(1R, 6R)-2, 2, 6-Trimethyl-3-oxabicyclo[4.2.0]octan-4-one, a new monoterpene lactone produced by males of the cocoa borer Conotrachelus humeropictus (Col.: Curculionidae). Issue 26 (29th June 2016)

• Record Type: Journal Article
• Authors: Szczerbowski, Daiane; Torrens, Gabriela G.; Rodrigues, Mauro A.C.M.; Trevisan, Olzeno; Gomes, Sandra M.S.; Tröger, Armin; Mori, Kenji; Francke, Wittko; Zarbin, Paulo H.G.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 26(2016)
• Page Start: 2842
• Page End: 2844
• Publication Date: 2016-06-29
• Subjects: Conotrachelus humeropictus -- Semiochemicals -- Grandisoic acid -- Grandisol -- Grandisolide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.036
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Identification of three male specific compounds for Conotrachelus humeropictus. A novel natural product was identified and characterized. Grandisolide is the first monoterpene lactone identified in beetles. Abstract: The cocoa weevil Conotrachelus humeropictus is an economically most important pest on cocoa ( Theobroma cacao ) and cupuaçu ( Theobroma grandiflorum ) cultures. Knowledge on the pheromone system of this insect is prerequisite for the development of an integrated pest management system. GC/MS-analysis of headspace volatiles revealed the presence of three male specific compounds, which were identified to be (1 R, 2 S )-grandisol, (1 R, 2 S )-grandisoic acid, and the new bicyclic terpene lactone (1 R, 6 R )-2, 2, 6-trimethyl-3-oxabicyclo[4.2.0]octan-4-one, which we term grandisolide.