Institut für Organische Chemie, Technische Universität Braunschweig , Hagenring 30, 38106 Braunschweig, Germany.
J Nat Prod. 2013 Sep 27;76(9):1548-58. doi: 10.1021/np400131q. Epub 2013 Sep 4.
Acoustic and, to a lesser degree, visual signals are the predominant means of signaling in frogs. Nevertheless, certain lineages such as the mantelline frogs from Madagascar use the chemical communication channel as well. Males possess femoral glands on the hind legs, which recently have been shown to contain volatile compounds used in communication as pheromones. Many mantelline species occur in sympatry, and so far species recognition is regarded to occur mainly by acoustic signals. The analysis of the gland constituents of Mantidactylus femoralis by GC/MS revealed the presence of volatile macrolides and secondary alcohols. The new natural products mantidactolides A (4) and B (6), as well as several methyl carbinols, were identified, and their structures were confirmed by synthesis. The analysis of individuals from different locations of Madagascar revealed the presence of two groups characterized by specific patterns of compounds. While one group contained the alcohols and mantidactolide B, the other showed specific presence of the macrolides phoracantholide I (1) and mantidactolide A (4). Genetic analysis of some individuals showed no congruence between genetic relatedness and gland constituents. Several other individuals from related species had different gland compositions. This suggests that a basic set of biosynthetic machinery might be available to a broader group of related species.
声学和在较小程度上的视觉信号是青蛙中主要的信号方式。然而，某些谱系，如马达加斯加的 mantelline 青蛙，也使用化学通讯通道。雄性后腿有股部腺，最近的研究表明这些腺包含用于通讯的挥发性化合物作为信息素。许多 mantelline 物种共存，到目前为止，物种识别主要被认为是通过声学信号发生的。通过 GC/MS 对 Mantidactylus femoralis 的腺体成分进行分析，发现了存在挥发性大环内酯和二级醇。鉴定了新的天然产物 mantidactolide A（4）和 B（6），以及几种甲基甲醇，并通过合成确定了它们的结构。对来自马达加斯加不同地区的个体进行分析，发现存在两组具有特定化合物模式的特征。一组含有醇和 mantidactolide B，而另一组则显示出大环内酯 phoracantholide I（1）和 mantidactolide A（4）的特定存在。对一些个体的遗传分析表明，遗传相关性和腺体成分之间没有一致性。来自相关物种的其他几个个体具有不同的腺体组成。这表明，一组基本的生物合成机制可能对更广泛的相关物种都可用。
