CN102342945A - Application of Cortex Ilicis Rotundae saponin compound in preparing anti-inflammatory and analgetic medicament - Google Patents
Application of Cortex Ilicis Rotundae saponin compound in preparing anti-inflammatory and analgetic medicament Download PDFInfo
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Abstract
The invention provides an application of a Cortex Ilicis Rotundae saponin compound in preparing an anti-inflammatory and analgetic medicament, relates to the field of medicine and particularly relates to an application of a Cortex Ilicis Rotundae saponin compound. The Cortex Ilicis Rotundae saponin compound can be used for preparing the anti-inflammatory and analgetic medicament, wherein the Cortex Ilicis Rotundae saponin compound is shown in a formula disclosed in the specification, wherein R is H or/and R is beta-D-glucose. In terms of the extraction of the active components of the medicament, raw materials can be obtained easily, the process is simple, the operation is convenient, and batch production can be realized; the product quality can be controlled easily; and the anti-inflammatory and analgetic medicament is low in toxicity, less in side effect and effective.
Description
Technical field
The present invention relates to field of medicaments, be specifically related to a kind of purposes of Cortex Ilicis Rotundae saponin compound, be used to prepare anti-inflammation analgesis medicament.
Background technology
The Chinese crude drug Cortex Ilicis Rotundae is the dry bark of holly plant Ilex rotunda Thunb. (Ilex rotunda Thunb.); Be distributed widely in the southern china each province; Main product in Guangxi, Guangdong Province; The heat-clearing and toxic substances removing that is usually used among the people, reducing swelling and alleviating pain, heating cures cold; Acute, chronic hepatitis; Acute gastroenteritis, gastric and duodenal ulcers, rheumatic arthritis.The chemical constitution study report of Cortex Ilicis Rotundae is few; At document " Cortex Ilicis Rotundae The Chemical Constituents " (Chinese herbal medicine; 1991; 22 (6): reported 246-248) that containing rotundic acid in the Cortex Ilicis Rotundae is that rotundicacid, Peltatin glucoside are pedunculoside; Rotundic acid isopropylidene ketal, ligustrin, sinapyladehyde, sinapyladehyde glucoside, syringic aldehyde, 3 one acetyloleanolic acids and stearic acid etc.
Contain a large amount of pentacyclic triterpene saponins in the Cortex Ilicis Rotundae; According to document " content of Peltatin glucoside in the high effective liquid chromatography for measuring Cortex Ilicis Rotundae medical material " special product research 2007; The 4:45-47 report; The content of Peltatin glucoside is up to 8.8% in the Cortex Ilicis Rotundae medical material; If add the content of its aglycon rotundicacid, its total saponin content is higher.Therefore, the development and use of pentacyclic triterpenoid have good economic worth in the Cortex Ilicis Rotundae.
Cortex Ilicis Rotundae is the medical material that extensive use is arranged, and at present its Pharmacological action study is mainly concentrated on cardiovascular system, secondly is some researchs of vitro antibacterial activity, but the relevant pharmacologically active report of the chemical constituent of extracting from Cortex Ilicis Rotundae is less.Disclose the method for preparing and the application of Peltatin glucoside at Chinese patent CN101033245A, disclose Peltatin glucoside and can be used for treating coronary heart disease, angina pectoris, apoplexy, the cerebral infarction diseases of cardiovascular and cerebrovascular systems of waiting indefinitely.Chinese patent CN101342186A discloses Peltatin glucoside and rotundicacid is used to treat hyperlipemia.
Anti-inflammation analgesia medicine is one type of common drug with antiinflammatory, analgesic, analgesia and anti rheumatism action.Because this type of medicine has glucocorticoids and claims steroidal class appearance antiinflammatory, anti rheumatism action again; But it is different with the chemical constitution of steroidal class anti-inflammation analgesis medicament; So a type medicine is claimed nonsteroidal anti-inflammatory analgetic again; Extensive use and active chronic inflammation and treatment of pain clinically; But life-time service is prone to cause the untoward reaction of tissues such as gastrointestinal tract, kidney, liver and blood system and system and sees document: the contemporary Chinese medicinal application; 2008,2 (15): 111-112.The anti-inflammation analgesis medicament of Chinese medicine is main with compound recipe mostly, but because unknown effective ingredient, quality is restive.Therefore, exploitation is safe, effective, the little anti-inflammation analgesia medicine medicine of untoward reaction has great importance, and vast market prospect is arranged.
Summary of the invention
The objective of the invention is that the extraction separation effective ingredient is used to prepare anti-inflammation analgesis medicament from holly plant Ilex rotunda Thunb. (Ilex rotunda Thunb.) plant.
Technical scheme of the present invention is: get the Cortex Ilicis Rotundae saponin compound and be used to prepare anti-inflammation analgesis medicament, said Cortex Ilicis Rotundae saponin compound is meant with the chemical compound shown in the following formula
Wherein: R be H or/and R is β-D-glucose, the structural formula of β-D-glucose is:
Cortex Ilicis Rotundae saponin compound when the R in the formula is H is called rotundicacid (Rotundic acid); Be called rotundic acid again; When the Cortex Ilicis Rotundae saponin compound by name Peltatin glucoside (pedunculoside) of R in the formula when being β-D-glucosyl group, be called pedunculoside again.
The Cortex Ilicis Rotundae saponin compound can be that extraction separation makes the Cortex Ilicis Rotundae medical material from the dry bark of holly plant Ilex rotunda Thunb. (Ilex rotunda Thunb.); See document: Chinese herbal medicine; 1991; 22 (6): 246-248), also can obtain from the medicinal residues extraction separation behind the Cortex Ilicis Rotundae water extraction.
Get the ethanol extraction of Cortex Ilicis Rotundae medical material (Ilex rotunda Thunb.) with 90-95%; Concentrate; Concentrate adds water; Filter; Getting insoluble matter is that precipitate is a crude extract; This extract disperses the back in continuous extraction separator with kieselguhr or silica gel or quartz sand; Low polar organic solvent in using earlier; Like dichloromethane, chloroform, a kind of or two kinds of mixed solvent heating and refluxing extraction of petroleum ether etc.; Solvent recovery; Get the Cortex Ilicis Rotundae acid crude, reuse organic solvent recrystallization gets rotundicacid, and content reaches more than 98%; The stronger polar solvent of residue reuse in the separator; Like ethyl acetate; Ethanol; A kind of or two kinds of mixed solvent heating and refluxing extraction of methanol etc.; Reclaim solvent, obtain the Peltatin glucoside crude product, use concentration to be the 30-80% ethyl alcohol recrystallization as methanol or the concentration of 30-80%; Obtain Peltatin glucoside, content reaches more than 98%.
Peltatin glucoside and rotundicacid also can obtain by extraction separation from Folium Ilicis Purpureae, after promptly Folium Ilicis Purpureae is pulverized, use acetone extraction; Extracting solution reclaims solvent; Concentrate, filter, filtrating is through Sephadex LH-20 column chromatography; Water-methanol-eluted fractions; Separation obtains, and sees document: Zhao Haoru etc., CHINA JOURNAL OF CHINESE MATERIA MEDICA; 1993,18 (4): 226-228.
When the R in the formula is β-D-glucosyl group; Chemistry Peltatin glucoside (pedunculoside) by name; It can be that extraction separation makes the Cortex Ilicis Rotundae medical material from the dry bark of holly plant Ilex rotunda Thunb. (Ilex rotunda Thunb.), can be according to the method for preparing preparation of the disclosed Peltatin glucoside of patent CN101033245A.
Below the purposes that is used to prepare anti-inflammation analgesis medicament through evidence Cortex Ilicis Rotundae saponin compound provided by the invention.
Test Example 1The anti-inflammatory and analgesic effect of Peltatin glucoside and rotundicacid
1. material
1.1 laboratory animal: cleaning level ICR mice and SD rat are provided the quality certification number: SYXK (Soviet Union) 2007-0009 by Yangzhou University comparative medicine center.Complete feed is fed, and free diet drinking-water gives substantial light and shines.
1.2 reagent and instrument:
1.2.1 be subjected to the reagent thing: rotundicacid, Peltatin glucoside.
1.2.3 ELX800UV microplate reader: U.S. BIO-TEK company.
2. method
2.1 mice caused by dimethylbenzene xylene auricle edema
60 of ICR mices, ♀, ♂ half and half are divided into 6 groups at random, 10 every group, are respectively blank group, aspirin group (100 mg/kg), rotundicacid, Peltatin glucoside low, high (50,100mg/kg) dose groups.The aspirin group is irritated stomach (ig) aspirin CMC-Na solution 0.1ml/10g, the CMC-Na solution 0.1ml/10g of rotundicacid, Peltatin glucoside ig variable concentrations, and the CMC-Na solution of blank group ig respective volume, every day 1 time, for three days on end.1h evenly smears xylene 0.05ml in the two sides after the last administration before and after mouse right ear; Left side ear compares; 1.5h after mice taken off neck put to death; Cut two ears along the auricle baseline; Card punch with diameter 8mm is laid round auricle at same position respectively; Using scales/electronic balance weighing, is the swelling degree with the difference of left and right sides auricle weight.
2.2 acetic acid hyperamization pipe permeability increases test
60 of ICR mices, ♀, ♂ half and half, animal divides into groups and administration (with 2.1).1h after the last administration, tail vein injection 0.5% Evans blue solution 0.1ml/10g, lumbar injection 0.6% acetic acid 0.1ml/10g immediately; Behind the 20min; Take off cervical vertebra and put to death, lumbar injection 6ml normal saline is gently rubbed abdominal part; Cut off the abdominal cavity; With suction pipe sucking-off cleaning mixture, add normal saline to 10ml, the centrifugal 15min of 3000rpm; Get supernatant, the 590nm place surveys the OD value.
2.3 carrageenin causes the swelling of rat toes
60 of SD rats, ♀, ♂ half and half, animal divides into groups and administration (with 2.1), successive administration 1w.1h causes inflammation in the right back toes subcutaneous injection 1% carrageenin solution 0.1ml of every Mus after the last administration, with toes volume determination appearance measure respectively cause scorching before with cause scorching back 1,3,5,7h toes volume, with each Mus cause scorching before and after volumetrical difference be the swelling degree.
2.4 rat granuloma is swollen
60 of SD rats; ♀, ♂ half and half; Animal divides into groups and administration (with 2.1), and with 3% pentobarbital sodium 0.15ml/100g intraperitoneal injection of anesthesia, dorsal position is fixed; Under aseptic condition; (each cotton balls drips ampicillin 1mg/0.1ml behind 121 ℃ of autoclaving 30min for each 50 ± 1mg, profile unanimity with aseptic cotton balls; 50 ℃ of oven dry) implantation rat groin is subcutaneous, drips a small amount of penicillin in the wound and protects from infection.Perform the operation and began ig administration, one week of successive administration the same day.Rat was taken off neck in the 8th day and put to death, take out cotton balls, put 60 ℃ of baking boxs and bake, deduct the raw cotton ball weight, be the granuloma net weight, represent with granuloma net weight mg/100g body weight to constant weight.
2.5 mice hot plate test
Through 60 of 55 ℃ of hot plates screening pain threshold, 5～30s ICR female mices, be divided into the blank group at random, aspirin group, rotundicacid, Peltatin glucoside low, high (50,100mg/kg) dose groups, 10 every group.Each mice is surveyed 2 pain thresholds, gets average as basic pain threshold, respectively organizes mice gastric infusion respectively then, and volume is 0.1ml/10g, successive administration 5d.After the last administration 1,2,3,4h measures the mice pain threshold respectively.
2.6 mice acetic acid twisting test
60 of ICR mices, ♀, ♂ half and half, animal divides into groups and administration (with 2.1).Every day 1 time, continuous 5 days, 0.5h after the last administration, every mouse peritoneal is injected 0.7% acetum 0.2ml, and the writhing response that mice occurs in the counting 15min (stretching hind leg, abdominal part indent and buttocks raises) number of times calculates the analgesia rate.
2.7 statistical method:
All data are all handled with the SPSS10.0 statistical software.Count indicators used (
± S) representation.Mean relatively adopts one factor analysis of variance between group, and < 0.05 has statistical significance to P.
3. result
3.1 rotundicacid, Peltatin glucoside are to the influence of mice auricle swelling
The result sees table 1, and xylene is the inducing mouse ear swelling obviously.Cause scorching before successive administration 3d, finding rotundicacid, Peltatin glucoside (50,100mg/kg) xylol causes the Mice Auricle acute inflammation has inhibitory action in various degree, mice ear has obvious inhibitory action.
3.2 rotundicacid, Peltatin glucoside are to the influence of vascular permeability
The result sees table 1.Experiment shows; The absorbance of Evans Blue is starkly lower than blank (p < 0.01) in rotundicacid, Peltatin glucoside high dose group and the aspirin group peritoneal exudate, and the difference of rotundicacid, Peltatin glucoside low dose group and blank group absorbance has significance meaning (p < 0.05).Hence one can see that, and the capillary permeability increase has inhibitory action due to rotundicacid, the Peltatin glucoside Dichlorodiphenyl Acetate.
Table 1 rotundicacid, Peltatin glucoside are to the influence of mice auricle swelling and vascular permeability
（
±S，n=10）
Annotate: compare with the blank group: * P 0.05, * * P < 0.01;
3.3 rotundicacid, Peltatin glucoside on Carrageenan cause the influence of rat toes swelling
Result such as table 2, carrageenin cause scorching back 1h, and the rat toes begin variations such as acute inflammation appearance is red, swollen, and about 3h swelling reaches the peak.Rotundicacid, Peltatin glucoside begin to produce curative effect in causing scorching back 1h, at 1h, 3h, 5h, the inductive rat paw edema of each time point on Carrageenan of 7h inhibitory action are significantly arranged all.
Table 2 Rescue will be sour, with habitat holly glucoside on rat paw paw edema volume effect (
± S, n = 10)
Annotate: compare with the blank group: * P 0.05, * * P < 0.01
3.4 rotundicacid, Peltatin glucoside are to the bullate influence of rat granuloma
The result is as shown in table 3, and rotundicacid, Peltatin glucoside high dose have inhibitory action to the rat granuloma hypertrophy.
Table 3 Rescue Bing acid, glycosides with habitat holly effects on rat granuloma (
± S, n = 10)
Annotate: compare with the blank group: * P 0.05, * * P < 0.01
3.5 rotundicacid, Peltatin glucoside are to the influence of hot plate test mice pain threshold
The result is as shown in table 4, behind Cortex Ilicis Rotundae I, the continuous ig administration of the Cortex Ilicis Rotundae II 5d, with the blank group relatively, each dose groups all can obviously prolong mice hot plate reaction incubation period, improves pain threshold.
3.6 rotundicacid, Peltatin glucoside Dichlorodiphenyl Acetate cause the influence of mouse writhing reaction
The result sees table 5, and behind rotundicacid, the continuous ig administration of the Peltatin glucoside 5d, each dose groups all can reduce the mouse writhing reaction times due to the acetic acid, has analgesic activity, compares significant difference with the blank group, and high dose analgesia rate is higher than 50%.Show that the pain that rotundicacid, Peltatin glucoside cause chemical irritation has the obvious suppression effect.
Table 4? Save Bing acid glycosides on mice with habitat holly pain threshold effect (
± S, n = 10)
Annotate: compare with the blank group: * P 0.05, * * P < 0.01
Table 5 Rescue Bing acid, glycosides with habitat holly writhing on the impact (
± S, n = 10)
Annotate: compare with the blank group: * P 0.05, * * P < 0.01
4. conclusion
Rotundicacid, Peltatin glucoside can reduce and ooze out, and alleviate acute inflammation, and chronic inflammatory disease is had effect.Rotundicacid, Peltatin glucoside have analgesic activity.
Test Example 2
The acute toxicity test in mice of rotundicacid, Peltatin glucoside
Rotundicacid, Peltatin glucoside, dosage are respectively 1.25,2.5,5,10g/kg, give mouse stomach respectively, do not see in two weeks that death and other abnormal response take place, and can't measure the LD50 that is subjected to reagent thing mouse stomach.Mice is with Cmax, maximum volume, and no overt toxicity reaction does not also have dead behind interior three gastric infusions of 24h in one week.Record the maximum dosage-feeding of mouse stomach administration, rotundicacid is 60 g/kg.Peltatin glucoside is 60 g/kg.
More than test tentatively shows Peltatin glucoside, rotundicacid, can be used to prepare hypotoxic anti-inflammation analgesis medicament.Can use by single component, or two compositions merge application.The convenience of taking for the patient and according to the characteristic of chemical compound; Chemical compound can be added various conventional adjuvant required when preparing different dosage form; Process any oral formulations such as tablet, hard capsule, soft capsule, granule, chewable tablet by the process of Chinese medicine preparation of routine; Buccal tablet; Drop pill or slow releasing tablet etc. also can be made into injection.
Medicine of the present invention has anti-inflammatory and analgesic effect.Beneficial effect of the present invention: 1, the extraction of active constituents of medicine, raw material is easy to get, and technology is simple, easy to operate, can put into production in enormous quantities; 2, product quality is easy to control; 3, be that toxicity is low, side effect is little, effectively anti-inflammation analgesis medicament.
The specific embodiment
Embodiment 1The preparation of Peltatin glucoside and rotundicacid
Get Cortex Ilicis Rotundae medical material (Ilex rotunda Thunb.) 20Kg with 95% ethanol extraction; Extracting solution is concentrated into 5.6Kg; Add 16Kg water, filter, getting insoluble matter is that precipitate is a crude extract; This extract disperses the back in continuous extraction separator with silica gel; Earlier use the dichloromethane heating and refluxing extraction, solvent recovery gets the Cortex Ilicis Rotundae acid crude; Reuse dichloromethane recrystallization gets rotundicacid, reaches 98.8% with high effective liquid chromatography for measuring content; Residue in separator ethyl acetate heating and refluxing extraction reclaims solvent, obtains the Peltatin glucoside crude product, and product obtains Peltatin glucoside with 60% ethanol liquid recrystallization, reaches 99.2% with high effective liquid chromatography for measuring content.
Embodiment 2The preparation of Peltatin glucoside capsule
Get Peltatin glucoside 210g, be ground into fine powder, add the about 150g of 20% gelatinized corn starch, mix, 14 mesh sieves are granulated, and in 100 ℃ of dryings, granulate adds starch 20g, magnesium stearate 2g, and mixing incapsulates, and processes 1000, promptly gets.Every heavy 0.25g contains Peltatin glucoside 200mg.
Embodiment 3The preparation of rotundicacid tablet
Get rotundicacid 160g, be ground into fine powder, add the about 150g of 20% gelatinized corn starch, mix, 14 mesh sieves are granulated, and in 100 ℃ of dryings, granulate adds starch 20g, magnesium stearate 2g, and mixing is pressed into 1000, promptly gets.Every heavy 0.2g contains rotundicacid 150mg.
Embodiment 4The preparation of Peltatin glucoside tablet
Get Peltatin glucoside 100g, get rotundicacid 100g, be ground into fine powder, add the about 150g of 20% gelatinized corn starch, mix, 14 mesh sieves are granulated, and in 100 ℃ of dryings, granulate adds starch 20g, magnesium stearate 2g, and mixing is pressed into 1000, promptly gets.Every heavy 0.25g contains Peltatin glucoside 100mg, rotundicacid 100mg.
Embodiment 5The rotundicacid preparation of soft capsule
Get rotundicacid 16g, add propylene glycol 0.2g, lecithin 0.9g, soybean oil 18g, vibromill ultra micro 20 minutes makes mixing, processes 100 of soft capsules, promptly gets.The tolerant heavy 0.35g of every intragranular contains rotundicacid 150mg.
Embodiment 6The preparation of Peltatin glucoside granule
Get Peltatin glucoside 20.5g, be ground into fine powder, add dextrin 25g, lactose 455g, mix homogeneously is granulated, in 80 ℃ of dryings, granulate, packing, system 100 bags promptly get.The heavy 5g of every bag contains Peltatin glucoside 200mg.
Embodiment 7The preparation of rotundicacid slow releasing tablet
Get rotundicacid 12g, be ground into fine powder, cross 100 mesh sieves; HPMC 10.3g, lactose 16g, sodium lauryl sulphate 1g crosses 100 mesh sieves; Mix homogeneously adds 2% polyvidone (95% ethanol) adhesive system soft material, crosses 20 mesh sieves and granulates; In 50 ℃ of dryings, cross 18 mesh sieve granulate, dried granule adopts outer addition to add 2% magnesium stearate; Mixing; Tabletting is processed 100 of slow releasing tablet, promptly gets.Every heavy 500mg contains rotundicacid 120mg.
Embodiment 8The rotundicacid drop pill is preparation
Get rotundicacid 10.5g, be ground into fine powder, other gets 24.6g Macrogol 4000 heating and melting, adds rotundicacid, and vibromill ultra micro 20 minutes makes mix homogeneously, drips and processes drop pill, promptly gets.The heavy 0.35g of every ball,, contain rotundicacid 100mg.
Claims (1)
1. the Cortex Ilicis Rotundae saponin compound is used to prepare anti-inflammation analgesis medicament, and said Cortex Ilicis Rotundae saponin compound is meant with chemical compound shown in the following formula
Wherein: R be H or/and R is β-D-glucosyl group, the structural formula of β-D-glucosyl group is:
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| CN105125567A (en) * | 2015-09-09 | 2015-12-09 | 安士制药（中山）有限公司 | New anti-inflammation purpose of pedunculoside |
| CN110638910A (en) * | 2019-08-26 | 2020-01-03 | 白银香生物科技有限公司 | A breath freshener with antiviral, antibacterial and antiinflammatory effects, and its preparation method |
| CN111135179A (en) * | 2020-01-19 | 2020-05-12 | 广西中医药大学 | Application of iron wintergreen acid in preparation of medicine for treating pneumonia |
| CN111607638A (en) * | 2020-06-19 | 2020-09-01 | 吉林大学 | Experimental method for treating mastitis disease by pedunculoside |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103191159A (en) * | 2012-08-02 | 2013-07-10 | 徐文霞 | Inflammation-diminishing bacterium-inhibition preparation and its preparation method and use |
| CN103191159B (en) * | 2012-08-02 | 2014-12-10 | 徐文霞 | Inflammation-diminishing bacterium-inhibition preparation and its preparation method and use |
| CN105125567A (en) * | 2015-09-09 | 2015-12-09 | 安士制药（中山）有限公司 | New anti-inflammation purpose of pedunculoside |
| CN110638910A (en) * | 2019-08-26 | 2020-01-03 | 白银香生物科技有限公司 | A breath freshener with antiviral, antibacterial and antiinflammatory effects, and its preparation method |
| CN111135179A (en) * | 2020-01-19 | 2020-05-12 | 广西中医药大学 | Application of iron wintergreen acid in preparation of medicine for treating pneumonia |
| CN111135179B (en) * | 2020-01-19 | 2021-06-15 | 广西中医药大学 | Application of iron wintergreen acid in preparation of medicine for treating pneumonia |
| CN111607638A (en) * | 2020-06-19 | 2020-09-01 | 吉林大学 | Experimental method for treating mastitis disease by pedunculoside |
| CN111607638B (en) * | 2020-06-19 | 2023-05-16 | 吉林大学 | Experimental method for treating mastitis by using pedunculoside |
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