title: Phytal: a candidate sex pheromone component of the moroccan locust dociostaurus maroccanus.
abstract: 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.
authors.affiliation: Department of Biological Chemistry and Molecular Modelling, IQAC (CSIC) c/ Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: Benjamin
authors.initials: B
authors.lastname: Fürstenau
authors.forename: Lourdes
authors.initials: L
authors.lastname: Muñoz
authors.forename: Milagro
authors.initials: M
authors.lastname: Coca-Abia
authors.forename: Gloria
authors.initials: G
authors.lastname: Rosell
authors.forename: Angel
authors.initials: A
authors.lastname: Guerrero
authors.forename: Carmen
authors.initials: C
authors.lastname: Quero
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004224:Diterpenes / Q000737:chemistry*; D005260:Female; D006110:Grasshoppers / Q000737:chemistry*; D008297:Male; D015394:Molecular Structure; D009018:Morocco; D012724:Sex Attractants / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C586672:3,7,11,15-tetramethylhexadec-2-enal; D000447:Aldehydes; D004224:Diterpenes; D012724:Sex Attractants
keywords: behavior; biosynthesis; locusts; pheromones; structure elucidation