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Isorhamnetin, molecular formula C16H12O7, CAS 480-19-3, is a flavonoid compound and a powerful antioxidant that can scavenge oxygen free radicals and prevent cell and tissue damage caused by aging. Isorhamneti is a flavonoid compound separated and purified from ginkgo biloba, seabuckthorn and other medicinal plants, and also widely exists in flowers, fruits and leaves of many other plants. Isorhamneti has a variety of biological activities, including cardiovascular protection (anti myocardial hypoxia, ischemia, relieving angina pectoris, anti arrhythmia, lowering serum cholesterol, promoting blood flow patency, etc.), antioxidant, anti-tumor, anti-inflammatory, anti-virus, anti allergy, and regulating immune function. Especially in the protection of cardiovascular, it has multiple functions, such as expanding blood vessels, reducing blood pressure, preventing coronary atherosclerotic heart disease, reducing myocardial hypertrophy, inhibiting vascular smooth muscle cell proliferation and hypertrophy, anti thrombosis, and has broad application prospects.
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Chemical Formula |
C16H12O7 |
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Exact Mass |
316 |
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Molecular Weight |
316 |
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m/z |
316 (100.0%), 317 (17.3%), 318 (1.4%), 318 (1.4%) |
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Elemental Analysis |
C, 60.76; H, 3.82; O, 35.41 |
Isorhamnetin has an inhibitory effect on the proliferation of skin cancer cells cultured in vitro and can induce cell apoptosis; In vivo studies have also shown that isorhamneti can inhibit the proliferation of skin cancer cells. Its mechanism is that isorhamneti reduces the degree of protein phosphorylation in cancer cells at the cellular level, effectively regulating the activity of protein tyrosine kinase (PTK), including epidermal growth factor receptor EGFR.
pharmacological action
Antibacterial and antiviral effects: ISO has a broad-spectrum antibacterial effect and is widely used in bacterial and fungal infections, including inhibiting the growth of bacteria such as Staphylococcus, Salmonella, Bacillus, Pseudomonas fluorescens, and Clostridium botulinum in food. Studies have shown that bacterial cells injected with extracts containing isorhamneti exhibit a certain reduction in intracellular proteins and carbohydrates, ultimately leading to cell death. In addition, isorhamneti also has significant anti influenza virus effects, which can directly or indirectly inhibit the expression of HA and NA genes of the virus, suppress virus induced autophagy, ROS production, and EPK phosphorylation. Isorhamneti has a certain therapeutic effect on bacterial induced skin infections, urinary tract infections, and digestive tract infections.
Antitumor effect: Isorhamneti inhibits the growth of colon tumor cells through the PI3K Akt mTOR pathway and has potential anti-tumor activity against BEL-7402 cells. Mitochondrial cytochrome C-caspase-9 regulates apoptosis induced by isorhamneti. Research has shown that isorhamneti can induce apoptosis by reducing the expression of the apoptosis inhibiting gene Bcl-2 and increasing the number of pro apoptotic protein Bax. Isorhamneti can significantly inhibit the proliferation of gastric cancer SGC7901 cells, reduce telomerase activity, induce apoptosis, and exhibit concentration - and time-dependent effects. The possible mechanism is to block the progression of cells from G0 phase to S phase, forming G0 arrest phase, causing G0 phase cell accumulation arrest and blocking cell DNA synthesis and replication.
Antioxidant effect: Isorhamneti is a natural antioxidant that can replace synthetic substances as a food additive. In vivo experiments have shown that isorhamneti has antioxidant enzyme activity against cholesterol and peroxidized lipids in plasma and liver.
Cardiovascular protection: isorhamneti can prevent endothelial dysfunction, inhibit the production of superoxide and the overexpression of p47phox caused by angiotensin II, and inhibit macrophage apoptosis through PI3K/AKT activation and HO-1 induction, thereby alleviating atherosclerosis.
ISO is a flavonoid compound that is widely present in the flowers, fruits, and leaves of various plants in nature, particularly abundant in ginkgo and seabuckthorn. This compound has attracted much attention due to its various biological activities such as antioxidant, anti-inflammatory, anti-tumor, antiviral, and endothelial cell protection. The following are the main food sources of ISO:
Sea buckthorn is a perennial shrub or tree in the family Elapidae, and its fruit is one of the important sources of ISO. Sea buckthorn fruit is rich in various bioactive substances, among which total flavonoids of sea buckthorn are its main component, and ISO is an important monomer component in total flavonoids of sea buckthorn. Research has shown that ISO in seabuckthorn has significant cardiovascular protective effects, such as antioxidant, endothelial cell protection, inhibition of endothelial cell monocyte adhesion, reduction of lipid deposition, inhibition of vascular smooth muscle cell proliferation and migration, and anti thrombotic effects. These effects make seabuckthorn and its extracts show great potential in the prevention and treatment of cardiovascular diseases such as atherosclerosis (AS).
Sea buckthorn is widely distributed and has a variety of species in China. Its plants can grow up to 5-10 meters tall and have thick thorns. Sea buckthorn fruit can not only be consumed directly, but also processed into various foods, beverages, and health products, providing abundant ISO and other nutrients for the human body.
Ginkgo biloba is another plant rich in isorhamnetin. The content of ISO in Ginkgo biloba leaf extract is relatively high. Ginkgo biloba leaf extract has a wide range of applications in the fields of medicine, health products, and cosmetics. Among them, the antioxidant and anti-inflammatory biological activities of ISO make Ginkgo biloba leaf extract significantly effective in anti-aging, improving blood circulation, and preventing cardiovascular diseases.
The ISO in Ginkgo biloba extract can exert protective effects through various pathways, such as inhibiting lipid peroxidation, reducing blood viscosity, and improving microcirculation. These effects make ginkgo biloba extract become one of the important natural drugs to prevent and treat chronic diseases such as cardiovascular and cerebrovascular diseases and diabetes.
In addition to seabuckthorn and ginkgo, ISO is also widely present in various other plants, such as Rhodiola rosea and hawthorn. Although the content of ISO in these plants may not be as high as sea buckthorn and ginkgo, they still have various biological activities that are beneficial to human health.
For example, ISO in Rhodiola extract has antioxidant, anti fatigue, and immune enhancing effects; The ISO in hawthorn has the effects of lowering blood pressure, regulating blood lipids, and promoting digestion. These plants and their extracts also have a wide range of applications in the fields of food and health products.
Although ISO is widely present in various plants, the content and biological activity of ISO may vary among different plants. Therefore, when choosing foods rich in ISO, attention should be paid to its source and quality. Meanwhile, as ISO is a natural compound, its intake and safety also need to be controlled within a reasonable range.
Generally speaking, consuming plant-based foods rich in ISO through daily diet is safe and effective. For example, one can consume foods rich in ISO such as sea buckthorn fruit, ginkgo leaf products, and Rhodiola products in moderation. In addition, health supplements containing extracts of these plants can also be chosen to supplement ISO. However, it should be noted that excessive intake of any nutrient may have adverse effects on health, so intake should be controlled reasonably.
ISO is a flavonoid compound widely present in various plants, with multiple biological activities and benefits for human health. Consuming plant-based foods rich in ISO through daily diet is an effective way to obtain this nutrient. When choosing food, attention should be paid to its source and quality, and the intake should be reasonably controlled to ensure health.
Synthesis path 1:
Mix 2-butanone and benzyl chloride evenly, add 2,4,6-trihydroxyacetophenone and anhydrous K2CO3, add water and stir, dissolve the obtained white mixture and vanillin in anhydrous ethanol, add KOH aqueous solution, acidify with hydrochloric acid to obtain 3 '- methoxy-4', 5,7-triphenylchalcone, then dissolve the ketone in ethyl acetate, under palladium carbon catalysis, hydrogenation reduction, obtain 3 '- methoxy-4', 5,7-trihydroxychalcone, add 3 '- methoxy-4', 5,7-trihydroxychalcone to a mixed solvent of dichloromethane and acetone, add buffer solution and stir evenly, add KHSO4 composite salt solution to obtain Isorhamnetin. This four step synthesis method has simple process operation, low production cost, high product purity, and is easy to industrialize production.
Step 1: Benzylation reaction
Detailed steps:
Chemical equation:
2-butanone+benzyl chloride+K2CO3 → benzylated ketone+NaCl+CO2+H2O
Note: This equation is for illustration only, and the actual product structure may be more complex and may contain multiple isomers.
Preparation of reactants:
Mix 2-butanone, benzyl chloride, 2,4,6-trihydroxyacetophenone, and anhydrous potassium carbonate (K2CO3) in a dry reaction flask in a certain proportion.
Stirring and Heating:
Under the protection of inert gas (such as nitrogen), heat the reaction mixture to an appropriate temperature (usually reflux temperature) while vigorously stirring to ensure sufficient contact between the reactants.
Reaction proceeds:
Under anhydrous conditions, potassium carbonate acts as a base catalyst to promote the substitution of the chlorine atom of benzyl chloride by the hydrogen atom on the alpha carbon of 2-butanone, forming a benzylated ketone intermediate. Meanwhile, 2,4,6-trihydroxyacetophenone may participate in the reaction in some way, but the specific mechanism needs further experimental confirmation.
Post processing:
After the reaction is completed, unreacted raw materials and by-products are removed by distillation or extraction to obtain benzylated ketone crude products.
Step 2: Clemenson condensation reaction
Detailed steps:
Chemical equation (also hypothetical):
Benzyl ketones+vanillin+KOH → 3 '- methoxy-4', 5,7-triphenylchalcone+H2O
Note: This reaction may involve multiple steps and intermediate products, and the formation of chalcones is typically achieved through a condensation reaction between the alpha position of an aldehyde or ketone and the beta position of another ketone or aldehyde. But here, we have simplified this process.
1. Dissolution and mixing:
Dissolve the crude benzylated ketone obtained in the previous step with vanillin in anhydrous ethanol, and add an appropriate amount of potassium hydroxide (KOH) aqueous solution.
2. Heating reflux:
Under inert gas protection, heat the reaction mixture to reflux temperature and maintain it for a period of time to ensure sufficient reaction.
3. Acidification:
After the reaction is complete, acidify the reaction solution with dilute hydrochloric acid to precipitate the generated product.
4. Extraction and purification:
Pure 3 '- methoxy-4', 5,7-triphenylchalcone is obtained through steps such as extraction, washing, drying, and crystallization.
Step 3: Hydrogenation reduction reaction
Detailed steps:
Chemical equation (taking the reduction of chalcone double bonds as an example):
3'-Methoxy-4',5,7-Tribenzylchalcone+H2 → Reduction product
Note: The structure of the reduction product here depends on which functional groups in the chalcone are reduced. In practical situations, further experiments may be necessary to determine the specific reduction products.
1. Dissolution:
Dissolve the 3 '- methoxy-4',5,7-triphenylchalcone obtained in the previous step in ethyl acetate.
2. Catalyst addition:
Add an appropriate amount of palladium carbon (Pd/C) as a catalyst to the reaction solution.
3. Hydrogenation:
Under a hydrogen atmosphere, pressurized hydrogenation of the reaction mixture is usually carried out at a certain temperature and pressure.
4. Filtration and Purification:
After the reaction is complete, the catalyst is removed by filtration, and the product is purified through washing, drying, and possible recrystallization steps to obtain the reduced product.
Step 4: Salt formation or extraction reaction
Detailed steps (due to unclear specific reaction details, the following is a possible hypothesis):
Dissolve the reduction product obtained in the previous step in a mixed solvent of dichloromethane and acetone.
Add an appropriate amount of buffer solution (such as phosphate buffer solution) to the reaction solution to adjust the pH value of the solution.
Detailed steps (continued hypothetical description):
Add KHSO4 composite saline solution: Slowly add KHSO4 composite saline solution while stirring. This step may be to adjust the ionic strength of the solution, promote changes in the solubility of certain compounds, or facilitate the precipitation of the target product through ion exchange and other methods. It should be noted that the specific role of KHSO4 here may depend on the chemical properties of the target product isorhamneti and its dissolution behavior in different solvents and conditions.
Continue stirring the reaction mixture for a period of time to ensure that all components are fully in contact and possible interactions occur. Then, let the reaction mixture stand still so that the target product can precipitate or stratify.
The target product is separated from the reaction mixture by filtration, centrifugation, or liquid separation methods. Subsequently, the product undergoes purification steps such as washing, drying, and possible recrystallization to obtain high-purity ISO.
Synthesis path 2:
Extracting isorhamneti from seabuckthorn fruit residue, including
(1) cold extraction: quantitatively weigh seabuckthorn fruit residue, add ethanol and extract at room temperature, then vacuum filter the extract and collect the filtrate; Add ethanol to the filter residue, repeat the extraction at room temperature twice, then vacuum filter the extraction solution, collect the filtrate, and discard the filter residue;
(2) Concentrate: Draw the filtrate extracted twice into a concentration tank, recover the solvent under reduced pressure, and concentrate to obtain a paste;
(3) Oil removal: Use dichloromethane to remove oil from the obtained paste while it is still hot, filter it, and obtain crude crystals;
(4) Recrystallization: Dissolve the obtained crude crystals in organic solvents, dry the crystals, and obtain isorhamneti.
Here are detailed answers for each step:
Objective: To dissolve the active ingredients such as isorhamneti in seabuckthorn fruit residue through ethanol extraction at room temperature.
Steps:
Quantitatively weigh the seabuckthorn fruit residue to ensure consistent extraction of raw materials each time, in order to control extraction efficiency and product quality.
Adding an appropriate amount of ethanol (usually anhydrous ethanol or a certain concentration of ethanol solution), ethanol can effectively dissolve polar compounds such as isorhamneti in seabuckthorn fruit residue as a solvent.
Extract at room temperature and allow ethanol to fully contact with seabuckthorn fruit residue through stirring or standing, promoting the dissolution of active ingredients.
After soaking for a period of time, the extract is vacuum filtered to remove solid impurities and collect the filtrate containing isorhamneti.
Perform secondary and tertiary ethanol extraction on the filter residue, repeat the above operation to extract as much isorhamneti as possible from the seabuckthorn fruit residue.
Collect all extracts and discard the filter residue.
Objective: To remove ethanol from the extract by reducing pressure and recovering the solvent, and obtain a paste containing isorhamneti.
Steps:
Combine the filtrate obtained from two or more extractions and draw it into a concentration tank.
Heat under reduced pressure to evaporate ethanol and recover it. Reducing pressure can lower the boiling point of the solvent, enabling rapid recovery of the solvent at lower temperatures, while reducing the damage of high temperatures to active ingredients such as isorhamneti.
As ethanol evaporates, the extract gradually concentrates, ultimately yielding a paste containing isorhamneti.
Objective: To remove impurities such as oil and fat from the extract and improve the purity of isorhamneti.
Steps:
Add the obtained extract to dichloromethane while it is still hot. Dichloromethane is a non-polar solvent with good solubility for non-polar impurities such as oils and fats, but poor solubility for polar compounds such as isorhamneti.
By stirring, ensure sufficient contact between dichloromethane and the extract, and dissolve impurities such as oils and fats in dichloromethane.
Filter and remove the dichloromethane solution containing oil to obtain relatively pure crude crystals of isorhamneti.
Objective: To further improve the purity and crystallinity of isorhamneti through recrystallization.
Steps:
Dissolve the obtained crude crystals in an appropriate amount of organic solvent (such as ethanol, acetone, etc.). When selecting a solvent, consideration should be given to its solubility in isorhamneti and its ability to separate impurities.
Perform crystallization operations under appropriate conditions, such as slow cooling, adding seeds, etc., to promote the crystallization and precipitation of isorhamneti.
Filter and collect the crystals, and wash with a small amount of solvent to remove surface impurities.
Dry the crystal to a constant weight to obtain high-purity isorhamnetin product.
Through the above four steps, isorhamneti can be effectively extracted from seabuckthorn fruit residue, and a product with high purity can be obtained.
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