Department of Fisheries and Wildlife, Michigan State University, East Lansing, Michigan, United States of America.
PLoS One. 2013 Jul 9;8(7):e68157. doi: 10.1371/journal.pone.0068157. Print 2013.
A sulphate-conjugated bile alcohol, 3,12-diketo-4,6-petromyzonene-24-sulfate (DKPES), was identified using bioassay-guided fractionation from water conditioned with sexually mature male sea lamprey (Petromyzon marinus). The structure and relative stereochemistry of DKPES was established using spectroscopic data. The electro-olfactogram (EOG) response threshold of DKPES was 10(-7) Molar (M) and that of 3-keto petromyzonol sulfate (3 KPZS; a known component of the male sea lamprey sex pheromone) was 10(-10) M. Behavioural studies indicated that DKPES can be detected at low concentrations by attracting sexually mature females to nests when combined with 3 KPZS. Nests baited with a mixture of DKPES and 3 KPZS (ratio 1∶29.8) attracted equal numbers of sexually mature females compared to an adjacent nest baited with 3 KPZS alone. When DKPES and 3 KPZS mixtures were applied at ratios of 2∶29.8 and 10∶29.8, the proportion of sexually mature females that entered baited nests increased to 73% and 70%, respectively. None of the sexually mature females released were attracted to nests baited with DKPES alone. These results indicated that DKPES is a component of the sex pheromone released by sexually mature male sea lamprey, and is the second biologically active compound identified from this pheromone. DKPES represents the first example that a minor component of a vertebrate pheromone can be combined with a major component to elicit critical sexual behaviors. DKPES holds considerable promise for increasing the effectiveness of pheromone-baited trapping as a means of sea lamprey control in the Laurentian Great Lakes.
从用性成熟的雄性海七鳃鳗 conditioning 的水中，利用生物测定指导的分级分离，鉴定出一种硫酸盐结合的胆甾醇，3,12-二酮-4,6-海七鳃鳗烯-24-硫酸盐（DKPES）。使用光谱数据确定了 DKPES 的结构和相对立体化学。DKPES 的电嗅觉图（EOG）响应阈值为 10（-7）摩尔（M），而 3-酮 petromyzonol 硫酸盐（3KPZS；已知的雄性海七鳃鳗性信息素的组成部分）的响应阈值为 10（-10）M。行为研究表明，当与 3KPZS 结合时，DKPES 可以以低浓度吸引性成熟的雌性进入巢穴。用 DKPES 和 3KPZS（比例 1∶29.8）混合物诱饵的巢穴吸引了与单独用 3KPZS 诱饵的相邻巢穴相同数量的性成熟雌性。当 DKPES 和 3KPZS 混合物以 2∶29.8 和 10∶29.8 的比例应用时，进入诱饵巢穴的性成熟雌性的比例分别增加到 73%和 70%。没有一只性成熟的雌性被单独用 DKPES 诱饵的巢穴吸引。这些结果表明，DKPES 是性成熟雄性海七鳃鳗释放的性信息素的组成部分，是从这种性信息素中鉴定出的第二种具有生物活性的化合物。DKPES 代表了脊椎动物信息素的次要成分可以与主要成分结合以引发关键性行为的第一个例子。DKPES 有望提高性信息素诱饵诱捕作为控制大湖地区海七鳃鳗的方法的有效性。
