PREPARATION AND CHARACTERIZATION OF RESVERATROL/HYDROXYPROPYL‐β‐CYCLODEXTRIN INCLUSION COMPLEX USING SUPERCRITICAL ANTISOLVENT TECHNOLOGY

Abstract

The inclusion complex of resveratrol (RV) and hydroxypropyl‐β‐cyclodextrin (HP‐β‐CD) prepared by supercritical antisolvent (SAS) process was investigated to improve its aqueous solubility. The phase solubility diagram with HP‐β‐CD was classified as AL type, and the calculated apparent complexation constant (KC) was 5,988 M−1 at 298K. Inclusion complexes were analyzed by differential scanning calorimetry (DSC), powder X‐ray diffractometry (PXRD), Fourier‐transform infrared spectroscopy (FT‐IR) and scanning electron microscopy (SEM). No endothermic and characteristic diffraction peaks corresponding to RV were observed for the inclusion complex in DSC and PXRD. FT‐IR study demonstrated the presence of intermolecular hydrogen bonds between RV and HP‐β‐CD in inclusion complex, resulting in the formation of amorphous form. Furthermore, the SAS‐processed RV/ HP‐β‐CD powders showed a significant enhancement in the solubility of RV (up to 25.13 mg/mL) in an aqueous medium. The percent dissolution of RV increased considerably and about 100% of RV was dissolved within 5–10 min. PRACTICAL APPLICATIONS In this study, the supercritical antisolvent (SAS) process was effectively utilized to prepare solid‐state inclusion complexes of resveratrol (RV) and hydroxypropyl‐β‐cyclodextrin (HP‐β‐CD). The SAS‐processed RV/HP‐β‐CD powders showed a significant enhancement in the solubility of RV (up to 25.13 mg/mL) in an aqueous medium. The percent dissolution of RV increased considerably and about 100% of RV was dissolved within 5–10 min. This work thoroughly overcomes the high hydrophobicity and sensitivity of resveratrol to air and light, so that obviously enlarges the application in pharmaceutical, chemical, food and cosmetic industries.

Physico-chemical studies of resveratrol, methyl-jasmonate and cyclodextrin interactions: an approach to resveratrol bioproduction optimization

“…22 Conversely, Zhou et al obtained similar results to ours with b-CD and HP-b-CD in the same range of concentrations. 28 Moreover, it is oen assumed that the linear trend of the phase solubility diagram indicates the formation of a 1 : 1 complex. For a guest molecule with limited aqueous solubility such as RSV (0.1 mM at saturation), it is well-known that the association constant value cannot be determined accurately with this method (Table SI †) and the notion of Complexation Efficiency (CE) was introduced by Losson et al to compare the solubilizing effect of different CDs on a guest molecule.…”

Encapsulation and protection of resveratrol in kafirin and milk protein nanoparticles

“…IR spectra of kafirin, β‐Lg and casein showed the characteristic absorption bands of proteins, with the peaks for O–H around 3300 cm −1 and the peaks for stretching of CH 3 and CH 2 between 2925 and 2960 cm −1 , and the amide I and II peaks around 1650 and 1540 cm −1 (Chen & Zhong, ). Most of the characteristic peaks of resveratrol (1606, 1586, 1384 and 965 cm −1 ) disappeared when the polyphenol was encapsulated in kafirin/β‐Lg and kafirin/casein nanoparticles, in line with the polyphenol complexation with hydroxypropyl‐β‐cyclodextrin (Zhou et al ., ) and encapsulation in zein‐casein and gliadin‐pectin nanoparticles (Davidov‐Pardo et al ., ). The disappearance of resveratrol peaks was due to the reduced stretching and bending of resveratrol bonds and transformation of resveratrol from crystalline to amorphous state (Davidov‐Pardo et al ., ).…”

“…However, its application in food and pharmaceutical industries is limited due to poor hydro-solubility, chemical instability and low bioavailability (Summerlin et al, 2015). The limitations for the use of resveratrol as a nutraceutical could be overcome to some extent by complexation with hydroxypropyl-b-cyclodextrin and b-Lg and by encapsulation using liposomes, calciumalginate submicron particles, zein-and gliadin-based nanoparticles, nanoemulsions and solid lipid nanoparticles (Liang et al, 2008;Zhou et al, 2012;Sessa et al, 2014;Davidov-Pardo et al, 2015b;Isteni c et al, 2015).…”

Formation of Rutin–β-Cyclodextrin Inclusion Complexes by Supercritical Antisolvent Precipitation

“…The characteristic bands of RUT are evident in the spectrum of RUT + β-CD physical mixture unlike the spectra of SAS-processed powders RUT–β-CD both at 1:2 mol/mol and 1:1 mol:mol. The disappearance of absorption bands or the reduction in peak intensity in the FT-IR spectra of active compound–β-CD samples can be attributed to the formation of inclusion complexes [ 20 , 31 , 32 , 33 , 34 , 46 ], since the active compound (guest) is incorporated into the β-CD cavity (host). In addition to the partial or complete disappearance of RUT bands, like those at 1169, 1362, and 1654 cm −1 , it is possible to note a shift of the RUT band at 1600 cm −1 towards slightly higher wavenumbers, as observable in the enlargement of FT-IR spectra reported in Figure 7 b.…”

“…A possible solution that aims at the coprecipitation with a lower quantity of polymeric carrier consists of the use of CDs. However, the SAS technique was applied to prepare CD-based inclusion complexes in a limited number of literature studies [ 20 , 31 , 32 , 33 , 34 , 35 , 36 ]. Moreover, in none of them, the preparation of inclusion complexes containing RUT was attempted, despite the numerous benefits offered by RUT for human health.…”