Compositions containing polyphenols

Abstract

To provide a polyphenol-containing composition which can be used in various applications.SOLUTION: The present application relates to a composition including chlorogenic acid, caffeic acid, and quinic acid. The polyphenol-containing composition of the present application can be used in applications involving an off-taste or off-flavor to be reduced. In addition, the polyphenol-containing composition of the present application can be used in a preservative of a product, in particular an antioxidant or browning inhibitor of a product.SELECTED DRAWING: None

Description

Technical Field

[0004] ,

[0001] This application relates to a composition containing polyphenols and its uses.

Background Art

[0002] Polyphenols are compounds contained in plants such as fruits and leafy vegetables. To date, more than thousands of types of polyphenols have been identified. Typically, flavonoids, anthocyanins, tannins, catechins, isoflavones, lignans, resveratrols, etc. can be mentioned. The numerous hydroxyl groups (-OH) present in polyphenols have the property of easily binding to many compounds and are excellent in antioxidant effects and anti-cancer and anti-inflammatory effects. <00,00011> Polyphenols can exhibit effects even as single substances, but it is known that the effects can be enhanced by combining each substance, and the combination is important (Korean Patent Publication No. 10-2015-0016343). However, the types of polyphenols are diverse, and it is difficult to confirm the enhancing effect due to the combination.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] One object of this application is to provide a composition containing polyphenols that can be used for various purposes.

Means for Solving the Problems

[0006] To achieve the aforementioned objectives, one aspect of this application provides a composition comprising chlorogenic acid, caffeic acid, and quinic acid.

[0007] Furthermore, in order to achieve the aforementioned objectives, another aspect of this application provides a method for reducing off-flavors or off-odors, comprising the step of adding a composition containing chlorogenic acid, caffeic acid, and quinic acid to a substance that generates off-flavors or off-odors.

[0008] Furthermore, in order to achieve the aforementioned objectives, another aspect of this application provides a method for producing a substance that reduces off-flavors or off-odors, comprising the step of adding a composition containing chlorogenic acid, caffeic acid, and quinic acid to a substance that generates off-flavors or off-odors.

[0009] Furthermore, in order to achieve the aforementioned objectives, another aspect of this application provides a use as a flavoring or odorant for compositions containing chlorogenic acid, caffeic acid, and quinic acid.

[0010] Furthermore, in order to achieve the aforementioned objectives, another aspect of this application provides a preservation composition for products comprising chlorogenic acid, caffeic acid, and quinic acid.

[0011] Furthermore, in order to achieve the aforementioned objectives, another aspect of this application provides a method for preventing oxidation of a product, comprising the step of adding a composition containing chlorogenic acid, caffeic acid, and quinic acid to the product.

[0012] Furthermore, in order to achieve the aforementioned objectives, another aspect of this application provides a method for suppressing browning of a product, comprising the step of adding a composition containing chlorogenic acid, caffeic acid, and quinic acid to the product. [Effects of the Invention]

[0013] The composition comprising chlorogenic acid, caffeic acid, and quinic acid described in this application can be used in a variety of applications.

[0014] The composition of this application can be used for reducing off-flavors or off-odors. The composition of this application is extremely effective in reducing trimethylamine (TMA), which is a substance that causes off-flavors or off-odors, and has an outstanding effect in reducing off-flavors or off-odors by inducing changes in various volatile fragrance components.

[0015] Furthermore, unlike conventional off-flavor or off-odor reducing substances, the composition of this application has the advantage of being able to be applied to the manufacturing process of processed products in very small amounts, without affecting the original characteristics of the product, and without affecting the original characteristics of the product.

[0016] Furthermore, the composition comprising chlorogenic acid, caffeic acid, and quinic acid of this application can be used for product preservation purposes, specifically for preventing oxidation or inhibiting browning of products.

[0017] As confirmed by its DPPH radical scavenging ability, the polyphenol composition of this application exhibits excellent antioxidant effects, superior oxidative stability, high polyphenol oxidase inhibitory activity, and browning suppression activity.

[0018] Furthermore, unlike conventional antioxidants or browning inhibitors, the composition of this application has the advantage of leaving very little residue in the product, not affecting the original characteristics of the product, and being easy to apply to the manufacturing process of processed products.

[0019] However, the effects of this application are not limited to those mentioned above, and any other effects not mentioned will be clearly understood by those skilled in the art from the following description. [Modes for carrying out the invention]

[0020] The present application will be described in detail below.

[0021] According to one aspect of this application, the application provides a composition comprising chlorogenic acid, caffeic acid, and quinic acid.

[0022] The active ingredients of this application, chlorogenic acid, caffeic acid, and quinic acid, are polyphenol components.

[0023] As used in this application, the term "polyphenol" means a compound containing one or more phenols having one or more hydroxy groups in the molecule. The term "polyphenol" in this specification is used to mean not only the polyphenol itself but also derivatives such as its glycosides, its alkylated compounds, and its esterified compounds.

[0024] In this application, chlorogenic acid is a compound formed by an ester bond between caffeic acid and quinic acid, and is represented by the following Chemical Formula 1.

[0025] [Chem.]

[0026] In this application, caffeic acid is a compound classified as hydroxycinnamic acid, and is represented by the following Chemical Formula 2.

[0027] [Chem.]

[0028] In this application, quinic acid is represented by the following Chemical Formula 3.

[0029] [Chem.]

[0030] In this application, the chlorogenic acid, caffeic acid, and quinic acid used can be not only substances derived from natural products but also artificially synthesized substances.

[0031] The aforementioned natural products may be plants, but are not limited to any substance containing chlorogenic acid, caffeic acid, and / or quinic acid. Specifically, aloe, anise seed, elder, Eleutherococcus senticosus, plantain, orange blossom, allspice, oregano, senna, chamomile, capsicum pepper, cardamom, cassia, garlic, caraway seed, clove, cumin seed, cola, coriander seed, sumac, saffron, sansho pepper, juniper berry, cinnamon, ginger, star anise, St. John's walnut, celery seed, savory, sesame, rhubarb. Tarragon, turmeric, thistle, dill seeds, nutmeg, nettle, hibiscus, witch hazel, birch, basil, bitter orange, fennel, primrose, fenugreek, verbena, bay laurel, hops, Bordeaux, wasabi, poppy seeds, gallnuts, marigold, chestnut, marjoram, mustard, millefoil, mint leaves, melsa, mace, linden, gentian, rosehip, rosemary, rosemary, sunflower seeds, grape skins, apple, carrot leaves, banana, strawberry, apricot, peach, plum, pineapple, pear, persimmon, cherry, papaya, mango, avocado, melon, loquat, fig, kiwi, prune, blueberry, blackberry, raspberry, cranberry, coffee beans, cocoa beans, grape seeds, grey Fruit seeds, pecans, cashews, chestnuts, coconuts, peanuts, walnuts, green tea leaves, black tea leaves, oolong tea leaves, tobacco, shiso leaves, thyme, sage, lavender, spearmint, peppermint, santosou, hyssop, basil, marigold, dandelion, artichoke, German chamomile, goldenrod, licorice, anise, yarrow, eucalyptus, wormwood, aromatic oils, angelica, fenugreek, shishito peppers, fennel, chili peppers, coriander seeds, caraway seeds, fennel seeds, ginger, horseradish, oregano marjoram, oregano (origanum valgare), mustard, parsley, pepper, savory, tarragon, turmeric, wasabi, dill seeds, or citrus fruits.

[0032] Products separated and purified from the aforementioned natural products by methods known to the industry, such as known extraction methods, can be used.

[0033] In the composition of this application, chlorogenic acid, caffeic acid, and quinic acid may be used in any ratio without limitation, but the total content of chlorogenic acid and caffeic acid based on 100 parts by weight of quinic acid may be 0.1 parts by weight, 0.3 parts by weight, 0.4 parts by weight, 0.5 parts by weight, 0.7 parts by weight, 0.8 parts by weight, 0.9 parts by weight, 1 part by weight, 1.1 parts by weight, 1.2 parts by weight, 1.3 parts by weight, 1.4 parts by weight, 1.5 parts by weight, 10 parts by weight, 50 parts by weight, and 1 part by weight. The range may consist of one lower limit selected from 00 parts by weight, and / or one upper limit selected from 700 parts by weight, 600 parts by weight, 500 parts by weight, 480 parts by weight, 470 parts by weight, 460 parts by weight, 450 parts by weight, 400 parts by weight, 350 parts by weight, 330 parts by weight, 320 parts by weight, 310 parts by weight, 300 parts by weight, 250 parts by weight, 240 parts by weight, 230 parts by weight, 210 parts by weight, 200 parts by weight, and 100 parts by weight. For example, the amounts may be 0.1 to 700 parts by weight, 0.3 to 600 parts by weight, 0.5 to 600 parts by weight, 0.7 to 500 parts by weight, 0.7 to 470 parts by weight, 0.7 to 460 parts by weight, 0.8 to 460 parts by weight, 0.8 to 450 parts by weight, 0.8 to 310 parts by weight, 0.8 to 300 parts by weight, 0.8 to 270 parts by weight, 0.8 to 250 parts by weight, or 0.9 to 240 parts by weight.

[0034] The ratio of chlorogenic acid to caffeic acid content may be within a range defined by one lower limit selected from 10, 30, 35, 37, 39, 40, 45, 49, 50, and 70 parts by weight of caffeic acid, and / or one upper limit selected from 400, 300, 200, 150, 120, 110, and 100 parts by weight, based on 100 parts by weight of chlorogenic acid. For example, the range may be 10 to 400 parts by weight, 30 to 300 parts by weight, 35 to 200 parts by weight, 35 to 150 parts by weight, 39 to 150 parts by weight, 39 to 120 parts by weight, 39 to 110 parts by weight, or 40 to 100 parts by weight.

[0035] The combined effect of polyphenols can be achieved depending on the content ratio of chlorogenic acid, caffeic acid, and quinic acid.

[0036] The above composition can be used without restriction by adjusting the caffeic acid, chlorogenic acid, and quinic acid content depending on the application, but the total content of caffeic acid, chlorogenic acid, and quinic acid based on the composition may be within a range defined by one lower limit selected from 0.1 ppm, 0.5 ppm, 1 ppm, 10 ppm, 20 ppm, 40 ppm, 50 ppm, 80 ppm, 100 ppm, 120 ppm, 140 ppm, 145 ppm, 149 ppm, and 150 ppm, and / or one upper limit selected from 5,000 ppm, 2,000 ppm, 1,000 ppm, 500 ppm, 300 ppm, 250 ppm, 230 ppm, and 200 ppm. For example, the ranges may be 0.1 ppm to 5,000 ppm, 1 ppm to 2,000 ppm, 50 ppm to 1,000 ppm, 100 ppm to 1,000 ppm, 120 ppm to 1,000 ppm, 120 ppm to 500 ppm, 140 ppm to 300 ppm, 140 ppm to 250 ppm, 140 ppm to 230 ppm, 145 ppm to 230 ppm, 145 ppm to 200 ppm, 149 ppm to 200 ppm, or 150 ppm to 200 ppm. The ppm values ​​may also be weight ratios (w / w).

[0037] The composition of this application may further contain other polyphenols other than chlorogenic acid, caffeic acid, and quinic acid.

[0038] Other polyphenols may include, without limitation, phenolic acids, flavonoids, stilbenes, lignans, etc., such as isorhamnetin, isorhamnetin glycoside, catechin, epicatechin, gallocatechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, ellagic acid, catechol, caffeic acid ester, kaempferol, kaempferol glycoside, quercetin, quercetin glycoside, quercetagenin, genicetin, genicetin glycoside, tannic acid, anthocyanins, hydroquinone, hesperetin, hesperidin, and gallic acid. Examples include, but are not limited to, gallate esters (lauryl gallate, propyl gallate, butyl gallate), 4-methylcatechol, 5-methylcatechol, 4-methoxycatechol, 5-methoxycatechol, methylcatechol-4-carboxylic acid, 2-methylresorcinol, 5-methylresorcinol, lignin, limositrin, limositrin glycoside, limositrol, luteolin, luteolin glycoside, luteolininidin, luteolininidin glycoside, rutin, resorcinol, resveratrol, resorcinol, leucocyanidin, or leucodelfinidin.

[0039] In addition to polyphenol components, the compositions of this application may further contain a variety of nutrients, vitamins, electrolytes, flavoring agents, coloring agents, pectinic acid, salts of pectinic acid, alginic acid, salts of alginic acid, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, or carbonating agents.

[0040] Specifically, the composition of this application may contain vitamins A, C, D, E, B1, B2, B6, B12, niacin, biotin, folate, pantothenic acid, etc. It may also contain minerals such as zinc (Zn), iron (Fe), calcium (Ca), chromium (Cr), magnesium (Mg), manganese (Mn), and copper (Cu). It may also contain amino acids such as lysine, tryptophan, cysteine, and valine. Furthermore, it may contain monosaccharides such as glucose and fructose; disaccharides such as maltose and sucrose; polysaccharides such as dextrin and cyclodextrin; and sugar alcohols such as xylitol, sorbitol, and erythritol. Furthermore, it may contain food additives such as: preservatives (potassium sorbate, sodium benzoate, salicylic acid, sodium dehydroacetate, etc.); disinfectants (bleaching powder, high-grade bleaching powder, sodium hypochlorite, etc.); antioxidants (butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), etc.); colorants (tar dyes); color fixatives (sodium nitrite, sodium nitrite); bleaching agents (sodium sulfite); flavorings (MSG, monosodium glutamate); sweeteners (natural sweeteners such as thaumatin and stevia extract, synthetic sweeteners such as saccharin and aspartame); flavorings (vanillin, lactones); leavening agents (alum, potassium bitartrate D); and fortifiers, emulsifiers, thickeners, coating agents, gum bases, foam inhibitors, solvents, and improvers.

[0041] The aforementioned additives may be selected and used in appropriate amounts depending on the type of food.

[0042] In one embodiment, the composition of this application may be used for the purpose of reducing off-flavors or off-odors.

[0043] In this application, "off-flavor" means a taste that causes discomfort or aversion resulting from the components contained in the product themselves, secondary chemical changes of these components, or substances introduced from outside.

[0044] In this application, "unpleasant odor" means an unpleasant or off-putting smell caused by the components contained in the product themselves, secondary chemical changes of these components, or substances introduced from outside.

[0045] The substances that produce the aforementioned off-flavor or off-odor may, for example, be nitrogen compounds, sulfur compounds, lower fatty acids, carbonyl compounds, esters, phenols, alcohols, hydrocarbons, or chlorine compounds.

[0046] Specifically, the aforementioned odor may be a fishy smell. The aforementioned fishy smell is a fishy smell originating from plants or marine products, and specifically, it may be a fishy smell originating from fish.

[0047] The nitrogen compound may include any substance that can produce an unpleasant odor, such as ammonia, trimethylamine, piperidine, or trimethyl oxide, without limitation, but it may specifically be trimethylamine.

[0048] The substance that produces the aforementioned off-flavor or off-odor may be a volatile fragrance component. The volatile fragrance component may be, but is not limited to, one or more compounds selected from the group consisting of hexylaldehyde (hexanal), heptanal, 2-nonenal ((Z)-), 2,4-heptadienal ((E,E)-), 2-hexenal ((E)-), 2,6-nonadienal ((E,Z)-), 2-nonanone, 2-pentenal ((E)-), 1-penten-3-one, disulfide compounds, and dimethyl compounds.

[0049] The chlorogenic acid, caffeic acid, and quinic acid-containing composition of this application can be usefully used to reduce off-flavors or off-odors.

[0050] In other aspects of this application, this application provides a method for reducing off-flavors or off-odors, comprising the step of adding the aforementioned composition of this application to a substance that generates off-flavors or off-odors.

[0051] In another aspect of this application, this application provides a method for producing a substance that reduces off-flavors or off-odors, comprising the step of adding the aforementioned composition of this application to a substance that generates off-flavors or off-odors.

[0052] In other aspects of this application, this application provides a preservation composition for products comprising chlorogenic acid, caffeic acid, and quinic acid.

[0053] In one embodiment, the purpose of preserving the product may be to prevent oxidation or to suppress browning of the product.

[0054] In other embodiment, the target products for preservation, oxidation prevention, or browning inhibition may be food, animal feed, household goods, or industrial goods.

[0055] In the preservation composition for the product of this application, chlorogenic acid, caffeic acid, and quinic acid may be used in any ratio without limitation, but the total content of chlorogenic acid and caffeic acid based on 100 parts by weight of quinic acid may be 0.1 parts by weight, 0.3 parts by weight, 0.4 parts by weight, 0.5 parts by weight, 0.7 parts by weight, 1 part by weight, 1.1 parts by weight, 1.3 parts by weight, 1.4 parts by weight, 10 parts by weight, 50 parts by weight, 100 parts by weight, and 1 part by weight. The range may consist of one lower limit selected from 50 parts by weight, and / or one upper limit selected from 700 parts by weight, 600 parts by weight, 500 parts by weight, 450 parts by weight, 400 parts by weight, 350 parts by weight, 340 parts by weight, 330 parts by weight, 320 parts by weight, 310 parts by weight, 300 parts by weight, 250 parts by weight, 240 parts by weight, 230 parts by weight, 210 parts by weight, 200 parts by weight, and 150 parts by weight. For example, it may be 0.1 to 700 parts by weight, 0.3 to 600 parts by weight, 0.5 to 600 parts by weight, 1 to 500 parts by weight, 10 to 450 parts by weight, 50 to 450 parts by weight, 100 to 400 parts by weight, 150 to 350 parts by weight, 200 to 350 parts by weight, or 200 to 300 parts by weight.

[0056] The ratio of chlorogenic acid to caffeic acid content may be within a range defined by one lower limit selected from 10, 30, 35, 39, 40, 45, 49, 50, 70, 80, and 90 parts by weight of caffeic acid, and / or one upper limit selected from 400, 300, 200, 150, 140, 130, 120, 110, and 100 parts by weight, based on 100 parts by weight of chlorogenic acid. For example, the amounts may be 10 to 400 parts by weight, 30 to 300 parts by weight, 35 to 200 parts by weight, 40 to 150 parts by weight, 50 to 140 parts by weight, 60 to 130 parts by weight, 70 to 120 parts by weight, or 80 to 120 parts by weight.

[0057] With regard to product preservation compositions, which is one aspect of this application, matters concerning polyphenol components, matters concerning other components other than polyphenol components, and matters concerning their content, the same content as described in the other aspect of this application, "Compositions containing chlorogenic acid, caffeic acid, and quinic acid," will be referred to and will not be explained again to avoid complexity in the specification.

[0058] The chlorogenic acid, caffeic acid, and quinic acid-containing composition of this application has excellent antioxidant effects and can therefore be used as an antioxidant.

[0059] The chlorogenic acid, caffeic acid, and quinic acid-containing composition of this application can replace synthetic antioxidants such as BHA (butylated hydroxyanisole), BHT (butylated hydroxytoluene), or TBHQ (tertiary butylhydropuinone).

[0060] In one embodiment, the composition of this application has the activity to efficiently suppress the oxidation of fats or proteins by free radical inhibitory activity.

[0061] The chlorogenic acid, caffeic acid, and quinic acid-containing composition of this application can be used as a browning inhibitor.

[0062] The composition of this application has excellent polyphenol oxidase inhibitory activity, and therefore has excellent browning suppression activity.

[0063] In this application, the browning inhibitor may be one that suppresses the browning itself caused by the oxidation of phenolic compounds, or it may be one that suppresses the browning reaction that occurs in the reaction of sugars, amino acids, etc.

[0064] In other aspects of this application, this application provides a method for preventing oxidation of a product, comprising the step of adding a composition comprising chlorogenic acid, caffeic acid, and quinic acid to the product.

[0065] In another aspect of this application, the application provides a method for suppressing browning of a product, comprising the step of adding a composition comprising chlorogenic acid, caffeic acid, and quinic acid to the product.

[0066] The composition comprising chlorogenic acid, caffeic acid, and quinic acid described in this application can be applied to a variety of products.

[0067] The compositions of this application can be applied without limitation to foods, feeds, household goods, industrial products, etc. Specific examples of the aforementioned foods or feeds include, but are not limited to, processed grains, vegetables, fruits, dried or cut vegetable products, fruit juices, vegetable juices, mixed vegetable and fruit juices, chips, noodles, processed livestock products, processed seafood products, processed dairy products, fermented dairy products, microbially fermented foods, confectionery and bread products, spices, processed fish / meat products, acidic drinking water, processed foods, ready-to-eat foods, licorice products, herbs, insect feeds, livestock feeds, pet feeds, etc.

[0068] The aforementioned processed fish / meat products refer to ham, sausages, bacon, dried preserved meats, seasoned meats, packaged meats, ground meat products, kalbi products, meat extract products, edible beef fat, edible pork fat, chunks of fish meat, etc., processed using meat or fish meat as raw materials. The aforementioned "meat" may, but is not limited to, meats, edible organs, and by-products commonly used in dietary customs, such as beef, pork, sheep, goats, rabbits, chickens, turkeys, ducks, pheasants, and quail. The forms of processed meat products include, but are not limited to, sterilized meat products, hams, pressed hams, mixed pressed hams, sausages, mixed sausages, dried sausages (dried mixed sausages), semi-dried sausages (semi-dried mixed sausages), heated and frozen sausages, bacon, dried preserved meats, seasoned meats, ground products, kalbi products, packaged meats, and other processed meat products.

[0069] When the composition of this application is used in a manner suitable for the intended purpose, it may be formulated in various forms such as liquid, solid, or powder in a convenient and suitable manner for the intended purpose. The composition of this application may be blended together with the raw materials during the manufacturing process, and it can be uniformly applied to food by immersing the food in the composition of this application, mixing it after immersion, sprinkling the composition on, or direct mixing.

[0070] In another embodiment of this application, a composition for reducing off-flavors or off-odors containing quinic acid is provided.

[0071] The details regarding compositions for reducing off-flavors or off-odors of quinic acid are as described above.

[0072] The aforementioned composition for reducing off-flavors or off-odors containing quinic acid may further contain polyphenols from which quinic acid has been removed, specifically phenolic acid and / or quinic acid derivatives.

[0073] The aforementioned quinic acid-containing composition for reducing off-flavors or off-odors may contain 10% or more, 30% or more, 50% or more, 70% or more, 90% or more, or 99% or more by weight, based on 100% by weight of polyphenols.

[0074] The present application will be described in detail below with reference to examples. However, the following examples are for illustrative purposes only, and the content of the present application is not limited to the following examples.

[0075] Examples

[0076] Experimental Example 1: Production of Polyphenol-Containing Composition

[0077] 1. Experimental materials

[0078] The polyphenols used in the experiment were chlorogenic acid, caffeic acid, gallic acid, catechin, ferulic acid, and quinic acid, purchased as single compounds from Sigma-Aldrich (St. Louis, Mo, USA).

[0079] 2. Composition of polyphenol-containing compositions

[0080] Three polyphenol single compounds were mixed at the same concentration of 50 ppm, as shown in Table 1 below, to produce polyphenol-containing compositions T1 to T6.

[0081] [Table 1]

[0082] 3. Composition of polyphenol-containing compositions by component content ratio

[0083] Among the polyphenol mixed compositions, composition T1 showed the best effect. By adjusting the ratio of chlorogenic acid, caffeic acid, and quinic acid content (unit: ppm), various polyphenol-containing compositions S1 to S6 shown in Table 2 below were produced.

[0084] [Table 2]

[0085] Experimental Example 2: Trimethylamine (TMA) Analysis

[0086] 1. Preparation of Trimethylamine (TMA) Standard Material

[0087] The trimethylamine (TMA) used in the experiment was purchased as a 30% concentration product from Doxan Chemical (Ansan, South Korea). To confirm the reduction effect of TMA, a standard aqueous solution was prepared by diluting the standard reagent, 30% trimethylamine, in distilled water to a concentration of 100 ppm. The prepared standard aqueous solution was used as a solvent when preparing the test polyphenol composition to produce a polyphenol composition sample containing trimethylamine, which was then used for GC / MS analysis.

[0088] 2. Analysis of Trimethylamine (TMA) Component and Content

[0089] The trimethylamine (TMA) component in the polyphenol composition was identified via the following method. For adsorption for analysis of volatile substances, SPME (Solid Phase Microextraction Fiber Holder, Supelco., Bellefonte, PA, USA) was pre-treated with DVB / CAR / PDMS (50 / 30 μm). 1 mL of the pre-treated composition was placed in a 20 mL EPA vial and capped with PTFE / Silicon. After inserting the SPME needle into the vial containing the composition, adsorption was performed at 60°C for 30 minutes, and then the vial was used for GC / MS analysis.

[0090] GC / MS analysis was performed using an Agilent gas chromatograph (GC2010 plus, Agilent, USA) with a DB-5MS column (thickness: 0.25 μm, length: 30 m, diameter: 0.25 mm). He was used as the carrier gas, and the column oven temperature was set to 100°C, the injection temperature to 200°C, the total flow rate to 1.10 mL / min, and the total program time to 37 minutes before the analysis was performed. The TMA content in the composition was quantified by comparing the peak areas of 1 g of sample and 1 g of 100 mg / L TMA, and calculating the content of volatile aroma components in the sample as comparative relative quantification.

[0091] Experimental Example 3: Effect of polyphenol composition on reducing trimethylamine (TMA)

[0092] To confirm the superiority of the combination of chlorogenic acid, caffeic acid, and quinic acid, we investigated the TMA reduction effect, which is known to be an effect of polyphenols. Specifically, we confirmed the trimethylamine (TMA) reduction effect of each polyphenol composition prepared in Experimental Examples 1 and 2 using the method of Experimental Example 2.

[0093] [Table 3]

[0094] As confirmed in the results in Table 3 above, the combination of chlorogenic acid, caffeic acid, and quinic acid (composition T1) was found to be the most effective in reducing TMA compared to other polyphenol combinations.

[0095] Experimental Example 4: Effect of TMA reduction on the composition ratio of polyphenol compositions

[0096] The effect of reducing trimethylamine (TMA) was confirmed in polyphenol compositions prepared with different component contents according to item 3 of Experimental Example 1, using the method of Experimental Example 2.

[0097] [Table 4]

[0098] As can be seen in Table 4 above, we confirmed that the TMA reduction effect is maintained even when the content of chlorogenic acid, caffeic acid, and quinic acid in the composition is changed.

[0099] Experiment Example 5: Analysis of Volatile Fragrance Components

[0100] 1. Experimental Method

[0101] To confirm the effect of the polyphenol composition on reducing rancid odor, the composition was applied to fish oil, and then the volatile aroma components were analyzed.

[0102] For adsorption analysis of volatile substances, SPME (Solid Phase Microextraction Fiber Holder, Supelco., Bellefonte, PA, USA) was pre-treated using DVB / CAR / PDMS (50 / 30 μm). The sample used in the experiment consisted of fish oil to which a polyphenol composition had been added, followed by accelerated oxidation in a 45°C incubator for 72 hours. 1 g of this oil was placed in a 20 mL EPA vial and capped with PTFE / Silicon. After inserting the SPME needle into the vial containing the sample, adsorption was performed at 60°C for 30 minutes before use for GC / MS analysis.

[0103] GC / MS analysis was performed using an Agilent gas chromatograph (GC2010 plus, Agilent, USA) with a DB-5MS column (thickness: 0.25 μm, length: 30 m, diameter: 0.25 mm). He was used as the carrier gas, the column oven temperature was set to 100°C, the injection temperature to 200°C, the total flow rate to 1.10 mL / min, and the total program time to 37 min. The results obtained from the analysis were converted to peak area values ​​and compared. The experimental results identified compounds with rancid odor characteristics and confirmed the reduction effect of the polyphenol composition.

[0104] 2. Analysis of experimental results

[0105] The biggest obstacle to using fish oil is the development of a fishy and rancid odor. This is thought to be due to the high content of highly unsaturated fatty acids in fish oil, and the low content of natural antioxidants such as tocopherol. As a result, nitrogen compounds contained in fish oil combine with highly unsaturated fatty acids and are oxidized, accelerating the development of rancid odor.

[0106] Table 5 below shows the results of measuring the changes in major volatile aroma components generated by applying a polyphenol composition to fish oil (unit: peak area / 10000).

[0107] [Table 5]

[0108] In Table 5 above, the positive (+) control group is the group to which L-ascorbic acid was added, and the negative (-) control group is the group to which antioxidants or polyphenols were not added.

[0109] As shown in Table 5, hexanal, which is identified as an indicator of rancidity, showed low intensity in the positive control group, and in the case of the T1 composition, it showed low intensity at a similar level to the positive control group.

[0110] Components responsible for characteristic grassy odors like heptanal and the fishy smell of fish oil were also reduced in all polyphenol compositions compared to the negative control group, with composition T1 showing the most superior reduction effect.

[0111] The component 2,4-Heptadienal,(E,E)- is known to induce a strong fatty and fishy odor, and it has been reported that while present in fresh seafood, its content increases due to the auto-oxidation of highly unsaturated fatty acids. When the polyphenol composition was treated, particularly the T1 composition, the production of 2,4-Heptadienal,(E,E)- was suppressed more significantly than in the positive control group.

[0112] Furthermore, enal and dienal compounds appear to play an important role as volatile components in fish, contributing to the formation of the fishy odor. Disulfide and dimethyl compounds were also identified as strong malodorous components. When polyphenol compositions were treated, the generation of enal, dienal, disulfide, and dimethyl compounds, which are involved in rancid odor, was generally inhibited.

[0113] Table 6 below shows the results of measuring the changes in volatile aroma components of T1 polyphenol compositions prepared with different polyphenol content.

[0114] [Table 6]

[0115] According to the results in Table 6, it was confirmed that even when the content of each component of chlorogenic acid, caffeic acid, and quinic acid in the T1 composition was changed, there was no significant difference in the effect of altering the volatile fragrance components.

[0116] Experimental Example 6: Method for Measuring the Preservative Effect of Polyphenol-Containing Compositions

[0117] To confirm the preservative effect of compositions containing polyphenol compounds, antioxidant and browning inhibitory effects were measured. Antioxidant effects were confirmed by measuring DPPH radical scavenging ability, and the Rancimat method, which can also be used to accelerate the rancidity of fats and confirm oxidative stability, was employed. Browning inhibitory effects were confirmed by measuring polyphenol oxidase inhibitory activity.

[0118] Experimental Example 7: Measurement of DPPH radical scavenging ability

[0119] A 4 mM DPPH ethanol solution was prepared and its absorbance was adjusted to 1.000 ± 0.1. 0.2 ml of each sample was added to a test tube, mixed with 2.8 ml of DPPH solution, and reacted for 10 minutes. The absorbance was then measured at 517 nm using a microplate reader (M2, Molecular Device, Canada). For the positive control group, the DPPH radical scavenging activity was calculated using L-ascorbic acid from the following formula.

[0120] DPPH radical scavenging activity(%)= [1-(A / B)]×100

[0121] (A: Absorbance of the group with added sample, B: Absorbance of the group without added sample)

[0122] The results of the analysis of DPPH radical scavenging ability are shown in Table 7 below. Differences were observed depending on the polyphenol composition, with composition T1 showing the highest scavenging ability, and radical scavenging effects were also observed in the remaining compositions, excluding composition T3.

[0123] [Table 7]

[0124] *Duncan's multiple range test at p<0.05

[0125] In composition T1, which showed the best effect, we examined the change in radical scavenging effect by varying the content ratio of polyphenol components. The results showed that the effect tended to be higher when the composition ratio of the three types of polyphenols was adjusted to be similar. In particular, as shown in Table 8, the scavenging effect was high when chlorogenic acid and caffeic acid were mixed in similar ratios.

[0126] [Table 8]

[0127] *Duncan's multiple range test at p<0.05

[0128] Experimental Example 8: Measurement of Oxidative Stability by Rancimat Method

[0129] The oxidative stability of the oils and fats was analyzed using the Lancimat method (743 Metrohm Co., Herisau, Switzerland). 2.5 g of fish oil (Sigma-Aldrich, St. Louis, MO, USA) containing 2% polyphenol composition was placed in a reaction vessel, and the oil was oxidized on an aluminum heating block adjusted to 100°C while injecting air at 20 L / hr. The volatile oxidation products generated were transferred to an absorption vessel containing 60 mL of distilled water, and the degree of antioxidant activity was measured during an induction period automatically calculated according to the change in electrical conductivity. The antioxidant capacity was compared using the Antioxidative Index (AI), calculated using the following formula, with the oil sample without the added polyphenol composition as the control group. L-ascorbic acid was used as a positive control group.

[0130] Antioxidant index (AI) = IG / IC (IG: control group, IC: treated group)

[0131] The results of testing the oxidative stability after adding each polyphenol composition to fish oil are shown in Table 5. As shown in Table 9, most compositions showed similar or higher oxidative stability than the control group, with composition T1 showing the highest oxidative stability. The overall trend showed a pattern similar to that of the DPPH radical scavenging ability, which was measured for antioxidant capacity.

[0132] [Table 9]

[0133] *Duncan's multiple range test at p<0.05

[0134] Table 10 below shows the results of preparing compositions with different polyphenol content in the T1 composition, which exhibited the highest oxidative stability, and then adding these compositions to a sample and measuring their oxidative stability. As shown in the results in Table 10, when chlorogenic acid and caffeic acid were mixed in similar ratios, superior oxidative stability was observed.

[0135] [Table 10]

[0136] *Duncan's multiple range test at p<0.05

[0137] Experimental Example 9: Measurement of Polyphenol Oxidase (PPO) Inhibitory Activity

[0138] After mixing 1.7 ml of 50 mM phosphate buffer (pH 6.5) with 0.2 ml of PPO (4,276 units / mg), 0.1 ml of each polyphenol composition was added, and the mixture was left to stand in a constant temperature water bath adjusted to 25°C for 15 minutes. Then, 1 ml of 4 mM catechin solution was added to each as a substrate. Next, the change in absorbance over 5 minutes at 420 nm was measured using a microplate reader (M2, Molecular Device, Canada). Enzyme inhibitory activity was expressed as the percentage decrease in absorbance using the following formula.

[0139] Inhibition of PPO activity(%)=[1-(A / B)]×100

[0140] [A: Absorbance of the sample, B: Absorbance of the blank solution]

[0141] Table 11 shows the results of measuring the polyphenol oxidase inhibitory activity of each polyphenol composition. According to the results shown in Table 11, composition T1 exhibited the best polyphenol oxidase inhibitory activity.

[0142] [Table 11]

[0143] *Duncan's multiple range test at p<0.05

[0144] Table 12 shows the results of measuring the polyphenol oxidase inhibitory activity of compositions with different polyphenol content in composition T1, which exhibited the most excellent polyphenol oxidase inhibitory activity. As shown in the results in Table 12, when chlorogenic acid and caffeic acid were mixed in similar ratios, the polyphenol oxidase inhibitory activity was best exhibited.

[0145] [Table 12]

[0146] *Duncan's multiple range test at p<0.05

[0147] While the above has provided illustrative examples of typical embodiments of this application, the scope of this application is not limited to such specific embodiments, and any person with ordinary skill in the art could appropriately modify the claims of this application.

Claims

1. A preservation composition for a product containing chlorogenic acid, caffeic acid, and quinic acid, wherein the preservation of the product is for preventing oxidation of the product, and the total content of chlorogenic acid and caffeic acid is 200 to 210 parts by weight based on 100 parts by weight of quinic acid, and the content of caffeic acid is 100 to 110 parts by weight based on 100 parts by weight of chlorogenic acid.

2. A preservation composition for a product containing chlorogenic acid, caffeic acid, and quinic acid, wherein the preservation of the product is for inhibiting browning of the product, the total content of chlorogenic acid and caffeic acid is 200 to 210 parts by weight based on 100 parts by weight of quinic acid, the content of caffeic acid is 100 to 110 parts by weight based on 100 parts by weight of chlorogenic acid, and the browning is browning caused by oxidation of phenolic compounds by polyphenol oxidase.

3. The preservative composition according to claim 1, wherein the product is food, animal feed, household goods, or industrial goods.

4. A method for preventing oxidation of a product, comprising the step of adding a composition containing chlorogenic acid, caffeic acid, and quinic acid to the product, wherein the composition has a total content of chlorogenic acid and caffeic acid of 200 to 210 parts by weight based on 100 parts by weight of quinic acid, and a content of caffeic acid of 100 to 110 parts by weight based on 100 parts by weight of chlorogenic acid.

5. The method for preventing oxidation of the product described in claim 4, wherein the product is food, animal feed, household goods, or industrial goods.

6. A method for suppressing browning of a product, comprising the step of adding a composition containing chlorogenic acid, caffeic acid, and quinic acid to the product, wherein in the composition, the total content of chlorogenic acid and caffeic acid is 200 to 210 parts by weight based on 100 parts by weight of quinic acid, and the content of caffeic acid is 100 to 110 parts by weight based on 100 parts by weight of chlorogenic acid, and the browning is browning caused by oxidation of a phenolic compound by polyphenol oxidase.

7. The method for suppressing browning of the product described in claim 6, wherein the product is food, animal feed, household goods, or industrial goods.

8. The preservative composition according to claim 2, wherein the product is food, animal feed, household goods, or industrial goods.

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