CN110833541A - Preparation method of ferulic acid butyl ester and functional application of ferulic acid butyl ester in treating or preventing Alzheimer's disease - Google Patents

Preparation method of ferulic acid butyl ester and functional application of ferulic acid butyl ester in treating or preventing Alzheimer's disease Download PDF

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CN110833541A
CN110833541A CN201910798146.8A CN201910798146A CN110833541A CN 110833541 A CN110833541 A CN 110833541A CN 201910798146 A CN201910798146 A CN 201910798146A CN 110833541 A CN110833541 A CN 110833541A
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ferulic acid
butyl ester
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石玉刚
吴煜
朱陈敏
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Zhejiang Gongshang University
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    • A—HUMAN NECESSITIES
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    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
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    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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    • C12P7/62—Carboxylic acid esters

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Abstract

The invention discloses a green preparation method of ferulic acid butyl ester and application thereof, experimental results show that ferulic acid butyl ester has better effect of preventing and treating Alzheimer's disease, ferulic acid butyl ester can effectively inhibit β -amyloid monomer aggregation, and simultaneously, ferulic acid butyl ester can achieve treatment effect by removing oxygen free radicals in nerve cells and activating an intracellular antioxidant stress system2Preparing Pickering emulsion, constructing a macroscopic continuous flow column type reaction system by using the Pickering emulsion, and breaking through reaction balance, catalyst separation and traditional batch reactionThe limitation of the device. The method has the advantages of simple operation, high conversion rate, high enzyme activity durability, high repeated utilization rate and cost saving.

Description

Preparation method of ferulic acid butyl ester and functional application of ferulic acid butyl ester in treating or preventing Alzheimer's disease
Technical Field
The invention relates to the fields of functional food additives, medicines and the like, and relates to preparation of a ferulic acid ester compound and functional application of the ferulic acid ester compound in preventing and treating Alzheimer's disease.
Background
According to the research of World Health Organization (WHO), about forty million patients with Alzheimer's disease are existed all over the world, however, no drug can effectively treat the disease, with the deep research, it is found that β -deposition of amyloid protein outside Neuron cells and Neurofibrillary Tangles (NTFs) formed by abnormal phosphorylation of Tau protein lead to nerve cell damage (Acta Neurophophathol.1991, 82, 239-.
At present, the pathogenesis related to AD is mainly the neurotoxic effect of A β precipitate, oxygen pressure and the formation of Reactive Oxygen Species (ROS), wherein the abnormal precipitation of A β in the brain is one of the important causes of nerve injury, excessive A β leads to the formation of increased oxygen pressure related to A β, which causes the accumulation of intracellular ROS, which is also the pathogenesis of several diseases in human, such as cancer and neurological diseases, therefore, the development of antioxidant strategies, the capture of intracellular ROS by antioxidants, and the inhibition or reduction of oxygen pressure, is also an effective method for preventing and treating AD (Pharmaceutical Research,2011,28(11), 2771-shaped 2779).
Experiments of the subject find that the hydrophilic lipophilic property of phenolic acid in a food system and a cell system can be effectively changed by grafting an alkyl chain on a hydroxyl group of the phenolic acid, so as to enhance the antibacterial effect (Journal of agricultural and food Chemistry,2018, 66(45),12088-12101.) and the antioxidant capacity (Pharmaceutical Research,2013,30, 1979-1989.) at present, application Research of alkyl ferulate is mainly focused on the antioxidant performance of the alkyl ferulate in the food system, Research on neuroprotection and prevention or treatment of Alzheimer's disease is limited, particularly related mechanism Research is less, it is reported that ferulic acid in animal experiments has the effect of protecting nerve damage caused by amyloid β (prepared by Toxosan, H.S.., 2004,27, 120. Ethyl ferulate has the effect of inhibiting the nerve damage caused by amyloid protein β (European stress-induced by European stress-induced protein kinase, European stress-induced cell repair, European stress-induced amyloid protein (European stress-induced amyloid protein) and the effect of inhibiting the antioxidant activity of amyloid protein (European stress-induced by European stress-induced amyloid polypeptide kinase, European stress-induced amyloid polypeptide, European stress-induced cell repair, European stress-induced protein, European stress-induced cell repair, European stress-induced injury, induced injury.
Disclosure of Invention
The invention aims to provide a new application of ferulic acid butyl ester, and experimental results show that ferulic acid butyl ester has a neuroprotective effect and has great potential for preventing and treating Alzheimer's disease.
The technical scheme of the invention is as follows:
the application of ferulic acid butyl ester in the preparation of functional additives can be used for preventing and treating Alzheimer's disease.
Experimental results show that the ferulic acid butyl ester can inhibit β -amyloid protein deposition, reduce the accumulation of intracellular ROS, activate an antioxidant stress system, protect nerve cells and achieve the effect of preventing and treating the Alzheimer's disease.
The invention also provides a green and efficient preparation method of the ferulic acid butyl ester, which comprises the following steps:
preferably, the silica nanoparticles are modified by the Stoer method, 1g of the modified silica nanoparticles are dried at 120 ℃ for 4h and uniformly dispersed in 12mL of toluene with the aid of ultrasound.
To the above suspension was added 3mmol (CH)3)2SiCl2And 6mmol CH3(CH2)5NH2And stirring for 4 hours at the constant temperature of 60 ℃ under the protection of nitrogen. Centrifuging to obtain solid particlesThe solid particles were washed with toluene and methanol to give dimethyl-modified silica particles.
0.01mol of dodecyl betaine was dissolved in 20mL of methanol. Adding equal molar amount of ferulic acid into the solution, stirring at 25 deg.C for 1 hr, removing methanol by rotary evaporation, and vacuum drying the solid at 25 deg.C for 24 hr to obtain [ C ]12Bet][Fal]。
0.195g of the above dimethyl-modified silica particles was uniformly dispersed in 2.4mL of n-octane, and 6.5g of an ionic liquid [ C ] was added to the solution12Bet][Fal]And 80. mu.L of Candida antarctica enzyme (lipase CALB) at a concentration of 4mg/mL pH 8.0, followed by homogenization in a homogenizer (8000rpm, 2min) to give a Pickering emulsion.
And adding the solution into a packed column with the bottom provided with a pore diameter of 4.5-9 mu m and the inner diameter of 2cm to obtain the ion droplet microreactor packed column.
Simultaneously injecting 0.4M n-butanol-n-octane solution and 0.1M n-octane solution of ferulic acid into the packed column by pump, controlling flow rate of both at 2mL/h, and keeping the packed column at constant temperature of 45 deg.C. Collecting the effluent, then using silica gel as a stationary phase and petroleum ether/ethyl acetate as a mobile phase, and carrying out gradient elution to separate and purify a target product, namely ferulic acid butyl ester (FAC 4).
Experimental results show that compared with ferulic acid in the prior art, the ferulic acid butyl ester can more effectively inhibit β -amyloid from precipitating, has a better inhibition effect on intracellular ROS (reactive oxygen species) triggered by 6-ODHA (deoxyribose nucleic acid) in a PC12 neuroma cell, and has a stronger inhibition effect on intracellular ROS triggered by β -amyloid in a PC12 neuroma cell, so that the ferulic acid butyl ester can be used as a functional additive with higher potential for preventing and treating Alzheimer's disease.
Drawings
FIG. 1 shows the results of experiments on the inhibition of β -amyloid protein deposition by ferulic acid and ferulic acid ester derivatives thereof according to the invention.
FIG. 2 is the experimental results of the inhibition of intracellular ROS induced by 6-ODHA by ferulic acid butyl ester and ferulic acid of the invention in PC12 neuroma cells;
FIG. 3 is a graph showing the experimental results of the inhibition of intracellular ROS induced by β -amyloid in PC12 neuroma cells by ferulic acid butyl ester and ferulic acid of the present invention;
FIG. 4 is an image of a hyperendocrinological imaging system of butyl ferulate and ferulic acid of the invention on intracellular ROS induced by β -amyloid in PC12 neuroma cells;
FIG. 5 is a Western blot of the butyl ferulate of the invention in PC12 neuroma cells against activation of the oxidative stress system by β -amyloid.
Detailed Description
The invention is further described with reference to specific examples.
EXAMPLE 1 Green preparation of butyl Ferulate
Modifying the silicon dioxide nano particles by a Stoer method, taking 1g of modified silicon dioxide nano particles, drying at 120 ℃ for 4h, and uniformly dispersing in 12mL of toluene under the assistance of ultrasound.
To the above suspension was added 3mmol (CH)3)2SiCl2And 6mmol CH3(CH2)5NH2And stirring for 4 hours at the constant temperature of 60 ℃ under the protection of nitrogen. The solid particles were obtained by centrifugation, and the solid particles were washed with toluene and methanol to obtain dimethyl-modified silica particles.
0.01mol of dodecyl betaine was dissolved in 20mL of methanol. Adding equal molar amount of ferulic acid into the solution, stirring at 25 deg.C for 1 hr, removing methanol by rotary evaporation, and vacuum drying the solid at 25 deg.C for 24 hr to obtain [ C ]12Bet][Fal]。
0.195g of the above dimethyl-modified silica particles was uniformly dispersed in 2.4mL of n-octane, and 6.5g of an ionic liquid [ C ] was added to the solution12Bet][Fal]And 80. mu.L of Candida antarctica enzyme (lipase CALB) at a concentration of 4mg/mL pH 8.0, followed by homogenization in a homogenizer (8000rpm, 2min) to give a Pickering emulsion.
And adding the solution into a packed column with the bottom provided with a pore diameter of 4.5-9 mu m and the inner diameter of 2cm to obtain the ion droplet microreactor packed column.
Simultaneously injecting 0.4M n-butanol-n-octane solution and 0.1M n-octane solution of ferulic acid into the packed column by pump, controlling flow rate of both at 2mL/h, and keeping the packed column at constant temperature of 45 deg.C. Collecting the effluent, then using silica gel as a stationary phase and petroleum ether/ethyl acetate as a mobile phase, and carrying out gradient elution to separate and purify a target product, namely ferulic acid butyl ester (FAC 4).
EXAMPLE 2 comparative study of the ability of Ferulic acid ester derivatives (FAC2-FAC10) to inhibit β -amyloid deposition
Adding 100 μ L of β -amyloid protein with concentration of 50 μ M into a 96-well black-bottom transparent plate, adding ferulic acid and ferulic acid ester series derivatives (ferulic acid ethyl ester FAC2, ferulic acid butyl ester FAC4, ferulic acid hexyl ester FAC6, ferulic acid octyl ester FAC8 and ferulic acid decyl ester FAC10) into the wells to make the final concentrations thereof respectively 5 μ M, culturing in a 37 ℃ incubator for 48h, adding 100 μ L of thioflavin T solution with concentration of 10mM into each well, incubating in the dark for 1h, and determining the fluorescence value.
The obtained ferulic acid and ferulic acid ester series derivatives can inhibit β -amyloid protein aggregation as shown in figure 1.
Comparative example 1 Ferulic acid inhibited β -amyloid protein precipitation
The comparative example is different from example 1 only in that ferulic acid is used as the substrate used in the comparative example, and the results are shown in FIG. 1.
Example 3 inhibition of intracellular ROS induced by 6-ODHA by butyl ferulate in PC12 neuroma cells
PC12 cells were seeded into 96-well plates at 1X 10 cells per well4Placing a cell culture box (5% CO)2Cells were allowed to adhere by overnight culture at 37 ℃. After overnight incubation, ferulate was added to the wells to give final concentrations of 10,50, 100. mu.M in the wells (parallel 6 groups) and incubated for 24 h. 6-OHDA was added to each well at a final concentration of 20. mu.M, and the mixture was cultured for 24 hours. Remove the medium from the wells, add DCFH-DA fluorescent probe, incubate for 30 minutes in the dark. Excess probe was washed off with PBS and its fluorescence was measured.
The resulting different concentrations of ferulic acid butyl ester on intracellular ROS inhibition induced by 6-ODHA in PC12 neuroma cells is shown in FIG. 2.
Comparative example 2 inhibition of intracellular ROS induced by 6-ODHA by Ferulic acid in PC12 neuroma cells
This comparative example is different from example 3 only in that ferulic acid was used as the substrate used in the comparative example. The resulting differential concentrations of ferulic acid on intracellular ROS inhibition induced by 6-ODHA in PC12 neuroma cells are shown in FIG. 2.
Example 4 inhibition of intracellular ROS induced by β -amyloid protein by butyl Ferulate in PC12 neuroma cells
PC12 cells were seeded into 96-well plates at 1X 10 cells per well4Placing a cell culture box (5% CO)2At 37 ℃, overnight culture is carried out to allow cells to adhere to the walls, after the overnight culture, ferulic acid butyl ester is respectively added into the holes to lead the final concentration in the holes to be respectively 10,50 and 100 mu M (parallel 6 groups), the cells are cultured for 24h, β -amyloid protein is respectively added into each hole, the final concentration in the holes is 5 mu M, the cells are cultured for 24h, the culture medium in the holes is removed, DCFH-DA fluorescent probes are added, the cells are incubated for 30 min in the dark, redundant probes are washed by PBS, and the fluorescence value is measured.
The resulting differential concentrations of ferulic acid butyl ester on inhibition of intracellular ROS induced by β -amyloid in PC12 neuroma cells are shown in FIG. 3.
COMPARATIVE EXAMPLE 3 intracellular ROS elicited by β -amyloid in PC12 neuroma cells
This comparative example is compared to example 4, except that it is not treated with butyl ferulate.
The results are shown in FIG. 3 for the β -amyloid-induced intracellular ROS in PC12 neuroma cells.
Comparative example 4 inhibition of intracellular ROS induced by β -amyloid by Ferulic acid in PC12 neuroma cells
This comparative example is different from example 4 only in that the substrate used in the comparative example is ferulic acid.
The resulting differential concentrations of ferulic acid on the inhibition of intracellular ROS induced by β -amyloid in PC12 neuroma cells are shown in FIG. 3.
Example 5 high content imaging System imaging of intracellular ROS induced by β -amyloid in PC12 neuroma cells
Referring to the procedure of example 4, after washing off the fluorescent probe, a photograph was taken with a high content imaging system.
The resulting high content imaging system image of different concentrations of ferulic acid butyl ester on β -amyloid-induced intracellular ROS in PC12 neuroma cells is shown in FIG. 4.
Comparative example 5 high content imaging System imaging of intracellular ROS in PC12 neuroma cells
This comparative example is compared to example 5, except that the comparative example was not treated with β -amyloid and ferulic acid butyl ester.
The resulting image of the high content imaging system of intracellular ROS in PC12 neuroma cells is shown in fig. 4.
Comparative example 6 high content imaging System imaging of β -amyloid-induced intracellular ROS in PC12 neuroma cells
This comparative example is compared to example 5, except that the comparative example was not treated with the substrate.
The resulting imaging of β -amyloid-induced intracellular ROS in PC12 neuroma cells is shown in FIG. 4.
Comparative example 7 imaging of high content imaging System of Ferulic acid on β -amyloid-induced intracellular ROS in PC12 neuroma cells
This comparative example is different from example 5 only in that ferulic acid was used as the substrate used in the comparative example.
The resulting high content imaging system image of different concentrations of ferulic acid on β -amyloid-induced intracellular ROS in PC12 neuroma cells is shown in FIG. 4.
Example 6 Western immunoblotting of butyl ferulate against activation of the oxidative stress System by β -amyloid in PC12 neuroma cells
PC12 cells were seeded into 6-well plates at 5X 10 cells per well5Placing a cell culture box (5% CO)2Cells were allowed to adhere by overnight culture at 37 ℃. After overnight incubation, ferulate was added to the wells to give final concentrations of 0,5,10,50,100 μmM (parallel 6 groups), culturing for 24h, adding β -amyloid to each well to make the final concentration in the well 5 μ M, culturing for 24h, removing the culture medium in the well, extracting the protein in the cell, and obtaining the experimental result by using the Western blotting technology.
The Western blot of different concentrations of ferulic acid butyl ester obtained in PC12 neuroma cells against activation of the oxidative stress system by β -amyloid is shown in FIG. 5.
According to the results of examples 1 to 6 and comparative examples 1 to 7, the modified ferulic acid butyl ester has better effects on protecting cells and inhibiting β -amyloid protein deposition compared with ferulic acid.

Claims (5)

1. The application of the ferulic acid butyl ester in the preparation of the functional additive is characterized in that the functional additive is used for preventing and treating the Alzheimer disease.
2. The use of ferulic acid butyl ester of claim 1 in the preparation of a functional additive, wherein the functional additive is used to inhibit β amyloid protein from precipitating as a more neurotoxic oligomer.
3. The use of ferulic acid butyl ester according to claim 1, for the preparation of a functional additive for scavenging reactive oxygen species, ROS, accumulated in nerve cells.
4. The use of ferulic acid butyl ester according to claim 1 in the preparation of a functional additive, wherein the functional additive is used to activate antioxidant stress systems in nerve cells.
5. The preparation method of the ferulic acid butyl ester is characterized by comprising the following steps:
(1) drying the silicon dioxide nanoparticles at 100-120 ℃ for 4-10 hours, and uniformly dispersing the silicon dioxide nanoparticles in toluene under the assistance of ultrasound to obtain a suspension;
(2) to the above suspensionAdding (CH)3)2SiCl2And CH3(CH2)5NH2Stirring for 4-10 h at the constant temperature of 50-60 ℃ under the protection of nitrogen, centrifuging to obtain solid particles, and flushing the solid particles with toluene and methanol to obtain dimethyl modified silicon dioxide particles;
(3) dissolving dodecyl betaine in methanol, adding equal molar amount of ferulic acid into the solution, stirring at 25 deg.C for 1 hr, removing methanol by rotary evaporation, vacuum drying the solid at 25 deg.C for 24 hr to obtain ionic liquid [ C12Bet][Fal]；
(4) Uniformly dispersing the dimethyl modified silicon dioxide particles into n-octane, and adding ionic liquid [ C ] into the solution12Bet][Fal]Mixing with candida antarctica enzyme, and homogenizing in a homogenizer to obtain pickering emulsion;
(5) adding the solution into a packed column with the bottom having an aperture of 4.5-9 μm and an inner diameter of 2cm to obtain an ion droplet microreactor packed column;
(6) simultaneously injecting a 0.4M n-butanol-n-octane solution and a 0.1M n-octane solution of ferulic acid into the packed column through a pump, controlling the flow rates of the two solutions to be 2mL/h, keeping the packed column at a constant temperature of 45 ℃, collecting an effluent, then taking silica gel as a stationary phase and petroleum ether/ethyl acetate as a mobile phase, and separating and purifying a target product of ferulic acid butyl ester according to gradient elution.
CN201910798146.8A 2019-08-27 2019-08-27 Preparation method of ferulic acid butyl ester and functional application of ferulic acid butyl ester in treating or preventing Alzheimer's disease Pending CN110833541A (en)

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Application publication date: 20200225