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首页> 外文会议>Emerging trends in dietary components for preventing and combating disease. >Isolation, Structure Elucidation, Synthesis, and Cytotoxic Activity of Polyacetylenes and Polyenes from Echinacea pallida
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Isolation, Structure Elucidation, Synthesis, and Cytotoxic Activity of Polyacetylenes and Polyenes from Echinacea pallida

机译：紫锥菊中聚乙炔和多烯的分离，结构鉴定，合成及细胞毒活性

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This study focuses on presenting an overview of recent results on the cytotoxic activity of polyacetylenes and polyenes isolated from Echinacea pallida. In a search for biologically active compounds from plants of the genus Echinacea, the lipophilic extract from E. pallida roots was characterized by a higher cytotoxic activity if compared with the other tested species. A subsequent bioassay-guided fractionation allowed the isolation and structure elucidation of ten polyacetylenes and polyenes from E. pallida roots. The isolated secondary metabolites were tested for their cytotoxic activity on selected human cancer cell lines and (8Z,13Z)-pentadeca-8,13-dien-11-yn-2-one was the most active constituent, particularly on the colonic COLO320 cancer cells (IC_(50) = 2.3 ± 0.3 μM) and breast carcinoma MCF-7 cancer cells (IC_(50) = 2.5 ± 0.7 μM). Arrest of cell cycle in the G1 phase and induction of apoptosis were found to be involved in its mechanism of action. Due to the difficult purification of this compound from the plant material, its first total synthesis was also described. A HPLC stability study of this natural product finally indicated that its cytotoxic activity can be mainly attributed to the genuine, not oxidized, molecule. These results indicated that polyacetylenes and polyenes from E. pallida are effective in inhibiting cancer cell proliferation and incorporation of enriched fractions of these compounds in the diet may be useful for cancer prevention. The most active compound represents also an interesting lead structure for the development of new antiproliferative agents.
机译：这项研究的重点是对从紫锥菊中分离出的聚乙炔和多烯的细胞毒性活性的最新研究结果进行概述。在寻找紫锥菊属植物中的生物活性化合物时，如果与其他受试物种相比，则从大肠埃希菌根的亲脂性提取物具有更高的细胞毒性。随后的生物测定指导的分级分离允许从大肠埃希氏菌根中分离和阐明十种聚乙炔和多烯。测试了分离出的次级代谢产物对选定的人类癌细胞系的细胞毒活性，并且（8Z，13Z）-pentadeca-8,13-dien-11-yn-2-one是活性最高的成分，尤其是对结肠COLO320癌症细胞（IC_（50）= 2.3±0.3μM）和乳腺癌MCF-7癌细胞（IC_（50）= 2.5±0.7μM）。发现G1期细胞周期的阻滞和凋亡的诱导与其作用机制有关。由于难以从植物材料中纯化该化合物，因此还描述了其第一次全合成。对该天然产物的HPLC稳定性研究最终表明，其细胞毒性活性主要归因于真正的而非氧化分子。这些结果表明，来自大肠埃希氏菌的聚乙炔和多烯可有效抑制癌细胞的增殖，并且将这些化合物的富集级分掺入饮食中可用于预防癌症。最具活性的化合物也代表了开发新的抗增殖剂的有趣的先导结构。

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