Head and Tail Oxidized Terpenoid Esters from Androconia of Heliconius erato Butterflies,Journal of Natural Products

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Head and Tail Oxidized Terpenoid Esters from Androconia of Heliconius erato Butterflies
Journal of Natural Products ( IF 3.3 ) Pub Date : 2022-05-19 , DOI: 10.1021/acs.jnatprod.2c00300
Daiane Szczerbowski ₁ , Stephanie Ehlers ₁ , Kathy Darragh ₂ , Chris Jiggins ₃ , Stefan Schulz ₁

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Heliconius erato is a neotropical butterfly species that is part of a complex mimicry ring, with colorful wing patterns. For intraspecific communication, males use pheromones that are released from two different scent-emitting structures. Scent glands located near the abdominal claspers of males, containing antiaphrodisiac pheromones, release a highly complex mixture of compounds that is transferred to females during mating, rendering them unattractive to other males. On the other hand, androconia, scent-emitting scale areas on the wings of male butterflies, release a structurally more restricted set of compounds that likely serves an aphrodisiac role. We report here on two structurally related compounds that are the major androconial constituents, produced in high amounts and are not volatile due to their high molecular mass. Their structures were established by extensive analysis of mass, infrared, and NMR spectra, as well as microderivatization reactions of the natural extract. After establishing synthetic access, the compounds were unequivocally identified as two unusual head and tail oxidized terpenoids, (4E,8E,12E)-4,8,12-trimethyl-16-oxoheptadeca-4,8,12-trien-1-yl oleate (1) and stearate (2). Although behavioral assays are necessary to fully comprehend their role in the chemical communication of the species, hypotheses for their use by the butterflies are also discussed.

中文翻译：

Heliconius erato 蝴蝶 Androconia 的头尾氧化萜类酯

蜗牛是一种新热带蝴蝶物种，是一个复杂的拟态环的一部分，具有五颜六色的翅膀图案。对于种内交流，雄性使用从两种不同的气味发射结构释放的信息素。位于雄性腹部扣环附近的气味腺含有抗春药信息素，会释放出一种高度复杂的化合物混合物，在交配过程中会转移到雌性身上，使它们对其他雄性没有吸引力。另一方面，雄性蝴蝶翅膀上散发气味的鳞片区域雄蕊花会释放出一组结构上更受限制的化合物，这些化合物可能起到壮阳作用。我们在此报告了两种结构相关的化合物，它们是主要的雄性成分，大量生产并且由于它们的高分子量而不易挥发。它们的结构是通过对质量、红外和 NMR 光谱以及天然提取物的微衍生化反应的广泛分析确定的。在建立合成途径后，这些化合物被明确鉴定为两种不寻常的头尾氧化萜类化合物（4E ,8 E ,12 E )-4,8,12-trimethyl-16-oxoheptadeca-4,8,12-trien-1-yl oleate ( 1 ) 和硬脂酸酯 ( 2 )。虽然行为分析对于充分理解它们在物种化学通讯中的作用是必要的，但也讨论了蝴蝶使用它们的假设。

更新日期：2022-05-19

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