JPS6263581A - ５，７，３′，４′，５′―ペンタヒドロキシフラボノールの分離精製法 - Google Patents

５，７，３′，４′，５′―ペンタヒドロキシフラボノールの分離精製法

Info

Publication number: JPS6263581A
Authority: JP; Japan
Prior art keywords: solvent; aqueous solution; water; soluble; layer
Prior art date: 1985-09-17
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

Application number

JP60203286A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0582390B2 (cs

Inventor

Kazuo Suzuki

和男鈴木

Susumu Kuraishi

倉石　晉

Toshio Fujikura

藤倉　敏夫

Tsukasa Matsumoto

司松本

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cosmo Co Ltd

Original Assignee

Cosmo Co Ltd

Priority date (The priority date 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 date listed.)

1985-09-17

Filing date

1985-09-17

Publication date

1987-03-20

1985-09-17 Application filed by Cosmo Co Ltd filed Critical Cosmo Co Ltd

1985-09-17 Priority to JP60203286A priority Critical patent/JPS6263581A/ja

1987-03-20 Publication of JPS6263581A publication Critical patent/JPS6263581A/ja

1993-11-18 Publication of JPH0582390B2 publication Critical patent/JPH0582390B2/ja

Status Granted legal-status Critical Current

Links

GCWMEFUMPZHUFF-UHFFFAOYSA-N 3,5,7-trihydroxy-2-(2,4,5-trihydroxyphenyl)chromen-4-one Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C=C1O GCWMEFUMPZHUFF-UHFFFAOYSA-N 0.000 title claims 2
238000000746 purification Methods 0.000 title description 3
238000000926 separation method Methods 0.000 title description 3
239000007864 aqueous solution Substances 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 20
239000003021 water soluble solvent Substances 0.000 claims abstract description 15
239000002904 solvent Substances 0.000 claims abstract description 14
239000000243 solution Substances 0.000 claims abstract description 13
238000002523 gelfiltration Methods 0.000 claims abstract description 11
238000009835 boiling Methods 0.000 claims abstract description 8
238000000638 solvent extraction Methods 0.000 claims abstract description 6
239000000284 extract Substances 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
244000042324 Trifolium repens Species 0.000 abstract description 13
235000013540 Trifolium repens var repens Nutrition 0.000 abstract description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 12
241000196324 Embryophyta Species 0.000 abstract description 7
230000002401 inhibitory effect Effects 0.000 abstract description 7
239000002798 polar solvent Substances 0.000 abstract description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
229920005654 Sephadex Polymers 0.000 abstract description 6
239000012507 Sephadex™ Substances 0.000 abstract description 6
150000001875 compounds Chemical class 0.000 abstract description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract description 4
230000032823 cell division Effects 0.000 abstract description 4
238000001704 evaporation Methods 0.000 abstract description 3
230000008020 evaporation Effects 0.000 abstract description 3
238000004821 distillation Methods 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 abstract description 2
235000017557 sodium bicarbonate Nutrition 0.000 abstract description 2
235000010729 Trifolium repens Nutrition 0.000 abstract 1
238000000605 extraction Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000005194 fractionation Methods 0.000 description 6
239000000499 gel Substances 0.000 description 6
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
239000010931 gold Substances 0.000 description 6
229910052737 gold Inorganic materials 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000007863 gel particle Substances 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
230000002441 reversible effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000000872 buffer Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
235000014593 oils and fats Nutrition 0.000 description 2
239000003002 pH adjusting agent Substances 0.000 description 2
238000004810 partition chromatography Methods 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000003799 water insoluble solvent Substances 0.000 description 2
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
239000006171 Britton–Robinson buffer Substances 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
240000007015 Melilotus indicus Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
244000046101 Sophora japonica Species 0.000 description 1
235000010586 Sophora japonica Nutrition 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
240000002913 Trifolium pratense Species 0.000 description 1
235000015724 Trifolium pratense Nutrition 0.000 description 1
241000700605 Viruses Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000005377 adsorption chromatography Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000013040 bath agent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229940117955 isoamyl acetate Drugs 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000021374 legumes Nutrition 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 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
230000000394 mitotic effect Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
231100001083 no cytotoxicity Toxicity 0.000 description 1
231100000065 noncytotoxic Toxicity 0.000 description 1
230000002020 noncytotoxic effect Effects 0.000 description 1
-1 octadecyl silicate Chemical compound 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
MGRFDZWQSJNJQP-UHFFFAOYSA-N triethyl arsorate Chemical compound CCO[As](=O)(OCC)OCC MGRFDZWQSJNJQP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pyrane Compounds (AREA)
Medicines Containing Plant Substances (AREA)

JP60203286A 1985-09-17 1985-09-17 ５，７，３′，４′，５′―ペンタヒドロキシフラボノールの分離精製法 Granted JPS6263581A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60203286A JPS6263581A (ja)	1985-09-17	1985-09-17	５，７，３′，４′，５′―ペンタヒドロキシフラボノールの分離精製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60203286A JPS6263581A (ja)	1985-09-17	1985-09-17	５，７，３′，４′，５′―ペンタヒドロキシフラボノールの分離精製法

Publications (2)

Publication Number	Publication Date
JPS6263581A true JPS6263581A (ja)	1987-03-20
JPH0582390B2 JPH0582390B2 (cs)	1993-11-18

Family

ID=16471528

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60203286A Granted JPS6263581A (ja)	1985-09-17	1985-09-17	５，７，３′，４′，５′―ペンタヒドロキシフラボノールの分離精製法

Country Status (1)

Country	Link
JP (1)	JPS6263581A (cs)

1985
- 1985-09-17 JP JP60203286A patent/JPS6263581A/ja active Granted

Also Published As

Publication number	Publication date
JPH0582390B2 (cs)	1993-11-18

Legal Events

Date	Code	Title	Description
2004-11-18	LAPS	Cancellation because of no payment of annual fees

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