WO1984004683A1 - Method for isolating allergenes from arnica flowers by means of high pressure co2-extraction - Google Patents
Method for isolating allergenes from arnica flowers by means of high pressure co2-extraction Download PDFInfo
- Publication number
- WO1984004683A1 WO1984004683A1 PCT/EP1984/000151 EP8400151W WO8404683A1 WO 1984004683 A1 WO1984004683 A1 WO 1984004683A1 EP 8400151 W EP8400151 W EP 8400151W WO 8404683 A1 WO8404683 A1 WO 8404683A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- arnica
- extraction
- extracted
- flowers
- high pressure
- Prior art date
Links
- 238000000605 extraction Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 8
- 241000086254 Arnica montana Species 0.000 title description 3
- 241000208983 Arnica Species 0.000 claims abstract description 24
- 239000000341 volatile oil Substances 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 11
- 229940079593 drug Drugs 0.000 claims abstract description 11
- 230000002009 allergenic effect Effects 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 4
- 229930009674 sesquiterpene lactone Natural products 0.000 claims description 11
- 150000002107 sesquiterpene lactone derivatives Chemical class 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 7
- 239000013566 allergen Substances 0.000 claims description 4
- 239000000284 extract Substances 0.000 abstract description 16
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000013543 active substance Substances 0.000 abstract description 2
- -1 sesquiterpenlactones Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229930182486 flavonoid glycoside Natural products 0.000 description 7
- 150000007955 flavonoid glycosides Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- BLZVCIGGICSWIG-UHFFFAOYSA-N 2-aminoethoxydiphenylborane Chemical compound C=1C=CC=CC=1B(OCCN)C1=CC=CC=C1 BLZVCIGGICSWIG-UHFFFAOYSA-N 0.000 description 1
- 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
- DCNRYQODUSSOKC-HKHYKUHTSA-N Angustibalin Chemical compound C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@H](OC(C)=O)[C@]2(C)C(=O)C=C[C@@H]12 DCNRYQODUSSOKC-HKHYKUHTSA-N 0.000 description 1
- OSSDUQKWVVZIGP-UHFFFAOYSA-N Aromaticin Natural products CC1CC2OC(=O)C(=C)C2CC2(C)C(=O)C=CC12 OSSDUQKWVVZIGP-UHFFFAOYSA-N 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- MQVRGDZCYDEQML-UHFFFAOYSA-N Astragalin Natural products C1=CC(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 MQVRGDZCYDEQML-UHFFFAOYSA-N 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000628997 Flos Species 0.000 description 1
- ZVLOPMNVFLSSAA-UHFFFAOYSA-N Heleanalin Natural products CC1CC2OC(=O)C(=C)C2C(O)C2(C)C(=O)C=CC12 ZVLOPMNVFLSSAA-UHFFFAOYSA-N 0.000 description 1
- RFBYGVGDYMSKTD-UHFFFAOYSA-N Helenalin Natural products CC1CC2OC(=O)C(=C)C2C(O)C3C(C)C(=O)C=C13 RFBYGVGDYMSKTD-UHFFFAOYSA-N 0.000 description 1
- OVSQVDMCBVZWGM-IDRAQACASA-N Hirsutrin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)C1=C(c2cc(O)c(O)cc2)Oc2c(c(O)cc(O)c2)C1=O OVSQVDMCBVZWGM-IDRAQACASA-N 0.000 description 1
- FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 description 1
- AFTUDGRDUWDYHE-UHFFFAOYSA-N Mexicanin I Natural products CC1CC2OC(=O)C(=C)C2C(O)C3(C)C1CC=C3C AFTUDGRDUWDYHE-UHFFFAOYSA-N 0.000 description 1
- DCNRYQODUSSOKC-UHFFFAOYSA-N Mexicanin-I-acetat Natural products CC1CC2OC(=O)C(=C)C2C(OC(C)=O)C2(C)C(=O)C=CC12 DCNRYQODUSSOKC-UHFFFAOYSA-N 0.000 description 1
- HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 description 1
- USRAFFQOAADTTD-OJIWXCRVSA-N [(3ar,5r,5ar,8ar,9r,9ar)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] 2-methylprop-2-enoate Chemical compound C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@@H](OC(=O)C(C)=C)[C@]2(C)C(=O)C=C[C@@H]12 USRAFFQOAADTTD-OJIWXCRVSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- ZVLOPMNVFLSSAA-XEPQRQSNSA-N helenalin Chemical compound C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@H](O)[C@]2(C)C(=O)C=C[C@@H]12 ZVLOPMNVFLSSAA-XEPQRQSNSA-N 0.000 description 1
- USRAFFQOAADTTD-UHFFFAOYSA-N helenalin methacrylate Natural products CC1CC2OC(=O)C(=C)C2C(OC(=O)C(C)=C)C2(C)C(=O)C=CC12 USRAFFQOAADTTD-UHFFFAOYSA-N 0.000 description 1
- GXMWXESSGGEWEM-UHFFFAOYSA-N isoquercitrin Natural products OCC(O)C1OC(OC2C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C1O GXMWXESSGGEWEM-UHFFFAOYSA-N 0.000 description 1
- JPUKWEQWGBDDQB-QSOFNFLRSA-N kaempferol 3-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O JPUKWEQWGBDDQB-QSOFNFLRSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0203—Solvent extraction of solids with a supercritical fluid
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/35—Allergens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Definitions
- Arnica montana L. (Compositae family) has been one of the most important medicinal plants of the Central European medicinal treasure for many centuries, monographs of arnica flowers (Flores Arnicae) can be found in all German pharmacopoeias. Numerous medicinal preparations contain extracts from Arnica montana. The main focus of the use of arnica preparations is external use. The effect is described as antiseptic and anti-inflammatory and promotes blood coagulation, arnica extracts are therefore mainly used in wound and healing ointments, but also in hair oils, hair lotions, herbal shampoos and the like. When used internally, a breathing and circulatory and absorption-promoting effect is seen.
- sesquiterpene lactones can be extracted quantitatively by suitable treatment of arnica flowers with liquid or fluid CO 2 , without other ingredients which are important for the pharmacological effect, such as the flavonoid glycosides and part of the essential oil, also being included.
- the invention thus relates to a process for the separation of allergens from arnica flowers, characterized in that dried arnica flowers are subjected to a high-pressure extraction with supercritical CO 2 at 7o-5oo bar and 31-9o ° C and the extracted allergenic substances and any co-extracted essential oil Deposits pressure and / or temperature reduction.
- the dried arnica flowers can be broken up by crushing, for example using a smooth roller under high pressure.
- this has the disadvantage that, in addition to the allergenic sesquiterpene lactones, the essential oil is also extracted quantitatively. It is therefore more advantageous to subject the uncrushed flowers to the extraction, the sesquiterpene lactone component also being removed quantitatively, while a substantial proportion of the essential oil remains in the extracted drug in addition to the other pharmacologically active substances. This is then used in the usual way for the extraction and production of allergen-free arnica extracts, tinctures, etc.
- the extraction takes place with supercritical CO 2 , at pressures between 7o and 5oo bar, preferably at 3oo bar and temperatures between 31 and 9o ° C, preferably at 5o - 7o ° C.
- the separation of the extracts takes place by lowering the pressure and temperature. It takes about 3 to 6 hours to extract the uncrushed drug.
- the determination of the ingredients in the drug before or after the extraction is carried out qualitatively by thin layer chromatography.
- the completeness of the extraction can be assessed by appropriate examination of the CO 2 extract.
- Dried arnica flowers (Arnica. Montana, Flos) are extracted for testing for flavonoids with methanol (lg drug with 20 ml of methanol). It is then filtered and ⁇ s filtrate concentrated to 2 ml.
- the extracts are dissolved in chloroform / methanol (3: 1), 1oo ⁇ l sample are applied to a silica gel GF 254 plate and developed by means of thin layer chromatography with ethyl acetate / formic acid (anhydrous) / acetic acid / H 2 O (100: 11: 11: 25) . Detection is carried out by spraying with a 1% solution of diphenylboryloxyethylamine in methanol.
- the samples (2o - 3O ⁇ l) are applied to a silica gel F 254 thin-layer plate (Merck) and developed with n-pentane / ether (8:17).
- the detection takes place in UV light after spraying with
- the essential oil content is determined in accordance with DAB 8.
- Sesquiterpene lactones can be detected by thin layer chromatography
- the extract contained the total amount of sesquiterpene lactones and 2.2 ml / 100 g of essential oil corresponding to 0.14 ml / 100 g of dried raw material. Flavonoid glycosides could not be detected.
- Sesquiterpene lactones were no longer detectable in the extracted drug, while the essential oil content was 0.02 ml / 100 g. The flavonoid glycosides were completely preserved.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833319184 DE3319184A1 (de) | 1983-05-27 | 1983-05-27 | Verfahren zur abtrennung von allergenen aus arnikablueten mittels co(pfeil abwaerts)2(pfeil abwaerts)-hochdruckextraktion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1984004683A1 true WO1984004683A1 (en) | 1984-12-06 |
Family
ID=6199971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1984/000151 WO1984004683A1 (en) | 1983-05-27 | 1984-05-19 | Method for isolating allergenes from arnica flowers by means of high pressure co2-extraction |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0387952A1 (en) * | 1989-03-16 | 1990-09-19 | Laboratorios Leti, S.A. | Primary toxic chemical compounds or allergens, which may be isolated from plant material as well as methods for their preparation and application |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190129B (it) * | 1986-06-17 | 1988-02-10 | Indena Spa | Procedimento di estrazione di frutti oleaginosi |
| DE3637826C1 (en) * | 1986-11-06 | 1988-05-11 | Hopfenextraktion Hvg Barth | Process for extracting natural dyes from walnut shells and henna |
| AU607027B2 (en) * | 1987-12-16 | 1991-02-21 | Unilever Plc | Process for the extraction of lactones from lipid material and use of the extract thus obtained for flavouring foodstuffs |
| ES2075187T3 (es) * | 1990-07-05 | 1995-10-01 | Indena Spa | Extractos de equinaceas, un procedimiento para su preparacion y formulaciones que los contienen. |
| US5120558A (en) * | 1991-05-01 | 1992-06-09 | Norac Technologies Inc. | Process for the supercritical extraction and fractionation of spices |
| CA2072400C (en) | 1991-07-05 | 2003-08-19 | Jayaprakash B. Nair | Supercritical extraction of taxanes |
| FR2843125B1 (fr) | 2002-08-02 | 2012-11-16 | Coletica | Principes actifs stimulant les beta-defensives humaines de type 2 et/ou de type 3, et compositions cosmetiques ou pharmaceutiques comprenant de tels principes actifs |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2153171A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-09-22 | 1973-05-04 | Sori Sa | |
| EP0010665A1 (de) * | 1978-10-13 | 1980-05-14 | HAG Aktiengesellschaft | Verfahren zur extraktiven Bearbeitung von pflanzlichen und tierischen Materialien |
| EP0023680A1 (de) * | 1979-08-02 | 1981-02-11 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von Gewürzextrakten |
| EP0058365A1 (de) * | 1981-02-16 | 1982-08-25 | Degussa Aktiengesellschaft | Verfahren zur Gewinnung von Inhaltsstoffen der Kamille durch Extraktion mit Kohlendioxid |
-
1983
- 1983-05-27 DE DE19833319184 patent/DE3319184A1/de not_active Withdrawn
-
1984
- 1984-05-19 JP JP59502195A patent/JPS60501456A/ja active Granted
- 1984-05-19 EP EP84901998A patent/EP0144368A1/de not_active Withdrawn
- 1984-05-19 WO PCT/EP1984/000151 patent/WO1984004683A1/de not_active Application Discontinuation
- 1984-05-25 IT IT21097/84A patent/IT1180170B/it active
- 1984-05-25 ES ES532847A patent/ES532847A0/es active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2153171A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-09-22 | 1973-05-04 | Sori Sa | |
| EP0010665A1 (de) * | 1978-10-13 | 1980-05-14 | HAG Aktiengesellschaft | Verfahren zur extraktiven Bearbeitung von pflanzlichen und tierischen Materialien |
| EP0023680A1 (de) * | 1979-08-02 | 1981-02-11 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von Gewürzextrakten |
| EP0058365A1 (de) * | 1981-02-16 | 1982-08-25 | Degussa Aktiengesellschaft | Verfahren zur Gewinnung von Inhaltsstoffen der Kamille durch Extraktion mit Kohlendioxid |
Non-Patent Citations (2)
| Title |
|---|
| Biological Abstracts. Vol. 67, No. 10, 1979, (Philadelphia, PA, US), H.D. HERMANN et al. "Helenalinmethacrylate, a new Pseudoguaianolide from the Flowers of Arnica Montana and the Sensitizing Capacity of their Sesquiterpene Lactones", see Abstract 58244, & Planta Med. 34 (3) :299-304, 1978 * |
| CHEMICAL ABSTRACTS, Vol. 70, No. 20, 19 May 1969 (Columbus, Ohio, US), see page 240, Abstract 90729s SU, 227527 (V.P. KIGHIGIN et al.) 25-09-1968 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0387952A1 (en) * | 1989-03-16 | 1990-09-19 | Laboratorios Leti, S.A. | Primary toxic chemical compounds or allergens, which may be isolated from plant material as well as methods for their preparation and application |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0144368A1 (de) | 1985-06-19 |
| IT8421097A1 (it) | 1985-11-25 |
| IT8421097A0 (it) | 1984-05-25 |
| ES8502864A1 (es) | 1985-02-01 |
| DE3319184A1 (de) | 1984-11-29 |
| JPH0460451B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-09-28 |
| ES532847A0 (es) | 1985-02-01 |
| JPS60501456A (ja) | 1985-09-05 |
| IT1180170B (it) | 1987-09-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE4202657C2 (de) | Pharmazeutisch wirksame Zusammensetzung aus Tanacetum parthenium sowie Verfahren zu deren Extraktion und mit der pharmazeutisch wirksamen Zusammensetzung hergestelltes Arzneimittel | |
| DE3783809T2 (de) | Extraktionsverfahren fuer oelhaltige fruechte. | |
| WO1984004683A1 (en) | Method for isolating allergenes from arnica flowers by means of high pressure co2-extraction | |
| DE3935772C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0904092A1 (de) | Gereinigter extrakt von harpagophytum procumbens und/oder harpagophytum zeyheri dence, verfahren zu seiner herstellung und seine verwendung | |
| EP0285752B1 (de) | Kamillenöle mit hohem Gehalt an natürlichen Polyinen und Verfahren zu deren Herstellung | |
| DE69720234T2 (de) | Verfahren zur herstellung von einem valeriana officinalis extrakt mit hohem gehalt an valerensäure | |
| DE2652380A1 (de) | Verfahren zur isolation von uteroevakuierenden substanzen aus der zoapatlepflanze | |
| DE69710488T2 (de) | Verfahren zur herstellung eines ganodericsäure enthaltenden extraktes aus ganoderma lucidum | |
| DE69618665T2 (de) | Neuartige pflanzenextrakte, herstellungsmethode für dieselben sowie verwendung in kosmetika | |
| DE3874468T2 (de) | Verfahren zur herstellung eines jasminextraktes und der so gewonnene extrakt. | |
| EP0508330B1 (de) | Verfahren zur Herstellung von Extrakten aus Rhizoma Petasitidis mit Kohlendioxid | |
| DE4205783C1 (en) | Prepn. of liquid plant extracts, e.g. contg. pharmaceuticals or perfumes - involves use of an aq. soln. of a nonionic surfactant e.g. fatty acid glycerine polyethylene glycol ester | |
| DE3112737C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0547465B1 (de) | Verfahren zur Herstellung von Extrakten aus Rhizoma Petasitidis | |
| DE2165633C3 (de) | Geruchsverbesserte isopropanolhaltige Kamillenextrakte | |
| DE2515670A1 (de) | Verfahren zur extraktion, isolation und reinigung von praeparaten mit uteroevakuierender wirkung aus der zoapatl- pflanze | |
| DE4221537A1 (de) | Hamamelis-Trockenextrakt, Verfahren zu seiner Herstellung und seine Verwendung als Arzneimittel | |
| CH660966A5 (en) | Process for obtaining a petasites extract with high therapeutic activity from Petasites hybridus, with a content of from 60 to 75% petasin | |
| DE4101841C2 (de) | Verwendung von Sabal-Extrakten zum Behandeln von Mammakarzinomen | |
| DE10056902A1 (de) | Verfahren zur Gewinnung von Triterpenen aus Pflanzen sowie deren Verwendung | |
| DE3901275A1 (de) | Verfahren zur herstellung von oeligem kamillenextrakt | |
| DE604498C (de) | Verfahren zur Herstellung von Frucht- und Pflanzenessenzen | |
| DE2646321A1 (de) | Kosmetisches mittel | |
| WO2003084554A1 (de) | Weidenextrakt |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Designated state(s): JP US |
|
| AL | Designated countries for regional patents |
Designated state(s): AT BE CH DE FR GB NL |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 1984901998 Country of ref document: EP |
|
| WWP | Wipo information: published in national office |
Ref document number: 1984901998 Country of ref document: EP |
|
| WWW | Wipo information: withdrawn in national office |
Ref document number: 1984901998 Country of ref document: EP |