Arid
DOI10.1002/cbic.201300247
Phytal: A Candidate Sex Pheromone Component of the Moroccan Locust Dociostaurus maroccanus
Fuerstenau, Benjamin1; Munoz, Lourdes1; Coca-Abia, Milagro2; Rosell, Gloria3; Guerrero, Angel1; Quero, Carmen1
通讯作者Guerrero, Angel
来源期刊CHEMBIOCHEM
ISSN1439-4227
EISSN1439-7633
出版年2013
卷号14期号:12页码:1450-1459
英文摘要

Outbreaks of locusts cause enormous economic losses to agriculture in many countries. To develop environmentally friendly strategies for their control, much research has been focused on the factors that influence locust biology, particularly infochemical-mediated interactions. We present herein the identification and synthesis of both Z and E isomers of phytal (3,7,11,15-tetramethylhexadec-2-enal, 1), which are involved in chemical communication and behaviour of the Moroccan locust, Dociostaurus maroccanus, a serious agricultural pest. The compound was identified by comparison of its chromatographic and spectrometric features and microchemical reactions with those of a synthetic sample. The natural compound was shown to have the R,R configuration by chiral HPLC analysis, and its structure is unique as an insect pheromone component. Both isomers of phytal are produced by sexually mature adult males and elicit electroantennographic responses in antennae of both sexes. In two-choice olfactometer bioassays, males and females significantly preferred the stream enriched with racemic phytal to the control. In contrast, hydrogenated phytal was behaviourally inert. Both isomers of phytal are specific to D. maroccanus as they are absent in the closely related, habitat-sharing species Dociostaurus jagoi and Calliptamus wattenwylianus. Legs and wings are the main release sites of the compound: approximately 90% of that emitted by living individuals. In biosynthetic studies, phytal appears to proceed from oxidation of phytol (2) after injection of deuterated phytol into the abdomen of the insect or after administration in the diet. Our results demonstrate that phytal is a candidate sex pheromone component of the Moroccan locust; it is produced by mature males, and might be eavesdropped upon by conspecific males.


英文关键词behavior biosynthesis locusts pheromones structure elucidation
类型Article
语种英语
国家Spain
收录类别SCI-E
WOS记录号WOS:000323099500016
WOS关键词SCHISTOCERCA-GREGARIA FORSKAL ; COURTSHIP-INHIBITION PHEROMONE ; DESERT LOCUST ; ALDEHYDES ; PHENYLACETONITRILE ; AGGREGATION ; OXIDATION ; UPDATE ; SYSTEM ; ESTERS
WOS类目Biochemistry & Molecular Biology ; Chemistry, Medicinal
WOS研究方向Biochemistry & Molecular Biology ; Pharmacology & Pharmacy
资源类型期刊论文
条目标识符http://119.78.100.177/qdio/handle/2XILL650/176360
作者单位1.CSIC, IQAC, Dept Biol Chem & Mol Modelling, ES-08034 Barcelona, Spain;
2.Ctr Invest & Tecnol Agroalimentaria, Dept Ind & Innovac DGA, Unidad Sanidad Vegetal, Zaragoza 50059, Spain;
3.Univ Barcelona, Fac Pharm, Unity Associated CSIC, Dept Pharmacol & Therapeut Chem, E-08028 Barcelona, Spain
推荐引用方式
GB/T 7714
Fuerstenau, Benjamin,Munoz, Lourdes,Coca-Abia, Milagro,et al. Phytal: A Candidate Sex Pheromone Component of the Moroccan Locust Dociostaurus maroccanus[J],2013,14(12):1450-1459.
APA Fuerstenau, Benjamin,Munoz, Lourdes,Coca-Abia, Milagro,Rosell, Gloria,Guerrero, Angel,&Quero, Carmen.(2013).Phytal: A Candidate Sex Pheromone Component of the Moroccan Locust Dociostaurus maroccanus.CHEMBIOCHEM,14(12),1450-1459.
MLA Fuerstenau, Benjamin,et al."Phytal: A Candidate Sex Pheromone Component of the Moroccan Locust Dociostaurus maroccanus".CHEMBIOCHEM 14.12(2013):1450-1459.
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