CN104610273B - Method of extracting gambogic acid and neogambogic acid from gamboge - Google Patents
Method of extracting gambogic acid and neogambogic acid from gamboge Download PDFInfo
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- CN104610273B CN104610273B CN201510077377.1A CN201510077377A CN104610273B CN 104610273 B CN104610273 B CN 104610273B CN 201510077377 A CN201510077377 A CN 201510077377A CN 104610273 B CN104610273 B CN 104610273B
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- acid
- gamboge
- gambogicacid
- neo
- ethanol
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- GEZHEQNLKAOMCA-RRZNCOCZSA-N (-)-gambogic acid Chemical compound C([C@@H]1[C@]2([C@@](C3=O)(C\C=C(\C)C(O)=O)OC1(C)C)O1)[C@H]3C=C2C(=O)C2=C1C(CC=C(C)C)=C1O[C@@](CCC=C(C)C)(C)C=CC1=C2O GEZHEQNLKAOMCA-RRZNCOCZSA-N 0.000 title claims abstract description 35
- GEZHEQNLKAOMCA-UHFFFAOYSA-N epiisogambogic acid Natural products O1C2(C(C3=O)(CC=C(C)C(O)=O)OC4(C)C)C4CC3C=C2C(=O)C2=C1C(CC=C(C)C)=C1OC(CCC=C(C)C)(C)C=CC1=C2O GEZHEQNLKAOMCA-UHFFFAOYSA-N 0.000 title claims abstract description 35
- GEZHEQNLKAOMCA-GXSDCXQCSA-N gambogic acid Natural products C([C@@H]1[C@]2([C@@](C3=O)(C\C=C(/C)C(O)=O)OC1(C)C)O1)[C@H]3C=C2C(=O)C2=C1C(CC=C(C)C)=C1O[C@@](CCC=C(C)C)(C)C=CC1=C2O GEZHEQNLKAOMCA-GXSDCXQCSA-N 0.000 title claims abstract description 35
- QALPNMQDVCOSMJ-UHFFFAOYSA-N isogambogic acid Natural products CC(=CCc1c2OC(C)(CC=C(C)C)C=Cc2c(O)c3C(=O)C4=CC5CC6C(C)(C)OC(CC=C(C)/C(=O)O)(C5=O)C46Oc13)C QALPNMQDVCOSMJ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 241000598860 Garcinia hanburyi Species 0.000 title claims abstract description 31
- 229940117709 gamboge Drugs 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title abstract description 18
- BLDWFKHVHHINGR-FYJGNVAPSA-N neo-gambogic acid Chemical compound C1C2C(C)(C)OC3(C\C=C(/C)C(O)=O)C(=O)C1C=C1C(=O)C(C(O)=C4C(O)CC(OC4=C4CC=C(C)C)(C)CCC=C(C)C)=C4OC123 BLDWFKHVHHINGR-FYJGNVAPSA-N 0.000 title abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000000284 extract Substances 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000874 microwave-assisted extraction Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 239000003208 petroleum Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 238000001179 sorption measurement Methods 0.000 claims description 10
- GMWTXQKKRDUVQG-WOPPDYDQSA-N 4-amino-5-bromo-1-[(2r,3s,4s,5r)-4-hydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]pyrimidin-2-one Chemical compound C[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C(Br)=C1 GMWTXQKKRDUVQG-WOPPDYDQSA-N 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 7
- 239000003463 adsorbent Substances 0.000 claims description 6
- 238000003795 desorption Methods 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000008213 purified water Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 4
- 239000002250 absorbent Substances 0.000 claims description 4
- 230000002745 absorbent Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000002386 leaching Methods 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 102000011759 adducin Human genes 0.000 description 3
- 108010076723 adducin Proteins 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 241000345998 Calamus manan Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- XTVYWYLMVSZOSU-LPYMAVHISA-N allogambogic acid Chemical compound O1C2(C(C3=O)(C\C=C(/C)C(O)=O)OC4(C)C)C4CC3C=C2C(=O)C2=C1C(CC=C(C)C)=C(O)C1=C2OC(CCC=C(C)C)(C)C=C1 XTVYWYLMVSZOSU-LPYMAVHISA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 235000012950 rattan cane Nutrition 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000593508 Garcinia Species 0.000 description 1
- 235000000885 Garcinia xanthochymus Nutrition 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000012846 chemical reference substance Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 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
- 235000013312 flour Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000002607 hemopoietic effect Effects 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201510077377.1A CN104610273B (en) | 2015-02-13 | 2015-02-13 | Method of extracting gambogic acid and neogambogic acid from gamboge |
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CN201510077377.1A CN104610273B (en) | 2015-02-13 | 2015-02-13 | Method of extracting gambogic acid and neogambogic acid from gamboge |
Publications (2)
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CN104610273A CN104610273A (en) | 2015-05-13 |
CN104610273B true CN104610273B (en) | 2017-01-18 |
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CN201510077377.1A Active CN104610273B (en) | 2015-02-13 | 2015-02-13 | Method of extracting gambogic acid and neogambogic acid from gamboge |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107137392A (en) * | 2017-06-02 | 2017-09-08 | 南方医科大学 | Neo-garcinolic acid is preparing the application in suppressing hepatoma cell proliferation, migration and liver cancer apoptosis reducing medicine |
CN110229169A (en) * | 2019-06-27 | 2019-09-13 | 济宁医学院 | A kind of method Neo-garcinolic acid separation and its prepare the new gamboge amide of N- aryl |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101781309B (en) * | 2010-02-09 | 2013-04-24 | 夏伦祝 | Method for extracting gambogic acid and neo-gambogic acid in traditional Chinese medicine gamboge by using supercritical fluid |
CN102617590A (en) * | 2012-03-07 | 2012-08-01 | 广州牌牌生物科技有限公司 | Preparation process for neogambogic acid |
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2015
- 2015-02-13 CN CN201510077377.1A patent/CN104610273B/en active Active
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Address after: 011517, building 3, unit 7, Wanda District, Wanda Plaza, Xinhua East Street, the Inner Mongolia Autonomous Region, Hohhot, 602, China Applicant after: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Address before: 011517 building 3, unit 7, building 602B, unit 3, building 7, Wanda Plaza, Xinhua District, Xinhua East Street, the Inner Mongolia Autonomous Region, Hohhot, 602, China, B Applicant before: INNER MONGOLIA CHANGHUI BIOLOGICAL TECHNOLOGY Co.,Ltd. |
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Address after: 028400 no.0427, Dongjiao Industrial Park, Kailu Town, Kailu County, Tongliao City, Inner Mongolia Autonomous Region Patentee after: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Address before: 011517 Wanda Plaza, Xinhua East Street, Hohhot, Inner Mongolia Patentee before: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. |
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Denomination of invention: A method for extracting gambogic acid and neogambogic acid from Gamboge Effective date of registration: 20210222 Granted publication date: 20170118 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY Co.,Ltd. Registration number: Y2021150000016 |
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Date of cancellation: 20220321 Granted publication date: 20170118 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2021150000016 |
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Denomination of invention: A method for extracting gambogic acid and neogambogic acid from tenghuang Effective date of registration: 20220330 Granted publication date: 20170118 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2022150000027 |
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Denomination of invention: A method for extracting gambogic acid and neogambogic acid from gambog Effective date of registration: 20230307 Granted publication date: 20170118 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000031 |
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Date of cancellation: 20231031 Granted publication date: 20170118 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000031 |
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Denomination of invention: A method for extracting gambogic acid and neogambogic acid from gambog Effective date of registration: 20231101 Granted publication date: 20170118 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000154 |
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