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Aromatic-substituted glucose-like compound as well as preparation method of pharmaceutical compositions thereof and analgesia application of compound

A compound and drug technology, applied in the field of natural medicinal chemistry, can solve the problems of no analgesic activity and achieve good analgesic activity

Active Publication Date: 2019-05-28
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Aromatic-substituted glucose-like compound as well as preparation method of pharmaceutical compositions thereof and analgesia application of compound
  • Aromatic-substituted glucose-like compound as well as preparation method of pharmaceutical compositions thereof and analgesia application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Extraction, separation and purification of compound 1-19 of the present invention:

[0030] will thick skin fragrant [ Ternstroemia gymnanthera (Wight et Arn.) Bedd.] The aerial part (14kg) of the plant was dried in the shade, crushed to 30 mesh, extracted three times with 95% ethanol at room temperature, 60 L each time, 24 h, combined the extracts, and reduced pressure Concentrate the extract to obtain the extract, suspend it with appropriate amount of water, and distribute it with ethyl acetate for 6 times to obtain ethyl acetate extract (726 g), dissolve the extract with appropriate amount of chloroform / acetone and mix the sample with silica gel 80-100 mesh , and then use 650 g of silica gel 200-300 mesh to carry out column chromatography for rough separation, and carry out gradient elution with chloroform / methanol (1 : 0-0 : 1) to obtain 7 main fractions. Silica gel column chromatography, 8 : 2 chlorine / A fraction and 7 : 3 chlorine / A fraction were carried out ...

Embodiment 2

[0032] Physical and spectral data of compounds 1-19 of the present invention:

[0033] Compound 1: brown solid. UV (MeOH) lambda max (log ε ): 223 (4.12), 291 (3.58) nm; HR-ESI-MS m / z : 315.1405 [M-H] - (calcd for C 14 h 19 o 8 , 315.1402); 1 H-NMR (400 MHz, CD 3 OD) δ : 6.62 (1H, d, J = 2.1 Hz, H-2'), 6.61 (1H, d, J = 8.1 Hz, H-5'), 6.49 (1H, dd, J = 8.0, 2.1 Hz, H-6'), 4.23 (1H, d, J = 7.8 Hz, H-1), 3.96 (1H, m, H-8’a), 3.80 (1H, dd, J = 11.9, 1.9 Hz, H-6a), 3.62 (2H, overlap, H-6b, 8'b), 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, 7.8 Hz, H-2), 2.71 (2H, m, H 2 -7'); 13 C-NMR (100 MHz, CD 3 OD) δ: 104.3 (d, C-1), 75.0 (d, C-2), 77.8 (d, C-3), 71.5 (d, C-4), 78.0 (d, C-5), 62.6 (d, C-6), 131.4 (s, C-1'), 116.3 (d, C-2'), 146.0 (s, C-3'), 144.6 (s, C-4'), 117.1 (d, C -5'), 121.2 (d, C-6'), 36.6 (t, C-7'), 72.1 (t, C-8').

[0034] Compound 2: brown solid. UV (MeOH) lambda max (log ...

Embodiment 3

[0053] The analgesic activity detection of compound of the present invention:

[0054] 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, with 6 mice in each group. The dose of 200 mg / kg was intragastrically administered, the negative control group was given the same amount of normal saline, and the positive drug group was given aspirin. After 40 min of administration, each mouse was intraperitoneally injected with 0.6% glacial acetic acid solution 0.2 mL / 10g. After 3-5 min of glacial acetic acid, observe and record the number of writhing of the mice within 15 min, and calculate the inhibition rate of the test substance on the mouse acetic acid writhing according to the following formula, so as to evaluate the analgesic effect of th...

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Abstract

The invention relates to an aromatic-substituted glucose-like compound as well as a preparation method of a pharmaceutical composition thereof and analgesia application of the compound, and belongs tothe field of chemistry of natural medicines. According to the aromatic-substituted glucose-like compound shown in a formula (1), the preparation method of the pharmaceutical composition using the compound as an active ingredient comprises the following steps: taking aboveground parts or whole plants of ternstroemia gymnanthera plants; directly performing assisted extraction including cold soaking or thermal refluxing or ultrasonic treatment or microwave treatment and the like on the aboveground parts or whole plants by using an organic solvent such as dichloromethane or chloroform or ethyl acetate or acetone or methanol or ethanol or water, or performing the assisted extraction including cold soaking or refluxing or ultrasonic treatment or microwave treatment and the like on the aboveground parts or whole plants by firstly using the organic solvent or the water and then performing extraction by using ethyl acetate to obtain total extractum; and performing repeated chromatography on the total extractum to obtain the compound disclosed by the invention. The invention discloses the pharmaceutical composition using the compound as the active ingredient for analgesia and application of the compound to preparation of an analgesic agent. The formula (1) is shown in the description.

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. technical background: [0002] thick skin incense [ Ternstroemia gymnanthera (Wight et Arn.) Bedd.] Synonymous Baihuaguo, Ganhong, Mohong, Camellia, Zhuxuechai, Qixueteng, Dawuweiteng, etc., are shrubs or small trees of the genus Pachyderm in the family Theaceae, 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 (Yu...

Claims

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Application Information

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Patent Type & Authority Applications(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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