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Ferulic acid powder, with chemical name of 3-methoxy-4-hydroxycinnamic acid and chemical formula of C10H10O4, CAS 1135-24-6, is one of the derivatives of cinnamic acid. Yellow powder, soluble in hot water, ethanol, ethyl acetate, slightly soluble in petroleum ether, benzene. It has high content in Ferula, Angelica, Ligusticum chuanxiong, Cimicifuga, Semen Ziziphi spinosae and other traditional Chinese medicines, and is one of the effective ingredients of these traditional Chinese medicines. It has cis and trans isomers, both of which are light yellow solids.
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Chemical Formula |
C10H10O4 |
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Exact Mass |
194.06 |
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Molecular Weight |
194.19 |
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m/z |
194.06 (100.0%), 195.06 (10.8%) |
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Elemental Analysis |
C, 61.85; H, 5.19; O, 32.96 |
Radiation induced organ failure is largely caused by chronic oxidative damage. Radiation damage to the body can be divided into direct damage and indirect damage. Direct damage, that is, radiation directly causes the breakage of some sensitive molecules in cells; Indirect injury is caused by radiolysis of water, which leads to the increase of intracellular reactive oxygen species and then changes the subcellular structure. Therefore, antioxidants are widely used in the treatment of radiation injury.
To protect cells from reactive oxygen species (ROS) damage, it is necessary to maintain the homeostatic endogenous thiol pool, especially the content of glutathione (GSH) and nicotinamide adenine dinucleotide phosphate (NADPH).
Glutathione provides the reduction equivalent for the conversion of hydrogen peroxide and lipid peroxide into water and lipid alcohol, and protects the sulfhydryl protein group from oxidative damage. The rate limiting reaction of glutathione biosynthesis is catalyzed by glutamate cysteine ligase (GCL), which is composed of a catalytic subunit (GCLC) and a regulatory subunit (GCLM). Nicotinamide adenine dinucleotide phosphate is an important antioxidant in tissues, which can maintain the redox potential of cells by reducing the reduction equivalent of glutathione reductase and thioredoxin.
Ferulic acid powder, as a phenolic plant component, has a strong antioxidant activity and has a great role in promoting human health. Ferulic acid can significantly increase the content of glutathione and nicotinamide adenine dinucleotide phosphate in irradiated cells, and has a protective effect on irradiated endothelial cells. Heme oxygenase is an antioxidant enzyme, which can convert heme into biliverdin and eventually into antioxidant bilirubin. Ferulic acid can well regulate the expression of this enzyme, thus playing a protective role in radiation protection.
2. Antioxidant function
Metabolism is a characteristic of life. At the same time, life is always attacked by active oxygen substances (molecules or free radicals that are more active than molecular oxygen directly or indirectly converted from molecular oxygen) and free radicals (also called free radicals, which refer to atoms, atomic clusters or molecules in special states with unpaired electrons in the outer orbit). Both of these substances can directly participate in the formation of tumors or induce the generation of carcinogens, The key to prevent and cure related diseases is to change the DNA of life, activate proto oncogenes, and thus promote the body to produce cancer cells to reduce antioxidant damage.
Some studies have shown that ferulic acid can kill free radicals skillfully and restore the normal functions of life. Ferulic acid can inhibit the enzymes that produce free radicals in life. On this basis, it can also increase the enzymes that eliminate free radicals. At the same time, ferulic acid can greatly enhance the activities of anabolic enzyme and gluten glycation sulfotransferase, and control the proportion of active tyrosinase. The research shows that ferulic acid has a significant antioxidant effect, and has a good scavenging effect on ammonia peroxide, superoxide free radicals, hydroxyl free radicals, peroxynitro, etc.
3. Antibacterial and anti-virus functions
The study found that after the macrophages of the test mice were infected with influenza virus, the blank control was set without treatment, and the test group was treated with ferulic acid and isoferulic acid. According to the analysis of the results, the production of interferon in the test group decreased rapidly. In recent years, there have been many reports about the significant inhibition of ferulic acid on cold virus (IV), respiratory syncytial virus (RSV) and HIV. The relationship between ferulic acid and inflammatory proteins has been studied in the same cell line. As a result, ferulic acid can dramatically reduce the production of this protein.
Among them, ferulic acid has an inhibitory effect on HIV, which makes it possible for ferulic acid to become a future chemotherapeutic agent. It is speculated that the inhibition mechanism of ferulic acid on viruses is related to its ability to reduce the activity of xanthine oxidase. This is because this kind of enzyme can generally lead to some inflammation. It is speculated that the antibacterial function of ferulic acid is mainly due to its strong inhibition on the N-acetyltransferase in bacteria.
Synthesis Methods
Direct extraction from plants
Ferulic acid powder can be obtained from plants in three ways: first, from the combination of ferulic acid and some small molecules, second, from plant cell walls, and third, through tissue culture. In plants, ferulic acid is usually cross-linked with polysaccharides and lignin through ester bonds or self esterification or etherification to form ferulic acid. Generally, the ester bonds are broken by alkali method and enzyme method to release ferulic acid, and then the appropriate solvent is used for extraction.
Ferulic acid from the cell wall can be released when 4% sodium hydroxide is used to react at room temperature for 24 h under the condition of nitrogen. Recent studies have found that most ferulic acid in wheat bran can be released in a short time by increasing the extraction temperature and adding suitable protective agents. A low concentration of sodium hydroxide solution can release most of ferulic acid from wheat bran at an appropriate extraction temperature. Adding sodium sulfite in the extraction process can increase the recovery rate of ferulic acid. Due to the complex composition of the alkali liquor, especially the pigment material, at present, the separation method of ferulic acid in the alkali liquor is mainly the activated carbon adsorption method. The oryzanol contains the structural unit of ferulic acid, which exists in the form of ester and is easy to decompose. Therefore, the oryzanol can be hydrolyzed by alkali and then acidified to prepare ferulic acid. The reactive hydrolysis of oryzanol to prepare ferulic acid is easy to operate, and the yield is up to 85.7%. The by-product is napalm alcohol. Moreover, oryzanol has a wide source, large output and moderate price.
Ferulic acid esterase is an enzyme that can free ferulic acid from methyl ferulate, oligosaccharide ferulate and polysaccharide ferulic acid. Fungi, bacteria and yeast can secrete ferulate esterase. The mixed enzyme preparation containing ferulase and arabinoxylanase was prepared by submerged fermentation with Aspergillus niger as the strain. The mixed enzyme preparation was used to act on the starchy wheat bran. It was found that the degradation rate of wheat bran after three times of degradation was 55.46%.
Using plant tissue culture is an important way to obtain ferulic acid. Some studies have shown that tissue culture of some plants can produce ferulic acid derivatives with high yield. For example, water soluble glucose ferulate and sucrose ferulate can be obtained by cell suspension culture of sugar beet and corn, with the content as high as 20.0 μ Mol/g callus (dry weight). In the direct extract, the content of ferulic acid is relatively low, which needs further purification.
Chemical synthesis method
The chemical synthesis of ferulic acid takes vanillin as the basic raw material, and the main organic reactions are Wittig Horner reaction and Kneoevenagel reaction.
The Wittig Horner reaction of triethyl phosphite acetate and acetyl vanillin takes place in a strong base system, and ferulic acid is obtained by acidification with concentrated hydrochloric acid. This method needs to protect phenolic hydroxyl in advance, otherwise, due to the existence of strong base, the generation of sodium phenolate will inhibit the reaction between carbonyl group and carbon anion, and it is easy to generate impurities through side reactions.
A small amount of organic base is added in pyridine solvent as catalyst, vanillin and malonic acid undergo Kneoevenagel reaction to generate ferulic acid, and the catalysts include piperidine and aniline. However, the reaction time is long, up to three weeks, and the mixture of trans and cis ferulic acid is obtained.
Biosynthesis is to use several microorganisms to convert ferulic acid precursor into ferulic acid, such as eugenol cinnamate extracted from clove oil into ferulic acid. Biosynthesis is a clean and effective synthesis method, but there is no mass production method yet.
Separation and purification method
At present, there are not many methods to purify ferulic acid. It mainly includes solvent extraction method and adsorption method.
The commonly used solvent for extracting ferulic acid mainly includes ethanol, ethyl acetate, etc. The principle is to extract ferulic acid from the extraction solution with a solvent with high solubility of ferulic acid, and then remove the solvent by vacuum distillation to obtain the finished ferulic acid product. The process is simple, but the yield is low, and the energy consumption is large. It is the most commonly used method to purify ferulic acid.
Adsorption is a purification method that has been studied more frequently at present. The principle is to add adsorption materials to adsorb and enrich ferulic acid in solution, and then use eluent to elute the adsorbed ferulic acid. The activated carbon, polystyrene cross-linked resin, PVPP and other adsorption media were screened. The study showed that the activated carbon was the best adsorption medium for ferulic acid because of its high adsorption capacity (22g per 100g), no combination of monosaccharide molecules, easy elution and other advantages. After the activated carbon adsorption is completed, the adsorbed ferulic acid can be washed off with ethanol. In addition, the activated carbon is also an excellent adsorption material. After the extraction solution is adsorbed by the activated carbon, when the activated carbon reaches the adsorption saturation, the relatively pure ferulic acid can be obtained from the extraction solution through elution.
Quality & Analysis
High performance liquid chromatography:
The content of Ferulic acid powder was determined by HPLC. The method is simple, rapid, accurate and precise. According to the literature, the mobile phase mainly adopts acidic system, mainly including methanol water phosphoric acid system, methanol water glacial acetic acid system, methanol acetonitrile water glacial acetic acid system, etc. The amount of methanol can be appropriately adjusted in the test. The content of ferulic acid in compound ginkgo oral liquid was determined by HPLC. The mobile phase was methanol: 1% glacial acetic acid (45:55), the detection wavelength was 320 nm, the flow rate was 1.0 mL/min, and the column temperature was 25 ℃. Ferulic acid oxygen intake is 0.176-0.88 μ The linearity is good within the rangeg.
Thin layer scanning method:
Thin layer scanning is also one of the commonly used methods to determine the content of ferulic acid. This method is rapid, but its sensitivity is not ideal. Benzene glacial acetic acid chloroform (6:0.5:3.5) was used as developing agent, and single wavelength reflection was used for sawtooth scanning. The scanning wavelength was 325 nm. Good stability.
Thin layer spectrophotometer method
The qualitative determination of ferulic acid extracted from rye bran, an agricultural by-product, was carried out by thin layer chromatography spectrophotometer. The developer was dichloromethane: acetonitrile: formic acid=75:25:10; The results showed that although the spectrophotometer method was easily interfered by other components, the relative error of HPLC was about 7% and the reproducibility was good.
High performance capillary electrophoresis:
Capillary zone electrophoresis is the most widely used separation mode of capillary electrophoresis. It is characterized by simple, efficient, fast, less sample consumption and automatic operation. The content of ferulic acid in angelica preparations was detected by hollow fused silica capillary, and it was found that μ It can be quantitatively detected in the range of g/mL, with good repeatability.
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