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Monocyclic monoterpene glycoside compound and its preparation method and use

A technology of monoterpene glycosides and compounds, applied in the field of three monocyclic monoterpene glycosides and their preparation

Active Publication Date: 2022-06-24
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nitric oxide has a killing effect on bacteria, fungi, parasites, tumor cells, and has a toxic effect on tumor cells, but at the same time as it has an immune effect, it is also toxic to those cells expressing nitric oxide synthase and their surrounding cells effect

Method used

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  • Monocyclic monoterpene glycoside compound and its preparation method and use
  • Monocyclic monoterpene glycoside compound and its preparation method and use
  • Monocyclic monoterpene glycoside compound and its preparation method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0037] A, get the aerial part 2kg of blue orchid plant Dracocephalum komarovi Lipsky, after pulverizing with 5 times the volume concentration of 70% ethanol aqueous solution at room temperature, cold immersion extraction is 3 times, and the solvent is evaporated to dryness under reduced pressure to obtain extract;

[0038] b. The extract obtained in step a is separated by a normal-phase silica gel column, and the gradient elution is carried out with n-hexane-ethyl acetate in a volume ratio of 100:1-1:1, and the fraction is analyzed by silica gel thin layer chromatography (TLC) , the same fractions were combined to obtain 9 components (F1-F9); component F4 was subjected to reverse phase silica gel column chromatography, eluted with methanol-water with a volume ratio of 10%-100%, and the obtained fractions were Prepare a reversed-phase column (C 18 , 5μm, 10 × 150mm), separated by isocratic elution with methanol-water solution with a concentration of 40% to obtain the compound o...

Embodiment 2

[0040] A, get the aerial part 2kg of blue orchid plant Dracocephalum komarovi Lipsky, after pulverizing, use 6 times of volume concentration to be 70% ethanol-water solution temperature 80 ℃ of reflux extraction 3 times, evaporate the solvent under reduced pressure to obtain extract;

[0041] b. The extract obtained in step a is separated with a normal-phase silica gel column, and the gradient elution is carried out with cyclohexane-acetone in a volume ratio of 100:1-1:1, and the fraction is analyzed by silica gel thin layer chromatography (TLC), The same fractions were combined to obtain 9 components (F1-F9); component F4 was subjected to reverse phase silica gel column chromatography, eluted with methanol-water with a volume ratio of 10%-100%, and the obtained fractions were prepared using Reversed-phase column (C 18 , 5μm, 10 × 150mm), separated by isocratic elution with methanol-water solution with a concentration of 40% to obtain the compound of formula (I) terpineol-8-O-...

Embodiment 3

[0043] A, get the aerial part 2kg of blue orchid plant Dracocephalum komarovi Lipsky, after pulverizing, use the dehydrated alcohol of 7 times of volume concentration to percolate and extract 3 times at room temperature, evaporate the solvent to dryness under reduced pressure to obtain extract;

[0044] b. The extract obtained in step a is separated by a normal-phase silica gel column, and the gradient elution is carried out with n-hexane-ethyl acetate in a volume ratio of 100:1-1:1, and the fraction is analyzed by silica gel thin layer chromatography (TLC) , the same fractions were combined to obtain 9 components (F1-F9); component F4 was separated by a Sephadex LH-20 gel column, and eluted with methanol-water with a volume ratio of 10%-100%. Preparative reversed-phase column (C 18 , 5 μm, 10 × 150 mm), separated by isocratic elution with methanol-water solution with a concentration of 40% to obtain the compound of formula (I) as terpineol-8-O-D-glucopyranosyl-(1→2)-β -D-glu...

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Abstract

The present invention relates to a monocyclic monoterpene glycoside compound and its preparation method and application. The monocyclic monoterpene glycoside compound is obtained from Dracocephalum komarovi The aerial part of Lipsky was detected and analyzed by thin layer chromatography and analytical high performance liquid chromatography, extracted with organic solvent, and then condensed by normal phase silica gel column chromatography, reversed phase silica gel column chromatography, Sephadex LH‑20 Three to four methods of gel column chromatography and semi-preparative high-performance liquid chromatography were used to separate three new monoterpene glycoside monomer compounds, and three monoterpene glycoside monomer compounds were determined by high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy. The body compound was a new monocyclic monoterpene glycoside, and its structure was identified. In addition, the anti-inflammatory activity of these monocyclic monoterpene glycosides was determined, and the results showed that: the monocyclic monoterpene glycosides have relatively significant anti-inflammatory activity and can be used for the preparation of anti-inflammatory drugs.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to three monocyclic monoterpene glycoside compounds and a preparation method thereof. Background technique [0002] Lamiaceae plants include about 220 genera and 3,500 species distributed around the world, of which the most widespread in Dihai and Asia, and 96 genera and 807 species of plants in China. The genus Dracocephalum includes 70 species of plants, 35 of which are distributed in China and 9 in Uzbekistan. Orchid is widely used in traditional medicine to treat gastric ulcers, laryngitis, headaches, acute respiratory infections, diarrhea, and rheumatoid arthritis. Dracocephalum komarovi Lipsky is a perennial shrub that grows in thickets and forests at an altitude of 2300-3600 meters. It is a species of pandan endemic to Uzbekistan. In Uzbekistan, the plant is called "buzbosh", and its aerial parts are used in the folk to treat inflammation and other related diseases. [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/203C07H1/08A61K31/7034A61K31/7032A61P29/00
CPCC07H15/203C07H1/08A61P29/00
Inventor 阿吉艾克拜尔·艾萨扎克尔·托斯玛多夫李俊
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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