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[1]周强,王淳,李云萍,等.黄酮醇类化合物的合成与抗菌活性[J].应用与环境生物学报,2017,23(2):232-237.[doi:10.3724/SP.J.1145.2016.04019]
 ZHOU Qiang,WANG Chun**,et al.Synthesis and antibacterial activity of flavonols[J].Chinese Journal of Applied & Environmental Biology,2017,23(2):232-237.[doi:10.3724/SP.J.1145.2016.04019]
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黄酮醇类化合物的合成与抗菌活性()
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《应用与环境生物学报》[ISSN:1006-687X/CN:51-1482/Q]

卷:
23卷
期数:
2017年第2期
页码:
232-237
栏目:
研究论文
出版日期:
2017-04-25

文章信息/Info

Title:
Synthesis and antibacterial activity of flavonols
作者:
周强王淳李云萍蒲文臣
中国科学院成都生物研究所 成都 610041 2中国科学院大学 北京 100049
Author(s):
ZHOU Qiang1 2 WANG Chun1** LI Yunping1 & PU Wenchen1
1Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China 2University of Chinese Academy of Sciences, Beijing 100049, China
关键词:
黄酮醇合成抗菌活性枯草芽孢杆菌构效关系
Keywords:
flavonol synthesis antibacterial activity Bacillus subtilis structure-activity relationship
分类号:
R914.5
DOI:
10.3724/SP.J.1145.2016.04019
摘要:
以邻羟基苯乙酮和苯甲醛为原料,采用Algar-Flynn-Oyamada(AFO)反应,通过一锅法和分步法合成化合物;进一步用牛津杯法以甲氧西林为细菌阳性试验对照、DMSO为阴性对照,检测合成化合物对枯草芽孢杆菌、酿酒酵母菌、黑曲霉菌的抑菌能力. 共合成20种黄酮醇类化合物,其中包括1个新化合物;合成化合物对酿酒酵母菌和黑曲霉菌并无明显抑制效果(d < 9 mm),而对枯草芽孢杆菌具有不同程度的抑制作用,其中含卤素取代的黄酮醇对枯草芽孢杆菌具有显著的抑制作用(d > 15 mm). 构效关系研究表明,黄酮醇类化合物能有效对枯草芽孢杆菌形成抑制作用,且黄酮醇骨架上含有卤素取代(化合物7、8、17、19、20)表现出较好的抑菌作用;5-甲氧基取代黄酮醇(11、12、13、14)类化合物尽管不是活性最好的,但与相应的5位无取代的黄酮醇比较,如12 vs 2、13 vs 3、14 vs 1,活性有所提高. 本研究获得了一些具有较好抗菌活性的黄酮醇化合物,可为药物发现和合成提供结构依据. (图2 表2 参19)
Abstract:
Flavonol, also known as 3-hydroxylflavonone, is a kind of natural flavonoid compounds that have various important physiological and pharmacological activities. This study aimed to establish the structure-activity relationship of flavonols against antibacterial activity, in order to provide the basis for further drug design. In all, 20 flavonols were synthesized, and their antibacterial activities were identified. Twenty flavonols, including 1 new compound, were synthesized by using the one-pot method or three-step approach, based on the Algar–Flynn–Oyamada (AFO) reaction. Their anti-microbial activities against Bacillus subtilis, Saccharomycetes, and Aspergillus niger were subsequently evaluated using the Oxford cup method by using dimethyl sulfoxide as a negative control and methicillin as a positive control. Our results indicated that these flavonols possess satisfactory antibacterial activity to Bacillus subtilis, but have no obvious inhibitive effect against Saccharomycetes and Aspergillus niger. Structure-activity relationship indicated that halo-substitution at either A- or B-ring (compounds 7, 8, 17, 19, and 20) might strengthen the antibacterial activity. In addition, 5-methoxy-substituted flavonols (compounds 12, 13, and 14) exhibited improved antibacterial activities relative to the ones with non-substitution at the 5-position (12 vs. 2, 13 vs. 3, 14 vs. 1). Our results provide preliminary data for designing and discovering new leading compounds with antibacterial activities.

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更新日期/Last Update: 2017-04-25