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首页> 美国卫生研究院文献>Molecules >Antifeedant Effects of Essential Oil Extracts and Isolated Sesquiterpenes from Pilgerodendron uviferum (D. Don) Florin Heartwood on Red Clover Borer Hylastinus obscurus (Coleoptera: Curculionidae)
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Antifeedant Effects of Essential Oil Extracts and Isolated Sesquiterpenes from Pilgerodendron uviferum (D. Don) Florin Heartwood on Red Clover Borer Hylastinus obscurus (Coleoptera: Curculionidae)

机译：紫罗兰（D. Don）弗罗林心材精油提取物和分离的倍半萜类对红三叶草Bor虫Hylastinus obscurus（鞘翅目：Curculionidae）的拒食作用

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The beetle Hylastinus obscurus Marsham (Coleoptera: Curculionidae), endemic to Europe and Northern Africa, is one of the most important red clover pests in Chile. As commercial insecticides are less effective against this pest, plant secondary metabolites have been considered as an alternative for its control. Here, we have investigated the chemical composition of essential oil (EO), petroleum ether extract (PEE), and dichloromethane extract (DCME) from Pilgerodendron uviferum heartwood. Additionally, the effects of EO and extracts on the feeding behavior (% of weight shift) of H. obscurus have been evaluated. The composition of EO, PEE, and DCME were analyzed using gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The results showed the presence of a similar mixture of sesquiterpenes in the essential oil and in both of the extracts, which accounted for circa 60% of the total mixture. Sesquiterpenes were further isolated using chromatographic methods and were structurally characterized by optical rotation, GC–MS, FTIR, and 1D and 2D NMR experiments. The physicochemical properties of the isolated sesquiterpenes, including lipophilicity and vapor pressure, were also determined. The sesquiterpenes were identified as the following: (−)-trans-calamenene (>1), cadalene (>2), (−)-cubenol (>3), (−)-epi-cubenol (>4), (−)-torreyol (>5), and (−)-15-copaenol (>6). The antifeedant activity of EO, extracts, and isolated sesquiterpenes were evaluated using artificial diets in a non-choice test. Relative to the control, the EO, DCME extract, and the isolated sesquiterpenes, namely, (−)-trans-calamenene (>1), cadalene (>2), and (>5) torreyol, were found to be the most effective treatments against H. obscurus. Our study showed that the compounds occurring in P. uviferum heartwood were effective in reducing the adult growth of H. obscurus. The physicochemical properties of the isolated sesquiterpenes might have been associated with antifeedant effects.
机译：欧洲和北非特有的甲虫Hylastinus obscurus Marsham（鞘翅目：Curculionidae）是智利最重要的红三叶草害虫之一。由于商业杀虫剂对这种害虫的效力较弱，因此植物次生代谢产物已被认为是控制其的替代方法。在这里，我们已经研究了来自Pilgerodendron uviferum心材的精油（EO），石油醚提取物（PEE）和二氯甲烷提取物（DCME）的化学成分。另外，已经评估了EO和提取物对暗纹嗜血杆菌的进食行为（体重变化％）的影响。使用气相色谱（GC）和气相色谱/质谱（GC / MS）分析EO，PEE和DCME的组成。结果表明，香精油和两种提取物中均存在类似的倍半萜类混合物，约占总混合物的60％。倍半萜通过色谱方法进一步分离，并通过旋光，GC-MS，FTIR以及1D和2D NMR实验对其结构进行了表征。还确定了分离的倍半萜的理化性质，包括亲脂性和蒸气压。倍半萜烯的鉴定如下：（-）-反式cal草烯（> 1 ），降钙素（> 2 ），（-）-小茴香酚（> 3 ），（-）-表古苯酚（> 4 ），（-）-三苯甲基酚（> 5 ）和（-）-15-copaenol（> 6 ）。在非选择测试中，使用人工饮食评估了EO，提取物和分离的倍半萜的拒食活性。相对于对照，EO，DCME提取物和分离出的倍半萜烯，即（-）-反式-卡拉曼烯（> 1 ），降钙素（> 2 ）和（发现> 5 ）甲苯酚是最有效的抗隐孢子虫的治疗方法。我们的研究表明，在体育紫罗兰心材中存在的化合物可有效减少隐匿性嗜血杆菌的成虫生长。分离出的倍半萜的理化性质可能与拒食作用有关。

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