SE437829B - Sett att isolera alkaloidkomponenter ur vinca rosea l - Google Patents
Sett att isolera alkaloidkomponenter ur vinca rosea lInfo
- Publication number
- SE437829B SE437829B SE7805900A SE7805900A SE437829B SE 437829 B SE437829 B SE 437829B SE 7805900 A SE7805900 A SE 7805900A SE 7805900 A SE7805900 A SE 7805900A SE 437829 B SE437829 B SE 437829B
- Authority
- SE
- Sweden
- Prior art keywords
- vinblastine
- leurosine
- mixture
- anhydrovinblastine
- catarantine
- Prior art date
Links
- 240000001829 Catharanthus roseus Species 0.000 title claims description 7
- 229930013930 alkaloid Natural products 0.000 title description 32
- 150000003797 alkaloid derivatives Chemical class 0.000 title description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- LPGWZGMPDKDHEP-GKWAKPNHSA-N Leurosine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@]6(CC)O[C@@H]6[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C LPGWZGMPDKDHEP-GKWAKPNHSA-N 0.000 claims description 39
- LPGWZGMPDKDHEP-HLTPFJCJSA-N Leurosine Chemical compound C([C@]1([C@@H]2O1)CC)N(CCC=1C3=CC=CC=C3NC=11)C[C@H]2C[C@]1(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC LPGWZGMPDKDHEP-HLTPFJCJSA-N 0.000 claims description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000284 extract Substances 0.000 claims description 24
- 239000012452 mother liquor Substances 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 19
- FFRFGVHNKJYNOV-DOVUUNBWSA-N 3',4'-Anhydrovinblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C=C(C2)CC)N2CCC2=C1NC1=CC=CC=C21 FFRFGVHNKJYNOV-DOVUUNBWSA-N 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 229960004528 vincristine Drugs 0.000 claims description 15
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 15
- WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 claims description 14
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 14
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229960003048 vinblastine Drugs 0.000 claims description 13
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 12
- GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 claims description 11
- 238000001704 evaporation Methods 0.000 claims description 11
- 230000008020 evaporation Effects 0.000 claims description 11
- CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 9
- OBEIXXHHUOSBLA-UQUCNHJPSA-N n-deformylvincristine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OBEIXXHHUOSBLA-UQUCNHJPSA-N 0.000 claims description 8
- 241000196324 Embryophyta Species 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 239000011833 salt mixture Substances 0.000 claims description 7
- LVINNLJJGRZGKQ-VMJLQBTBSA-N 4-Desacetoxyvinblastine Natural products CC[C@]1(O)C[C@@H]2CN(CC[C@H]3[C@@H](Nc4ccccc34)[C@@](C2)(C(=O)OC)c5cc6c(cc5OC)N(C)[C@H]7[C@](O)(C[C@]8(CC)C=CCN9CC[C@]67[C@H]89)C(=O)OC)C1 LVINNLJJGRZGKQ-VMJLQBTBSA-N 0.000 claims description 6
- -1 catarantine Chemical compound 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- OBMKRZCOTHZPOB-UDMDOTTKSA-N 4-desacetoxyvinblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@](C[C@@]6(C=CCN([C@H]56)CC4)CC)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OBMKRZCOTHZPOB-UDMDOTTKSA-N 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- NDMPLJNOPCLANR-PETVRERISA-N deacetylvinblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 NDMPLJNOPCLANR-PETVRERISA-N 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- SASWULSUPROHRT-MCIGMTSASA-N Vindorosine Natural products CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC=CC=C3[C@@]11CCN3CC=C[C@]2(CC)[C@@H]13 SASWULSUPROHRT-MCIGMTSASA-N 0.000 claims description 3
- CXBGOBGJHGGWIE-ACSXSLCXSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-ACSXSLCXSA-N 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 229950001104 anhydrovinblastine Drugs 0.000 description 7
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229910021653 sulphate ion Inorganic materials 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- RVCKCEDKBVEEHL-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzyl alcohol Chemical compound OCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl RVCKCEDKBVEEHL-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011426 transformation method Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- OBMKRZCOTHZPOB-NZSNZZHBSA-N methyl (1R,9R,10R,12R,19S)-12-ethyl-4-[(13S,15R,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate Chemical compound CC[C@]1(O)C[C@@H]2CN(C1)CCc1c([nH]c3ccccc13)[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N(C)[C@@H]1[C@]22CCN3CC=C[C@@](CC)(C[C@]1(O)C(=O)OC)[C@@H]23 OBMKRZCOTHZPOB-NZSNZZHBSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000004027 organic amino compounds Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 229940043266 rosin Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Extraction Or Liquid Replacement (AREA)
- Compounds Of Unknown Constitution (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77RI638A HU178084B (en) | 1977-05-31 | 1977-05-31 | New process for the extraction of native vindoline,catharantine,3',4'-anhydrovinblastine,leurosine and,if desired,of other diinodle alkaloids from vinca rosea l.drogue |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7805900L SE7805900L (sv) | 1978-12-01 |
| SE437829B true SE437829B (sv) | 1985-03-18 |
Family
ID=11001035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7805900A SE437829B (sv) | 1977-05-31 | 1978-05-23 | Sett att isolera alkaloidkomponenter ur vinca rosea l |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4172077A (de) |
| JP (1) | JPS5439100A (de) |
| AT (1) | AT364469B (de) |
| AU (1) | AU515713B2 (de) |
| BE (1) | BE867670A (de) |
| CA (1) | CA1094552A (de) |
| CH (1) | CH640861A5 (de) |
| DD (1) | DD136139A5 (de) |
| DE (1) | DE2823461A1 (de) |
| DK (1) | DK146765C (de) |
| FR (1) | FR2393002A1 (de) |
| GB (1) | GB1602633A (de) |
| HU (1) | HU178084B (de) |
| IL (1) | IL54761A (de) |
| IT (1) | IT1096605B (de) |
| NL (1) | NL7805881A (de) |
| SE (1) | SE437829B (de) |
| SU (1) | SU867313A3 (de) |
| YU (1) | YU129378A (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2296418B1 (de) * | 1974-12-30 | 1978-07-21 | Anvar | |
| FR2544318B1 (fr) * | 1983-04-14 | 1985-08-16 | Fabre Sa Pierre | Procede de preparation de vindoline et de catharanthine |
| US4778885A (en) * | 1986-09-18 | 1988-10-18 | Allelix Inc. | Production of alkaloid dimers using ferric ion |
| US4749787A (en) * | 1986-10-23 | 1988-06-07 | Harbor Branch Oceanographic Institution, Inc. | Process of isolating vinblastine from the plant catharanthis roseus |
| US4831133A (en) * | 1987-05-01 | 1989-05-16 | Allelix, Inc. | Extraction of alkaloids of Catharanthus roseus tissue |
| US5907044A (en) * | 1997-07-30 | 1999-05-25 | Degussa Aktiengellschaft | Method of isolating 1- N2 -((S)-ethoxycarbonyl)-3-phenylpropyl)-N6 -trifluoroacetyl!-L-lysyl-L-proline (lisinopril (TFA) ethyl ester, LPE) |
| AU5240999A (en) * | 1998-07-31 | 2000-02-21 | Goldsmith Seeds Inc. | Trimeric and polymeric alkaloids |
| CA2385528C (en) | 1999-10-01 | 2013-12-10 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| WO2005030237A1 (en) * | 2003-09-26 | 2005-04-07 | Señor Rafael Phil. Inc. | A pharmaceutical composition comprising catharanthus roseaus, (vinca rosea), its preparation and use thereof |
| CN100374446C (zh) * | 2005-12-19 | 2008-03-12 | 东北林业大学 | 一种从长春花中分离文多灵、长春质碱、长春碱和长春新碱的方法 |
| CN104262362B (zh) * | 2014-09-01 | 2017-02-15 | 海南希源化工科技有限公司 | 一种长春碱的提取及纯化方法 |
| CN104370910B (zh) * | 2014-12-13 | 2016-08-31 | 海南大学 | 一种文多林的提取及纯化方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097137A (en) * | 1960-05-19 | 1963-07-09 | Canadian Patents Dev | Vincaleukoblastine |
| US3205220A (en) * | 1961-10-26 | 1965-09-07 | Lilly Co Eli | Leurosidine and leurocristine and their production |
| US3392173A (en) * | 1964-03-09 | 1968-07-09 | Lilly Co Eli | Novel acyl derivatives of desacetyl-vincaleukoblastine and processes for their preparation |
| US3352868A (en) * | 1964-04-01 | 1967-11-14 | Lilly Co Eli | Dihydrovinblastine |
| US3370057A (en) * | 1964-04-27 | 1968-02-20 | Lilly Co Eli | Leurosine |
| US3225030A (en) * | 1965-02-15 | 1965-12-21 | Lilly Co Eli | Method of preparing leurosine and vincaleukoblastine |
| US3422112A (en) * | 1968-01-22 | 1969-01-14 | Lilly Co Eli | Indolyl vindolines |
| AT313485B (de) * | 1971-09-17 | 1974-02-25 | Richter Gedeon Vegyeszet | Verfahren zur selektiven Gewinnung von Vinblastin, Vinleurosin und Vinchristin oder deren Salzen |
| US3932417A (en) * | 1973-10-24 | 1976-01-13 | Eli Lilly And Company | Dimeric indole alkaloid purification process |
-
1977
- 1977-05-31 HU HU77RI638A patent/HU178084B/hu not_active IP Right Cessation
-
1978
- 1978-05-22 US US05/908,584 patent/US4172077A/en not_active Expired - Lifetime
- 1978-05-22 IL IL54761A patent/IL54761A/xx not_active IP Right Cessation
- 1978-05-23 SE SE7805900A patent/SE437829B/sv not_active IP Right Cessation
- 1978-05-26 CH CH580878A patent/CH640861A5/de not_active IP Right Cessation
- 1978-05-30 AU AU36649/78A patent/AU515713B2/en not_active Expired
- 1978-05-30 AT AT0391578A patent/AT364469B/de not_active IP Right Cessation
- 1978-05-30 NL NL7805881A patent/NL7805881A/xx not_active Application Discontinuation
- 1978-05-30 CA CA304,370A patent/CA1094552A/en not_active Expired
- 1978-05-30 DD DD78205659A patent/DD136139A5/de unknown
- 1978-05-30 GB GB24214/78A patent/GB1602633A/en not_active Expired
- 1978-05-30 DE DE19782823461 patent/DE2823461A1/de not_active Ceased
- 1978-05-30 YU YU01293/78A patent/YU129378A/xx unknown
- 1978-05-30 FR FR7816106A patent/FR2393002A1/fr active Granted
- 1978-05-30 DK DK239178A patent/DK146765C/da not_active IP Right Cessation
- 1978-05-30 SU SU782621102A patent/SU867313A3/ru active
- 1978-05-31 BE BE188205A patent/BE867670A/xx not_active IP Right Cessation
- 1978-05-31 IT IT24055/78A patent/IT1096605B/it active
- 1978-05-31 JP JP6443378A patent/JPS5439100A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5439100A (en) | 1979-03-24 |
| NL7805881A (nl) | 1978-12-04 |
| GB1602633A (en) | 1981-11-11 |
| ATA391578A (de) | 1981-03-15 |
| IL54761A0 (en) | 1978-07-31 |
| HU178084B (en) | 1982-03-28 |
| IL54761A (en) | 1981-09-13 |
| AU3664978A (en) | 1979-12-06 |
| FR2393002A1 (fr) | 1978-12-29 |
| FR2393002B1 (de) | 1983-05-20 |
| DE2823461A1 (de) | 1978-12-14 |
| US4172077A (en) | 1979-10-23 |
| DK239178A (da) | 1978-12-01 |
| SE7805900L (sv) | 1978-12-01 |
| CH640861A5 (de) | 1984-01-31 |
| YU129378A (en) | 1983-10-31 |
| DD136139A5 (de) | 1979-06-20 |
| BE867670A (fr) | 1978-09-18 |
| DK146765C (da) | 1984-06-04 |
| IT7824055A0 (it) | 1978-05-31 |
| CA1094552A (en) | 1981-01-27 |
| AT364469B (de) | 1981-10-27 |
| AU515713B2 (en) | 1981-04-16 |
| SU867313A3 (ru) | 1981-09-23 |
| DK146765B (da) | 1983-12-27 |
| IT1096605B (it) | 1985-08-26 |
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