Antioxidant and cytotoxic activity of polyphenolic compounds isolated from the leaves of Leucenia leucocephala

Pharm Biol. 2011 Nov;49(11):1103-13. doi: 10.3109/13880209.2011.568623. Epub 2011 May 20.

Abstract

Context: Cancer is a serious clinical problem to the health care system. Anticancer drugs have been extracted from plants containing phenolic compounds. Leucenia species (Fabaceae) contain a variety of bioactive components of numerous biological and pharmacological properties.

Objective: This study explored the constitutive polyphenols of Leucenia leucocephala Lam. growing in Egypt and evaluated the antioxidant and cytotoxic activity.

Materials and methods: Chemical structures of the isolated compounds from the leaves of L. leucocephala were established by spectral techniques (UV, (1)H, and (13)C NMR, MS).

Results: Chromatographic separation of 80% MeOH extract of the leaves of L. leucocephala have resulted in a novel flavonoid-galloyl glycoside [myricetin 3-O-(2',3'4'-tri-O-galloyl)-α-L-rhamnopyranoside] with three known polyphenolic compounds isolated for the first time from this species (apigenin 7-O-β-D-glucuronopyranoside methyl ester, luteolin 7-O-β-D-glucuronopyranoside methyl ester, and 1,3,6-tri-O-galloyl-β-D-glucopyranose) and seven known previously isolated compounds. Also, 80% methanol extract exhibited high antioxidant activity (SC(50) = 3.94 µg/ml), which is correlated with its phenolic content. The extract also showed cytotoxic activity against Hep G2 (IC(50) value 1.41 µg/ml) confirming its anticancer activity against hepatocellular carcinoma. Among the tested compounds (4-8) for antioxidant property, compound 7 was the most active compound (SC(50) = 2.49 µg/ml). Also compounds 7 and 8 exhibited high cytotoxic activity (IC(50) = 2.41 and 2.81 µg/ml, respectively).

Discussion and conclusion: These findings demonstrate that the leaves of L. leucocephala contain a considerable amount of polyphenolic compounds with high antioxidant properties, thus it has great potential as a source for natural health products.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / chemistry
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Egypt
  • Fabaceae* / chemistry
  • Hep G2 Cells
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Methanol / chemistry
  • Molecular Structure
  • Picrates / chemistry
  • Plant Leaves
  • Plants, Medicinal
  • Polyphenols / chemistry
  • Polyphenols / isolation & purification
  • Polyphenols / pharmacology*
  • Solvents / chemistry
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Biphenyl Compounds
  • Picrates
  • Polyphenols
  • Solvents
  • 1,1-diphenyl-2-picrylhydrazyl
  • Methanol