Development of a myricetin/hydroxypropyl-β-cyclodextrin inclusion complex: preparation, characterization, and evaluation

Carbohydr Polym. 2014 Sep 22:110:329-37. doi: 10.1016/j.carbpol.2014.04.006. Epub 2014 Apr 18.

Abstract

Myricetin shows low oral bioavailability (<10%) in rats due to poor aqueous solubility, though it has various pharmacological activities. Complexation with cyclodextrins (CDs) is a potent pharmaceutical method to enhance the bioavailability of poorly soluble compounds. The myricetin/HP-β-CD inclusion complex was prepared and confirmed by DSC, PXRD, and SEM. Here, the inclusion mode is described in detail with regard to structural and energetic aspects using a phase solubility diagram and 1H NMR, NOESY, and FT-IR spectra. The water solubility and dissolution rate of myricetin were greatly enhanced by forming the myricetin/HP-β-CD inclusion complex. Consequently, the oral bioavailability of the myricetin/HP-β-CD inclusion complex in rats was effectively increased 9.4-fold over free myricetin, and its antioxidant activity was also improved. The present study provides useful information for the potential application of complexation with myricetin, a naturally occurring hydrophobic phenolic compound in herbal medicine.

Keywords: Characterization; Hydroxypropyl-β-cyclodextrin; In vitro dissolution; Inclusion complex; Myricetin; Pharmacokinetics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Hydroxypropyl-beta-cyclodextrin
  • Administration, Oral
  • Animals
  • Antioxidants / administration & dosage*
  • Antioxidants / chemistry
  • Antioxidants / pharmacokinetics*
  • Antioxidants / pharmacology
  • Biological Availability
  • Biphenyl Compounds / chemistry
  • Drug Carriers / chemistry*
  • Flavonoids / administration & dosage*
  • Flavonoids / chemistry
  • Flavonoids / pharmacokinetics*
  • Flavonoids / pharmacology
  • Male
  • Picrates / chemistry
  • Rats
  • Rats, Sprague-Dawley
  • Solubility
  • beta-Cyclodextrins / chemistry*

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Drug Carriers
  • Flavonoids
  • Picrates
  • beta-Cyclodextrins
  • 2-Hydroxypropyl-beta-cyclodextrin
  • myricetin
  • 1,1-diphenyl-2-picrylhydrazyl