Epicatechin (EC) is a natural plant flavanol compound with the chemical formula C15H14O6. It is white crystals, easily soluble in water and methanol. It is collectively referred to as catechin compounds along with epigallocatechin (EGC), catechin gallate (CG), epicatechin gallate (ECG), and epigallocatechin gallate (EGCG). It is an isomer of catechin.
Epicatechin is widely found in Chinese medicinal materials such as Sendeng, Aconite, Polygonum multiflorum, Millettia reticulata, Euonymus japonicus, and Lily and Lily. It is also an important active ingredient in Chinese medicine compound preparations such as catechu formula granules, Weimaining capsules, Longxiang ointment, Qili powder, and Juanbi Kangsheng pills, and is an important indicator for evaluating the quality of drugs. It is also present in large quantities in foods such as litchi, propolis, beer, grape seeds, and red wine. The molecular structure of epicatechin has multiple reactive groups and active sites, which can cause epicatechin to undergo a variety of phenolic reactions. Modern pharmacological research has shown that epicatechin and other flavonoids have antioxidant, free radical scavenging, metabolism enhancement, immune regulation and anti-tumor functions. The antioxidant capacity of epicatechin is believed to be the combination of the phenolic hydroxyl group in the molecule and the free radical to achieve the free radical scavenging effect, while the anti-tumor effect is to affect the cycle process of tumor cells and inhibit the cycle growth of tumor cells. At the same time, it also has many spectrum antibacterial effects, and is considered to have great disease prevention potential.
Physical and chemical properties
Melting point: 240 °C (dec.)(lit.)
Storage conditions: 2-8°C
Merck: 13,1912
Structure of epicatechin
There are 12 types of catechins isolated from tea leaves, and the main classification methods of catechins include the number of hydroxyl groups connected to the B ring, whether there are isomers at the 2nd and 3rd positions of the C ring, and whether there is gallic acid at the 3rd position.
Epicatechin belongs to the catechin class and has the basic flavanol-3-ol molecular structure of catechin. Its basic structure is 2-phenylbenzopyran, a low-symmetry polycyclic macromolecular structure. The three rings A, B, and C constitute the mother ring of epicatechin. Each ring is connected to a hydroxyl group, and there is a hydrogen bond between molecules. The B ring of epicatechin is connected to two hydroxyl groups, so it is also classified as a B-ring dihydroxy catechin; the C ring of epicatechin is a benzo heterocycle, and its spatial structure is not in the same plane. It exists in a chair conformation, and its 2 and 3 positions are connected to different substituents, so epicatechin is also a cis-catechin; depending on whether there is a gallic ester group at the 3rd position of the C ring, catechin can be an ester type or a non-ester type catechin. The 3rd position of the C ring of epicatechin is connected to a hydroxyl group, so epicatechin belongs to a non-ester type catechin.
As a flavonoid substance, epicatechin has many physiological activities, such as anti-oxidation, lipid-lowering and blood sugar-lowering, cardiovascular disease prevention, anti-inflammatory, nerve protection, antibacterial and other effects.
Antioxidant effect
When the concentration of free radicals in the body is too high, the risk of disease will increase. The antioxidant activity of epicatechin is believed to be the ability to capture free radicals carrying chains by providing phenolic hydrogen atoms in the A ring and the B ring. Due to the presence of phenolic hydroxyl groups in the molecular structure of epicatechin, especially the ortho-hydroxyl groups in catechol or pyrogallol, it is easy to be oxidized to quinone structures, which makes it have a strong ability to capture free radicals such as active oxygen, and thus has the function of efficiently scavenging free radicals and lipid free radicals.
Reduce lipids and blood sugar and reduce insulin resistance
Obese individuals often induce the occurrence of chronic diseases such as diabetes. BETTAIEB et al. found that adding 20 mg/kg body weight of epicatechin to the diet of adult rats on a high-fructose diet can reduce the damage of the insulin signaling cascade (IR, IRK-1, Akt, ERK1/2), and reduce the upregulation of negative regulators (PKC, IKK, JNK and PTP1B) in rat adipose tissue, indicating that epicatechin alleviates insulin resistance through its redox regulation mechanism.
Prevention of cardiovascular disease
Compared with the control group of mice on a high-cholesterol diet, the area of atherosclerotic lesions in the epicatechin-added group of mice was reduced by 27%, and the formation of plasma SAA and human-CRP induced by the diet was inhibited, and there was no effect on plasma lipids. At the same time, the anti-atherogenic effect of epicatechin is specific to severe injury types and has almost no effect on mild injuries, which indicates that epicatechin tends to alleviate severe cardiovascular lesions.
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