WO2000056347A1 - Fraction enrichie preparee a partir de phyllanthus amarus pour le traitement de l'hepatite et preparation de cette fraction - Google Patents
Fraction enrichie preparee a partir de phyllanthus amarus pour le traitement de l'hepatite et preparation de cette fraction Download PDFInfo
- Publication number
- WO2000056347A1 WO2000056347A1 PCT/IN2000/000029 IN0000029W WO0056347A1 WO 2000056347 A1 WO2000056347 A1 WO 2000056347A1 IN 0000029 W IN0000029 W IN 0000029W WO 0056347 A1 WO0056347 A1 WO 0056347A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methanol
- extract
- plant material
- fraction
- aqueous portion
- Prior art date
Links
- 244000173207 Phyllanthus amarus Species 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 208000006454 hepatitis Diseases 0.000 title claims abstract description 8
- 231100000283 hepatitis Toxicity 0.000 title claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000000284 extract Substances 0.000 claims abstract description 30
- 241000196324 Embryophyta Species 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 22
- 238000000746 purification Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000000605 extraction Methods 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 9
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 238000004587 chromatography analysis Methods 0.000 claims description 14
- JQQBXPCJFAKSPG-SVYIMCMUSA-N Geraniin Chemical compound OC1=C(O)C(O)=CC(C(=O)O[C@H]2[C@@H]3OC(=O)C=4C=C(O)C(O)=C5O[C@@]6(O)C(=O)C=C([C@@H](C5=4)C6(O)O)C(=O)O[C@H]4[C@@H]3OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC[C@H]4O2)=C1 JQQBXPCJFAKSPG-SVYIMCMUSA-N 0.000 claims description 12
- 229920000061 Geraniin Polymers 0.000 claims description 12
- GJMUCSXZXBCQRZ-UHFFFAOYSA-N geraniin Natural products Oc1cc(cc(O)c1O)C(=O)OC2OC3COC(=O)c4cc(O)c(O)c(O)c4c5cc(C(=O)C67OC3C(O6)C2OC(=O)c8cc(O)c(O)c9OC%10(O)C(C(=CC(=O)C%10(O)O)C7=O)c89)c(O)c(O)c5O GJMUCSXZXBCQRZ-UHFFFAOYSA-N 0.000 claims description 12
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 229940093499 ethyl acetate Drugs 0.000 claims description 8
- 235000019439 ethyl acetate Nutrition 0.000 claims description 8
- 239000002038 ethyl acetate fraction Substances 0.000 claims description 8
- 229920005654 Sephadex Polymers 0.000 claims description 6
- 239000012507 Sephadex™ Substances 0.000 claims description 6
- 239000003463 adsorbent Substances 0.000 claims description 5
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 4
- 229920002786 Corilagin Polymers 0.000 claims description 4
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 claims description 4
- 229920002079 Ellagic acid Polymers 0.000 claims description 4
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 claims description 4
- TUSDEZXZIZRFGC-XIGLUPEJSA-N corilagin Chemical compound O([C@H]1[C@H](O)[C@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC[C@@H](O1)[C@H]2O)C(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-XIGLUPEJSA-N 0.000 claims description 4
- CPWYQGWOJMNXGJ-UHFFFAOYSA-N corilagin Natural products OC1C2COC(=O)c3c(O)c(O)c(O)c(O)c3c4c(O)c(O)c(O)c(O)c4C(=O)OC1C(O)C(OC(=O)c5cc(O)c(O)c(O)c5)O2 CPWYQGWOJMNXGJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960002852 ellagic acid Drugs 0.000 claims description 4
- 235000004132 ellagic acid Nutrition 0.000 claims description 4
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 claims description 4
- ZOEGQXCAXOUFHN-UHFFFAOYSA-N Furosin Natural products OC1C2OC(=O)C(C=3C4C5(O)O)=CC(O)=C(O)C=3OC5(O)C(=O)C=C4C(=O)OC1C(CO)OC2OC(=O)C1=CC(O)=C(O)C(O)=C1 ZOEGQXCAXOUFHN-UHFFFAOYSA-N 0.000 claims description 3
- CXTMLIMZRPKULL-YXYYPBJFSA-N dnc013643 Chemical compound O([C@@H]1O[C@@H]([C@H]2OC(=O)C=3[C@@H]4C(C(C(=O)C=3)(O)O)(O)OC=3C(O)=C(O)C=C(C4=3)C(=O)O[C@@H]1[C@H]2O)CO)C(=O)C1=CC(O)=C(O)C(O)=C1 CXTMLIMZRPKULL-YXYYPBJFSA-N 0.000 claims description 3
- 230000027455 binding Effects 0.000 description 15
- 230000000694 effects Effects 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229920001864 tannin Polymers 0.000 description 3
- 235000018553 tannin Nutrition 0.000 description 3
- 239000001648 tannin Substances 0.000 description 3
- 239000002034 butanolic fraction Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 208000002672 hepatitis B Diseases 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 241000283923 Marmota monax Species 0.000 description 1
- 241001130943 Phyllanthus <Aves> Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/47—Euphorbiaceae (Spurge family), e.g. Ricinus (castorbean)
Definitions
- his invention relates to a simple process for preparing reproducibly an active fraction rrom
- Phyllanthus amanis with an assured in vitro HBs ⁇ g binding activity which can be used in the treatment of Hepatitis viruses, especially Hepatitis B.
- Siddha as powdered whole plant, paste of fresh plant and decoctions to treat jaundice of varied aetiology.
- This extract showed both Hbs ⁇ g binding and HBV DN ⁇ polymcrase inhibitory activity.
- the active constituents have not been identified by Blumberg et at Mehrotra et al (Indian J. Med. Res. [A] 93, 71-73 March 1991) have fractionated cold ethanolic extract of whole plant of Phyllanthus amarus followed by solvent fractionarion and shown that the butanol fraction showed maximum in vitro Hbs ⁇ g binding, I IbeAg binding and maximum inhibitory activity against HBV DNA.
- the butanol extract was further fractionated; however no active constituents were identified.
- the process for the preparation of an enriched fraction from Phyllanthus amarus for use in the treatment of hepatitis comprises the steps of carrying out at least one extraction of the plant material with a solvent selected from (I) methanol (ii) methanol-water mixture containing at least 30% of methanol; removing the methanol from the extract of the plant material; and fractionating the residual aqueous portion of the said extract by purification procedures.
- the plant material and solvent in the process as set out against item (a) above are preferably in the proportion 1:5 to 1:10 weight/volume.
- the methanol-water mixture preferably contains 50% of methanol.
- the purification procedure comprises the steps of carrying out three to five extractions of the residual aqueous portion of the extract of the extract of plant material with ethyl acetate after carrying out three to five preliminary extractions of the said residual aqueous portion of the extract of plant material with hexane and chloroform.
- the residual aqueous portion of the extract of plant material and ethyl acetate, in the process as set out against item (e) above, are preferably in the proportion of 1:0.5 to 1 :3 by volume.
- the residual aqueous portion of the extract of plant material and hexane, in the process as set out against item (c) or (f) above, are preferably in the proportion 1:0.5 to 1:3 by volume, (h).
- the residual aqueous portion of the extract of plant material and chloroform, in the process as set out against items (e) to (g) above, are preferably in the proportion of 1:0.5 to 1:3 by volume.
- the purification procedure according to the process set out against any one of the items (e) to (h) above, comprises the steps of chromatography of the ethyl acetate fraction over Sephadex LH-20 or other polymeric adsorbents such as Sephadex G -25, MCI Gel CHP-20P or DIAION HP-20.
- the purification procedure according to the process set out against any one of the items (a) to (d) above comprises the steps of separating the residual aqueous portion by chromatography over Sephadex LH-20 or other polymeric adsorbents such as Sephadex G- 25, MCI Gel CHP-20 P or DIAION HP-20. (k).
- one of the fractions obtained after chromatography is further fractionated by chromatography over Sephadex LH-20 using methanol to give a fraction containing substantially geraniin identified as the major active principle.
- the other fraction ⁇ further purified by chromatography over Sephadex LH-20 using methanol to give an active fraction comprising major amounts of corilagin, furosin and ellagic acid.
- powdered aerial parts of Phyllanthus amarus were extracted with methanol:water containing from 30 to 100% of methanol.
- the methanol was removed under reduced pressure and the aqueous phase extracted successively with hexane, chloroform and ethylacetate.
- Hbs ⁇ g binding activity is concentrated in the ethylacetate fraction.
- fracrionation by twice chromatography on LH-20 leads to a further enrichment of activity and increased percentage of geraniin in the active fractions.
- suitable procedure for obtaining active fractions is illustrated in Fig .3.
- Example -1 This example describes the preparation of the active extract of Phyllanthus amarus and method of fractionation to get enriched fractions containing geraniin which were tested to determine the HbsAg binding activity.
- Aerial parts of Phyllanthus amarus were dried and powdered. 250 g of the powdered material was extracted with 2x1750 ml of methanol : water (1:1) at ambient temperature for 2x24 hours.
- HbsAg binding activity was found in two fractions each weighing about 110 mg and 260 g.
- Phyllanthus amarus was extracted as under Example- 1.
- the extract (I >t-2) was concentrated under reduced pressure to remove methanol and loaded directly on Sephadex LH-20. Elution was done using water followed by increasing amounts of methanol in water. Two fractions with significantly enhanced Hbs ⁇ g binding activity each weighing 386mg and 600mgwere obtained.
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
L'invention concerne un procédé permettant de préparer une fraction enrichie de Phyllanthus amarus servant au traitement de l'hépatite. Ce procédé comprend les étapes suivantes : on procède à au moins une extraction de la matière végétale à l'aide d'un solvant sélectionné parmi (i) le méthanol, (ii) un mélange méthanol eau contenant au moins 30 % de méthanol, on sépare le méthanol de l'extrait de matière végétale et on fractionne la portion aqueuse résiduelle de cet extrait par des procédures de purification. L'invention concerne également une fraction enrichie préparée au moyen du procédé ci-dessus.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU49477/00A AU4947700A (en) | 1999-03-24 | 2000-03-23 | An enriched fraction prepared from phyllanthus amarus for the treatment of hepatitis and the preparation thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN339MA1999 | 1999-03-24 | ||
| IN339/MAS/99 | 1999-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2000056347A1 true WO2000056347A1 (fr) | 2000-09-28 |
Family
ID=11094863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2000/000029 WO2000056347A1 (fr) | 1999-03-24 | 2000-03-23 | Fraction enrichie preparee a partir de phyllanthus amarus pour le traitement de l'hepatite et preparation de cette fraction |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU4947700A (fr) |
| WO (1) | WO2000056347A1 (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000061161A2 (fr) * | 1999-04-12 | 2000-10-19 | University Of Madras | Formulation pharmaceutique utile pour le traitement de l'hepatite b, de l'hepatite c et d'autres infections virales du foie ; procede de preparation de cette formulation pharmaceutique |
| WO2002087600A1 (fr) * | 2001-04-26 | 2002-11-07 | Phytrix Ag | Utilisation d'elements de phyllanthus pour traiter ou prevenir des infections provoquees par un virus d'hepatite b |
| DE10155517A1 (de) * | 2001-11-13 | 2003-05-28 | Metanomics Gmbh & Co Kgaa | Verfahren zur Extraktion von Inhaltsstoffen aus organischem Material |
| US7074436B2 (en) * | 2000-10-06 | 2006-07-11 | Phytrix, Inc. | Method for the production of phyllanthus extracts |
| CN110964030A (zh) * | 2019-12-19 | 2020-04-07 | 浙江工业大学 | 一种从叶下珠中分离制备鞣花酸的球磨辅助提取方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0199429A2 (fr) * | 1985-04-26 | 1986-10-29 | Fox Chase Cancer Center | Préparation d'un médicament pour traiter l'hépatite virale |
-
2000
- 2000-03-23 AU AU49477/00A patent/AU4947700A/en not_active Abandoned
- 2000-03-23 WO PCT/IN2000/000029 patent/WO2000056347A1/fr active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0199429A2 (fr) * | 1985-04-26 | 1986-10-29 | Fox Chase Cancer Center | Préparation d'un médicament pour traiter l'hépatite virale |
Non-Patent Citations (2)
| Title |
|---|
| ANUPAMA MUNSHI ET AL.: "Evaluation of Anti-Hepadnavirus Activity of Phyllanthus amarus and Phyllanthus maderaspatensis in Duck Hepatitis B Virus Carrier Pekin Ducks", JOURNAL OF MEDICAL VIROLOGY., vol. 41, no. 4, December 1993 (1993-12-01), NEW YORK, NY., US, pages 275 - 281, XP000929885 * |
| R. MEHROTRA ET AL: "In vitro effect of Phyllanthus amarus on hepatitis B virus", JOURNAL OF THE INDIAN MEDICAL ASSOCIATION., vol. 93, March 1991 (1991-03-01), INDIAN MEDICAL ASSOCIATION, CALCUTTA., IN, pages 71 - 73, XP000929883, ISSN: 0019-5847 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000061161A2 (fr) * | 1999-04-12 | 2000-10-19 | University Of Madras | Formulation pharmaceutique utile pour le traitement de l'hepatite b, de l'hepatite c et d'autres infections virales du foie ; procede de preparation de cette formulation pharmaceutique |
| WO2000061160A2 (fr) * | 1999-04-12 | 2000-10-19 | University Of Madras | Formulation pharmaceutique utile pour traiter l'hepatite b, l'hepatite c et d'autres infections hepatiques, et procede de preparation |
| WO2000061160A3 (fr) * | 1999-04-12 | 2001-01-25 | Univ Madras | Formulation pharmaceutique utile pour traiter l'hepatite b, l'hepatite c et d'autres infections hepatiques, et procede de preparation |
| WO2000061161A3 (fr) * | 1999-04-12 | 2001-02-08 | Univ Madras | Formulation pharmaceutique utile pour le traitement de l'hepatite b, de l'hepatite c et d'autres infections virales du foie ; procede de preparation de cette formulation pharmaceutique |
| US6589570B1 (en) | 1999-04-12 | 2003-07-08 | University Of Madras | Pharmaceutical formulation useful for the treatment of hepatitis B, hepatitis C and other viral infections of the liver and a process for its preparation |
| GB2355932B (en) * | 1999-04-12 | 2004-01-07 | Univ Madras | A pharmaceutical formulation suitable for the treatment of hepatitis B, hepatitis C and other viral infections of the liver and a process for its preparation |
| US7074436B2 (en) * | 2000-10-06 | 2006-07-11 | Phytrix, Inc. | Method for the production of phyllanthus extracts |
| WO2002087600A1 (fr) * | 2001-04-26 | 2002-11-07 | Phytrix Ag | Utilisation d'elements de phyllanthus pour traiter ou prevenir des infections provoquees par un virus d'hepatite b |
| DE10155517A1 (de) * | 2001-11-13 | 2003-05-28 | Metanomics Gmbh & Co Kgaa | Verfahren zur Extraktion von Inhaltsstoffen aus organischem Material |
| CN110964030A (zh) * | 2019-12-19 | 2020-04-07 | 浙江工业大学 | 一种从叶下珠中分离制备鞣花酸的球磨辅助提取方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4947700A (en) | 2000-10-09 |
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