有机化学 ›› 2020, Vol. 40 ›› Issue (1): 201-208.DOI: 10.6023/cjoc201907027 上一篇    下一篇

研究简报

5'位羟基异戊烯基查尔酮类天然产物的合成及其抗菌活性研究

付林a, 孙炳夏a, 翟佳黛b, 李媛媛a, 刘信强a, 宋如a, 石冠群a, 李娇娜a, 宋远霞a, 桑锋a   

  1. a 山东理工大学生命科学学院 山东淄博 255049;
    b 天津大学药物科学与技术学院 天津 300072
  • 收稿日期:2019-07-19 修回日期:2019-09-01 出版日期:2020-01-25 发布日期:2019-09-25
  • 通讯作者: 桑锋 E-mail:fengsang@sdut.edu.cn
  • 基金资助:
    山东省自然科学基金(No.ZR2016HQ04)、国家自然科学基金(No.81602962)和中国博士后科学基金(No.2019M652461)资助项目.

Synthesis and Antibacterial Activity Study of Natural 5'-Hydroxyisoprenyl Chalcones

Fu Lina, Sun Bingxiaa, Zhai Jiadaib, Li Yuanyuana, Liu Xinqianga, Song Rua, Shi Guanquna, Li Jiaonaa, Song Yuanxiaa, Sang Fenga   

  1. a School of Life Science, Shandong University of Technology, Zibo, Shangdong 255049;
    b School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072
  • Received:2019-07-19 Revised:2019-09-01 Online:2020-01-25 Published:2019-09-25
  • Supported by:
    Project supported by the Natural Science Foundation of Shandong Province (No. ZR2016HQ04), the National Natural Science Foundation of China (No. 81602962) and the China Postdoctoral Science Foundation (No. 2019M652461).

首次合成了Bartericin A(1),2',6'-二羟基-5'-(2"-羟基-3"-甲基-3"-丁烯基)-4'-甲氧基查尔酮(2),Xanthohumol D(3)和Angusticornin B(4)4个羟基异戊烯基查尔酮类天然产物.为了探讨天然产物中不同官能团对其核心骨架结构抗菌活性的影响,设计合成了衍生物6.所合成的目标产物和未知中间体化合物经过1H NMR、13C NMR、IR、HRMS进行了确证.选取大肠杆菌[CMCC(B)44102]、绿脓杆菌[CMCC(B)10104]、金黄色葡萄球菌[CMCC(B)260003]和枯草芽孢杆菌[CMCC(B)63 501],采用稀释点样法对所合成的4个天然产物及1个新型衍生物进行了抗菌活性评估.结果显示,天然产物14和衍生物6对革兰氏阳性菌金黄色葡萄球菌和枯草芽孢杆菌表现出了一定的抑制活性.天然产物3对枯草芽孢杆菌表现出了较为明显的抑制活性,但对其他3种菌株无抑制活性(最小抑菌浓度>200 μg/mL).

关键词: 羟基异戊烯基, 查尔酮, 天然产物, 抗菌活性

Four natural chalcones, bartericin A (1), 2',6'-dihydroxy-5'-(2"-hydroxy-3"-methyl-3"-butenyl)-4'-methoxychalcone (2), xanthohumol D (3) and angusticornin B (4) were synthesized for the first time and all of them shared 5'-hydroxyisoprenyl group in common. One of their deriative, compound 6, was also prepared in order to investigate the effect of different functional group in natural products on antibacterial activity of the core structure. After confirming their structures by 1H NMR, 13C NMR, IR and HRMS, 1~4 and 6 were evaluated for their antibacterial activities against Bacillus subtilis[CMCC(B)63 501], Staphylococcus aureus[CMCC(B)260003], Escherichia coli[CMCC(B)44102] and Pseudomonas aeruginosa[CMCC(B)10104]. In this assay micro-dilution method was employed. The results showed that compounds 1, 4 and 6 exhibited moderate activity against gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. Meanwhile compound 3 showed significant activity towards Bacillus subtilis but no activity to the other 3 strains even in 200 μg/mL concentration.

Key words: hydroxyisoprenyl, chalcone, natural product, antibacterial activity