CN109320575B - Pseudo-ginsenoside 12-ketone-PF 11, extraction method and medical application thereof - Google Patents
Pseudo-ginsenoside 12-ketone-PF 11, extraction method and medical application thereof Download PDFInfo
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Abstract
本发明涉及拟人参皂苷12‑酮‑PF11及提取方法及其医药用途，属医药领域。取西洋参花蕾适量，加3～5倍量的80～95％乙醇加热回流提取，每次2～4小时，共提取3～5次，提取液回收溶剂至干后，依次以大孔吸附树脂、硅胶柱层析、C18反相硅胶开放柱或者中压制备柱分离，甲醇等有机溶剂重结晶得到拟人参皂苷12‑酮‑PF11。本发明进行了动物模型实验，能降低小鼠过敏性休克的死亡率，减轻迟发型超敏反应小鼠耳肿胀度，并抑制5‑羟色胺和组胺导致的小鼠毛细血管通透性增加。本发明的拟人参皂苷12‑酮‑PF11作为药物活性成分，有望开发成为用于预防和治疗过敏性疾病的新型药物，为过敏性疾病的预防和治疗提供临床指导与依据，进而减轻患者痛苦，改善患者生活质量。The invention relates to a pseudoginsenoside 12-ketone-PF11, an extraction method and medicinal use thereof, and belongs to the field of medicine. Take an appropriate amount of American ginseng flower buds, add 3 to 5 times the amount of 80 to 95% ethanol for heating and reflux extraction, each time for 2 to 4 hours, and extract 3 to 5 times in total. Silica gel column chromatography, C 18 reversed-phase silica gel open column or medium pressure preparative column separation, and recrystallization from organic solvents such as methanol to obtain pseudoginsenoside 12-ketone-PF11. The invention has carried out animal model experiments, which can reduce the mortality rate of anaphylactic shock in mice, reduce the ear swelling of mice with delayed type hypersensitivity reaction, and inhibit the increase of capillary permeability of mice caused by serotonin and histamine. The pseudoginsenoside 12-ketone-PF11 of the present invention is expected to be developed into a new type of drug for the prevention and treatment of allergic diseases as a pharmaceutical active ingredient, and provides clinical guidance and basis for the prevention and treatment of allergic diseases, thereby reducing the suffering of patients, Improve patients' quality of life.
Description
Technical Field
The invention belongs to the field of medicines, and particularly relates to pseudoginsenoside 12-ketone-PF 11, an extraction method thereof and application thereof in preparing a medicine for treating allergic diseases.
Background
Allergic diseases are type I allergic diseases caused by contacting the body with external allergens, and are also called immediate-type or allergic diseases. Clinically, the allergic diseases comprise various diseases such as urticaria, eczema, characteristic dermatitis, allergic asthma, allergic rhinitis and the like. With the social development, the accelerated industrialization process and the change of life style of people, the prevalence rate of allergic diseases is continuously improved, and the life quality of patients is seriously affected by the allergic diseases. The current medicines commonly used for clinically treating allergic diseases are antihistamine, corticosteroid hormone, immunosuppressant and the like. However, the above treatment has the following problems: short drug action time, high price and long period, and the long-term use of corticosteroid hormone and immunosuppressant can aggravate side effects of microvascular injury, corticosteroid suffering and body immune system destruction. Therefore, the research on the medicaments for treating the disease needs to be strengthened, and the search for effective treatment methods is of great significance.
Modern pharmacological research shows that the ginseng of the Araliaceae family and the saponin and polysaccharide components thereof have the treatment effect on allergic diseases: the red ginseng can reduce scratching caused by mouse characteristic dermatitis allergy, relieve characteristic dermatitis-like skin lesion symptoms and relieve allergic rhinitis; ginsenoside Rh2 and Rd can relieve anaphylaxis caused by Compound48/80 and IgE; ginsenoside Rg3, Rf and Rg5 can inhibit IgE-induced passive skin anaphylaxis; the ginsenoside Rg5 and Rh3 can relieve the symptoms of chronic dermatitis; the ginsenoside Rh2 and Rh1 can relieve airway inflammatory reaction of a mouse asthma model and have a therapeutic effect on asthma; the ginsenoside Rh1 can inhibit rat anaphylaxis by acting on mast cells, and simultaneously resist Ig-E induced passive skin hypersensitivity of mice; the panaxan reduces the occurrence of asthma reaction in mice; american ginseng root polysaccharide extract patent product CVT-E002
Can reduce the virus infection of human airways clinically, and experimental research shows that the anaphylactic reaction of mice can be reduced. The research results for treating allergic diseases show that the components such as ginsenoside and polysaccharide in the araliaceae plant have potential effects on treating allergic diseases.
American ginseng (Panax quinquefolius L.) is a perennial plant of Panax of Araliaceae, is native to Canada and USA, and is planted in Changbai mountain and other places in China. The American ginseng flower bud is a traditional Chinese medicine storage organ of American ginseng plant nutrient components, and the content of active components, such as saponin, is higher than that of other growing parts (roots, stems, leaves and fruits). CVT-E002 extracted from radix Panacis Quinquefolii except the above polysaccharide extract
In addition, the research of American ginseng in allergic diseases is rarely reported, and the research of the unique octreotide-type saponin in American ginseng in allergic diseases is blank.
Disclosure of Invention
The invention provides pseudoginsenoside 12-ketone-PF 11, an extraction method and medical application thereof, and the medical application is application in preparing medicines for treating allergic diseases.
The invention adopts the technical scheme that the pseudoginsenoside 12-ketone-PF 11 has the following formula:
molecular weight: 798.5
Chemical name: 6-O- [ α -L-rhamnopyranosyl- (1-2) - β -D-glucopyranosyl ] -dammara-12-one-20S, 24R-epoxy-3 β,6 α, 25-triol;
the molecular formula is as follows: c42H70O14
White powder, easily soluble in methanol and pyridine. TLC detection, 10% H2SO4The ethanol solution is a color developing agent, and is heated to be purple at 105 ℃.
The extraction method of the pseudoginsenoside 12-ketone-PF 11 comprises the following steps:
taking dried American ginseng flower buds, crushing, adding 3-5 times of 80-95% ethanol, heating, refluxing and extracting for 3-5 times each time for 2-4 hours, extracting for 3-5 times, combining extracting solutions, recovering a solvent to be dry, suspending the solvent with water, adding the suspending solution into D-101 or AB-8 macroporous adsorption resin, firstly washing with water, then eluting with 30-45% ethanol, then eluting with 70-85% ethanol, collecting 70-85% ethanol eluent, recovering the solvent to be dry, then carrying out 2-3 times of 200-mesh 400-mesh silica gel column chromatography, and eluting with an eluent: n-butanol or dichloromethane or chloroform: ethyl acetate or ethanol or methanol: water (5-20): (1-5); (1-5), concentrating the eluent under reduced pressure, recovering to dryness, and carrying out C18Separating with reverse phase silica gel open column or medium pressure preparative column, eluting with methanol or acetonitrile: and (25-75) of water, (25-75), recovering under reduced pressure to dryness, and recrystallizing with methanol, ethanol, ethyl acetate or acetonitrile to obtain the pseudoginsenoside 12-ketone-PF 11.
Preferably:
taking dried American ginseng flower buds, crushing, adding 3 times of 80% ethanol, heating, refluxing and extracting for 4 hours each time for 3 times, combining extracting solutions, recovering a solvent to be dry, suspending the extracting solution by using water, adding the suspending solution into D-101 macroporous adsorption resin, firstly washing by using water, then eluting by using 45% ethanol, then eluting by using 70% ethanol, collecting 70% ethanol eluent, recovering the solvent to be dry, then carrying out 2 times of 400-mesh silica gel column chromatography, and eluting: n-butanol: ethyl acetate: concentrating the eluate under reduced pressure to dry, and performing C18Separating by a reverse phase silica gel medium pressure preparation column, wherein the eluent is methanol: and (3) recovering water at a ratio of 50:50 under reduced pressure to dryness, and recrystallizing with ethanol to obtain the pseudoginsenoside 12-keto-PF 11.
The invention relates to application of pseudoginsenoside 12-ketone-PF 11 in preparing a medicament for treating allergic diseases.
When the invention is used for preparing the medicament for treating the allergic diseases, the oral administration or the parenteral administration is safe. In the case of oral administration, it may be administered in any conventional form, such as powder, granule, tablet, capsule, pill, drop pill, soft capsule, floating agent, oral liquid, suspension, syrup, buccal tablet, spray or aerosol, etc.; when the drug is administered parenterally, it may take any conventional form, such as injections: such as intravenous injection, ointment, suppository, transdermal administration, inhalant, etc.
The present invention relates to a pharmaceutical composition for treating allergic diseases, which comprises a single active ingredient or a combination of an active ingredient and a solid or liquid excipient, wherein the solid or liquid excipient is well known in the art, and the solid excipient is selected from lactose, starch, dextrin, calcium carbonate, synthetic or natural aluminum sulfate, magnesium chloride, magnesium stearate, sodium bicarbonate, dried yeast and other liquid excipients, such as water, glycerin, propylene glycol, simple syrup, ethanol, ethylene glycol, polyethylene glycol, sorbitol and other ointments.
The invention has the beneficial effects that the novel compound pseudo-ginsenoside 12-ketone-PF 11 is obtained by first separation and is used for treating allergic diseases, can be used for preparing medicines for treating the allergic diseases and has the characteristic of remarkable curative effect. The dosage of the effective substance may vary depending on the administration mode, the age and weight of the patient, the severity of the condition, and other similar factors.
Drawings
FIG. 1 is a drawing of a compound of the present invention1H NMR spectrum;
FIG. 2 is a drawing of a compound of the present invention13C NMR spectrum;
FIG. 3 is an HSQC spectrum of a compound of the present invention;
FIG. 4 is an HMBC spectrum of a compound of the present invention;
FIG. 5 is a drawing of a compound of the present invention1H-1H COSY spectrogram;
FIG. 6 is a MS spectrum of a compound of the present invention;
FIG. 7 is a graph showing the effect of pseudoginsenoside 12-keto-PF 11 on the survival rate of a mouse model of anaphylactic shock.
Detailed Description
Example 1
Taking dried western medicine10kg of American ginseng bud, crushing, adding 4 times of 85% ethanol, heating and refluxing for extraction, extracting for 4 times each time for 3 hours, combining extracting solutions, recovering a solvent to be dry, suspending the extracting solution by using water, adding the suspending solution into AB-8 macroporous adsorption resin, firstly washing by using water, then eluting by using 40% ethanol, then eluting by using 75% ethanol, collecting 75% ethanol eluent, recovering the solvent to be dry, and then carrying out 2 times of 200-mesh silica gel column chromatography, wherein the eluent comprises the following components: trichloromethane: methanol: water 10: 3; 1, concentrating the eluent under reduced pressure and recovering the eluent to be dry, and carrying out C18Separating by using a reverse phase silica gel open column or a medium-pressure preparation column, wherein the eluent is acetonitrile: water-40: 60, recovering under reduced pressure to dryness, and recrystallizing with ethyl acetate to obtain pseudoginsenoside 12-ketone-PF 11;
structure identification is carried out by adopting a spectroscopy method:
HR-ESI-MS spectrum gives a molecular weight of 799.4841[ M + H ]]+(calculated value 799.4844, C42H71O14) Quasi-molecular ion peak of (3), binding1H NMR、13C NMR spectrum to confirm the molecular formula as C42H70O14. Positive by Libermann-Burchard, 10% H by TLC2SO4Heating the ethanol solution as developer at 105 deg.C to purple to indicate ginsenoside compounds; performing gas mass spectrometry on the acid hydrolysis product of the compound, and comparing and analyzing by using a standard substance to confirm that the connected glycosyl is D-glucose and L-rhamnose;
1H NMR(600MHz,pyridine-d5): high field gives 9 methyl signals: δ 0.85(3H, s),0.99(3H, s),1.21(3H, s),1.36(3H, s),1.37(3H, s),1.40(3H, s),1.42(3H, s),2.10(3H, s),1.87(3H, d, J ═ 6.2 Hz); no alkene hydrogen proton signal is given; the midfield gives two terminal proton signals for β -D-glucose and α -L-rhamnose: δ 5.29(1H, d, J ═ 6.9Hz),6.49(1H, s); the proton signal at the H-6 position appears at delta 4.76(1H, m), indicating that 6 position has-OH substitution, suggesting possible triol type ginsenoside; the hydrogen spectrum of this compound does not give a proton signal of H-12, and the proton chemical shifts of H-11 and H-13 are biased to low fields, compared to pseudoginsenoside F11: δ 2.33(2H, m, H-11), 3.10(1H, m, H-13), suggesting that the 12-position may be a carbonyl group;1in the H NMR spectrumOther proton signals are also given;
13C NMR(150MHz,pyridine-d5): giving a total of 48 carbon signals; the chemical shifts of C-7 and C-8 are delta 45.6 and 42.0 respectively, and the conclusion that the compound is triol type ginsengenin is verified; compared with 20S protopanaxatriol saponin, the C-16 position in the compound is shifted by about 1ppm to delta 25.6 in high field, and two oxygen connecting carbon signals of delta 85.8(C-20) and 85.1(C-24) indicate the existence of a C-17 side chain furan ring, so that the compound is the oxtriptolone type ginsenoside; the chemical shifts of the A, B, D ring, the 17-position side chain and two sugars of the compound are basically consistent with the literature report of the pseudoginsenoside F11, but a signal of carbonyl carbon delta 210.8(C-12) appears, and the chemical shifts of the carbons at 9, 10, 11, 13 and 14 positions on the C ring are biased to low fields: δ 54.2, 40.0, 40.5, 57.3, 56.1, indicating a carbonyl group at position 12; the HMBC spectrum gives the following main correlations that demonstrate the presence of a proton at the 12-carbonyl group with the carbon signal: H-11/C-12; H-13/C-12, C-14, C-17, C-20, C-30; H-15/C-17; H-21/C-17, C-20, C-22; H-24/C-26; H-26/C-25, C-27; H-27/C-25, C-24; h-1 '/C-6, C-2'; h-1 '/C-2 ', C-2 '. According to HSQC, HMBC and1H-1h COSY spectrogram, the hydrocarbon signal of the compound is subjected to full attribution, and the data are shown in Table 1.
Comprehensive analysis, and the compound is identified to be 6-O- [ alpha-L-rhamnopyranosyl- (1-2) -beta-D-glucopyranosyl ] -dammar-12-one-20S, 24R-epoxy-3 beta, 6 alpha, 25-triol. The SciFinder search does not find a literature report about the compound, and the compound is a new compound and is named as pseudo-ginsenoside 12-ketone-PF 11.
Of the compound1H NMR spectrum,13C NMR spectrum, HSQC spectrum, HMBC spectrum, C-NMR spectrum, HSQC spectrum, HSBC spectrum, HSQC spectrum, HSC spectrum,1H-1the H COSY spectrogram and the MS spectrogram are shown in figures 1-6 respectively.
TABLE 1 NMR data of pseudoginsenoside 12-keto-PF 11 correlated with HMBC
1H NMR(600MHz,pyridine-d5)；13C NMR(150MHz,pyridine-d5)
Example 2
Taking 20kg of dried American ginseng flower buds, crushing, adding 3 times of 80 ethanol, heating, refluxing and extracting for 4 hours each time for 5 times, combining extracting solutions, recovering a solvent to be dry, suspending the extracting solution by using water, adding the suspending solution into D-101 macroporous adsorption resin, firstly washing by using water, then eluting by using 30% ethanol, then eluting by using 70% ethanol, collecting 70% ethanol eluent, recovering the solvent to be dry, then carrying out 2 times of 200-mesh silica gel column chromatography, and eluting: n-butanol: ethyl acetate: water 5: 1; 3, concentrating the eluent under reduced pressure and recovering the eluent to be dry, and performing C18Separating with reverse phase silica gel open column or medium pressure preparative column, eluting with methanol: and (5) recovering water at a ratio of 25:75 under reduced pressure to dryness, and crystallizing by using ethanol to obtain the pseudoginsenoside 12-keto-PF 11.
Example 3
Taking 5kg of dried American ginseng flower buds, crushing, adding 5 times of 95% ethanol, heating, refluxing and extracting for 2 hours each time for 3 times, combining extracting solutions, recovering a solvent to be dry, suspending the solvent by water, adding the suspending solution into D-101 macroporous adsorption resin, firstly washing by water, then eluting by 45% ethanol, then eluting by 85% ethanol, collecting 85% ethanol eluent, recovering the solvent to be dry, and then carrying out 3 times of 400-mesh silica gel column chromatography, eluting by an eluent: dichloromethane: ethanol: 20 parts of water: 5; concentrating the eluate under reduced pressure, recovering to dryness, and performing step C18Separating by using a reverse phase silica gel open column or a medium-pressure preparation column, wherein the eluent is acetonitrile: and (5) recovering water at a ratio of 75:25 under reduced pressure until the water is dried, and recrystallizing the water by using methanol to obtain the pseudoginsenoside 12-keto-PF 11.
Example 4
Pulverizing dried bud of radix Panacis Quinquefolii 3kg, adding 3 times of 80% ethanol, heating and reflux extracting for 4 hr each timeExtracting for 3 times, mixing extractive solutions, recovering solvent to dry, suspending with water, adding into D-101 macroporous adsorbent resin, washing with water, eluting with 45% ethanol, eluting with 70% ethanol, collecting 70% ethanol eluate, recovering solvent to dry, and performing 400-mesh silica gel column chromatography for 2 times to obtain eluent: n-butanol: ethyl acetate: concentrating the eluate under reduced pressure to dry, and performing C18Separating by a reverse phase silica gel medium pressure preparation column, wherein the eluent is methanol: and (3) recovering water at a ratio of 50:50 under reduced pressure to dryness, and recrystallizing with ethanol to obtain the pseudoginsenoside 12-keto-PF 11.
The effects of the present invention are further illustrated by the pharmacodynamic test examples below.
Test example 1: effect of pseudoginsenoside 12-keto-PF 11 on anaphylactic shock in mice caused by Compound 48/80.
A type I hypersensitivity shock model was established for BALB/c mice using Compound 48/80. BALB/c mice 60, half male and half female, were randomly divided into normal group, model group, positive drug chlorpheniramine group (4mg/kg) pseudoginsenoside 12-ketone-PF 11 low, medium and high dose groups (10 mg/kg; 20 mg/kg; 40 mg/kg). The normal control group and the model group are respectively administered with equal volume of physiological saline, positive drug and pseudoginsenoside 12-ketone-PF 11 by intragastric administration once a day for 7 days. Mice were observed for mortality within 15, 30, 45, 60min after intraperitoneal injection of Compound48/80(10mg/kg) after l h last dose, and survival was recorded.
As a result: as shown in fig. 7, table 2, Compound48/80 at 10mg/kg can cause mice to shock, die (statistically significant differences compared to normal groups,###P<0.001); the administration of the pseudoginsenoside 12-ketone-PF 11 can reduce the death number of shock reaction of mice in a dose-dependent manner and improve the survival rate; the high-dose administration of the pseudoginsenoside 12-ketone-PF 11 has the best effect on resisting anaphylactic shock, the effect on resisting anaphylactic shock is equivalent to that of a positive drug chlorpheniramine, the death number of the pseudoginsenoside 12-ketone-PF 11 high-dose group is remarkably different from that of a model group (the difference has statistical significance,*P<0.05)。
TABLE 2 Effect of pseudoginsenoside 12-keto-PF 11 on Compound48/80 induced anaphylactic shock in mice
And (4) conclusion: the pseudoginsenoside 12-ketone-PF 11 can reduce the death rate of anaphylactic shock of mice caused by Compound48/80 and improve the survival rate.
Test example 2: effect of pseudoginsenoside 12-keto-PF 11 on ear swelling in a delayed type hypersensitivity mouse model.
A delayed type hypersensitivity model is established for BALB/c mice by adopting a Dinitrochlorobenzene (DNCB) method. 50 BALB/c mice, half male and half female, were randomly divided into model group, positive drug chlorphenamine group (4mg/kg), and low, medium and high dose groups (10 mg/kg; 20 mg/kg; 40mg/kg) of pseudoginsenoside 12-one-PF 11. The model group is administrated by respectively intragastrically administering equal volume of physiological saline, positive medicine and pseudoginsenoside 12-ketone-PF 11 once a day for 7 days. The molding method comprises the following steps: on the 1 st day of the experiment, 50 μ L of 2% DNCB solution was injected subcutaneously into the back of the mouse, on the 6 th day, 20 μ L of 2% DNCB solution was applied evenly to both sides of the auricle of the left ear of the mouse, the mouse was sacrificed by removing the cervical spine after 24 hours, the left and right ears of the mouse were subjected to ear punching with a punch (8mm) and weighed, the difference between the left and right ears was taken as the swelling degree, and the swelling inhibition rate was calculated.
As a result: as shown in table 3, ear swelling occurred in DNCB-modeled mice, and a delayed-type hypersensitivity model was successfully established; the pseudoginsenoside 12-ketone-PF 11 can reduce the swelling degree of mouse ear in a dose-dependent manner; the high dose of the pseudoginsenoside 12-ketone-PF 11 has the best effect on the delayed hypersensitivity (compared with a model group, the significant difference has statistical significance,*P<0.05)。
TABLE 3 Effect of pseudoginsenoside 12-one-PF 11 on ear swelling in delayed type hypersensitivity mouse model
And (4) conclusion: the pseudoginsenoside 12-ketone-PF 11 can relieve swelling degree of ear of delayed type hypersensitivity mouse.
Test example 3: effect of pseudoginsenoside 12-keto-PF 11 on the increase in mouse capillary permeability caused by 5-hydroxytryptamine.
A model of increased capillary permeability was established for BALB/c mice using 5-hydroxytryptamine. BALB/c mice 60, half male and half female, were randomly divided into normal group, model group, positive drug chlorpheniramine group (4mg/kg), pseudoginsenoside 12-keto-PF 11 low, medium and high dose groups (10 mg/kg; 20 mg/kg; 40 mg/kg). The normal control group and the model group are respectively administered with equal volume of physiological saline, positive drug and pseudoginsenoside 12-ketone-PF 11 by intragastric administration once a day for 7 days. The molding method comprises the following steps: the abdominal hair of the mice is shaved off by a hair shaver in the morning on the 7 th day, L h of the last medicine is injected into the tail of each mouse, 1% Evans blue solution (800 mu L/10g) is injected into the tail of each mouse, 0.2mL of 0.1% hydroxytryptamine creatinine sulfate solution is injected into the belly depilated position subcutaneously, the mice are killed after cervical vertebra is removed after 30min, the belly is cut open, the belly is taken down by a puncher (8mm), the belly blue-stained skin is cut up and placed in 1.5mL of acetone-physiological saline (1:1) solution, the mixture is homogenized at 4 ℃ and then soaked and stored at 20 ℃ for 24h, the mixture is centrifuged at 3000rpm for 10min under the condition of 4 ℃ after vortexing, the supernatant is taken, and the absorbance value is measured at 620nm by an enzyme-labeling.
As a result: as shown in table 4, 5-hydroxytryptamine resulted in a significant increase in the permeability of the mouse capillaries (the difference was statistically significant,###P<0.001); the application of the pseudoginsenoside 12-keto-PF 11 can reduce the permeability of mouse capillary vessels in a dose-dependent manner, and the high-dose effect of the pseudoginsenoside 12-keto-PF 11 is the best (compared with a model group, the significant difference has statistical significance,*P<0.05)。
TABLE 4 Effect of pseudoginsenoside 12-keto-PF 11 on 5-hydroxytryptamine induced increased mouse capillary permeability model
And (4) conclusion: the pseudoginsenoside 12-ketone-PF 11 has certain inhibition effect on the increase of the capillary permeability of mice caused by 5-hydroxytryptamine.
Test example 4: the effect of pseudoginsenoside 12-keto-PF 11 on the increase in mouse capillary permeability caused by histamine.
A model of increased capillary permeability was established in BALB/c mice using histamine. The animal groups and administration methods and dosages were the same as in test example 3. The molding method comprises the following steps: the same procedures as in test example 3 were carried out except that 0.2mL of each 0.1% hydroxytryptamine creatinine sulfate solution in test example 3 was changed to 0.1mL of each 0.1% histamine phosphate solution.
As a result: as shown in table 5, histamine caused a significant increase in the permeability of the mouse capillaries (the difference was statistically significant,###P<0.001); the pseudo-ginsenoside 12-ketone-PF 11 can reduce the permeability of mouse capillary blood vessel in a dose-dependent manner, and the middle dose group and the high dose group have significant difference compared with the model group (the difference has statistical significance,**P<0.01，***P<0.001) and the effect is best when the pseudo-ginsenoside 12-keto-PF 11 is administered at high dose.
TABLE 5 Effect of pseudoginsenoside 12-keto-PF 11 on increased mouse capillary permeability caused by Histamine
And (4) conclusion: the pseudoginsenoside 12-ketone-PF 11 has certain inhibition effect on the increase of mouse capillary permeability caused by histamine.
Claims (4)
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