Isopentene flavonol glycoside derivative and preparation method and application thereof

A technology for isopentenyl flavonol glycosides and derivatives, which is applied in the field of medicine and can solve the problems of high price, uncertain long-term efficacy, large toxic and side effects, and the like

Active Publication Date: 2012-03-28
GUOYAOJITUAN TONGJITANG (GUIZHOU) PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs can prevent and treat osteoporosis to varying degrees, relieve pain, and reduce the incidence of fractures, but they also have many disadvantages such as large toxic and side effects, uncertain long-term curative effect, and high price.

Method used

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  • Isopentene flavonol glycoside derivative and preparation method and application thereof
  • Isopentene flavonol glycoside derivative and preparation method and application thereof
  • Isopentene flavonol glycoside derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: Preparation of prenyl flavonol glycoside derivatives of the present invention

[0056] 1. Take 2 kg of dry Epimedium pilosa aerial parts (aerial parts except the root diameter, etc.), heat and reflux extract 2 times with 60% ethanol of 8 times the amount, each time for 2 hours, and the extract is evaporated to dryness under reduced pressure Afterwards, extract 245g is obtained;

[0057] 2. Suspend the extract in 5L of water, filter it, put the filtrate on a macroporous adsorption resin HP-20 chromatographic column (Ф9×70cm), and wash it with water, 30%, 95% (v / v) ethanol-water in sequence , wherein, 95% (v / v) ethanol-water elution part obtains 80g altogether;

[0058] 3. Separate 80 g of 95% (v / v) ethanol-water eluted part with silica gel open column chromatography, adopt chloroform-methanol solvent system gradient elution, and collect the eluent with each 1 / 3 column retention volume as a part, The eluents were combined according to the different spots o...

experiment example 2

[0085] Experimental Example 2: Effects of the compounds and analogs obtained in Example 1 on the alkaline phosphatase activity (ALP) of the osteoblast-like cell line MC3T3-E1 cells.

[0086] With the ALP activity of osteoblast-like cell line MC3T3-E1 cells, evaluate the promotion of osteoblasts by the compounds obtained in Example 1 and structural analogues Epimedin A, Epimedin B, Epimedin C and Icariin The role of differentiation.

[0087] MC3T3-E1 cells were seeded in 24-well plates (1×10 5 cells / well), cultured in α-MEM medium containing 10% FBS (fetal bovine serum) (37°C, humidity 95%, 5% CO 2 ).

[0088] After 2 days, the MC3T3-E1 cells were replaced with α-MEM medium containing 0.3% FBS and different concentrations of compounds (0.01 μmol / L, 0.1 μmol / L, 1 μmol / L). Cultured in α-MEM medium with %FBS as the blank group, continued to culture for 10 days.

[0089] After the culture, discard the original culture medium, fix the cells with 0.2% Nonidet P-40 (2 mL), and aft...

experiment example 3

[0092] Experimental example 3: Effect on the promotion rate of calcium nodule formation of osteoblast-like cell line MC3T3-E1 cells

[0093] With the calcium nodule formation rate of osteoblast-like cell line MC3T3-E1 cells, evaluate the activity of promoting osteoblast calcification of the compound obtained in Example 1 and structural analogs epimedin C and icariin, the specific method is :

[0094] MC3T3-E1 cells were seeded in 12-well plates (1×10 5 cells / well), cultured in α-MEM medium containing 10% FBS (37°C, humidity 95%, 5% CO 2 ).

[0095] Two days later, the cells were replaced with α-MEM medium containing 1 μmol / L compound or blank solvent, and 10 mmol / L β-glycerophosphate sodium and 50 μg / mL ascorbic acid solution were added to induce mineralization.

[0096] The culture medium was replaced every other day, and the culture was terminated after 12 days. Alizarin red staining was used for morphometric analysis. Taking the mineralized area (A) as an index, calcula...

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Abstract

The invention relates to an isopentene flavonol glycoside derivative with a structure shown as a general formula (I) and a preparation method and application thereof. In the isopentene flavonol glycoside derivative, R1 refers to rhamnosyl, R2, R3, R4 and R7 refer to H, R5 refers to methoxyl, and R6 refers to hydroxyl; or R1, R4, R6 and R7 refer to H, R2 refers to xylosyl, R3 refers to acetyl, and R5 refers to hydroxyl; or R1, R3, R6 and R7 refer to H, R2 refers to xylosyl, R4 refers to glucosyl, and R5 refers to hydroxyl; or R1 refers to rhamnosyl, R2, R3 and R6 refer to H, R4 refers to glucosyl, R5 refers to methoxyl, and R7 refers to hydroxyl. The invention further relates to application of the isopentene flavonol glycoside derivative to the prevention and treatment of osteoporosis.

Description

technical field [0001] The invention relates to the field of medical inventions, in particular to a prenyl flavonol glycoside derivative for preventing and treating osteoporosis, a preparation method thereof and a pharmaceutical composition containing the compound. Background technique [0002] Osteoporosis is a systemic metabolic skeletal disease characterized by decreased bone mass and destruction of bone microstructure, which is manifested by increased bone fragility and easily induced fractures. According to statistics, about 200 million people in the world suffer from osteoporosis, and its incidence rate ranks seventh among common diseases and frequently-occurring diseases. The World Health Organization predicts that by 2050, the number of fractures caused by osteoporosis will rise from 1 million cases in 1990 to 6 million cases, and the high-incidence areas will also shift from the current Europe and North America to Asia, Africa and South America. Osteoporotic fractu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/07C07H1/08A61K31/7048A61P19/10
Inventor 姚新生秦岭屠凤娟王新峦戴毅周宁
Owner GUOYAOJITUAN TONGJITANG (GUIZHOU) PHARMA CO LTD
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