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Luteolin-4'-o-(6"-o-acetyl)-β-d-glucoside and its preparation method and application

A technology of luteolin and glucoside, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problem of few box fruit vines, and the effective chemical composition and action mechanism of box fruit vines are not clear and cannot be realized. Large-scale extraction and application, etc., to achieve the effect of high extraction rate, strong anti-inflammatory activity, and inhibition of NO release

Active Publication Date: 2021-12-07
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few researches on the vine, and the effective chemical components and mechanism of action of the vine are not yet clear, so it is impossible to achieve large-scale extraction and application

Method used

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  • Luteolin-4'-o-(6"-o-acetyl)-β-d-glucoside and its preparation method and application
  • Luteolin-4'-o-(6"-o-acetyl)-β-d-glucoside and its preparation method and application
  • Luteolin-4'-o-(6"-o-acetyl)-β-d-glucoside and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of luteolin-4'-O-(6"-O-acetyl)-β-D glucoside:

[0037] Get 2.5kg of box fruit vine coarse powder, reflux extraction with 10 times of 95% and 70% ethanol successively for three times, concentrate under reduced pressure to obtain 500g of total extract, suspend with water, and use petroleum ether, ethyl acetate, n-butanol successively The extraction was repeated, and the solvent was recovered to obtain 40 g of petroleum ether, 48 g of ethyl acetate, and 200 g of n-butanol.

[0038] Take 200g of n-butanol part extract, separate with macroporous resin column chromatography, water-ethanol (100:0→70:30→50:50→30:70→10:90→0:100) gradient elution, get Fractions D1-D5 and D2 were separated by MCI reverse-phase column chromatography, using water-methanol (100:0→80:20→70:30→60:40→50:50→30:70→0:100 ) for gradient elution to obtain fractions E1-E7, and E3 was subjected to semi-preparative high performance liquid chromatography (water-methanol=44:56) to obtain 3.2 mg of th...

Embodiment 2

[0040] Structural identification of luteolin-4′-O-(6”-O-acetyl)-β-D glucoside:

[0041] The compound product of Example 1 is a yellow powder, insoluble in petroleum ether and chloroform, and easily soluble in methanol. Hydrochloric acid-magnesium powder reaction and Molish reaction were all positive, presumably flavonoid glycosides.

[0042] HR-ESI-MS (m / z): 513.1005[M+Na]+(clacd for C 23 h 22 o 12 Na,513.1009), comprehensive 1 H-NMR and 13 C-NMR can speculate that the molecular formula of the compound is C 23 h 22 o 12 , with a molecular weight of 490 and a degree of unsaturation of 13.

[0043] 1 H-NMR (500MHz, CD 3 OD) δ: 7.40 (1H, d, J = 2.1 Hz), 7.39 (1H, dd, J = 8.4, 2.1 Hz), 7.22 (1H, d, J = 8.5 Hz) indicates the existence of an ABX system. 6.56 (1H, s) is H-3, 6.41 (1H, brs, H-8), 6.19 (1H, d, J=1.8Hz) shows that ring A is 5,7-disubstituted. δ4.93(1H,brs,H-1”) is the signal of sugar anogroup; 2.09(3H,s) is -COCH 3 Signal.

[0044] 13 C-NMR and DEPT spect...

Embodiment 3

[0053] Anti-inflammatory activity of luteolin-4′-O-(6”-O-acetyl)-β-D glucoside as a drug

[0054] 1. Using the CCK8 method to determine the effect of the luteolin-4'-O-(6"-O-acetyl)-β-D glucoside sample of Example 1 on cell activity

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Abstract

The invention discloses a luteolin-4'-O-(6"-O-acetyl)-β-D glucoside and its preparation method and application; Concentrate after extraction to obtain the total extract; the resulting total extract is repeatedly extracted with petroleum ether, ethyl acetate, and n-butanol to obtain the n-butanol fraction; the resulting n-butanol fraction is separated and washed by macroporous resin column chromatography The yellow powder obtained by stripping, MCI reverse-phase column chromatographic separation and elution, and semi-preparative high-performance liquid chromatography separation is the luteolin-4'-O-(6"-O-acetyl)-β-D glucoside . The present invention extracts the active ingredient luteolin-4'-O-(6"-O-acetyl)-β-D glucoside by extracting the vine as a raw material, the steps are simple and efficient, and the development and application of the vine are promoted. When the present invention is used as a medicine, it can significantly inhibit the release of NO, and exhibits dose dependence, and shows strong anti-inflammatory activity.

Description

technical field [0001] The invention relates to the technical field of medicine extraction, more specifically, the invention relates to a luteolin-4'-O-(6"-O-acetyl)-β-D glucoside. Background technique [0002] Zhuang medicine box fruit vine is the dry aboveground part of Convolvulaceae plant box fruit vine Operculinaturpethum (Linn.) S.Manso, which is distributed in China's Taiwan, Yunnan, Guangxi and other places. Traditional Chinese medicine believes that it has diuresis, swelling, relaxing tendons and activating collaterals. The effect of purging and guiding stagnation is used for edema, difficulty in urination, difficulty in flexion and extension of muscles and bones, spasm of hands and feet and other diseases. [0003] At present, there are few researches on the vine, and the effective chemical components and mechanism of action of the vine have not yet been clarified, so large-scale extraction and application cannot be realized. Contents of the invention [0004] I...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26C07H1/08A61P29/00
CPCA61P29/00C07H1/08C07H15/26
Inventor 李兵李俊卢汝梅廖广凤陈文雅温海成潘月梅徐念智
Owner GUANGXI UNIV OF CHINESE MEDICINE
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