Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA.
Mar Drugs. 2018 Sep 1;16(9):308. doi: 10.3390/md16090308.
Three novel bile acid derivatives, petromylidenes A⁻C (⁻), featuring uncommon alkylidene adductive scaffolds, were isolated from water conditioned with sexually mature male sea lampreys (). Their structures were elucidated by mass spectrometry and NMR spectroscopy, and by comparison to spectral data of related structures. The identification of compounds ⁻, further illustrates the structural diversity of the 5α bile salt family. Compounds ⁻ exhibited notable biological properties as well, including high olfactory potencies in adult sea lampreys and strong behavioral attraction of ovulated female sea lampreys. Electro-olfactogram recordings indicated that the limit of detection for was 10 M, was 10 M, and was less than 10 M. These results suggested ⁻ were likely male pheromones, which guide reproductive behaviors in the sea lamprey.
从性成熟的雄性海七鳃鳗（Petromyzon marinus）产生的水中分离到三种新型胆酸衍生物，petromylidenes A-C（1-3），它们具有不常见的亚烷基加合物支架。通过质谱和 NMR 光谱以及与相关结构的光谱数据比较，阐明了它们的结构。化合物 1-3 的鉴定进一步说明了 5α 胆盐家族的结构多样性。化合物 1-3 还表现出显著的生物学特性，包括在成年海七鳃鳗中具有较高的嗅觉效力，以及对产卵的雌性海七鳃鳗的强烈行为吸引力。电嗅觉图记录表明，对 1 的检测限为 10M，对 2 的检测限为 10M，对 3 的检测限小于 10M。这些结果表明 1-3 可能是雄性信息素，它们指导海七鳃鳗的生殖行为。
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