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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 1: 201 - 208

DOI: https://doi.org/10.6023/cjoc201907027

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

  • Fu Lin ,
  • Sun Bingxia ,
  • Zhai Jiadai ,
  • Li Yuanyuan ,
  • Liu Xinqiang ,
  • Song Ru ,
  • Shi Guanqun ,
  • Li Jiaona ,
  • Song Yuanxia ,
  • Sang Feng
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  • a School of Life Science, Shandong University of Technology, Zibo, Shangdong 255049;
    b School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072

Received date: 2019-07-19

  Revised date: 2019-09-01

  Online 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).

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Abstract

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

Cite this article

Fu Lin , Sun Bingxia , Zhai Jiadai , Li Yuanyuan , Liu Xinqiang , Song Ru , Shi Guanqun , Li Jiaona , Song Yuanxia , Sang Feng . Synthesis and Antibacterial Activity Study of Natural 5'-Hydroxyisoprenyl Chalcones[J]. Chinese Journal of Organic Chemistry, 2020 , 40(1) : 201 -208 . DOI: 10.6023/cjoc201907027

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