萜类驱避化合物与引诱物缔合作用对驱避活性影响的定量计算

发布时间：2018-01-18 14:09

本文关键词：萜类驱避化合物与引诱物缔合作用对驱避活性影响的定量计算　出处：《江西农业大学》2013年硕士论文　论文类型：学位论文

【摘要】：蚊虫是主要的卫生媒介害虫之一,可以传播多种致命疾病,严重危害人类健康,因此蚊虫防治一直以来都是有害生物防治的重要任务。蚊虫驱避剂对蚊虫具有良好的驱避能力,且使用方便安全,但其作用机理仍然没有明确的定论。驱避化合物与引诱物缔合作用对驱避活性具有重要影响,但相关研究非常薄弱。本研究以22个萜类驱避化合物和5种主要引诱物(乳酸、氨、1-辛烯-3-醇、甲酸和碳酸)为研究对象,探究萜类驱避化合物与主要蚊虫引诱物的缔合作用,并研究这种缔合作用对蚊虫驱避活性的影响,以期为蚊虫驱避作用机理的揭示寻找新的理论依据。本文的研究过程和结果如下：借助理论计算的的方法研究驱避化合物与主要引诱物物缔合作用的强度和形式。利用Gaussian View 4.1、Gaussian 03 W和AMPAC软件进行结构构建和优化。结构优化结束后,获得键长、键角等几何参数；通过计算相互作用前后能量变化,获得缔合能量。结果表明：22个萜类驱避化合物和5种主要引诱物之间存在一定强度的缔合作用,可形成稳定的缔合体,相互作用的形式主要为氢键。乳酸、甲酸和碳酸由于分子内羰基的影响,导致它们与驱避化合物相互作用的强度要高于氨和1-辛烯-3-醇与驱避化合物的相互作用。乳酸、氨和碳酸由于分子内有多个可以参与氢键相互作用的羟基或碳氢基团,导致它们与驱避化合物相互作用的形式要多于1-辛烯-3-醇和甲酸。借助定量构效关系计算方法研究缔合作用对驱避活性的影响。利用AMPAC和CODESSA 2.7.10计算驱避化合物自身结构描述符、缔合体结构描述符及特征区域描述符。应用启发式回归从这些描述符中筛选与驱避活性显著相关的描述符,以萜类驱避化合物对白蚊伊蚊Aedes albopictus的校正驱避率的对数值为活性数据,建立描述符与驱避活性的定量构效关系(quantitative structure-activity relationship, QSAR)模型,模型的稳定性采用“留一法”交叉检验和3重内部检验进行验证。结果表明：在获得的5个理想的QSAR模型中,有3个“三描述符模型”,2个“四描述符模型”,相关系数都在0.9以上。模型检验显示,5个模型都具有良好的稳定性。分析建模的描述符可知,任意一个模型中至少有一个描述符是来至缔合体或特征区域,意味着缔合体或特征区域的结构与驱避活性显著相关,对这些描述符的含义进行分析,可以推测缔合体的形状、构象、自旋性质以及缔合部位的静电能对驱避活性存在显著影响。综上所述,萜类驱避化合物与5种引诱物(L-乳酸、氨、1-辛烯-3-醇、甲酸和碳酸)之间存在一定强度的分子间氢键作用,这种作用可以对驱避活性产生显著影响。
[Abstract]:Mosquitoes are one of the major health vector pests, which can spread many deadly diseases and seriously harm human health. Therefore, mosquito control has always been an important task of pest control. Mosquito repellent has good repellent ability to mosquitoes, and its use is convenient and safe. However, there is still no clear conclusion on the mechanism of its action. The association of repellent compounds with attractant has an important effect on repellent activity. In this study, 22 terpenoid repellent compounds and 5 main attractants (lactic acid, ammonia 1-octene-3-ol, formic acid and carbonic acid) were studied. To explore the association of terpene repellent compounds with the main mosquito attractant and to study the effect of this association on repellent activity of mosquitoes. In order to find a new theoretical basis for revealing the mechanism of repellent action of mosquitoes, the research process and results of this paper are as follows:. The strength and form of association between repellent compounds and main attractants were studied by means of theoretical calculation. Gaussian View 4.1 was used. Gaussian 03 W and AMPAC are used to construct and optimize the structure. After the structure optimization is finished, the geometric parameters such as bond length and bond angle are obtained. The association energy was obtained by calculating the energy changes before and after the interaction. The results showed that there was a strong association between 22 terpenoid repellent compounds and 5 main attractants, which could form a stable association. The main forms of interaction are hydrogen bonds. Lactic acid formic acid and carbonic acid are affected by intramolecular carbonyl groups. As a result, their interaction with repellent compounds is stronger than that of ammonia and 1-octene-3-ol with repellent compounds. Ammonia and carbonic acid have many hydroxyl or hydrocarbon groups within the molecule that can participate in the hydrogen bond interaction. As a result, they interact with repellent compounds in more forms than 1-octene-3-alcohols and formic acid. The effect of association on repellent activity is studied by means of quantitative structure-activity relationship calculation. AMPAC and COD are used to study the effect of association on repellent activity. ESSA. 2.7.10 calculation of the structure descriptor of the repellent compound itself. Association structure descriptors and feature region descriptors. Heuristic regression was applied to screen descriptors from these descriptors that were significantly related to repellent activity. The logarithmic values of the corrected repellent rate of terpenoid repellent compound to Aedes albopictus of Aedes albopictus were used as the activity data. The quantitative structure-activity relationship between descriptors and repellent activity was established. QSAR) model, the stability of the model is verified by "left one method" cross test and triple internal test. The results show that: in the obtained five ideal QSAR models. There are three "three descriptor models" and two "four descriptor models" with correlation coefficients above 0.9. The model tests show that all the five models have good stability. In any model, at least one descriptor is from association or feature region, which means that the structure of association or feature region is significantly related to repellent activity, and the meaning of these descriptors is analyzed. It can be inferred that the shape, conformation, spin properties and electrostatic energy of association sites have significant effects on repellent activity. In conclusion, terpene repellent compounds and five attractants, L-lactic acid, ammonia. There is a strong intermolecular hydrogen bond between 1-octene-3-ol, formic acid and carbonic acid, which has a significant effect on repellent activity.
【学位授予单位】：江西农业大学
【学位级别】：硕士
【学位授予年份】：2013
【分类号】：TQ453.2;R184.31

【共引文献】