title: A new class of mealybug pheromones: a hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi.
abstract: Mealybugs, which include several agricultural pests, are small sap feeders covered with a powdery wax. They exhibit clear sexual dimorphism; males are winged but fragile and short lived, whereas females are windless and less mobile. Thus, sex pheromones emitted by females facilitate copulation and reproduction by serving as a key navigation tool for males. Although the structures of the hitherto known mealybug pheromones vary among species, they have a common structural motif; they are carboxylic esters of monoterpene alcohols with irregular non-head-to-tail linkages. However, in the present study, we isolated from the Matsumoto mealybug, Crisicoccus matsumotoi (Siraiwa), a pheromone with a completely different structure. Using gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy, we identified the pheromone as 3-methyl-3-butenyl 5-methylhexanoate. Its attractiveness to males was confirmed in a series of field trapping experiments involving comparison between the isolated natural product and a synthetic sample. This is the first report of a hemiterpene mealybug pheromone. In addition, the acid moiety (5-methylhexanoate) appears to be rare in insect pheromones.
authors: National Institute for Agro-Environmental Sciences, 3-1-3 Kannondai, Tsukuba, Ibaraki, 305-8604, Japan. jtabata@affrc.go.jp
authors: Jun
authors: J
authors: Tabata
authors: Yutaka
authors: Y
authors: Narai
authors: Nobuo
authors: N
authors: Sawamura
authors: Syuntaro
authors: S
authors: Hiradate
authors: Hajime
authors: H
authors: Sugie
mesh_terms: D000818:Animals; D004952:Esters / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006430:Hemiptera / Q000737:chemistry* / Q000187:drug effects / Q000502:physiology*; D008297:Male; D012724:Sex Attractants / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D004952:Esters; D012724:Sex Attractants