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

Abstract

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 <i>C. langsdorffii</i> 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 (<b>1</b>) and afzelin (<b>2</b>) and 3-<i>O</i>-(3-<i>O</i>-methyl-galloyl)­quinic acid (<b>3</b>), respectively. The H₂O-soluble fraction furnished 3,4-di-<i>O</i>-(3-<i>O</i>-methyl-galloyl)­quinic acid (<b>4</b>), 3,5-di-<i>O</i>-(galloyl)-4-<i>O</i>-(3-<i>O</i>-methyl-galloyl)­quinic acid (<b>5</b>), and 3,5-di-<i>O</i>-(3-<i>O</i>-methyl-galloyl)-4-<i>O</i>-(galloyl)­quinic acid (<b>6</b>). Their chemical structures were elucidated by NMR means