| Autor: |
Melo DJ; Universidade Federal do Paraná, Departamento de Química, 81531-990 Curitiba, Brazil., Borges EO; Universidade Federal do Paraná, Departamento de Zoologia, 81531-990 Curitiba, Brazil., Szczerbowski D; Universidade Federal do Paraná, Departamento de Química, 81531-990 Curitiba, Brazil.; Technische Universität Braunschweig, Institute of Organic Chemistry, 38106 Braunschweig, Germany., Vidal DM; Universidade Federal de Minas Gerais, Departamento de Química, 31270-901 Belo Horizonte, Brazil., Schulz S; Technische Universität Braunschweig, Institute of Organic Chemistry, 38106 Braunschweig, Germany., Zarbin PHG; Universidade Federal do Paraná, Departamento de Química, 81531-990 Curitiba, Brazil. |
| Abstrakt: |
Investigation of the contents of the scent glands of the heliconiine butterfly Heliconius erato phyllis via gas chromatography/electroantennography revealed an unprecedented active compound. The males transfer this compound to females during mating. The structure of (2 R ,6 E ,10 R )-2,6-dimethyl-6-undecen-10-olide, a derivative of geranylacetone, was proposed on the basis of infrared and mass spectrometry spectra and microderivatization and confirmed by racemic and stereoselective syntheses. Bioassays with the synthetic macrolide showed the repellency of this compound, termed phyllisolide, when applied to scent glands of females, identifying it as an anti-aphrodisiac pheromone. |
