An experimental implementation of chemical subtraction

J Pharm Biomed Anal. 2008 Mar 13;46(4):692-8. doi: 10.1016/j.jpba.2007.12.014. Epub 2007 Dec 17.

Abstract

A preparative analytical method was developed to selectively remove ("chemically subtract") a single compound from a complex mixture, such as a natural extract or fraction, in a single step. The proof of concept is demonstrated by the removal of pure benzoic acid (BA) from cranberry (Vaccinium macrocarpon Ait.) juice fractions that exhibit anti-adhesive effects versus uropathogenic Escherichia coli. Chemical subtraction of BA, representing a major constituent of the fractions, eliminates the potential in vitro interference of the bacteriostatic effect of BA on the E. coli anti-adherence action measured in bioassays. Upon BA removal, the anti-adherent activity of the fraction was fully retained, 36% inhibition of adherence in the parent fraction at 100mug/mL increased to 58% in the BA-free active fraction. The method employs countercurrent chromatography (CCC) and operates loss-free for both the subtracted and the retained portions as only liquid-liquid partitioning is involved. While the high purity (97.47% by quantitative (1)H NMR) of the subtracted BA confirms the selectivity of the method, one minor impurity was determined to be scopoletin by HR-ESI-MS and (q)HNMR and represents the first coumarin reported from cranberries. A general concept for the selective removal of phytoconstituents by CCC is presented, which has potential broad applicability in the biological evaluation of medicinal plant extracts and complex pharmaceutical preparations.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Bacterial Adhesion / drug effects*
  • Benzoic Acid / isolation & purification*
  • Benzoic Acid / pharmacology
  • Beverages / analysis*
  • Countercurrent Distribution / methods*
  • Escherichia coli / drug effects
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Urinary Tract
  • Vaccinium macrocarpon / chemistry*

Substances

  • Benzoic Acid