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The synthetic method of resveratrol
Resveratrol is an inhibitor of many oxidative metabolism enzymes of aromatic carcinogens. It is named as the natural chemopreventive agents of cardiovascular and cerebrovascular diseases and cancer. Many studies have shown that resveratrol also has many functions, such as anti-mutagenic activity, protecting cell toxicity induced by the oxidation of lipoprotein, inhibiting tumor cell reproduction, and so on.
Human separated resveratrol from the root of veratrum grandiflorum for the first time in 1940. Researchers currently has found resveratrol from at least 21 families and 31 genera of 72 species of plants, such as grape vine genus, vitis snake, legumes arachis, cassia, sophora, polygonum, and so on. Because of the low concentration of resveratrol in the plant and the high extraction cost, using chemical, biological, genetic engineering and other methods to obtain resveratrol has become an indispensable means for its development process. The roadmap to synthesis resveratrol is as follows:
3,5-dihydroxybenzoic acid (3) forms 3,5-dihydroxybenzoic acid methyl ester (4) by esterification reaction. Choose methyl ether as phenolic hydroxyl-protecting groups. (4) reacts with dimethyl sulfate to get 3,5-di-methoxybenzoate (5). (5) generates the corresponding benzene methanol (6) after reduction, and forms 3, 5-dimethoxy benzyl bromide (7) through further bromination. Then diethyl (3,5-dimethoxy benzyl) phosphonate (8) can be get by roman abramovich's reaction. (8) reacts with p-anisaldehyde to form the key intermediate 3,4,5-trimethoxy-trans-stilbene (9) via Wittig-Honer reaction. Finally, methyl can be removed by freshly prepared aluminum triiodide. Then the aimed product resveratrol can be separated by thin layer chromatography.
ChEBI: A resveratrol in which the double bond has E configuration.
Polygonum cuspidatum is the rhizome of polygonaceae polygonum cuspidatum. Polygonum cuspidatum rhizome contains free anthraquinone and anthraquinone glycosides, whch mainly are emodin ether, rhubarb phenol, anthracene glycosides A and B, etc. It also contains resveratrol glycosides, polydatin, protocatechuic acid, dextrose catechin, tree anthrone-8-glucosidecassia, β-sitosterol glucoside and glucose, rhamnose, ginger candy, amino acids, tannin and copper, iron, manganese, zinc, potassium and potassium salts, etc.
Figure 1 is Polygonum cuspidatum plant
Resveratrol (Res) is a non-flavonoid polyphenol compound. It is considered as a phytoalexin, which is generated when the plant is attacked by pathogenic, or in the poor environment. It is mainly found in grapes, giant knotweed, peanuts, mulberry, pine, Gnetum, Korea Huaifrom 12 families and 31 genera of 72 species of plants.
Extraction of the natural plant: polygonum cuspidatum is used as raw material, extracted, extracted resveratrol crude, and then purified. Crude extraction technologies include organic solvent extraction method, the new method of alkaline extraction and enzymatic extraction method. New methods like microwave-assisted extraction, CO2 supercritical extraction and ultrasonic extraction are also applied. The main purpose of purification is to extract cis-resveratrol and trans-resveratrol and polydatin from raw resveratrol to obtain trans-resveratrol. Common methods of purification are chromatography, silica gel column chromatography, thin-layer chromatography, high performance liquid chromatography and the like.
Resveratrol had significant antioxidant activity on animal fats. Sample of 240mg/kg shows the strongest antioxidant activity during the three samples whose concentration of resveratrol is respectively 120 mg/kg, 240mg/kg, 360mg/kg. In antioxidant tests on lard, the antioxidant effect of resveratrol is stronger than polyphenols with same concentration.
A phytoestrogen with antitumor, antioxidant, antiplatelet, anti-inflammatory and antifungal effects. Inhibits cytochrome P450 1A1 (IC 50 = 23 μ M) and displays mixed agonist/antagonist actions at ER α and ER β estrogen receptors. Converted into the anticancer agent piceatannol (4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol ) by cytochrome P450 1B1
Resveratrol is not only the chemopreventive agents of neoplastic diseases, but also the chemopreventive agents to reduce platelet aggregation and prevent and treat atherosclerosis, cardiovascular and cerebrovascular disease. In the 1990s, studies of science and technology workers on resveratrol have advanced, and reveal its pharmacological effects. It can inhibit normal platelet aggregation, prevent myocardial cram, cerebral embolism. It has a protective effect on cardiac hypoxia, restore decline of cardiac output which is caused by burn or hemorrhagic shock, and can expand arteries and improve microcirculation.
In 1998, United States Al.Mindell listed resveratrol as one of “the 100 most popular and effective anti-aging substance” when he compiled the anti-aging Scripture. Peanut oil, peanut butter and other foods rich in resveratrol will be the new fashion of nutrition and health in the 21st century. Resveratrol is the chemopreventive agents of neoplastic diseases, but also the chemopreventive agents to reduce platelet aggregation and prevent and treat atherosclerosis, cardiovascular and cerebrovascular disease. Resveratrol shows some inhibitory effect on staphylococcus aureus, the card he bacteria, escherichia coli, pseudomonas aeruginosa, and has a stronger inhibitory effect on the orphan virus, herpes simplex virus, and enteroviruses, coxsackie a, b groups.
- Resveratrol is a natural antioxidant. It can reduce blood viscosity, inhibit platelet aggregation and vasodilation, keep the blood flowing and prevent the occurrence and development of cancer. It has the function to prevent and treat atherosclerosis, coronary heart disease, ischemic heart disease and high blood cholesterol. It has an effect on suppressing tumor. Resveratrol also has estrogen-like effects that can be used to treat breast cancer and other diseases. It can retard aging and prevent cancer. Red grape skins, red wine and grape juice have high concentrations of resveratrol. Studies have shown that the integrity of the chromosomes will be destroyed as the human aging. But resveratrol can activate proteins that can repair chromosome, thus delaying aging.
- Resveratrol is a polyphenolic phytoalexin. It is also classified as a stilbenoid, a derivate of stilbene, and is produced in plants with the help of the enzyme stilbene synthase. The levels of resveratrol found in food varies greatly. Red wine contains between 0. 2 and 5. 8 mg/L depending on the grape variety, while white wine has much less. The reason for this difference is that red wine is fermented with grape skins, allowing the wine to absorb the resveratrol, whereas white wine is fermented after the skin has been removed.
- Resveratrol is a very effective anti-oxidant with 95% efficiency in preventing lipid peroxidation as compared with 37% for Vitamin C or 65% for Vitamin E. It has very strong peroxyl radical scavenging abilities, more than gallic and ellagic acids and epicatechins. Resveratrol has been shown to protect against UVB mediated skin damage in mice by boosting anti-oxidant defenses, and it has been shown to help alleviate skin wounds.
- Resveratrol is effective against photoaging due, in part, to its anti-oxidant properties, and is recommended for use in pre- or post-sun exposure products. Resveratrol can pass through the stratum corneum to be found in the dermis and epidermis. It has been shown to preserve dermal collagen, and may be effective in enhancing glycosaminoglycans, which enhance tissue hydration. It has been shown to stimulate skin’s cellular renewal, and help increase skin's thickness. And it has been shown to inhibit tyrosinase, which indicates its use for reducing hyperpigmentation.
Possible Side effects
Little is known about the safety of long-term or high dose use of resveratrol.
Since resveratrol might act like estrogen, some medical experts recommend that people with hormone-sensitive cancers (condition such as breast cancer, uterine cancer, ovarian cancer, endometriosis, or uterine fibroids), pregnant women, and children avoid taking resveratrol.
In addition, resveratrol could interact with blood thinners like warfarin, aspirin, and ibuprofen by slow blood clotting, which may increase the risk of bleeding in people with bleeding disorders.
According to one study, high-dose resveratrol supplementation was associated with fever, reduced blood cells, and decreased blood pressure.
There is some concern that high doses of resveratrol supplements could lead to kidney problems in some people.
Contents determination method
C18 column, mobile phase consisted of acetonitrile and water (volume ratio 30: 70), and UV detection at 30 6nm are used to detect. The results show that if the concentration of resveratrol is in 10~250 μg/mL, concentration and peak area show a good linear relationship (r = 0.9999); the recovery is 925% to 1026%; the lowest detectable concentration is 0.6mg/g. The flow rate can be adjusted to detect the enzymatic conversion of polydatin and resveratrol at the same time.
- Resveratrol can prevent the oxidation of low density lipoprotein, and has the potential effect on preventing cardiovascular disease, cancer, antivirus and immune regulation. Its main role is antioxidant properties.
- Cardiovascular drugs. It can reduce hematic fat and prevent heart disease. It also has the effect on AIDS.
- Antioxidants and the activity in anti-inflammatory, antithrombotic, anti-cancer, anti-cancer, anti hyperlipidemia and antibacterial.
- Anti-aging, regulating blood lipid, cardiovascular protection, anti-hepatitis.
- Resveratrol is a phytoalexin produced naturally by several plants with anti-cancer, anti-inflammatory, blood-sugar-lowering and other beneficial cardiovascular effects.
Resveratrol is a kinds of natural antioxidants that presents in grapes, red wine, mulberries, peanuts and polygonum cuspidatum. It is polyphenols. It is soluble in organic solvents but insoluble in water. Its dissolved order in organic solvents is: acetone > ethanol> methanol> ethyl acetate> ether> chloroform.
Resveratrol Benefits and ralting biological activities
Much of the research pointing to the benefits have been laboratory or animal-based studies. So far, research on resveratrol's effectiveness in humans has yielded mixed results.
Anti-Aging and Anti-Cancer Effects
- Effects on biotransformation enzymes
- Inhibition of proliferation and induction of apoptosis
- Inhibition of tumor invasion and angiogenesis
Helps Protect the Brain and Cognitive/Mental Health
- Protects Cardiovascular Health
- Inhibition of vascular cell adhesion molecule (VCAM) expression
- Inhibition of vascular smooth muscle cell (VSMC) proliferation
- Stimulation of endolethelial nitric oxide synthase (eNOS) activity
- Inhibition of platelet activiation and aggregation
- Stimulation of neurogenesis and microvessel formation
- Stimulation of β-amyloid peptide clearance
- Inhibition of neuroinflammation
- Reduction of oxidative stress
Minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet aggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity
of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion and progression.
raw material for Tamiflu; Oseltamivir
resveratrol sources plants
Resveratrol is anthraquinone terpenoids. It mainly comes from rhizome extract of polygonum cuspidatum. Polygonum cuspidatum: Shrubby perennial herb, up to 1 meter or more. Rhizome lying underground, wood brown, section significantly. Stems erect and cylindrical, surface glabrous, scattered with most red spots, hollow. Leaves alternate, broadly ovate to nearly circular, long 7-12cm, width 5-9cm, apex mucronate, base rounded or cuneate; petiole 1-1.5cm sheath care quality, brown, early fall. Flowering is from July to September, and fruiting from September to October. Spring and autumn can be excavated, cut and dried. Polygonum cuspidatum is born in the valley, creek or shore.