CA1090781A - Chrysanthellum plant extract - Google Patents
Chrysanthellum plant extractInfo
- Publication number
- CA1090781A CA1090781A CA294,559A CA294559A CA1090781A CA 1090781 A CA1090781 A CA 1090781A CA 294559 A CA294559 A CA 294559A CA 1090781 A CA1090781 A CA 1090781A
- Authority
- CA
- Canada
- Prior art keywords
- extract
- chrysanthellum
- plant
- organic solvent
- whenever prepared
- 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
- 241000020085 Chrysanthellum Species 0.000 title claims abstract description 26
- 239000000419 plant extract Substances 0.000 title claims abstract description 8
- 239000000284 extract Substances 0.000 claims abstract description 42
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims abstract description 12
- YKOPWPOFWMYZJZ-FMMUPTMQSA-N Echinocystic acid Natural products C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)C[C@H](O)[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C YKOPWPOFWMYZJZ-FMMUPTMQSA-N 0.000 claims abstract description 10
- YKOPWPOFWMYZJZ-UHFFFAOYSA-N Echinocystsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CC(O)C5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C YKOPWPOFWMYZJZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- FHICGHSMIPIAPL-HDYAAECPSA-N [2-[3-[6-[3-[(5R,6aS,6bR,12aR)-10-[6-[2-[2-[4,5-dihydroxy-3-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]ethoxy]ethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carbonyl]peroxypropyl]-5-[[5-[8-[3,5-dihydroxy-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]octoxy]-3,4-dihydroxy-6-methyloxan-2-yl]methoxy]-3,4-dihydroxyoxan-2-yl]propoxymethyl]-5-hydroxy-3-[(6S)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]oxy-6-methyloxan-4-yl] (2E,6S)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoate Chemical compound C=C[C@@](C)(O)CCC=C(C)C(=O)OC1C(OC(=O)C(\CO)=C\CC[C@](C)(O)C=C)C(O)C(C)OC1COCCCC1C(O)C(O)C(OCC2C(C(O)C(OCCCCCCCCC3C(C(OC4C(C(O)C(O)CO4)O)C(O)CO3)O)C(C)O2)O)C(CCCOOC(=O)C23C(CC(C)(C)CC2)C=2[C@@]([C@]4(C)CCC5C(C)(C)C(OC6C(C(O)C(O)C(CCOCCC7C(C(O)C(O)CO7)OC7C(C(O)C(O)CO7)O)O6)O)CC[C@]5(C)C4CC=2)(C)C[C@H]3O)O1 FHICGHSMIPIAPL-HDYAAECPSA-N 0.000 claims abstract description 8
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 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 abstract 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 abstract 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 abstract description 6
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims abstract description 6
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 6
- 239000008103 glucose Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002244 precipitate Substances 0.000 claims description 11
- 241000196324 Embryophyta Species 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003495 polar organic solvent Substances 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 6
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 6
- 235000000346 sugar Nutrition 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- KVIPHDKUOLVVQN-UHFFFAOYSA-N ethene;hydrate Chemical compound O.C=C KVIPHDKUOLVVQN-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 16
- 230000000144 pharmacologic effect Effects 0.000 abstract description 6
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 230000000767 anti-ulcer Effects 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 4
- 229930182470 glycoside Natural products 0.000 abstract description 2
- 150000002338 glycosides Chemical class 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- 206010030113 Oedema Diseases 0.000 description 7
- 238000007912 intraperitoneal administration Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000700157 Rattus norvegicus Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- 239000000679 carrageenan Substances 0.000 description 5
- 229940113118 carrageenan Drugs 0.000 description 5
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 5
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 description 5
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000004856 capillary permeability Effects 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- MCHWKJRTMPIHRA-UHFFFAOYSA-N n-(pyrrolidin-2-ylmethyl)aniline Chemical compound C1CCNC1CNC1=CC=CC=C1 MCHWKJRTMPIHRA-UHFFFAOYSA-N 0.000 description 4
- 230000010412 perfusion Effects 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 3
- 238000000611 regression analysis Methods 0.000 description 3
- 229930182490 saponin Natural products 0.000 description 3
- 150000007949 saponins Chemical class 0.000 description 3
- 235000017709 saponins Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003648 triterpenes Chemical class 0.000 description 3
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 2
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 229940117173 croton oil Drugs 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- 231100000021 irritant Toxicity 0.000 description 2
- 231100000682 maximum tolerated dose Toxicity 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QGPZXNSBZMHHSR-UHFFFAOYSA-N 2-carboxybenzoate;phenylazanium Chemical compound NC1=CC=CC=C1.OC(=O)C1=CC=CC=C1C(O)=O QGPZXNSBZMHHSR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010057267 Periphlebitis Diseases 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- 206010038669 Respiratory arrest Diseases 0.000 description 1
- 206010046996 Varicose vein Diseases 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- -1 aliphatic ester Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000037037 animal physiology Effects 0.000 description 1
- 239000008430 aponin Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 210000001630 jejunum Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 231100000668 minimum lethal dose Toxicity 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 208000001297 phlebitis Diseases 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000037039 plant physiology Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229930002600 steroidal saponin Natural products 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229930182493 triterpene saponin Natural products 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 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
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)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7701488A FR2378044A1 (fr) | 1977-01-20 | 1977-01-20 | Nouvel extrait vegetal a partir de varietes de chrysanthellum |
| FR7701488 | 1977-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1090781A true CA1090781A (en) | 1980-12-02 |
Family
ID=9185685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,559A Expired CA1090781A (en) | 1977-01-20 | 1978-01-09 | Chrysanthellum plant extract |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4146615A (en:Method) |
| BE (1) | BE862852A (en:Method) |
| CA (1) | CA1090781A (en:Method) |
| CH (1) | CH630528A5 (en:Method) |
| DE (1) | DE2801186A1 (en:Method) |
| ES (1) | ES466222A1 (en:Method) |
| FR (1) | FR2378044A1 (en:Method) |
| NL (1) | NL7800030A (en:Method) |
| OA (1) | OA05861A (en:Method) |
| PT (1) | PT67534B (en:Method) |
| ZA (1) | ZA78300B (en:Method) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2456116A1 (fr) * | 1979-05-11 | 1980-12-05 | Sarget Lab | Nouvelle saponine triterpenique derivee de la caulophyllogenine et ses applications therapeutiques |
| US4501734A (en) * | 1981-03-06 | 1985-02-26 | Wakunaga Yakuhin Kabushiki Kaisha | Promotion of absorption of drugs administered through the alimentary system |
| JPS5857400A (ja) * | 1981-09-30 | 1983-04-05 | Wakunaga Yakuhin Kk | 薬物吸収補助剤 |
| JPS58152817A (ja) * | 1982-03-08 | 1983-09-10 | Wakunaga Yakuhin Kk | 薬物吸収補助剤 |
| FR2579907A1 (en) * | 1985-04-09 | 1986-10-10 | Couderc Pierre | Method for enriching chrysantellum with active ingredients by physical processes |
| FR2618071B1 (fr) * | 1987-07-17 | 1991-05-24 | Guillot Bernard | Compositions cosmetiques et dermatologiques a base d'extraits de chrysanthellum |
| NL8900652A (nl) * | 1989-03-16 | 1990-10-16 | Leti Lab | Primair-toxische stoffen of allergenen, isoleerbaar uit plantaardig materiaal, alsmede werkwijzen ter bereiding ervan en de toepassing ervan. |
| JPH07583B2 (ja) * | 1990-11-21 | 1995-01-11 | 北海道糖業株式会社 | 水溶性五環性トリテルペン包接化合物及びその製造方法並びにそれを利用した食品、飲料、口腔用組成物 |
| FR2755609B1 (fr) * | 1996-11-14 | 1998-12-24 | Lanatech | Composition pour la prevention du vieillissement cutane |
| WO1998055497A1 (en) * | 1997-06-04 | 1998-12-10 | Cornell Research Foundation, Inc. | Betulinol derivatives |
| US20060148732A1 (en) | 2000-11-17 | 2006-07-06 | Gutterman Jordan U | Inhibition of NF-kappaB by triterpene compositions |
| FR2842109B1 (fr) * | 2002-07-11 | 2007-06-08 | Sicobel Lab | Utilisation d'un extrait de chrysanthellum |
| US20050042233A1 (en) * | 2003-08-21 | 2005-02-24 | Christopher Marrs | Stabilized compositions containing an oxygen-labile active agent and a fungal extract |
| US20050042306A1 (en) * | 2003-08-21 | 2005-02-24 | Christopher Marrs | Stabilized compositions containing an oxygen-labile active agent |
| WO2005112929A2 (en) * | 2004-05-20 | 2005-12-01 | Cornell Research Foundation, Inc. | Anti-hiv-1 activity of betulinol derivatives |
| EP2289485A1 (en) * | 2009-08-31 | 2011-03-02 | Cognis IP Management GmbH | Cosmetic compositions comprising Manilkara multinervis and extracts thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2096902A1 (en) * | 1970-07-15 | 1972-03-03 | Couderc Pierre | Aqs alcoholic extract of chrysanthellum americanum vatke - - active in intestinal disorders |
| FR2276060A1 (fr) * | 1974-06-27 | 1976-01-23 | Cortial | Procede de purification d'extraits de chrysanthellum et produits en resultant |
-
1977
- 1977-01-20 FR FR7701488A patent/FR2378044A1/fr active Granted
-
1978
- 1978-01-02 NL NL7800030A patent/NL7800030A/xx not_active Application Discontinuation
- 1978-01-09 CA CA294,559A patent/CA1090781A/en not_active Expired
- 1978-01-12 DE DE19782801186 patent/DE2801186A1/de active Granted
- 1978-01-12 BE BE184267A patent/BE862852A/xx unknown
- 1978-01-12 CH CH33078A patent/CH630528A5/fr not_active IP Right Cessation
- 1978-01-16 PT PT67534A patent/PT67534B/pt unknown
- 1978-01-17 ZA ZA00780300A patent/ZA78300B/xx unknown
- 1978-01-19 US US05/870,649 patent/US4146615A/en not_active Expired - Lifetime
- 1978-01-19 OA OA56382A patent/OA05861A/xx unknown
- 1978-01-20 ES ES466222A patent/ES466222A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7800030A (nl) | 1978-07-24 |
| ES466222A1 (es) | 1978-10-16 |
| CH630528A5 (fr) | 1982-06-30 |
| US4146615A (en) | 1979-03-27 |
| PT67534A (fr) | 1978-02-01 |
| DE2801186C2 (en:Method) | 1989-04-13 |
| BE862852A (fr) | 1978-05-02 |
| OA05861A (fr) | 1981-05-31 |
| ZA78300B (en) | 1979-02-28 |
| FR2378044A1 (fr) | 1978-08-18 |
| DE2801186A1 (de) | 1978-07-27 |
| FR2378044B1 (en:Method) | 1979-05-11 |
| PT67534B (fr) | 1979-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1090781A (en) | Chrysanthellum plant extract | |
| Thomas et al. | Anti-inflammatory actions of tannins isolated from the bark of Anacardwm occidentale L | |
| Diallo et al. | Polysaccharides from the roots of Entada africana Guill. et Perr., Mimosaceae, with complement fixing activity | |
| Funayama et al. | Hypotensive principles of Diospyros kaki leaves | |
| CN104688782B (zh) | 一种从茯苓皮中高效提取三萜类活性成分的方法 | |
| Speroni et al. | Effects of differential extraction of Verbena officinalis on rat models of inflammation, cicatrization and gastric damage | |
| CA1148936A (en) | Triterpenic saponin having pharmacological potency | |
| JP2006515290A (ja) | ウィタニアソムニフェラ組成物、それを得るための方法、並びにその医薬製剤、栄養剤およびパーソナルケア製剤 | |
| EP1848449A2 (en) | Bioactive complex of triterpene acids, its production process and medicinal products with therapeutical uses | |
| JP2019509332A (ja) | バイカリンマグネシウム化合物、その製造方法及び使用 | |
| CN103804443A (zh) | 黄酮苷类化合物及其制备方法 | |
| CN104644882A (zh) | 一种含苯乙醇苷的裸花紫珠提取物及其制备方法 | |
| Yang et al. | Structural identification and anti-neuroinflammatory effects of a pectin–arabinoglucuronogalactan complex, AOPB-1-1, isolated from Asparagus officinalis | |
| CN108101955A (zh) | 文冠果果壳中的化合物及其制备方法和用途 | |
| US3551408A (en) | Triterpene derivatives,process for preparing same,and applications thereof | |
| Ahmed et al. | A contribution to the chemistry and toxicology of the root of Pbytolacca americana, L. | |
| Koca et al. | Evaluation of in vivo and in vitro biological activities of different extracts of Cuscuta arvensis | |
| Gujral et al. | Antiarthritic activity of Glycyrrhiza glabra Linn | |
| El-Moghazy et al. | Chemical constituents of ornamental pomegranate and its antioxidant and anti-inflammatory activities in comparison with edible pomegranate | |
| Muhamad Ibrahim et al. | Swertiamarin ointment: a traditional approach in cutaneous wound healing | |
| JURD | The sterol and carbohydrate constituents of the walnut (Juglans regia) | |
| KR20030091405A (ko) | 해동피의 에틸아세테이트 가용추출물 및 그로부터 분리된칼로파낙스 사포닌 에이 유도체를 포함하는 관절염 예방및 치료용 조성물 | |
| Mahran et al. | Isolation and quantitative estimation of plumierid from the different organs of Plumeria rubra and Plumeria rubra var. alba | |
| KR0137422B1 (ko) | 아랄로사이드 a를 유효 성분으로 하는 위장 질환 치료제 | |
| EP2649991B1 (en) | Extracts and isolated compounds from Euphorbia granulata Forrsk. for treatment of ulcerative colitis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |