CN111423424A - 一种高纯芒果苷结晶的制备方法 - Google Patents
一种高纯芒果苷结晶的制备方法 Download PDFInfo
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- CN111423424A CN111423424A CN202010065516.XA CN202010065516A CN111423424A CN 111423424 A CN111423424 A CN 111423424A CN 202010065516 A CN202010065516 A CN 202010065516A CN 111423424 A CN111423424 A CN 111423424A
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- mangiferin
- purity
- extract
- crude product
- crystal
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- AEDDIBAIWPIIBD-ZJKJAXBQSA-N mangiferin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=C(OC=2C(=CC(O)=C(O)C=2)C2=O)C2=C1O AEDDIBAIWPIIBD-ZJKJAXBQSA-N 0.000 title claims abstract description 401
- YWQSXCGKJDUYTL-UHFFFAOYSA-N Mangiferin Natural products CC(CCC=C(C)C)C1CC(C)C2C3CCC4C(C)(C)CCCC45CC35CCC12C YWQSXCGKJDUYTL-UHFFFAOYSA-N 0.000 title claims abstract description 200
- 229940043357 mangiferin Drugs 0.000 title claims abstract description 200
- 239000013078 crystal Substances 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 37
- 235000004936 Bromus mango Nutrition 0.000 claims abstract description 25
- 241001093152 Mangifera Species 0.000 claims abstract description 25
- 235000014826 Mangifera indica Nutrition 0.000 claims abstract description 25
- 235000009184 Spondias indica Nutrition 0.000 claims abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 54
- 239000012043 crude product Substances 0.000 claims description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 238000001914 filtration Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 239000003208 petroleum Substances 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 14
- 239000012046 mixed solvent Substances 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 7
- 238000007602 hot air drying Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 238000003760 magnetic stirring Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 abstract description 10
- 238000001953 recrystallisation Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 33
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001533085 Aquilaria sinensis Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004185 countercurrent chromatography Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- SOZJOEXYKMDOMP-UHFFFAOYSA-N 3,4,5,6-tetrahydroxypyran-2-one Chemical compound OC=1OC(=O)C(O)=C(O)C=1O SOZJOEXYKMDOMP-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 240000006053 Garcinia mangostana Species 0.000 description 1
- 235000017048 Garcinia mangostana Nutrition 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 241001530209 Swertia Species 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000010262 high-speed countercurrent chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000007365 immunoregulation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- -1 mangiferin compound Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000513 principal component analysis Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (7)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112321577A (zh) * | 2020-11-09 | 2021-02-05 | 湖南原草生物技术有限公司 | 一种从芒果叶中提取高纯芒果苷的方法 |
CN113416182A (zh) * | 2021-05-28 | 2021-09-21 | 西安金泰生物技术有限公司 | 一种芒果苷及其制备方法 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4518592A (en) * | 1980-07-16 | 1985-05-21 | Rusakova Svetlana V | Process for preparing mangiferin |
RU2032413C1 (ru) * | 1991-09-06 | 1995-04-10 | Научно-производственное объединение "Всероссийский научно-исследовательский институт лекарственных и ароматических растений" | Способ получения мангиферина |
CN101671330A (zh) * | 2009-10-13 | 2010-03-17 | 刘全胜 | 芒果苷的制备方法 |
CN102408415A (zh) * | 2010-09-21 | 2012-04-11 | 昆明制药集团股份有限公司 | 一种芒果苷的制备方法 |
CN104530022A (zh) * | 2015-01-07 | 2015-04-22 | 泉州师范学院 | 纤维酶辅助的芒果叶中芒果苷和槲皮素的提取方法 |
CN106831738A (zh) * | 2017-01-23 | 2017-06-13 | 攀枝花学院 | 一种从芒果叶中提取分离芒果苷的方法 |
CN107266509A (zh) * | 2017-07-20 | 2017-10-20 | 广西南宁桂知科技有限公司 | 一种采用芒果叶制取芒果甙的工艺 |
CN109081859A (zh) * | 2018-09-27 | 2018-12-25 | 那坡康正天然植物提取有限责任公司 | 芒果甙的生产方法 |
CN109678850A (zh) * | 2019-03-06 | 2019-04-26 | 云南中医学院 | 一种从芒果叶中提取纯化芒果苷的制备方法 |
-
2020
- 2020-01-20 CN CN202010065516.XA patent/CN111423424B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4518592A (en) * | 1980-07-16 | 1985-05-21 | Rusakova Svetlana V | Process for preparing mangiferin |
RU2032413C1 (ru) * | 1991-09-06 | 1995-04-10 | Научно-производственное объединение "Всероссийский научно-исследовательский институт лекарственных и ароматических растений" | Способ получения мангиферина |
CN101671330A (zh) * | 2009-10-13 | 2010-03-17 | 刘全胜 | 芒果苷的制备方法 |
CN102408415A (zh) * | 2010-09-21 | 2012-04-11 | 昆明制药集团股份有限公司 | 一种芒果苷的制备方法 |
CN104530022A (zh) * | 2015-01-07 | 2015-04-22 | 泉州师范学院 | 纤维酶辅助的芒果叶中芒果苷和槲皮素的提取方法 |
CN106831738A (zh) * | 2017-01-23 | 2017-06-13 | 攀枝花学院 | 一种从芒果叶中提取分离芒果苷的方法 |
CN107266509A (zh) * | 2017-07-20 | 2017-10-20 | 广西南宁桂知科技有限公司 | 一种采用芒果叶制取芒果甙的工艺 |
CN109081859A (zh) * | 2018-09-27 | 2018-12-25 | 那坡康正天然植物提取有限责任公司 | 芒果甙的生产方法 |
CN109678850A (zh) * | 2019-03-06 | 2019-04-26 | 云南中医学院 | 一种从芒果叶中提取纯化芒果苷的制备方法 |
Non-Patent Citations (2)
Title |
---|
TANG-BIN ZOU,等: "Ultrasound-Assisted Extraction of Mangiferin from Mango (Mangifera indica L.) Leaves Using Response Surface Methodology", 《MOLECULES》 * |
韦会平等: "酯提除杂法高效提取分离芒果叶芒果苷", 《南方农业学报》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112321577A (zh) * | 2020-11-09 | 2021-02-05 | 湖南原草生物技术有限公司 | 一种从芒果叶中提取高纯芒果苷的方法 |
CN112321577B (zh) * | 2020-11-09 | 2022-02-01 | 湖南原草生物技术有限公司 | 一种从芒果叶中提取高纯芒果苷的方法 |
CN113416182A (zh) * | 2021-05-28 | 2021-09-21 | 西安金泰生物技术有限公司 | 一种芒果苷及其制备方法 |
CN113416182B (zh) * | 2021-05-28 | 2022-03-29 | 西安金泰生物技术有限公司 | 一种芒果苷及其制备方法 |
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