| 冯爽,李阳杰,刁冉冉,王昭阳,冯亚莉,颜子童,翟广玉.化学通报,2022,85(4):470-479. |
| 槲皮素-3-O-丙基衍生物的合成及生物活性研究 |
| Synthesis and Biological Activity of Quercetin-3-O-Propyl Derivatives |
| 投稿时间：2021-07-26 修订日期：2021-09-03 |
| DOI： |
| 中文关键词: 黄酮 槲皮素 衍生物 合成 抗肿瘤 抗菌 |
| 英文关键词:flavonoids quercetin derivatives synthesis antitumor antibacterial |
| 基金项目:郑州市高等学校名师技术技能工作室(郑教高[2015]70号) |
|
| 摘要点击次数: 503 |
| 全文下载次数: 0 |
| 中文摘要: |
| 槲皮素属于黄酮类化合物,具有丰富的生物活性,是一种非常有前途的植物化学物质。本文以槲皮素为先导物,选择性对C环3位羟基进行修饰。以廉价的芦丁为原料,经苄基选择性保护、Williamson成醚反应,再经Pd/C催化加氢脱苄基得到28个槲皮素-3-O-丙基衍生物,均未见文献报道,目标产物结构经1H NMR、13C NMR、ESI-MS确证。采用MTT法考察了28个槲皮素-3-O-丙基衍生物对人食管鳞癌(EC109),人胃癌(HGC27),人乳腺癌(MCF-7),小鼠黑色素瘤(B16-F10)的增殖抑制作用。结果显示,通过化学方法对槲皮素进行结构修饰后,其体外抗肿瘤活性增强。其中,化合物F3(5.229±0.371)、F7(2.628±0.087)对小鼠黑色素瘤(B16-F10)抑制作用比5-氟尿嘧啶(5-FU)(14.376±0.272)好一些,值得进一步的研究。采用肉汤稀释法来对合成的化合物进行了抗菌活性的评价,用测定MIC值来具体恒量某种药物的抑菌能力大小。合成的大部分的化合物的抗菌活性强于槲皮素,但是与上市药物左氧氟沙星相比活性差很多,抗菌活性普遍不好. |
| 英文摘要: |
| Quercetin is a flavonoid compound with rich biological activity and is a very promising phytochemical. In this paper, quercetin was used as the leader to selectively modify the hydroxyl group at the 3-position of the C ring. Using cheap rutin as raw material, selective protection of benzyl group, Williamson ether formation reaction, and Pd/C catalyzed hydrogenation and debenzylation to obtain 28 quercetin-3-O-propyl derivatives, none of them According to literature reports, the structure of the target product was confirmed by 1H NMR, 13C NMR, and ESI-MS. MTT method was used to investigate the effects of 28 quercetin-3-O-propyl derivatives on human esophageal squamous cell carcinoma (EC109), human gastric cancer (HGC27), human breast cancer (MCF-7), mouse melanoma (B16- F10) the proliferation inhibitory effect. The results showed that after structural modification of quercetin by chemical methods, its anti-tumor activity in vitro was enhanced. Among them, the inhibitory effect of compound F3 (5.229±0.371) and F7 (2.628±0.087) on mouse melanoma (B16-F10) is better than 5-fluorouracil (5-FU) (14.376±0.272), which is worthy of further study. The broth dilution method was used to evaluate the antibacterial activity of the synthesized compounds, and the MIC value was measured to determine the antibacterial ability of a certain drug in a constant amount. The antibacterial activity of most of the synthesized compounds is stronger than that of quercetin, but compared with the marketed drug levofloxacin, the activity is much lower, and the antibacterial activity is generally not good. |
| 查看全文 查看/发表评论 下载PDF阅读器 |
| 关闭 |
|
|
|