Interactions of cyanidin and cyanidin 3-O-β-glucopyranoside with model lipid membranes
Cyanidin and cyanidin 3-O-β-glucopyranoside (Cy3Glc) are flavonoids that have several biological properties, including as antioxidants. The interactions of cyanidin and Cy3Glc with model lipid membranes differing in surface charge and phase state were investigated using differential scanning calorimetry and fluorescence emission polarization spectrometry. Differential scanning calorimetry shows that cyanidin and Cy3Glc have no effects on the phase transition of zwitterionic liposomes composed of the 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and negatively charged liposomes composed of 1,2-dipalmitoyl-sn-glycero-3-phosphoglycerol (DPPG) at pH 7.0. Emission polarization spectrometry using 1,6-diphenyl-1,3,5-hexatriene (DPH) and N,N,N-trimethyl-4-(6-phenyl-1,3,5-hexatrien-1-yl)phenylammonium p-toluenesulfonate (TMA-DPH) probes shows that cyanidin slightly increases the polarization of DPPC and DPPG liposomes in the gel state at 298.15 K. Significant ordering effects of cyanidin on DPPC liposomes in the liquid state at 318.15 K and no effect on the liquid state of DPPG at 318.15 K were observed using the DPH and TMA-DPH probes. Cy3Glc causes no change in polarization regardless the gel or liquid-disordered state of DPPC or DPPG liposomes. Cy3Glc due to its glucoside moiety is too bulky to partition into water–lipid interface or between the nonpolar acyl chains of membranes. The results of this work may contribute to understanding the low bioavailability of glycosides.
KeywordsCyanidin Cyanidin 3-glucoside DPPC and DPPG model membranes DSC Fluorescence emission polarization of DPH and TMA-DPH
The study was financially supported by Slovenian Research Agency through the research program P4-0121 (N.P.U.) and the bilaterally project between Republic of Slovenia and Republic of Serbia BI-RS/12-13-015 (N.P.U. and D.S). V.R. was partly financed by the CEPUS SI-8402/2010—bilateral scholarship.
- 18.Manach C, Williamson G, Morand C, Scalbert A, Rémésy C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr. 2005;81:230S–42S.Google Scholar
- 19.Keller RB, editor. Flavonoids: biosynthesis, biological effects and dietary sources. New York: Nova Science Publishers, Inc.; 2009.Google Scholar
- 36.Lasic DD. Liposomes: from physics to applications. 1st ed. Amsterdam: Elsevier Science Ltd; 1993.Google Scholar
- 49.PubChem [Internet]. [cited 2014 Aug 25]. https://pubchem.ncbi.nlm.nih.gov/search/#collection=compounds.
- 50.Smith EA, Dea PK. Differential scanning calorimetry studies of phospholipid membranes: the interdigitated gel phase. In: Elkordy AA, editor. Applications of calorimetry in a wide context—Differential scanning calorimetry, isothermal titration calorimetry and microcalorimetry. InTech; 2013. p. 407–44.Google Scholar