白藜芦醇及其衍生物的抑菌活性及对番茄早疫病菌的作用机理研究
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摘要
植物源杀菌剂因作用广谱、资源丰富、可再生、与环境相容性好等优点成为农药研究领域的热点,目前人们已发现了很多具有抑菌、杀菌活性的植物种类,且分离出的活性物质涉及酚类、萜类、黄酮类等化合物。芪类化合物便是众多植物源活性成分中的一种,具有一定的抑菌活性,白藜芦醇是该类化合物的典型代表。研究表明,白藜芦醇具有丰富的生物学活性和药理作用,但在农业方面的研究相对较少,为了明确芪类化合物在农业病害中的防治前景,为该类化合物的深入研究提供探索依据,本论文选择白藜芦醇及其衍生物为研究对象,明确了其对供试病原真菌在离体、活体条件下的毒力,初步探讨了其作用机理及毒力稳定性,并测定了与其它杀菌剂混用的联合毒力,主要结果如下：
1.白藜芦醇及其衍生物抑菌谱测定结果：5个供试化合物对9类植物上的6种供试病原真菌均有一定的抑制作用,其中3,5-二羟基-4'-甲氧基二苯乙烯(Ⅲ)的活性最高,其对番茄早疫病菌菌丝生长的抑制效果亦为最好,EC5o为3.31μg/mL,对苹果霉心病菌次之,EC5o为18.53μg/mL,对苹果炭疽病菌最差,EC5o仅为87.50μg/mL.5个化合物均对番茄早疫病菌呈现出较高的抑制活性,EC5o值在3.31～32.96μg/mL之间,对番茄灰霉病菌的EC5o在18.58-49.83μg/mL之间,对其余原真菌的抑制活性各不相同,无明显规律。,
2.测定了抑菌活性最高的3,5-二羟基-4'-甲氧基二苯乙烯对番茄灰霉病菌生物学性状的影响,其中对产孢的抑制活性最高,12.5μg/mL下产孢抑制率即达到了67.96%,200μg/mL下几乎没有孢子产生；菌丝生长量和孢子萌发的EC5o值分别为32.7070μg/mL、48.3867μg/mL;菌核是该菌株最耐药的营养体,菌核萌发的EC5o值为77.2078μg/mL但菌核生成数量及重量与药剂浓度无明显的正相关关系。
3.白藜芦醇对番茄早疫病菌的离体活性测定结果：包括白藜芦醇在内的5种供试药剂中,异菌脲对番茄早疫病菌的抑制活性最高,EC5o为1.1196μg/mL,其活性是白藜芦醇的40.5倍,活性最低的是多菌灵,EC5o为51.4314μg/mL。白藜芦醇对菌丝生长表现为抑菌作用,导致了菌丝的畸形,100μg/mL的菌丝干重抑制率达到65.0%,抑制50%菌丝生长的浓度为40.0039μg/mL；白藜芦醇200μg/mL对孢子萌发的抑制率为69.70%,EC5o为113.7339μg/mL,代森锰锌对番茄早疫病菌孢子萌发的抑制活性远远高于白藜芦醇,其浓度为0.5μg/mL时,孢子萌发抑制率就达到了86.59%,两种药剂均未对孢子形态造成影响。
4.活体条件下白藜芦醇对番茄早疫病菌的活性测定结果：采用接种菌饼的叶片法和接种孢子的温室盆栽法进行毒力测定。先用白藜芦醇处理后接种的情况下,叶片上的病斑直径或病情指数随着白藜芦醇浓度的增大有所减弱,叶片法中0～1000μg/mL白藜芦醇的防治效果分布于8.14～60.31%,EC50为661.7178μg/mL;温室盆栽法中白藜芦醇的浓度设置为0～5000μg/mL,100μg/mL的防治效果为15.33%,5000μg/mL的防治效果仅为54.56%,由此可见,叶片法的防效略高于盆栽法。先进行接种,后用白藜芦醇处理,两种方法的防治效果均不理想。
5.测定了白藜芦醇对番茄早疫病菌菌丝体细胞膜通透性、可溶性蛋白和DNA生成的影响。试验结果显示,包括对照在内,番茄早疫病菌菌丝的电导率均随着处理时间的推移而升高,白藜芦醇能够增加菌丝细胞膜的通透性,导致电解质渗漏,200μg/mL处理180min后,电导率的增加幅度达到了218.2%。经白藜芦醇处理7d后,番茄早疫病菌菌丝体内可溶性蛋白含量较对照有所下降,随着处理浓度的增大,蛋白含量有所减少,100μg/mL时,蛋白含量为0.709mg/g,抑制率达到了70.00%,但在在设定的剂量范围内,白藜芦醇未能抑制番茄早疫病菌菌丝体内DNA的合成。
6.pH值和紫外线能够影响白藜芦醇的活性,在pH值为6的情况下白藜芦醇对菌丝生长和孢子萌发的抑制作用最明显,此时20μg/mL鲜重抑制率为12.01%,干重抑制率为30.42%,50μg/mL孢子萌发抑制率为3.24%,显著高于其他处理；随着紫外线照射时间的延长,番茄早疫病菌的菌落直径逐渐增大,由照射0.5h的2.60cm增大到照射4h时的3.40cm。温度能够引起白藜芦醇微弱的降解,避光保存8d,4℃、25℃、35℃的降解率分别为1.43%、2.05%、5.60%。
7.白藜芦醇与代森锰锌、异菌脲混用表现出了一定的增效作用,而与多菌灵、百菌清混用则具有拮抗作用。其中,白藜芦醇与代森锰锌混用的增效作用最显著,在试验配比下,代森锰锌：白藜芦醇=7：1的增效作用最好,EC5o值为2.2790μg/mL,共毒系数为863.93,1：7的EC5o值为21.2359μg/mL,共毒系数为172.34,亦为增效作用；异菌脲与白藜芦醇在1：7和7：1时表现出微弱的增效作用,EC5o值分别为5.6331μg/mL、1.0194μg/mL,共毒系数分别为134.35、125.05,其余配比下的共毒系数均小于120,为拮抗作用。
Due to the advantages of broad-spectrum, aboundresources, renewable and environmentally, botanical fungicide become a hot area of pesticide research. People have found many plant species with antibacterial or bactericidal activity, from which active substances separated involving pHenols, terpenes, flavonoids and other compounds. Stilbene compound is one of the botanical active ingredient with antibacterial activity and resveratrol is a typical representative of these compounds. Studies have shown that resveratrol has a wealth of biological activity and pharmacological effects, but relatively little research in agriculture. In order to clear the future of stilbene compounds in agricultural disease prevention and provide theoretical basis for in-depth study of these compounds, resveratrol was preferred as research object and cleared the virulence of pathogenic fungi tested in vitro and in vivo conditions, explored its mechanism of action and stability of the virulence, and determined joint virulence mixed with other fungicides. The main results are as follows:
1. Results of the inhibitory spectrum of resveratrol and its analogues results:five tested compounds have a certain inhibitory effect on six pathogenic fungi of nine plant categories, including the highest activity of3,5-dihydroxy-4'-methoxy-stilbene (Ⅲ), which had the best inhibition on mycelial growth of tomato early blight with EC50up to3.31μg/mL, followed by apple mildew heart with EC5018.53μg/mL and Apple anthrax bacteria with EC5087.50μg/mL. Five compounds all showed high inhibitory activity on A. solani with EC50values between3.31～32.96μg/mL, and EC50values against B. cinerea between18.58～49.83μg/mL. The inhibitory activity on the rest of pathogenic fungi are different and no obvious rule.
2. The effects of3,5-dihydroxy-4'-methoxy-stilbene on biological charcateristics against B.cinerea were tested. The highest inhibitory activity was on sporulation with67.96%inhibition rate at12.5μg/mL and nearly no sporulation at200μg/mL. EC50values of mycelial growth and spore germination were32.7070μg/mL and48.3867μg/mL. Sclerotia were the most tolerant vegetative part of the strain with sclerotia germination EC5077.2078μg/mL. There was no significant correlation between concentration and sclerotia quantity and weight.
3. In vitro bioactivity of resveratrol against A. solani:iprodione showed the highest inhibitory activity on A. solani with EC501.1196μg/mL,40.5times higher than resvaratrol while the activity of carbendazim was the lowest with EC5051.4314μg/mL. Resveratrol performed fungistasis on mycelial growth, leading to hyphal abnormality, while the inhibition of100μg/mL was65.0%with EC5051.4314μg/mL. The EC50of resveratrol on spore germination was113.7339μg/mL and inhibition at200μg/mL was69.70%. The activity of mancozeb on spore germination was far higher than resveratrol, with86.59%inhibition rate at0.5μg/mL. Both resveratrol and mancozeb had no effect on spore morphology.
4. Determination of activity of resveratrol in vivo:leaf method inoculanted with hyphal disc and pot-culture method inoculant with spores were used to test the bioactivity of resveratrol in vivo. In the case of resveratrol used befor inoculation, spot diameter on leaf or disease index was decreased with the increase of resveratrol. Control effects of resveratrol at0～1000μg/mL was between8.14～60.31%, with EC50661.7178μg/mL in leaf method, while control effect was15.33%at100μg/mL and54.56%at5000μg/mL in pot-culture method, of which the concentration was setted between0～5000μg/mL, so there was a conclusion that the control effect got by leaf method was higher than that of pot-culture method. Control effects were not ideal in the event of inoculation followed by resveratrol.
5. The effects of resveratrol on cell membrane permeability, contents of soluble protein and DNA of A. solani were determined. Results showed that:conductivities of all treatments including control increased over processing time, and resveratrol could add the permeability of mycelia, resulting in electrolyte leakage and electrical conductivity increased by218.2%after treated180min at200μg/mL. After7days, compared with control soulbe protein contents of hypha treated by resveratrol declined. As the concentration increases, the protein content decreased. The protein content was0.709mg/g at100μg/mL with inhibitory rate70.00%, but resveratrol failed to inhibit DNA synthesis in the dose range.
6. pH value and UV rays can affect the activity of resveratrol. Resvaratrol behaved the most notable inhibitory action on mycelial growth and spore germination at pH value6, at the moment fresh weight inhibition rate was12.01%, dry weight inhibition rate was30.42%at20μg/mL, and spore germination inhibition rate was3.24%at50μg/mL. Colony diameter enlarged as the irradiation time increased. As time increase from0.5to4h, the colony diameter increased from2.60cm to3.40cm.Temperature can cause faint degration of resveratrol, afer stocked in dark places for8days, degradation rates of4℃、25℃、35℃was1.43%、2.05%、5.60%separately.
7. There was a certain synergism of resveratrol mixed with mancozeb and iprodione separately, but antagonism with carbendazim and chlorothalonil. Among them, the mixture of resveratrol and mancozeb had the most significantly synergism with proportioning ratio of7:1was the best proportion showing additive effect with EC50value2.2790μg/mL and CTC863.93, while1:7was the worst propotion with EC50value21.2359μg/mL and CTC172.34. There were weak synergistic effects of iprodione mixtured with resveratrol at1:7and7:1, with EC50value5.6331μg/mL、1.0194μg/mL and CTC134.35、125.05, while remaining ratio showed antagonism with CTC less than120.
1.白藜芦醇及其衍生物抑菌谱测定结果：5个供试化合物对9类植物上的6种供试病原真菌均有一定的抑制作用,其中3,5-二羟基-4'-甲氧基二苯乙烯(Ⅲ)的活性最高,其对番茄早疫病菌菌丝生长的抑制效果亦为最好,EC5o为3.31μg/mL,对苹果霉心病菌次之,EC5o为18.53μg/mL,对苹果炭疽病菌最差,EC5o仅为87.50μg/mL.5个化合物均对番茄早疫病菌呈现出较高的抑制活性,EC5o值在3.31～32.96μg/mL之间,对番茄灰霉病菌的EC5o在18.58-49.83μg/mL之间,对其余原真菌的抑制活性各不相同,无明显规律。,
2.测定了抑菌活性最高的3,5-二羟基-4'-甲氧基二苯乙烯对番茄灰霉病菌生物学性状的影响,其中对产孢的抑制活性最高,12.5μg/mL下产孢抑制率即达到了67.96%,200μg/mL下几乎没有孢子产生；菌丝生长量和孢子萌发的EC5o值分别为32.7070μg/mL、48.3867μg/mL;菌核是该菌株最耐药的营养体,菌核萌发的EC5o值为77.2078μg/mL但菌核生成数量及重量与药剂浓度无明显的正相关关系。
3.白藜芦醇对番茄早疫病菌的离体活性测定结果：包括白藜芦醇在内的5种供试药剂中,异菌脲对番茄早疫病菌的抑制活性最高,EC5o为1.1196μg/mL,其活性是白藜芦醇的40.5倍,活性最低的是多菌灵,EC5o为51.4314μg/mL。白藜芦醇对菌丝生长表现为抑菌作用,导致了菌丝的畸形,100μg/mL的菌丝干重抑制率达到65.0%,抑制50%菌丝生长的浓度为40.0039μg/mL；白藜芦醇200μg/mL对孢子萌发的抑制率为69.70%,EC5o为113.7339μg/mL,代森锰锌对番茄早疫病菌孢子萌发的抑制活性远远高于白藜芦醇,其浓度为0.5μg/mL时,孢子萌发抑制率就达到了86.59%,两种药剂均未对孢子形态造成影响。
4.活体条件下白藜芦醇对番茄早疫病菌的活性测定结果：采用接种菌饼的叶片法和接种孢子的温室盆栽法进行毒力测定。先用白藜芦醇处理后接种的情况下,叶片上的病斑直径或病情指数随着白藜芦醇浓度的增大有所减弱,叶片法中0～1000μg/mL白藜芦醇的防治效果分布于8.14～60.31%,EC50为661.7178μg/mL;温室盆栽法中白藜芦醇的浓度设置为0～5000μg/mL,100μg/mL的防治效果为15.33%,5000μg/mL的防治效果仅为54.56%,由此可见,叶片法的防效略高于盆栽法。先进行接种,后用白藜芦醇处理,两种方法的防治效果均不理想。
5.测定了白藜芦醇对番茄早疫病菌菌丝体细胞膜通透性、可溶性蛋白和DNA生成的影响。试验结果显示,包括对照在内,番茄早疫病菌菌丝的电导率均随着处理时间的推移而升高,白藜芦醇能够增加菌丝细胞膜的通透性,导致电解质渗漏,200μg/mL处理180min后,电导率的增加幅度达到了218.2%。经白藜芦醇处理7d后,番茄早疫病菌菌丝体内可溶性蛋白含量较对照有所下降,随着处理浓度的增大,蛋白含量有所减少,100μg/mL时,蛋白含量为0.709mg/g,抑制率达到了70.00%,但在在设定的剂量范围内,白藜芦醇未能抑制番茄早疫病菌菌丝体内DNA的合成。
6.pH值和紫外线能够影响白藜芦醇的活性,在pH值为6的情况下白藜芦醇对菌丝生长和孢子萌发的抑制作用最明显,此时20μg/mL鲜重抑制率为12.01%,干重抑制率为30.42%,50μg/mL孢子萌发抑制率为3.24%,显著高于其他处理；随着紫外线照射时间的延长,番茄早疫病菌的菌落直径逐渐增大,由照射0.5h的2.60cm增大到照射4h时的3.40cm。温度能够引起白藜芦醇微弱的降解,避光保存8d,4℃、25℃、35℃的降解率分别为1.43%、2.05%、5.60%。
7.白藜芦醇与代森锰锌、异菌脲混用表现出了一定的增效作用,而与多菌灵、百菌清混用则具有拮抗作用。其中,白藜芦醇与代森锰锌混用的增效作用最显著,在试验配比下,代森锰锌：白藜芦醇=7：1的增效作用最好,EC5o值为2.2790μg/mL,共毒系数为863.93,1：7的EC5o值为21.2359μg/mL,共毒系数为172.34,亦为增效作用；异菌脲与白藜芦醇在1：7和7：1时表现出微弱的增效作用,EC5o值分别为5.6331μg/mL、1.0194μg/mL,共毒系数分别为134.35、125.05,其余配比下的共毒系数均小于120,为拮抗作用。
Due to the advantages of broad-spectrum, aboundresources, renewable and environmentally, botanical fungicide become a hot area of pesticide research. People have found many plant species with antibacterial or bactericidal activity, from which active substances separated involving pHenols, terpenes, flavonoids and other compounds. Stilbene compound is one of the botanical active ingredient with antibacterial activity and resveratrol is a typical representative of these compounds. Studies have shown that resveratrol has a wealth of biological activity and pharmacological effects, but relatively little research in agriculture. In order to clear the future of stilbene compounds in agricultural disease prevention and provide theoretical basis for in-depth study of these compounds, resveratrol was preferred as research object and cleared the virulence of pathogenic fungi tested in vitro and in vivo conditions, explored its mechanism of action and stability of the virulence, and determined joint virulence mixed with other fungicides. The main results are as follows:
1. Results of the inhibitory spectrum of resveratrol and its analogues results:five tested compounds have a certain inhibitory effect on six pathogenic fungi of nine plant categories, including the highest activity of3,5-dihydroxy-4'-methoxy-stilbene (Ⅲ), which had the best inhibition on mycelial growth of tomato early blight with EC50up to3.31μg/mL, followed by apple mildew heart with EC5018.53μg/mL and Apple anthrax bacteria with EC5087.50μg/mL. Five compounds all showed high inhibitory activity on A. solani with EC50values between3.31～32.96μg/mL, and EC50values against B. cinerea between18.58～49.83μg/mL. The inhibitory activity on the rest of pathogenic fungi are different and no obvious rule.
2. The effects of3,5-dihydroxy-4'-methoxy-stilbene on biological charcateristics against B.cinerea were tested. The highest inhibitory activity was on sporulation with67.96%inhibition rate at12.5μg/mL and nearly no sporulation at200μg/mL. EC50values of mycelial growth and spore germination were32.7070μg/mL and48.3867μg/mL. Sclerotia were the most tolerant vegetative part of the strain with sclerotia germination EC5077.2078μg/mL. There was no significant correlation between concentration and sclerotia quantity and weight.
3. In vitro bioactivity of resveratrol against A. solani:iprodione showed the highest inhibitory activity on A. solani with EC501.1196μg/mL,40.5times higher than resvaratrol while the activity of carbendazim was the lowest with EC5051.4314μg/mL. Resveratrol performed fungistasis on mycelial growth, leading to hyphal abnormality, while the inhibition of100μg/mL was65.0%with EC5051.4314μg/mL. The EC50of resveratrol on spore germination was113.7339μg/mL and inhibition at200μg/mL was69.70%. The activity of mancozeb on spore germination was far higher than resveratrol, with86.59%inhibition rate at0.5μg/mL. Both resveratrol and mancozeb had no effect on spore morphology.
4. Determination of activity of resveratrol in vivo:leaf method inoculanted with hyphal disc and pot-culture method inoculant with spores were used to test the bioactivity of resveratrol in vivo. In the case of resveratrol used befor inoculation, spot diameter on leaf or disease index was decreased with the increase of resveratrol. Control effects of resveratrol at0～1000μg/mL was between8.14～60.31%, with EC50661.7178μg/mL in leaf method, while control effect was15.33%at100μg/mL and54.56%at5000μg/mL in pot-culture method, of which the concentration was setted between0～5000μg/mL, so there was a conclusion that the control effect got by leaf method was higher than that of pot-culture method. Control effects were not ideal in the event of inoculation followed by resveratrol.
5. The effects of resveratrol on cell membrane permeability, contents of soluble protein and DNA of A. solani were determined. Results showed that:conductivities of all treatments including control increased over processing time, and resveratrol could add the permeability of mycelia, resulting in electrolyte leakage and electrical conductivity increased by218.2%after treated180min at200μg/mL. After7days, compared with control soulbe protein contents of hypha treated by resveratrol declined. As the concentration increases, the protein content decreased. The protein content was0.709mg/g at100μg/mL with inhibitory rate70.00%, but resveratrol failed to inhibit DNA synthesis in the dose range.
6. pH value and UV rays can affect the activity of resveratrol. Resvaratrol behaved the most notable inhibitory action on mycelial growth and spore germination at pH value6, at the moment fresh weight inhibition rate was12.01%, dry weight inhibition rate was30.42%at20μg/mL, and spore germination inhibition rate was3.24%at50μg/mL. Colony diameter enlarged as the irradiation time increased. As time increase from0.5to4h, the colony diameter increased from2.60cm to3.40cm.Temperature can cause faint degration of resveratrol, afer stocked in dark places for8days, degradation rates of4℃、25℃、35℃was1.43%、2.05%、5.60%separately.
7. There was a certain synergism of resveratrol mixed with mancozeb and iprodione separately, but antagonism with carbendazim and chlorothalonil. Among them, the mixture of resveratrol and mancozeb had the most significantly synergism with proportioning ratio of7:1was the best proportion showing additive effect with EC50value2.2790μg/mL and CTC863.93, while1:7was the worst propotion with EC50value21.2359μg/mL and CTC172.34. There were weak synergistic effects of iprodione mixtured with resveratrol at1:7and7:1, with EC50value5.6331μg/mL、1.0194μg/mL and CTC134.35、125.05, while remaining ratio showed antagonism with CTC less than120.
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