« Previous Abstract"A new lavandulol-related monoterpene in the sex pheromone of the grey pineapple mealybug, Dysmicoccus neobrevipes"    Next AbstractGenetic Basis Underlying Structural Shift of Monoterpenoid Pheromones in Mealybugs »

J Chem Ecol

Title:		"(1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata"
Author(s):		Tabata J; Ichiki RT;
Address:		"National Agriculture and Food Research Organization, 3-1-3 Kannondai, Tsukuba, Ibaraki, 305-8604, Japan. jtabata@affrc.go.jp. National Agriculture and Food Research Organization, 3-1-3 Kannondai, Tsukuba, Ibaraki, 305-8604, Japan"
Journal Title:		J Chem Ecol
Year:		2017
Volume:		20170819
Issue:		8
Page Number:		745 - 752
DOI:		10.1007/s10886-017-0879-z
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,3R)-trans configuration. Interestingly, chrysanthemic acid-related structures are also found in insect sex pheromones; carboxylic esters of (1R,3R)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol (chrysanthemyl alcohol) have been reported from two mealybug species. In the present study, another ester of chrysanthemyl alcohol was discovered from the striped mealybug, Ferrisia virgata (Cockerell), as its pheromone. By means of gas chromatography-mass spectrometry, nuclear magnetic resonance spectrometry, and high-performance liquid chromatography analyses using a chiral stationary phase column and authentic standards, the pheromone was identified as (1S,3R)-(-)-cis-chrysanthemyl tiglate. The (1S,3R)-enantiomer strongly attracted adult males in a greenhouse trapping bioassay, whereas the other enantiomers showed only weak activity. The cis configuration of the chrysanthemic acid-related structure appears to be relatively scarce in nature, and this is the first example reported from arthropods"
Keywords:		"Animals Chromatography, High Pressure Liquid Crotonates/*chemistry/pharmacology Female Gas Chromatography-Mass Spectrometry Hemiptera/*chemistry/physiology Hemiterpenes Magnetic Resonance Spectroscopy Male Pyrethrins/chemistry/pharmacology Sex Attractants;"
Notes:		"MedlineTabata, Jun Ichiki, Ryoko T eng 16K08103/Japan Society for the Promotion of Science/ 2017/08/22 J Chem Ecol. 2017 Aug; 43(8):745-752. doi: 10.1007/s10886-017-0879-z. Epub 2017 Aug 19"