新型含α-氨基膦酸酯的氰基丙烯酸酯类化合物抗病毒活性筛选及其作用机理初步研究
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摘要
本论文采用室内半叶枯斑法对本课题组合成的新型含α-氨基膦酸酯的氰基丙烯酸酯类化合物进行了抗烟草花叶病毒活性初步筛选。筛选出具有较好抗TMV活性的合成的新型含α-氨基膦酸酯的氰基丙烯酸酯类化合物2007270:3-甲硫基-3-(二正丁氧基膦酰基-1-苯基-甲氨基)-2-氰基丙烯酸甲酯。生测结果表明:化合物2007270在500μg/mL剂量下对烟草花叶病毒、黄瓜花叶病毒、马铃薯Y病毒、马铃薯X病毒四种植物病毒表现出了较好的活体治疗活性,抑制率分别为53.2%、51.5%、46.2%、53.5%。
进行了室内抗烟草花叶病毒病盆栽药效试验研究,化合物2007270处理的普通烟的病情指数和烟草叶片内病毒浓度均明显低于空白对照处理的,说明化合物2007270对TMV的增殖有明显的抑制作用,在烟草上喷施化合物2007270可降低烟草体内病毒的含量,减轻病害症状。
以烟草花叶病毒为作用对象,并以商品药剂宁南霉素(2%W/W)为对照,对化合物2007270的作用机理进行初步研究。结果表明:化合物2007270(500μg/mL)处理的接种TMV的烟草叶片中防御酶(PAL、POD、PPO、SOD)、几丁质酶、β-1,3-葡聚糖酶、硝酸还原酶、叶绿素、丙二醛、脯氨酸、可溶性糖、可溶性蛋白、胞间病程相关蛋白这些调控物质在一定的时间内都具有相关性。化合物2007270对TMV粒体具有一定的体外钝化作用,体外钝化后的枯斑抑制率为72.9%。化合物2007270与TMV混合后透析病毒其侵染力有一定程度的恢复,化合物2007270对TMV外壳蛋白的体外聚合过程有明显的抑制作用,对TMV-RNA有一定的体外抑制侵染作用。TMV与化合物2007270混合后用RNase处理,测得侵染率与未用RNase处理的相差不大,由此说明化合物2007270不具有体外脱衣壳作用。
The effect of new cyanoacrylate derivatives was tested against TMV by using the half-leaf method in the laboratory.Preliminary bioassay tests showed that some compounds such as compound 2007270:((Z)-methyl 3-((dibutoxyphosphoryl)-(phenyl)methylamino)-2-isocyano-3-(methylthioacrylate)) possessed good antiviral activities against TMV at 500μg/mL in vivo.Further bioassays disclosed that title compound 2007270 showed remarkable inhibitory effect on all kinds of the tested plant virus.Compound 2007270 possesses good curative effects at 500μg/mL against TMV,CMV,PVY,PVX in vivo with inhibitory rates of 53.2%,51.5%,46.2%,and 53.5%,respectively.
A potted plant survey on the bioactivity studies of different compounds against TMV on Nicotiana glutinosa,was conducted under an indoor environment.Compared with blank control,compound 2007270 significantly decreased the disease index and the concentration of TMV in tobacco leaves.Results indicated that compound 2007270 could inhibit multiplication of TMV in infected leaves.Spraying of compound 2007270 on Nicotiana tobacum can reduce the mass concentration of TMV in the tobacco with alleviation of the symptoms.
Mechanism of action of compound 2007270 against TMV was studied with Ningnanmycin(2%W/W) serving as the control.It was observed that the resistance of tobacco against the virus attack of TMV was significantly enhanced after treating infected tobacco by compound 2007270 at 500μg/mL According to the study,the amonialyase(PAL),peroxidase(POD),polypheuoloxidase(PPO),superoxide(SOD), chitinase,β-1,3-glucanases,nitrate reductase,chlorophyll,malondildehyde,proline, soluble sugar,soluble protein,and intercellular protein of the compound treated plant showed some kind of relevance with lapse of time.The compound 2007270 could strongly inactivate TMV particles,and the inhibition rate reached up to 72.9%.A certain part of the compound not affected by TMV was recovered by dialysis of the virus-compound suspension in vitro,which showed that the compound 2007270 had some direct viricidal effect,although not appreciable.Compound 2007270 significantly inhibited TMV-coat protein polymerization in vitro,and could obviously influence the infectivity of TMV-RNA.When RNase was added to the mixture of TMV and compound 2007270,the infection rate of TMV was 72.9%,decreased by 6.4%.
进行了室内抗烟草花叶病毒病盆栽药效试验研究,化合物2007270处理的普通烟的病情指数和烟草叶片内病毒浓度均明显低于空白对照处理的,说明化合物2007270对TMV的增殖有明显的抑制作用,在烟草上喷施化合物2007270可降低烟草体内病毒的含量,减轻病害症状。
以烟草花叶病毒为作用对象,并以商品药剂宁南霉素(2%W/W)为对照,对化合物2007270的作用机理进行初步研究。结果表明:化合物2007270(500μg/mL)处理的接种TMV的烟草叶片中防御酶(PAL、POD、PPO、SOD)、几丁质酶、β-1,3-葡聚糖酶、硝酸还原酶、叶绿素、丙二醛、脯氨酸、可溶性糖、可溶性蛋白、胞间病程相关蛋白这些调控物质在一定的时间内都具有相关性。化合物2007270对TMV粒体具有一定的体外钝化作用,体外钝化后的枯斑抑制率为72.9%。化合物2007270与TMV混合后透析病毒其侵染力有一定程度的恢复,化合物2007270对TMV外壳蛋白的体外聚合过程有明显的抑制作用,对TMV-RNA有一定的体外抑制侵染作用。TMV与化合物2007270混合后用RNase处理,测得侵染率与未用RNase处理的相差不大,由此说明化合物2007270不具有体外脱衣壳作用。
The effect of new cyanoacrylate derivatives was tested against TMV by using the half-leaf method in the laboratory.Preliminary bioassay tests showed that some compounds such as compound 2007270:((Z)-methyl 3-((dibutoxyphosphoryl)-(phenyl)methylamino)-2-isocyano-3-(methylthioacrylate)) possessed good antiviral activities against TMV at 500μg/mL in vivo.Further bioassays disclosed that title compound 2007270 showed remarkable inhibitory effect on all kinds of the tested plant virus.Compound 2007270 possesses good curative effects at 500μg/mL against TMV,CMV,PVY,PVX in vivo with inhibitory rates of 53.2%,51.5%,46.2%,and 53.5%,respectively.
A potted plant survey on the bioactivity studies of different compounds against TMV on Nicotiana glutinosa,was conducted under an indoor environment.Compared with blank control,compound 2007270 significantly decreased the disease index and the concentration of TMV in tobacco leaves.Results indicated that compound 2007270 could inhibit multiplication of TMV in infected leaves.Spraying of compound 2007270 on Nicotiana tobacum can reduce the mass concentration of TMV in the tobacco with alleviation of the symptoms.
Mechanism of action of compound 2007270 against TMV was studied with Ningnanmycin(2%W/W) serving as the control.It was observed that the resistance of tobacco against the virus attack of TMV was significantly enhanced after treating infected tobacco by compound 2007270 at 500μg/mL According to the study,the amonialyase(PAL),peroxidase(POD),polypheuoloxidase(PPO),superoxide(SOD), chitinase,β-1,3-glucanases,nitrate reductase,chlorophyll,malondildehyde,proline, soluble sugar,soluble protein,and intercellular protein of the compound treated plant showed some kind of relevance with lapse of time.The compound 2007270 could strongly inactivate TMV particles,and the inhibition rate reached up to 72.9%.A certain part of the compound not affected by TMV was recovered by dialysis of the virus-compound suspension in vitro,which showed that the compound 2007270 had some direct viricidal effect,although not appreciable.Compound 2007270 significantly inhibited TMV-coat protein polymerization in vitro,and could obviously influence the infectivity of TMV-RNA.When RNase was added to the mixture of TMV and compound 2007270,the infection rate of TMV was 72.9%,decreased by 6.4%.
引文
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