Insect-Plant Interactions − Metabolism of Plant Compounds to Pheromones and Allomones by Lepidoptera and Leaf Beetles

Schulz, Stefan

doi:10.1002/(sici)1099-0690(199801)1998:1<13::aid-ejoc13>3.0.co;2-r

Cited by 65 publications

(41 citation statements)

References 75 publications

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“…Many reviews on the activity of pyrrolizidine alkaloids in chemical defense and the role of these alkaloids in pheromone biosynthesis in Lepidoptera are available 21,22,[57][58][59][60][61][62] . Pyrrolizidine alkaloids are a diverse class of natural compounds based on a [3.3.0] azabicyclo ring, generally occurring as esters of a "necine base" with "necic acids" as mono-or diesters (Figure 3, 10-13) 63 .…”

Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%

The chemistry of antipredator defense by secondary compounds in neotropical lepidoptera: facts, perspectives and caveats

Trigo

2000

J. Braz. Chem. Soc.

102

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Defesas químicas em lepidópteros contra predadores têm sido observadas desde o século XIX. O caso clássico de proteção química contra predadores é o da borboleta monarca, Danaus plexippus, cuja larva seqüestra cardenolidas de sua planta hospedeira Asclepias curassavica e transfere-as para os adultos tornando-os impalatáveis para pássaros. Entretanto diversas outras substâncias podem estar envolvidas na proteção química de lepidópteros neotropicais (glicosídeos iridóides, glicosídeos cianogênicos, glicosinolatos, alcalóides pirrolizidínicos e tropânicos, ácidos aristolóquicos, inibidores de glicosidase, pirazinas). Esses compostos podem ser seqüestrados da planta hospedeira larval, obtidos de fontes vegetais visitadas por adultos ou biossintetizados de novo. Os lepidópteros conhecidos como impalatáveis para predadores vertebrados e/ou invertebrados são as borboletas Troidini (Papilionidae), Pierinae (Pieridae), Eurytelinae, Melitaeinae, Danainae, Ithomiinae, Heliconiinae e Acraeinae (Nymphalidae) e mariposas Arctiidae. Entretanto informações sobre as substâncias que são responsáveis pela impalatabilidade e como elas são adquiridas nem sempre são obtidas. Esse artigo de revisão aborda principalmente observações de campo e laboratório sobre a rejeição de borboletas e mariposas neotropicais por predadores, correlações entre impalatabilidade e substâncias químicas encontradas nos insetos e bioensaios que demonstrem a atividade dessas substâncias contra predadores. Perspectivas são sugeridas para esses tópicos.Chemical defense against predation in butterflies and moths has been studied since nineteenth century. A classical example is that of the larvae of the monarch butterfly Danaus plexippus, which feed on leaves of Asclepias curassavica (Asclepiadaceae), sequestering cardenolides. The adults are protected against predation by birds. Several other substances may be involved in chemical defense, such as iridoid glycosides, cyanogenic glycosides, glucosinolates, pyrrolizidine and tropane alkaloids, aristolochic acids, glycosidase inhibitors and pyrazines. The acquisition of these substances by lepidopterans can be due to sequestration from larval or adult host plants or de novo biosynthesis. Many Lepidoptera are known to be unpalatable, including the butterflies Troidini (Papilionidae), Pierinae (Pieridae), Eurytelinae, Melitaeinae, Danainae, Ithomiinae, Heliconiinae and Acraeinae (Nymphalidae), and Arctiidae moths, but knowledge of the chemical substances responsible for property is often scarce. This review discusses mainly three topics: field and laboratory observations on rejection of butterflies and moths by predators, correlation between unpalatability and chemicals found in these insects, and bioassays that test the activity of these chemicals against predators. Perspectives and future directions are suggested for this subject.

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Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%

The chemistry of antipredator defense by secondary compounds in neotropical lepidoptera: facts, perspectives and caveats

Trigo

2000

J. Braz. Chem. Soc.

102

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“…Foraging caterpillars, for example, respond to host plant pyrrolizidine alkaloids as contact chemical cues and feeding stimulants (Bernays et al, 2000;Bernays et al, 2002). Once consumed, however, the alkaloids are sequestered by caterpillars in their own defense (Hartmann and Witte, 1995;Schulz, 1998;Nishida, 2002). Later in life, they are used by post-metamorphic adult female moths as precursors for the synthesis of mate attractants (Bell and Meinwald, 1986;Schulz et al, 1993).…”

Section: Introductionmentioning

confidence: 99%

The scent of danger: arginine as an olfactory cue of reduced predation risk

Ferrer

Zimmer

2007

Journal of Experimental Biology

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SUMMARY Animal perception of chemosensory cues is a function of ecological context. Larvae of the California newt (Taricha torosa), for example, exhibit predator-avoidance behavior in response to a chemical from cannibalistic adults. The poison tetrodotoxin (TTX), well known as an adult chemical defense, stimulates larval escape to refuges. Although they are cannibals,adult newts feed preferentially on worms (Eisenia rosea) over conspecific young. Hence, larval avoidance reactions to TTX are suppressed in the presence of odor from these alternative prey. The free amino acid,arginine, is abundant in fluids emitted by injured worms. Here, we demonstrate that arginine is a natural suppressant of TTX-stimulated larval escape behavior. Compared to a tapwater control, larvae initiated vigorous swimming in response to 10–7 mol l–1 TTX. This excitatory response was eliminated when larval nasal cavities were blocked with an inert gel, but not when gel was placed on the forehead (control). In additional trials, a binary mixture of arginine and 10–7 mol l–1 TTX failed to induce larval swimming. The inhibitory effect of arginine was, however, dose dependent. An arginine concentration as low as 0.3-times that of TTX was significantly suppressant. Further analysis showed that suppression by arginine of TTX-stimulated behavior was eliminated by altering the positively-charged guanidinium moiety, but not by modifying the carbon chain, carboxyl group, or amine group. These results are best explained by a mechanism of competitive inhibition between arginine and TTX for common, olfactory receptor binding sites. Although arginine alone has no impact on larval behavior, it nevertheless signals active adult predation on alternative prey, and hence, reduced cannibalism risk.

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“…The females receive PAs from males during copulation and transmit them together with their own load to the eggs (Dussourd et al 1988(Dussourd et al , 1991. Most likely the same courtship behavior exists in ithomiines, which are also known to synthesize PAderived male pheromones (Schulz 1998). C]senecionine; composition (relative abundance, %) of the recovered radioactivity.…”

Section: Discussionmentioning

confidence: 99%

“…These pheromones are derived from the two building blocks of PAs of the lycopsamine type. The necine base is the precursor of hydroxydanaidal and the unique necic acid provides the carbon skeleton for the ithomiine k-lactone (Edgar et al 1976;Boppré 1990;Schulz 1998). It seems possible that the k-lactone or similar structures, although not known from plants (Schulz 1998), are formed in decaying plant materials as a specific bait for ithomiines.…”

Section: Discussionmentioning

confidence: 99%

Storage and metabolism of radioactively labeled pyrrolizidine alkaloids by butterflies and larvae of Mechanitis polymnia (Lepidoptera: Nymphalidae, Ithomiinae)

Brückmann¹,

Trigo²,

Foglio

et al. 2000

Chemoecology

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Tracer feeding studies with radioactively labeled pyrrolizidine alkaloids (PAs) were performed to attain experimental information about the specificity and mechanisms of uptake, metabolism and storage of PAs in the alkaloid sequestering ithomiine butterfly Mechanitis polymnia. Adult butterflies easily ingest the tracers offered dissolved in a saturated sugar solution. Feeding of [ 14 C]rinderine (free base) confirmed that M. polymnia is well adapted to sequester and maintain PAs of the lycopsamine type. Approximately 80% of the ingested radioactivity can be recovered in methanol extracts of the butterflies over a period of at least 6 hours. Labeled rinderine is efficiently N-oxidized and transformed into a metabolite of still unknown structure. These two metabolites are formed in almost equal amounts and account for more than 90% of total radioactivity. After four hours the toxic free base is only detectable in traces. Radioactively labeled senecioylretronecine (free base), a PA that often accompanies PAs of the lycopsamine type in plants, is metabolized in a different manner. The toxic free base disappeared as fast as the tertiary rinderine, but the final products which accumulated in a stable ratio after 12 hours were mainly two polar metabolites of unknown structure; senecioylretronecine N-oxide accounts for less than 10% of total PAs. Labeled senecionine a macrocyclic PA, which never has been found in wild caught M. polymnia is only slowly N-oxidized. In females ca 50% of the ingested senecionine is still present as free base after 24 hours, whereas under the same conditions in males this percentage is only ca 20%. This difference in N-oxidation was the only significant sex-specific difference observed in various experiments. Larvae of M. polymnia which feed on Solanum tabacifolium, a plant that does not contain PAs, are able to sequester and partly N-oxidize labeled senecioylretronecine and senecionine. However, the storage is not very efficient; with the two tracers less than 5% of radioactivity remained in the bodies after 24 hours.

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Insect-Plant Interactions − Metabolism of Plant Compounds to Pheromones and Allomones by Lepidoptera and Leaf Beetles

Cited by 65 publications

References 75 publications

The chemistry of antipredator defense by secondary compounds in neotropical lepidoptera: facts, perspectives and caveats

The chemistry of antipredator defense by secondary compounds in neotropical lepidoptera: facts, perspectives and caveats

The scent of danger: arginine as an olfactory cue of reduced predation risk

Storage and metabolism of radioactively labeled pyrrolizidine alkaloids by butterflies and larvae of Mechanitis polymnia (Lepidoptera: Nymphalidae, Ithomiinae)

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