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Identification and Composition of Clasper Scent Gland Components of the Butterfly Heliconius erato and Its Relation to Mimicry.

Published version
Peer-reviewed

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Authors

Ehlers, Stephanie 
Szczerbowski, Daiane  ORCID logo  https://orcid.org/0000-0002-3733-2960
Harig, Tim 
Hötling, Susan 

Abstract

The butterfly Heliconius erato occurs in various mimetic morphs. The male clasper scent gland releases an anti-aphrodisiac pheromone and additionally contains a complex mixture of up to 350 components, varying between individuals. In 114 samples of five different mimicry groups and their hybrids 750 different compounds were detected by gas chromatography/mass spectrometry (GC/MS). Many unknown components occurred, which were identified using their mass spectra, gas chromatography/infrared spectroscopy (GC/IR)-analyses, derivatization, and synthesis. Key compounds proved to be various esters of 3-oxohexan-1-ol and (Z)-3-hexen-1-ol with (S)-2,3-dihydrofarnesoic acid, accompanied by a large variety of other esters with longer terpene acids, fatty acids, and various alcohols. In addition, linear terpenes with up to seven uniformly connected isoprene units occur, e. g. farnesylfarnesol. A large number of the compounds have not been reported before from nature. Discriminant analyses of principal components of the gland contents showed that the iridescent mimicry group differs strongly from the other, mostly also separated, mimicry groups. Comparison with data from other species indicated that Heliconius recruits different biosynthetic pathways in a species-specific manner for semiochemical formation.

Description

Keywords

GC/IR, biosynthesis, pheromones, terpenoids, volatile esters, Animals, Butterflies, Gas Chromatography-Mass Spectrometry, Pheromones, Scent Glands

Journal Title

Chembiochem

Conference Name

Journal ISSN

1439-4227
1439-7633

Volume Title

Publisher

Wiley
Sponsorship
Deutsche Forschungsgemeinschaft (Schu984/12-1)