Procyanidin
Procyanidin
CAS: 4852-22-6
Molecular Formula: C30H26O13
Procyanidin - Names and Identifiers
| Name | Procyanidin |
| Synonyms | Procyanidin PROCYANIDINE Procyanidin 4852-22-6 Procyanidin (water soluble) Moringa oleifera seed extract 2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroMan-3-yl)oxy)chroMan-3,4,5,7-tetraol 2-(3,4-dihydroxyphenyl)-2-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl]oxy}-3,4-dihydro-2H-chromene-3,4,5,7-tetrol 2-(3,4-Dihydroxyphenyl)-2-((2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl)oxy)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol 2H-1-Benzopyran-3,4,5,7-tetrol,2-(3,4-dihydroxyphenyl)-2-[[2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2H-1-benzopyran-3-yl]oxy]-3,4-dihydro-(9CI) |
| CAS | 4852-22-6 |
| EINECS | 1806241-263-5 |
| InChI | InChI=1/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2 |
Procyanidin - Physico-chemical Properties
| Molecular Formula | C30H26O13 |
| Molar Mass | 594.52 |
| Density | 1.87g/cm3 |
| Boling Point | 986.4°C at 760 mmHg |
| Flash Point | 550.3°C |
| Solubility | Soluble in water and most organic solvents |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Reddish brown powder |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.876 |
| Physical and Chemical Properties | Soluble in water and most organic solvents. Derived from grape seed extract or French Coast pine bark extract. |
Procyanidin - Introduction
Pharmacological effects: Proanthocyanidins (grape seed extract) is a new type of high-efficiency antioxidant, is the most powerful free radical scavenger found so far, and has very strong in vivo activity. It is used to improve blood circulation, treat diabetic retinopathy, reduce edema and inhibit varicose veins, prevent complications after cataract surgery in diabetic patients, eliminate edema, and moisturize the skin. The combination of anthocyanins and vitamin C can break down cholesterol and act as a cardioprotective agent.
Last Update：2022-10-16 17:25:25
Procyanidin - Reference Information
| Overview | Proanthocyanidins are a large class of widely existing in plants with similar structures and anthocyanins. They are polyphenols formed by condensation of flavan-3-ol monomers. It has strong antioxidant activity and has been widely used in food, medicine, cosmetics and other fields. |
| Plant source | It is now found that a variety of plants contain proanthocyanidins. The extracted plants include grapes, English hawthorn, peanuts, ginkgo, Japanese Rohan cypress, North American Thuja, Blueberry and black beans, etc. Grape seed is the main by-product of grape wine making, and it accounts for 65% in grape skin residue. The content of polyphenols in grape seed can reach 5% ~ 8%. Among these polyphenols, the content of proanthocyanidins is the highest, reaching 80% ~ 85%. Anthocyanins are widely found in the nuclei, skins or seeds of various plants. Figure 2 shows blueberry, a common source of proanthocyanidins. |
| determination method | 1. benzyl mercaptan (or phloroglucinol) acid degradation method in the presence of benzyl mercaptan, phloroglucinol and other nucleophiles, procyanidins were acidolysis treatment before determination. 2. n-butanol-hydrochloric acid degradation method the principle is that proanthocyanidins are degraded in the presence and heating of inorganic acids to produce red anthocyanins with maximum absorption at 550nm. This method is specific and selective. 3. high performance liquid chromatography reversed-phase high performance liquid chromatography (RP-HPLC) has been proved to be an effective method for analyzing phenolic substances. it can better separate the monomers, dimers and a small amount of trimers of proanthocyanidins, and is often used to analyze low molecular weight proanthocyanidins. 4. Vanillin method Using proanthocyanidin flavone ring in strong acid medium to react with aromatic aldehyde to form colored adducts for determination, the total content of monomer and polymer can be determined at the same time, usually using catechins as the standard substance. |
| preparation method | 1. plant extraction method 1.1 extraction at present, the commonly used process is degreasing method including pressing method, solvent method and supercritical CO2 extraction method. among them, supercritical CO2 extraction method is the best, not only has high oil extraction rate, but also has the smallest destructive effect on proanthocyanidins and good quality. 1.2 separation purified procyanidins monomer substances are usually separated by column chromatography, of which polyamide, SephadexLH-20 and ToyopealHW-40 are the most effective fillers. For compounds that are difficult to separate or require less, they can be prepared by semi-preparative reversed-phase high performance liquid chromatography (RP-HPLC) and normal-phase high performance liquid chromatography (NP-HPLC). As the degree of polymerization increases, the number of isomers of procyanidins increases geometrically, and it is very difficult to separate and purify such macromolecules. For multimers, they can be segmented by molecular weight (degree of polymerization) size. At present, the established classification methods include solvent precipitation and various chromatography methods, such as thin layer chromatography, normal phase high performance liquid chromatography, gel exclusion chromatography, countercurrent chromatography, etc. 2. Biosynthesis method The main product of reducing (2R,3R)-dihydro-3 ′,4 ′,3,5, 7-pentahydroxyflavane by sodium borohydride as a reducing agent is the 2,3-trans -3,4-trans isomer of white cyanidin (Leucocyanidin), and the reduction product of the enzyme is 2,3-trans -3,4-cisomer. Under the condition of micro-acid, the 3,4-trans isomer may be partially converted to the 3,4-cis isomer. The 3,4-cis isomer is more acidic than the 3,4-trans isomer, and it is easy to react with thiol and diol reductase. The conditions required for enzyme synthesis are relatively harsh, and there is also a problem of cis-trans isomers. At present, this method is not yet mature. |
| Pharmacological activity | 1. Antioxidant activity Proanthocyanidins have strong antioxidant activity and are the strongest and most effective free radical scavengers discovered by humans so far. One, especially its in vivo activity, the antioxidant activity of proanthocyanidins presents a dose-effect relationship, but if it exceeds a certain concentration, its antioxidant activity will decrease with increasing concentration. Antioxidant characteristics and mechanism: ①Effectively scavenge superoxide anion radicals and hydroxyl radicals, etc., and can also interrupt the free radical chain reaction; ②Participate in the metabolism and protein phosphorylation of phospholipids and arachidonic acid, Protect lipids from peroxidation damage; ③It is a powerful metal chelating agent that can chelate metal ions and form inert compounds in the body; ④Protect and stabilize vitamin C, which helps the absorption of vitamin C. 2. Anti-tumor activity Proanthocyanidins have significant killing effects on a variety of tumor cells, and have significant inhibitory effects on a variety of carcinogens in the initiation and cancer promotion stages. Proanthocyanidins can inhibit the growth of cancer cells and induce apoptosis. In addition, for liver cancer, prostate cancer, skin cancer, etc., they all show good anti-cancer activity. With the deepening of research, procyanidins will play a greater role in the prevention and treatment of cancer. Treatment brings good news. 3. Anti-inflammatory, anti-allergic, anti-edema activity Proanthocyanidins can reduce the increase in capillary permeability caused by inflammatory mediators such as histamine and bradykinin, reduce the fragility of the capillary wall, and make the capillary The tension and permeability of the blood vessels are reduced, and the material transport capacity of the capillaries is protected, thereby playing anti-inflammatory activity. In addition, procyanidins can also inhibit the activity of histamine decarboxylase, limit the effect of hyaluronidase, and have a significant effect on various arthritis and gastric and duodenal ulcers. 4. other proanthocyanidins also have immunomodulatory activity, anti-radiation effect, anti-mutation, anti-diarrhea, anti-bacterial and anti-virus, anti-dental caries, improve visual function, prevent senile dementia, and treat sports injuries. |
| cardiovascular protection | 1. anti-myocardial ischemia-reperfusion injury procyanidins can significantly reduce the incidence and duration of ventricular tachycardia and ventricular fibrillation, reduce the area of myocardial infarction, promote the recovery of cardiac contractile function after ischemia-reperfusion, and have a protective effect on myocardium after ischemia-reperfusion. 2. anti-atherosclerosis by inhibiting the oxidation of LDL in the arterial wall, play an anti-AS role. 3. lipid-lowering effect hypercholesterolemia is an independent risk factor for coronary atherosclerotic heart disease. In the foam cells intervened by grape seed proanthocyanidins, the accumulation of total cholesterol, esterified cholesterol and triglycerides is reduced, that is, the formation of foam cells is reduced by down-regulating the key genes that regulate cholesterol, so as to achieve the effect of preventing. 4. Antihypertensive effect Proanthocyanidins can not only antagonize the effect of histamine or prostaglandin constricting arteries, but also inhibit the activity of angiotensin-converting enzyme, a key enzyme in elevated blood pressure, thus reducing and maintaining normal blood pressure. 5. antiplatelet aggregation proanthocyanidin B2-S can inhibit TXB2HHT formation through platelets treated with exogenous arachidonic acid. The mechanism of inhibiting platelet aggregation is to inhibit the biosynthesis of thromboxane. 6. protective effect on vascular endothelial cells procyanidins can antagonize oxidative damage of vascular endothelial cells, significantly improve cell survival rate, reduce lactate dehydrogenase (LDH) release and reduce MDA production. It has obvious inhibitory effect on collagenase, elastase and hyaluronidase, thereby reducing the damage of these enzymes to collagen, elastin, hyaluronic acid and other important components of the inner wall of blood vessels. |
| pharmacokinetics, toxicology, dose | procyanidins can be rapidly absorbed in gastrointestinal tract, reaching a peak value in 45min with a half-life of 5h. 14% is excreted in bile within 1lh, excreted in the form of CO2, urine and feces after 24h of 70%, and non-specific binding in blood, liver and kidney, in the skin, blood vessel wall, gastrointestinal mucosa for specific binding, and are characterized by elevated levels of glucosamine, its main target organ for connective tissue, its metabolism has important intestinal-liver circulation. Rats and mice oral LD50 were above 4000mg/kg, good tolerance, no teratogenic, mutagenic effect. Extensive tests have proved that it is non-toxic, non-carcinogenic, non-antigenic, and does not cause fetal malformation. In most clinical reports, adults take between 100 and 200 mg per day. |
| application field | 1. health food at present, health food (mainly oligomer capsules or tablets) with procyanidins as the main ingredient in the domestic and foreign markets can prevent and treat heart disease, arteriosclerosis and phlebitis related to free radicals by scavenging oxygen free radicals. Proanthocyanidins can also be used as a natural preservative to extend the shelf life of food and eliminate the food safety risks that may be caused by synthetic preservatives. Because it also has the effect of lowering blood lipids, anti-cancer activity, lowering blood pressure, etc., it is widely used abroad in health foods such as lowering blood pressure, lowering blood lipids, anti-tumor, and strengthening the brain. It is also used as an ingredient or additive for ordinary foods. 2. Pharmaceutical industry Grape seed proanthocyanidins were first used to treat hay fever and allergies in the 1960s. With the in-depth research on it, their therapeutic effects on vascular diseases were confirmed in the 1980s. In recent years, grape seed proanthocyanidins are also used to treat ocular keratopathy, retinal diseases, and prevent periodontal disease and cancer. Foreign markets use it to treat microcirculation diseases (eye and peripheral capillary permeability diseases and venous and lymphatic insufficiency), etc. 3. Cosmetics industry proanthocyanidins have anti-oxidation, free radical scavenging ability, anti-elastic enzyme activity and improve microcirculation activity, which has opened up a wide range of application prospects in cosmetics. Skin care products containing proanthocyanidins can inhibit the generation of peroxides caused by oxygen free radicals produced by ultraviolet radiation, and have obvious effects on improving skin inflammation, preventing blackening, and anti-aging. At present, in France, Italy and Japan, there have been night cream, hair cream, mouthwash, skin whitening agent, anti-inflammatory agent and oral deodorant made of proanthocyanidins. |
| development trend | procyanidins have undergone more than 30 years of research, development, clinical application and experiments, and are favored by people for their superior antioxidant activity. High-quality OPC is widely used in drugs, cosmetics, functional foods and other fields due to its good solubility in water and alcohol, bright color, rich resources, significant curative effect and minor side effects. Therefore, it is of great value to explore new mechanisms of action, find new resources and study new acquisition methods (biological enzyme method) and develop procyanidins products. |
| Polymerization mechanism | Proanthocyanidins are a kind of polyphenolic compounds synthesized through the secondary metabolic pathway of plant flavonoids. They are flavan-3-alcohols such as catechins and oligomers of epatechins or polymers. Biosynthesis all starts from phenylalanine. Hypotheses about its polymerization mechanism include: the polymerization of proanthocyanidins occurs in the central large vacuole of plant cells, and the precursors of extension units during condensation may be colorless anthocyanins, flavan-3-ol and anthocyanins. The condensation enzymes that catalyze the polymerization reaction may include: plant polyphenol oxidase, plant laccase and plant peroxidase. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: Proanthocyanidins (grape seed extract) is a new type of high-efficiency antioxidant, is the most powerful free radical scavenger found so far, and has very strong in vivo activity. It is used to improve blood circulation, treat diabetic retinopathy, reduce edema and inhibit varicose veins, prevent complications after cataract surgery in diabetic patients, eliminate edema, and moisturize the skin. The combination of anthocyanins and vitamin C can break down cholesterol and act as a cardioprotective agent. |
Last Update：2024-04-09 21:54:55
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