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Preparation method of quercetin-3-O-beta-D-glucuronic acid

A technology of glucuronic acid and quercetin, applied in the field of preparation of quercetin-3-O-β-D-glucuronic acid reference substance, can solve the problems of large amount of organic solvent, high cost, high toxicity, etc. Achieve the effect of simple operation, high cost and high toxicity

Inactive Publication Date: 2016-10-05
GUANGDONG HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

We use liquid chromatography-mass spectrometry on-line analysis technology (see attached figure 1 ) found that the main flavonoid component of kelp is quercetin-3-O-β-D-glucuronic acid, but previous reports on the flavonoids of kelp are mostly quercetin 3-O-β-D-glucose Quercetin 3-O-β-D-glucuronic acid derivatives and their aglycon quercetin [5-7], the analysis may be caused by severe derivatization or hydrolysis of quercetin 3-O-β-D-glucuronic acid during the separation or extraction process to generate artificial products To
However, the current preparation method for the separation and preparation of quercetin-3-O-β-D-glucuronic acid (patent number: CN 101851261A) from the scorpion needs to use high-concentration ethanol extraction, organic solvent extraction, and repeated silica gel column chromatography. and other tedious operations, and the amount of organic solvent is large, toxic and costly

Method used

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  • Preparation method of quercetin-3-O-beta-D-glucuronic acid
  • Preparation method of quercetin-3-O-beta-D-glucuronic acid
  • Preparation method of quercetin-3-O-beta-D-glucuronic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Take 400g (about 4cm / segment) of the medicinal herbs of the barbangui, add 8 times the amount of water, boil and reflux for 2 times, each time for 1 hour, filter with gauze, concentrate to the equivalent concentration of 0.8g / ml of medicinal materials, add ethanol to adjust the The concentration is 50%, stand at low temperature until the precipitation is complete, the supernatant is filtered, concentrated, the sample is dissolved in 20% methanol, placed on an ODS open chromatography column (diameter 5cm × length 32cm), methanol-0.05% acetic acid water (20: 80→35:65→45:55) gradient elution, each half column volume is 1 elution fraction, each ratio elutes 2 column volumes, 45% methanol eluted fractions are concentrated under reduced pressure, and methanol is reconstituted. Sol, TLC, CHCl 3 -MeOH-H 2 O-HCOOH (7:3:0.5:0.2) was developed, there were obvious dark spots at 254nm (the ratio shift value Rf was about 0.4), the fraction was allowed to stand at low temperature, an...

Embodiment 2

[0024] Take 400g (about 4cm / segment) of the medicinal herbs of the barbangui, add 8 times the amount of 30% ethanol, heat and reflux for 2 times, 1 hour each time, filter with gauze, concentrate to the equivalent concentration of medicinal materials 0.8g / ml, add ethanol Adjust its concentration to 50%, stand at low temperature, wait until the precipitation is complete, filter the supernatant, concentrate, dissolve the sample in 20% methanol, and apply it to an ODS open chromatographic column (diameter 5cm×length 32cm), methanol-water (20:80→ 30:70→40:60) gradient elution, one elution fraction per half column volume, each fraction was concentrated under reduced pressure, reconstituted in methanol, thin chromatography, CHCl 3 -MeOH-H 2 O-HCOOH (7: 3: 0.5: 0.2) was developed, and there were obvious dark spots at 254 nm, which were the target fluid content (ratio shift value Rf was about 0.4), stand at low temperature, a large amount of light yellow powder was precipitated, and th...

Embodiment 3

[0026]Take 400g (about 4cm / segment) of the medicinal herbs of the barbangui, add 8 times the amount of water, boil and reflux for 2 times, each time for 1 hour, filter with gauze, concentrate to the equivalent concentration of 0.8g / ml of medicinal materials, add ethanol to adjust the The concentration is 50%, stand at low temperature until the precipitation is complete, the supernatant is filtered, concentrated, the sample is dissolved in 20% methanol, placed on an ODS medium and low pressure chromatography column (diameter 4cm × length 33cm), methanol-0.05% acetic acid water (20 :80→30:70→40:60) gradient elution, 40% methanol elution fractions were concentrated under reduced pressure, reconstituted in methanol, thin chromatography, CHCl 3 -MeOH-H 2 O-HCOOH (7:3:0.5:0.2) was developed, there were obvious dark spots at 254nm (the ratio shift value Rf was about 0.4) and the fraction was left to stand at low temperature. After a large amount of light yellow powder was precipitate...

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Abstract

The invention discloses a preparation method of quercetin-3-O-β-D-glucuronic acid. It extracts the traditional Chinese medicine barley as a raw material, and the obtained extract is filtered and concentrated, and the ethanol content is adjusted to 40 ~80%, remove impurities, concentrate the supernatant to dryness, dissolve in methanol-water, reverse phase column chromatography, elute with 20-70% methanol, detect by thin chromatography, recrystallize and depigment the fraction containing the target stream, After drying, the pure quercetin-3-O-β-D-glucuronic acid with a purity greater than 99% can be obtained in batches. The invention has the advantages of less consumption of organic solvent, low toxicity, simple operation, low cost, and easy laboratory small-scale preparation and pilot production.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a preparation method of a quercetin-3-O-β-D-glucuronic acid reference substance. Background technique [0002] Quercetin-3-O-βD-glucuronic acid (structure as follows) is a flavonoid active ingredient that exists in nature or is metabolized by quercetin in vivo, and has anti-oxidative stress and inflammation [Wang Min, Liu Baolin, Guo Xudan. Quercetin and its metabolites inhibit oxidative stress and inflammation. food science. 2013, 34(15): 256-260], anti-senile dementia [Ho M, Ferruzzi M.G, Janle E.M, et al.Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease. FASEB, 2013, 27, 1-13], anti-lipoxidation [Janisch K.M, Williamson G, Need P, et al. Properties of quercetin conjugates: Modulation of LDL oxidation and binding to human serum albumin. Free Radical Research. 2004, 38 (8), 877-884.], anti-platelet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/08
Inventor 黎雄黄闰月赵亚曾星赵晋苏子仁
Owner GUANGDONG HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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