BE528006A - - Google Patents
Info
- Publication number
- BE528006A BE528006A BE528006DA BE528006A BE 528006 A BE528006 A BE 528006A BE 528006D A BE528006D A BE 528006DA BE 528006 A BE528006 A BE 528006A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- alkaloids
- solution
- mycelium
- ergot
- Prior art date
Links
- 229930013930 alkaloids Natural products 0.000 claims description 53
- 241000221751 Claviceps purpurea Species 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 10
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 claims 432
- 239000000243 solution Substances 0.000 claims 42
- 229910001868 water Inorganic materials 0.000 claims 40
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 24
- 235000015097 nutrients Nutrition 0.000 claims 22
- 229960004943 Ergotamine Drugs 0.000 claims 21
- OFKDAAIKGIBASY-VFGNJEKYSA-N Ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 claims 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 20
- 150000003797 alkaloid derivatives Chemical class 0.000 claims 19
- 239000000126 substance Substances 0.000 claims 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 11
- WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 claims 10
- 238000006243 chemical reaction Methods 0.000 claims 10
- 239000000284 extract Substances 0.000 claims 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 239000003960 organic solvent Substances 0.000 claims 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 8
- 239000011701 zinc Substances 0.000 claims 8
- 229910052725 zinc Inorganic materials 0.000 claims 8
- 229940083253 Ergot alkaloid peripheral vasodilators Drugs 0.000 claims 7
- 229940051869 antimigraine Ergot alkaloids Drugs 0.000 claims 7
- 230000000295 complement Effects 0.000 claims 7
- 229960003133 ergot alkaloids Drugs 0.000 claims 7
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- 239000007864 aqueous solution Substances 0.000 claims 6
- 238000000338 in vitro Methods 0.000 claims 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 6
- 229910052742 iron Inorganic materials 0.000 claims 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 238000004587 chromatography analysis Methods 0.000 claims 5
- 238000001704 evaporation Methods 0.000 claims 5
- 239000007788 liquid Substances 0.000 claims 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 5
- 229960001367 tartaric acid Drugs 0.000 claims 5
- 235000002906 tartaric acid Nutrition 0.000 claims 5
- 239000011975 tartaric acid Substances 0.000 claims 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 4
- 241000221760 Claviceps Species 0.000 claims 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 4
- DCXYFEDJOCDNAF-UHFFFAOYSA-N DL-asparagine Chemical compound OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 4
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims 4
- 229960002685 biotin Drugs 0.000 claims 4
- 235000020958 biotin Nutrition 0.000 claims 4
- 239000011616 biotin Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 235000018417 cysteine Nutrition 0.000 claims 4
- 238000000354 decomposition reaction Methods 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 4
- 238000002844 melting Methods 0.000 claims 4
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 4
- 230000003287 optical Effects 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 4
- 235000011152 sodium sulphate Nutrition 0.000 claims 4
- 238000003756 stirring Methods 0.000 claims 4
- 239000005720 sucrose Substances 0.000 claims 4
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims 4
- 235000019157 thiamine Nutrition 0.000 claims 4
- 239000011721 thiamine Substances 0.000 claims 4
- 229910000368 zinc sulfate Inorganic materials 0.000 claims 4
- BGNGWHSBYQYVRX-UHFFFAOYSA-N Para-Dimethylaminobenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims 3
- 238000004458 analytical method Methods 0.000 claims 3
- 238000004364 calculation method Methods 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 238000004737 colorimetric analysis Methods 0.000 claims 3
- 238000002425 crystallisation Methods 0.000 claims 3
- 230000005712 crystallization Effects 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 238000002955 isolation Methods 0.000 claims 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000463 material Substances 0.000 claims 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 3
- 239000001187 sodium carbonate Substances 0.000 claims 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 3
- WVVSZNPYNCNODU-CJBNDPTMSA-N Ergometrine Natural products C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-CJBNDPTMSA-N 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L Iron(II) sulfate Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims 2
- YDOTUXAWKBPQJW-VQZFRJCTSA-N Isoergokryptine Chemical compound C1=CC(C=2[C@@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-VQZFRJCTSA-N 0.000 claims 2
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims 2
- 210000004291 Uterus Anatomy 0.000 claims 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N Vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims 2
- 239000006286 aqueous extract Substances 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000010828 elution Methods 0.000 claims 2
- 229960001405 ergometrine Drugs 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 229960001340 histamine Drugs 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- -1 iron ions Chemical class 0.000 claims 2
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 claims 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000003208 petroleum Substances 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims 2
- 210000004215 spores Anatomy 0.000 claims 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 2
- UPKBEIIDYOMDQW-UKRRQHHQSA-N Agroclavine Chemical compound C1=CC=C2[C@H]3C=C(C)CN(C)[C@@H]3CC3=CN=C1[C]32 UPKBEIIDYOMDQW-UKRRQHHQSA-N 0.000 claims 1
- 241000931365 Ampelodesmos mauritanicus Species 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 210000001772 Blood Platelets Anatomy 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 240000000218 Cannabis sativa Species 0.000 claims 1
- 241000700199 Cavia porcellus Species 0.000 claims 1
- 241000219760 Cytisus scoparius Species 0.000 claims 1
- XLMJRFCCCWFQRE-SJRQCXNHSA-N Ecboline Chemical compound C([C@H]1[C@]2(O)O3)CCN1C(=O)CN2C(=O)[C@]3(C(C)C)NC(=O)[C@@H](CN(C)[C@@H]1C2)C=C1C1=C3C2=CNC3=CC=C1 XLMJRFCCCWFQRE-SJRQCXNHSA-N 0.000 claims 1
- IAOSEBXZNXDPEE-UKRRQHHQSA-N Elymoclavine Chemical compound C1=CC=C2[C@H]3C=C(CO)CN(C)[C@@H]3CC3=CN=C1[C]32 IAOSEBXZNXDPEE-UKRRQHHQSA-N 0.000 claims 1
- 239000007836 KH2PO4 Substances 0.000 claims 1
- 241001074441 Leymus mollis Species 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M Monopotassium phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 claims 1
- 241000209504 Poaceae Species 0.000 claims 1
- 235000010495 Sarothamnus scoparius Nutrition 0.000 claims 1
- 241000209056 Secale Species 0.000 claims 1
- 235000007238 Secale cereale Nutrition 0.000 claims 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L Zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 229950001817 alpha-Ergocryptine Drugs 0.000 claims 1
- NHJPVZLSLOHJDM-UHFFFAOYSA-N azane;butanedioic acid Chemical compound [NH4+].[NH4+].[O-]C(=O)CCC([O-])=O NHJPVZLSLOHJDM-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 230000001809 detectable Effects 0.000 claims 1
- 230000002196 ecbolic Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 claims 1
- YREISLCRUMOYAY-IIPCNOPRSA-N ergometrine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 YREISLCRUMOYAY-IIPCNOPRSA-N 0.000 claims 1
- 230000001747 exhibiting Effects 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 238000003306 harvesting Methods 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 235000019796 monopotassium phosphate Nutrition 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- 230000001264 neutralization Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 235000008935 nutritious Nutrition 0.000 claims 1
- 244000045947 parasites Species 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000002250 progressing Effects 0.000 claims 1
- 230000005180 public health Effects 0.000 claims 1
- 229910052904 quartz Inorganic materials 0.000 claims 1
- 239000010453 quartz Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 210000001519 tissues Anatomy 0.000 claims 1
- 229960003732 tyramine Drugs 0.000 claims 1
- 229940117960 vanillin Drugs 0.000 claims 1
- 235000012141 vanillin Nutrition 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
- 239000011686 zinc sulphate Substances 0.000 claims 1
- 235000009529 zinc sulphate Nutrition 0.000 claims 1
- YDOTUXAWKBPQJW-NSLWYYNWSA-N α-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
- C12P17/183—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system containing an indolo[4,3-F,G]quinoleine nucleus, e.g. compound containing the lysergic acid nucleus as well as the dimeric ergot nucleus
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE528006A true BE528006A (xx) |
Family
ID=161450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE528006D BE528006A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE528006A (xx) |
-
0
- BE BE528006D patent/BE528006A/fr unknown
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