Inclusion complex of ellagic acid with β-cyclodextrin: Characterization and in vitro anti-inflammatory evaluation

Bulani, Vipin D.; Kothavade, Pankaj S.; Kundaikar, Harish; Gawali, Nitin B.; Chowdhury, Amrita A.; Degani, Mariam S.; Juvekar, Archana R.

doi:10.1016/j.molstruc.2015.08.054

Cited by 72 publications

(41 citation statements)

References 39 publications

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“…The OCD/VE inclusion complex appeared in the form of an irregular dense block, with distinct edges and corners in which the original morphology of OCD disappeared and multilayered aggregates of pieces were present. Similar results have been previously reported, namely that the changes in the surface morphology of the crystal provide strong evidence of the formation of the inclusion complex [20,21].…”

Section: Sem Analysissupporting

confidence: 91%

Preparation and Characterization of Octenyl Succinate β-Cyclodextrin and Vitamin E Inclusion Complex and Its Application in Emulsion

Chen

Yun

et al. 2020

Molecules

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Vitamin E (VE) and β-cyclodextrin (β-CD) can form an inclusion complex; however, the inclusion rate is low because of the weak interaction between VE and β-CD. The results of a molecular docking study showed that the oxygen atom in the five-membered ring of octenyl succinic anhydride (OSA) formed a strong hydrogen bond interaction (1.89 Å) with the hydrogen atom in the hydroxyl group of C-6. Therefore, β-CD was modified using OSA to produce octenyl succinic-β-cyclodextrin (OCD). The inclusion complexes were then prepared using OCD with VE. The properties of the inclusion complex were investigated by Fourier-transform infrared spectroscopy (FT-IR), 13C CP/MAS NMR, scanning electron microscopy (SEM), and atomic force microscopy (AFM). The results demonstrated that VE had been embedded into the cavity of OCD. Furthermore, the emulsifying properties (particle size distribution, ζ-potential, and creaming index) of the OCD/VE inclusion-complex-stabilized emulsion were compared with that stabilized by β-CD, OCD, and an OCD/VE physical mixture. The results showed that the introduction of the OS group and VE could improve the physical stability of the emulsion. In addition, the OCD/VE inclusion complex showed the strongest ability to protect the oil in the emulsion from oxidation. OCD/VE inclusion complex was able to improve the physical and oxidative stability of the emulsion, which is of great significance to the food industry.

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Section: Sem Analysissupporting

confidence: 91%

Preparation and Characterization of Octenyl Succinate β-Cyclodextrin and Vitamin E Inclusion Complex and Its Application in Emulsion

Chen

Yun

et al. 2020

Molecules

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“…On the other hand, particle appearance, shape and size were quite different between EOO-HP-β-CD complexes, in that, those obtained by SL displayed an even larger difference than those obtained by KND compared to HP-β-CD. As suggested by Bulani et al [37], such modifications in particle shape and aspect may be taken as a proof of the formation of inclusion complex with CD, thereby confirming the insights emerged from FT-IR spectroscopy. qualitatively identical spectra, with the characteristic HP-β-CD bands at 3358 and 1018 cm −1 corresponding to O-H and C-O-C vibrations, respectively, while the EOO characteristic bands had decreased intensity ( Figure 2F,G).…”

Section: Fourier Transform Infrared Spectroscopy (Ft-ir)supporting

confidence: 74%

Development and Evaluation of Antimicrobial and Modulatory Activity of Inclusion Complex of Euterpe oleracea Mart Oil and β-Cyclodextrin or HP-β-Cyclodextrin

Magalhães

Macedo

Pacheco

et al. 2020

IJMS

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The development of inclusion complexes is used to encapsulate nonpolar compounds and improve their physicochemical characteristics. This study aims to develop complexes made up of Euterpe oleracea Mart oil (EOO) and β-cyclodextrin (β-CD) or hydroxypropyl-β-cyclodextrin (HP-β-CD) by either kneading (KND) or slurry (SL). Complexes were analyzed by molecular modeling, Fourier-transform infrared spectroscopy, scanning electron microscopy, powder X-ray diffraction, thermogravimetry analysis and differential scanning calorimetry. The antibacterial activity was expressed as Minimum Inhibitory Concentration (MIC), and the antibiotic resistance modulatory activity as subinhibitory concentration (MIC/8) against Escherichia coli, Streptomyces aureus, Pseudomonas aeruginosa and Enterococcus faecalis. Inclusion complexes with β-CD and HP-β-CD were confirmed, and efficiency was proven by an interaction energy between oleic acid and β-CD of −41.28 ± 0.57 kJ/mol. MIC values revealed higher antibacterial activity of complexes compared to the isolated oil. The modulatory response of EOO and EOO-β-CD prepared by KND as well as of EOO-β-CD and EOO-HP-β-CD prepared by SL showed a synergistic effect with ampicillin against E. coli, whereas it was not significant with the other drugs tested, maintaining the biological response of antibiotics. The antimicrobial response exhibited by the complexes is of great significance because it subsidizes studies for the development of new pharmaceutical forms.

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“…Oral treatment with 10 or 20 mg/kg EA-HP-β-CD resulted more efficacious than the administration of EA alone or of 10 mg/kg indomethacin as indicated by the measure of paw edema volume. The feasibility of using β-CD as complexing agent for EA was also investigated with less satisfactory results [61]. The complex was less soluble, leading to a total EA concentration up to 39.14 µg/mL, lower than that obtained in the previous study with HP-β-CD, due to the lower β-CD solubility.…”

Section: Ea Inclusion In Cyclodextrins (Cd)mentioning

confidence: 95%

“…Among CD, hydroxypropyl-β-CD (HP-β-CD) is characterized by better inclusion ability and higher complex solubility. In order to investigate the feasibility and the stoichiometry of inclusion complex formation of EA in HP-β-CD, phase solubility studies were carried out in water at 30 °C for 72 h to reach the equilibrium [60]. The obtained solubility curve of EA showed a linear Preprints (www.preprints.org) | NOT PEER-REVIEWED | Posted: 7 April 2020 doi:10.20944/preprints202004.0100.v1…”

Section: Ea Inclusion In Cyclodextrins (Cd)mentioning

confidence: 99%

Formulation Strategies to Improve Oral Bioavailability of Ellagic Acid

Zuccari¹,

Baldassari²,

Ailuno³

et al. 2020

Preprint

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Featured Application: An updated description of pursued approaches for efficiently resolving the low bioavailability issue of ellagic acid. Abstract: Ellagic acid, a polyphenolic compound present in fruits and berries, has recently been object of extensive research for its antioxidant activity, which might be useful for the prevention and treatment of cancer, cardiovascular pathologies, and neurodegenerative disorders. Its protective role justifies numerous attempts to include it in functional food preparations and in dietary supplements not only to limit the unpleasant collateral effects of chemotherapy. However, ellagic acid use as chemopreventive agent has been debated because of its poor bioavailability associated to low solubility, limited permeability, first pass effect, and interindividual variability in gut microbial transformations. To overcome these drawbacks, various strategies for oral administration including solid dispersions, micro-nanoparticles, inclusion complexes, selfemulsifying systems, polymorphs have been proposed. Here, we have listed an updated description of pursued micro/nanotechnological approaches focusing on the fabrication processes and the features of the obtained products, as well as on the positive results yielded by in vitro and in vivo studies in comparison to the raw material. The micro/nano-sized formulations here described might be exploited for pharmaceutical delivery of this active, as well as for the production of nutritional supplements or for the enrichment of novel foods.

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Inclusion complex of ellagic acid with β-cyclodextrin: Characterization and in vitro anti-inflammatory evaluation

Cited by 72 publications

References 39 publications

Preparation and Characterization of Octenyl Succinate β-Cyclodextrin and Vitamin E Inclusion Complex and Its Application in Emulsion

Preparation and Characterization of Octenyl Succinate β-Cyclodextrin and Vitamin E Inclusion Complex and Its Application in Emulsion

Development and Evaluation of Antimicrobial and Modulatory Activity of Inclusion Complex of Euterpe oleracea Mart Oil and β-Cyclodextrin or HP-β-Cyclodextrin

Formulation Strategies to Improve Oral Bioavailability of Ellagic Acid

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