Fukinanolide compounds and pharmaceutical application thereof

A technology of butterbur lactone and compounds, applied in the field of chemical structure of four new butterbur lactone compounds

Inactive Publication Date: 2009-10-28
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there is no literature reporting butterbur lactone components (sesquiterpene lactones) in butterbur plants as both antihistamines and leukotrienes or 5-lipoxygenase inhibitors. Drugs used in the preparation of drugs for the prevention and treatment of diseases that may be related to histamine and / or leukotrienes

Method used

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  • Fukinanolide compounds and pharmaceutical application thereof
  • Fukinanolide compounds and pharmaceutical application thereof
  • Fukinanolide compounds and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076]35Kg of dried leaves of Butterbur was extracted three times with ethanol under reflux, and the amount of ethanol was 5 times, 2 times, and 1 times that of the rhizome, and the extraction time was 2 hours, 1 hour, and half an hour, respectively. The extract was concentrated under reduced pressure and dissolved in water to form a suspension, which was extracted with petroleum ether and ethyl acetate to obtain petroleum ether extract and ethyl acetate extract respectively. The ethyl acetate extract was subjected to silica gel column chromatography (chromatographic silica gel 200-300 mesh, Shandong Yantai Zhifu Huangwu Silica Gel Development and Test Factory), and washed with n-hexane-ethyl acetate (8:1 to 1:1) solvent system According to thin-layer chromatography monitoring, the eluates were combined into thirteen parts. The fourth part was subjected to silica gel column chromatography, eluted with n-hexane-ethyl acetate (20:1), and the eluate was concentrated and then subjecte...

Embodiment 2

[0079] 5 kg of dry rhizomes of hairy butterbur, add 10 liters of ethanol, infiltrate 3 times. Combine the percolates and concentrate under reduced pressure to a certain volume to obtain a crude extract of total butterbur lactone. Dissolve the crude butterbur lactone extract with water, and then pass the macroporous adsorption resin (D101 type, Tianjin Zhengtiancheng Clarification Technology Co., Ltd., or other brands, such as AB-8, D4020, 860021, HP20, SP825) Etc.), rinse with water or dilute ethanol, and then rinse with concentrated ethanol, and recover the concentrated ethanol to rinse part under reduced pressure to obtain the butterbur lactone mixture. The mixture was subjected to silica gel column chromatography and eluted with petroleum ether-acetone (50-5:1) to obtain Homofukinolide (7.9 mg), butterburide-Ia (29 mg) and butterburide-IIa ( 65mg), butterbur lactone-B (1.6g), butterbur lactone-IIIa (2.8g), butterbur lactone-IVa (2.9g), butterbur lactone-D (2.6g) .

Embodiment 3

[0081] The dry rhizome of butterbur was 5Kg, extracted three times with methanol reflux, the amount of methanol was 5 times, 2 times, and 1 times that of the rhizome, and the extraction time was 2 hours, 1 hour, and half an hour, respectively. The extract was concentrated under reduced pressure and dissolved in water to form a suspension, which was extracted with petroleum ether and ethyl acetate to obtain petroleum ether extract and ethyl acetate extract respectively. The petroleum ether extract was chromatographed on silica gel column (chromatographic silica gel 200-300 mesh, Shandong Yantai Zhifu Huangwu Silica Gel Development and Test Factory), and eluted with a gradient of n-hexane-ethyl acetate (20:1 to 1:1). The compounds butterburide A (6.1mg), Homofukinolide (6.9mg), butterburide-Ia (5mg) and butterburide-IIa (6.3mg), butterburide-Fa were sequentially obtained (6.2mg), butterbur lactone-Fb (26.9 mg), butterbur lactone-I (14.3 mg), butterbur lactone-J (7.2 mg), butterbur l...

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Abstract

The present invention relates to the technical field of natural medicinal chemistry, and discloses the structures and extraction and separation methods of four new butterbur lactone compounds as shown in formula (1) extracted and separated from Petasites tricholobus Franch.; and Including the four new compounds, its general chemical structure is the butterbur lactone compound of formula (1), which may be related to histamine and / or leukotriene components in the preparation treatment and prevention, including asthma , seasonal and perennial allergic rhinitis, sinusitis, conjunctivitis, food allergy, scombroids, psoriasis, urticaria, itching, eczema, rheumatoid arthritis, inflammatory bowel disease, chronic obstructive pulmonary disease, neuropathy, psychosis and otitis media and other diseases, including drug applications.

Description

Technical field [0001] The present invention relates to the field of natural medicine chemistry and medical technology, and relates to the chemical structure of four new butterbur lactone compounds extracted and separated from Petasites tricholobus Franch., and including the new compound and its derivatives. The application of butterbur lactone compounds in the preparation of medicines for the treatment and prevention of diseases that may be related to histamine and / or leukotriene components. Background technique [0002] Bronchial asthma (BA) and allergic rhinitis (AR) are common complications and often coexist in the same patients. At least 70% of BA patients have AR, and about 20% to 50% of AR patients have BA. The latest research in airway cell and molecular biology confirms that inflammation plays a key role in the pathogenesis of AR and BA. They are all immunological diseases accompanied by mucosal allergic inflammation. Therefore, effective treatment of allergic rhinitis a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94A61P29/00
Inventor 郭美丽王玉亮张戈李润平刘宏艳
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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