title: New methylcyclopentanoid terpenes from the larval defensive secretion of a chrysomelid beetle (Plagiodera versicolora).
abstract: The defensive secretion of larvae of the chrysomelid beetle Plagiodera versicolora contains two unstable, volatile methylcyclopentanoid terpenes: a dialdehyde (chrysomelidial) isomeric with dolichodial and anisomorphal, and a closely related enol lactone (plagiolactone). Chrysomelidial and plagiolactone are shown to have structures III and IV on the basis of a detailed analysis of their spectra, coupled with chemical transformations to products of known structure.
mesh_terms: D000818:Animals; D002849:Chromatography, Gas; D001517:Coleoptera / Q000378:metabolism*; D003517:Cyclopentanes; D007814:Larva / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D013056:Spectrophotometry, Ultraviolet; D013729:Terpenes
chemical_list: D003517:Cyclopentanes; D013729:Terpenes
references.citation: Tetrahedron. 1965 Nov;21(11):3121-6
references.pmid: 5879263
references.citation: Science. 1964 Dec 4;146(3649):1318-20
references.pmid: 14207462