CN102199092A - Production technology for acquiring two antioxidant agents from Rosmarinus officinalis L. - Google Patents
Production technology for acquiring two antioxidant agents from Rosmarinus officinalis L. Download PDFInfo
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- CN102199092A CN102199092A CN201010132432XA CN201010132432A CN102199092A CN 102199092 A CN102199092 A CN 102199092A CN 201010132432X A CN201010132432X A CN 201010132432XA CN 201010132432 A CN201010132432 A CN 201010132432A CN 102199092 A CN102199092 A CN 102199092A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
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Abstract
The invention discloses a production technology employing a ultrasonic countercurrent extraction process and a membrane separation (molecular sieve) process to acquire two antioxidants from Rosmarinus officinalis L. The production technology comprises adding 30 to 85% of edible alcohol into fresh rosemary branches and leaves, carrying out a ultrasonic counter current extraction process for a mixture of the edible alcohol and the fresh rosemary branches and leaves to obtain an extracted liquid with a solid-to-liquid ratio of from 1:10 to 1:30, and carrying out a membrane separation (molecular sieve) process to separate two antioxidant agents consisting of a rosemary fat-soluble antioxidant agent (comprising carnosic acid as a representative) and a rosemary water-soluble antioxidant agent (comprising rosmarinic acid as a representative) from the extracted liquid, wherein a heating time of the extracted liquid can be reduced through the membrane separation (molecular sieve) process thus a conversion ratio of rosmarinic acid to carnosol is reduced. A content of carnosic acid in the rosemary fat-soluble antioxidant agent is increased through a CO2 supercritical extraction process. The rosemary water-soluble antioxidant agent (comprising rosmarinic acid as a representative) is separated from a liquid obtained through a concentration process under reduced pressure and a solid-liquid separation process, and a content of rosmarinic acid in the rosemary water-soluble antioxidant agent is increased through recrystallization from ethanol. The production technology has the advantages of simple processes, low energy consumption, high production efficiency, production safety, and no harmful residual solvent due to single edible alcohol usage during all production processes.
Description
Technical field:
The extraction separation that the invention belongs to the high-activity natural antioxidant substance is made the field, and special design separates the production technique that obtains two kinds of antioxidants in the labiate Rosmarinus officinalis.
Background technology:
Rosmarinus officinalis (Rosmarinus officinalis L) is a labiate, be the perennial evergreen undershrub, the country of origin is Europe, north African and Mediterranean Sea bank, and main product state is France, Spain, Yugoslavia and Italy etc., and extensively cultivate various countries, the whole world now.
It is documented that in three state King Wen Wei periods, Rosmarinus officinalis is introduced China from the Western Regions, " the Rosmarinus officinalis tax " of Cao Zhi is exactly good proof.Beijing plant institute of the Chinese Academy of Sciences has successfully introduced a fine variety Rosmarinus officinalis in 1981.This plant requires very low to soil, be suitable for the cultivation of deserted mountain and dead soil, and the bright product of per mu yield can reach more than 1500 kilograms.Because of Rosmarinus officinalis can give out unique fragrance, and have higher ornamental value,, some or soil and slope protection, the desirable kind of controlling soil erosion are arranged wherein so it becomes the common afforestation cultivated plant of Mediterranean Sea coastwise contries.Warm, the sunny airy environment of Rosmarinus officinalis happiness.Anti-morning, winter resistance are good, and general temperature can normally survived the winter more than～10 ℃, intolerant to waterlogging, and the month seedling jaundice fallen leaves of excessive rainfall, well developed root system divides principal stresses strong.
Rosmarinus officinalis effective constituent
1. flavonoid
6 one chrysoeriols, 5-hydroxyl one 7,4 one dimethoxy flavones, 5,4 one dihydroxyl, one 7 one methoxy flavones.
2. terpene
2.1 monoterpene and sesquiterpenoids are the derived essential oil of common aromatising flavour.
2.2 diterpenes: be mainly the diterpene phenolic compound.Diterpenes is oxidation resistant main active ingredient: Rosmarinus officinalis phenol, table Rosmarinus officinalis phenol, carnosol, Rosmarinus officinalis dialdehyde, Salvin, Rosmarinus officinalis diphenol etc.
3. acidic component: rosmarinic acid, ursolic acid, neat big and heavy stone tartaric acid, coffic acid, chlorogenic acid etc.
As far back as twentieth century beginning of the fifties, people such as Chipault study with regard to the anti-oxidant activity of 32 kinds of spices, and Rosmarinus officinalis and Salvia japonica Thunb. are very praised highly.The Rosmarinus plant by many developed countries in the world or area drop into a large amount of financial resources as the economical plant of preciousness, manpower is studied, and has obtained very big achievement.It is documented these researchs comprise fundamental research by the forming of the extraction of Rosmarinus officinalis effective constituent and effective constituent, antioxidation mechanism etc.; Applied research comprises foodstuffs industry, daily-use chemical industry, medicines and health protection etc.Wherein, France, the U.S. and Japan starting drop into maximumly the earliest, and the scope of research mainly concentrates on cultivation technique, cottage propagation, tissue culture fast-propagation and in the comprehensive exploitation utilisation technology of environmental improvement, medicine, aspect such as anticorrosion etc.1980, the investment that the U.S. is used for this intermediate item reaches 5,400 ten thousand dollars, since the eighties, the U.S. and Japan have tentatively finished the extraction process of antioxidant, successively release the Rosmarinus officinalis series product, be widely used in being favourably welcome in American-European market on fried food product, rich oil food, each quasi-grease preservation and medicine, the makeup, just progressively replace the synthetic antioxidant at present.
Synthetic antioxidant butyl hydroxyanisole (BHA), butylated hydroxytoluene (BHT), Tenox PG (PG) and Tert. Butyl Hydroquinone (TBHQ) cause savings to poison to liver and kidney.Present many countries have limited the quantity of or have banned use of synthetic antioxidant to the human body toxic side effect, have banned use of BHA, BHT, TBHQ such as Northern Europe, the use of also having limited the quantity of of the U.S., Japan and the Western European countries.Rosemary antioxidant is in animal-plant oil, rich oil food and meat product, has the effect that prevention and delay are become sour or prolonged preservation period, and the toxic side effect of synthetized oxidation preventive agent and the weakness that heat is decomposed have thoroughly been avoided, the fried test of toxicological experiment and high temperature shows for 240 ℃, safe, efficient, heat-resisting, characteristics such as antioxidant effect is good, wide spectrum that rosemary antioxidant has, LD50 is the 20g/kg body weight.
Modern pharmacological research proves: contained diterpene phenols composition in the Rosmarinus officinalis, have significantly anti-oxidant, antitumor, anti AIDS virus, keep away mosquito and other multiple microbic activity, except that using, be expected to develop antitumor, the anti-AIDS that becomes high-efficiency low-toxicity, keep away medicine such as mosquito as antioxidant.
Rosmarinus officinalis resistance of oxidation have anti-aging effects, the Chinese medicine voluminous dictionary: Rosmarinus officinalis has strong function.Anti-hepatitis and hepatoprotective effect and the ability of relieving the effect of alcohol.Enzyme falls, to fall turbid effect remarkable, the fine selection of treatment fatty liver alcoholic liver, prevention liver cirrhosis.
That rosmarinic acid has is significantly analgesic, analgesia, anti-inflammatory, anti-oxidant, antithrombotic and fibrinolytic activity, and Germany puts on market as analgesic, analgesia, anti-inflammatory drug at present, and is expected exploitation and becomes the antithrombotic new drug.Nineteen eighty-three, European countries just extracted the medicine that drug development goes out to treat varix, hemorrhoid, eczema, psoriasis, psoriatic and skin infections etc. with Rosmarinus officinalis.
Current rosemary antioxidant production technology defective:
The main antioxidant composition of Rosmarinus officinalis is Salvin and rosmarinic acid, Salvin is extremely unstable, endophytic enzyme, temperature, oxygen in the extracting solution etc. all can cause the conversion of Salvin, studies show that: the Rosmarinus officinalis leaf is in drying, distillation, in the crushing process, the content of Salvin descends about 10～20%, from to Salvin in the Rosmarinus officinalis and carnosol mass ratio, bright leaf is 10: 1, shady and cool cured leaf 8: 1, extract 6: 1, the rosemary antioxidant product of some company can reach 1: 1, this explanation Salvin is very easy to transform to carnosol, in addition the rosemary extract of some company with the content of carnosol as product index.
So reduce the conversion of Salvin to carnosol, the content that improves Salvin is exactly advanced part of the present invention.
Summary of the invention:
The present invention adopts ultrasonic adverse current and membrane sepn (molecular sieve) technological method, directly from the bright branches and leaves of Rosmarinus officinalis, add 30～85% and use alcohol, under lower temperature, from extracting solution once, isolate two kinds of components, Rosmarinus officinalis fat-soluble (Salvin is representative) and water-soluble (rosmarinic acid is representative) antioxidant have reduced the conversion of rosmarinic acid to carnosol.The strong cavitation effect that ultrasonic wave produces forms many little holes in the medium, several thousand atmospheric pressure of these little hole closed generations of moment impel plant cell tissue's broken wall, quicken stripping, the diffusion of effective constituent.Adopt ultrasonic reverse flow technique to solve bright Rosmarinus officinalis raw material and be difficult for the lixiviate problem, the solid-liquid ratio that strengthens material can obtain higher concentration difference, helps the diffusion and the dissolving of target component, helps carrying out under lower temperature environments.
Membrane separation technique can separate under the normal temperature in molecular range and concentrate, and this process is a kind of physical process, the variation of phase need not take place and add auxiliary agent, the difference (or being called molecular weight cut-off) according to its aperture can be divided into film microfiltration membrane, ultra-filtration membrane, nanofiltration membrane and reverse osmosis membrane; Chlorophyll is the major impurity composition of rosemary extract, and molecular weight is bigger, adopts membrane sepn to remove effectively, and the efficient in operation under the normal temperature prevents the conversion of Salvin.
Supercritical CO
2Fluid extraction (SFE) is directly used in the extraction of Rosmarinus officinalis raw material, and cost is very high; But promoting product quality for the thick rosemary extract of content 20～40% as raw material is extraordinary selection.
Overall this invented technology is simple, energy consumption is low, production efficiency increases substantially, because whole process is only used edible ethanol, so the exhausted deleterious vehicle substance of noresidue of extract, thereby prevented the existence of harmful thing in the leaching process and, guaranteed 100% pure natural property the pollution of environment.
1, raw material directly adopts bright leaf or bright branches and leaves, is cut into section greater than 0.25cm with the bright leaf of Rosmarinus officinalis or with the bright branches and leaves of Rosmarinus officinalis.
2, use ultrasonic countercurrent extraction, extraction solvent is 30～85% edible ethanols, and the solid-liquid ratio is 1: 10～1: 30, extracts 15～65 ℃ of temperature, 30 minutes extraction times.
3, (membrane pore size is at 10nm～50nm) filter, and filtrate refilters and the sodium filter through rolled film, obtains holding back of different molecular weight through tubular membrane or ceramic membrane for extracting solution.
4, the non-liquid that sees through is evaporated to the appearance precipitation or does not have the ethanol flavor, and solid-liquid separation obtains solid substance A and liquid B.
5, the spray-dried Rosmarinus officinalis fat-soluble antioxidant (Salvin content 20～40%) that obtains of solid substance A, resultant Rosmarinus officinalis fat-soluble antioxidant is through CO
2Overcritical extracting and separating again obtains the Rosmarinus officinalis fat-soluble antioxidant of Salvin high-content (40～80%).
6, liquid B is used macroporous resin adsorption, and 40,50,60,70,80% ethanol gradient desorption is attached, and desorb attached liquid concentrating under reduced pressure after the spraying drying, is used the dehydrated alcohol recrystallization, obtains the above product of rosmarinic acid 90% content.
Case study on implementation 1
100 kilograms on the bright leaf of Rosmarinus officinalis, ultrasonic counter-current extraction, extraction solvent is 65% alcohol, extract 40 ℃ of temperature, solid-liquid ratio 1: 25, the extracting solution centrifugation, with 50nm aperture membrane filtration, filtrate is through 50000 molecular weight and 10000 molecular weight, again to 500 molecular weight, do not see through liquid and be evaporated to alcohol-free flavor, solid-liquid separation, appropriate amount of deionized water washing, resulting liquid is deposited standby in addition, the solid substance spraying drying obtains Salvin content and is 3.5 kilograms of 20～40% Rosmarinus officinalis fat-soluble antioxidants (crude product), crude product CO
2Supercritical extraction obtains 1.1 kilograms of the Rosmarinus officinalis fat-soluble antioxidants of Salvin content 60～80%.
Above-mentioned standby liquid is used macroporous resin adsorption, and 40,50,60,70,80% ethanol gradient desorption is attached, and desorb attached liquid concentrating under reduced pressure after the spraying drying, is used the dehydrated alcohol recrystallization, obtains 0.8 kilogram of the above product of rosmarinic acid 90% content.
Case study on implementation 2
200 kilograms in the bright branches and leaves of Rosmarinus officinalis, segment 0.5～5cm, ultrasonic counter-current extraction, extraction solvent is 65% alcohol, extract 40 ℃ of temperature, solid-liquid ratio 1: 30, extracting solution centrifugation, with 50nm aperture membrane filtration, filtrate, does not see through liquid and is evaporated to alcohol-free flavor again to 500 molecular weight through 50000 molecular weight and 10000 molecular weight, solid-liquid separation, the appropriate amount of deionized water washing, resulting liquid is deposited standby in addition, the solid substance spraying drying, obtain Salvin content and be 3.5 kilograms of 20～40% Rosmarinus officinalis fat-soluble antioxidants (crude product), crude product CO
2Supercritical extraction obtains 1.1 kilograms of the Rosmarinus officinalis fat-soluble antioxidants of Salvin content 60～80%.
Above-mentioned standby liquid is used macroporous resin adsorption, and 40,50,60,70,80% ethanol gradient desorption is attached, and desorb attached liquid concentrating under reduced pressure after the spraying drying, is used the dehydrated alcohol recrystallization, obtains 0.8 kilogram of the above product of rosmarinic acid 90% content.
Claims (6)
1. extract the production technique of antioxidant in the Rosmarinus officinalis, be primarily characterized in that technique manufacturing method is as follows:
(1) raw material directly adopts bright leaf or bright branches and leaves, is cut into section greater than 0.25cm with the bright leaf of Rosmarinus officinalis or with the bright branches and leaves of Rosmarinus officinalis;
(2) use ultrasonic countercurrent extraction, extraction solvent is 30～85% edible ethanols, and the solid-liquid ratio is 1: 10～1: 30, extracts 15～75 ℃ of temperature, 30 minutes extraction times;
(3) (membrane pore size is at 10nm～50nm) filter, and filtrate refilters and the sodium filter through rolled film, obtains holding back of different molecular weight through tubular membrane or ceramic membrane for extracting solution;
(4) the non-liquid that sees through is evaporated to the appearance precipitation or does not have the ethanol flavor, and solid-liquid separation obtains solid substance A and liquid B.
(5) the spray-dried Rosmarinus officinalis fat-soluble antioxidant (Salvin content 20～40%) that obtains of solid substance A, resultant Rosmarinus officinalis fat-soluble antioxidant is through CO
2Overcritical extracting and separating again obtains the Rosmarinus officinalis fat-soluble antioxidant of Salvin high-content (40～80%);
(6) liquid B is used macroporous resin adsorption, and 40,50,60,70,80% ethanol gradient desorption is attached, and desorb attached liquid concentrating under reduced pressure after the spraying drying, is used the dehydrated alcohol recrystallization, obtains the above product of rosmarinic acid 90% content.
2. according to (1) bright leaf of claims 1 or be cut into bright branches and leaves of section greater than 0.25cm.
3. according to (2) the ultrasonic countercurrent extraction method and the ethanol concn 30～85% of claims 1, extract liquid measure by strengthening, reverse flow technique obtains the concentration difference of bigger Rosmarinus officinalis with extracting solution, reduces Rosmarinus officinalis extraction time, thereby reduces the carnosol that is converted into of Salvin.
4. (3) membrane sepn according to claims 1 concentrates and the separation method use.
5. according to the spray drying process and the CO of (5) of claims 1
2Supercritical extraction separates the method for low levels rosemary antioxidant to be used.
6. echoing the dehydrated alcohol recrystallization method according to 40,50,60,70,80% ethanol gradient desorption in (6) of claims 1 uses.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010132432XA CN102199092A (en) | 2010-03-26 | 2010-03-26 | Production technology for acquiring two antioxidant agents from Rosmarinus officinalis L. |
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| CN201010132432XA CN102199092A (en) | 2010-03-26 | 2010-03-26 | Production technology for acquiring two antioxidant agents from Rosmarinus officinalis L. |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103966027A (en) * | 2014-05-15 | 2014-08-06 | 嘉兴市得百科新材料科技有限公司 | Preparation method of compound rosemary extract |
| CN104939267A (en) * | 2014-03-25 | 2015-09-30 | 湖南今汉生物医药技术有限公司 | Rosemary extract composition and application thereof as preservative |
| CN106831403A (en) * | 2017-01-18 | 2017-06-13 | 河南佳尚农业科技发展有限公司 | It is a kind of that fat-soluble and water soluble antioxidant method is extracted from rosemary |
| CN107739306A (en) * | 2017-09-11 | 2018-02-27 | 湖南鑫利生物科技有限公司 | A kind of processing method for preparing refined Rosmarinus officinalis extract |
| CN107739305A (en) * | 2017-09-11 | 2018-02-27 | 湖南鑫利生物科技有限公司 | A kind of method for improving carnosic acid content in rosemary fat-soluble antioxidant |
| CN108048220A (en) * | 2017-12-19 | 2018-05-18 | 贵州航天乌江机电设备有限责任公司 | A kind of method of low temperature extraction rosemary oil |
| CN108338406A (en) * | 2018-02-13 | 2018-07-31 | 玉溪开元金蓝生物科技有限责任公司 | A kind of quick-fried pearl of rosemary antioxidant and its application in cigarette filter rod |
| CN110100910A (en) * | 2019-05-30 | 2019-08-09 | 河南农业大学 | A kind of woody edible oil and its processing method |
| CN110862315A (en) * | 2019-12-06 | 2020-03-06 | 湖南先伟实业有限公司 | By using supercritical CO2Method for extracting carnosic acid from rosemary leaves |
| WO2021038340A1 (en) * | 2019-08-26 | 2021-03-04 | Tübi̇tak | Carnosic acid, carnosol and rosmarinic acid isolation method |
| CN113200857A (en) * | 2021-03-19 | 2021-08-03 | 河南华牧生物科技有限公司 | Process for purifying origanum rosemarium acid antioxidant by two-phase solvent extraction method |
| CN113480592A (en) * | 2021-06-09 | 2021-10-08 | 湖南鑫利生物科技有限公司 | Method for preparing rosemary ursolic acid |
| CN114702378A (en) * | 2022-05-10 | 2022-07-05 | 南京泛成生物科技有限公司 | Method for preparing rosemary extract by using two-aqueous-phase extraction method |
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| CN1441030A (en) * | 2003-01-20 | 2003-09-10 | 马文彬 | Method of extracting rosemary as matural antioxidant |
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| CN104939267B (en) * | 2014-03-25 | 2019-07-23 | 湖南今汉药业有限公司 | A kind of rosemary extraction composition and its application as antistaling agent |
| CN104939267A (en) * | 2014-03-25 | 2015-09-30 | 湖南今汉生物医药技术有限公司 | Rosemary extract composition and application thereof as preservative |
| CN103966027B (en) * | 2014-05-15 | 2016-06-29 | 青岛金智高新技术有限公司 | A kind of preparation method of the composite extract of Herba Rosmarini Officinalis |
| CN103966027A (en) * | 2014-05-15 | 2014-08-06 | 嘉兴市得百科新材料科技有限公司 | Preparation method of compound rosemary extract |
| CN106831403A (en) * | 2017-01-18 | 2017-06-13 | 河南佳尚农业科技发展有限公司 | It is a kind of that fat-soluble and water soluble antioxidant method is extracted from rosemary |
| CN107739306A (en) * | 2017-09-11 | 2018-02-27 | 湖南鑫利生物科技有限公司 | A kind of processing method for preparing refined Rosmarinus officinalis extract |
| CN107739305A (en) * | 2017-09-11 | 2018-02-27 | 湖南鑫利生物科技有限公司 | A kind of method for improving carnosic acid content in rosemary fat-soluble antioxidant |
| CN107739306B (en) * | 2017-09-11 | 2021-02-09 | 湖南鑫利生物科技有限公司 | A method for preparing refined herba Rosmarini officinalis extract |
| CN108048220A (en) * | 2017-12-19 | 2018-05-18 | 贵州航天乌江机电设备有限责任公司 | A kind of method of low temperature extraction rosemary oil |
| CN108338406A (en) * | 2018-02-13 | 2018-07-31 | 玉溪开元金蓝生物科技有限责任公司 | A kind of quick-fried pearl of rosemary antioxidant and its application in cigarette filter rod |
| CN110100910A (en) * | 2019-05-30 | 2019-08-09 | 河南农业大学 | A kind of woody edible oil and its processing method |
| WO2021038340A1 (en) * | 2019-08-26 | 2021-03-04 | Tübi̇tak | Carnosic acid, carnosol and rosmarinic acid isolation method |
| CN110862315A (en) * | 2019-12-06 | 2020-03-06 | 湖南先伟实业有限公司 | By using supercritical CO2Method for extracting carnosic acid from rosemary leaves |
| CN113200857A (en) * | 2021-03-19 | 2021-08-03 | 河南华牧生物科技有限公司 | Process for purifying origanum rosemarium acid antioxidant by two-phase solvent extraction method |
| CN113200857B (en) * | 2021-03-19 | 2024-04-09 | 河南华牧生物科技有限公司 | Process for purifying origanum rosmarinic acid antioxidant by two-phase solvent extraction method |
| CN113480592A (en) * | 2021-06-09 | 2021-10-08 | 湖南鑫利生物科技有限公司 | Method for preparing rosemary ursolic acid |
| CN114702378A (en) * | 2022-05-10 | 2022-07-05 | 南京泛成生物科技有限公司 | Method for preparing rosemary extract by using two-aqueous-phase extraction method |
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Application publication date: 20110928 |