« Previous AbstractOlfactory cues from plants infected by powdery mildew guide foraging by a mycophagous ladybird beetle    Next AbstractSex pheromone of a coccoid insect with sexual and asexual lineages: fate of an ancestrally essential sexual signal in parthenogenetic females »

J Chem Ecol

Title:		"Sex Pheromone of the Cotton Mealybug, Phenacoccus solenopsis, with an Unusual Cyclobutane Structure"
Author(s):		Tabata J; Ichiki RT;
Address:		"National Agriculture and Food Research Organization (NARO), 3-1-3 Kannondai, Tsukuba, Ibaraki, 305-8604, Japan. jtabata@affrc.go.jp. Japan International Research Center for Agricultural Sciences, Ohwashi 1-1, Tsukuba, Ibaraki, 305-8686, Japan"
Journal Title:		J Chem Ecol
Year:		2016
Volume:		20161022
Issue:		11
Page Number:		1193 - 1200
DOI:		10.1007/s10886-016-0783-y
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"The cotton mealybug, Phenacoccus solenopsis, the distribution of which was formerly limited to Nearctic and Neotropical regions, recently invaded many countries in various regions including Asia, Africa, and the Pacific. More recently, P. solenopsis was newly recorded in Japan and is currently an emerging pest of agricultural crops. In this study, we determined the structure of a sex pheromone of P. solenopsis in order to develop an effective lure for monitoring this pest. From volatiles emitted by virgin adult females, we isolated a compound attractive to males. By means of coupled gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy, we identified this as (2,2-dimethyl-3-isopropylidenecyclobutyl)methyl 3-methylbut-2-enoate. This compound was synthesized and shown to be attractive to male P. solenopsis. Analysis by gas chromatography using an enantioselective stationary phase and polarimetry analyses of the natural pheromone and synthetic enantiomers showed the natural compound to be the (R)-(-)-enantiomer. This compound is an ester of maconelliol, which has an unusual cyclobutane structure found in sex pheromones of other mealybug species, and senecioic acid, also found in the pheromones of other mealybug species. However, this is the first example of the ester of maconelliol and senecioic acid as a natural product"
Keywords:		Animals Cyclobutanes/*chemistry/pharmacology Female Hemiptera/*chemistry/drug effects Male Sex Attractants/*chemistry/pharmacology Stereoisomerism Cyclobutanoid monoterpene Phenacoccus gossypiphilous Phenacoccus solenopsis Sex pheromone;
Notes:		"MedlineTabata, Jun Ichiki, Ryoko T eng 2016/10/25 J Chem Ecol. 2016 Nov; 42(11):1193-1200. doi: 10.1007/s10886-016-0783-y. Epub 2016 Oct 22"