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CN1055859C - Application of stilbene compound and its derivative in preparation of endothelium element antagonist agent - Google Patents

Application of stilbene compound and its derivative in preparation of endothelium element antagonist agent Download PDF

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CN1055859C
CN1055859C CN97103928A CN97103928A CN1055859C CN 1055859 C CN1055859 C CN 1055859C CN 97103928 A CN97103928 A CN 97103928A CN 97103928 A CN97103928 A CN 97103928A CN 1055859 C CN1055859 C CN 1055859C
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laws
craib
plant
cissus
cissus assamica
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CN1196245A (en
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杨连春
王峰
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AIR FORCE GENERAL HOSPITAL PLA
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Abstract

The present invention discloses a medicinal preparation containing the effective component of a Chinese herbal medicine plant Cissus assamica (Laws.) Craib, and an extraction method of the Cissus assamica (Laws.) Craibeffective component. The present invention also relates to the new medicinal purposes of a stilbene compound and derivatives thereof, particularly to the application of the stilbene compound and the derivatives thereof in the preparation of endothelin antagonists especially the application of 3, 4', 5-trihydroxy trans-stilbene in the preparation of endothelin antagonists.

Description

The application in the preparation endothelin antagonist of stilbene compound and derivant thereof
The present invention relates to a kind of pharmaceutical preparation and Cissus assamica (Laws.) Craib extraction of effective components that contains Chinese herbal medicine Cissus assamica (Laws.) Craib effective ingredient; The invention still further relates to the new medicine use of stilbenes compound and derivant thereof, the application that specifically is stilbenes compound and derivant thereof in the preparation endothelin antagonist, particularly 3,4 ', the application of 5-trihydroxy trans-stilben in the preparation endothelin antagonist belongs to drug world.
Cissus assamica (Laws.) Craib [Cissus assamica (Laws.) Craib] is Vitaceae (Vitaceae) Cissus (Cissus L.) plant, among the peoplely is used for the treatment of traumatic injury, sprains, rheumatic arthritis pain, fracture and carbuncle pyogenic infections from tumour or sore.Guangxi one band is used for the treatment of venom and has good effect.The extraction and the The Chemical Constituents of relevant this plant effective site are not appeared in the newspapers so far as yet.
Endothelin is a kind of bioactive substance of latest report in the world.The generation development and the Endothelin of many cardiovascular and cerebrovascular diseases have confidential relation, and as hypertension, coronary heart disease, cerebrovascular accident, heart failure etc., Endothelin participates in pathology, the physiological process of these diseases.Many countries are the pathological index of Endothelin as diseases such as hypertension, coronary heart disease, cerebrovascular accident, heart failure, and treat above-mentioned disease by the biological agent of regulating Endothelin.Therefore, screening is a kind of can the bioactive medicine of antagonism Endothelin be present extremely important and significant thing.
Stilbenes compound is that the structural formula parent nucleus is a compounds of stilbene.Its structural formula is a following general formula I:
Figure C9710392800031
Wherein 3,4,5,2 ', 3 ', 4 ', 5 ', 6 ' diverse location, the not isoplastic replacement on two phenyl ring constituted numerous stilbenes compounds.This compounds can be known as medicine, and still, up to the present, relevant this compounds of Shang Weijian is used to prepare the report that endothelin antagonist is used.
One of the object of the invention provides a kind of pharmaceutical preparation, and it contains the effective component extracts of Chinese herbal medicine Cissus assamica (Laws.) Craib.
Another object of the present invention provides Chinese herbal medicine Cissus assamica (Laws.) Craib extraction of effective components.
Another object of the present invention provides stilbenes compound and the application of derivant in the preparation endothelin antagonist thereof.
Furtherly, another object of the present invention provides 3, and 4 ', the application of 5-trihydroxy trans-stilben in the preparation endothelin antagonist.
We had once carried out the pharmacological research of antagonism Endothelin (ET) to the Cissus assamica (Laws.) Craib plant; find the contraction of the isolated aorta bar that its can antagonism be caused by ET; and to due to whole animal death have protective effect; and then it the extraction and the mask work of chemical constituent have been carried out; in the hope of the effective ingredient of discovery antagonism ET, thereby finished the present invention.
Pharmaceutical preparation of the present invention contains the effective extract part of Cissus assamica (Laws.) Craib plant for the treatment of effective dose.
Medicine of the present invention preferably contains effective extract part of the Cissus assamica (Laws.) Craib plant of 0.1-99.9% weight portion.
Medicine of the present invention more preferably contains effective extract part of the Cissus assamica (Laws.) Craib plant of 10-90% weight portion.
Medicine of the present invention further preferably contains effective extract part of the Cissus assamica (Laws.) Craib plant of 15-80% weight portion.
Medicine the best of the present invention contains effective extract part of the Cissus assamica (Laws.) Craib plant of 20-70% weight portion.
Effective extract part of the said Cissus assamica (Laws.) Craib plant of the present invention is the effective extract that extracts with following method:
Get 10 kilograms of the roots (dry product) of Cissus assamica (Laws.) Craib plant, pulverize the back with 95% alcohol reflux 3 times, merge extractive liquid,, decompression and solvent recovery obtains paste; Add the abundant dispersed with stirring of equivalent distilled water, fully extract with petroleum ether, chloroform, ethyl acetate successively, collecting ethyl acetate extraction part is effective extract part of Cissus assamica (Laws.) Craib.
Effective extract part of above-mentioned Cissus assamica (Laws.) Craib is a kind of extraction mixture, according to the pharmaceutical preparation technology of routine, can add conventional excipient with it as effective ingredient, is prepared into any pharmaceutical preparation that is suitable for using clinically.For example, pill, tablet, capsule, oral liquid, injection, powder, unguentum, aerosol etc.Preparing these pharmaceutical preparatioies is those of ordinary skills' technical activity routinely.
Effective extract part for above-mentioned Cissus assamica (Laws.) Craib plant, we have carried out further purification, by extraction, separation and spectroscopic data analysis, obtained monomeric compound 3,4 ', 5-trihydroxy trans-stilben, this chemical compound confirms through the inside and outside pharmacological evaluation, ET being had have the biological effect antagonism, is the effective ingredient of the anti-ET of Cissus assamica (Laws.) Craib plant.
Therefore, the invention provides and a kind ofly from the Cissus assamica (Laws.) Craib plant, extract 3,4 ', the method for 5-trihydroxy trans-stilbene, this method is:
Get 10 kilograms of the roots (dry product) of Cissus assamica (Laws.) Craib plant, pulverize the back with 95% alcohol reflux 3 times, merge extractive liquid,, decompression and solvent recovery obtains paste; Add the abundant dispersed with stirring of equivalent distilled water, fully extract with petroleum ether, chloroform, ethyl acetate successively, collecting ethyl acetate extraction part is the active site of Cissus assamica (Laws.) Craib.This position is preferably carried out three times and is separated through silica gel H column chromatography for separation repeatedly, and (9: 1-5: 5) gradient elution obtains crystallization with petroleum ether-ethyl acetate again.
This crystallization is white in color, and is blue-fluorescence under the fusing point, ultraviolet light.
Its spectroscopic data is as follows:
EI-MS m/z:228 (M +), 211,199,181,157,115,91, molecular formula is C 14H 12O 3, degree of unsaturation Ω=9.
IR(KBr)cm -1：3280，1600，1580，1410，1150。
1H-NMR(DMSO-d 6)δppm：9.50(1H，s)，9.20(2H，s)，7.40(2H，d，J＝8.5Hz)，6.90(1H，d，J＝16Hz)，6.80(1H，d，J＝16Hz)，6.70(2H，d，J＝8.5Hz)，6.40(2H，d，J＝1.8Hz)，6.10(1H，s)。
13C-NMR(DMSO-d 6)δppm：158.4，157.1，139.1，127.9，127.8，127.7，125.6，1154，104.2，101.7。
Can be accredited as 3,4 ' by above data, 5-trihydroxy trans-stilbene, structural formula is as follows:
Figure C9710392800051
3,4 ', 5-trihydroxy trans-stilbene is a new structure type in the endothelin antagonist as the representative of stilbene compound.Show that through experiment stilbene compound all has the effect of antagonism Endothelin.
Said stilbene compound of the present invention and derivant thereof are the compounds with following general formula I I:
Wherein, the R group be H or-OR ', described R ' is selected from H ,-CH 3, or glucoside any or more than one group.
The above-mentioned general formula I I of the present invention is during by following expression
Figure C9710392800062
Wherein preferred following compounds:
4-hydroxyl Stilbene;
3,5-dihydroxy Stilbene;
4,4 '-dihydroxy Stilbene;
3,5,4 '-trihydroxy stilbene;
3,5,3 ', 4 '-tetrahydroxy Stilbene;
3,5,2 ', 4 '-tetrahydroxy Stilbene;
3,5-pinosylvin monomethyl ether;
3 '-methoxyl group-4 '-hydroxyl Stilbene;
Rhapontigenin;
4,3 '-dimethoxy-4 ' '-the hydroxyl Stilbene;
The butterfly Stilbene;
3,3 '-dimethoxy-4 ', 4 '-dihydroxy Stilbene;
3,4,2 ', 4 ', 6 '-pentamethoxyl Stilbene;
The resveratrol glucoside;
5,3 ', 4 '-trihydroxy-3-hydroxyl Stilbene glucoside;
3,5-dihydroxy Stilbene monomethyl ether glucoside;
3 '-methoxyl group-4 '-hydroxyl Stilbene glucoside;
5,3 '-dihydroxy-4 '-methoxyl group-3-hydroxyl Stilbene glucoside;
4,3 '-dimethoxy-4 ' '-hydroxyl Stilbene glucoside.
Most preferred compound is 3 in the general formula compound of the present invention, 4 ', and 5-trihydroxy trans-stilben.
Embodiment 1
Get 10 kilograms of the roots (dry product) of Cissus assamica (Laws.) Craib plant, pulverize the back with 95% alcohol reflux 3 times, merge extractive liquid,, decompression and solvent recovery obtains paste; Add the abundant dispersed with stirring of equivalent distilled water, fully extract with petroleum ether, chloroform, ethyl acetate successively, collecting ethyl acetate extraction part is effective extract part of Cissus assamica (Laws.) Craib.Get effective extract part 100 grams, add starch 500 grams, mix homogeneously, pelletize, granulate, tabletting, sugar coating gets tablet.
Embodiment 2
Get 10 kilograms of the roots (dry product) of Cissus assamica (Laws.) Craib plant, pulverize the back with 95% alcohol reflux 3 times, merge extractive liquid,, decompression and solvent recovery obtains paste; Add the abundant dispersed with stirring of equivalent distilled water, fully extract with petroleum ether, chloroform, ethyl acetate successively, collecting ethyl acetate extraction part is the active site of Cissus assamica (Laws.) Craib.This position is preferably carried out three times and is separated through silica gel H column chromatography for separation repeatedly, and (9: 1-5: 5) gradient elution obtains crystallization with petroleum ether-ethyl acetate again.
Get crystallization 10 grams, add 100 gram starch, go into the blender mixing, encapsulated, every powder charge powder 1 gram makes capsule.
In the pharmacological evaluation data, for convenience, with chemical compound 3,4 ' of the present invention, 5-trihydroxy trans-stilben is abbreviated as CA-1201, and therefore, in following experimental example, this term " CA-1201 " is meant 3,4 ', 5-trihydroxy trans-stilben.Following experimental example has described chemical compound 3,4 ' of the present invention in detail, the effect of 5-trihydroxy trans-stilben antagonism endothelin-1 biological effect.Experimental example 1 CA-1201 causes the protective effect of death of mice to endothelin-1
40 of ♂ Kunming mouses, body weight 20 ± 2g, after fasting was supplied water 18 hours, CA-1201 was with the 10mg/kg lumbar injection after 15 minutes, the ET-1 of tail vein injection 6mmol/kg, surpassing 15 minutes with the time-to-live be survival, writes down death time of animal and death toll.
CA-1201 is after the abdominal cavity gives 10mg/kg dosage; death time of animal obviously prolongs; behind the matched group (intravenous injection ET-1); the time of animal dead is 3.22 ± 0.62 minutes; and in advance with after the CA-1201 protection; death time of animal is 11.52 ± 4.50 minutes, learns by statistics and handles, and the two has significant difference (p＜0.05).
Table 1.CA1201 causes the death of mice protective effect to ET1
Matched group CA-1201 group
Body weight death time body weight death time
(g) (min) (g) (min)
23.0 4.17 21.0 15
21.5 4.10 22.5 4.88
23.0 3.03 20.5 7.08
19.0 2.13 21.0 6.97
21.0 3.15 21.5 15
23.0 3.00 21.0 4.95
22.0 3.93 18.5 12.92
21.0 3.18 19.0 15
19.0 3.28 20.5 15
20.0 3.33 20.5 15
The tremulous pulse flesh bar perfusion experiment 3.22 ± 0.62 11.52 ± 4.50 experimental example 2 exsomatizes
♂ SD rat, body weight 230 ± 10g,, with winning thoracic aorta fast after the rat stunning, after separating connective tissue, be cut into the long vascular ring of 2～3mm, place Krebs-Henseleit physiological solution (K-H liquid, pH7.40 ± 0.05,95%O respectively 2+ 5%CO 2, 37.0 ± 0.5 ℃) in, stablize, add 2g basis tension force, with 10 -7The M norepinephrine adds ET-1 10 after swashing secondary, balance in advance -9M, wait to reach the maximum collapse effect after, add the CA-1201 (is solvent with 2%DMSO, experiment compare) of variable concentrations respectively with 2%DMSO, connect desk-top balance recorder through tonotransducer, record blood vessel isotonic contraction and diastole situation.
In the environment that exsomatizes, CA-1201 (10 -8M and 10 -9M) rat chest aorta that all can antagonism ET-1 the causes vascular effect that contracts is compared with matched group, and this makes apparatus significance meaning (p＜0.05); And the CA-1201 antagonism ET-1 vascular effect tool dose dependent that contracts.
Table 2.CA-1201 is to the contract antagonism of vascular effect of ET-1
Group concentration antiotasis
ET-1 10 -9M 100.00±3.28
ET-1+CA-1201 10 -9M 55.76±8.93 *
ET-1+CA-1201 10 -8M 32.48 ± 3.19 *The effect of 3 pairs of blood pressures of experimental example
♂ SD rat, body weight 230 ± 10g, supply water on an empty stomach behind the 18h, behind CA-1201 tail vein injection 5 and the 10mg/kg, give ET-16 μ g/kg again from the tail vein at once, observe the variation of blood pressure, use Impedance Determination rat arteria caudalis blood pressure, and changing value and matched group are compared.The results are shown in table 3-5.
Table 3 matched group blood pressure situation
Time matched group (Δ SBP mmHg)
1 2 3 4 5 M±SD
0 0 0 0 0 0 0
5 35 35 35 40 35 36±2.24
10 55 50 50 60 60 55±5.00
15 60 55 60 80 80 67±12.04
20 40 45 40 45 55 45±6.12
25 35 40 35 45 45 39±4.18
30 20 25 25 30 35 27±5.70
45 10 15 15 15 15 14±2.24
60 0 0 0 5 3 1.6±2.30
The heavy dose of group of table 4 CA-1201 (10mg/kg) blood pressure situation
Time Δ SBP (mmHg)
1 2 3 4 5 M±SD
0 0 0 0 0 0 0
5 3 15 19 10 8 11±6.20
10 8 25 25 15 17 18±7.21
15 3 20 25 19 23 18±8.72
20 3 20 28 15 20 17.2±9.20
25 7 15 25 13 16 15.2±6.50
30 13 17 27 12 13 16.4±6.23
45 18 13 25 10 10 15.2±6.38
60 13 5 10 7 5 10.4±3.25
Table 5 CA-1201 small dose group (5mg/kg) blood pressure situation
Time Δ SBP (mmHg)
1 2 3 4 5 M±SD
0 0 0 0 0 0 0
5 30 28 25 30 20 26.6±4.22
10 50 50 45 45 40 46.0±4.18
15 48 55 50 55 47 51.0±3.81
20 50 55 45 45 45 48.0±4.47
25 45 48 37 35 40 41.0±5.43
30 20 45 32 32 35 32.8±8.93
45 25 15 24 25 25 22.8±4.38
60 10 10 10 10 15 11.0±2.24
As can be seen from the above table, the pressor effect that heavy dose of CA-1201 (10mg/kg) causes ET-1 has tangible antagonism, compare this antagonism with matched group tangible dose dependent is arranged, but low dose of CA-1201 (5mg/kg) has the trend of the boosting of passivation ET-1, but does not have the significance meaning.Experimental example 4 CA-1201 are to the arrhythogenic antagonism of ET-1
The SD rat, body weight 250 ± 50g, after fasting was supplied water 18 hours, after 846 animal compound anesthetic intramuscular injection, back of the body position was fixing, and II leads the variation of recording ecg with the standard limbs.After treating that electrocardiogram is stable, intravenous injection ET-10.6nmol/kg, the electrocardiogram of record after the administration gives the CA-1201 of various dose group ( intravenous injection 10,30,90 and intramuscular injection 10 μ g/kg) then, observes and respectively organize Electrocardiographic variation in whole experiment (60 minutes).
CA-1201 has tangible antagonism to various types of arrhythmia that endothelin-1 causes, effect to ventricular arrhythmia is comparatively obvious, after the intramuscular injection, the also arrhythmia that causes of antagonism ET-1 effectively is better than intravenous injection to the antagonism trend of chamber property and atrial arrhythmia.
Accompanying drawing 1 is to be used to illustrate that the CA-1201 intravenous injection is to the influence of ET-1 boosting (n=5, x ± SD).

Claims (6)

1, a kind of endothelin antagonist is characterized in that it contains the effective extract part of Cissus assamica (Laws.) Craib plant for the treatment of effective dose, and described effective extract part is the extract that extracts with following method:
Get the root of Cissus assamica (Laws.) Craib plant, pulverize the back with 95% alcohol reflux 3 times, merge extractive liquid,, decompression and solvent recovery obtains paste; Add the abundant dispersed with stirring of equivalent distilled water, fully extract with petroleum ether, chloroform, ethyl acetate successively, collecting ethyl acetate extraction part is effective extract part of Cissus assamica (Laws.) Craib.
2,, it is characterized in that it contains effective extract part of the Cissus assamica (Laws.) Craib plant of 0.1-99.9% weight portion according to the endothelin antagonist of claim 1.
3,, it is characterized in that it contains effective extract part of the Cissus assamica (Laws.) Craib plant of 10-90% weight portion according to the endothelin antagonist of claim 1.
4,, it is characterized in that it contains effective extract part of the Cissus assamica (Laws.) Craib plant of 15-80% weight portion according to the endothelin antagonist of claim 1.
5,, it is characterized in that it contains effective extract part of the Cissus assamica (Laws.) Craib plant of 20-70% weight portion according to the endothelin antagonist of claim 1.
6, a kind of extracting method of endothelin antagonist is characterized in that this method comprises:
Get the dry root of Cissus assamica (Laws.) Craib plant, pulverize the back with 95% alcohol reflux 3 times, merge extractive liquid,, decompression and solvent recovery obtains paste; Add the abundant dispersed with stirring of equivalent distilled water, fully extract with petroleum ether, chloroform, ethyl acetate successively, collecting ethyl acetate extraction part is the active site of Cissus assamica (Laws.) Craib, and this position is through the silica gel H column chromatography for separation, (9: 1-5: 5) gradient elution obtains crystallization with petroleum ether-ethyl acetate again.7,3,4 ', the application of 5-trihydroxy trans-stilbene in preparation endothelin antagonist medicine.
CN97103928A 1997-04-16 1997-04-16 Application of stilbene compound and its derivative in preparation of endothelium element antagonist agent Expired - Fee Related CN1055859C (en)

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US6361815B1 (en) * 1998-12-21 2002-03-26 Pure World Botanicals, Inc. Products comprising trihydroxystilbenes and derivatives thereof and methods for their manufacture and use
CN1398838A (en) 2001-07-26 2003-02-26 中国人民解放军军事医学科学院放射医学研究所 Diphenylethylene compound and its prepn and application in preventing and treating diabetes
ITRM20130596A1 (en) * 2013-10-29 2015-04-30 Bridgestone Corp NEW CLASS OF ANTI-AGING AGENTS FOR RUBBER PRODUCTS
CN105055449B (en) * 2015-07-27 2019-08-09 中国科学院西北高原生物研究所 A kind of Sialon bone extract with anti-inflammatory and analgesic activity, preparation method and traditional Chinese medicine preparation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04159280A (en) * 1990-10-24 1992-06-02 Tsumura & Co 5-lipoxygenase inhibitor containing hydroxystilbene-based compound as active ingredient
JPH0624967A (en) * 1992-03-05 1994-02-01 Yushiro Chem Ind Co Ltd Substance having mutagen-suppressing action

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04159280A (en) * 1990-10-24 1992-06-02 Tsumura & Co 5-lipoxygenase inhibitor containing hydroxystilbene-based compound as active ingredient
JPH0624967A (en) * 1992-03-05 1994-02-01 Yushiro Chem Ind Co Ltd Substance having mutagen-suppressing action

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
中国药房，第8卷4期 1997.7.1 王峰等，红背丝绸拮抗内皮素-1生物效庆的研究 *

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