TWI772956B - Composition comprising polyphenols - Google Patents

Abstract

The present application relates to a composition containing chlorogenic acid, caffeic acid, and quinic acid. The polyphenol-containing composition of the present application may be used for reducing an off-taste or off-flavor. In addition, the polyphenol-containing composition of the present application may be used as a preservative of a product, in particular an antioxidant or browning inhibitor of a product.

Description

Compositions containing polyphenols

The present application relates to a composition comprising polyphenols and uses thereof. Cross-references to related applications

This application claims Korean Patent Application No. 10-2019-0142992 filed on November 08, 2019, Korean Patent Application No. 10-2020-0123836 filed on September 24, 2020, and Korean Patent Application No. 10-2020-0123836 filed on September 20, 2020 Korean Patent Application No. 10-2020-0123837 filed on March 24 has priority in the Korean Intellectual Property Office, the disclosures of which are incorporated herein by reference.

Polyphenols are compounds contained in plants such as fruits or leafy vegetables, and thousands of polyphenols have been identified so far. Examples of representative polyphenols include flavonoids, anthocyanins, tannins, catechins, isoflavones, xylan, resveratrol, and the like. Multiple hydroxyl groups (-OH) present in polyphenols have the property of being easily bonded to various compounds and have excellent antioxidant, anticancer, and anti-inflammatory effects.

Although a single polyphenol can exhibit an effect as a single substance, the effect can be enhanced by using each polyphenol in combination with other polyphenols, so it is known that the combination is important (Korean Patent Publication No. 10-2015-0016343). However, since there are various types of polyphenols, it is difficult to confirm the synergistic effect of the combination.

[PRIOR ART DOCUMENT]

[patent document]

Korean Patent Publication No. 10-2015-0016343

technical problem

One aspect of the present application provides a polyphenol-containing composition that can be used for a variety of purposes. technical solutions

According to an aspect of the present application, a composition containing chlorogenic acid, caffeic acid and quinic acid is provided.

According to another aspect of the present application, there is provided a method for reducing off-flavor or off-flavor, the method comprising adding a composition containing chlorogenic acid, caffeic acid and quinic acid to an off-flavor or off-flavor producing material.

According to another aspect of the present application, there is provided a method of preparing an off-flavor or off-flavor reducing material, the method comprising adding a composition containing chlorogenic acid, caffeic acid and quinic acid to the off-flavor or off-flavor producing material.

According to another aspect of the present application, there is provided a use of a composition containing chlorogenic acid, caffeic acid and quinic acid as an odor reducing agent or an off-flavor reducing agent.

According to another aspect of the present application, there is provided a composition for preserving a product, the composition containing chlorogenic acid, caffeic acid and quinic acid.

According to another aspect of the present application, there is provided a method for preventing oxidation of a product, the method comprising adding a composition containing chlorogenic acid, caffeic acid and quinic acid to the product.

According to another aspect of the present application, there is provided a method for inhibiting browning of a product, the method comprising adding a composition containing chlorogenic acid, caffeic acid and quinic acid to the product. favorable effect

The composition containing chlorogenic acid, caffeic acid and quinic acid of the present application can be used for various purposes.

The compositions of the present application can be used to reduce off-flavors or off-flavors. The composition of the present application has an excellent ability to reduce trimethylamine (TMA) as an off-flavor or off-flavor-inducing material and an excellent effect of reducing off-flavor or off-flavor by inducing changes in various volatile aroma components.

In addition, unlike conventionally used materials for reducing off-flavor or off-flavor, the composition of the present application remains in the product very little, and thus it does not affect the original properties of the product and can be easily applied to the manufacturing process of the processed product.

In addition, the compositions of the present application containing chlorogenic acid, caffeic acid, and quinic acid can be used to preserve products, and in particular, to prevent product oxidation or inhibit product browning.

The polyphenol composition of the present application has excellent antioxidant effect, excellent oxidative stability, and high polyphenol oxidase inhibitory activity, as evidenced by the DPPH radical scavenging ability, and thus has browning inhibitory activity.

Furthermore, unlike conventional antioxidants or browning inhibitors, the composition of the present application remains in the product very little, and thus it does not affect the original properties of the product and can be easily applied to the manufacturing process of the processed product.

However, the effects of the present application are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those having ordinary knowledge in the technical field from the following description.

Hereinafter, the present application will be described in detail.

According to an aspect of the present application, a composition containing chlorogenic acid, caffeic acid and quinic acid is provided.

Chlorogenic acid, caffeic acid and quinic acid, which are the active ingredients of the present application, are polyphenol components.

The term "polyphenol" as used in this application refers to a compound containing one or more phenols with one or more hydroxyl groups in the molecule. In this specification, the term "polyphenol" is used to include not only the polyphenol itself but also its derivatives, such as glycosides, alkylated compounds, esterified compounds and the like.

In the present application, chlorogenic acid is an ester compound between caffeic acid and quinic acid and is represented by the following formula 1: [Formula 1]

In the present application, caffeic acid is a compound classified as hydroxycinnamic acid and represented by the following formula 2: [Formula 2]

In the present application, quinic acid is represented by the following formula 3: [Formula 3]

The chlorogenic acid, caffeic acid and quinic acid used in the present application may be chlorogenic acid, caffeic acid and quinic acid derived from natural products and synthetic chlorogenic acid, caffeic acid and quinic acid.

Natural products may include, but are not limited to, any substance containing chlorogenic acid, caffeic acid, and/or quinic acid, but may be plants. In particular, examples of plants include aloe vera, anise seed, elderberry, fenugreek, psyllium, orange blossom, allspice, hyssop, valerian, chamomile, capsicum, cardamom, cinnamon, garlic, caraway Seeds, cloves, cumin seeds, kola, coriander seeds, rosacea, saffron, peppercorns, juniper berries, cinnamon, ginger, star anise, St. John's wort, celery seeds, mint, sesame seeds, edible Yellow, tansy, turmeric, thistle, dill seed, nutmeg, nettle, hibiscus, witch hazel, birch, basil, lime, fennel, primrose, fenugreek, verbena, bay, hops, bordeaux, Horseradish, poppy seeds, gall, marigold, pumpkin, marjoram, mustard seeds, yarrow, mint leaves, lemon balm, nutmeg, elixir, gentian, rose hips, rosemary (rosemary/Rosmarinus officinalis) , sunflower seed, grape peel, apple, carrot leaf, banana, strawberry, apricot, peach, plum, pineapple, pear, persimmon, cherry, papaya, mango, avocado, melon, loquat, fig, kiwi, dried plum, blueberry , blackberry, raspberry, cranberry, coffee beans, cocoa beans, grape seeds, grapefruit seeds, pecans, cashews, chestnuts, coconuts, peanuts, walnuts, green tea leaves, black tea leaves, oolong tea leaves, tobacco, basil leaves, Garden thyme, sage, lavender, spearmint, peppermint, spotted thistle, hyssop, sweet basil, marigold, dandelion, artichoke, sage, dragon sprout, licorice, anise, Eucalyptus, eucalyptus, absinthe, perfume mint, angelica, fenugreek, paprika, fennel, red pepper, coriander seeds, caraway seeds, fennel seeds, ginger, horseradish, marjoram, oregano, mustard seeds , parsley, pepper, mint, tansy, turmeric, horseradish, dill seeds, citrus fruits and the like.

Chlorogenic acid, caffeic acid, and quinic acid can be isolated and purified from natural products by methods known in the art, such as known extraction methods.

The content ratio of chlorogenic acid, caffeic acid and quinic acid in the composition of the present application is not limited. Based on 100 parts by weight of quinic acid, the total content of chlorogenic acid and caffeic acid may be within a range consisting of a lower limit and/or an upper limit selected from 0.1 part by weight, 0.3 part by weight, 0.4 part by weight, 0.5, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 10, 50, and 100 parts by weight parts, the upper limit is 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, based on 100 parts by weight of quinic acid, the total content of chlorogenic acid and caffeic acid 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 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 .

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

The effect of the combination of polyphenols can be shown by the content ratio of chlorogenic acid, caffeic acid and quinic acid.

The contents of caffeic acid, chlorogenic acid and quinic acid can be adjusted without limitation in view of the use of the composition. Based on the composition, the total content of caffeic acid, chlorogenic acid and quinic acid may be within a range consisting of a lower limit and/or an upper limit selected from the group consisting of 0.1 ppm, 0.5 ppm, 1 ppm, 10 ppm, 20 ppm ppm, 40 ppm, 50 ppm, 80 ppm, 100 ppm, 120 ppm, 140 ppm, 145 ppm, 149 ppm and 150 ppm, the upper limit being 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 total content of caffeic acid, chlorogenic acid and quinic acid 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 by composition 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. "ppm" may refer to a weight ratio (w/w).

The composition of the present application may further comprise other polyphenols in addition to chlorogenic acid, caffeic acid and quinic acid.

In particular, examples of other polyphenols include, but are not limited to, phenolic acids, flavonoids, stilbenes, lignins, and the like. For example, other polyphenols include, but are not limited to, isorhamnetin, isorhamnetin glycosides, catechin, epicatechin, gallocatechin, epicatechin gallate, epigallocatechin Catechin, Epigallocatechin Gallate, Turkish Tannin, Catechol, Caffeate, Kaempferol, Kaempferol Glycoside, Quercetin, Quercetin Glycoside, Hydroxyquercetin, Dyes Lignin, genistein glycosides, tannic acid, anthocyanins, hydroquinone, hesperetin, hesperidin, gallic acid, gallic acid esters (lauryl gallate, propyl gallate , butyl gallate), 4-methylcatechol, 5-methylcatechol, 4-methoxycatechol, 5-methoxycatechol, methoxycatechol- 4-carboxylic acid, 2-methylresorcinol, 5-methylresorcinol, lignin, limonin, limonin glucoside, methyl limonene, luteolin, luteolin glucoside, luteolin Ding, luteolin glycosides, rutin, resorcin, resveratrol, resorcinol, cyanidin, delphinidin and the like.

In addition to the polyphenol component, the composition of the present application may further contain various nutritional supplements, vitamins, electrolytes, flavors, colorants, pectic acid and its salts, alginic acid and its salts, organic acids, protective Colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerol, alcohols, carbonating agents and the like.

In particular, the compositions of the present application may include vitamin A, vitamin C, vitamin D, vitamin E, vitamin B1, vitamin B2, vitamin B6, vitamin B12, niacin, biotin, folic acid, pantothenic acid, and the like . In addition, the composition of the present application may include minerals such as zinc (Zn), iron (Fe), calcium (Ca), chromium (Cr), magnesium (Mg), manganese (Mn), copper (Cu) and the like similar. Additionally, the compositions of the present application may include amino acids such as lysine, tryptophan, cysteine, valine, and the like. Additionally, the compositions of the present application may include monosaccharides, such as glucose and fructose; disaccharides, such as maltose and sucrose; polysaccharides, such as dextrins and cyclodextrins; and sugar alcohols, such as xylitol, sorbitol, and erythritol Fucitol. In addition, the composition of the present application may include food additives, such as preservatives, including potassium sorbate, sodium benzoate, salicylic acid, sodium dehydroacetate, etc.; disinfectants, including bleaching powder and advanced bleaching powder, sodium hypochlorite, etc.; antioxidants, including Butylated hydroxymethoxybenzene (BHA), butylated hydroxytoluene (BHT), etc.; colorants, including tar pigments; color-fixing agents, including sodium nitrite and sodium acetate; bleaching agents, including sodium sulfite; flavoring agents, including sodium glutamate (MSG); sweeteners, including natural sweeteners, such as thomastin and stevia extract, and synthetic sweeteners, such as saccharin and aspartame; flavors, including vanillin and lactones; bulking agents, including Alum and D-potassium hydrogen tartrate; strengthening agents, emulsifiers, thickener/thickening agents, coating agents, gum bases, defoamers, solvents, modifiers and the like.

The additive can be selected according to the type of food and used in an appropriate amount.

In one embodiment, the compositions of the present application can be used to reduce off-flavors or off-flavors.

For the purposes of this application, "off-taste" means an unpleasant or distasteful person caused by a component contained in a product itself or by a secondary chemical change of that component, or by substances incorporated from outside sense of taste.

For the purposes of this application, "off-flavor" refers to the production of unpleasant or Disgusting smell.

Examples of odor-causing or off-flavor materials include nitrogen-containing compounds, sulfur compounds, lower fatty acids, carbonyl compounds, esters, phenols, alcohols, hydrocarbons, or chlorine compounds.

Specifically, the off-flavor may be a fishy smell. Fishy odors can be of vegetable or seafood origin, and in particular, fish.

The nitrogen-containing compound may include, but is not limited to, any substance that may cause an unpleasant odor, such as ammonia, trimethylamine, piperidine, trimethyl oxide, and the like, and in particular, it may be trimethylamine.

Off-flavor or off-flavor materials may be volatile odor components. The volatile odor component may be, but is not limited to, one or more compounds selected from the group consisting of: hexaldehyde/hexanal, heptanal, 2-nonenal ((Z)-), 2,4-heptaldehyde Dienal ((E,E)-), 2-hexenal ((E)-), 2,6-nonadienal ((E,Z)-), 2-nonanone, 2-pentene Aldehydes ((E)-), 1-penten-3-ones, disulfides and dimethyl compounds.

The composition containing chlorogenic acid, caffeic acid and quinic acid of the present application can be effectively used to reduce odor or off-flavor.

According to another aspect of the present application, there is provided a method for reducing odor or off-taste, the method comprising adding the above-mentioned composition of the present application to a material that produces off-flavor or off-flavor.

According to another aspect of the present application, there is provided a method for preparing a material for reducing off-flavor or off-taste, the method comprising adding the above-mentioned composition of the present application to the off-flavor or off-flavor producing material.

According to another aspect of the present application, there is provided a composition for preserving a product, the composition containing chlorogenic acid, caffeic acid and quinic acid.

In one embodiment, the composition for preserving the product can be used to prevent product oxidation or inhibit product browning.

In other specific examples, the product to be preserved, prevented from oxidation, or inhibited from browning may be a food product, feed product, household item, or industrial item.

The content ratio of chlorogenic acid, caffeic acid and quinic acid in the composition for preservation of the product of the present application is not limited. Based on 100 parts by weight of quinic acid, the total content of chlorogenic acid and caffeic acid may be within a range consisting of a lower limit and/or an upper limit selected from 0.1 part by weight, 0.3 part by weight, 0.4 part 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 150 parts by weight, the upper limit is selected from 700 parts by weight, 600 parts by weight parts, 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, based on 100 parts by weight of quinic acid, the total content of chlorogenic acid and caffeic acid 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 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.

Regarding the content ratio of chlorogenic acid and caffeic acid, based on 100 parts by weight of chlorogenic acid, the content of caffeic acid may be within a range consisting of a lower limit and/or an upper limit, the lower limit being selected from 10 parts by weight, 30 parts by weight parts, 35 parts by weight, 39 parts by weight, 40 parts by weight, 45 parts by weight, 49 parts by weight, 50 parts by weight, 70 parts by weight, 80 parts by weight and 90 parts by weight, the upper limit is selected from 400 parts by weight, 300 parts by weight, 200 parts by weight, 150 parts by weight, 140 parts by weight, 130 parts by weight, 120 parts by weight, 110 parts by weight and 100 parts by weight. For example, based on 100 parts by weight of chlorogenic acid, the content of caffeic acid may be 10-400 parts by weight, 30-300 parts by weight, 35-200 parts by weight, 40-150 parts by weight, 50-140 parts by weight, 60 to 130 parts by weight, 70 to 120 parts by weight, or 80 to 120 parts by weight.

With regard to the composition for the preservation of the product, according to one aspect of the present application, for the same, in particular details on the polyphenol component, details on components other than the polyphenol component and details on the content thereof , as in the above description of the "composition containing chlorogenic acid, caffeic acid and quinic acid" according to another aspect of the present application, citations to the described description are used and will not be repeated in order to avoid Complexity.

The composition of the present application containing chlorogenic acid, caffeic acid and quinic acid has excellent antioxidant effect, and thus can be used as an antioxidant.

The composition of the present application containing chlorogenic acid, caffeic acid and quinic acid can replace synthetic antioxidants such as butylated hydroxymethoxybenzene (BHA), butylated hydroxytoluene (BHT), tertiary butylhydroquinone (TBHQ) and the like.

In a specific example, the composition of the present application has an activity of effectively inhibiting the oxidation of fat or protein due to the free radical inhibiting activity.

The composition containing chlorogenic acid, caffeic acid and quinic acid of the present application can be used as a browning inhibitor.

The composition of the present application has significant polyphenol oxidase inhibitory activity, and thus has excellent browning inhibitory activity.

The browning inhibitor in the present application may be an inhibitor that inhibits the browning itself caused by the oxidation of phenolic compounds and an inhibitor that inhibits the browning caused by the reaction between sugars, amino acids and the like.

According to another aspect of the present application, there is provided a method for preventing oxidation of a product, the method comprising adding a composition containing chlorogenic acid, caffeic acid and quinic acid to the product.

According to another aspect of the present application, there is provided a method for inhibiting browning of a product, the method comprising adding a composition containing chlorogenic acid, caffeic acid and quinic acid to the product.

The composition containing chlorogenic acid, caffeic acid and quinic acid of the present application can be applied to various products.

The composition of the present application can be applied to, but not limited to, food, feed products, household items, industrial items, and the like. Specific examples of food or feed products include, but are not limited to, processed grain products, vegetables, fruits, dried or cut products of vegetables, fruit juices, vegetable juices, mixed juices of vegetables and fruits, potato chips, noodles, processed livestock and poultry foods, processed seafood , processed dairy products, fermented dairy products, microbial fermented foods, confectionery and bakery products, condiments, processed fish/meat products, acidic beverages, processed foods, convenience foods, licorice, herbal medicine, insect feed, livestock feed, pet food, etc.

Processed fish/meat products means ham, sausage, bacon, dried and stored meat, seasoned meat, packaged meat, ground meat products, processed pork ribs products, products extracted from meat, which are processed by using meat or fish meat as raw materials , edible tallow, edible lard, fish pieces, etc. "Meat" may be, but not limited to, meat commonly used in dietary habits, edible organs and by-products of cattle, pigs, sheep, goats, rabbits, chickens, turkeys, ducks, pheasants and quails. Types of processed meat products include, but are not limited to, pasteurized meat products, hams, pressed hams, mixed pressed hams, sausages, mixed sausages, dry sausages (mixed dry sausages), semi-dried sausages (mixed semi-dried sausages), heated frozen sausages, bacon , Store dried meat, seasoned meat, ground meat products, processed spareribs products, packaged meat and other processed meat products.

The compositions of the present application can be variously formulated for a particular application by using convenient and appropriate methods in the form of liquid, solid, powder, or the like. The composition of the present application can be combined with the raw materials during the preparation process and uniformly distributed on the food product by immersion, by stirring after immersion, by spraying, or by direct mixing.

According to another specific example of the present application, there is provided a quinic acid-containing composition for reducing off-flavor or off-flavor.

The description of the quinic acid-containing composition for reducing off-flavor or off-flavor is as described above.

The quinic acid-containing composition for reducing off-flavor or off-flavor may further contain polyphenols other than quinic acid, specifically, phenolic acid and/or quinic acid derivatives.

The quinic acid-containing composition for reducing off-flavor or off-flavor may be 10 wt% or more, 30 wt% or more, 50 wt% or more, 70 wt% or more based on 100 wt% of polyphenols more, 90 wt% or more, or 99 wt% or more.

Hereinafter, the present application will be described in detail by way of examples. However, the following examples specifically illustrate the present application, and the contents of the present application are not limited by the following examples.

Example

Experimental example 1 : Preparation of polyphenol-containing composition

1. Experimental Materials

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

2. containing polyphenols composition

In the compositions shown in Table 1 below, the polyphenol-containing compositions of T1 to T6 were prepared by mixing the same content of 50 ppm of three separate polyphenol compounds.

Table 1 Numbering composition T1 T2 T3 T4 T5 T6 1 Polyphenol 1 Chlorogenic acid Chlorogenic acid - Chlorogenic acid Catechin Chlorogenic acid 2 Polyphenol 2 caffeic acid caffeic acid - caffeic acid caffeic acid Catechin 3 Polyphenol 3 Quinic acid - Quinic acid Ferulic acid Quinic acid Quinic acid

3. Content ratio of polyphenol-containing composition

According to the T1 composition showing the best effect in the mixed polyphenol composition, the ratio of the content (unit: ppm) of chlorogenic acid, caffeic acid and quinic acid was adjusted to prepare S1 to S6 shown in Table 2 below of various polyphenol-containing compositions.

Table 2 Numbering composition S1 S2 S3 S4 S5 S6 1 Chlorogenic acid 50 1.5 1.04 0.74 81.8 56.3 2 caffeic acid 50 0.6 1.04 0.74 40.9 56.3 3 Quinic acid 50 147.9 148 148.51 27.3 37.5

Experimental example 2 : Trimethylamine ( TMA ) analyze

1. Trimethylamine ( TMA ) Standard preparation

A 30% strength trimethylamine product was purchased from Duksan Chemistry (Ansan, Republic of Korea) and used in the experiments. To determine the TMA reduction effect, a standard reagent of 30% trimethylamine was diluted to 100 ppm with distilled water to prepare a standard aqueous solution. The prepared standard aqueous solution was used as the solvent to prepare the test polyphenol composition, and the trimethylamine containing polyphenol composition sample was prepared and used for GC/MS analysis.

2. p-trimethylamine ( TMA ) Analysis of components and content

The trimethylamine (TMA) component was determined from the polyphenol composition via the following method. For adsorption of volatiles for analysis, a solid phase microextraction fiber holder (SPME, Supelco., Bellefonte, PA, USA) was pretreated by using DVB/CAR/PDMS (50/30 μm). 1 mL of the pretreated composition was placed in a 20 mL EPA vial, which was then capped with PTFE/silicon. A SPME needle was inserted into the vial to which the composition was added and used for GC/MS analysis after adsorption at 60°C for 30 minutes.

For GC/MS analysis, an Agilent gas chromatograph (GC2010 plus, Agilent, USA) was used 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 was set to 200°C, the total flow was set to 1.10 mL/min, and the total program time was set to 37 minutes before analysis. The amount of TMA in the composition was calculated by comparing the peak areas of 1.0 g of sample and 1 g of 100 mg/L TMA relative to each other and performing a comparative relative quantification of the content of volatile odor components in the samples.

Experimental example 3 : Polyphenol composition p-trimethylamine ( TMA ) reduced impact

To determine the superiority of the combination of chlorogenic acid, caffeic acid, and quinic acid, the TMA-reducing effect, known as the effect of polyphenols, was evaluated. Specifically, the trimethylamine (TMA) reducing effect of each polyphenol composition prepared in Experimental Example 1-2 was evaluated through the method of Experimental Example 2.

table 3 composition reduce(%) T1 80.36 T2 65.45 T3 57.66 T4 43.96 T5 40.13 T6 41.31

As determined by the results in Table 3 above, it was found that the combination of chlorogenic acid, caffeic acid, and quinic acid (T1 composition) exhibited the most excellent TMA reduction effect compared to other polyphenol combinations.

Experimental example 4 : Compositional ratio of polyphenol composition to trimethylamine ( TMA ) reduced impact

The trimethylamine (TMA) reducing effects of the polyphenol compositions having different component contents prepared in Experimental Examples 1-3 were evaluated by the method of Experimental Example 2.

Table 4 composition reduce(%) S1 90.55 S2 94.99 S3 98.32 S4 91.85 S5 74.61 S6 88.45

As can be seen in Table 4 above, it was found that the TMA reducing effect was maintained even if the contents of chlorogenic acid, caffeic acid and quinic acid were changed.

Experimental example 5 : Analysis of volatile odor components

1. experiment method

To determine the rancidity-reducing effect of polyphenolic compositions, these compositions were applied to fish oil, and analysis of volatile odor components was subsequently performed.

For adsorption of volatiles for analysis, a solid phase microextraction fiber holder (SPME, Supelco., Bellefonte, PA, USA) was pretreated by using DVB/CAR/PDMS (50/30 μm). For the samples used in the experiments, the polyphenol composition was added to fish oil, and then 1 g of fish oil (in which accelerated oxidation was induced in a 45°C incubator for 72 hours) was placed in a 20 mL EPA vial, followed by PTFE /silicon cover. The SPME needle was inserted into the vial to which the sample was added and used for GC/MS analysis after adsorption at 60°C for 30 minutes.

For GC/MS analysis, an Agilent gas chromatograph (GC2010 plus, Agilent, USA) was used with a DB-5MS column (thickness: 0.25 μm, length: 30 m, diameter: 0.25 mm). . He was used as carrier gas, and the column oven temperature was set to 100°C, the injection temperature was set to 200°C, the total flow was set to 1.10 mL/min, and the total program time was set to 37 minutes before analysis. The resulting values obtained were converted to peak area values and compared. As a result of the experiment, a compound having a rancid taste was identified, and a rancidity reducing effect was found.

2. to the experimental results analyze

The biggest obstacle to the use of fish oil is the fishy and rancid smell. This is due to the high content of polyunsaturated fatty acids in fish oil. Therefore, it appears that the content of natural antioxidants such as tocopherols is small, and the nitrogenous compounds contained in fish oil are bound to polyunsaturated fatty acids and oxidized to accelerate the appearance of rancidity.

The results of measuring the changes in the main volatile odor components resulting from the application of the polyphenol composition to fish oil are shown in Table 5 below (unit: peak area/10000).

table 5 compound (+) Control (-) control T1 T2 T3 T4 T5 T6 hexanal 12,289 17,596 12,285 15,074 15,202 14,669 14,773 15,061 Heptanal 19,778 27,217 19,562 26,472 24,068 23,556 23,985 23,551 2-Nonenal, (Z)- 6,678 7,038 6,002 6,773 6,480 6,193 6,690 6,456 2,4-Heptadienal, (E,E)- 50,063 51,784 40,137 49,414 49,408 47,646 47,391 51,436 2-Hexenal, (E)- 10,341 12,989 10,300 12,638 12,240 12,080 12,483 12,827 2,6-Nonadienal, (E,Z)- 5,540 5,491 4,498 5,253 5,149 5,422 4,852 5,470 2-nonanone 3,433 3,550 3,055 3,426 3,477 3,233 3,388 3,738 2-Pentenal, (E)- 25,577 38,026 27,287 36,002 33,736 31,754 31,830 33,584 1-Penten-3-one 11,944 17,721 12,762 16,680 15,810 14,719 14,839 15,338 Disulfides, Dimethyls 870 1,086 903 1,040 1,031 972 948 1,042

In Table 5 above, the positive (+) control is the group to which L-ascorbic acid is added, and the negative (-) control is the group to which no antioxidant or polyphenol is added.

From the results shown in Table 5, it was found that hexanal, which is an indicator of rancidity, exhibited low intensity in the positive control, and the T1 composition exhibited low intensity hexanal similar to the positive control.

Components involved in fish oil's fishy odor and characteristic grassy odor, such as heptanal, were reduced in all polyphenolic compositions compared to the negative control. Among all the polyphenol compositions, the T1 composition exhibited the most excellent reduction effect.

The component 2,4-heptadienal ((E,E)-) is known to cause strong fatty and fishy odors and has been reported to be composed of polyunsaturated fatty acids despite being present in fresh seafood The self-oxidation produced, and the content increased. The production of 2,4-heptadienal ((E,E)-) was highly inhibited by treatment with the polyphenolic composition (especially with the T1 composition) compared to the positive control.

In addition, alkenal and dienal compounds are volatile components of fish and appear to play an important role in the development of fishy odors. In addition, components such as disulfides and dimethyls were identified as strong off-odor components. It has been found that treatment with a polyphenolic composition inhibits the overall appearance of the alkenal, dienal, disulfide and dimethylate components involved in the suppression of rancidity.

Measurement results of changes in volatile odor components of compositions prepared by varying the content of the polyphenol component of the T1 polyphenol composition are shown in Table 6 below.

Table 6 compound S1 S2 S3 S4 S5 S6 hexanal 12,285 13,523 13,222 13,533 12,933 12,308 Heptanal 19,562 21,684 21,341 21,253 20,432 19,784 2-Nonenal, (Z)- 6,002 7,032 6,885 6,730 6,681 6,650 2,4-Heptadienal, (E,E)- 40,137 52,939 52,425 51,386 49,480 49,147 2-Hexenal, (E)- 10,300 10,155 11,323 11,410 11,479 10,370 2,6-Nonadienal, (E,Z)- 4,498 5,786 5,634 5,571 5,566 5,510 2-nonanone 3,055 3,504 3,347 3,327 3,323 3,280 2-Pentenal, (E)- 27,287 29,737 31,320 29,807 28,474 27,454 1-Penten-3-one 12,762 14,649 15,006 13,538 13,443 12,767 Disulfides, Dimethyls 903 1,535 1,081 977 933 923

According to the results in Table 6 above, it was found that even if the contents of chlorogenic acid, caffeic acid and quinic acid contained in the T1 composition were changed, there was no significant difference in the efficacy of changing the volatile odor components.

Experimental example 6 : A method for measuring the preservative effect of a polyphenol-containing composition

In order to confirm the preservative effect of the polyphenol compound-containing composition, the antioxidant effect and the browning inhibitory effect were measured. Antioxidative effect was determined by measuring DPPH free radical scavenging activity, and additionally using the Rancimat measurement method, in which oxidative stability can be determined by accelerated induction of fatty acid decay. The browning inhibitory effect was determined by measuring the polyphenol oxidase inhibitory activity.

Experimental example 7 : DPPH free radicals scavenging activity measurement

A 4 mM DPPH ethanol solution was prepared and used after adjusting the absorbance to 1.000 ± 0.1. 0.2 mL of each sample was added to the tube, 2.8 mL of DPPH solution was mixed and allowed to react for 10 minutes, and the absorbance was measured at 517 nm by using a microplate reader (M2, Molecular Device, Canada). L-Ascorbic acid was used as a positive control. The DPPH free radical scavenging activity was calculated according to the following formula:

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

(A: the absorbance of the group with added sample, B: the absorbance of the group without added sample)

The results of analyzing the DPPH free radical scavenging activity are shown in Table 7 below. There are differences depending on the polyphenol composition. Among the compositions, the T1 composition exhibited the highest scavenging activity, and the other compositions except the T3 composition exhibited free radical scavenging activity.

Table 7 ( + ) control ( - ) control T1 T2 T3 T4 T5 T6 DPPH ( % ) 81.07± ^0.59a 0.00±0.00 ^e 36.73± ^2.95b 29.14± ^2.36c 0.60±1.04 ^e 32.80± ^1.45bc 29.05± ^2.73c 22.06± ^4.71d *Duncan's multiple range test, p<0.05

As a result of measuring the change in the radical scavenging effect by changing the content ratio of the polyphenol component in the T1 composition exhibiting the most excellent effect, when the composition ratio of the three polyphenols was similarly adjusted, the effect tended to increase. Specifically, as shown in the results in Table 8, when the contents of chlorogenic acid and caffeic acid were mixed in similar ratios, the scavenging effect was high.

Table 8 S1 S6 DPPH ( % ) 36.73± ^2.95a 23.93± ^0.66b *Duncan's multiple range test, p<0.05

Experimental example 8 : by Rancimat Determination of oxidative stability by method

The oxidative stability of lipids was analyzed by using the Rancimat (743 Metrohm Co., Herisau, Switzerland) method. 2.5 g of fish oil [Sigma-Aldrich (St. Louis. MO, USA)] containing 2% polyphenol composition was placed in a reaction vessel, and air was heated to 20 L on an aluminum heating block controlled at 100 °C. /hr into lipids to oxidize lipids. The volatile oxidation products produced during this time were transferred to an absorption vessel containing 60 mL of distilled water, and the degree of anti-oxidation was determined by automatic calculation from the conductivity change through the induction period. In order to compare the antioxidant activity, the antioxidant index (AI) was calculated from the following formula by using a lipid sample without the addition of the polyphenol composition as a control: In addition, L-ascorbic acid was used as a positive control.

Antioxidative index (AI) = IG/IC (IG: control group, IC: treatment group)

The results of determining the oxidative stability after adding each polyphenol composition to fish oil are shown in Table 9. As shown in Table 9, most of the compositions exhibited similar or higher oxidative stability than the control, and in particular, the T1 composition had the highest oxidative stability. The overall trend shows a pattern similar to the results of measuring the antioxidant activity of DPPH free radical scavenging activity.

Table 9 ( + ) control ( - ) control T1 T2 T3 T4 T5 T6 IP ( min ) 90.53± ^1.37c 74.26±1.05 ^f 93.00± ^0.50b 88.33± ^0.90d 77.23± ^1.05e 88.10± ^0.75d 86.73± ^0.55d 77.13± ^0.73e AI 1.22± ^0.03c 1.00±0.00 ^f 1.25± ^0.11b 1.19± ^0.01d 1.04±0.01 ^e 1.18± ^0.01d 1.17± ^0.01d 1.04±0.01 ^e *Duncan's multiple range test, p<0.05

The results obtained by adding compositions prepared by varying the content of the polyphenol component in the T1 composition with the highest oxidative stability to the samples and then measuring the oxidative stability of the samples are shown in Table 10 below. As shown in the results in Table 10, when the contents of chlorogenic acid and caffeic acid were mixed in similar ratios, the oxidation stability was excellent.

Table 10 S1 S6 IP ( min ) 93.00±0.50 ^a 89.56± ^0.40b AI 1.21± ^0.15a 1.17± ^0.01b *Duncan's multiple range test, p<0.05

Experimental example 9 : Polyphenol oxidase ( PPO ) Determination of inhibitory activity

1.7 mL of 50 mM phosphate buffer (pH 6.5) and 0.2 mL of PPO (4,276 units/mg) were mixed, 0.1 mL of each polyphenol composition was added, and the mixture was allowed to stand for 15 minutes in a constant temperature water bath controlled at 25°C , and 1 mL of 4 mM catechin solution was added to each as substrate. Subsequently, absorbance changes were measured at 420 nm for 5 minutes by using a microplate reader (M2, Molecular Device, Canada). Enzyme inhibitory activity was expressed as a decrease in absorbance (%) expressed by the following formula:

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

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

Table 11 shows the results of measuring the polyphenol oxidase inhibitory activity of each polyphenol composition. According to the results shown in Table 11, the T1 composition exhibited the most excellent polyphenol oxidase inhibitory activity.

Table 11 ( + ) control ( - ) control T1 T2 T3 T4 T5 T6 PPO ( % ) 22.86± ^0.70a 0.00± ^0.00g 22.40± ^0.88a 17.97± ^0.46d 19.47± ^0.75c 10.57± ^0.75e 8.16± ^0.24f 9.58± ^0.49e *Duncan's multiple range test, p<0.05

The results of measuring the polyphenol oxidase inhibitory activity of the compositions prepared by varying the content of the polyphenol component in the T1 composition having the highest polyphenol oxidase inhibitory activity are shown in Table 12. As shown in the results in Table 12, when the contents of chlorogenic acid and caffeic acid were mixed in a similar ratio, the polyphenol oxidase inhibitory activity was excellent.

Table 12 S1 S6 PPO ( % ) 22.86±0.70 ^a 14.96± ^0.61b *Duncan's multiple range test, p<0.05

Although the representative embodiments of the present application have been described above, the scope of the present application is not limited to the specific embodiments as described above, and those of ordinary skill in the art can understand the scope of the claims of the present application. change within the scope of the description in this application.

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Claims (6)

A use of a composition comprising chlorogenic acid, caffeic acid and quinic acid for reducing off-taste or off-flavor. The use of the composition of claim 1, wherein based on 100 parts by weight of the quinic acid, the total content of the chlorogenic acid and the caffeic acid is 0.1 to 700 parts by weight. The use of the composition of claim 1, wherein the content of the caffeic acid is 10 to 400 parts by weight based on 100 parts by weight of the chlorogenic acid. The use of the composition of claim 1, wherein the off-flavor is a fishy smell. The use of the composition of claim 1, wherein the off-flavor is produced by nitrogen-containing compounds. Use of the composition of claim 1, wherein the off-flavor is produced by one or more compounds selected from the group consisting of: hexaldehyde/hexanal, heptanal, 2-nonenal ((Z)-) , 2,4-heptadienal ((E,E)-), 2-hexenal ((E)-), 2,6-nonadienal ((E,Z)-), 2-nonanal Ketones, 2-pentenal ((E)-), 1-penten-3-one, disulfides and dimethyl compounds.