Tyria jacobaeae, pyrrolizidine alkaloids

Macel G L, Klinkhamer P, Vrieling K and van der Meijden E (2002), Diversity of pyrrolizidine alkaloids in Senecio species does not affect the specialist herbivore Tyria jacobaeae , Oecologia, 133, 541-550. 

Ehmke, A., Witte, L., Biller, A. and Hartmann, T. (1990). Sequestration, A-oxidation, and transformation of plant pyrrolizidine alkaloids by the arctiid moth Tyria jacobaeae... 

Vrieling, K., Smit, W. and Van der Meijden, E. 1991. Three-trophic interactions with pyrrolizidine alkaloids lead to general variation in PA concentrations between aphid species (Aphis jacobaea) and Tyria jacobaeae. Oecologia 86, 177-182... 

The presence of pyrrolizidine alkaloids in arctiid moths that had been reared on Senecio and Crotalaria species has been established by Rothschild et al.4S These alkaloids are stored in the moths, and serve as a deterrent to vertebrate predators and as precursors for insect sex pheromones. A pyrrolizidine alkaloid metabolite from the Cinnabar moth (Tyria jacobaea L.), named callimorphine, has been shown to have the structure (49) on the basis of mass-spectral and degradative evidence.46 The structure (49) was confirmed by synthesis of callimorphine and a diastereo-isomer by treatment of 9-chlororetronecine with the sodium salt of ( )-2-acetoxy-2-methylbutanoic acid. 

NAUMANN, C., HARTMANN, T., OBER, D., Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae. Proc. Natl. Acad. Sci. U. S. A., 2002,99, 6085-6090. 

Figure 1 Oviposition stimulants for Idea leuconoe (danaine butterfly upper) and Tyria jacobaeae (arctiid moth lower) feeding on pyrrolizidine alkaloid-containing plants.

The best-studied group of acquired alkaloids are the pyrrolizidines, which are produced by plants, especially in the families Asteraceae and Boraginaceae (502). Some arctiid larvae of Tyria Jacobaea, Cycnia men-dica, Amphicallia bellafrix, Arginia cribaria, and Arctia caja were shown... 

Analyses of the cinnibar moth, Tyria jacobaeae, revealed an interesting example for sequestration of defensive terpenoids. As with many other moths found within the family Actiidae, larvae of this species are able to sequester pyrrolizidine alkaloids (also see Section 2.04.6.4) from their plant host, in this case species from the genus Senecio. A population of T. jacobaeae was recendy identified, however, which lives on plants from the genus Petasites, from which it instead sequesters terpenoids such as petasol (26) and related compounds (Figure 9). ... 

Pyrrolizidine alkaloids Senecionine (D 17.1) Taken up by larvae of the moth s Arctia caja and Tyria jacobaeae from food source Senecio sp.), stored in the body, deterring birds... 

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