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Application of a naringenin (4-o-methyl) glucoside compound in the 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 problem of lipid-lowering activity of methyl glycosidation derivatives which are rarely reported, naringenin The anti-inflammatory activity of derivatives is rarely reported and other issues

Active Publication Date: 2022-07-19
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 endogenous Antioxidant enzymes resist doxorubicin (DOX) toxicity, and can also prevent cardiomyocytes from DOX-induced toxicity by stabilizing cell membranes and reducing the production of reactive oxygen species (ROS), but their methyl glycosidation derivatives have little lipid-lowering activity There are reports

Method used

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  • Application of a naringenin (4-o-methyl) glucoside compound in the preparation of anti-inflammatory or lipid-lowering drugs
  • Application of a naringenin (4-o-methyl) glucoside compound in the preparation of anti-inflammatory or lipid-lowering drugs
  • Application of a naringenin (4-o-methyl) glucoside compound in the 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 China Agricultural Microorganism Collection Center (ACCC). Compounds: purchased from Shanghai Yuanye Biotechnology Co., Ltd. (Shanghai, China). The reagents used in the experiments were all domestic analytically pure products. 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 solid medium, add 2 % agar powder.

[0021] High performance liquid chromatography (Agilent, Agilent 1260 Infinity II HPLC and Agilent 1290 Infinity 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 company, DL-400); circu...

Embodiment 2

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

[0031] 2.1 Instruments and materials

[0032] Chromatographic pure water, chromatographic acetonitrile, analytically pure ethyl acetate, chromatographic or ordinary pure methanol, dichloromethane, etc. used in the laboratory were purchased from Fisher (USA) Company; column chromatography silica gel (100-200 mesh) was purchased from Qingdao Ocean chemical plant company. BUCHIDL-400 type rotary evaporator, produced by Swiss BUCHI company. The circulating cooler is produced by Zhengzhou Great Wall Technology Industry and Trade Co., Ltd. The semi-automatic preparative liquid chromatograph was Agilent 1260Infinity II, and the C18 chromatographic column was Eclipse XDB-C18, 5 μm, 9.4×250 mm. Sample purity testing was performed using an Agilent 1260 Infinity II analytical HPLC instrument equipped with a Poroshell 120SB-C18 reversed-phase column (2.7 μm, 4.6 mm×150 mm). The detection conditio...

Embodiment 3

[0050] Embodiment 3 Solubility test of naringenin and its glycoside compounds

[0051] 3.1 Experimental purpose

[0052] To determine the effect of glycomethylation on the solubility of naringenin in different solvents.

[0053] 3.2 Experimental method

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

[0055] 3.3 Experimental results and analysis

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

[0057] Table 3 Solubility of Naringenin, Compounds 1b and 1c in Different Solvents

[0058]

[0059]

[0060]...

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PUM

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Abstract

The invention discloses a kind of naringenin (4- O The application of -methyl) glucoside compound in the preparation of anti-inflammatory or lipid-lowering drugs, in the biological activity test, the compound showed down-regulation or inhibition of the production of certain inflammatory factors produced by mouse RAW264.7 macrophages , for example: nitric oxide (NO); also shown to downregulate or inhibit the proliferation of mouse 3T3‑L1 preadipocytes and significantly reduce the number of lipid droplets produced during cell differentiation. Its effect is better than that of aglycone, and compared with aglycone, the water solubility of the compound is significantly enhanced; compared with glucoside, the compound has higher conversion efficiency and higher yield; compared with glucoside, the compound has less toxicity, It has wider application value.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to the use of naringenin (4-O-methyl) glucoside compounds in anti-inflammatory or lipid-lowering medicines. Background technique [0002] Naringenin (Naringenin) is a common natural flavonoid plant secondary metabolite, mainly in the form of glycosides in naringenin, more restricted distribution than other flavonoids, and specific to citrus fruits . Naringenin is considered to have various biological and pharmacological activities on human health, such as antioxidant, anti-inflammatory, hypolipidemic, bacteriostatic, tumor growth inhibition, hepatocyte protection, platelet aggregation inhibition and other activities, so it has received extensive 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, and is easily affected by various factors from living organisms and the outside world, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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