Hesperidin and hesperetin membrane interaction: understanding the role of 7-O-glycoside moiety in flavonoids.
Citrus species contain various typical flavonoids. However, absorption and metabolism of flavonoids are complex processes that determine its bioavailability which remain not clear until now. The aim of this study was to investigate the interactions among dimyristoyl-phosphatidyl choline (DMPC) liposomes and the flavanones hesperidin (glycoside) and hesperetin (aglycone). The results describe the molecular details of these interactions and the consequences for the membranes properties, by using differential scanning calorimetry (DSC), atomic force microscopy (AFM), fluorescence (using MC540 as probe), X-ray diffraction and theoretical study. The results show that hesperetin interacts with membranes stronger than hesperidin. It is possible to hypostatize that hesperidin, due to its rutinoside moiety, is located at the level of polar head whereas hesperetin interacts better with acyl chains and adopts a more planar conformation. The findings of this work may contribute to explain the high bioavailability of aglycones due to better membrane interaction.
Londoño-Londoño
Julián
J
Universidad de Antioquia, Grupo de Investigación en Sustancias Bioactivas, Sede de Investigación Universitaria (SIU), A.A. 1226 Medellín, Colombia. jalondo@gmail.com
Lima
Vânia Rodrigues De
VR
Jaramillo
Consuelo
C
Creczynski-Pasa
Tânia
T
D001682:Biological Availability; D002152:Calorimetry, Differential Scanning; D002957:Citrus / Q000737:chemistry; D004134:Dimyristoylphosphatidylcholine; D006027:Glycosides / Q000737:chemistry; D006569:Hesperidin / Q000737:chemistry* / Q000493:pharmacokinetics; D006801:Humans; D008081:Liposomes; D008564:Membrane Potentials; D008567:Membranes, Artificial; D018625:Microscopy, Atomic Force; D008958:Models, Molecular; D033362:Powder Diffraction; D013050:Spectrometry, Fluorescence; D014961:X-Ray Diffraction
D006027:Glycosides; D008081:Liposomes; D008567:Membranes, Artificial; D006569:Hesperidin; C013015:hesperetin; D004134:Dimyristoylphosphatidylcholine