DE2609533C3 - Verfahren zur Extraktion von Wirkstoffen, insbesondere von Heterosidestern der Kaffeesäure, sowie diese Verbindungen enthaltende Arzneimittel - Google Patents
Verfahren zur Extraktion von Wirkstoffen, insbesondere von Heterosidestern der Kaffeesäure, sowie diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE2609533C3 DE2609533C3 DE19762609533 DE2609533A DE2609533C3 DE 2609533 C3 DE2609533 C3 DE 2609533C3 DE 19762609533 DE19762609533 DE 19762609533 DE 2609533 A DE2609533 A DE 2609533A DE 2609533 C3 DE2609533 C3 DE 2609533C3
- Authority
- DE
- Germany
- Prior art keywords
- caffeic acid
- extract
- heteroside
- dopa
- extraction
- 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
- 150000002148 esters Chemical class 0.000 title claims description 12
- 239000003814 drug Substances 0.000 title claims description 9
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 title description 31
- 238000000034 method Methods 0.000 title description 23
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 title description 13
- 229940074360 caffeic acid Drugs 0.000 title description 13
- 235000004883 caffeic acid Nutrition 0.000 title description 13
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 title description 13
- 230000008569 process Effects 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 title description 9
- 238000000605 extraction Methods 0.000 title description 8
- 239000013543 active substance Substances 0.000 title 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 claims description 7
- 239000008103 glucose Substances 0.000 claims description 7
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 6
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims description 6
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000284 extract Substances 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 235000013824 polyphenols Nutrition 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 24
- 150000008442 polyphenolic compounds Chemical class 0.000 description 24
- 230000000694 effects Effects 0.000 description 19
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- PZTVNHKDWVHORF-FMEUUFJCSA-N Orobanchoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](OC(=O)\C=C\C=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@H]1OC[C@@H](O)C1=CC=C(O)C(O)=C1 PZTVNHKDWVHORF-FMEUUFJCSA-N 0.000 description 12
- PZTVNHKDWVHORF-HDKCILJWSA-N orobanchoside Natural products C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OC(=O)C=Cc3ccc(O)c(O)c3)[C@@H](CO)O[C@H]2OC[C@H](O)c4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O PZTVNHKDWVHORF-HDKCILJWSA-N 0.000 description 12
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 11
- KDSWDGKIENPKLB-QJDQKFITSA-N verbascoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC(=O)CCC=2C=C(O)C(O)=CC=2)[C@@H](CO)O[C@@H](OCCC=2C=C(O)C(O)=CC=2)[C@@H]1O KDSWDGKIENPKLB-QJDQKFITSA-N 0.000 description 11
- QFRYQWYZSQDFOS-UHFFFAOYSA-N verbascoside Natural products CC1OC(COC2C(O)C(COC3OC(C(O)C(O)C3O)C(=O)O)OC(Oc4cc(O)cc5OC(=CC(=O)c45)c6ccc(O)c(O)c6)C2O)C(O)C(O)C1O QFRYQWYZSQDFOS-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241001508464 Orobanche Species 0.000 description 9
- 230000001476 alcoholic effect Effects 0.000 description 8
- 208000018737 Parkinson disease Diseases 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 241000207965 Acanthaceae Species 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 238000005238 degreasing Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 230000004899 motility Effects 0.000 description 5
- 102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000308150 Orobanchaceae Species 0.000 description 4
- 241000207844 Scrophulariaceae Species 0.000 description 4
- 108010035075 Tyrosine decarboxylase Proteins 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000207923 Lamiaceae Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 206010044565 Tremor Diseases 0.000 description 3
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241001530097 Verbascum Species 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000005242 cardiac chamber Anatomy 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229960004502 levodopa Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000004622 sleep time Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- YAHHFDSODKFKOV-OTEWLTGOSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(2r,3r,4s,5s)-2,3,4,5-tetrahydroxyhexanal Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O YAHHFDSODKFKOV-OTEWLTGOSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010015548 Euthanasia Diseases 0.000 description 1
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 101100332755 Mus musculus Edar gene Proteins 0.000 description 1
- 241001337946 Orobanche hederae Species 0.000 description 1
- 241000263388 Orobanche rapum-genistae Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- 241001613786 Phelipanche Species 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- 241001314298 Verbascum sinuatum Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- -1 ethanol or methanol Chemical compound 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- SWUARLUWKZWEBQ-VQHVLOKHSA-N phenethyl caffeate Chemical compound C1=C(O)C(O)=CC=C1\C=C\C(=O)OCCC1=CC=CC=C1 SWUARLUWKZWEBQ-VQHVLOKHSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000004458 spent grain Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7507316A FR2302745A1 (fr) | 1975-03-07 | 1975-03-07 | Esters heterosidiques d'acide cafeique, leurs procedes de preparation e |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2609533A1 DE2609533A1 (de) | 1976-09-16 |
| DE2609533B2 DE2609533B2 (de) | 1980-02-21 |
| DE2609533C3 true DE2609533C3 (de) | 1980-10-09 |
Family
ID=9152305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762609533 Expired DE2609533C3 (de) | 1975-03-07 | 1976-03-08 | Verfahren zur Extraktion von Wirkstoffen, insbesondere von Heterosidestern der Kaffeesäure, sowie diese Verbindungen enthaltende Arzneimittel |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2609533C3 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2302745A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU670742B2 (en) * | 1991-03-21 | 1996-08-01 | Parfums Christian Dior | Novel derivative of caffeic acid, oraposide, cosmetic or pharmaceutical, particularly dermatological, composition containing it |
| US6991812B2 (en) * | 2000-09-05 | 2006-01-31 | Kao Corporation | Agent for preventing, improving or treating hypertension |
| JP2002363075A (ja) * | 2001-06-05 | 2002-12-18 | Kao Corp | 高血圧症予防・治療剤 |
| EP2527315B1 (en) * | 2002-05-31 | 2014-03-19 | Proteotech Inc. | Compounds, compositions and methods for the treatment of amyloid diseases and synucleinopathies such as Alzheimer's disease, type 2 diabetes and Parkinson's disease |
| CN107400151B (zh) * | 2016-11-18 | 2020-04-24 | 中国科学院西北高原生物研究所 | 一种斑唇马先蒿中六种抗氧化活性成份的筛选及分离方法 |
-
1975
- 1975-03-07 FR FR7507316A patent/FR2302745A1/fr active Granted
-
1976
- 1976-03-08 DE DE19762609533 patent/DE2609533C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2302745A1 (fr) | 1976-10-01 |
| FR2302745B1 (cg-RX-API-DMAC10.html) | 1978-08-04 |
| DE2609533A1 (de) | 1976-09-16 |
| DE2609533B2 (de) | 1980-02-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69927125T2 (de) | Zusammensetzung gegen Erhöhung oder zur Herabsetzung des Blutzuckerspiegels | |
| DE69317494T2 (de) | Zusammensetzungen, die mono oder polyhydroxylierte Aminosäuren zur Behandlung des Insulinunabhängigen Diabetes Mellitus enthalten | |
| DE60109938T2 (de) | Zusammenstellungen die aktive stilbenoidverbindungen enthalten zur senkung des triglyceridspiegels | |
| DE69830578T2 (de) | Forskolin zur entwicklung magerer körpermasse | |
| DE60110438T2 (de) | Zusammensetzungen enthaltend stilbenoide mit einer hypoglykämischen wirkung | |
| US5674900A (en) | Terpenoid-type quinones for treatment of diabetes | |
| DE69633345T2 (de) | Verfahren zur herstellung von rg3 und rg5 ginsenosiden | |
| DE69705159T2 (de) | Verfahren zur Extrahierung von polyphenolischen Verbindungen von Catechin-Typ aus pflanzenartigen Quellen, die erhaltene Extrakte und deren Verwendung | |
| DE3511609C2 (cg-RX-API-DMAC10.html) | ||
| CH647534A5 (de) | Cyclodextrin-kamillen-inklusionskomplexe, verfahren zur herstellung der komplexe und die komplexe enthaltenden praeparate. | |
| DE3603576A1 (de) | Verwendung von gerbstoffen und/oder chlorogensaeure sowie nahrungs-, genuss- und/oder arzneimittel mit gerbstoff- und/oder chlorogensaeurezusatz | |
| DE3014045A1 (de) | Fuer kosmetische zwecke verwendbare praeparate und verfahren zur herstellung der wirkstoffe dieser praeparate | |
| Gharaibeh et al. | Anorexic effect of Teucrium polium in rats | |
| DE60308045T2 (de) | Pflanzenextrakte aus argyrolobium roseum zur behandlung von diabetes | |
| DE2817133C2 (cg-RX-API-DMAC10.html) | ||
| DE2609533C3 (de) | Verfahren zur Extraktion von Wirkstoffen, insbesondere von Heterosidestern der Kaffeesäure, sowie diese Verbindungen enthaltende Arzneimittel | |
| DE1467800A1 (de) | Verfahren zur Behandlung von insbesondere saponinhaltigen Pflanzen | |
| CH621333A5 (cg-RX-API-DMAC10.html) | ||
| DE60215060T2 (de) | Kräuterpräparat zur behandlung von herz-kreislauf- sowie neurologischen erkrankungen | |
| DE2656602A1 (de) | 2-hydroxymethyl-3,4,5-trihydroxypiperidin, extraktionsverfahren zu seiner herstellung und seine verwendung als arzneimittel | |
| DE4102054A1 (de) | Verwendung der pflanze euphorbia hirta l. und ihrer extrakte sowie ihrer wirkstoffe | |
| EP2793917B1 (de) | Extrakt aus rhus copallina zur verwendung als arzneimittel | |
| DE2659465C2 (de) | Pflanzliche Wirkstoffextrakte aus Hypoxidaceen und ihre Anwendung | |
| AT282055B (de) | Verfahren zur Herstellung neuer Valepotriate | |
| DE3546505C2 (cg-RX-API-DMAC10.html) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |