JPS5951931B2 - 植物抽出物からの子宮−エバキユアントの単離 - Google Patents
植物抽出物からの子宮−エバキユアントの単離Info
- Publication number
- JPS5951931B2 JPS5951931B2 JP52079558A JP7955877A JPS5951931B2 JP S5951931 B2 JPS5951931 B2 JP S5951931B2 JP 52079558 A JP52079558 A JP 52079558A JP 7955877 A JP7955877 A JP 7955877A JP S5951931 B2 JPS5951931 B2 JP S5951931B2
- Authority
- JP
- Japan
- Prior art keywords
- alumina
- uterus
- mixture
- evacuant
- column
- 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.)
- Expired
Links
- 238000002955 isolation Methods 0.000 title description 2
- 239000000419 plant extract Substances 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 241000196324 Embryophyta Species 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 241000396685 Montanoa Species 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 241000401894 Montanoa tomentosa Species 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- -1 aliphatic ethers Chemical class 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 210000004291 uterus Anatomy 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 244000269722 Thea sinensis Species 0.000 description 5
- 230000035935 pregnancy Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 210000003101 oviduct Anatomy 0.000 description 4
- 239000013014 purified material Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- XJWOWXZSFTXJEX-UHFFFAOYSA-N phenylsilicon Chemical compound [Si]C1=CC=CC=C1 XJWOWXZSFTXJEX-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- 206010000234 Abortion spontaneous Diseases 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 208000031271 Unwanted pregnancy Diseases 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- JRQSTWLYBFBPDX-UMKHLJCSSA-N helian Natural products OC[C@H]1O[C@@H](O[C@@H](C=C/CCCC=C)C#CC#C[C@@H](O)C=C)[C@H](O)[C@@H](O)[C@@H]1O JRQSTWLYBFBPDX-UMKHLJCSSA-N 0.000 description 1
- 235000012171 hot beverage Nutrition 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000002175 menstrual effect Effects 0.000 description 1
- 230000003821 menstrual periods Effects 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 208000015994 miscarriage Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001215 vagina Anatomy 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)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medical Informatics (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Alternative & Traditional Medicine (AREA)
- Reproductive Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pregnancy & Childbirth (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US000000703160 | 1976-07-07 | ||
| US05/703,160 US4061739A (en) | 1976-07-07 | 1976-07-07 | Isolation of utero-evacuant substances from plant extracts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS539310A JPS539310A (en) | 1978-01-27 |
| JPS5951931B2 true JPS5951931B2 (ja) | 1984-12-17 |
Family
ID=24824268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52079558A Expired JPS5951931B2 (ja) | 1976-07-07 | 1977-07-05 | 植物抽出物からの子宮−エバキユアントの単離 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4061739A (Direct) |
| JP (1) | JPS5951931B2 (Direct) |
| AT (1) | AT360642B (Direct) |
| AU (1) | AU516055B2 (Direct) |
| BE (1) | BE856590A (Direct) |
| CA (1) | CA1085300A (Direct) |
| DE (1) | DE2730378A1 (Direct) |
| FR (1) | FR2357255A1 (Direct) |
| GB (1) | GB1582963A (Direct) |
| GR (1) | GR62450B (Direct) |
| IE (1) | IE45391B1 (Direct) |
| IL (1) | IL52459A (Direct) |
| NL (1) | NL7707583A (Direct) |
| NZ (1) | NZ184498A (Direct) |
| PH (1) | PH12356A (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4491593A (en) * | 1983-01-27 | 1985-01-01 | Gallegos Alfredo J | Compositions and methods for fertility control |
| EP0669151B1 (en) * | 1994-02-24 | 2003-03-26 | Matsushita Electric Industrial Co., Ltd. | Method for extracting organic substance, solvent for use in said method, and method for measuring content of organic substance |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2115670C2 (de) * | 1971-03-31 | 1981-06-04 | Siemens AG, 1000 Berlin und 8000 München | Schaltungsanordnung für Fernsprechstationen mit überspannungsgeschützten und polungsunabhängigen Mikrofonverstärkern in integrierter monolithischer Technik |
| US3996132A (en) * | 1974-07-18 | 1976-12-07 | Ortho Pharmaceutical Corporation | Purification of utero-evacuant extracts from plant substances |
-
1976
- 1976-07-07 US US05/703,160 patent/US4061739A/en not_active Expired - Lifetime
-
1977
- 1977-06-28 GB GB27102/77A patent/GB1582963A/en not_active Expired
- 1977-06-28 NZ NZ184498A patent/NZ184498A/xx unknown
- 1977-06-29 CA CA281,716A patent/CA1085300A/en not_active Expired
- 1977-07-05 DE DE19772730378 patent/DE2730378A1/de not_active Ceased
- 1977-07-05 JP JP52079558A patent/JPS5951931B2/ja not_active Expired
- 1977-07-05 AU AU26756/77A patent/AU516055B2/en not_active Expired
- 1977-07-05 IL IL52459A patent/IL52459A/xx unknown
- 1977-07-06 AT AT483177A patent/AT360642B/de not_active IP Right Cessation
- 1977-07-06 FR FR7720802A patent/FR2357255A1/fr active Granted
- 1977-07-06 GR GR53898A patent/GR62450B/el unknown
- 1977-07-06 IE IE1400/77A patent/IE45391B1/en unknown
- 1977-07-07 BE BE179165A patent/BE856590A/xx not_active IP Right Cessation
- 1977-07-07 NL NL7707583A patent/NL7707583A/xx not_active Application Discontinuation
- 1977-07-07 PH PH7719965A patent/PH12356A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ184498A (en) | 1979-08-31 |
| GB1582963A (en) | 1981-01-21 |
| US4061739A (en) | 1977-12-06 |
| FR2357255B1 (Direct) | 1983-10-28 |
| GR62450B (en) | 1979-04-12 |
| DE2730378A1 (de) | 1978-01-12 |
| AU516055B2 (en) | 1981-05-14 |
| FR2357255A1 (fr) | 1978-02-03 |
| CA1085300A (en) | 1980-09-09 |
| IE45391B1 (en) | 1982-08-11 |
| PH12356A (en) | 1979-01-29 |
| JPS539310A (en) | 1978-01-27 |
| ATA483177A (de) | 1980-06-15 |
| NL7707583A (nl) | 1978-01-10 |
| IL52459A (en) | 1980-03-31 |
| AT360642B (de) | 1981-01-26 |
| AU2675677A (en) | 1979-01-11 |
| IL52459A0 (en) | 1977-10-31 |
| BE856590A (fr) | 1978-01-09 |
| IE45391L (en) | 1978-01-07 |
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