CN104788515A - 一种减压超声辅助提取制备高纯度水溶性橄榄苦甙的方法 - Google Patents
一种减压超声辅助提取制备高纯度水溶性橄榄苦甙的方法 Download PDFInfo
- Publication number
- CN104788515A CN104788515A CN201510162732.5A CN201510162732A CN104788515A CN 104788515 A CN104788515 A CN 104788515A CN 201510162732 A CN201510162732 A CN 201510162732A CN 104788515 A CN104788515 A CN 104788515A
- Authority
- CN
- China
- Prior art keywords
- oleuropein
- ethyl acetate
- condition
- extraction
- temperature
- Prior art date
- 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.)
- Granted
Links
- RFWGABANNQMHMZ-UHFFFAOYSA-N 8-acetoxy-7-acetyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline Natural products CC=C1C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O RFWGABANNQMHMZ-UHFFFAOYSA-N 0.000 title claims abstract description 60
- HKVGJQVJNQRJPO-UHFFFAOYSA-N Demethyloleuropein Natural products O1C=C(C(O)=O)C(CC(=O)OCCC=2C=C(O)C(O)=CC=2)C(=CC)C1OC1OC(CO)C(O)C(O)C1O HKVGJQVJNQRJPO-UHFFFAOYSA-N 0.000 title claims abstract description 60
- RFWGABANNQMHMZ-HYYSZPHDSA-N Oleuropein Chemical compound O([C@@H]1OC=C([C@H](C1=CC)CC(=O)OCCC=1C=C(O)C(O)=CC=1)C(=O)OC)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RFWGABANNQMHMZ-HYYSZPHDSA-N 0.000 title claims abstract description 60
- 235000011576 oleuropein Nutrition 0.000 title claims abstract description 60
- RFWGABANNQMHMZ-CARRXEGNSA-N oleuropein Natural products COC(=O)C1=CO[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(=CC)[C@H]1CC(=O)OCCc3ccc(O)c(O)c3 RFWGABANNQMHMZ-CARRXEGNSA-N 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000002137 ultrasound extraction Methods 0.000 title abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 23
- 238000005516 engineering process Methods 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001953 recrystallisation Methods 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 114
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000000284 extract Substances 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 24
- 240000007817 Olea europaea Species 0.000 claims description 23
- 235000002725 Olea europaea Nutrition 0.000 claims description 21
- 238000000967 suction filtration Methods 0.000 claims description 19
- 239000012043 crude product Substances 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000706 filtrate Substances 0.000 claims description 15
- 230000001476 alcoholic effect Effects 0.000 claims description 13
- 230000006837 decompression Effects 0.000 claims description 12
- 239000012535 impurity Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 238000004090 dissolution Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000001186 cumulative effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 238000002203 pretreatment Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 238000000746 purification Methods 0.000 abstract description 9
- 238000000926 separation method Methods 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 238000004042 decolorization Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 238000002604 ultrasonography Methods 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000002131 composite material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 6
- 239000002024 ethyl acetate extract Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 210000000630 fibrocyte Anatomy 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940114496 olive leaf extract Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 210000004927 skin cell Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 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
- 241000894006 Bacteria Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor 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
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 208000013507 chronic prostatitis Diseases 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000003248 hydroxytyrosol Nutrition 0.000 description 1
- 229940095066 hydroxytyrosol Drugs 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims (11)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510162732.5A CN104788515B (zh) | 2015-04-08 | 2015-04-08 | 一种减压超声辅助提取制备高纯度水溶性橄榄苦甙的方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510162732.5A CN104788515B (zh) | 2015-04-08 | 2015-04-08 | 一种减压超声辅助提取制备高纯度水溶性橄榄苦甙的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104788515A true CN104788515A (zh) | 2015-07-22 |
CN104788515B CN104788515B (zh) | 2020-09-01 |
Family
ID=53553745
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510162732.5A Expired - Fee Related CN104788515B (zh) | 2015-04-08 | 2015-04-08 | 一种减压超声辅助提取制备高纯度水溶性橄榄苦甙的方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104788515B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106046078A (zh) * | 2016-06-28 | 2016-10-26 | 郭舒洋 | 一种从油橄榄叶中提取橄榄苦苷的方法 |
CN107652336A (zh) * | 2017-11-01 | 2018-02-02 | 安徽龙津生物科技有限公司 | 一种高收率、高纯度橄榄苦苷的提取方法 |
CN109125182A (zh) * | 2018-10-16 | 2019-01-04 | 阿谷巴科技(唐山)有限公司 | 一种具有抑菌作用的橄榄苦甙护肤膏及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102702287A (zh) * | 2012-06-21 | 2012-10-03 | 桂林三宝药业有限公司 | 从橄榄叶中提取纯化橄榄苦甙的方法 |
CN102850416A (zh) * | 2012-09-07 | 2013-01-02 | 中国林业科学研究院林产化学工业研究所 | 一种油橄榄叶提取物的制备方法及所用装置 |
-
2015
- 2015-04-08 CN CN201510162732.5A patent/CN104788515B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102702287A (zh) * | 2012-06-21 | 2012-10-03 | 桂林三宝药业有限公司 | 从橄榄叶中提取纯化橄榄苦甙的方法 |
CN102850416A (zh) * | 2012-09-07 | 2013-01-02 | 中国林业科学研究院林产化学工业研究所 | 一种油橄榄叶提取物的制备方法及所用装置 |
Non-Patent Citations (1)
Title |
---|
谢普军等: "橄榄苦苷提取工艺的研究进展", 《生物质化学工程》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106046078A (zh) * | 2016-06-28 | 2016-10-26 | 郭舒洋 | 一种从油橄榄叶中提取橄榄苦苷的方法 |
CN107652336A (zh) * | 2017-11-01 | 2018-02-02 | 安徽龙津生物科技有限公司 | 一种高收率、高纯度橄榄苦苷的提取方法 |
CN109125182A (zh) * | 2018-10-16 | 2019-01-04 | 阿谷巴科技(唐山)有限公司 | 一种具有抑菌作用的橄榄苦甙护肤膏及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN104788515B (zh) | 2020-09-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101323648B (zh) | 一种桑黄粗多糖的提取方法及桑黄多糖的纯化方法 | |
CN108752231B (zh) | 从甜茶中提取茶氨酸以及同时提取甜茶苷和茶多酚的方法 | |
CN102250195B (zh) | 一种文冠果壳苷的生产方法 | |
CN102816066B (zh) | 一种从金银花叶中提取绿原酸和金丝桃苷的方法 | |
CN102532244A (zh) | 一种制备高纯度积雪草苷的方法 | |
CN102718737B (zh) | 一种用刺梨果肉制备刺梨原花青素的方法 | |
CN101797447A (zh) | 一种分离和提纯天然产物中有效成分的方法 | |
CN102617468A (zh) | 一种超声辅助提取高乌甲素的方法 | |
CN102106928B (zh) | 一种高纯度油茶皂苷的制备方法 | |
CN104098641B (zh) | 一种从罗汉果中提取罗汉果甙v的方法 | |
CN102432535A (zh) | 从千层塔中提取分离石杉碱甲和石杉碱乙的方法 | |
CN101982471B (zh) | 一种从杜仲果中提取桃叶珊瑚苷的工艺方法 | |
CN103012544B (zh) | 一种从油茶籽饼粕中提取皂素和多糖的方法 | |
CN104788515A (zh) | 一种减压超声辅助提取制备高纯度水溶性橄榄苦甙的方法 | |
CN102060856B (zh) | 一种从马铃果中提取柳叶水甘草碱的方法 | |
CN102093748A (zh) | 用红心萝卜制备萝卜红色素单聚体及萝卜原花青素的方法 | |
CN101967119A (zh) | 一种槟榔碱的提纯方法 | |
CN102060905A (zh) | 利用鲜海参加工废液制备海参皂苷Holotoxin A1对照品的工艺方法 | |
CN104119229A (zh) | 一种制取纯品绿原酸的工艺 | |
CN103044504B (zh) | 一种从草苁蓉中提取草苁蓉甙的方法 | |
CN105732741A (zh) | 紫苏叶提取花色苷和熊果酸的方法 | |
CN103333213B (zh) | 从油橄榄叶中提取橄榄苦甙的方法 | |
CN104876999A (zh) | 一种亚临界水提取白桦脂酸的方法 | |
CN104774139A (zh) | 一种超声辅助原位萃取天然羟基酪醇的方法 | |
CN101696381B (zh) | 青稞黄酮提取物的制备工艺及其在保健酒中的应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
DD01 | Delivery of document by public notice |
Addressee: Chen Fuwen Document name: Notification of Passing Preliminary Examination of the Application for Invention |
|
C06 | Publication | ||
PB01 | Publication | ||
DD01 | Delivery of document by public notice |
Addressee: Chen Fuwen Document name: Notification of Publication of the Application for Invention |
|
CB03 | Change of inventor or designer information |
Inventor after: Shi Gaofeng Inventor after: Chen Fuwen Inventor after: Wang Guoying Inventor after: Yao Ruixing Inventor before: Chen Fuwen Inventor before: Shi Gaofeng Inventor before: Wang Guoying Inventor before: Zhao Guochao Inventor before: Yao Ruixing |
|
CB03 | Change of inventor or designer information | ||
TA01 | Transfer of patent application right | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20170926 Address after: 730050 Qilihe, Gansu Province Lan Ping Ping Road, No. 287, No. Applicant after: Lanzhou University Of Technology Address before: 730900 incubator base of hi tech Industrial Park, Baiyin District, Baiyin, Gansu Applicant before: Chen Fuwen |
|
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20200901 Termination date: 20210408 |
|
CF01 | Termination of patent right due to non-payment of annual fee |