Adsorption chromatography separation of the flavonols kaempferol, quercetin and myricetin using cross‐linked collagen fibre as the stationary phase

Ding, Pingping; Liao, Xuepin; Shi, Bi

doi:10.1002/jsfa.5924

Cited by 10 publications

(15 citation statements)

References 29 publications

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“…Decoration with oxides Enhancing the surface roughness [127,185] Coating of low surface energy substances Reducing the surface energy [127,[130][131][132][133][134]185] Coordination with metal ions Enhancing hydrophilicity, regulating surface charges, and improving thermal and chemical stability [129,157,158,160,164,167,168] Incorporation with carbon materials Adsorbing surfactants stabilized with emulsion droplets, enhancing surface roughness, and regulating surface charges [130][131][132] In-situ growth of metal-organic frameworks Size-sieving-based demulsification, and enhancing the surface roughness [133,134] Cross-linked with aldehydes Enhancing the thermal and chemical stability [135][136][137][138][139][140] Non-covalent modification with tannins Chelating with metal ions [142][143][144][145][146]150,151,153,156] Hydrolysis by enzyme Generating more functional groups [146,148,156] Chemical grafting Increasing the number of functional groups [141,149] Alkali activation Increasing the number of functional groups…”

Section: Functionalization Role Referencesmentioning

confidence: 99%

“…Ding and co‐workers developed a type of chromatographic separation packing materials by using glutaraldehyde to cross‐link with CFs for the separation and purification of flavonoids. [ 139 ] In their investigations, the polar groups contained in CFs were prone to form hydrogen bonds with the OH of flavonoids. As for various flavonoids, their hydroxyl contents and positions are varied, which leaded to the differences in the interaction strengths of the hydrogen bonds formed by each type of flavonoid with CFs, thereby facilitating the separation of mixed flavonoids.…”

Section: Separation Of Natural Productsmentioning

confidence: 99%

“…[127][128][129][130][131][132][133][134] The high affinity of CFs toward amphiphilic compounds allowed for highly efficient separation of natural products. [135][136][137][138][139][140] The noncovalent binding ability of CFs with plant polyphenols provided facile alternatives for adsorptive separation of metal ions. [141][142][143][144][145][146][147][148][149][150][151][152][153][154][155][156] The coordinating ability of CFs with metal ions permitted convenient tuning of their surfaces charges and the binding sites for the separation of anionic contaminants, [157][158][159][160][161][162][163][164][165][166] as well as, the purification of proteins.…”

Section: Introductionmentioning

confidence: 99%

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Collagen Fiber‐Based Advanced Separation Materials: Recent Developments and Future Perspectives

et al. 2022

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Separation plays a critical role in a broad range of industrial applications. Developing advanced separation materials is of great significance for the future development of separation technology. Collagen fibers (CFs), the typical structural proteins, exhibit unique structural hierarchy, amphiphilic wettability, and versatile chemical reactivity. These distinctive properties provide infinite possibilities for the rational design of advanced separation materials. During the past 2 decades, many progressive achievements in the development of CFs‐derived advanced separation materials have been witnessed already. Herein, the CFs‐based separation materials are focused on and the recent progresses in this topic are reviewed. CFs widely existing in animal skins display unique hierarchically fibrous structure, amphiphilicity‐enabled surface wetting behaviors, multi‐functionality guaranteed covalent/non‐covalent reaction versatility. These outstanding merits of CFs bring great opportunities for realizing rational design of a variety of advanced separation materials that were capable of achieving high‐performance separations to diverse specific targets, including oily pollutants, natural products, metal ions, anionic contaminants and proteins, etc. Besides, the important issues for the further development of CFs‐based advanced separation materials are also discussed.

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Section: Functionalization Role Referencesmentioning

confidence: 99%

Section: Separation Of Natural Productsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Collagen Fiber‐Based Advanced Separation Materials: Recent Developments and Future Perspectives

et al. 2022

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“…20,21 Kaempferol and quercetin, which are two typical flavonoid aglycones with the difference of one hydroxyl group, were separated only by a collagen fiber column with the length−diameter ratio up to 60. 21 Separation on a column with an excessively high length− diameter ratio not only costs time but also requires a special separation equipment and site.…”

Section: Introductionmentioning

confidence: 99%

Controllably Adjusting the Hydrophobicity of Collagen Fibers for Enhancing the Adsorption Rate, Retention Capacity, and Separation Performance of Flavonoid Aglycones

Zhang

Sun

Wang

et al. 2023

ACS Appl. Mater. Interfaces

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Collagen fibers (CFs) were previously used as packing materials for the separation of flavonoids based on hydrogen bond and hydrophobic interactions. However, as for flavonoid aglycones, CFs presented unsatisfactory adsorption capacity and separation efficiency due to the fact that they include limited hydroxyls and phenyls. In order to improve the adsorption capacity and separation efficiency, the hydrophobic modification strategy was employed in this research to enhance the hydrophobic interaction of CF with flavonoid aglycones by using silane coupling agents with different alkyl chains (isobutyl, octyl, and dodecyl). FT-IR analysis, DSC, TG, SEM, EDS mapping, water contact angle, and absorption time of solvent proved the successful grafting of alkyl chains on the CF without disturbing its special fiber structure, leading to the significantly enhanced hydrophobicity of the CF. The dynamic adsorption and elution behavior of kaempferol and quercetin (the typical flavonoid aglycones) on the hydrophobic CF showed that the adsorption rate and retention rate were largely increased in comparison with the CF without modification. Molecular dynamic simulations indicated that the CF grafted with isobutyls could interact with flavonoid aglycones through the highest synergetic effect of hydrophobic and hydrogen bond interactions, which exhibited the strongest retention to flavonoid aglycones. On further increasing the alkyl length (octyl and dodecyl), the hydrophobic interaction was further enhanced, but the hydrogen bonds were significantly weakened by steric hindrance, which showed that the retention to flavonoid aglycones was appropriately increased but without causing peak tailing. In the column separation of kaempferol and quercetin, the CF with hydrophobic modification presented a greater separation efficiency, with the purity of kaempferol increased from 71.99 to 86.57–97.50% and the purity of quercetin increased from 82.69 to 88.07–99.37%, which was much better than that of polyamide and close to that of sephadex LH 20. Therefore, the hydrophobicity of the CF could be controllably adjusted to enhance the adsorption rate and retention capacity, specifically improving the separation efficiency of flavonoid aglycones.

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“…1). Currently, conventional methods, such as column chromatography, preparative/semipreparative reversed-phase liquid chromatography, macroporous resin and traditional liquidliquid extraction, are used for the isolation and purification of flavonoids (Ding et al, 2013). However, these methods require multiple chromatographic steps that are not only cumbersome, but also time-consuming and organic solvent-consuming.…”

Section: Introductionmentioning

confidence: 99%

Competitive cocrystallization and its application in the separation of flavonoids

Xia

Wei

Chen

et al. 2021

Int Union Crystallogr J

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Recently, cocrystallization has been widely employed to tailor physicochemical properties of drugs in the pharmaceutical field. In this study, cocrystallization was applied to separate natural compounds with similar structures. Three flavonoids [baicalein (BAI), quercetin (QUE) and myricetin (MYR)] were used as model compounds. The coformer caffeine (CAF) could form cocrystals with all three flavonoids, namely BAI–CAF (cocrystal 1), QUE–CAF (cocrystal 2) and MYR–CAF (cocrystal 3). After adding CAF to methanol solution containing MYR and QUE (or QUE and BAI), cocrystal 3 (or cocrystal 2) preferentially formed rather than cocrystal 2 (or cocrystal 1), indicating that flavonoid separation could be achieved by competitive cocrystallization. After co-mixing the slurry of two flavonoids with CAF followed by centrifugation, the resolution ratio that could be achieved was 70–80% with purity >90%. Among the three cocrystals, cocrystal 3 showed the lowest formation constant with a negative Gibbs free energy of nucleation and the highest energy gap. Hirshfeld surface analysis and density of states analysis found that cocrystal 3 had the highest strong interaction contribution and the closest electronic density, respectively, followed by cocrystal 2 and cocrystal 1, suggesting CAF could competitively form a cocrystal with MYR much more easily than QUE and BAI. Cocrystallization is a promising approach for green and effective separation of natural products with similar chemical structures.

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Adsorption chromatography separation of the flavonols kaempferol, quercetin and myricetin using cross‐linked collagen fibre as the stationary phase

Abstract: GCF is a promising adsorbent for use as a stationary phase in the chromatographic separation of flavonols from their mixtures.

Cited by 10 publications

References 29 publications

Collagen Fiber‐Based Advanced Separation Materials: Recent Developments and Future Perspectives

Collagen Fiber‐Based Advanced Separation Materials: Recent Developments and Future Perspectives

Controllably Adjusting the Hydrophobicity of Collagen Fibers for Enhancing the Adsorption Rate, Retention Capacity, and Separation Performance of Flavonoid Aglycones

Competitive cocrystallization and its application in the separation of flavonoids

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