Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
Department of Zoology, University of Cambridge, Cambridge, United Kingdom.
Chembiochem. 2023 Nov 16;24(22):e202300537. doi: 10.1002/cbic.202300537. Epub 2023 Sep 27.
Male Heliconius butterflies possess two pheromone emitting structures, wing androconia and abdominal clasper scent glands. The composition of the clasper scent gland of males of 17 Heliconius and Eueides species from an overlapping area in Ecuador, comprising three mimicry groups, was investigated by GC/MS. The chemical signal serves as an anti-aphrodisiac signal that is transferred from males to females during mating, indicating the mating status of the female to prevent them from harassment by other males. In addition, the odour may also serve in predator defence. There is potential for convergence driven by mimicry, although, such convergence might be detrimental for species recognition of the butterflies within the mimicry ring, making mating more difficult. More than 500 compounds were detected, consisting of volatile, semi-volatile or non-volatile compounds, including terpenes, fatty acid esters or aromatic compounds. Several novel esters were identified by GC/MS and GC/IR data, microderivatisation and synthesis, including butyl (Z)-3-dodecenoate and other (Z)-3-alkenoates, 3-oxohexyl citronellate and 5-methylhexa-3,5-dienyl (E)-2,3-dihydrofarnesoate. The secretions were found to be species specific, potentially allowing for species differentiation. Statistical analysis of the compounds showed differentiation by phylogenetic clade and species, but not by mimicry group.
雄凤蝶拥有两种信息素分泌结构,即翅膀的性标和腹部的抱握腺 scent glands。本研究采用 GC/MS 对来自厄瓜多尔重叠区域的 17 种凤蝶属和 Eueides 属的 17 种雄性凤蝶的抱握腺 scent glands 的化学成分进行了分析。该化学信号作为一种抗性欲信息素,在交配过程中从雄性传递给雌性,表明了雌性的交配状态,以防止它们受到其他雄性的骚扰。此外,这种气味可能也有助于防御捕食者。尽管存在因模拟而导致的趋同进化的可能性,但这种趋同进化可能会对模拟环内蝴蝶的物种识别造成不利影响,使交配更加困难。检测到超过 500 种化合物,包括挥发性、半挥发性或非挥发性化合物,如萜烯、脂肪酸酯或芳香族化合物。通过 GC/MS 和 GC/IR 数据、微量衍生化和合成,鉴定出几种新型酯,包括丁酸(Z)-3-十二烯酯和其他(Z)-3-链烯酸酯、3-氧代己基香茅酯和 5-甲基-3,5-二烯基(E)-2,3-二氢法呢酯。这些分泌物具有物种特异性,可能允许物种分化。化合物的统计分析显示,化合物的分化与系统发育分支和物种有关,而与模拟群无关。