Structural Elucidation of a New Flavolignan Acylglycoside from Fallen Needles of Pinus banksiana

A new flavolignan acylglycoside, namely phillygenin 4-O-(2′′-trans-cinnamoyl)- α -L-rhamnopyranoside ( 1 ), along with a known phenolic acid (ellagic acid, 2 ) and three known flavonol glycosides (kaempferol 3-O- β -D-glucopyranoside ( 3 ), kaempferol 3-O- α -L-rhamnopyranoside ( 4 ), and quercetin 3-O- β -D-glucopyranoside ( 5 ), was isolated and purified from the fallen needles of Pinus banksiana by repeated column chromatography. The structures of these secondary metabolites were mainly elucidated by the extensive use of 1D and 2D NMR experiments, together with IR, UV, and FAB MS spectra. Among the four known compounds, 2 and 4 have never been found in this conifer species previously.