A novel isopentenyl flavonoid compound and its preparation method and application

A technology of prenyl flavonoids and compounds, which is applied in the field of novel prenyl flavonoids and their preparation, and achieves the effects of clear transformation mechanism, simple transformation method and convenient preparation method

Active Publication Date: 2022-08-02
劲牌持正堂药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned prior art does not mention the precursor components converted into icariin

Method used

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  • A novel isopentenyl flavonoid compound and its preparation method and application
  • A novel isopentenyl flavonoid compound and its preparation method and application
  • A novel isopentenyl flavonoid compound and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0027] (1) Preparation of compounds

[0028] Take 100 g of the dried Epimedium medicinal material, crush it, and extract it by ultrasonic with 80% ethanol aqueous solution for a total of 3 times, 2 hours each time, filter, combine the extracts, and recover the solvent under reduced pressure to obtain the extract. After the extract was dissolved in 1L of water, it was applied to a D101 resin column (200g filler). After the sample was loaded, gradient elution was carried out. Each gradient is one component. After concentrating the components eluted with 30:70 water-ethanol, the concentrated solution is separated by gradient elution of ODS column, and the eluents used are 50:50, 45:55, 40 : 60, 35:55, 30:70 water-methanol, the water-methanol 30:70 eluent fraction was concentrated, purified by high-efficiency preparative liquid phase after concentration, and an octadecyl-bonded silica gel chromatographic column was used. Water-acetonitrile 30:70 (V / V) is the mobile phase, the det...

Embodiment 2

[0038] Weigh 10 mg of 6"'-deoxy-4"'-carbonyl-2"'-β-D-allosyl icariin sample, add 10 mL of 50% ethanol aqueous solution to dissolve, and add 10 μL of molar concentration It is a 1 mol / L aqueous hydrogen chloride solution, stirred at 50 °C for 20 min, and after the reaction is completed, 6.0 mg of icariin can be obtained by semi-preparative liquid phase separation and purification, and lyophilized by a freeze dryer.

Embodiment 3

[0040] Weigh 10 mg of 6"'-deoxy-4"'-carbonyl-2"'-β-D-allosyl icariin sample, add 10 mL of 10% ethanol aqueous solution to dissolve, and add it to a pressurized tank Inside, when the temperature in the tank reaches 140° C., the treatment is carried out for 2 hours. After the reaction is completed, 5.7 mg of icariin can be obtained by semi-preparative liquid phase separation and purification, and lyophilized by a freeze dryer.

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Abstract

The invention discloses a novel isopentenyl flavonoid compound, which is prepared by adopting the following steps: (1) taking Epimedium medicinal materials, pulverizing or not pulverizing, and extracting 1-3 times with a solvent, extracting 0.2-3 times each time After 3 hours, the two extracts were combined and concentrated under reduced pressure to obtain an extract; (2) water was added to the extract to obtain a suspension, the suspension was separated by gradient elution of macroporous resin, and then passed through an ODS column Gradient elution separation was performed, and finally the prenyl flavonoids were purified by high performance preparative liquid phase. The isopentenyl flavonoids can be converted into icariin under the conditions of heating, acid treatment, enzyme treatment, alkali treatment and the like. The invention is easy to operate, and the prepared compound has high purity.

Description

technical field [0001] The invention belongs to the technical field of preparation of medical compounds, and in particular relates to a novel isopentenyl flavonoid compound and a preparation method and application thereof. Background technique [0002] Epimedium is widely used in my country as a tonic, aphrodisiac and anti-rheumatic. Epimedium includes 40 species and is widely distributed throughout China. In addition, Epimedium arrowleaf, Epimedium korea, Epimedium pilosa and Epimedium wushan have been included in the 2015 edition of the Chinese Pharmacopoeia. [0003] Studies have shown that Epimedium has various biological activities, such as anti-osteoporosis, sexual function improvement, neuroprotection, antidepressant, antirheumatic activity and antitumor activity. Through the analysis and research on the components of Epimedium, it is found that its main active ingredients are flavonoids with icariin as the main component, so icariin has been included in the Chinese...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/07C07H1/08C07H1/00C12P19/60
CPCC07H17/07C07H1/08C07H1/00C12P19/60
Inventor 李名洁李昌瑜陈志元孙代华马闯张露明王泽霞
Owner 劲牌持正堂药业有限公司
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