Flavonoids and Methoxy-galloylquinic Acid Derivatives from the Leaf Extract of Copaifera langsdorffii Desf.

Despite reports on the pharmacological potential of Copaifera langsdorffii Desf. (Leguminosae-Caesalpinioideae) leaf extract, little is known about its chemical composition. In this work, a phytochemical study from the C. langsdorffii ethanol/H2O 7:3 (v/v) extract was undertaken. Separation was performed by high-speed counter-current (HSCCC) and Sephadex LH-20 column chromatographies, followed by preparative HPLC. The EtOAc- and H2O-soluble fractions of the extract furnished the flavonoids quercitrin (1) and afzelin (2) and 3-O-(3-O-methyl-galloyl)quinic acid (3), respectively. The H2O-soluble fraction furnished 3,4-di-O-(3-O-methyl-galloyl)quinic acid (4), 3,5-di-O-(galloyl)-4-O-(3-O-methyl-galloyl)quinic acid (5), and 3,5-di-O-(3-O-methyl-galloyl)-4-O-(galloyl)quinic acid (6). Their chemical structures were elucidated by NMR means.