CN100395258C - Loquat leaf triterpene acid composition and its uses in preparation of medicine against inflammation and antitussive - Google Patents
Loquat leaf triterpene acid composition and its uses in preparation of medicine against inflammation and antitussive Download PDFInfo
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- CN100395258C CN100395258C CNB031211755A CN03121175A CN100395258C CN 100395258 C CN100395258 C CN 100395258C CN B031211755 A CNB031211755 A CN B031211755A CN 03121175 A CN03121175 A CN 03121175A CN 100395258 C CN100395258 C CN 100395258C
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Abstract
The present invention relates to a total triterpenic acid component which is extracted and separated from Chinese medicinal herb loquat leaves. The chemical composition of the total triterpenic acid component comprises ursolic acid, oleanolic acid, 2-alpha-hydroxy ursolic acid, 2 alpha-hydroxy oleanolic acid, pomolic acid, rosolic acid, etc. The chemical structure of the present invention discloses in general formula I; the present invention has the activity of resisting inflammation and relieving cough; the present invention also relates to the application of the total triterpenic acid component to medicine preparation, particularly to the application to the preparation of medicines for resisting inflammation and relieving cough, etc.
Description
Technical field:
The present invention relates to a kind of total triterpene acid component and the application aspect the preparation medicine thereof, the particularly application aspect preparation anti-inflammatory, cough suppressing medicine of extraction separation from the Chinese medicine Loquat Leaf.
Background technology:
The dry leave of loquat leaf system Rosaceae Rosaceae loquat platymiscium loquat Eriobotrya japonica (Thunb.) Lindl..It is very wide to distribute in China, mainly is distributed in East China, Central-South, southwest.Loquat Leaf is the conventional Chinese medicine simply of China, records in going through edition Chinese Pharmacopoeia and uses for tcm clinical practice, and its property hardship is slightly cold, and attaches to the lung and stomach meridians removing heat from the lung to relieve cough, stopping nausea and vomiting by lowering the adverse flow of QI.Be used for the cough due to lung-heat, the circulation of vital energy in the wrong direction is breathed heavily urgency, and stomach energy is vomitted contrary, and dysphoria with smothery sensation is thirsty.
Fully excavate the natural resources of Chinese medicinal materials of China's abundant, utilize the modern science and technology means, it is necessary developing clinical effective medicine.Yet a kind of total triterpene acid component of extraction separation is used to prepare medicine and particularly prepares anti-inflammatory, cough suppressing medicine aspect from the Chinese medicine Loquat Leaf, has had not yet to see report.
One of purpose of the present invention is, a kind of total triterpene acid component is provided, and its chemical ingredients mainly comprises urson, 2 Alpha-hydroxy ursons, 2 Alpha-hydroxy Oleanolic Acids, also contains compositions such as Oleanolic Acid, Rialic acid A and Jacaric acid in addition.This total triterpene acid component, its content reaches more than 50%, and wherein urson, 2 Alpha-hydroxy ursons and 2 Alpha-hydroxy Oleanolic Acid proportions are respectively 30-60%, 5-20% and 5-20%.
Two of purpose of the present invention is that the application of a kind of total triterpene acid component aspect the preparation medicine, the particularly application aspect preparation anti-inflammatory, cough suppressing medicine are provided.
Summary of the invention:
Chemical ingredients in the total triterpene acid component prescription of the present invention comprises urson, Oleanolic Acid, 2 Alpha-hydroxy ursons, 2 Alpha-hydroxy Oleanolic Acids, Rialic acid A and Jacaric acid etc., and it has formula (1) chemical structure of general formula,
Formula (1)
In the formula: R
1R
3, R
4Be H or OH; R
2Be α-OH or β-OH.
In order to inquire into the basic substance of its drug action, to seek with this Chinese medicine function and cure mainly the effective constituent that matches, chemical ingredients and anti-inflammatory, antibechic pharmacology activity research have been carried out to it in this laboratory.Preliminary pharmacological screening experiment shows that the mice ear that Loquat Leaf ethanol extraction p-Xylol causes has obvious restraining effect, and the guinea pig cough that spraying causes to citric acid has tangible antitussive action.Then its ethanol extraction is carried out separation and purification, through the macroporous resin removal of impurities, the aluminum oxide decolouring, methyl alcohol or acetone crystallization obtain the total triterpene acid component; It is separated obtain 6 triterpenic acid compounds, be accredited as respectively urson (ursolic acid, I), 2 Alpha-hydroxy ursons (2 α-hydroxyursolic acid, II), 2 Alpha-hydroxy Oleanolic Acids (maslinic acid, III), Oleanolic Acid (oleanolic acid, IV), Rialic acid A (pomolic acid, V) and Jacaric acid (euscaphic acid, VI); Wherein, Rialic acid A is to separate first to obtain from this plant.The present invention has carried out the HPLC analysis with separating 6 kinds of compositions obtaining as standard substance to total triterpene acid, and the result shows: the total amount that contains Compound I-VI in the total triterpene acid reaches 86.8%; Each composition urson, Oleanolic Acid, 2 Alpha-hydroxy ursons, 2 Alpha-hydroxy Oleanolic Acids, Rialic acid A and Jacaric acid ratio are followed successively by 47.9%, 1.5%, 10.0%, 11.1%, 3.6% and 12.7%.
Deep pharmacodynamic experiment studies show that: the total triterpene acid component, and the mice ear that urson and 2 Alpha-hydroxy Oleanolic Acid p-Xylol cause shows very strong anti-inflammatory activity; The former two guinea pig cough that spraying causes to citric acid has shown antitussive action.
Technical scheme of the present invention comprises following steps according to this:
One, the preparation of total triterpene acid:
[Eriobotrya japonica (Thunb.) Lindl.] is raw material with Loquat Leaf, and with 95% alcohol reflux 2 times, each two hours, united extraction liquid reclaimed solvent, medicinal extract.Medicinal extract is dissolved with suitable quantity of water, handle with the D101 macroporous adsorbent resin, first water wash-out is used the 95%EtOH wash-out again, the partially recycled solvent of latter's wash-out gets brown eluate, use dissolve with ethanol, the triplication neutral alumina is mixed sample, volatilizes behind the solvent with one times of amount neutral alumina column chromatography, methanol-eluted fractions, reclaim solvent and get unformed powder,, promptly get total triterpene acid through methyl alcohol or acetone treatment.
Two, pharmacodynamics test:
1, experiment material:
Mouse, Kunming kind, male and female half and half, body weight 25～30g, secondary animal (conformity certification number: SCXK1100-0006); Cavy, regular grade; All available from Chinese Academy of Medical Sciences's Experimental Animal Center.
2, experimental technique and result
1), the extraction position p-Xylol of oral Loquat Leaf ethanol extraction causes that the influence of mice ear gets mouse, body weight 25～30g is divided into 4 groups at random, every group 14, male and female are given physiological saline, the 2nd～4 group for half and half, the 1 group, gavage the suspension aqueous solution that Loquat Leaf respectively extracts position medicinal extract respectively, each organizes gastric infusion 1 time every day, and continuous 3 times, in the last administration after 45 minutes, with 5 seconds of dimethylbenzene cotton balls contact mouse right ear, the post-tensioning cervical vertebra was put to death mouse in 15 minutes respectively.With diameter 8mm punch tool the mouse ears are downcut with the position, measure left and right sides ear weight difference, statistical treatment is respectively organized data and is calculated and press down swollen rate.The result shows that the mice ear that EJ-02 and EJ-03 part p-Xylol cause has the obvious suppression effect, shows anti-inflammatory activity (table 1).
The extraction position p-Xylol of the oral Loquat Leaf ethanol extraction of table 1 cause mice ear influence (X ± SD, n=14)
Annotate: compare with the physiological saline group
*P＜0.05
2), the extraction position of oral Loquat Leaf ethanol extraction is to the antitussive action of cavy
Adopt the citric acid spraying to draw the method for coughing, get cavy, body weight 190～220g is divided into 5 groups at random, and 8 every group, male and female half and half.The 1st group of oral normal saline, the 2nd～4 group, oral respectively Loquat Leaf respectively extracts the suspension aqueous solution of position medicinal extract, the 5th group of oral morphine monomethyl ether aqueous solution, gastric infusion was put into experimental installation with cavy after 1 hour, use the ultrasound medical spraying gun, spray into the atomizing gas of 17.5% citric acid solution, sprayed for 40 seconds, write down cough latent period and the cough number of times of every cavy in 5 minutes.The result shows that EJ-02 and EJ-03 part all have tangible antitussive action (table 2) to cavy.
The extraction position of the oral Loquat Leaf ethanol extraction of table 2. to the antitussive action of cavy (X ± SD, n=8)
Annotate: compare with the physiological saline control group
*P＜0.05,
* *P＜0.001.
3), oral urson, 2 Alpha-hydroxy Oleanolic Acids and total triterpene acid p-Xylol cause the influence of mice ear
Kunming mouse, body weight 28～30g is divided into 9 groups at random, and 14 every group, male and female half and half.The 1st group of oral normal saline, the 2nd group of oral aspirin aqueous solution, the 3rd～5 group, the aqueous solution of high, medium and low three the dosage groups of the oral urson of difference, the 6th group of oral 2 Alpha-hydroxy Oleanolic Acid aqueous solution, the 7th～9 group, the aqueous solution of high, medium and low three the dosage groups of the oral total triterpene acid of difference, other method is described with 4.1.The result shows that the mice ear that urson, 2 Alpha-hydroxy Oleanolic Acids and the equal p-Xylol of total triterpene acid cause has obvious restraining effect (table 3).
The oral urson of table 3,2 Alpha-hydroxy Oleanolic Acids and total triterpene acid p-Xylol cause the influence (X ± SD) of mice ear
Annotate: compare with the physiological saline control group
*P＜0.05,
*P＜0.01,
* *P＜0.001.
4) urson in the Loquat Leaf, total triterpene acid are to the antitussive action of cavy
Get cavy, body weight 200～230g is divided into 9 groups at random, and 8 every group, male and female half and half.The 1st group of oral normal saline, the 2nd group of oral morphine monomethyl ether aqueous solution, the 3rd group of oral benproperine phosphate aqueous solution, the 4th～6 group, the aqueous solution of high, medium and low three the dosage groups of the oral urson of difference, the aqueous solution of the 7th～9 group of high, medium and low three the dosage groups of the oral total triterpene acid of difference, other method is the same.As a result, urson, total triterpene acid have shown antitussive action (table 4) to cavy in the Loquat Leaf.
Urson in the oral Loquat Leaf of table 4, total triterpene acid to the antitussive action of cavy (X ± SD, n=8)
Annotate: compare with the physiological saline control group
*P＜0.05,
*P＜0.01,
* *P＜0.001.
Three, the component analysis of total triterpene acid
Above pharmacodynamic experiment result shows that urson has very strong anti-inflammatory action, and its activity is better than the acetylsalicylic acid control group, and 2 Alpha-hydroxy Oleanolic Acids and total triterpene acid also show stronger anti-inflammatory action; Urson and total triterpene acid also show corresponding antitussive action.Of the present invention studies show that, Loquat Leaf be in the different acquisition phase in the different places of production, the same place of production, or from the commodity (honey is processed) of pharmacy's buying mensuration urson content in the 0.59-0.76% scope.
1, instrument and material
The present invention has adopted U.S. Waters 600 type high performance liquid chromatographs, diode-array detector, 2010 data processing softwares; TCQ-250 ultrasonic cleaner (Beijing medical facilities two factories); Methyl alcohol is chromatographically pure, the water steaming distilled water of attaching most importance to; Phosphoric acid is analytical pure.
2, chromatographic condition
Chromatographic column: Nova-pakC
18(3.9mm * 150mm, 4 μ m); Moving phase: CH
3OH-H
2O-H
3PO
4(80: 20: 0.075); Flow velocity: 1ml/min; Column temperature: 25 ℃; Detect wavelength: 205nm.
3, the preparation of triterpenic acid sample and compound 1-6 standard solution
Get total triterpene acid or compound 1-6 standard substance 0.70mg, accurate title is fixed to be put the 1ml measuring bottle and adds methanol solution and be diluted to scale to 0.01mg, shakes up promptly.
4, the preparation of Loquat Leaf sample liquid
The about 0.8g of sample thief Loquat Leaf (crossing sieve No. 3), accurate title is fixed to place the 25ml volumetric flask to 0.0001g, adds chloroform 20ml, and weighing is sealed film and is sealed.Soak 30min, supersound extraction 20min intermittently behind the 10min, continues supersound extraction 20min, weighs, and mends to weigh, and weight is the same before and after making.Filter, get subsequent filtrate 5ml and volatilize, dissolve with methanol repeatedly is transferred in the 5ml volumetric flask methanol constant volume on a small quantity.
5, the component analysis of total triterpene acid
Get compound 1-6 standard solution sample introduction 20 μ l respectively, by above-mentioned chromatographic condition mensuration retention time separately; The total triterpene acid sample liquid is with the method sample introduction, and the peak position of its color atlas and compound 1-6 is shown in (Fig. 1).Measure the peak area integrated value with normalization method, the total amount that contains compound 1-6 in the total triterpene acid reaches 86.8%; Each composition urson, Oleanolic Acid, 2 Alpha-hydroxy ursons, 2 Alpha-hydroxy Oleanolic Acids, Rialic acid A and Jacaric acid ratio are followed successively by 47.9%, 1.5%, 10.0%, 11.1%, 3.6% and 12.7%.
The invention advantage:
The invention has the advantages that; compared with prior art; overcome traditional Chinese medicine and mostly be compound or make oral granule or thick paste and cause lacking reliable quality control and take, carry and transport defective such as inconvenience, adopted modern science and technology can prepare safer, effective, stable, controlled and take pharmaceutical preparation easily with simple extraction crude extract.
Description of drawings:
Fig. 1: total triterpene acid sample high pressure liquid chromatography figure
Wherein: the 1-urson; The 2-Oleanolic Acid; 3-2 Alpha-hydroxy urson;
4-2 Alpha-hydroxy Oleanolic Acid; The 5-Rialic acid A; The 6-Jacaric acid.
Claims (2)
1. a total triterpene acid component that obtains in Loquat Leaf mainly comprises urson, 2 Alpha-hydroxy ursons, 2 Alpha-hydroxy Oleanolic Acids, Oleanolic Acid, Rialic acid A and Jacaric acid, and its chemical structure of general formula is:
Formula (1)
In the formula: R
1, R
3, R
4Be H or OH, R
2Be α-OH or β-OH
Above-mentioned total triterpene acid component, its content reaches more than 50%, and wherein urson, 2 Alpha-hydroxy ursons and 2 Alpha-hydroxy Oleanolic Acid proportions are respectively 30-60%, 5-20% and 5-20%.
2. the application of total triterpene acid component as claimed in claim 1 in preparation anti-inflammatory, antibechic clinical treatment medicine.
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100360551C (en) * | 2003-12-19 | 2008-01-09 | 杨庆尧 | Acid-base process for preparing ursolic acid |
| CN1315865C (en) * | 2004-01-08 | 2007-05-16 | 中国科学院上海药物研究所 | Loguat leaf total dehydrocamphenilic acid and its preparation method and use |
| RO120950B1 (en) * | 2005-02-18 | 2006-10-30 | Biotehnos S.A. | Bioactive complex of triterpene acids, process of preparation, medicinal products with therapeutical applications |
| CN1943647B (en) * | 2006-10-13 | 2011-06-15 | 福州大学 | The method for preparing triterpenic acid extract from the loquat leaves |
| CN102048851B (en) * | 2009-11-09 | 2013-03-13 | 臻里生物科技股份有限公司 | Loquat leaf cell extract for protecting liver and/or reducing fat and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1303850A (en) * | 1999-10-26 | 2001-07-18 | 上海长海医院 | Method for producing oleanolic acid |
| CN1307869A (en) * | 2000-12-29 | 2001-08-15 | 南京大学 | Depression treating medicine |
| CN1386744A (en) * | 2002-05-22 | 2002-12-25 | 吉林天药科技股份有限公司 | Process for extracting triterpenic acid from gleditschia, and medical use and Chinese medicine of triterpenic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1303850A (en) * | 1999-10-26 | 2001-07-18 | 上海长海医院 | Method for producing oleanolic acid |
| CN1307869A (en) * | 2000-12-29 | 2001-08-15 | 南京大学 | Depression treating medicine |
| CN1386744A (en) * | 2002-05-22 | 2002-12-25 | 吉林天药科技股份有限公司 | Process for extracting triterpenic acid from gleditschia, and medical use and Chinese medicine of triterpenic acid |
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