Preparative isolation and identification of tyrosinase inhibitors from the seeds of Garcinia kola by high-speed counter-current chromatography

J Chromatogr A. 2007 Jun 1;1151(1-2):45-50. doi: 10.1016/j.chroma.2007.02.085. Epub 2007 Mar 1.

Abstract

In continuation of our search for bioactive natural products that can be used for the treatment of dermatological disorders associated with melanin hyperpigmentation, 50 extracts/fractions from 21 families of medicinal plants from West and Central Africa were evaluated for inhibitory activity against tyrosinase (E:C:1.14.18.1), the rate-limiting enzyme in melanin synthesis. Four extracts including the methanol extract of Garcinia kola seeds at 100 microg/ml displayed >60% inhibition of tyrosinase activity. Preparative high-speed counter-current chromatography with solvent system composed of n-hexane-ethyl acetate-methanol-water (3:5:3:5) successfully separated the most active extract from G. kola seed. By stepwise increase of the flow-rate of the mobile phase, five major biflavanones including GB-I-glucoside (1) GB-1a (2), GB-1 (3), GB-2 (4), kolaflavonone (5) were successfully isolated in 6 h. Compound (4) was the most potent (IC(50) 582 microM) and compared favorably with a reference tyrosinase inhibitor (kojic acid, IC(50) 130 microM).

MeSH terms

  • Countercurrent Distribution / methods*
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification
  • Garcinia kola / chemistry*
  • Molecular Structure
  • Peptides / chemistry
  • Peptides / isolation & purification*
  • Reproducibility of Results
  • Seeds / chemistry*

Substances

  • Flavonoids
  • Peptides