天然产物LC化学结构修饰及对稻瘟病菌的生物活性研究
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摘要
天然产物LC为无环单萜类化合物,具有一定的生物活性。研究发现,LC对真菌具有较好的抑菌杀菌效果。稻瘟病是为害水稻生产最严重的病害之一,目前主要是用化学农药防治,但是稻瘟病菌(Pyricularia oryzae(Hebert)Barr.)对一些常用药剂(如稻瘟灵)产生了抗药性,需要开发新颖、安全、高效、低残留的绿色农药来防治稻瘟病。本论文在实验室天然产物LC前期研究的基础上,主要做了以下三个方面的工作。
一、比较研究了亚硫酸氢钠加成法提取LC与亚硫酸钠加成法提取LC的差异,及微波条件下与传统条件下用亚硫酸氢钠加成法提取LC的差异。结果表明,用亚硫酸氢钠加成法提取得到的LC纯度达到96.23%,亚硫酸钠加成法所得LC的含量可达96.74%,采用微波法提取出的LC含量高达97.28%。微波萃取与传统的提取方法相比,具有选择性高、操作时间短,溶剂耗量少、有效成分收率高、节能环保的特点。
二、为了寻求高效、稳定、安全的新化合物,利用天然产物LC生物活性物质模型和亚结构连接法设计合成了缩醛类化合物和席夫碱类化合物,共计13种。
1.合成了LC二甲缩醛等4个LC缩醛类化合物,通过元素分析、IR、~1H-NMR对其结构进行了表征。
2.合成了LC缩苯胺席夫碱等6个LC缩芳胺类席夫碱化合物,通过IR对其结构进行了表征。
3.合成了水杨醛缩柠檬胺及其金属配合物共3个。先将LC肟化,还原为柠檬胺,然后与水杨醛缩合,得水杨醛缩柠檬胺席夫碱,再以之为配体,分别与过渡金属离子Cu~(2+)和Zn~(2+)配合生成金属配合物,通过IR对其结构进行了表征,并讨论了化合物的配位情况。
三、将天然产物LC和所得的目标合成物对稻瘟病菌进行菌丝生长抑制试验。
1.以天然产物LC为标准对照,其在500mg/L和31.25mg/L时的抑菌效果分别为90.31%和34.8%,其EC_(50)为50.43mg/L。
2.缩醛类化合物均有一定的抑菌效果。浓度为500mg/L时,LC缩乙二醇的抑菌效果最佳,为80.27%。
3.席夫碱类化合物具有较好的抑菌活性,抑菌效果为32.27%～94.88%。浓度为500mg/L时,LC缩磺胺的抑菌效果最佳,可达94.88%。浓度为31.25mg/L时,席夫碱类化合物中抑菌效果最高的为水杨醛缩柠檬胺合铜(Ⅱ),为56.91%。
4.试验发现,合成的缩醛类化合物的抑菌效果均低于天然产物LC,其相对毒力指数为21.45～25.42;席夫碱类化合物的抑菌效果则普遍优于天然产物LC。还发现席夫碱与金属离子配合后,抑菌活性都有不同程度的提高。
Natural product LC is a kind of acyclic monoterpeniod and has specific bioactivities. As studies show,LC can effect and eliminate epiphyte perfect.However,rice blast is one of the most diseases which effect rice,and chemical methods are the main way to protect from kinds of virus.But rice blast fungus(Pyricularia oryzae(Hebert) Barr.) has better resistance to some common pesticides such as Isoprothiolane.So novel, effective and low residue pesticides and compounds are need to protect rice blast badly.Based on the former results of our laboratory,three main aspects of this paper's research are below.
First,comparing and studying the differences between methods of extracting LC by sodium bisulfite and sodium sulfite.Also we have found the differences of methods of extracting LC by sodium bisulfite under both conditions of microwave and tradition. The results showed that the purity of LC can be reached to 96.23%by the condition of sodium bisulfite.The purity of LC can be reached to 96.74%by the condition of sodium sulfite.Also the content of LC can be reached to 97.28%under the condition of microwaves.In comparison,it has several characteristics such as high selection, short periods of operation,little consumption,high rate of recycle and environmental protection under the condition of microwave.
Secondly,in order to seek novel,effective and safe compounds,we used the principle of model natural product LC active material and linking inferior structure to design and synthesize thirteen acetal and Schiff base compounds in total.
1.Synthesizing four LC acetal compounds,such as LC dimethyl acetal.Identifying their structures by IR,~1H-NMR and elements analysis.
2.Synthesizing six LC Schiff base compounds,such as LC anil Schiff base. Identifying their structures by IR.
3.LC was reduced into limo-amine by cyclohexfanone oximation of LC and condensation with salicylaldehyde.Then we got salicylaldehyde limo-amine Schiff base compound.Based on that compound,it was mixed into coordination compound with Cu~(2+) and Zn~(2+).Identifying their structures by IR and discussing the coordination of those compounds.
Third,all the purposed compounds and natural product LC were operated into the experiment of inhibiting the mycelial growth of Magnaporthe grisea(Hebert) Barr.
1.The inhibitory results of natural product LC(500 mg/L and 31.25 mg/L) were 90.31 and 34.8%respectively.EC_(50) was 50.43 mg/L。
2.All the acetal compounds had certain effective inhibitory results.At the concentration of 500 mg/L,LC butanediol acetal had the best inhibitory result in the acetal compounds.It was 80.27%.
3.Schiff base compounds also had sound inhibitory results.They were 32.27%～94.88%.At the concentration of 500 mg/L,LC sulfanilamide had the best inhibitory result in the Schiff base compounds.It was 94.88%.At the concentration of 31.25 mg/L,Salicylaldehyde-lemon amine complexes of copper had the best inhibitory result in the Schiffbase compounds.It was 56.91%.
4.Results of research showed that natural product LC had better inhibitory results than that of acetal compounds.Relative toxicity index of compounds were 21.45～25.42.Moreover,the inhibitory results of Schiff base compounds were better than that of natural product LC.And it was improved to eliminate rice blast fungus,when Schiffbasses were mixed with metal ions.
一、比较研究了亚硫酸氢钠加成法提取LC与亚硫酸钠加成法提取LC的差异,及微波条件下与传统条件下用亚硫酸氢钠加成法提取LC的差异。结果表明,用亚硫酸氢钠加成法提取得到的LC纯度达到96.23%,亚硫酸钠加成法所得LC的含量可达96.74%,采用微波法提取出的LC含量高达97.28%。微波萃取与传统的提取方法相比,具有选择性高、操作时间短,溶剂耗量少、有效成分收率高、节能环保的特点。
二、为了寻求高效、稳定、安全的新化合物,利用天然产物LC生物活性物质模型和亚结构连接法设计合成了缩醛类化合物和席夫碱类化合物,共计13种。
1.合成了LC二甲缩醛等4个LC缩醛类化合物,通过元素分析、IR、~1H-NMR对其结构进行了表征。
2.合成了LC缩苯胺席夫碱等6个LC缩芳胺类席夫碱化合物,通过IR对其结构进行了表征。
3.合成了水杨醛缩柠檬胺及其金属配合物共3个。先将LC肟化,还原为柠檬胺,然后与水杨醛缩合,得水杨醛缩柠檬胺席夫碱,再以之为配体,分别与过渡金属离子Cu~(2+)和Zn~(2+)配合生成金属配合物,通过IR对其结构进行了表征,并讨论了化合物的配位情况。
三、将天然产物LC和所得的目标合成物对稻瘟病菌进行菌丝生长抑制试验。
1.以天然产物LC为标准对照,其在500mg/L和31.25mg/L时的抑菌效果分别为90.31%和34.8%,其EC_(50)为50.43mg/L。
2.缩醛类化合物均有一定的抑菌效果。浓度为500mg/L时,LC缩乙二醇的抑菌效果最佳,为80.27%。
3.席夫碱类化合物具有较好的抑菌活性,抑菌效果为32.27%～94.88%。浓度为500mg/L时,LC缩磺胺的抑菌效果最佳,可达94.88%。浓度为31.25mg/L时,席夫碱类化合物中抑菌效果最高的为水杨醛缩柠檬胺合铜(Ⅱ),为56.91%。
4.试验发现,合成的缩醛类化合物的抑菌效果均低于天然产物LC,其相对毒力指数为21.45～25.42;席夫碱类化合物的抑菌效果则普遍优于天然产物LC。还发现席夫碱与金属离子配合后,抑菌活性都有不同程度的提高。
Natural product LC is a kind of acyclic monoterpeniod and has specific bioactivities. As studies show,LC can effect and eliminate epiphyte perfect.However,rice blast is one of the most diseases which effect rice,and chemical methods are the main way to protect from kinds of virus.But rice blast fungus(Pyricularia oryzae(Hebert) Barr.) has better resistance to some common pesticides such as Isoprothiolane.So novel, effective and low residue pesticides and compounds are need to protect rice blast badly.Based on the former results of our laboratory,three main aspects of this paper's research are below.
First,comparing and studying the differences between methods of extracting LC by sodium bisulfite and sodium sulfite.Also we have found the differences of methods of extracting LC by sodium bisulfite under both conditions of microwave and tradition. The results showed that the purity of LC can be reached to 96.23%by the condition of sodium bisulfite.The purity of LC can be reached to 96.74%by the condition of sodium sulfite.Also the content of LC can be reached to 97.28%under the condition of microwaves.In comparison,it has several characteristics such as high selection, short periods of operation,little consumption,high rate of recycle and environmental protection under the condition of microwave.
Secondly,in order to seek novel,effective and safe compounds,we used the principle of model natural product LC active material and linking inferior structure to design and synthesize thirteen acetal and Schiff base compounds in total.
1.Synthesizing four LC acetal compounds,such as LC dimethyl acetal.Identifying their structures by IR,~1H-NMR and elements analysis.
2.Synthesizing six LC Schiff base compounds,such as LC anil Schiff base. Identifying their structures by IR.
3.LC was reduced into limo-amine by cyclohexfanone oximation of LC and condensation with salicylaldehyde.Then we got salicylaldehyde limo-amine Schiff base compound.Based on that compound,it was mixed into coordination compound with Cu~(2+) and Zn~(2+).Identifying their structures by IR and discussing the coordination of those compounds.
Third,all the purposed compounds and natural product LC were operated into the experiment of inhibiting the mycelial growth of Magnaporthe grisea(Hebert) Barr.
1.The inhibitory results of natural product LC(500 mg/L and 31.25 mg/L) were 90.31 and 34.8%respectively.EC_(50) was 50.43 mg/L。
2.All the acetal compounds had certain effective inhibitory results.At the concentration of 500 mg/L,LC butanediol acetal had the best inhibitory result in the acetal compounds.It was 80.27%.
3.Schiff base compounds also had sound inhibitory results.They were 32.27%～94.88%.At the concentration of 500 mg/L,LC sulfanilamide had the best inhibitory result in the Schiff base compounds.It was 94.88%.At the concentration of 31.25 mg/L,Salicylaldehyde-lemon amine complexes of copper had the best inhibitory result in the Schiffbase compounds.It was 56.91%.
4.Results of research showed that natural product LC had better inhibitory results than that of acetal compounds.Relative toxicity index of compounds were 21.45～25.42.Moreover,the inhibitory results of Schiff base compounds were better than that of natural product LC.And it was improved to eliminate rice blast fungus,when Schiffbasses were mixed with metal ions.
引文
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