The scent chemistry of butterflies

Ehlers, Stephanie; Schulz, Stefan

doi:10.1039/d2np00067a

Cited by 5 publications

(7 citation statements)

References 239 publications

(618 reference statements)

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“…Previous results suggest that most CSG compounds are indeed biosynthesised de novo. [20,48,55] The current analyses and previous work [9,15,20,23] indicate that some compounds or groups are particularly important, in addition to those with proven function (1)(2)(3)(4)(5). These include (E)-β-ocimene (1), (E,E)-α-farnesene and the corresponding epoxidation products, several short alkan-3ones/alk-1-en-3-ones, β-ionone and its dihydro derivative 4, 4hydroxy-isophorone (23), benzyl salicylate (5), [23] as well as several short chain esters (Table 2).…”

Section: Compounds Of the Csgsmentioning

confidence: 80%

“…The M + ‐ions at m/z 254 for A and 280/282 for B/B’ , indicated that these compounds were butyl, hexenyl and hexyl dodecenoates, respectively, with an uncertain double bond position. The leaf alcohol ( Z )‐3‐hexenol is a common plant constituent formed by lipid degradation, e. g. induced by insect feeding, and has previously been reported in many Heliconius esters [9,19,23] . To determine the double bond position, dimethyl disulfide derivatisation of the CSG extract was performed, yielding a major derivative with a main fragment ion at m/z 173 (SI, Figure S8), indicating a likely double bond at C‐3 of the acid moiety.…”

Section: Resultsmentioning

confidence: 99%

“…The leaf alcohol (Z)-3-hexenol is a common plant constituent formed by lipid degradation, e. g. induced by insect feeding, and has previously been reported in many Heliconius esters. [9,19,23] To determine the double bond position, dimethyl disulfide derivatisation of the CSG extract was performed, yielding a major derivative with a main fragment ion at m/z 173 (SI, Figure S8), indicating a likely double bond at C-3 of the acid moiety. The IR spectrum of A (SI, Figure S16) showed characteristic bands for a disubstituted (Z)double bond at 3025 and 1693/1663 cm À 1 .…”

Section: Dennis-ray Mimicry Groupmentioning

confidence: 99%

“…[6] In this context, mimetic convergence between co-occurring species, especially closely related species in the same mimicry ring, may cause courtship problems. [6,7] In contrast to moths, visual communication appears to be predominant in butterflies, but many species also use volatile or lipophilic compounds to convey information, [8,9] including Heliconius, where other signals such as pheromones are likely to mediate short-distance recognition and mating, [10][11][12][13] particularly in co-mimics where visual cues alone are not sufficient to identify conspecifics. [12,14,15] Heliconius butterflies can be divided into two clades with different mating behaviour.…”

Section: Introductionmentioning

confidence: 99%

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Variation of Clasper Scent Gland Composition of Heliconius Butterflies from a Biodiversity Hotspot

Ehlers,

Blow,

Szczerbowski

et al. 2023

ChemBioChem

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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 more than 500 compounds showed differentiation by phylogenetic clade and species, but not by mimicry group.

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Section: Compounds Of the Csgsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Section: Dennis-ray Mimicry Groupmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Variation of Clasper Scent Gland Composition of Heliconius Butterflies from a Biodiversity Hotspot

Ehlers,

Blow,

Szczerbowski

et al. 2023

ChemBioChem

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“…In addition, we incorporated all compounds that were consistently found within a species, including non-pyrrolizidine alkaloid derived compounds. Ithomiini male androconial extracts are dominated by pyrrolizidine alkaloid derivatives, and these are presumed to be the main signalling media (Ehlers & Schulz, 2022; Eisner & Meinwald, 1987; Stefan Schulz et al, 2004). However, recent studies have also found non-pyrrolizidine alkaloid related compounds in the androconial extracts of certain Ithomiini species (Mann et al, 2020; Stamm et al, 2019).…”

Section: Discussionmentioning

confidence: 99%

Phylogeny not mimicry drives chemical variation in tropical aposematic butterflies

Blow,

Ehlers,

Warren

et al. 2023

Preprint

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Chemical signals serve a vast array of functions for both intra- and interspecific communication and defence. Chemically defended, aposematic insects will advertise their noxiousness to predators with warning signals and it has been suggested that volatile compounds shared between species could send a common signal to deter avian predators, similar to colour pattern mimicry. This is exemplified in the bright, mimetic warning colours of toxic heliconiine and ithomiine butterflies. Besides defence, males in these groups also use chemicals to communicate with potential female mates and male competitors. Here, we characterise chemical profiles of male Heliconiini and Ithomiini species from a range of mimicry rings. We find that chemical distances between species are not associated with mimicry and instead show a strong phylogenetic signal. In addition, we show that the distribution of specific shared compounds does not correlate with mimicry. We propose chemical signals in these groups are primarily used for intraspecific communication and highlight the potential selective mechanisms driving chemical profile evolution, such as selection for species-specific pheromone concentrations and collective male deterrent compounds. Our findings imply that chemical profile variation among butterfly species is the product of shared ancestry. However, more research is required on the behavioural significance of compounds among butterflies and predator perception of olfactory warning signals to identify which selective pressures are exerted on specific chemical traits.

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Sexual behavior and chemical signaling in Opsiphanes cassina (Lepidoptera: Nymphalidae)

Bustos-Cortés,

Aldana-De la Torre,

Morales-Rodríguez

et al. 2023

Chemoecology

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Behavior modification using chemical stimuli is a promising tactic for integrated management of lepidopteran pests. Therefore, this approach was evaluated for the management of the butterfly Opsiphanes cassina Felder 1862, a defoliating pest in oil palm plantations. To achieve this aim, we observed adults’ sexual behavior under laboratory conditions and identified glandular structures in the abdomen and hind wings of males that are associated with the production of sexual pheromones in taxonomically related insects. It was also determined that male calls to females occur at 18:00 h when they fill their glandular structures, tremble, and make abdominal movements while possibly releasing pheromones. The hairpencils of the hind wings are also exposed during this time. Furthermore, the analysis using Gas Chromatography-Mass Spectrometry (GC–MS) on the samples obtained by Solvent Assisted Extraction (SAE) revealed the identification of three male-specific volatile organic compounds (VOCs), including (E)-nerolidol, vanillin, and (Z)-7-heptadecene. The Electroantennographic (EAG) evaluation demonstrated that females respond to the compounds, indicating their likely involvement in intraspecific interactions of the species. However, the behavioral evaluation did not confirm their attractive effect under the conditions employed. Nevertheless, the identified male-specific semiochemicals could be an alternative for inclusion in integrated pest management (IPM) of this pest in oil palm crops. Therefore, it is recommended to evaluate them under field conditions.

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The scent chemistry of butterflies

Abstract: Butterflies use structurally highly diverse volatile compounds for communication, in addition to visual signals. These compounds originate from plants or a formed de novo especially by male butterflies that possess specific scent organs.

Cited by 5 publications

References 239 publications

Variation of Clasper Scent Gland Composition of Heliconius Butterflies from a Biodiversity Hotspot

Variation of Clasper Scent Gland Composition of Heliconius Butterflies from a Biodiversity Hotspot

Phylogeny not mimicry drives chemical variation in tropical aposematic butterflies

Sexual behavior and chemical signaling in Opsiphanes cassina (Lepidoptera: Nymphalidae)

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