CN111995501B - Method for extracting resveratrol as natural feed additive - Google Patents
Method for extracting resveratrol as natural feed additive Download PDFInfo
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- CN111995501B CN111995501B CN202011167705.4A CN202011167705A CN111995501B CN 111995501 B CN111995501 B CN 111995501B CN 202011167705 A CN202011167705 A CN 202011167705A CN 111995501 B CN111995501 B CN 111995501B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/163—Sugars; Polysaccharides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/174—Vitamins
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/88—Use of additives, e.g. for stabilisation
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Abstract
The invention relates to a method for extracting natural product resveratrol, which comprises the following steps of; pretreating peanut roots and/or stems, and performing enzymolysis to obtain an enzymolysis product; adding quaternary ammonium salt and a stabilizer into the obtained enzymolysis product, inactivating, adding a solvent, and performing reduced pressure reflux extraction to obtain a crude product solution; the obtained crude product solution is desolventized and is post-treated to obtain the product. The invention also discloses a feed composition containing the resveratrol prepared by the method. The technical scheme of the invention has the advantages of high trans-body content of resveratrol, high yield, and difficult configuration change under the illumination condition, so that abundant crop waste resources are effectively and reasonably utilized, and the quality of livestock and poultry products can be effectively improved.
Description
Technical Field
The invention belongs to the technical field of natural feed additive extraction, and particularly relates to a method for extracting resveratrol serving as a natural feed additive.
Background
Resveratrol, also known as resveratrol, is known as 3,4, 5-trihydroxy-1, 2-stilbene. In nature, resveratrol exists in four forms of cis-resveratrol, trans-resveratrol and cis-and trans-polydatin, the trans-structure is the main source of antioxidant activity, the activity of a monomer is stronger than that of glucoside, and the trans-structure has the possibility of being converted into the cis-structure under illumination.
Since resveratrol was first found in grapes in the last 70 th century, it has been determined that about 72 kinds of plants containing resveratrol are present in succession in giant knotweed rhizome, peanut, mulberry and the like. Wherein, the resveratrol content in the giant knotweed is the highest, and is particularly obvious in the plant new tissues such as fresh root buds and the like; the content of resveratrol in grape skin is higher than that in other parts. However, the plants, medicinal materials or fruits which can be eaten fresh or used for brewing wine belong to parts with high economic value in crops, researches on extraction of resveratrol contained in peanuts are gradually increased recently, and particularly, the fact that the content of resveratrol in stems and roots of the peanuts is not as small as imagination is found, and the parts belong to parts with low economic value of the peanuts, so that the improvement of the utilization rate of the roots and stems of the peanuts has great significance, but at present, no method for extracting resveratrol by taking the roots and/or stems of the peanuts as raw materials and the content of trans-forms of the resveratrol in products is provided.
Disclosure of Invention
The invention aims to provide an extraction method of natural product resveratrol, and the resveratrol prepared by the technical scheme of the invention has the advantages of high trans-body content, stable configuration, high yield, high purity and simple post-treatment, can effectively and reasonably utilize abundant crop waste resources, and can effectively improve the quality of livestock products.
The technical scheme adopted by the invention for realizing the purpose is as follows: a method for extracting natural product resveratrol comprises the following steps;
1) pretreating peanut roots and/or stems, and performing enzymolysis to obtain an enzymolysis product;
2) adding quaternary ammonium salt and a stabilizer into the enzymolysis product obtained in the step 1), inactivating, adding a solvent, and performing reflux extraction to obtain a crude product solution;
3) desolventizing the crude product solution obtained in the step 2) and carrying out post-treatment to obtain a product;
further, the step 1) is specifically as follows: the step 1) is specifically as follows: cleaning peanut roots and/or stems, soaking, carrying out ultrasonic treatment, crushing, adding a complex enzyme solution, carrying out enzymolysis for 1-10h at 40-70 ℃, standing or centrifuging, and taking supernate, namely an enzymolysis product;
further, before adding the complex enzyme solution, adding water to soak the peanut roots and/or stems, wherein the soaking temperature is room temperature, and the soaking time is 0.5-3 h;
further, the peanut roots and/or stems are harvested peanut roots and/or stems;
further, the ultrasonic treatment is 300W ultrasonic treatment for 30min at the temperature of 60 ℃;
further, the complex enzyme solution comprises the following specific components: 0.5-5% aqueous solution with the mass concentration of cellulase, hemicellulase and beta-glucosidase in a mass ratio of 1-5:1-5: 1-5;
further, the cellulase is 400U/mg, the hemicellulase is 5U/mg, and the beta-glucosidase is 10U/mg;
further, the step 2) is specifically as follows: adding quaternary ammonium salt and a stabilizing agent into the enzymolysis product obtained in the step 1), heating to inactivate enzyme, adding a solvent, and performing reflux extraction for 2-5 hours under a reduced pressure condition to obtain a crude product solution;
further, the quaternary ammonium salt is preferably betaine;
further, the stabilizer is aromatic carboxylic acid;
still further, the stabilizer is nicotinic acid;
further, the solvent in the step 2) is water and glycerol in a mass ratio of 5-10: 1-2.
The invention also provides a feed composition, which contains the resveratrol prepared by the method;
further, it contains aromatic carboxylic acid;
still further, the aromatic carboxylic acid is nicotinic acid;
further, the mass ratio of the nicotinic acid to the resveratrol is 1: 5-30;
further, the mass ratio of the nicotinic acid to the resveratrol is 1: 5-15;
still further, the trans-configuration resveratrol in the feed composition accounts for more than 90% of all configuration resveratrol;
further, esters are contained;
still further, the ester is propylene glycol alginate.
In summary, due to the adoption of the technical scheme, the invention has the beneficial effects that:
(1) the method is characterized in that resveratrol mainly exists in a trans-configuration in nature, the trans-configuration proportion of resveratrol in peanut roots and stems is high, but the trans-configuration is easy to have configuration transformation under illumination, particularly ultraviolet light irradiation, the yield and stability of the trans-configuration are not additionally concerned in the traditional resveratrol extraction method, and the applicant unexpectedly finds that a reagent with an aromatic carboxylic acid structure is added in the resveratrol extraction process to form a hydrogen bond with resveratrol, and the aromatic ring structure of the reagent can also effectively limit the configuration change of the resveratrol, so that the stability of the trans-configuration resveratrol is effectively improved, the oxidation loss of the resveratrol is reduced to the maximum extent, certain help is provided for the resveratrol in the trans-configuration, and the condition that the resveratrol is degraded by heating is improved;
(2) aiming at the characteristics of extraction raw materials, a complex enzyme solution system of cellulase, hemicellulase and glucosidase is adopted, so that cell walls are more fully damaged, the resistance of outward dissolution of substances in cells can be effectively reduced, the subsequent extraction process is more facilitated, the crushing uniformity of materials can be improved by ultrasonic waves, and the exposure of resveratrol is facilitated by combining with enzyme extraction;
(3) the peanut rootstock is soaked in the aqueous solution added with the quaternary ammonium salt, so that the cell wall and the intercellular structure generate local loosening, swelling and other changes, thereby being more beneficial to improving the later enzymolysis efficiency; the water solubility and stability of the resveratrol can be improved after the enzymatic hydrolysate is added into the quaternary ammonium salt and the stabilizer, and the extraction efficiency can be effectively improved; the solvent mixed with water and glycerol is used in the reflux extraction process, which greatly helps the resveratrol to be extracted from plants in a trans-configuration, and the reduced pressure condition is provided, so that the boiling point of the solvent can be reduced, and the extraction rate of the resveratrol with biological activity can be further improved; in addition, the bioavailability of the resveratrol can be improved by adding the nicotinic acid and the propylene glycol ester into the premix added with the resveratrol.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The method for extracting the resveratrol by taking the waste peanut root after the harvest period of No. 6 Luhua as the raw material comprises the following specific operations:
taking 2kg of peanut roots (the content of resveratrol detected by HPLC is about 950 mug/g), washing with clear water, removing impurities such as soil, adding 2kg of water, soaking for about 2 hours, performing ultrasonic treatment, heating to 60 ℃ under the condition of 300W, and crushing after ultrasonic treatment for 30 min. Adding 0.5L of complex enzyme solution (5% aqueous solution with cellulase, hemicellulase and beta-glucosidase mass ratio of 5:5:1, wherein cellulase is 400U/mg, hemicellulase is 5U/mg and beta-glucosidase is 10U/mg) into the obtained mixture, performing enzymolysis at 50 deg.C for 2h, adding 0.1g betaine and 0.15g nicotinic acid, stirring, heating to 80 deg.C, and keeping the temperature for 10min to inactivate enzyme. 18kg of a solvent obtained by mixing water and glycerol at a volume ratio of 7:2 was added, and the mixture was reduced to 100mmHg and heated to reflux (about 60 ℃ C.) to extract for 3 hours to obtain a crude solution. Centrifuging the obtained crude product solution for 10 minutes at 3000r/min, separating supernatant, distilling under reduced pressure to dryness to obtain off-white solid 1.85g, dissolving with methanol as solvent, and metering to volume of 10 mL.
By HPLC detection (concentration and peak area standard curve is prepared by resveratrol reference substance solutions with different mass concentrations to calculate the content), the yield of resveratrol is 83.38%, the content is 85.63%, and trans-resveratrol accounts for 91.28% of all resveratrol.
Example 2
The method for extracting the resveratrol by taking the waste peanut stems after the harvest period of Luhua No. 6 as the raw materials comprises the following specific operations:
taking 2kg of peanut stem (resveratrol content is about 370 mu g/g by HPLC), washing with clear water, removing impurities such as soil, adding 2kg of water, soaking for about 2 hours, performing ultrasonic treatment, heating to 60 deg.C under 300W, and crushing after ultrasonic treatment for 30 min. Adding 0.5L of complex enzyme solution (5% aqueous solution with cellulase, hemicellulase and beta-glucosidase mass ratio of 5:5:1, wherein cellulase is 400U/mg, hemicellulase is 5U/mg and beta-glucosidase is 10U/mg) into the obtained mixture, performing enzymolysis at 50 deg.C for 2h, adding 0.05g betaine and 0.1g nicotinic acid, stirring, heating to 80 deg.C, and keeping the temperature for 10min to inactivate enzyme. 18kg of a solvent obtained by mixing water and glycerol at a volume ratio of 7:2 was added, and the mixture was reduced to 100mmHg and heated to reflux (about 60 ℃ C.) to extract for 3 hours to obtain a crude solution. Centrifuging the obtained crude product solution for 10 minutes at 3000r/min, separating supernatant, distilling under reduced pressure to dryness to obtain off-white solid 0.72g, dissolving with methanol as solvent, and metering to 10 mL.
By HPLC detection (concentration and peak area standard curve is prepared by resveratrol reference substance solutions with different mass concentrations to calculate the content), the yield of resveratrol is 80.11%, the content is 82.34%, and trans-resveratrol accounts for 88.56% of all resveratrol.
Comparative example 1
The method for extracting the resveratrol by taking the waste peanut root after the harvest period of No. 6 Luhua as the raw material comprises the following specific operations:
the same operation as in example 1 was repeated except that betaine was not added to the reaction solution, to obtain 1.32g of an off-white solid.
HPLC detection shows that the yield of resveratrol is 54.34%, the content is 78.22%, and trans-resveratrol accounts for 84.25% of all resveratrol.
Comparative example 2
The method for extracting the resveratrol by taking the waste peanut root after the harvest period of No. 6 Luhua as the raw material comprises the following specific operations:
the same procedures as in example 1 were repeated except that nicotinic acid was not added to the reaction solution to obtain 1.75g of an off-white solid.
HPLC detection shows that the yield of resveratrol is 74.22%, the content is 80.58%, and trans-resveratrol accounts for 76.75% of all resveratrol.
Example 3
Pork pig feeding test:
70 healthy Du-growing three-way hybrid pigs with the weight of 60 plus or minus 2kg and the age of days close (18 plus or minus 1 week) are selected and randomly divided into 7 groups, and 10 pigs in each group. Premix I-V group and control group I-II are set, and fed with basal ration,
the basic ration comprises the following components: 68.5% of corn, 12.5% of wheat bran, 1% of alfalfa meal, 10% of soybean meal, 2% of fish meal, 2% of soybean oil and 4% of premix.
The premixes of the premix I-VI and the control I are provided by research and development centers of big premix (Tianjin) Co., Ltd.), resveratrol (7.5 g/kg) is additionally added into the premix of the premix I, resveratrol (7.5 g/kg) + nicotinic acid (1.5 g/kg) is additionally added into the premix of the premix II, resveratrol (7.5 g/kg) + nicotinic acid (0.5 g/kg) is additionally added into the premix of the premix III, resveratrol (7.5 g/kg) + nicotinic acid (0.25 g/kg) is additionally added into the premix of the premix IV, resveratrol (7.5 g/kg) + nicotinic acid (1.5 g/kg) + propylene glycol alginate (1.5 g/kg) is additionally added into the premix of the premix V, resveratrol (7.5 g/kg) + nicotinic acid (1.5 g/kg) + propylene glycol alginate (0.5 g/kg) is additionally added into the premix VI, the control group did not additionally contain any additives. The pre-feeding period was 49 days.
TABLE 1 pig carcass quality control for each test group
The back fat thickness is measured by taking the back edge of the scapula, the position of the last rib and the position of the waist-shoulder junction 4 cm away from the back median line as measurement points of the fat thickness and taking the average value of the three points.
The test results show that compared with the premix I group and the control group, the premix II, III, IV, V and VI groups have the advantages that the backfat thickness is obviously reduced, the lean meat percentage is obviously improved, and the bioavailability of the resveratrol in the premix II-VI groups is relatively high.
Example 4
Pork pig stress test:
selecting 30 healthy Du-growing three-way hybrid pigs with the weight of 60 plus or minus 2kg and the age of days close (18 plus or minus 1 week), randomly dividing the pigs into 3 groups, and 10 pigs in each group. The premix group and the control groups I-II are set and fed with basic ration,
the basic ration comprises the following components: 68.5% of corn, 12.5% of wheat bran, 1% of alfalfa meal, 10% of soybean meal, 2% of fish meal, 2% of soybean oil and 4% of premix.
The premixes of the premix groups I-III and the control group are provided by research and development centers of big premixes (Tianjin) Limited, resveratrol (5 g/kg) is additionally added into the premix of the premix group I, resveratrol (5 g/kg) + nicotinic acid (1 g/kg) is additionally added into the premix of the premix group II, resveratrol (5 g/kg) + nicotinic acid (1 g/kg) + propylene glycol alginate (1 g/kg) is additionally added into the premix group III, and no additive is additionally added into the control group. The pre-feeding period is 49 days, the feeding temperature is 30 ℃, and the weight is weighed on an empty stomach 8:00 before the first week of the test 1 week and 8:00 before the second week of the test 7 week.
TABLE 2 pig production Performance control for each test group
The test results show that compared with premix I and control group, premix II and III have obviously improved stress resistance.
The above embodiments are only for illustrating the technical concept and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention accordingly, and not to limit the protection scope of the present invention accordingly. All equivalent changes or modifications made in accordance with the spirit of the present disclosure are intended to be covered by the scope of the present disclosure.
Claims (5)
1. A method for extracting natural product resveratrol is characterized by comprising the following steps;
1) pretreating peanut roots and/or stems, and performing enzymolysis to obtain an enzymolysis product;
2) adding betaine and a stabilizing agent nicotinic acid into the enzymolysis product obtained in the step 1), inactivating, adding a solvent, and performing reflux extraction to obtain a crude product solution;
3) desolventizing the crude product solution obtained in the step 2) and carrying out post-treatment to obtain the product.
2. The method according to claim 1, wherein step 1) is specifically: cleaning peanut roots and/or stems, soaking, carrying out ultrasonic treatment, crushing, adding a complex enzyme solution, carrying out enzymolysis for 2 hours at 50 ℃, standing or centrifuging, and taking supernate, namely an enzymolysis product.
3. The method of claim 2, wherein the complex enzyme solution comprises the following specific components: 5% aqueous solution with the mass concentration of cellulase, hemicellulase and beta-glucosidase in a mass ratio of 5:5: 1; wherein the cellulase is 400U/mg, the hemicellulase is 5U/mg, and the beta-glucosidase is 10U/mg.
4. The method according to claim 1, wherein the step 2) is specifically: adding betaine and a stabilizing agent nicotinic acid into the enzymolysis product obtained in the step 1), heating to inactivate enzyme, adding a solvent, and performing reflux extraction for 3 hours under a reduced pressure condition to obtain a crude product solution.
5. The method of claim 1, wherein the solvent in step 2) is water and glycerol at a mass ratio of 7: 2.
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| CN113832198B (en) * | 2021-10-11 | 2023-09-19 | 武夷学院 | Method for extracting resveratrol from giant knotweed |
| CN116806884B (en) * | 2023-07-04 | 2024-04-26 | 河南工业大学 | Preparation method of peanut oil rich in resveratrol |
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