CN114315566B - Method for preparing rosemary water-soluble and fat-soluble antioxidants simultaneously - Google Patents
Method for preparing rosemary water-soluble and fat-soluble antioxidants simultaneously Download PDFInfo
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Abstract
本申请公开一种同时制备迷迭香水溶性和脂溶性抗氧化剂的方法，包括以下步骤：获取干燥的迷迭香的茎和叶作为原材料；采用乙醇水作为提取溶剂浸泡所述原材料成为固液混合物；采用层析柱将所述固液混合物洗脱出混合提取液；采用旋转蒸发法分离所述混合提取液中的水溶性成分和脂溶性成分；所述水溶性成分含有迷迭香水溶性抗氧化剂；所述脂溶性成分含有迷迭香脂溶性抗氧化剂。本申请的制备方法工艺过程简单、高效，提取率高，产量大，易于实现工业化和批量生产，产品安全性好，制备过程中使用的溶剂可回收利用，生产成本低，产生危废少，对环境污染小。
The present application discloses a method for preparing rosemary water-soluble and fat-soluble antioxidants at the same time, comprising the following steps: obtaining dried rosemary stems and leaves as raw materials; using ethanol water as an extraction solvent to soak the raw materials into a solid-liquid mixture; using a chromatography column to elute a mixed extract from the solid-liquid mixture; using a rotary evaporation method to separate the water-soluble components and fat-soluble components in the mixed extract; the water-soluble components contain rosemary water-soluble antioxidants; and the fat-soluble components contain rosemary fat-soluble antioxidants. The preparation method of the present application has a simple and efficient process, a high extraction rate, a large output, is easy to realize industrialization and mass production, has good product safety, the solvent used in the preparation process can be recycled, has low production cost, generates less hazardous waste, and has little environmental pollution.
Description
Technical Field
The application relates to the technical field of separation and purification of natural compounds, in particular to a method for simultaneously preparing rosemary water-soluble and fat-soluble antioxidants.
Background
In recent years, with the continuous improvement of the living standard of people, the problem of using safety of artificial preservatives in foods, cosmetics and daily necessities is increasingly receiving attention, and the research and development and application of pure natural antioxidants are becoming research hotspots in the fields of foods and chemical industry. Rosemary is a plant of the genus Labiatae, is a plant which has higher antioxidation effect, is safe and nontoxic, is praised as a third-generation green food antioxidant, and has wide application prospect and great market potential. Currently, commercially available rosemary antioxidants include both lipid-soluble antioxidants and water-soluble antioxidants. According to the food additive rosemary extract of GB 1886.172-2016 national food safety standards, the content of the main active ingredient rosemary acid in the water-soluble antioxidant is not less than 5%, the rosemary acid has strong antioxidation and antibacterial capability and can resist high temperature of more than 100 ℃, and can be widely applied to various beverages, aquatic products and natural water-soluble pigments, the content of the main active ingredient carnosic acid in the fat-soluble antioxidant is not less than 10%, and the heat stability is good, so that the rosemary acid can resist high temperature of 190-240 ℃, and is mainly applied to foods such as grease, dairy products, oil-rich foods, candies, baking and the like.
At present, the research on rosemary extract mainly comprises the preparation and application of a fat-soluble antioxidant, and the main preparation method is an ethanol extraction method or a supercritical CO2 extraction method. The preparation of the fat-soluble antioxidant by adopting an ethanol extraction method generally requires that the rosemary essential oil is separated by steam distillation, carnosic acid is easily oxidized and degraded in the production process, the yield and the antioxidation effect of the extract are affected, and the preparation of the fat-soluble antioxidant by adopting a supercritical CO2 extraction method has high production cost, single product and deeper color, and is difficult to realize industrial production. The rosemary water-soluble antioxidant is usually a byproduct of rosemary essential oil and fat-soluble antioxidant production, the content of rosmarinic acid in the extract is low, the subsequent purification and refining steps are complex, and the production cost is high.
Disclosure of Invention
The application aims at overcoming the defects of the prior art and provides a method for simultaneously preparing water-soluble and fat-soluble antioxidants of rosemary.
In order to achieve the technical purpose, the application adopts the following technical scheme:
a method for simultaneously preparing rosemary water soluble and fat soluble antioxidants, comprising the steps of:
obtaining dried stems and leaves of rosemary as raw materials;
soaking the raw materials by adopting ethanol water as an extraction solvent to form a solid-liquid mixture;
Eluting the solid-liquid mixture by adopting a chromatographic column to obtain a mixed extracting solution;
separating water-soluble components and fat-soluble components in the mixed extracting solution by adopting a rotary evaporation method;
the water-soluble component contains rosemary water-soluble antioxidant;
the fat-soluble component contains rosemary fat-soluble antioxidant.
Preferably, the raw materials are crushed before being soaked and then pass through a 20-40 mesh sieve.
Optionally, the ethanol water is an ethanol water solution with the volume percentage of 50% -95%.
Further preferably, the soaking time is 2-4 hours.
Further alternatively, the packing diameter-to-height ratio of the solid-liquid mixture in the chromatographic column is 1:2.5-10.
Further, the eluent of the solid-liquid mixture is the extraction solvent, the elution flow rate is 1-3 BV/h, and the elution is carried out at room temperature.
Preferably, the rotary evaporation method is performed at 40-50 ℃, the collected evaporation liquid is dissolved into an aqueous phase to obtain the water-soluble component, and the collected precipitate is dissolved into an ethanol phase to obtain the fat-soluble component.
Further, after the water-soluble component and the fat-soluble component are decolorized and dried, respectively, a rosemary water-soluble antioxidant extract and a rosemary fat-soluble antioxidant extract are obtained.
Optionally, the decoloring adopts a decoloring agent for pigment adsorption, and the decoloring agent is any one of activated carbon, activated clay and macroporous resin.
Compared with the prior art, the application has the following advantages:
The application takes dried rosemary stems and leaves as materials, prepares rosemary mixed extract by using a column chromatography extraction method, carries out rotary evaporation on the mixed extract, can separate water-soluble components and fat-soluble components in the mixed extract, and respectively stands the water-soluble components and the fat-soluble components to obtain the rosemary water-soluble and fat-soluble antioxidant. The preparation method has the advantages of simple and efficient technical process, high extraction rate, high yield, easy realization of industrialization and mass production, good product safety, recyclable solvent used in the preparation process, low production cost, less hazardous waste and less environmental pollution.
According to the column chromatography extraction technology adopted by the application, the raw materials fully soaked by the extracting solution are directly filled into the chromatographic column for eluting, the water-soluble antioxidant (rosmarinic acid) and the liposoluble antioxidant (carnosic acid) of rosemary can be simultaneously and efficiently extracted by controlling the eluting conditions, the extracting conditions are mild, the process is simple, the cost is low, the yield is high, the degradation of rosmarinic acid and carnosic acid can be effectively prevented, and the method is suitable for large-scale industrial production.
The whole process of the application is green and environment-friendly, the solvent is only ethanol water solution, the application is nontoxic and has low peculiar smell, and the safety of the two antioxidants as food additives is ensured.
Drawings
FIG. 1 is a process flow diagram of the method of the present application for simultaneously preparing rosemary water soluble and fat soluble antioxidants.
FIG. 2 shows the results of thin layer chromatography analysis of rosemary extract and antioxidant obtained by the method of the present application.
FIG. 3 shows the results of HPLC analysis of water-soluble and fat-soluble components of rosemary obtained by the method of the present application.
Detailed Description
The application is described in further detail below with reference to the drawings and detailed description.
Referring to fig. 1, in one possible embodiment of the method for simultaneously preparing water-soluble and fat-soluble antioxidants of rosemary according to the present application, the following steps are used for simultaneous extraction of the water-soluble antioxidants and the fat-soluble antioxidants of rosemary:
s01, obtaining stems and leaves of dried rosemary as raw materials;
After the stems and leaves of the rosemary are harvested, the stems and leaves of the rosemary are dried at a low temperature (about 50 ℃), so that decay and mildew of fresh materials are avoided, obvious loss of volatile oil components is prevented, and various components in the rosemary can be conveniently extracted through different technical paths, such as extracting essential oil, antioxidant components or medicinal components of the rosemary.
In the preparation method, the dried rosemary raw material is required to be crushed and passes through a 20-40 mesh sieve, so that the contact surface area is increased in the subsequent contact process with the extraction solvent, the target extract is conveniently dissolved into the extraction solvent, the crushed particles are not required to be too small, otherwise, the extraction solvent is difficult to pass through the particle gaps, and sufficient elution cannot be realized.
S02, soaking the raw materials into a solid-liquid mixture by adopting ethanol water as an extraction solvent;
The water-soluble antioxidant in rosemary is mainly rosemaric acid, which is an acid containing polyphenol hydroxyl, and is obtained by separating and extracting rosemary plant for the first time in 1958. Rosmarinic acid is widely distributed from lower moss to higher dicotyledons, mainly in Labiatae, boraginaceae, cucurbitaceae, tiliaceae, and Umbelliferae. The rosmarinic acid is water-soluble, the low-content rosmarinic acid is light yellow to brown powder, the high-content rosmarinic acid is white powder, the rosmarinic acid is easy to absorb moisture, has special herbal smell of rosmarinic acid, and shows blue-green color when meeting ferric trichloride-potassium ferricyanide solution.
The liposoluble antioxidant in rosemary is mainly carnosic acid, which is named as carnosic acid bitter lactone, is easily dissolved in grease and water, is colorless to pale yellow powder crystal, and has the characteristics of high efficiency, oxidation resistance, safety, no toxicity, high temperature resistance and the like.
According to the characteristics of the rosmarinic acid and the carnosic acid, in the step, the water-soluble rosmarinic acid and the fat-soluble carnosic acid are required to be leached out of the raw materials at the same time, so that an ethanol water-ethanol water solution with the volume percentage of 50% -95% is adopted as an extraction solvent. In the next step, the soaking time of the raw materials and the ethanol water should be at least 2 hours, so that the raw materials are fully swelled, the soaking time is not suitable for being too long, the dissolution efficiency of the target extract has a peak value, the too long soaking time is not beneficial to optimizing the input-output ratio of the whole preparation process, and the soaking time is not suitable for exceeding 4 hours through experimental verification. Further, in order to increase the concentration of the target extract in the subsequent eluent, the ethanol water used during soaking should not be excessive, and the ethanol water just falls out of the raw materials in a state of fully swelling the raw materials, thereby meeting the requirements.
S03, eluting the solid-liquid mixture by adopting a chromatographic column to obtain a mixed extract;
For ease of observation, embodiments of the present application preferably employ a glass chromatographic column to elute the target extract from the immersed solid-liquid mixture. Specifically, referring to a column packing method of a stationary phase of a column chromatography, a solid-liquid extract is packed into a glass chromatographic column, so that the packing diameter-to-height ratio of a solid-liquid mixture in the chromatographic column is 1:2.5-10.
Alternatively, the dried and crushed raw materials and the extraction solvent can be loaded into a glass chromatographic column, and the soaking process is carried out in the glass chromatographic column, if bubbles or gaps appear in the solid-liquid mixture, the solid-liquid mixture can be treated by vibration or vacuumizing.
During elution, the ethanol water is used as an eluent, the eluting flow rate is controlled to be 1-3 BV/h, the elution is carried out at room temperature, and the eluted liquid is a mixed extract mixed with water-soluble components and fat-soluble components. The volume ratio of ethanol in the ethanol water in the elution process can be properly adjusted to control the harvest amount and the washing time of the water-soluble component and the fat-soluble component respectively.
Referring to fig. 2, thin layer chromatography analysis is performed on eluents flowing out at different times, in ethanol water eluents with fixed ethanol-water volume ratio, water-soluble rosmarinic acid is eluted preferentially, and fat-soluble carnosic acid is still collected in the second half of the elution, which gives two points that firstly, compared with rosmarinic acid, the enrichment degree of fat-soluble carnosic acid in stems and leaves of rosemary is higher, and secondly, the volume ratio of ethanol in ethanol water can be adjusted in the elution process, so that the enrichment degree of rosmarinic acid and carnosic acid in the eluents collected at different times is higher, thereby being beneficial to simplifying the subsequent purification steps.
S04, separating water-soluble components and fat-soluble components in the mixed extracting solution by adopting a rotary evaporation method;
The prior art measures that the boiling point of rosmarinic acid is 694.7 +/-55.0 ℃ (760 mmHg), the boiling point of carnosic acid is 490.0+/-45.0 ℃, and the rosmarinic acid and carnosic acid can be separated by a rotary evaporation method by utilizing the difference of the boiling points of rosmarinic acid and carnosic acid. The temperature of rotary evaporation is controlled to be 40-50 ℃, under the condition, the water-soluble component becomes an evaporation solution to leave the mixed extracting solution, and the fat-soluble component becomes a precipitate to stay in the round-bottom flask.
S05-1 and S05-2, respectively redissolving the evaporation liquid and the precipitate;
after rotary evaporation, the collected evaporation liquid was dissolved in an aqueous phase to obtain a water-soluble component, and the collected precipitate was dissolved in an ethanol phase to obtain a fat-soluble component.
Referring to fig. 3, high performance liquid chromatography analysis was performed on the water-soluble component (water-soluble extract) and the fat-soluble component (fat-soluble extract), respectively, to confirm that rosmarinic acid was present only in the water-soluble component, and that rosmarinic acid was contained in the water-soluble component in addition to other active substances, corresponding to the experimental result of thin layer chromatography, and that carnosic acid was present only in the fat-soluble component, and that other active substances were less in the fat-soluble component, corresponding to the experimental result of thin layer chromatography.
It follows that the water-soluble component contains rosemary water-soluble antioxidants and the fat-soluble component contains rosemary fat-soluble antioxidants.
S06-1& S06-2, refining the re-dissolved water-soluble component and fat-soluble component respectively.
Specifically, after the water-soluble component and the fat-soluble component are decolorized and dried, respectively, a rosemary water-soluble antioxidant extract and a rosemary fat-soluble antioxidant extract are obtained. Since the preceding steps have performed maximum enrichment and removal of impurities from the target extract, the purpose of the so-called refining is to make the product more excellent in its quality and more stable in its quality. The decoloring adopts a decoloring agent for pigment adsorption, and the decoloring agent is any one of active carbon, activated clay and macroporous resin.
The method of the present application for preparing both water-soluble and fat-soluble antioxidants of rosemary is described below by way of specific examples.
Example 1
A process for preparing the water-soluble and fat-soluble antioxidants of rosemary includes such steps as pulverizing 10g of dried rosemary stem and leaf, sieving with 20-mesh sieve, immersing the pulverized rosemary material in 70% (V/V) alcohol for 2 hr, loading it in glass chromatographic column, eluting with 70% (V/V) alcohol water solution as eluting liquid, eluting at 1 BV/hr to obtain aqueous phase, rotary evaporating 10BV eluting liquid to obtain aqueous phase, adding 10% (m/V) active clay, decoloring at 40 deg.C for 1 hr, concentrating, drying to obtain rosemary water-soluble antioxidants, depositing, dissolving in alcohol, adding 10% (m/V) active clay, decoloring at 40 deg.C for 1 hr, concentrating, and drying.
Example 2
A method for preparing water-soluble and fat-soluble rosemary antioxidant comprises the following steps of (1) taking 5g of dried rosemary stems and leaves, crushing, sieving with a 20-mesh sieve, (2) soaking crushed rosemary material in 50% (V/V) ethanol water, fully swelling for 2h, loading into a glass chromatographic column, carrying out column chromatography extraction by taking 50% (V/V) ethanol water solution as eluent and having an aspect ratio of 1:10 and an elution flow rate of 2BV/h, (3) collecting 8BV eluent, rotationally evaporating to obtain a water phase, adding 10% (m/V) active carbon, decolorizing at 40 ℃ for 1h, concentrating and drying to obtain the rosemary water-soluble antioxidant, (4) collecting precipitate in (3), adding 10% (m/V) active carbon, decolorizing at 40 ℃ for 1h, concentrating and drying to obtain the rosemary fat-soluble antioxidant.
In summary, the method for preparing the rosemary water-soluble and fat-soluble antioxidants simultaneously takes dried rosemary stems and leaves as materials, utilizes a column chromatography extraction method to prepare rosemary extract, rotationally evaporates the extract to a water phase, precipitates are redissolved by ethanol, and the water phase and the ethanol phase are decolorized and dried respectively to obtain the rosemary water-soluble and fat-soluble antioxidants. The preparation method disclosed by the application has the advantages of simple and efficient technical process, high extraction rate, high yield, easiness in realizing industrialization and batch production, good product safety, recyclable solvent used in the preparation process, low production cost, less hazardous waste and less environmental pollution.
The above embodiments are preferred embodiments of the present application, but are not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principles of the present application should be made therein and are intended to be equivalent substitutions within the scope of the present application.
Claims (6)
1. A method for simultaneously preparing rosemary water-soluble and fat-soluble antioxidants, comprising the steps of:
The method comprises the steps of obtaining dried stems and leaves of rosemary as raw materials, crushing the raw materials before soaking, and sieving the raw materials with a 20-40-mesh sieve;
Soaking the dried crushed raw materials into a solid-liquid mixture by using ethanol water as an extraction solvent, wherein the solid-liquid mixture is in a state that the extraction solvent just drops out of the swollen raw materials in a state that the dried crushed raw materials are fully swollen;
Filling the solid-liquid mixture into a chromatographic column without using a stationary phase according to a stationary phase column filling method of column chromatography, so that the column filling diameter-to-diameter ratio of the solid-liquid mixture in the chromatographic column is 1:2.5-10, or filling the dried crushed raw materials and an extraction solvent into the chromatographic column, and performing a soaking process in the chromatographic column, so that the column filling diameter-to-diameter ratio of a solid-liquid extract formed by soaking is 1:2.5-10;
Eluting the solid-liquid mixture by using the extraction solvent as an eluent to obtain a mixed extract, wherein the elution flow rate of the solid-liquid mixture is 1-3 BV/h, and the mixed extract is eluted at room temperature, and the mixed extract comprises a water-soluble component enriched part, a fat-soluble component enriched part and a fat-soluble component containing part which are respectively obtained at different elution times by using the extraction solvents with different ethanol volume ratios;
separating the water-soluble component and the fat-soluble component in the fraction containing the water-soluble component and the fat-soluble component by a rotary evaporation method;
The water-soluble component-enriched fraction and the fraction comprising the water-soluble component and the fat-soluble component comprise rosemary water-soluble antioxidants;
The fat-soluble component in the fat-soluble component-enriched fraction and the fraction comprising the water-soluble component and the fat-soluble component contains rosemary fat-soluble antioxidants.
2. The method of claim 1, wherein the ethanol water is an aqueous ethanol solution having a volume percent of 50% -95%.
3. The method of claim 1, wherein the soaking time is 2-4 hours.
4. The method according to claim 1, wherein the rotary evaporation method is performed at 40-50 ℃, the collected evaporation liquid is dissolved in an aqueous phase to obtain the water-soluble component, and the collected precipitate is dissolved in an ethanol phase to obtain the fat-soluble component.
5. The method of claim 4, wherein the water-soluble and fat-soluble ingredients are decolorized and dried, respectively, to obtain rosemary water-soluble antioxidant extract and rosemary fat-soluble antioxidant extract.
6. The method of claim 5, wherein the decolorizing employs a decolorizing agent selected from the group consisting of activated carbon, activated clay, and macroporous resin for pigment adsorption.
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| CN1466971A (en) * | 2002-07-08 | 2004-01-14 | 贵州昱华实业有限公司产品技术研究所 | Production process for extracting liposoluble and water soluble antioxidant from rosemary |
| CN104447334A (en) * | 2014-12-22 | 2015-03-25 | 付大亮 | Comprehensive extraction technology of rosmarinic acid, ursolic acid, oleanolic acid and carnosic acid |
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| US9376351B2 (en) * | 2010-10-25 | 2016-06-28 | Kalamazoo Holdings, Inc. | Simple process to produce and separate water soluble and oil soluble antioxidative flavoring compositions from labiatae herbs using green solvents |
| CN104490994A (en) * | 2014-12-18 | 2015-04-08 | 民权鼎昕生物科技有限公司 | Method for extracting lipid-soluble and water-soluble antioxidant from rosemary |
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| CN1466971A (en) * | 2002-07-08 | 2004-01-14 | 贵州昱华实业有限公司产品技术研究所 | Production process for extracting liposoluble and water soluble antioxidant from rosemary |
| CN104447334A (en) * | 2014-12-22 | 2015-03-25 | 付大亮 | Comprehensive extraction technology of rosmarinic acid, ursolic acid, oleanolic acid and carnosic acid |
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