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Pure resveratrol powder, CAS 501-36-0, The chemical formula is C14H12O3, which is a non flavonoid polyphenolic organic compound and an antitoxin produced by various plants when stimulated. White to light yellow powder, odorless, insoluble in water, soluble in organic solvents such as ether, chloroform, methanol, ethanol, acetone, ethyl acetate, etc. It can be synthesized in grape leaves and skins and is a bioactive ingredient in wine and grape juice. After oral administration, it is easily absorbed and metabolized before being excreted through urine and feces.
In vitro and animal experiments have shown that resveratrol has antioxidant, anti-inflammatory, anticancer, and cardiovascular protective effects. It also has other biological activities such as antibacterial, antioxidant, immune regulation, anti asthma, etc. Due to its various biological activities, resveratrol is highly sought after by people
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Chemical Formula |
C14H12O3 |
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Exact Mass |
228 |
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Molecular Weight |
228 |
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m/z |
228 (100.0%), 229 (15.1%), 230 (1.1%) |
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Elemental Analysis |
C, 73.67; H, 5.30; O, 21.03 |
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In 2003, Harvard University professor David Sinclair and his team discovered that resveratrol can activate acetyltransferase, increase the lifespan of yeast, and sparked a wave of research on resveratrol's anti-aging properties. Howitz et al. found that resveratrol can act as the strongest activator of the silent information regulation 2 homolog1 (SIRT1), simulating the anti-aging response of calorie restriction (CR) and participating in the regulation of the average lifespan of organic organisms.
CR is a strong inducer of SIRT1, which can increase the expression of SIRT1 in organs and tissues such as brain, heart, intestine, kidney, muscle, and fat. CR can cause physiological changes that delay aging and prolong lifespan, with the most significant extension being 50%. Research has confirmed that resveratrol has the effect of prolonging the lifespan of yeast, nematodes, fruit flies, and lower fish species.
Pure resveratrol powder has significant inhibitory effect on a variety of tumor cells, such as hepatocellular carcinoma, breast cancer, colon cancer, gastric cancer, leukemia, etc. Scholars have confirmed through MTT assay and flow cytometry that resveratrol has a significant inhibitory effect on melanoma cells.
There are reports showing that resveratrol can enhance cancer radiotherapy, exert a "1+1>2" effect, and effectively inhibit the action of cancer stem cells. However, so far, due to the complexity of the anti-tumor mechanism of resveratrol, researchers have not reached a consensus on its mechanism of action.
Anti cancer mechanism
Resveratrol can have antioxidant, anti cardiovascular disease, anti-cancer, antibacterial, anti platelet aggregation, antibacterial, anti-aging effects, etc. It can block pathways such as apoptosis, NF - κ B, PI3K/Akt, MAPK, etc. and resist tumors. It is a plant antitoxin, anti-tumor enhancer and sensitizer, found in resveratrol, Polygonum cuspidatum, grapes, peanuts, pine trees, mulberry flowers, etc. It can play a preventive and therapeutic role in the initiation, occurrence, and spread of tumors, promote the expression of apoptosis inhibitory proteins (IAPs), tumor necrosis factor related apoptosis inducing ligands (TRAIL), trigger the degradation of survival factors, downregulate anti apoptosis protein Bcl xL Mcl-1,ERK1/2.
The level of heat shock protein 70 increases the expression of pro apoptotic proteins Bax, Bak, Bid, Bad, and sirtuinl (activating FoxO p53), Inducing tumor cell apoptosis. Resveratrol inhibits TNF-a induced IrB, inhibits NF-B phosphorylation activation, activates histone deacetylase, and has anti-inflammatory, anti proliferative, and anticancer effects. Resveratrol can inhibit NF-B inducers such as phorbol ester, lipopolysaccharides, ceramides IL-1β, Inhibiting COX-2 production of reactive oxygen species can inhibit the PI3K/Akt and ERK1/2 pathways, promote the synthesis of p53, Rb, FoxO, TRAIL, DR4, DR5, p21, and p27, mediate cell apoptosis, reduce the synthesis of E2F, cyclin, CDK, AP-1, Egrl, and EGF, and inhibit cell proliferation.
Preventing and treating cardiovascular diseases
Pure resveratrol powder studies have found that the "French paradox" phenomenon, that is, the French eat a lot of fat every day, but the incidence rate and mortality of cardiovascular diseases are significantly lower than those in other European countries, may be related to their daily consumption of wine, and resveratrol may be its main active protective factor. Research has shown that resveratrol can regulate cholesterol levels in the blood by binding to estrogen receptors in the human body, inhibiting platelet formation and blood clot adhesion to blood vessel walls, thereby inhibiting and reducing the occurrence and development of cardiovascular disease, and reducing the risk of cardiovascular disease in the human body.
Introduction to related majors
Test method:
The commonly used methods for detecting resveratrol include high-performance liquid chromatography, gas chromatography-mass spectrometry, capillary electrophoresis, thin-layer fluorescence scanning, and ultraviolet spectrophotometry. The detection results of high-performance liquid chromatography are accurate and precise, but the steps are complicated, time-consuming, and costly. Gas chromatography-mass spectrometry (GC-MS) has the advantages of less time consumption, less sample usage, and less loss of the tested components. However, if the sample is directly injected without derivatization, the chromatographic peak tailing is severe, and the processed sample is prone to water carryover. The detection sensitivity of thin-layer fluorescence scanning method is low and its applicability is narrow. UV spectrophotometry is simple to operate and cost-effective, but it has a large detection error. During detection, corresponding purification and concentration measures should be taken based on the physical and chemical properties of each component to reduce the influence of interfering substances and improve the detection effect.
Resveratrol has relatively low bioavailability in the body, and studies have shown that the bioavailability of its metabolites in the small intestine and liver is approximately 1%. Resveratrol is rapidly metabolized in animal bodies, reaching its peak in plasma within 5 minutes. Research on animal metabolism has found that resveratrol is mainly metabolized in the form of sulfated and glucuronide products in mammals such as mice, pigs, and dogs. Research has confirmed that resveratrol is distributed in different tissues of mammals in a conjugated form, and it is more absorbed and distributed in organs with abundant blood flow, such as the liver, kidneys, heart, and brain.
Through the study of the metabolism of resveratrol in the human body, it was found that there is a "bimodal phenomenon" in the plasma concentration of resveratrol in normal individuals after oral administration, while there is no such phenomenon in IV administration (intravenous injection); After oral administration, the metabolic products of resveratrol in plasma are mainly glucuronidation and sulfation. After oral administration of resveratrol in patients with colorectal cancer, the absorption of resveratrol in the left colon is lower than that in the right colon, and six metabolic products, including resveratrol sulfate and glucuronide compounds such as resveratrol 3-O-glucuronide, resveratrol 4 ′ - O-glucuronide, resveratrol 3-O-sulfate, and resveratrol 4 ′ - O-sulfate, are obtained.
Preparation method of pure resveratrol powder:
Solvent extraction is one of the most widely used extraction methods at home and abroad. The commonly used solvent extraction methods mainly include three kinds: percolation method, extraction method and reflux method. The commonly used solvents for reflux extraction of resveratrol include methanol, ethanol, acetone, ethyl acetate, etc. Among them, 60%~90% ethanol aqueous solution is the most commonly used solvent for reflux extraction of resveratrol original plants. Other solvents are rarely used because of their low efficiency or relatively high toxicity.
Resveratrol exists in many plants in the form of resveratrol glycoside, which can be hydrolyzed into resveratrol by enzyme, and then the free resveratrol can be extracted. With this method, higher yield can be obtained, so some researchers have adopted the method of enzymatic hydrolysis to extract resveratrol. There are three sources of enzyme in enzymatic extraction: using plant self enzyme, adding external enzyme and producing enzyme by inoculating microorganism.
Microwave extraction is a method for extracting effective components from plants because the temperature of plant cells rises rapidly after absorbing microwave energy in the microwave field and the cells swell and break. This method is commonly used in laboratory research.
Supercritical CO2 extraction is a process of extracting or separating some components in the mixture with CO2 fluid in the supercritical state as the solvent. Supercritical CO2 is characterized by stable property, non-toxic, non polluting environment, strong permeability and solubility, as well as good transmissibility and fluidity.
Conversion synthesis of pure resveratrol powder:
The content of resveratrol in natural organisms is not high, which can be transformed by various methods.
The conversion of resveratrol mainly refers to the conversion of resveratrol glycosides in plants into their aglycones, which is usually achieved by acid hydrolysis or alkali hydrolysis. However, the acid alkali hydrolysis reaction is generally required to be carried out under high temperature and pressure, which requires severe conditions and high equipment requirements, causing certain damage to the environment.
The method of biotransformation of resveratrol is relatively mild and easy to operate. Therefore, enzymatic hydrolysis and microbial fermentation are generally used to transform resveratrol at this stage. In recent years, there are many research reports on enzymatic hydrolysis of Polygonum cuspidatum, such as the use of its own enzyme, cellulase β- Resveratrol was obtained by enzymatic hydrolysis of glucosidase. The yield of resveratrol in Polygonum cuspidatum can also be greatly improved by microbial fermentation. Some scholars used rhizobacteria to carry out liquid fermentation on the crude extract of polydatin, and transformed polydatin into resveratrol, with a conversion rate of 95.8%.
Resveratrol can also be obtained through the transformation of polymers in grapes. The content of resveratrol in grape is relatively small, but it contains a series of resveratrol derivatives produced by dehydrogenation and polymerization of resveratrol in plants, such as heyneanol A, dimer ε- Viniferin and δ- viniferin, trimer α- Viniferin, tetramer laevifenol, higher oligomer, etc. Studies have shown that resveratrol derivatives have similar biological activities to resveratrol, and some of these compounds are even more active, selective and stable than resveratrol. These polymers can be converted into resveratrol under certain conditions. For example, by adjusting temperature, ultraviolet radiation and other conditions, it can stimulate the accumulation of resveratrol in grapes.
In 1940, Japanese scholar Michio Takaoka first isolated resveratrol from the plant Veratrum album in the Liliaceae family. Later, in 1963, resveratrol was isolated from the Polygonum cuspidatum plant in the Polygonaceae family.
In 1976, resveratrol was also discovered in grape leaves. It is an antitoxin secreted by plants in adversity or when they encounter pathogen invasion. Its synthesis increases sharply under UV irradiation, mechanical damage, and fungal infection, hence it is called phytoflexin.
The initial understanding of resveratrol was limited to its ability to enhance plant resistance to pathogenic attacks and environmental degradation, and it was not until 1992 that it was discovered that wine's ability to prevent cardiovascular disease was due to the presence of resveratrol, which attracted the attention of scholars around the world. The research on resveratrol has become a hot topic in drug research, and it has been found to have various biological functions such as immune regulation, anti-aging, prevention of cardiovascular and cerebrovascular diseases and neurodegenerative diseases, prevention of tumor formation, anti-inflammatory, antimicrobial, antiviral, etc. Resveratrol is also used as a dietary supplement for human health and disease prevention. After oral administration, resveratrol is metabolized in the liver with a bioavailability of only 1%, which limits its application. The chemical synthesis, structural modification, and preparation of derivatives using resveratrol as a lead compound have also become a hot research topic. A large number of resveratrol structural analogues have been obtained, and industrial production of resveratrol has been achieved.
In April 2016, a paper published by Chongqing Third Military Medical University in the journal Molecular Biotechnology (mBio) was the first to explore the mechanism by which resveratrol can alter gut bacteria and reduce the risk of heart disease.
As of 2021, resveratrol is widely distributed in plants, it has been found in more than 70 plants from 21 families, especially in Vitis, Ampelopsis, Polygonum, Arachis, Cassia, Sophora, Veratrum, Eucalyptus plants. Representative plants containing resveratrol include grapes, Polygonum cuspidatum, peanuts, cassia seed, etc. There is already a simple and mature chemical synthesis method for resveratrol with high product yield and low production cost, which is used for industrial large-scale preparation, making the acquisition of resveratrol no longer dependent on extraction and separation from plants. The synthesis process of resveratrol often uses the Wittig reaction to achieve the splicing of two benzene rings, with a yield of over 50%.
FAQ
What is resveratrol good for?
In this sense, the present review summarizes resveratrol' beneficial health effects, including anticancer, antimicrobial, neuroprotective, antiaging, anti-inflammatory, cardioprotective and blood-sugar lowering properties, as also life-prolonging effects.
Who should not use resveratrol?
Hormone-sensitive condition such as breast cancer, uterine cancer, ovarian cancer, endometriosis, or uterine fibroids: Resveratrol might act like estrogen. If you have any condition that might be made worse by exposure to estrogen, don't use resveratrol.
What foods are high in resveratrol?
In general, the resveratrol content of red wine is higher than that of white wine. Other primary dietary sources of resveratrol include peanuts, mulberries, blueberries, and strawberries.
Is resveratrol a blood thinner?
Due to resveratrol's blood-thinning properties, you should stop taking any resveratrol supplements two weeks before surgery. Resveratrol slows blood clotting. If taken with anticoagulant (non-clotting) medications, you are at increased risk of bleeding.
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