DE3031745A1 - Extrakte von marsdenia cundurango reichenbach fil, verfahren zu deren herstellung, antitumormittel und arzneimittel, die diese extrakte enthalten, und anwendung der extrakte zur behandlung von tumoren - Google Patents
Extrakte von marsdenia cundurango reichenbach fil, verfahren zu deren herstellung, antitumormittel und arzneimittel, die diese extrakte enthalten, und anwendung der extrakte zur behandlung von tumorenInfo
- Publication number
- DE3031745A1 DE3031745A1 DE19803031745 DE3031745A DE3031745A1 DE 3031745 A1 DE3031745 A1 DE 3031745A1 DE 19803031745 DE19803031745 DE 19803031745 DE 3031745 A DE3031745 A DE 3031745A DE 3031745 A1 DE3031745 A1 DE 3031745A1
- Authority
- DE
- Germany
- Prior art keywords
- extract
- chloroform
- methanol
- carbon tetrachloride
- fraction
- 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.)
- Withdrawn
Links
- 239000000284 extract Substances 0.000 title claims description 196
- 241001347462 Marsdenia cundurango Species 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 20
- 206010028980 Neoplasm Diseases 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229940126601 medicinal product Drugs 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 148
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 53
- 238000010586 diagram Methods 0.000 claims description 51
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000003480 eluent Substances 0.000 claims description 18
- 238000001514 detection method Methods 0.000 claims description 17
- 238000010828 elution Methods 0.000 claims description 17
- 239000000945 filler Substances 0.000 claims description 16
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 241001247900 Marsdenia Species 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 230000000259 anti-tumor effect Effects 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- 238000004811 liquid chromatography Methods 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 208000006268 Sarcoma 180 Diseases 0.000 description 4
- 238000000967 suction filtration Methods 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- -1 pentane Chemical class 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 210000004013 groin Anatomy 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 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
- 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
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- 230000001154 acute effect Effects 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000004067 bulking agent Substances 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
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 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
- 150000008266 deoxy sugars Chemical class 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
- 239000007884 disintegrant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- TWAOQVMPIYQPKG-UHFFFAOYSA-N ethanone Chemical compound C[C+]=O TWAOQVMPIYQPKG-UHFFFAOYSA-N 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
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 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
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000004904 shortening Methods 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
- 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
- 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000012795 verification 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)
- 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)
- 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 |
| JP2769780A JPS56123999A (en) | 1980-03-05 | 1980-03-05 | Cundurango glycoside, its preparation and antitumor agent comprising it |
| JP2769680A JPS56123998A (en) | 1980-03-05 | 1980-03-05 | Cundurango extract, 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 |
|---|---|
| DE3031745A1 true DE3031745A1 (de) | 1981-05-27 |
Family
ID=27520957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803031745 Withdrawn DE3031745A1 (de) | 1979-08-23 | 1980-08-22 | Extrakte von marsdenia cundurango reichenbach fil, verfahren zu deren herstellung, antitumormittel und arzneimittel, die diese extrakte enthalten, und anwendung der extrakte zur behandlung von tumoren |
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) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1144136B (it) * | 1980-03-05 | 1986-10-29 | Zenyaku Kogyo Kk | Glucosidi di condurango agenti antitumorali che li comprendono e procedimento per la loro preparazione |
-
1980
- 1980-08-22 SE SE8005919A patent/SE8005919L/ not_active Application Discontinuation
- 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 FR FR8018419A patent/FR2463620A1/fr active Pending
- 1980-08-22 DE DE19803031745 patent/DE3031745A1/de not_active Withdrawn
- 1980-08-22 PL PL22636980A patent/PL226369A1/xx unknown
- 1980-08-22 GB GB8027337A patent/GB2060379A/en not_active Withdrawn
- 1980-08-25 IT IT68313/80A patent/IT1141617B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1141617B (it) | 1986-10-01 |
| GB2060379A (en) | 1981-05-07 |
| NL8004751A (nl) | 1981-02-25 |
| CA1144917A (en) | 1983-04-19 |
| IT8068313A0 (it) | 1980-08-25 |
| PL226369A1 (enrdf_load_stackoverflow) | 1981-05-22 |
| FR2463620A1 (fr) | 1981-02-27 |
| SE8005919L (sv) | 1981-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8181 | Inventor (new situation) |
Free format text: MITSUHASHI, HIROSHI, SAPPORO, HAKKAIDO, JP MIZUNO, DENICHI, KAMAKURA, KANAGAWA, JP HAYASHI, KOJI, SAPPORO, HOKKAIDO, JP ABE, SHIGERU, TOKYO, JP TAKASE, MUNEAKI NARITA, TOSHIHARU, HIGASHIMURAYAMA, TOKYO, JP |
|
| 8139 | Disposal/non-payment of the annual fee |