Antiaphrodisiacs in Pierid Butterflies: A Theme with Variation!
Department of Chemistry, Organic Chemistry, Group of Ecological Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden. Journal of Chemical Ecology
(Impact Factor: 2.75).
07/2003; 29(6):1489-99. DOI: 10.1023/A:1024277823101
Male Pieris napi butterflies previously have been shown to synthesize and transfer an antiaphrodisiac, methyl salicylate (MeS), to females at mating. This substance curtails courtship and decreases the likelihood of female remating. Here, we show that similar systems occur in Pieris rapae and Pieris brassicae. In P. rapae, 13C-labeling studies showed that males utilize the amino acids phenylalanine and tryptophan as precursors to MeS and indole, respectively. These volatiles are transferred to females at mating and function as antiaphrodisiacs, as demonstrated by field tests entailing painting MeS, indole, or a mixture on the abdomens of virgin females and assessing their attractiveness to wild males. With P. brassicae, 13C-labeling studies showed that males use phenylalanine as a precursor to synthesize benzyl cyanide, which was demonstrated to function as an antiaphrodisiac by field tests similar to those for P. rapae. This communication system exhibits both similarities and differences among the three species; in P. napi and P. rapae, males are fragrant but transfer a volatile antiaphrodisiac to females that is completely different from the male odor, whereas in P. brassicae the antiaphrodisiac transferred by male to female is identical with male odor.
Available from: Natasha Tigreros
- "We controlled for any possible interference of the NaOH treatment with male-female chemical communication by only using virgin females, who lack the male-transferred pheromone. Additionally, treatment with NaOH would be unlikely to mimic P. rapae antiaphrodisiac pheromone, which is a methyl salicylate and indole solution (Andersson et al. 2003). As expected, spectra from pteridine-extracted females presented higher UV and lower long-wave reflectance than those from control females (Fig. 1). "
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ABSTRACT: While the phenomenon of male mate choice has attracted considerable attention in the last two decades, whether this sexual selection mechanism could drive the evolution of female ornaments remains poorly understood. Here, we used experimental manipulation of female wing coloration to investigate male mate choice in Pieris rapae, a gift-giving butterfly. Further, we tested whether males’ nutritional status influenced their mating preferences by subjecting larvae to short periods of starvation. We found that males showed significantly more mating approaches toward control females with more colorful wings (higher pteridine content), and that this preference was strongest in low-nutrition males. Additionally, a study of field-collected females revealed that pteridine-based wing coloration was positively correlated with female egg load, which suggests such ornaments may signal female quality. Pteridine-based ornaments are widespread in nature, however their potential as honest signals in male mate choice remains largely unexplored. This work furthers our understanding of how male mate choice and female ornamentation may evolve in species whose mating systems include nutritional nuptial gifts.
09/2014; 68(9). DOI:10.1007/s00265-014-1764-1
Available from: Oskar Brattström
- "napi (Andersson et al. 2007; Bergström and Lundgren 1973), P. rapae and P. brassicae (Andersson et al. 2003; Yildizhan et al. 2009) from the subfamily Pierinae. In contrast to moths that generally use de novo synthesised compounds to produce volatile signals, butterflies often utilize chemical substances acquired from plants in scent production (Boppré 1984; Schulz et al. 2004). "
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ABSTRACT: Representatives of the highly speciose tropical butterfly genus Bicyclus (Lepidoptera: Nymphalidae) are characterized by morphological differences in the male androconia, a set of scales and hair pencils located on the surface of the wings. These androconia are assumed to be associated with the release of courtship pheromones. In the present study, we report the identification and biosynthetic pathways of several novel esters from the wings of male B. martius sanaos. We found that the volatile compounds in this male butterfly were similar to female-produced moth sex pheromones. Components associated with the male wing androconial areas were identified as ethyl, isobutyl and 2-phenylethyl hexadecanoates and (11Z)-11-hexadecenoates, among which the latter are novel natural products. By topical application of deuterium-labelled fatty acid and amino acid precursors, we found these pheromone candidates to be produced in patches located on the forewings of the males. Deuterium labels from hexadecanoic acid were incorporated into (11Z)-11-hexadecenoic acid, providing experimental evidence of a Δ11-desaturase being active in butterflies. This unusual desaturase was found previously to be involved in the biosynthesis of female-produced sex pheromones of moths. In the male butterflies, both hexadecanoic acid and (11Z)-11-hexadecenoic acid were then enzymatically esterified to form the ethyl, isobutyl and 2-phenylethyl esters, incorporating ethanol, isobutanol, and 2-phenylethanol, derived from the corresponding amino acids L-alanine, L-valine, and L-phenylalanine.
Electronic supplementary material
The online version of this article (doi:10.1007/s10886-014-0452-y) contains supplementary material, which is available to authorized users.
06/2014; 40(6). DOI:10.1007/s10886-014-0452-y
Available from: Roger Vila
- "Gas chromatography–mass spectrometry (GC-MS) analyses A solid-phase microextraction (SPME) method using polydimethylsiloxane-divinylbenzene fibers (PDMS/DVB, 65 μm×2 cm) was coupled to a gas chromatograph-mass spectrometer (GC-MS) in order to sample the volatile components from the scent organs, following a procedure very similar to that described by Andersson et al. (2003). Vials containing the samples and the PDMS/DVB fibres were equilibrated at 60 °C for 30 min in order to adsorb the volatile components from the samples to the fibres and afterwards the volatile components were desorbed by heating the vials at 250 °C for 5 min in the GC injector with a 1 ml/min He gas flow. "
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ABSTRACT: Chemical communication in the family
Hesperiidae (Lepidoptera) is practically unstudied, even
though this group includes approximately 4,000 species and
represents a fifth of the world’s butterfly fauna.We present the
first comparative morphological and chemical analysis of
scent organs for nine species in the genus Pyrgus, the most
species-rich hesperiid genus in the Palearctic region. Our
results show that the morphology of the two main male scent
organs—the costal fold and the tibial tufts—does not differ
between species. The chemical analyses detected a total of
125 different compounds exclusively present in these organs.
We document great interspecific differences and much
narrower intraspecific variability in the chemical profiles.
The dynamics of chemical versus genetic distances indicate
two different phases: a faster (but more variable) initial chemical
divergence at lower genetic divergences (probably related
to speciation) and a slower but more constant differentiation
(drift). As a result most species can be identified based on their
chemical profiles, except for a closely related species pair
(P. malvae/P. malvoides) for which hybridisation is common
in the contact zone. Our results suggest that the Hesperiidae is
a group with great potential for the study of chemical communication
that deserves further attention.
03/2014; 14(3). DOI:10.1007/s13127-014-0170-x
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