Biochemistry Group Department of Chemistry, Montana State University, 59717, Bozeman, Montana.
J Chem Ecol. 1985 Sep;11(9):1197-208. doi: 10.1007/BF01024108.
The male-produced aggregation pheromone ofDrosophila virilis was found to contain five ester components, in addition to a previously identified hydrocarbon, (Z)-10-heneicosene (Z10-21). The five esters were: the methyl, ethyl, and 1-methylethyl (isopropyl) esters of 2-methyl-(E)-2-butenoic (tiglic) acid and the methyl and ethyl esters of hexanoic acid. The esters were not detected in females. Each ester was active by itself in laboratory bioassay tests, and each increased the number of flies responding toZ10-21 ca. 4-5 times. In comparisons among the five esters at 10 ng per compound, ethyl tiglate was the most active, and methyl tiglate, the least. No mixture of esters was found to be significantly more active than ethyl tiglate alone. In a doseresponse study, bioassay activity increased with dose for both ethyl tiglate andZ10-21. Newly emerged males did not have detectable levels of the esters. All five esters increased as sexual maturity was approached. Ethyl tiglate and ethyl hexanoate were the most abundant in mature males, usually over 15 ng per individual. Ratios among the esters were variable. Male flies also contained an as yet unidentified attractant(s) still more polar than the esters, which was synergistic with the esters and hydrocarbon. Food odors also synergized the synthetic compounds.
雄蝇产生的聚集信息素除了先前鉴定出的(Z)-10-二十一碳烯(Z10-21)外,还含有五种酯类成分。这五种酯类是:2-甲基-(E)-2-丁烯酸(tiglic)的甲酯、乙酯和 1-甲基乙基(异丙基)酯,以及己酸的甲酯和乙酯。这些酯类在雌蝇中没有被检测到。每种酯类在实验室生物测定试验中都具有活性,并且每种酯类都使对 Z10-21 有反应的果蝇数量增加了约 4-5 倍。在对 10ng 每化合物的五种酯类的比较中,乙酯 tiglate 最活跃,而甲酯 tiglate 最不活跃。没有发现任何酯类混合物的活性明显高于单独的乙酯 tiglate。在剂量反应研究中,生物测定活性随着乙酯 tiglate 和 Z10-21 的剂量增加而增加。新出现的雄蝇没有检测到酯类。随着性成熟的接近,所有五种酯类的含量都增加了。在成熟的雄蝇中,乙酯 tiglate 和乙酯 hexanoate 含量最高,通常每个个体超过 15ng。酯类之间的比例是可变的。雄蝇还含有一种尚未鉴定的比酯类更具极性的引诱剂(或引诱剂),它与酯类和碳氢化合物具有协同作用。食物气味也与合成化合物协同作用。