What Are the Medicinal Uses of Anthraquinone?

Anthraquinone (Anthraquinone, chemical formula: C14H8O2), also transliterated as Antaraguinon, is a quinone chemical. Anthraquinone complexes exist in nature and can also be artificially synthesized. Anthraquinones include products and dimers of different degrees of reduction, such as anthracenol, anthracene oxide, anthrone, etc., as well as glycosides of these compounds. In natural products, anthraquinone is often found in metabolites of higher plants and lower plants lichens and fungi. Anthraquinones have hemostatic, antibacterial, detoxifying, laxative, and diuretic effects.

Chinese name: Anthraquinones
English name: Anthraquinone
nickname: Go back to Antara

Chemical formula: C14H8O2
Density: Dissolved in water
Application: Hemostasis, antibacterial, laxative, diuretic effects

Brief introduction of anthraquinones

Anthraquinones (anthraquinones) are the largest number of compounds among various natural quinones. A long time ago, anthraquinones were used as natural dyes, but later they have been found to have many medicinal values and have been valued. The higher anthraquinone content in higher plants is in Rubiaceae. Anthraquinones are also higher in Rhamnaceae, Leguminosae (mainly lentils), Rareaceae, Purple Tibetaceae, Verbenaceae, Scrophulariaceae and Liliaceae, and anthraquinone compounds are also present in lower plants Lichens and fungus metabolites.

In natural products, anthraquinone is often found in metabolites of higher plants such as Polygonaceae, Leguminosae, Rubiaceae and lower plants lichens and fungi.

Most of the anthraquinone derivatives in botanicals are hydroxyanthraquinone and their glycosides. Most anthraquinone glycosides are formed by the condensation of anthraquinone's hydroxyl and sugar, and a few are formed by the direct connection of sugar with the carbon atom of anthraquinone. Generally, the molecular weight of anthraquinone is less than 500, and it is soluble in water and organic solvents. The molecular weight of free anthraquinone is about 300. , Sodium hydroxide solution, etc., insoluble in water.

Anthraquinone physical and chemical properties

Anthraquinone

Physicochemical properties of anthraquinones Anthraquinones contained in natural plants are mainly monoanthracene cores, double anthracene cores, anthraquinone derivatives, and their dimers dianthracene. Anthraquinones can exist freely in plants, or they can be combined with sugars to form anthraside. Free anthraquinones are less polar and are generally soluble in organic solvents such as methanol, ethanol, ethyl acetate, ether, benzene, and chloroform. They are slightly soluble or insoluble in water. After combining with sugar to form a glycoside, it becomes more polar, easily soluble in methanol and ethanol, and also soluble in hot water, but has low solubility in cold water, and is hardly soluble in non-polar solvents such as benzene, ether, and chloroform. Both free anthraquinone and bound anthraquinone have phenolic hydroxyl groups, and they are acidic. They can form salts with different bases. They are much more soluble in alkaline solutions than in neutral organic solvents. Free anthraquinone and its reduced anthraquinone are soluble in acetone, methanol, and ethanol, slightly soluble in benzene, ether, and chloroform, and hardly soluble in water. Combined with anthraquinone (including reduced type), it is easily soluble in methanol, ethanol, acetone, ethyl acetate, and also in cold water, and is almost insoluble in benzene, ether, chloroform, etc.

Free anthraquinone and bound anthraquinone have phenolic hydroxyl groups, so they have a certain acidity and can form salts with different bases. Therefore, the solubility in alkaline solutions is much greater than in neutral organic solvents, but the acidity is large. It can vary with the number and position of phenolic hydroxyl groups. The order of acidity from strong to weak is:

-COOH (soluble in NaHCO 3 solution)> 2 or more -phenolic hydroxyl groups (soluble in Na 2 CO 3)> 1 -phenolic hydroxyl group (soluble in 1% NaOH)> 2 or more -phenolic hydroxyl groups (soluble in 5% NaOH solution)

Anthraquinone identification reaction

1.Color reaction with alkali

Hydroxyanthraquinones can be dissolved in alkali solution, and show red or purplish red. The color disappears after adding acid, and if you add alkali, it will show red. Anthraphenol, anthrone, and dianthrone must be oxidized to anthraquinone before they can react positively. This reaction can be carried out on the cross section of the crude drug, powder, or extracting droplets of crude drug on filter paper.

2.Borntr? Ger's reaction

Take a small amount of crude drug powder in a test tube, add a few milliliters of lye, shake and filter to obtain a red filtrate. After acidification with hydrochloric acid, the solution turns yellow. Add 2 ml of ether. After shaking, let stand and separate. Separate the ether layer into another test tube, shake with lye, and the water layer will be red. The presence of hydroxyanthraquinones was shown.

3.Magnesium acetate reaction

Take the ethanol extract of the crude drug powder in a test tube, add the magnesium acetate methanol solution, and heat for a while to develop the color. This reaction can also be carried out on filter paper, that is, the ethanol leaching liquid droplets of the crude drug are dropped on the filter paper, and the magnesium acetate methanol solution is sprayed after drying, and the color is developed after heating for a while.

Anthraquinone pharmacological effects

1. Hemostasis: Anthraquinones can promote platelet formation, significantly increase fibrinogen, shorten clotting time, reduce capillary permeability, improve vascular fragility, increase vasoconstrictive activity, and thus promote blood coagulation.

2. Antibacterial effect: Anthraquinone compounds have various degrees of inhibition on various bacteria. Among them, Staphylococcus and Streptococcus are the most sensitive. Shigella, diphtheria, subtilis, and typhoid are also more sensitive. The bacteriostatic mechanism is mainly to inhibit the oxidation and dehydrogenation of bacterial sugars and metabolic intermediates, and can inhibit the synthesis of proteins and nucleic acids, so it can avoid the side effects and drug resistance of certain antibiotics in clinical.

Antibacterial and anti-inflammatory effects Anthraquinones in rhubarb can inhibit various bacteria to varying degrees. Rhubarb not only has a broad-spectrum antibacterial effect, but also has synergistic effects on other antibacterial drugs, and is not prone to drug resistance. The main antibacterial ingredients are: 3-carboxyrhein, hydroxyaloe-emodin, and hydroxyemodin, among which aloe-emodin is the strongest. Experiments have shown that the anthraquinones in rhubarb, that is, emodin, aloe-emodin, emodin, and rhein, all have a strong inhibitory effect on Helicobacter pylori, and some ingredients without antibacterial effects (such as emodin) have The growth of Helicobacter pylori is also inhibited.

3. Diarrhea effect: Due to the protection of glycosyl groups, most of the bound anthraquinone glycosides reach the large intestine without absorption, and are decomposed into aglycones and sugars by bacterial enzymes in the intestine. Aglycones stimulate the mucosa of the large intestine, and inhibit the absorption of sodium ions from the intestinal cavity, increase the water content in the large intestine, cause peristalsis and cause diarrhea.

4. Diuretic effect: Anthraquinones can increase urine output and promote peristalsis of the ureter. Sodium and potassium in the urine also increase significantly, resulting in diuretic and hypotensive effects. Its role is to reduce the reabsorption of intestinal amino acids, inhibit the synthesis of urea in liver and kidney tissues, increase the concentration of free essential amino acids in the blood, use the urea nitrogen synthesis protein in the body and inhibit the decomposition of muscle proteins, and increase the excretion of urea and creatinine To complete.

5.Antiviral effect Andersen et al performed antiviral screening on a variety of anthraquinones and their derivatives, and the results showed that emodin type anthracene derivatives with hydroxyl and methyl substitution were effective against membrane viruses such as herpes stomatitis virus and herpes simplex Virus (HSV-1, 2), parainfluenza virus, etc. all have inhibitory effects. Studies show that anthraquinone has antiviral effects in aloe. Andersen et al screened various anthraquinones and their derivatives for antiviral screening, and the results showed that emodin-type anthracene derivatives with hydroxyl and methyl substitutions were effective against membrane viruses such as herpes. Stomatitis virus, herpes simplex virus (HSV-1, 2), parainfluenza virus, etc. all have inhibitory effects. Studies have shown that anthraquinones in aloe have inhibitory effects on herpes zoster virus, enveloped virus, chickenpox, pseudorabies virus, and so on. Electron microscopy showed that the herpes simplex virus (HSV) membrane was partially damaged. Therefore, it is suggested that rhubarb anthraquinones have a direct killing effect on membrane viruses. Under the influence of light, emodin showed a strong inactivation effect on HSV-1, and its derivatives also inhibited human macrophage virus. Studies have found that rhubarb anthraquinones have a strong anti-influenza virus effect in vitro. As the rhubarb anthraquinones concentration increases, the virus inhibition rate increases.

6. Anti-cancer effect. Experiments have shown that [6] emodin is an ideal anti-cancer biochemical regulator. When combined with 5-Fu, cisplatin, mitoxin C, methotrexate, and adriamycin, it can produce synergistic effects. It can effectively inhibit the cell division and transplantation of melanoma and human lung cancer A549, enhance the cytotoxicity of human liver cancer BEL7402, and synergistically kill lung cancer cells with overexpression of oncogene HER-2 / N CU effect. It was found through experiments that the anthraquinone compounds in aloe had antitumor effects. Galasinski [8] and other studies reported that aloin and aloe-emodin inhibit tumor cell proliferation by inhibiting the activity of peptide chain elongation factor eEF-2 and peptide transferase required for tumor cell protein synthesis.

7. Hepatoprotective and choleretic effects experiments showed that after 7 days of continuous use of rhein in mice, the alanine aminotransferase (A LT) in the model of acute liver injury induced by CC l4 was reduced from 191.32 g to 178.1 g, which resulted in malondiamine. Aldehyde (M DA) decreased from 2.209 nmol / L to 1.194 nmol·L -1 (P <0.01), and SOD increased from 44.8 ng ). Through research on rhubarb, it was found that anthraquinone had a strong inhibitory effect on liver cell color P450 (C YP450) (42.4 mg per kilogram of body weight, reducing CYP450 by 41.7%; 47 mg per kilogram of body weight, making CYP450 A decrease of 51.9%; 40 mg of aloe-emodin per kg of body weight reduced CYP450 by 66.3%), and could delay the reduction of reduced coenzyme CYP450, eliminate circulation disorders, increase liver blood flow, Arosio et al. Found that aloe-emodin had Acute liver damage induced by CC l 4 in mice has a protective effect, not only can prevent the death of liver cells, but also has a protective effect on the inflammatory response caused by lipid peroxidation.

8.Bright eye effectAnimal experiments show that anthraquinone has a clear eye effect, can activate LD H activity in the eye, promote anaerobic glycolysis, reduce the amount of glucose in the crystals, produce more ATP, expand peripheral blood vessels, and improve the retina and nerve blood circulation Promote edema absorption.
9.Effects of chronic renal failure studies show that emodin can inhibit the proliferation of human embryonic kidney fibroblasts (KFB) and induce apoptosis by promoting high-level expression of c-myc protein, and inhibit human mesangial cells Secretes fibronectin (FN); can inhibit the expression of c-myc gene and block cell proliferation; and emodin can significantly reduce the deposition of fibronectin on mesangial cells and reduce the production of cell matrix; can inhibit renal hypertrophy , Reduce glomerular hyperfiltration, reduce proteinuria, mediate lipid metabolism disorders, and inhibit the increase of extracellular matrix. Studies have shown that rhubarb anthraquinones can inhibit the metabolism of hyperactive cells, while reducing the oxygen consumption of the cells, it also affects the synthesis of DNA and RNA in renal mesangial cells, thereby reducing renal sclerosis and delaying renal failure. Studies have suggested that rhein can reverse GF-1 induced proximal renal tubular epithelial cell hypertrophy and inhibit TGF-1 stimulated ECM synthesis. This may be one of the effects of rhein in preventing or improving diabetic nephropathy and delaying the progression of diabetic nephropathy.

10. Nootropic and anti-aging effects Chen Shi et al. Studied the sonotropic activity and action mechanism of emodin-8-O--D-glucopyranoside (PM EG), and found that PM EG can improve normal mice The learning and memory function has protective effect on learning and memory impairment caused by scopolamine. The mechanism may be the reversible inhibition of cholinesterase. Anthraquinone nuclear ortho- and meta-hydroxy groups have obvious anti-peroxidative lipid (LPO) effect, which is better than the same dose of vitamin E, has a strong free radical scavenging effect, and relieves free radicals on brain mitochondria, synaptosome membranes and liver During the oxidation process of microsomes, MDA and other harmful substances are produced, which obviously inhibits the reduction of H2O2 induced brain mitochondria and synaptosomes (GSH), thereby protecting the brain and important organs, and achieving the purpose of delaying aging and prolonging life.
11. Effect on muscle mitochondria LewisDC et al reported that emodin can inhibit the redox activities of NADH, cytochrome C and coenzyme Q in mitochondria of bovine and pig hearts.
12. Anti-mutagenicity: Jae Sue Choi and other experiments showed that chrysophanol in Cassia seed has a significant anti-mutagenic effect in the reaction of aflatoxin B1 (AFB1) to Salmonella typhimurium AT100 or TA98. The mechanism may be It is anthraquinone that inactivates toxin key enzymes in strain mitochondria.
13. Anti-ultraviolet effect Anthraquinones are added to skin care cosmetics. By detecting and analyzing the content and properties of anthraquinone compounds in cosmetics, it can be used to evaluate the content of effective components in cosmetics and the beauty and health care effects of cosmetics.

In addition, anthraquinone also has effects of promoting blood circulation, promoting sleep, lowering blood lipids and increasing immune function. ^[1]

Anthraquinones precautions

The products extracted from natural products containing anthraquinones are mainly crude extracts of Chinese herbal medicine, and the total anthraquinone content of the crude extract is not more than 20%. Organic solvents such as diethyl ether, benzene, and chloroform are often used for the refining of anthraquinones in Chinese herbal medicines, although the total anthraquinone content of the obtained Chinese medicine extract can reach more than 50%. However, these organic solvents are flammable and explosive poisonous and harmful reagents. For example, if the residual amount of solvent in the extract is not controlled well, it will cause great harm to the human body. Moreover, this method is dangerous and pollutes the environment. It is not suitable for large-scale production.