KR102273578B1 - Antioxidant composition comprising epigallocatechin gallate as effective gradient and method for preparing the same - Google Patents
Antioxidant composition comprising epigallocatechin gallate as effective gradient and method for preparing the same Download PDFInfo
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- KR102273578B1 KR102273578B1 KR1020190154479A KR20190154479A KR102273578B1 KR 102273578 B1 KR102273578 B1 KR 102273578B1 KR 1020190154479 A KR1020190154479 A KR 1020190154479A KR 20190154479 A KR20190154479 A KR 20190154479A KR 102273578 B1 KR102273578 B1 KR 102273578B1
- Authority
- KR
- South Korea
- Prior art keywords
- emulsifier
- antioxidant
- browning
- epigallocatechin gallate
- composition
- Prior art date
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Abstract
본 발명은 유층 유화제, 수층 유화제 및 항갈변제를 포함하고, 에멀젼화된 에피갈로카테킨갈레이트를 포함하고, 수층 유화제는 사이클로덱스트린, 펙틴, 말토덱트트린, 알지네이트 및 스테비오사이드 중에서 선택된 1종 이상이고, 항갈변제는 비타민 C 및 갈산 중에서 선택된 1종 이상인, 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물에 관한 것이다. 이에 의하여, 에피갈로카테킨갈레이트(EGCG)의 음용소재로 적용시 단점인 불용성, 갈변, 항산화 효능 저화와 같은 문제를 해결하도록 유층 유화제, 수층 유화제 및 항갈변제의 적절한 처리함으로써 갈변현상이 억제되며, 항산화 기능이 향상되며 유지될 수 있고, 이와 같은 조성물은 식품, 음료, 약품 등에 적용될 수 있다.The present invention includes an oil layer emulsifier, a water layer emulsifier and an anti-browning agent, and an emulsified epigallocatechin gallate, and the water layer emulsifier is at least one selected from cyclodextrin, pectin, maltodectrin, alginate and stevioside. And, the anti-browning agent relates to an antioxidant composition comprising at least one selected from vitamin C and gallic acid, epigallocatechin gallate as an active ingredient. Accordingly, the browning phenomenon is suppressed by appropriate treatment of the oil layer emulsifier, the water layer emulsifier and the anti-browning agent to solve problems such as insolubility, browning, and lowering of antioxidant efficacy, which are disadvantages when applying epigallocatechin gallate (EGCG) as a drinking material. and the antioxidant function can be improved and maintained, and such a composition can be applied to food, beverage, medicine, and the like.
Description
본 발명은 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물 및 이의 제조방법에 관한 것으로, 더욱 상세하게는 유층 수화제, 수층 수화제 및 항갈변제 처리한 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물 및 이의 제조방법에 관한 것이다.The present invention relates to an antioxidant composition comprising epigallocatechin gallate as an active ingredient and a method for preparing the same, and more particularly, to epigallocatechin gallate treated with an oily wetting agent, an aqueous wetting agent, and an anti-browning agent as an active ingredient. It relates to an antioxidant composition comprising and a method for preparing the same.
최근, 화장품, 식품, 의약품, 생활용품 등의 산업에서는 생리활성소재의 발굴을 위하여 인체에 대한 생리활성이 뛰어날 뿐만 아니라, 생체적합성 및 생체안전성이 우수한 천연성분의 개발이 더욱 큰 중요성을 갖게 되었다. 녹차의 떫은맛을 내는 카테킨은 타닌 또는 폴리페놀이라고 불리는 것의 구성요소로, 산화되어 홍갈색을 낸다. 카테킨은 차의 성분 중 가장 많은 부분을 차지하며, 화학 구조상 수산기 -OH를 많이 가지고 있어 여러 가지 물질과 쉽게 결합할 수 있다. 이러한 성질이 체내 중금속 제거나 활성산소를 제거하는 항산화 작용을 한다. 적정량의 활성산소는 생체 내 면역기능에 관계된 식세포 등의 살균작용 등에서 긍정적인 효과를 나타내는 것으로 알려져 있지만, 과다한 양의 활성산소는 산화-항산화의 균형을 깨트려 단백질의 변성이나 생체 내의 지질산화, DNA의 파괴 등을 일으켜 산화적 스트레스를 일으키는 원인이 되는데, 녹차 카테킨은 이러한 활성산소를 제거하는 능력이 탁월한 것으로 알려져 있다. Recently, in industries such as cosmetics, food, pharmaceuticals, and household goods, the development of natural ingredients with excellent biocompatibility and biosafety as well as excellent bioactivity for the human body for the discovery of bioactive materials has become more important. Catechins, which give green tea astringent taste, are components of what are called tannins or polyphenols, which are oxidized to give them a reddish-brown color. Catechin accounts for the largest portion of tea, and has many hydroxyl groups -OH in its chemical structure, so it can be easily combined with various substances. These properties act as antioxidants to remove heavy metals or free radicals from the body. It is known that an appropriate amount of active oxygen has a positive effect on the sterilization of phagocytes related to the immune function in vivo, but an excessive amount of active oxygen disrupts the balance between oxidation and antioxidant, resulting in protein denaturation, in vivo lipid oxidation, DNA Green tea catechins are known to have excellent ability to remove these free radicals.
특히 녹차에 존재하는 카테킨류는 EC(Epicatechin), EGC(Epigallocatechin), ECG(Epicatechin gallate), EGCG(Epigallocatechin gallate)와 이들의 광학 이성질체 등이다. 일반적으로 이 네 가지가 녹차 카테킨으로 불리워지며, 이 중에서도 EGCG가 가장 많은 양을 차지하고, 가장 강력한 항산화 능력을 나타내는 등 생리활성이 가장 높은 것으로 알려져 있으며, EGCG는 지방세포에서 렙틴(leptin), HSL, Resistin mRNA 발현에 영향을 끼쳐 지방 대사를 조절하는데 즉, 중성지방 분해 및 지방산화를 촉진하여 체지방을 증가시킴으로써 지방이 감소되는 것으로 3T3-L1 지방 세포주에서 고농도의 EGCG가 지방 분해에 있다는 보고는 널리 알려진 결과이다. (Lin et al. , 2005; Wu et al. , 2005) 피부에 적용할 경우, 콜라겐(collagen)의 생성을 촉진하고 자외선에 의한 피부자극 및 피부손상을 막아주는 역할을 할 뿐만 아니라, 피부의 미백 및 주름 등에 우수한 효과가 있다는 연구결과들이 발표되고 있어, 화장품뿐만 아니라, 의약품 및 생활용품 등에 적용할 경우 우수한 기능을 발현할 수 있을 것으로 기대된다. In particular, catechins present in green tea include EC (Epicatechin), EGC (Epigallocatechin), ECG (Epicatechin gallate), EGCG (Epigallocatechin gallate), and optical isomers thereof. In general, these four are called green tea catechins, and among them, EGCG accounts for the largest amount and is known to have the highest physiological activity such as showing the strongest antioxidant ability. It is widely known that high concentration of EGCG in 3T3-L1 adipocyte line is in lipolysis, which affects the expression of Resistin mRNA and regulates fat metabolism, that is, increases body fat by promoting triglyceride decomposition and fatty acidization. It is the result. (Lin et al., 2005; Wu et al., 2005) When applied to the skin, it promotes the production of collagen and prevents skin irritation and skin damage caused by UV rays, as well as whitening the skin. And research results have been published that it has an excellent effect on wrinkles, etc., so it is expected that excellent functions can be expressed when applied not only to cosmetics, but also to pharmaceuticals and household products.
그러나, 녹차 EGCG는 그 자체가 강력한 항산화제로서의 기능을 가지기 때문에, 광, 활성산소, 열 등과 같은 외부의 산화적 스트레스에 의해 쉽게 산화되어 파괴되고 변색되는 등의 특성을 가지고 있다. EGCG는 물에 극히 소량만이 용해되는 난용성의 특성을 가지고 있으며, 수계에 존재하는 산화적 스트레스에 의해 빠르게 산화되어 심한 변색을 유발하며 의약품, 식품, 화장품, 생활용품 등에서 유효성분로서의 활용에 많은 제약을 가지고 있는 것으로 알려져 왔다.However, since green tea EGCG itself has a function as a strong antioxidant, it is easily oxidized and destroyed by external oxidative stress such as light, free radicals, heat, etc., and has characteristics such as discoloration. EGCG has the property of being poorly soluble in that only a very small amount is dissolved in water, and it is rapidly oxidized by oxidative stress in the water system, causing severe discoloration, and is widely used as an active ingredient in medicines, foods, cosmetics, and household products. known to have limitations.
녹차유래 EGCG의 안정성을 증가시키기 위한 여러 방법들이 고안되고 있다. 예를 들면 EGCG의 유도체를 사용하는 방안이나, 친유성 마이크로캡슐을 이용하는 방법이 제안되어 있지만, 이러한 방안들은 매우 한정적인 경우에만 그 안정성을 보장할 수 있는 한계점을 가지고 있다. 또한, EGCG를 양이온성 고분자 또는 음이온성 고분자, 산화안정화제 등을 이용하여 수상에서도 안정화하는 방법을 제안하였지만, 안정화 제형에 다른 극성물질이 첨가될 경우 양이온성 고분자 또는 음이온성 고분자, 항산화제 등과 매우 강하게 상호작용을 하게 되면, 안정화의 정도가 감소되는 단점이 있다. 또한, EGCG를 양극성 또는 음극성 고분자, 산화안정화제, 수불용성고분자 등을 이용한 수불용성 캡슐에 가두어 수상에서 안정화하는 방안도 제안된 바 있으나, 이는 수불용성인 특성을 갖는 캡슐이기 때문에, 수상에서 침전이 발생하거나, 현탁한 성상을 갖는 등 화장품, 의약품, 식품 및 생활용품 등의 분야에서 투명하게 용해되는 조건을 요구하는 용도 즉, 투명스킨, 투명세럼, 투명음료 등으로의 활용에는 커다란 제약을 갖는 문제점이 있다.Several methods have been devised to increase the stability of green tea-derived EGCG. For example, a method using a derivative of EGCG or a method using a lipophilic microcapsule has been proposed, but these methods have a limitation in that they can ensure the stability only in very limited cases. In addition, a method for stabilizing EGCG in aqueous phase using a cationic or anionic polymer, an oxidation stabilizer, etc. has been proposed. However, when other polar substances are added to the stabilization formulation, it is highly effective with cationic or anionic polymers, antioxidants, etc. If there is a strong interaction, there is a disadvantage in that the degree of stabilization is reduced. In addition, a method for stabilizing EGCG in an aqueous phase by confining it in a water-insoluble capsule using an anode or cathodic polymer, an oxidation stabilizer, a water-insoluble polymer, etc. has been proposed, but since this is a capsule having a water-insoluble property, it precipitates in the aqueous phase There are great restrictions on applications that require transparent dissolution conditions in the fields of cosmetics, pharmaceuticals, food and household products, such as transparent skin, transparent serum, transparent beverage, etc. There is a problem.
본 발명의 목적은 에피갈로카테킨갈레이트(EGCG)의 음용소재로 적용시 단점인 불용성, 갈변, 항산화 효능 저화와 같은 문제점을 해결하기 위한 것으로 유층 유화제, 수층 유화제 및 항갈변제의 적절한 처리에 의해 에멀젼화함으로써 EGCG의 갈변 현상을 억제하며, 항산화 활성을 향상하고 이를 유지할 수 있는 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물을 제공하는 데 있다.An object of the present invention is to solve problems such as insolubility, browning, and lowering of antioxidant efficacy, which are disadvantages when applying epigallocatechin gallate (EGCG) as a drinking material. An object of the present invention is to provide an antioxidant composition comprising epigallocatechin gallate as an active ingredient, which can suppress the browning phenomenon of EGCG by emulsifying it by EGCG, and improve antioxidant activity and maintain it.
본 발명의 일 측면에 따르면,According to one aspect of the present invention,
유층 유화제, 수층 유화제 및 항갈변제를 포함하고, 에멀젼화된 에피갈로카테킨갈레이트를 포함하고,oil-layer emulsifier, water-layer emulsifier and anti-browning agent, and emulsified epigallocatechin gallate;
상기 수층 유화제는 사이클로덱스트린, 펙틴, 말토덱트트린, 알지네이트 및 스테비오사이드 중에서 선택된 1종 이상이고,The aqueous emulsifier is at least one selected from cyclodextrin, pectin, maltodextrin, alginate and stevioside,
상기 항갈변제는 비타민 C 및 갈산 중에서 선택된 1종 이상인, 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물이 제공된다.The anti-browning agent is provided with an antioxidant composition comprising at least one selected from vitamin C and gallic acid, epigallocatechin gallate as an active ingredient.
바람직하게는, 상기 유층 유화제는 레시틴, 토코페롤, 및 올레산 중에서 선택된 어느 하나일 수 있다.Preferably, the oil layer emulsifier may be any one selected from lecithin, tocopherol, and oleic acid.
더욱 바람직하게는, 상기 유층 유화제는 레시틴일 수 있다.More preferably, the oil layer emulsifier may be lecithin.
바람직하게는, 상기 수층 유화제는 펙틴, 사이클로덱스트린, 및 말토덱스트린 중에서 선택된 어느 하나일 수 있다.Preferably, the aqueous emulsifier may be any one selected from pectin, cyclodextrin, and maltodextrin.
더욱 바람직하게는, 상기 수층 유화제는 펙틴일 수 있다.More preferably, the aqueous layer emulsifier may be pectin.
바람직하게는, 상기 수층 유화제로 펙틴, 항갈변제로 갈산을 동시에 사용할 수 있다.Preferably, pectin as the aqueous emulsifier and gallic acid as the anti-browning agent may be used simultaneously.
상기 항산화 조성물은 에피갈로카테킨갈레이트 100중량부에 대하여 유층 유화제 5 내지 20중량부, 수층 유화제 0.05 내지 2중량부, 및 항갈변제 0.05 내지 2중량부를 포함할 수 있다.The antioxidant composition may include 5 to 20 parts by weight of an oil emulsifier, 0.05 to 2 parts by weight of an aqueous emulsifier, and 0.05 to 2 parts by weight of an anti-browning agent based on 100 parts by weight of epigallocatechin gallate.
본 발명의 다른 측면에 따르면,According to another aspect of the present invention,
상기 항산화 조성물을 포함하는, 항산화 활성을 갖는 식품 또는 음료 조성물이 제공된다.A food or beverage composition having antioxidant activity, comprising the antioxidant composition, is provided.
본 발명의 다른 또 하나의 측면에 따르면,According to another aspect of the present invention,
상기 항산화 조성물을 포함하는, 항산화 활성을 갖는 약학 조성물이 제공된다.A pharmaceutical composition having antioxidant activity, comprising the antioxidant composition, is provided.
본 발명의 다른 또 하나의 측면에 따르면,According to another aspect of the present invention,
상기 항산화 조성물을 포함하는, 항산화 활성을 갖는 화장료 조성물이 제공된다.A cosmetic composition having antioxidant activity, comprising the antioxidant composition, is provided.
본 발명의 다른 또 하나의 측면에 따르면,According to another aspect of the present invention,
(a) 에피갈로카테킨갈레이트와 유층 유화제를 첨가한 물을 혼합함으로써 1차 에멀젼을 제조하는 단계;(a) preparing a primary emulsion by mixing epigallocatechin gallate and water to which an oil emulsifier is added;
(b) 상기 1차 에멀젼에 수층 유화제를 첨가하여 혼합함으로써 2차 에멀젼을 제조하는 단계; 및(b) preparing a secondary emulsion by adding and mixing a water-layer emulsifier to the primary emulsion; and
(c) 상기 2차 에멀젼에 항갈변제를 첨가하여 혼합함으로써 3차 에멀젼을 제조하는 단계;를 포함하고,(c) preparing a tertiary emulsion by adding and mixing an anti-browning agent to the secondary emulsion;
상기 수층 유화제는 사이클로덱스트린(b-cyclodextrin), 알지네이트(alginate), 펙틴(pectin) 및 스테비오사이드(stevioside) 중에서 선택된 1종 이상이고,The aqueous emulsifier is at least one selected from cyclodextrin (b-cyclodextrin), alginate, pectin and stevioside,
상기 항갈변제는 비타민 C 및 갈산(gallic acid) 중에서 선택된 1종 이상인, 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물의 제조방법이 제공된다.The anti-browning agent provides a method for preparing an antioxidant composition comprising at least one selected from vitamin C and gallic acid, epigallocatechin gallate as an active ingredient.
바람직하게는, 상기 유층 유화제는 레시틴, 토코페롤, 및 올레산 중에서 선택된 어느 하나일 수 있다.Preferably, the oil layer emulsifier may be any one selected from lecithin, tocopherol, and oleic acid.
더욱 바람직하게는, 상기 유층 유화제는 레시틴일 수 있다.More preferably, the oil layer emulsifier may be lecithin.
바람직하게는, 상기 수층 유화제는 펙틴, 사이클로덱스트린, 및 말토덱스트린 중에서 선택된 어느 하나의 수층 유화제를 포함할 수 있다.Preferably, the aqueous layer emulsifier may include any one aqueous layer emulsifier selected from pectin, cyclodextrin, and maltodextrin.
바람직하게는, 상기 수층 유화제로 펙틴, 항갈변제로 갈산을 동시에 사용할 수 있다.Preferably, pectin as the aqueous emulsifier and gallic acid as the anti-browning agent may be used simultaneously.
상기 항산화 조성물은 에피갈로카테킨갈레이트 100중량부에 대하여 유층 유화제 5 내지 20중량부, 수층 유화제 0.05 내지 2중량부, 및 항갈변제 0.05 내지 2중량부를 포함될 수 있다.The antioxidant composition may include 5 to 20 parts by weight of an oil emulsifier, 0.05 to 2 parts by weight of an aqueous emulsifier, and 0.05 to 2 parts by weight of an anti-browning agent based on 100 parts by weight of epigallocatechin gallate.
본 발명의 다른 또 하나의 측면에 따르면,According to another aspect of the present invention,
상기 항산화 조성물의 제조방법을 포함하는 항산화 활성을 갖는 식품 또는 음료 조성물의 제조방법이 제공된다.There is provided a method for preparing a food or beverage composition having antioxidant activity, including the method for preparing the antioxidant composition.
본 발명의 다른 또 하나의 측면에 따르면,According to another aspect of the present invention,
상기 항산화 조성물의 제조방법을 포함하는 항산화 활성을 갖는 약학 조성물의 제조방법이 제공된다.There is provided a method for preparing a pharmaceutical composition having antioxidant activity, including the method for preparing the antioxidant composition.
본 발명의 다른 또 하나의 측면에 따르면,According to another aspect of the present invention,
상기 항산화 조성물의 제조방법을 포함하는 항산화 활성을 갖는 화장료 조성물의 제조방법이 제공된다.There is provided a method for preparing a cosmetic composition having antioxidant activity, including the method for preparing the antioxidant composition.
본 발명의 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물은 에피갈로카테킨갈레이트(EGCG)의 음용소재로 적용시 단점인 불용성, 갈변, 항산화 효능 저화와 같은 문제를 해결하도록 유층 유화제, 수층 유화제 및 항갈변제를 첨가하여 에멀젼화함으로써 EGCG의 갈변현상이 억제되며, 항산화 기능이 향상 및 유지될 수 있고, 이와 같은 조성물은 항산화 활정을 갖는 건강식품, 음료, 약품 등에 적용될 수 있다.The antioxidant composition comprising epigallocatechin gallate as an active ingredient of the present invention is an oil layer emulsifier to solve problems such as insolubility, browning, and reduced antioxidant efficacy, which are disadvantages when applied as a drinking material of epigallocatechin gallate (EGCG). , a water layer emulsifier and an anti-browning agent are added to emulsify, thereby inhibiting the browning of EGCG, improving and maintaining the antioxidant function, and such a composition can be applied to health foods, beverages, pharmaceuticals, etc. having antioxidant activity.
도 1은 실험예 1의 갈변 방지제에 따른 항갈변 효과 분석 결과이다.
도 2는 실험예 2의 유화제에 따른 항갈변 효과 분석 결과이다.
도 3은 실험예 3의 유화제와 항갈변제 동시 첨가시 항갈변 효과 분석 사진이다.
도 4 및 도 5는 실험예 3의 유화제와 항갈변제 동시 첨가시 항갈변 효과 분석 결과이다.
도 6은 실험예 4의 총페놀 함유량 측정 결과이다.
도 7은 실험예 4의 총 플라보노이드 함유량 측정 결과이다.
도 8은 실험예 4의 DPPH 라디칼 소거능 측정 결과이다.
도 9는 실험예 4의 ABTS 라디칼 소거능 측정 결과이다.1 is an analysis result of the anti-browning effect of the anti-browning agent of Experimental Example 1. FIG.
2 is an analysis result of the anti-browning effect according to the emulsifier of Experimental Example 2.
3 is a photograph of the analysis of the anti-browning effect when the emulsifier and the anti-browning agent of Experimental Example 3 are simultaneously added.
4 and 5 are analysis results of the anti-browning effect when the emulsifier and the anti-browning agent of Experimental Example 3 are simultaneously added.
6 is a measurement result of the total phenol content of Experimental Example 4.
7 is a measurement result of the total flavonoid content of Experimental Example 4.
8 is a measurement result of the DPPH radical scavenging ability of Experimental Example 4.
9 is a measurement result of ABTS radical scavenging ability of Experimental Example 4.
본 발명은 다양한 변환을 가할 수 있고 여러 가지 실시예를 가질 수 있는 바, 특정 실시예들을 도면에 예시하고 상세한 설명에 상세하게 설명하고자 한다. 그러나, 이는 본 발명을 특정한 실시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술 범위에 포함되는 모든 변환, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다. 본 발명을 설명함에 있어서 관련된 공지 기술에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우 그 상세한 설명을 생략한다.Since the present invention can apply various transformations and can have various embodiments, specific embodiments are illustrated in the drawings and described in detail in the detailed description. However, this is not intended to limit the present invention to specific embodiments, and it should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention. In describing the present invention, if it is determined that a detailed description of a related known technology may obscure the gist of the present invention, the detailed description thereof will be omitted.
본 출원에서 사용한 용어는 단지 특정한 실시예를 설명하기 위해 사용된 것으로, 본 발명을 한정하려는 의도가 아니다. 단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 출원에서, "포함하다" 또는 "가지다" 등의 용어는 명세서상에 기재된 특징, 숫자, 단계, 구성요소, 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 구성요소, 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.
The terms used in the present application are only used to describe specific embodiments, and are not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly dictates otherwise. In the present application, terms such as “comprise” or “have” are intended to designate that a feature, number, step, element, or combination thereof described in the specification is present, and includes one or more other features or numbers, It should be understood that it does not preclude the possibility of the presence or addition of steps, components, or combinations thereof.
이하, 본 발명의 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물에 대해 설명하도록 한다.Hereinafter, an antioxidant composition comprising epigallocatechin gallate of the present invention as an active ingredient will be described.
본 발명의 재료로 사용된 에피갈로카테킨갈레이트는 녹차로부터 추출된 카테킨이며, 정제수, 글리세린, 부틸렌글라이콜, 헥산디올, 메칠프로판디올, 프로판디올, 프로필렌글라이콜, 에탄올, 메탄올, 에틸아세테이트, 디클로로메탄, 에틸에테르, 헥산 등의 추출용매에 의해 추출될 수 있고, 더욱 바람직하게는 정제수, 메칠프로판디올, 헥산디올에 이해 추출된 것일 수 있으나, 본 발명의 범위가 여기에 한정되지 않으며, 식물 재료의 추출에 사용될 수 있는 다양한 추출용매를 사용할 수 있다.Epigallocatechin gallate used as the material of the present invention is catechin extracted from green tea, purified water, glycerin, butylene glycol, hexanediol, methylpropanediol, propanediol, propylene glycol, ethanol, methanol, ethyl It may be extracted with an extraction solvent such as acetate, dichloromethane, ethyl ether, hexane, and more preferably, it may be extracted with purified water, methylpropanediol, or hexanediol, but the scope of the present invention is not limited thereto. , various extraction solvents that can be used for extraction of plant material can be used.
본 발명의 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물은 유층 유화제, 수층 유화제 및 항갈변제를 포함하고, 에멀젼화된 에피갈로카테킨갈레이트를 포함하는 것을 특징으로 한다.The antioxidant composition comprising epigallocatechin gallate as an active ingredient of the present invention comprises an oil layer emulsifier, a water layer emulsifier and an anti-browning agent, and is characterized in that it comprises an emulsified epigallocatechin gallate.
유화제(emulsifying agent)는 서로 혼합하지 않는 두 종의 액체를 안정한 에멀션(유탁액)으로 만드는 제3의 물질을 의미한다. 본 발명에서 유층 유화제는 HLB(Hydrophile Lipophile Balance) 값이 3 내지 7 범위에 있는 유화제로 정의한다. 또한, 수층 유화제는 HLB 값이 8 내지 18 범위에 있는 유화제로 정의한다.An emulsifying agent refers to a third substance that converts two immiscible liquids into a stable emulsion (emulsion). In the present invention, the oil layer emulsifier is defined as an emulsifier having a Hydrophile Lipophile Balance (HLB) value in the range of 3 to 7. A water layer emulsifier is also defined as an emulsifier having an HLB value in the range of 8 to 18.
상기 수층 유화제는 사이클로덱스트린, 펙틴, 말토덱트트린, 알지네이트 및 스테비오사이드 중에서 선택된 1종 이상이고, 상기 항갈변제는 갈변을 방지하는 성분으로 비타민 C 및 갈산(gallic acid) 중에서 선택된 1종 이상인 것을 특징으로 한다.The aqueous layer emulsifier is at least one selected from cyclodextrin, pectin, maltodextrin, alginate and stevioside, and the anti-browning agent is a component that prevents browning and is at least one selected from vitamin C and gallic acid. do it with
바람직하게는, 상기 유층 유화제는 레시틴, 토코페롤, 올레산 등일 수 있으며, 더욱 바람직하게는 레시틴 일 수 있다.Preferably, the oil layer emulsifier may be lecithin, tocopherol, oleic acid, etc., and more preferably lecithin.
바람직하게는 상기 수층 유화제는 펙틴, 사이클로덱스트린, 및 말토덱스트린 중에서 선택된 어느 하나일 수 있고, 더욱 바람직하게는 펙틴 일 수 있다.Preferably, the aqueous layer emulsifier may be any one selected from pectin, cyclodextrin, and maltodextrin, and more preferably pectin.
한편, 상기 수층 유화제로 펙틴, 항갈변제로 갈산을 동시에 사용하는 것이 항갈변 효능을 향상시키기 위해 바람직하다.On the other hand, it is preferable to simultaneously use pectin as the aqueous emulsifier and gallic acid as the anti-browning agent to improve the anti-browning effect.
바람직하게는, 에피갈로카테킨갈레이트 100중량부에 대하여 유층 유화제 5 내지 20중량부, 수층 유화제 0.05 내지 2중량부, 항갈변제 0.05 내지 2중량부로 사용될 수 있고, 더욱 바람직하게는 유층 유화제 7 내지 15중량부, 수층 유화제 0.1 내지 1.5중량부, 항갈변제 0.1 내지 1.5중량부를 사용할 수 있고, 더욱 더 바람직하게는 유층 유화제 8 내지 12중량부, 수층 유화제 0.2 내지 1.2중량부, 항갈변제 0.2 내지 1.2중량부를 사용할 수 있다. 가장 바람직하게는 에피갈로카테킨갈레이트 100중량부에 대하여 유층 유화제인 레시틴 9 내지 11중량부, 수층 유화제인 펙틴 0.3 내지 1중량부, 항갈변제인 갈산 0.3 내지 1중량부를 사용할 수 있다. 이와 같은 함량비일 때 항산화 기능 및 항갈변 특성이 향상되고 에피갈로카테킨갈레이트의 가용화가 최적화되어 조성물의 상태가 안정적일 수 있다.
Preferably, 5 to 20 parts by weight of an oil layer emulsifier, 0.05 to 2 parts by weight of an aqueous layer emulsifier, and 0.05 to 2 parts by weight of an anti-browning agent may be used based on 100 parts by weight of epigallocatechin gallate, and more preferably, an
이하 본 발명의 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물의 제조방법에 대해 설명하도록 한다.Hereinafter, a method for preparing an antioxidant composition comprising epigallocatechin gallate of the present invention as an active ingredient will be described.
먼저, first, 에피갈로카테킨갈레이트와Epigallocatechin gallate and 유층oil layer 유화제를 첨가한 물을 혼합함으로써 1차 First by mixing water with emulsifier added 에멀젼을emulsion 제조한다(단계 a). prepared (step a).
상기 유층 유화제는 레시틴, 토코페롤, 및 올레산 중에서 선택된 어느 하나인 것이 바람직하고, 더욱 바람직하게는 레시틴을 사용할 수 있다.The oil layer emulsifier is preferably any one selected from lecithin, tocopherol, and oleic acid, and more preferably lecithin.
다음으로 상기 1차 Next, the first 에멀젼에in emulsion 수층water layer 유화제를 첨가하여 혼합함으로써 2차 Secondary by adding and mixing an emulsifier 에멀젼을emulsion 제조한다(단계 b). prepared (step b).
상기 수층 유화제는 상기 수층 유화제는 사이클로덱스트린(b-cyclodextrin), 알지네이트(alginate), 펙틴(pectin) 및 스테비오사이드(stevioside) 중에서 선택된 1종 이상일 수 있고, 바람직하게는 펙틴, 사이클로덱스트린, 및 말토덱스트린 중에서 선택된 어느 하나일 수 있고, 더욱 바람직하게는 펙틴을 사용할 수 있다.The aqueous emulsifier may be at least one selected from cyclodextrin (b-cyclodextrin), alginate, pectin and stevioside, preferably pectin, cyclodextrin, and maltodextrin. It may be any one selected from among, more preferably pectin may be used.
가장 바람직하게는, 상기 수층 유화제로 펙틴, 항갈변제로 갈산을 동시에 사용할 수 있다.Most preferably, pectin as the aqueous emulsifier and gallic acid as the anti-browning agent may be used at the same time.
이후, 상기 2차 After that, the second 에멀젼에in emulsion 항갈변제를anti-browning drug 첨가하여 혼합함으로써 3차 3rd by adding and mixing 에멀젼을emulsion 제조한다(단계 c). prepared (step c).
상기 항갈변제는 비타민 C 및 갈산(gallic acid) 중에서 선택된 1종 이상일 수 있다.The anti-browning agent may be at least one selected from vitamin C and gallic acid.
상기 혼합에 의한 에멀젼화는 초음파 처리에 의할 수 있다.
The emulsification by the mixing may be performed by ultrasonication.
본 발명은 상기 항산화 조성물을 포함하는 항산화 활성을 갖는 식품 또는 음료 조성물을 제공한다.The present invention provides a food or beverage composition having antioxidant activity comprising the antioxidant composition.
본 발명에 따른 식품 또는 음료 조성물은 기능성 식품 또는 음료로 이용하거나, 각종 식품 또는 음료에 첨가할 수 있다. 본 발명의 조성물을 첨가할 수 있는 식품 또는 음료로는 예를 들어, 음료류, 알코올 음료류, 과자류, 다이어트바, 유제품, 육류, 초코렛, 피자, 빵류 라면, 기타 면류, 껌류, 아이스크림류, 비타민 복합제, 건강보조식품류 등이 있다.The food or beverage composition according to the present invention may be used as a functional food or beverage, or may be added to various foods or beverages. Foods or beverages to which the composition of the present invention can be added include, for example, beverages, alcoholic beverages, confectionery, diet bars, dairy products, meat, chocolate, pizza, bread noodles, other noodles, gums, ice creams, vitamin complexes, There are health supplements, etc.
본 발명의 식품 조성물은 유효성분으로서 유화제 및 항갈변제 처리된 에피갈로카테킨갈레이트뿐만 아니라, 식품 제조 시에 통상적으로 첨가되는 성분을 포함할 수 있으며, 예를 들어, 단백질, 탄수화물, 지방, 영양소, 조미제 및 향미제를 포함한다. 상술한 탄수화물의 예는 모노사카라이드, 예를 들어, 포도당, 과당 등; 디사카라이드, 예를 들어 말토스, 슈크로스, 올리고당 등; 및 폴리사카라이드, 예를 들어 덱스트린, 사이클로덱스트린 등과 같은 통상적인 당 및 자일리톨, 소르비톨, 에리트리톨 등의 당알콜이다. 향미제로서 천연 향미제 [타우마틴, 스테비아 추출물 (예를 들어 레바우디오시드 A, 글리시르히진 등]) 및 합성 향미제(사카린, 아스파르탐 등)를 사용할 수 있다. 예컨대, 본 발명의 식품 조성물이 드링크제와 음료류로 제조되는 경우에는 유화제 및 항갈변제 처리된 에피갈로카테킨갈레이트 이외에 구연산, 액상과당, 설탕, 포도당, 초산, 사과산, 과즙, 및 각종 식물 추출액 등을 추가로 포함시킬 수 있다.
The food composition of the present invention may include not only epigallocatechin gallate treated with an emulsifier and anti-browning agent as an active ingredient, but also ingredients commonly added during food production, for example, protein, carbohydrate, fat, Nutrients, seasonings and flavoring agents. Examples of the above-mentioned carbohydrates include monosaccharides such as glucose, fructose and the like; disaccharides such as maltose, sucrose, oligosaccharides and the like; and polysaccharides, for example, conventional sugars such as dextrin, cyclodextrin, and the like, and sugar alcohols such as xylitol, sorbitol, and erythritol. As flavoring agents, natural flavoring agents [taumatine, stevia extract (eg, rebaudioside A, glycyrrhizin, etc.)) and synthetic flavoring agents (saccharin, aspartame, etc.) can be used. For example, when the food composition of the present invention is prepared as a drink or beverage, in addition to epigallocatechin gallate treated with an emulsifier and an anti-browning agent, citric acid, fructose liquid, sugar, glucose, acetic acid, malic acid, fruit juice, and various plant extracts, etc. may be additionally included.
본 발명은 상기 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 활성을 갖는 식품 또는 음료 조성물을 포함하는 건강기능식품 또는 건강기능음료를 제공한다. The present invention provides a health functional food or health functional beverage comprising a food or beverage composition having antioxidant activity comprising the epigallocatechin gallate as an active ingredient.
건강기능식품 또는 음료이란, 유화제 및 항갈변제 처리된 에피갈로카테킨갈레이트를 음료, 차류, 향신료, 껌, 과자류 등의 식품소재에 첨가하거나, 캡슐화, 분말화, 현탁액 등으로 제조한 식품으로, 이를 섭취할 경우 건강상 특정한 효과를 가져오는 것을 의미하나, 일반 약품과는 달리 식품을 원료로 하여 약품의 장기 복용 시 발생할 수 있는 부작용 등이 없는 장점이 있다. 이와 같이 하여 얻어지는 본 발명의 건강기능식품 또는 음료는, 일상적으로 섭취하는 것이 가능하기 때문에 매우 유용하다. 이와 같은 건강기능식품 또는 음료에 있어서의 유화제 및 항갈변제 처리된 에피갈로카테킨갈레이트의 첨가량은, 대상인 건강기능식품 또는 음료의 종류에 따라 달라 일률적으로 규정할 수 없지만, 식품 본래의 맛을 손상시키지 않는 범위에서 첨가하면 되며, 대상 식품에 대하여 통상 0.01 내지 50 중량%, 바람직하기로는 0.1 내지 20 중량%의 범위이다. 또한, 환제, 과립제, 정제 또는 캡슐제 형태의 건강기능식품의 경우에는 통상 0.1 내지 100 중량% 바람직하기로는 0.5 내지 80 중량%의 범위에서 첨가하면 된다. 한 구체예에서, 본 발명의 건강기능식품은 환제, 정제, 캡슐제 또는 음료의 형태일 수 있다.
Health functional food or beverage is a food manufactured by adding epigallocatechin gallate treated with an emulsifier and anti-browning agent to food materials such as beverages, teas, spices, gums, and confectionery, or encapsulating, powdering, or suspension. , it means that certain health effects are obtained when ingested, but unlike general drugs, it has the advantage of not having side effects that may occur when taking the drug for a long time using food as a raw material. The health functional food or beverage of the present invention obtained in this way is very useful because it can be ingested on a daily basis. The amount of epigallocatechin gallate treated with an emulsifier and anti-browning agent in such a health functional food or beverage cannot be uniformly defined as it varies depending on the type of health functional food or beverage to be used. It may be added in a range that does not damage it, and is usually in the range of 0.01 to 50% by weight, preferably 0.1 to 20% by weight, based on the target food. In addition, in the case of a health functional food in the form of pills, granules, tablets or capsules, it is usually added in an amount of 0.1 to 100% by weight, preferably 0.5 to 80% by weight. In one embodiment, the health functional food of the present invention may be in the form of a pill, tablet, capsule or beverage.
또한, 본 발명은 상기 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물을 포함하는 항산화 활성을 갖는 약학 조성물을 제공한다. In addition, the present invention provides a pharmaceutical composition having antioxidant activity comprising the antioxidant composition comprising the epigallocatechin gallate as an active ingredient.
본 발명의 약학 조성물은 상기 유효 성분 이외에 약학으로 적합하고 생리학적으로 허용되는 보조제를 사용하여 제조될 수 있으며, 상기 보조제로는 부형제, 붕해제, 감미제, 결합제, 피복제, 팽창제, 윤활제, 활택제 또는 향미제 등을 사용할 수 있다.The pharmaceutical composition of the present invention may be prepared using pharmaceutically suitable and physiologically acceptable adjuvants in addition to the active ingredients, and the adjuvants include excipients, disintegrants, sweeteners, binders, coating agents, swelling agents, lubricants, and lubricants. Or a flavoring agent or the like may be used.
상기 약학 조성물은 투여를 위해서 상기 기재한 유효 성분 이외에 추가로 약학으로 허용 가능한 담체를 1종 이상 포함하여 약학 조성물로 바람직하게 제제화할 수 있다.The pharmaceutical composition may be preferably formulated as a pharmaceutical composition by including one or more pharmaceutically acceptable carriers in addition to the active ingredients described above for administration.
상기 약학 조성물의 제제 형태는 액제, 시럽, 즙, 현탁제, 유제, 점적제 또는 등이 될 수 있다. 예를 들어, 또한, 필요한 경우, 적합한 결합제, 윤활제, 붕해제 및 발색제 또한 혼합물로 포함될 수 있다. 적합한 결합제는 이에 제한되는 것은 아니나, 녹말, 젤라틴, 글루코스 또는 베타-락토오스와 같은 천연 당, 옥수수 감미제, 아카시아, 트래커캔스 또는 소듐올레이트와 같은 천연 및 합성 검, 소듐 스테아레이트, 마그네슘 스테아레이트, 소듐 벤조에이트, 소듐 아세테이트, 소듐 클로라이드 등을 포함한다. 붕해제는 이에 제한되는 것은 아니나, 녹말, 메틸 셀룰로스, 아가, 벤토니트, 잔탄 검 등을 포함한다.Formulations of the pharmaceutical composition may be solutions, syrups, juices, suspensions, emulsions, drops, or the like. For example, if necessary, suitable binders, lubricants, disintegrants and coloring agents may also be included in the mixture. Suitable binders include, but are not limited to, starch, gelatin, natural sugars such as glucose or beta-lactose, corn sweeteners, natural and synthetic gums such as acacia, tracacanth or sodium oleate, sodium stearate, magnesium stearate, sodium benzoate, sodium acetate, sodium chloride, and the like. Disintegrants include, but are not limited to, starch, methyl cellulose, agar, bentonite, xanthan gum, and the like.
본 발명의 약학 조성물은 경구 투여에 의하는 것이 바람직하다.
The pharmaceutical composition of the present invention is preferably administered orally.
또한, 본 발명은 상기 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물을 포함하는 항산화 활성을 갖는 화장료 조성물을 제공한다. In addition, the present invention provides a cosmetic composition having antioxidant activity comprising the antioxidant composition comprising the epigallocatechin gallate as an active ingredient.
상기 화장료 조성물은 항산화 활성을 갖는 것을 특징으로 한다.The cosmetic composition is characterized in that it has antioxidant activity.
상기 화장료 조성물은 혼합물의 유화제 및 항갈변제 처리된 에피갈로카테킨갈레이트이거나 상기 유화제 및 항갈변제 처리된 에피갈로카테킨갈레이트를 진공, 농축 후 동결 건조시킨 분말이거나, 상기 분말을 추출용매와 배합한 배합물일 수 있다.The cosmetic composition may be epigallocatechin gallate treated with an emulsifier and an anti-browning agent of the mixture, or a powder obtained by freeze-drying the emulsifier and anti-browning agent-treated epigallocatechin gallate in a vacuum and concentration, or extracting the powder as an extraction solvent It may be a combination combined with.
상기 유화제 및 항갈변제 처리된 에피갈로카테킨갈레이트는 바람직하게는 화장료 조성물의 총 중량에 대하여 0.0001 내지 90중량%의 함량으로 포함될 수 있다. 왜냐하면, 혼합물의 추출물 함량이 0.0001중량% 미만인 경우에는 항산화 효과가 나타나기 어렵고, 90중량% 이상인 경우에는 제형 상의 안정성이 저하될 수 있다.
The emulsifier and anti-browning agent-treated epigallocatechin gallate may preferably be included in an amount of 0.0001 to 90% by weight based on the total weight of the cosmetic composition. Because, when the content of the extract of the mixture is less than 0.0001% by weight, the antioxidant effect is difficult to appear, and when it is more than 90% by weight, the stability of the formulation may be reduced.
본 발명의 화장료 조성물에 포함되는 성분은 유효성분으로서 상기 유효성분 이외에 화장품 조성물에 통상적으로 이용되는 성분들을 포함하며, 예를 들어서 항산화제, 안정화제, 용해화제, 비타민, 향료와 같은 통상적인 보조제, 그리고 담제를 포함한다. 본 발명의 화장료 조성물은 당 업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어 용액, 현탁액, 유탁액, 페이스트, 젤, 크림, 로션, 파우더, 비누, 계면활성제 함유 클렌징, 오일, 분말파운데이션, 유탁액 파운데이션, 왁스 파운데이션 증으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는 세안용 클렌징, 로션, 크림, 마사지 크림, 아이크림, 에센스, 젤, 팩, 스프레이, 파우더, 선크림 등의 제형으로 제조될 수 있다.The ingredients included in the cosmetic composition of the present invention include ingredients commonly used in cosmetic compositions in addition to the active ingredients as an active ingredient, for example, conventional auxiliary agents such as antioxidants, stabilizers, solubilizers, vitamins, and fragrances; and containment agents. The cosmetic composition of the present invention may be prepared in any formulation conventionally prepared in the art, for example, a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil , powder foundation, emulsion foundation, or wax foundation, but is not limited thereto. More specifically, it may be prepared in the form of cleansing, lotion, cream, massage cream, eye cream, essence, gel, pack, spray, powder, sun cream, etc.
본 발명의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로 식물성유, 왁스, 전분, 셀룰로오스, 실리콘, 벤토나이트, 실리카, 산화아연 등이 이용될 수 있고, 제형이 파우더 경우에는 담체 성분으로서 락토스, 실리카, 알루미늄 히드록사이드, 칼슘 실리케이트 등의 파우더가 이용될 수 있다. 본 발명의 제형이 용액 또는 유탁액인 경우에는 담체 성분으로서 용매, 용해화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 글리세린, 에틸 카보네이트, 에틸 아세테이트, 프로필렌글라이콜, 부틸렌글라이콜, 1,2-헥산디올, 글리세롤 지방족 에스테르, 소르비탄 지방산 에스테르가 있다. When the formulation of the present invention is a paste, cream, or gel, vegetable oil, wax, starch, cellulose, silicone, bentonite, silica, zinc oxide, etc. may be used as carrier components, and when the formulation is powder, lactose, silica as a carrier component , aluminum hydroxide, calcium silicate, and the like powder may be used. When the formulation of the present invention is a solution or emulsion, a solvent, solubilizer or emulsifier is used as a carrier component, for example, water, ethanol, glycerin, ethyl carbonate, ethyl acetate, propylene glycol, butylene glycol, 1 ,2-hexanediol, glycerol fatty esters, and sorbitan fatty acid esters.
본 발명의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올, 프로필렌글라이콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소 결정성 셀룰로오스, 알루미늄 메타히드록사이드, 벤토나이트, 아가 등이 이용될 수 있다. 또한 제형이 계면활성제 함유 클렌징인 경우에는 담체 성분으로서 지방족 알코올 설페이트, 지방족 알코올 에테르 설페이트, 설포숙신산 모노에스테르, 이세치오네이트, 메칠타우레이트, 사르코시네이트, 알킬아미도베타인, 지방족 알코올, 지방산 글리세라이드, 식물성유 또는 에톡실화 글리세롤 지방산 에스테르 등이 이용될 수 있다.
When the formulation of the present invention is a suspension, as a carrier component, a liquid diluent such as water, ethanol, or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester; Microcrystalline cellulose, aluminum metahydroxide, bentonite, agar, and the like can be used. In addition, when the formulation is a cleansing agent containing surfactant, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, methyltaurate, sarcosinate, alkylamidobetaine, aliphatic alcohol, fatty acid glycer Ride, vegetable oil, or ethoxylated glycerol fatty acid ester may be used.
[[ 실시예Example ]]
재료 및 시약Materials and reagents
본 시험에서 사용한 EGCG(Epigallocatechin gallate)는 참녹 네물차에서 추출된 순도 92%의 물질로 추출 후 동결건조해 분말화하여 사용하였다. 레시틴, 토코페롤, 올레산, 사이클로덱스트린, 알지네이트, 펙틴, 스테비오사이드, 비타민 C, 갈산 등 표준품들은 Sigama Chemical Co. (St Louis, MO, USA)에서 메탄올, 에틸아세테이트 등 용매는 HPLC 용으로 Mallinchrodt Baker Inc. (Phillipsburg, NJ, USA) 제품을 사용하였다. 항갈변효과를 위한 PPO (polypheonol oxidase) 와 카테킨 기질은 Sigma- Aldrich (St. Luis, MO, USA)에서 구입하였다. 항산화능 측정용 시약으로 ABTS와 1,1-diphenyl-2-picrylhydrazyl (DPPH)은 Sigma Chemical Co. 제품을 사용하였다. 모든 분석시약은 90% 이상 순도인 시약을 사용하였다.
EGCG (Epigallocatechin gallate) used in this test was extracted from green nemulcha with 92% purity, and then lyophilized and powdered for use. Standards such as lecithin, tocopherol, oleic acid, cyclodextrin, alginate, pectin, stevioside, vitamin C, and gallic acid are supplied by Sigama Chemical Co., Ltd. (St Louis, MO, USA) solvents such as methanol and ethyl acetate were prepared by Mallincrodt Baker Inc. for HPLC. (Phillipsburg, NJ, USA) product was used. Polypheonol oxidase (PPO) and catechin substrates for anti-browning effect were purchased from Sigma-Aldrich (St. Luis, MO, USA). As reagents for measuring antioxidant activity, ABTS and 1,1-diphenyl-2-picrylhydrazyl (DPPH) were manufactured by Sigma Chemical Co., Ltd. product was used. All analytical reagents were used with a purity of 90% or more.
실시예Example 1: One: EGCGEGCG 에멀젼emulsion 제조 Produce
에피갈로카테킨갈레이트(EGCG)(10 ~ 30%, w/v) 에탄올 혼합물을 가용화하기 위해 1차로 EGCG (10%, w/v)를 기준으로 유층 유화제 1%(w/v)를 첨가하고 혼합 후 10배의 증류수에 5 분간 초음파처리 하였다. 2차로 수층에서의 EGCG 가용화 촉진제로 수층 유화제(0.1%, w/v)을 1차 용액에 5분간 초음파처리 하였다. 3차로 항갈변제(0.1%, w/v)을 2차 용액에 5 분간 초음파처리 하였다.Epigallocatechin gallate (EGCG) (10 to 30%, w/v) 1% (w/v) of an oil emulsifier based on EGCG (10%, w/v) was added first to solubilize the ethanol mixture. After mixing, it was sonicated in 10 times distilled water for 5 minutes. Second, the aqueous layer emulsifier (0.1%, w/v) was sonicated for 5 minutes in the first solution as an EGCG solubilization accelerator in the aqueous layer. Third, an anti-browning agent (0.1%, w/v) was sonicated in the secondary solution for 5 minutes.
유층 유화제로 레시틴(lecithin)을 사용하였다. Lecithin was used as an oil emulsifier.
수층 유화제는 사이클로덱스트린(cyclodextrin), 알지네이트(alginate), 펙틴(pectin), 스테비오사이드(stevioside)를 사용하였다.As the aqueous emulsifier, cyclodextrin, alginate, pectin, and stevioside were used.
항갈변제는 비타민 C, 갈산(gallic acid)을 사용하였다.As an anti-browning agent, vitamin C and gallic acid were used.
초음파 처리 조건은 30% power (700W 100%), 3초 on /1초 off 5 분간 (50 cycles)로 에멀젼화하였으며, 사용기기는 John Morris Ultrasonic processor 750 watts, 20khz with CV334 converter & 630-0220 (1/2'') 13mm probe를 사용하였다.
Ultrasonic treatment conditions were emulsified at 30% power (700W 100%), 3 sec on /1 sec off 5 min (50 cycles), and the equipment used was John Morris Ultrasonic processor 750 watts, 20khz with CV334 converter & 630-0220 ( 1/2'') 13mm probe was used.
[[ 실험예Experimental example ]]
실험예Experimental example 1: 갈변 방지제에 따른 1: According to the anti-browning agent 항갈변anti-browning 효과 분석 Effect analysis
갈변 방지제인 비타민 C와 갈산을 식품에 사용 가능한 범위에서 각각 EGCG (10%, w/v)를 기준으로 0.005~0.1%(w/v) 농도별로 PPO(polyohenol oxidase inhibition) 저해 활성을 측정하여 그 결과를 아래의 표 1 및 도 1에 나타내었다. The anti-browning agents vitamin C and gallic acid were measured by measuring PPO (polyohenol oxidase inhibition) inhibitory activity at each concentration of 0.005 to 0.1% (w/v) based on EGCG (10%, w/v) within the range that can be used in food. The results are shown in Table 1 and FIG. 1 below.
이에 따르면, Vit C 와 갈산의 농도별 PPO저해 활성을 측정한 결과 0.1% 이하의 낮은 농도에서도 80~90% 이상의 PPO저해 활성을 가지는 것으로 나타났다.
According to this, as a result of measuring the PPO inhibitory activity for each concentration of Vit C and gallic acid, it was found to have PPO inhibitory activity of 80 to 90% or more even at a low concentration of 0.1% or less.
실험예Experimental example 2: 유화제에 따른 2: according to the emulsifier 항갈변anti-browning 효과 분석 Effect analysis
유층 유화제 또는 수층 유화제로 사용된 사이클로덱스트린, 알지네이트, 펙틴, 스테비오사이드, 레시틴을 EGCG (10%, w/v)를 기준으로 0.001~0.1%(w/v) 농도별 (w/v)로 항갈변 효능을 조사하여 그 결과를 도 2에 나타내었다. 이에 따르면, 사이클로덱스트린 외에는 항갈변 효과가 거의 나타나지 않았다. 즉, 유화제의 사용만으로는 항갈변 효과를 나타내기 어려움을 알 수 있었다.
Cyclodextrin, alginate, pectin, stevioside, and lecithin used as oil emulsifiers or water emulsifiers are EGCG (10%, w/v) based on 0.001 to 0.1% (w/v) concentration (w/v) The browning efficacy was investigated and the results are shown in FIG. 2 . According to this, there was almost no anti-browning effect except for cyclodextrin. That is, it was found that it was difficult to exhibit the anti-browning effect only by using the emulsifier.
실험예Experimental example 3: 유화제와 3: with emulsifier 항갈변제antibrowning agent 동시 첨가시 Simultaneous addition 항갈변anti-browning 효과 분석 Effect analysis
유화제와 항갈변제를 동시 첨가하는 경우의 항갈변 효과를 분석하였다. 이에 따른 유화제 및 항갈변제 종류에 따른 갈변 정도의 사진을 도 3에 나타내고, EGCG 항갈변효과 조사 위한 수용성 유화제 6종 (0.1%(w/v)) 항갈변제 2종 비타민 C, 갈산 (0.1%(w/v)) 첨가 후 50℃에 48시간 반응 후 갈변도(420nm)를 도 4와 hunter color value를 조사한 결과를 아래의 표 2에 나타내었다.The anti-browning effect of simultaneous addition of an emulsifier and an anti-browning agent was analyzed. According to this, a photograph of the degree of browning according to the type of emulsifier and anti-browning agent is shown in FIG. 3, and 6 types of water-soluble emulsifiers (0.1% (w/v)) for investigation of EGCG anti-browning effect, 2 types of anti-browning agents, vitamin C, gallic acid (0.1 % (w/v)) after the addition and reaction at 50° C. for 48 hours, the browning degree (420 nm) is shown in FIG. 4 and the results of investigating the hunter color value are shown in Table 2 below.
이에 따르면 항갈변제와 함께 사용하는 경우, 유화제 종류별로는 펙틴이 항갈변 효과가 가장 우수하였고 사이클로덱스트린과 말토덱스트린도 갈변 억제 효과를 나타내었다. 특히 색차계를 이용해 조사한 결과에서 펙틴은 다른 유화제를 사용한 경우보다 밝기가 가장 높게 측정되었고, 색별로 전체적인 변화를 나타내는 지표인 △E 또한 가장 낮아 항갈변 효과가 가장 높은 것으로 나타났다. 항갈변제는 비타민 C보다는 갈산이 더 높은 효과를 나타내었다.According to this, when used together with an anti-browning agent, pectin showed the best anti-browning effect by type of emulsifier, and cyclodextrin and maltodextrin also exhibited an anti-browning effect. In particular, in the results of investigation using a colorimeter, the brightness of pectin was measured to be the highest compared to the case of using other emulsifiers, and ΔE, an index indicating the overall change by color, was also the lowest, indicating the highest anti-browning effect. Anti-browning agents showed a higher effect of gallic acid than vitamin C.
한편, 유화제 중 가장 항갈변 효과가 높게 측정된 펙틴(PT)과 항갈변제의 동시 첨가시 50 ℃에서의 시간별 갈변도(420nm)를 측정한 결과를 도 5에 나타내었다. 펙틴은 갈산과 혼합 조건에서 항갈변제로 상승 효과를 나타내었다.
Meanwhile, the results of measuring the browning degree (420 nm) over time at 50° C. when pectin (PT), which has the highest anti-browning effect among the emulsifiers, and the anti-browning agent are simultaneously added is shown in FIG. 5 . Pectin exhibited a synergistic effect as an anti-browning agent in a mixed condition with gallic acid.
실험예Experimental example 4: 항산화 효과 분석 4: Antioxidant effect analysis
총 페놀 함량은 Folin-Denis법(1915)을 일부 변형하여 메탄올 추출물 시료 0.0625 ㎖에 1 N Folin-Denies reagent 0.0625 ㎖를 첨가하고 충분히 혼합한 다음 6분간 암실에서 반응시켰다. 그 후 7% Na2CO3 0.0625 ㎖와 증류수 1.5 ㎖를 첨가하여 실온의 암소에서 60분간 반응시킨 후 microplate spectrophotometer(Biotek Epoch., USA)를 이용하여 760 nm에서 흡광도를 측정하였다. 총 페놀 함량은 갈산 10 mg을 메탄올 10 ㎖에 용해한 표준용액을 사용하여 작성한 표준곡선으로부터 계산하였다.For the total phenol content, the Folin-Denis method (1915) was partially modified, and 0.0625 ml of 1 N Folin-Denies reagent was added to 0.0625 ml of a methanol extract sample, thoroughly mixed, and then reacted in the dark for 6 minutes. After that, 0.0625 ml of 7% Na 2 CO 3 and 1.5 ml of distilled water were added and reacted for 60 minutes in a dark place at room temperature. The absorbance was measured at 760 nm using a microplate spectrophotometer (Biotek Epoch., USA). The total phenol content was calculated from a standard curve prepared by using a standard solution in which 10 mg of gallic acid was dissolved in 10 ml of methanol.
총 플라보노이드 함량은 Abeysinghe 등(2007)의 방법을 일부 변형하여 측정하였다. 96 웰 플레이트에 시료와 90% 디에틸렌글리콜(diethylene glycol)을 넣고 3분 동안 microplate agitater(Titamax 101, Heidolph, Schwabach, Germany)를 이용하여 흔들어주었다. 2 N NaOH 용액을 각 웰에 넣은 후 37 ℃에서 30분간 반응시킨 후 420 nm에서 흡광도를 측정하였다. 총 플라보노이드 함량은 quercetin 10 mg을 메탄올 10 ㎕에 용해한 표준용액을 사용하여 작성한 표준곡선으로부터 계산하였다.The total flavonoid content was measured with some modifications of the method of Abeysinghe et al. (2007). Samples and 90% diethylene glycol were put in a 96-well plate and shaken for 3 minutes using a microplate agitator (Titamax 101, Heidolph, Schwabach, Germany). After putting 2 N NaOH solution into each well and reacting at 37 °C for 30 minutes, absorbance was measured at 420 nm. The total flavonoid content was calculated from a standard curve prepared by using a standard solution in which 10 mg of quercetin was dissolved in 10 μl of methanol.
DPPH 라디칼 소거활성은 Blois (1958)의 방법을 일부 변형하여 2,2-diphenyl-1-picryl-hydrazyl(DPPH)의 환원력을 이용하여 96 웰 플레이트에 시료를 분주하여 측정하였다. 1 mM DPPH reagent 250 ㎕와 메탄올 추출물 50 ㎕를 혼합, 37 ℃에서 10분 동안 반응시킨 후 microplate spectrophotometer(Biotek Epoch., USA)로 517 nm에서 흡광도를 측정하였다. 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) 라디칼 소거활성은 Re 등(1999)의 방법을 96 웰 플레이트에 맞게 수정하여 실시하였다. 7 mM ABTS(Sigma-Aldrich Co.)와 2.5 mM 과황화칼륨(potassium persulfate)을 최종 농도로 혼합하여 4 ℃ 냉장실에서 12시간 이상 보관하여 ABTS+을 형성시킨 후 735 nm에서 흡광도 값이 0.90±0.15가 되게 phosphate buffer saline (PBS, pH 7.4)으로 희석하였다. 이 ABTS+ 용액을 ethanol과 1:3 혼합한 후 plate에 1.25 ㎖를 넣고 735 nm에서 흡광도를 측정하였다. 96 well plate에 희석 된 ABTS+ 용액 250 ㎕와 물 추추출물 50 ㎕를 혼합하여 암소에서 30분 방치한 다음 microplate spectrophotometer(Biotek Epoch., USA)를 이용하여 735 nm에서 흡광도를 측정하였다. 이때 표준품으로 아스코르브산(ascorbic acid)을 사용하였으며 DPPH와 ABTS 라디칼 소거 활성은 추출물의 첨가 전과 후의 차이를 아래와 같은 식으로 계산하였다.DPPH radical scavenging activity was measured by dispensing a sample in a 96-well plate using the reducing power of 2,2-diphenyl-1-picryl-hydrazyl (DPPH) by partially modifying the method of Blois (1958). 250 μl of 1 mM DPPH reagent and 50 μl of methanol extract were mixed, reacted at 37° C. for 10 minutes, and absorbance was measured at 517 nm with a microplate spectrophotometer (Biotek Epoch., USA). 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging activity was performed by modifying the method of Re et al. (1999) for a 96-well plate. 7 mM ABTS (Sigma-Aldrich Co.) and 2.5 mM potassium persulfate were mixed to a final concentration and stored in a refrigerator at 4 ° C for 12 hours or more to form ABTS + , and the absorbance value at 735 nm was 0.90 ± 0.15 It was diluted with phosphate buffer saline (PBS, pH 7.4). After mixing this ABTS + solution with ethanol 1:3, 1.25 ml was added to the plate, and absorbance was measured at 735 nm. 250 μl of the diluted ABTS + solution and 50 μl of the water extract were mixed in a 96-well plate, left in the dark for 30 minutes, and then absorbance was measured at 735 nm using a microplate spectrophotometer (Biotek Epoch., USA). At this time, ascorbic acid was used as a standard product, and the difference between DPPH and ABTS radical scavenging activity before and after addition of the extract was calculated in the following way.
[식][expression]
Free radical scavenging activity=(1-Atest/Acontrol)×100
Free radical scavenging activity=(1-A test /A control )×100
EGCG (10%, w/v)에 대하여 유화제 및 항갈변제를 각각 0.1%(w/v) 동시 첨가시 총페놀 함유량을 측정하여 도 6에 나타내었고, 총 플라보노이드 함유량을 측정하여 도 7에 나타내었다. 또한, 50 ℃에서 48시간 반응 후 DPPH 소거능을 측정하여 도 8에 나타내었고, ABTS 소거능을 측정하여 도 9에 나타내었다.When 0.1% (w/v) of an emulsifier and an anti-browning agent were simultaneously added to EGCG (10%, w/v), the total phenol content was measured and shown in FIG. 6 , and the total flavonoid content was measured and shown in FIG. 7 . It was. In addition, the DPPH scavenging ability was measured and shown in FIG. 8 after the reaction at 50° C. for 48 hours, and the ABTS scavenging ability was measured and shown in FIG. 9 .
도 6에 따르면, 총페놀과 총플라보노이드 함량은 전체적으로 비타민 C를 첨가한 경우 모든 시료가 20% 가량 증가 되었으며 이는 비타민 자체가 가진 구조상의 성분 때문으로 보인다, According to FIG. 6, the total phenol and total flavonoid contents were increased by about 20% in all samples when vitamin C was added as a whole, which seems to be due to structural components of the vitamin itself
도 7에 따르면 총 플라보노이드는 펙틴과 갈산을 동시 첨가한 경우 126.7 mg/g으로 모든 시료 중 가장 높은 함유량을 보였다. According to FIG. 7, the total flavonoids showed the highest content among all samples as 126.7 mg/g when pectin and gallic acid were simultaneously added.
도 8 및 도 9에 따르면, 항산화 효과는 DPPH 소거능과 ABTS 소거능 측정시 항갈변제로 비타민 C나 갈릭산의 효과가 유사하였으며, 유화제별로 조사할 경우 펙틴과 스테비오사이드의 항산화 효과가 가장 높았으며 특히, ABTS 소거능에서 갈산과 펙틴 동시 첨가한 경우 가장 높은 효과를 나타내는 것으로 나타났다.According to FIGS. 8 and 9, the antioxidant effect was similar to that of vitamin C or gallic acid as an anti-browning agent when measuring DPPH scavenging ability and ABTS scavenging ability, and when investigated by emulsifier, the antioxidant effects of pectin and stevioside were the highest, and in particular, In the ABTS scavenging ability, it was found that the highest effect was obtained when gallic acid and pectin were added simultaneously.
한편, EGCG(30%, w/v)에 유층 유화제 레시틴 3%(w/v)를 첨가하고, 수층 유화제 펙틴 0.1%(w/v), 항갈변제 갈산 0.1%(w/v)를 첨가하여 EGCG 에멀젼하고, 상기 레시틴, 펙틴, 갈산 중 하나 이상을 생략한 에멀젼을 비교군으로 하여 50 ℃에서 5일 반응시켜 DPPH 소거능의 변화를 측정하여 비교군과 함께 그 결과를 아래의 표 3에 나타내었다.On the other hand, 3% (w/v) of lecithin, an oil emulsifier, was added to EGCG (30%, w/v), and 0.1% (w/v) of pectin, an aqueous emulsifier, and 0.1% (w/v) of gallic acid, an anti-browning agent, was added. EGCG emulsion, and the emulsion omitting at least one of lecithin, pectin, and gallic acid was reacted at 50 ° C for 5 days as a comparison group to measure the change in DPPH scavenging ability. It was.
(%)DPPH scavenging ability
(%)
이에 따르면, DPPH 소거능은 본 발명의 실시예에 따른 EGCG + 레시틴 + 펙틴 + 갈산 처리군에서 현저히 높으며, 5일이 경과한 DPPH 소거능이 높게 유지됨을 확인할 수 있었다.
According to this, DPPH scavenging ability was significantly higher in the EGCG + lecithin + pectin + gallic acid treatment group according to the embodiment of the present invention, and it was confirmed that the DPPH scavenging ability after 5 days was maintained high.
모든 실험 결과들은 3회 반복 측정하여 평균값과 표준편차로 나타냈으며, 각 처리별 평균치간의 유의성 검정은 SAS 프로그램(Package relwase 8.01)을 이용하여 분산분석(ANOVA)을 실시하였다. 평균간 유의적 차이가 있는 항목에 대해서는 Duncan's multiple range test로 p<0.05 수준에서 유의성 검정을 실시하였다.
All experimental results were measured three times and expressed as the mean and standard deviation, and the analysis of variance (ANOVA) was performed to test the significance between the mean values for each treatment using the SAS program (Package relwase 8.01). For items with significant differences between the means, a significance test was performed at p<0.05 level using Duncan's multiple range test.
이상, 본 발명의 실시예들에 대하여 설명하였으나, 해당 기술 분야에서 통상의 지식을 가진 자라면 특허청구범위에 기재된 본 발명의 사상으로부터 벗어나지 않는 범위 내에서, 구성 요소의 부가, 변경, 삭제 또는 추가 등에 의해 본 발명을 다양하게 수정 및 변경시킬 수 있을 것이며, 이 또한 본 발명의 권리범위 내에 포함된다고 할 것이다.
In the above, although embodiments of the present invention have been described, those of ordinary skill in the art can add, change, delete or add components within the scope that does not depart from the spirit of the present invention described in the claims. The present invention may be variously modified and changed by, etc., and this will also be included within the scope of the present invention.
Claims (19)
상기 수층 유화제는 사이클로덱스트린, 펙틴, 말토덱트트린, 알지네이트 및 스테비오사이드 중에서 선택된 1종 이상이고,
상기 유층 유화제는 레시틴이고,
상기 항갈변제는 비타민 C 및 갈산 중에서 선택된 1종 이상인,
에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물.oil-layer emulsifier, water-layer emulsifier and anti-browning agent, and emulsified epigallocatechin gallate;
The aqueous emulsifier is at least one selected from cyclodextrin, pectin, maltodextrin, alginate and stevioside,
The oil emulsifier is lecithin,
The anti-browning agent is at least one selected from vitamin C and gallic acid,
An antioxidant composition comprising epigallocatechin gallate as an active ingredient.
상기 수층 유화제는 펙틴, 사이클로덱스트린, 및 말토덱스트린 중에서 선택된 어느 하나의 수층 유화제를 포함하는 것을 특징으로 하는 항산화 조성물.According to claim 1,
The water-layer emulsifier is an antioxidant composition comprising any one water-layer emulsifier selected from pectin, cyclodextrin, and maltodextrin.
상기 수층 유화제는 펙틴인 것을 특징으로 하는 항산화 조성물.5. The method of claim 4,
The water-layer emulsifier is an antioxidant composition, characterized in that pectin.
상기 수층 유화제로 펙틴, 항갈변제로 갈산을 동시에 사용하는 것을 특징으로 하는 항산화 조성물.According to claim 1,
Antioxidant composition, characterized in that the simultaneous use of pectin as the water-layer emulsifier and gallic acid as an anti-browning agent.
상기 항산화 조성물은 에피갈로카테킨갈레이트 100중량부에 대하여 유층 유화제 5 내지 20중량부, 수층 유화제 0.05 내지 2중량부, 및 항갈변제 0.05 내지 2중량부를 포함하는 것을 특징으로 하는 항산화 조성물.According to claim 1,
The antioxidant composition comprises 5 to 20 parts by weight of an oil emulsifier, 0.05 to 2 parts by weight of an aqueous emulsifier, and 0.05 to 2 parts by weight of an anti-browning agent based on 100 parts by weight of epigallocatechin gallate.
(b) 상기 1차 에멀젼에 수층 유화제를 첨가하여 혼합함으로써 2차 에멀젼을 제조하는 단계; 및
(c) 상기 2차 에멀젼에 항갈변제를 첨가하여 혼합함으로써 3차 에멀젼을 제조하는 단계;를 포함하고,
상기 유층 유화제는 레시틴이고,
상기 수층 유화제는 사이클로덱스트린(b-cyclodextrin), 알지네이트(alginate), 펙틴(pectin) 및 스테비오사이드(stevioside) 중에서 선택된 1종 이상이고,
상기 항갈변제는 비타민 C 및 갈산(gallic acid) 중에서 선택된 1종 이상인, 에피갈로카테킨갈레이트를 유효성분으로 포함하는 항산화 조성물의 제조방법.(a) preparing a primary emulsion by mixing epigallocatechin gallate and water to which an oil emulsifier is added;
(b) preparing a secondary emulsion by adding and mixing a water-layer emulsifier to the primary emulsion; and
(c) preparing a tertiary emulsion by adding and mixing an anti-browning agent to the secondary emulsion;
The oil emulsifier is lecithin,
The aqueous emulsifier is at least one selected from cyclodextrin (b-cyclodextrin), alginate, pectin and stevioside,
The anti-browning agent is at least one selected from vitamin C and gallic acid, a method for producing an antioxidant composition comprising epigallocatechin gallate as an active ingredient.
상기 수층 유화제는 펙틴, 사이클로덱스트린, 및 말토덱스트린 중에서 선택된 어느 하나의 수층 유화제를 포함하는 것을 특징으로 하는 항산화 조성물의 제조방법.12. The method of claim 11,
The water-layer emulsifier is a method for producing an antioxidant composition, characterized in that it comprises any one water-layer emulsifier selected from pectin, cyclodextrin, and maltodextrin.
상기 수층 유화제로 펙틴, 항갈변제로 갈산을 동시에 사용하는 것을 특징으로 하는 항산화 조성물의 제조방법.15. The method of claim 14,
Method for producing an antioxidant composition, characterized in that the simultaneous use of pectin as the aqueous emulsifier and gallic acid as an anti-browning agent.
상기 항산화 조성물은 에피갈로카테킨갈레이트 100중량부에 대하여 유층 유화제 5 내지 20중량부, 수층 유화제 0.05 내지 2중량부, 및 항갈변제 0.05 내지 2중량부를 포함하는 것을 특징으로 하는 항산화 조성물의 제조방법.12. The method of claim 11,
The antioxidant composition comprises 5 to 20 parts by weight of an oil emulsifier, 0.05 to 2 parts by weight of an aqueous emulsifier, and 0.05 to 2 parts by weight of an anti-browning agent based on 100 parts by weight of epigallocatechin gallate Way.
17. A method for producing a cosmetic composition having antioxidant activity, comprising the method for preparing the antioxidant composition of any one of claims 11 and 14 to 16.
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