Creatonotos transiens

Bell, T. W. and Meinwald, J. (1986). Pheromones of two arctiid moths (Creatonotos transiens and C. gangis) chiral components from both sexes and achiral female components. Journal of Chemical Ecology 12 385 109. 

Bell, T. W Boppre, M., Schneider, D. and Meinwald, J. (1984). Stereochemical course of pheromone biosynthesis in the arctiid moth, Creatonotos transiens. Experientia 40 713-714. 

Wink, M. L Schneider, D. and Witte, L. (1988). Biosynthesis of pyrrolizidine alkaloid-derived pheromones in the arctiid moth, Creatonotos transiens stereochemical conversion of heliotrine. Zeitschrift fiir Naturforschung 43c 737-741. 

A number of chemical and biochemical questions are raised in light of the preceding discussion. Preliminary results suggested that Creatonotos transiens can produce 7R-(-)-hydroxydanaidal (XIII) from PA esters based either on retronecine (XIV), which has the same absolute configurations as XIII at the... 

Schulz S., Francke W., Boppre M., Eisner T. and Meinwald J. (1993) Insect pheromone biosynthesis stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera Arctiidae). Proc. Natl. Acad. Sci. USA 90, 6834-6838. 

Larvae of the Arctiidae are able to locate PA-containing plants. Creatonotos transiens larvae, for example, are strongly attracted by PAs that act as strong... 

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]. 

Larvae of the arctiid moth Creatonotos transiens accumulate pyrrolizidine alkaloids when they feed on plants containing these compounds. Other types of alkaloids tested were excreted in the frass (Wink and Schneider, 1988). Pyrrolizidine alkaloids act as precursors for pheromones, but also as morphogens for the development of the male scent organ (Wink and Schneider, 1988). 

Fig. 12. Biosynthesis of the male courtship pheromone hydroxydanaidal from C-7 deuterated (7R)- and (7S)-heliotrine orally fed to larvae of Creatonotos transiens. Epimerization of the (7S)-configurated alkaloid occurs in the larvae, whereas the further steps occur just prior to eclosion of the pupae [101]...

Fig. 13. Insect PAs synthesized in Creatonotos transiens by esterification of retronecine derived from plant ingested PAs and necic acids produced by the insect [103]. Biosynthesis is restricted to the early stages of pupation. All insect PAs are present as AT-oxides 1 and 2 = callimorphine and isocallimorphine 3 and 4 = creatonotine and isocreatonotine 5 and 6 = 09- and 07-(2-hydroxyisovaleryl)retronecine 7 and 8 = 09- and 07-(2-hydroxypropionyl) retronecine...

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