Complexation of tyrosol with cyclodextrins

García-Padial, M.; Martínez-Ohárriz, María Cristina; Isasi, José Ramón; Vélaz, Itziar; Zornoza, Arantza

doi:10.1007/s10847-011-0095-3

Cited by 8 publications

(14 citation statements)

References 19 publications

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“…Observed changes might be explained by the strong binding capacity of bile salts that can interact with phenolic hydroxyl groups to form hydrogen/ionic bonds [37]. Formation of inclusion complexes or aggregates of TS with bCD and hpbCD [38] might prevent adsorption resulting in increased bioavailability. Despite the significant increase of TS amount in all samples, their antioxidative potential did not change significantly which could be a confirmation of its weak antioxidant potential.…”

Section: Bioaccessibility Of Olive Pomace Polyphenolsmentioning

confidence: 99%

Influence of Pomace Matrix and Cyclodextrin Encapsulation on Olive Pomace Polyphenols’ Bioaccessibility and Intestinal Permeability

2020

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Olive pomace is a rich source of biologically active compounds, mainly polyphenols. Recently, an efficient and sustainable cyclodextrin (CD)-enhanced extraction was developed. It enabled a relatively simple formulation of high-quality olive pomace extracts (OPEs) that can be used as alternative sources of olive-derived polyphenols in the nutrition and pharma industries. However, biological effects and nutraceutical potential of OPEs are primarily limited by generally low oral bioavailability of major polyphenols (hydroxytyrosol and its derivatives) that can be significantly influenced by OPE matrix and the presence of CDs in formulation. The major goal of this research was to investigate the impact of complex matrix and different types of CDs on gastrointestinal stability and intestinal permeability of major OPE polyphenols, and provide additional data about mechanisms of absorption and antioxidant activity in gut lumen. Obtained results showed high bioaccessibility but relatively low permeability of OPE polyphenols, which was negatively affected by OPE matrix. CDs improved antioxidant efficiency of tested OPEs and tyrosol gastrointestinal stability. Effects of CDs on permeability and the metabolism of particular OPE polyphenols were CD-and polyphenol-specific.Nutrients 2020, 12, 669 2 of 16 oxidative stress in the intestine is particularly important given that numerous studies have shown that oxidative stress is directly linked to the development of diseases of the GI tract, such as inflammatory bowel disease and tumor colon. The intestine is the site that was shown to be extremely susceptible to oxidative stress. Namely, lipid peroxidation (as a chain reaction that lead to deleterious cell membrane damage) can be initiated by dietary fats.Considering its phenolic composition, olive pomace is very similar to olive oil and represents an inexpensive and readily available source of HTS derivatives. In the last decade, the potential of the olive pomace as a rich source of biologically active compounds has been recognized in scientific and professional literature, resulting in the development of a large number of effective extraction procedures [6,7]. However, the poor technological properties of raw olive pomace extracts (OPE) limit their wider application as nutraceuticals and food additives [7]. The main prerequisites for obtaining usable OPE are high yield of HTS derivatives, stability, and satisfactory technological properties of dry extracts. In this regard, cyclodextrins (CDs) were successfully applied for achieving higher polyphenol yields and the formulation of stable and organoleptically acceptable olive pomace extracts (OPEs) [7]. Moreover, α-CD, β-CD, and γ-CD are listed on the generally regarded as safe (GRAS) list of the U.S. Food and Drug Administration (FDA) for use as a food additive [8][9][10].In addition to demonstrating favorable chemical composition and technological properties, the quality of OPE is significantly determined by bioavailability and biological activity of its main active components...

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Section: Bioaccessibility Of Olive Pomace Polyphenolsmentioning

confidence: 99%

Influence of Pomace Matrix and Cyclodextrin Encapsulation on Olive Pomace Polyphenols’ Bioaccessibility and Intestinal Permeability

2020

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“…Hence, it can be suggested that solid β-CD does not express selectivity in its extraction of Tyr or HT despite the higher affinity of the former for β-CD in aqueous solution, which is reflected by a ca. 10 times higher binding constant [ 21 ]. This is an indication that extraction does not proceed by the encapsulation of the phenols inside the β-CD cavity (as in aqueous solution) but rather by adsorption on the macrocycle’s surface, probably by hydrogen bonding.…”

Section: Resultsmentioning

confidence: 99%

“…Only a few studies have focused on the complexes of HT and Tyr with β-CD in the solid state. For instance, Garcia-Padial et al [ 21 ] prepared the solid Tyr-β-CD complex by co-evaporation and kneading.…”

Section: Introductionmentioning

confidence: 99%

One-Step Extraction of Olive Phenols from Aqueous Solution Using β-Cyclodextrin in the Solid State, a Simple Eco-Friendly Method Providing Photochemical Stability to the Extracts

et al. 2021

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The extraction of phenolic compounds from olive mill wastes is important, not only to avoid environmental damages, but also because of the intrinsic value of those biophenols, well-known for their high antioxidant potential and health benefits. This study focuses on tyrosol (Tyr) and hydroxytyrosol (HT), two of the main phenolic compounds found in olive mill wastes. A new, simple, and eco-friendly extraction process for the removal of phenolic compounds from aqueous solutions using native β-cyclodextrin (β-CD) in the solid state has been developed. Several β-CD/biophenol molar ratios and biophenol concentrations were investigated, in order to maintain β-CD mostly in the solid state while optimizing the extraction yield and the loading capacity of the sorbent. The extraction efficiencies of Tyr and HT were up to 61%, with a total solid recovery higher than 90% using an initial concentration of 100 mM biophenol and 10 molar equivalents of β-CD. The photochemical stability of the complexes thus obtained was estimated from ∆E*ab curve vs. illumination time. The results obtained showed that the phenols encapsulated into solid β-CD are protected against photodegradation. The powder obtained could be directly developed as a safe-grade food supplement. This simple eco-friendly process could be used for extracting valuable biophenols from olive mill wastewater.

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“…Briefly, equimolar quantities of βCD (569 mg) and TYR (70 mg) were mixed in an agate mortar and pestle with minimum amount of the solvent (H 2 O:EtOH 7:3 v/v) for 30 min. The paste was dried to constant weight in a high vacuum pump [ 27 ].…”

Section: Methodsmentioning

confidence: 99%

Encapsulation of the Natural Product Tyrosol in Carbohydrate Nanosystems and Study of Their Binding with ctDNA

et al. 2020

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Tyrosol, a natural product present in olive oil and white wine, possesses a wide range of bioactivity. The aim of this study was to optimize the preparation of nanosystems encapsulating tyrosol in carbohydrate matrices and the investigation of their ability to bind with DNA. The first encapsulation matrix of choice was chitosan using the ionic gelation method. The second matrix was β-cyclodextrin (βCD) using the kneading method. Coating of the tyrosol-βCD ICs with chitosan resulted in a third nanosystem with very interesting properties. Optimal preparation parameters of each nanosystem were obtained through two three-factor, three-level Box-Behnken experimental designs and statistical analysis of the results. Thereafter, the nanoparticles were evaluated for their physical and thermal characteristics using several techniques (DLS, NMR, FT-IR, DSC, TGA). The study was completed with the investigation of the impact of the encapsulation on the ability of tyrosol to bind to calf thymus DNA. The results revealed that tyrosol and all the studied systems bind to the minor groove of ctDNA. Tyrosol interacts with ctDNA via hydrogen bond formation, as predicted via molecular modeling studies and corroborated by the experiments. The tyrosol-chitosan nanosystem does not show any binding to ctDNA whereas the βCD inclusion complex shows analogous interaction with that of free tyrosol.

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Complexation of tyrosol with cyclodextrins

Cited by 8 publications

References 19 publications

Influence of Pomace Matrix and Cyclodextrin Encapsulation on Olive Pomace Polyphenols’ Bioaccessibility and Intestinal Permeability

Influence of Pomace Matrix and Cyclodextrin Encapsulation on Olive Pomace Polyphenols’ Bioaccessibility and Intestinal Permeability

One-Step Extraction of Olive Phenols from Aqueous Solution Using β-Cyclodextrin in the Solid State, a Simple Eco-Friendly Method Providing Photochemical Stability to the Extracts

Encapsulation of the Natural Product Tyrosol in Carbohydrate Nanosystems and Study of Their Binding with ctDNA

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