Powdered bilberry extract (United States Pharmacopoeia, USP35-NF30), which is prepared from ripe bilberry fruits (Vaccinium myrtillus L.), is the main ingredient of drugs alleviating visual fatigue and diabetic retinopathy because of the rich anthocyanins (purity of 36%). In this study, a method based on a macroporous polymeric adsorbent was established to obtain anthocyanin compounds from bilberry, in which the purity of the anthocyanins was improved to 96%, conducive to further pharmacological research and improvement of the efficiency of the drug. On the basis of the structure of anthocyanins, we designed a series of macroporous polymeric adsorbents based on the copolymerization of divinylbenzene (DVB) and ethylene glycol dimethyl acrylate (EGDMA). In this situation, EGDMA not only regulated the polarity of the adsorbent but also acted as the cross-linking agent to ensure the matrix structure of the adsorbent, which had a high specific surface area and could provide more interaction sites during adsorption with anthocyanins. Among the synthesized polymeric adsorbents with different contents of EGDMA, the one with 20% EGDMA content (DE-20) was demonstrated to exhibit optimal adsorption capacity and selectivity to anthocyanins compared to various commercial adsorbents through static adsorption and desorption experiments. In addition, the optimum condition of the dynamic adsorption–desorption experiment was further explored. The results indicated that the purity of anthocyanins after rinsing with 20% ethanol was determined to be approximately 96% at a desorption ratio of 83%, which was clearly higher than that in powdered bilberry extract. The established separation and purification method of anthocyanins with high purity is expected to be applied in industrial production.

•A method for separation of RA glycoside from Steviol glycoside using a polymeric adsorbent-bonding polyethylene polyamine is proposed.•The mechanism relies on the synergetic interaction of multi-hydrogen in the non-aqueous system.•Under the optimized gradient elution conditions, highly purified RA glycoside was obtained, and the adsorption–desorption process is superior for industrial applications.Rebaudioside A (RA) and stevioside (SS) are the primary effective glycoside components in Stevia Rebaudiana. The RA glycoside is sweeter, and it tastes similarly to sucrose. Because extracts with a high RA content can be used as natural sweeteners for food additives approved by the FAO and FDA, RA should generate high market demand. In this study, an efficient method for separating RA was established based on the synergistic multi-hydrogen bonding interaction between a polymeric adsorbent and the RA glycoside. To overcome the destruction of the hydrophobic affinity required for the selective adsorption of RA, an innovative non-aqueous environment was established for adsorption and separation. To this end, an initial polymeric adsorbent composed of a glycidyl methacrylate and trimethylolpropane trimethacrylate (GMA-co-TMPTMA) copolymer matrix was synthesized, and polyethylene polyamine was employed as a functional reagent designed to react with the epoxy group on GME-co-TMPTMA to form a highly selective macroporous adsorbent. The effects of the different functional reagents and the solvent polarity on the adsorption selectivity for RA and SS, respectively, were investigated. Matching the structure of the polyethylene polyamine and sugar ligand on the glycoside molecule was essential in ensuring that the maximum synergistic interaction between adsorbent and adsorbate would be achieved. Moreover, the hydrogen-bonding force was observed to increase when the polarity of the adsorption solvent decreased. Therefore, among the synthesized macroporous polymeric adsorbents, the GTN4 adsorbent-bonding tetraethylenepentamine functional group provided the best separation in an n-butyl alcohol solution. Under the optimized gradient elution conditions, RA and SS can be effectively separated, and the contents of RA and SS increased from 33.5% and 51.5% in the initial crude extract to 95.4% and 78.2% after separation, respectively. Compared to conventional methods, the adsorption–desorption process is more advanced due to its procedural simplicity, low cost and adaptability for industrial production.

The heterogenization of a polyoxometalate (POM) catalyst by direct covalent immobilization in polymer matrices with uniform macropores and high specific surface areas was reported. Via click chemistry, organically modified POM clusters were mainly “clicked” on the functionalized channel surface of a macroporous resin. The appraisement of the catalytic performance via catalysis on tetrahydrothiophene (THT) oxidation, demonstrates that the solid catalyst is efficient and has a high selectivity. More attractively, it could be reused several times without detectable catalytic activity loss. And no POM species were detected in the filtrate, stemming from the strong covalent bonding between the POM clusters and the macroporous resin surface. Evidently, such a catalyst heterogenization strategy helps to overcome the fatal leaching problem. Therefore the POM heterogeneous material can become an ideal candidate for industrial processes and will also have great potential in practical application not only for oxidative catalysis.

In this study, with flavonol glycosides (FG) and terpene lactones (TL) in ginkgo biloba extract (GBE) as the targets for separation, we investigated the effectiveness of molecular docking in adsorbent screening. Several polyamine-modified methyl acylate-co-divinylbenzene (MA-co-DVB) adsorbent models were built, and their affinity to rutin, quercetin and ginkgolide B (GB) was evaluated via molecular docking. The model of ethylenediamine-modified adsorbent showed the largest difference in affinity between to GB and to quercetin as well as rutin, and thus this adsorbent could have the best separation performance. The results of the subsequently conducted static adsorption and dynamic adsorption experiments correlated well with docking results. Finally, using ethylenediamine-modified MA-co-DVB adsorbent, nearly complete separation of the FG and TL in GBE was simply achieved by one step of adsorption–desorption. Thus, the reported molecular docking method is expected to be helpful for rapid adsorbent screening.

The individual flavonoid component, scutellarin, scutellarein, luteolin and apigenin, in Scutellaria barbata plant was isolated based on the macro porous adsorbent with high adsorption selectivity. These adsorbents were synthesized based on the copolymerization of methyl acrylate and divinylbenzene (MA-co-DVB). So the polarity and the adsorption affinity of these adsorbents can be adjusted through changing MA content in the adsorbents. And then the ability of the adsorbent with different MA contents for isolation of these four individual flavonoid was also investigated. Adsorbents M2 and M4, with MA content of 25% and 45%, respectively, demonstrated the best separation ability. Complete separation of the four flavone compounds was achieved in a continuous process based on combination of adsorbents with different polarities (M2 and M4). Gradient elution using adsorbent M4 separated the four flavonoids into three fractions, which were determined to contain scutellarin, scutellarein and a mixture of luteolin and apigenin. The latter was separated completely by adsorbent M2 subsequently. All four compounds were obtained at high resolution and high recovery yield (96.7%, 94.1%, 95.8% and 93.8%, respectively), suggesting the efficiency of sequentially combined columns with different segregation patterns.