Collect. Czech. Chem. Commun. 1986, 51, 2884-2895

Constituents of frontal gland secretion of peruvian termites Nasutitermes ephratae

Irena Valterová, Soňa Vašíčková, Miloš Buděšínský and Jan Vrkoč

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


The defense secretion of Nasutitermes ephratae soldiers was analyzed and its constituents were identified. The volatile fraction contains monoterpenic hydrocarbons α-pinene, camphene, sabinene, β-pinene, myrcene, 4-carene, 3-carene, α-terpinene, limonene, γ-terpinene, β-phellandrene, and terpinolene. From the non-volatile fraction four alcohols derived from trinervitane skeleton were isolated: 1(15),8(19)-trinervitadien-3α-ol (I), 1(15),8(19)-trinervitadien-2β,3α-diol (II) and its 2α,3α- (III) and 2α,3β- (IV) isomers. 3α-Hydroxy-1(15),8(19)-trinervitadien-2-one (V), which was also isolated, is probably an artefact formed during the work-up of the extract. The structure of 3β-hydroxy-1(15),8(19)-trinervitadien-2-one (VI) was determined on the basis of mass, IR and 1H NMR spectra, comparison with model compounds and analogy with the literature. The absolute configuration of the trinervitane skeleton was studied by CD spectra of tris(2,2,6,6-tetramethyl-3,5-heptanedionato)praseodymium complexes of the 2,3-diols II-IV and by the 1H NMR spectra of esters of the alcohol I with (R)- and (S)-α-methoxy-α-(trifluoromethyl)phenylacetic acid. The results obtained by both methods are identical and confirm the earlier suggested absolute configuration of the trinervitane skeleton.