Design, Synthesis, and Antitobacco Mosaic Virus Activity of Water-Soluble Chiral Quaternary Ammonium Salts of Phenanthroindolizidines Alkaloids

被引：26

作者：

Han, Guifang ^{[1
]}

Chen, Linwei ^{[1
]}

Wang, Qiang ^{[1
]}

Wu, Meng ^{[1
]}

Liu, Yuxiu ^{[1
]}

Wang, Qingmin ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Res Inst Elementoorgan Chem,Coll Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2018年 / 66卷 / 04期

基金：

中国国家自然科学基金;

关键词：

phenanthroindolizidines alkaloids; quaternary ammonium salts; derivatives; anti-TMV; structure-activity relationship; stability; solubility; ANTIVIRAL ACTIVITY; ANTITUMOR AGENTS; TYLOPHORINE ANALOG; FICUS-SEPTICA; DERIVATIVES; ANTOFINE; CRYPTOPLEURINE; TYLOCREBRINE; POTENT; SARS;

D O I：

10.1021/acs.jafc.7b03418

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

To study the influence of the substituent at the N-10 position on antiviral activity, the chiral quaternary ammonium salt derivatives of R-and S-tylophorine were designed, synthesized, and evaluated for antiviral activity against tobacco mosaic virus (TMV). The bioassay results indicated that most of the designed structural analogues showed good in vivo anti-TMV activity, among which propargyl quaternary ammonium salt compound S-7b showed the best anti-TMV activities (80.5%, 77.6%, 76.6%, 82.1%) at 500 mu g/mL both in vitro and in vivo in the laboratory. In the field trials of antiviral efficacy against TMV, S-7b as well exhibited better activities than control plant virus inhibitors. The stability of compound S-7b was obviously increased, and its solubility was more than 500-times higher than that of S-tylophorine. Therefore, chiral quaternary ammonium salt S-7b was expected to be developed as a promising candidate as an inhibitor of plant virus.

引用

页码：780 / 788

页数：9

共 33 条

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