Defense Mechanisms of Arthropods. 83. α- and β-Necrodol, Novel Terpenes from a Carrion Beetle (Necrodes surinamensis, Silphidae, Coleoptera)

Article abstract of DOI:10.1021/jo00300a020

The defensive secretion obtained from the rectal gland of the carrion beetle Necrodes surinamensis has been found to consist of a mixture of aliphatic acids and terpene alcohols.Octanoic acid, decanoic acid, (Z)-3-decenoic acid, (Z)-4-decenoic acid, hexadecanoic acid, and octadecanoic acid are the chief acidic components.The three major terpenes are lavandulol and α- and β-necrodol.The necrodols were shown to have a 1,2,2,3,4-pentamethylcyclopentane framework not previously found among natural monoterpenes.Formulas 9 and 10 are derived for α- and β-necrodol, respectively, chiefly on the basis of mass spectrometric and NMR spectroscopic analysis.