Zhiqiao Tan , Cong Chen , Lu Chen , Jia Zeng , Wenxin Zhang , Jingwen Xu , Xiangjiu He , Yihai Wang
{"title":"Cytotoxic and anti-inflammatory polyacetylenes from Tridax procumbens L","authors":"Zhiqiao Tan , Cong Chen , Lu Chen , Jia Zeng , Wenxin Zhang , Jingwen Xu , Xiangjiu He , Yihai Wang","doi":"10.1016/j.phytochem.2024.114191","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, 17 previously undescribed polyacetylenes and 9 known ones were isolated from <em>Tridax procumbens</em> L. Their structures were identified using spectroscopic techniques (NMR, UV, IR, MS and optical rotation), the modified Mosher method, electronic circular dichroism (ECD) data and ECD calculation. The cytotoxicity of polyacetylenes on six human tumour cell lines (K562, K562/ADR, AGS, MGC-803, SPC-A-1 and MDA-MB-231) was evaluated. (3<em>S</em>,10<em>R</em>)-tridaxin B (<strong>2a</strong>), (3<em>S</em>,10<em>S</em>)-tridaxin B (<strong>2b</strong>) and tridaxin F (<strong>8</strong>) demonstrated substantial cytotoxic effects against the K562 cell line, with half-maximal inhibitory concentration (IC<sub>50</sub>) values of 2.62, 14.43 and 17.91 μM, respectively. Cell and nucleus morphology assessments and Western blot analysis confirmed that the cytotoxicity of the three polyacetylenes on K562 cells was mediated through a dose-dependent apoptosis pathway. Furthermore, (3<em>S</em>,10<em>R</em>)-tridaxin A (<strong>1a</strong>) and tridaxin G (<strong>9</strong>) exhibited considerable inhibitory effects on lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages, with IC<sub>50</sub> values of 15.92 and 20.35 μM, respectively. Further investigations revealed that <strong>9</strong> exerted anti-inflammatory activities by impeding the nuclear translocation of NF-<em>κ</em>B and down-regulating the expression of pro-inflammatory factors, including those of iNOS, COX-2, IL-1<em>β</em> and IL-6, in a concentration-dependent manner. The study provides evidence that polyacetylenes from <em>T. procumbens</em> may serve as a potential source of anti-tumour or anti-inflammatory agents for treating related diseases.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-06-18","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/S0031942224002280","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
Herein, 17 previously undescribed polyacetylenes and 9 known ones were isolated from Tridax procumbens L. Their structures were identified using spectroscopic techniques (NMR, UV, IR, MS and optical rotation), the modified Mosher method, electronic circular dichroism (ECD) data and ECD calculation. The cytotoxicity of polyacetylenes on six human tumour cell lines (K562, K562/ADR, AGS, MGC-803, SPC-A-1 and MDA-MB-231) was evaluated. (3S,10R)-tridaxin B (2a), (3S,10S)-tridaxin B (2b) and tridaxin F (8) demonstrated substantial cytotoxic effects against the K562 cell line, with half-maximal inhibitory concentration (IC50) values of 2.62, 14.43 and 17.91 μM, respectively. Cell and nucleus morphology assessments and Western blot analysis confirmed that the cytotoxicity of the three polyacetylenes on K562 cells was mediated through a dose-dependent apoptosis pathway. Furthermore, (3S,10R)-tridaxin A (1a) and tridaxin G (9) exhibited considerable inhibitory effects on lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages, with IC50 values of 15.92 and 20.35 μM, respectively. Further investigations revealed that 9 exerted anti-inflammatory activities by impeding the nuclear translocation of NF-κB and down-regulating the expression of pro-inflammatory factors, including those of iNOS, COX-2, IL-1β and IL-6, in a concentration-dependent manner. The study provides evidence that polyacetylenes from T. procumbens may serve as a potential source of anti-tumour or anti-inflammatory agents for treating related diseases.
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.