FR2463620A1 - Extraits de marsdenia cindurango reichenbach fil, des procedes de preparation de ceux-ci, des agents anti-tumeur les contenant et des compositions les contenant - Google Patents
Extraits de marsdenia cindurango reichenbach fil, des procedes de preparation de ceux-ci, des agents anti-tumeur les contenant et des compositions les contenant Download PDFInfo
- Publication number
- FR2463620A1 FR2463620A1 FR8018419A FR8018419A FR2463620A1 FR 2463620 A1 FR2463620 A1 FR 2463620A1 FR 8018419 A FR8018419 A FR 8018419A FR 8018419 A FR8018419 A FR 8018419A FR 2463620 A1 FR2463620 A1 FR 2463620A1
- Authority
- FR
- France
- Prior art keywords
- extract
- fraction
- soluble
- collect
- chloroform
- 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.)
- Pending
Links
- 239000000284 extract Substances 0.000 title claims abstract description 166
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 4
- 239000000203 mixture Substances 0.000 title claims description 50
- 241001247900 Marsdenia Species 0.000 title description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 53
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 45
- 241001347462 Marsdenia cundurango Species 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 12
- 150000001298 alcohols Chemical class 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 135
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 43
- 238000010586 diagram Methods 0.000 claims description 40
- 238000010828 elution Methods 0.000 claims description 19
- 239000003480 eluent Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 239000003643 water by type Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000001514 detection method Methods 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 7
- -1 aliphatic ester Chemical class 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 230000000259 anti-tumor effect Effects 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 22
- 239000000843 powder Substances 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 16
- 206010028980 Neoplasm Diseases 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000006268 Sarcoma 180 Diseases 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000004305 normal phase HPLC Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000208327 Apocynaceae Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- SGDAJMSNTKLPML-SKMKETMKSA-N Condurangogenin A Chemical compound O([C@@H]1[C@H]([C@@H]2[C@@]3(C)CC[C@H](O)C[C@@H]3CC[C@H]2[C@@]2(O)CC[C@@H]([C@]21C)C(C)=O)OC(=O)C)C(=O)\C=C\C1=CC=CC=C1 SGDAJMSNTKLPML-SKMKETMKSA-N 0.000 description 1
- NUPFZNSJJIZBGR-DSXGPZHDSA-N Condurangogenin C Chemical compound O([C@@H]1[C@@H](OC(C)=O)[C@@H]2[C@@]3(C)CC[C@H](O)C[C@@H]3CC[C@H]2[C@@]2(O)CC[C@@H]([C@@]12C)C(O)C)C(=O)\C=C\C1=CC=CC=C1 NUPFZNSJJIZBGR-DSXGPZHDSA-N 0.000 description 1
- 101000874334 Dalbergia nigrescens Isoflavonoid 7-O-beta-apiosyl-glucoside beta-glycosidase Proteins 0.000 description 1
- 101000757733 Enterococcus faecalis (strain ATCC 700802 / V583) Autolysin Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101000757734 Mycolicibacterium phlei 38 kDa autolysin Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- FKXVPEBFIHNLPS-UHFFFAOYSA-N condurangogenin C Natural products CC(=O)OC1C2(C)C(C(O)C)CCC2(O)C2CCC3CC(O)CCC3(C)C2C1OC(=O)C=CC1=CC=CC=C1 FKXVPEBFIHNLPS-UHFFFAOYSA-N 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 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)
- A61K36/27—Asclepiadaceae (Milkweed family), e.g. hoya
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Engineering & Computer Science (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10736679A JPS5630924A (en) | 1979-08-23 | 1979-08-23 | Extract of marsdenia condurango reichenbach fil., antitumor agent cosisting of the same and its preparation |
| JP13606179A JPS5659713A (en) | 1979-10-22 | 1979-10-22 | Antitumor agent and its preparation |
| JP2769680A JPS56123998A (en) | 1980-03-05 | 1980-03-05 | Cundurango extract, its preparation, and antitumor agent comprising it |
| JP2769780A JPS56123999A (en) | 1980-03-05 | 1980-03-05 | Cundurango glycoside, its preparation and antitumor agent comprising it |
| JP5209780A JPS56147721A (en) | 1980-04-19 | 1980-04-19 | Condurango extract, its production and antitumorigenic agent therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2463620A1 true FR2463620A1 (fr) | 1981-02-27 |
Family
ID=27520957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8018419A Pending FR2463620A1 (fr) | 1979-08-23 | 1980-08-22 | Extraits de marsdenia cindurango reichenbach fil, des procedes de preparation de ceux-ci, des agents anti-tumeur les contenant et des compositions les contenant |
Country Status (8)
| Country | Link |
|---|---|
| CA (1) | CA1144917A (enrdf_load_stackoverflow) |
| DE (1) | DE3031745A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2463620A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2060379A (enrdf_load_stackoverflow) |
| IT (1) | IT1141617B (enrdf_load_stackoverflow) |
| NL (1) | NL8004751A (enrdf_load_stackoverflow) |
| PL (1) | PL226369A1 (enrdf_load_stackoverflow) |
| SE (1) | SE8005919L (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054570A1 (en) * | 1980-03-05 | 1982-06-30 | Zenyaku Kogyo Kabushiki Kaisha | Novel condurango glycosides, process for their preparation, antineoplastic agent, and composition containing same |
-
1980
- 1980-08-22 SE SE8005919A patent/SE8005919L/ not_active Application Discontinuation
- 1980-08-22 DE DE19803031745 patent/DE3031745A1/de not_active Withdrawn
- 1980-08-22 GB GB8027337A patent/GB2060379A/en not_active Withdrawn
- 1980-08-22 FR FR8018419A patent/FR2463620A1/fr active Pending
- 1980-08-22 CA CA000358853A patent/CA1144917A/en not_active Expired
- 1980-08-22 NL NL8004751A patent/NL8004751A/nl not_active Application Discontinuation
- 1980-08-22 PL PL22636980A patent/PL226369A1/xx unknown
- 1980-08-25 IT IT68313/80A patent/IT1141617B/it active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054570A1 (en) * | 1980-03-05 | 1982-06-30 | Zenyaku Kogyo Kabushiki Kaisha | Novel condurango glycosides, process for their preparation, antineoplastic agent, and composition containing same |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL PHARMACEUTICAL BULLETIN, vol. 28, no. 6, juin 1980, TOKYO (JP); KOJI HAYASHI et al.:"Antitumor active glycosides from condurango Cortex", pages 1954-1958. * |
| P.H. LIST et L. H\RHAMMER:"Hagers Handbuch der Pharmazeutischen Praxis", vollst{ndige (vierte) Neuausgabe, f}nfter Band, Chemikalien und Drogen, 1976, Springer Verlag, BERLIN (DE), pages 706-708. * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3031745A1 (de) | 1981-05-27 |
| NL8004751A (nl) | 1981-02-25 |
| CA1144917A (en) | 1983-04-19 |
| IT8068313A0 (it) | 1980-08-25 |
| PL226369A1 (enrdf_load_stackoverflow) | 1981-05-22 |
| IT1141617B (it) | 1986-10-01 |
| SE8005919L (sv) | 1981-03-27 |
| GB2060379A (en) | 1981-05-07 |
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