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

doi:10.6023/cjoc201907027

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

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

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 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 Lin^a, Sun Bingxia^a, Zhai Jiadai^b, Li Yuanyuan^a, Liu Xinqiang^a, Song Ru^a, Shi Guanqun^a, Li Jiaona^a, Song Yuanxia^a, Sang Feng^a

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).

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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.

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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

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

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