Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 201-208.DOI: 10.6023/cjoc201907027 Previous Articles     Next Articles


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 发布日期:2019-09-25
  • 通讯作者: 桑锋
  • 基金资助:

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 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).

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