Issue 1, 2017

An integral study of cyclodextrins as solubility enhancers of α-methylstilbene, a resveratrol analogue

Abstract

trans-α-Methylstilbene (tMS), a resveratrol analogue, has recently been studied in a search for new bioactivities. However, such studies do not take into account that the poor solubility of tMS in aqueous solutions could affect its bioactivity. For this reason, we propose, for the first time, using cyclodextrins (CDs) as solubilizers to increase tMS solubility, in aqueous solutions. The HPLC-RP results obtained, point to a 1 : 1 stoichiometry for all the natural (α-, β- and γ-CD) and modified (HPβCD and MβCD) CDs tested. The KFapp (apparent formation constant) for the tMS–CD complexes was seen to be closely dependent on several factors, including the temperature and type of CD. Indeed, the highest KFapp value was obtained for MβCD, while the KFapp decreased with increasing temperature. In addition, the results showed negative entropy (−8.86 × 10−3 ± 0.40 kJ mol−1 K−1) and enthalpy (−16.70 ± 0.98 kJ mol−1) changes and a negative Gibbs free energy value at 25 °C (−14.00 ± 0.55 kJ mol−1) for the encapsulation process. A computational study carried out using molecular docking calculations showed a high degree of correlation between the computed scores and experimental values. Finally, the complexation of trans-stilbene and pinosylvin with HPβCD was compared with tMS.

Graphical abstract: An integral study of cyclodextrins as solubility enhancers of α-methylstilbene, a resveratrol analogue

Supplementary files

Article information

Article type
Paper
Submitted
16 Nov 2016
Accepted
06 Dec 2016
First published
06 Dec 2016

Food Funct., 2017,8, 270-277

An integral study of cyclodextrins as solubility enhancers of α-methylstilbene, a resveratrol analogue

A. Matencio, S. Hernández-García, F. García-Carmona and J. M. López-Nicolás, Food Funct., 2017, 8, 270 DOI: 10.1039/C6FO01677D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements