Isolation of six anthraquinone diglucosides from cascara sagrada bark by high-performance countercurrent chromatography

J Sep Sci. 2020 Nov;43(21):4036-4046. doi: 10.1002/jssc.202000597. Epub 2020 Sep 21.

Abstract

In this study, high-performance countercurrent chromatography was employed to isolate six anthraquinone diglucosides, namely, cascarosides A-F, from cascara sagrada (Rhamnus purshiana DC [Rhamnaceae]) bark. The n-butanol-soluble extract of cascara sagrada was separated by off-line two-dimensional high-performance countercurrent chromatography. The first-dimensional high-performance countercurrent chromatography resolved the n-butanol-soluble extract (510 mg) of cascara sagrada using the flow-rate gradient method with a chloroform-methanol-isopropanol-water (6:6:1:4, v/v/v/v, normal-phase mode) system to afford four anthraquinone diglucoside fractions (groups I [cascarosides C-D, 71 mg], II [cascarosides E-F, 56 mg], III [cascaroside A, 53 mg], and IV [cascaroside B, 31 mg]). Groups I and II were separated by the second-dimensional high-performance countercurrent chromatography using an ethyl acetate-n-butanol-water (7:3:10, v/v/v, normal-phase mode) system to yield cascarosides C (34 mg), D (26 mg), E (19 mg), and F (15 mg). Additionally, one-step preparative-scale high-performance countercurrent chromatography method was developed to isolate large amounts of cascarosides A (389 mg) and B (187 mg) from the water-soluble extract (2.1 g) of cascara sagrada using an ethyl acetate-n-butanol-water (2:8:10, v/v/v, normal-phase mode) system. The current study demonstrated that high-performance countercurrent chromatography is a powerful technique for the isolation of marker compounds from herbal materials.

Keywords: anthraquinone diglucoside; cascara sagrada; cascarosides A-F; high-performance countercurrent chromatography.

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Chromatography, High Pressure Liquid
  • Countercurrent Distribution
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Molecular Conformation
  • Plant Bark / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Rhamnus / chemistry*
  • Stereoisomerism

Substances

  • Anthraquinones
  • Glucosides
  • Plant Extracts