Creatonotos

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. 

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. 

The biology of Creatonotos (Lepidoptera Arctiidae) with special reference to the androconial system. Zoological Journal of the Linnaean Society 96 339-356. 

Schmitz, B., Buck, M., Egelhaaf, A. and Schneider, D. (1989). Ecdysone and a dietary alkaloid interact in the development of the pheromone gland of a male moth ([Creatonotos, Lepidoptera Arctiidae). Roux s Archives of Developmental Biology 198 1-7. 

Creatonotos moths regulation by pyrrolizidine alkaloids. Science 215 1264-1265. 

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... 

Does this biosynthetic plasticity reflect the ability of Creatonotos to sequester and exploit a wide range of naturally occurring PAs for defensive purposes It is interesting to note that Utetheisa seems to be restricted to the use of 7R alkaloids (monocrotaline, usaramine) present in its food plants, and unable to produce 7-hydroxydanaidal from heliotrine, a 7S-PA. This inability may well reflect a lack of evolutionary exposure to dietary 7S-PAs (Schulz et al., 1993). 

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... 

VON NICKISCH-ROSENEGK, E SCHNEIDER, D., WINK, M Time-course of pyrrolizidine alkaloid processing in the alkaloid exploiting arctiid moth Creatonotos trcmsiens. Z Naturforsch., C Biosci., 1990,45, 881-894. 

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). 

Schneider, D., M. Boppre, J. Zweig, S.B. Horsley, T.W. Bell, J. Meinwald, K. Hansen, and E.W. Diehl Scent Organ Development in Creatonotos Moths Regulation by Pyrrolizidine Alkaloids. Science 215, 1264-1265 (1982). 

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. 

Schneider, D., Boppre, M., Zweig, J., Horsley, S. B., Bell, T. W., Meinwald, J., Hansen, K., Diehl, E. W. Scent organ development in Creatonotos moths regulation by pyrrolizidine alkaloids. Science 215, 1264-1265 (1982)... 

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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