NMR structure determination of (11 E)-trinervita-1(14),2,11-triene, a new diterpene from sexual glands of termites

• Published in: Tetrahedron Vol. 61; no. 45; pp. 10699 - 10704
• Main Authors: Buděšínský, Miloš, Valterová, Irena, Sémon, Etienne, Cancello, Eliana, Bordereau, Christian
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 07.11.2005; Elsevier
• Subjects: 1H and 13C NMR; Chemical and Process Engineering; Chemistry; Chemistry, Organic; Diterpene hydrocarbon; Engineering Sciences; Female tergal gland; Food engineering; Life Sciences; Pheromone; Physical Sciences; Science & Technology; Termite; Trinervitane; Termite; Trinervitane; Pheromone; 1H and 13C NMR; Diterpene hydrocarbon; Female tergal gland; NEOCEMBRENE-A; trinervitane; ISOPTERA; SECRETIONS; diterpene hydrocarbon; female tergal gland; TRAIL-FOLLOWING PHEROMONE; termite; pheromone; NASUTITERMITINAE; H-1 and C-13 NMR; SOLDIERS; PHEROMONE; TRINERVITANE; FEMALE TERGAL GLAND; DITERPENIQUE; 1H-RMN; 13C-RMN; DITERPENE HYDROCARBON; 1H and 13C; GLANDE TERGALE FEMELLE; TERMITE
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2005.08.084

Female alates of Nasutitermes ephratae termites from Guadeloupe and Nasutitermes sp. from Brazil produce a diterpene hydrocarbon of the molecular formula C 20H 30 as the main component of their tergal gland secretion. Analysis of NMR, IR, and mass spectra of the diterpene led to a structure of (11 E)-trinervita-1(14),2,11-triene. Based on a comparison with the published oxygenated trinervitane skeleton from termites we prefer the enantiomer with absolute configurations (4 R,7 S,8 R,15 S,16 S). The suggested structure is supported by ab initio quantum chemical calculation of 1H and 13C chemical shifts for the optimized geometry of the molecule. Graphical Abstract