Department of Neurobiology, Harvard Medical School, 220 Longwood Avenue, Boston, MA 02115, USA.
Curr Biol. 2009 Aug 11;19(15):1245-54. doi: 10.1016/j.cub.2009.06.037. Epub 2009 Jul 16.
In many insect species, cuticular hydrocarbons serve as pheromones that can mediate complex social behaviors. In Drosophila melanogaster, several hydrocarbons including the male sex pheromone 11-cis-vaccenyl acetate (cVA) and female-specific 7,11-dienes influence courtship behavior and can function as cues for short-term memory associated with the mating experience. Behavioral and physiological studies suggest that other unidentified chemical communication cues are likely to exist. To more fully characterize the hydrocarbon profile of the D. melanogaster cuticle, we applied direct ultraviolet laser desorption/ionization orthogonal time-of-flight mass spectrometry (UV-LDI-o-TOF MS) and analyzed the surface of intact fruit flies at a spatial resolution of approximately 200 mum.
We report the chemical and spatial characterization of 28 species of cuticular hydrocarbons, including a new major class of oxygen-containing compounds. Via UV-LDI MS, pheromones previously shown to be expressed exclusively by one sex, e.g., cVA, 7,11-heptacosadiene, and 7,11-nonacosadiene, appear to be found on both male and female flies. In males, cVA colocalizes at the tip of the ejaculatory bulb with a second acetylated hydrocarbon named CH503. We describe the chemical structure of CH503 as 3-O-acetyl-1,3-dihydroxy-octacosa-11,19-diene and demonstrate a behavioral role for this compound as a long-lived inhibitor of male courtship. Like cVA, CH503 is transferred from males to females during mating. Unlike cVA, CH503 remains on the surface of females for at least 10 days.
Oxygenated hydrocarbons comprise a major previously undescribed class of compounds on the Drosophila cuticular surface. A newly discovered long-chain acetate, CH503, serves as a mediator of courtship-related chemical communication.
在许多昆虫物种中,表皮碳氢化合物作为信息素,可以介导复杂的社会行为。在黑腹果蝇中,几种碳氢化合物,包括雄性感诱剂 11-顺式-十一烯基乙酸酯(cVA)和雌特异性 7,11-二烯,影响求偶行为,并可作为与交配经历相关的短期记忆的线索。行为和生理研究表明,可能存在其他未被识别的化学通讯线索。为了更全面地描述黑腹果蝇表皮的碳氢化合物图谱,我们应用直接紫外激光解吸/电离正交飞行时间质谱(UV-LDI-o-TOF MS),并以大约 200 µm 的空间分辨率分析完整果蝇的表面。
我们报告了 28 种表皮碳氢化合物的化学和空间特征,包括一类新的含氧化合物。通过 UV-LDI MS,先前显示仅由一种性别表达的信息素,例如 cVA、7,11-二十七碳二烯和 7,11-二十九碳二烯,似乎存在于雄性和雌性果蝇上。在雄性中,cVA 与另一种名为 CH503 的乙酰化碳氢化合物在射精球的尖端共定位。我们将 CH503 的化学结构描述为 3-O-乙酰基-1,3-二羟基-二十八碳-11,19-二烯,并证明该化合物作为雄蝇求偶的长寿命抑制剂具有行为作用。与 cVA 一样,CH503 在交配过程中从雄性转移到雌性。与 cVA 不同,CH503 在雌性表面至少保留 10 天。
含氧碳氢化合物构成了果蝇表皮表面以前未被描述的主要化合物类别。一种新发现的长链乙酸酯 CH503,作为与求偶相关的化学通讯的介质。