Fast-Dissolving, Prolonged Release, and Antibacterial Cyclodextrin/Limonene-Inclusion Complex Nanofibrous Webs via Polymer-Free Electrospinning

J Agric Food Chem. 2016 Oct 5;64(39):7325-7334. doi: 10.1021/acs.jafc.6b02632. Epub 2016 Sep 21.

Abstract

We have proposed a new strategy for preparing free-standing nanofibrous webs from an inclusion complex (IC) of a well-known flavor/fragrance compound (limonene) with three modified cyclodextrins (HPβCD, MβCD, and HPγCD) via electrospinning (CD/limonene-IC-NFs) without using a polymeric matrix. The experimental and computational modeling studies proved that the stoichiometry of the complexes was 1:1 for CD/limonene systems. MβCD/limonene-IC-NF released much more limonene at 37, 50, and 75 °C than HPβCD/limonene-IC-NF and HPγCD/limonene-IC-NF because of the greater amount of preserved limonene. Moreover, MβCD/limonene-IC-NF has released only 25% (w/w) of its limonene, whereas HPβCD/limonene-IC-NF and HPγCD/limonene-IC-NF released 51 and 88% (w/w) of their limonene in 100 days, respectively. CD/limonene-IC-NFs exhibited high antibacterial activity against E. coli and S. aureus. The water solubility of limonene increased significantly and CD/limonene-IC-NFs were dissolved in water in a few seconds. In brief, CD/limonene-IC-NFs with fast-dissolving character enhanced the thermal stability and prolonged the shelf life along with antibacterial properties could be quite applicable in food and oral care applications.

Keywords: antibacterial activity; computational modeling; electrospinning; essential oil; modified cyclodextrins.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Computers, Molecular
  • Crystallography, X-Ray
  • Cyclodextrins / chemistry*
  • Cyclohexenes / chemistry*
  • Drug Carriers / chemistry*
  • Drug Liberation
  • Drug Stability
  • Escherichia coli / drug effects
  • Limonene
  • Magnetic Resonance Spectroscopy
  • Microscopy, Electron, Scanning
  • Nanofibers / chemistry*
  • Oils, Volatile / chemistry
  • Particle Size
  • Solubility
  • Staphylococcus aureus / drug effects
  • Terpenes / chemistry*
  • Thermogravimetry

Substances

  • Anti-Bacterial Agents
  • Cyclodextrins
  • Cyclohexenes
  • Drug Carriers
  • Oils, Volatile
  • Terpenes
  • Limonene