A new class of mealybug pheromones

A hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi

Jun Tabata, Yutaka Narai, Nobuo Sawamura, Syuntaro Hiradate, Hajime Sugie

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)567-574
Number of pages8
JournalNaturwissenschaften
Volume99
Issue number7
DOIs
Publication statusPublished - Jul 1 2012

Fingerprint

Pseudococcidae
sex pheromone
sex pheromones
pheromone
pheromones
ester
esters
insect pheromones
waxes
monoterpenoids
sexual dimorphism
copulation
sap
monoterpene
linkage (genetics)
trapping
nuclear magnetic resonance spectroscopy
wax
alcohols
pests

All Science Journal Classification (ASJC) codes

  • Ecology, Evolution, Behavior and Systematics

Cite this

A new class of mealybug pheromones : A hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi. / Tabata, Jun; Narai, Yutaka; Sawamura, Nobuo; Hiradate, Syuntaro; Sugie, Hajime.

In: Naturwissenschaften, Vol. 99, No. 7, 01.07.2012, p. 567-574.

Research output: Contribution to journalArticle

Tabata, Jun ; Narai, Yutaka ; Sawamura, Nobuo ; Hiradate, Syuntaro ; Sugie, Hajime. / A new class of mealybug pheromones : A hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi. In: Naturwissenschaften. 2012 ; Vol. 99, No. 7. pp. 567-574.
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