UA81085C2 - Process for isolation of ergot alkaloids from ergot (variants) - Google Patents
Process for isolation of ergot alkaloids from ergot (variants) Download PDFInfo
- Publication number
- UA81085C2 UA81085C2 UAA200610038A UAA200610038A UA81085C2 UA 81085 C2 UA81085 C2 UA 81085C2 UA A200610038 A UAA200610038 A UA A200610038A UA A200610038 A UAA200610038 A UA A200610038A UA 81085 C2 UA81085 C2 UA 81085C2
- Authority
- UA
- Ukraine
- Prior art keywords
- toluene
- extract
- alkaloid
- extraction
- aqueous
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000002955 isolation Methods 0.000 title claims description 10
- 229960003133 ergot alkaloid Drugs 0.000 title abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 103
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 229930013930 alkaloid Natural products 0.000 claims abstract description 52
- 239000000284 extract Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000012485 toluene extract Substances 0.000 claims abstract description 21
- 238000002425 crystallisation Methods 0.000 claims abstract description 10
- 230000008025 crystallization Effects 0.000 claims abstract description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 22
- 238000000605 extraction Methods 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 240000004385 Centaurea cyanus Species 0.000 claims description 20
- 235000005940 Centaurea cyanus Nutrition 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 20
- 239000006286 aqueous extract Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 9
- 230000008020 evaporation Effects 0.000 claims description 9
- 239000011260 aqueous acid Substances 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 239000012141 concentrate Substances 0.000 claims 2
- 241000256856 Vespidae Species 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 abstract description 8
- 238000000622 liquid--liquid extraction Methods 0.000 abstract description 7
- 241000221751 Claviceps purpurea Species 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- 229960004943 ergotamine Drugs 0.000 description 7
- 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 description 7
- XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OWEUDBYTKOYTAD-MKTPKCENSA-N ergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@@H]1C=C2C3=CC=CC4=NC=C([C]34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 OWEUDBYTKOYTAD-MKTPKCENSA-N 0.000 description 6
- HEFIYUQVAZFDEE-UHFFFAOYSA-N ergocristinine Natural products N12C(=O)C(C(C)C)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 HEFIYUQVAZFDEE-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- XLMJRFCCCWFQRE-SJRQCXNHSA-N ecboline Chemical class 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 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 208000003643 Callosities Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- LIMAOLZSWRJOMG-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C(C)C)C1=CC=CC=C1 LIMAOLZSWRJOMG-HJPBWRTMSA-N 0.000 description 1
- 229960004318 dihydroergocristine Drugs 0.000 description 1
- 229960004704 dihydroergotamine Drugs 0.000 description 1
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine 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]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 229930015720 peptide alkaloid Natural products 0.000 description 1
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
- 229960004851 pergolide Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 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
-
- 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
- C07D519/02—Ergot alkaloids of the cyclic peptide type
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G5/00—Alkaloids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Extraction Or Liquid Replacement (AREA)
- Medicines Containing Plant Substances (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54656104P | 2004-02-20 | 2004-02-20 | |
| PCT/US2005/005059 WO2005082910A1 (en) | 2004-02-20 | 2005-02-17 | Process for isolation of ergot alkaloids from ergot |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA81085C2 true UA81085C2 (en) | 2007-11-26 |
Family
ID=34910788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200610038A UA81085C2 (en) | 2004-02-20 | 2005-02-17 | Process for isolation of ergot alkaloids from ergot (variants) |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20070161795A1 (de) |
| EP (1) | EP1742953B1 (de) |
| JP (1) | JP2007523174A (de) |
| KR (1) | KR20070030176A (de) |
| CN (1) | CN1946728A (de) |
| AT (1) | ATE391720T1 (de) |
| BR (1) | BRPI0506861A (de) |
| CA (1) | CA2556776A1 (de) |
| DE (1) | DE602005005980D1 (de) |
| RU (1) | RU2334750C2 (de) |
| UA (1) | UA81085C2 (de) |
| WO (1) | WO2005082910A1 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012170520A1 (en) | 2011-06-09 | 2012-12-13 | Micromidas Inc. | Utilizing a multiphase reactor for the conversion of biomass to produce substituted furans |
| AR093155A1 (es) | 2012-10-26 | 2015-05-20 | Micromidas Inc | Metodos para la produccion de 5-(halometil)furfural |
| BR112015023313B8 (pt) | 2013-03-14 | 2022-12-13 | Micromidas Inc | Métodos para purificação de 5-(halometil)furfural |
| JP2016512548A (ja) | 2013-03-14 | 2016-04-28 | マイクロマイダス，インコーポレイテッド | 固体形態の５−（ハロメチル）フルフラールおよびその製造方法 |
| EP4166546A1 (de) | 2013-09-20 | 2023-04-19 | Origin Materials Operating, Inc. | Verfahren zur herstellung von 5-(halomethyl)furfural |
| CN113652443B (zh) * | 2021-08-05 | 2023-06-06 | 中国科学院微生物研究所 | 菌株及其发酵生产麦角生物碱的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB809912A (en) * | 1954-09-07 | 1959-03-04 | Ciba Ltd | Active substance from plants of the rauwolfia species and process for manufacturing same |
| FR2089081A5 (de) * | 1970-04-02 | 1972-01-07 | Lek Tovarna Farmacevtskih | |
| FR2460955A1 (fr) * | 1979-07-10 | 1981-01-30 | Fabre Sa Pierre | Procede de preparation de l'ergotamine et des alcaloides du groupe ergotoxine |
| RU2058151C1 (ru) * | 1994-07-07 | 1996-04-20 | Научно-производственное объединение "Всероссийский научно-исследовательский институт лекарственных и ароматических растений" | Способ выделения суммы эргоалкалоидов |
-
2005
- 2005-02-17 JP JP2006554205A patent/JP2007523174A/ja active Pending
- 2005-02-17 CA CA002556776A patent/CA2556776A1/en not_active Abandoned
- 2005-02-17 US US10/589,769 patent/US20070161795A1/en not_active Abandoned
- 2005-02-17 RU RU2006133551/04A patent/RU2334750C2/ru not_active IP Right Cessation
- 2005-02-17 EP EP05713729A patent/EP1742953B1/de not_active Expired - Lifetime
- 2005-02-17 DE DE602005005980T patent/DE602005005980D1/de not_active Expired - Lifetime
- 2005-02-17 BR BRPI0506861-4A patent/BRPI0506861A/pt not_active Application Discontinuation
- 2005-02-17 AT AT05713729T patent/ATE391720T1/de not_active IP Right Cessation
- 2005-02-17 CN CNA2005800123265A patent/CN1946728A/zh active Pending
- 2005-02-17 WO PCT/US2005/005059 patent/WO2005082910A1/en not_active Ceased
- 2005-02-17 KR KR1020067018667A patent/KR20070030176A/ko not_active Withdrawn
- 2005-02-17 UA UAA200610038A patent/UA81085C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1946728A (zh) | 2007-04-11 |
| WO2005082910A1 (en) | 2005-09-09 |
| JP2007523174A (ja) | 2007-08-16 |
| RU2006133551A (ru) | 2008-03-27 |
| RU2334750C2 (ru) | 2008-09-27 |
| ATE391720T1 (de) | 2008-04-15 |
| EP1742953A1 (de) | 2007-01-17 |
| US20070161795A1 (en) | 2007-07-12 |
| KR20070030176A (ko) | 2007-03-15 |
| EP1742953B1 (de) | 2008-04-09 |
| BRPI0506861A (pt) | 2007-06-05 |
| DE602005005980D1 (de) | 2008-05-21 |
| CA2556776A1 (en) | 2005-09-09 |
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