Novel isopentenyl flavonoid compound and preparation method and application thereof

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: 2020-10-30
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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  • Novel isopentenyl flavonoid compound and preparation method and application thereof
  • Novel isopentenyl flavonoid compound and preparation method and application thereof
  • Novel isopentenyl flavonoid compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] (1) Preparation of compounds

[0028] Take 100 g of dried epimedium, pulverize it, and ultrasonically extract it with 80% ethanol aqueous solution for 3 times, each time for 2 hours, filter, combine the extracts, recover the solvent under reduced pressure, and obtain the extract. After the extract was dissolved in 1L of water, put it on a D101 resin column (200g packing). After loading, gradient elution was carried out. Each gradient is a component. After the 30:70 water-ethanol eluted component is concentrated, the concentrated solution is separated by ODS column gradient elution, and the eluents used are 50:50, 45:55, 40 :60, 35:55, 30:70 water-methanol, concentrate the water-methanol 30:70 eluent components, and then use high-efficiency preparative liquid phase purification after concentration, using octadecyl bonded silica gel chromatography column to Water-acetonitrile 30:70 (V / V) is the mobile phase, the detection wave is 254nm, Capcell pak AQ column (250×10mm, 5...

Embodiment 2

[0038] Weigh 10 mg of 6"'-deoxy-4"'-carbonyl-2"'-β-D-allosyl icariin sample, add 10 mL of ethanol solution with a volume fraction of 50% to dissolve, add 10 μL of molar concentration It is a 1mol / L hydrogen chloride aqueous solution, stirred at 50°C for 20 minutes, after the reaction is completed, separated and purified by semi-preparative liquid phase, and lyophilized with a lyophilizer to obtain 6.0 mg of icariin.

Embodiment 3

[0040] Weigh 10 mg of 6"'-deoxy-4"'-carbonyl-2"'-β-D-allosyl icariin sample, add 10 mL of ethanol solution with a volume fraction of 10% to dissolve, and add to a pressurized tank In the tank, when the temperature in the tank reaches 140°C, it is treated for 2 hours. After the reaction is completed, it is separated and purified by semi-preparative liquid phase, and lyophilized with a lyophilizer to obtain 5.7 mg of icariin.

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Abstract

The invention discloses a novel isopentenyl flavonoid compound which is prepared by the following steps: (1) taking herba epimedii, crushing or not crushing, extracting with a solvent for 1-3 times, extracting for 0.2-3 hours each time, combining extracting solutions obtained by two times, and concentrating the extracting solutions under reduced pressure to obtain extract, and (2) adding water into the extract to prepare a suspension, carrying out gradient elution separation on the suspension by using macroporous resin, carrying out gradient elution separation by using an ODS column, and finally purifying the isopentenyl flavonoid compound by using an efficient preparative liquid phase. The isopentenyl flavonoid compound can be converted into icariin under the conditions of heating, acid treatment, enzyme treatment, alkali treatment and the like. The method is simple and convenient 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 prenyl flavonoid compound and its preparation method and application. Background technique [0002] Epimedium is widely used in my country as a tonic, aphrodisiac and antirheumatic drug. The genus Epimedium includes 40 species, which are widely distributed throughout China. And Epimedium sagitta, Epimedium Korean, Epimedium vellus and Epimedium Wushanii have been included in the 2015 edition of "Chinese Pharmacopoeia". [0003] Studies have shown that Epimedium has various biological activities, such as anti-osteoporosis, improvement of sexual function, neuroprotection, antidepressant, antirheumatic activity and antitumor activity. Through the analysis and research on the components of Epimedium, it was found that the main active ingredient is 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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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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