CN1110303C - Application of eight precious extract in preparing antiviral medicine - Google Patents
Application of eight precious extract in preparing antiviral medicine Download PDFInfo
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- CN1110303C CN1110303C CN 99112550 CN99112550A CN1110303C CN 1110303 C CN1110303 C CN 1110303C CN 99112550 CN99112550 CN 99112550 CN 99112550 A CN99112550 A CN 99112550A CN 1110303 C CN1110303 C CN 1110303C
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- China
- Prior art keywords
- compound
- isopropylidene
- hylotelephium
- application
- sedoheptulosan
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to a compound with antiviral activity, which is obtained by once condensing propanone and sedoheptulose anhydride extracted and separated from hylotelephium extracts of crassulaceae plants or from the whole herbs of fimbriae orostachys or hylotelephium. The compound is isopropylidene sedoheptulose anhydride, namely hylotelephium by structural identification, wherein a structural formula is disclosed in the specification. The compound can be used for preparing novel antivirus medicine for resisting hepatitis B, bidirectional immunization, etc.
Description
The application is dividing an application of " a kind of method for making of antiviral compound Isopropylidene Sedoheptulosan " application for a patent for invention, and former denomination of invention is " a kind of method for making and a preparation thereof of new antiviral compound Isopropylidene Sedoheptulosan ", and original application day is 960726, application number 96115901.4.The present invention relates to field of medicaments, is to have the active chemical compound of antiviral property, a kind of anti-hepatitis B virus and a two-way immunoregulatory reactive compound of being used for of more specifically saying so about a kind of.
Hepatitis B is one of main infectious disease of harm humans health, and 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 specific drug so far.The Crassulaceae plant is used at Ceng Zuowei heat-clearing and toxic substances removing among the people, dissipating blood stasis for subsidence of swelling and traumatic injury Chinese herbal medicine, but to all not further investigations of its intrinsic pharmaceutically active.
The object of the present invention is to provide a kind of new chemical compound with anti-hepatitis B activity, and the method for synthesizing this chemical compound from the Crassulaceae plant extract.
The anti-hepatitis B activity chemical compound of the present invention development is extraction in the herb of long medicine Hylotelephium erythrostictum (Miq.) H.Ohba (H.spectabile) or Crassulaceae plant Hylotelephium erythrostictum (Miq.) H.Ohba (Hylotelephium erythrosticlum) or Herba Orostachyos plants such as (Orostachys fimbriatus), separation and purification and obtain scape ketose acid anhydride, obtain to have active chemical compound, called after Isopropylidene Sedoheptulosan (Hylotelephin) here with this scape ketose anhydridization compound and acetone one step condensation again.Synthetic this reactive compound mainly comprises following operating procedure:
1, pulverizes dry Crassulaceae plant herb, with the boiling water leaching, generally leach twice earlier, merge leaching liquid;
2, leaching liquid is about 1/5th of a former leaching liquid volume to be evaporated to concentrated back volume earlier through thin film concentration thereafter again.The ethanol standardize solution that adds equivalent is about about 50% alcoholic degree, places;
3, get supernatant, by strong-acid type cation exchange fat post, handle by the strong basic type anion-exchange resin post more earlier;
4, effluent steams and removes ethanol, and reclaims ethanol, obtains extractum;
5, extractum with kieselguhr and acidic alumina spice after, last alumina column with ethanol elution, obtains scape ketose acid anhydride;
6, the ketose acid anhydride of finding a view in the presence of an amount of sulphuric acid, adds acetone one and goes on foot condensation and obtain Isopropylidene Sedoheptulosan;
This antiviral activity chemical compound Isopropylidene Sedoheptulosan that obtains as stated above.With chemistry, infrared, modern spectral methods such as nuclear magnetic resonance, NMR and mass spectrum, the structure of this chemical compound is identified that qualification result is as follows:
Isopropylidene Sedoheptulosan is a white, needle-shaped crystals, m.p224-225 ℃, distils [α] during fusion
D 28=-125.2 ° (aqueous solution), molecular formula C
10H
16O
6, M+232.Elementary analysis: value of calculation, C51.72%, H6.94%; Measured value C51,32%, H6.74%, Molish reacts strong positive, orcin reacting positive, Liebermaon-Burchard reacting positive, the anisaldehyde-sulfuric acid reaction positive.
1R (ν cm): 3,410 3280 (wide) 1,380 1,365 982 955 932 850 820 810,785 740 720
H-NMR L (CD
3)
2SO adds trifluoracetic acid δ:
1.31(S，3H，-CH
3)，1.43(S，3H，-CH
3)，3.43(d，1H，J＝12，C
1-H)，3.65(d，1H，C
1-H)，3.61(d，1H，J
3，4＝5，C3-H)，3.73(d，1H，J
6，7＝5，4，C
7-H
ax)，3.85(d，1H，J
6，7 an＝1.5，C
7-H
an)，4.01(q，1H，J
4，5＝6，C
4-H)，4.21(q，1H，J
5，6＝1.2，C
5-H)4.78(m，1H，C
6-H)
MS m/e (%) electron bombard: 232 (M
+0.17), 217 (100), 156 (11.2), 101 (27.0), 85 (6.99), 70 (46.3), 59 (48.6), 43 (35.6); Field desorption: 217 (100, m-CH
3), 232 (10.7, M
+), 233 (16, M
+ 1), 234 (29, M
+ 2)
13C-NMR：δ(OFR)61.4(1，c-1)，110.9(s，c-2)，73.30(d，c-3)，76.79(d，c-4)，74.85(d，c-5)，79.47(d，c-6)，67.78(t，c-7)，108.05(s，c-8)，26.55)q，c-9)，28.17(q，c-10)。
Through the ownership of chemical reaction and spectral data, and with known allied compound relatively, the structural formula of this reactive compound is decided to be:
Chemistry isopropylidene scape ketose acid anhydride (Isopropylidene Sedoheptulosan) by name, this chemical compound can be used as the preparation of anti-DHB of preparation and two-way immune new drug.
For the therapeutic effect of proof the present invention, in duck hepatitis B virus infection duck body, carry out the therapeutic effect test both at home and abroad with the animal experimental model of recognizing altogether at present to DHB.An age in days Beijing duck intravenous injection DHB is adopted in experiment, begin after seven days to duck lumbar injection injection of the present invention, one day twice, administration 10 days (Bidx10) or 14 days (Bidx14) is observed medicine to toxicity of duck and the influence of the clear DHB DNA of Sanguis Anas domestica (DHBV-DNA).Experimental result shows, 200,100 and 50mg/kg dosage group, one day secondary, 10 days or 14 days, equal avirulence, two dosage groups of 200mg/kg and 100mg/kg all can reduce DHBA infected duck serum DHBR-DNA level, doing in groups with the virus control group, statistical analysis compares administration the 7th day (T7) or the 14th day (T
14) DHBV-DNA has significance to reduce, 50mg/kg dosage group, significant difference does not appear in the experiment, show that injection of the present invention has inhibitory action to the clear DHBV-DNA of Sanguis Anas domestica, simultaneously, experimental result also shows, injection of the present invention, under this experiment condition, its 200mg/kg and 100mg/kg group are the effective dose of treatment DHB.
Further observed the immunoregulatory activity of injection of the present invention to body with kunming mice.In vivo test of the present invention has tangible potentiation (P＜0.01) to Turnover of Mouse Peritoneal Macrophages lysosomal enzyme-acid phosphatase (ACP) activity.The activity of cell membrane enzyme-alkali phosphatase (AKP) has tangible immunoregulation effect.To tumor ring necrosis factor (TNF) activity, tangible potentiation (P＜0.01) is also arranged, experiment in vitro shows that the present invention and CONA and LPS share, can strengthen the two silk, split former effect, promote lymphocyte transformation, both have share synergism (the P value is respectively＜0.01 and＜0.05), and therefore, injection of the present invention is biological response modifier (Biological Response Modifer, BRM) immunomodulator in and/or immunostimulant have two-way immunologic function.
Concrete instance of following reuse is extracted scape ketose acid anhydride to the present invention in the Crassulaceae plant, further the method for synthetic Isopropylidene Sedoheptulosan is further described.
Get Hylotelephium erythrostictum (Miq.) H.Ohba (or Herba Orostachyos, long medicine Hylotelephium erythrostictum (Miq.) H.Ohba) (50kg, be ground into coarse powder, added water boil 1 hour, emit leaching liquid after, added water boil again 1 hour, merging leaching liquid twice, earlier through thin film concentration, is about 1/5th of former leaching liquid volume through being evaporated to liquid volume again, the 95% ethanol standardize solution that adds equivalent, determining alcohol is about about 50%, places, get supernatant earlier by highly acid H
+The exchange of type cation exchange resin column, effluent are again by strong basicity OH
-The exchange of type anion-exchange resin column.Effluent steams ethanol, and reclaims the ethanol reuse, makes extractum.Gained extractum with kieselguhr and acidic alumina spice after, last alumina column, with ethanol elution, can get scape ketose acid anhydride about 50 the gram.
Get above scape ketose acid anhydride 4 grams, add 80 milliliters in acetone, add an amount of sulphuric acid, electromagnetic agitation was placed after 24 hours, promptly had Isopropylidene Sedoheptulosan acicular crystal to separate out, and reclaimed acetone, got product 4.1 grams, and yield is greater than 85%.
After quality inspection is qualified, under aseptic condition, be sub-packed in the penicillin peace bottle of 10ml capacity, every 100mg 105 ℃ of heating disinfections 20 minutes, promptly gets the Isopropylidene Sedoheptulosan injection.
During use, after facing with before adding about 5 milliliters of sterilizeds water for injection, making dissolving, intravenous drip, 200-300mg on the one.
The present invention extracts scape ketose acid anhydride from Crassulaceae plant Hylotelephium erythrostictum (Miq.) H.Ohba or long medicine Hylotelephium erythrostictum (Miq.) H.Ohba in the herb of plants such as Herba Orostachyos, the resynthesis Isopropylidene Sedoheptulosan has significant antiviral activity and two-way immunologic function through this chemical compound of experiment confirm to hepatitis B virus.Can be used as the bidirectional immune regulator for the treatment of diseases such as hepatitis B.
Claims (2)
1, the application of Isopropylidene Sedoheptulosan in preparation treatment hepatitis B medicament.
2, the application of Isopropylidene Sedoheptulosan in preparation biological response modifier medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99112550 CN1110303C (en) | 1999-11-17 | 1999-11-17 | Application of eight precious extract in preparing antiviral medicine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99112550 CN1110303C (en) | 1999-11-17 | 1999-11-17 | Application of eight precious extract in preparing antiviral medicine |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96115901A Division CN1054606C (en) | 1996-07-26 | 1996-07-26 | Preparation method of antiviral compound eight-treasures extract |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1277020A CN1277020A (en) | 2000-12-20 |
| CN1110303C true CN1110303C (en) | 2003-06-04 |
Family
ID=5275846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 99112550 Expired - Lifetime CN1110303C (en) | 1999-11-17 | 1999-11-17 | Application of eight precious extract in preparing antiviral medicine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1110303C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012012390A1 (en) | 2010-07-19 | 2012-01-26 | Marvphyt Development Llc | Botanical composition and methods of manufacture and use |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010066075A1 (en) * | 2008-12-10 | 2010-06-17 | 广东粤龙药业有限公司 | The use of hylotelephin in preparing medicaments for treating hbeag positive chronic hepatitis b in human |
-
1999
- 1999-11-17 CN CN 99112550 patent/CN1110303C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012012390A1 (en) | 2010-07-19 | 2012-01-26 | Marvphyt Development Llc | Botanical composition and methods of manufacture and use |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1277020A (en) | 2000-12-20 |
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Owner name: GUANGDONG YUELONG PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: DARI BIOLOGY CHEMICALS MEDICINE CO., LTD., GUANGDONG PROVINCE Effective date: 20080801 |
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| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20080801 Address after: Green Industrial Park, Jiedong County, Jieyang, Guangdong Patentee after: Guangdong Yuelong Pharmaceutical Co., Ltd. Address before: Swallow pond Industrial Zone, Guangzhou, Guangdong, Tianhe District Patentee before: Dari Biological Chemical Pharmceutical Co., Ltd., Guangdong Prov. |
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| CX01 | Expiry of patent term |
Granted publication date: 20030604 |
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