Idea leuconoe

From the hair-pencils of butterflies in Danainae and Ithomiinae (Papilion-oidea Nymphalidae), a wider variety of pyrrolizines (la-d, and 6a-d) have been identified than from Arctiidae moths. These compounds are biosynthesized from pyrrolizidine alkaloids, which are included in host plants fed by the larvae and protect them from the attacks of other herbivores [122]. In addition to novel lactones (7, 8a, and 8b) derived from an acid part of the alkaloids, many volatiles of more than 100 compounds (aromatics, terpenoids, hydrocarbons, and others) constitute scent bouquets of the male butterflies [123]. For example, the hair-pencil of Idea leuconoe (Danainae) which is distributed in South-East Asia contained 16 compounds (6b, 8a, 8b, 9, and others), and a mixture of the major volatiles applied to a butterfly dummy elicited an abdomen-curling acceptance posture in the females as a crude extract of the male hair-pencils did [ 124]. A chiral GC analysis revealed the absolute config-... 

P" and S-lactones present in the pheromone system of the giant white butterfly, Idea leuconoe, were synthesized. 

Nishida, R Schulz, S., Kim, C. S. et al. (1996). Male sex pheromone of a giant danaine butterfly, Idea leuconoe. Journal of Chemical Ecology 22 949-972. 

Nishida R., Kim C. S., Fukami H. and Irie R. (1991) Ideamine V-oxides pyrrolizidine alkaloids sequestered by the danaine butterfly, Idea leuconoe. Agric. Biol. Chem., 55, 1787-1792. 

Viridifloric /3-lactone, 143, has been identified as one of the pheromone components of a complex mixture of volatiles released by the pheromone glands of the male Idea leuconoe butterfly during courtship <1996BMC341>. A racemic mixture of both diastereoisomers was synthesized in four steps from the dilithio salt of 3-methylbutyric acid 144 alkylation with ethanal, dehydration of the secondary alcohol with phosphorus pentoxide, dihydroxylation of the C-C double bond with osmium tetraoxide, and finally formation of the /3-lactone by cyclization with sulfonyl chloride. By comparison with the sample isolated from I. leuconoe, the absolute configuration was established to be (2V,3V)-2-hydroxy-2-(l-methylethyl)-3-butanolide 143. 

T17 Pityogenes T18 Leptogenys T19. Idea leuconoe, quadridens, diminuta, ant 509 butterfly 510 bark beetle 508... 

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

An interesting sidelight on the metabolism of pyrrolizidines is that several butterfly and moth larvae that feed on plants containing these alkaloids metabolize them to products that serve the insects as pheromones or defensive substances. Thus the butterfly Idea leuconoe converts alkaloids from Parsonia laevigata to N-oxides [121]. The moth Creatonotos transiens makes its pheromone, R(-)-hydroxydanaidal from7(S)-heliotrine found in its host plant, Senecio jacobaea [122]. 

A number of male courtship pheromones are known to be synthesized from the necine base moiety of plant-acquired PAs by certain alkaloid sequestering Arctiidae, Danainae, and Ithomiinae [75,96] (Fig. 11). The giant white danaine butterfly Idea leuconoe [97,98] and most ithomiine butterflies even use lactones as pheromones derived from necic acids such as the (-)-viridifloric acid from... 

Scheme 22 Synthesis of 5-lactones present in the white butterfly Idea leuconoe...

In 1999, Schulz reported on the synthesis of (S,S)- or (/ ,/f)-6-hydroxyalkan-4-olides, components of the pheromonal secretion of the butterfly Idea leuconoe. The enantioselective hydrogenation reaction of methyl 4,6-... 

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