What are the active groups of oleanolic acid structure?

Oleanolic acid product name Oleanolic acid

English name oleanolic acid

The chemical name is 3β- hydroxy-oleic acid-12- ene -28- acid.

Oleanolic acid, carnation, Astrantigeninc, Giganteumgeninc.

C A SNo。 508-02- 1

The source is pentacyclic triterpenoids, which exist in many plants in the form of free bodies and sugar conjugates. Mainly extract leaves from Olea europaea of Oleaceae; Ligustrum lucidum. Fruit; The whole grass of Gentianaceae; French wormwood. ; Leaves and roots of Umbelliferae plant Astrantia Major L.; Root bark and stem bark of Araliaceae Aralia elata; Tuberous roots of Cucurbitaceae plants, such as Xuedan, Xuedan and Xuedan. Scarab, Luoguodi.

Score C30H48O3

Molecular weight 456.75438+0

Physical properties white needle-like crystals (ethanol); Odorless and tasteless, soluble in methanol, ethanol, benzene, ether, acetone and chloroform, almost insoluble in water, unstable to acid and alkali. Melting point: 308℃ ~ 3 10℃, [α] 20d+68 to +78 (c = 0. 15, chloroform).

Classification of pentacyclic triterpenoids

Instrument 95%, > 98%

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Identification (1) Take about 50mg of this product, add 2ml of chloroform to dissolve it, add 2 drops of sulfuric acid, shake well, and let it stand. The chloroform solution gradually turns from colorless (or light yellow) to light red.

(2) Take a small amount of this product, add acetic anhydride lml, slightly heat it to dissolve, and add 1 drop of sulfuric acid, which is purple-red, and the color gradually darkens after standing.

(3) Take a small amount of this product, add 0.2ml of glacial acetic acid solution of vanillin (0.5g of vanillin, 10ml of glacial acetic acid dissolved), add 0.8ml of perchloric acid, and heat it in boiling water bath for a few minutes, which is purple. Add 2ml of ethyl acetate, and purple will dissolve in ethyl acetate and remain unchanged.

(4) The main absorption peaks shown in the infrared absorption spectrum of this product should be consistent with the reference substance.

Check chloride. Take 50mg of this product, add 25ml of water, shake vigorously for 65438 05min, filter, and check the filtrate according to law (China Pharmacopoeia 1977 Edition, Appendix 4). If turbidity occurs, it should be less concentrated (0. 14%) than the control solution made of 7ml standard sodium chloride solution.

Take this product as the relevant impurity, add the same amount of ethanol and chloroform to make a solution containing lmg per lml, test it according to the thin-layer chromatography (China Pharmacopoeia 1977 Edition Appendix 38), absorb the above solution 10 ml, spot it on the thin-layer plate of silica gel G, and use chloroform: acetone (10: 1). After color development, take out the volatile solvent, spray 5% phosphomolybdic acid ethanol solution for color development, and heat for several minutes at 120℃. You cannot display other points except the main point.

Loss on drying takes about 0.5g of this product and dries it to constant weight at 105℃, and the weight loss shall not exceed 0.5% (Appendix 44 of China Pharmacopoeia 1977).

Residue on ignition shall not exceed 0. 1% (page 45 of appendix I of China Pharmacopoeia 1977).

Determination of content: take about 0. 15g of this product, weigh it accurately, add 20ml anhydrous ethanol and 5ml benzene, dissolve it with slight heat, add 8 drops of phenolphthalein indicator, titrate it with 0.05ml ethanol-made potassium hydroxide solution, and make blank test correction, thus obtaining (0.05ml ethanol-made potassium hydroxide solution is equivalent to containing 22.84mg c 30h 48 o 3 per lml).

Pharmacological efficacy

Oleanolic acid has the effects of protecting liver, reducing enzyme, promoting hepatocyte regeneration, anti-inflammatory, cardiotonic, diuretic and anti-tumor. It also has hypoglycemic, hypolipidemic and sedative effects, and is an effective component for developing drugs for treating liver diseases and reducing blood sugar.

1. Alleviate liver injury: Oleanolic acid is a pentacyclic triterpene compound, which has obvious protective effect on acute and chronic liver injury caused by carbon tetrachloride in rats. After treatment, swollen mitochondria and expanded rough endoplasmic reticulum were restored. It can also significantly reduce balloon degeneration, necrosis and inflammatory reaction of liver cells in acute and chronic liver injury. The accumulation of triglycerides in the liver decreased and the amount of glycogen increased.

2. Reduce the activity of alanine aminotransferase in plasma: Oleanolic acid can obviously reduce the enzyme activity of animals with acute and chronic hepatitis and cirrhosis.

3. Decrease serum r- globulin, which is consistent with the reduction of liver-related inflammatory reaction observed by histology.

4. Promoting hepatocyte regeneration: Oleanolic acid can significantly increase the mitotic phase number of rat remnant liver, and the degree of regeneration is higher than that of the control group, suggesting that it can promote cell regeneration.

5. Reduce the level of kynurenine in brain homogenate of rats with liver cirrhosis: Because the level of kynurenine in brain homogenate is obviously reduced, it can inhibit the production of false neurotransmitters, so it is beneficial to the prevention and treatment of hepatic encephalopathy.

6. Inhibition of hepatic fibrosis: Liver fibrosis in rats treated with oleanolic acid was severe and obviously relieved, and the content of liver collagen decreased, suggesting that it has the effect of preventing and treating liver cirrhosis.

7. Oleanolic acid has obvious inhibitory effect on mononuclear phagocyte system, macrophage phagocytosis and experimental arthritis in mice, but it has influence on humoral immune function and antigen-binding cells. Enhance immunity and inhibit the growth of S 180 tumor strain.

8. It can protect chromosome damage, prevent experimental atherosclerosis and correct protein's metabolic disorder.

The adverse reaction was 1. A few patients have dry mouth, diarrhea and upper abdominal discomfort, which can disappear after symptomatic treatment.

2. A few patients have mild thrombocytopenia, which can be recovered after drug withdrawal.

Clinical application: This product is an auxiliary drug for liver diseases. Clinically, it is used to treat infectious acute icteric hepatitis, and has obvious effects on reducing alanine aminotransferase and yellowing, and improving symptoms, signs and liver function of patients with viral and chronic persistent hepatitis. It can also be used for treating psoriasis, rheumatoid arthritis, nephritis edema, ascites due to liver cirrhosis, acute and chronic hepatitis, stomachache, turbid urine, bloody collapse, traumatic injury, carbuncle, soreness of waist and knees, and fetal restlessness.

280 cases of acute icteric hepatitis were observed and treated by Shanghai Infectious Disease Hospital and other units. The cure rate is 64.8% and the total effective rate is 94.4%. Significantly higher than 44% and 88.1%of the western medicine control group; 2. 298 cases of chronic hepatitis were treated. The results showed that the effective rate was 43.7% and the total effective rate was 69.8%.

Usage and dosage: acute hepatitis 30mg once, 90mg once a day; Chronic hepatitis: 50 mg once, 200 mg a day.

Store in a cool and dry place, away from light.