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Identification of Zingiberenol and Murgantiol as Components of the Aggregation-Sex Pheromone of the Rice Stink Bug, Mormidea v-luteum (Heteroptera: Pentatomidae)
Journal of Chemical Ecology ( IF 2.3 ) Pub Date : 2020-11-02 , DOI: 10.1007/s10886-020-01231-0
Antonioni Acacio Campos Moliterno , Douglas José De Melo , Paulo Henrique Gorgatti Zarbin

Mormidea v-luteum (Lichtenstein, 1796) feeds on commercial crops, such as rice and ryegrass, causing damage that slows growth and reduces productivity. With the aim of developing an eco-friendly control technique, we investigated the compounds involved in chemical communication in this species. The volatiles produced by a group of seven males or females allocated to different aerated glass chambers were collected for 24 h and analyzed by gas chromatograph/mass spectrometry and gas chromatography/Fourier transform infrared spectroscopy. The analyses showed six male-specific compounds, identified as two isomers of zingiberenol (compounds 1 and 2), three isomers of murgantiol (3, 5 and 6) and sesquipiperitol (4). Compounds 1 and 5 were the major components and were produced in a ratio of 6:4. The absolute stereochemistry of the two isomers of zingiberenol was established as (1S,4R,1’S)-1 and (1R,4R,1’S)-2 by chiral gas chromatography. Stereochemistry was not determined for all the other molecules. To confirm the attractiveness of these chemicals, bioassays were performed in a Y-tube olfactometer, first using crude extracts and, subsequently, synthetic compounds. Male volatiles were attractive to both sexes, demonstrating an aggregation pheromone. In bioassays with synthetic compounds, (1’S)-zingiberenol was highly attractive to both males and females. However, when (1’S)-murgantiol was tested, only females were attracted. Interestingly, when a mixture of zingiberenol and murgantiol isomers was tested, it was attractive to both sexes, with females more attracted to the mixture than to zingiberenol alone; males did not distinguish between treatments. Thus, the bioassay data suggest that the molecules have different functions in chemical communication of this species: zingiberenol acts primarily as an aggregation pheromone, while murgantiol plays a role as a sex pheromone.



中文翻译:

鉴定姜黄烯醇和Murgantiol是稻臭虫Mormidea v-luteum(Heteroptera:Pentatomidae)的聚集性信息素的成分。

Mormidea v-luteum(Lichtenstein,1796)以商业作物为食,例如水稻和黑麦草,造成损害,减缓了生长并降低了生产力。为了开发一种生态友好的控制技术,我们研究了该物种化学通讯中涉及的化合物。收集由分配给不同充气玻璃室的七个雄性或雌性组成的组产生的挥发物,持续24小时,并通过气相色谱/质谱和气相色谱/傅里叶变换红外光谱进行分析。分析结果显示6雄性特异性化合物,鉴定为zingiberenol的两种异构体(化合物12),murgantiol(的三种异构体356)和倍半萜糖醇(4)。化合物15是主要成分,以6:4的比例生产。姜黄烯醇的两个异构体的绝对立体化学确定为(1 S, 4 R, 1 'S-1和(1 R, 4 R, 1 'S-2通过手性气相色谱法。尚未确定所有其他分子的立体化学。为了确认这些化学药品的吸引力,首先使用粗提物,然后使用合成化合物,在Y型管嗅觉仪中进行生物测定。男性挥发物对男女都有吸引力,表明聚集信息素。在具有合成化合物的生物测定中,(1 'S)-姜黄烯醇对男性和女性均极具吸引力。但是,当(1 'S)-murgantiol经过测试,只有雌性被吸引。有趣的是,当测试姜丁烯醇和丁香酚异构体的混合物时,它对两性都具有吸引力,与单独使用姜丁烯醇相比,雌性对混合物的吸引力更大。男性没有区别对待。因此,生物测定数据表明该分子在该物种的化学通讯中具有不同的功能:姜丁烯醇主要起聚集信息素的作用,而丁香醇则起性信息素的作用。

更新日期:2020-11-02
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