CN1277203A - Preparation and use of Moluxin glucoside - Google Patents
Preparation and use of Moluxin glucoside Download PDFInfo
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- CN1277203A CN1277203A CN 99108174 CN99108174A CN1277203A CN 1277203 A CN1277203 A CN 1277203A CN 99108174 CN99108174 CN 99108174 CN 99108174 A CN99108174 A CN 99108174A CN 1277203 A CN1277203 A CN 1277203A
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- compound
- morusin
- glycoside
- glucose
- aids
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Abstract
AIDS is one immune system disease caused by HIV virus infection and results in high death rate. The compound of the present invention can inhibit the activity of HIV virus and can be used to prevent and treat AIDS. The compound is Moluxin glycoside prepared with Moluxin as one known compound.
Description
The invention relates to the compound that suppresses the viral HIV of people's AIDS (AIDS), particularly use known compound Mo Luxin synthetic new compound Morusin-4'-O-glucose (Morusin-4 '-O-glucose), have the activity of inhibition of virus HIV of AIDS.
In order to prevent or treat the infection that HIV (human immunodeficiency virus) HIV causes, the treatment AIDS was once used chemical compound pyrimidine, indoles, hormonal compounds, adenosine deaminase, AZT, peptide class, plant milk extract tonka bean camphor, pelargonin class.The chemical ingredients of White Mulberry Root-bark morus alba L. was once studied by Japan, extracted, separates, identified Mo Luxin (Morusin), (ChemPharmBull24 (11) 1976P
2898-2900).But also use its inhibition of virus HIV of AIDS with the synthetic Morusin-4'-O-glucose of Mo Luxin, the infection that prevention or treatment are caused by HIV, the treatment AIDS then is not reported.
The present invention be intended to the synthetic a kind of new compound Morusin-4'-O-glucose of Mo Luxin (Morusin-4 '-O-glucose), and be used to suppress the viral HIV of people's AIDS (AIDS), with the infection that prevention or treatment are caused by HIV, the treatment AIDS.
Compound, morus ignin glycoside of the present invention (Morusin-4 '-the O-glycoside) be to be dissolved in the 15ml methylene dichloride with Mo Luxin (Morusin) 210mg, add 1.4g1-bromo 2 again, 3,4,6-tetrem acyl glucose and 1.1g silver carbonate, room temperature refluxes and stirred 2 hours in nitrogen atmosphere, and then adding 0.5g1-bromo 2,3,4,6-tetrem acyl glucose and 0.5g silver carbonate, room temperature reflux and stirred 3 hours, then the reaction product filtration under diminished pressure are drained, gained is drained thing 5ml dissolve with methanol, and add the saturated sodium methylate of 5ml, after stirring at room refluxed 20 minutes, feed carbon dioxide to solution pH value and equal till the 8-9, then with this solution decompression evaporate to dryness, the evaporate to dryness thing that obtains separates (solvent systems is a methylene dichloride 100+ methyl alcohol 5) with the preparation of silica gel chromatography, obtains product and be Morusin-4'-O-glucose (Morusin-4 '-O-glycoside) 16.7mg, and the molecular formula of this compound is C
31H
34O
11, molecular weight is 582, structural formula is
Be yellow powder, fusing point is 125-131 ℃, water soluble, and methyl alcohol is insoluble to chloroform.
Figure one is this compound test result curve figure.
Embodiment
With the compound, morus ignin glycoside (Morusin-4 '-O-glucose) with dimethyl sulfoxide (DMSO) (DMSO) dissolving, be made into the solution A that concentration is 2mg/ml, A liquid water is diluted to many groups diluent that concentration is 1 μ g/ml-1mg/ml respectively, on Fig. 1, makes abscissa with the log value of its concentration.Get 9 groups, the diluent of different concns carries out toxicity test.Get human lymphoid T4 cell and be divided into 9 groups, the diluent that adds above-mentioned 9 groups of different concns was respectively cultivated 7 days, and the surviving rate of observing these 9 groups of cells is made ordinate with 0-100% on Fig. 1, obtain 9 experimental points, and each point is linked to be curve.By this curve toxicity of this compound pair cell (among Fig. 1 shown in the thick line) as can be seen.When cell survival rate was 50%, the compound concentration of this point was called IC50.
Get human lymphoid T4 cell, after the viral HIV of personnel selection AIDS (AIDS) infects, be divided into 9 groups, carry out of the inhibition experiment of this compound HIV.The diluent that adds above-mentioned 9 groups of different concns was respectively cultivated the surviving rate of observing these 9 groups of cells 7 days.On Fig. 1, make ordinate with 0--100%, obtain 9 experimental points, each point is linked to be curve.Can see the surviving rate of infected cells under the compound effects of different concns (among Fig. 1 shown in the fine rule) by this curve.When surviving rate was 50%, the compound concentration of this point was called EC50, and the surviving rate of human lymphoid T4 cell under the compound effects of this concentration that promptly infected by HIV of meaning is 50% (surviving rate of HIV cells infected that does not add the control group of compound is 0).
Data shown in the table 1 are the raw data of above-mentioned two groups of experiments, make graphic representation 1 with these data.Abscissa is the log value of compound concentration μ g/ml among Fig. 1.Value 0 is 1 μ g/ml, and value 1 is 10 μ g/ml, and value 2 is 100 μ g/ml, and value 3 is 1000 μ g/ml.Ordinate is the surviving rate of human lymphoid T4 cell.Value 0 expression cell is all dead, and value 50 expression cell survival rates are 50%, and value 100 expression cell survival rates are 100%.By the thick line toxicity of this compound pair cell as can be seen, by fine rule as can be seen this compound to the restraining effect of HIV (human immunodeficiency virus) HIV.IC/EC=TI represents the therapeutic index of this compound.
As seen from Figure 1, compound, morus ignin glycoside of the present invention (Morusin-4 '-O-glucose) concentration just can suppress 50% HIV (human immunodeficiency virus) HIV about 5 μ g/ml.
Test-results numbering concentration unit data results CV value inverse amplification factor IND
Be subjected to HIV cells infected dosing experimental result
50 90 10002-G11 cell concentration l 1.766 0.320 0.167 infect--EC value * 7.47E+0001-G01 reagent concentration 0.145 0.006 0.039 does not infect--IC value * 2.29E+01 * 5.83E+01 * 1.23E+0203-C03 1.95E+00u l 0.767 0.170 0.188 43.4 TI value * 3.07E+0004-C04 3.90E+00u l 0.788 0.031 0.034 44.6*05-C05 7.81E+00u l 1.309 0.193 0.134 74.1*06-C06 1.56E+01u l 1.419 0.081 0.052 80.407-C07 3.12E+01u l 0.300 0.054 0.125 17.008-C08 6.25E+01u l 0.166 0.013 0.04 4 9.409-C09 1.25E+02u l 0.030 0.001 0.009 1.710-C10 2.50E+02u l 0.008 0.000 0.000 0.502-E11 VIRUS CNTRL 0.786 0.191 0.206 44.5
Be not subjected to HIV to infect 02-G11 cell concentration l 1.766 0.320 0.15703-F03 1.95E+00u l 1.977 0.000 0.000 111.904-F04 3.90E+00u l 1.907 0.000 0.000 108.005-F05 7.81E+00u l 1.829 0.000 0.000 103.506-F06 1.56E+01u l 1.621 0.000 0.000 91.8*07-F07 3.12E+01u l 0.290 0.000 0.000 16.4*08 F08 6.25E+01u l 0.164 0.000 0.000 9.309-F09 1.25E+02u l 0.003 0.000 0.000-0.210-F10 2.50E+02u l 0.003 0.000 0.000-0.2 table one
Claims (3)
1, a kind of compound, morus ignin glycoside (Morusin-4 '-O-glucose), it is characterized in that molecular formula is C
31H
34O
11, molecular weight is 582, structural formula is
Be yellow powder, fusing point is 125-131 ℃, water soluble, and methyl alcohol is insoluble to chloroform;
2, a kind of preparation method of compound, morus ignin glycoside, it is characterized in that: be dissolved in the 15ml methylene dichloride with Mo Luxin (Morusin) 210mg, add 1.4g1-bromo 2 again, 3,4,6-tetrem acyl glucose and 1.1g silver carbonate, room temperature refluxes and stirred 2 hours in nitrogen atmosphere, and then adding 0.5g1-bromo 2,3,4,6-tetrem acyl glucose and 0.5g silver carbonate, room temperature refluxes and stirred 3 hours, then the reaction product filtration under diminished pressure is drained, gained is drained thing 5ml dissolve with methanol, and adds the saturated sodium methylate of 5ml, after stirring at room refluxed 20 minutes, feeding carbon dioxide to solution pH value equals till the 8-9, then with this solution decompression evaporate to dryness, the evaporate to dryness thing that obtains separates (solvent systems is a methylene dichloride 100+ methyl alcohol 5) with the preparation of silica gel chromatography, obtains product and be Morusin-4'-O-glucose (Morusin-4 '-O-glycoside) 16.7mg;
3, a kind of purposes of compound, morus ignin glycoside is characterized in that: the activity that is used for suppressing the viral HIV of people's AIDS (AIDS).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99108174 CN1277203A (en) | 1999-06-11 | 1999-06-11 | Preparation and use of Moluxin glucoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99108174 CN1277203A (en) | 1999-06-11 | 1999-06-11 | Preparation and use of Moluxin glucoside |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1277203A true CN1277203A (en) | 2000-12-20 |
Family
ID=5273180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 99108174 Pending CN1277203A (en) | 1999-06-11 | 1999-06-11 | Preparation and use of Moluxin glucoside |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1277203A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101787030A (en) * | 2010-03-09 | 2010-07-28 | 周英 | Preparation and application methods of anti-HIV compound, morus ignin L |
-
1999
- 1999-06-11 CN CN 99108174 patent/CN1277203A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101787030A (en) * | 2010-03-09 | 2010-07-28 | 周英 | Preparation and application methods of anti-HIV compound, morus ignin L |
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| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |