Enantioseparation of racemic trans-δ-viniferin using high speed counter-current chromatography based on induced circular dichroism technology

•A new method for chiral separation of TVN racemate using HSCCC was established.•Induced circular dichroism was first applied to optimize the chiral HSCCC conditions.•This method could be applied to improve the production rate of the chiral separation. A preparative chiral high speed counter-current...

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Published in	Journal of Chromatography A Vol. 1324; pp. 164 - 170
Main Authors	Han, Chao, Xu, Jinfang, Wang, Xiaobing, Xu, Xiaoming, Luo, Jianguang, Kong, Lingyi
Format	Journal Article
Language	English
Published	Amsterdam Elsevier B.V 10.01.2014 Elsevier
Subjects	2-Hydroxypropyl-beta-cyclodextrin Analytical chemistry aqueous solutions Benzofurans - chemistry Benzofurans - isolation & purification beta-Cyclodextrins - chemistry Biological and medical sciences Chemistry Chiral separation Chromatographic methods and physical methods associated with chromatography Chromatography Chromatography, Liquid - methods Circular Dichroism - methods circular dichroism spectroscopy Circularity countercurrent chromatography Countercurrent Distribution - methods Dichroism Enantiomers Exact sciences and technology General pharmacology High speed High speed counter-current chromatography Hydroxypropyl-β-cyclodextrin Induced circular dichroism spectrum Medical sciences Optimization Other chromatographic methods Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Resorcinols - chemistry Resorcinols - isolation & purification Selectors Separation solvents Stereoisomerism Stilbenes - chemistry Stilbenes - isolation & purification temperature Trans-δ-viniferin Trans-δ-viniferin High speed counter-current chromatography Hydroxypropyl-β-cyclodextrin Induced circular dichroism spectrum Chiral separation Countercurrent chromatography Separation Temperature effect Chiral selector Enantiomer Circular dichroism spectrometry Trans stereoisomer Resveratrol Preparative chromatography Stilbene derivatives Operating conditions Cyclodextrin Ultraviolet detector Optical resolution Phytoalexin Concentration effect Phenols Dimer Benzofuran derivatives Inclusion compound
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Abstract	•A new method for chiral separation of TVN racemate using HSCCC was established.•Induced circular dichroism was first applied to optimize the chiral HSCCC conditions.•This method could be applied to improve the production rate of the chiral separation. A preparative chiral high speed counter-current chromatography (HSCCC) method based on induced circular dichroism (ICD) spectrum was developed to separate trans-δ-viniferin (TVN) enantiomers successfully. The important parameters for the chiral HSCCC separation process, including the type of chiral selector (CS), the concentration of chiral selector and the equilibrium temperature, were optimized using induced circular dichroism spectrum. The final separation procedure was established with a biphasic solvent system composed of n-hexane–ethyl acetate–25mmolL−1 hydroxypropyl-β-cyclodextrin aqueous solution (5:5:10, v/v/v) in the head-to-tail elution mode at 5°C. Under optimum chiral HSCCC separation conditions, 8.2mg of (7S, 8S)-TVN (1) and 9.4mg of (7R, 8R)-TVN (2) were successfully separated from 20mg TVN enantiomers with the purity of 99.51% and 99.36%, respectively.
AbstractList	A preparative chiral high speed counter-current chromatography (HSCCC) method based on induced circular dichroism (ICD) spectrum was developed to separate trans- delta -viniferin (TVN) enantiomers successfully. The important parameters for the chiral HSCCC separation process, including the type of chiral selector (CS), the concentration of chiral selector and the equilibrium temperature, were optimized using induced circular dichroism spectrum. The final separation procedure was established with a biphasic solvent system composed of n-hexane-ethyl acetate-25 mmol L-1 hydroxypropyl- beta -cyclodextrin aqueous solution (5:5:10, v/v/v) in the head-to-tail elution mode at 5 degree C. Under optimum chiral HSCCC separation conditions, 8.2 mg of (7S, 8S)-TVN (1) and 9.4 mg of (7R, 8R)-TVN (2) were successfully separated from 20 mg TVN enantiomers with the purity of 99.51% and 99.36%, respectively. A preparative chiral high speed counter-current chromatography (HSCCC) method based on induced circular dichroism (ICD) spectrum was developed to separate trans-δ-viniferin (TVN) enantiomers successfully. The important parameters for the chiral HSCCC separation process, including the type of chiral selector (CS), the concentration of chiral selector and the equilibrium temperature, were optimized using induced circular dichroism spectrum. The final separation procedure was established with a biphasic solvent system composed of n-hexane–ethyl acetate–25mmolL⁻¹ hydroxypropyl-β-cyclodextrin aqueous solution (5:5:10, v/v/v) in the head-to-tail elution mode at 5°C. Under optimum chiral HSCCC separation conditions, 8.2mg of (7S, 8S)-TVN (1) and 9.4mg of (7R, 8R)-TVN (2) were successfully separated from 20mg TVN enantiomers with the purity of 99.51% and 99.36%, respectively. •A new method for chiral separation of TVN racemate using HSCCC was established.•Induced circular dichroism was first applied to optimize the chiral HSCCC conditions.•This method could be applied to improve the production rate of the chiral separation. A preparative chiral high speed counter-current chromatography (HSCCC) method based on induced circular dichroism (ICD) spectrum was developed to separate trans-δ-viniferin (TVN) enantiomers successfully. The important parameters for the chiral HSCCC separation process, including the type of chiral selector (CS), the concentration of chiral selector and the equilibrium temperature, were optimized using induced circular dichroism spectrum. The final separation procedure was established with a biphasic solvent system composed of n-hexane–ethyl acetate–25mmolL−1 hydroxypropyl-β-cyclodextrin aqueous solution (5:5:10, v/v/v) in the head-to-tail elution mode at 5°C. Under optimum chiral HSCCC separation conditions, 8.2mg of (7S, 8S)-TVN (1) and 9.4mg of (7R, 8R)-TVN (2) were successfully separated from 20mg TVN enantiomers with the purity of 99.51% and 99.36%, respectively. A preparative chiral high speed counter-current chromatography (HSCCC) method based on induced circular dichroism (ICD) spectrum was developed to separate trans-δ-viniferin (TVN) enantiomers successfully. The important parameters for the chiral HSCCC separation process, including the type of chiral selector (CS), the concentration of chiral selector and the equilibrium temperature, were optimized using induced circular dichroism spectrum. The final separation procedure was established with a biphasic solvent system composed of n-hexane-ethyl acetate-25 mmol L(-1) hydroxypropyl-β-cyclodextrin aqueous solution (5:5:10, v/v/v) in the head-to-tail elution mode at 5 °C. Under optimum chiral HSCCC separation conditions, 8.2mg of (7S, 8S)-TVN (1) and 9.4 mg of (7R, 8R)-TVN (2) were successfully separated from 20mg TVN enantiomers with the purity of 99.51% and 99.36%, respectively.
Author	Luo, Jianguang Han, Chao Xu, Xiaoming Xu, Jinfang Kong, Lingyi Wang, Xiaobing
Author_xml	– sequence: 1 givenname: Chao surname: Han fullname: Han, Chao – sequence: 2 givenname: Jinfang surname: Xu fullname: Xu, Jinfang – sequence: 3 givenname: Xiaobing surname: Wang fullname: Wang, Xiaobing – sequence: 4 givenname: Xiaoming surname: Xu fullname: Xu, Xiaoming – sequence: 5 givenname: Jianguang surname: Luo fullname: Luo, Jianguang email: luojg99@163.com – sequence: 6 givenname: Lingyi surname: Kong fullname: Kong, Lingyi email: cpu_lykong@126.com
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Keywords	Trans-δ-viniferin High speed counter-current chromatography Hydroxypropyl-β-cyclodextrin Induced circular dichroism spectrum Chiral separation Countercurrent chromatography Separation Temperature effect Chiral selector Enantiomer Circular dichroism spectrometry Trans stereoisomer Resveratrol Preparative chromatography Stilbene derivatives Operating conditions Cyclodextrin Ultraviolet detector Optical resolution Phytoalexin Concentration effect Phenols Dimer Benzofuran derivatives Inclusion compound
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Snippet	•A new method for chiral separation of TVN racemate using HSCCC was established.•Induced circular dichroism was first applied to optimize the chiral HSCCC... A preparative chiral high speed counter-current chromatography (HSCCC) method based on induced circular dichroism (ICD) spectrum was developed to separate...
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SubjectTerms	2-Hydroxypropyl-beta-cyclodextrin Analytical chemistry aqueous solutions Benzofurans - chemistry Benzofurans - isolation & purification beta-Cyclodextrins - chemistry Biological and medical sciences Chemistry Chiral separation Chromatographic methods and physical methods associated with chromatography Chromatography Chromatography, Liquid - methods Circular Dichroism - methods circular dichroism spectroscopy Circularity countercurrent chromatography Countercurrent Distribution - methods Dichroism Enantiomers Exact sciences and technology General pharmacology High speed High speed counter-current chromatography Hydroxypropyl-β-cyclodextrin Induced circular dichroism spectrum Medical sciences Optimization Other chromatographic methods Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Resorcinols - chemistry Resorcinols - isolation & purification Selectors Separation solvents Stereoisomerism Stilbenes - chemistry Stilbenes - isolation & purification temperature Trans-δ-viniferin
Title	Enantioseparation of racemic trans-δ-viniferin using high speed counter-current chromatography based on induced circular dichroism technology
URI	https://dx.doi.org/10.1016/j.chroma.2013.11.037 https://www.ncbi.nlm.nih.gov/pubmed/24315679 https://www.proquest.com/docview/1635021116 https://www.proquest.com/docview/1800426678 https://www.proquest.com/docview/2101349127
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