Zhiqiao Tan , Cong Chen , Lu Chen , Jia Zeng , Wenxin Zhang , Jingwen Xu , Xiangjiu He , Yihai Wang
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(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":"{\"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}","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
摘要
利用光谱技术(核磁共振、紫外、红外、质谱和旋光)、改良莫舍法、电子圆二色性(ECD)数据和 ECD 计算确定了它们的结构。评估了聚乙炔类化合物对六种人类肿瘤细胞系(K562、K562/ADR、AGS、MGC-803、SPC-A-1 和 MDA-MB-231)的细胞毒性。(3S,10R)-tridaxin B (2a)、(3S,10S)-tridaxin B (2b) 和 tridaxin F (8) 对 K562 细胞株具有显著的细胞毒性作用,其半最大抑制浓度 (IC50) 值分别为 2.62、14.43 和 17.91 μM。细胞和细胞核形态评估以及 Western 印迹分析证实,这三种多乙酰烯类化合物对 K562 细胞的细胞毒性是通过剂量依赖性凋亡途径介导的。此外,(3S,10R)-三萜类化合物 A(1a)和三萜类化合物 G(9)对脂多糖刺激 RAW 264.7 巨噬细胞产生一氧化氮具有相当大的抑制作用,IC50 值分别为 15.92 和 20.35 μM。进一步研究发现,9 通过阻碍 NF-κB 的核转位和下调促炎因子(包括 iNOS、COX-2、IL-1β 和 IL-6 的表达)的表达,以浓度依赖性的方式发挥抗炎活性。该研究提供的证据表明,普鲁卡因中的多乙酰烯类可能是治疗相关疾病的抗肿瘤或抗炎药物的潜在来源。
Cytotoxic and anti-inflammatory polyacetylenes from Tridax procumbens L
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.