CN112409440A - Method for producing ursolic acid emulsion by using rosemary ointment as raw material - Google Patents
Method for producing ursolic acid emulsion by using rosemary ointment as raw material Download PDFInfo
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- CN112409440A CN112409440A CN202110001010.7A CN202110001010A CN112409440A CN 112409440 A CN112409440 A CN 112409440A CN 202110001010 A CN202110001010 A CN 202110001010A CN 112409440 A CN112409440 A CN 112409440A
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- rosemary
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- 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
Abstract
The invention discloses a method for producing ursolic acid emulsion by using rosemary oil paste byproducts as raw materials, which comprises the following steps: (1) and (3) processing rosemary oil paste byproducts: selecting rosemary oil paste byproducts containing certain content of ursolic acid, adding a certain amount of ethanol solution for dissolving, and then filtering, (2) mutual dissolution of the rosemary oil paste byproducts: adding a certain amount of Tween-80 as surfactant into the filtrate, and adding polyethylene glycol-400 solution in an amount corresponding to the weight of the rosemary ointment byproduct to dissolve the rosemary ointment byproduct in the solution; (3) and (3) ultrafiltration impurity removal: centrifuging, wherein the centrifugate passes through a ceramic membrane ultrafiltration system, and filtering and separating most macromolecular impurities, (4) concentrating: concentrating the filtrate to one fifth of the original volume, filtering, and filtering residual ethanol residue by nanofiltration to obtain the ursolic acid emulsion product.
Description
Technical Field
The invention belongs to the field of plant extraction, and particularly discloses a method for producing ursolic acid emulsion by using rosemary ointment as a raw material.
Background
Rosemary (Rosmarinus officinalis L.) is an evergreen shrub of Rosmarinus of Labiatae (Labiatae), is native to Mediterranean region, and is cultivated in Xinjiang, Yunnan, Guizhou, etc. of China at present. The tea has warm nature and pungent taste, is mainly prepared from leaves, has the effects of invigorating stomach, refreshing brain, tranquilizing and allaying excitement and the like, has a certain treatment effect on nervous, digestive and respiratory system diseases, and is also a traditional spice and a food additive.
Rosemary is rich in multiple antioxidant components, has strong antioxidant capacity, and is a plant which is recognized at present and has high-efficiency antioxidant effect. Rosemary was successfully introduced in 1981 by the institute of plant of Chinese academy of sciences, aromatic oil was extracted from stems and leaves of Rosemary by supercritical CO2 extraction, and edible antioxidant was extracted. The main components of rosemary for resisting oxidation are phenolic acids, diterpene phenols, flavonoids and a small amount of triterpenoids, the mechanism of rosemary is that the rosemary can cut off the automatic oxidation chain of grease and chelate metal ions, the probability of containing strong carcinogens is greatly reduced, cells can be protected, carcinogens are not easy to attach to the cells, thus DNA is prevented from being damaged by oxidation, and the possibility of cancer occurrence is reduced. It has been also shown that rosemary contains an acetylcholine inhibitor which prevents the decomposition of acetylcholine, a neurotransmitter affecting mental function, and that low levels of acetylcholine are associated with the deterioration of memory due to normal aging and the development of senile dementia.
The rosemary ointment byproduct is an oily ointment byproduct containing relatively high ursolic acid, which is obtained in the ursolic acid production process, has remarkable antioxidant and antibacterial effects, and is widely applied in the field of foods.
Disclosure of Invention
In order to solve the problems, the invention provides a method for preparing ursolic acid emulsion by taking rosemary oil paste byproducts as raw materials, which comprises the steps of utilizing polyethylene glycol-400 to be mutually soluble with the rosemary oil paste byproducts, and dispersing the rosemary oil paste byproducts in an aqueous solution in a mode of recovering an ethanol solvent, thereby finally obtaining an ursolic acid emulsion product with good water solubility.
The technical scheme of the invention is as follows:
a method for preparing ursolic acid emulsion from rosemary oil paste byproduct comprises the following steps
(1) And (3) processing rosemary oil paste byproducts: selecting rosemary oil paste byproduct containing certain content of ursolic acid, adding a certain amount of ethanol solution for dissolving, filtering,
(2) mutual solubility of rosemary ointment by-products: adding a certain amount of Tween-80 as surfactant into the filtrate, and adding polyethylene glycol-400 solution in an amount corresponding to the weight of the rosemary ointment byproduct to dissolve the rosemary ointment byproduct in the solution;
(3) and (3) ultrafiltration impurity removal: centrifuging, passing the centrifugate through a ceramic membrane ultrafiltration system, filtering to remove most macromolecular impurities,
(4) concentration: concentrating the filtrate to one fifth of the original volume, filtering, and filtering the residual ethanol by nanofiltration. Obtaining the ursolic acid emulsion product.
Preferably, the method for preparing the ursolic acid emulsion by using the rosemary oil paste byproduct as the raw material comprises the following specific steps:
(1) and (3) processing rosemary oil paste byproducts: selecting rosemary ointment byproduct containing certain content of ursolic acid, adding proper amount of ethanol for dissolving, and filtering with filter paper after dissolving. The rosemary oil paste byproduct has some ethanol insoluble impurities in the production and storage process, and needs to be dissolved and filtered, so that the subsequent steps can not cause equipment blockage;
(2) dissolution of rosemary ointment by-product: adding a proper amount of Tween-80 into the ethanol solution of the rosemary oil paste byproduct obtained in the step (1), uniformly stirring, then adding polyethylene glycol-400, and controlling the adding speed under the stirring state to completely dissolve the Tween-80, wherein the Tween-80 is relatively common and very safe nonionic surface activity, and the purpose of adding the Tween-400 is to improve the surface tension in the rosemary oil paste byproduct solution so as to ensure that the whole system is smoothly dissolved, and the polyethylene glycol-400 is a carrier material which is relatively widely applied, has extremely excellent alcohol solubility and water solubility and is suitable for the production process of the process;
(3) and (3) ultrafiltration impurity removal: passing the solution obtained in the step 2 through a horizontal centrifuge, transferring the centrifugate into an ultrafiltration system, controlling the molecular weight of an ultrafiltration membrane to obtain the ursolic acid emulsion after ultrafiltration, wherein ultrafiltration can filter out most macromolecular substances which are easy to cause precipitation, so that the stability of the product is reduced;
(4) concentration: and (3) concentrating the ursolic acid emulsion obtained in the step (3), filtering by using filter paper after concentrating to one fifth of the original volume, adding the filtrate into nanofiltration equipment, controlling the molecular weight cut-off of the nanofiltration membrane, filtering at a speed, and filtering most of ethanol residues to obtain the ursolic acid emulsion product.
Preferably; in the step 1, rosemary ointment byproduct treatment: selecting rosemary ointment byproduct with ursolic acid content of 10-15% (preferably 12%), adding 70% ethanol in an amount of 10-15BV (1 BV based on the weight of rosemary ointment byproduct, 10BV means adding 10 times the weight of solution relative to rosemary ointment byproduct) (preferably 15 BV), dissolving, and filtering with 20-25 μm filter paper. (preferably 25 μm).
Preferably; the step 2, the dissolving process of the rosemary ointment byproduct comprises the following steps: adding Tween-80 in an amount of 5-10% (preferably 5%) of rosemary ointment byproduct, and adding polyethylene glycol-400 in an amount of 1.2-1.5BV (preferably 1.2 BV) of rosemary ointment byproduct.
Preferably; in the ultrafiltration impurity removal process in the step 3, the rotating speed of the horizontal centrifuge is 2500-.
Preferably; in the step 4 concentration process: the concentration condition is-0.07-0.09 MPa (preferably-0.08 MPa), and the concentration temperature is 55-60 ℃ (preferably 55 ℃). The filter paper has the filter diameter of 20-25 μm (preferably 25 μm), and the nanofiltration membrane is controlled at 200-500Da (preferably 300 Da). The nanofiltration speed is controlled to be 50-70% of the maximum filtration speed of the nanofiltration equipment. (preferably 60%)
Compared with the prior art, the invention has the beneficial effects that:
the present invention is a result of improvement and development of products due to problems in actual product sales. Belongs to the technology of the technical formula of plant extracts. The product is mainly oriented to the food industry and is used in various scenes needing the ursolic acid emulsion with better water dispersibility.
This product was developed because this company, when selling the water-dispersible rosemary oil paste byproduct powder, communicated with customers after sale, found that the customers needed to dissolve our product in a low-temperature aqueous solution, and found that the product was slowly dispersed in a low-temperature aqueous solution after the test. Before use, the mixture must be stirred uniformly in normal-temperature water, and then the mixture is added into the low-temperature water for further dispersion usually by stirring for 10-20min, and the addition amount needs to be calculated in advance. The whole operation process becomes complicated. The time consumption is also long. In view of these problems, the present company has developed a method for preparing the water-soluble ursolic acid emulsion through a long-term research and development.
The water-soluble ursolic acid emulsion prepared by the method has the following specific advantages:
1. excellent water dispersibility. The product can be directly used, can also be added into water at different temperatures, has extremely high dispersion speed, and does not have obvious layering phenomenon. The operation difficulty in the production process is greatly simplified.
2. The product stability is strong. The product is more difficult to precipitate compared with the commonly used dispersing agent process because a mature dissolving process is used. And the content change of the ursolic acid is verified to be within 5 percent by an accelerated experiment (120 hours at the temperature of 60 ℃). Indicating that the product has excellent stability.
3. Compared with powdery water-soluble rosemary ointment byproduct powder, the product greatly reduces the existence of solvent residues due to the addition of a nanofiltration step, and the safety of the product is ensured.
Drawings
FIG. 1 is a process flow diagram of the present invention.
FIG. 2 shows HPLC chromatogram of ursolic acid standard;
FIG. 3 is an HPLC chromatogram of the content of ursolic acid emulsion in example 1;
fig. 4 is a finished product display of example 1.
Detailed Description
The technical solution of the present invention will be further described in detail with reference to specific embodiments. The following examples are merely illustrative and explanatory of the present invention and should not be construed as limiting the scope of the invention. All the technologies realized based on the above-mentioned contents of the present invention are covered in the protection scope of the present invention.
Unless otherwise indicated, the raw materials and reagents used in the following examples are all commercially available products or can be prepared by known methods.
The overall process is shown in fig. 1, and specifically includes the following steps:
1. and (3) processing rosemary oil paste byproducts: selecting rosemary ointment byproduct containing certain content of ursolic acid, adding ethanol with a proper amount of time to dissolve, and filtering by using filter paper after dissolving;
preferably; in the treatment of the rosemary ointment byproduct: selecting rosemary ointment byproduct with ursolic acid content of 10-15% (preferably 12%), adding 70% ethanol in an amount of 10-15BV (1 BV based on the weight of rosemary ointment byproduct, 10BV means adding 10 times the weight of solution relative to rosemary ointment byproduct) (preferably 15 BV), dissolving, and filtering with 20-25 μm filter paper. (preferably 25 μm).
2. Dissolution of rosemary ointment by-product: adding a proper amount of Tween-80 into the ethanol solution of the rosemary oil paste byproduct obtained in the step 1, uniformly stirring, adding polyethylene glycol-400, and controlling the adding speed under the stirring state to completely dissolve the mixture;
preferably; the rosemary ointment byproduct comprises: adding Tween-80 in an amount of 5-10% (preferably 5%) of rosemary ointment byproduct, and adding polyethylene glycol-400 in an amount of 1.2-1.5BV (preferably 1.2 BV) of rosemary ointment byproduct.
3. And (3) ultrafiltration impurity removal: passing the solution obtained in the step 2 through a horizontal centrifuge, transferring the centrifugate into an ultrafiltration system, and controlling the molecular weight of an ultrafiltration membrane to obtain an ultrafiltrated ursolic acid emulsion;
preferably; in the ultrafiltration impurity removal process, the rotating speed of the horizontal centrifuge is 2500-.
4. Concentration: and (3) concentrating the ursolic acid emulsion obtained in the step (3), filtering by using filter paper after concentrating to one fifth of the original volume, adding the filtrate into nanofiltration equipment, controlling the molecular weight cut-off of the nanofiltration membrane, filtering at a speed, and filtering most of ethanol residues to obtain the ursolic acid emulsion product.
Preferably; in the step 4: the concentration condition is-0.07-0.09 MPa (preferably-0.08 MPa), and the concentration temperature is 55-60 ℃ (preferably 55 ℃). The filter paper has the filter diameter of 20-25 μm (preferably 25 μm), and the nanofiltration membrane is controlled at 200-500Da (preferably 300 Da). The nanofiltration speed is controlled to be 50-70% of the maximum filtration speed of the nanofiltration equipment. (preferably 60%).
Example 1
1: selecting 100kg rosemary oil ointment byproduct with ursolic acid content of 12.6%, adding 1000kg70% ethanol solution, stirring for dissolving, stirring for half an hour, filtering with rapid filter paper (filter diameter 25 μm), and discarding insoluble components.
2: 6kg of Tween-80 is added into the filtrate obtained in the step 1, and after the Tween-80 is dissolved completely by slight stirring, 120kg of polyethylene glycol-400 is slowly added. Stirring for 30min after completely adding to dissolve completely.
3: and (3) enabling the solution obtained in the step (2) to pass through a horizontal centrifugal device, controlling the rotating speed of a centrifugal machine to be 3000r/min, enabling the centrifugate to directly enter an ultrafiltration system, controlling the designed maximum flow of the ultrafiltration system to be 200L/h, controlling the outflow speed to be 70L/min, and enabling the cutoff molecular weight of the ultrafiltration membrane to be 100kDa, and effectively cutting off substances exceeding the molecular weight, wherein the part of molecules are easy to precipitate, so that the stability of the product is reduced.
4: and (3) concentrating the solution obtained in the step (3) to one fifth of the original volume under the concentration condition of 55 ℃ and the concentration pressure of-0.08 MPa, wherein a small amount of precipitate is separated out after concentration, and at the moment, filtering by using filter paper, wherein the filter paper adopts quick filter paper (the filter diameter is 25 mu m), and the filter paper is added into nanofiltration equipment after filtration. The nanofiltration equipment is designed to have the maximum filtration rate of 500L/h, the filtration rate is controlled to be 300L/h, the molecular weight cut-off of a nanofiltration membrane is controlled to be 300Da, the solution which does not pass through the membrane is the obtained ursolic acid emulsion product, 268L of final product is obtained, HPLC detection is carried out, as shown in a standard graph in figure 2 and a detection graph in figure 3, the same peak is generated at the 9.4min position, the ursolic acid content in the final determination product is 55.3mg/mL, the requirement of most of the products on the market for the ursolic acid content in the water-soluble rosemary ointment by-product is met, and as shown in figure 4, the ursolic acid emulsion sample obtained in the embodiment is.
The foregoing is only a preferred embodiment of the present invention. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. A method for preparing ursolic acid emulsion by using rosemary oil paste byproducts as raw materials is characterized by comprising the following steps:
(1) and (3) processing rosemary oil paste byproducts: selecting rosemary oil paste byproduct containing certain content of ursolic acid, adding a certain amount of ethanol solution for dissolving, filtering,
(2) mutual solubility of rosemary ointment by-products: adding a certain amount of Tween-80 as surfactant into the filtrate, and adding polyethylene glycol-400 solution in an amount corresponding to the weight of the rosemary ointment byproduct to dissolve the rosemary ointment byproduct in the solution;
(3) and (3) ultrafiltration impurity removal: centrifuging, passing the centrifugate through a ceramic membrane ultrafiltration system, filtering to remove most macromolecular impurities,
(4) concentration: concentrating the filtrate to one fifth of the original volume, filtering, and filtering the residual ethanol residue by nanofiltration to obtain the ursolic acid emulsion product.
2. The method for preparing ursolic acid emulsion from rosemary oil paste byproduct as raw material according to claim 1, wherein said step comprises the following specific steps:
(1) and (3) processing rosemary oil paste byproducts: selecting rosemary ointment byproduct containing certain content of ursolic acid, adding ethanol with a proper amount of time to dissolve, and filtering by using filter paper after dissolving;
(2) mutual solubility of rosemary ointment by-products: adding a proper amount of Tween-80 into the ethanol solution of the rosemary oil paste byproduct obtained in the step 1, uniformly stirring, adding a polyethylene glycol-400 solution, and controlling the adding speed under the stirring state to completely dissolve the Tween-80 and the polyethylene glycol-400 solution;
(3) and (3) ultrafiltration impurity removal: passing the solution obtained in the step 2 through a horizontal centrifuge, transferring the centrifugate into an ultrafiltration system, and controlling the molecular weight of an ultrafiltration membrane to obtain an ultrafiltrate;
(4) concentration: concentrating the ultrafiltrate to one fifth of the original volume, filtering with filter paper, adding the filtrate into nanofiltration equipment, controlling the molecular weight cut-off and the filtering speed of the nanofiltration membrane, and filtering out most ethanol residues to obtain the ursolic acid emulsion product.
3. The method of claim 2, wherein the rosemary ointment byproduct is treated in the step 1 by selecting rosemary ointment byproduct with ursolic acid content of about 10-15%, adding 70% ethanol solution for 10-15BV, dissolving and filtering with 20-25 μm filter paper.
4. The method for preparing ursolic acid emulsion from rosemary oil paste byproduct as a raw material according to claim 2, wherein in the step 2, the rosemary oil paste byproduct dissolution: adding Tween-80 in an amount of 5-10% of the rosemary ointment byproduct, adding polyethylene glycol-400 in an amount of 1.2-1.5 times of the rosemary ointment byproduct, and slowly adding under stirring until completely dissolving.
5. The method for preparing ursolic acid emulsion from rosemary oil paste byproduct as raw material according to claim 2, wherein in the step 3, the ultrafiltration and impurity removal step: the rotating speed of the horizontal centrifuge is 2500-.
6. The method of claim 2, wherein the step 4 comprises concentrating: the concentration condition is-0.07-0.09 MPa, and the concentration temperature is 55-60 ℃;
the specification of the filter paper filtered by the filter paper is 20-25 μm, and the nanofiltration membrane is controlled at 200-500 Da;
the nanofiltration speed is controlled to be 50-70% of the maximum filtration speed of the nanofiltration equipment.
7. The method for preparing an ursolic acid emulsion from rosemary oil paste byproduct as a raw material according to any one of claims 1 to 6, wherein the ursolic acid emulsion is a water soluble emulsion.
8. The method for preparing ursolic acid emulsion from rosemary oil paste byproduct as raw material according to any one of claims 1-6, wherein said ursolic acid emulsion is applied in food industry.
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