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Preparation of cucurbitacin compounds and application of cucurbitacin compounds to medicines

A technology of cucurbitacins and compounds, which is applied in the field of medicine, can solve the problems of NGF being expensive, having a large relative molecular weight, and not being able to pass through the blood-brain barrier, and achieve significant nerve growth factor-mimicking activity, easy access, new drugs for prevention and treatment The effect of development

Inactive Publication Date: 2013-10-23
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as an effective method for the possible treatment of AD, NGF is expensive, has a large molecular weight, cannot penetrate the blood brain barrier (Blood Brain Barrier, BBB), and can only be injected intraventricularly. There are many technical problems in long-term treatment.

Method used

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  • Preparation of cucurbitacin compounds and application of cucurbitacin compounds to medicines
  • Preparation of cucurbitacin compounds and application of cucurbitacin compounds to medicines
  • Preparation of cucurbitacin compounds and application of cucurbitacin compounds to medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1 Preparation of Cucurbitacin Compounds

[0047] 1) Crushing and extraction:

[0048] After pulverizing 500 g of the traditional Chinese medicine melon pedicle, use 12.5 L of ethanol (industrial grade) to shake and extract at room temperature for 3 days. After suction filtration and concentration, 93.4 g of crude ethanol extract was obtained.

[0049] 2) Extraction, separation and purification:

[0050] Carry out solvent distribution 2 times with 80% methanol aqueous solution and normal hexane (volume ratio=1: 1) with the thick sample (90g) of melon pedicle ethanol extract, the 80% methanol aqueous solution layer sample of gained carries out rotary evaporation, obtains concentrated material (72.5g). The concentrate was separated by normal phase silica gel chromatography (silica gel, 200-300 mesh) column (solvent system was n-hexane: ethyl acetate = 90: 10, 80: 20, 70: 30, 40: 60, 0: 100, 100 % methanol), to obtain a cucurbitacin mixture (22.5g). Wherein a p...

Embodiment 2

[0052] Embodiment 2 Qualitative identification of the physical and chemical characteristics and chemical structure of compound 1-7 obtained in embodiment 1:

[0053] The chemical structures of compounds 1-7 have been 1 H NMR, 13 C NMR, MS test, and confirmed after comparison with literature data.

[0054] Physicochemical properties of compound (1): white solid, 13 C NMR (125MHz, in CD 3 OD): 215.8(C-11), 214.0(C-3), 205.3(C-22), 171.9(C-31), 151.6(C-24), 142.1(C-5), 122.7(C-23 ), 121.3(C-6), 81.1(C-25), 80.3(C-20), 72.9(C-2), 72.8(C-16), 60.0(C-17), 51.8(C-13) , 51.7(C-4), 50.0(C-9), 49.4(C-12), 49.4(C-14), 46.5(C-15), 44.2(C-8), 37.1(C-1), 34.9(C-10), 29.9(C-28), 26.9(C-27), 26.4(C-26), 25.3(C-21), 24.9(C-7), 21.9(C-29), 21.6 (C-32), 20.7(C-18), 20.1(C-19), 19.5(C-30); ESI-MS m / z: 499[M+H-AcOH] + .

[0055] Physicochemical properties of compound (2): white powder, 13 C NMR (125MHz, in CDCl 3 ): 214.0(C-22), 212.9(C-3), 212.8(C-11), 170.2(C-31), 140.5(C-5), 121.0...

Embodiment 3

[0061] The biological activity of the cucurbitacin compounds derived from the stalk of Chinese medicine melon in embodiment 3

[0062] Studies have found that in animal models of neurodegeneration, NGF can prevent or reduce the degeneration of neurons, prevent the progression of AD to a certain extent, and has the effect of promoting neurotrophy and neuroprotection. PC 12 cells are a successful in vitro model widely used to simulate neurons. It is derived from the pheochromocytoma of the rat adrenal medulla. Like sympathetic neurons and sensory neurons, it originates from the neural crest. After NGF treatment, the cells stop proliferating and grow neurites, showing the appearance of mature sympathetic neurons. cell phenotype. Therefore, using the PC 12 cell biological activity identification system to screen the active ingredients with neuromimetic growth factor activity from natural products will become an effective drug for the prevention and treatment of Alzheimer's diseas...

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PUM

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Abstract

The invention provides a preparation method of cucurbitacin compounds, which comprises the following steps: pulverizing and leaching traditional Chinese medicine muskmelon pedicel, carrying out solvent partitioning on the crude leaching sample with a methanol water solution and n-hexane, concentrating, respectively separating the concentrate with a normal-phase silica gel chromatographic column, and purifying by high performance liquid chromatography to obtain the purified cucurbitacin compounds. The cucurbitacin compounds obtained in the invention have obvious quasi-nerve growth factor activity, and can be applied to preparation of medicines for preventing senile dementia and other neurodegenerative diseases and especially to preparation of medicines for treating Alzheimer's disease and other neurodegenerative diseases. The invention develops pharmaceutical application of effective component cucurbitacin compounds. The raw material-traditional Chinese medicine muskmelon pedicel has wide sources and is convenient to take; and the preparation method is simple and can easily implement industrial production. The structural general formula is disclosed in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a preparation method of cucurbitacin compounds and their application in the preparation of drugs for preventing and treating neurodegenerative diseases such as senile dementia. Background technique [0002] Alzheimer's disease (AD) is a degenerative disease of the central nervous system that occurs in the early and old age and is characterized by progressive dementia and abnormal mental behavior. It is second only to heart disease, tumor and stroke among the causes of death in the elderly. fourth place. According to the 2010 report of the International Alzheimer's Association, there were 35.56 million Alzheimer's patients in the world in 2010, and it is expected to increase to 65.69 million by 2030, and 115 million by 2050. The cost of dementia reached $604 billion in 2010 and continues to increase at an alarming rate. As China's society is gradually aging, Alzheimer's disease...

Claims

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Application Information

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IPC IPC(8): C07J9/00A61K31/575A61P25/28
Inventor 戚建华高丽娟陈欢向兰孙恺悦罗燕
Owner ZHEJIANG UNIV
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