CN-116589514-B - Guaiane type sesquiterpene glycoside in rhizoma atractylodis, and preparation method and application thereof

Abstract

The invention belongs to the technical field of medicines, and relates to a guaiane type sesquiterpene glycoside compound Guanzan atractylode glycoside II extracted and separated from rhizome of rhizoma atractylodis by utilizing technologies such as macroporous resin, normal phase silica gel, reverse phase silica gel, sephadex column chromatography, recrystallization and the like, wherein the molecular formula of the compound is C 21 H 36 O 8 , and in-vitro anti-tumor activity research shows that the compound has good anti-tumor activity, and has obvious inhibition effects on human gastric cancer cells BGC-823, human liver cancer cells HepG-2 and human lung cancer cells A549. The invention can provide a basic source of drug effect substances for the development of anti-tumor drugs and has development and application prospects.

Inventors

• ZHOU YUANYUAN
• PAN JUAN
• SUN YANPING
• LIU YUAN
• WU JIATONG
• ZHANG XIAOJUAN

Assignees

• 黑龙江中医药大学

Dates

Publication Date

20260512

Application Date

20230523

Claims (3)

1. 1. A guaiane compound separated from rhizome of rhizoma atractylodis has a molecular formula of C 21 H 36 O 8 , and is named guaiane glycoside II of rhizoma atractylodis, and has a structural formula as follows: 。
2. 2. The preparation method of the compound of claim 1, wherein the Guanzhong guaiang glycoside II is prepared from rhizoma atractylodis rhizome by macroporous resin, normal phase silica gel, reverse phase silica gel and sephadex column chromatography and recrystallization treatment, and comprises the following specific preparation steps: (1) Ethanol extraction, namely, taking dry rhizome of rhizoma atractylodis as a raw material, appropriately crushing, adopting 70% ethanol for reflux extraction for 3 times, filtering, combining 3 times of filtrate, recovering solvent under reduced pressure, and drying to obtain extractum extract; (2) Enriching and purifying, namely dispersing the extractum extract obtained in the step (1) with water to a solution with the relative density of 1.25+/-0.05 g/mL, enriching and purifying by using AB-8 macroporous resin column chromatography, eluting with water, 30% ethanol, 50% ethanol and 95% ethanol in sequence respectively, collecting 50% ethanol eluent, and recovering the solvent under reduced pressure to obtain a 50% ethanol eluting part; (3) Carrying out normal phase silica gel column chromatography, namely carrying out system gradient elution on a 50% ethanol elution part obtained in the step (2) by adopting a normal phase silica gel column, sequentially adopting a mixed solution of dichloromethane and methanol with the volume ratio of 8:1, a mixed solution of dichloromethane and methanol with the volume ratio of 5:1 and a mixed solution of dichloromethane and methanol with the volume ratio of 3:1, collecting fraction liquid with the volume ratio of 3:1, and recovering a solvent under reduced pressure; (4) Performing reverse phase silica gel column chromatography, namely eluting the fraction prepared in the step (3) by reverse phase silica gel ODS column chromatography sequentially by using a mixed solution of methanol and water with a volume ratio of 1:2, a mixed solution of methanol and water with a volume ratio of 1:1 and a mixed solution of methanol and water with a volume ratio of 2:1, collecting elution parts of the mixed solution of methanol and water with the volume ratio of 1:1, combining the elution parts after the elution parts are detected by reverse phase silica gel thin layer chromatography, and sequentially obtaining three parts Fr.1, F.2 and Fr.3; (5) Performing Sephadex column chromatography, namely taking the Fr.2 part obtained in the step (4), performing isocratic elution by using methanol-water with the volume ratio of 1:1.5 as a mobile phase through the Sephadex column, collecting eluent, and recovering a solvent to obtain a crude product; (6) And (3) recrystallizing the crude product obtained in the step (5) by using a two-phase solvent system of methanol-dichloromethane=5:1 for two times to obtain the pure product of the compound.
3. 3. The use of the compound atractylis lancea-guaiacin II in the manufacture of a medicament for the treatment of a tumor, wherein the tumor is gastric cancer, liver cancer and lung cancer.

Description

Guaiane type sesquiterpene glycoside in rhizoma atractylodis, and preparation method and application thereof Technical Field The invention particularly relates to a guaiane type sesquiterpene glycoside compound with a tumor cell inhibition effect. Background Rhizoma atractylodis (Atractylodes japonica Koidz. Ex Kitam.) is a herb of Compositae, and is used as a medicine with dried rhizome, and in northeast China, wild resources are abundant, and the rhizoma atractylodis is grown on wild forest edges with the altitude of 200-800 m and sandy loam containing more humus, such as under forests, hillsides, terraces and the like. The rhizoma atractylodis has the effects of strengthening spleen, eliminating dampness, drying soil, promoting diuresis, improving eyesight, dispelling wind and avoiding dirty qi, and is mainly used for treating various clinical symptoms such as inappetence, gastric dyspepsia, rheumatic arthritis, common cold and the like. Modern pharmacological research shows that the traditional Chinese medicine composition has great development potential in the aspects of resisting tumor, resisting inflammation, resisting bacteria, protecting and repairing gastric mucosa tissues and the like. In both countries of Japanese and Korean, the rhizome of Atractylodes lancea is not only used as a medicine for the Atractylodes macrocephala, but also used as a health food for eating. The volatile oil component in rhizoma atractylodis is mainly sesquiterpene hydrocarbons, the main types of the volatile oil component are eucalyptus type, guaiane type and the like from the structural classification, some representative compounds are subjected to related pharmacological activity researches, for example, atractylone has the effects of protecting liver, resisting viruses and eliminating inflammation, apiadione can inhibit capillary permeability from being hyperfunctional and eliminate inflammation, atractylone I has the effects of improving amylase activity, enhancing intestinal digestion and absorption functions and regulating spleen and stomach, atractylone II has an inhibitory effect on human colorectal cancer cells Lovo, atractylone III also has an antiviral effect, and the number of reported compounds of the components in rhizoma atractylodis is small. Disclosure of Invention The invention aims to provide a novel guaiane type sesquiterpene glycoside compound and a preparation method and application thereof. In order to achieve the above purpose, the invention is realized by adopting the following technical scheme: the invention discloses a guaiane type sesquiterpene glycoside, which has a molecular formula of C 21H36O8, is commonly known as guarana guaiana glycoside II, and has the following structural formula: The invention also provides a preparation method of the atractylis ovata guaiac glucoside II, which is obtained through macroporous resin, normal phase silica gel, reverse phase silica gel and sephadex column chromatography and recrystallization treatment, and comprises the following specific preparation steps: (1) Ethanol extraction, namely, taking dry rhizome of rhizoma atractylodis as a raw material, appropriately crushing, adopting 70% ethanol for reflux extraction for 3 times, filtering, combining 3 times of filtrate, recovering solvent under reduced pressure, and drying to obtain extractum extract; (2) Enriching and purifying, namely dispersing the extractum extract obtained in the step (1) with water to a solution with the relative density of 1.25+/-0.05 g/mL, enriching and purifying by using AB-8 macroporous resin column chromatography, eluting with water, 30% ethanol, 50% ethanol and 95% ethanol in sequence respectively, collecting 50% ethanol eluent, and recovering the solvent under reduced pressure to obtain a 50% ethanol eluting part; (3) Carrying out normal phase silica gel column chromatography, namely carrying out system gradient elution on a 50% ethanol elution part obtained in the step (2) by adopting a normal phase silica gel column, sequentially adopting a mixed solution of dichloromethane and methanol with the volume ratio of 8:1, a mixed solution of dichloromethane and methanol with the volume ratio of 5:1 and a mixed solution of dichloromethane and methanol with the volume ratio of 3:1, collecting fraction liquid with the volume ratio of 3:1, and recovering a solvent under reduced pressure; (4) Performing reverse phase silica gel column chromatography, namely eluting the fraction prepared in the step (3) by reverse phase silica gel ODS column chromatography sequentially by using a mixed solution of methanol and water with a volume ratio of 1:2, a mixed solution of methanol and water with a volume ratio of 1:1 and a mixed solution of methanol and water with a volume ratio of 2:1, collecting elution parts of the mixed solution of methanol and water with the volume ratio of 1:1, combining the elution parts after the elution parts are detected by reverse phase silica gel thin layer chroma