| Title: | Identification and Synthesis of a Macrolide as an Anti-aphrodisiac Pheromone from Males of Heliconius erato phyllis |
| Author(s): | Melo DJ; Borges EO; Szczerbowski D; Vidal DM; Schulz S; Zarbin PHG; |
| Address: | "Universidade Federal do Parana, Departamento de Quimica, 81531-990 Curitiba, Brazil. Universidade Federal do Parana, Departamento de Zoologia, 81531-990 Curitiba, Brazil. Technische Universitat Braunschweig, Institute of Organic Chemistry, 38106 Braunschweig, Germany. Universidade Federal de Minas Gerais, Departamento de Quimica, 31270-901 Belo Horizonte, Brazil" |
| DOI: | 10.1021/acs.orglett.2c01160 |
| ISSN/ISBN: | 1523-7052 (Electronic) 1523-7052 (Linking) |
| Abstract: | "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 (2R,6E,10R)-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" |
| Keywords: | Animals Aphrodisiacs/chemistry *Butterflies/chemistry Female *Macrolides/chemistry Male *Pheromones/chemistry *Scent Glands/chemistry; |
| Notes: | "MedlineMelo, Douglas J Borges, Eliane O Szczerbowski, Daiane Vidal, Diogo M Schulz, Stefan Zarbin, Paulo H G eng Research Support, Non-U.S. Gov't 2022/05/25 Org Lett. 2022 Jun 3; 24(21):3772-3775. doi: 10.1021/acs.orglett.2c01160. Epub 2022 May 24" |
