The obligate pollination mutualism between Yucca and yucca moths is a classical example of coevolution. Oviposition and active pollination by female yucca moths occur at night when Yucca flowers are open and strongly scented. Thus, floral volatiles have been suggested as key sensory signals attracting yucca moths to their host plants, but no bioactive compounds have yet been identified. In this study, we showed that both sexes of the pollinator moth Tegeticula yuccasella are attracted to the floral scent of the host Yucca filamentosa. Chemical analysis of the floral headspace from six Yucca species in sections Chaenocarpa and Sarcocarpa revealed a set of novel tetranorsesquiterpenoids putatively derived from (E)-4,8-dimethyl-1,3,7-nonatriene. Their structure elucidation was accomplished by NMR analysis of the crude floral scent sample of Yucca treculeana along with GC/MS analysis and confirmed by total synthesis. Since all these volatiles are included in the floral scent of Y. filamentosa, which has been an important model species for understanding the pollination mutualism, we name these compounds filamentolide, filamentol, filamental, and filamentone. Several of these compounds elicited antennal responses in pollinating (Tegeticula) and non-pollinating (Prodoxus) moth species upon stimulation in electrophysiological recordings. In addition, synthetic (Z)-filamentolide attracted significant numbers of both sexes of two associated Prodoxus species in a field trapping experiment. Highly specialized insect-plant interactions, such as obligate pollination mutualisms, are predicted to be maintained through “private channels” dictated by specific compounds. The identification of novel bioactive tetranorsesquiterpenoids is a first step in testing such a hypothesis in the Yucca-yucca moth interaction.

丝兰和丝兰蛾之间的专性授粉共生是共同进化的经典例子。当丝兰花开放并散发出强烈香味时，雌性丝兰蛾会在夜间产卵和主动授粉。因此，花挥发物被认为是将丝兰蛾吸引到寄主植物的关键感官信号，但尚未鉴定出具有生物活性的化合物。在这项研究中，我们发现传粉蛾Tegeticula yuccasella 的两性都被寄主丝兰丝兰的花香所吸引。六株丝兰花卉顶空的化学分析Chaenocarpa 和 Sarcocarpa 部分中的物种揭示了一组推定来自 ( E )-4,8-​​二甲基-1,3,7-壬三烯的新型四诺倍半萜类化合物。它们的结构解析是通过对丝兰粗花香样品的 NMR 分析以及 GC/MS 分析完成的，并通过全合成进行确认。由于所有这些挥发物都包含在Y. filamentosa的花香中，它一直是了解授粉共生的重要模型物种，我们将这些化合物命名为 filamentolide、filamentol、filamental 和 filamentone。这些化合物中的一些在授粉（Tegeticula）和非授粉（Prodoxus）中引起触角反应) 电生理记录中刺激后的蛾类。此外，在田间诱捕实验中，合成的 ( Z )-filamentolide 吸引了大量两种相关Prodoxus物种的两性。高度专业化的昆虫-植物相互作用，例如专性授粉互惠，预计将通过特定化合物指定的“私人渠道”维持。鉴定新型生物活性四诺倍半萜是在丝兰-丝兰蛾相互作用中测试这种假设的第一步。