VOLATILE CONSTITUENTS OF BALSAM POPLAR: THE PHENOL GLYCOSIDE CONNECTION

Article abstract of DOI:10.1016/S0031-9422(00)81813-0

Key Word Index - Populus balsamifera; Salicaceae; balsam poplar; phenol glycosides; 6-hydroxycyclohex-2-enone; cyclohexan-1,2-dione; salicortin; trichocarpin; trichocarpigenin.The volatile metabolites of balsam poplar winter-domant buds are a complex array of mono- and sesquiterpenoids with 1,8-cineol, trans-nerolidol and (+)-(1R,1'R)-α-bisabolol being the major components.On the other hand the volatiles of internodes (stems between buds) consist mainly of salicaldehyde and (+)-6-hydroxycyclohexanone with minor amounts of cyclohexan-1,2-dione and an unidentified compound.This is the first report of these cyclohexanones as natural products; salicortin, a phenol glycoside, appears to be their biosynthetic precursor.A second phenol glycoside, trichocarpin, is present in poplar internodes; and it is the progenitor of trichocarpigenin (benzyl gentisate), an easily formed artifact.