Chiral chromatographic separation and analysis method of dihydromyricetin enantiomer

A technique for separation and analysis of dihydromyricetin, applied in the field of chiral chromatographic separation, can solve the problems of physiological activity, toxicity and clinical efficacy, difficult elution and separation of mobile phases, etc., and achieve good chiral separation and analytical separation. Fast speed and improved peak broadening

Active Publication Date: 2016-01-13
GUANGDONG YANJIE PHARMA TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Since the dihydromyricetin molecule contains multiple hydroxyl groups and aromatic rings, it is easy to generate strong hydrogen bonds and π-π interactions with chiral selectors and silica gel, and it is difficult to be eluted and resolved by mobile phases. Research Report on Chiral Analysis and Separation of Dihydromyricetin Using Chiral Chromatographic Columns Directly
On the other hand, the stereo configuration of chiral compounds may have a great impact on their physiological activity, toxicity and clinical efficacy

Method used

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  • Chiral chromatographic separation and analysis method of dihydromyricetin enantiomer
  • Chiral chromatographic separation and analysis method of dihydromyricetin enantiomer
  • Chiral chromatographic separation and analysis method of dihydromyricetin enantiomer

Examples

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Embodiment 1

[0087] Example 1 in Enantiopak TM Chiral Separation of Dihydromyricetin Enantiomers on AD Column

[0088] Firstly, the dihydromyricetin sample (purity>98%) was dissolved in the mobile phase to prepare a concentration of 0.50 mg·mL -1 solution; on the Agilent 1200 Series HPLC, using Enantiopak TM AD chromatographic column (150×4.6mm), n-hexane: trifluoroacetic acid: ethanol=80:0.1:20 (v / v / v) as the mobile phase, the flow rate is 1.0mL min -1 , the column temperature was 25° C. and the detection wavelength was 290 nm, and the above sample solution was chromatographically separated.

[0089] Such as figure 1 As shown, two chromatographic peaks appeared in the dihydromyricetin sample at 11.26min and 14.25min respectively, and the resolution was 1.95.

Embodiment 2

[0090] Example 2 in Enantiopak TM Chiral Separation of Dihydromyricetin Samples on AD Chromatographic Column

[0091] Firstly, dihydromyricetin sample (purity>98%) was dissolved in mobile phase to prepare a concentration of 10 mg·mL -1 solution; on the Agilent 1200 Series HPLC, using Enantiopak TM AD chromatographic column (150×4.6mm), n-hexane: trifluoroacetic acid: ethanol=80:0.1:20 (v / v / v) as the mobile phase, the flow rate is 1.0mL min -1 The dihydromyricetin sample was chromatographically separated at a column temperature of 25°C, and the separation of the sample was monitored by a CHIRALYSER-MP polarimetric detector.

[0092] Such as figure 2 As shown, two chromatographic peaks occurred in the sample at 11.14min and 12.25min, and the peak time was close to that of Example 1. The optical rotation of the isomer eluting first is negative, and the isomer eluting later is positive. The detection of the sample by an optical rotation detector shows that the dihydromyricet...

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Abstract

The invention provides a chiral chromatographic separation and analysis method of dihydromyricetin enantiomer. The method comprises the following steps: dissolving a dihydromyricetin sample into the mobile phase, taking polysaccharide derivatives as the chiral stationary phase, and carrying out liquid chromatogram (LC) separation and analysis; wherein the mobile phase is a mixed solution of n-hexane and lower alcohols, and the polysaccharide derivative chiral stationary phase is one of stationary phases, which are individually covered by tri(3,5-dimethylphenylcarbamyl) straight-chain starch, tri((S)-(alpha)- phenylethylcarbamyl) straight-chain starch, tri(3,5- dimethylphenylcarbamyl)cellulose and tri(4- methylphenylcarbamyl)cellulose. According to the provided chiral separation and analysis method, the maximal separation degree of dihydromyricetin enantiomer is 1.95, and the maximal selection factor is 1.36.

Description

technical field [0001] The invention belongs to the technical field of chiral chromatographic separation, and more specifically relates to a chiral chromatographic separation and analysis method of dihydromyricetin enantiomers. Background technique [0002] Dihydromyricetin (see formula I(a)) is a flavonoid compound with the chemical name (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxy hydroxyphenyl)chroman-4-one. In 1940, Kotake and Kubota were first isolated from the leaves of A. Meliaefolia. As a rare natural active substance, dihydromyricetin has anti-inflammatory, anti-allergic and anti-oxidative properties [Modern Food Science and Technology, 2014, (10): 36-41; Food Science, 2014, (20): 69-71 ], cough and expectorant [Chinese Journal of National Medicine, 1998, (3): 42-44], analgesia [Fujian Medical Miscellaneous Science, 1995, (4): 39-40], antibacterial [Food Science and Technology, 2008, ( 4): 140-143], hypolipidemic [Tea Science, 2007, (3): 221-225], anti-lipid pero...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/34
Inventor 章伟光李丽群范军
Owner GUANGDONG YANJIE PHARMA TECH CO LTD
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