betadex and caffeic-acid

Green coffee beans are rich in polyphenol chlorogenic acids (CGAs), which are decomposed to give caffeic acid (CFA) and quinic acid (QNA) upon roasting. CGA, CFA and QNA primarily confer the bitterness, astringency and acidity to the coffee brew. Aiming at the structural and thermodynamic insights into the β-cyclodextrin (β-CD) encapsulation of key compounds in coffee (CGA 1, CFA 2, and QNA 3), a systematic, comprehensive study using single-crystal X-ray diffraction and DFT calculation has been undertaken. Scrutinizing the X-ray-derived inclusion structures of 1-3 reveals that the CFA moiety plays a determinant role in complexation, in agreement with the DFT-derived relative thermodynamic stabilities. The guest molecules gain stability through OH⋯O hydrogen bonding with β-CD and are well shielded in the β-CD wall. The three stable β-CD inclusion complexes with coffee key compounds suggest the implications of CDs as encapsulating agents for improving bioactivities and masking bitter taste in foods.

Topics: Antioxidants; beta-Cyclodextrins; Caffeic Acids; Chemistry, Pharmaceutical; Chlorogenic Acid; Coffee; Crystallography, X-Ray; Density Functional Theory; Hydrogen Bonding; Quinic Acid; Taste; Thermodynamics

Alperujo-a two-phase olive mill waste that is composed of olive vegetation water and solid skin, pulp, and seed fragments - is a highly valuable olive by-product due to its high content in phenolic compounds. In this study, we assessed whether β-cyclodextrin (β-CD), which is used to extract and protect alpejuro phenolic compounds (hydroxytyrosol-

Topics: Antioxidants; beta-Cyclodextrins; Biological Availability; Caco-2 Cells; Caffeic Acids; Coumaric Acids; Glucosides; Humans; Olea; Phenols; Phenylethyl Alcohol; Plant Extracts; Propionates

Caffeic acid is described as antibacterial, but this bioactive molecule has some issues regarding solubility and stability to environmental stress. Thus, encapsulation devices are required.. The aim of this work was to study the effect of the caffeic acid encapsulation by cyclodextrins on its antibacterial activity.. The interactions between the caffeic acid and three cyclodextrins (β-cyclodextrin (βCD), 2-hydroxypropyl-β-cyclodextrin (HPβCD) and methyl-β-cyclodextrin were study.. The formation of an aqueous soluble inclusion complex was confirmed for βCD and HPβCD with a 1:1 stoichiometry. The βCD/caffeic acid complex showed higher stability than HPβCD/caffeic acid. Caffeic acid antibacterial activity was similar at pH 3 and pH 5 against the three bacteria (K. pneumoniae, S. epidermidis and S. aureus).. The antibacterial activity of the inclusion complexes was described here for the first time and it was shown that the caffeic acid activity was remarkably enhanced by the cyclodextrins encapsulation.

Topics: Anti-Bacterial Agents; Bacteria; beta-Cyclodextrins; Caffeic Acids; Drug Evaluation, Preclinical; Hydrogen-Ion Concentration

Although the separation efficiency of capillary electrophoresis (CE) is much higher than that of other chromatographic methods, it is sometimes difficult to adequately separate the complex ingredients in biological samples. This article describes how one effective and simple way to develop the separation efficiency in CE is to add some modifiers to the running buffer. The suitable running buffer modifier β-cyclodextrin (β-CD) was explored to fast and completely separate four phenylethanoid glycosides and aglycones (homovanillyl alcohol, hydroxytyrosol, 3,4-dimethoxycinnamic acid, and caffeic acid) in Lamiophlomis rotata (Lr) and Cistanche by capillary zone electrophoresis with ultraviolet (UV) detection. It was found that when β-CD was used as running buffer modifier, a baseline separation of the four analytes could be accomplished in less than 20 min and the detection limits were as low as 10(-3) mg L(-1). Other factors affecting the CE separation, such as working potential, pH value and ionic strength of running buffer, separation voltage, and sample injection time, were investigated extensively. Under the optimal conditions, a successful practical application on the determination of Lr and Cistanche samples confirmed the validity and practicability of this method.

Topics: beta-Cyclodextrins; Buffers; Caffeic Acids; Cinnamates; Cistanche; Electrophoresis, Capillary; Glycosides; Hydrogen-Ion Concentration; Lamiaceae; Limit of Detection; Phenylethyl Alcohol

This research reports the first application of β-cyclodextrin (β-CD) complexes as a new method for generation of three way data, combined with second-order calibration methods for quantification of a binary mixture of caffeic (CA) and vanillic (VA) acids, as model compounds in fruit juices samples. At first, the basic experimental parameters affecting the formation of inclusion complexes between target analytes and β-CD were investigated and optimized. Then under the optimum conditions, parallel factor analysis (PARAFAC) and bilinear least squares/residual bilinearization (BLLS/RBL) were applied for deconvolution of trilinear data to get spectral and concentration profiles of CA and VA as a function of β-CD concentrations. Due to severe concentration profile overlapping between CA and VA in β-CD concentration dimension, PARAFAC could not be successfully applied to the studied samples. So, BLLS/RBL performed better than PARAFAC. The resolution of the model compounds was possible due to differences in the spectral absorbance changes of the β-CD complexes signals of the investigated analytes, opening a new approach for second-order data generation. The proposed method was validated by comparison with a reference method based on high-performance liquid chromatography photodiode array detection (HPLC-PDA), and no significant differences were found between the reference values and the ones obtained with the proposed method. Such a chemometrics-based protocol may be a very promising tool for more analytical applications in real samples monitoring, due to its advantages of simplicity, rapidity, accuracy, sufficient spectral resolution and concentration prediction even in the presence of unknown interferents.

Topics: Algorithms; beta-Cyclodextrins; Beverages; Caffeic Acids; Calibration; Chromatography, High Pressure Liquid; Fruit; Least-Squares Analysis; Multivariate Analysis; Reproducibility of Results; Spectrophotometry; Vanillic Acid

Caffeic acid has been described as active against bacteria commonly isolated from wound infections. However, its low stability and poor solubility reduce caffeic acid applicability as a pharmaceutical product. These parameters can be enhanced by complexation with cyclodextrin. The main goal of the present work was to incorporate caffeic acid on cyclodextrin-based hydrogels capable of controlled delivery, in order to be used as antibacterial wound dressing.. Cyclodextrin-based hydrogels were prepared by direct crosslinking of β-cyclodextrin or hydroxypropyl-β-cyclodextrin with 1,4-butanediol diglycidyl ether in the presence of hydroxypropyl methylcellulose.. The hydrogels obtained combine good physicochemical properties (viscoelasticity, superabsorbency and high ability to retain and deliver caffeic acid) with the preservation of caffeic acid' antibacterial activity and effect on fibroblasts, with gel-β-cyclodextrin the most suited.. The hydrogels obtained could be useful as caffeic acid delivery-system devices for the treatment of wound infections.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; 3T3 Cells; Animals; Anti-Bacterial Agents; Bacteria; Bandages; beta-Cyclodextrins; Butylene Glycols; Caffeic Acids; Cell Proliferation; Cell Survival; Chemistry, Pharmaceutical; Cross-Linking Reagents; Delayed-Action Preparations; Drug Carriers; Drug Stability; Elasticity; Fibroblasts; Hydrogels; Hypromellose Derivatives; Kinetics; Mice; Solubility; Technology, Pharmaceutical; Viscosity

Tyrosol and caffeic acid are biophenols that contribute to the beneficial properties of virgin olive oil. The influence of hydroxypropyl-β-cyclodextrin (HPβ-CD) on their respective antioxidant capacities was analyzed. The ORAC antioxidant activity of tyrosol (expressed as μM Trolox equivalents/μM Tyrosol) was 0.83 ± 0.03 and it increased up to 1.20 ± 0.11 in the presence of 0.8 mM HPβ-CD. However, the ORAC antioxidant activity of caffeic acid experienced no change. The different effect of HPβ-CD on each compound was discussed. In addition, the effect of increasing concentrations of different cyclodextrins in the development of ORAC-fluorescence (ORAC-FL) assays was studied. The ORAC signal was higher for HPβ-CD, followed by Mβ-CD, β-CD, γ-CD and finally α-CD. These results could be explained by the formation of inclusion complexes with fluorescein.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Antioxidants; beta-Cyclodextrins; Caffeic Acids; Cyclodextrins; Phenylethyl Alcohol; Spectrometry, Fluorescence

The inclusion complexation behavior of caffeic acid (CA) with hydroxypropyl-beta-cyclodextrin (HP-beta-CD) was studied by UV-vis, fluorescence spectroscopy and nuclear magnetic resonance spectroscopy (NMR). Experimental conditions including the concentration of HP-beta-CD and media acidity were investigated in detail. The result suggested HP-beta-CD was more suitable for including CA in acidity solution. The binding contants (K) of the inclusion complexes were determined by linear regression analysis and the inclusion ratio was found to be 1:1. The water solubility of CA was increased by inclusion with HP-beta-CD according to the phase-solubility diagram. The spatial configuration of complex has been proposed based on (1)H NMR and two-dimensional (2D) NMR, the result suggested that CA was entrapped inside the hydrophobic core of HP-beta-CD with the lipophilic aromatic ring and the portion of ethylene.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Caffeic Acids; Hydrogen-Ion Concentration; Macromolecular Substances; Magnetic Resonance Spectroscopy; Models, Biological; Phase Transition; Polymers; Solubility; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet