CN109924390B - Preparation method of biological natural preservative and application of biological natural preservative in sturgeon caviar - Google Patents
Preparation method of biological natural preservative and application of biological natural preservative in sturgeon caviar Download PDFInfo
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Abstract
A preparation method of a biological natural preservative and application of the biological natural preservative in sturgeon caviar. The invention discloses a natural preservative of octyl gallate/2-hydroxypropyl-beta-cyclodextrin inclusion compound, which is prepared by encapsulating octyl gallate and 2-hydroxypropyl-beta-cyclodextrin according to the molar ratio of 1: 0.5-1.5. Also discloses a method for preparing the octyl gallate by an enzymatic method in a deep eutectic solvent. In addition, the application of the preservative in the preservation of the sturgeon caviar is also disclosed, and the treated caviar can keep the efficacy for a long time and effectively reduce the storage cost. The preservative is tasteless, nontoxic and edible, the components are green, safe and environment-friendly, the water solubility and the bacteriostatic effect of the octyl gallate are improved, the pollution of pathogenic bacteria in the storage and transportation processes of aquatic products is effectively inhibited, the shelf life can be effectively prolonged, and the application range of the octyl gallate as the preservative in the field of foods is expanded.
Description
Technical Field
The invention relates to a food preservative, in particular to a bacteriostatic agent, which is particularly applied to the preservation of aquatic products.
Background
Sturgeon Caviar (Caviar) is an expensive aquatic product prepared by screening and salting sturgeon roe, and is also a main product in sturgeon processing industry. The sturgeon roe sauce is rich in various amino acids and highly unsaturated fatty acids (EPA, DHA) necessary for human bodies, inorganic salts, vitamins A, B and D, and trace elements such as calcium, copper, magnesium, iron and selenium, and has health care effects and potential for developing skin care products. China is also one of the countries with the most sturgeon varieties and has the natural advantages of developing caviar products.
In the prior art, the caviar is eaten more and the boric acid is a traditional raw material for preparing the caviar. Boric acid is prohibited from being added to the food. At present, caviar is generally pickled by salt, vacuumized and stored in a sealed manner at 0 ℃, so that the shelf life is short and the taste and mouthfeel are influenced. Therefore, the application of the natural plant source and animal source food preservative in the process of preserving the caviar becomes a hotspot of research of people. Octyl gallate (GAC8) has good bacteriostatic activity and can be used as a natural preservative in the field of food, but the poor water solubility of the octyl gallate limits the application range of the octyl gallate in the field of aquatic products.
Beta-cyclodextrin molecules have special structures and properties of 'hydrophobic inner cavity and hydrophilic outer wall', and meanwhile, have good crystallization performance, are easy to purify and low in cost, so that the beta-cyclodextrin molecules are often used for improving the solubility of substances. Compared with the like products, the water solubility of the beta-cyclodextrin is poorer, the modified 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CD) has a special structure and very stable characteristics, is not easily influenced by external conditions such as pH, enzyme, heat and the like, and a hydrophobic inner cavity can provide an ideal action site to be combined with a hydrophobic object (such as an organic molecule, an inorganic ion, a biological small molecule, a complex or even inert gas and the like) with a certain size and shape to form a host-object inclusion compound, so that the physicochemical property of the object molecule is changed, the effects of shielding, controlled release, activity protection and the like are achieved, and the application field of the object molecule is expanded.
In the preparation process of functional molecules, enzymatic reaction is widely used for replacing traditional organic reaction due to various advantages of the enzymatic reaction, such as low reaction temperature, short reaction time, high production efficiency, recyclable biological enzyme preparation and the like. In particular, enzymatic reactions in non-aqueous media, such as functional ionic liquids, have significant advantages over traditional organic solvents; and the other kind of non-aqueous medium, Deep Eutectic Solvent (DES), has the advantages of no toxicity, easy preparation, low price, biodegradability, 100% atom utilization rate in the synthetic process, etc., and the application research thereof is widely concerned. The deep eutectic solvent is a novel solvent consisting of a hydrogen bond acceptor (quaternary ammonium salt) and a hydrogen bond donor (urea, carboxylic acid, polyhydric alcohol and the like) in a certain metering ratio, and has wide research and application prospects in the field of enzyme catalysis.
The subject group prepares the GAC8 by enzymatic conversion in a deep cosolvent, further prepares the GAC 8/HP-beta-CD by a freeze-drying method, is used as a food preservative for storage and preservation of sturgeon caviar, solves the problem of poor water solubility of the GAC8, improves the original antibacterial efficiency, is colorless and tasteless, does not influence the quality of the caviar during storage, and can effectively prolong the shelf life. Therefore, the caviar preservative with higher efficiency and higher quality is provided.
Disclosure of Invention
According to the defects of the prior art, the invention aims to provide the natural biological preservative for the sturgeon caviar, which is healthy and safe, has excellent preservative and preservative effects and is wide in bacteriostatic application.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a preparation method of octyl gallate/2-hydroxypropyl-beta-cyclodextrin supermolecule biological natural preservative comprises the following steps:
s1, preparing octyl gallate by utilizing enzymatic reaction in a deep eutectic solvent;
s2, stirring and encapsulating octyl gallate and 2-hydroxypropyl-beta-cyclodextrin in 30% ethanol solution, and freeze-drying to obtain the biological natural preservative.
Preferably, the biological natural preservative exists in the form of solid powder, and the molar ratio of the GAC8 to the HP-beta-CD in the solid is 1 (0.5-1.5).
The invention also provides a method for preparing the GAC8 through an enzymatic reaction in the deep eutectic solvent, which comprises the following steps:
mixing acetylcholine with two hydrogen bond donor urea and glycerol (1:1:1), stirring at 80 deg.C for 2 hr to obtain transparent liquid, i.e. deep eutectic solvent with water content of 10% (w/w). Catalyzing the transesterification of methyl gallate and octanol in a deep eutectic solvent by using lipase (Novo 435,10mg) to form a coarse octyl gallate product, further purifying by using a chromatographic column, collecting a product phase, and removing the solvent under reduced pressure to obtain a GAC8 pure product (> 98%, HPLC).
Preferably, in step S2,
adding HP-beta-CD into deionized water, and magnetically stirring at room temperature until the HP-beta-CD is completely dissolved; then slowly dripping the GAC8 absolute ethyl alcohol solution into the HP-beta-CD aqueous solution, and continuously stirring; removing ethanol by using a rotary evaporator; refrigerating overnight in a refrigerator at-20 deg.C, and freeze drying to obtain GAC 8/HP-beta-CD powder.
Preferably, the stirring conditions are as follows: 60 ℃ for 24 h.
Preferably, the freeze-drying conditions are as follows: 36h at-50 ℃.
The invention also provides the biological natural preservative prepared by the preparation method.
The invention further provides application of the biological natural preservative in keeping sturgeon caviar fresh.
Preferably, the specific application method is as follows: and spraying the water solution formed by the biological natural preservative on the surface of the fish roe, stirring, infiltrating, and then packaging to obtain a finished product.
Compared with the prior art, the invention has the beneficial effects that:
the GAC8 is prepared through enzymatic reaction in the deep eutectic solvent, so that the method is efficient, rapid, green and environment-friendly, and reduces the production cost; the obtained GAC8 is effective in prolonging shelf life of product. However, the poor water solubility of the GAC8 limits the application of the GAC8 in the preservation of aquatic products. The GAC 8/HP-beta-CD encapsulate obtained by utilizing the encapsulation effect of the HP-beta-CD cavity not only improves the water solubility of the GAC8, but also improves the bacteriostatic activity of the GAC8 and reduces the dosage of additives.
Drawings
FIG. 1 is a line graph of esterification yield of methyl gallate and octanol in a molar ratio of 1 (2-10) in example 1 of the present invention.
FIG. 2 is a graph showing the change in the number of colonies of the sturgeon caviar obtained in examples 2 to 5 of the present invention and in control group 1.
Fig. 3 is a line graph showing the variation of TBA value during cold storage of sturgeon caviar obtained in example 6 of the present invention and control group 2.
Detailed Description
The invention is further described with reference to specific examples.
Example 1
The steps for preparing GAC8 by an enzymatic method in a deep eutectic solvent are as follows:
mixing acetylcholine with two hydrogen bond donor urea and glycerol (molar weight is 1:1:1), stirring at 80 deg.C for 2h to obtain transparent liquid, i.e. deep eutectic solvent, wherein the water content in the deep eutectic solvent is 10% (w/w). Catalyzing transesterification reaction of methyl gallate and octanol (molar ratio is 1: 2-10) in a deep eutectic solvent by using lipase (Novo 435,10mg) to form a coarse octyl gallate product, further purifying by using a chromatographic column, collecting a product phase, and removing the solvent under reduced pressure to obtain a GAC8 pure product (> 98%, HPLC). The esterification yield obtained is shown in FIG. 1.
Example 2
A natural biological antistaling agent exists in the form of solid powder, and the molar ratio of the components GAC8 and HP-beta-CD in the powder is 1: 1.5.
The preparation and application of the biological natural preservative comprise the following steps:
(1) adding HP-beta-CD into deionized water, and magnetically stirring at room temperature until the HP-beta-CD is completely dissolved; then slowly dripping the GAC8 absolute ethyl alcohol solution into the HP-beta-CD aqueous solution, and continuously stirring; removing ethanol by using a rotary evaporator; refrigerating overnight at-20 deg.C, and freeze drying (-50 deg.C, 36h) to obtain GAC 8/HP-beta-CD powder.
(2) A processing method for spraying a green preservative to sturgeon caviar and prolonging the storage period of the sturgeon caviar comprises the following steps:
(3) selecting materials: selecting a female sturgeon with proper gonad development as a parent fish to pick eggs, wherein the egg diameter is more than 2-8 mm.
(4) Taking eggs and separating fish roes: soaking parent fish in ice water at 5-8 ℃ for 30-60 min, and carrying out in-vitro shaping on roe by using ice anesthesia on the parent fish so as to be convenient to take out; the ovaries were removed from the abdomen and pressed against a sterilized sieve to obtain roes.
(5) Rinsing: repeatedly rinsing with ice water until the roe is clear.
(6) Selecting: draining off water and picking out impurities.
(7) Preservative treatment: classifying the fish roes according to grades, uniformly spraying an aqueous solution of a preservative of 2mg/mL on the surface of the fish roes, uniformly stirring, and soaking for 15-20 min.
(8) Packaging and storing finished products: storing the mixture in a sterilized storage tank, and after air is exhausted, sealing the storage tank and performing cold storage at the temperature of-2 to 2 ℃.
(9) The storage period of the product obtained by the method reaches 3-6 months.
The colony number variation curve of the obtained product is shown in FIG. 2.
Example 3
A natural biological antistaling agent exists in the form of solid powder, and the molar ratio of GAC8 and HP-beta-CD in the powder is 1:1.2
The preparation and application of the biological natural preservative comprise the following steps:
(1) adding HP-beta-CD into deionized water, magnetically stirring at room temperature to dissolve completely, slowly adding dropwise GAC8 anhydrous ethanol solution into the HP-beta-CD aqueous solution prepared previously, stirring, removing ethanol by using a rotary evaporator, refrigerating at-20 deg.C overnight, and freeze-drying at (-50 deg.C, 36h) to obtain GAC 8/HP-beta-CD powder.
(2) A processing method for spraying a green preservative to sturgeon caviar and prolonging the storage period of the sturgeon caviar comprises the following steps:
(3) selecting materials: selecting a female sturgeon with proper gonad development as a parent fish to pick eggs, wherein the egg diameter is more than 2-8 mm.
(4) Taking eggs and separating fish roes: soaking parent fish in ice water at 5-8 ℃ for 30-60 min, and carrying out in-vitro shaping on roe by using ice anesthesia on the parent fish so as to be convenient to take out; the ovaries were removed from the abdomen and pressed against a sterilized sieve to obtain roes.
(5) Rinsing: repeatedly rinsing with ice water until the roe is clear.
(6) Selecting: draining off water and picking out impurities.
(7) Preservative treatment: classifying the fish roes according to grades, uniformly spraying an aqueous solution of a preservative of 2mg/mL on the surface of the fish roes, uniformly stirring, and soaking for 15-20 min.
(8) Packaging and storing finished products: storing the mixture in a sterilized storage tank, and after air is exhausted, sealing the storage tank and performing cold storage at the temperature of-2 to 2 ℃.
(9) The storage period of the product obtained by the method reaches 5-7 months.
The colony number variation curve of the obtained product is shown in FIG. 2.
Example 4
A natural biological antistaling agent exists in the form of solid powder, and the molar ratio of GAC8 and HP-beta-CD in the powder is 1:1
The preparation and application of the biological natural preservative comprise the following steps:
(1) adding HP-beta-CD into deionized water, and magnetically stirring at room temperature until the HP-beta-CD is completely dissolved; then slowly dripping the same molar weight of GAC8 absolute ethyl alcohol solution into the HP-beta-CD aqueous solution prepared previously, and continuously stirring; removing ethanol by using a rotary evaporator; refrigerating overnight in a refrigerator at-20 deg.C, and freeze-drying (-50 deg.C, 36h) to obtain GAC 8/HP-beta-CD powder.
(2) A processing method for spraying a green preservative to sturgeon caviar and prolonging the storage period of the sturgeon caviar comprises the following steps:
(3) selecting materials: selecting a female sturgeon with proper gonad development as a parent fish to pick eggs, wherein the egg diameter is more than 2-8 mm.
(4) Taking eggs and separating fish roes: soaking parent fish in ice water at 5-8 ℃ for 30-60 min, and carrying out in-vitro shaping on roe by using ice anesthesia on the parent fish so as to be convenient to take out; the ovaries were removed from the abdomen and pressed against a sterilized sieve to obtain roes.
(5) Rinsing: repeatedly rinsing with ice water until the roe is clear.
(6) Selecting: draining off water and picking out impurities.
(7) Preservative treatment: classifying the fish roes according to grades, uniformly spraying an aqueous solution of a preservative of 2mg/mL on the surface of the fish roes, uniformly stirring, and soaking for 15-20 min.
(8) Packaging and storing finished products: storing the mixture in a sterilized storage tank, and after air is exhausted, sealing the storage tank and performing cold storage at the temperature of-2 to 2 ℃.
(9) The storage period of the product obtained by the method reaches 6-8 months.
The colony number variation curve of the obtained product is shown in FIG. 2.
Example 5
A natural biological antistaling agent exists in the form of solid powder, and the molar ratio of GAC8 and HP-beta-CD in the powder is 1:0.5
The preparation and application of the biological natural preservative comprise the following steps:
(1) adding HP-beta-CD into deionized water, and magnetically stirring at room temperature until the HP-beta-CD is completely dissolved; then slowly dripping the GAC8 absolute ethyl alcohol solution into the HP-beta-CD aqueous solution prepared previously, and continuously stirring; removing ethanol by using a rotary evaporator; refrigerating overnight in a refrigerator at-20 deg.C, and freeze-drying (-50 deg.C, 36h) to obtain GAC 8/HP-beta-CD powder.
(2) A processing method for spraying a green preservative to sturgeon caviar and prolonging the storage period of the sturgeon caviar comprises the following steps:
(3) selecting materials: selecting a female sturgeon with proper gonad development as a parent fish to pick eggs, wherein the egg diameter is more than 2-8 mm.
(4) Taking eggs and separating fish roes: soaking parent fish in ice water at 5-8 ℃ for 30-60 min, and carrying out in-vitro shaping on roe by using ice anesthesia on the parent fish so as to be convenient to take out; the ovaries were removed from the abdomen and pressed against a sterilized sieve to obtain roes.
(5) Rinsing: repeatedly rinsing with ice water until the roe is clear.
(6) Selecting: draining off water and picking out impurities.
(7) Preservative treatment: classifying the fish roes according to grades, uniformly spraying an aqueous solution of a preservative of 2mg/mL on the surface of the fish roes, uniformly stirring, and soaking for 15-20 min.
(8) Packaging and storing finished products: storing the mixture in a sterilized storage tank, and after air is exhausted, sealing the storage tank and performing cold storage at the temperature of-2 to 2 ℃.
(9) The storage period of the product obtained by the method reaches 5-7 months.
The colony number variation curve of the obtained product is shown in FIG. 2.
Comparative example 1
Referring to the preparation method of example 2, but without the treatment step of the preservative in the step (7), the colony count variation curve of the obtained product was shown in FIG. 2, when it was directly packaged and stored.
Example 6
Adding GAC 8/HP-beta-CD (molar ratio of GAC8 to HP-beta-CD is 1:1) biological natural preservative and boric acid into sturgeon caviar (0.2mg/g), respectively, performing tracking determination of fat oxidation (TBA value) of the caviar under the condition of 0 ℃ refrigeration, and determining for 8 months. The results of the change in TBA value during the cold storage of the obtained sturgeon roe paste are shown in fig. 3.
Comparative example 2
The results of the variation in TBA value during 0 ℃ cold storage of the obtained sturgeon caviar are shown in fig. 3 with reference to the method of example 6 without adding any fresh-keeping agent.
Claims (5)
1. The application of the biological natural preservative in the preservation of the sturgeon caviar is characterized in that the preparation method of the biological natural preservative comprises the following steps:
s1, preparing octyl gallate by an enzymatic method in a deep eutectic solvent;
s2, stirring and encapsulating the prepared octyl gallate and 2-hydroxypropyl-beta-cyclodextrin in 30% ethanol solution, and freeze-drying to obtain the biological natural preservative;
in step S2, the preparation of the encapsulate is as follows:
adding 2-hydroxypropyl-beta-cyclodextrin into deionized water at room temperature, and magnetically stirring until the 2-hydroxypropyl-beta-cyclodextrin is completely dissolved; then adding an octyl gallate absolute ethyl alcohol solution, slowly dripping the octyl gallate absolute ethyl alcohol solution into the 2-hydroxypropyl-beta-cyclodextrin aqueous solution, and continuously stirring; removing absolute ethyl alcohol by rotary evaporation; -20oRefrigerating the mixture overnight in a refrigerator, and freeze-drying the mixture to obtain biological natural preservative powder;
the temperature of freeze-drying is-50 deg.CoAnd C, the freeze-drying time is 36 h.
2. The use of the biological natural preservative according to claim 1 in the preservation of sturgeon caviar, characterized in that the biological natural preservative is present in the form of solid powder after freeze-drying.
3. The application of the biological natural preservative in the preservation of sturgeon caviar according to claim 1, wherein the octyl gallate and the 2-hydroxypropyl-beta-cyclodextrin are encapsulated according to a molar ratio of 1 (0.5-1.5).
4. The application of the biological natural preservative in the preservation of sturgeon caviar according to claim 1, which is characterized in that the step of preparing octyl gallate by using the deep eutectic solvent is as follows:
in a deep eutectic solvent prepared by mixing acetylcholine, two hydrogen bond donor urea and glycerol, catalyzing methyl gallate and octanol by using lipase to perform transesterification to form a coarse product of octyl gallate, further purifying by using a chromatographic column, collecting a product phase, and removing the solvent under reduced pressure to obtain a pure product of octyl gallate;
the molar ratio of the gallic acid methyl ester to the octanol is 1 (2-10).
5. The application of the biological natural preservative in keeping sturgeon caviar fresh according to any one of claims 1 to 4, characterized in that an aqueous solution formed by the biological natural preservative is sprayed on the surface of roes, stirred, soaked and then packaged to obtain a finished product.
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