CN112494478A - Composition with anti-inflammatory synergistic effect and application thereof - Google Patents
Composition with anti-inflammatory synergistic effect and application thereof Download PDFInfo
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Abstract
The invention discloses a composition with an anti-inflammatory synergistic effect, which consists of licochalcone A and licoflavone B in a molar ratio (1-7): (1-3). Compared with licochalcone A or licoflavone B, the anti-inflammatory activity of the composition provided by the invention is obviously enhanced, and is superior to other flavone compounds and compositions, so that the composition has an obvious anti-inflammatory synergistic effect. Different inflammation models prove that the anti-inflammatory synergistic effect is obvious when the licochalcone A and the licoflavone B are combined, the licoflavone B obviously influences the anti-inflammatory activity of the licochalcone A or other compositions, and the defect that the licochalcone A has obvious anti-inflammatory activity only when the content of the licochalcone A is higher than or obviously higher than that of the licoflavone B according to the prejudice of the prior art is overcome. Particularly, when the combination ratio of licochalcone A and licoflavone B is 1: 1, the composition has the highest anti-inflammatory activity and has wide application value in the anti-inflammatory field.
Description
Technical Field
The invention belongs to the field of medicine research, and mainly relates to a composition with an anti-inflammatory synergistic effect and the technical field of application thereof.
Technical Field
The flavonoid compounds generally have anti-inflammatory activity, but the anti-inflammatory activity of the flavonoid compounds is closely related to the chemical structure of the flavonoid compounds, and the flavonoid parent nucleus, substituent groups, substitution patterns and number of the flavonoid compounds can influence the anti-inflammatory activity. For example, glycosyl can significantly affect the anti-inflammatory activity of flavonoid carbon glycosides, and its contribution to anti-inflammatory activity is much greater than that of phenolic hydroxyl; as the number of sugar groups increases, the anti-inflammatory activity of the compound also increases, and the less polar the substituent group of the sugar, the less anti-inflammatory activity of the compound; moreover, the anti-inflammatory activity of the flavonoid-carbon glycoside is stronger than that of the flavonoid-oxygen glycoside, and further proves that the influence of the anti-inflammatory effect of glycosyl and phenolic hydroxyl is avoided. For another example, the differences in anti-inflammatory activity between luteolin and its 3 flavonoid glycosides (luteolin, orientin, isoorientin) are: although luteolin and 3 flavonoid glycosides thereof can inhibit HTP-1 cell inflammatory reaction induced by LPS, the inhibition effect of luteolin on proinflammatory cytokines TNF-alpha, IL-6 and the like is obviously better than that of 3 flavonoid glycosides thereof, 5 mu M luteolin has the same effect as 10 mu M NF-kappa B inhibitor, and the inhibition effect on phosphorylation of I kappa B alpha and I kappa B beta is the best of luteolin and orientin.
Because the flavonoid compounds have wider application value, the researchers never stop extracting, separating, synthesizing and modifying the flavonoid compounds, and a large amount of flavonoid active compounds are discovered along with the more intensive research on the flavonoid compounds. But because the structure is complex, the effect difference is large, the synergistic effect is strong or weak, and the flavone compound or the flavone composition which can be really applied is not much, thereby preventing the more extensive and deep development and utilization of the flavone medicament.
Licoflavone (LFs) is a group of flavonoids isolated from Licorice, and about 300 kinds of flavonoids are isolated from Licorice, including different types of flavonoids such as flavanone, chalcone, isoflavone, etc. Licochalcone A (Licochalcone A, molecular formula: C)21H22O4Molecular weight: 338.4) is the chalcone with the highest content separated and identified from liquorice, is regarded as the characteristic component of G.inflata Bat, has multiple biological activities such as antioxidation, anti-inflammation, antibiosis, antitumor and immunity promotion, and is applied to skin care, food and medicine industries at present. Modern pharmacological studies have shown that licochalcone A can inhibit secretion of inflammatory factors IL-1 beta and IL-6 of RAW264.7 cells induced by LPS. Moreover, licochalcone A can also strongly inhibit NF-kB signal channel activation induced by TNF-alpha, and inhibit IKK activation to prevent transcription of NF-kB so as to play an anti-inflammatory role. Licoflavone B (Licoflavone B, molecular formula: C)25H26O4Molecular weight: 390.5) has protective effect on LPS-induced endotoxin shock in BALB/c mice. Licoflavone (Licoflavone, molecular formula: C)20H18O4Molecular weight: 322.4), Liquiritin (Liquiritin, molecular formula: c21H22O9Molecular weight: 418.4) has antidepressant and anti-pharyngitis effects, and Isoliquiritigenin (Isooliquitinigenin, molecular formula: c15H12O4Molecular weight: 256.2) has good effects in the aspects of tumor resistance, inflammation resistance, bacteria resistance, virus resistance and the like.
Although research proves that most flavone compounds in liquorice have certain anti-inflammatory effect, the research on whether each flavone compound has anti-inflammatory synergistic effect or not and how to combine each flavone compound to improve the anti-inflammatory synergistic effect is not seen. The prior literature reports that the activity of licorice total flavonoids or a single licorice flavonoid compound in the anti-inflammatory aspect is mostly reported, and the combined application of the licorice flavonoid compound is rarely reported. The literature (research on the treatment effect and molecular mechanism of liquorice total flavonoids and liquorice chalcone A on ulcerative colitis, Liudong Yu, Beijing collaborating and medical college Master graduation paper, 2016) reports that liquorice total flavonoids have the treatment effect on ulcerative colitis, and component analysis shows that the liquorice total flavonoids contain liquorice chalcone A and liquorice flavonoid B (the ratio is 23.2: 4.3) and also contain other flavonoid compounds and terpenoid compounds, which indicates that the main component of the liquorice total flavonoids is liquorice chalcone A and has anti-inflammatory activity only when the content of the liquorice chalcone A reaches a certain standard. It is not mentioned whether licochalcone a and licoflavone B have anti-inflammatory synergy or what kind of synergy mechanism.
Disclosure of Invention
Aiming at the problem that the activity intensity of most flavone monomeric compounds cannot meet the application requirements easily, no document and no patent report whether licochalcone A and licoflavone B have a synergistic effect in the anti-inflammatory aspect, how to play the synergistic effect and the influence of the compatibility proportion on the anti-inflammatory synergistic effect of the licochalcone A and the licoflavone B are disclosed. Therefore, how to overcome the existing technologies, for example, the literature ("research on therapeutic effect and molecular mechanism of licochalcone a on ulcerative colitis", liu dong yu, beijing synergetics and medical college major graduate treatise in 2016) indicates that licochalcone a, the main component of licochalcone a in licoflavone, has anti-inflammatory effect only when the content of licochalcone a reaches a certain standard and is much higher than that of other flavone compounds or terpenoids. The invention aims to provide a composition with anti-inflammatory synergistic effect and application thereof, wherein the composition consists of licochalcone A and licoflavone B which are prepared according to a specific molar ratio. Different inflammation models prove that when the licochalcone A and the licoflavone B are combined, the anti-inflammatory synergistic effect is obvious: comparing the anti-inflammatory activity of 5 flavone compounds and 6 different compositions, the result shows that the composition (licochalcone A + licoflavone B) of the invention has the most significant anti-inflammatory activity compared with each flavone compound and other compositions, and licoflavone B plays a main role in anti-inflammatory synergistic effect, and the anti-inflammatory activity of each flavone compound and other compositions is significantly influenced by whether licoflavone B is used in a compatible way or not. Further animal experiments confirm that when the combination ratio of licochalcone A and licoflavone B is 1: the composition has the best anti-inflammatory activity in 1 hour, can remarkably reduce the granuloma index (P <0.01) of an inflammatory mouse, is remarkably improved (P <0.05) compared with that of a single use of licochalcone A or licoflavone B, can remarkably reduce the histamine content (P <0.05) and remarkably reduce the 5-hydroxytryptamine content (P <0.01), and shows that the composition has the highest anti-inflammatory activity and has wide application value in the anti-inflammatory field.
The invention particularly provides a composition with an anti-inflammatory synergistic effect, which consists of licochalcone A and licoflavone B in a molar ratio (1-7): (1-3).
Preferably, the composition with the anti-inflammatory synergistic effect comprises licochalcone A and licoflavone B according to a molar ratio of 1: 1, was prepared.
In the invention, licochalcone A and licoflavone B are obtained by a common purification method, wherein the licochalcone A and the licoflavone B are obtained by extracting the swollen liquorice or liquorice slag with an ethanol solution, concentrating the extract, passing the concentrated extract through a macroporous resin column, removing impurities, eluting the concentrated extract with the ethanol solution and collecting the eluted extract.
The invention is prepared by preferably adopting licochalcone A and licoflavone B: extracting distending fruit liquorice or liquorice residues with 85% ethanol solution, concentrating, extracting with ethyl acetate, passing through a silica gel column, performing gradient elution with a petroleum ether-acetone system (100:0-2:1), and respectively collecting the components in the ratio of 8: 1, concentrating and drying an eluted part to obtain A, and collecting 6: concentrating and drying the eluted part of the eluent 1 to obtain a compound B, wherein the content of licochalcone A in the compound A is more than 70 percent, and the content of licoflavone B in the compound B is more than 70 percent. Licochalcone A and licoflavone B are mixed according to a molar ratio (1-7): (1-3) combining A, B parts to obtain the composition with the anti-inflammatory synergistic effect.
Further, the invention provides application of the composition with the anti-inflammatory synergistic effect in preparing anti-inflammatory drugs.
By implementing the content of the invention through the technical scheme provided by the invention, the following beneficial effects can be achieved:
(1) the invention provides a composition with an anti-inflammatory synergistic effect, which consists of licochalcone A and licoflavone B in a molar ratio (1-7): the anti-inflammatory activity of the composition is obviously enhanced compared with that of licochalcone A or licoflavone B, and the composition is superior to that of each flavone compound and other compositions, so that the obvious anti-inflammatory synergistic effect exists between the licochalcone A and the licoflavone B. Different inflammation models prove that when the licochalcone A and the licoflavone B are combined, the anti-inflammatory synergistic effect is obvious: compared with various flavone compounds and other compositions, the composition (licochalcone A and licoflavone B) has the most obvious anti-inflammatory activity, and licoflavone B plays a main role in anti-inflammatory synergistic effect, and the anti-inflammatory activity of various flavone compounds and other compositions is obviously influenced by compatibility of licoflavone B. Overcomes the prejudice of the prior art that the licochalcone A content is higher or obviously higher than the licoflavone B to have obvious anti-inflammatory activity.
(2) The composition with the anti-inflammatory synergistic effect provided by the invention comprises licochalcone A and licoflavone B according to a molar ratio (1-7): the composition obtained by the (1-3) can obviously or very obviously reduce the granuloma index (P <0.05 or P <0.01) of an inflammatory mouse, obviously reduce the histamine content (P <0.05) and very obviously reduce the 5-hydroxytryptamine content (P <0.01), and shows the synergistic effect of the two on the anti-inflammatory aspect. Particularly, when the molar ratio of licochalcone A to licoflavone B is 1: 1, the composition has the highest anti-inflammatory activity and has wide application value in the anti-inflammatory field.
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Detailed Description
The present invention will be described below by way of examples, but the present invention is not limited to the following examples. All the raw and auxiliary materials selected in the invention are well known and selected in the field.
Example 1: composition with anti-inflammatory synergistic effect
The composition consists of licochalcone A and licoflavone B, wherein the molar ratio of the licochalcone A to the licoflavone B is 50: 50.
Example 2: composition with anti-inflammatory synergistic effect
The composition consists of licochalcone A and licoflavone B according to a molar ratio of 60: 40.
Example 3: composition with anti-inflammatory synergistic effect
The composition consists of licochalcone A and licoflavone B according to a molar ratio of 56: 44.
Example 4: composition with anti-inflammatory synergistic effect
The composition consists of licochalcone A and licoflavone B, wherein the two are mixed according to a molar ratio of 67: 33.
Example 5: composition with anti-inflammatory synergistic effect
The composition consists of licochalcone A and licoflavone B, wherein the two are mixed according to a molar ratio of 70: 30.
Example 6: comparison of antiinflammatory Activity of Flavonoids and composition
This example compares the anti-inflammatory and anti-inflammatory synergy of the compositions provided by the present invention with each of the flavonoid compounds and other compositions based on examples 1-5.
(1) Comparison of anti-inflammatory Activity of Flavonoids
Establishing a TNF-alpha induced IEC-6 inflammatory cell model. C1 (licochalcone A, C) was examined separately with positive drug as control (SASP)21H22O4) C2 (licoflavone B, C)25H26O4) C3 (licoflavone, C)20H18O4) C4 (glycyrrhizin, C)21H22O9) C5 (isoliquiritigenin, C)15H12O4) The results of the inhibition effect on the proinflammatory factor IL-6 are shown in the table 1.
Table 1: effect of Flavonoids on TNF-alpha induced IEC-6 inflammatory cells
Note: tangle-solidup, P <0.05 compared to blank; Δ compared to model group, P < 0.05; T.T.compared to the positive drug intervention group, P < 0.05.
The data in Table 1 show that IEC-6 cells induced by TNF-alpha secrete a large amount of proinflammatory factors (P <0.05), and early intervention by C1, C2, C3, C4 and C5 can remarkably inhibit IL-6 secretion (P <0.05), and the inhibition effect of C2 and C3 is strongest, and the inhibition effect of 20 mu M of C2 and C3 on IL-6 is even better than that of a positive drug (P < 0.05).
(2) Comparison of anti-inflammatory Activity of compositions
On the basis of test 1, the effects of different compositions prepared with C1, C2, C3, C4 and C5, respectively, on TNF- α induced IEC-6 inflammatory cells were further examined, and the specific results are shown in tables 2-3.
Table 2: effect of different compositions on TNF-alpha induced IEC-6 inflammatory cells
Table 3: effect of different compositions on TNF-alpha induced IEC-6 inflammatory cells
Note: tangle-solidup, P <0.05 compared to blank; Δ compared to model group, P < 0.05; T.T.compared to the positive drug intervention group, P < 0.05; p <0.05 compared to group C1+ C3+ C4+ C5
As can be seen from the data in tables 3-4, the anti-inflammatory activity of the different compositions is different and not any two or more of the components can be combined to exert a synergistic effect: the effect of C1+ C2 is better than that of C1+ C3, C1+ C4 and C1+ C5, the inhibition effect on inflammatory factors under the concentration of 10 mu M is better than that of positive drugs (P is less than 0.05), and the inhibition effect is obviously better than that of singly using C1 and C2, which shows that the two have synergistic effect; the anti-inflammatory activity of the C3 is equivalent to that of the C2, but compared with the C1+ C3, the C1 and the C3 are not obviously changed, which shows that the two have no synergistic effect basically; c1+ C4 is slightly improved compared with C4, C1+ C5 is equivalent to C5, and the C4, C5 and C1 have no synergistic effect; c1+ C3+ C4+ C5 are slightly improved in the two concentrations compared with C3, C4 and C5 which are used alone, but the effects are similar to those of C1 which shows that C3, C4 and C5 do not particularly contribute to the improvement of the activity of C1. However, after C2 is added into C1+ C3+ C4+ C5, namely the anti-inflammatory activity of C1+ C2+ C3+ C4+ C5 is greatly improved (P is less than 0.05), the activity is obviously superior to that of each compound which is singly used and superior to that of a positive drug (P is less than 0.05), and more importantly, no significant difference exists between the anti-inflammatory activity and a blank group (P is more than 0.05), and the inflammatory response level can be greatly reduced by adding C2, namely licoflavone B, so that the secretion of proinflammatory factors is restored to a normal level.
Example 7: comparison of antiinflammatory Activity of Flavonoids and composition
This example compares the anti-inflammatory and anti-inflammatory synergy of the compositions provided by the present invention with each of the flavonoid compounds and other compositions based on examples 1-5.
Establishing a Hacat inflammatory cell model induced by TNF-alpha. C1 (licochalcone A, C) was examined separately with positive drug as control (DMX)21H22O4) C2 (licoflavone B, C)25H26O4) C3 (licoflavone, C)20H18O4) C4 (glycyrrhizin, C)21H22O9) C5 (isoliquiritigenin, C)15H12O4) The results of the inhibition effect on the proinflammatory factor IL-6 are shown in a table 4.
Table 4: effect of Flavonoids on TNF-alpha induced IEC-6 inflammatory cells
Note: tangle-solidup, P <0.05 compared to blank; Δ compared to model group, P < 0.05; T.T.compared to the positive drug intervention group, P < 0.05.
As shown in the data in Table 4, the Hacat cells induced by TNF-alpha can secrete a large amount of proinflammatory factors (P <0.05), and if C1, C2, C3, C4 and C5 intervene in advance, the secretion of IL-6 (P <0.05) can be remarkably inhibited, the inhibition effect of C2 and C3 is strongest, and the inhibition effect of 20 mu M C2 and C3 on IL-6 is even better than that of a positive drug (P < 0.05).
(2) Comparison of anti-inflammatory Activity of compositions
On the basis of test 1, the effect of different compositions prepared with C1, C2, C3, C4, C5, respectively, on TNF- α induced Hacat inflammatory cells was further examined, see tables 5-6 for specific results.
Table 5: effect of different compositions on TNF-alpha induced Hacat inflammatory cells
Table 6: effect of different compositions on TNF-alpha induced Hacat inflammatory cells
Note: tangle-solidup, P <0.05 compared to blank; Δ compared to model group, P < 0.05; T.T.compared to the positive drug intervention group, P < 0.05; p <0.05 compared to group C1+ C3+ C4+ C5
As can be seen from the data in tables 5-6, the trend of intervention of the different compositions on TNF- α induced Hacat inflammatory cells was similar to that of IEC-6 inflammatory cells of example 6, and not every composition had an enhanced anti-inflammatory activity, i.e., not the anti-inflammatory components combined together could exert a synergistic effect: the effect of C1+ C2 is better than that of C1+ C3, C1+ C4 and C1+ C5, and is obviously better than that of C1 and C2 which are used independently, the anti-inflammatory activity is better than that of a positive drug (P is less than 0.05) at the concentration of 10 mu M, and no significant difference (P is more than 0.05) exists between the anti-inflammatory activity and a blank group at the concentration of 20 mu M, namely, the anti-inflammatory factor can be restored to a normal level by C1+ C2, and the anti-inflammatory agent has good synergistic effect; c1+ C3 and C1+ C4 are only slightly improved compared with C3 and C4 which are used independently, and C1+ C5 is equivalent to C5, namely C3, C4, C5 and C1 do not play a synergistic effect in combination; c1+ C3+ C4+ C5 is improved compared with C4 and C5 which are used independently, but is basically equivalent to C1 and C3 which are used independently, and no obvious synergistic effect exists among C1, C3, C4 and C5; however, after C2 is added into C1+ C3+ C4+ C5, namely the anti-inflammatory activity of C1+ C2+ C3+ C4+ C5 is greatly improved (P is less than 0.05), the activity is obviously superior to that of each compound which is singly used and is obviously superior to that of a positive drug (P is less than 0.05), no significant difference exists between the anti-inflammatory activity and a blank group (P is more than 0.05), and the inflammatory response level can be greatly reduced by adding C2, namely licoflavone B, so that the secretion of proinflammatory factors is restored to a normal level.
Combining all data, C1 and C2 are considered to have obvious synergistic effect on anti-inflammatory.
Example 8: application of the anti-inflammatory synergistic composition
This example is based on examples 1-5, and optimizes the composition ratio by comparing the synergistic effect difference of the compositions in different proportions in anti-inflammatory aspect.
Establishing a granuloma inflammation mouse model, taking a positive drug as a control (DMX, 5mg/kg), administering the positive drug at a dose of 20mg/kg, administering the positive drug with the same dose of normal saline to the model group, performing intragastric administration for 1 time every day, continuously administering the normal saline for 7 days, and respectively inspecting C1 (licochalcone A, C)21H22O4) C2 (licoflavone B, C)25H26O4) A-C1+ C2 (50: 50) B-C1+ C2 (56: 44) C-C1+ C2 (60: 40) D-C1+ C2 (67: 33) E-C1+ C2(70:30) with the results shown in tables 7-8.
Table 7: effect of the compositions of the invention on granuloma index
| Grouping | Granuloma index (mg/g) |
| Model set | 3.11±0.54 |
| Positive drug group | 1.67±0.56ΔΔ |
| Group C1 | 2.14±0.48Δ |
| Group C2 | 2.06±0.35Δ |
| A-C1+C2 | 1.31±0.37ΔΔ* |
| B-C1+C2 | 1.39±0.73ΔΔ |
| C-C1+C2 | 1.39±0.87ΔΔ |
| D-C1+C2 | 1.46±0.56ΔΔ |
| E-C1+C2 | 1.48±0.41ΔΔ |
Note: Δ compared to model group, P < 0.05; Δ P <0.01 compared to model group; p <0.05 compared to group C1/C2.
As can be seen from the data in Table 7, positive drug DMX significantly reduced the granuloma index of cotton balls (P <0.01) compared to the model group. C1, C2 also significantly reduced the granuloma index (P <0.05), whereas composition A, B, C, D, E both significantly reduced the granuloma index of cotton boll (P <0.01), and composition a was significantly improved over C1, C2 alone (P <0.05), indicating that C1 and C2 have significant synergistic effects in anti-inflammatory and are present in a molar ratio of 50: 50 is the best.
Table 8: effect of the compositions of the present invention on Histamine and 5-hydroxytryptamine in varying proportions
| Grouping | Histamine (ug/100 ul) | 5-hydroxytryptamine (μ g/100ul) |
| Model set | 5.21±1.09 | 12.23±1.06 |
| Positive drug group | 3.01±0.91Δ | 7.45±1.15Δ |
| Group C1 | 4.46±0.93 | 7.41±0.89Δ |
| Group C2 | 4.52±1.09 | 7.22±0.72Δ |
| A-C1+C2 | 3.27±0.22Δ | 6.07±0.90ΔΔ |
| B-C1+C2 | 3.33±0.78Δ | 6.18±0.37ΔΔ |
| C-C1+C2 | 3.32±0.21Δ | 6.16±0.60ΔΔ |
| D-C1+C2 | 3.40±0.33Δ | 6.29±0.67ΔΔ |
| E-C1+C2 | 3.40±0.47Δ | 6.37±1.05ΔΔ |
Note: Δ compared to model group, P < 0.05; Δ P <0.01 in comparison with the model group
As can be seen from the data in table 8, the positive drug DMX significantly reduced histamine and 5-hydroxytryptamine levels compared to the model group (P < 0.05). C1 and C2 only have significant difference (P <0.05) in the effect of 5-hydroxytryptamine, while composition A, B, C, D, E can both significantly reduce histamine content (P <0.05) and significantly reduce 5-hydroxytryptamine content (P < 0.01). The synergistic effect of C1 and C2 on anti-inflammation is further proved.
In summary, C1, C2, C1 and C2 all have an inflammation-inhibiting effect on granulomatous mice and are achieved by modulating histamine and 5-hydroxytryptamine. Meanwhile, the proportions of C1 and C2 are (1-7): (1-3) when the two are combined, the anti-inflammatory activity of the composition can be obviously improved, and the anti-inflammatory activity of the composition have an obvious synergistic effect, wherein when the molar ratio of C1 to C2 is 50: at 50, the anti-inflammatory activity of the composition is highest, so the composition has wide application value in the field of preparing medicaments for preventing and treating inflammatory diseases.
The above examples are merely illustrative for clearly illustrating the present invention and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications can be made while remaining within the scope of the present invention.
Claims (3)
1. The composition with the anti-inflammatory synergistic effect is characterized by consisting of licochalcone A and licoflavone B according to a molar ratio (1-7): (1-3).
2. The anti-inflammatory synergistic composition of claim 1, wherein the composition comprises licochalcone a and licoflavone B in a molar ratio of 1: 1, was prepared.
3. Use of a composition with antiinflammatory synergistic effect according to claim 1 for the preparation of an antiinflammatory medicament.
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