6533b7d6fe1ef96bd126660c

RESEARCH PRODUCT

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

Milos BudesinskyChristian BordereauEtienne SémonIrena ValterováEliana M. Cancello

subject

0106 biological sciencesStereochemistryAb initio1H and 13C010402 general chemistry01 natural sciencesBiochemistry1H-RMN; 13C-RMNTerpene03 medical and health scienceschemistry.chemical_compoundDrug Discovery[SDV.IDA]Life Sciences [q-bio]/Food engineeringNasutitermesOrganic chemistryMoleculeDITERPENE HYDROCARBONPHEROMONE[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process EngineeringGLANDE TERGALE FEMELLEDITERPENIQUE030304 developmental biologyFEMALE TERGAL GLANDchemistry.chemical_classification0303 health sciencesbiology010405 organic chemistryChemical shiftOrganic ChemistryTERMITEGeneral Medicinebiology.organism_classification0104 chemical sciences010602 entomologyHydrocarbonchemistryTRINERVITANEMass spectrumEnantiomerDiterpene

description

Graphical Abstract Full-size image; International audience; Female alates of Nasutitermes ephratae termites from Guadeloupe and Nasutitermes sp. from Brazil produce a diterpene hydrocarbon of the molecular formula C20H30 as the main component of their tergal gland secretion. Analysis of NMR, IR, and mass spectra of the diterpene led to a structure of (11E)-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 (4R,7S,8R,15S,16S). The suggested structure is supported by ab initio quantum chemical calculation of 1H and 13C chemical shifts for the optimized geometry of the molecule.

yearjournalcountryeditionlanguage
2005-01-01
10.1016/j.tet.2005.08.084https://hal.inrae.fr/hal-02681181