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Preparation method and analgesic application of aromatic substituted glucose compound and pharmaceutical composition thereof

A technology of glucose and compound, applied in the field of natural medicinal chemistry, can solve the problem of no analgesic activity and other problems

Active Publication Date: 2022-02-15
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there is no research report on the aromatic substituted glucose compounds and their analgesic activity

Method used

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  • Preparation method and analgesic application of aromatic substituted glucose compound and pharmaceutical composition thereof
  • Preparation method and analgesic application of aromatic substituted glucose compound and pharmaceutical composition thereof
  • Preparation method and analgesic application of aromatic substituted glucose compound and pharmaceutical composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Extraction, separation and purification of compound 1-14 of the present invention:

[0026] Dry the above-ground part (14kg) of Ternstroemia gymnanthera (Wight et Arn.) Bedd.] plant in the shade, crush it to 30 mesh, extract it three times with 95% ethanol at room temperature, 60L each time, 24h, extract The liquids were combined, and the extract was concentrated under reduced pressure to obtain a medicinal extract, then suspended with an appropriate amount of water, and then distributed 6 times with ethyl acetate to obtain an ethyl acetate extract (726g). Mix the sample with 100 mesh, and then use 650g silica gel 200-300 mesh to carry out column chromatography for rough separation, and use chloroform / methanol (1:0-0:1) for gradient elution to obtain 7 main parts. Chloroform / methanol fractions, 8:2 chloroform / methanol fractions and 7:3 chloroform / methanol fractions were subjected to silica gel column chromatography, and gradient elution was performed with 100:1-1:1 chlo...

Embodiment 2

[0028] Physical and spectral data of compounds 1-14 of the present invention:

[0029] Compound 1: brown solid. UV(MeOH)λ max (logε):223(4.11),290(3.55)nm; HR-ESI-MS m / z:329.3205[M-H] - (calcd for C 14 h 17 o 9 ,329.3202); 1 H-NMR (400MHz, CD 3 OD)δ: 7.08(2H,d,J=10.2Hz,H-2',6'),6.12(2H,d,J=10.2Hz,H-3',5'),4.43(1H,dd, J=11.9,2.1Hz,H-6a),4.15(1H,d,J=7.8Hz,H-1),4.21(1H,overlap,H-6b),3.30(1H,overlap,H-5), 3.25(1H, overlap, H-4), 3.21(1H, overlap, H-3), 3.13(1H, dd, J=9.0, 7.8Hz, H-2), 2.75(2H, s, H 2 -7'); 13 C-NMR (100MHz, CD 3 OD)δ: 102.3(d,C-1),75.1(d,C-2),77.9(d,C-3),71.4(d,C-4),78.2(d,C-5),64.6 (d,C-6),68.1(s,C-1'),152.3(d,C-2',6'),128.0(d,C-3',5'),187.6(s,C- 4'), 45.5(t, C-7'), 170.9(s, C-8').

[0030] Compound 2: brown solid. UV(MeOH)λ max (logε):222(4.03),290(3.48)nm; HR-ESI-MS m / z:343.3505[M-H] - (calcd for C 15 h 19 o 9 ,343.3512); 1 H-NMR (400MHz, CD 3OD)δ:6.74(1H,d,J=2.1Hz,H-2'),6.69(1H,d,J=8.1Hz,H-5'),6.59(1H,d,J=8.1,2.1Hz ,H-6'),4.45(1H,dd,J=11....

Embodiment 3

[0044] The analgesic activity detection of compound of the present invention:

[0045] The analgesic activity of the extract of the present invention was determined by acetic acid writhing test. Kunming mice were half male and half male, weighing 18-22 g, fasted and watered 12 hours before the experiment, and randomly divided into control group, sample group and positive drug group, 6 mice in each group. Intragastric administration with a dose of 200 mg / kg, the negative control group was given the same amount of normal saline, and the positive drug group was given aspirin. After 40 minutes of administration, each mouse was intraperitoneally injected with 0.6% glacial acetic acid solution 0.2mL / 10g, and injected with glacial acetic acid. After 3 to 5 minutes, observe and record the number of writhing times of the mice within 15 minutes, and calculate the inhibition rate of the test substance on the mouse acetic acid writhing according to the following formula, so as to evaluate...

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Abstract

The invention relates to a preparation method and analgesic application of an aromatic substituted glucose compound and a pharmaceutical composition thereof, and belongs to the field of natural medicinal chemistry. Aromatic substituted glucose compound 1-14, a pharmaceutical composition with this type of compound as an active ingredient, and a preparation method thereof, taking Houpixiang[ Ternstroemia gymnanthera (Wight et Arn.) Bedd.] plant aerial part or whole plant, with organic solvent dichloromethane or chloroform or ethyl acetate or acetone or methanol or ethanol or water direct cold dipping or heat reflux or ultrasound or microwave-assisted extraction, Or use the above-mentioned organic solvent or water cooling or reflux or ultrasonic or microwave-assisted extraction to obtain the total extract, and the total extract is subjected to repeated chromatography to obtain the compound of the present invention. An analgesic drug compound containing the compound of the present invention as an active ingredient. Application of the compound of the present invention in the preparation of analgesics.

Description

Technical field: [0001] The invention belongs to the field of natural medicinal chemistry, and in particular relates to a class of aromatic substituted glucose compounds, a preparation method thereof, a drug combination with the compounds as active ingredients, and an analgesic application thereof. [0002] technical background: [0003] Houpixiang [Ternstroemia gymnanthera (Wight et Arn.) Bedd.] synonymous white flower fruit, called stem red, mohong cut, camellia tree, pig blood wood, Qixueteng, Dawuwei vine, etc. It is a shrub or small tree, 1.5-10 meters high, sometimes up to 15 meters. Widely distributed in Xiuning in southern Anhui, Zhejiang, Jiangxi, Fujian, southwestern Hubei, southern and northwestern Hunan, Guangdong, northern and eastern Guangxi, Yunnan, Bijie in northeastern and northwestern Guizhou, and southern Sichuan. Growing in mountainous forests, forest edge roadsides or sparse forests near mountain tops at an altitude of 200-1400 meters (Yunnan can be dist...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/04C07H15/18C07H1/08A61K31/7024A61K31/7032A61P29/00
Inventor 姜北肖朝江李骅轩沈磊董相王敏江世智
Owner DALI UNIV
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