Strategies to improve the solubility and stability of stilbene antioxidants: A comparative study between cyclodextrins and bile acids

•Novel HPLC-DAD method for the simultaneous determination of 3 trans-stilbenes.•Comparison of stilbene solubility in inclusion complexes and micellar systems.•Cyclodextrins increased stilbene solubility up to 6 log-fold increase.•Cyclodextrin-stilbene interaction occurs mainly through the double bon...

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Bibliographic Details
Published in:Food chemistry 2014-02, Vol.145, p.115-125
Main Authors: Silva, Filomena, Figueiras, Ana, Gallardo, Eugenia, Nerín, Cristina, Domingues, Fernanda C.
Format: Article
Language:English
Subjects:
Antioxidants - analysis
Bile Acids and Salts - chemistry
Bile salts
Biological and medical sciences
Calorimetry, Differential Scanning
Chromatography, High Pressure Liquid
Cyclodextrins
Cyclodextrins - chemistry
Food toxicology
HPLC-DAD
Inclusion complexes
Magnetic Resonance Spectroscopy
Medical sciences
Micelles
Photostability
Solubility
Solutions
Spectroscopy, Fourier Transform Infrared
Stilbenes
Stilbenes - analysis
Toxicology
X-Ray Diffraction
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Summary:•Novel HPLC-DAD method for the simultaneous determination of 3 trans-stilbenes.•Comparison of stilbene solubility in inclusion complexes and micellar systems.•Cyclodextrins increased stilbene solubility up to 6 log-fold increase.•Cyclodextrin-stilbene interaction occurs mainly through the double bond protons.•Stilbene photostability was increased due to the inclusion in CDs. Aiming at the development of an active food packaging, the goal of this study was to increase stilbenes (resveratrol (RV), pterostilbene (PT) and pinosylvin (PS)) aqueous solubility and stability using hydropropyl-cyclodextrins (HP-CDs) and bile salts. To evaluate stilbene concentration, an HPLC-DAD method was validated. Stilbene solubility was improved by the formation of inclusion complexes and micellar systems with higher solubility values obtained for the inclusion complexes with cyclodextrins. Inclusion complexes revealed a 1:1 stoichiometry for RV and PT and a 1:2 for PS. Solid state characterisation was carried out using X-ray diffraction, Fourier transform infrared spectroscopy and differential scanning calorimetry. 1H NMR studies were also performed to characterise the prepared complexes. Photostability studies revealed that CDs were able to increase stilbene photostability at 4°C. This work showed that stable stilbene solutions can be achieved using hydroxypropyl-CDs, contributing for their incorporation in several materials for the food and pharmaceutical industries.
ISSN:0308-8146
1873-7072
DOI:10.1016/j.foodchem.2013.08.034