JPS6150921A - バイカリンの精製化法 - Google Patents
バイカリンの精製化法Info
- Publication number
- JPS6150921A JPS6150921A JP59173538A JP17353884A JPS6150921A JP S6150921 A JPS6150921 A JP S6150921A JP 59173538 A JP59173538 A JP 59173538A JP 17353884 A JP17353884 A JP 17353884A JP S6150921 A JPS6150921 A JP S6150921A
- Authority
- JP
- Japan
- Prior art keywords
- baicalin
- water
- crude
- night
- purity
- 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.)
- Granted
Links
- IPQKDIRUZHOIOM-UHFFFAOYSA-N Oroxin A Natural products OC1C(O)C(O)C(CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IPQKDIRUZHOIOM-UHFFFAOYSA-N 0.000 title claims abstract description 66
- IKIIZLYTISPENI-ZFORQUDYSA-N baicalin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IKIIZLYTISPENI-ZFORQUDYSA-N 0.000 title claims abstract description 66
- 229960003321 baicalin Drugs 0.000 title claims abstract description 66
- AQHDANHUMGXSJZ-UHFFFAOYSA-N baicalin Natural products OC1C(O)C(C(O)CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 AQHDANHUMGXSJZ-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000746 purification Methods 0.000 title abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000000706 filtrate Substances 0.000 claims abstract description 13
- 239000004952 Polyamide Substances 0.000 claims abstract description 11
- 238000009835 boiling Methods 0.000 claims abstract description 11
- 229920002647 polyamide Polymers 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 8
- 239000001913 cellulose Substances 0.000 claims abstract description 5
- 229920002678 cellulose Polymers 0.000 claims abstract description 5
- 229920005654 Sephadex Polymers 0.000 claims description 2
- 239000012507 Sephadex™ Substances 0.000 claims description 2
- 239000012847 fine chemical Substances 0.000 claims description 2
- 241000207929 Scutellaria Species 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 abstract description 7
- 238000007796 conventional method Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000010330 ougon Substances 0.000 abstract 2
- 240000004534 Scutellaria baicalensis Species 0.000 abstract 1
- 235000017089 Scutellaria baicalensis Nutrition 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 238000002523 gelfiltration Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- NIFIFKQPDTWWGU-UHFFFAOYSA-N pyrite Chemical compound [Fe+2].[S-][S-] NIFIFKQPDTWWGU-UHFFFAOYSA-N 0.000 description 10
- 229910052683 pyrite Inorganic materials 0.000 description 10
- 239000011028 pyrite Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000005238 degreasing Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 244000140786 Brassica hirta Species 0.000 description 4
- 235000011371 Brassica hirta Nutrition 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241001061264 Astragalus Species 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 3
- 229920000299 Nylon 12 Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000006533 astragalus Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 210000004233 talus Anatomy 0.000 description 3
- 244000291564 Allium cepa Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- 208000003251 Pruritus Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000012136 culture method Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000002969 egg yolk Anatomy 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- TZJALUIVHRYQQB-UHFFFAOYSA-N Icarin Chemical compound C1=CC(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(C)O2)O)C(=O)C2=C(O)C=C(OC3C(C(O)C(O)C(CO)O3)O)C(CC=C(C)C)=C2O1 TZJALUIVHRYQQB-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- RHOSDCYBAWJKFR-UHFFFAOYSA-N [NH4+].[O-]I=O Chemical compound [NH4+].[O-]I=O RHOSDCYBAWJKFR-UHFFFAOYSA-N 0.000 description 1
- 239000002156 adsorbate Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000012443 analytical study Methods 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000029087 digestion Effects 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
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59173538A JPS6150921A (ja) | 1984-08-20 | 1984-08-20 | バイカリンの精製化法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59173538A JPS6150921A (ja) | 1984-08-20 | 1984-08-20 | バイカリンの精製化法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6150921A true JPS6150921A (ja) | 1986-03-13 |
| JPS6232173B2 JPS6232173B2 (enrdf_load_stackoverflow) | 1987-07-13 |
Family
ID=15962387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59173538A Granted JPS6150921A (ja) | 1984-08-20 | 1984-08-20 | バイカリンの精製化法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6150921A (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996002528A1 (fr) * | 1994-07-14 | 1996-02-01 | Tsumura & Co. | Procede de separation et de recuperation de composes de la flavone a structure glycosidique et composes de la flavone ne presentant pas de structure glycosidique |
| WO2003086434A1 (en) * | 2002-04-15 | 2003-10-23 | Tetsuo Santo | Drinking tea for treating dermatitis |
| WO2005077929A1 (en) * | 2004-02-09 | 2005-08-25 | Cargill, Incorporated | Phenolic compound purification |
| EP2108370A1 (en) | 2002-04-30 | 2009-10-14 | Unigen Pharmaceuticals, Inc. | Formulation of a mixture of free-B-ring flavonoids and flavans as a therapeutic agent |
| CN102311469A (zh) * | 2011-09-16 | 2012-01-11 | 陕西科技大学 | 一种利用黄芩毛状根生产黄芩苷的方法 |
| CN103694294A (zh) * | 2014-01-10 | 2014-04-02 | 河南智晶生物科技有限公司 | 利用闪提技术提取黄芩苷的方法 |
| US8771761B2 (en) | 2006-10-12 | 2014-07-08 | Unigen, Inc. | Composition for treating atopic dermatitis comprising extracts of bamboo and scutellaria |
| US8945518B2 (en) | 2002-04-30 | 2015-02-03 | Unigen, Inc. | Formulation of dual eicosanoid system and cytokine system inhibitors for use in the prevention and treatment of oral diseases and conditions |
| CN104650165A (zh) * | 2015-02-27 | 2015-05-27 | 山东省分析测试中心 | 一种高纯度黄芩苷的制备方法 |
| US9061039B2 (en) | 2002-03-01 | 2015-06-23 | Unigen, Inc. | Identification of Free-B-Ring flavonoids as potent COX-2 inhibitors |
| US9168242B2 (en) | 2002-03-22 | 2015-10-27 | Unigen, Inc. | Isolation of a dual COX-2 and 5-lipdxygenase inhibitor from Acacia |
| US9622964B2 (en) | 2003-04-04 | 2017-04-18 | Unigen, Inc. | Formulation of dual cycloxygenase (COX) and lipoxygenase (LOX) inhibitors for mammal skin care |
| CN109320569A (zh) * | 2017-08-01 | 2019-02-12 | 湘潭大学 | 一种从黄芩中提取高纯度黄芩苷的方法 |
| JP2019509332A (ja) * | 2016-02-01 | 2019-04-04 | 承徳医学院 | バイカリンマグネシウム化合物、その製造方法及び使用 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04103977U (ja) * | 1991-02-18 | 1992-09-08 | 株式会社ニフコ | ラツチ装置 |
| JP3722536B2 (ja) * | 1996-02-09 | 2005-11-30 | サンスター株式会社 | 毛母細胞賦活剤およびそれを配合してなる養毛剤組成物 |
-
1984
- 1984-08-20 JP JP59173538A patent/JPS6150921A/ja active Granted
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996002528A1 (fr) * | 1994-07-14 | 1996-02-01 | Tsumura & Co. | Procede de separation et de recuperation de composes de la flavone a structure glycosidique et composes de la flavone ne presentant pas de structure glycosidique |
| US9061039B2 (en) | 2002-03-01 | 2015-06-23 | Unigen, Inc. | Identification of Free-B-Ring flavonoids as potent COX-2 inhibitors |
| US9168242B2 (en) | 2002-03-22 | 2015-10-27 | Unigen, Inc. | Isolation of a dual COX-2 and 5-lipdxygenase inhibitor from Acacia |
| WO2003086434A1 (en) * | 2002-04-15 | 2003-10-23 | Tetsuo Santo | Drinking tea for treating dermatitis |
| JPWO2003086434A1 (ja) * | 2002-04-15 | 2005-08-18 | 哲夫 山東 | 皮膚炎治療用飲用茶 |
| US7615239B2 (en) | 2002-04-15 | 2009-11-10 | Tetsuo Santo | Tea for treating dermatitis comprising herbal extracts |
| US8945518B2 (en) | 2002-04-30 | 2015-02-03 | Unigen, Inc. | Formulation of dual eicosanoid system and cytokine system inhibitors for use in the prevention and treatment of oral diseases and conditions |
| US9655940B2 (en) | 2002-04-30 | 2017-05-23 | Unigen, Inc. | Formulation of a mixture of free-B-ring flavonoids and flavans as a therapeutic agent |
| US9849152B2 (en) | 2002-04-30 | 2017-12-26 | Unigen, Inc. | Formulation of a mixture of Free-B-ring flavonoids and flavans as a therapeutic agent |
| US9370544B2 (en) | 2002-04-30 | 2016-06-21 | Unigen, Inc. | Formulation of a mixture of free-B-ring flavonoids and flavans as a therapeutic agent |
| EP2108370A1 (en) | 2002-04-30 | 2009-10-14 | Unigen Pharmaceuticals, Inc. | Formulation of a mixture of free-B-ring flavonoids and flavans as a therapeutic agent |
| US9622964B2 (en) | 2003-04-04 | 2017-04-18 | Unigen, Inc. | Formulation of dual cycloxygenase (COX) and lipoxygenase (LOX) inhibitors for mammal skin care |
| WO2005077929A1 (en) * | 2004-02-09 | 2005-08-25 | Cargill, Incorporated | Phenolic compound purification |
| US9623068B2 (en) | 2006-10-12 | 2017-04-18 | Unigen, Inc. | Composition for treating atopic dermatitis comprising extracts of bamboo and scutellaria |
| US8771761B2 (en) | 2006-10-12 | 2014-07-08 | Unigen, Inc. | Composition for treating atopic dermatitis comprising extracts of bamboo and scutellaria |
| CN102311469A (zh) * | 2011-09-16 | 2012-01-11 | 陕西科技大学 | 一种利用黄芩毛状根生产黄芩苷的方法 |
| CN103694294A (zh) * | 2014-01-10 | 2014-04-02 | 河南智晶生物科技有限公司 | 利用闪提技术提取黄芩苷的方法 |
| CN104650165A (zh) * | 2015-02-27 | 2015-05-27 | 山东省分析测试中心 | 一种高纯度黄芩苷的制备方法 |
| JP2019509332A (ja) * | 2016-02-01 | 2019-04-04 | 承徳医学院 | バイカリンマグネシウム化合物、その製造方法及び使用 |
| CN109320569A (zh) * | 2017-08-01 | 2019-02-12 | 湘潭大学 | 一种从黄芩中提取高纯度黄芩苷的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6232173B2 (enrdf_load_stackoverflow) | 1987-07-13 |
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