Investigation of the inclusion behavior of chlorogenic acid with hydroxypropyl-β-cyclodextrin

Chao, Jianbin; Wang, Hongfang; Zhao, Wei; Zhang, Min; Zhang, Liwei

doi:10.1016/j.ijbiomac.2011.11.008

Cited by 48 publications

(28 citation statements)

References 20 publications

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“…The extraction process used might also lead to degradation of the bioactive molecules, thus hampering their bioavailability. CDs are known for their capability to form inclusion complexes between bioactive compounds and their characteristic hydrophobic cavity, thereby enhancing the solubility, stability and bioavailability of the bioactives (Chao et al 2012;Lucas-Abellán et al 2011;Mercader-Ros et al 2010;Šmidovnik et al 2010). The impact of number of glucose residues in three CD forms (α-, β-, γ-) and two derivatives (HPβ-and RMβ-CDs) at 0.025 mol L −1 and a comparison with sonication-assisted organic solvent-based extraction was investigated for the comparison of recovery of total polyphenols (flavonols + dihydrochalcones + phenolic acids + flavanols) from apple pomace powder.…”

Section: Resultsmentioning

confidence: 99%

“…Although there have been several studies focusing on flavonoid encapsulation in different types of CDs for improving quality (Karangwa et al 2012), physico-chemical stability (Chao et al 2012;Mercader-Ros et al 2010), solubility (Lucas-Abellán et al 2011) and bio-availability (Šmidovnik et al 2010), to the best of our knowledge, there are no reports available on the use of CDs in recovering flavonols from apple pomace. Therefore, the current study was carried out to compare the flavonol extraction efficiencies of α-, β-, γ-CDs, two derivatives of β-CD and solvents from apple pomace and to optimize β-CD-based flavonol extraction conditions using response surface methodology.…”

Section: Introductionmentioning

confidence: 99%

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Optimization of β-cyclodextrin-based flavonol extraction from apple pomace using response surface methodology

2014

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The present study investigated five cyclodextrins (CDs) for the extraction of flavonols from apple pomace powder and optimized β-CD based extraction of total flavonols using response surface methodology. A 2(3) central composite design with β-CD concentration (0-5 g 100 mL(-1)), extraction temperature (20-72 °C), extraction time (6-48 h) and second-order quadratic model for the total flavonol yield (mg 100 g(-1) DM) was selected to generate the response surface curves. The optimal conditions obtained were: β-CD concentration, 2.8 g 100 mL(-1); extraction temperature, 45 °C and extraction time, 25.6 h that predicted the extraction of 166.6 mg total flavonols 100 g(-1) DM. The predicted amount was comparable to the experimental amount of 151.5 mg total flavonols 100 g(-1) DM obtained from optimal β-CD based parameters, thereby giving a low absolute error and adequacy of fitted model. In addition, the results from optimized extraction conditions showed values similar to those obtained through previously established solvent based sonication assisted flavonol extraction procedure. To the best of our knowledge, this is the first study to optimize aqueous β-CD based flavonol extraction which presents an environmentally safe method for value-addition to under-utilized bio resources.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Optimization of β-cyclodextrin-based flavonol extraction from apple pomace using response surface methodology

2014

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“…Apesar dos relatos na literatura indicarem que essas substâncias possuem atividade antimicrobiana (GARAMBONE; ROSA, 2007;CHAO et al, 2012;CLAUDIO et al, 2013), os resultados obtidos no presente trabalho demostraram que não houve ação inibitória dos extratos oleosos frente aos microrganismos testados. O extrato hidroetanólico que apresentou maior concentração de cafeína (etanol 40%) também foi testado, porém, utilizando o método de micro diluição.…”

Section: Determinação In Vitro Da Atividade Antimicrobiana Dos Extratunclassified

Extração e caracterização de compostos do resíduo vegetal casca de café.

et al. 2017

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A quantidade de resíduos gerados durante o beneficiamento do café no Brasil (principalmente casca) representa aproximadamente 50% da produção. Visando diminuir este problema, o objetivo deste trabalho foi obter diferentes extratos das cascas de café, avaliar sua composição e atividade antimicrobiana. Utilizando extrações por Soxhlet, com solventes de diferentes polaridades e seletividades e analisando estes extratos por Cromatografia Gasosa acoplada à Espectrometria de Massas e Espectroscopia de Infravermelho com Transformada de Fourier, foi possível observar que os extratos diferiam em composição química e que apenas clorofórmio e diclorometano foram capazes de extrair a cafeína, devido a seletividades destes solventes. Os componentes hidrofílicos foram extraídos utilizando diferentes proporções de etanol e água, a temperatura ambiente e a 40 °C. A cafeína presente nestes extratos foi quantificada por Cromatografia Líquida de Alta Eficiência. A mudança na composição do solvente e temperatura não alteraram a composição química dos extratos, porém alteraram a quantidade de cafeína extraída. Nenhum dos extratos testados demonstrou atividade contra os microrganismos Salmonella typhimurium (ATCC 14028), Escherichia coli (ATCC 25922), Staphylococcus aureus (ATCC 25923), Pseudomonas aeruginosa (ATCC 27853) e Bacillus cereus (ATCC 14579). Pode-se concluir que as cascas de café apresentam grande potencial para a extração de cafeína, agregando valor a este resíduo vegetal e contribuindo para o aproveitamento dos resíduos produzidos no beneficiamento do café, o que diminuiria o impacto ambiental gerado pelo descarte destes.

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“…On the internal surface of the CD cavity, the H 3 and H 5 protons of the oligosaccharide can be found, while on the external surface are the H 1 , H 2 , H 4 , and H 6 protons (Mura, 2014;Zoppi, Quevedo, & Longhi, 2008 (Chao, Wang, Zhao, Zhang, & Zhang, 2012;Pedotti et al, 2015).…”

Section: H-nmr Spectroscopy and 2d-roesy Spectramentioning

confidence: 99%

Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone

Araújo

Zoppi

Barbosa

et al. 2016

Carbohydrate Polymers

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A second compound is generally associated with oligosaccharides as a strategy to maximize the solubilizing effect for nonpolar compounds. This study elucidated the role and the mechanism whereby liquid compounds interact in these supramolecular aggregates in the solubilization of triamcinolone. Three different oligosaccharides (beta-cyclodextrin, 2-hydroxipropil-beta-cyclodextrin, and randomly methylated beta-cyclodextrin) and two potent co-solvents (triethanolamine and N-methyl pyrrolidone) were carefully evaluated by using three distinct experimental approaches. Incredibly stable complexes were formed with cyclodextrins (CDs). The structure of the complexes was elucidated by magnetic resonance spectra 2D-ROESY. The interactions of the protons of ring "A" of the drug with H(3) and H(5) protons of the CD cavity observed in the binary complexes remained in both ternary complexes. Unlike the observed ternary associations with triethanolamine, N-methyl pyrrolidone competed with the triamcinolone CD cavity and considerably decreased the stability of the complex and the solubility of the drug. The molecular dynamics (MD) and quantum mechanics:molecular mechanics (QM:MM) calculations supported that triethanolamine stabilized the drug-CD interactions for the conformer identified in the 2D-ROESY experiments, improving the quality and uniformity of the formed complex. The role played by the co-solvent in the ternary complexes depends on its specific ability to interact with the CD cavity in the presence of the drug, which can be predicted in theoretical studies to select the best candidate.

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Investigation of the inclusion behavior of chlorogenic acid with hydroxypropyl-β-cyclodextrin

Cited by 48 publications

References 20 publications

Optimization of β-cyclodextrin-based flavonol extraction from apple pomace using response surface methodology

Optimization of β-cyclodextrin-based flavonol extraction from apple pomace using response surface methodology

Extração e caracterização de compostos do resíduo vegetal casca de café.

Supramolecular aggregates of oligosaccharides with co-solvents in ternary systems for the solubilizing approach of triamcinolone

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