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Naturwissenschaften

Title:		A new class of mealybug pheromones: a hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi
Author(s):		Tabata J; Narai Y; Sawamura N; Hiradate S; Sugie H;
Address:		"National Institute for Agro-Environmental Sciences, 3-1-3 Kannondai, Tsukuba, Ibaraki, 305-8604, Japan. jtabata@affrc.go.jp"
Journal Title:		Naturwissenschaften
Year:		2012
Volume:		20120701
Issue:		7
Page Number:		567 - 574
DOI:		10.1007/s00114-012-0935-z
ISSN/ISBN:		1432-1904 (Electronic) 0028-1042 (Linking)
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"
Keywords:		Animals Esters/*chemistry/isolation & purification/pharmacology Female Gas Chromatography-Mass Spectrometry Hemiptera/*chemistry/drug effects/*physiology Male Sex Attractants/*chemistry/isolation & purification/pharmacology;
Notes:		"MedlineTabata, Jun Narai, Yutaka Sawamura, Nobuo Hiradate, Syuntaro Sugie, Hajime eng Research Support, Non-U.S. Gov't Germany 2012/07/04 Naturwissenschaften. 2012 Jul; 99(7):567-74. doi: 10.1007/s00114-012-0935-z. Epub 2012 Jul 1"