KR102635424B1 - Composition Comprising Polyphenol - Google Patents

Composition Comprising Polyphenol Download PDF

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KR102635424B1
KR102635424B1 KR1020200123837A KR20200123837A KR102635424B1 KR 102635424 B1 KR102635424 B1 KR 102635424B1 KR 1020200123837 A KR1020200123837 A KR 1020200123837A KR 20200123837 A KR20200123837 A KR 20200123837A KR 102635424 B1 KR102635424 B1 KR 102635424B1
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acid
parts
weight
composition
product
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KR1020200123837A
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KR20210056222A (en
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한진희
박성용
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씨제이제일제당 (주)
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Priority to JP2022526253A priority Critical patent/JP7400098B2/en
Priority to TW109138796A priority patent/TWI772956B/en
Priority to CA3160517A priority patent/CA3160517A1/en
Priority to PCT/KR2020/015546 priority patent/WO2021091322A1/en
Priority to AU2020379492A priority patent/AU2020379492A1/en
Priority to US17/774,073 priority patent/US20220400727A1/en
Publication of KR20210056222A publication Critical patent/KR20210056222A/en
Priority to JP2023205326A priority patent/JP2024028851A/en
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Publication of KR102635424B1 publication Critical patent/KR102635424B1/en

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/20Removal of unwanted matter, e.g. deodorisation or detoxification
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00Function of food ingredients
    • A23V2200/02Antioxidant
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00Function of food ingredients
    • A23V2200/04Colour
    • A23V2200/048Preventing colour changes
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00Function of food ingredients
    • A23V2200/10Preserving against microbes
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00Function of food ingredients
    • A23V2200/15Flavour affecting agent
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00Food ingredients
    • A23V2250/20Natural extracts
    • A23V2250/21Plant extracts
    • A23V2250/2132Other phenolic compounds, polyphenols

Abstract

본 출원은 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물에 관한 것이다. 본 출원의 폴리페놀 함유 조성물은 제품의 보존제, 특히 제품의 산화방지제 또는 갈변억제제로 사용될 수 있다. This application relates to compositions comprising chlorogenic acid, caffeic acid, and quinic acid. The polyphenol-containing composition of the present application can be used as a preservative for products, especially as an antioxidant or browning inhibitor for products.

Description

폴리페놀을 포함하는 조성물{Composition Comprising Polyphenol}Composition Comprising Polyphenol}

본 출원은 폴리페놀을 포함하는 조성물의 보존제, 구체적으로는 제품의 보존제, 보다 구체적으로는 제품의 산화방지제 또는 갈변억제제로서의 용도에 관한 것이다. This application relates to the use of a composition containing polyphenols as a preservative, specifically as a preservative for products, and more specifically as an antioxidant or browning inhibitor for products.

폴리페놀(polyphenols)은 과일이나 엽채류 등의 식물에 함유되어 있는 화합물로 현재까지 확인되는 폴리페놀의 종류는 수천가지가 넘으며, 대표적으로 플라보노이드(flavonoids), 안토시아닌(anthocyanins), 타닌(tannins), 카테킨(catechins), 이소플라본(isoflavones), 리그난(lignans), 레스베라트롤(resveratrols) 등을 들 수 있다. 폴리페놀에 존재하는 다수의 히드록실기(-OH)는 여러 화합물과 쉽게 결합하는 특성을 가지고 있고, 항산화 효과 및 항암, 항염 효과가 뛰어나다. Polyphenols are compounds contained in plants such as fruits and leafy vegetables. There are over thousands of types of polyphenols identified to date, and representative examples include flavonoids, anthocyanins, tannins, Examples include catechins, isoflavones, lignans, and resveratrols. The numerous hydroxyl groups (-OH) present in polyphenols have the property of easily combining with various compounds and have excellent antioxidant, anti-cancer and anti-inflammatory effects.

폴리페놀은 단독 물질로도 효과를 보일 수 있으나, 각 물질을 조합에 의해서 효과가 상승할 수 있어서, 그 조합이 중요함이 알려져있으나(대한민국 공개특허 제 10-2015-0016343 호), 폴리페놀의 종류가 다양하여 그 조합에 의한 상승 효과를 확인하기에 어려움이 있다.Polyphenol can be effective as a single substance, but the effect can be increased by combining each substance, so it is known that the combination is important (Korean Patent Publication No. 10-2015-0016343), but polyphenol There are so many different types that it is difficult to confirm the synergistic effect of their combination.

대한민국 공개특허 제10-2015-0016343호Republic of Korea Patent Publication No. 10-2015-0016343

본 출원의 일 목적은 제품의 보존제, 또는 제품의 산화방지제 또는 갈변억제제의 용도로 사용될 수 있는 폴리페놀을 포함하는 조성물을 제공하는 것에 있다. One object of the present application is to provide a composition containing polyphenols that can be used as a preservative for products, or as an antioxidant or browning inhibitor for products.

상술한 목적을 달성하기 위해, 본 출원의 일 측면은 클로로젠산, 카페산, 및 퀴닌산을 포함하는 제품의 보존용 조성물을 제공한다. In order to achieve the above-described object, one aspect of the present application provides a composition for preserving products containing chlorogenic acid, caffeic acid, and quinic acid.

또한, 상술한 목적을 달성하기 위하여, 본 출원의 다른 측면은 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물을 제품에 첨가하는 단계를 포함하는 제품의 산화를 방지하는 방법을 제공한다. In addition, in order to achieve the above-described object, another aspect of the present application provides a method for preventing oxidation of a product comprising adding a composition containing chlorogenic acid, caffeic acid, and quinic acid to the product.

또한, 상술한 목적을 달성하기 위하여, 본 출원의 또 다른 측면은 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물을 제품에 첨가하는 단계를 포함하는 제품의 갈변을 억제하는 방법을 제공한다. In addition, in order to achieve the above-described object, another aspect of the present application provides a method of inhibiting browning of a product comprising adding a composition comprising chlorogenic acid, caffeic acid, and quinic acid to the product. .

본 출원의 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물은 제품의 보존 용도, 구체적으로 제품의 산화방지 또는 갈변억제 용도에 사용될 수 있다. The composition containing chlorogenic acid, caffeic acid, and quinic acid of the present application can be used for product preservation, specifically for preventing oxidation or browning of products.

본 출원의 폴리페놀 조성물은 DPPH 라디칼 소거능에서 확인되는 바와 같이산화방지효과가 매우 우수하며, 산화 안정성이 뛰어나고, 폴리페놀 옥시다아제 저해 활성이 높아 갈변억제활성을 가진다. As can be seen from the DPPH radical scavenging ability, the polyphenol composition of the present application has an excellent antioxidant effect, excellent oxidation stability, and has high polyphenol oxidase inhibitory activity and browning inhibition activity.

또한, 종래의 산화 방지제 또는 갈변 억제제와는 달리 제품에 잔존하는 양이 매우 적어 제품 본래 특징에 영향을 주지 않고, 가공제품 제조 공정에 적용하기 쉬운 이점을 가진다. In addition, unlike conventional antioxidants or browning inhibitors, the amount remaining in the product is very small, so it does not affect the original characteristics of the product and has the advantage of being easy to apply in the manufacturing process of processed products.

다만, 본 출원의 효과는 상기에서 언급한 효과로 제한되지 아니하며, 언급되지 않은 또 다른 효과들은 하기의 기재로부터 당업자에게 명확히 이해될 수 있을 것이다. 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 skilled in the art from the following description.

이하, 본 출원을 구체적으로 설명한다. Hereinafter, this application will be described in detail.

본 출원의 일 측면에 따르면, 본 출원은 클로로젠산, 카페산, 및 퀴닌산을 포함하는 제품의 보존용 조성물을 제공한다. According to one aspect of the present application, the present application provides a composition for preserving a product containing chlorogenic acid, caffeic acid, and quinic acid.

일 구현예에서, 상기 제품의 보존용은 제품의 산화방지용 또는 갈변억제용 일 수 있다. In one embodiment, the preservation of the product may be for preventing oxidation or browning of the product.

다른 구현예에서, 상기 보존용, 산화방지용 또는 갈변억제용의 대상 제품은 식품, 사료, 생활용품 또는 공업용품일 수 있다. In another embodiment, the target product for preservation, antioxidant or browning inhibition may be food, feed, household goods, or industrial products.

본 출원의 활성성분인 클로로젠산, 카페산, 및 퀴닌산은 폴리페놀 성분이다.The active ingredients of this application, chlorogenic acid, caffeic acid, and quinic acid, are polyphenol components.

본 출원에서 사용되는 용어 "폴리페놀"은 분자내에 하나 이상의 히드록시기를 갖는 페놀을 하나 이상 포함하는 화합물을 의미한다. 상기 폴리페놀은 폴리페놀 자체 및 이의 배당체, 이의 알킬화 화합물, 이의 에스터화 화합물 등 유도체(derivatives)도 포함하는 개념이다. The term “polyphenol” used in this application refers to a compound containing one or more phenols having one or more hydroxy groups in the molecule. The polyphenol is a concept that also includes polyphenol itself and derivatives such as its glycoside, its alkylated compound, and its esterified compound.

본 출원에서 클로로젠산(chlorogenic acid)은 카페산(caffeic acid)와 퀴닌산(quinic acid)이 에스테르 결합으로 구성된 화합물이며 아래의 화학식 1로 표시된다. In this application, chlorogenic acid is a compound composed of an ester bond of caffeic acid and quinic acid and is represented by the formula 1 below.

[화학식 1][Formula 1]

본 출원에서 카페산은 하이드록시 신남산으로 분류되는 화합물로서, 아래의 화학식 2로 표시된다. In this application, caffeic acid is a compound classified as hydroxycinnamic acid and is represented by Chemical Formula 2 below.

[화학식 2] [Formula 2]

본 출원에서 퀴닌산(quinic acid)은 아래의 화학식 3으로 표시된다. In this application, quinic acid is represented by Chemical Formula 3 below.

[화학식 3] [Formula 3]

본 출원에서 사용되는 클로로젠산, 카페산 및 퀴닌산은 천연물로부터 유래된 물질 뿐만 아니라 인공적으로 합성된 물질도 사용할 수 있다. Chlorogenic acid, caffeic acid, and quinic acid used in this application may be materials derived from natural products as well as artificially synthesized materials.

상기 천연물은 클로젠산, 카페산 및/또는 퀴닌산을 포함하는 어느 물질이든 제한없이 이용가능하나, 식물일 수 있다. 구체적으로 알로에, 아니스 씨드, 딱총나무, 가시오가피, 차전자피, 오렌지 플라워, 피멘토나무, 오레가노, 쥐오줌풀, 캐모마일, 캅사이신 페퍼, 카다몬, 계수나무, 마늘, 캐러웨이 씨드, 정향, 커민 씨드, 콜라나무, 고수풀 씨드, 붉나무, 사프란, 산초나무, 쥬니퍼 베리, 시나몬, 생강, 팔각, 세인트 존스 워트, 셀러리 씨드, 세이보리, 참깨, 식용 대황, 타라곤, 터메릭, 엉겅퀴, 딜 씨드, 육두구, 쐐기풀, 하이비스커스, 풍년화, 자작나무, 바질, 비터 오렌지, 회향, 앵초, 호로파, 버베나, 월계수, 홉, 볼도, 와사비, 양귀비 씨드, 오배자, 매리골드, 마롱, 마조람, 머스터드, 밀푀유, 민트 잎, 멜리사, 육두구, 린덴, 용담, 로즈힙, 로즈마리, 로즈마리너스 오피시널리스, 해바라기 씨드, 그레이프 과피, 사과, 당근 잎, 바나나, 딸기, 살구나무, 복숭아, 자두, 파인애플, 나시배, 감나무, 체리, 파파야, 망고, 아보카도, 멜론, 비파나무, 무화과, 키위, 푸룬, 블루베리, 블랙베리, 라즈베리, 크랜베리, 커피콩, 카카오콩, 그레이프 씨드, 그레이프 프루트 씨드, 피칸 넛, 캐슈 넛, 밤, 코코넛, 피넛, 월넛, 녹차잎, 홍차잎, 우롱차잎, 담배, 들깨잎, 가든타임, 세이지, 라벤더, 스페아민트, 페퍼민트, 스팟 엉겅퀴, 히솝, 스위트 바질, 매리골드, 민들레, 아티초크, 저맨캐모마일, 짚신나물, 감초, 아니스, 서양톱풀, 유칼립투스, 쓴쑥, 밭삼, 땅두릅, 호로파, 꽃고추, 회향, 고추, 고수풀 씨드, 캐러웨이 씨드, 회향 씨드, 생강, 겨자무, 오레가노 마조람, 오레가노(origanum valgare), 머스터드, 파슬리, 후추, 세이보리, 타라곤, 쿠르크마, 고추냉이, 딜 씨드, 또는 감귤류 과일 등일 수 있다. The natural product may be any substance including clogenic acid, caffeic acid, and/or quinic acid without limitation, but may be a plant. Specifically, aloe, anise seed, elderberry, acanthus ginseng, psyllium husk, orange flower, pimento tree, oregano, valerian, chamomile, capsaicin pepper, cardamom, cassia, garlic, caraway seed, clove, cumin seed, and kola tree. , coriander seed, rhubarb, saffron, saffron, juniper berry, cinnamon, ginger, star anise, St. John's wort, celery seed, savory, sesame, edible rhubarb, tarragon, turmeric, thistle, dill seed, nutmeg, nettle, hibiscus, Wildflowers, birch, basil, bitter orange, fennel, primrose, fenugreek, verbena, laurel, hops, boldo, horseradish, poppy seeds, gallnut, marigold, maroon, marjoram, mustard, millefeuille, mint leaves, melissa, Nutmeg, linden, gentian, rosehip, rosemary, Rosmarinus officinalis, sunflower seeds, grape peel, apple, carrot leaf, banana, strawberry, apricot tree, peach, plum, pineapple, nashi pear, persimmon tree, cherry, papaya, Mango, avocado, melon, loquat tree, fig, kiwi, prune, blueberry, blackberry, raspberry, cranberry, coffee bean, cacao bean, grape seed, grapefruit seed, pecan nut, cashew nut, chestnut, coconut, peanut, Walnut, green tea leaves, black tea leaves, oolong tea leaves, tobacco, perilla leaves, garden thyme, sage, lavender, spearmint, peppermint, spotted thistle, hyssop, sweet basil, marigold, dandelion, artichoke, German chamomile, paramecium, Licorice, anise, yarrow, eucalyptus, bitter mugwort, field ginseng, ground aralia, fenugreek, cauliflower, fennel, red pepper, coriander seed, caraway seed, fennel seed, ginger, horseradish, oregano marjoram, oregano (origanum valgare), mustard. , parsley, pepper, savory, tarragon, curcuma, horseradish, dill seeds, or citrus fruits.

상기 천연물로부터 당업계에 공지된 방법, 예를 들어 공지된 추출방법에 의해 분리 정제한 것을 사용할 수 있다. A product separated and purified from the above natural product by a method known in the art, for example, a known extraction method, can be used.

본 출원의 조성물에서 클로로젠산, 카페산 및 퀴닌산은 그 함량 비율이 제한없이 이용될 수 있으나, 퀴닌산 100 중량부 기준 클로로젠산 및 카페산의 함량 합계가 0.1 중량부, 0.3 중량부, 0.4 중량부, 0.5 중량부, 0.7 중량부, 1 중량부, 1.1 중량부, 1.3 중량부, 1.4 중량부 10 중량부, 50 중량부, 및 100 중량부, 및 150 중량부 중에서 선택되는 하나의 하한선, 및/또는 700 중량부, 600 중량부, 500 중량부, 450 중량부, 400 중량부, 350 중량부, 340 중량부, 330 중량부, 320 중량부, 310 중량부, 300 중량부, 250 중량부, 240 중량부, 230 중량부, 210 중량부, 200 중량부, 및 150 중량부 중에서 선택되는 하나의 상한선으로 구성된 범위일 수 있다. 일례로 0.1 내지 700 중량부, 0.3 내지 600 중량부, 0.5 내지 600 중량부, 1 내지 500 중량부, 10 내지 450 중량부, 50 내지 450 중량부, 100 내지 400 중량부, 150 내지 350 중량부, 200 내지 350, 또는 200 내지 300 중량부일 수 있다. In the composition of the present application, chlorogenic acid, caffeic acid, and quinic acid can be used without limitation in their content ratios, but the total content of chlorogenic acid and caffeic acid based on 100 parts by weight of quinic acid is 0.1 part by weight, 0.3 part by weight, and 0.4 part by weight. a lower limit selected from 10 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, and 100 parts by weight, and 150 parts by weight, and/or 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, 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, It may be 200 to 350, or 200 to 300 parts by weight.

상기 클로로젠산, 카페산의 함량 비율은 클로로젠산 100 중량부 기준 카페산 함량이 10 중량부, 30 중량부, 35 중량부, 39 중량부, 40 중량부, 45 중량부, 49 중량부, 50 중량부, 70 중량부 80 중량부 및 90 중량부로부터 선택되는 하나의 하한선, 및/또는 400 중량부, 300 중량부, 200 중량부, 150 중량부, 140 중량부, 130중량부, 120 중량부, 110 중량부 및 100 중량부로부터 선택되는 하나의 상한선으로부터 구성된 범위일 수 있다. 일례로 10 중량부 내지 400 중량부, 30 중량부 내지 300 중량부, 35 중량부 내지 200 중량부, 40 중량부 내지 150 중량부, 50 중량부 내지 140 중량부, 60 중량부 내지 130 중량부, 70 중량부 내지 120 중량부, 또는 80 중량부 내지 120 중량부일 수 있다. The content ratio of chlorogenic acid and caffeic acid is 10 parts by weight, 30 parts by weight, 35 parts by weight, 39 parts by weight, 40 parts by weight, 45 parts by weight, 49 parts by weight, based on 100 parts by weight of chlorogenic acid. A lower limit selected from 50 parts by weight, 70 parts by weight, 80 parts by weight and 90 parts by weight, and/or 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. parts, 110 parts by weight, and 100 parts by weight. For example, 10 parts by weight to 400 parts by weight, 30 parts by weight to 300 parts by weight, 35 parts by weight to 200 parts by weight, 40 parts by weight to 150 parts by weight, 50 parts by weight to 140 parts by weight, 60 parts by weight to 130 parts by weight, It may be 70 parts by weight to 120 parts by weight, or 80 parts by weight to 120 parts by weight.

상기 클로로젠산, 카페산, 퀴닌산의 함량비율에서 폴리페놀 조합의 효과가 발현될 수 있다. The effect of the polyphenol combination can be expressed in the content ratio of chlorogenic acid, caffeic acid, and quinic acid.

상기 조성물은 카페산, 클로로젠산, 퀴닌산 함량을 조절하여 사용할 수 있으나, 조성물 기준 카페산, 클로로젠산 및 퀴닌산의 함량 합계가 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 및 150 ppm 중에서 선택되는 하나의 하한선, 및/또는 5,000 ppm, 2,000 ppm, 1,000 ppm, 500 ppm, 300 ppm, 250 ppm, 230 ppm 및 200 ppm 중에서 선택되는 하나의 상한선으로 구성된 범위일 수 있다. 일례로 0.1 ppm 내지 5,000 ppm, 1 ppm 내지 2,000 ppm, 50 ppm 내지 1,000 ppm, 100 ppm 내지 1,000 ppm, 120 ppm 내지 1,000 ppm, 120 ppm 내지 500 ppm, 140 ppm 내지 300 ppm, 140 ppm 내지 250 ppm, 140 ppm 내지 230 ppm, 145 ppm 내지 230 ppm, 145 ppm 내지 200 ppm, 149 ppm 내지 200 ppm, 또는 150 ppm 내지 200 ppm일 수 있다. 상기 ppm 은 중량비(w/w)일수도 있다. The composition can be used by adjusting the content of caffeic acid, chlorogenic acid, and quinic acid, but the total content of caffeic acid, chlorogenic acid, and quinic acid based on the composition is 0.1 ppm, 0.5 ppm, 1 ppm, 10 ppm, 20 ppm, a lower limit selected from 40 ppm, 50 ppm, 80 ppm, 100 ppm, 120 ppm, 140 ppm, 145 ppm, 149 ppm, and 150 ppm, and/or 5,000 ppm, 2,000 ppm, 1,000 ppm, 500 ppm, 300 ppm , 250 ppm, 230 ppm, and 200 ppm. For example, 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, It can be 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 may also be a weight ratio (w/w).

본 출원의 조성물은 클로로젠산, 카페산, 퀴닌산을 제외한 다른 폴리페놀을 추가로 더 포함할 수 있다. The composition of the present application may further include other polyphenols other than chlorogenic acid, caffeic acid, and quinic acid.

다른 폴리페놀은 구체적으로, 페놀릭산(Phenolic acid), 플라보노이드(Flavoids), 스틸벤(stilbens), 리그난(lignin) 등 제한없이 포함될 수 있으며, 일례로 이소람네틴, 이소람네틴 글리코사이드, 카테킨, 에피카테킨, 갈로카테킨, 에피카테킨 갈레이트, 에피갈로카테킨, 에피갈로카테킨 갈레이트, 엘라그산, 카테콜, 카페산 에스테르, 켐페롤, 켐페롤 글리코사이드, 퀘르세틴, 퀘르세틴 글리코사이드, 퀘르세타게닌, 게니세틴, 게니세틴 글리코사이드, 탄닌산, 안토시아닌, 하이드로퀴논, 헤스페레틴, 헤스페리딘, 갈산, 갈산 에스테르(갈산 라우릴, 갈산 프로필, 갈산 부틸), 4-메틸카테콜, 5-메틸카테콜, 4-메톡시카테콜, 5-메톡시카테콜, 메틸카테콜-4-카복실산, 2-메틸레조르시놀, 5-메틸레조르시놀, 리그닌, 리모시트린, 리모시트린 글리코사이드, 리모시트롤, 루테올린, 루테올린 글리코사이 드, 루테올리니딘, 루테올리니딘 글리코사이드, 루틴, 레조르신, 레스베라트롤, 레조르시놀, 로이코시아니딘, 또는 로이코델피니딘 등을 들 수 있으나, 이에 한정되지 않는다. Other polyphenols may be specifically included without limitation, such as phenolic acid, flavonoids, stilbens, and lignin, and examples include isorhamnetin, isorhamnetin glycoside, catechin, Epicatechin, gallocatechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, ellagic acid, catechol, caffeic acid ester, kaempferol, kaempferol glycoside, quercetin, quercetin glycoside, quercetagenin, Genisetin, genisetin glycoside, tannic acid, anthocyanin, hydroquinone, hesperetin, hesperidin, gallic acid, gallic acid esters (lauryl gallate, propyl gallate, butyl gallate), 4-methylcatechol, 5-methylcatechol, 4 -Methoxycatechol, 5-methoxycatechol, methylcatechol-4-carboxylic acid, 2-methylresorcinol, 5-methylresorcinol, lignin, rimocitrin, rimocitrin glycoside, rimocitrol, lute. Examples include, but are not limited to, olin, luteolin glycoside, luteolinidin, luteolinidin glycoside, rutin, resorcin, resveratrol, resorcinol, leucocyanidin, or leucodelphinidin.

본 출원의 조성물은 폴리페놀 성분 이외에 여러 가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산, 펙트산의 염, 알긴 산, 알긴산의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알코올 또는 탄산화제 등을 추가로 함유할 수 있다. In addition to the polyphenol component, the composition of the present application contains various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid, salts of pectic acid, alginic acid, salts of alginic acid, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, It may additionally contain preservatives, glycerin, alcohol, or carbonating agents.

구체적으로, 본 출원의 조성물은 비타민 A, C, D, E, B1, B2, B6, B12, 니아신(niacin), 비오틴(biotin), 폴레이트 (folate), 판토텐산(panthotenic acid) 등을 포함할 수 있다. 또한, 아연(Zn), 철(Fe), 칼슘(Ca), 크롬(Cr), 마그네슘(Mg), 망간(Mn), 구리(Cu), 크륨(Cr) 등의 미네랄을 포함할 수 있다. 또한, 라이신, 트립토판, 시스테인, 발린 등의 아미노산을 포함할 수 있다. 또한, 포도당, 과당과 같은 모노사카라이드; 말토스, 슈크로스와 같은 다이사카라이드; 덱스트린, 사이클로덱스트린과 같은 폴리사카라이드; 자일리톨, 소르비톨, 에리트리톨 등의 당알콜을 포함할 수 있다. 또한, 방부제로서 소르빈산 칼륨, 벤조산나트륨, 살리실산, 데히드로초산나트륨 등; 살균제로서 표백분과 고도 표백분, 차아염소산나트륨 등; 산화방지제로서 부틸히드록시아니졸(BHA), 부틸히드록시톨류엔(BHT) 등; 착색제로서 타르색소; 발색제로서, 아질산 나트륨, 아초산 나트륨; 표백제로서 아황산나트륨; 조미료로서, MSG 글루타민 산나트륨; 감미료로서 타우마틴, 스테비아 추출물과 같은 천연 감미제, 사카린, 아스파르탐과 같은 합성 감미제; 향료로서 바닐린, 락톤류; 팽창제로서 명반, D주석산수소칼륨; 강화제, 유화제, 증점제(호료), 피막제, 검기초제, 거품억제제, 용제, 개량제 등의 식품 첨가물(food additives)을 포함할 수 있다. Specifically, the composition of the present application may include vitamins A, C, D, E, B1, B2, B6, B12, niacin, biotin, folate, pantothenic acid, etc. You can. Additionally, it may contain minerals such as zinc (Zn), iron (Fe), calcium (Ca), chromium (Cr), magnesium (Mg), manganese (Mn), copper (Cu), and chromium (Cr). Additionally, it may contain amino acids such as lysine, tryptophan, cysteine, and valine. Additionally, monosaccharides such as glucose and fructose; Disaccharides such as maltose and sucrose; polysaccharides such as dextrins and cyclodextrins; It may contain sugar alcohols such as xylitol, sorbitol, and erythritol. Additionally, as preservatives, potassium sorbate, sodium benzoate, salicylic acid, sodium dehydroacetate, etc.; As disinfectants, bleaching powder, advanced bleaching powder, sodium hypochlorite, etc.; Antioxidants such as butylhydroxyanisole (BHA) and butylhydroxytoluene (BHT); Tar coloring as a colorant; As a coloring agent, sodium nitrite, sodium nitrite; Sodium sulfite as a bleaching agent; As a seasoning, MSG monosodium glutamate; Sweeteners include natural sweeteners such as thaumatin and stevia extract, and synthetic sweeteners such as saccharin and aspartame; Vanillin and lactones as fragrances; Alum, potassium bitartrate as leavening agents; It may contain food additives such as strengtheners, emulsifiers, thickeners (grease), coating agents, gum base agents, anti-foam agents, solvents, and improvers.

상기 첨가물은 식품의 종류에 따라 선별되고 적절한 양으로 사용될 수 있다.The additives can be selected depending on the type of food and used in an appropriate amount.

본 출원의 클로로젠산, 카페산 및 퀴닌산 함유 조성물은 뛰어난 항산화 효과를 가지므로, 산화 방지제로 사용될 수 있다. The composition containing chlorogenic acid, caffeic acid, and quinic acid of the present application has excellent antioxidant effects and can be used as an antioxidant.

본 출원의 클로로젠산, 카페산 및 퀴닌산 함유 조성물은, BHA(butylated hydroxyanisole), BHT(butylated hydroxytoluene) 또는 TBHQ(tertiary butylhydropuinone) 등과 같은 합성 항산화제를 대체할 수 있다. The composition containing chlorogenic acid, caffeic acid, and quinic acid of the present application can replace synthetic antioxidants such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), or tertiary butylhydropuinone (TBHQ).

일 구현예에서, 본 출원의 조성물은 자유 라디칼 억제 활성으로 인해 지방 또는 단백질의 산화를 효율적으로 억제하는 활성을 가진다. In one embodiment, the composition of the present application has the activity of efficiently inhibiting the oxidation of fat or protein due to its free radical inhibition activity.

본 출원의 클로로젠산, 카페산 및 퀴닌산 함유 조성물은 갈변억제제로 사용될 수 있다. The composition containing chlorogenic acid, caffeic acid, and quinic acid of the present application can be used as a browning inhibitor.

본 출원의 조성물은 뛰어난 폴리페놀 옥시다아제(polyphenol oxidase) 저해 활성을 가지므로, 우수한 갈변억제 활성을 갖는다. The composition of the present application has excellent polyphenol oxidase inhibitory activity, and therefore has excellent browning inhibition activity.

본 출원에서 갈변 억제제는 페놀성 화합물의 산화에 의해 생기는 갈변 자체를 억제하는 것일 수 있고, 당류, 아미노산 등의 반응으로 발생하는 갈변 반응을 억제하는 것일 수 있다. In the present application, the browning inhibitor may be one that inhibits the browning itself caused by oxidation of phenolic compounds, or may be one that inhibits the browning reaction that occurs in reactions with sugars, amino acids, etc.

본 출원의 다른 측면에 따르면, 본 출원은 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물을 제품에 첨가하는 단계를 포함하는 제품의 산화를 방지하는 방법을 제공한다. According to another aspect of the present application, the present application provides a method of preventing oxidation of a product comprising adding to the product a composition comprising chlorogenic acid, caffeic acid, and quinic acid.

본 출원의 또 다른 측면에 따르면, 본 출원은 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물을 제품에 첨가하는 단계를 포함하는 제품의 갈변을 억제하는 방법을 제공한다.According to another aspect of the present application, the present application provides a method of inhibiting browning of a product comprising adding to the product a composition comprising chlorogenic acid, caffeic acid, and quinic acid.

본 출원의 조성물이 적용될 수 있는 제품은 식품, 사료, 생활용품, 공업용품 등 제한 없이 적용될 수 있다. Products to which the composition of this application can be applied can be applied without limitation, such as food, feed, household goods, and industrial products.

상기 식품 또는 사료의 구체적인 예로는, 곡류가공품, 야채, 과일, 야채의 건조제품이나 절단제품, 과일쥬스, 야채쥬스, 야채와 과일의 혼합쥬스, 칩류, 면류, 축산가공식품, 수산가공식품, 유가공식품, 발효유식품, 미생물발효식품, 제과제빵, 양념류, 어/육가공류, 산성음료수, 가공식품류, 간편식류, 감초류, 허브류, 곤충 사료류, 가축 사료류, 애완동물 사료류 등이 있으나 이에 제한되는 것은 아니다. Specific examples of the above food or feed include processed grain products, vegetables, fruits, dried or cut vegetables, fruit juice, vegetable juice, mixed juice of vegetables and fruits, chips, noodles, processed livestock food, processed fishery food, and dairy products. Foods, fermented milk foods, microbial fermented foods, confectionery and bakery products, seasonings, fish/meat products, acidic beverages, processed foods, convenience foods, licorice, herbs, insect feeds, livestock feeds, pet feeds, etc., but limited to these. It doesn't work.

상기 어/육가공류은 식육 또는 어육을 원료로 하여 가공한 햄류, 소시지류, 베이컨류, 건조저장육류, 양념육류, 포장육, 분쇄가공육제품, 갈비가공품, 식육추출가공품, 식용우지, 식용돈지, 어육의 육괴 등을 의미한다. 상기 '식육'은 소, 돼지, 양, 염소, 토끼, 닭, 칠면조, 오리, 꿩, 메추리 등의 식생활 관습상 일반적으로 사용되는 육류와 식용 가능한 장기류 및 부산물일 수 있으나, 이에 제한되지 않는다. 육가공품의 형태로는 멸균 식육제품, 햄류, 프레스햄, 혼합프레스햄, 소시지, 혼합소시지, 건조소시지(건조혼합소시지), 반건조소시지(반건조혼합소시지), 가열냉동소시지, 베이컨류, 건조저장육, 양념육, 분쇄가공품, 갈비가공품, 포장육 및 기타 식육가공품 등을 포함하며, 이에 제한되지 않는다. The above fish/meat products include ham, sausages, bacon, dried stored meat, seasoned meat, packaged meat, ground and processed meat products, rib products, processed meat extract products, edible beef tallow, edible pork, and fish meat processed using edible meat or fish meat as a raw material. It means mass, etc. The 'edible meat' may include meat commonly used in dietary customs such as cattle, pigs, sheep, goats, rabbits, chickens, turkeys, ducks, pheasants, and quail, as well as edible organs and by-products, but is not limited thereto. Forms of processed meat products include sterilized meat products, ham, pressed ham, mixed pressed ham, sausage, mixed sausage, dried sausage (dry mixed sausage), semi-dried sausage (semi-dried mixed sausage), heated and frozen sausage, bacon, and dry storage. Includes, but is not limited to, meat, seasoned meat, ground and processed products, processed ribs, packaged meat and other processed meat products.

본 출원의 조성물이 용도에 맞게 사용되는 경우, 용도에 맞게 편리하고 적합한 방법으로 액상, 고상, 파우더 형태 등으로 다양하게 제제화될 수 있다. 본 출원의 조성물은 제조 공정시 원료와 함께 배합할 수 있으며, 식품을 본 출원의 조성물에 담그거나, 담근 후 휘젓거나, 조성물을 뿌리거나, 직접 혼합함으로써 이를 식품에 고르게 적용될 수 있도록 할 수 있다. When the composition of the present application is used for its intended purpose, it can be formulated in various forms such as liquid, solid, or powder in a convenient and suitable manner for the intended purpose. The composition of the present application can be mixed with raw materials during the manufacturing process, and can be evenly applied to the food by dipping the food in the composition of the present application, stirring it after soaking, spraying the composition, or directly mixing it.

이하, 본 출원을 실시예에 의하여 상세히 설명한다. Hereinafter, the present application will be described in detail through examples.

단, 하기 실시예는 본 출원을 구체적으로 예시하는 것이며, 본 출원의 내용이 하기 실시예에 의해 한정되지 아니한다. However, the following examples specifically illustrate the present application, and the content of the present application is not limited by the following examples.

실험예 1: 폴리페놀 함유 조성물의 제조 Experimental Example 1: Preparation of polyphenol-containing composition

1. 실험 재료 1. Experimental Materials

실험에 사용한 폴리페놀인 클로로젠산, 카페산, 갈산, 카테킨, 페룰린산, 퀴닌산은 Sigma-aldrich社(USA)에서 구입하여 사용하였다. The polyphenols used in the experiment, chlorogenic acid, caffeic acid, gallic acid, catechin, ferulic acid, and quinic acid, were purchased from Sigma-aldrich (USA).

2. 폴리페놀 함유 조성물의 성분 구성 2. Composition of polyphenol-containing composition

아래 표 1에 나타낸 성분 구성으로 50 ppm의 동일한 함량으로 3가지의 폴리페놀 단일 화합물들을 혼합하여 T1 내지 T6의 폴리페놀 함유 조성물들을 제조하였다. Polyphenol-containing compositions of T1 to T6 were prepared by mixing three polyphenol single compounds at the same content of 50 ppm with the component composition shown in Table 1 below.

NoNo 구성 composition T1T1 T2T2 T3T3 T4T4 T5T5 T6T6 1One 폴리페놀1polyphenol 1 클로로젠산chlorogenic acid 클로로젠산chlorogenic acid -- 클로로젠산chlorogenic acid 카테킨catechin 클로로젠산chlorogenic acid 22 폴리페놀2polyphenol 2 카페산caffeic acid 카페산caffeic acid -- 카페산caffeic acid 카페산caffeic acid 카테킨catechin 33 폴리페놀3polyphenol 3 퀴닌산Quinic acid -- 퀴닌산Quinic acid 페룰린산Ferulic acid 퀴닌산Quinic acid 퀴닌산Quinic acid

3. 폴리페놀 함유 조성물의 성분 함량비 구성 3. Composition of component content ratio of polyphenol-containing composition

폴리페놀들의 혼합 조성물 중에서 가장 좋은 효과를 나타낸 T1 조성물에서 클로로젠산, 카페산, 퀴닌산의 함량(ppm) 비율을 조절하여, 아래 표 2의 S1 및 S2 폴리페놀 함유 조성물들을 제조하였다. The S1 and S2 polyphenol-containing compositions shown in Table 2 below were prepared by adjusting the contents (ppm) of chlorogenic acid, caffeic acid, and quinic acid in the T1 composition, which showed the best effect among the mixed compositions of polyphenols.

NoNo 구성composition S1S1 S2S2 1One 클로로젠산chlorogenic acid 5050 56.356.3 22 카페산caffeic acid 5050 56.356.3 33 퀴닌산Quinic acid 5050 37.537.5

실험예 2: 폴리페놀 함유 조성물의 보존 효과의 측정 방법 Experimental Example 2: Method for measuring the preservation effect of polyphenol-containing compositions

폴리페놀 화합물을 함유하는 조성물의 보존 효과를 확인 하기 위해 산화방지 효과와 갈변 저해 효과를 측정하였다. 산화방지 효과는 DPPH 라디칼 소거능을 측정하여 확인하였으며, 추가로 지방의 산패여부를 가속으로 유도하여 산화안정성을 확인할 수 있는 Rancimat 측정 방법을 사용하였다. 갈변 저해 효과는 폴리페놀 옥시다아제(polyphenol oxidase) 저해 활성의 측정을 통해 확인하였다. To confirm the preservation effect of the composition containing polyphenol compounds, the antioxidant effect and browning inhibition effect were measured. The antioxidant effect was confirmed by measuring the DPPH radical scavenging ability, and in addition, the Rancimat measurement method was used to check the oxidation stability by inducing accelerated rancidity of fat. The browning inhibition effect was confirmed through measurement of polyphenol oxidase inhibitory activity.

실험예 3: DPPH 라디칼 소거능 측정 Experimental Example 3: Measurement of DPPH radical scavenging ability

4 mM의 DPPH 에탄올 용액을 제조하여 흡광도를 1.000±0.1로 조절하여 사용하였다. 각각의 시료 0.2㎖를 시험관에 가하고 DPPH 용액 2.8㎖를 혼합하여 10분간 반응시킨 후 517nm에서 마이크로플레이트 리더(Microplate reader; M2, Molecular Device, Canada)를 이용하여 흡광도를 측정하였다. 양성 대조군은 L-아스코르브산(L-ascorbic acid)을 이용하였으며, 다음의 식으로부터 DPPH 라디칼 소거활성을 계산하였다. A 4mM DPPH ethanol solution was prepared and used with the absorbance 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, reacted for 10 minutes, and the absorbance was measured using a microplate reader (M2, Molecular Device, Canada) at 517 nm. L-ascorbic acid was used as a positive control, and DPPH radical scavenging activity was calculated from the following equation.

DPPH radical scavenging activity(%) = [1-(A/B)]Х100 DPPH radical scavenging activity(%) = [1-(A/B)]Х100

(A: 시료 첨가구의 흡광도, B: 시료 무첨가구의 흡광도) (A: Absorbance of sample-added section, B: Absorbance of sample-free section)

DPPH 라디칼 소거능을 분석한 결과는 아래 표 3에 나타내었다. 폴리페놀 조성물에 따라 차이를 보였으며, 조성물들 중에서 T1 조성물이 소거능이 가장 높게 나타났으며, T3 조성물을 제외한 나머지 조성물에서도 라디칼 소거 효과가 나타났다. The results of analyzing the DPPH radical scavenging ability are shown in Table 3 below. There was a difference depending on the polyphenol composition, and among the compositions, the T1 composition showed the highest scavenging ability, and the remaining compositions except the T3 composition also showed a radical scavenging effect.

  (+)대조군(+)Control group (-)대조군(-)Control group T1T1 T2T2 T3T3 T4T4 T5T5 T6T6 DPPH(%) DPPH(% ) 81.07±0.59a 81.07± 0.59a 0.00±0.00e 0.00± 0.00e 36.73±2.95b 36.73± 2.95b 29.14±2.36c 29.14± 2.36c 0.60±1.04e 0.60± 1.04e 32.80±1.45bc 32.80±1.45 b.c. 29.05±2.73c 29.05± 2.73c 22.06±4.71d 22.06± 4.71d

* Duncan's multiple range test at p<0.05 * Duncan's multiple range test at p<0.05

가장 우수한 효과를 나타낸 T1 조성물에서 폴리페놀 성분들의 함량 비율을 달리하여 라디칼 소거효과의 변화를 확인한 결과, 3가지 폴리페놀의 조성비율을 유사하게 조절하였을 때 그 효과가 높아지는 경향을 보였다. 특히, 표 4의 결과에서와 같이, 클로로젠산과 카페인산의 함량을 유사한 비율로 혼합하였을때 소거효과가 높게 나타났다. As a result of checking the change in radical scavenging effect by varying the content ratio of polyphenol components in the T1 composition, which showed the best effect, the effect tended to increase when the composition ratio of the three polyphenols was adjusted similarly. In particular, as shown in the results in Table 4, the scavenging effect was high when chlorogenic acid and caffeic acid were mixed in similar ratios.

S1S1 S2S2 DPPH (%) DPPH (% ) 36.73±2.95a 36.73± 2.95a 23.93±0.66b 23.93± 0.66b

* Duncan's multiple range test at p<0.05 * Duncan's multiple range test at p<0.05

실험예 4: Rancimat 방법에 의한 산화 안정성 측정 Experimental Example 4: Measurement of oxidation stability by Rancimat method

유지의 산화안정성은 Rancimat(743 MetrohmCo., Herisau, Switzerland)방법을 이용해 분석하였다. 반응 용기에 폴리페놀 조성물 2%가 포함된 어유[fish oil, Sigma-Aldrich Co.(St. Louis. MO,USA)] 2.5g을 넣고 100℃로 조절된 알루미늄 히팅 블록상에서 20L/hr로 공기를 주입하면서 유지를 산화시켰다. 이때 발생하는 휘발성 산화 생성물을 60mL의 증류수가 들어 있는 흡수 용기(absorption vessel)에 이행시켜 전기 전도도의 변화에 따라 자동적으로 산출된 유도기간으로 항산화 정도를 측정하였으며, 항산화력의 비교는 폴리페놀 조성물을 첨가하지 않은 유지 시료를 대조군으로 하여 산출한 항산화지수(Antioxidative Index, AI)로써 아래의 식으로 계산하여 표시하였다. 또한, 양성 대조군으로 L-아스코르브산(L-ascorbic acid)를 사용하였다. The oxidation stability of oil was analyzed using the Rancimat (743 MetrohmCo., Herisau, Switzerland) method. 2.5 g of fish oil (Sigma-Aldrich Co. (St. Louis. MO, USA)) containing 2% of polyphenol composition was added to the reaction vessel, and air was blown at 20 L/hr on an aluminum heating block adjusted to 100°C. The oil was oxidized during injection. The volatile oxidation product generated at this time was transferred to an absorption vessel containing 60 mL of distilled water, and the degree of antioxidant was measured using an induction period automatically calculated according to the change in electrical conductivity. Comparison of antioxidant power was performed using the polyphenol composition. The antioxidant index (AI) calculated using the unadded oil sample as a control was calculated and expressed using the formula below. Additionally, L-ascorbic acid was used as a positive control.

항산화 지수(AI) = IG/IC ( IG : 대조군, IC : 처리군) Antioxidant index (AI) = IG/IC (IG: control group, IC: treatment group)

어유에 각 폴리페놀 조성물를 첨가한 후 산화안정성을 확인한 결과는 표 5에 나타냈다. 표 5에 나타난 바와 같이, 대부분의 조성물에서 대조군과 유사하거나 높은 산화안정성을 보였으며, 특히 T1 조성물이 산화안정성이 가장 높았다. 전반적인 경향은 항산화능을 측정한 DPPH 라디칼 소거능 결과와 유사한 패턴을 보였다.The results of confirming oxidation stability after adding each polyphenol composition to fish oil are shown in Table 5. As shown in Table 5, most compositions showed oxidation stability similar to or higher than that of the control group, and in particular, the T1 composition had the highest oxidation stability. The overall trend showed a similar pattern to the results of DPPH radical scavenging ability, which measured antioxidant ability.

(+)대조군(+)Control group (-)대조군(-)Control group T1T1 T2T2 T3T3 T4T4 T5T5 T6T6 IP (min)IP (min) 90.53±1.37c 90.53± 1.37c 74.26±1.05f 74.26±1.05 f 93.00±0.50b 93.00± 0.50b 88.33±0.90d 88.33± 0.90d 77.23±1.05e 77.23±1.05 e 88.10±0.75d 88.10± 0.75d 86.73±0.55d 86.73± 0.55d 77.13±0.73e 77.13± 0.73e AIA.I. 1.22±0.03c 1.22± 0.03c 1.00±0.00f 1.00± 0.00f 1.25±0.11b 1.25± 0.11b 1.19±0.01d 1.19± 0.01d 1.04±0.01e 1.04± 0.01e 1.18±0.01d 1.18± 0.01d 1.17±0.01d 1.17± 0.01d 1.04±0.01e 1.04± 0.01e

* Duncan's multiple range test at p<0.05 * Duncan's multiple range test at p<0.05

표 6에는 산화안정성이 가장 높게 나타난 T1 조성물에서 폴리페놀 성분의 함량을 다르게 하여 조성물을 제조하고, 이 조성물을 시료에 첨가하여 산화안정성을 측정한 결과를 나타냈다. 표 6의 결과에서와 같이, 클로로젠산과 카페인산의 함량을 유사한 비율로 혼합하였을 때 산화안정성이 우수하게 나타났다. Table 6 shows the results of measuring oxidation stability by preparing compositions with different contents of polyphenol components in the T1 composition, which showed the highest oxidation stability, and adding this composition to the sample. As shown in the results in Table 6, oxidation stability was excellent when the contents of chlorogenic acid and caffeic acid were mixed in similar ratios.

S1S1 S2S2 IP (min)IP (min) 93.00±0.50a 93.00± 0.50a 89.56±0.40b 89.56± 0.40b AIA.I. 1.21±0.15a 1.21± 0.15a 1.17±0.01b 1.17± 0.01b

* Duncan's multiple range test at p<0.05 * Duncan's multiple range test at p<0.05

실험예 5: 폴리페놀 옥시다아제 (Polyphenol oxidase, PPO) 저해 활성 측정 Experimental Example 5: Measurement of polyphenol oxidase (PPO) inhibitory activity

50mM 포스페이트 완충액(phosphate buffer; pH 6.5) 1.7㎖와 PPO(4,276 units/㎎) 0.2 ㎖를 혼합한 후, 각 폴리페놀 조성물을 0.1㎖를 첨가하여 25℃로 조절된 항온수조에서 15분간 방치하고, 기질로서 4mM 카테킨(catechin) 용액 1㎖를 각각 첨가하였다. 이어서, 마이크로플레이트 리더(Microplate reader, M2, Molecular Device, Canada)를 이용하여 420nm에서 5분간의 흡광도 변화를 측정하였다. 효소 저해활성은 다음식에 의해 흡광도 감소량%로 나타내었다. After mixing 1.7 ml of 50mM phosphate buffer (pH 6.5) and 0.2 ml of PPO (4,276 units/mg), 0.1 ml of each polyphenol composition was added and left in a constant temperature water bath adjusted to 25°C for 15 minutes. As a substrate, 1 ml of 4mM catechin solution was added to each. Next, the change in absorbance was measured at 420 nm for 5 minutes using a microplate reader (M2, Molecular Device, Canada). Enzyme inhibitory activity was expressed as percent reduction in absorbance using the following equation.

Inhibition of PPO activity(%)=[1-(A/B)]Х100 Inhibition of PPO activity(%)=[1-(A/B)]Х100

[A: 시료의 흡광도, B: 맹검액(blank solution)의 흡광도] [A: Absorbance of sample, B: Absorbance of blank solution]

표 7에는 각각의 폴리페놀 조성물에 따른 폴리페놀 옥시다아제 저해 활성을 측정한 결과를 나타내었다. 표 7에 나타난 결과에 따르면, T1 조성물이 폴리페놀 옥시다아제 저해 활성이 가장 우수하였다. Table 7 shows the results of measuring the polyphenol oxidase inhibitory activity of each polyphenol composition. According to the results shown in Table 7, the T1 composition had the best polyphenol oxidase inhibitory activity.

(+)대조군(+)Control group (-)대조군(-)Control group T1T1 T2T2 T3T3 T4T4 T5T5 T6T6 PPO(%)PPO(%) 22.86±0.70a 22.86± 0.70a 0.00±0.00g 0.00±0.00 g 22.40±0.88a 22.40± 0.88a 17.97±0.46d 17.97± 0.46d 19.47±0.75c 19.47± 0.75c 10.57±0.75e 10.57± 0.75e 8.16±0.24f 8.16± 0.24f 9.58±0.49e 9.58± 0.49e

* Duncan's multiple range test at p<0.05 * Duncan's multiple range test at p<0.05

표 8에는 폴리페놀 옥시다아제 저해활성이 가장 우수하게 나타난 T1 조성물에서 폴리페놀 성분의 함량을 달리한 조성물들의 폴리페놀 옥시다아제 저해활성을 측정한 결과를 나타냈다. 표 8의 결과에서와 같이, 클로로젠산과 카페인산의 함량을 유사한 비율로 혼합하였을 때 폴리페놀 옥시다아제 저해활성이 우수하게 나타났다. Table 8 shows the results of measuring the polyphenol oxidase inhibitory activity of compositions with different contents of polyphenol components in the T1 composition, which showed the best polyphenol oxidase inhibitory activity. As shown in the results in Table 8, the polyphenol oxidase inhibitory activity was excellent when the contents of chlorogenic acid and caffeic acid were mixed in similar ratios.

S1S1 S2S2 PPO(%)PPO(%) 22.86±0.70a 22.86± 0.70a 14.96±0.61b 14.96± 0.61b

* Duncan's multiple range test at p<0.05 * Duncan's multiple range test at p<0.05

상기에서는 본 출원의 대표적인 실시예를 예시적으로 설명하였으나, 본 출원의 범위는 상기와 같은 특정 실시예만 한정되지 아니하며, 해당 분야에서 통상의 지식을 가진 자라면 본 출원의 청구범위에 기재된 범주 내에서 적절하게 변경이 가능할 것이다. In the above, representative embodiments of the present application have been described by way of example, but the scope of the present application is not limited to the specific embodiments described above, and those skilled in the art will understand that the scope of the present application is within the scope stated in the claims of the present application. It will be possible to change it appropriately.

Claims (9)

클로로젠산, 카페산, 및 퀴닌산을 포함하는 제품의 보존용 조성물로서, 상기 제품의 보존용은 상기 제품의 산화방지용이고,
상기 퀴닌산 100 중량부에 대해 클로로젠산과 카페산의 함량의 합계가 190 - 210 중량부이고, 상기 클로로젠산 100 중량부에 대해 카페산의 함량이 90 - 110 중량부인 것인, 보존용 조성물.
A composition for preserving a product containing chlorogenic acid, caffeic acid, and quinic acid, wherein the purpose of preserving the product is to prevent oxidation of the product,
A composition for preservation, wherein the total content of chlorogenic acid and caffeic acid is 190 to 210 parts by weight based on 100 parts by weight of quinic acid, and the content of caffeic acid is 90 to 110 parts by weight based on 100 parts by weight of chlorogenic acid. .
클로로젠산, 카페산, 및 퀴닌산을 포함하는 제품의 보존용 조성물로서, 상기 제품의 보존용은 상기 제품의 갈변억제용이고,
상기 퀴닌산 100 중량부에 대해 클로로젠산과 카페산의 함량의 합계가 190 - 210 중량부이고, 상기 클로로젠산 100 중량부에 대해 카페산의 함량이 90 - 110 중량부이고, 상기 조성물은 페놀성 화합물이 폴리페놀 옥시다아제에 의해 산화되는 것에 의해 발생되는 갈변을 억제하는 것인, 보존용 조성물.
A composition for preserving a product containing chlorogenic acid, caffeic acid, and quinic acid, wherein the purpose of preserving the product is to inhibit browning of the product,
The total content of chlorogenic acid and caffeic acid is 190 to 210 parts by weight based on 100 parts by weight of quinic acid, the content of caffeic acid is 90 to 110 parts by weight based on 100 parts by weight of chlorogenic acid, and the composition contains phenol A composition for preservation, which suppresses browning caused by oxidation of a chemical compound by polyphenol oxidase.
청구항 1 또는 청구항 2에 있어서, 상기 제품은 식품, 사료, 생활용품 또는 공업용품인 것인, 보존용 조성물. The composition for preservation according to claim 1 or 2, wherein the product is food, feed, household goods, or industrial products. 삭제delete 삭제delete 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물을 제품에 첨가하는 단계를 포함하는, 제품의 산화를 방지하는 방법으로서,
상기 조성물에서
상기 퀴닌산 100 중량부에 대해 클로로젠산과 카페산의 함량의 합계가 190 - 210 중량부이고, 상기 클로로젠산 100 중량부에 대해 카페산의 함량이 90 - 110 중량부인 것인, 제품의 산화를 방지하는 방법.
A method of preventing oxidation of a product comprising adding to the product a composition comprising chlorogenic acid, caffeic acid, and quinic acid, comprising:
In the composition
Oxidation of the product, wherein the total content of chlorogenic acid and caffeic acid is 190 to 210 parts by weight based on 100 parts by weight of quinic acid, and the content of caffeic acid is 90 to 110 parts by weight based on 100 parts by weight of chlorogenic acid. How to prevent it.
청구항 6에 있어서, 상기 제품은 식품, 사료, 생활용품 또는 공업용품인 것인, 제품의 산화를 방지하는 방법. The method of claim 6, wherein the product is food, feed, household goods, or industrial products. 클로로젠산, 카페산, 및 퀴닌산을 포함하는 조성물을 제품에 첨가하는 단계를 포함하는, 제품의 갈변을 억제하는 방법으로서,
상기 조성물에서
상기 퀴닌산 100 중량부에 대해 클로로젠산과 카페산의 함량의 합계가 190 - 210 중량부이고, 상기 클로로젠산 100 중량부에 대해 카페산의 함량이 90 - 110 중량부이고,
상기 갈변의 억제는 페놀성 화합물이 폴리페놀 옥시다아제에 의해 산화되는 것에 의해 발생되는 갈변의 억제인 것인, 제품의 갈변을 억제하는 방법.
A method of inhibiting browning of a product comprising adding a composition comprising chlorogenic acid, caffeic acid, and quinic acid to the product, comprising:
In the composition
The total content of chlorogenic acid and caffeic acid is 190 to 210 parts by weight based on 100 parts by weight of quinic acid, and the content of caffeic acid is 90 to 110 parts by weight based on 100 parts by weight of chlorogenic acid,
A method for inhibiting browning of a product, wherein the inhibition of browning is inhibition of browning caused by oxidation of a phenolic compound by polyphenol oxidase.
청구항 8에 있어서, 상기 제품은 식품, 사료, 생활용품 또는 공업용품인 것인, 제품의 갈변을 억제하는 방법. The method of claim 8, wherein the product is food, feed, household goods, or industrial products.
KR1020200123837A 2019-11-08 2020-09-24 Composition Comprising Polyphenol KR102635424B1 (en)

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JP2022526253A JP7400098B2 (en) 2019-11-08 2020-11-06 Compositions containing polyphenols
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CA3160517A CA3160517A1 (en) 2019-11-08 2020-11-06 A composition for use in reducing an off-taste or off-flavor comprising chlorogenic acid, caffeic acid, and quinic acid
PCT/KR2020/015546 WO2021091322A1 (en) 2019-11-08 2020-11-06 Composition containing polyphenol
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JP2005179373A (en) 1993-12-06 2005-07-07 Nikka Whisky Distilling Co Ltd Polyphenol derived from apple fruit and use thereof
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AU2016317931B2 (en) * 2015-09-04 2021-01-28 Coffee Fruit Holdings Pty. Ltd. Preparation of coffee fruit extracts and powders

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JP2005179373A (en) 1993-12-06 2005-07-07 Nikka Whisky Distilling Co Ltd Polyphenol derived from apple fruit and use thereof
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