Abstract
Resveratrol (RES) is a naturally occurring product with numerous biological activities. Despite its potential benefits, its use is limited due to its low aqueous stability and solubility in its native form. The porous sol–gel silica materials which are able to entrap different organic molecules represent new studied release carriers. The aim of this work was to generate a solid matrix to encapsulate RES ensuring protection, increased solubility and release in solutions. A non-toxic ingredient, namely β-cyclodextrin (β-CD), able to form inclusion complexes (ICs) with RES has been used. Ecological formulations have been processed by entrapping the RES containing ICs in silica matrices obtained from a silica colloidal sol by the aqueous route of the sol–gel method. Characterization methods (DSC, FTIR, UV–Vis, fluorescence studies, SEM) have evidenced the presence of RES–β-CD inclusion complex in the silica powder, RES stability in the matrix and its release in aqueous and organic solutions, and the morphology of the carrier. An evaluation of the antioxidant activity of RES in the present formulation was performed by the chemiluminescence assay and RES release profile in aqueous solutions was obtained by HPLC–MS. The resulted materials can find applications in different domains.
Graphic abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alecu A, Albu C, Litescu SC, Eremia SAV, Radu GL (2016) Phenolic and anthocyanin profile of Valea Calugareasca red wines by HPLC-PDA-MS and MALDI-TOF analysis. Food Anal Methods 9:300–310. https://doi.org/10.1007/s12161-015-0197-4
Bertacche V, Lorenzi N, Nava D, Pini E, Sinico C (2006) Host-guest interaction study of resveratrol with natural and modified cyclodextrins. J Incl Phenom Macrocycl Chem 55:279–287. https://doi.org/10.1007/s10847-006-9047-8
Camont L, Collin F, Couturier M, Thérond P, Jore D, Gardès-Albert M, Bonnefont-Rousselot D (2012) Radical-induced oxidation of trans-resveratrol. Biochimie 94:741–747. https://doi.org/10.1016/j.biochi.2011.11.005
Cássia da Silva R, Teixeira JA, Nunes WDG, Zangaro GAC, Pivatto M, Caires FG, Ionashiro M (2017) Resveratrol: a thermoanalitycal study. Food Chem 237:561–565. https://doi.org/10.1016/j.foodchem.2017.05.146
Chakraborty S, Mitra MK, Chaudhuri MG, Sa B, Das S, Dey R (2012) Study of the release mechanism of Terminalia chebula extract from nanoporous silica gel. Appl Biochem Biotechnol 168:2043–2056. https://doi.org/10.1007/s12010-012-9916-0
Davidov-Pardo G, McClements DJ (2014) Resveratrol encapsulation: designing delivery systems to overcome solubility, stability and bioavailability issues. Trends Food Sci Technol 38(2):88–103. https://doi.org/10.1016/j.tifs.2014.05.003
Hernandez-Montelongo J, Naveas JN, Degoutin S, Tabary N, Chai F, Spampinato V, Ceccone G, Rossi F, Torres-Costa V, Manso-Silvan M, Martel B (2014) Porous silicon-cyclodextrin based polymer composites for drug delivery applications. Carbohydr Polym 110:238–252. https://doi.org/10.1016/j.carbpol.2014.04.002
López-Nicolás JM, García-Carmona F (2008a) Rapid, simple and sensitive determination of the apparent formation constants of trans-resveratrol complexes with natural cyclodextrins in aqueous medium using HPLC. Food Chem 109:868–875. https://doi.org/10.1016/j.foodchem.2008.01.022
López-Nicolás JM, García-Carmona F (2008b) Aggregation State and pKa values of (E)-Resveratrol as determined by fluorescence spectroscopy and UV-visible absoption. J Agric Food Chem 56:7600–7605. https://doi.org/10.1021/jf800843e
Lu Z, Cheng B, Hu Y, Zhang Y, Zou G (2009) Complexation of resveratrol with cyclodextrins: solubility and antioxidant activity. Food Chem 113:17–20. https://doi.org/10.1016/j.foodchem.2008.04.042
Lucas-Abellán C, Fortea I, López-Nicolás JM, Núňez-Delicado E (2007) Cyclodextrins as resveratrol carrier system. Food Chem 104:39–44. https://doi.org/10.1016/j.foodchem.2006.10.068
Maleki A, Kettiger H, Schoubben A, Rosenholm JM, Ambrogi V, Hamidi M (2017) Mesoporous silica materials: from physico-chemical properties to enhanced dissolution of poorly water-soluble drugs. J Control Release 262:329–347. https://doi.org/10.1016/j.jconrel.2017.07.047
Parfenyuk EV, Dolinina ES (2014) Design of silica carrier for controlled release of molsidomine: effect of preparation methods of silica matrices and their composites with molsidomine on the drug release kinetics in vitro. Eur J Pharm Biopharm 88(3):1038–1045. https://doi.org/10.1016/j.ejpb.2014.09.007
Popova M, Szegedi A, Mavrodinova V, Tušar NN, Mihály J, Klébert S, Benbassat N, Yoncheva K (2014) Preparation of resveratrol-loaded nanoporous silica materials with different structures. J Solid State Chem 219:37–42. https://doi.org/10.1016/j.jssc.2014.07.002
Răileanu M, Todan L, Voicescu M, Ciuculescu C, Maganu M (2013) A way for improving the stability of the essential oils in an environmental friendly formulation. Mater Sci Eng C 33:3281–3288. https://doi.org/10.1016/j.msec.2013.04.012
Roik NV, Belyakova LA (2011) Thermodynamic, IR spectral and X-ray diffraction studies of the “β-cyclodextrin-para-aminobenzoic acid” inclusion complex. J Incl Phenom Macrocycl Chem 69:315–319. https://doi.org/10.1007/s10847-010-9737-0
Salehi B, Mishra AP, Nigam M, Sener B, Kilic M, Sharifi-Rad M, Fokou PVT, Martins N, Sharifi-Rad J (2018) Resveratrol: a double-edged sword in health benefits. Biomedicine 6(3):91. https://doi.org/10.3390/biomedicines6030091
Santos AC, Pereira I, Pereira-Silva M, Ferreira L, Caldas M, Collado-González M, Magalhães M, Figueiras A, Ribeiro AJ, Veiga F (2019a) Nanotechnology-based formulations for resveratrol delivery: effect on resveratrol in vivo bioavailability and bioactivity. Colloids Surf B Biointerfaces 180:127–140. https://doi.org/10.1016/j.colsurfb.2019.04.030
Santos AC, Pereira I, Pereira-Silva M, Ferreira L, Caldas M, Magalhães M, Figueiras A, Ribeiro AJ, Veiga F (2019b) Nanocarriers for resveratrol delivery: impact on stability and solubility concerns. Trends Food Sci Technol 91:483–497. https://doi.org/10.1016/j.tifs.2019.07.048
Summerlin N, Soo E, Thakur S, Qu Z, Jambhrunkar S, Popat A (2015) Resveratrol nanoformulations: challenges and opportunities. Int J Pharm 479(2):282–290. https://doi.org/10.1016/j.ijpharm.2015.01.003
Tabibiazar M, Mohammadifar MA, Roufegarinejad L, Ghorbani M, Hashemi M, Hamishehkar H (2019) Improvement in dispersibility, stability and antioxidant activity of resveratrol using a colloidal nanodispersion of BSA-resveratrol. Food Biosci 27:46–53. https://doi.org/10.1016/j.fbio.2018.10.015
Todan L, Andronescu C, Vuluga DM, Culita DC, Zaharescu M (2013) Thermal behavior of silicophosphate gels obtained from different precursors. J Therm Anal Calorim 114:91–99. https://doi.org/10.1007/s10973-012-2875-4
Vasilescu M, Voicescu M, Lemmetyinen H, Meghea A (2004) The oxidative activity of riboflavin studied by luminescence methods. Rom J Biochem 41:51–63. https://doi.org/10.1016/j.colsurfb.2017.01.019
Veres P, Kéri M, Bányai I, Lázár I, Fábián I, Domingo C, Kalmár J (2017) Mechanism of drug release from silica-gelatin aerogel—relationship between matrix structure and release kinetics. Colloids and Surf B Biointerfaces 152:229–237
Voicescu M, Ionita G, Constantinescu T, Vasilescu M (2006a) The oxidative activity of riboflavin studied by luminescence methods: the effect of cysteine, arginine, lysine and histidine amino acids. Rev Roum Chim 51:683–690
Voicescu M, Ionita G, Vasilescu M, Meghea A (2006b) The effect of cyclodextrins on the luminol-hydrogen peroxide chemiluminescence. J Incl Phenom Macrocyclic Chem 54:217–219. https://doi.org/10.1007/s10847-005-7390-9
Voicescu M, Ionita G, Beteringhe A, Vasilescu M, Meghea A (2008) The antioxidative activity of riboflavin in the presence of antipyrine. Spectroscopic studies. J Fluoresc 18:953–959. https://doi.org/10.1007/s10895-008-0354-x
Voicescu M, Ion R, Meghea A (2010) Evaluation of the oxidative activity of some free base porphyrins by a chemiluminescence method. J Serb Chem Soc 75:333–341
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
On behalf of all authors, the corresponding author states that there is no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Todan, L., Voicescu, M., Culita, D.C. et al. Ecological formulation for improving resveratrol stability and release in aqueous environment. Chem. Pap. 75, 2033–2041 (2021). https://doi.org/10.1007/s11696-020-01409-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-020-01409-6