Danaus gilippus

Danaidone (25), which was first isolated from Lycorea ceres ceres (55) and Danaus gilippus berenice 59) by J. Meinwald et al., has been shown to act as an aphrodisiac pheromone necessary for successful courtship in D. gilippus berenice (57) and in D. chrysippus (56), since danaidone-lacking males have reduced courtship success 57,60). It seems likely that a similar role will be found for the closely related aldehydes, hydroxydanaidal (26) and danaidal (27). 

Dussourd, D. E Harvis, C. A. and Eisner, T. (1989). Paternal allocation of sequestered plant pyrrolizidine alkaloid to eggs in the danaine butterfly, Danaus gilippus. Experientia 45 896-898. 

What kindled our interest in this area of research was the seminal paper by Brower et al. (1965) on the courtship of the queen butterfly, Danaus gilippus, and the motion picture that these investigators made of this behavior. Their data showed clearly that the two brush-like structures, or hairpencils, that the males ordinarily kept tucked away in their abdomen are in fact everted and splayed during courtship, and brushed against the female prior to copulation. Glandular in nature, the hairpencils seemed to function as an aphrodisiac device that effected its action chemically. But the nature of the presumed pheromone and its precise communicative significance remained unknown. 

Danaidone proven pheromonal function (Danaus gilippus)... 

Brower L. P., Brower J. V. Z. and Cranston F. P. (1965) Courtship behavior of the queen butterfly, Danaus gilippus berenice. Zoologica 50, 1-39. 

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,... 

Euploea spec Danaus plexippus Danaus gilippus Papilio machaon Manduca sexta... 

Pheromonal Secretion of Monardi and Queen Butterfly.—New synthetic routes have been outlined to the degraded terpenoid compounds (198a) and (198b) isolated from the pheromonal secretion of the Monarch butterfly Danausplexippus) and of the related diol (198c) from the male Queen butterfly Danaus gilippus bermice)P ... 

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