CN101555242B - Dibenzocyclooctadiene lignan, preparation method and use thereof - Google Patents
Dibenzocyclooctadiene lignan, preparation method and use thereof Download PDFInfo
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- CN101555242B CN101555242B CN 200910027427 CN200910027427A CN101555242B CN 101555242 B CN101555242 B CN 101555242B CN 200910027427 CN200910027427 CN 200910027427 CN 200910027427 A CN200910027427 A CN 200910027427A CN 101555242 B CN101555242 B CN 101555242B
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- chloroform
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Abstract
The invention discloses a dibenzocyclooctadiene lignan and a preparation method thereof. The preparation method comprises the following steps of taking roots and stems of Kadsura coccinea (Lem.) A C. as raw materials, smashing the raw materials, then using acetone water solution with the volume concentration of 50-95 percent for extracting for 1-10 times with each time lasting 5-50 hours, merging extract liquid, concentrating, obtaining a liquid extract, then sequentially using cyclohexane, chloroform, ethyl acetate and n-butanol for extracting, and carrying out column chromatography on the part of a chloroform layer by using a silica gel column, thereby obtaining the dibenzocyclooctadiene lignan. The lignan has good anti-inflammation effect and good application prospect in the prepration of anti-inflammation drugs, thereby having significant and positive significance.
Description
Technical field
The invention belongs to the Chinese materia medica technical field, be specifically related to a kind of Dibenzocyclooctene lignan, Its Preparation Method And Use.
Background technology
Caulis Kadsurae Coccineae Kadsura coccinea (Lem.) A C., another name kadsurae coccineae, Root-bark of Monkshoodvine rattan etc., belong to Schisandraceae, its root skin is dry, and appearance is slightly coarse, matter is crisp, be brown, internal surface reddish-brown, gas fragrance, mildly bitter flavor is puckery, mainly is distributed in the ground such as Hubei, Guangdong, Guangxi, Sichuan, Yunnan, Guizhou; Be mainly used in treating treating rheumatic ostealgia, fall the diseases such as the servant sprains, dysmenorrhes, chronic gastritis, root extract has certain calmness and antiinflammation.Yet Caulis Kadsurae Coccineae always uses as a kind of ethnic drug, and the medicinal research of the chemical constitution of the extract of its root and stem is had no report.
Summary of the invention
The purpose of this invention is to provide a kind of by extracting isolated Dibenzocyclooctene lignan, Its Preparation Method And Use in the Caulis Kadsurae Coccineae.
To achieve the above object of the invention, the technical solution used in the present invention is: a kind of Dibenzocyclooctene lignan, and structural formula is:
Wherein: R
1For
The present invention asks for protection the preparation method of above-mentioned Dibenzocyclooctene lignan simultaneously; may further comprise the steps: take the root of Caulis Kadsurae Coccineae Kadsura coccinea (Lem.) A C. and stem as raw material; be 50～95% aqueous acetone solution extraction 1～10 time with volumetric concentration after pulverizing; each 5～50 hours; united extraction liquid; obtain medicinal extract after concentrated; extract with hexanaphthene, chloroform, ethyl acetate and propyl carbinol successively again; the chloroform layer part is carried out column chromatography with silicagel column, namely obtain described Dibenzocyclooctene lignan.
Above, the extracting mode of described aqueous acetone solution can be cold carrying, and also can be that heat is carried, and is preferably cold carrying.
In the technique scheme, the solvent systems of described column chromatography is the mixed solvent of chloroform-methanol, and take chloroform: the ratio of methyl alcohol was carried out gradient elution by volume as 100: 0～0: 100.
In the technique scheme, the volumetric concentration of described aqueous acetone solution is 70～90%, extracts each 24 hours 1～3 time.
The present invention asks for protection the application of above-mentioned Dibenzocyclooctene lignan in the preparation anti-inflammatory drug simultaneously.
Because the employing of technique scheme, compared with prior art, the present invention has following advantage:
1. the present invention extracts in the root of Caulis Kadsurae Coccineae and stem and isolates a kind of new Dibenzocyclooctene lignan, evidence, and this lignanoid has good anti-inflammatory efficacy, has a good application prospect in the preparation anti-inflammatory drug, has significant positive effect.
2. preparation method of the present invention is simple, easy handling, and cost is lower, is suitable for applying.
Embodiment
The invention will be further described below in conjunction with embodiment:
Embodiment one
A kind of preparation method of Dibenzocyclooctene lignan, may further comprise the steps: take the root of Caulis Kadsurae Coccineae Kadsuracoecinea (Lem.) A C. and stem as raw material, be 80% aqueous acetone solution extraction 3 times with volumetric concentration after pulverizing, each 24 hours, united extraction liquid obtains medicinal extract after concentrating, and extracts with hexanaphthene, chloroform, ethyl acetate and propyl carbinol successively again, the chloroform layer part is carried out column chromatography with silicagel column, namely obtain described Dibenzocyclooctene lignan.The solvent systems of described column chromatography is the mixed solvent of chloroform-methanol, and take chloroform: the ratio of methyl alcohol was carried out gradient elution by volume as 100: 0～0: 100.
Above-mentioned Dibenzocyclooctene lignan, structural formula is:
Wherein: R
1For
The application of above-mentioned Dibenzocyclooctene lignan in the preparation anti-inflammatory drug.
The present invention has also measured the nuclear magnetic data of above-claimed cpd, and the result is as shown in the table:
| δ c | δ H(mult；J，Hz) | δ c | δ H(mult；J，Hz) | ||
| 1 | 146.8 | 16 | 116.7 | ||
| 2 | 133.5 | 17 | 15.0 | 0.98，d(7.0) | |
| 3 | 150.5 | 18 | 19.8 | 1.11，d(6.9) | |
| 4 | 106.9 | 6.38，s | 19 | 101.2 | 5.98，5.94，each 1H(1.6) |
| 5 | 133.3 | 1’ | 167.1 | ||
| 6 | 38.6 | 2.64，m | 2’ | 131.6 | |
| 7 | 34.7 | 2.11，m | 3’ | 136.3 | 6.14，m |
| 8 | 41.6 | 2.11，m | 4’ | 99.3 | 4.94，d(6) |
| 9 | 84.0 | 5.57，s | 5’ | 52.2 | 3.45，s |
| 10 | 135.5 | 6’ | 52.0 | 3.24，s | |
| 11 | 102.8 | 6.54，s | 7’ | 13.0 | 1.51，d(1.02) |
| 12 | 148.9 | 2-OCH 3 | 60.6 | 3.85，s | |
| 13 | 136.1 | 3-OCH 3 | 55.6 | 3.87，s | |
| 14 | 141.1 | 14-OCH 3 | 59.7 | 3.83，s | |
| 15 | 119.1 | 1-OH | 5.51，s |
The present invention has also measured the above-claimed cpd anti-inflammatory activity, and activity determination method is as follows:
Adopt the RAW246.7 cell, adjust cell concn to 1.2 * 10
6/ mL, every hole 200 μ L are inoculated in 96 well culture plates, 5%CO
2, 37 ℃, cultivated 2 hours, add LPS (10 μ g/mL), IFN-γ (33ng/mL) 2 μ L, sample DMSO solution 0.4 μ L cultivated 16 hours.(LPS final concentration 100ng/mL, INF-γ final concentration is 100ng/mL, the DMSO of dissolution sample is 0.2% with respect to the content of substratum).Get supernatant liquor 100 μ L, add the Griess reagent that mixes up in advance, measure absorbancy with enzyme-linked immunosorbent assay instrument at 570nm (contrast 655nm).The cells survival rate is measured with mtt assay,
Test-results: have no cytotoxicity;
Test-results: the compound that the present embodiment obtains is 50.2 μ M to the inhibiting rate IC50 of NO.Certain anti-inflammatory activity that this compound has is described.
Claims (4)
1. a couplet benzene ring octadiene system lignans is characterized in that, structural formula is:
Wherein: R
1For
2. the preparation method of couplet benzene ring octadiene system lignans claimed in claim 1, it is characterized in that, may further comprise the steps: take the root of Caulis Kadsurae Coccineae Kadsura coccinea (Lem.) A C. and stem as raw material, be 50～95% aqueous acetone solution extraction 1～10 time with volumetric concentration after pulverizing, each 5～50 hours, united extraction liquid, obtain medicinal extract after concentrated, extract with hexanaphthene, chloroform, ethyl acetate and propyl carbinol successively again, the chloroform layer part is carried out column chromatography with silicagel column, namely obtain described couplet benzene ring octadiene system lignans; The solvent systems of described column chromatography is the mixed solvent of chloroform-methanol, and take chloroform: the ratio of methyl alcohol was carried out gradient elution by volume as 100: 0～0: 100.
3. the preparation method of couplet benzene ring octadiene system lignans according to claim 2, it is characterized in that: the volumetric concentration of described aqueous acetone solution is 70～90%, extracts each 24 hours 1～3 time.
4. the application of couplet benzene ring octadiene system lignans claimed in claim 1 in the preparation anti-inflammatory drug.
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| CN 200910027427 CN101555242B (en) | 2009-05-05 | 2009-05-05 | Dibenzocyclooctadiene lignan, preparation method and use thereof |
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| CN 200910027427 CN101555242B (en) | 2009-05-05 | 2009-05-05 | Dibenzocyclooctadiene lignan, preparation method and use thereof |
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| CN101555242A CN101555242A (en) | 2009-10-14 |
| CN101555242B true CN101555242B (en) | 2013-03-06 |
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| CN102249908B (en) * | 2011-05-12 | 2014-12-10 | 苏州大学 | Dibenzocyclooctene compound, and preparation and application thereof |
| CN103126945A (en) * | 2011-11-29 | 2013-06-05 | 株式会社爱茉莉太平洋 | Skin whitening composition containing thick-leaf Chinese magnolivine fruit extract powder |
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Address after: Suzhou City, Jiangsu province 215137 Xiangcheng District Ji Road No. 8 Patentee after: Soochow University Address before: 215123 Suzhou City, Suzhou Province Industrial Park, No. love road, No. 199 Patentee before: Soochow University |
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Granted publication date: 20130306 Termination date: 20180505 |