <em>Solanum</em> erianthum afforded five pairs of lignanamide enantiomers and a previously undescribed phenolic amide (<strong>3</strong>). Particularly, two pairs of previously undescribed lignanamide racemates (<strong>1a/1b</strong>–<strong>2a/2b</strong>) represent the first case of natural products that feature an unreported 5/5-fused <em>N</em>/<em>O</em>-biheterocyclic core. Their structures, including the absolute configurations, were determined unambiguously by using spectroscopic analyses and electronic circular dichroism calculations. A speculative biogenetic pathway for <strong>1</strong>–<strong>3</strong> was proposed. Interestingly, these lignanamides exhibited enantioselective antiplasmodial activities against drug-sensitive <em>Plasmodium falciparum</em> 3D7 strain and chloroquine-resistant <em>Plasmodium falciparum</em> Dd2 strain, pointing out that chirality plays an important role in drug development.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942224002000","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
Stereochemical investigations on the twigs and leaves of Solanum erianthum afforded five pairs of lignanamide enantiomers and a previously undescribed phenolic amide (3). Particularly, two pairs of previously undescribed lignanamide racemates (1a/1b–2a/2b) represent the first case of natural products that feature an unreported 5/5-fused N/O-biheterocyclic core. Their structures, including the absolute configurations, were determined unambiguously by using spectroscopic analyses and electronic circular dichroism calculations. A speculative biogenetic pathway for 1–3 was proposed. Interestingly, these lignanamides exhibited enantioselective antiplasmodial activities against drug-sensitive Plasmodium falciparum 3D7 strain and chloroquine-resistant Plasmodium falciparum Dd2 strain, pointing out that chirality plays an important role in drug development.
期刊介绍:
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.