CN109824489A - A kind of compound with anti-inflammatory activity extracted from Radix Glycyrrhizae and its application - Google Patents
A kind of compound with anti-inflammatory activity extracted from Radix Glycyrrhizae and its application Download PDFInfo
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Abstract
The present invention discloses a kind of compound with anti-inflammatory activity extracted from Radix Glycyrrhizae and its application.Compound of the present invention is noval chemical compound, and the noval chemical compound includes dihydro stilbenes compound and furoflavone compound；The dihydro stilbenes compound includes the component with the structure as shown in formula 1 and formula 2:The wherein R of formula 11=OH, R2=OCH3, R3=OH, R4=OH；The wherein R of formula 21=OH, R2=OCH3, R3=OH；The furoflavone compound includes the component with the structure as shown in formula 3 and formula 4:The wherein R of formula 31=H, R2=OH, R3=OH, R4=OH, R5=OH, R6=OH；The wherein R of formula 41=OCH3, R2=OH, R3=H, R4=OH, R5=OH, R6=OH；And such as its pharmaceutically acceptable salt of formula 1-4.The noval chemical compound that the present invention obtains has good prospects in terms of researching and developing novel anti-inflammatory medicine and rationally utilizing Licorice to inflammatory factor nitric oxide inhibiting rate with higher.
Description
Technical field
The invention belongs to technical field of traditional Chinese medicines, it is related to a kind of compound and its application, specifically one kind is from Radix Glycyrrhizae
The compound with anti-inflammatory activity extracted and its application.
Background technique
Radix Glycyrrhizae derives from pulse family glycyrrhiza genus Radix Glycyrrhizae (Glycyrrhiza uralensis Fisch.), glycyrrhiza glabra
The root and rhizome of (G.glabra L.) and swollen fruit Radix (G.inflata Bat.).Modern pharmacology research shows that Radix Glycyrrhizae has
The multiple pharmacological effects such as liver protection, anti-inflammatory, anti-oxidant, anticancer, antitumor and antibacterial.Separation identifies 400 from Radix Glycyrrhizae at present
A variety of chemical components.However, it is relatively fewer for the research of Radix Glycyrrhizae aerial part, it results in waste of resources.From Radix Glycyrrhizae aerial part
Separated to identify a compound more than 300, main includes flavones ingredient 61, dihydro Stilbene constituents 11, volatile oil at
Divide 215,17 kinds of Amino acids, wherein flavone compound and dihydro stilbenes compound are as main active, tool
There are antitumor, resisting pathogenic microbes, resistance prostatitis isoreactivity.
Diseases associated with inflammation can cause infection, metabolic disease, cancer etc..Macrophage is the weight in a kind of nearly all tissue
Want immune effector cell that can discharge various media, including proinflammatory enzyme, cell factor and other media.From gramnegative bacterium
Lipopolysaccharides (LPS) various inflammatory reactions can be caused with activated macrophage, including release pro-inflammatory mediator and cell because
Son, such as tumor necrosis factor-alpha, interleukins, chemotactic factor (CF) and nitric oxide synthase type (iNOS).Immunocyte swashs
After work, a large amount of nitric oxide (NO) can be generated under iNOS effect in specific organization, a large amount of NO can be damaged with induced oxidation.
Inhibit nitric oxide production to generate for inhibiting inflammation and its complication significant.
Summary of the invention
It is an object of the invention to propose a kind of compound with anti-inflammatory activity extracted from Radix Glycyrrhizae and its application, institute
State compound on inflammation factor NO inhibiting rate with higher, therefore the present invention provides in Radix Glycyrrhizae monomeric compound in anti-inflammatory drug
In application.
To achieve the above object, a kind of compound of the present invention, it is characterised in that: the compound is dihydro Stilbene class
Closing object includes the component with the structure as shown in formula 1 and formula 2:
The wherein R of formula 11=OH, R2=OCH3, R3=OH, R4=OH；
The wherein R of formula 21=OH, R2=OCH3, R3=OH.
The compound of the formula 1:
Or its pharmaceutically acceptable salt, in which: the R of formula 11=OH, R2=OCH3, R3=OH, R4=OH；
The compound of the formula 2:
Or its pharmaceutically acceptable salt, in which: the R of formula 21=OH, R2=OCH3, R3=OH.
The compound is that furoflavone compound includes the component with the structure as shown in formula 3 and formula 4:
The wherein R of formula 31=H, R2=OH, R3=OH, R4=OH, R5=OH, R6=OH；
The wherein R of formula 41=OCH3, R2=OH, R3=H, R4=OH, R5=OH, R6=OH.
The compound of the formula 3:
Or its pharmaceutically acceptable salt, in which: the R of formula 31=H, R2=OH, R3=OH, R4=OH, R5=OH, R6=
OH；
The compound of the formula 4:
Or its pharmaceutically acceptable salt, in which: the R of formula 41=OCH3, R2=OH, R3=H, R4=OH, R5=OH, R6=
OH。
The dosage form of the compound or its pharmaceutically acceptable salt is tablet, capsule, powder, particle, granule, syrup
Agent, solution, transdermal patch, any dosage form of suppository.
The compound effective component treats or prevents the application in anti-inflammatory drugs in preparation.
The compound has the function of inhibiting NO.
The extracting method of the compound realizes that steps are as follows:
(1) Radix Glycyrrhizae 8kg is weighed, is impregnated with 80% ethyl alcohol, filtrate decompression concentration is impregnated and distills to obtain ethanol extract, add 900ml
Water is suspended, and is extracted with isometric organic solvent, obtains extractive with organic solvent；
(2) extractive with organic solvent is taken to be separated with silica gel column chromatography:
Firstly, obtaining 9 parts (Fr.A-I) using petroleum ether-ethyl acetate 100:1-0:100 gradient elution；
Then, Fr.D petroleum ether-ethyl acetate silica gel column chromatography gradient elution, obtains 6 parts (Fr.D1-D6)；Fr.G
With the open ODS column chromatography gradient elution of methanol-water, 8 parts (Fr.G1-G8) is obtained；
Last Fr.D5 is obtained through petroleum ether-acetone silica gel column chromatography gradient elution and half preparation HPLC75% methanol purifying
Dihydro stilbenes compound；Fr.G5 is pure through methylene chloride-methanol silica gel column chromatography gradient elution and half preparation HPLC60% methanol
Change, obtains furoflavone compound.
The extraction raw material is Radix Glycyrrhizae or Leaves of Glycyrrhiza Uralensis Fisch.
With 80% ethyl alcohol extraction time be 3-5 times in the step (1), 80% ethanol consumption for Leaves of Glycyrrhiza Uralensis Fisch weight 8-12
Times；Organic solvent is chloroform, ethyl acetate and n-butanol in the step (1)；Organic solvent extraction in the step (1)
Are as follows: successively with isometric chloroform, ethyl acetate and extracting n-butyl alcohol 3-4 times.
A kind of compound with anti-inflammatory activity extracted from Radix Glycyrrhizae of the present invention and its application, its advantages exist
In: the compound that the present invention obtains be noval chemical compound, the noval chemical compound be dihydro stilbenes compound with anti-inflammatory activity and
Furoflavone compound and its pharmaceutically acceptable salt.The present invention is with the byproduct Leaves of Glycyrrhiza Uralensis Fisch in Radix Glycyrrhizae production process
Raw material, extracting method is easy to operate, and extracts obtained compound purity height, and purposes is wider, and effect is preferable.The compound
To inflammatory factor nitric oxide inhibiting rate with higher, in research and development novel anti-inflammatory medicine and reasonable prospect in terms of utilizing Licorice
Well.
Specific embodiment
Embodiment 1
A kind of method extracted from Radix Glycyrrhizae with antiinflammatory active compound of the present invention, operating procedure are as follows:
1, instrument and material
AVANCE AV III-400 nuclear magnetic resonance chemical analyser (Brooker,Switzerland company)；Ultra high efficiency Two-dimensional Liquid Chromatography-
Gas phase spectrometer-level four bars time of flight ion mobility mass spectrograph (Agilent company of the U.S.)；Semipreparative high performance liquid chromatography instrument
(Shanghai Tong Wei analytical technology Co., Ltd)；EasySepTM-1050 semi-preparative liquid chromatography instrument dedicated solvent infusion pump；
The dedicated ultraviolet/visible light detector of EasySepTM-1050 semi-preparative liquid chromatography instrument；Preparative scale chromatography column (COSMOSIL-
pack 5C18-MS-Ⅱ)；Thin-layer chromatography silica GF254 and column chromatography silica gel (200-300 mesh, the limited public affairs of Qingdao Haiyang chemical industry
Department)；Agents useful for same is to analyze pure (Tianjin Fu Yu Fine Chemical Co., Ltd).
2, it extracts and separates:
Leaves of Glycyrrhiza Uralensis Fisch 8kg is weighed, after drying, is impregnated 3 times with 80% ethyl alcohol, 24 hours every time, merging filtrate was concentrated under reduced pressure
Ethanol extract is distilled to obtain, suitable quantity of water is added to be suspended, respectively three times with isometric chloroform, ethyl acetate and extracting n-butyl alcohol, is obtained
Chloroform extract 349.44g, ethyl acetate extract 92.27g, n-butanol extract 95.04g.
Ethyl acetate extract 91g is taken to be separated with silica gel column chromatography, using petroleum ether-ethyl acetate (100:1-0:100)
Gradient elution obtains 9 parts (Fr.A-I), and Fr.D silica gel column chromatography (petroleum ether-ethyl acetate) gradient elution obtains 6
Divide (Fr.D1-D6), Fr.D5 is pure through silica gel column chromatography (petroleum ether-acetone) gradient elution and half preparation HPLC (75% methanol)
Change, obtain dihydro stilbenes compound, the obtained dihydro stilbenes compound is compound 1 (formula 1), compound 2 (formula 2)；
Open ODS column chromatography (methanol-water) gradient elution of Fr.G, obtains 8 parts (Fr.G1-G8), Fr.G5 is through silica gel column chromatography (two
Chloromethanes-methanol) gradient elution and half preparation HPLC (60% methanol) purifying, furoflavone compound is obtained, it is described to obtain
Furoflavone compound is compound 3 (formula 3), compound 4 (formula 4).
3, structure and identification:
Compound 1: brown oil.Molecular formula C25H32O4；HR-ESI-MS m/z:397.2362[M+H]+；1H-NMR
(400MHz,DMSO-d6) δ: 6.54 (1H, d, J=1.6Hz, H-2), 6.40 (1H, d, J=1.6Hz, H-6), 6.13 (2H, s,
H-10,H-14),5.17(2H,m,H-2′,H-2"),3.64(3H,s,4-OCH3), 3.19 (2H, d, J=7.2Hz, H-1 '),
3.12 (2H, d, J=6.8Hz, H-1 "), 2.57 (4H, m, H-7, H-8), 1.67 (6H, s, H-4 ', H-5 '), 1.59 (3H, s, H-
4"),1.68(3H,s,H-5")；13C-NMR(100MHz,DMSO-d6)δ:155.3(C-11,C-13),149.7(C-3),143.6
(C-4),139.6(C-9),137.1(C-1),134.3(C-5),131.0(C-3′),129.0(C-3"),123.9(C-2"),
123.5(C-2′),119.6(C-6),114.3(C-2),111.7(C-12),106.2(C-10,C-14),59.6(4-OCH3),
37.1(C-8),36.7(C-7),28.3(C-1′),25.5(C-5′,C-5"),21.9(C-1"),17.7(C-4′,C-4")。
Compound 2: brown oil.Molecular formula C22H24O4；HR-ESI-MS m/z:353.1742[M+H]+,375.1564
[M+Na]+；1H-NMR(400MHz,DMSO-d6) δ: 7.71 (1H, d, J=2.0Hz, H-2 "), 6.83 (1H, d, J=2.0Hz, H-
), 1 " 6.75 (1H, d, J=0.8Hz, H-12), 6.58 (2H, br s, H-2, H-14), 6.43 (1H, d, J=1.6Hz, H-6),
5.16 (1H, t, J=7.2Hz, H-2 '), 3.64 (3H, s, 4-OCH3), 3.18 (2H, d, J=7.2Hz, H-1 '), 2.93 (2H,
m,H-8),2.73(2H,m,H-7),1.66(6H,s,H-4′,5′)；13C-NMR(100MHz,DMSO-d6)δ:155.4(C-11),
155.4(C-13),149.7(C-3),143.7(C-4),143.4(C-16),136.9(C-9),135.0(C-1),134.3(C-
5),130.9(C-3′),123.5(C-2′),119.8(C-6),118.6(C-10),114.5(C-2),111.7(C-14),
105.1(C-15),95.4(C-12),59.6(4-OCH3),35.7(C-7),34.6(C-8),28.3(C-1′),25.5(C-
5′),17.7(C-4′)。
Compound 3: brownish-yellow powder.Molecular formula C20H18O8；HR-ESI-MS m/z:387.1068[M+H]+；1H-NMR
(400MHz,DMSO-d6) δ: 7.69 (1H, s, H-3), 7.54 (1H, d, J=8.8Hz, H-6 '), 6.88 (1H, d, J=8.8Hz,
H-5 '), 6.52 (1H, s, H-8), 4.73 (1H, t, J=8.4Hz, H-2 "), 3.06 (2H, d, J=8.4Hz, H-1 "), 1.14
(3H,s,H-4"),1.16(3H,s,H-5")；13C-NMR(100MHz,DMSO-d6)δ:176.0(C-4),166.2(C-7),
156.1(C-9),154.8(C-5),147.8(C-2),146.9(C-2′),145.1(C-4′),135.8(C-3′),122.0(C-
6′),119.9(C-1′),115.6(C-3),115.2(C-5′),108.4(C-6),103.9(C-10),91.5(C-2"),88.4
(C-8),70.1(C-3"),25.0(C-4"),25.8(C-1"),25.9(C-5").
Compound 4: yellow powder.Molecular formula C21H20O8；HR-ESI-MS m/z:401.1221[M+H]+；1H-NMR
(400MHz,DMSO-d6) δ: 7.55 (1H, d, J=1.6Hz, H-2 '), 7.44 (1H, dd, J=1.6Hz, 8.4Hz, H-6 '),
6.91 (1H, d, J=8.4Hz, H-5 '), 6.52 (1H, s, H-8), 4.74 (1H, t, J=8.4Hz, H-2 "), 3.78 (1H, s, 3-
OCH3) 3.05 (2H, d, J=8.4Hz, H-1 "), 1.14 (3H, s, H-4 "), 1.15 (3H, s, H-5 ")；13C-NMR(100MHz,
DMSO-d6)δ:178.1(C-4),166.3(C-7),156.3(C-9),155.6(C-2),155.3(C-5),115.5(C-2′),
148.7(C-4′),145.3(C-3′),120.8(C-6′),120.5(C-1′),137.7(C-3),115.7(C-5′),108.4
(C-6),105.1(C-10),91.6(C-2"),88.6(C-8),70.1(C-3"),59.7(3-OCH3),24.9(C-4"),
25.8(C-1"),25.9(C-5")。
Embodiment 2
The anti-inflammatory activity evaluation for inhibiting RAW264.7 macrophage nitric oxide (NO) to generate:
With contain 10% fetal calf serum DMEM culture medium, in 37 DEG C, 5%CO2Under the conditions of cultivate RAW264.7 macrophage.
By the test sample (1,3,5 μ g/ml) of LPS (1 μ g/mL) and the various concentration for being dissolved in DMSO, it is added to cell culture fluid together
In, it cultivates under the same conditions for 24 hours.It takes 100 μ L of cell conditioned medium culture solution to be placed in 96 new orifice plates, Griess reagent is added
(1% P-aminobenzene-sulfonamide containing 5% phosphoric acid, each 50 μ L of 0.1% naphthodiamide hydrochloride).It is grasped according to NO kit specification
Make, 3 parallel holes are arranged in each concentration, and experiment is repeated 3 times.NaNO is used simultaneously2Standard solution calculate NO2 -The standard of concentration is bent
Line is negative right not to be loaded the cell culture fluid of product not add the cell culture fluid of LPS, Quercetin and sample as blank
According to using Quercetin as positive control.
Experimental result is as shown in Table 1, compared with positive control Quercetin (13.32 μM of half-inhibitory concentration), dihydro Stilbene class
Have the function of that stronger inhibition nitric oxide generates with furoflavone compound.
Table 1: compound anti-inflammatory activity measured value
Claims (10)
1. a kind of compound, it is characterised in that: the compound is that dihydro stilbenes compound includes having as shown in formula 1 and formula 2
The component of structure:
The wherein R of formula 11=OH, R2=OCH3, R3=OH, R4=OH；
The wherein R of formula 21=OH, R2=OCH3, R3=OH.
2. a kind of compound as described in claim 1, it is characterised in that:
The compound of the formula 1:
Or its pharmaceutically acceptable salt, in which: the R of formula 11=OH, R2=OCH3, R3=OH, R4=OH；
The compound of the formula 2:
Or its pharmaceutically acceptable salt, in which: the R of formula 21=OH, R2=OCH3, R3=OH.
3. a kind of compound, it is characterised in that: the compound includes having such as 4 institute of formula 3 and formula for furoflavone compound
Show the component of structure:
The wherein R of formula 31=H, R2=OH, R3=OH, R4=OH, R5=OH, R6=OH；
The wherein R of formula 41=OCH3, R2=OH, R3=H, R4=OH, R5=OH, R6=OH.
4. a kind of compound as claimed in claim 3, it is characterised in that:
The compound of the formula 3:
Or its pharmaceutically acceptable salt, in which: the R of formula 31=H, R2=OH, R3=OH, R4=OH, R5=OH, R6=OH；
The compound of the formula 4:
Or its pharmaceutically acceptable salt, in which: the R of formula 41=OCH3, R2=OH, R3=H, R4=OH, R5=OH, R6=OH.
5. the application of any compound as described in claim 1-4, it is characterised in that: the compound or its can pharmaceutically connect
The dosage form for the salt received be tablet, capsule, powder, particle, granule, syrup, solution, transdermal patch, suppository it is any
Dosage form.
6. the application of any compound as described in claim 1-4, it is characterised in that: prepared by the compound effective component
Treat or prevent the application in anti-inflammatory drugs.
7. the application of any compound as described in claim 1-4, it is characterised in that: the compound has the work for inhibiting NO
With.
8. the extracting method of any compound as described in claim 1-4, it is characterised in that: realize that steps are as follows:
(1) Radix Glycyrrhizae 8kg is weighed, is impregnated with 80% ethyl alcohol, filtrate decompression concentration is impregnated and distills to obtain ethanol extract, add 900ml water mixed
It is outstanding, it is extracted with isometric organic solvent, obtains extractive with organic solvent；
(2) extractive with organic solvent is taken to be separated with silica gel column chromatography:
Firstly, obtaining 9 parts (Fr.A-I) using petroleum ether-ethyl acetate 100:1-0:100 gradient elution；
Then, Fr.D petroleum ether-ethyl acetate silica gel column chromatography gradient elution, obtains 6 parts (Fr.D1-D6)；Fr.G first
The open ODS column chromatography gradient elution of alcohol-water, obtains 8 parts (Fr.G1-G8)；
Last Fr.D5 obtains dihydro through petroleum ether-acetone silica gel column chromatography gradient elution and half preparation HPLC75% methanol purifying
Stilbenes compound；Fr.G5 is obtained through methylene chloride-methanol silica gel column chromatography gradient elution and half preparation HPLC60% methanol purifying
To furoflavone compound.
9. the extracting method of any compound as described in claim 1-4, it is characterised in that: the extraction raw material be Radix Glycyrrhizae or
Leaves of Glycyrrhiza Uralensis Fisch.
10. the extracting method of any compound as claimed in claim 8, it is characterised in that: with 80% second in the step (1)
Alcohol extracting number is 3-5 times, and 80% ethanol consumption is 8-12 times of Leaves of Glycyrrhiza Uralensis Fisch weight；Organic solvent is chlorine in the step (1)
Imitative, ethyl acetate and n-butanol；Organic solvent extraction in the step (1) are as follows: successively with isometric chloroform, acetic acid second
Ester and extracting n-butyl alcohol 3-4 times.
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| CN114573430A (en) * | 2022-03-10 | 2022-06-03 | 中国科学院华南植物园 | Licorice anti-inflammatory substance and preparation method thereof |
| CN114869831A (en) * | 2022-05-26 | 2022-08-09 | 江苏巴帝恩生物科技有限公司 | A method for preparing cosmetic composition containing natural plants |
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| CN110396097A (en) * | 2019-09-03 | 2019-11-01 | 河南中医药大学 | Isopentene group flavone compound Chinese podophyllum root ketone U and its preparation method and application |
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| CN114573430A (en) * | 2022-03-10 | 2022-06-03 | 中国科学院华南植物园 | Licorice anti-inflammatory substance and preparation method thereof |
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| CN114869831A (en) * | 2022-05-26 | 2022-08-09 | 江苏巴帝恩生物科技有限公司 | A method for preparing cosmetic composition containing natural plants |
| CN114869831B (en) * | 2022-05-26 | 2024-04-30 | 江苏巴帝恩生物科技有限公司 | A method for preparing cosmetic composition containing natural plants |
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Application publication date: 20190531 |