CN100357251C - Technique for producing purple common perilla rosemary acid - Google Patents
Technique for producing purple common perilla rosemary acid Download PDFInfo
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- CN100357251C CN100357251C CNB200410075747XA CN200410075747A CN100357251C CN 100357251 C CN100357251 C CN 100357251C CN B200410075747X A CNB200410075747X A CN B200410075747XA CN 200410075747 A CN200410075747 A CN 200410075747A CN 100357251 C CN100357251 C CN 100357251C
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- rosmarinic acid
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- 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 title claims abstract description 97
- 238000000034 method Methods 0.000 title description 8
- 244000124853 Perilla frutescens Species 0.000 title description 3
- 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 claims abstract description 47
- 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 claims abstract description 47
- 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 claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000284 extract Substances 0.000 claims abstract description 10
- 239000011347 resin Substances 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000004347 Perilla Nutrition 0.000 claims abstract description 9
- 241000229722 Perilla <angiosperm> Species 0.000 claims abstract description 9
- 238000001179 sorption measurement Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012074 organic phase Substances 0.000 claims abstract description 6
- 239000003208 petroleum Substances 0.000 claims abstract description 5
- 238000003795 desorption Methods 0.000 claims abstract 3
- 239000000243 solution Substances 0.000 claims description 7
- 238000010828 elution Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 4
- 239000012141 concentrate Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000490 cosmetic additive Substances 0.000 abstract 1
- 239000003480 eluent Substances 0.000 abstract 1
- 235000013373 food additive Nutrition 0.000 abstract 1
- 239000002778 food additive Substances 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000009834 vaporization Methods 0.000 description 4
- 230000008016 vaporization Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- -1 phenolic acid compound Chemical class 0.000 description 2
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 1
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 1
- 108090000565 Capsid Proteins Proteins 0.000 description 1
- 102100023321 Ceruloplasmin Human genes 0.000 description 1
- 102000016942 Elastin Human genes 0.000 description 1
- 108010014258 Elastin Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000032041 Hearing impaired Diseases 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 241000207923 Lamiaceae Species 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 235000011449 Rosa Nutrition 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 1
- 229940074393 chlorogenic acid Drugs 0.000 description 1
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 1
- 235000001368 chlorogenic acid Nutrition 0.000 description 1
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920002549 elastin Polymers 0.000 description 1
- 210000003725 endotheliocyte Anatomy 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
本发明涉及一种可实现工业化大规模生产的紫苏迷迭香酸的生产工艺，以紫苏叶子为原料，将紫苏叶子浸泡于酸水中，过滤提取，将提取液上大孔吸附树脂柱吸附后解吸；将解吸液减压蒸发，得到纯度为10%的迷迭香酸产品；将10%纯度的迷迭香酸产品溶液用石油醚萃取，有机相减压蒸发浓缩得到纯度为50%的迷迭香酸产品；将50%纯度的迷迭香酸产品上吸附树脂柱，用不同浓度的乙醇溶液梯度洗脱，将95%组分洗脱液减压浓缩后结晶，即得到纯度为95%的迷迭香酸产品。本发明生产工艺简单，易操作，生产成本低，产品规格多，安全可靠，可用作食品添加剂、医药中间体和化妆品添加剂等领域。The invention relates to a production process of perilla rosmarinic acid capable of realizing industrialized large-scale production. Perilla leaves are used as raw materials, and the perilla leaves are soaked in acid water, filtered and extracted, and the extract is put on a macroporous adsorption resin column. Desorption after adsorption; evaporate the desorption solution under reduced pressure to obtain a rosmarinic acid product with a purity of 10%; extract the rosmarinic acid product solution with a purity of 10% with petroleum ether, and evaporate and concentrate the organic phase under reduced pressure to obtain a rosmarinic acid product with a purity of 50%. The rosmarinic acid product; the rosmarinic acid product of 50% purity is put on the adsorption resin column, and is eluted with the ethanol solution gradient of different concentrations, and 95% of the component eluent is concentrated under reduced pressure and then crystallized to obtain a purity of 95% rosmarinic acid product. The invention has simple production process, easy operation, low production cost, multiple product specifications, safety and reliability, and can be used in the fields of food additives, pharmaceutical intermediates, cosmetic additives and the like.
Description
Technical field:
But the present invention relates to a kind of technology of large-scale industrial production purple common perilla rosemary acid, belong to natural crops deep process technology field.
Technical background:
Rosmarinic acid (Rosmarinic acid is called for short RosA) is a kind of multi-functional phenolic acid compound, exists in the various plants of Labiatae, and it has multiple biological activity.Rosmarinic acid has the activity of extremely strong removing interior free yl as antioxidant, and its anti-oxidant activity is better than coffic acid, chlorogenic acid, folic acid, forulic acid, vitamin-E etc.; Rosmarinic acid can also suppress the oxidation of the low-density lipoprotein of endotheliocyte adjusting as antioxidant.Rosmarinic acid also has antiviral activity, and the pure water extract of discovery wood marchs such as Arda has the activity of anti-HIV, and the essential substance that wherein works is a rosmarinic acid; The research of Mazumder etc. shows that further rosmarinic acid can suppress the activity of HIV-1 (humanimmunodeficiency virus) intergrase; The research of Borkowski etc. shows that also rosmarinic acid is a kind of effective constituent of control simplexvirus, and its antiviral activity is except that the activity that suppresses virus some enzyme in life cycle, and it can also combine with virus capsid protein rapidly, thereby makes virally inactivated.In addition, rosmarinic acid also has otherwise function, and the extract that discoveries such as Lopes contain rosmarinic acid has good treatment effect to auditory disorder and hemorrhoid, and is free from side effects.Rosmarinic acid can suppress acute and chronic infection as the additive of makeup, and uvioresistant suppresses the degraded of elastin, increases cell membrane stability.Rosmarinic acid in the discovery reds sage root such as Zou Zhengwu also has the effect of antithrombotic and anti-platelet aggregation.The domestic and international at present research about rosmarinic acid has shown that it has important use and is worth in fields such as pharmacy, food, makeup, therefore many investigators are arranged all at chemosynthesis and the biosynthetic means of studying rosmarinic acid, but its method is loaded down with trivial details, the cost height is difficult to realize suitability for industrialized production.Also few to the research of extensive separating and purifying rosmarinic acid both at home and abroad now, therefore set up a kind of technology that can fast, simply produce rosmarinic acid and be necessary.
Summary of the invention:
Purpose of the present invention aims to provide a kind of technology that can the large-scale industrial production rosmarinic acid, this production technique is a raw material with natural phant purple perilla leaf, adopt acid extraction, absorption with macroporous adsorbent resin, wash-out, concentrate, steps such as extraction, crystallization, produce the rosmarinic acid of different purity, product safety is reliable, environmental protection can be widely used in various fields such as foodstuff additive, cosmetics additive and pharmaceutical.
In order to realize the foregoing invention purpose, concrete production technique of the present invention is as follows: (1) is soaked in the purple perilla leaf in the sour water, filters and extracts clear aqueous solution, and repeated multiple times is extracted, and with macroporous adsorptive resins absorption on the extracting solution, uses 95% alcohol desorb again; (2), obtain purity and be 10% rosmarinic acid product with the stripping liquid reduction vaporization; (3) with the rosmarinic acid product solution petroleum ether extraction of 10% purity, the organic phase reduction vaporization concentrates and obtains purity is 50% rosmarinic acid product; (4) with adsorption resin column on the rosmarinic acid product of 50% purity, use Different concentrations of alcohol solution gradient wash-out respectively, with 95% component elutriant concentrating under reduced pressure, crystallization under 4 ℃ of temperature condition obtains purity and is 95% rosmarinic acid product.
The outstanding advantage that the present invention compared with prior art has is: only promptly obtain purity by a cover technology and be respectively 10%, 50%, 95% rosmarinic acid, product specification is abundant, production technique is simple, and production cost is lower, is fit to realize the demand of large-scale industrial production.
Embodiment:
Below by embodiment production technique of the present invention is described further.
Embodiment 1:
The sour water of 20 kilograms of purple perilla leaves with pH2-4 extracted 4 hours under 40 ℃ of temperature condition, repeat to extract 3 times, XAD-4 macroporous adsorbent resin (10 * 80cm) on the united extraction liquid, use 95% alcohol desorb again, obtain 4 kilograms of stripping liquids, with stripping liquid concentrating under reduced pressure to 0.5 kilogram, promptly obtain purity and be 10% rosmarinic acid product; With the rosmarinic acid product petroleum ether extraction secondary of 200 grams, 10% purity, the organic phase reduction vaporization concentrates and to obtain 15 to restrain purity be 50% rosmarinic acid product; With AB-8 polymeric adsorbent (5 * 60cm) posts on the rosmarinic acid product of 4 grams, 50% purity, it with concentration respectively 30%, 95% ethanolic soln stepwise elution, with 95% component concentrating under reduced pressure to 3mL, crystallization under 4 ℃ of temperature condition, obtaining 1.9 gram purity is 95% rosmarinic acid product.
Embodiment 2:
The sour water of 300 kilograms of purple perilla leaves with pH2-4 extracted 4 hours under 40 ℃ of temperature condition, extract repeatedly 3 times, XAD-4 macroporous adsorptive resins (30 * 150cm) on the united extraction liquid, use 95% alcohol desorb again, obtain 40 kilograms of stripping liquids, with stripping liquid concentrating under reduced pressure to 3 kilogram, obtain purity and be 10% rosmarinic acid product; The rosmarinic acid of 2 kilogram of 10% purity with distilled water diluting to 5 kilogram, is used 2 kilograms of petroleum ether extractions three times respectively, merge organic phase, the organic phase reduction vaporization is concentrated to 0.38 kilogram, obtain purity and be 50% rosmarinic acid product; With AB-8 adsorption resin column on the rosmarinic acid of 100 grams, 50% purity, it with concentration respectively 30%, 95% ethanolic soln stepwise elution, again with 95% component elutriant concentrating under reduced pressure, crystallization under 4 ℃ of temperature condition obtains 45 gram purity and is 95% rosmarinic acid product.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200410075747XA CN100357251C (en) | 2004-12-23 | 2004-12-23 | Technique for producing purple common perilla rosemary acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200410075747XA CN100357251C (en) | 2004-12-23 | 2004-12-23 | Technique for producing purple common perilla rosemary acid |
Publications (2)
| Publication Number | Publication Date |
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| CN1796362A CN1796362A (en) | 2006-07-05 |
| CN100357251C true CN100357251C (en) | 2007-12-26 |
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| CNB200410075747XA Expired - Fee Related CN100357251C (en) | 2004-12-23 | 2004-12-23 | Technique for producing purple common perilla rosemary acid |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101186572B (en) * | 2007-12-19 | 2010-05-19 | 天津大学 | Method for one-step separation and purification of salvianolic acid from water extract of salvia miltiorrhiza |
| CN101401632B (en) * | 2008-04-14 | 2012-05-16 | 浙江工业大学 | Perilla seasoning liquid and preparation method thereof |
| CN102952018B (en) * | 2011-08-17 | 2014-08-27 | 湖北中烟工业有限责任公司 | Purification method of antioxidant rosmarinic acid for tobacco |
| CN102850219B (en) * | 2012-09-28 | 2014-06-18 | 中北大学 | Method for extracting rosmarinic acid from folia perillae acutae |
| CN103848740B (en) * | 2012-11-30 | 2015-12-09 | 沈阳药科大学 | A method for preparing rosmarinic acid from vegetable oil residue |
| CN103099845B (en) * | 2013-02-25 | 2015-03-11 | 中国农业科学院农业质量标准与检测技术研究所 | Method for extracting perillaseed hydrophilic chemical component from perillaseed oil residue |
| CN105315706B (en) * | 2015-12-11 | 2017-07-04 | 杨永 | A kind of natural pigment color stabilizer, preparation method and application |
| CN106565489A (en) * | 2016-10-10 | 2017-04-19 | 广西来宾绿翔生物科技有限公司 | Process for extracting rosmarinic acid from perilla |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1306815A (en) * | 2000-01-25 | 2001-08-08 | 殷芳 | Skin care cream with medical effect and its preparation |
| JP2001342489A (en) * | 2000-03-31 | 2001-12-14 | Sanei Gen Ffi Inc | Agent for suppressing deterioration of taste and flavor and method for suppressing deterioration of taste and flavor |
-
2004
- 2004-12-23 CN CNB200410075747XA patent/CN100357251C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1306815A (en) * | 2000-01-25 | 2001-08-08 | 殷芳 | Skin care cream with medical effect and its preparation |
| JP2001342489A (en) * | 2000-03-31 | 2001-12-14 | Sanei Gen Ffi Inc | Agent for suppressing deterioration of taste and flavor and method for suppressing deterioration of taste and flavor |
Non-Patent Citations (2)
| Title |
|---|
| 分光光度法测定苏叶中的迷迭香酸含量 杜桂彩等.青岛大学学报，第18卷第4期 2003 * |
| 紫苏愈伤组织迷迭香酸的纯化及抗菌活性研究 李荣贵等.微生物学报，第27卷第5期 2000 * |
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Application publication date: 20060705 Assignee: Shandong Tianyin Biotechnology Co., Ltd. Assignor: Qingdao University Contract record no.: 2010370000088 Denomination of invention: Technique for producing purple common perilla rosemary acid Granted publication date: 20071226 License type: Exclusive License Record date: 20100319 |
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