- Aggregation pheromone activity of the female sex pheromone, β-acaridial, in Caloglyphus polyphyllae (Acari: Acaridae)
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Caloglyphus (= Sancasania) polyphyllae discharges from a pair of opisthonotal glands a characteristic set of volatiles, i.e. three monoterpenes and seven hydrocarbons. Among them, β-acaridial, which is known as the female sex pheromone of the species and has antifungal activity, was newly identified as the aggregation pheromone for unfeeding and unmating mites. Feeding mites, however, exhibited sexually aroused behavior instead of the tendency to cluster when exposed to β-acaridial. This is the first example of the compound demonstrating two pheromone functions depending upon the circumstances faced by the mites.
- Shimizu, Nobuhiro,Mori, Naoki,Kuwahara, Yasumasa
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- Simple synthesis of mite pheromone beta-acaridial and its analogs in the secretion of Caloglyphus polyphyllae (Acari: Acaridae).
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A simple synthesis of beta-acaridial [(E)-1], the active principle of the sex, alarm and aggregation pheromone among astigmatid mites, was achieved in 5 steps from 1,2,4-butanetriol 2 in a 19% overall yield. Its analog, beta-acariolal 8, was also prepared in a 63% yield by oxidation of the intermediate, beta-acaridiol [(E)-7], with pyridinium dichromate (PDC). This synthetic route also gave beta-(Z)-acaridiol [(Z)-7] by using a Z-selective base in the Wittig reaction. (Z)-7 was oxidized to give a new monoterpene, beta-(Z)-acaridial [(Z)-1], which was detected as a trace component in the secretion of Caloglyphus polyphyllae, together with 8.
- Shimizu, Nobuhiro,Mori, Naoki,Kuwahara, Yasumasa
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- 2(E)-(4-Methyl-3-pentenylidene)-butanedial, β-Acaridial: A New Type of Monoterpene from the Mold Mite Tyrophagus putrescentiae (Acarina, Acaridae)
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The natural product chemistry of opisthonotal gland excretion was studied for the mold mite Tyrophagus putrescentiae.The secretion contained a new type of monoterpene dial, 2(E)-(4-methyl-3-pentenylidene)-butanedial (1), which we gave the trivial name β-a
- Leal, Walter Soares,Kuwahara, Yasumasa,Suzuki, Takahisa
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p. 875 - 878
(2007/10/02)
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