Lepidoptera pyrrolizidine alkaloids

Pyrrolizidine alkaloids (PAs) such as senecionine (159) (Fig. 29) are also taken up from plants by various butterflies and moths belonging to the Danainae, Ithomiinae, and Arctiidae. The chemical ecology of PAs and their role in the interaction between plants and adapted Lepidoptera were reviewed several times in details during the last decade [155-159]. These insects use them for defense and for the production of male pheromones. 

Bentley, M. D., Leonard, D. E., Stoddard, W. F. and Zalkow, L. H. (1984). Pyrrolizidine alkaloids as larval feeding deterrents for spruce budworm, Choristoneura fumiferana (Lepidoptera Tortricidae). Annals of the Entomological Society of America 77 393-397. 

Lepidoptera and pyrrolizidine alkaloids exemplification of complexity in chemical ecology. Journal of Chemical Ecology 16 165-185. 

Boppre, M. and Schneider, D. (1985). Pyrrolizidine alkaloids quantitatively regulate both scent organ morphogenesis and pheromone biosynthesis in male Creatonotos moths (Lepidoptera Arctiidae). Journal of Comparative Physiology A 157 569-577. 

Pliske, T. E. (1975a). Attraction of Lepidoptera to plants containing pyrrolizidine alkaloids. Environmental Entomology 4 455-473. 

Pyrrolizidine alkaloids differential acquisition and use patterns in Apocynaceae and Solanaceae feeding ithomiine butterflies (Lepidoptera Nymphalidae). Biological Journal of the Linnaean Society 58 99-123. 

Orr A. B., Trigo J. R., Witte L. and Hartmann T. (1996) Sequestration of pyrrolizidine alkaloids by larvae of Tellervo zoilus (Lepidoptera Ithomiinae) and their role in the chemical protection of adult against the spider Nephila maculata (Araneidae). Chemoecol. 7, 68-73. 

Trigo J. R., Brown K. S., Jr, Witte L., Hartmann T., Ernst L. and Barata L. E. S. (1996) Pyrrolizidine alkaloids different acquisition and use patterns in Apocynaceae and Solanaceae feeding ithomiine butterflies (Lepidoptera Nymphalidae). Biol. J. Linnean... 

Trivers R. L. (1985) Social Evolution. Benjamin Cummings, Menlo Park, CA. von Nickisch-Rosenegk E. and Wink M. (1993) Sequestration of pyrrolizidine alkaloids in several arctiid moths (Lepidoptera Arctiidae). J. Chem. Ecol. 19, 1889-1903. Vasconcellos-Neto J. and Lewinsohn T. M. (1984) Discrimination and release of unpalatable butterflies by Nephila clavipes, a neotropical orb-weaving spider. Ecol. Entomol. 9, 337-344. 

IV). Delle piante zoidifile. Atti della Societa Italiana Sc. Nat. 16, 151-349. DeVries P. J. and Stiles F. G. (1990) Attraction of pyrrolizidine alkaloid seeking Lepidoptera to Epidendrum paniculatum orchids. Biotropica 22, 290-291. 

Pliske T. E. (1992) Pollination of pyrrolizidine alkaloid-containing plants by male Lepidoptera. Environ. Entomol. 4, 474-479. 

Species in a relatively small number of herbivorous families dominate the list of plant feeders associated with alkaloid-rich foods. Lepidoptera (butterflies and moths) have catholic tastes when it comes to alkaloid-fortified plants, being represented by the families Nymphalidae (calystegine A-3, pyrrolizidine alkaloids lycopsamine type, harman), Arctiidae (senecionine type), Papilionidae (synephrine, isoquinolines), and Pterophoridae (monoterpene alkaloid rhexifoline).6 In addition, beetles (Chrysomelidae) sequester PAs (senecionine), grasshoppers (Acrididae) store senecionine, and aphids (Aphididae) sequester QAs (sparteine and diterpene alkaloids). 

Insects have evolved mechanisms to tolerate plant toxins. Such mechanisms enable them to use a plant as a food source that is avoided by other herbivores, and provides the herbivore with its own ecological niche.9 For example, insects may prevent accumulation of detrimental alkaloids in the hemolymph by efficient excretion. Larvae of Spodoptera littoralis (Lepidoptera, Noctuidae) feed freely on plants containing pyrrolizidine alkaloids that are rapidly excreted and only transiently detectable in the hemolymph. Even pyrrolizidine alkaloids directly injected into the hemolymph are efficiently excreted.48 The same has been observed... 

An even higher level of specialization is realized by those insects that are attracted by alkaloid containing plants, not for feeding but to sequester them for defense purposes. Adults of some species of the Danaidae and Ihomiinae (butterflies, Lepidoptera) have evolved this special behavior and are attracted by pyrrolizidines and ingest them frequently from dead parts of pyrrolizidine alkaloid containing... 

HARTMANN, T., BILLER, A., WITTE, L., ERNST, L BOPPRE, M., Transformation of plant pyrrolizidine alkaloids into novel insect alkaloids by arctiid moths (Lepidoptera). Biochem. Syst. Ecol., 1990,18, 549-554. 

Wink, M. and von Nickisch-Rosenegk, E. (1997) Sequence data of mitochondrial 16S rDNA of Arctiidae and Nymphalidae (Lepidoptera) evidence for a convergent evolution of pyrrolizidine alkaloid and cardiac glycoside sequestration.. Chem. EcoL, 23, 1549-68. 

The occurrence of pyrrolizidine derivatives in the Lepidoptera is not confined to butterflies, but has also been observed in the tiger moth, where their function may be similar to that established in one species of butterfly. Male tiger moths (fam. Arctiidae) possess scent organs in the form of inflatable coremata which have a pheromone-distributing function. Some of these species are known to use plants containing pyrrolizidine alkaloids, e.g. Heliotropium europaeum and Echium... 

Pliske, T. Attraction of Lepidoptera to Plants Containing Pyrrolizidine Alkaloids. Environ. Entomol. 4, 455-473 (1975). 

A small example, similar to the conversion of pyrrolizidine alkaloids to male copulating pheromones by some Lepidoptera, is the conversion of flower compounds to attractants by males of the oriental fruit fly Bactrocera dorsalis. These adult males feed on the fragrant flowers of Fagraea berteriana which contain (if)-3,4-dimethoxycinnamyl alcohol and smaller amounts of ( )-3,4-dimethoxycinnamyl acetate (Figure... 

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