Separation and identification of anthocyanin extracted from mulberry fruit and the pigment binding properties toward human serum albumin

J Agric Food Chem. 2014 Jul 16;62(28):6813-9. doi: 10.1021/jf500705s. Epub 2014 Jul 7.

Abstract

Purple pigments were isolated from mulberry extracts using preparative high-speed countercurrent chromatography (HSCCC) and identified by ESI-MS/MS and high performance liquid chromatography (HPLC) techniques. The solvent system containing methyl tert-butyl ether, 1-butanol, acetonitrile, water, and trifluoroacetic acid (10:30:10:50:0.05; %, v/v) was developed in order to separate anthocyanins with different polarities. Cyanidin 3-O-(6″-O-α-rhamnopyranosyl-β-galactopyranoside) (also known as keracyanin) is the major component present in mulberry (41.3%). Other isolated pigments are cyanidin 3-O-(6″-O-α-rhamnopyranosyl-β-glucopyranoside) and petunidin 3-O-β-glucopyranoside. The binding characteristics of keracyanin with human serum albumin (HSA) were investigated by fluorescence and circular dichroism (CD) spectroscopy. Spectroscopic analysis reveals that HSA fluorescence quenched by keracyanin follows a static mode. Binding of keracyanin to HSA mainly depends on van der Waals force or H-bonds with average binding distance of 2.82 nm. The results from synchronous fluorescence, three-dimensional fluorescence, and CD spectra show that adaptive structure rearrangement and decrease of α-helical structure occur in the presence of keracyanin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthocyanins / analysis*
  • Anthocyanins / chemistry
  • Anthocyanins / isolation & purification
  • Anthocyanins / metabolism*
  • Chemical Phenomena
  • Chromatography, High Pressure Liquid / methods
  • Circular Dichroism
  • Countercurrent Distribution / methods
  • Fluorescence Resonance Energy Transfer
  • Fruit / chemistry*
  • Humans
  • Hydrogen Bonding
  • Morus / chemistry*
  • Protein Binding
  • Protein Structure, Secondary
  • Serum Albumin / chemistry
  • Serum Albumin / metabolism*
  • Spectrometry, Mass, Electrospray Ionization
  • Tandem Mass Spectrometry

Substances

  • Anthocyanins
  • Serum Albumin
  • keracyanin