CN1680392A - 一种高纯度银杏内酯的制备方法 - Google Patents
一种高纯度银杏内酯的制备方法 Download PDFInfo
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- CN1680392A CN1680392A CN 200510023164 CN200510023164A CN1680392A CN 1680392 A CN1680392 A CN 1680392A CN 200510023164 CN200510023164 CN 200510023164 CN 200510023164 A CN200510023164 A CN 200510023164A CN 1680392 A CN1680392 A CN 1680392A
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- ginkgolide
- bilobalide
- high purity
- volume ratio
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- 238000002360 preparation method Methods 0.000 title claims description 32
- 229930184727 ginkgolide Natural products 0.000 title claims description 7
- 235000008100 Ginkgo biloba Nutrition 0.000 claims abstract description 37
- 241000218628 Ginkgo Species 0.000 claims abstract description 36
- 235000011201 Ginkgo Nutrition 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 23
- MOLPUWBMSBJXER-YDGSQGCISA-N bilobalide Chemical compound O([C@H]1OC2=O)C(=O)[C@H](O)[C@@]11[C@@](C(C)(C)C)(O)C[C@H]3[C@@]21CC(=O)O3 MOLPUWBMSBJXER-YDGSQGCISA-N 0.000 claims description 101
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- SQOJOAFXDQDRGF-WJHVHIKBSA-N ginkgolide B Natural products O=C1[C@@H](C)[C@@]2(O)[C@@H]([C@H](O)[C@]34[C@@H]5OC(=O)[C@]23O[C@H]2OC(=O)[C@H](O)[C@@]42[C@H](C(C)(C)C)C5)O1 SQOJOAFXDQDRGF-WJHVHIKBSA-N 0.000 claims description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000004615 ingredient Substances 0.000 claims description 24
- SQOJOAFXDQDRGF-MMQTXUMRSA-N ginkgolide-b Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13[C@@H](O)[C@@H]1OC(=O)[C@@H](C)[C@]21O SQOJOAFXDQDRGF-MMQTXUMRSA-N 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 23
- FPUXKXIZEIDQKW-VKMVSBOZSA-N ginkgolide-a Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13C[C@@H]1OC(=O)[C@@H](C)[C@]21O FPUXKXIZEIDQKW-VKMVSBOZSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- FPUXKXIZEIDQKW-MFJLLLFKSA-N ginkgolide A Natural products O=C1[C@H](C)[C@@]2(O)[C@@H](O1)C[C@]13[C@@H]4OC(=O)[C@]21O[C@@H]1OC(=O)[C@H](O)[C@]31[C@@H](C(C)(C)C)C4 FPUXKXIZEIDQKW-MFJLLLFKSA-N 0.000 claims description 21
- 150000002596 lactones Chemical class 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 238000002474 experimental method Methods 0.000 claims description 12
- -1 aliphatic ketones Chemical class 0.000 claims description 9
- USRQFWVIFMOEHL-UHFFFAOYSA-N ethanol ethyl acetate hexane hydrate Chemical compound O.CCO.CCCCCC.CCOC(C)=O USRQFWVIFMOEHL-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
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- 230000033228 biological regulation Effects 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
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- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 16
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 1
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- 244000194101 Ginkgo biloba Species 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
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- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 3
- YXHVCZZLWZYHSA-UHFFFAOYSA-N (Z)-6-[8-pentadecenyl]salicylic acid Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1C(O)=O YXHVCZZLWZYHSA-UHFFFAOYSA-N 0.000 description 2
- YXHVCZZLWZYHSA-FPLPWBNLSA-N Ginkgoic acid Chemical compound CCCCCC\C=C/CCCCCCCC1=CC=CC(O)=C1C(O)=O YXHVCZZLWZYHSA-FPLPWBNLSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 229930182478 glucoside Natural products 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 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
- UFJORDZSBNSRQT-UHFFFAOYSA-N 3-(4-oxo-2-phenylchromen-3-yl)-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C=2C(C3=CC=CC=C3OC=2C=2C=CC=CC=2)=O)=C1C1=CC=CC=C1 UFJORDZSBNSRQT-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000009429 Ginkgo biloba extract Substances 0.000 description 1
- 241000218791 Ginkgoaceae Species 0.000 description 1
- AMOGMTLMADGEOQ-FNZROXQESA-N Ginkgolide C Chemical compound O([C@H]1O2)C(=O)[C@H](O)C31[C@]14[C@@H](O)[C@@H]5OC(=O)[C@@H](C)[C@]5(O)[C@@]12C(=O)O[C@@H]4[C@@H](O)[C@H]3C(C)(C)C AMOGMTLMADGEOQ-FNZROXQESA-N 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
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- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 229930003935 flavonoid Natural products 0.000 description 1
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- AMOGMTLMADGEOQ-DPFZUGDXSA-N ginkgolide C Natural products O=C1[C@@H](C)[C@]2(O)[C@H]([C@H](O)[C@@]34[C@H]5[C@H](O)[C@@H](C(C)(C)C)[C@]63[C@H](O)C(=O)O[C@H]6O[C@@]24C(=O)O5)O1 AMOGMTLMADGEOQ-DPFZUGDXSA-N 0.000 description 1
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- 235000008777 kaempferol Nutrition 0.000 description 1
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Landscapes
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CNB2005100231647A CN100497344C (zh) | 2005-01-07 | 2005-01-07 | 一种高纯度银杏内酯的制备方法 |
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CNB2005100231647A CN100497344C (zh) | 2005-01-07 | 2005-01-07 | 一种高纯度银杏内酯的制备方法 |
Publications (2)
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CN1680392A true CN1680392A (zh) | 2005-10-12 |
CN100497344C CN100497344C (zh) | 2009-06-10 |
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101134758B (zh) * | 2007-10-15 | 2010-04-14 | 桂林市振达生物科技有限责任公司 | 从银杏叶中提取分离银杏内酯a、b、c、j及白果内酯单体的方法 |
CN101392000B (zh) * | 2008-09-25 | 2010-12-22 | 成都普思生物科技有限公司 | 银杏内酯a、b、c、j和白果内酯单体的高效分离纯化方法 |
CN102093379A (zh) * | 2010-12-30 | 2011-06-15 | 上海同田生物技术有限公司 | 一种高纯度佛手柑内酯和补骨脂素的制备方法 |
CN102464666A (zh) * | 2010-11-09 | 2012-05-23 | 上海医药工业研究院 | 一种银杏内酯c的制备方法 |
CN102477023A (zh) * | 2010-11-30 | 2012-05-30 | 上海中药制药技术有限公司 | 高纯度5-羟基-3,7,4′-三甲氧基黄酮的制备方法 |
CN105061458A (zh) * | 2015-09-01 | 2015-11-18 | 合肥工业大学 | 一种无毒、高纯银杏总内酯及其单体的制备方法 |
CN105801600A (zh) * | 2016-04-14 | 2016-07-27 | 江苏康缘药业股份有限公司 | 一种白果内酯、银杏内酯a、银杏内酯b和银杏内酯c的制备方法 |
CN107129505A (zh) * | 2017-06-01 | 2017-09-05 | 陕西理工大学 | 一种银杏叶提纯物中内酯类成分高纯单体的工业制备方法 |
CN109053433A (zh) * | 2018-07-27 | 2018-12-21 | 山东省分析测试中心 | 一种组合制备银杏酸的方法 |
CN109053417A (zh) * | 2018-07-27 | 2018-12-21 | 山东省分析测试中心 | 一种高纯度银杏酸的制备方法 |
CN109303333A (zh) * | 2018-09-12 | 2019-02-05 | 珠海霍普金斯医药研究院股份有限公司 | 一种改善睡眠的保健品组合物 |
CN113801133A (zh) * | 2021-10-28 | 2021-12-17 | 江苏得乐康生物科技有限公司 | 一种银杏内酯及其所含单体的制备方法 |
-
2005
- 2005-01-07 CN CNB2005100231647A patent/CN100497344C/zh active Active
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101134758B (zh) * | 2007-10-15 | 2010-04-14 | 桂林市振达生物科技有限责任公司 | 从银杏叶中提取分离银杏内酯a、b、c、j及白果内酯单体的方法 |
CN101392000B (zh) * | 2008-09-25 | 2010-12-22 | 成都普思生物科技有限公司 | 银杏内酯a、b、c、j和白果内酯单体的高效分离纯化方法 |
CN102464666A (zh) * | 2010-11-09 | 2012-05-23 | 上海医药工业研究院 | 一种银杏内酯c的制备方法 |
CN102464666B (zh) * | 2010-11-09 | 2015-04-08 | 上海医药工业研究院 | 一种银杏内酯c的制备方法 |
CN102477023A (zh) * | 2010-11-30 | 2012-05-30 | 上海中药制药技术有限公司 | 高纯度5-羟基-3,7,4′-三甲氧基黄酮的制备方法 |
CN102477023B (zh) * | 2010-11-30 | 2014-04-09 | 上海中药制药技术有限公司 | 5-羟基-3,7,4′-三甲氧基黄酮的制备方法 |
CN102093379A (zh) * | 2010-12-30 | 2011-06-15 | 上海同田生物技术有限公司 | 一种高纯度佛手柑内酯和补骨脂素的制备方法 |
CN102093379B (zh) * | 2010-12-30 | 2015-08-05 | 上海同田生物技术股份有限公司 | 一种高纯度佛手柑内酯和补骨脂素的制备方法 |
CN105061458A (zh) * | 2015-09-01 | 2015-11-18 | 合肥工业大学 | 一种无毒、高纯银杏总内酯及其单体的制备方法 |
CN105801600A (zh) * | 2016-04-14 | 2016-07-27 | 江苏康缘药业股份有限公司 | 一种白果内酯、银杏内酯a、银杏内酯b和银杏内酯c的制备方法 |
CN107129505A (zh) * | 2017-06-01 | 2017-09-05 | 陕西理工大学 | 一种银杏叶提纯物中内酯类成分高纯单体的工业制备方法 |
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