Semiochemicals derived from pyrrolizidine alkaloids in male ithomiine butterflies (Lepidoptera: Nymphalidae: Ithomiinae)

Schulz, Stefan; Beccaloni, George; Brown, Keith S.; Boppré, Michael; Freitas, André Victor Lucci; Ockenfels, Peter; Trigo, José Roberto

doi:10.1016/j.bse.2003.12.004

Cited by 53 publications

(87 citation statements)

References 27 publications

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“…For example, male Danaini (Nymphalidae: Danainae) have complex and often species‐specific abdominal hairpencil structures and aphrodisiac pheromones that are used during courtship (Boppré, 1984; Boppré & Vane‐Wright, 1989). Similarly, Ithomiini (Nymphalidae: Danainae) males sequester pyrrolizine alkaloids from plants and use them for defence and as precursors of pheromones (Brown, 1984; Schulz et al. , 2004).…”

Section: Discussionmentioning

confidence: 99%

Interspecific sexual attraction because of convergence in warning colouration: is there a conflict between natural and sexual selection in mimetic species?

Estrada

Jiggins

2008

J of Evolutionary Biology

112

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When species converge in their colour patterns because of mimicry, and those patterns are also used in mate recognition, there is a probability of conflicting selection pressures. Closely related species that mimic one another are particularly likely to face such confusion because of similarities in their courtship behaviour and ecology. We conducted experiments in greenhouse conditions to study interspecific attraction between two mimetic butterfly species, Heliconius erato and Heliconius melpomene. Both species spent considerable time approaching and courting females of the co‐mimic species. Experiments using wing models demonstrated the importance of colour pattern in this interspecific attraction. Although males of H. melpomene were attracted to their co‐mimics as much as to their own females, H. erato males were more efficient at distinguishing conspecifics, possibly using wing odours. Although preliminary, these results suggest that the use of additional cues may have evolved in H. erato to reduce the cost of convergence in visual signals with H. melpomene. Overall, our results showed that there might be a cost of mimetic convergence because of a reduction in the efficiency of species recognition. Such cost may contribute to explain the apparently stable diversity in Müllerian mimetic patterns in many tropical butterfly assemblages.

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Section: Discussionmentioning

confidence: 99%

Interspecific sexual attraction because of convergence in warning colouration: is there a conflict between natural and sexual selection in mimetic species?

Estrada

Jiggins

2008

J of Evolutionary Biology

112

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“…As previous Schulz et al (2004) found 6 compounds in male hairpencel components of 54 species in genera of Ithomiinae butterflies that have not been reported before from insects. In insects semiochmicals are either synthesized de novo or derived from dietary precursors utilized directly or altered minimally by insect enzymatic systems (Tillman et al, 1999).…”

Section: Chemicals Not Reported In Insectsmentioning

confidence: 57%

Age-related changes in the chemical composition of female pheromone gland of the Egyptian cotton leafworm, Spodoptera littoralis (Lepidoptera: Noctuidae)

El-Gashingy¹,

Naiem²,

Seada³

et al. 2018

Egypt. J. Exp. Biol. (Zoo.)

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Do h a H e s h a m E l -Ga s h i n g y El-S a e i d A h me d N a i e m M e r v a t Ra f e i k A b o u S e a d a A m a l I b r a h i m S e i fAge-related changes in the chemical composition of female pheromone glands of the Egyptian cotton leafw orm, Spodoptera littoralis (Lepidoptera: Noctuidae) ABSTRACT:The Egyptian cotton leafworm, Spodoptera littoralis (Lepidoptera: Noctuidae) is a serious pest that attacks a wide range of crops in Egypt. To relate the age with the chemical composition of the pheromone glands of the female S. littoralis, the chemical components of the glands were analyzed using gas chromatography coupled to mass spectrometry (GC -MS). The pheromone glands of the females were excised at four different ages: newly emerged (D 0 v), one-dayold (D1v), two-day-old (D2v), three-day-old (D3v) and three-day-old mated females (D3m). The pheromone glands contained 54 compounds in the hexane extract, (1 ketone, 1 acetate, 2 fatty acids, 3 esters, 6 aldehydes, 12 alcohols and 29 hydrocarbons). The presence and relative amounts of th ese compounds in the gland varied with age. Few compounds were observed in the glands of D0v, increased in D1v, D2v, and D3v, and remained almost constant in D 3 m. Fifteen compounds were previously identified as sex pheromone components in other Lepidoptera ; the major compounds were the two hydrocarbons, hentriacontane and heptacosane. Another fifteen components were previously identified from different insect orders other than Lepidoptera. The other twenty-four compounds were identified for the first time in insects. Determination and identification the sex pheromones of S. littoralis may present safe biologically active compounds that could be used in the management programs for this pest in Egypt. KEY WORDS:Spodoptera littoralis, Pheromone glands, Gas chromatography and Lepidoptera CORRESPONDENCE:Do h a H e s h a m E l -Ga s h i n g y Entomology Section, Zoology Department, Faculty of Science, Tanta University, Egypt INTRODUCTION:In the last four decades, there have been extensive researches on insect semiochemicals "The Pherobaseˮ (El-Sayed, 2014).They are chemical compounds implicated in the transfer of information from one individual to another to trigger a behavioral and physiological response in one or both insects (Dicke and Sabelis, 1988 and W olf, 1988; Ando et al., 2004). In Lepidoptera these compounds "The Pherobaseˮ (El-Sayed, 2014) play different roles.Virgin Lepidoptera females emit sex pheromones which cause attraction of males to the location of the female and subsequently, mating takes place (Kingan et al., 1993).In moths pheromone communication signals, both quantitative and qualitative intraspecific differences have been found across geographic regions (Klun, 1975;Roelofs et al., 1985). Such variation has generally been hypothesized to be due to selection and genetic control of these differences (Vogel et al., 2010). The composition of the female pheromone glands S. littoralis is highly dependent on the origin of the strain and its geographical distri...

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“…In danaine and ithomiine butterflies and arctiine moths, all dihydropyrrolizine male pheromones identified have 7R configuration. [6][7][8] As the clades danaine/ ithomiine and arctiine are not monophyletic, 36 the 7R trait may have evolved twice, independently. Trigo et al 35 suggested that ancestral PA-plants with 7R alkaloids may have molded this trait.…”

Section: Discussionmentioning

confidence: 99%

“…1,5 Arctiine moths and danaine and ithomiine butterflies also use PAs as precursors of male sexual pheromones, such as the dihydropyrrolizine hydroxydanaidal. [6][7][8] PAs were also recorded in the grasshopper Zonocerus variegatus, the aphid Aphis jacobaeae, the bug Largus rufipennis, and the coccide Ceroplastes albolineatus. 1 PA-containing insects are generally aposematic, i.e., their unpalatability is associated with warning signals alerting predators of this trait; warning signals can be visual, sonorous, or odorant.…”

Section: Introductionmentioning

confidence: 99%

“…Stereochemical inversion must take place in Arctiini, since a general feature of male sexual pheromones seems to be the 7R configuration. [6][7][8][16][17][18][19] Although Arctiini comprises around 11,000 species, only a small fraction was studied regarding PAs. 16,22 For instance, in Pericopina, a single species, Hyalurga syma, was studied in relation to PA profile and chemical defense.…”

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confidence: 99%

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Pyrrolizidine Alkaloids in the Pericopine MothScearctia figulina(Erebidae: Arctiinae): Metabolism and Chemical Defense

Martins

Trigo

2016

Journal of the Brazilian Chemical Society

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Pyrrolizidine alkaloids (PAs) are defensive compounds present in several plant families. However, some specialist herbivore insects have overcome these toxic compounds and sequester PAs converted to N-oxide as a defense against predators and a precursor of male sexual pheromones. In this context, we investigated PA sequestration by the specialist pericopine moth Scearctia figulina (Erebidae: Arctiinae), which feeds on leaves of Heliotropium transalpinum (Boraginaceae) as larvae. Additionally, we examined the role of PAs against different predators. The PAs sequestered from the host plant were metabolized by larvae and transferred to adults via two main pathways: (i) rinderine and its acetyl derivative (7S,3'R) were epimerized to intermedine (7R,3'R) and lycopsamine (7R,3'S), and (ii) insect PAs were biosynthesized from necine bases obtained from plant-acquired PAs, with necic acids of insect origin. Both metabolic products may be related to the biosynthesis of 7R male pheromone and to chemical defense. Larvae and adults were chemically protected against the spiders Nephila clavipes and Lycosa erythrognatha and the chick Gallus gallus, and this defense may be associated to PAs. Keywords: callimorphine, Heliotropium transalpinum, insect PAs, lycopsamine, predation IntroductionPyrrolizidine alkaloids, particularly 1,2-dehydropyrrolizidines (hereafter PAs), are powerful defensive compounds in several plant taxa, such as Eupatorieae and Senecioneae (Asteraceae), Boraginaceae, and Crotalarieae (Leguminosae).1,2 However, specialized herbivores, such as arctiine moths, danaine and ithomiine butterflies and chrysomeline beetles, among others, are able to cope with pro-toxic free-base PAs from these plants, converting them into non-toxic N-oxides.3,4 These insects sequester PA N-oxides, incorporating them into their tissues, and this renders chemical protection against predators and parasitoids.1,5 Arctiine moths and danaine and ithomiine butterflies also use PAs as precursors of male sexual pheromones, such as the dihydropyrrolizine hydroxydanaidal.6-8 PAs were also recorded in the grasshopper Zonocerus variegatus, the aphid Aphis jacobaeae, the bug Largus rufipennis, and the coccide Ceroplastes albolineatus.1 PA-containing insects are generally aposematic, i.e., their unpalatability is associated with warning signals alerting predators of this trait; warning signals can be visual, sonorous, or odorant. 9Among arctiine moths, 10 PAs were found in the tribes Amerilini and Arctiini (subtribes Callimorphina, Arctiina, Pericopina, Ctenuchina, Euchromiina, and Phaegopterina), but not in Lithosiini and Syntomini. 11 Three PA acquisition strategies were found in these moths: (i) PA-obtained as adults, (ii) PA-specialist feeding as larvae, and (iii) PA-generalist feeding as larvae.11 In the first syndrome, adults either feeding on nectar containing PAs or display a pharmacophagous behavior, or obtaining the alkaloid visiting withered PA-containing plants. 2,12,13 This syndrome was widely found in Ctenuchina, Euchromiina, an...

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Semiochemicals derived from pyrrolizidine alkaloids in male ithomiine butterflies (Lepidoptera: Nymphalidae: Ithomiinae)

Cited by 53 publications

References 27 publications

Interspecific sexual attraction because of convergence in warning colouration: is there a conflict between natural and sexual selection in mimetic species?

Interspecific sexual attraction because of convergence in warning colouration: is there a conflict between natural and sexual selection in mimetic species?

Age-related changes in the chemical composition of female pheromone gland of the Egyptian cotton leafworm, Spodoptera littoralis (Lepidoptera: Noctuidae)

Pyrrolizidine Alkaloids in the Pericopine MothScearctia figulina(Erebidae: Arctiinae): Metabolism and Chemical Defense

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