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入侵粉蚧（德洛托）性信息素的绝对构型：两种对映体的合成与生物测定

Absolute Configuration of the Invasive Mealybug (De Lotto) Sex Pheromone: Synthesis and Bioassay of Both Enantiomers.

作者信息

Marzo Bargues Javier, Vacas Sandra, Navarro Fuertes Ismael, Primo Jaime, Abad-Somovilla Antonio, Navarro-Llopis Vicente

机构信息

Ecología y Protección Agrícola SL, Pol. Ind. Ciutat de Carlet, 46240 Carlet, Valencia, Spain.

Departamento de Química Orgánica, Universitat de València, Dr Moliner 50, 46100 Burjassot, Valencia, Spain.

出版信息

J Agric Food Chem. 2024 Oct 2;72(39):21488-21494. doi: 10.1021/acs.jafc.4c05469. Epub 2024 Sep 19.

DOI:10.1021/acs.jafc.4c05469
PMID:39297604
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11450821/
Abstract

The mealybug (De Lotto) (Hemiptera: Pseudococcidae) is an invasive pest reported in Europe at the end of the first decade of the 2000s, causing severe damage to citrus production in eastern Spain. In a previous work, (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl)methyl acetate was identified as the sex pheromone emitted by females, a new compound with an unusual β-necrodol skeleton possessing one stereocenter. This compound was assigned to the (-)-enantiomer but the absolute configuration was then not reported. In the present study, enantiomeric pure samples of both enantiomers were synthesized. X-ray diffraction analysis allowed the (-)-enantiomer, identical to the one emitted by virgin females, to be unequivocally identified as (-)-()-(4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl)methyl acetate. Bioassays carried out to test the activity of both enantiomers under field conditions suggest that the presence of the (+)-()-enantiomer has detrimental effects on the activity of the racemates.

摘要

粉蚧（德洛托）（半翅目：粉蚧科）是21世纪第一个十年末在欧洲被报道的一种入侵性害虫，对西班牙东部的柑橘生产造成了严重损害。在之前的一项研究中，（4,5,5-三甲基-3-亚甲基环戊-1-烯-1-基）甲基乙酸酯被鉴定为雌虫释放的性信息素，这是一种具有不寻常β-坏死醇骨架且含有一个立体中心的新化合物。该化合物被指定为（-）-对映体，但当时未报道其绝对构型。在本研究中，合成了两种对映体的对映体纯样品。X射线衍射分析使得（-）-对映体（与未交配雌虫释放的对映体相同）被明确鉴定为（-）-（）-（4,5,5-三甲基-3-亚甲基环戊-1-烯-1-基）甲基乙酸酯。在田间条件下进行的测试两种对映体活性的生物测定表明，（+）-（）-对映体的存在对消旋体的活性有不利影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/a95cb6e1056d/jf4c05469_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/113edfab747c/jf4c05469_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/5fddf5cda690/jf4c05469_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/c08d6d94f03c/jf4c05469_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/6a19a2a50dc4/jf4c05469_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/ad0228e08b98/jf4c05469_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/4520a98907a4/jf4c05469_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/a95cb6e1056d/jf4c05469_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/113edfab747c/jf4c05469_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/5fddf5cda690/jf4c05469_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/c08d6d94f03c/jf4c05469_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/6a19a2a50dc4/jf4c05469_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/ad0228e08b98/jf4c05469_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/4520a98907a4/jf4c05469_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/de2b/11450821/a95cb6e1056d/jf4c05469_0007.jpg

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J Agric Food Chem. 2019 Aug 28;67(34):9441-9449. doi: 10.1021/acs.jafc.9b01443. Epub 2019 Aug 19.
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