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Sesquiterpenoids in zedoary as well as preparation method and application of sesquiterpenoids

A technology of sesquiterpenoids and compounds, applied in the separation/purification of carbonyl compounds, digestive system, organic chemistry, etc., to achieve the effect of novel structure

Active Publication Date: 2014-11-26
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the guaiacane-type and eucalyptane-type novel compounds disclosed in this patent and their compositions inhibit the release of nitric oxide (NO) from RAW 264.7 cells induced by LPS has not yet been reported.

Method used

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  • Sesquiterpenoids in zedoary as well as preparation method and application of sesquiterpenoids
  • Sesquiterpenoids in zedoary as well as preparation method and application of sesquiterpenoids
  • Sesquiterpenoids in zedoary as well as preparation method and application of sesquiterpenoids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Extracting and separating sesquiterpenoids from Ezhu

[0028] Curcuma longa ( Curcuma ) Perennial herbaceous plant Zezhu Curcuma phaeocaulis The dried stems of Val (10Kg) were extracted with 90% (V / V) ethanol-water heating and reflux, the extract was concentrated, and ethyl acetate and n-butanol were used to extract equal volumes for 3 times respectively. From the total sesquiterpene fraction (262 g) of Zedoary Curcuma, 100 g of the sample was subjected to silica gel column chromatography and gradient elution with cyclohexane-acetone (98:2~0:100) to obtain 9 sub-fractions (Fr.1~Fr. 9). Subfraction Fr.3 (12 g) was eluted with petroleum ether-ethyl acetate (98:2~0:100) gradient to obtain 6 subfractions (Fr.3-1~Fr.3-6). Fr.3-3 (3 g) was subjected to Sephadex LH-20 column chromatography, eluted with chloroform-methanol (1:1), and then preparative thin-layer chromatography (petroleum ether-ethyl acetate) to obtain compound 5 (144 mg) and Compound 10 (280 mg)...

Embodiment 2

[0048] Embodiment 2: Sesquiterpene 1-16 in Curcumae inhibits the release of nitric oxide (NO) from lipopolysaccharide-induced mouse mononuclear macrophage RAW 264.7

[0049] Mouse mononuclear macrophages RAW 264.7 (ATCC TIB-71) were cultured in 10% heat-inactivated (56°C, 30min) fetal bovine serum (FBS), 100 U / mL penicillin sodium (Gibco), 100 μg / mL chain Mycin (Gibco) in RPMI 1640 (Gibco) medium at 37°C, 5% CO 2 grown in a constant temperature incubator. Because NO is extremely unstable, it is quickly metabolized into nitrous acid (NO2) in the cell culture supernatant. - ), so the Griess method was used to measure NO2 in the sample - concentration as an indicator of NO levels. Griess reagent A: 0.1% N-naphthylene diamine dihydrochloride dissolved in water; Griess reagent B: 1% sulfanilamide dissolved in 5% H 3 PO 4 middle. Mix reagents A and B in equal volumes before use. RAW 264.7 cells were diluted to a concentration of 5×105 cells / mL with RPMI 1640 culture medium,...

Embodiment 3

[0051] Embodiment 3: the preparation of granule

[0052] Take 1 g of the total sesquiterpene parts of Curcuma curcuma obtained in Example 1, mix with 29 g of starch, add water to make a soft material, pass through a 12-mesh sieve for granulation, and obtain granules after drying. This granule contains 10 mg of total sesquiterpene parts per 300 mg.

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Abstract

The invention belongs to the technical field of medicines, and discloses a guaiane-type and selinane-type sesquiterpenoids in zedoary as well as a preparation method and an application of the sesquiterpenoids. The invention also relates to a composition using the two compounds as the main ingredients as well as a preparation method and an application of the composition. The sesquiterpenoids have a structure shown in formula (I) and formula (II), and the meanings of the group are shown in the specification. The composition of the guaiane-type and selinane-type sesquiterpenoids is prepared by extracting the raw material of plant zedoary by using an organic solvent and / or water and separating by using a chromatographic separation method and / or an extraction method. The composition of the sesquiterpenoids can be used for treating diseases such as cancer, phlogosis and immune diseases associated with metabolic disorder of nitric oxide.

Description

technical field [0001] The present invention belongs to the technical field of medicine, in particular to sesquiterpenoids in zedoary and its preparation method and use, and also includes its pharmaceutical composition, to be exact, sesquiterpenoids in zedoary and its composition inhibit LPS-induced RAW 264.7 Effects of cellular production of nitric oxide (NO), and methods of preparing such compositions. Background technique [0002] As a new type of signaling molecule, nitric oxide (NO) can regulate the functions of endothelial cells, smooth muscle cells and nerve cells, and participate in the recovery of inflammation and tissue damage, (Chen Minzhu, Nitric Oxide and Inflammatory Immune Cells, Chinese Pharmacology Bulletin, 1992.8 .409-415) play an important role in the physiology, pathology and related clinical diseases of multiple systems such as respiration, digestion, circulation and immunity. [0003] Nitric oxide (NO) is formed from the oxidation of arginine guanidin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94C07D493/20C07D209/90C07C49/733C07C49/743C07C45/78A61K31/403A61K31/365A61P3/00A61P9/12A61P9/04A61P1/16A61P11/06A61P11/00A61P3/10A61P19/02A61P19/08A61P17/06A61P25/16A61P25/24A61P35/02A61P35/00
Inventor 邱峰刘越康宁陈丽霞赵烽吴博
Owner SHENYANG PHARMA UNIVERSITY