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 language | English |
|---|---|
| Pages (from-to) | 567-574 |
| Number of pages | 8 |
| Journal | Naturwissenschaften |
| Volume | 99 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - Jul 1 2012 |
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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 journal › Article
}
TY - JOUR
T1 - A new class of mealybug pheromones
T2 - A hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi
AU - Tabata, Jun
AU - Narai, Yutaka
AU - Sawamura, Nobuo
AU - Hiradate, Syuntaro
AU - Sugie, Hajime
PY - 2012/7/1
Y1 - 2012/7/1
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=84863982368&partnerID=8YFLogxK
U2 - 10.1007/s00114-012-0935-z
DO - 10.1007/s00114-012-0935-z
M3 - Article
VL - 99
SP - 567
EP - 574
JO - Die Naturwissenschaften
JF - Die Naturwissenschaften
SN - 0028-1042
IS - 7
ER -