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

J Agric Food Chem. 2015 Aug 12;63(31):6939-45. doi: 10.1021/acs.jafc.5b01588. Epub 2015 Aug 3.

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 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.

Keywords: 3-O-methyl-galloylquinic acid; Copaifera langsdorffii; HSCCC; afzelin; quercitrin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fabaceae / chemistry*
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Leaves / chemistry*
  • Quinic Acid / chemistry*
  • Quinic Acid / isolation & purification

Substances

  • Flavonoids
  • Plant Extracts
  • Quinic Acid