CN1068782C - Anti-cancer medicine with extracts from goldenrain and the preparation thereof - Google Patents
Anti-cancer medicine with extracts from goldenrain and the preparation thereof Download PDFInfo
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- CN1068782C CN1068782C CN96104672A CN96104672A CN1068782C CN 1068782 C CN1068782 C CN 1068782C CN 96104672 A CN96104672 A CN 96104672A CN 96104672 A CN96104672 A CN 96104672A CN 1068782 C CN1068782 C CN 1068782C
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Abstract
The present invention discloses a goldenrain extract and a medicinal preparation containing the goldenrain extract. The extract and the medicinal preparation thereof have the functions of cancer resistance, immunity suppression, virus resistance, free radical removal, platelet coacervation resistance and thrombogenesis resistance.
Description
The present invention relates to a kind of serves as the anticarcinogen of effectively total composition with the Luan Shu extract, and the preparation method of this medicine; The invention still further relates to the anticancer active component that from Luan Shu, extracts and the extracting method of this active component.
Sapindaceae goldenrain tree Pterostyrax (Koelreuteria Laxm) plant, the whole world has 4 kinds, in homemade 3 kinds, 1 mutation, another kind originates in Fiji Islands.Machaka is to arbor, and is wild in mountain forest or cultivate in garden.Wherein extensively there is distribution in southwest, south China to North China, Liaoning to Luan Shu (Koelreuteria paniculata Laxm) certainly, Taiwan Luan Shu (Koelreuteria henryiDummer) solely originates in Taiwan Province, Radix Seu Flos Koelreuteriae Bipinnatae (Koelreuteria bipinnataFraneh) originates in Guangdong, Guangxi, East China and southwest, and popular name is called money tree.Wherein mutation koelreuteria integrifoliola tree (Koelreuteria bipinnata var.integrifoliola (Merr) T.Chen) then is common in Anhui, zhejiang and other places.This plant resources is abundant.
People find that very early this platymiscium has certain medical value.Put down in writing its " argument pain, the corner of the eyes is hindered in lacrimation, the order that disappears is swollen " in the Shennong's Herbal; The Tang Materia Medica record " is fried in shallow oil altogether with Rhizoma Coptidis, is treated redness and ulceration of eyelids ", among the people being used for " wind and heat dispersing, detoxifcation parasite killing ".But, about the chemistry and the bioactivity research of this platymiscium, domestic and international all understatement roads.Chirva in 1070, V.Ya. etc. are separated to koelreuteria saponin A and B from seed, and to measure its chemical constitution be triterpenoid saponin (V.Ya.Chirva, P.K.Kintya, andV.A.sosnovski, Khim.Prir.soedin, 6,328 (1970)).Nineteen fifty-one Carlson, people such as H.J. find to contain among the Luan Shuye gallicin, and multiple bacterium especially fungus is had certain inhibitory action (H.J.Carlson et al.Antibiotics andChemotheropy, vol.1, pp.431-442,1951; CA1952,46:6188c).Chen Guolian in 1985 etc. have confirmed that further the extract of this leaves of plants has certain inhibitory action to staphylococcus aureus, Staphylococcus albus and Bacillus proteus, but do not see the report (" the Shaanxi traditional Chinese medical science " 1985,6 (3) 144) of effective ingredient.Japanese hutano in 1991, T. etc. are reported in the Galla Turcica (Galla Helepensis) acyl quercitrin (Planta Medica, Vol.57 (1) 83-84,1991) that Luan Shuzhong has found xanthine oxidase (XOD) free radical is had scavenging action.Abou-Shoer.M. in 1993 etc. are separated to from the goldenrain tree tree branches and leaves of Taiwan has inhibiting flavone compound (J.Nat.Prod., 56 (6) 967-969,1993) to the tyrosine protein kinase (PTK) with related to cancer.Song YN in 1994 etc. are separated to 3 kinds of external ring lignin chemical compounds that 8 kinds of cell strains such as people's pulmonary carcinoma (A-549), human breast carcinoma (MCF-7) and large intestine adenocarcinoma (HT-29) had cytotoxicity and microtubule polymerization enzyme inhibition from the weakly polar component of Taiwan Luan Shu alcohol extract, close with anticancer podophyllotoxin, but all belong to fat-soluble lignin chemical compound, develop limited.But do not see relevant Luan Shu ethyl acetate extraction component YQE and purified components YQE1, YQE2 and YQE3 have inhibiting report to the laboratory animal tumor in vivo.
We have carried out comparatively systematic research to this platymiscium, therefrom separate obtaining the multiple bioactive total active component of having of ethyl acetate extraction and having carried out a series of pharmacodynamic experiments, confirm that this effective ingredient has multiple pharmacological effect; We have made pharmaceutical preparation with this active component.
Therefore, the present invention seeks to prepare a kind of medicine anticancer and immunosuppressive action, antivirus action, free radical scavenging effect and function of promoting blood circulation to disperse blood clots that has.
The present invention also provides the separation method of Luan Shu extract active component and the preparation method of this medicine of the present invention.
The extracts active ingredients step of medicine of the present invention is as follows:
1, branch and leaf, flower, the fruit of getting raw medicinal material Luan Shu adds 10-80% ethanol water reflux, extract, or soaks percolation and extract, extracting solution, concentrating under reduced pressure boils off alcohol and obtains the said extracting solution A of the present invention;
2, said extracted liquid A, extract respectively with organic solvent successively, obtain different active components, water-soluble as extract A, after filtering decontamination, use petroleum ether, dichloromethane, ethyl acetate and butyl alcohol extraction successively, obtain extracting solution B1 (ligroin extraction), extracting solution B2 (dichloromethane extract), extracting solution C (ethyl acetate and butanol extract), extracting solution D (water extract) respectively;
3, collect ethyl acetate and butyl alcohol extraction liquid C liquid, be evaporated to driedly, obtain the said active component extract of the present invention YQ-E (the application is with this extract called after YQE).
4, with solvent YQE is extracted, obtain the said purification active component of the present invention extract (the application is with this extract called after YQE1 and YQE2).
5, YQE carries out column chromatography purification with chromatography, obtains the said purification active component of the present invention extract (the application is with this extract called after YQE3).
Used extraction solvent can be water or 1-4 carbon alcohol, the pure acetone that contains 10-80% water and the acetone that contains 20-30% water thereof in the above-mentioned steps 1.
Organic solvent in the above-mentioned steps 2,4 comprises the alkane of C6-C7, as, hexane, cyclohexane extraction, petroleum ether; Halogenated hydrocarbon, as, dichloromethane, dichloroethanes, chloroform, carbon tetrachloride; Ether and organic acid esters, as, ether, ethyl acetate, butyl acetate, pentyl acetate; The aliphatic alcohol of C3-C5 etc.
Chromatogram purification in the above-mentioned steps 5 comprises absorption and partition chromatography purification such as macroporous resin, silica gel, aluminium oxide.For example, behind the D101 macroporous resin, use the 0-90% ethanol elution in the elder generation, collect the 30-50% eluent, be concentrated into driedly, promptly get purified components YQE3.
Purification effective ingredient YQE1 of the present invention, YQE2, YQE3 contain progallin A, gallic acid and Luan Shu polyphenol compound (polyphenols), totally constitute active component YQE of the present invention.
Can be effective ingredient with Luan Shu extract of the present invention, make medicament commonly used clinically according to the preparation process of routine.This medicament contains the described Luan Shu extract of 0.01-99.9% weight portion, preferably contains the described Luan Shu extract of 1-80% weight portion, and the best contains the described Luan Shu extract of 10-60% weight portion.
Luan Shu extract of the present invention also can be formed compound medicine with other Chinese medicines or extract compatibility, for example:
1, shared with activating blood and removing stasis drug, as, and be selected from following one or more drug matching and form compound medicine: Radix Notoginseng, Flos Carthami, Radix Angelicae Sinensis, Radix Salviae Miltiorrhizae, Radix Paeoniae Rubra, Rhizoma Curcumae, Rhizoma Corydalis, Olibanum, Myrrha;
2, shared with the benefiting QI and nourishing blood medicine, as, and be selected from following one or more drug matching and form compound medicine: Radix Ginseng, Radix Codonopsis, the Radix Astragali, Fructus Schisandrae Chinensis;
3, shared with heat and toxic materials clearing away medicine and antitumor Chinese herbal medicine, as, and be selected from following one or more drug matching and form compound medicine: Rhizoma Coptidis, Radix Et Rhizoma Rhei, Radix Scutellariae, Radix Sophorae Tonkinensis, Radix Sophorae Flavescentis, Herba Hedyotidis Diffusae, Herba Scutellariae Barbatae, Herba Lobeliae Chinensis, Spica Prunellae;
4, shared with the softening the hard mass cancer-eliminating medicine, as, and be selected from following one or more drug matching and form compound medicine: Sargassum, Thallus Laminariae (Thallus Eckloniae) etc.
In the preparation process of above-mentioned folk prescription or compound medicine, according to the needs of dosage form and clinical use, can add various excipient, for example, binding agent, disintegrating agent, filler, wetting agent, solvent, correctives, emulsifying agent, antiseptic etc.
The said pharmaceutical dosage form of the present invention can be tablet, pill, capsule, electuary, spray, oral liquid, suspension, externally applied liniment, transdermal absorption formulation and injection etc.
Medicine of the present invention has antitumor action, immunosuppressive action, antivirus action, free radical scavenging effect, anti thrombotic action, anticoagulant effect.
One, the antitumor action of Luan Shu extract YQE2
1, YQE2 is to the antitumor action of Mice Bearing Lewis Lung Cancer
Material and method
Laboratory animal C
57/ BL mice is provided by Chinese Academy of Sciences's Shanghai Experimental Animal Center, the middle section moving pipe meeting quality certification: 005.
Tumor kind Lewis lung cancer.
Medicine YQE2 is a pale yellow powder, uses DMSO, and it is standby that tween 80 and normal saline are made into suspensoid.
After the method mouse inoculation tumor, random packet begins the lumbar injection treatment next day, successive administration 10 days, and dissect the tumor weight of weighing next day after the drug withdrawal, and compare with control group mice, calculates administration group tumor control rate.
The result be by can seeing in table 1, table 2, the table 3, YQE2 when dosage 70mg/kg, to the mouse tumor suppression ratio more than 40%.
Table 1 YQE2 begins to begin at last last X ± SD (g) %NS 0.2 to the heavy tumour inhibiting rate P of antitumor action group dosed administration number of animals body weight (g) the tumor value mg/kg approach of Mice Bearing Lewis Lung Cancer
*I.p 10 10 16.2 20.1 2.67 ± 0.7--and-BYQE 35 i.p 88 15.9 19.8 2.19 ± 0.56 18.0＜0.001BYQE, 70 i.p 88 16.0 18.3 1.57 ± 0.58 41.2＜0.01CTX, 30 i.p 88 16.0 18.9 1.57 ± 0.61 41.2＜0.01*:ml/ are only
The conclusion experimental result shows YQE2, and 70mg/kg has obvious antineoplastic to Mice Bearing Lewis Lung Cancer.
2, YQE is to the vitro inhibition effect of P388 mouse leukemia cell
Sample and oncocyte effect 24 hours, % represents with suppression ratio, the results are shown in Table 5.
Table 5 money tree extract position is to In-vitro Inhibitory Effect sample 1000 μ g/ml 100 μ g/ml 10 μ g/mlBLS-I-32A 45.7 27.2 12.1BLS-I-32B, 100 95.3 67.7BLS-I-32C (YQE) 100 58.2 78.9BLS-I-32D 79.9 62.9 59.1 of P388 mouse leukemia cell
Conclusion: Luan Shu extract components B2, C (YQE) and D all can significantly suppress the propagation of P388 mouse leukemia cell in 10 μ g/ml concentration, are the best with C (YQE) wherein.
Two, the Luan Shu extract is to Immune Effects
1, Luan Shu spends 70% ethanol extraction (YQH) according to 5 times of dilutions, least concentration 0.128ng/ml, maximum concentration 500ng/ml.Fig. 1 is seen in its effect to human tonsil's mononuclear cell propagation, and BYH has the obvious suppression effect when 100 μ g/ml and 500 μ g/ml concentration.
2, goldenrain tree tree branches and leaves extract YQE (comprising YQE1, YQE2 or YQE3) is according to the doubling dilution dilution, and least concentration is 0.31 μ g/ml, maximum concentration 100 μ g/ml.Wherein, YQE1 shows comparatively obvious suppression proliferation function to human tonsil's mononuclear cell propagation in 6.25-100 μ g/ml concentration range, and YQE2 also shows certain inhibition propagation trend at 100 μ g/ml, sees Fig. 2.
3, goldenrain tree tree branches and leaves extraction component (YQE) is seen Fig. 3 to the effect of the inductive mouse boosting cell propagation of ConA.In 100-500 μ g/ml concentration range, show comparatively obvious suppression proliferation function.
4, Luan Shu seed extract (YQZ) is seen Fig. 4 to the influence of the inductive mouse boosting cell proliferation function of ConA, also shows the obvious suppression proliferation function in 100-500 μ g/ml concentration range.
In sum, Luan Shu extract of the present invention has tangible immunosuppressive action.
Three, antivirus action
Virus is one of carcinogenic factor, and the active component of Luan Shu extract has inhibitory action to several viruses, and its ethyl acetate extraction component YQE is 0.062-0.50mg/ml to herpesvirus I and II type minimum inhibitory concentration.To the inhibitory action of HIV-RT enzyme, IC50 is 0.033.0.012mg/ml。In addition, the crow hepatovirus is also had certain inhibitory action, when extract concentrations during at 1.0-2.0mg/ml its suppression ratio can reach 74.6-42.6%.
Four, free radical scavenging effect
At present free radical and cancer and aging theory in close relations in the world have been widely accepted and have been applied to clinical, and the growth that not only suppresses cell in anticancer therapy is most important, and it also is vital protecting normal cell and tissue to be without prejudice simultaneously.To the scavenging action of oxygen-derived free radicals and hydroxyl radical free radical clearly, its minimal effective concentration that superoxide anion and hydroxyl radical free radical are removed is respectively 12ng/ml and 1.7ng/ml to the Luan Shu extract in experiment.
Five, function of promoting blood circulation to disperse blood clots
Motherland's medical science generally adopts blood circulation promoting and blood stasis dispelling to treatment for cancer, heat-clearing and toxic substances removing, medicine such as hard masses softening and resolving and strengthening vital QI to eliminate pathogenic factors and prescription thereof, and obtained certain progress, many blood-activating and stasis-removing that studies show that have a potentiation [Deng Youan etc. to anticancer, blood-activating and stasis-removing adds anticancer drug therapy acute leukemia observation of curative effect, the Shanxi medical magazine, 1988,17 (2), P79], there are some researches show that it can realize antitumor hematogenous metastasis [Hu Sukun, the experimental study of Radix Paeoniae Rubra 801 antineoplastic by improving mice with tumor blood coagulation state and platelet function, the Chinese Medicine journal, 1990,5 (3), P22].Luan Shu extract of the present invention has the platelet aggregation effect that obvious suppression ADP brings out, and the laser-induced thrombosis is prevented effect, thereby point out it to have function of promoting blood circulation to disperse blood clots.
In sum, Luan Shu extract and pharmaceutical preparation thereof have anticancer and immunosuppressive action, antivirus action, free radical scavenging effect and anti-platelet aggregation and anti-thrombosis function.
Description of drawings:
Fig. 1 is that Luan Shu spends the effect of 70% ethanol extraction (YQH) to human tonsil's mononuclear cell propagation.
Fig. 2 is the effect of goldenrain tree tree branches and leaves extract YQE to human tonsil's mononuclear cell propagation.
Fig. 3 is that the goldenrain tree tree branches and leaves extracts the effect of component (YQE) to the inductive mouse boosting cell propagation of ConA.
Fig. 4 is the influence of Luan Shu seed extract (YQZ) to the inductive mouse boosting cell proliferation function of ConA.
Embodiment 1
1), get 0.2 kilogram in the branch and leaf of raw medicinal material Luan Shu, add 1.6 liters of 70% ethanol waters, flood after 48 hours, inclining leachate, adds 1.6 liters of 70% ethanol again, soaks 24 hours, inclining leachate, merges, and boils off ethanol, must about 400 ml water solution A;
2), 400 ml water solution A filter, and add 200 milliliters of petroleum ether (60-90 ℃) extracting twice in separatory funnel, vibrate 5 minutes at every turn, leave standstill 30 minutes, layering divides and removes upper strata extracting solution (B1);
3), with above-mentioned 2) in the lower aqueous solution 200 milliliters of extracting twice that in separatory funnel, add methylene chloride, vibrated 5 minutes at every turn, left standstill 30 minutes, layering divides sub-cloud dichloromethane extract (B2);
4), with above-mentioned 3) at the middle and upper levels aqueous solution place separatory funnel, add 200 milliliters of ethyl acetate extractions 4 times, vibrated 5 minutes at every turn, left standstill 30 minutes, the upper strata acetic acid ethyl acetate extract is got in layering; The combined ethyl acetate extracting solution, be evaporated to dried, pale brown toner end 14 grams, be the said active component extract of the present invention YQE.
Embodiment 2
With the extract YQE10 gram that obtains in the foregoing description 1,350 milliliters of adding distil waters, heating for dissolving is put cold, add 100 milliliters of extracted with diethyl ether 2 times, each 5 minutes, left standstill 30 minutes, get ether layer, after adding 25 milliliters in water and washing, be concentrated into dried, pale brown toner end 3.3 grams (YQE1); Water layer adds 150 milliliters of extractions of ethyl acetate 4 times, each 10 minutes, left standstill 30 minutes, the combined ethyl acetate extracting solution adds water and washes for 50 milliliters, left standstill 30 minutes, branch vibration layer, acetic acid ethyl acetate extract add anhydrous magnesium sulfate drying, filtration, are evaporated to dried, get pale brown toner end 5.3 grams, be the said active component extract of the present invention YQE2.
Embodiment 3
The active component extract YQE10 gram of getting embodiment 1 preparation adds 100 milliliters of dissolvings of water, last D101 macroporous resin column (3 * 30cm), with 0-90% ethanol water gradient elution, collect the eluent of 30-50% ethanol water, be evaporated to dried, the said active component extract of the present invention YQE3 5.5 gram.
Embodiment 4
Get active component extract YQE2 of the present invention 90 grams of embodiment 1 preparation, add starch 10 grams, magnesium stearate 0.1 gram, mix homogeneously is crossed 60 mesh sieves, and fine powder is encapsulated, and every capsules loading amount 0.3 gram contains YQE2 0.25-0.30 gram.Oral adult every day 1-3 time, each 1-5 grain.
Embodiment 5
Get the Radix Astragali, Radix Salviae Miltiorrhizae, Radix Paeoniae Rubra, Rhizoma Curcumae, each 1000 gram of Herba Hedyotidis Diffusae, it is extracted twice with water-boiling method, extracting solution is concentrated into extractum, oven dry, and pulverize, cross the 80-100 mesh sieve.Get YQE2 250 grams of embodiment 2 preparation, the Radix Astragali, Radix Salviae Miltiorrhizae, Radix Paeoniae Rubra, Rhizoma Curcumae, Herba Hedyotidis Diffusae extract powder mix homogeneously with preparation add dry starch 10% mixing, are that wetting agent is made soft material with 95% ethanol, cross the granulation of 16 mesh sieves, dry, granulate.Add magnesium stearate 1%, mixing, it is heavy to calculate sheet, makes every to contain Luan Shu extract 0.07 gram, tabletting, sugar coating.Every day 2-3 time, each 1-5 sheet, or follow the doctor's advice.
Claims (12)
1. medicine that contains the Luan Shu extract, it is characterized in that it contains the following Luan Shu extract of 0.01-99.9% weight portion, this Luan Shu extract is the active component that extracts from Sapindaceae goldenrain tree Pterostyrax (Koelreuteria Laxm) plant, and wherein main component is gallic acid, progallin A, gallic acid glucoside, gallic acid flavone polyphenol compound; Its physical and chemical parameter is: be pale brown toner powder, meet ferric chloride reagent and be blue green, hydrochloric acid magnesium powder reacting positive is cherry-red; Ultraviolet spectra is λ max (methanol): 215 and the 217nm place maximum absorption band is arranged, 215nmE
%1Value is about 1.02,271nmE
%1Value is about 0.44; Infrared spectrum is cm
-1(KBr tabletting): 3700-2500 (OH), 1700 (O-C=O), 1600,1510,1520,1440 (aromatic protons), 1300,1200,1090 (C-O-) have located absworption peak.
2. according to the medicine of claim 1, it is characterized in that it contains the described Luan Shu extract of 1-80% weight portion.
3. according to the medicine of claim 1, it is characterized in that it contains the described Luan Shu extract of 10-60% weight portion.
4. according to the medicine of claim 1, the dosage form that it is characterized in that this medicine is any in tablet, pill, capsule, electuary, spray, oral liquid, suspension, externally applied liniment, transdermal absorption formulation and the injection.
5. a Luan Shu extract is characterized in that it is to extract branch and leaf, flower, fruit and the bark of Sapindaceae Luan Shu platymiscium Luan Shu, the extract of root gained with solvent.
6. according to the extract of claim 5, it is characterized in that extracting with solvent is water or 1-4 carbon alcohol that contains 10-80% water or pure acetone or the acetone that contains 20-30% water.
7. according to the extract of claim 6, it is characterized in that the purification of this extract is obtained different active components with different organic solvent extractions, said solvent comprises: the alkane of C6-C7, halogenated hydrocarbon, ether and organic acid esters, the aliphatic alcohol of C3-C5.
8. according to the extract of claim 6, it is characterized in that said solvent comprises hexane, cyclohexane extraction, petroleum ether, dichloromethane, dichloroethanes, chloroform, carbon tetrachloride, ether, ethyl acetate, butyl acetate, pentyl acetate.
9. according to the extract of claim 6, it is characterized in that this extract is to the extract reuse organic solvent of organic solvent extraction or with the extract of chromatography purification, said purification is meant with solvent and further extracts that said solvent comprises alkane, halogenated hydrocarbon, ether and the organic acid esters of C6-C7, the aliphatic alcohol of C3-C5; Or with the method purification that is selected from macroporous resin, silica gel, alumina adsorption and partition chromatography.
10. according to the extract of claim 6, it is characterized in that said solvent comprises hexane, cyclohexane extraction, petroleum ether, dichloromethane, dichloroethanes, chloroform, carbon tetrachloride, ether, ethyl acetate, butyl acetate, pentyl acetate.
11. a Luan Shu extract is characterized in that it is the active component that extracts with following method:
1), branch and leaf, flower, the fruit of getting raw medicinal material Luan Shu add 10-80% ethanol water reflux, extract, or soak percolation and extract, extracting solution concentrates removes alcohol, extracting solution A;
2), the aqueous solution of extract A is used petroleum ether, dichloromethane, ethyl acetate and just-butanols water extraction successively, obtain extracting solution B1, extracting solution B2, extracting solution C and extracting solution D respectively;
3), collect acetic acid ethyl acetate extract C liquid and concentrate, extract E (calling YQ-E in the following text);
4), the further solvent extraction of extract E (YQ-E), obtain purification active component extract (YQ-E1 and YQ-E2), with chromatography extracting solution E is carried out column chromatography purification, obtain purification active component extract (YQ-E3).
12. a Luan Shu extract is characterized in that it is the active component that extracts with following method:
1), branch and leaf, flower, the fruit of getting raw medicinal material Luan Shu soak percolation and extract, filter, concentrating under reduced pressure, extracting solution A:
2), add water with said extracted liquid A dilution, add petroleum ether then, extract, standing demix divides and removes upper strata petroleum ether liquid;
3), with above-mentioned 2) in lower floor's extracting solution of keeping, adding methylene chloride extracts, standing demix divides the sub-cloud dichloromethane extract;
4) with above-mentioned 3) in the upper water solution that keeps add ethyl acetate again and extract, standing demix, it is standby to collect the upper strata ethyl acetate;
5) with above-mentioned 4) in standby acetic acid ethyl acetate extract be concentrated into dried (YQE), after being dissolved in water, last macroporous resin chromatography carries out chromatography purification, with moisture 0-90% ethanol elution, collect the 30-50% ethanol elution, be evaporated to driedly, obtain purification active component extract (YQ-E3).
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| WO2007014515A1 (en) * | 2005-08-02 | 2007-02-08 | Shenghua (Guangzhou) Pharmaceutical Science & Technology Co., Ltd. | Use of hydroxybenzoic acid ester and analogues for the manufacture of a mendicament for the prevention and treatment of virus infection |
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| US8044098B2 (en) | 2005-08-02 | 2011-10-25 | Shenghua Guangzhou Pharmaceutical Science & Technology Co., Ltd. | Use of hydroxybenzoic acids and their esters and analogues for preventing or treating virus infection |
| CN105560438B (en) * | 2015-12-01 | 2019-10-25 | 西北大学 | A method of it extracted from Mel Jujubae, purify phenolic compound |
| CN108566992A (en) * | 2017-03-08 | 2018-09-25 | 周森荣 | Goldenrain tree seeds of trees vegetable oil |
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| Title |
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| 陕西中医.1985.6 1985.1.1 陈国联30种太白草药抗菌作用的实验研究简报 * |
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|---|---|---|---|---|
| WO2007014515A1 (en) * | 2005-08-02 | 2007-02-08 | Shenghua (Guangzhou) Pharmaceutical Science & Technology Co., Ltd. | Use of hydroxybenzoic acid ester and analogues for the manufacture of a mendicament for the prevention and treatment of virus infection |
| EA016576B1 (en) * | 2005-08-02 | 2012-06-29 | Шенгхуа (Гуанчжоу) Фармасьютикал Саенс Энд Текнолоджи Ко., Лтд. | Use of hydroxybenzoic acid ester for the manufacture of a medicament for the prevention and treatment of human virus infection |
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