Two new flavone C-glycoside compounds as well as preparation method and application thereof

A flavonoid carbon glycoside compound and its application technology, applied in the field of medicine, can solve the problems of high incidence of adverse reactions, and achieve the effects of good anti-inflammatory activity, good medicinal prospects, and low toxic and side effects

Inactive Publication Date: 2012-08-15
GUANGXI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the high incidence of adverse reactions caused by NSAIDs cannot be ignored.

Method used

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  • Two new flavone C-glycoside compounds as well as preparation method and application thereof
  • Two new flavone C-glycoside compounds as well as preparation method and application thereof
  • Two new flavone C-glycoside compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Take 5 kg of dry whole herb of Nervilia fordii (Hance) Schltr., add 10 times the amount of 60% ethanol to reflux and extract 3 times, each time for 2 hours, combine the extracts, and use a rotary evaporator at a temperature lower than 45 ° C. After recovering ethanol under reduced pressure, 600 g of extract was obtained; the extract was suspended in water to obtain an aqueous suspension of extract, and the aqueous suspension of extract was extracted three times with cyclohexane, and the cyclohexane layers were combined; Ethyl extracts the aqueous extract suspension after extracting the extract aqueous suspension with cyclohexane three times, and combines the ethyl acetate layer; then uses n-butanol to extract the extract aqueous suspension with ethyl acetate The extract water suspension was extracted three times, and the n-butanol layers were combined; the cyclohexane layer solvent cyclohexane, the ethyl acetate layer solvent ethyl acetate, and the After the butanol lay...

Embodiment 2

[0060] Take 10kg of dried Nervilia fordii (Hance) Schltr. whole herb, add 7 times the amount of 80% ethanol to reflux and extract twice, each time for 3 hours, combine the extracts, and use a rotary evaporator at a temperature lower than 45°C After recovering ethanol under reduced pressure, 1200 g of extract was obtained. Suspend the extract in water to obtain an aqueous suspension of extract, extract the aqueous suspension of extract three times with cyclohexane, combine the cyclohexane layers; then extract the aqueous extract with cyclohexane with ethyl acetate The aqueous extract suspension after the suspension was extracted three times, and the ethyl acetate layer was combined; then, the aqueous extract suspension was extracted three times with n-butanol after the aqueous extract suspension was extracted with ethyl acetate, and the normal ethyl acetate layer was combined. butanol layer; use a rotary evaporator to recover the cyclohexane layer solvent cyclohexane, the ethyl...

experiment example 1

[0065] Nervilifordin J, yellow powder, odorless, crystallized in methanol Melting point: 207°C-208°C. Solubility: easily soluble in dimethyl sulfoxide, soluble in methanol, insoluble in petroleum ether and chloroform. High-resolution ESI-MS gives molecular weight: [M+H]+m / z 771.3141; molecular formula: C 37 h 38 o 18 . IR spectrum at 3299cm -1 There is a strong broad peak, suggesting that there is a hydroxyl group in the molecule, 1650cm -1 The strong absorption peak at the point indicates that there is a carbonyl group in the structure. Maximum absorption wavelength λ of UV spectrum (methanol as solvent) max (logε) are 331 (4.25), 278 (4.04), 219 (4.37), respectively, which are the absorption spectra of typical flavonoids.

[0066] In the 1HNMR (600MHz, DMSO-d6) of the compound, δ12.82 (1H, s) is the characteristic signal of the 5-position hydroxyl proton of flavone; δ6.87 (1H, s) is the signal of the 3-position proton of flavone; δ8.38 (2H , d, J=8.9Hz), 6.91 (2H, d,...

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Abstract

The invention discloses two new flavone C-glycoside compounds as well as a preparation method and application thereof. In the two new flavone C-glycosides compounds, the chemical name of the first flavone C-glycoside compound is apigenin-6-C-beta-arabinoseyl-8-C-(2''-O-sinapine)-beta-galactoside, and the first flavone C-glycosides compound is named nervilifordin J, and the chemical name of the second flavone C-glycoside compound is apigenin-6-C-beta-arabinoseyl-8-C-(2''-O-(E)-ferulic acid)-beta-galactoside, and the second flavone C-glycoside compound is named nervilifordin K. The preparation method of the two new flavone C-glycoside compounds is finished by the following steps of: based on dried nervilia fordii herb as a raw material 1) preparing extractum; 2) preparing cyclohexane layer extractum, ethyl acetate layer extractum, n-butyl alcohol layer extractum and water layer extractum; and 3) preparing apigenin-6-C-beta-arabinoseyl-8-C-(2''-O-sinapine)-beta-galactoside and apigenin-6-C-beta-arabinoseyl-8-C-(2''-O-(E)-ferulic acid)-beta-galactoside. The two flavone C-glycosides compounds are used for preparing anti-inflammatory medicaments.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to two new flavonoid carbon glycoside compounds and their preparation method and application. Background technique [0002] Inflammation plays an important role in medicine, and it is the basic pathological process of many diseases. Inflammation's role in diseases is thought to trap the body with an overactive immune system, such as asthma, allergies and rheumatoid arthritis. Anti-inflammatory drugs are divided into steroidal anti-inflammatory drugs and non-steroidal anti-inflammatory drugs, and the use of non-steroidal anti-inflammatory drugs by humans has a history of more than 100 years since the discovery of salicylic acid. NSAIDs have established anti-inflammatory and analgesic effects. In addition, in recent years, people are gradually recognizing that inflammation and chronic infection are one of the important factors in the occurrence of different human tumors....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/04A61K31/352A61P29/00
Inventor 谢集照焦杨邱莉谢云峰邱少玲
Owner GUANGXI MEDICAL UNIVERSITY
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