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Monocyclic monoterpene glycoside compound and preparation method and applications thereof

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

Active Publication Date: 2019-08-20
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 preparation method and applications thereof
  • Monocyclic monoterpene glycoside compound and preparation method and applications thereof
  • Monocyclic monoterpene glycoside compound and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] a. Get 2 kg of the above-ground part of Dracocephalum komarovi Lipsky, pulverize it, and use 5 times the volume concentration of 70% ethanol aqueous solution to extract by cold soaking at room temperature for 3 times, and evaporate the solvent under reduced pressure to obtain the extract;

[0038] b. The extract obtained in step a is separated with a normal phase silica gel column, and gradient elution is carried out with n-hexane-ethyl acetate with a volume ratio of 100:1-1:1, and the fraction is analyzed by silica gel thin layer chromatography (TLC) , combined the same fractions to obtain 9 fractions (F1-F9); the fraction F4 was eluted with methanol-water with a volume ratio of 10%-100% through reverse-phase silica gel column chromatography, and the fractions obtained were eluted with Preparative reversed-phase column (C 18 , 5 μm, 10 × 150mm) separation, with a concentration of 40% methanol-water solution isocratic elution, to obtain formula (I) compound terpineol-8-...

Embodiment 2

[0040] a. Take 2 kg of the above-ground part of Dracocephalum komarovi Lipsky, pulverize it, and use 6 times the volume concentration of 70% ethanol-water solution to reflux and extract at 80° C. for 3 times, and evaporate the solvent under reduced pressure to obtain the extract;

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

Embodiment 3

[0043] a. Get 2 kg of the aerial part of Dracocephalum komarovi Lipsky, pulverize it, and extract it by percolation at room temperature with 7 times the volume concentration of dehydrated alcohol for 3 times, and evaporate the solvent under reduced pressure to obtain the extract;

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

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Abstract

The invention relates to a monocyclic monoterpene glycoside compound and a preparation method and applications thereof. The monocyclic monoterpene glycoside compound is prepared by the following steps: detecting and analyzing aerial parts of a Dracocephalum plant Dracocephalum komarovi Lipsky by using a thin-layer chromatography method and an analytical high-performance liquid chromatography, performing extraction by using organic solvents, performing separation by using three to four methods among a normal-phase silica gel column chromatography, a reverse-phase silica gel column chromatography, a Sephadex LH-20 gel column chromatography and a semi-preparative high-performance liquid chromatography so as to obtain three novel monoterpene glycoside monomer compounds, determining the three monomer compounds to be novel monocyclic monoterpene glycosides by methods such as high resolution mass spectrum and nuclear magnetic resonance spectrum, and carrying out structural identification. Inaddition, the anti-inflammatory activity of the monocyclic monoterpene glycosides is determined, and the result shows that the monocyclic monoterpene glycosides have significant anti-inflammatory activity and can be used for preparing 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 3500 species distributed all over the world, among which 96 genera and 807 species are distributed in China. The genus Dracocephalum includes 70 species of plants, of which 35 species are distributed in China and 9 species are distributed in Uzbekistan. Orchids are 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 plant that grows in shrubs and understory at an altitude of 2300-3600 meters. It is a unique pandan plant in Uzbekistan. In Uzbekistan, the plant is known as "buzbosh" and its aerial parts are used folkly to treat inflammation and related diseases. [0003] Mono...

Claims

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Application Information

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Patent Type & Authority Applications(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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