Danaid butterflies

Defensive/ants, birds, monk isopr. (cardenolide steroids C 8.1.1) danaid butterflies larvae. Ins., as plant dietary metabolites... 

M. (1979). Chemical communication, plant relationships, and mimicry in the evolution of danaid butterflies. Entomologia Experimentalis et Applicata 24 264-277. 

Availability of biosynthetic precursors from food, as in some danaid butterflies and arctiid moths, which modify plant pyrrolizidine alkaloids into volatile derivatives that are used as male pheromones (e.g. Schneider et al., 1975). In... 

Edgar J. A., Culvenor C. C. J. and Smith L. W. (1971) Dihydropyrrolizine derivatives in hairpencil secretion of danaid butterflies. Experientia 27, 761-762. 

Meinwald J., Boriack C. J., Schneider D., Boppre M., Wood D. F. and Eisner T. (1974) Volatile ketones in the hairpencil secretion of danaid butterflies (Amauris and Danaus). 

Structural investigations on the sex pheromones of male butterflies have yielded several unique insect exocrine products. The major components in the hair pencils of the danaid Lycorea ceres ceres are cetyl acetate, (Z)-vaccenyl acetate, and 2,3-dihydro-7-methyl pyrrolizin-l-one (XXIV) (103) The dihydropyrrol izi none, as well as ( , )-3,7-dimethyldeca-2,6-dien-l,10-diol, have been identified from the hair pencils of the queen butterfly, Danaus gilippus (104), and the former compound possesses pheromonal activity when evaluated electrophysiologically (105) and behaviorally (106). The hair pencils of the monarch butterfly, Danaus plexippus, have yielded ( ,E)-10-hydroxy-3,7-dimethyl-2,6-deca dienoic acid (107) and (E,15)-3,7-dimethyl-2,6-decadien-l,10-dioic acid (108). On the other hand, the Old World monarch, Danaus chrysippus, contains (E)-3,7-dimethyloct-2-en-l,8-diol as well as the pyrrolizinone (XXIV) (109). Recently,... 

T56 Kheper, dung beetles 555 danaid butterflies,539 Tetranychus urticae, spider mite 556... 

Several p3nroIizidine bases have now been found free in the plant. (+ )-Isoretronecanol has been found free in the roots, and as the esters thesine and thesinine in the aerial portion of Thesium minkwitzianum (96). Retronecine N-oxide has been isolated from Crotalaria retusa. It is of interest that l-methyl-2,3,8,l-didehydropyrrolizid-7-one (XIV) has been isolated from the exocrine secretion of danaid butterflies (108). 

The Monarch butterfly Danaus plexippus) was found to sequester and store pyrrolizidine alkaloids when fed on homogenized leaves of Senecio vulgaris. It is thought that the presence of these alkaloids in the butterfly may contribute towards its defence mechanism, by making it unpalatable to potential predators. Unlike many other danaids, the Monarch is not dependent on pyrrolizidine alkaloids as precursors of its sex pheromones. 

Dimenna GP, Krick TP, Segall HJ (1980) Rapid high-performance liquid chromatography isolation of monoesters, diesters and macrocyclic diester pyrrolizidine alkaloids from Senecio jacobaea an Amsinckia intermedia. J Chromatogr 192 474-478 Edgar JA, Culvenor CCJ (1974) Pyrrolizidine ester alkaloid in danaid butterflies. Nature 248 614-616... 

Danaid butterflies can metabolically alter pyrrolizidine alkaloids without apparent harm. Individuals of the American monarch butterfly, Danaus plexippus, captured in the field were found to contain pyrrolizidine alkaloids that were present in food plants at the capture sites. Adults of D. plexippus were able to store alkaloids for several days. Unlike certain other species, however, these male butterflies do not secrete alkaloid-derived substances on their hairpencils, nor do the hairpencils figure prominently in courtship. It has been suggested that the alkaloids may contribute to the lack of palatibility of the butterflies to potential predators (Edgar et al., 1976 Pliske, 1975). 

Pyrrolizidine Alkaloids in Parsonsia Species (Family Apocynaceae) which Attract Danaid Butterflies. Experientia 31, 393-394 (1975). 

Sex pheromones of Danaid butterflies, produced from pyrrolizidine ester alkaloids taken up from food source (Senecio sp.)... 

Most pheromones are synthesized de novo in the animal body. Some, however, are taken up from plant sources and are used directly or in a modified form (cf. the pyrrolizidines secreted as sex pheromones from male Danaid butterflies and myrcene used as sex pheromone of Dehdroctonus brevicomis Table 66). In Creatonotos moths, pyrrolizidine alkaloids ingested by the larvae with the diet, in addition to their action as pheromone precursors, show hormone-like activity and control the morphogenesis of the scent organs. 

Marsh, N. A., Clarke, C. A., Rothschild, M. and Kellett, D. N. (1977) Hypolimnas bolina (L.), a mimic of danaid butterflies, and its model Euploea core (Cram.) store cardioactive substances. Nature, 268, 726-8. 

Mendez JM, Flores B, Leon F, Martinez ME, Vazquez A, Garcia GA, Salmon M (1996) A new synthesis of monosubstituted succinaldehydes and 3-substituted pyrroles from acetonitriles. Formal synthesis of 2,3-dihydro-7-methyl-2H-pyrrolizidin-l-one (Danaldone), a semiochemical of danaid butterflies. Tetrahedron Lett 37(24) 4099-4102 Chichibabin AE (1924) Uber Kondensation der Aldehyde mit Ammoniak zu Pyridinbasen. J fur Praktlsche Chemie 107(1 ) 122-128... 

Figure 10.4 Some examples ofpyrrolizidine alkaloids and the sex attractants made from them by danaid butterflies and ornate moths. The biosynthesis in plants of the retronedne part of the pyrrolizidine alkaloids begins with reaction between putrescine (from ornithine, Chapter 9) and spermidine...

---