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春尺蠖性信息素的成分鉴定及类似物的合成
闫祺
学位类型硕士
导师侯雪玲 ; 阿吉艾克拜尔·艾萨
2011-06-03
学位授予单位中国科学院研究生院
学位授予地点北京
学位专业有机化学
关键词春尺蠖 性信息素 成分鉴定 性信息素类似物 合成
摘要春尺蠖(Apocheima cinerarius Erschoff)属鳞翅目(Lepidoptera)尺蛾科(Geometridae),近年来在新疆胡杨防护林带危害严重,以化学农药为主的防治手段对生态环境造成一定的破坏。本文通过对春尺蠖雌蛾性信息素进行研究,旨在阐明其成分,为利用性信息素进行害虫防治提供依据。 本实验运用气相色谱-触角电位联用仪(gas chromatography-electroantenno graphic detection, GC-EAD)测定春尺蠖雄蛾触角对雌蛾性信息素腺体提取物的活性反应;运用气相色谱-质谱联用仪(gas chromatograph-mass spectrum, GC-MS)鉴定性信息素成分;对性信息素类似物进行合成与筛选。研究内容如下: 1. 春尺蠖雌蛾性信息素成分的提取 通过对春尺蠖求偶节律的观察表明,雌蛾羽化后的第一个暗期便进入求偶期,是雌蛾性信息素提取的最佳时间。采用正己烷浸提雌蛾性信息素腺体的方法取得了对雄蛾触角有显著电生理反应的的活性提取物。 2. 春尺蠖雌蛾性信息素成分的鉴定 GC-EAD结果显示在两处不同的保留时间均存在能引起雄蛾触角电生理反应的活性物质,说明雌蛾性信息素至少含有两种成分。GC-MS分析表明活性成分之一为含有十四个碳原子直链结构的不饱和乙酸酯,其双键位置通过合成的化合物的活性筛选得到确定。 3. 春尺蠖雌蛾性信息素类似物的合成与活性筛选 运用炔烃偶联路线和Wittig反应路线合成了相关信息素类似物,并对合成化合物进行GC-EAD分析,结果显示化合物Z4-14:OAc和Z6-14:OAc均能引起雄蛾触角电生理反应,且在保留时间上和腺体提取物中的活性成分保持一致,因此确定这两种化合物均为春尺蠖雌蛾信息素中的活性成分。 本文首次对春尺蠖性信息素进行了研究,确定了雌蛾性信息素中两种活性成分的结构,为进一步的田间诱引实验提供了方向,为利用春尺蠖性信息素进行害虫无公害防治奠定基础。
其他摘要Apocheima cinerarius Erschoff (Lepidoptera: Geometridae), a polyphagous defoliator pest, multiplied on the most important shelterbelt in Xinjiang recent years, the pesticide-based control on the larvae caused serious damage to the ecological environment. For the purpose of identify the components of sex pheromone and establish the foundation for integrated pest management (IPM) with sex pheromone of A. cinerarius, the sex pheromone of female moth was studied in this paper, The reaction of male moth antenna to the extracts from sex pheromone gland of virgin female moth was analyzed by GC-EAD, and the components of the sex pheromone were identified by GC-MS and synthetic pheromone candidates. The main contents are as follows: 1. Extraction of active components of sex pheromone from A. cinerarius females By observation of biological rhythm of A. cinerarius, the results showed that after the first dark period, the female moths come into the estrous cycle, and it’s the best time for pheromone extract. It’s effectively using hexane to extract the active components from sex pheromone gland of virgin female moths. The sensitive reaction of antennae of male moths to crude extracts was detected. 2. Identification of active components of sex pheromone from A. cinerarius females The GC-EAD results indicated that sensitive electrophysiological reaction of male moth antenna was detected at the two different retention times in the extracts. The sex pheromone would have two or more components. Based on GC-MS data of authentic standards, one or two unsaturated acetate with 14 carbons straight chain was identified as the active components of sex pheromone, and the position of double bond has already identified through synthetic pheromone candidates. 3. Synthesis and GC-EAD analysis of pheromone candidates Using Wittig route and alkyne coupling route, fourteen pheromone candidates were synthesized and analyzed by GC-EAD. The results radiated that two synthetic pheromone candidates, Z4-14:OAc and Z6-14:OAc, both can cause sensitive electrophysiological reaction of male moth antenna, and Rt time conform to the gland extract. So it’s certain that Z4-14:OAc and Z6-14:OAc are the active components of sex pheromone in female A. cinerarius. It is the first time to research on sex pheromone of A. cinerarius, and two active components of sex pheromone were identified. The results not only provide the direction in field tests, but also establish the foundation for providing an efficiency and environmental protection method in pest control of A. cinerarius.
文献类型学位论文
条目标识符http://ir.xjipc.cas.cn/handle/365002/4436
专题资源化学研究室
作者单位中国科学院新疆理化技术研究所
推荐引用方式
GB/T 7714
闫祺. 春尺蠖性信息素的成分鉴定及类似物的合成[D]. 北京. 中国科学院研究生院,2011.
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