Preparation of the high purity gingerols from ginger by dummy molecularly imprinted polymers

Ji, Wenhua; Ma, Xiao; Zhang, Jinghua; Xie, Hong‐Kai; Li, Feng; Xiao, Wang

doi:10.1016/j.chroma.2015.02.002

Cited by 34 publications

(27 citation statements)

References 34 publications

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“…By combining two carbonyl units, the reaction affords β-hydroxyketones which can possess up to two stereo centres. These compounds are found both naturally in polyketides and gingerol or can be prepared synthetically in compounds like atorvastatin (Lipitor)-used in the treatment of blood cholesterol and hydrocortisone-a steroid hormone amongst many others [1][2][3][4][5]. One of the most commonly used catalysts for such reactions includes l-proline due to its inexpensive and environmentally safe nature [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

The effect of the sol–gel structure on the catalysis performance of l-proline

et al. 2019

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Two sol-gel materials based on tetraethylorthosilicate (TEOS) and a combination of methacryloxypropyltrimethoxysilane and zirconium propoxide were developed and used as host matrices for the organic catalyst (l-proline) and iron oxide nanoparticles with the objective of formulating a magnetic sol-gel catalyst. In order to investigate the effect of the sol-gel condensation process on the catalyst recyclability and the effect of the dopants on the structure of the sol-gel matrices, iron oxide nanoparticles and l-proline were introduced in the sol-gel matrices either during the sol-gel synthesis or at the end of the sol-gel synthesis. While both systems were successfully recycled three times when applied to the Aldol reaction, the TEOS based sol-gel material with the dopants introduced at the end of the sol-gel synthesis showed excellent reaction efficiency and recyclability with 99% conversion. In parallel, the zirconium sol-gel-based material did not enable any conversion. Remarkably, it is demonstrated that the process of introducing the dopants strongly effects the condensation of the inorganic networks of the sol-gel matrix by involving the organic catalyst in the catalysis of the condensation of the inorganic moieties. Furthermore, this condensation process is shown to play a major role in the mobility of the organic catalyst and therefore on its ability to be recycled. This study is, to our knowledge, the first that investigates the effect of the morphology and structure of sol-gel matrices on the catalytic performance of an organic catalyst.

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Section: Introductionmentioning

confidence: 99%

The effect of the sol–gel structure on the catalysis performance of l-proline

et al. 2019

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“…This approach has been widely used as an alternative cleanup step in place of traditional procedures involving SPE and LLE, filtration, and centrifugation [20]. The potential of MISPE in the selective extraction of active substances from medicinal plants has been demonstrated previously [21][22][23][24][25][26][27][28], but the preparation of highpurity IGs using MIPs has not been reported. This is perhaps in part because of the difficulty of obtaining template molecules and need for the MIPs to recognize a family of IGs, rather than one single compound.…”

Section: Introductionmentioning

confidence: 99%

Preparation of five high‐purity iridoid glycosides from Gardenia jasminoides Eills by molecularly imprinted solid‐phase extraction integrated with preparative liquid chromatography

Chen

Wang

Cui

et al. 2018

J of Separation Science

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Five iridoid glycosides were prepared using molecularly imprinted solid-phase extraction combined with preparative high-performance liquid chromatography. Hydrophilic molecularly imprinted polymers were synthesized using α-1-allyl-2-N-acetyl glucosamine, which introduced an abundance of hydrophilic groups into the polymers. Using molecularly imprinted solid-phase extraction as the sample pretreatment procedure, five iridoid glycosides, gardenoside, geniposide, shanzhiside, geniposidic acid, and genipin-1-O-gentiobioside, were selectively enriched from Gardenia fructus extracts. Preparative high-performance liquid chromatography then provided iridoid glycosides with a purity >98%. The structures were elucidated by using nuclear magnetic resonance spectroscopy, optical rotation and melting point measurements, and mass spectrometry. The results demonstrate that molecularly imprinted solid-phase extraction combined with preparative high-performance liquid chromatography was an efficient, rapid, and economical method for the preparation of bioactive compounds from natural products.

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“…The adsorption mechanism of the MIPs could be explained using two models: the one binding site model described by Langmuir equation and the continuous distribution model described by Freundlich equation [37,38]. The binding data for MIPs and NIPs toward OC were further processed according to the Langmuir and Freundlich equation, and the results were shown in Figure S7.…”

Section: Adsorption Isothermmentioning

confidence: 99%

“…After equilibration for 2 h at room temperature, the free and bound OC concentrations were quantified following the same procedure as mentioned earlier. The data from the batch rebinding experiments were further processed according to the following Langmuir and Freundlich equations (3,4) [37,38,42]:…”

Section: Adsorption Isothermsmentioning

confidence: 99%

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Molecularly Imprinted Polymers for Selective Extraction of Oblongifolin C from <em>Garcinia yunnanensis</em> Hu

Wang¹,

Wenwei²,

Shen³

et al. 2017

Preprint

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Molecularly imprinted polymers (MIPs) were synthesized and applied for the selective extraction of oblongifolin C (OC) from fruit extracts of Garcinia yunnanensis Hu. A series of experiments and computational approaches were employed to improve the efficiency of screening for optimal MIP systems in the study. The molar ratio (1:4) was chosen at last based on the comparison of the binding energy of the complexes between the template (OC) and functional monomers using density functional theory (DFT) at the RI-PBE-D3-gCP/def2-TZVP level of theory. The binding characterization and the molecular recognition mechanism of MIPs were further explained using the molecular modeling method and NMR and IR spectra data. The reusability of this approach was demonstrated in over 20 batch rebinding experiments. 140.5 mg of OC (>95% purity) was obtained from the 5 g extracts with 2 g of MIPs with the best binding properties through gradient elution program from 35% to 70% methanol-water solution. At the same time, another structural analog, 46.5 mg of guttiferone K (GK) (>88% purity), was also obtained by the gradient elution procedure. Our results showed that the structural analogs could be separated from the crude extracts by the molecularly imprinted solid-phase extraction (MISPE) using a gradient elution procedure for the first time.

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Preparation of the high purity gingerols from ginger by dummy molecularly imprinted polymers

Cited by 34 publications

References 34 publications

The effect of the sol–gel structure on the catalysis performance of l-proline

The effect of the sol–gel structure on the catalysis performance of l-proline

Preparation of five high‐purity iridoid glycosides from Gardenia jasminoides Eills by molecularly imprinted solid‐phase extraction integrated with preparative liquid chromatography

Molecularly Imprinted Polymers for Selective Extraction of Oblongifolin C from <em>Garcinia yunnanensis</em> Hu

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