Application of naringenin(4-O-methyl) glucoside compound in preparation of anti-inflammatory or lipid-lowering drugs

A technology of glucoside and anti-inflammatory drugs, which is applied in the field of application of naringenin glucoside compounds in anti-inflammatory or lipid-lowering drugs, and can solve the rare reports of anti-inflammatory activity of naringenin derivatives, methyl glycosidation There are few reports on the lipid-lowering activity of derivatives, etc.

Active Publication Date: 2021-02-12
INST OF CROP SCI CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the anti-inflammatory activity of naringenin derivatives is rarely reported
[0004] In addition, naringenin glucoside also shows certain lipid-lowering and hypoglycemic activities, for example, naringenin-7-O-glucoside has anti-diabetic and/or anti-obesity effects, can prevent cardiomyocyte apoptosis and induce

Method used

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  • Application of naringenin(4-O-methyl) glucoside compound in preparation of anti-inflammatory or lipid-lowering drugs
  • Application of naringenin(4-O-methyl) glucoside compound in preparation of anti-inflammatory or lipid-lowering drugs
  • Application of naringenin(4-O-methyl) glucoside compound in preparation of anti-inflammatory or lipid-lowering drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Methyl glycosylation modification of naringenin by Isaria fumosorosea ACCC 37814

[0019] 1.1 Instruments and materials

[0020] The strain used in the experiment: Isaria fumosorosea ACCC 37814 was obtained from the China Agricultural Microorganism Culture Collection Center (ACCC). Compounds: purchased from Shanghai Yuanye Biotechnology Co., Ltd. (Shanghai, China). The reagents used in the experiment were domestic analytically pure products. Culture medium: the fungal medium is potato dextrose agar (PDA, Difco, Sparks, MD, USA) medium and potato dextrose broth (PDB, Difco, Sparks, MD, USA) medium, if making solid medium, add 2 % agar powder.

[0021] High performance liquid chromatography (Agilent, Agilent 1260Infinity II HPLC and Agilent1290Infinity II HPLC), C 18Chromatographic columns (Agilent, Poroshell 120SB-C18, 2.7 μm, 4.6 mm×150 mm and Zorbax SB-C18, 1.8 μm, 2.1×50 mm). Mass spectrometry (Agilent, Agilent QTOF 6530). Rotary evaporator (BUCHI comp...

Embodiment 2

[0030] Example 2 Extraction, separation and structural identification of compounds 1a-1d

[0031] 2.1 Instruments and materials

[0032] Chromatographic pure water, chromatographic acetonitrile, analytical pure ethyl acetate, chromatographic or ordinary pure methanol, dichloromethane, etc. used in the laboratory were purchased from Fisher (USA); column chromatography silica gel (100-200 mesh) was purchased from Qingdao Ocean Chemical Plant Company. BUCHIDL-400 rotary evaporator, produced by Swiss BUCHI company. The circulating cooler is produced by Zhengzhou Great Wall Science, Industry and Trade Co., Ltd. The semi-automatic preparative liquid chromatograph is Agilent 1260Infinity II, and the C18 chromatographic column is Eclipse XDB-C18, 5μm, 9.4×250mm. The Agilent 1260 Infinity II analytical HPLC instrument equipped with a Poroshell 120SB-C18 reversed-phase column (2.7 μm, 4.6 mm×150 mm) was used for sample purity detection, no impurity peaks were required, and pure sampl...

Embodiment 3

[0050] Embodiment 3 Solubility test of naringenin and glycosides thereof

[0051] 3.1 Purpose of the experiment

[0052] Determination of the effect of sugar methylation on the solubility of naringenin in different solvents.

[0053] 3.2 Experimental method

[0054] Weigh 0.5mg each of naringenin and compounds 1b and 1c, place them in 500uL of different solvents at 25°C±2°C, shake vigorously for 30s every 5min; observe the dissolution within 30min, if no solute particles or liquid When dripping, it is considered to be completely dissolved. The selected solvents are distilled water, methanol, ethanol, etc.

[0055] 3.3 Experimental results and analysis

[0056] Table 3 shows the solubility of naringenin and its glycosylated derivatives (compound 1c) and sugar methylated derivatives (compound 1b) in different solvents.

[0057] Table 3 Solubility of naringenin, compound 1b and 1c in different solvents

[0058]

[0059]

[0060] Note: insoluble-; slightly soluble-+; p...

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Abstract

The invention discloses an application of naringenin(4-O-methyl) glucoside compounds in preparation of anti-inflammatory or lipid-lowering drugs; in a biological activity test, the compounds show down-regulation or inhibition of generation of certain inflammatory factors generated by mouse RAW264.7 macrophages, such as nitric oxide (NO); the compound also shows down-regulation or inhibition of mouse 3T3-L1 precursor adipocyte proliferation and significant reduction of the number of lipid droplets generated in the cell differentiation process. The effect of the compound is superior to that of aglycone, and compared with aglycone, the water solubility of the compound is remarkably enhanced; compared with glucoside, the compound is higher in conversion efficiency and higher in yield; comparedwith glucoside, the compound has the toxicity weakened, and has a wider application value.

Description

technical field [0001] The invention belongs to the field of medicines, in particular to the application of naringenin (4-O-methyl) glucoside compounds in anti-inflammatory or lipid-lowering medicines. Background technique [0002] Naringenin, a common natural flavonoid secondary metabolite, mainly exists in the form of glycosides in pomelo peel, has a more restricted distribution than other flavonoids, and is specific to citrus fruits . Naringenin is considered to have a variety of biological and pharmacological activities on human health, such as anti-oxidation, anti-inflammation, lowering blood fat, antibacterial, inhibiting tumor growth, protecting liver cells, and inhibiting platelet aggregation, etc., so it has attracted widespread attention , can be used in medicine, food and other fields. However, naringenin is only slightly soluble in water, and has poor metabolic stability in mammals. It is easily affected by various factors from organisms and the outside world, ...

Claims

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Application Information

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IPC IPC(8): C07H15/26C07H17/07A61K31/7048A61P29/00A61P3/04
CPCC07H15/26C07H17/07A61P29/00A61P3/04
Inventor 顿宝庆窦方敏王智幺杨李桂英
Owner INST OF CROP SCI CHINESE ACAD OF AGRI SCI
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