CA1060891A - Vincadioline - Google Patents
VincadiolineInfo
- Publication number
- CA1060891A CA1060891A CA225,299A CA225299A CA1060891A CA 1060891 A CA1060891 A CA 1060891A CA 225299 A CA225299 A CA 225299A CA 1060891 A CA1060891 A CA 1060891A
- Authority
- CA
- Canada
- Prior art keywords
- alkaloid
- extracting
- aqueous
- vincadioline
- water
- 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
- IFGMHVGAHYXLIZ-UHFFFAOYSA-N methyl 11-acetyloxy-12-ethyl-4-(17-ethyl-16,17-dihydroxy-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 OC1C(CC)(O)CN(CCC=2C3=CC=CC=C3NC=22)CC1CC2(C(=O)OC)C1=CC(C23C(C(C(OC(C)=O)C4(CC)C=CCN(C34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC IFGMHVGAHYXLIZ-UHFFFAOYSA-N 0.000 title claims abstract description 28
- CTODJDOCNIIUTR-UHFFFAOYSA-N Vincadioline Natural products CCC1(O)CC2CN(CCc3c([nH]c4ccccc34)C(C2)(C(=O)OC)c5cc6c(cc5OC)N(C)C7(O)C(O)(C(OC(=O)C)C8(CC)C=CCN9CCC67C89)C(=O)OC)C1 CTODJDOCNIIUTR-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229930013930 alkaloid Natural products 0.000 claims abstract description 49
- 150000003797 alkaloid derivatives Chemical class 0.000 claims abstract description 23
- 239000000284 extract Substances 0.000 claims abstract description 18
- 240000001829 Catharanthus roseus Species 0.000 claims abstract description 9
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000010410 layer Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkaloid sulfate salt Chemical class 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 238000001228 spectrum Methods 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 238000002270 exclusion chromatography Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000012062 aqueous buffer Substances 0.000 claims 2
- 238000004458 analytical method Methods 0.000 claims 1
- 229930005303 indole alkaloid Natural products 0.000 claims 1
- UKTNDLHXQNQKBH-UHFFFAOYSA-N 2,3-dihydro-1h-indole;1h-indole Chemical class C1=CC=C2NCCC2=C1.C1=CC=C2NC=CC2=C1 UKTNDLHXQNQKBH-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002927 anti-mitotic effect Effects 0.000 abstract description 2
- 230000001376 precipitating effect Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 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 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229960003048 vinblastine Drugs 0.000 description 12
- 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 description 12
- 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 description 10
- 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 description 9
- 229960004528 vincristine Drugs 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 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 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine 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-CFWMRBGOSA-N 0.000 description 6
- JXLYSJRDGCGARV-KSNABSRWSA-N ac1l29ym 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-KSNABSRWSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 230000031864 metaphase Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229950003670 vinrosidine Drugs 0.000 description 3
- JXLYSJRDGCGARV-PJXZDTQASA-N Leurosidine 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-PJXZDTQASA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 229940122803 Vinca alkaloid Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HETLRUWISYTARN-UHFFFAOYSA-N dichloromethane;ethyl acetate;hydrate Chemical compound O.ClCCl.CCOC(C)=O HETLRUWISYTARN-UHFFFAOYSA-N 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 230000036210 malignancy Effects 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000976924 Inca Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003080 antimitotic agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003976 antineoplastic alkaloid Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YCWXIQRLONXJLF-FOVAWKNMSA-N g7e5nu015t Chemical compound OS(O)(=O)=O.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.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 YCWXIQRLONXJLF-FOVAWKNMSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- GLDSBTCHEGZWCV-HLTPFJCJSA-N leuroformine 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=O)=C2C=C1OC GLDSBTCHEGZWCV-HLTPFJCJSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US466939A US3887565A (en) | 1974-05-06 | 1974-05-06 | Vincadioline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1060891A true CA1060891A (en) | 1979-08-21 |
Family
ID=23853659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,299A Expired CA1060891A (en) | 1974-05-06 | 1975-04-23 | Vincadioline |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3887565A (en, 2012) |
| JP (1) | JPS50154406A (en, 2012) |
| BE (1) | BE828211A (en, 2012) |
| CA (1) | CA1060891A (en, 2012) |
| CH (1) | CH613708A5 (en, 2012) |
| DE (1) | DE2519533A1 (en, 2012) |
| FR (1) | FR2269942B1 (en, 2012) |
| GB (1) | GB1503577A (en, 2012) |
| HU (1) | HU170135B (en, 2012) |
| IE (1) | IE40837B1 (en, 2012) |
| IL (1) | IL46877A (en, 2012) |
| NL (1) | NL7505348A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115388A (en) * | 1977-03-30 | 1978-09-19 | Eli Lilly And Company | 3'-Oxygenated derivatives of 4'-deoxy VLB "A" and "B" and related 1-formyl compounds |
| US4110330A (en) * | 1977-05-27 | 1978-08-29 | Eli Lilly And Company | 5'-Acetonylvincristine and related compounds |
| US4166810A (en) * | 1978-04-20 | 1979-09-04 | Eli Lilly And Company | Derivatives of 4-desacetyl VLB C-3 carboxyhydrazide |
| US6326402B1 (en) | 1998-08-12 | 2001-12-04 | Octamer, Inc. | Methods for treating viral infections using a compound capable of inhibiting microtubules |
| EP2266607A3 (en) | 1999-10-01 | 2011-04-20 | Immunogen, Inc. | Immunoconjugates for treating cancer |
| US8858953B2 (en) * | 2011-05-09 | 2014-10-14 | Yu-Hwa Peter Sheng | Herbal composition for treating cancer |
-
1974
- 1974-05-06 US US466939A patent/US3887565A/en not_active Expired - Lifetime
-
1975
- 1975-03-18 IE IE585/75A patent/IE40837B1/xx unknown
- 1975-03-20 IL IL46877A patent/IL46877A/en unknown
- 1975-04-21 JP JP50048559A patent/JPS50154406A/ja active Pending
- 1975-04-22 BE BE1006605A patent/BE828211A/xx unknown
- 1975-04-22 FR FR7512531A patent/FR2269942B1/fr not_active Expired
- 1975-04-23 CA CA225,299A patent/CA1060891A/en not_active Expired
- 1975-04-29 CH CH546475A patent/CH613708A5/xx not_active IP Right Cessation
- 1975-05-02 GB GB18323/75A patent/GB1503577A/en not_active Expired
- 1975-05-02 DE DE19752519533 patent/DE2519533A1/de not_active Withdrawn
- 1975-05-05 HU HUEI616A patent/HU170135B/hu unknown
- 1975-05-06 NL NL7505348A patent/NL7505348A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HU170135B (en, 2012) | 1977-04-28 |
| IL46877A0 (en) | 1975-05-22 |
| IE40837B1 (en) | 1979-08-29 |
| IE40837L (en) | 1975-11-06 |
| GB1503577A (en) | 1978-03-15 |
| FR2269942A1 (en, 2012) | 1975-12-05 |
| NL7505348A (nl) | 1975-11-10 |
| CH613708A5 (en, 2012) | 1979-10-15 |
| FR2269942B1 (en, 2012) | 1978-08-04 |
| US3887565A (en) | 1975-06-03 |
| JPS50154406A (en, 2012) | 1975-12-12 |
| BE828211A (fr) | 1975-10-22 |
| IL46877A (en) | 1977-12-30 |
| DE2519533A1 (de) | 1975-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kupchan et al. | Isolation and structural elucidation of allamandin, and antileukemic iridoid lactone from Allamanda cathartica | |
| US3803124A (en) | Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives | |
| Ghosal et al. | Alkaloids of Crinum latifolium | |
| CA1060891A (en) | Vincadioline | |
| US3944554A (en) | 4-Desacetoxy-3-hydroxyvinblastine | |
| US4172077A (en) | Process for the isolation of alkaloid components from the plant Vinca Rosea L. | |
| Lyle et al. | The Alkaloids of Nerine bowdenii W. Wats. and Crinum moorei JD Hook. | |
| US3370057A (en) | Leurosine | |
| US3225030A (en) | Method of preparing leurosine and vincaleukoblastine | |
| US4749787A (en) | Process of isolating vinblastine from the plant catharanthis roseus | |
| US3890325A (en) | Leurocolombine | |
| Harken et al. | Interconversions in the pluviine-lycorenine series | |
| US3932417A (en) | Dimeric indole alkaloid purification process | |
| Burnell et al. | Alkaloids of Tabernaemontana psychotrifolia HBK | |
| US3954773A (en) | 4-Desacetoxyvinblastine | |
| US4189432A (en) | N-formyl and N-desmethyl leurosine derivatives | |
| Kutney et al. | Studies on natural products from Cuban plants. Alkaloids from Tabernaemontana citrifolia | |
| Martinez et al. | Alkaloids from Rauwolfia cubana stem bark | |
| EP1118616B1 (en) | Process for the production of 5'-nor-anhydrovinblastine ditartrate from plants of genus catharanthus | |
| Rolfsen et al. | New tertiary alkaloids of Strychnos decussata | |
| Dwuma-Badu et al. | Constituents of West African medicinal plants XXV. Isolation of oblongine from Tiliacora dinklagei and the synthesis of oblongine and related benzylisoquinoline alkaloids | |
| Mulchandani et al. | Physalin D, a New 13, 14–Seco–16, 24–Cyclo Steroid from Physalis minima | |
| US4078145A (en) | Phytoquinoid possessing anti-tumor activity | |
| CA1061785A (en) | Acid and ester derivatives of vinblastine, vincristine and leurosidine | |
| El Moghazi et al. | Investigation of the alkaloidal constituents of Crinum bulbispermum |