Oleogelling agent production method

Abstract

The purpose of the present invention is to provide a new oleogelling agent. A dehydration product of a hydrogel prepared using a multicopper oxidase and a polysaccharide having a phenolic hydroxyl group is useful as an oleogelling agent.

Description

Method of manufacturing the oleogelator

[0001] The present invention relates to a method for producing an oleogelator.

[0002] Animal fats contain a lot of saturated fatty acids, which increase cholesterol, and are considered to be a factor in causing obesity and lifestyle-related diseases. With the recent increase in health consciousness, there are concerns about increased health risks due to excessive intake of foods containing saturated fatty acids. In addition, meat substitutes, which are attracting attention worldwide, use coconut oil, which is solid at room temperature, as a vegetable fat, but coconut oil is composed mostly of saturated fatty acids, so it poses the same concerns as animal fats.

[0003] Therefore, various technologies for gelling liquid vegetable oils (forming oleogel) have been developed for the purpose of reducing or replacing fats containing a large amount of saturated fatty acids. For example, hydroxypropyl methylcellulose (HPMC) has been studied as an oleogelator. Specifically, it has been reported that an oleogel containing HPMC and xanthan gum as a substitute for coconut oil did not impair the texture and flavor of chocolate cream (Non-Patent Document 1), that an oleogel prepared from HPMC and methylcellulose (MC) effectively extended the shelf life of peanut butter (Non-Patent Document 2), that in the formulation of muffins, hydroxypropyl methylcellulose oleogel improved the breathability of the product without adversely affecting the softness and chewiness of the muffins (Non-Patent Document 3), and that the use of canola oil gelled with HPMC as a beef tallow substitute in meat patties resulted in a 15% reduction in saturated fat and a reduction in cooking loss compared to beef tallow samples (Non-Patent Document 4).

[0004] Food Science and Technology, 135, Article 110228.Food Hydrocolloids, 61, 399-408Food Hydrocolloids, 77, 796-802.Food Research International Volume 122, August 2019, Pages 566-572

[0005] Although there have been many reports on the creation of oleogel, only a few have been approved as gelling agents. Furthermore, its application to food is extremely limited, and its application to meat substitutes in particular has not progressed sufficiently. This is likely because existing oleogels do not yet possess a structure that functions well in food applications such as meat substitutes. To keep up with the diversification of foods, including meat substitutes, new options for oleogelators are desired.

[0006] Therefore, an object of the present invention is to provide a new oleogelator.

[0007] The present inventors have found that a water-removed product of a hydrogel prepared using a multicopper oxidase and a polysaccharide having a phenolic hydroxyl group is useful as an oleogelator. The present invention was completed based on this finding and through further investigation. Specifically, the present invention provides the following aspects.

[0008] Item 1. A method for producing an oleogelator, comprising the steps of: allowing a multicopper oxidase to act on a polysaccharide having phenolic hydroxyl groups in an aqueous solvent to form a hydrogel; and removing water from the resulting hydrogel. Item 2. The method according to Item 1, wherein the polysaccharide having phenolic hydroxyl groups is a cell wall-derived polysaccharide having phenolic hydroxyl groups. Item 3. The method according to Item 1 or 2, wherein the polysaccharide having phenolic hydroxyl groups is a polysaccharide containing a phenolic ester sugar residue. Item 4. The method according to any one of Items 1 to 3, wherein the multicopper oxidase is laccase. Item 5. The method according to any one of Items 1 to 4, wherein the amount of phenolic hydroxyl groups contained in 100 g of the polysaccharide having phenolic hydroxyl groups is 1.5 to 15.5 mmol. Item 6. An oleogelator comprising a product obtained by removing water from a hydrogel of a crosslinked polysaccharide having phenolic hydroxyl groups. Item 7. Item 8. An oleogel comprising a liquid oil and the oleogelator according to Item 6. Item 9. The oleogel according to Item 7, wherein the liquid oil is a vegetable oil. Item 10. A food product comprising the oleogel according to Item 8. Item 11. The food product according to Item 9, further comprising a textured vegetable protein.

[0009] According to the present invention, a new oleogelator is provided.

[0010] 1 shows photographs of the appearance of canola oil (Comparative Example 1), canola oil processed with beet pectin (Comparative Example 2), and canola oil processed with a dried cross-linked beet pectin hydrogel (oleogel, Example 1). Cooking loss (%) due to heating is shown for an alternative patty using canola oil (Comparative Example 4), an alternative patty using a canola oil oleogel with a dried cross-linked beet pectin hydrogel (Example 2), an alternative patty using a canola oil oleogel with HPMC (Comparative Example 5), and an alternative patty using beef tallow, which is a solid fat (Reference Example 1).

[0011] 1. Method for Producing an Oleogelator The method for producing an oleogelator of the present invention is characterized by comprising the steps of: allowing a multicopper oxidase to act on a polysaccharide having a phenolic hydroxyl group in an aqueous solvent to form a hydrogel; and removing water from the resulting hydrogel. The method for producing an oleogelator of the present invention is described in detail below.

[0012] 1-1. Hydrogelation Process In the hydrogelation process, a polysaccharide having phenolic hydroxyl groups is subjected to the action of a multicopper oxidase in an aqueous solvent to form a hydrogel. That is, a polysaccharide having phenolic hydroxyl groups is treated with the multicopper oxidase in an aqueous solvent to form a hydrogel. Specifically, a mixture containing a polysaccharide having phenolic hydroxyl groups and the multicopper oxidase in water can be subjected to hydrogelation conditions.

[0013] 1-1-1. Polysaccharides Having Phenolic Hydroxyl Groups There are no particular limitations on polysaccharides having phenolic hydroxyl groups, as long as they have a structure in which a compound having a phenolic hydroxyl group is covalently bonded to the polysaccharide. Polysaccharides having phenolic hydroxyl groups exhibit amphiphilicity due to the hydrophobic nature of the benzene ring portion and the hydrophilic nature of the polysaccharide portion.

[0014] Examples of polysaccharides include cell wall-derived polysaccharides. Furthermore, the polysaccharides may be thickening polysaccharides or may not be thickening polysaccharides. Specific examples of polysaccharides include pectin (for example, a polygalacturonic acid-based pectin; it may be HM pectin with a methyl esterification degree of 50% or more, or LM pectin with a methyl esterification degree of less than 50%), hemicellulose (for example, a polysaccharide containing arabinoxylan), cellulose, etc.

[0015] Examples of compounds having a phenolic hydroxyl group include phenolic acids (monophenolic acids (e.g., ferulic acid, coumaric acid, etc.), polyphenolic acids (e.g., lignin, etc.)), peptides or proteins (i.e., containing a tyrosine residue having a phenolic hydroxyl group and an asparagine residue, serine residue, and / or threonine residue bound to a sugar), etc.

[0016] The type of covalent bond may vary depending on the compound having a phenolic hydroxyl group, but examples include an ester bond (when the compound having a phenolic hydroxyl group is a monophenolic acid or a polyphenolic acid), an ether bond (when the compound having a phenolic hydroxyl group is a polyphenolic acid, a peptide, or a protein), and an amide bond (when the compound having a phenolic hydroxyl group is a peptide or a protein).

[0017] The polysaccharide having a phenolic hydroxyl group may be any combination of the above-mentioned phenolic hydroxyl group, the above-mentioned covalent bond, and the polysaccharide, and a specific combination may be used alone, or two or more different combinations may be used in combination.

[0018] Specific examples of polysaccharides having a phenolic hydroxyl group include polysaccharides containing phenolic acid ester sugar residues, polysaccharides in which lignin is ether-bonded, and proteoglycans, and preferred examples include pectin having a phenolic hydroxyl group and polysaccharides containing phenolic acid ester sugar residues.

[0019] A preferred example of a polysaccharide having a phenolic hydroxyl group is pectin having a phenolic hydroxyl group. Pectin having a phenolic hydroxyl group is a pectin to which the above-mentioned compound having a phenolic hydroxyl group is bound via the above-mentioned covalent bond, and the above-mentioned compound having a phenolic hydroxyl group and the type of covalent bond can be arbitrarily selected from the above-mentioned examples. The origin of pectin having a phenolic hydroxyl group is not particularly limited, but preferred examples include beet (Beta vulgaris ssp. vulgaris var. Altissima; also known as sugar beet).

[0020] Preferred examples of polysaccharides having phenolic hydroxyl groups include polysaccharides containing phenolic acid ester sugar residues. Polysaccharides containing phenolic acid ester sugar residues are those in which the carboxyl group of a phenolic acid is ester-bonded to the hydroxyl group of the polysaccharide, and the type of polysaccharide and phenolic acid can be arbitrarily selected from the above-mentioned examples. Preferred examples of polysaccharides containing phenolic acid ester sugar residues include polysaccharides containing monophenolic acid ester residues. Preferred examples of polysaccharides containing monophenolic acid ester residues include pectin and / or arabinoxylan containing ferulic acid ester residues and / or coumaric acid ester residues, and more preferably pectin containing ferulic acid ester residues. A specific example of pectin containing ferulic acid ester residues is the above-mentioned beet-derived pectin.

[0021] The amount of phenolic hydroxyl groups contained in 100 g of a polysaccharide having phenolic hydroxyl groups is not particularly limited as long as an oleogelator can be produced by subjecting the polysaccharide to the production method of the present invention, but may be, for example, 1.5 to 15.5 mmol, preferably 2 to 10 mmol, and more preferably 2.5 to 5 mmol. For example, the content of monophenolic acid in a polysaccharide containing a monophenolate ester residue may be, for example, 0.3 to 3 wt %, preferably 0.4 to 2 wt %, and more preferably 0.5 to 1 wt %.

[0022] The content of the polysaccharide having a phenolic hydroxyl group in the mixed solution (the mixed solution containing the polysaccharide having a phenolic hydroxyl group and the multicopper oxidase in water) is, for example, 0.1 to 10 wt %, preferably 0.5 to 5 wt %, more preferably 1 to 4 wt %, and even more preferably 1.5 to 3 wt %.

[0023] 1-1-2. Multicopper oxidase Multicopper oxidase is a group of enzymes that contain multiple copper atoms in the molecule and catalyze the four-electron reduction of oxygen molecules to water molecules via the oxidation of substrate molecules. The number of copper atoms contained in previously known enzymes is typically 2 to 8, but this number is not particularly limited because it varies depending on the state of the enzyme preparation at the time of analysis and the analytical method. In the present invention, multicopper oxidase is an enzyme that crosslinks phenolic hydroxyl groups together.

[0024] Examples of enzymes classified as multicopper oxidases include laccase, bilirubin oxidase, ascorbic acid oxidase, ceruloplasmin, Fet3p, CueO, CotA, stellacyanin, tyrosinase, catechol oxidase, and nitrite reductase.

[0025] The origin of the multicopper oxidase is not particularly limited, and examples thereof include multicopper oxidases derived from the genera Aspergillus, Neurospora, Podospora, Botrytis, Collybia, Formes, Lentinus, Pleurotus, Pycnoporus, Pyricularia, Trametes, Rhizoctonia, Rigidoporus, Coprinus, Psatyrella, Myceliophtera, Schtalidium, Polyporus, Phlebia, Coriolus, and Bacillus.

[0026] These multicopper oxidases may be used singly or in combination. Among these multicopper oxidases, preferred are laccase, bilirubin oxidase, ascorbic acid oxidase, and tyrosinase, with laccase (EC 1.10.3.2) being particularly preferred. Furthermore, among laccases, preferred are laccases derived from the genus Trametes and laccases derived from the genus Aspergillus (more preferably Aspergillus oryzae), with laccases derived from the genus Trametes being particularly preferred.

[0027] The amount of multicopper oxidase used is not particularly limited, as long as it is sufficient to produce an oleogelator.

[0028] For example, the amount of multicopper oxidase used per millimole of phenolic hydroxyl groups in a polysaccharide having phenolic hydroxyl groups is, for example, 1,500 to 20,000 U, 2,000 to 17,000 U, preferably 2,500 to 15,000 U, 3,000 to 14,500 U, 4,000 to 14,000 U, more preferably 5,000 to 13,500 U, 5,500 to 13,000 U, and even more preferably 5,700 to 12,500 U, or 5,800 to 12,000 U.

[0029] The amount of multicopper oxidase used per gram of polysaccharide having a phenolic hydroxyl group is, for example, 100 to 10,000 U, 100 to 7,000 U, or 100 to 5,000 U, preferably 150 to 3,000 U, 150 to 2,000 U, or 150 to 1,000 U, more preferably 200 to 700 U, 200 to 500 U, and even more preferably 250 to 400 U or 250 to 350 U.

[0030] The activity of multicopper oxidase was measured under the following conditions: 2.5 ml of a substrate solution was prepared by mixing 0.25 mol / L phenol test solution, 0.009 mol / L 4-aminoantipyrine test solution, and 1 mol / L acetic acid / sodium acetate buffer (pH 4.5) in a volume ratio of 1:1:0.5; this was preheated at 30°C; 0.5 ml of an enzyme solution diluted to a specified concentration was added; the mixture was stirred and incubated at 30°C; and the absorbance at 505 nm was measured after 10 seconds and 40 seconds. The amount of enzyme contained in 1 ml of the reaction solution was defined as 1 unit (U) when the absorbance increased by 0.1 per minute.

[0031] 1-1-3. Hydrogelation It is believed that polysaccharides having phenolic hydroxyl groups undergo cross-linking between the phenolic hydroxyl groups in the presence of multicopper oxidase, resulting in a three-dimensional structure, which then leads to hydrogelation.

[0032] The conditions for hydrogelation (pH, temperature, time) can be appropriately set depending on the enzymatic properties of the multicopper oxidase, the reaction scale, etc.

[0033] The temperature can be set appropriately taking into account the optimal temperature of the multicopper oxidase, and can be, for example, 10 to 80°C, 10 to 70°C, 10 to 60°C, or 10 to 50°C, preferably 15 to 40°C, and more preferably 20 to 30°C. The pH can be set appropriately taking into account the optimal pH of the multicopper oxidase, and can be, for example, 3 to 9, preferably 4 to 8, more preferably 5 to 7.5, and even more preferably 6 to 7 or 6.5 to 7 at 25°C. The time can be, for example, 30 seconds to 48 hours, preferably 30 seconds to 24 hours, more preferably 1 minute to 12 hours, 1 minute to 6 hours, 1 minute to 3 hours, 1 minute to 1 hour, 1 to 30 minutes, or 1 to 10 minutes. Optimal conditions for these hydrogelation conditions can be determined through preliminary experiments.

[0034] In the water removal step, water is removed from the hydrogel obtained in the hydrogelation step. The extent of water removal is not particularly limited as long as the water-removed product functions as an oleogelator.

[0035] The method for removing water may be either dehydration or drying, preferably drying. Methods for drying include freeze-drying and vacuum drying, preferably freeze-drying.

[0036] The water-removed product may or may not contain water. Specific examples of the water content in the water-removed product include 10% by weight or less (i.e., 0 to 10% by weight, or more than 0% by weight and 10% by weight or less; the same applies to the following numerical ranges related to the water content), preferably 7.0% by weight or less, more preferably 5.0% by weight or less, even more preferably 3.0% by weight or less, and even more preferably 2.0% by weight or less, 1.0% by weight or less, and 0.5% by weight or less.

[0037] The obtained water-removed product may be used as an oleogelator as it is, or may be used as an oleogelator after being subjected to a physical treatment step described below.

[0038] 1-3. Other Steps In addition to the oleogelation step and the water removal step described above, the method for producing the oleogelator of the present invention may include any other steps, as long as the oleogelator is obtained. Examples of such other steps include a step of inactivating the multicopper oxidase and a step of physically treating the water-removed product. The method for producing the oleogelator of the present invention may include only one of these other steps, or both, or none of the other steps.

[0039] The step of inactivating the multicopper oxidase can be carried out, for example, after the oleogelation step and before the water removal step. The conditions for inactivation can be appropriately determined depending on the action temperature and / or action pH of the multicopper oxidase used. Preferably, the inactivation step is carried out by heat inactivation.

[0040] The physical treatment step of the dehydrated product is carried out after the water removal step. Specific examples of the physical treatment include crushing, pulverization, etc. Crushing and pulverization may be carried out using a known device such as a mixer.

[0041] 2. Oleogelators The oleogelators of the present invention comprise the water-removed product of a cross-linked phenolic hydroxyl-containing polysaccharide hydrogel.

[0042] In the oleogelator of the present invention, the polysaccharide having phenolic hydroxyl groups forms a three-dimensional structure in which the phenolic hydroxyl groups are crosslinked with each other. Therefore, the amphiphilic nature of the polysaccharide, which combines the hydrophobic properties of the benzene ring moiety with the hydrophilic properties of the polysaccharide moiety, chemically agglutinates the liquid oil, and the three-dimensional structure physically retains the liquid oil, thereby reducing or eliminating the fluidity of the liquid oil and exhibiting excellent oleogelating ability. The oleogelator of the present invention can be obtained by the above-mentioned "1. Method for producing oleogelator".

[0043] In a preferred embodiment, the oleogelator of the present invention exhibits antioxidant activity by donating hydrogen to free radicals via the remaining uncrosslinked phenolic hydroxyl groups.

[0044] The form of the oleogelator of the present invention is not particularly limited, but is typically a solid. Specific examples of the form of the oleogelator of the present invention include a block (plate-like, rod-like, irregularly shaped, granular), powder, etc.

[0045] The water content of the oleogelator of the present invention is not particularly limited as long as it does not impair the oleogelating ability, and examples thereof include 10% by weight or less (i.e., 0 to 10% by weight, or more than 0% by weight and 10% by weight or less; the same applies to the numerical ranges relating to the water content below), preferably 7.0% by weight or less, more preferably 5.0% by weight or less, even more preferably 3.0% by weight or less, and even more preferably 2.0% by weight or less, 1.0% by weight or less, or 0.5% by weight or less.

[0046] The oleogel of the present invention comprises a liquid oil and the oleogelator described above in "2. Oleogelator". That is, the oleogel of the present invention is based on a three-dimensional structure in which polysaccharides having phenolic hydroxyl groups are crosslinked with each other, and comprises a liquid oil as a continuous phase.

[0047] The liquid oil is not particularly limited as long as it is an oil that is fluid at 25°C. Preferred examples of the liquid oil include glycerides such as triglycerides. Specific examples of the liquid oil include vegetable oils, the origin of which is not particularly limited, and include soybean oil, rapeseed oil, corn oil, sesame oil, perilla oil, linseed oil, peanut oil, safflower oil, high oleic acid safflower oil, sunflower oil, high oleic acid sunflower oil, cottonseed oil, grapeseed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut oil, camellia oil, tea seed oil, perilla oil, borage oil, olive oil, rice bran oil, wheat germ oil, coconut oil, palm oil, palm kernel oil, and algae oil.

[0048] As the liquid oil, one of the above may be used alone or two or more may be used in combination. Among the liquid oils, vegetable oils are preferred, and canola oil, sunflower oil, soybean oil, and olive oil are more preferred.

[0049] The oleogel of the present invention is obtained by mixing a liquid oil with an oleogelator and then oleogelating the mixture.

[0050] The amount of oleogelator used relative to the liquid oil is not particularly limited, but may be such that the content of the oleogelator in the oleogel is, for example, 0.1 to 10% by weight, preferably 0.5 to 5% by weight, more preferably 1 to 4% by weight, and even more preferably 1.5 to 3% by weight.

[0051] The oleogelation conditions (temperature, time) are not particularly limited. For example, the temperature may be 10 to 80°C, 10 to 70°C, 10 to 60°C, or 10 to 50°C, preferably 15 to 40°C, and more preferably 20 to 30°C. The time may be 30 seconds to 48 hours, preferably 30 seconds to 24 hours, and more preferably 1 minute to 12 hours, 1 minute to 6 hours, 1 minute to 3 hours, 1 minute to 1 hour, or 10 to 30 minutes. Optimal oleogelation conditions can be determined through preliminary experiments.

[0052] The oleogel of the present invention contains an oleogelator having excellent oleogelating ability as described above in "2. Oleogelators", and therefore, in a preferred embodiment, when applied to food products, it exhibits excellent suppression of cooking loss due to heating.

[0053] In a preferred embodiment, the oleogel of the present invention contains an oleogel that exhibits antioxidant activity as described above in "2. Oleogelating Agent," and therefore has excellent oxidation inhibitory properties even when the oleogel is made from a vegetable oil that is rich in unsaturated fatty acids.

[0054] The oleogel of the present invention may be used for either food or non-food purposes (such as cosmetics or pharmaceuticals), but is preferably used for food purposes.

[0055] 4. Food The food of the present invention is a food comprising the above-mentioned "3. oleogel." Ingredients other than the oleogel in the food of the present invention are optional depending on the type of food, and conventional food ingredients can be appropriately selected. Therefore, the food of the present invention may further contain one or more of the following food ingredients: water, seasonings (salt, sugar, etc.), proteins, carbohydrates, lipids, amino acids, vitamins, milk, and flavorings. The proteins and lipids may be derived from plants or animals, or may be a combination of plant and animal origins. The plant-derived protein may be either a non-structured plant protein or a structured plant protein.

[0056] The origin of the vegetable protein is not particularly limited, and examples thereof include pulses such as soybeans, broad beans, peas, chickpeas, mung beans, lupin beans, and kidney beans; cereals such as barley, rice, wheat, rye, oats, buckwheat, barnyard millet, foxtail millet, teff, quinoa, and corn; nuts and seeds such as hemp (industrial hemp), canary seeds, flaxseed, almonds, cashew nuts, hazelnuts, pecan nuts, macadamia nuts, pistachios, walnuts, Brazil nuts, peanuts, coconuts, pili nuts, chestnuts, sesame seeds, and pine nuts; and algae. The food product of the present invention may contain one or more of the above vegetable proteins as the vegetable protein. Among these vegetable proteins, pulse proteins are preferred, soy protein and pea protein are more preferred, and soy protein is even more preferred.

[0057] The food product of the present invention preferably contains a textured vegetable protein, from the viewpoint of more effectively suppressing cooking loss due to heating. Textured vegetable protein is known as a meat substitute (imitation meat), and a typical example is a material that is textured like meat by extruding a raw material mixture containing vegetable protein and water using an extruder or the like, followed by drying or freezing.

[0058] The form of the textured vegetable protein includes granular and fibrous forms. The granular forms include block forms of various sizes such as small granules, large granules, and blocks (increasing in size from small granules to large granules and blocks), and flat forms of various sizes such as flakes, fillets, and slices (increasing in size from flakes to fillets and slices).

[0059] More specific examples of textured vegetable protein materials include granular vegetable protein and fibrous vegetable protein. Both granular vegetable protein and fibrous vegetable protein refer to those defined in the "Japanese Agricultural Standards for Vegetable Protein." However, the textured vegetable protein material used in the present invention is not limited to these, as long as it is a material that has a meat-like texture as described above.

[0060] Specific examples of the food of the present invention include fat products such as fat spreads, margarine, shortening, whitener, whipping cream, whipped cream, and chocolate; baking dough or premixes thereof, or baked products for bread, cakes, cookies, and the like, using the fat products; processed meat, poultry, and / or fish paste foods (including molded meat products such as hamburger steaks, meatballs, patties, meatloaf, minced meat cutlets, dim sum, and sausages); and processed meat substitute foods that imitate the processed foods using meat substitutes.

[0061] The present invention will be specifically described below with reference to examples, but the present invention should not be construed as being limited to the following examples.

[0062] [Materials and enzymes used]

[0063] [Laccase Activity Measurement Method] The reagent used to measure laccase activity was prepared based on the polyphenol oxidase activity measurement test method in the 9th edition of the Japanese Standards for Food Additives. Specifically, a substrate solution was prepared by mixing 0.25 mol / L phenol solution, 0.009 mol / L 4-aminoantipyrine solution, and 1 mol / L acetic acid / sodium acetate buffer (pH 4.5) in a volume ratio of 1:1:0.5. 2.5 ml of this substrate solution was placed in a cuvette and preheated to 30°C. 0.5 ml of a diluted enzyme solution was added, stirred, and incubated at 30°C. The absorbance at 505 nm was measured after 10 and 40 seconds. Under these conditions, an increase in absorbance of 0.1 per minute was defined as one unit (U) of enzyme content in 1 mL of reaction solution.

[0064] [Test Example 1] [1] Sample Preparation [1-1] Comparative Example 1 Canola oil was prepared in a microtube.

[0065] [1-2] Example 1 Two grams of beet-derived pectin was dissolved in 90 mL of distilled water, and laccase was added to a final concentration of 300 U per gram of beet-derived pectin (5,825 to 11,650 U per millimole of phenolic hydroxyl groups in beet-derived pectin). The total volume was then adjusted to 100 mL with water. Immediately after addition, the mixture was stirred and allowed to stand at pH 6.8 and 25°C for 3 minutes. After complete hydrogelation, the mixture was dried in a freeze dryer, and the resulting dried product was crushed in a mixer. This resulted in a crushed product (dried hydrogel of crosslinked beet pectin). Because this crushed product is in a dry state, it contains almost no water. The crushed product thus obtained was added to canola oil in a microtube to a final concentration of 2% by weight, stirred, and allowed to stand at 25°C for 10 minutes.

[0066] [1-3] Comparative Example 2: 2 g of beet-derived pectin was dissolved in 90 mL of distilled water, and then the solution was adjusted to 100 mL with water. The mixture was stirred immediately after addition, allowed to stand at pH 6.8 and 25°C for 3 minutes, then dried in a freeze dryer, and the resulting dried product was crushed in a mixer. The crushed product (redried beet pectin) thus obtained was added to canola oil in a microtube to a final concentration of 2 wt%, stirred, and allowed to stand at 25°C for 10 minutes.

[0067] [2] Evaluation of oleogelation ability The microtubes containing each sample were capped and inverted. The results are shown in Figure 1. As shown in Figure 1, canola oil (Comparative Example 1) was liquid. Similarly, the processed mixture of dried pectin and canola oil (Comparative Example 2) was liquid, and no oleogel formation was observed. On the other hand, the processed mixture of dried cross-linked pectin hydrogel and canola oil (Example 1) had no fluidity, and oleogel formation was observed.

[0068] Test Example 2: Instead of canola oil, sunflower oil, soybean oil, or olive oil was used, and the same treatment as in Example 1 was carried out. As a result, when any of the vegetable oils was used, oleogel formation was observed, as in Example 1.

[0069] Test Example 3 [1] Sample Preparation [1-1] Comparative Example 1 Canola oil was prepared.

[0070] [1-2] Example 1 The oleogel prepared in Example 1 of Test Example 1 was prepared.

[0071] [1-3] Comparative Example 3 Hydroxypropyl methylcellulose (Metolose, SFE-4000, Shin-Etsu Chemical Co., Ltd.) was added to canola oil to a final concentration of 2% by weight and stirred. The mixture was allowed to stand at 25°C for 10 minutes to obtain an oleogel.

[0072] [2] Evaluation of Oxidative Stress Resistance The peroxide value (POV) of each sample was measured in accordance with the international standard ISO 3960:2017. POV is defined as the amount of iodine molecules liberated when hydroperoxide is reacted with potassium iodide, expressed in milliequivalents (meq) per kg of sample. 5 g of sample was dissolved in 35 mL of an isooctane-acetic acid mixture (isooctane:glacial acetic acid = 2:3 (volume ratio)). 1 mL of saturated potassium iodide solution was added, the flask was immediately stoppered, and the flask was shaken for 1 minute and then allowed to stand for 5 minutes at room temperature in the dark. 75 mL of water was added, and the flask was shaken vigorously. 1 mL of 1 wt% starch solution was added, and the mixture was titrated with 0.01 mol / L sodium thiosulfate solution as an indicator. The titration was performed with thorough stirring, and the endpoint was the disappearance of the blue color due to the starch. The results are shown in Table 2.

[0073]

[0074]

[0075] As shown in Table 2, canola oil (Comparative Example 1) showed an extremely high peroxide value on the 14th day. Furthermore, the canola oil oleogel (Comparative Example 3) using HPMC showed a reduced peroxide value, demonstrating resistance to oxidative stress. On the other hand, the canola oil oleogel (Example 1) using the dried crosslinked beet pectin hydrogel showed a further reduced peroxide value, demonstrating improved resistance to oxidative stress. Although both Comparative Example 3 and Example 1 were oleogels, the higher antioxidant properties of Example 1 can be attributed to the residual phenolic hydroxyl groups of the ferulic acid ester sugar residues in the dried crosslinked beet pectin hydrogel used as the oleogelator.

[0076] [Test Example 4] [1] Preparation of Sample (Alternative Patty) [1-1] Example 2 Six times the weight of water was added to 10 g (dry weight) of a textured soy protein material, and the material was allowed to stand at 60°C for 60 minutes to swell, followed by rinsing with water. After draining the water, 25 g of the swollen textured vegetable protein material was mixed with 15 mL of water and methylcellulose (final concentration 2 wt%). Next, 7.5 g of the oleogel of Example 1 (canola oil oleogel made from a dried cross-linked beet pectin hydrogel) was added and thoroughly mixed. The mixture was molded into a patty shape to obtain an alternative patty (before baking). The alternative patty (before baking) was baked at 150°C for 10 minutes (5 minutes on each side) to obtain an alternative patty (after baking).

[0077] [1-2] Comparative Example 4 A substitute patty (before baking) and a substitute patty (after baking) were obtained in the same manner as in Example 2, except that the canola oil of Comparative Example 1 was used instead of the oleogel of Example 1.

[0078] [1-3] Comparative Example 5 A substitute patty (before baking) and a substitute patty (after baking) were obtained in the same manner as in Example 2, except that the oleogel of Comparative Example 3 (canola oil oleogel with HPMC) was used instead of the oleogel of Example 1.

[0079] [1-4] Reference Example 1 A substitute patty (before baking) and a substitute patty (after baking) were obtained in the same manner as in Example 2, except that beef tallow was used instead of the oleogel in Example 1.

[0080] [2] Evaluation of Cooking Loss Suppression Due to Heating The weight of the alternative patty (before baking) and the weight of the alternative patty (after baking) were measured, and the cooking loss (%) was calculated based on the following formula. The lower the cooking loss (%), the higher the suppression of cooking loss due to heating, and is generally an indicator of the juiciness of the food after baking. The results are shown in Figure 2.

[0081]

[0082] 2 , the alternative patty using canola oil, a liquid oil (Comparative Example 4), exhibited a large cooking loss, while the alternative patty using beef tallow, a solid fat (Reference Example 1), exhibited reduced cooking loss. The alternative patty using canola oil oleogel with HPMC (Comparative Example 5) also exhibited reduced cooking loss compared to Comparative Example 4, but not as effectively as Reference Example 1. On the other hand, the alternative patty using canola oil oleogel with a dried crosslinked beet pectin hydrogel (Example 2) not only exhibited reduced cooking loss compared to Comparative Example 4, but also exhibited a more effective suppression of cooking loss than Reference Example 1.

[0083] [3] Texture Profile Analysis of Baked Patties The substitute patties (after baking) of Comparative Example 4, Example 2, and Reference Example 1 were measured for cohesiveness, elasticity, and chewiness using a rheometer (manufactured by Sun Scientific Co., Ltd.). The results are shown in Table 3. Stress: Maximum force (N) recorded during the first compression Cohesiveness: Value obtained by dividing the working area during the second compression by the area during the first compression Elasticity: Value obtained by dividing the distance recorded during the second compression by the distance during the first compression Chewability: Stress (N) x Cohesiveness x Elasticity

[0084]

[0085] As shown in Table 3, the alternative patty (Example 2) using canola oil oleogel made from the dried cross-linked beet pectin hydrogel exhibited a softer, more elastic and superior texture than the alternative patty (Comparative Example 4) using canola oil, which is a liquid oil, and the degree of this was equal to or better than that of the alternative patty (Reference Example 1) using beef tallow, which is a solid fat.

Claims

1. A method for producing an oleogelator, comprising the steps of: allowing a polysaccharide having a phenolic hydroxyl group to undergo the action of a multicopper oxidase in an aqueous solvent to form a hydrogel; and removing water from the resulting hydrogel.

2. The method according to claim 1, wherein the polysaccharide having a phenolic hydroxyl group is a cell wall-derived polysaccharide having a phenolic hydroxyl group.

3. The method according to claim 1, wherein the polysaccharide having a phenolic hydroxyl group is a polysaccharide containing a phenolic acid ester sugar residue.

4. The method according to claim 1, wherein the multicopper oxidase is laccase.

5. The method according to claim 1, wherein the amount of phenolic hydroxyl groups contained in 100 g of the polysaccharide having phenolic hydroxyl groups is 1.5 to 15.5 mmol.

6. An oleogelator comprising a water-removed hydrogel of a cross-linked phenolic hydroxyl-containing polysaccharide.

7. An oleogel comprising a liquid oil and the oleogelator of claim 6.

8. The oleogel of claim 7, wherein the liquid oil is a vegetable oil.

9. A food product comprising the oleogel of claim 8.

10. The food product of claim 9, further comprising a textured vegetable protein.

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