CN1093362A - Novel anti-virus compound Methy Brevifolin-carboxlate and preparation method thereof - Google Patents
Novel anti-virus compound Methy Brevifolin-carboxlate and preparation method thereof Download PDFInfo
- Publication number
- CN1093362A CN1093362A CN 93115184 CN93115184A CN1093362A CN 1093362 A CN1093362 A CN 1093362A CN 93115184 CN93115184 CN 93115184 CN 93115184 A CN93115184 A CN 93115184A CN 1093362 A CN1093362 A CN 1093362A
- Authority
- CN
- China
- Prior art keywords
- carboxlate
- brevifolin
- methy
- chloroform
- methy brevifolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
A kind of novel anti-virus compound Methy Brevifolin-carboxlate, with the Common Leafflower Herb herb is raw material, by pulverizing, degreasing, methanol extraction, silicagel column low pressure chromatography, with chloroform-methanol-water gradient elution, make crude product, and with obtaining the pure product of Methy Brevifolin-carboxlate behind methyl alcohol-chloroform recrystallization.Experimental results show that this compound has significant antiviral activity.The basis that the present invention has established chemistry and biology for the new new antiviral drug of exploitation, and can be directly used in the exploitation new antiviral drug.
Description
The present invention relates to field of medicaments, is the compound that has antiviral activity about a kind of.
Hepatitis B is one of main transmissible disease of harm humans health.Domestic have 10% population to carry hepatitis B surface antigen approximately.Though the medicine of treatment hepatitis B and the research of Hepatitis B virus vaccine thereof get along with at present, still do not have good specifics so far.In order to study the medicine of treatment hepatitis B, very big manpower, financial resources have all been dropped in countries in the world.Doctor Bu Lunbai (Dr.B.Blumberg) of U.S. Philadelphia DKFZ adopts the plant amedica scalping, finds the Common Leafflower Herb crude extract, and the activity that suppresses hepatitis B surface antigen reaches 82%, but all belongs to crude extract.
The object of the present invention is to provide a kind of new compound with antiviral activity, and the method for from Common Leafflower Herb, extracting this new compound.
This antiviral activity compound that the present invention separates in Common Leafflower Herb, purifying obtains is Methy Brevifolin-carboxlate (Methy Brevifolin-carboxlate), and its structural formula is:
This compound can be used as the preparation new antiviral drug.
With modern spectral methods such as chemical reaction, ultraviolet, infrared, nucleus magnetic resonance and mass spectrums the All new compounds of extracting is identified.In structure is identified, also adopted two dimensional NMR and
1H-
1H COSY,
13C-
1HCOSY, long-range
13C-
1New technology, novel methods such as H and DEPT, INEPT, qualification result is as follows:
Methy Brevifolin-carboxlate is little yellow needle .m.p.200 ℃ (decomposing methyl-sulphoxide).High resolution mass spectrum provides molecular formula C
14H
10O
0(M306.0376, calculated value 306.0376).The ferric chloride reaction positive, the potassium hydroxide reacting positive.Displaing yellow fluorescence on the polyamide layer.
UV(λ
MEOH MaxNm, log ε): 218.5(4.57), 279.0(4.95), 349.0(4.62), 369.0(4.62) with ethyl brevifolincarboxylate (the ethyl brevifolinca rboxylate) basically identical of bibliographical information.
IR(V
KBr MaxCm
-1): 3387,3140(OH), 1720,1698(C=o), and 1634(C=C), 1598, the vibration of 1498(aromatic ring frame).
Comparison this product and short leaf wood phenol acetate
1H-NMR, its fragrant hydrogen signal δ 7.29(1H, S), phenolic hydroxyl group signal δ 10.20(3H, b) and the ABX system signal that is presented, δ 2.46(1H, dd, j=2HZ), 2.98(1H, dd, j=8HZ, 19HZ), 4.42(1H, dd, j=8HZ is 2HZ) all close with short Su Ye wood phenolic acid ethyl ester.Different is that ethyl brevifolincarboxylate presents OCH
2CH
3A
2X
3The signal of system, and this product replaces OCH
3δ 3.62(3H, S) hydrogen signal.
Comparison this product and ethyl brevifolincarboxylate
13C-NMR(sees Table-1).Ethyl brevifolincarboxylate has OCH
2CH
3In two carbon signals, and this product replaces OCH
3Carbon signal.Other carbon signal is identical.
Shown that by above deduction this product is leaf bush phenolic acid methyl esters (Methyl brevifolin carboxlate), is a new compound, its structural formula is:
1H-
1H COSY,
13C-
1H COSY, long-range
13C-
1H COSY has further verified the structure of Methy Brevifolin-carboxlate.And in view of the above to Methy Brevifolin-carboxlate
13C-NMR belongs to.Thereby by relatively to ethyl brevifolincarboxylate
13C-NMR has carried out belonging to (seeing Table-1) again.
The cleavage of mass spectrum rule of Methy Brevifolin-carboxlate of the present invention is seen accompanying drawing 1.
The high resolution fragment composition of Methy Brevifolin-carboxlate of the present invention sees Table-2.
Methy Brevifolin-carboxlate of the present invention
1H-
1H COSY spectrum is seen accompanying drawing 2;
13C-
1H COSY spectrum is seen accompanying drawing 3; Long-range
13C-
1H COSY spectrum is seen accompanying drawing 4; The DEPT spectrum is seen accompanying drawing 5.
The high resolution mass spectrum fragment of table-2 Methy Brevifolin-carboxlates is formed
Further measured the antiviral activity of new compound Methy Brevifolin-carboxlate.
By the method for measuring the medicine antiviral activity usually, measure medicine pair cell toxicity (TO with the human cervical carcinoma Hela cell
50), observe the antivirus action of medicine again to human herpes simplex vicus HSV-1 STAKER strain and HSV-2 SAR strain, measure ED
50, and calculate its protection index (PI).The positive control medicine adopts virazole, and (ribavirin, virazole), the result is shown in table 3,4,5,6,7.
Table 3, human herpes simplex vicus Hsv-1, Hsv-2 cause Hela cytopathy record (CPE)
HSV-1, HSV-2 are to Hela cell-lethal effect and TCID for table 4 people simple cell virus
50(mtt assay)
Table 5 different concns medicine is to the kill rate (%) and the TD of Hela cell
50
The anti-HSV-1 virus function of table 6 Methy Brevifolin-carboxlate (ED
50) and protection index (PI)
The anti-HSV-2 virus function of table 7 Methy Brevifolin-carboxlate (ED
50) and protection index (PI)
Table
3-7The result shows that Methy Brevifolin-carboxlate has sure and significant antiviral activity to human herpes simplex vicus HSV-1, HSV-2 strain.
Methy Brevifolin-carboxlate of the present invention is the new compound that extraction from Common Leafflower Herb, separation, purifying obtain.Common Leafflower Herb is an Euphorbiaceae phyllanthus emblica platymiscium, and the used Common Leafflower Herb of the present invention all adopts mountain area, Wuyi, Fujian, extracts this new compound and mainly comprises following step:
1, gets dry Common Leafflower Herb herb and be crushed to suitable fineness;
2, use petroleum ether degreasing earlier, and isolate degreasing fluid;
3, the isolated dregs of a decoction fully extract with methyl alcohol;
4, concentrate methanol extract liquid with underpressure distillation, obtain a kind of methyl alcohol medicinal extract;
5, add the water suspendible, medicinal extract also distributes with chloroform and propyl carbinol successively;
6, isolate propyl carbinol and distribute phase, concentrate again;
7, be that eluent carries out gradient elution and obtains the Methy Brevifolin-carboxlate crude product with the silica gel low pressure column chromatography and with chloroform-methanol-water;
8, secondary purification by silica gel column chromatography;
9, heavily tie product with methyl alcohol-chloroform, obtain pure Methy Brevifolin-carboxlate.
Below accompanying drawing is done an explanation:
Accompanying drawing 1 is the cleavage of mass spectrum figure of Methy Brevifolin-carboxlate of the present invention;
Accompanying drawing 2 is a Methy Brevifolin-carboxlate of the present invention
1H-
1The HCOSY spectrogram.
Accompanying drawing 3 is a Methy Brevifolin-carboxlate of the present invention
13C-
1The HCOSY spectrogram.
Accompanying drawing 4 is long-range for Methy Brevifolin-carboxlate of the present invention
13C-
1The HCOSY spectrogram.
Accompanying drawing 5 is the DEPT spectrogram of Methy Brevifolin-carboxlate of the present invention.
With a concrete instance the present invention extracts Methy Brevifolin-carboxlate in Common Leafflower Herb method is further described again below, gets dry Common Leafflower Herb herb, break into meal, insert in the extractor of the rope third constellations, after adding petroleum ether degreasing earlier,, fully extract with methyl alcohol again dregs of a decoction airing.Tell methanol extract liquid, concentrate methanol extract liquid, obtain methyl alcohol medicinal extract with underpressure distillation.This medicinal extract is added the suitable quantity of water suspendible, distribute with chloroform and propyl carbinol successively, after propyl carbinol taken out concentrating under reduced pressure, with silica gel and diatomite spice, the silica gel low pressure column chromatography is made gradient elution with chloroform-methanol-water, collects elutriant respectively, 250 milliliters every part, obtain the Methy Brevifolin-carboxlate crude product at the 36th part.It is secondarily purified that this raw product passes through silicagel column again, with methyl alcohol-chloroform recrystallization, promptly obtains pure Methy Brevifolin-carboxlate.
This Methy Brevifolin-carboxlate of the present invention to extract in the Common Leafflower Herb, has significant antiviral activity through this new compound of experiment confirm, thereby, and can be directly used in the exploitation new antiviral drug for this new new antiviral drug of exploitation has been established chemistry and biological basis.
Claims (2)
1, a kind of antiviral activity compound that extracts from Common Leafflower Herb is characterized in that said antiviral activity compound is a Methy Brevifolin-carboxlate, and its structural formula is:
This compound can be used as the preparation new antiviral drug.
2,, it is characterized in that comprising following extraction step according to the extracting method of the described antiviral activity compound of claim 1:
2-1, pulverizing exsiccant Common Leafflower Herb herb;
2-2, use petroleum ether degreasing, separate degreasing fluid;
2-3, leaching slag fully extract with methyl alcohol;
2-4, underpressure distillation concentrate methanol extract liquid, get methyl alcohol medicinal extract;
2-5, medicinal extract add the water suspendible;
2-6, distribute with chloroform and propyl carbinol successively;
2-7, isolate the n-butanol extraction liquid phase, and concentrate;
2-8, with the silica gel low pressure column chromatography;
2-9, with chloroform-methanol-water gradient elution, obtain the Methy Brevifolin-carboxlate crude product;
2-10, secondary purification by silica gel column chromatography;
2-11, with methyl alcohol-chloroform recrystallization, obtain pure Methy Brevifolin-carboxlate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN93115184A CN1048489C (en) | 1993-10-30 | 1993-10-30 | Novel anti-virus compound methyl brevifolin carboxylic ester and method for prepn. of same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN93115184A CN1048489C (en) | 1993-10-30 | 1993-10-30 | Novel anti-virus compound methyl brevifolin carboxylic ester and method for prepn. of same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1093362A true CN1093362A (en) | 1994-10-12 |
| CN1048489C CN1048489C (en) | 2000-01-19 |
Family
ID=4990862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93115184A Expired - Fee Related CN1048489C (en) | 1993-10-30 | 1993-10-30 | Novel anti-virus compound methyl brevifolin carboxylic ester and method for prepn. of same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1048489C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101278897B (en) * | 2008-04-25 | 2010-06-09 | 西安交通大学 | Process for preparing brevifolin solid lipid nano particle |
| CN101298450B (en) * | 2008-04-25 | 2010-07-21 | 西安交通大学 | Extraction and separation method of effective ingredients brevifolin and 8,9-single-epoxy brevifolin in phyllanthus simplex |
| CN109106712A (en) * | 2018-07-31 | 2019-01-01 | 南方医科大学 | Methy Brevifolin-carboxlate is preparing the application in anti-influenza virus medicament |
| CN112843079A (en) * | 2020-06-11 | 2021-05-28 | 广东盛普生命科技有限公司 | Application of galloyl caesalpinia caesalpina acyl-beta-D-glucopyranose in preparing anti-coronavirus medicine |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4111861A1 (en) * | 1991-04-11 | 1992-10-15 | Schwabe Willmar Gmbh & Co | BENZOPYRANONE, PROCESS FOR THEIR PREPARATION AND USE |
-
1993
- 1993-10-30 CN CN93115184A patent/CN1048489C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101278897B (en) * | 2008-04-25 | 2010-06-09 | 西安交通大学 | Process for preparing brevifolin solid lipid nano particle |
| CN101298450B (en) * | 2008-04-25 | 2010-07-21 | 西安交通大学 | Extraction and separation method of effective ingredients brevifolin and 8,9-single-epoxy brevifolin in phyllanthus simplex |
| CN109106712A (en) * | 2018-07-31 | 2019-01-01 | 南方医科大学 | Methy Brevifolin-carboxlate is preparing the application in anti-influenza virus medicament |
| CN112843079A (en) * | 2020-06-11 | 2021-05-28 | 广东盛普生命科技有限公司 | Application of galloyl caesalpinia caesalpina acyl-beta-D-glucopyranose in preparing anti-coronavirus medicine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1048489C (en) | 2000-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102058678B (en) | Medicine or health-care food composition for treating fatty liver | |
| CN103180334A (en) | Method for preparing albiflorin and paeoniflorin | |
| Yoshida et al. | Tannins and related polyphenols of rosaceous medicinal plants. IV. Roxbins A and B from Rosa roxburghii fruits | |
| CN103012356A (en) | Compound with alpha-glycosidase inhibitory activity, as well as preparation method and application of compound | |
| CN110305014B (en) | Cycloneolignanoid enantiomers, preparation and application thereof | |
| CN1093362A (en) | Novel anti-virus compound Methy Brevifolin-carboxlate and preparation method thereof | |
| Ouyang et al. | Anti-oxidative activity of glycosides from Ligustrum sinense | |
| CN108912049B (en) | Diterpene alkaloid compound extracted from aconitum sinomontanum nakai and preparation method and application thereof | |
| CN103896755B (en) | A kind of chalcone compounds preparation method | |
| CN113773409B (en) | Polysaccharide of radix scutellariae Siniperca and its application | |
| CN1048488C (en) | Novel compound for anti-virus and method for prepn. of same | |
| CN110551163A (en) | Method for extracting flavonoid glycoside compounds from fructus Podophylli and application thereof | |
| CN113200911B (en) | Quinoline alkaloid compound and preparation method and application thereof | |
| CN101787004B (en) | Lignanoid compounds contained in daphne odora, and preparation method and application thereof | |
| CN111253352B (en) | Compound extracted and separated from traditional Chinese medicine cymbidium maculatum, and preparation method and application thereof | |
| CN110759882B (en) | Dihydro agarofuran sesquiterpene and medical application thereof | |
| CN1837226A (en) | Separation of medical derivatives from phoenix-tail fern and use thereof | |
| CN101974008A (en) | Process for extracting and purifying podophyllotoxin from Dysosma difformis | |
| CN103113196B (en) | Glechoma longituba phenol, and preparation method and application thereof | |
| CN102050787B (en) | Guanidine derivatives and preparation, medicinal composition and application in preparation of medicaments for treating metabolic syndromes | |
| CN100341888C (en) | Anticancer new compound of Xiacaogan I, preparation method, and application in pharmacy | |
| CN110156854A (en) | A kind of dihydrophenanthrene glycoside compound and its purification methods and uses | |
| CN103483410B (en) | Xanthoceraside preparation method | |
| CN112661799B (en) | Method for separating and purifying protopteridoside in pteridophyte | |
| CN1110303C (en) | Application of eight precious extract in preparing antiviral medicine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |