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Vitamin D plays an important role in numerous cellular functions due to the ability to bind the Vitamin D receptor (VDR), which is present in different tissues. Several human diseases depend on low vitamin D3 (human isoform) serum level, and supplementation is necessary. However, vitamin D3 has poor bioavailability, and several strategies are tested to increase its absorption. In this work, the complexation of vitamin D3 in Cyclodextrin-based nanosponge (CD-NS, in particular, βNS-CDI 1:4) was carried out to study the possible enhancement of bioactivity. The βNS-CDI 1:4 was synthesized by mechanochemistry, and the complex was confirmed using FTIR-ATR and TGA. TGA demonstrated higher thermostability of the complexed form. Subsequently, in vitro experiments were performed to evaluate the biological activity of Vitamin D3 complexed in the nanosponges on intestinal cells and assess its bioavailability without cytotoxic effect. The Vitamin D3 complexes enhance cellular activity at the intestinal level and improve its bioavailability. In conclusion, this study demonstrates for the first time the ability of CD-NS complexes to improve the chemical and biological function of Vitamin D3.

Stilbenes are phenolic compounds naturally synthesized as secondary metabolites by the shikimate pathway in plants. Research on them has increased in recent years due to their therapeutic potential as antioxidant, antimicrobial, anti-inflammatory, anticancer, cardioprotective and anti-obesity agents. Amongst them, resveratrol has attracted the most attention, although there are other natural and synthesized stilbenes with enhanced properties. However, stilbenes have some physicochemical and pharmacokinetic problems that need to be overcome before considering their applications. Human clinical evidence of their bioactivity is still controversial due to this fact and hence, exhaustive basis science on stilbenes is needed before applied science. This review gathers the main physicochemical and biological properties of natural stilbenes, establishes structure-activity relationships among them, emphasizing the current problems that limit their applications and presenting some promising approaches to overcome these issues: the encapsulation in different agents and the structural modification to obtain novel stilbenes with better features. The bioactivity of stilbenes should move from promising to evident.

Gnetol is a stilbene whose characterization and bioactivity have been poorly studied. It shares some bioactivities with its analogue resveratrol, such as anti-inflammatory, anti-thrombotic, cardioprotective and anti-cancer activities. However, the low solubility of stilbenes may limit their potential applications in functional foods. Encapsulation in cyclodextrins could be a solution.The antioxidant activity of gnetol was evaluated by 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation and ferric reducing antioxidant power methods (Trolox equivalents 13.48 μmol LThese results could increase interest of gnetol as an alternative to the most studied stilbene, resveratrol, as well as aid in the development of more stable inclusion complexes that improve its aqueous solubility and stability so that it can be incorporated into functional foods. © 2022 The Authors. Journal of The Science of Food and Agriculture published by John WileySons Ltd on behalf of Society of Chemical Industry.

The food industry is constantly attempting to develop better products that will have a positive effect on health. Feiraco® and Clesa®, expressed their intention to create novel products using UNICLA® milk as a matrix to develop functional foods. In this respect, β-cyclodextrin (β-CD) at 1% was able to reduce the cholesterol concentration in Feiraco-UNICLA® milk products by around 87-85%. Products were fortified with omega-3 from fish oil with α- and β-CD acting as carriers. It was possible to add around 50% of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) Recommended Dietary Allowances (RDA), with a high diet proportion of fibre and similar organoleptic properties to commercial omega-3 products. 80% of a sensory panel found our formulations satisfactory. The final product was stable, and the bioaccessibilty of the fatty acids added to the milk was around 74%. These results as a whole satisfy the aid of Feiraco® and Clesa® to develop improved products.

Many nutraceuticals present problems due to their poor water solubility or stability, which prevents the final bioactivity achievement. For that reason, the oral administration of KYNA complexed with HPβ-CD and βNS-CDI nanosponges was evaluated in mice. The solvent-free technology was used to prepare the complexes in a complete comparison between kneading in ball milling and classical inclusion complex preparation. The solvent-free ones showed higher strength and efficiency with ball milling, considerably reducing time. A 50 mg KYNA/kg/day dosage was orally administered in formulations showing a higher bioavailability when the nutraceutical was complexed with βNS-CDI compared to HPβ-CD and free KYNA, respectively. Several antioxidant statuses demonstrated a higher global antioxidant level perfectly related to bioavailability. Finally, the formulation of KYNA reduced the temporal oxidative stress damage in the kidney and liver, making βNS-CDI the best formulation. These results suggest an important future application of cyclodextrin-based nanosponges for the oral delivery of nutraceuticals and their stabilization.

Neochlorogenic acid, a less-studied isomer of chlorogenic acid, has been seen to posses antioxidant, antifungal, anti-inflammatory and anticarcinogenic effects, which makes it an interesting candidate for incorporation in functional foods. However, its poor solubility in water and susceptibility to oxidation make such a task difficult. To overcome that, its encapsulation in cyclodextrins (CDs) is proposed. The fluorescence of neochlorogenic acid in different pH conditions was analyzed, and caffeic acid was proved to be the fluorescent moiety in the molecule. An encapsulation model whereby the ligand poses two potential complexation sites (caffeic and D-(-)-quinic moieties), showed that α-CD and HP-β-CD formed the best inclusion complexes with neochlorogenic acid, followed by M-β-CD, β-CD and γ-CD. Molecular docking with the two best CDs gave better scores for α-CD, despite HP-β-CD providing stabilization through H-bonds. The encapsulation of chlorogenic acid led to a similar CD order and scores, although constants were higher for α-CD, β-CD and M-β-CD, lower for HP-β-CD, and negligible for γ-CD. The protonation state affected these results leading to a different order of CD preference. The solubility and the susceptibility to oxidation of neochlorogenic acid improved after complexation with α-CD and HP-β-CD, while the antioxidant activity of both isomers was maintained.

This study aimed to design and fabricate novel hydroxypropyl-β-cyclodextrin-based hypercrosslinked polymers, called nanosponges, as carriers for anticancer hydrophobic agents and compare them with host–guest complexes of hydroxypropyl-β-cyclodextrin, a remarkable solubilizer, to investigate their application in improving the pharmaceutical properties of the flavonoid naringenin, a model hydrophobic nutraceutical with versatile anticancer effects. For this purpose, three new nanosponges, crosslinked with pyromellitic dianhydride, citric acid, and carbonyldiimidazole, were fabricated. The carbonate nanosponge synthesized by carbonyldiimidazole presented the highest naringenin loading capacity (≈19.42%) and exerted significantly higher antiproliferative effects against MCF-7 cancer cells compared to free naringenin. Additionally, this carbonate nanosponge formed a stable nanosuspension, providing several advantages over the naringenin/hydroxypropyl-β-cyclodextrin host–guest complex, including an increase of about 3.62-fold in the loading capacity percentage, sustained released pattern (versus the burst pattern of host–guest complex), and up to an 8.3-fold increase in antiproliferative effects against MCF-7 cancer cells. Both naringenin-loaded carriers were less toxic to L929 murine fibroblast normal cells than MCF-7 cancer cells. These findings suggest that hydroxypropyl-β-cyclodextrin-based carbonate nanosponges could be a good candidate as a drug delivery system with potential applications in cancer treatment.

The great variability of cancer types demands novel drugs with broad spectrum, this is the case of Nisin, a polycyclic antibacterial peptide that recently has been considered for prevention of cancer cells growth. As an accepted food additive, this drug would be very useful for intestinal cancers, but the peptide nature would make easier its degradation by digestion procedures. For that reason, the aim of present study to investigate the protective effect of two different β-cyclodextrin-based nanosponges (carbonyl diimidazole and pyromellitic dianhydride) and their anti-cancer enhancement effect of Nisin-Z encapsulated with against colon cancer cells (HT-29). To extend its possible use, a comparison with breast (MCF-7) cancer cell was carried out. The physicochemical properties, loading efficiency, and release kinetics of Nisin complex with nanosponges were studied. Then, tricin-SDS-PAGE electrophoresis was used to understand the effect of NSs on stability of Nisin-Z in the presence of gastric peptidase pepsin. In addition, the cytotoxicity and cell membrane damage of Nisin Z were evaluated by using the MTT and LDH assay, which was complemented via Annexin-V/ Propidium Iodide (PI) by using flowcytometry. CD-NS are able to complex Nisin-Z with an encapsulation efficiency around 90%. A protective effect of Nisin-Z complexed with CD-NSs was observed in presence of pepsin. An increase in the percentage of apoptotic cells was observed when the cancer cells were exposed to Nisin Z complexed with nanosponges. Interestingly, Nisin Z free and loaded on PMDA/CDI-NSs is more selectively toxic towards HT-29 cells than MCF-7 cancer cells. These results indicated that nanosponges might be good candidates to protect peptides and deliver drugs against intestinal cancers.

The ability of cyclodextrins to enhance the water solubility of lipophilic compounds is used to modify the water-based Oxygen Radical Absorbance Capacity (ORAC) method to measure antioxidant activity in vitro. However, the use of these solubility enhancers may alter fluorescent readings, which has led to contradictory results being described in the literature. The low specificity of these oligosaccharides and their controlled release effect can result in cyclodextrins forming inclusion complexes with other reagents in the assay, changing the kinetics. In this study, the cause of cyclodextrins' interference in the ORAC method is evaluated through a physicochemical and computational approach. Cyclodextrins showed a clear increase in the fluorescent signal both in the presence and absence of the antioxidant oxyresveratrol, the precise effect being dependent on the type and concentration of cyclodextrin. Although the glucidic nature of cyclodextrins could play a minimal role in this effect, it seems that the main cause was the encapsulation of other substrates in the reaction, fluorescein and AAPH.

In this article, we used monolayer two dimensional (2D) and 3D multicellular spheroid models to improve our understanding of the gene delivery process of a new modified cationic hyper-branched cyclodextrin-based polymer (Ppoly)-loaded plasmid encoding Enhanced Green Fluorescent Protein (EGFP). A comparison between the cytotoxicity effect and transfection efficiency of the plasmid DNA (pDNA)-loaded Ppoly system in 2D and 3D spheroid cells determined that the transfection efficiency and cytotoxicity of Ppoly–pDNA nanocomplexes were lower in 3D spheroids than in 2D monolayer cells. Furthermore, histopathology visualization of Ppoly–pDNA complex cellular uptake in 3D spheroids demonstrated that Ppoly penetrated into the inner layers. This study indicated that the Ppoly, as a non-viral gene delivery system in complex with pDNA, is hemocompatible, non-toxic, high in encapsulation efficiency, and has good transfection efficiency in both 2D and 3D cell cultures compared to free pDNA and lipofectamine (as the control).

Macrolides are widely used antibiotics with a broad spectrum of activity. The development of drug carriers to deliver this type of antibiotics has attracted much research. The present study aims at developing new swellable dextrin-based nanohydrogels for the topical delivery of rokitamycin, as model macrolide. Rokitamycin is a synthetic analogous of macrolides with advantageous characteristics as far as bacterial uptake and post-antibiotic effect are concerned. It is also indicated for the treatment of severe infections caused by Acanthamoeba and for topical infections. The nanohydrogels have been prepared from two types of cross-linked polymers obtained by using β-cyclodextrin or Linecaps® was provided by the Roquette Italia SPA (Cassano Spinola, Al, Italy) as building blocks. The cross-linked polymers have been then formulated into aqueous nanosuspensions refined and tuned to achieve the incorporation of the drug. Cross-linked β-cyclodextrin (β-CD) and Linecaps® (LC) polymers formed dextrin-based nanohydrogels with high swelling degree and mucoadhesion capability. Rokitamycin was loaded into the nanohydrogels displaying an average size around 200 nm with negative surface charge. In vitro kinetic profiles of free and loaded drug in nanohydrogels were compared at two pH levels. Interestingly, a sustained and controlled release was obtained at skin pH level due to the high degree of swelling and a pH responsiveness possibly. The results collected suggest that these nanohydrogels are promising for the delivery of rokitamycin and may pave the way for the topical delivery of other macrolide antibiotics.

Background 2-Phenylethanol (PEA) is a higher aromatic alcohol with a rose-like odor, which is used in several industries. Although PEA can be synthesized, consumers are increasingly concerned about the toxicity of chemically synthesized products, and prefer natural aroma compound. PEA occurs naturally in the environment but concentrations are too low to justify extraction. Results The present study offers a novel biological source of PEA: the filamentous fungi Monochaetinula geoffroeana. We report the highest recorded yield of PEA of fungal origin to date: 6.52 g L-1 . The volatility and low water solubility of PEA can affect its use in many industries, for which reason complexation studies of PEA and cyclodextrins were carried out using the phase solubility technique. PEA formed 1:1 stoichiometric inclusion complexes with natural and modified CDs, the highest encapsulation constant being obtained with MβCD (K1:1 = 299.88 L mol-1 ). The complexation process significantly increased the water solubility of PEA. A computational study showed a high degree of correlation between computed scores and experimental values. Furthermore, this study reports the role of salicylic acid as an effective elicitor for improved PEA production by the studied fungi. Supplementation with 10 μmol L-1 salicylic acid increased PEA production from 6.52 to 10.54 g L-1 . Conclusion The best treatment to enhance PEA production by M. geoffroeana under laboratory conditions was to use salicylic acid 10 μmol L-1 . Due to the commercial importance of PEA, further investigation is needed to improve PEA production by M. geoffroeana and to optimize culture conditions in order to standardize yields. © 2021 Society of Chemical Industry.

Cyclodextrin-based nanosponges (CD-NSs) have gained importance in drug delivery in the last years due to their easy synthesis and versatility. However, their use as carriers for the delivery of macromolecules such as proteins is less known and sometimes difficult to consider. In this entry, the authors summarize and highlight the multiple possibilities of CD-NSs to deliver active proteins, improving their activity or stability. Starting with a brief description of CD-NSs and their characteristics, the entry will be focused on several proteins, such as (1) Lipase, (2) Insulin and (3) Nisin, for chemical or pharmaceutical applications. The revised results demonstrated that CD-NSs can generate different and interesting applications with proteins. These results could be added to their uses with small drugs, being an interesting alternative for protein delivery and applicability.

Cyclodextrins (CDs) are a good alternative to reduce or enhance different biomolecule characteristics and have demonstrated great results in food science. However, CDs present intrinsic limitations that can be solved by derivative synthesis. This review represents a survey of the state of the art of CD-based materials and their uses in food science. A deep review of the structure is carried out and different groups for ordination are suggested. After that, different applications such as cholesterol complexation or its use as sensors are reviewed. The derivatives show novel and promising activities for the industry. A critical perspective of the materials suggests that they might not present toxicity, although more studies are required. These points suggest that the research in this field will be increased in the following years.

This study tested the anticoagulant effect of cyclodextrin (CD) hyper-branched-based polymers (HBCD-Pols). These polymers were synthesized and tested for their coagulant characteristics in vitro and in vivo. Due to their polymeric structure and anionic nature, the polymers can chelate Ca2+, reducing the free quantity in blood. HBCD-Pol increased the blood clotting time, PT, and aPTT 3.5 times over the control, showing a better effect than even ethylenediaminetetraacetic acid (EDTA), as occured with recalcification time as well. A titration of HBCD-Pol and EDTA showed exciting differences in the ability to complex Ca2+ between both materials. Before executing in vivo studies, a hemocompatibility study was carried out with less than 5% red blood cell hemolysis. The fibrinogen consumption and bleeding time were analyzed in vivo. The fibrinogen was considerably decreased in the presence of HBCD-Pol in a higher grade than EDTA, while the bleeding time was longer with HBCD-Pols. The results demonstrate that the anticoagulant effect of this HBCD-Pol opens novel therapy possibilities due to the possible transport of drugs in this carrier. This would give combinatorial effects and a potential novel anticoagulant therapy with HBCD-Pol per se.

Inflammation is a biological response of the immune system to harmful stimuli. Importantly, inflammation is also a hallmark of several human diseases such as cancer or diabetes. Novel drugs to treat this response are constantly researched, but the formulation is usually forgotten. Cyclodextrins (CDs) are a well-known excipient for complexing and drug delivery. Anti-inflammatory drugs and bioactive compounds with similar activities have been favored from these CD processes. CDs also illustrate anti-inflammatory activity per se. This review tried to describe the capacities of CDs in this field, and is divided into two parts: Firstly, a short description of the inflammation disease (causes, symptoms, treatment) is explained; secondly, the effects of different CDs alone or forming inclusion complexes with drugs or bioactive compounds are discussed.

Cyclodextrins (CDs) and cyclodextrin (CD)-based polymers are well-known complexing agents. One of their distinctive features is to increase the quantity of a drug in a solution or improve its delivery. However, in certain instances, the activity of the solutions is increased not only due to the increase of the drug dose but also due to the drug complexation. Based on numerous studies reviewed, the drug appeared more active in a complex form. This review aims to summarize the performance of CDs and CD-based polymers as activity enhancers. Accordingly, the review is divided into two parts, i.e., the effect of CDs as active drugs and as enhancers in antimicrobials, antivirals, cardiovascular diseases, cancer, neuroprotective agents, and antioxidants.

As the most common cancer in women, efforts have been made to develop novel nanomedicine-based therapeutics for breast cancer. In the present study, the in silico curcumin (Cur) properties were investigated, and we found some important drawbacks of Cur. To enhance cancer therapeutics of Cur, three different nonionic surfactants (span 20, 60, and 80) were used to prepare various Cur-loaded niosomes (Nio-Cur). Then, fabricated Nio-Cur were decorated with folic acid (FA) and polyethylene glycol (PEG) for breast cancer suppression. For PEG-FA@Nio-Cur, the gene expression levels of Bax and p53 were higher compared to free drug and Nio-Cur. With PEG-FA-decorated Nio-Cur, levels of Bcl2 were lower than the free drug and Nio-Cur. When MCF7 and 4T1 cell uptake tests of PEG-FA@Nio-Cur and Nio-Cur were investigated, the results showed that the PEG-FA-modified niosomes exhibited the most preponderant endocytosis. In vitro experiments demonstrate that PEG-FA@Nio-Cur is a promising strategy for the delivery of Cur in breast cancer therapy. Breast cancer cells absorbed the prepared nanoformulations and exhibited sustained drug release characteristics.

Most drugs or the natural substances reputed to display some biological activity are hydrophobic molecules that demonstrate low bioavailability regardless of their mode of absorption. Resveratrol and its derivatives belong to the chemical group of stilbenes; while stilbenes are known to possess very interesting properties, these are limited by their poor aqueous solubility as well as low bioavailability in animals and humans. Among the substances capable of forming nanomolecular inclusion complexes which can be used for drug delivery, cyclodextrins show spectacular physicochemical and biomedical implications in stilbene chemistry for their possible application in nanomedicine. By virtue of their properties, cyclodextrins have also demonstrated their possible use in green chemistry for the synthesis of stilbene glucosylated derivatives with potential applications in dermatology and cosmetics. Compared to chemical synthesis and genetically modified microorganisms, plant cell or tissue systems provide excellent models for obtaining stilbenes in few g/L quantities, making feasible the production of these compounds at a large scale. However, the biosynthesis of stilbenes is only possible in the presence of the so-called elicitor compounds, the most commonly used of which are cyclodextrins. We also report here on the induction of resveratrol production by cyclodextrins or combinatory elicitation with methyljasmonate in plant cell systems as well as the mechanisms by which they are able to trigger a stilbene response. The present article therefore discusses the role of cyclodextrins in stilbene chemistry both at the physico-chemical level as well as the biomedical and biotechnological levels, emphasizing the notion of "easy alliance" between these compounds and stilbenes. Part of this work is the result of an aid to the postdoctoral training and improvement abroad for Dr Adrián Matencio (number 21229/PD/19) and financed by the Fundación Séneca (Región de Murcia, Spain).

An antimicrobial is an agent that kills microorganisms or stops their growth. Although different strategies such as the use of a protective atmosphere are being developed, the use of antibacterial and/or antifungal substances in food science is increasing because of the need to transport one food product from a country to another. However, these molecules sometimes present solubility or stability problems that make their effective period shorter or give undesirable organoleptic characteristic to the products. Among the possible solutions, their complexation with cyclodextrins (CDs) is a good strategy to prevent any disadvantageous properties. For that reason, a description of the preparation, characteristics and application of antimicrobial complexes is described here. The common techniques to form the complexes are explained and the possible factors which could affect their encapsulation capacity and release properties are also illustrated. Finally, a complete report about possible applications is presented. CDs could be used to (1) increase the solubility of antimicrobials, (2) increase the stability of the same, (3) improve their release and delivery, (4) prevent volatilization, (5) modify their organoleptic properties, (6) extract antimicrobials from their source and (7) analyze their presence in foods. The complexation of these compounds with CDs can be considered a safe and easy alternative for prolonging the shelf-life of food products.

In recent years, the development of various cyclodextrin (CD)-based nanosponges (NSs) has gained great importance in the controlled and-or targeted release of drugs due to their versatility and simple preparation. In this chapter, an introduction of different administration routes is explained. Further, different ways to obtain CD-NSs and their classification are shown with a brief explanation of the characterization of the inclusion complexes. Finally, illustrative examples in diverse processes or diseases will be reviewed and explained to demonstrate the potential of CD-NSs. Therefore, this division will serve to compile information on CD-NSs in recent years and to illustrate to readers how to generate and apply different derivatives of interest.

The stilbenes are bioactive molecules with a big amount of health benefits and many possibilities in pharmaceutical industry. Several authors have reported a high number of properties for these compounds, including anticancer, antioxidant, anti-inflammatory, antidiabetic, neuroprotective or antimicrobial activities. However, their low aqueous solubility and their ease degradation could lead to low concentration of bioactive compound in the target tissue. For this reason, in the present study, the inclusion complexes of oxyresveratrol with α-, β-, and γ- cyclodextrins are characterized using DSC, TGA, SEM and molecular docking in order to increase the stability of the molecule. All these techniques showed that β-cyclodextrin (β-CD) forms the best complexes. The stability of oxyresveratrol and oxyresveratrol/ β-CD complexes in different aqueous solutions was evaluated by measuring oBrix, pH and UV-Vis spectra. The effect of encapsulation on the solubility and antioxidant activity of oxyresveratrol was also analysed. The results indicated that solutions were stable for at least five weeks, especially when stored in darkness, and that cyclodextrin supplementation leads to a higher concentration and antioxidant capacity of the solubilized bioactive compound than when it is not used. These results and the increase in antioxidant activity could be interesting for the pharmaceutical industry and for drugs enriched in oxyresveratrol.

Neochlorogenic acid, a less-studied caffeoylquinic acid, isomer of chlorogenic acid, has been seen to possess antioxidant, antifungal, anti-inflammatory and anticarcinogenic effects, which makes it an interesting bioactive compound for incorporation in drugs, nutraceuticals or functional foods. However, its poor solubility in water and susceptibility to oxidation make such a task difficult. To overcome that, its encapsulation in cyclodextrins (CDs) is proposed. The fluorescence of neochlorogenic acid in different pH conditions was analyzed, and caffeic acid was proved to be the fluorescent moiety in the molecule. An encapsulation model whereby the ligand poses two potential complexation sites (caffeic and D-(-)-quinic moieties), showed that α-CD and HP-β-CD formed the best inclusion complexes with neochlorogenic acid, followed by M-β-CD, β-CD and γ-CD. Molecular docking with the two best CDs gave better scores for α-CD, despite HP-β-CD providing stabilization through H-bonds. The encapsulation of chlorogenic acid led to a similar CD order and scores, although constants were higher for α-CD, β-CD and M-β-CD, lower for HP-β-CD, and negligible for γ-CD. The solubility and the susceptibility to oxidation of neochlorogenic acid improved after complexation with α-CD and HP-β-CD, while the antioxidant activity of both isomers was maintained. These results could lead to obtaining more stable inclusion complexes with caffeoylquinic acids for applications in the pharmaceutical industry.

Nutraceuticals are bioactive or chemical compounds acclaimed for their valuable biological activities and health-promoting effects. The global community is faced with many health concerns such as cancers, cardiovascular and neurodegenerative diseases, diabetes, arthritis, osteoporosis, etc. The effect of nutraceuticals is similar to pharmaceuticals, even though the term nutraceutical has no regulatory definition. The usage of nutraceuticals, to prevent and treat the aforementioned diseases, is limited by several features such as poor water solubility, low bioavailability, low stability, low permeability, low efficacy, etc. These downsides can be overcome by the application of the field of nanotechnology manipulating the properties and structures of materials at the nanometer scale. In this review, the linear and cyclic dextrin, formed during the enzymatic degradation of starch, are highlighted as highly promising nanomaterials- based drug delivery systems. The modified cyclic dextrin, cyclodextrin (CD)-based nanosponges (NSs), are well-known delivery systems of several nutraceuticals such as quercetin, curcumin, resveratrol, thyme essential oil, melatonin, and appear as a more advanced drug delivery system than modified linear dextrin. CD-based NSs prolong and control the nutraceuticals release, and display higher biocompatibility, stability, and solubility of poorly water-soluble nutraceuticals than the CD-inclusion complexes, or uncomplexed nutraceuticals. In addition, the well-explored CD-based NSs pathways, as drug delivery systems, are described. Although important progress is made in drug delivery, all the findings will serve as a source for the use of CD-based nanosystems for nutraceutical delivery. To sum up, our review introduces the extensive literature about the nutraceutical concepts, synthesis, characterization, and applications of the CD-based nano delivery systems that will further contribute to the nutraceutical delivery with more potent nanosystems based on linear dextrins.

At present, antibiotic resistance is considered a real problem. Therefore, for decades scientists have been looking for novel strategies to treat bacterial infections. Nisin Z, an antimicrobial peptide (AMP), can be considered an option, but its usage is mainly limited by the poor stability and short duration of its antimicrobial activity. In this context, cyclodextrin (CD)-based nanosponges (NSs), synthesized using carbonyldiimidazole (CDI) and pyromellitic dianhydride (PMDA), were chosen for nisin Z loading. To determine the minimum inhibitory of nisin Z loaded on CD-NS formulations, agar well diffusion plates were used. Then, the bactericide concentrations of nisin Z loaded on CD-NS formulations were determined against Gram-positive (Staphylococcus aureus) and -negative (Escherichia coli) bacteria, using microdilution brain heart infusion (BHI) and tetrazolium salt 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT). The minimum and bactericide inhibitory values of the nisin complex with NSs were potentially decreased against both bacteria, compared with the nisin-free sample, while the nisin complex with β-CD showed lower antibacterial activity. The antimicrobial effect was also demonstrated by free NSs. Furthermore, the total viable counts (TVCs) antibacterial experiment indicated that the combination of nisin Z in both PMDA and CDI β-CD-based NSs, especially CDI, can provide a better conservative effect on cooked chicken meat. Generally, the present study outcomes suggest that the cross-linked β-CD-based NSs can present their own antimicrobial potency or serve as promising carriers to deliver and enhance the antibacterial action of nisin Z.

Magnetically driven nanosponges with potential application as targeted drug delivery systems were prepared via the addition of magnetite nanoparticles to the synthesis of cyclodextrin and maltodextrin polymers crosslinked with 1,1′-carbonyldiimidazole. The magnetic nanoparticles were obtained separately via a coprecipitation mechanism involving inorganic iron salts in an alkaline environment. Four composite nanosponges were prepared by varying the content of magnetic nanoparticles (5 wt% and 10 wt%) in the cyclodextrin- and maltodextrin-based polymer matrix. The magnetic nanosponges were then characterised by FTIR, TGA, XRD, FESEM, and HRTEM analysis. The magnetic properties of the nanosponges were investigated via magnetisation curves collected at RT. Finally, the magnetic nanosponges were loaded with doxorubicin and tested as a drug delivery system. The nanosponges exhibited a loading capacity of approximately 3 wt%. Doxorubicin was released by the loaded nanosponges with sustained kinetics over a prolonged period of time.

Our desire to live longer has led to an ever-increasing number of novel antiaging products. However, few molecules have any real effect and new ones need to be studied before they can be used commercially. In this contribution, activation of the caloric restriction (CR) pathway was studied using different three (resveratrol, oxyresveratrol and piceatannol)&mdash, a family with demonstrated bioactivity on phosphodiesterase activity. The high-affinity phosphodiesterase type 2 (PDE2) of Saccharomyces cerevisiae was expressed in Escherichia coli, purified and characterized. The activity and the inhibitory activity of each stilbene was studied, and the findings were compared in vitro and in silico with those obtained with roflumilast&mdash, a human PDE4 inhibitor widely used in chronic obstructive pulmonary diseases. Finally, an in vivo chronological lifespan assay using WT S. cerevisiae and &Delta, PDE2 S. cerevisiae strains was carried out. It was demonstrated that stilbenes can modulate yPDE2 activity, increasing the lifespan of the yeast by 18% over a control (in combination with other pathways). In addition, roflumilast increased the lifespan in the WT strain. The findings as a whole would increase the range of lifespan products available and suggest novel uses for approved drugs.

There have been many reviews of the cyclic oligosaccharide cyclodextrin (CD) and CD-based materials used for drug delivery, but the capacity of CDs to complex different agents and their own intrinsic properties suggest they might also be considered for use as active drugs, not only as carriers. The aim of this review is to summarize the direct use of CDs as drugs, without using its complexing potential with other substances. The direct application of another oligosaccharide called cyclic nigerosyl-1,6-nigerose (CNN) is also described. The review is divided into lipid-related diseases, aggregation diseases, antiviral and antiparasitic activities, anti-anesthetic agent, function in diet, removal of organic toxins, CDs and collagen, cell differentiation, and finally, their use in contact lenses in which no drug other than CDs are involved. In the case of CNN, its application as a dietary supplement and immunological modulator is explained. Finally, a critical structure–activity explanation is provided.

Background The food industry is constantly attempting to develop better products that will have a positive effect on health (commonly known as functional foods). In this respect, cyclodextrins (CDs) could be of interest because they are tasteless, non-caloric and odourless molecules with several valuable characteristics, such as a capacity to separate chiral compounds and solubilize or stabilize bioactive compounds (BaC). Scope and approach This review represents a revision of the state-of-the-art of CDs and their uses in the food industry. Key findings and conclusions We analysed their metabolism and regulatory aspects of current applications of CDs: as carriers, for removing components, to produce or extract BaC, their use as nanosensors or in food packaging. We study how inclusion complexed are formed referring to the most common techniques and parameters Moreover, how inclusion complexes are formed will be studied with reference to the most common techniques and parameters. In conclusion, their applications in the food and other industries will increase in the coming years without a doubt.

In this work, the increase of the Caenorhabditis elegans (C. elegans) lifespan extension using hyper-branched cyclodextrin-based nanosponges (CD-NS) complexing oxyresveratrol (OXY), and the possible inhibition of C. elegans phosphodiesterase type 4 (PDE4) were evaluated. The titration displacement of fluorescein was used to calculate the apparent complexation constant (KF) between CD-NS and OXY. Moreover, PDE4 was expressed in E. coli, purified and refolded in presence of cyclodextrins (CDs) to study its possible inhibition as pharmacological target of OXY. The apparent activity was characterized and the inhibitory effect of OXY on PDE4 displayed a competitive in vitro inhibition corroborated in silico. A maximum increase of the in vivo life expectancy of about 9.6% of using OXY/CD-NS complexes in comparison with the control was obtained, in contrast to the 6.5% obtained with free OXY. No effect on lifespan or toxicity with CD-NS alone was found. These results as a whole represent new opportunities to use OXY and CD-NS in lifespan products.

Despite being saturated, a huge quantity of “novel” functional food products reaches the food market every day and companies are looking for new products to catch consumers’ attention. In the present study, the inclusion complexes of oxyresveratrol with α-, β- and γ-CD are characterized using DSC, TGA, SEM and molecular docking and their complexing capacities arecompared. As β-CD showed the best results, i) 0.2 mM oxyresveratrol alone, ii) 0.2 mM oxyresveratrol complexed with 8 mM β-CD and iii) 4 mM oxyresveratrol solubilized with 8 mM β-CD were used to fortify, juice and milk food models, and kept in typical storage conditions (darkness and/or refrigerated) conditions for one month. The results showed that CD supplementation leads to a higher oxyresveratrol concentration and antioxidant capacity than when not used. Oxyresveratrol/β-CD food models were stable for five weeks. The most typical variables measured were compared. In vitro digestion pointed to similar bioaccessibility. The bacteriostatic effect was also studied and the greater effectiveness of oversaturated solutions was demostrated. These results should be useful for the food industry for designing hydrophilic products containing oxyresveratrol.

In this work, the interaction between Kynurenic acid (KYNA) and several natural and modified cyclodextrins (CDs) is carried out. Among all the CD tested, HPβ-CD showed the strongest complexation constant (KF), with a value of 270.94 ± 29.80 M−1. Between natural (α- and β-) CDs, the complex of KYNA with β-CD was the most efficient. The inclusion complex of KYNA with CDs showed a strong influence of pH and temperature. The KF value decreased at high pH values, when the pKa was passed. Moreover, an increase of the temperature caused a decrease in the KF values. The thermodynamic parameters of the complexation (ΔH°, ΔS° and ΔG°) were studied with negative entropy, enthalpy and spontaneity of the process at 25 °C. Moreover, the inclusion complex was also characterized using FTIR and TGA. Finally, molecular docking calculations provided different interactions and their influence in the complexation constant.

This study was developed inside the European Project Life "Clean up" (LIFE 16 ENV/ES/000169) to search for suitable adsorbents to purify treated water from emerging pollutants. Notably, among pollutants, the attention was focused on Ciprofloxacin removal, selecting as recyclable adsorbent Cyclodextrin-based nanosponges, characterized by using FTIR-ATR, DSC, TG, SEM, EDX, gas-volumetric analysis, and XRD analyses. Indeed, the in-batch adsorption process was quite complete removing, in a few minutes, 90% of the pollutant from water, with a maximum adsorption capacity of 2 mg/g. A better comprehension of the adsorption mechanism was obtained by studying the effect of various experimental parameters on the process, i.e. ionic strength, pH values, adsorbent/pollutant ratio, and temperature values. The thermodynamics (?G°0), the adsorption isotherms (Langmuir, Freundlich, Temkin, and Dubinin-Radushkevich), and kinetics of the process were also investigated. In particular, the applicability of all the proposed isotherms, except the Langmuir model, was observed, and the finding highlighted the heterogeneous character of the adsorption process. The pseudo-second-order kinetic model well described the process and the application of the Weber-Morris model suggested that two main consecutive steps constituted the adsorption. Despite the relatively low adsorption capacity, desorption experiments, recycling 80% of the pollutant for each cycle, were performed, and for the purpose, 0.1 M NaCl was used, lowering the environmental impact. Moreover, other contaminants, such as Diclofenac, Carbendazim, Furosemide, and Sulfamethoxazole were successfully removed from the water, also if present in a quaternary mixture, opening the possibility to use this adsorbent for real water treatments.

The interaction between oxyresveratrol (a type of stilbene with high biological activity) and modified cyclodextrins (CDs) was studied. Using HPLC-RP, was seen to form a 1:1 complex with all the CDs tested. The best CD in this respect was MβCD (K F = 606.65 ± 30.18 M −1 ), the complexation showing a strong dependence on pH and temperature: The complexation constant (K F ) decreased as the pH and temperature increased. The thermodynamic parameters studied (ΔH°, ΔS° and ΔG°) showed negative entropy, enthalpy and Gibbs free energy change at 25 °C. In addition, fluorescence signal of oxyresveratrol increased when MβCD was added. The oxyresveratrol emission and excitation spectra were obtained for first time. A 1 H NMR was carried out to study the structure of the complex and, DSC studied demonstrated the complexation. A computational study by molecular docking was made to complement the structural study.

In this work the aggregation behavior of t10,c12 Conjugated linoleic acid (t10,c12-CLA) is presented for first time. The results show a c.m.c. of 25μM at pH 8 and 25°C. The encapsulation process with cyclodextrins (CDs) presented a 1:1 stoichiometry in all cases studied but the complexation constants were strongly dependent on the type of CDs used, the pH and temperature. Hydroxypropyl-beta-Cyclodextrin (HPβCD) was the best CD studied for encapsulating t10,c12-CLA. The resulting t10,c12-CLA-HPβCD complex showed a very high dependency on pH, which explains why a pKa of 4.08 was found for first time, which was very close to the simulated value. Furthermore, the effect of temperature on the t10,c12-CLA-HPβCD was studied. The complexation constant (KF) showed an increase behavior with the temperature. In addition, molecular docking calculations provided further insights into how the different interactions influence the complexation constant. Finally, a comparative study with rumenic acid, an isomer, was carried out.

In this work the aggregation behavior of Rumenic acid (RA) is presented for the first time. The results point to a c.m.c. of 35 μM at pH 8 and 25 °C. This behavior can be modified by introducing CDs into the system to encapsulate the RA. The encapsulation process presented a 1:1 stoichiometry in all the cases studied but the complexation constants were strongly dependent on the type of CDs used, the pH and temperature. Firstly, the effect of the type of CD on the encapsulation process was studied. Among the natural and modified CDs analyzed HPβCD was the best for encapsulating RA. The pKa determined for RA was 4.31. The KF showed different behavior below and above 25 °C due to changes in the stoichiometry. Finally, molecular docking calculations provided further insights into how the different interactions influence the complexation constant.

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.

Introduction Several authors have reported on the different bioactivities of methyl jasmonate (MeJA) stereoisomers. However, no simple, precise and cheap method for separating and identifying them using reversed-phase high performance liquid chromatography (RP-HPLC) has been developed. Objective (1) To create a simple, precise and cheap method for separating and identifying the four stereoisomers present in commercial racemic mixtures of MeJA and (2) to identify the four stereoisomers using molecular docking techniques and coinjection. Materials and Methods – RP-HPLC using a 250 mm C18 column and different proportions of cyclodextrins (CDs) and organic solvents was applied to a commercial sample of racemic MeJA. Results The results show that the best conditions for separating the MeJA stereoisomers are: 20% methanol in the mobile phase, a temperature of 45 °C and a 16 mM concentration of methyl-β-cyclodextrin (M-β-CD). A simple C18 250 mm column and a flow rate of 1.25 mL/min were used. The reduction in the retention time of MeJA observed when M-β-CD is added to the mobile phases was used to determine the complexation constants of the guest/CD complex and compared with the obtained when other CDs were used. The KF for M-β-CD (117.49 ± 5.9 1/M) was obtained with a 1:1 stoichiometry. The four stereoisomers were identified by molecular docking techniques and coinjection of a commercially available rosemary essential oil. Conclusion The new method identified and classified the four stereoisomers of MeJA in the following ordination: (−)epiMeJA, (−)MeJA; (+)MeJA and (+)epiMeJA. These results could be used to improve the elicitation of cell cultures with only the best isomer. Copyright © 2016 John Wiley & Sons, Ltd.

Roflumilast is an orally available inhibitor of phosphodiesterase (PDE) type 4, which is widely used in chronic obstructive pulmonary diseases. However, it has low solubility and adverse effects include diarrhea and nausea. Since its solubilization may improve treatment and, dismissing any adverse effects, its interaction with cyclodextrins (CDs) was studied. The Higuchi-Connors method was used to determine the complexation constant with different CDs, pH values and temperatures. Molecular docking was used to predict interaction between the complexes. An in vitro digestion experiment was carried out to test roflumilast protection. Finally, the photostability of the complex was evaluated. The complex formed with &beta, CD had the highest K11 value (646 &plusmn, 34 M&minus, 1), although this value decreased with increasing temperature. Similarly, K11 decreased as the pH increased. In vitro digestion showed that CDs protect the drug during digestion and even improve its bioaccessibility. Finally, CDs reduced the drug&rsquo, s extreme photosensitivity, originating a fluorescence signal, which is described for first time. The kinetic parameters of the reaction were obtained. This study not only completes the complexation study of roflumilast-CD, but also points to the need to protect roflumilast from light, suggesting that tablets containing the drug might be reformulated.

In this work we used natural and modified cyclodextrins (β-CD and HP-β-CD) as encapsulating agents to improve citronellal properties. Using fluorimetric techniques, its aggregation behavior was studied for the first time. Its critical micellar concentration was seen to vary with the presence of cyclodextrins, which form 1:1 stoichiometry complexes with citronellal. The encapsulation constants and the scores obtained by Molecular Docking were correlated. Chromatographic (GC–MS) and sensory analysis confirmed that cyclodextrins improve the persistence of the aroma. Finally, the antimicrobial effect of citronellal against Escherichia coli and Bacillus subtilis in the presence and absence of cyclodextrins was studied. A combinatorial effect of citronellal, HP-β-cyclodextrin and Glucobay® as an antimicrobial mixture was observed. The results of this study not only demonstrated the potential of CD mixtures, but also that the growth caused by CD digestion may sometimes be greater that the antimicrobial effect of the agents used in this study.

Resveratrol and oxyresveratrol are natural polyphenolic stilbenes with several important pharmacological activities. However, low solubility and aqueous instability are the major limitations in their drug delivery applications. In the present work, we demonstrated the encapsulation of resveratrol and oxyresveratrol with nanosponge to improve solubility and stability. Several characterization techniques were used to confirm the encapsulation of both drug molecules within the nanosponges. The high encapsulation efficiency of resveratrol (77.73%) and oxyresveratrol (80.33%) was achieved within the nanosponges. Transmission electron microscopy suggested uniform spherical size particles of resveratrol and oxyresveratrol loaded nanosponges. Compared to free drugs, better protection against UV degradation was observed for resveratrol-loaded nanosponge (2-fold) and oxyresveratrol-loaded nanosponge (3-fold). Moreover, a higher solubilization of resveratrol- and oxyresveratrol-loaded nanosponges lead to a better antioxidant activity compared to drug molecules alone. Cytotoxicity studies against DU-145 prostate cancer cell lines further suggested improved activity of both resveratrol and oxyresveratrol-loaded nanosponges without any significant toxicity of blank nanosponges.

The use of betalains as bioactive compounds has been widely investigated. However, their use as a functional food requires a more exhaustive study because of their photosensitivity and poor stability. For this reason, this works studies the stabilization of two highly bioactive betalain derivatives, phenylethylamine-betaxanthin (Ph-Bx) and indoline-betacyanin (In-Bc) by nanoencapsulation in natural a modified cyclodextrins (CDs). Methyl-β-CD (Mβ-CD) showed the best results for Ph-Bx while Hydroxypropyl-β-CD (HPβ-CD) was better in the case of In-Bc. In addition, the effect of pH and temperature on encapsulation was studied finding that the encapsulation constant (KF) value increased as the pH decreased in the case of Ph-Bx but not in the case of In-Bc. The KF decreased as the temperatures increased. The thermodynamic parameters, ΔH°, ΔS° and ΔG°, were also calculated. Molecular docking provided further insight into how the different interactions influenced the encapsulation constant. The results show that the presence of CDs during the biotechnological synthesis of Ph-Bx and In-Bc increased production by 51 and 26%, respectively, and also increased the stability of both derivatives. This study represents a first step towards increasing the production of this type of compound for introduction into functional foods.

Niemann Pick disease Type C (NPC) is a recessive rare disease caused by the mutation on NPC1 and/or NPC2 genes changing the processing of the Low-density proteins (LDL) resulting in an accumulation of lipids in the cells. Until today there is not a cure, the current treatment is based on palliative affairs to reduce the symptoms and prevent its appearance. Among all the treatments proposed the use of cyclodextrins (CDs), nanocarriers which can complex cholesterol, is one of the most useful alternatives. Indeed, for several years 2-hydroxypropyl-β-CD (HPβ-CD) is approved as orphan drug for FDA and EMA to the treatment. However, different CDs based materials are created each year to improve the cholesterol uptake. This review is focused on the novelty of CD based materials for NPC treatment.

The complexation of the bioactive compound oxyresveratrol (OXY) with a polymer called cyclodextrin-based nanosponge (CD-NS) and its application was studied.A new methodology is used to calculate, an apparent inclusion complex constant (KFapp) between a ligand and CD-NSs. Moreover, the KFapp of resveratrol was also evaluated and compared. The complex of OXY with the nanosponge β-CDI 1:4, was studied in vitro using DSC, TGA and FTIR techniques and its drug loading and release behavior were studied. An in vitro digestion showed higher protection of OXY complexed than free OXY. The bioactivity enhancing capacity of OXY was also studied against prostate (PC-3) and colon (HT-29 and HCT-116) cancer cell lines, where it showed stronger cell viability inhibition than the free drug. The findings as a whole represent a new opportunity for studying the complexation of drugs in CD-NSs and the use of oxyresveratrol as an ingredient in nutraceutical products.

Current HPLC methods for analyzing cAMP Phosphodiesterase activity (PDE) use salts, limiting the life of the columns. For this reason, we have developed an improved “ion pairing agent free” method, using a simple 150 mm C18-hydro column at 30 °C and two phases: (a) water with 0.1% acetic acid and (b) 85/15 w/w MeOH/tetrahydrofuran with 0.1% acetic acid. Using this method the peaks for cAMP and AMP were obtained with good resolution (R ≈ 1.35) and sensitivity (5·10−9 mols) in only 15 min. Moreover, the method was applied to the GMP/cGMP pair obtaining the same sensitivity and resolution (R ≈ 1.38). The precision and accuracy were tested and the method was verified with a Type IV Phosphodiesterase reaction, which produced AMP from cAMP. The method is cleaner and less aggressive, and represents an interesting alternative to currently used methods.

The food industry needs cheap, fast and sensitive methods to increase the number of analyses that are routinely carried out; for this reason, new methods are constantly being sought. This paper describes a novel fluorescent nanosensor based on cyclodextrin (CD) to determine ellagic acid (EA). The encapsulation of EA in the presence of borax was studied. Firstly, the complexation of EA–borax was tested. The stoichiometry of the EA–borax complex showed a 1 : 2 complex, with KF1 = 2548 ± 127 M−1 and KF2 = 302 ± 15 M−1. Different CDs were used to obtain a 1 : 1 : 1 CD–EA–borax complex with γ-CD providing the best complexation constant (KF3 = 364 ± 18 M−1). Furthermore, when the accuracy and sensitivity of the nanosensor were tested using a crude blueberry extract, the CD/borax mixture provided an 18 times stronger signal than with the crude extract alone and 7 times stronger than that obtained using borax alone.

Several authors have reported on the different bioactivities of methyl jasmonate (MeJA) stereoisomers. However, no simple, precise and cheap method for separating and identifying them using reversed-phase high performance liquid chromatography (RP-HPLC) has been developed.(1) To create a simple, precise and cheap method for separating and identifying the four stereoisomers present in commercial racemic mixtures of MeJA and (2) to identify the four stereoisomers using molecular docking techniques and coinjection. Materials and Methods - RP-HPLC using a 250 mm C18 column and different proportions of cyclodextrins (CDs) and organic solvents was applied to a commercial sample of racemic MeJA.The results show that the best conditions for separating the MeJA stereoisomers are: 20% methanol in the mobile phase, a temperature of 45 °C and a 16 mM concentration of methyl-β-cyclodextrin (M-β-CD). A simple C18 250 mm column and a flow rate of 1.25 mL/min were used. The reduction in the retention time of MeJA observed when M-β-CD is added to the mobile phases was used to determine the complexation constants of the guest/CD complex and compared with the obtained when other CDs were used. The KThe new method identified and classified the four stereoisomers of MeJA in the following ordination: (-)epiMeJA, (-)MeJA; (+)MeJA and (+)epiMeJA. These results could be used to improve the elicitation of cell cultures with only the best isomer. Copyright © 2016 John WileySons, Ltd.

In this work, an in-depth study of the interaction between piceatannol (a type of stilbene with high biological activity) and different natural and modified cyclodextrins (CDs) is made, using steady state fluorescence. This bioactive molecule forms a 1 : 1 complex with all the natural (α-CD, β-CD and γ-CD) and modified (HP-β-CD, HE-β-CD and M-β-CD) CDs tested. Among natural CDs, the interaction of piceatannol with β-CD was the most efficient. However, the modified CDs showed higher encapsulation constants (KF) than β-CD, except M-β-CD; the highest KF being found for HP-β-CD (14 048 ± 702 M(-1)). The encapsulation of piceatannol in the internal cavity of CDs showed a strong dependence on pH and temperature. The interaction between HP-β-CD and piceatannol was less effective in the pH region where the stilbene begins to suffer the deprotonation of its hydroxyl group. Moreover, the values of KF decreased as the system temperature increased. To obtain information on the mechanism involved in the piceatannol affinity for CD, the thermodynamic parameters of the complexation (ΔH°, ΔS° and ΔG°) were studied, the results showed a negative entropy (-3.7 ± 0.2 J mol(-1) K(-1)), enthalpy (-24.6 ± 1.2 kJ mol(-1)) and Gibbs free energy change at 25 °C (-23.5 ± 1.2 J mol(-1)). Finally, molecular docking calculations provided further insights into how the different interactions influence the complexation constant. A high degree of correlation was observed between the computed scores and experimental values.