WO2004060267A2 - Procede de production de fractions enrichies contenant jusqu'a 100 % de bacoside a et de bacoside b a partir de substances vegetales de l'espece bacopa - Google Patents
Procede de production de fractions enrichies contenant jusqu'a 100 % de bacoside a et de bacoside b a partir de substances vegetales de l'espece bacopa Download PDFInfo
- Publication number
- WO2004060267A2 WO2004060267A2 PCT/IN2003/000002 IN0300002W WO2004060267A2 WO 2004060267 A2 WO2004060267 A2 WO 2004060267A2 IN 0300002 W IN0300002 W IN 0300002W WO 2004060267 A2 WO2004060267 A2 WO 2004060267A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bacoside
- bacosides
- water
- solvent
- dried
- Prior art date
Links
- 229930193652 Bacoside Natural products 0.000 title claims abstract description 26
- LKCTWIIDXXXXAR-CYGHALRTSA-N Bacoside a Chemical compound CC(C)=CCC[C@](C)(O)[C@@H]1[C@H]2CC[C@H]3[C@@](C)(CC[C@H]4C(C)(C)C(CC[C@]34CO)O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4OC[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@]2(C)CC1=O LKCTWIIDXXXXAR-CYGHALRTSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 17
- GKLLCNWAEBKYGL-UHFFFAOYSA-N Bacoside B Natural products CC(=CCC(C)(O)C1C2CCC3C(C)(CCC4C(C)(C)C(CCC34CO)OC5C(O)C(O)C(OCC6OCC(O)C(O)C6O)OC5CO)C2(C)CC1=O)C GKLLCNWAEBKYGL-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 18
- 241000196324 Embryophyta Species 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000284 extract Substances 0.000 claims abstract description 13
- 238000013375 chromatographic separation Methods 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 6
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 4
- 239000002798 polar solvent Substances 0.000 claims abstract description 4
- 238000011097 chromatography purification Methods 0.000 claims abstract description 3
- 240000002999 Bacopa monnieri Species 0.000 claims abstract 2
- 235000015418 Bacopa monnieria Nutrition 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 241000295198 Bacopa Species 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 238000011210 chromatographic step Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000000419 plant extract Substances 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 230000000063 preceeding effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000000605 extraction Methods 0.000 abstract description 3
- 230000001476 alcoholic effect Effects 0.000 abstract description 2
- 239000000356 contaminant Substances 0.000 abstract description 2
- 238000003809 water extraction Methods 0.000 abstract 1
- 244000187129 Bacopa monnieria Species 0.000 description 12
- 229930182490 saponin Natural products 0.000 description 5
- 150000007949 saponins Chemical class 0.000 description 5
- 235000017709 saponins Nutrition 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 239000012675 alcoholic extract Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 239000000399 hydroalcoholic extract Substances 0.000 description 2
- 230000006883 memory enhancing effect Effects 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 241000894007 species Species 0.000 description 2
- TUWRBFMVJOJFCL-UHFFFAOYSA-N 4'-O-beta-D-Glucopyranoside,7-O-rutinoside-3',4',5,7-Tetrahydroxyflavone Natural products CC(=CC=CC(=C/C1CCC2C3(C)CCC(O)C(C)(C)C3CCC2(C)C14COC(=O)C4)C)C TUWRBFMVJOJFCL-UHFFFAOYSA-N 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 241000013557 Plantaginaceae Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000002012 ayurvedic medicine Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000009160 phytotherapy Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
- A61K36/80—Scrophulariaceae (Figwort family)
Definitions
- Bacopa monniera Linn Infusion or extract of the plant Bacopa monniera Linn has been used for centuries in traditional Ayurvedic medicines as a memory enhancing and rejuvenating agent.
- Bacopa monniera is known in Hindi and other local Indian lanugages as Brahmi and has been prescribed as a cure for mental disorders, weak intellect, anxiety and lack of concentration.
- Anti-inflammatory, analgesic, antipyretic and antiepileptic properties of an extract of Brahmi have also been recorded.
- Bacopa monniera Linn is from the family Scrophulariaceae and is a common creeping perennial herb that grows luxuriantly in moist, damp and marshy areas throughtout India and is commonly known as Brahmi or Jal Brahmi.
- An alcoholic extract of Bacopa monniera has shown improved acquisition, consolidation and retention of newly acquired behavioral responses in albino rats.
- Major chemical constituents of the alcoholic extracts are Saponins, Bacoside A and Bacoside B. These saponins have been established as the components reponsible for memory enhancing and the like properties (Singh and Dhawan, Indian Journal of Pharmacology, 29, S 359 - S 365, 1997; Singh, et al, Phytotherapy Research, 2, 70-75, 1988, published from the USA).
- a double-blind placebo controlled study carried out on 110 school children in the age group of 10-13 years to assess the effect of the extract of Bacopa monniera revealed significant enhancement in their arithmetic skills and memory ( R. Abhang, Journal of Research inAyurveda andSidda, 14, 10-24, 1993).
- Alcoholic extract obtained by extracting a dried plant material is found to contain two f actions designated as Bacoside A and Bacoside B. Both the fractions have same aglycone moities and sugar residues. Haemolytic activity of Bacoside B is found to be much higher than that of Bacoside A.
- Bacosides A and B are crystalline mixtures of hiteipeniod glycosides of the general formula I and II shown herein below. Bacoside A has been isolated in the pure state though Bacoside B has not yet been isolated in the pure state.
- These compounds have either jujobogenm or pseudojujobogenin skeleton and contains one or more arabinose or glucose units.
- R Sugar Unit
- R 1 H or Sugar Unit
- the sugar portion may contain one or more arabinose or glucose units.
- Fig. 1 Gross structures of Bacosides A and B
- Fig. 2 Acid hydrolysis product of Bacosides A and B Disclosure of the Invention:
- the present invention is aimed at eniiching the Bacoside A and B concentration in the plant extract and further separation of the individual saponins therefrom. This objective is achieved by using a combination of solvents for preliminary extraction from the plant source and thereafter by chromatographic separation process.
- Ethanolic or hydroethanolic extract obtained from dried plant material is dried preferably in vacuum. Fats and other contaminants are removed from the dry solid mass by treating the same from petroleum ether or hexane. The mass obtained after removal of fatty materials therefrom is extracted with a polar organic solvent selected from ethyl acetate, n-butyl acetate, ethyl propionate, isopropanol, n-butanol, n-pentanol or mixtures thereof.
- a polar organic solvent selected from ethyl acetate, n-butyl acetate, ethyl propionate, isopropanol, n-butanol, n-pentanol or mixtures thereof.
- Organic layer containing Bacoisdes is separated, washed with water to remove undesired water soluble impurities such as sugars and salts, and then concentrated and dried under vacuum to obtain an enriched fraction containing Bacosides A and B in the range of 30 to 80%.
- This enriched fraction is subjected to silica gel chromatography using as eluants, chlorof orm, methanol or water or a mixture of them to obtain a fraction containing 80% -100 % of the Bacosides. Rechromatography of this enriched fraction results in the separation of individual Bacoside A and B. It is possible to carry out this chromatographic separation on a reversed phase silica gel.
- This invention relates to a process for producing enriched fractions containing up to 100 % of Bacoside A and Bacoside B from plant materials of Bacopa species which comprises the steps of subjecting plant materials of Bacopa species to organic solvent extraction, drying said extract, washing said dried mass with non-polar organic solvents to remove f tty materials therefrom, extracting the residue with at least one organic polar solvent washing said extract with water, and concentrating the solvent fraction under vacuum to obtain a concentrate containing 30 to 80% of Bacosides A and B, subjecting said concentrate to chromatographic separation and purification using organic solvents and water or mixtures thereof to obtain a faction containing 80 to 100% of Bacosides A and B and subjecting said enriched fraction to rechromatography to separate Bacoside A from Bacoside B therefrom.
- the last two chromatographic steps could also be combined into a single chromatograpliic separation.
- This invention also includes Bacoside A and Bacoside B prepared and separated by the process described herein above.
- An alcoholic or hydroalcoholic extract is prepared in the conventional manner from dried plant materials of Bacopa monniera. After removing the solvents by evaporation preferably under vacuum a solid which contains a mixture of Bacoside A and Bacoside B is obtained. This mixture containing 20 to 30% of the saponins is then extracted with petroleum ether three times to remove fatty materials therefrom. The solid obtained after petroleum ether extraction is refluxed with ethyl acetate at least twice. The combined solvent extract is washed with water and then dried over sodium sulphate initially and then concentrated and dried under vacuum to give a fraction containing 60 to 65% Bacosides A and B.
- the saponin content may vary from species to species and will also depend on various other factors such as the state of growth of the plants.
- Enriched fractions of Bacosides or the pure Bacosides separated by this method could be used in lower dosage for therapeutic use.
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- 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)
- Steroid Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
L'invention concerne un procédé de production de fractions contenant Bacosides A et B à partir de substances végétales de l'espèce Bacopa, par extraction, concentration et séparation. Selon ce procédé, lesdites substances végétales séchées sont soumises à une extraction alcoolique, hydroalcoolique ou aqueuse, et un concentré est produit à partir de l'extrait obtenu. La masse solide ainsi produite est lavée au moyen d'un solvant organique non polaire pour supprimer les matières grasses qu'elle renferme, puis soumise à une extraction à l'aide d'un solvant polaire organique. L'extrait obtenu au moyen dudit solvant est lavé pour supprimer les impuretés hydrosolubles qu'il contient, puis séché sous vide. La fraction obtenue, qui est enrichie en Bacosides A et B, est soumise de manière répétée à une séparation chromatographique et à une purification pour obtenir Bacoside A et Bacoside B.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003201756A AU2003201756A1 (en) | 2003-01-03 | 2003-01-03 | A process for producing enriched fractions containing up to 100% of bacoside a and bacoside b |
| PCT/IN2003/000002 WO2004060267A2 (fr) | 2003-01-03 | 2003-01-03 | Procede de production de fractions enrichies contenant jusqu'a 100 % de bacoside a et de bacoside b a partir de substances vegetales de l'espece bacopa |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000002 WO2004060267A2 (fr) | 2003-01-03 | 2003-01-03 | Procede de production de fractions enrichies contenant jusqu'a 100 % de bacoside a et de bacoside b a partir de substances vegetales de l'espece bacopa |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2004060267A2 true WO2004060267A2 (fr) | 2004-07-22 |
| WO2004060267A3 WO2004060267A3 (fr) | 2004-11-04 |
Family
ID=32697207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2003/000002 WO2004060267A2 (fr) | 2003-01-03 | 2003-01-03 | Procede de production de fractions enrichies contenant jusqu'a 100 % de bacoside a et de bacoside b a partir de substances vegetales de l'espece bacopa |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2003201756A1 (fr) |
| WO (1) | WO2004060267A2 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006097043A1 (fr) * | 2005-03-15 | 2006-09-21 | Chengdu Wagott Pharmaceutical Co., Ltd. | Extrait de bacopa monnieri et son procede de preparation et d'utilisation |
| US8541381B2 (en) | 2005-05-03 | 2013-09-24 | Laila Impex | Process for producing enriched fractions containing up to 100% of bacopasaponins from the plant materials of bacopa species |
| CN111067965A (zh) * | 2019-12-29 | 2020-04-28 | 三原润禾生物科技有限公司 | 一种假马齿苋皂甙的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19654635C1 (de) * | 1996-12-28 | 1998-01-08 | Singh Verma Shyam B | Kosmetische Zubereitungen enthaltend Extrakte von Phyllanthus emblica und Centella asiatica |
| FR2774590B1 (fr) * | 1998-02-12 | 2001-07-13 | Sederma Sa | Compositions a usage cosmetique ou dermopharmaceutique contenant un extrait vegetal obtenu a partir bacopa monnieri (l.) |
-
2003
- 2003-01-03 WO PCT/IN2003/000002 patent/WO2004060267A2/fr not_active Application Discontinuation
- 2003-01-03 AU AU2003201756A patent/AU2003201756A1/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006097043A1 (fr) * | 2005-03-15 | 2006-09-21 | Chengdu Wagott Pharmaceutical Co., Ltd. | Extrait de bacopa monnieri et son procede de preparation et d'utilisation |
| CN1833692B (zh) * | 2005-03-15 | 2010-08-11 | 成都华高药业有限公司 | 一种假马齿苋提取物及其制备方法和用途 |
| US8541381B2 (en) | 2005-05-03 | 2013-09-24 | Laila Impex | Process for producing enriched fractions containing up to 100% of bacopasaponins from the plant materials of bacopa species |
| CN111067965A (zh) * | 2019-12-29 | 2020-04-28 | 三原润禾生物科技有限公司 | 一种假马齿苋皂甙的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003201756A8 (en) | 2004-07-29 |
| AU2003201756A1 (en) | 2004-07-29 |
| WO2004060267A3 (fr) | 2004-11-04 |
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