CN104592343B - 一种从夏枯草中提取齐墩果酸的方法 - Google Patents
一种从夏枯草中提取齐墩果酸的方法 Download PDFInfo
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- CN104592343B CN104592343B CN201510083053.9A CN201510083053A CN104592343B CN 104592343 B CN104592343 B CN 104592343B CN 201510083053 A CN201510083053 A CN 201510083053A CN 104592343 B CN104592343 B CN 104592343B
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- Prior art keywords
- oleanolic acid
- spica prunellae
- method extracting
- ethanol solution
- microwave
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 title claims abstract description 35
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 title claims abstract description 35
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229940100243 oleanolic acid Drugs 0.000 title claims abstract description 35
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000284 extract Substances 0.000 claims abstract description 10
- 239000003208 petroleum Substances 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 3
- 229960004756 ethanol Drugs 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000003463 adsorbent Substances 0.000 claims description 12
- 238000004064 recycling Methods 0.000 claims description 10
- 238000000874 microwave-assisted extraction Methods 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 238000001179 sorption measurement Methods 0.000 claims description 6
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 238000003795 desorption Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 238000004088 simulation Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 4
- 102000011759 adducin Human genes 0.000 description 3
- 108010076723 adducin Proteins 0.000 description 3
- 238000005516 engineering process Methods 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
- DOUMFZQKYFQNTF-WUTVXBCWSA-N (R)-rosmarinic acid Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-WUTVXBCWSA-N 0.000 description 2
- 206010018498 Goitre Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 201000003872 goiter Diseases 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 description 1
- 206010051625 Conjunctival hyperaemia Diseases 0.000 description 1
- 206010010726 Conjunctival oedema Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000037319 Hepatitis infectious Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001529739 Prunella <angiosperm> Species 0.000 description 1
- ZZAFFYPNLYCDEP-HNNXBMFYSA-N Rosmarinsaeure Natural products OC(=O)[C@H](Cc1cccc(O)c1O)OC(=O)C=Cc2ccc(O)c(O)c2 ZZAFFYPNLYCDEP-HNNXBMFYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 235000011869 dried fruits Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000004438 eyesight Effects 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
- 231100000869 headache Toxicity 0.000 description 1
- 208000005252 hepatitis A Diseases 0.000 description 1
- 238000010262 high-speed countercurrent chromatography Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 201000007227 lymph node tuberculosis Diseases 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002966 pentacyclic triterpenoids Chemical class 0.000 description 1
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DOUMFZQKYFQNTF-MRXNPFEDSA-N rosemarinic acid Natural products C([C@H](C(=O)O)OC(=O)C=CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 DOUMFZQKYFQNTF-MRXNPFEDSA-N 0.000 description 1
- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 description 1
- 229940096998 ursolic acid Drugs 0.000 description 1
- 125000002220 ursolic acid group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
Claims (7)
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CN201510083053.9A CN104592343B (zh) | 2015-02-16 | 2015-02-16 | 一种从夏枯草中提取齐墩果酸的方法 |
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CN201510083053.9A CN104592343B (zh) | 2015-02-16 | 2015-02-16 | 一种从夏枯草中提取齐墩果酸的方法 |
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CN104592343A CN104592343A (zh) | 2015-05-06 |
CN104592343B true CN104592343B (zh) | 2016-08-17 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109912679A (zh) * | 2019-04-09 | 2019-06-21 | 山西师范大学 | 柿蒂提取熊果酸和齐墩果酸的方法 |
-
2015
- 2015-02-16 CN CN201510083053.9A patent/CN104592343B/zh active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109912679A (zh) * | 2019-04-09 | 2019-06-21 | 山西师范大学 | 柿蒂提取熊果酸和齐墩果酸的方法 |
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CN104592343A (zh) | 2015-05-06 |
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Effective date of registration: 20160602 Address after: 011517 the Inner Mongolia Autonomous Region Helingeer County of Hohhot city Shengle Economic Zone Applicant after: INNER MONGOLIA CHANGHUI BIOLOGICAL TECHNOLOGY Co.,Ltd. Address before: 010010, building 3, unit 7, Wanda District, Wanda Plaza, Xinhua East Street, the Inner Mongolia Autonomous Region, Hohhot, 602, China Applicant before: Bai Xinliang |
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Address after: 011517 Hohhot city Helingeer County Inner Mongolia Shengle economic Park Applicant after: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Address before: 011517 Hohhot city Helingeer County Inner Mongolia Shengle economic Park 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 Hohhot city Helingeer County Inner Mongolia Shengle economic Park Patentee before: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. |
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Denomination of invention: A method of extracting oleanolic acid from Prunella vulgaris Effective date of registration: 20210222 Granted publication date: 20160817 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: 20160817 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2021150000016 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method for extracting oleanolic acid from Prunella vulgaris Effective date of registration: 20220330 Granted publication date: 20160817 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2022150000027 |
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Date of cancellation: 20230301 Granted publication date: 20160817 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 Oleanolic Acid from Prunella vulgaris Effective date of registration: 20230307 Granted publication date: 20160817 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: 20160817 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000031 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
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Denomination of invention: A Method for Extracting Oleanolic Acid from Prunella vulgaris Effective date of registration: 20231101 Granted publication date: 20160817 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000154 |