DEFENSE-MECHANISMS OF ARTHROPODS .83. ALPHA-NECRODOL AND BETA-NECRODOL, NOVEL TERPENES FROM A CARRION BEETLE (NECRODES-SURINAMENSIS, SILPHIDAE, COLEOPTERA)

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 a-and 3-necrodol. The necrodols were shown to have a 1,2,2,3,4-penta-methylcyclopentane framework not previously found among natural monoterpenes. Formulas 9 and 10 are derived for a-and 3-necrodol respectively, chiefly on the basis of mass spectrometric and NMR spectroscopic analysis. © 1990, American Chemical Society. All rights reserved.