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CN-121974968-A - Chalcone-lignan glycoside compound separated from semen Hoveniae and application thereof in relieving alcoholic intoxication and protecting liver

CN121974968ACN 121974968 ACN121974968 ACN 121974968ACN-121974968-A

Abstract

The invention discloses a chalcone-lignan glycoside compound separated from semen hoveniae and application thereof in dispelling the effects of alcohol and protecting liver. The aureonolignan glycoside compound shown in the structural formula I or pharmaceutically acceptable salt thereof: I. The chalcone-lignan glycoside compound can obviously shorten the sobering time of mice with acute alcoholism, reduce the number of autonomous activities of the mice, reduce the MDA content in the livers of the mice, raise the activities of ADH, SOD and GSH-Px in the livers of the mice, and has obvious functions of dispelling the effects of alcohol and protecting the livers. The invention discloses application of chalcone-lignan glycoside compounds in preparation of anti-hangover and liver-protecting medicines. The invention discloses application of chalcone-lignan glycoside compounds in preparing medicines for treating acute and chronic alcoholic liver injury.

Inventors

  • MA QINGE
  • WEI RONGRUI
  • Adomo Zili

Assignees

  • 武汉轻工大学

Dates

Publication Date
20260505
Application Date
20260126

Claims (10)

  1. 1. The aureonolignan glycoside compound shown in the structural formula I or pharmaceutically acceptable salt thereof: ; I。
  2. 2. a method for preparing a chalcone-lignan glycoside compound according to claim 1, which is characterized by comprising the following steps: Crushing dried semen hoveniae, soaking in 90-100% ethanol for 22-26 hours, and carrying out heating reflux extraction for 3-5 times, wherein each time lasts for 3-5 hours to obtain a semen hoveniae total extract; Concentrating and drying the total extract of the hovenia dulcis thunb under reduced pressure until no ethanol smell exists, so as to obtain dried total thick hovenia dulcis thunb paste; Uniformly suspending the hovenia dulcis thunb total thick paste in water, and sequentially extracting with petroleum ether, ethyl acetate and n-butanol to obtain petroleum ether extract, ethyl acetate extract and n-butanol extract respectively; step (4), subjecting the n-butanol extract to macroporous adsorption resin column, and sequentially performing gradient elution with 15% ethanol, 30% ethanol, 60% ethanol and 100% ethanol to obtain 4 fractions including fraction A, fraction B, fraction C and fraction D; Step (5), loading the fraction B on a medium-pressure liquid phase column to obtain 3 secondary fractions, namely a secondary fraction B-1, a secondary fraction B-2 and a secondary fraction B-3; step (6), performing normal phase silica gel column chromatography on the fraction B-2, and performing gradient elution by taking the volume ratio of dichloromethane to methanol (10:1-1:1) as an eluent to obtain 3 subfractions, namely subfractions B-2-1, subfractions B-2-2 and subfractions B-2-3; Step (7), loading the subfraction B-2-2 on a Sephadex LH-20 gel column, eluting with 80% methanol to 100% methanol to obtain 3 secondary fractions, namely secondary fraction B-2-2-1, secondary fraction B-2-2-2 and secondary fraction B-2-2-3; And (8) carrying out preparative liquid chromatography separation on the secondary fraction B-2-2-2 to obtain the chalcone-lignan glycoside compound.
  3. 3. The method for preparing the chalcone and lignan glycoside compound according to claim 2, wherein in the step (1), dried semen Hoveniae is crushed to 60-80 meshes.
  4. 4. The method for preparing chalcone-lignan glycoside compound according to claim 2, wherein in the step (4), the macroporous adsorption resin is AB-8 type macroporous adsorption resin.
  5. 5. The method for preparing A chalcone-lignan glycoside compound according to claim 2, wherein in the step (5), the medium-pressure liquid phase column is A YMC-Pack ODS-A column (250×50mm, 5 μm), the mobile phase is 20% methanol-40% methanol, the absorption wavelength is 200-400 nm, and the flow rate is 15-20 m/min.
  6. 6. The method for producing A chalcone-lignan glycoside compound according to claim 2, wherein in the step (8), the column for liquid chromatography is A YMC-Pack ODS-A column (250X 20 mm, 5 μm), the mobile phase is 20% methanol-40% methanol, the absorption wavelength is 200-280 nm, and the flow rate is 2-4 m/min.
  7. 7. The use of the chalcone-lignan glycoside compound of claim 1 in the preparation of anti-hangover and liver-protecting drugs.
  8. 8. The use of a chalcone-lignan glycoside compound according to claim 1 in the preparation of a medicament for treating acute and chronic alcoholic liver injury.
  9. 9. The method according to claim 7 or 8, wherein the drug is in the form of tablet, capsule, granule, pill, oral liquid, or suspension.
  10. 10. A pharmaceutical composition is characterized in that the pharmaceutical composition takes the chalcone-lignan glycoside compound as an active ingredient and is prepared into a pharmaceutically acceptable dosage form with pharmaceutically acceptable auxiliary materials.

Description

Chalcone-lignan glycoside compound separated from semen Hoveniae and application thereof in relieving alcoholic intoxication and protecting liver Technical Field The invention belongs to the field of medicines, relates to a novel chalcone-lignan glycoside compound separated from semen hoveniae and application thereof in anti-alcohol, rescuing and protecting liver, and in particular relates to a novel chalcone-lignan glycoside compound separated from a medicinal and edible traditional Chinese medicine, namely semen hoveniae, and a preparation method and application thereof in anti-alcohol and protecting liver. Technical Field In recent years, with the continuous improvement of living standard, the consumption of wine is increasing, and excessive drinking can damage the liver of human body, and liver fibrosis, liver cirrhosis and liver cancer are serious. The hovenia dulcis thunb as a common anti-alcoholic drug has long application history and is originally carried in Xin Xiu Ben Cao (newly revised materia Medica). The semen Hoveniae is fruit with flower axis of Hovenia dulcis Thunb (Hovenia dulcis th.) belonging to genus Hovenia of Rhamnaceae, and is called fructus Hoveniae, fructus Pyri, and papaw. It has mild nature and sweet taste, and has effects of relieving alcoholic intoxication, protecting liver, clearing heat, promoting urination, quenching thirst, relieving restlessness, etc. Early researches show that hovenia dulcis thunb contains rich chemical components, mainly including flavonoids, terpenes, lignans, alkaloids, phenolic acids and the like. Modern pharmacological researches show that semen hoveniae has the effects of dispelling effects of alcohol and protecting liver, resisting oxidation, resisting tumor, resisting bacteria, reducing uric acid, reducing blood pressure, reducing blood sugar and the like, and in particular, semen hoveniae is favored by researchers in dispelling effects of alcohol and protecting liver. Disclosure of Invention In order to further excavate potential anti-alcoholic liver-protecting active ingredients in the hovenia dulcis thunb, the inventor separates and purifies chemical ingredients of the hovenia dulcis thunb, and obtains a novel chalcone lignan glycoside compound from the hovenia dulcis thunb by utilizing a modern spectrum technology. Meanwhile, the inventor researches and evaluates the anti-hangover and liver-protecting activity of the chalcone lignan glycoside compound through an acute alcoholism experiment mouse experiment, the compound can obviously shorten the anti-hangover time of an acute alcoholism mouse, reduce the number of autonomous activities of the mouse, reduce the MDA content (P <0.05 or P < 0.01) in the liver of the mouse, raise the activities (P <0.05 or P < 0.01) of ADH, SOD and GSH-Px in the liver of the mouse, and has obvious anti-hangover and liver-protecting effects. The invention aims to provide a novel chalcone-lignan glycoside compound separated from a medicinal and edible traditional Chinese medicine-semen hoveniae, and a preparation method and application thereof in dispelling alcohol and protecting liver. In order to achieve the above purpose, the present invention adopts the following technical scheme: New chalcone lignan glycoside compound (compound I) with a structure shown in formula I or pharmaceutically acceptable salt thereof is separated from medicinal and edible traditional Chinese medicine-semen Hoveniae: I The molecular formula of the compound I is C 44H46O16. The chemical name of the compound I is 1-isopentenyl-2, 3- (4 '' '-hydroxy-9' '' -carbonyl-styryl) -5-hydroxy-6-rutinoside-7, 8- (13, 14-dimethyl-hexa-membered iridoid) -chalcone. The invention also aims to provide a preparation method of the novel chalcone-lignan glycoside compound, which comprises the following steps: Crushing dried semen hoveniae, soaking in 90-100% ethanol for 22-26 hours, and carrying out heating reflux extraction for 3-5 times, wherein each time lasts for 3-5 hours to obtain a semen hoveniae total extract; step (2), concentrating and drying the total extract of the hovenia dulcis thunb obtained in the step (1) under reduced pressure until no ethanol smell exists, so as to obtain dried total thick paste of the hovenia dulcis thunb; step (3), uniformly suspending the hovenia dulcis thunb total thick paste obtained in the step (2) in water, and sequentially extracting with petroleum ether, ethyl acetate and n-butanol to obtain petroleum ether extract, ethyl acetate extract and n-butanol extract respectively; Step (4), subjecting the n-butanol extract obtained in the step (3) to macroporous adsorption resin column, and sequentially performing gradient elution with 15% ethanol, 30% ethanol, 60% ethanol and 100% ethanol to obtain 4 fractions including fraction A, fraction B, fraction C and fraction D; Step (5), the fraction B obtained in the step (4) is put on a medium-pressure liquid phase column to obtain 3 secondary fractions B-1, B-2 and B-3; perfo