New honeysuckle chlorogenic acid ester saponin as well as preparation method and use thereof

Abstract

The invention relates to the field of natural pharmaceutical chemistry and discloses a chemical structure of a new honeysuckle chlorogenic acid ester saponin compound which is extracted and separated from lonicera macranthodes hand-mazz buds, and the compound has the structure as shown in the right formula. The invention further relates a preparation method of the compound and a use of the compound in the field of medicine, in particular to a use of the compound in preparation of cycloxygenase II inhibitors, matrix metalloproteinase-9 inhibitors or anti-tumor drugs.

Description

1. Technical field:

[0001] The invention relates to the field of natural medicinal chemistry, and discloses a new honeysuckle chloro orthoester saponin compound extracted and separated from the flower buds of Lonicera cinerea, as well as the preparation method of the compound and its application in the field of medicine, especially in the preparation of cyclic Use of an oxidase II inhibitor, a matrix metalloproteinase-9 inhibitor or an antineoplastic drug. 2. Technical background:

[0002] Honeysuckle is rich in chlorogenic acid and oleanolic acid saponins. Chlorogenic acid has the functions of antibacterial, anti-virus, increasing white blood cells, protecting liver and gallbladder, anti-tumor, lowering blood pressure, lowering blood fat, scavenging free radicals and stimulating the central nervous system; in recent years, reports have shown that chlorogenic acid has a strong inhibitory matrix Activity of metalloproteinase-9 (MMP-9) (Un-Ho, J., et al. Life Sciences, 2005, ...

Examples

Embodiment 1

[0021] Example 1. Isolation and identification of the compound Lonimacranthoide I from Lonicera cinerea

[0022] 10 kg of dried flower buds of Lonicerae pilosula were extracted with 100 kg of 95% (volume ratio) ethanol-water solution under reflux for 3 times, each time for 2 hours, and concentrated until there was no alcohol smell to obtain an extract (dry weight 1.7 kg); the obtained extract was added 10 times volume of water dissolved, filtered through filter paper to remove water-insoluble matter, the filtrate was adsorbed with macroporous resin HP-20, then eluted with water, 20%, 70% ethanol solution, combined with 70% ethanol solution eluate, concentrated to obtain gray felt Total saponins of Lonicerae pubescens 860g. The obtained total saponins of Lonicera tomentosa were subjected to silica gel column chromatography, and the eluent was chloroform-methanol-water (17:3:0.2→4:1:0.1→7:3:0.5→3:3:0.5), methanol Wherein chloroform-methanol-water (3: 3: 0.5) part carries out re...

Embodiment 2

[0031] Embodiment 2, water extraction method prepares Lonimacranthoide I from gray felt wool honeysuckle

[0032] 1 kg of dried flower buds of Lonicerae pilosula, heated and extracted three times with water, the water consumption was 10 liters, the extraction time was 2 hours, the extraction temperature was 100°C, the extract was absorbed by macroporous resin D101, and then washed with water, 15%, 75% ethanol Take off, and 75% ethanol eluent recovers solvent under reduced pressure to obtain 87g of total saponins of Lonicera tomentosa. The obtained total saponins of Lonicera tomentosa were subjected to silica gel column chromatography, and the mobile phase was chloroform-methanol-water (17:3:0.2→4:1:0.1→7:3:0.5→3:3:0.5), methanol; Among them, chloroform-methanol-water (3:3:0.5) was subjected to repeated reverse phase silica gel C-8 column chromatography (eluent was 30% ethanol-water solution) separation and gel column Sephdex LH-20 chromatography purification (elution The solv...

Embodiment 3

[0033] Embodiment 3, prepare Lonimacranthoide I from gray felt wool honeysuckle with methanol cold soaking extraction method

[0034] 1Kg of dried flower buds of Lonicerae pilosula, extracted three times by cold immersion in methanol, the amount of methanol used was 20 liters, the extraction time was 20 days, the extraction temperature was room temperature, and the extract was concentrated to an alcohol-free extract (dry weight was 120g); Add 10 times the volume of water to dissolve the extract, filter paper to remove water-insoluble matter, absorb the filtrate with macroporous resin AB-8, then elute with water, 10%, 80% ethanol solution, and combine the 80% ethanol solution eluent , and concentrated to obtain 81g of total saponins of Lonicerae cinerea. Gained total saponins of Lonicera tomentosa are subjected to column chromatography (silica gel column chromatography: chloroform-methanol-water gradient elution system, RP-C18 column chromatography: water-methanol system, gel c...

1. Technical field:

[0001] The invention relates to the field of natural medicinal chemistry, and discloses a new honeysuckle chloro orthoester saponin compound extracted and separated from the flower buds of Lonicera cinerea, as well as the preparation method of the compound and its application in the field of medicine, especially in the preparation of cyclic Use of an oxidase II inhibitor, a matrix metalloproteinase-9 inhibitor or an antineoplastic drug. 2. Technical background:

[0002] Honeysuckle is rich in chlorogenic acid and oleanolic acid saponins. Chlorogenic acid has the functions of antibacterial, anti-virus, increasing white blood cells, protecting liver and gallbladder, anti-tumor, lowering blood pressure, lowering blood fat, scavenging free radicals and stimulating the central nervous system; in recent years, reports have shown that chlorogenic acid has a strong inhibitory matrix Activity of metalloproteinase-9 (MMP-9) (Un-Ho, J., et al. Life Sciences, 2005, ...

Examples

Embodiment 1

[0021] Example 1. Isolation and identification of the compound Lonimacranthoide I from Lonicera cinerea

[0022] 10 kg of dried flower buds of Lonicerae pilosula were extracted with 100 kg of 95% (volume ratio) ethanol-water solution under reflux for 3 times, each time for 2 hours, and concentrated until there was no alcohol smell to obtain an extract (dry weight 1.7 kg); the obtained extract was added 10 times volume of water dissolved, filtered through filter paper to remove water-insoluble matter, the filtrate was adsorbed with macroporous resin HP-20, then eluted with water, 20%, 70% ethanol solution, combined with 70% ethanol solution eluate, concentrated to obtain gray felt Total saponins of Lonicerae pubescens 860g. The obtained total saponins of Lonicera tomentosa were subjected to silica gel column chromatography, and the eluent was chloroform-methanol-water (17:3:0.2→4:1:0.1→7:3:0.5→3:3:0.5), methanol Wherein chloroform-methanol-water (3: 3: 0.5) part carries out re...

Embodiment 2

[0031] Embodiment 2, water extraction method prepares Lonimacranthoide I from gray felt wool honeysuckle

[0032] 1 kg of dried flower buds of Lonicerae pilosula, heated and extracted three times with water, the water consumption was 10 liters, the extraction time was 2 hours, the extraction temperature was 100°C, the extract was absorbed by macroporous resin D101, and then washed with water, 15%, 75% ethanol Take off, and 75% ethanol eluent recovers solvent under reduced pressure to obtain 87g of total saponins of Lonicera tomentosa. The obtained total saponins of Lonicera tomentosa were subjected to silica gel column chromatography, and the mobile phase was chloroform-methanol-water (17:3:0.2→4:1:0.1→7:3:0.5→3:3:0.5), methanol; Among them, chloroform-methanol-water (3:3:0.5) was subjected to repeated reverse phase silica gel C-8 column chromatography (eluent was 30% ethanol-water solution) separation and gel column Sephdex LH-20 chromatography purification (elution The solv...

Embodiment 3

[0033] Embodiment 3, prepare Lonimacranthoide I from gray felt wool honeysuckle with methanol cold soaking extraction method

[0034] 1Kg of dried flower buds of Lonicerae pilosula, extracted three times by cold immersion in methanol, the amount of methanol used was 20 liters, the extraction time was 20 days, the extraction temperature was room temperature, and the extract was concentrated to an alcohol-free extract (dry weight was 120g); Add 10 times the volume of water to dissolve the extract, filter paper to remove water-insoluble matter, absorb the filtrate with macroporous resin AB-8, then elute with water, 10%, 80% ethanol solution, and combine the 80% ethanol solution eluent , and concentrated to obtain 81g of total saponins of Lonicerae cinerea. Gained total saponins of Lonicera tomentosa are subjected to column chromatography (silica gel column chromatography: chloroform-methanol-water gradient elution system, RP-C18 column chromatography: water-methanol system, gel c...

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