CN103145655A - 一种高纯度牛蒡苷元的制备方法 - Google Patents
一种高纯度牛蒡苷元的制备方法 Download PDFInfo
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- CN103145655A CN103145655A CN2013100061797A CN201310006179A CN103145655A CN 103145655 A CN103145655 A CN 103145655A CN 2013100061797 A CN2013100061797 A CN 2013100061797A CN 201310006179 A CN201310006179 A CN 201310006179A CN 103145655 A CN103145655 A CN 103145655A
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- Prior art keywords
- aretigenin
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- ethyl acetate
- sherwood oil
- arctigenin
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- 238000002360 preparation method Methods 0.000 title claims abstract description 39
- NQWVSMVXKMHKTF-UHFFFAOYSA-N L-Arctigenin Natural products C1=C(OC)C(OC)=CC=C1CC1C(CC=2C=C(OC)C(O)=CC=2)C(=O)OC1 NQWVSMVXKMHKTF-UHFFFAOYSA-N 0.000 title abstract description 11
- NQWVSMVXKMHKTF-JKSUJKDBSA-N (-)-Arctigenin Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1[C@@H](CC=2C=C(OC)C(O)=CC=2)C(=O)OC1 NQWVSMVXKMHKTF-JKSUJKDBSA-N 0.000 title abstract 7
- YYGRXNOXOVZIKE-UHFFFAOYSA-N Arctigenin Natural products COC1CCC(CC2COC(=O)C2CC3CCC(O)C(C3)OC)CC1OC YYGRXNOXOVZIKE-UHFFFAOYSA-N 0.000 title abstract 7
- OIFFJDGSLVHPCW-UHFFFAOYSA-N Guayarol Natural products COc1ccc(CC2C(Cc3ccc(O)c(O)c3)COC2=O)cc1OC OIFFJDGSLVHPCW-UHFFFAOYSA-N 0.000 title abstract 7
- NWFYESYCEQICQP-UHFFFAOYSA-N methylmatairesinol Natural products C1=C(OC)C(OC)=CC=C1CC1C(=O)OCC1CC1=CC=C(O)C(OC)=C1 NWFYESYCEQICQP-UHFFFAOYSA-N 0.000 title abstract 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 78
- 240000005528 Arctium lappa Species 0.000 claims abstract description 27
- 235000003130 Arctium lappa Nutrition 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000004262 preparative liquid chromatography Methods 0.000 claims abstract description 11
- 239000002024 ethyl acetate extract Substances 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 238000005238 degreasing Methods 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 239000000284 extract Substances 0.000 claims description 7
- 239000004519 grease Substances 0.000 claims description 6
- 238000010829 isocratic elution Methods 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000010298 pulverizing process Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- XOJVHLIYNSOZOO-SWOBOCGESA-N Arctiin Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1[C@@H](CC=2C=C(OC)C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=CC=2)C(=O)OC1 XOJVHLIYNSOZOO-SWOBOCGESA-N 0.000 abstract description 17
- BPYGTFFYYOWDBC-LOVSFRALSA-N arctiin Natural products COc1ccc(C[C@H]2COC(=O)[C@@H]2Cc3ccc(O[C@@H]4O[C@H](C)[C@@H](O)[C@H](O)[C@H]4O)c(OC)c3)cc1OC BPYGTFFYYOWDBC-LOVSFRALSA-N 0.000 abstract description 17
- 239000000470 constituent Substances 0.000 abstract description 7
- 238000002474 experimental method Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 235000008078 Arctium minus Nutrition 0.000 abstract description 3
- 238000004440 column chromatography Methods 0.000 abstract description 3
- 238000013461 design Methods 0.000 abstract description 3
- 239000012043 crude product Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000012071 phase Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000013078 crystal Substances 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
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- 239000003960 organic solvent Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 3
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- -1 4-hydroxy-3-methoxyphenyl Chemical group 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010007247 Carbuncle Diseases 0.000 description 1
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 1
- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 1
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 235000000604 Chrysanthemum parthenium Nutrition 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 101000925662 Enterobacteria phage PRD1 Endolysin Proteins 0.000 description 1
- 201000000297 Erysipelas Diseases 0.000 description 1
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- 108060004795 Methyltransferase Proteins 0.000 description 1
- 208000005647 Mumps Diseases 0.000 description 1
- 206010062575 Muscle contracture Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
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- 206010039966 Senile dementia Diseases 0.000 description 1
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- 241000700605 Viruses Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 208000006111 contracture Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 235000008384 feverfew Nutrition 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000010805 mumps infectious disease Diseases 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- 231100000765 toxin Toxicity 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103509741A (zh) * | 2013-08-22 | 2014-01-15 | 河北农业大学 | 布劳特菌auh-jld56及其在牛蒡苷元转化中的应用 |
CN104447234A (zh) * | 2014-12-08 | 2015-03-25 | 安徽万邦医药科技有限公司 | (3r,4r)-4-(3,4-二甲氧基苄基)-3-(4-羟基-3-甲氧基苄基)-二氢呋喃的制备方法 |
CN105001090A (zh) * | 2015-07-01 | 2015-10-28 | 安徽万邦医药科技有限公司 | 一种4-乙酰氧基-3-(3,4-二甲氧基-苄基)-2-(4-羟基-3-甲氧基-苄基)-丁-2-烯酸甲酯的制备方法 |
CN105503785A (zh) * | 2014-09-26 | 2016-04-20 | 山东新时代药业有限公司 | 一种工业化规模制备高纯度牛蒡子苷元的方法 |
CN108440459A (zh) * | 2018-04-03 | 2018-08-24 | 徐州工程学院 | 一种高效提取牛蒡子苷元的方法 |
CN109061021A (zh) * | 2018-07-09 | 2018-12-21 | 西南民族大学 | 一种从牛蒡中分离或分析酚酸类化合物的方法 |
CN112876444A (zh) * | 2021-01-15 | 2021-06-01 | 北京澳特舒尔保健品开发有限公司 | 一种二氢杨梅素和牛蒡苷的联合提取方法及其在清咽产品中的应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1569138A (zh) * | 2004-05-13 | 2005-01-26 | 上海交通大学 | 具有降血糖作用的牛蒡子提取物的制备方法 |
CN1864705A (zh) * | 2005-05-16 | 2006-11-22 | 上海诺仁生物医药技术有限公司 | 一种牛蒡子提取物及其制备方法和应用 |
KR20080107794A (ko) * | 2007-06-08 | 2008-12-11 | 경남대학교 산학협력단 | 우방자 추출물을 함유하는 항암 조성물 |
CN101748169A (zh) * | 2010-01-12 | 2010-06-23 | 南京泽朗医药科技有限公司 | 一种从牛蒡子中制备牛蒡子苷元的方法 |
-
2013
- 2013-01-09 CN CN201310006179.7A patent/CN103145655B/zh not_active Expired - Fee Related
Patent Citations (4)
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CN1569138A (zh) * | 2004-05-13 | 2005-01-26 | 上海交通大学 | 具有降血糖作用的牛蒡子提取物的制备方法 |
CN1864705A (zh) * | 2005-05-16 | 2006-11-22 | 上海诺仁生物医药技术有限公司 | 一种牛蒡子提取物及其制备方法和应用 |
KR20080107794A (ko) * | 2007-06-08 | 2008-12-11 | 경남대학교 산학협력단 | 우방자 추출물을 함유하는 항암 조성물 |
CN101748169A (zh) * | 2010-01-12 | 2010-06-23 | 南京泽朗医药科技有限公司 | 一种从牛蒡子中制备牛蒡子苷元的方法 |
Non-Patent Citations (2)
Title |
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SZOKOL-BORSODI LILLA 等: "Optimum yields of dibenzylbutyrolactone-type lignans from Cynareae fruits, during their ripening, germination and enzymatic hydrolysis processes, determined by on-line chromatographic methods", 《PHYTOCHEMICAL ANALYSIS: PCA》 * |
鞠玫君: "牛蒡子中木脂素类成分的提取工艺研究", 《医药卫生科技辑》 * |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103509741A (zh) * | 2013-08-22 | 2014-01-15 | 河北农业大学 | 布劳特菌auh-jld56及其在牛蒡苷元转化中的应用 |
CN103509741B (zh) * | 2013-08-22 | 2015-02-18 | 河北农业大学 | 布劳特菌auh-jld56及其在牛蒡苷元转化中的应用 |
CN105503785A (zh) * | 2014-09-26 | 2016-04-20 | 山东新时代药业有限公司 | 一种工业化规模制备高纯度牛蒡子苷元的方法 |
CN105503785B (zh) * | 2014-09-26 | 2019-05-10 | 山东新时代药业有限公司 | 一种工业化规模制备高纯度牛蒡子苷元的方法 |
CN104447234A (zh) * | 2014-12-08 | 2015-03-25 | 安徽万邦医药科技有限公司 | (3r,4r)-4-(3,4-二甲氧基苄基)-3-(4-羟基-3-甲氧基苄基)-二氢呋喃的制备方法 |
CN105001090A (zh) * | 2015-07-01 | 2015-10-28 | 安徽万邦医药科技有限公司 | 一种4-乙酰氧基-3-(3,4-二甲氧基-苄基)-2-(4-羟基-3-甲氧基-苄基)-丁-2-烯酸甲酯的制备方法 |
CN108440459A (zh) * | 2018-04-03 | 2018-08-24 | 徐州工程学院 | 一种高效提取牛蒡子苷元的方法 |
CN108440459B (zh) * | 2018-04-03 | 2021-03-02 | 徐州工程学院 | 一种提取牛蒡子苷元的方法 |
CN109061021A (zh) * | 2018-07-09 | 2018-12-21 | 西南民族大学 | 一种从牛蒡中分离或分析酚酸类化合物的方法 |
CN112876444A (zh) * | 2021-01-15 | 2021-06-01 | 北京澳特舒尔保健品开发有限公司 | 一种二氢杨梅素和牛蒡苷的联合提取方法及其在清咽产品中的应用 |
CN112876444B (zh) * | 2021-01-15 | 2022-02-01 | 北京澳特舒尔保健品开发有限公司 | 一种二氢杨梅素和牛蒡苷的联合提取方法及其在清咽产品中的应用 |
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