CN104529982A - 荸荠皮提取6-异戊烯基柚皮素的方法 - Google Patents
荸荠皮提取6-异戊烯基柚皮素的方法 Download PDFInfo
- Publication number
- CN104529982A CN104529982A CN201410833072.4A CN201410833072A CN104529982A CN 104529982 A CN104529982 A CN 104529982A CN 201410833072 A CN201410833072 A CN 201410833072A CN 104529982 A CN104529982 A CN 104529982A
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- Prior art keywords
- methyl alcohol
- crude product
- dry
- post
- elutriant
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- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 title claims abstract description 20
- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 235000007625 naringenin Nutrition 0.000 title claims abstract description 20
- 229940117954 naringenin Drugs 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 11
- 244000103152 Eleocharis tuberosa Species 0.000 title abstract description 5
- 235000014309 Eleocharis tuberosa Nutrition 0.000 title abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000000605 extraction Methods 0.000 claims abstract description 21
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 7
- 238000000746 purification Methods 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 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 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 105
- 235000003283 Pachira macrocarpa Nutrition 0.000 claims description 29
- 235000014364 Trapa natans Nutrition 0.000 claims description 29
- 235000009165 saligot Nutrition 0.000 claims description 29
- 241001083492 Trapa Species 0.000 claims description 27
- 239000012043 crude product Substances 0.000 claims description 24
- 239000000284 extract Substances 0.000 claims description 24
- 150000001408 amides Chemical class 0.000 claims description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- 239000012071 phase Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000005227 gel permeation chromatography Methods 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 3
- 238000000825 ultraviolet detection Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 229920002647 polyamide Polymers 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- -1 MCI Substances 0.000 abstract description 2
- 239000000287 crude extract Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000002953 preparative HPLC Methods 0.000 abstract 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 description 6
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 3
- 240000001085 Trapa natans Species 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229930003949 flavanone Natural products 0.000 description 3
- 235000011981 flavanones Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YHWNASRGLKJRJJ-KRWDZBQOSA-N 6-prenylnaringenin Chemical compound C1([C@H]2OC3=CC(O)=C(C(=C3C(=O)C2)O)CC=C(C)C)=CC=C(O)C=C1 YHWNASRGLKJRJJ-KRWDZBQOSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 241000628997 Flos Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000002207 flavanone derivatives Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 241000218235 Cannabaceae Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- FUSADYLVRMROPL-UHFFFAOYSA-N demethylxanthohumol Natural products CC(C)=CCC1=C(O)C=C(O)C(C(=O)C=CC=2C=CC(O)=CC=2)=C1O FUSADYLVRMROPL-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 206010013990 dysuria Diseases 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 206010036067 polydipsia Diseases 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- YHWNASRGLKJRJJ-UHFFFAOYSA-N sophoraflavanone B Natural products C1C(=O)C2=C(O)C(CC=C(C)C)=C(O)C=C2OC1C1=CC=C(O)C=C1 YHWNASRGLKJRJJ-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- ORXQGKIUCDPEAJ-YRNVUSSQSA-N xanthohumol Chemical compound COC1=CC(O)=C(CC=C(C)C)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1 ORXQGKIUCDPEAJ-YRNVUSSQSA-N 0.000 description 1
- UVBDKJHYMQEAQV-UHFFFAOYSA-N xanthohumol Natural products OC1=C(CC=C(C)C)C(OC)=CC(OC)=C1C(=O)C=CC1=CC=C(O)C=C1 UVBDKJHYMQEAQV-UHFFFAOYSA-N 0.000 description 1
- 235000008209 xanthohumol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410833072.4A CN104529982B (zh) | 2014-12-29 | 2014-12-29 | 荸荠皮提取6-异戊烯基柚皮素的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201410833072.4A CN104529982B (zh) | 2014-12-29 | 2014-12-29 | 荸荠皮提取6-异戊烯基柚皮素的方法 |
Publications (2)
Publication Number | Publication Date |
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CN104529982A true CN104529982A (zh) | 2015-04-22 |
CN104529982B CN104529982B (zh) | 2016-08-17 |
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CN201410833072.4A Active CN104529982B (zh) | 2014-12-29 | 2014-12-29 | 荸荠皮提取6-异戊烯基柚皮素的方法 |
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CN (1) | CN104529982B (zh) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101269161A (zh) * | 2008-05-20 | 2008-09-24 | 贺州学院 | 一种从荸荠皮中提取总黄酮的工艺 |
-
2014
- 2014-12-29 CN CN201410833072.4A patent/CN104529982B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101269161A (zh) * | 2008-05-20 | 2008-09-24 | 贺州学院 | 一种从荸荠皮中提取总黄酮的工艺 |
Non-Patent Citations (1)
Title |
---|
GE ZHAN ET AL: "《Study on antibacterial properties and major bioactive constituents of Chinese water chestnut (Eleocharis dulcis) peels extracts/fractions》", 《EUR. FOOD RES. TECHNOL》, vol. 238, 21 January 2014 (2014-01-21), pages 789 - 796 * |
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Publication number | Publication date |
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CN104529982B (zh) | 2016-08-17 |
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PB01 | Publication | ||
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C14 | Grant of patent or utility model | ||
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EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20150422 Assignee: Guangxi Hengfengda Supply Chain Management Co.,Ltd. Assignor: HEZHOU University Contract record no.: X2023980046610 Denomination of invention: Method for Extracting 6-Isopentenylnaringin from Water Chestnut Peel Granted publication date: 20160817 License type: Common License Record date: 20231108 Application publication date: 20150422 Assignee: Pingle Leyao Food Co.,Ltd. Assignor: HEZHOU University Contract record no.: X2023980046448 Denomination of invention: Method for Extracting 6-Isopentenylnaringin from Water Chestnut Peel Granted publication date: 20160817 License type: Common License Record date: 20231108 |
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EE01 | Entry into force of recordation of patent licensing contract |