Insect Chemical Ecology Laboratory U.S. Department of Agriculture, Agricultural Research Service Beltsville Agricultural Research Center, 20705, Beltsville, Maryland.
J Chem Ecol. 1992 Mar;18(3):283-98. doi: 10.1007/BF00994232.
Isomers of [11,12-(3)H2]-11-tetradecenyl acetate (57 Ci/mM) were synthesized. Behavioral assay of the two compounds using Z- and E-type European corn borer (ECB) males showed that introduction of tritons into the double bond of the pheromone caused a significant isotope effect in the E-type ECB but not in the Z-type ECB. Measurements of tritium associated with the male antennae after a 3-min exposure showed that radioactivity equivalent to 10(-7) mol pheromone was adsorbed onto male antennae. Time-course in vivo metabolic studies with picogram amounts of compound applied topically to antennae of E- and Z-type males and Z-type females showed that they metabolized pheromone similarly but females degraded pheromone more slowly than males. Pheromone was hydrolyzed, and the only other major radiolabeled metabolite observed by combined high-pressure liquid chromatography-radiodetection was tritiated water. Capillary gas chromatography and radiomonitoring permitted detection of a trace amount of 11-tetradecenoic acid, which indicated alcohol oxidase activity is associated with the antennae. Evidence shows that clearing of pheromone from the ECB male antennae involves hydrolysis and oxidation of the alcohol to fatty acid, which in turn is degraded, probably via β-oxidation, to carbon dioxide and water.
[11,12-(3)H2]-11-十四烯基乙酸酯（57 毫居/毫摩尔）的异构体被合成。使用 Z 型和 E 型欧洲玉米螟（ECB）雄虫对这两种化合物进行行为测定，结果表明，在信息素的双键中引入氚会导致 E 型 ECB 中产生显著的同位素效应，但在 Z 型 ECB 中则没有。对经过 3 分钟暴露后的雄虫触角中的氚进行测量，结果表明，相当于 10(-7)摩尔信息素的放射性物质被吸附到了雄虫的触角上。对应用于 E 型和 Z 型雄虫以及 Z 型雌虫触角的微克级化合物进行的体内代谢时程研究表明，它们代谢信息素的方式相似，但雌虫降解信息素的速度比雄虫慢。信息素被水解，通过结合高压液相色谱-放射性检测，观察到的唯一其他主要放射性标记代谢产物是氚化水。毛细管气相色谱和放射性监测允许检测到痕量的 11-十四烯酸，这表明醇氧化酶活性与触角有关。证据表明，从 ECB 雄虫触角中清除信息素涉及到醇的水解和氧化成脂肪酸，而脂肪酸反过来又被降解，可能通过β-氧化，生成二氧化碳和水。
