KR20180021578A - Composition for improving skin whitening and wrinkle comprising gallic acid glycoside as effective component - Google Patents
Composition for improving skin whitening and wrinkle comprising gallic acid glycoside as effective component Download PDFInfo
- Publication number
- KR20180021578A KR20180021578A KR1020160106326A KR20160106326A KR20180021578A KR 20180021578 A KR20180021578 A KR 20180021578A KR 1020160106326 A KR1020160106326 A KR 1020160106326A KR 20160106326 A KR20160106326 A KR 20160106326A KR 20180021578 A KR20180021578 A KR 20180021578A
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- KR
- South Korea
- Prior art keywords
- acid
- gallic acid
- composition
- enzyme
- glycoside
- Prior art date
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Images
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/318—Foods, ingredients or supplements having a functional effect on health having an effect on skin health and hair or coat
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/60—Sugars, e.g. mono-, di-, tri-, tetra-saccharides
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Mycology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
본 발명은 갈릭산 배당체를 유효성분으로 함유하는 피부 미백 및 주름 개선용 조성물에 관한 것이다.The present invention relates to a composition for improving skin whitening and wrinkles containing gallic acid glycoside as an active ingredient.
갈릭산(GA, 3,4,5-trihydroxybenzoic acid)은 녹차, 홍차, 포도주, 커피, 머루 등에 많이 함유되어 있는 탄닌(tannin)의 주요 구성성분으로 식료품뿐만 아니라 산수유, 오미자, 산사자, 오배자 등의 한약재에도 많이 함유되어 있는 것으로 알려져 있다. 갈릭산은 주로 활성산소제거, 손상된 DNA치유, 신경보호효과, 위장관 보호효과 및 항암효과와 같은 생리화학적 특성으로 잘 알려져 있다. 또한 이 물질은 미백, 항염작용이 보고돼 있는데, 특히 갈릭산이 과산화수소(hydrogen peroxide)로 인한 손상으로부터 피부 멜라닌세포를 보호하는 효과가 있음을 보고한 바 있으며, 발효차 중의 미량성분인 GA 산화물 푸르푸로갈린 카르복실산(purpurogallin carboxylic acid)이 항염 효능이 있음을 보고하였다. 갈릭산은 대개 장에서 중간산물인 4-O-메틸 갈릭산과 피로갈롤(pyrogallol)로 분해 소변으로 배출되는데 이들은 갈릭산 대비 현저히 낮은 항산화 효과 및 생체 효능을 보인다고 보고되고 있다. 갈릭산은 이처럼 다양한 효능을 보유함에도 불구하고 낮은 생체 이용율 및 낮은 용해도로 상업화에 제한이 있다.(GA, 3,4,5-trihydroxybenzoic acid) is a major constituent of tannin which is widely contained in green tea, black tea, wine, coffee, mulberry, etc. It is not only food, but also food such as corn oil, It is also known to be contained in many medicinal herbs. Galic acid is well known for its physiochemical properties such as active oxygen removal, damaged DNA healing, neuroprotective effects, gastrointestinal protective effects, and anti-cancer effects. In addition, this substance has been reported to be whitening and anti-inflammatory effect. In particular, gallic acid has been reported to protect skin melanocytes from damage caused by hydrogen peroxide, and GA oxide furfurosis, Purpurogallin carboxylic acid has anti-inflammatory activity. Galactic acid is usually released from the intestines into 4-O-methylgalic acid and pyrogallol, which are the intermediate products, and are released into the digested urine. They are reported to exhibit remarkably low antioxidative and biological efficacy compared to gallic acid. Galactic acid has such a wide range of potency, but has limited commercialization due to its low bioavailability and low solubility.
덱스트란수크라제(dextransucrase)는 mono-, di-, 또는 그 이상의 슈크로오스 단위를 다른 탄수화물 수용체(carbohydrate acceptors)에 글리코시드 결합(glycosidic linkages)을 통해 전달하는 효소로, 효소에 의한 배당체의 전달이 몇몇 바이오 활성 물질에 작용하여 그 기능적 특성을 변화시키려는 시도가 되어 왔다. Dextransucrase is an enzyme that transfers mono-, di-, or higher sucrose units to other carbohydrate acceptors via glycosidic linkages, There has been an attempt to alter the functional properties of the delivery by acting on some bioactive materials.
현재까지 덱스트란수크라제를 이용하여 갈릭산의 기능적 특성을 변화시키고 식품, 화장품 및 의약품 산업에 적용할 경우 그 물질적 특성을 증대시킨 종래기술은 없는 실정이다. 본 발명에서는 류코노스톡 메센테로이드(Leuconostoc mesenteroides) 유래의 덱스트란수크라제를 이용하여 갈릭산 당전이 유사체의 효소적 합성을 유도하여 총 갈릭산으로부터 38%의 수율이 가능한 최초의 시도임을 밝히고자 한다. 또한 수크로스, 효소, 갈릭산 농도의 20가지 조합을 이용한 반응표면분석을 통해 항산화, 지방산화, 미백 및 주름개선 효과가 뛰어난 갈릭산 당전이 유사체를 생산할 수 있는 최적의 생산조건을 확립하였다. There has been no conventional technology for improving functional properties of gallic acid by using dextran saccase and increasing its physical properties when it is applied to food, cosmetic and pharmaceutical industries. In order to elucidate the enzymatic synthesis of galactic acid glycoside analogues using dextran sucurase derived from Leuconostoc mesenteroides and to obtain a yield of 38% from total galactic acid, do. In addition, the optimum surface conditions for production of gallic acid analogues with excellent antioxidation, lipid oxidation, whitening and wrinkle - reducing effects were established through 20 reaction surface analysis using sucrose, enzyme and gallic acid concentrations.
한편, 한국등록특허 제0964944호에서는 '당전이 효소를 이용한 당전이 화합물의 유도체 제조방법 및 이로부터 제조된 유도체'가 개시되어 있고, 한국등록특허 제1374748호에서는 '아밀로수크라제를 이용한 카테킨 유도체의 제조방법 및 그로부터 제조된 카테킨 유도체'가 개시되어 있으나, 본 발명에서와 같이 갈릭산 배당체를 유효성분으로 함유하는 피부 미백 및 주름 개선용 조성물에 대해서는 개시된 바가 없다.Korean Patent No. 0964944 discloses a method for preparing a derivative of a herbal compound using the herbal composition and a derivative prepared therefrom, and Korean Patent No. 1374748 discloses a method for preparing a derivative of catechin using amylose sucrose And a catechin derivative prepared therefrom. However, the composition for improving skin whitening and wrinkles containing gallic acid glycoside as an active ingredient as in the present invention has not been disclosed.
본 발명은 상기와 같은 요구에 의해 도출된 것으로서, 본 발명에 기초한 최적화된 효소처리 조건을 바탕으로 높은 수율을 가지고 용해도 및 기호도가 증진되었을 뿐 아니라, 항산화, 지방산화, 미백 및 주름 개선 효과가 우수한 갈릭산 배당체를 생산할 수 있음을 확인함으로써, 본 발명을 완성하였다.The present invention has been made in view of the above-mentioned needs, and it is an object of the present invention to provide a novel enzyme treatment method and a process for producing the same which have high yield and high solubility and preference based on optimized enzyme treatment conditions based on the present invention, Galactic acid glycosides, and thus completed the present invention.
상기 과제를 해결하기 위해, 본 발명은 갈릭산 배당체를 유효성분으로 함유하는 피부 미백 및 주름 개선용 화장료 조성물을 제공한다.In order to solve the above problems, the present invention provides a cosmetic composition for skin whitening and wrinkle improvement, which contains galactic acid glycoside as an active ingredient.
또한, 본 발명은 갈릭산 배당체를 유효성분으로 함유하는 피부 미백 및 주름 개선용 건강식품 조성물을 제공한다.The present invention also provides a health food composition for whitening skin and improving wrinkles containing gallic acid glycoside as an active ingredient.
본 발명에 따른 효소적 반응을 통해 기능적 특성이 우수하면서도, 용해도 및 기호도 등의 식품, 화장품 및 의약품 용도로의 물리화학적 특성이 증진된 새로운 형태의 갈릭산을 생산할 수 있으며, 다양한 기능성을 지닌 화장품, 의약 원료 및 기능성 식품으로의 이용 시 특정 효능을 목적으로 하며 적용성을 증가시켜 새로운 기능성 원료를 개발할 수 있을 것으로 기대된다. The enzymatic reaction according to the present invention can produce a new type of gallic acid having improved functional and physico-chemical properties for foods, cosmetics and pharmaceuticals such as solubility and taste, It is expected that it will be possible to develop new functional raw materials by increasing the applicability for specific efficacy when used as pharmaceutical raw materials and functional foods.
도 1은 갈릭산에 당전이 시킨 후 황산발색(왼쪽) 또는 UV 245nm 이용(오른쪽)해 TLC로 확인한 결과이다. 1, 수크로스; 2, 프락토스; 3, 글루코스; 4, 덱스트란수크라제 효소; 5, 갈릭산 (GA); 6~7, 효소반응액, 37℃, 6시간 반응, 수크로스(355 mM) + 효소(덱스트란수크라제, 0.65 units/㎖), 갈릭산(322mM). 화살표는 갈릭산(Gallic acid)과 이에 당전이된 물질(GG)을 가리킨다.
도 2는 갈릭산 배당체를 C18 역상 칼럼 HPLC로 분리한 크로마토그램과 TLC 분석 결과이다.
도 3은 ESI(-)-MS/MS 분석에 의해 갈릭산 배당체의 분자량 및 성분 동정 결과이다.
도 4는 갈릭산 배당체의 반응표면분석에 의해 도출된 갈릭산 배당체 생성(24시간 반응시)의 3차원 그래프를 나타낸다.
도 5는 본 발명에 따른 갈릭산 배당체(GG)의 항산화 효과를 확인한 결과이다.
도 6은 본 발명에 따른 갈릭산 배당체(GG)의 항지질산패 효과를 확인한 결과이다.
도 7은 본 발명에 따른 갈릭산 배당체(GA-glc)의 아질산염 소거능을 확인한 결과이다.
도 8은 본 발명에 따른 갈릭산 배당체(GG)의 티로시나제 효소 억제 효과를 확인한 결과이다.
도 9는 본 발명에 따른 갈릭산 배당체(GG)의 콜라겐 생성 효과를 RT-PCR(A) 및 웨스턴 블롯(B)을 통하여 확인한 결과이다.
도 10은 본 발명에 따른 갈릭산 배당체(GG)의 MMP-1 생성억제 효과를 확인한 결과이다.FIG. 1 shows the results of TLC analysis of sulfuric acid (left) or UV 245 nm (right) after conversion to gallic acid. 1, sucrose; 2, fructose; 3, glucose; 4, dextran sucase enzyme; 5, gallic acid (GA); (355 mM) + enzyme (dextran sulcase, 0.65 units / ml) and galactic acid (322 mM) at 37 ° C for 6 hours. The arrows indicate gallic acid and the sugar-transferred substance (GG).
FIG. 2 is a chromatogram and TLC analysis of gallic acid glycoside separated by C 18 reverse phase column HPLC.
Figure 3 shows the results of molecular weight and component identification of gallic acid glycosides by ESI (-) - MS / MS analysis.
FIG. 4 shows a three-dimensional graph of gallic acid glycoside formation (at 24 hours reaction) derived from the reaction surface analysis of gallic acid glycosides. FIG.
FIG. 5 shows the result of confirming the antioxidative effect of gallic acid glycosides (GG) according to the present invention.
6 shows the result of confirming the anti-lipid peroxidation effect of gallic acid glycosides (GG) according to the present invention.
FIG. 7 shows the nitrite scavenging activity of gallic acid glycoside (GA-glc) according to the present invention.
FIG. 8 shows the results of confirming the tyrosinase inhibitory effect of the galactosyl glycoside (GG) according to the present invention.
FIG. 9 shows the results of confirming collagen production effect of gallic acid glycosides (GG) according to the present invention through RT-PCR (A) and Western blot (B).
Fig. 10 shows the results of confirming the effect of inhibiting MMP-1 production of gallic acid glycosides (GG) according to the present invention.
본 발명의 목적을 달성하기 위하여, 본 발명은 갈릭산 배당체를 유효성분으로 함유하는 피부 미백 및 주름 개선용 화장료 조성물을 제공한다.In order to accomplish the object of the present invention, the present invention provides a cosmetic composition for skin whitening and wrinkle improvement, which contains gallic acid glycoside as an active ingredient.
본 발명에서 사용되는 용어, "갈릭산(gallic acid)"은 페놀산(phenolic acid)으로 세 개의 히드록실기와 하나의 카르복실기가 붙어있는 링 구조를 가진다.The term "gallic acid" used in the present invention is a phenolic acid having a ring structure in which three hydroxyl groups and one carboxyl group are attached.
본 발명에서 사용되는 용어, "갈릭산 배당체(gallic acid glycoside(glucoside))"는 갈릭산이 당화 과정을 거쳐 생성되는 글리코시드를 의미한다. 본 발명에서는 갈릭산 당전이 유사체로 혼용되어진다. 구체적으로, 본 발명의 갈릭산 당체는 갈릭산-3-O-글루코시드, 갈릭산-4-O-글루코시드 등을 들 수 있으나, 이에 제한되지 않는다.As used herein, the term "gallic acid glycoside (glucoside)" means a glycoside produced through saccharification of gallic acid. In the present invention, galactic acid sugar is mixed with an analogue. Specifically, the galactic acid glycoside of the present invention includes, but is not limited to, galactic acid-3-O-glucoside, gallic acid-4-O-glucoside and the like.
본 발명의 갈릭산 배당체의 일 예로 하기 화학식 1로 표시되는 갈릭산-3-O-α-D-글루코피라노시드(gallic acid-3-O-α-D-glucopyranoside)를 사용할 수 있다.Working Examples of the gallic acid glycosides of the present invention may be used gallic acid -3- O-α -D- glucopyranoside (gallic acid-3- O-α -D-glucopyranoside) represented by the general formula (1).
본 발명의 일 구현예에 따르면, 덱스트란수크라제를 이용하여 생성된 갈릭산 배당체는 LC/MS/MS 를 통해 m/z 355 분자량과 (C13, H16, O10 Na)+ 구성을 확인했으며 생성물은 갈릭산에 글루코스가 한 개 붙어있으며 최종산물은 α-1,3 결합을 주로 하는 효소의 주요 특성을 통해 갈릭산-3-O-α-D-글루코피라노시드로 판정되었다.According to one embodiment of the present invention, the galactic acid glycoside produced using dextran saccase was confirmed to have a molecular weight of m / z 355 (C13, H16, O10 Na) + via LC / MS / Silver has one glucose attached to gallic acid, and the final product was determined to be gallic acid-3- O- alpha -D-glucopyranoside through the main properties of the enzyme, mainly alpha -1,3 linkage.
덱스트란수크라제는 효소 반응액 중에 설탕 외의 다른 화합물이 첨가될 경우 설탕의 글루코오스 단위를 첨가한 화합물에 전달하여 글리코실된 화합물을 합성하는 효소이다. 이때 첨가된 설탕 외의 화합물을 수용체라 하며 이 반응을 수용체 반응이라고 한다. 효소의 종류에 따라서 전이되는 글루코오스의 수용체와의 결합 구조와 수용체인 화합물과의 반응 효능이 다르며, 효소와 수용체와의 농도 비에 따라서도 생합성되는 수용체 산물의 종류가 다르다.Dextran sucrose is an enzyme that synthesizes a glycosylated compound by transferring glucose unit of sugar to a compound to which glucose is added when another compound other than sugar is added to the enzyme reaction solution. A compound other than sugar added at this time is called a receptor, and this reaction is called a receptor reaction. Depending on the type of the enzyme, the effect of the reaction between the binding structure of the glucose with the receptor and the compound as a receptor differs depending on the kind of the enzyme, and the kind of the receptor product to be biosynthesized varies depending on the concentration ratio between the enzyme and the receptor.
본 발명에 사용되는 덱스트란수크라제는 류코노스톡 메센테로이드(Leuconostoc mesenteroides) 종 균주로부터 얻어질 수 있다. 상기 미생물로부터 덱스트란수크라제의 분리는 예를 들어, 류코노스톡 메센테로이드 종 균주를 효모추출물, 펩톤, K2HPO4 및 수크로스를 함유하는 배지에 접종하여 배양한 후, 배양액에서 균체만을 분리하고 이로부터 덱스트란수크라제를 정제하여 이루어진다. 상기 덱스트란수크라제의 분리 및 정제는 이 기술 분야에 알려진 일반적인 방법에 의해 행해질 수 있다.The dextran sucrase used in the present invention can be obtained from strain Leuconostoc mesenteroides . For the isolation of dextran saccase from the microorganism, for example, a yeast extract, peptone, K 2 HPO 4, and sucrose are inoculated and cultured in a medium containing yeast extract, leukocytes, Followed by purification and purification of dextran sucrase. The separation and purification of dextran sucrase can be carried out by a general method known in the art.
상기 덱스트란수크라제를 0.1-1M 농도의 설탕이 함유된 용액에 첨가하고, 이를 갈릭산의 당 수용체와 반응시키면 설탕이 분해되어 설탕의 글루코오스가 상기 당 수용체에 전이되어 당전이 유사체가 합성된다. 이때 상기 덱스트란수크라제는 반응기 최종 활성 농도가 0.1-3.0 units/㎖이 되도록 하며, 0.5-1.0 units/㎖이 되도록 첨가하는 것이 가장 바람직하며, 상기 당 수용체는 최종 농도가 0.1~1M 농도가 되도록 첨가하는 것이 바람직하다. 또한 이때 상기 반응은 일반적으로 설탕이 모두 분해될 때까지, 바람직하게는 15-50℃에서, 보다 바람직하게는 28-38℃에서 2-24시간동안 행한다.The dextran sucrose is added to a solution containing sugar at a concentration of 0.1-1 M and reacted with the sugar receptor of gallic acid to decompose the sugar and glucose of the sugar is transferred to the sugar receptor to synthesize the sugar analogue . At this time, the dextran sucrase is most preferably added so that the final active concentration of the reactor is 0.1-3.0 units / ml, 0.5-1.0 units / ml, and the final concentration of the sugar receptor is 0.1-1M concentration . Also, at this time, the reaction is generally carried out until all of the sugar is decomposed, preferably at 15-50 DEG C, more preferably at 28-38 DEG C for 2-24 hours.
생성된 당전이 유사체는 통상적인 방법에 의해 분리 및 정제될 수 있다. 예를 들어, 겔투과크로마토그라피(Gel Permeation Chromatography)인 바이오겔 P-2 컬럼 크로마토그라피나 세파덱스 LH-20 컬럼 크로마토그라피로 1차 정제한 다음, HPLC(High Performance Liquid Chromatography)를 이용하여 각 유도체들을 단리할 수 있다. 사용된 컬럼은 μ-Bondapak C18-역상 컬럼이나 Hypersil APS-2 NH2 컬럼 등을 이용할 수 있다.The resulting glycosylated analogs can be isolated and purified by conventional methods. For example, first purification is carried out with Bio-gel P-2 column chromatography or Sephadex LH-20 column chromatography, which is Gel Permeation Chromatography, and then purified by HPLC (High Performance Liquid Chromatography) Can be isolated. The column used may be a μ-Bondapak C18-reversed-phase column or Hypersil APS-2 NH2 column.
본 발명의 일 구현예에 따르면, 본 발명은 류코노스톡 메센테로이드(Leuconostoc mesenteroides) 유래 덱스트란수크라제를 사용하여 갈릭산에 글루코스가 결합된 갈릭산 배당체를 합성하였다. 반응되지 않은 갈릭산 및 설탕은 에틸아세테이트(1:1, v/v)을 사용하여 제거하고, 상기 배당체를 부탄올/물 용출(butanol/water elution) 및 C18 역상 HPLC에 의해 분리하였으며, LC/MS/MS에 의해 추가로 확인하였다.According to one embodiment of the present invention, galactic acid glycosides conjugated with galactic acid were synthesized using dextran sucrose derived from Leuconostoc mesenteroides . Unreacted gallic acid and sugar were removed using ethyl acetate (1: 1, v / v) and the glycoside was isolated by butanol / water elution and C18 reverse phase HPLC and LC / MS / MS. ≪ / RTI >
본 발명의 갈릭산과 수크로오스를 덱스트란수그라제에 의한 억셉터 반응(acceptor reaction)을 통한 갈릭산 당전이 유사체의 최적 생성은 기질(X1), 효소(X2), 수용체 물질(X3)을 주요 변수로 하는 반응표면분석법에 의해 도출되는 하기의 회귀식에 의해 최적화되는 조건에 의해 제조되는 것을 특징으로 한다.The Optimal production of gallic acid glycosylation analogue by acceptor reaction of galactic acid and sucrose with dextran sulgase can be accomplished by the addition of substrate (X 1 ), enzyme (X 2 ) and receptor material (X 3 ) , Which is optimized by the following regression equation derived by the reaction surface analysis method.
Y = -158.9 + 0.32X1 + 0.24X2 + 0.63X3 - 0.00047X1 2 - 0.00013X2 2 - 0.00089X3 2 + 0.0000139X1X2 - 0.000011X1X3 - 0.000062X2X3.Y = -158.9 + 0.32X 1 + 0.24X 2 + 0.63X 3 - 0.00047X 1 2 - 0.00013X 2 2 - 0.00089X 3 2 + 0.0000139X 1 X 2 - 0.000011X 1 X 3 - 0.000062X 2 X 3 .
본 발명의 갈릭산 배당체는 갈릭산보다 용해도, 기호도, 항산화, 피부 미백 및 주름 개선 효과가 향상된 것을 특징으로 한다.The galactic acid glycosides of the present invention are characterized by improved solubility, preference, antioxidation, skin whitening and wrinkle-reducing effect than gallic acid.
본 발명의 일 구현예에서, 상기 갈릭산 배당체는 멜라닌 색소 생성에 중요한 효소인 티로시나아제(tyrosinase) 활성을 억제하여 미백 효과를 가질 수 있다. In one embodiment of the present invention, the galactic acid glycosides may have a whitening effect by inhibiting tyrosinase activity, an enzyme important for melanin pigment formation.
본 발명의 일 구현예에서, 상기 갈릭산 배당체는 타입 I 콜라겐 합성을 증가시키고, MMP-1(matrix metalloproteinase-1)의 발현을 억제함으로써 주름 개선 효과를 가질 수 있다.In one embodiment of the present invention, the galactic acid glycoside may have a wrinkle-reducing effect by increasing type I collagen synthesis and inhibiting the expression of MMP-1 (matrix metalloproteinase-1).
본 발명의 화장료 조성물에는 상기 유효성분 이외에 화장품 조성물에 통상적으로 이용되는 성분들을 포함하며, 예컨대 지방 물질, 유기 용매, 용해제, 농축제 및 겔화제, 연화제, 항산화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온 봉쇄제 및 킬레이트화제, 보존제, 비타민, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 지질 소낭과 같은 통상적인 보조제, 그리고 담체를 포함한다.The cosmetic composition of the present invention includes components commonly used in cosmetic compositions in addition to the above-mentioned effective components, and examples thereof include lipids, organic solvents, solubilizers, thickeners and gelling agents, softeners, antioxidants, suspending agents, stabilizers, surfactants, water, ionic or nonionic emulsifiers, fillers, sequestering and chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents , Conventional adjuvants such as lipid vesicles, and carriers.
본 발명의 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 스킨, 스킨 소프트너, 스킨토너, 아스트린젠트, 로션, 밀크로션, 모이스쳐로션, 영양로션, 마사지크림, 영양크림, 아이 크림, 모이스쳐 크림, 핸드크림, 에센스, 영양에센스, 팩, 클렌징폼, 클렌징 워터, 클렌징 로션, 클렌징 크림, 바디로션, 바디클렌져, 비누 및 파우더의 화장품 제형으로 제조될 수 있다.The composition of the present invention may be prepared in any form conventionally produced in the art and may be prepared in the form of a solution, suspension, emulsion, paste, gel, cream, lotion, powder, oil, powder foundation, emulsion foundation , A wax foundation, and a spray, but the present invention is not limited thereto. More specifically, the present invention relates to a cosmetic composition for skin, skin softener, skin toner, astringent, lotion, milk lotion, moisturizing lotion, nutrition lotion, massage cream, nutritional cream, eye cream, moisturizer cream, hand cream, essence, Foam, cleansing water, cleansing lotion, cleansing cream, body lotion, body cleanser, soap and powder.
또한, 본 발명은 갈릭산 배당체를 유효성분으로 함유하는 피부 미백 및 주름 개선용 건강식품 조성물을 제공한다.The present invention also provides a health food composition for whitening skin and improving wrinkles containing gallic acid glycoside as an active ingredient.
본 발명에서 '건강식품'이란, 상기 화합물을 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.In the present invention, the term 'health food' means a food prepared by adding the above compound to food materials such as beverage, tea, spice, gum and confection, or encapsulated, powdered or suspended, However, unlike general medicine, there is an advantage that there is no side effect that may occur when a food is used as a raw material for a long period of taking the medicine.
본 발명의 조성물이 건강식품 조성물로 사용되는 경우, 유효성분으로서 갈릭산 배당체 이외에 식품 제조 시에 통상적으로 첨가되는 성분, 예를 들어, 단백질, 탄수화물, 지방, 영양소, 조미제 및 향미제를 추가로 포함할 수 있다.When the composition of the present invention is used as a health food composition, in addition to the galactic acid glycoside as an active ingredient, there may be added, in addition to the ingredients normally added in the manufacture of food such as protein, carbohydrate, fat, nutrients, .
상기 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.Examples of such carbohydrates are monosaccharides, such as glucose, fructose, and the like; Disaccharides such as maltose, sucrose, oligosaccharides and the like; And polysaccharides such as dextrin, cyclodextrin and the like, and sugar alcohols such as xylitol, sorbitol and erythritol. Natural flavorings such as tau martin and stevia extract (e.g., rebaudioside A and glycyrrhizin) and synthetic flavors (saccharin, aspartame, etc.) may be used as flavorings.
상기 식품의 종류에는 특별한 제한이 없다. 본 발명의 갈릭산 배당체를 첨가할 수 있는 식품의 예로는 육류, 소세지, 빵, 쵸코렛, 캔디류, 스넥류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차, 드링크제, 알콜 음료 및 비타민 복합제 등이 있으며, 통상적인 의미에서의 건강식품을 모두 포함한다.There is no particular limitation on the kind of the food. Examples of the food to which the gallic acid glycosides of the present invention can be added include meat products, sausages, breads, chocolates, candies, snacks, confectionery, pizza, ramen noodles, other noodles, dairy products including ice- Tea, drink, alcoholic beverage, and vitamin complex, all of which include health foods in a conventional sense.
본 발명의 식품 조성물이 드링크제로 제조되는 경우에는 본 발명의 갈릭산 배당체 이외에 구연산, 액상과당, 설탕, 포도당, 초산, 사과산, 과즙, 식물 유래 추출액 등을 추가로 포함시킬 수 있다.When the food composition of the present invention is prepared as a drink, citric acid, liquid fructose, sugar, glucose, acetic acid, malic acid, fruit juice, and plant-derived extract may be further added in addition to the gallic acid glycoside of the present invention.
또한, 상기 식품 조성물은 상술한 성분 외에 여러 가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산음료에 사용되는 탄산화제 등을 함유할 수 있다. 그 밖에 본 발명의 식품 조성물은 천연 과일쥬스, 음료 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 이러한 성분은 독립적으로 또는 조합하여 사용할 수 있다.
In addition, the food composition may contain various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloid thickening agents, pH adjusting agents, stabilizers, preservatives, glycerin , Alcohols, carbonating agents used in carbonated drinks, and the like. In addition, the food composition of the present invention may contain flesh for the production of natural fruit juices, beverages and vegetable drinks. These components may be used independently or in combination.
이하, 본 발명을 실시예에 의해 상세히 설명한다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예에 한정되는 것은 아니다.
Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited to the following examples.
실시예 1. 갈릭산 배당체 생성Example 1. Galactic acid glycoside formation
당전이를 위한 덱스트란수크라제 효소는 L. mesenteroides을 발효배양한후, 30K cutoff hollow fiber를 이용 정제 후 Q-세파로스 칼럼(Q-sepharose column)을 이용 정제된 것을 사용하였다. 효소 활성은 37℃에서 기질로 100 mM 수크로스가 포함된 20 mM 소듐 아세테이트(pH 5.2) 완충액을 이용해 여러 가지 반응시간을 두어 측정하였다. 이 때 덱스트란수크라제 1 unit은 20 mM 소듐 아세테이트 완충용액(pH 5.2)을 사용, 37℃에서 분당 1 μmol 의 프락토스를 분해하는 효소의 활성을 말한다. 갈락산 배당체 생성조건은 총 500㎖에 0.32M 갈릭산(27.2 g), 0.35M 수크로스 (60.7 g), 그리고 덱스트란수크라제(0.65 units/㎖)를 혼합하였다. 반응액을 37℃에서 2~24시간 동안 설탕이 없어질 때까지 반응시켰다. 반응액을 5분간 효소를 불활성화 하기 위해 100℃에서 끓였다. TLC(Thin-Layer Chromatography)는 silica gel 60 F254 TLC plate (Merck Co.)를 이용해 분석하였다. 각 반응액을 실온에서 1㎕씩 실리카 겔 플레이트(silica gel plate)에 점적한 후 전개용매 ethyl acetate/acetic acid/water (3:1:1, v/v/v)을 이용 TLC 챔버(chamber)에 넣어 전개한 후 UV 254nm에서 검출하거나 황산발색용매 (0.3% N-1-naphthyl-ethylenediamine 및 5% 황산이 함유된 메탄올)에 5초간 담근 후 110℃ 건조 오븐에서 10분간 발색하였다. The dextran sucrose enzyme for the glycosyltransferase was obtained by fermentation of L. mesenteroides , purification using a 30K cutoff hollow fiber, and purification using a Q-sepharose column. Enzyme activity was measured at 37 째 C with various reaction times using 20 mM sodium acetate (pH 5.2) buffer containing 100 mM sucrose as a substrate. Here,
L. mesenteroides로부터 얻어진 덱스트란수크라제 효소와 기질로서 설탕을 이용해 항암물질인 갈릭산에 당전이를 시켜 TLC를 이용해 분석한 결과, 약 38%의 효과적인 배당체 생성 수율을 나타냈다(도 1).
The dextran sucrose enzyme obtained from L. mesenteroides and the sugar as a substrate were subjected to glycine transferring to gallic acid, which is an anticancer substance, and analyzed by TLC. As a result, an effective glycoside production yield of about 38% was obtained (FIG. 1).
실시예 2. 갈릭산과 갈릭산 배당체의 용매 추출Example 2. Solvent Extraction of Galic Acid and Galic Acid Glycoside
반응액에 존재하는 설탕이나 효소 등(dextran, fructose, 및 glucose)을 없애기 위해 비극성 용매 4가지(클로로포름, 헥산, 부탄올, 초산에틸)을 사용해 1대1로 섞은 후 200rpm에서 30분간 혼합한 후 원심분리해서(10,000 xg, 20분, 4℃) 상등액, 아래층, 침전물을 TLC 분석하였다. To remove the sugars and enzymes (dextran, fructose, and glucose) present in the reaction mixture, four nonpolar solvents (chloroform, hexane, butanol, ethyl acetate) were mixed one by one and mixed at 200 rpm for 30 minutes. Separation (10,000 xg, 20 min, 4 ° C) TLC analysis of supernatant, bottom layer, and precipitate.
그 결과, 도 2에 개시된 바와 같이 부탄올을 사용하였을 때 가장 효과적으로 배당체가 분리되는 것을 확인하였다. 이 때 갈릭산 배당체는 부탄올 추출 및 실리카 겔 칼럼으로 분리후 u-Bondapak C18 (300 x 19 mm) column으로 분리하였다. 분리조건은 A 용매(0.1% formic acid 함유된 물)와 B 용매(0.1% formic acid 함유된 메탄올)를 이용하였으며, 유속은 0.5 ㎖/min, UV 245nm에서 측정하였다.
As a result, it was confirmed that the glycosides were most effectively separated when butanol was used as shown in FIG. Galactic acid glycosides were separated by butanol extraction, silica gel column and u-Bondapak C18 (300 x 19 mm) column. Separation conditions were A solvent (water containing 0.1% formic acid) and B solvent (methanol containing 0.1% formic acid), flow rate was 0.5 ml / min and UV was measured at 245 nm.
실시예 3. 갈릭산 배당체 분리Example 3. Galactic acid glycoside separation
배당체 생성 후 부탄올 추출로 얻어진 상등액을 회전증발기(rotary evaporator)로 50℃에서 농축 후(50 ㎖) 실리카 겔 칼럼(50 x 900 mm)에 로딩하였다. 추출액에 남아있는 설탕이나 효소 등(dextran, fructose, 및 glucose)을 없애기 위해 칼럼을 3차 증류수로 씻은 후(총 500㎖, 유속 분당 1㎖) 연속적으로 50% (v/v) 메탄올로 (1 L)로 얻어냈다. 갈릭산, 갈릭산 배당체를 함유하고 있는 추출액은 다시 47℃, 회전증발기로 농축 후 HPLC on an PDA-MD2015 instrument(JASCO, 일본) 에 순수분리를 위해 로딩하였다. 칼럼은 u-Bondapak C18-reverse-phase column (300 x 19 mm i.d., Waters)를 사용해서 A 용매(0.1% formic acid가 함유된 물) 와 B 용매(0.1% formic acid가 함유된 메탄올)를 A 용매를 95%~85%까지 10분간, 85%~60% 10분간, 유속은 0.4㎖/min, 추출액은 254nm에서 MD2015 model PDA detector(JASCO)를 사용해서 분석하였다. 칼럼 오븐 온도는 40℃였다. 갈릭산 배당체는 LC/MS/MS 분석을 통해 분자량 및 분자식을 밝혔다. 배당체들은 ESI-MS/MS(electrospray ionization tandem mass spectrometry)를 사용했으며 Positive ESI-MS 분석은 Synapt HDMS system(Waters)을 사용, lock spray interface를 갖는 electro spray ionization source로 분석하였다.The supernatant obtained by the butanol extraction after the generation of the glycoside was loaded on a silica gel column (50 x 900 mm) after concentration (50 ml) at 50 ° C with a rotary evaporator. The column was washed with tertiary distilled water (total 500 ml, 1 ml per flow rate) to remove residual sugar and enzymes (dextran, fructose, and glucose) in the extract and successively washed with 50% (v / v) L). The extract containing galactic acid and gallic acid glycosides was again concentrated at 47 ° C on a rotary evaporator and then loaded on a HPLC on an PDA-MD2015 instrument (JASCO, Japan) for pure separation. The column was washed with A solvent (water containing 0.1% formic acid) and B solvent (methanol with 0.1% formic acid) using a u-Bondapak C18 reverse-phase column (300 x 19 mm id, Waters) The solvent was analyzed from 95% to 85% for 10 minutes, 85% to 60% for 10 minutes, the flow rate was 0.4 ml / min, and the extract was analyzed using MD2015 PDA detector (JASCO) at 254 nm. The column oven temperature was 40 占 폚. Galactic acid glycoside revealed molecular weight and molecular formula through LC / MS / MS analysis. ESI-MS / MS (electrospray ionization tandem mass spectrometry) was used for the glycosides. Positive ESI-MS analysis was performed using Synapt HDMS system (Waters) using electro spray ionization source with lock spray interface.
갈릭산 배당체를 부탄올, 실리카 겔 칼럼 및 C18-역상 HPLC를 이용하여 추출한 후, 분리해서 LC/MS/MS를 통해 구조를 분석한 결과, 배당체의 분자량은 355.06로 분자 조성은 C13H16O10Na으로 확인했으며, 생성물은 갈릭산에 글루코스가 한 개 붙어 있으며, 최종 산물은 α-1,3 결합을 주로 하는 효소의 주요 특성을 통해 갈릭산-3-O-α-D-글루코피라노시드(gallic acid-3-O-α-D-glucopyranoside, 화학식 1 참조)로 판명되었으며, 배당체 생성효율은 갈릭산 38% 또는 123 mM을 차지하였다(도 3 및 도 4).
The molecular weight of the glycosides was 355.06 and the molecular composition was C 13 H 16 O 10. The molecular weight of the glycosides was 355.06. The molecular weight of the glycosides was 355.06, Na, and the product is attached to galactic acid with one glucose, and the final product is the galactic acid-3- O- alpha -D-glucopyranoside (gallic acid-3- O- alpha -D-glucopyranoside, see Chemical Formula 1), and the glycoside production efficiency was 38% or 123 mM of gallic acid (FIGS. 3 and 4).
실시예Example 4. 4. 갈릭익산의Garlic Iksan 배당체 생성 최적화 (중심합성계획법과 반응표면 분석법) Optimization of glycoside production (central synthetic design and reaction surface analysis)
갈릭산의 배당체는 10~700 mM 수크로스와 61~1238 mU/㎖ 효소, 그리고 30~619 mM 갈릭산을 24시간 반응시켜 얻었다. 갈릭산의 배당체 생성 최적조건을 얻기 위해 반응표면 분석법(RSM)을 이용하였다. 갈릭산의 배당체 생성에 대한 실험계획은 중심합성계획법을 실시하여 생성 조건에 대한 중요한 독립변수로(Xi) 고려되는 인자, 즉 기질 농도(X1), 효소 농도(X2), 그리고 수용체 농도(갈릭산, X3)에 대한 실험범위를 설정하여 각 5단계로 부호화하여(표 1) 20 군으로 구분하였다(표 2). 그리고 이들 독립변수에 의해 영향 받는 종족변수(Yn), 즉 갈릭산 배당체의 생성농도를 측정하여 그 값을 회귀분석에 사용하였다.Galactic acid glycosides were obtained by reacting 10-700 mM sucrose, 61-1238 mU / ㎖ enzyme, and 30-619 mM gallic acid for 24 hours. Response surface methodology (RSM) was used to obtain optimum glycoside production of gallic acid. Experimental plan for the production of glycosides of glycyrrhiza was carried out by the central synthetic design method and the factors considered as important independent variables for the production conditions (X i ) were the factors considered: substrate concentration (X 1 ), enzyme concentration (X 2 ) (Galic acid, X 3 ) were set up and coded into 5 levels (Table 1) and classified into 20 groups (Table 2). In addition, the tributary variables (Yn) affected by these independent variables, ie, the production concentration of gallic acid glycosides, were measured and used for regression analysis.
최적 갈릭산 배당체의 생성조건은 반응표면분석으로 얻어진 수크로스 농도, 덱스트란수크라제 농도, 갈릭산 농도 등의 contour map을 superimaging했을 때 중복되는 부분의 범위로 예측하였다(도 4 참조). 통계 프로그램은 Design-Expert 6.0.11을 이용하여, regression 분석과 그래프를 얻기 위해 사용되었다.The optimum conditions for the production of galactic acid glycoside were predicted as overlapping regions when superimaging the contour map such as sucrose concentration, dextran sucrose concentration and gallic acid concentration obtained by the reaction surface analysis (see FIG. 4). The statistical program was used to obtain regression analysis and graphs using Design-Expert 6.0.11.
Y = -158.9 + 0.32X1 + 0.24X2 + 0.63X3 - 0.00047X1 2 - 0.00013X2 2 - 0.00089X3 2 + 0.0000139X1X2 - 0.000011X1X3 - 0.000062X2X3 Y = -158.9 + 0.32X 1 + 0.24X 2 + 0.63X 3 - 0.00047X 1 2 - 0.00013X 2 2 - 0.00089X 3 2 + 0.0000139X 1 X 2 - 0.000011X 1 X 3 - 0.000062X 2 X 3
(Y= 갈릭산 배당체 생성량(mM), X1=설탕 농도, X2=효소 농도, X3=갈릭산 농도)
(Y = amount of galactic acid glycosides produced (mM), X 1 = sugar concentration, X 2 = enzyme concentration, X 3 =
실시예Example 5. 5. 갈릭산Garlic Mountain 배당체의 기능성 조사 Functional investigation of glycoside
1) 항산화(Electron donating ability) 효과1) Electron donating ability effect
항산화 효능은 1,1-diphenyl-2-picrylhydrazyl(DPPH)을 이용하여 라디칼 소거능(radical scavenging activity)을 측정하였다. 96-웰 플레이트에 100 μM DPPH 에탄올 용액에 농도별로 희석한 시료용액을 가하여 37℃에서 30분 동안 반응시킨 후 VERSAmax, microplate reader(Molecular Devices, 미국)를 이용하여 515㎚에서 흡광도를 측정하였다. 항산화 효능은 흡광도가 50% 감소할 때 나타나는 시료의 라디칼 소거능(RC50)으로 표시하였으며, 3회 반복 실험하여 데이터를 구하였다.The antioxidant activity was measured by radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH). The diluted sample solution was added to 100 μM DPPH ethanol solution in a 96-well plate and incubated at 37 ° C for 30 minutes. Absorbance was measured at 515 nm using a VERSAmax microplate reader (Molecular Devices, USA). The antioxidant efficacy was expressed as the radical scavenging ability (RC50) of the sample when the absorbance was reduced by 50%, and data were obtained by repeating the experiment three times.
항산화력(DPPH법 이용)은 비타민 C의 RC50이 0.41 mM일 경우, 갈릭산 배당체의 RC50은 0.94 mM이고, 갈릭산의 RC50은 0.13 mM로 더 낮은 효과를 보였다(도 5).
When the RC50 of vitamin C was 0.41 mM, the antioxidant power (using the DPPH method) showed a lower effect of galactic acid glycosides RC50 of 0.94 mM and gallic acid RC50 of 0.13 mM (Fig. 5).
2) 아질산소거능 (nitrite scavenging ability) 측정2) Measurement of nitrite scavenging ability
Nitric oxide 소거능은 Marcocco 등의 방법에 의해 측정하였다. 10mM 니트로프루시드 나트륨(sodium nitroprusside) 수용액 2㎖에 0.01M 인산완충액(pH 7.4) 0.5㎖ 와 시료 용액 0.5㎖를 가하여 25℃에서 100 분간 반응시켰다. 이 반응액을 1㎖ 취해 술파닐산(sulfanilic acid)(0.33% in 20% acetic acid) 1㎖ 와 혼합한 후 5분간 방치하였다. 여기에 0.1%(w/v) 나프틸에틸렌-디아민 디하이드로클로라이드(naphthylethylene-diamine dihydrochloride) 용액(in 20% acetic acid)를 1㎖ 가하여 30분간 방치 후 540nm에서 흡광도를 측정하였다.Nitric oxide scavenging activity was measured by Marcocco et al. 0.5 ml of 0.01 M phosphate buffer solution (pH 7.4) and 0.5 ml of the sample solution were added to 2 ml of a 10 mM sodium nitroprusside aqueous solution and reacted at 25 ° C for 100 minutes. 1 ml of this reaction solution was taken and mixed with 1 ml of sulfanilic acid (0.33% in 20% acetic acid), and left for 5 minutes. 1 ml of a 0.1% (w / v) naphthylethylene-diamine dihydrochloride solution (in 20% acetic acid) was added and left for 30 minutes, and the absorbance was measured at 540 nm.
아질산소거능 효과는 1mM의 비타민 C가 69%의 소거능을 보였을 경우, 갈릭산과 갈릭산 배당체는 각각 61%와 67%을 나타내어 갈릭산 배당체의 소거능이 더 높았다(도 6).
The nitrite - scavenging activity of gallic acid and galactic acid was 61% and 67%, respectively, when 1 mM of vitamin C showed 69% cleavage (Fig. 6).
3) 지질산패억제 효과3) Effect of inhibition of lipid peroxidation
지질산패억제 효과는 화학발광(chemiluminescence)을 이용하는 항산화 측정 장치인 HP-CLA(일본)와 ABCD GmbH(독일)로부터 루미놀-자유 라디칼(luminol+free radical)이 들어있는 ARA-L kit가 사용되었다. 시료의 항지질산화력이 소모될 때까지 앰플 안에 있는 루미놀-자유 라디칼이 반응하여 광자(photons) 생성을 지연시킨다. 이때 생성된 그래프의 lag time(초)이 시료의 항산화력을 결정한다. 항산화력 표준곡선을 얻기 위해 비타민 E가 0, 10, 20, 30, 40, 50 μM로 첨가하였다. 시료 또는 표준물질은 20㎕를 첨가하였다.The effect of inhibiting lipid peroxidation was measured by HP-CLA (Japan), an antioxidant measuring device using chemiluminescence, and ARA-L kit containing luminol + free radical from ABCD GmbH (Germany). The luminol-free radical in the ampoule reacts to delay the photons generation until the sample's antioxidant capacity is consumed. The lag time (seconds) of the generated graph determines the antioxidant capacity of the sample. Vitamin E was added at 0, 10, 20, 30, 40, and 50 μM to obtain the antioxidant power standard curve. 20 μl of sample or reference material was added.
항산화 측정기, 화학발광제가 부착된 자유 라디칼 및 루미놀 사용시 항지질 산패효과는 1 mM 농도로 측정시, 갈릭산 배당체가 44.1μM 비타민 E 효과를 보여서 갈릭산의 33.9 μM 비타민 E 효과보다 높았다(도 7).
The effect of antioxidant, chemiluminescent free radicals and luminol on lipid peroxidation was higher than that of galactic acid (33.9 μM vitamin E) as shown by the effect of galactic acid glycosides 44.1 μM vitamin E (Fig.7) .
4) 티로시나제(tyrosinase) 효소 억제 효과 (미백효과)4) Tyrosinase enzyme inhibitory effect (whitening effect)
0.33mM 인산완충액(pH 7)에 3.3 mM L-DOPA(3-(3,4-dihydroxyphenyl)-L-alanine) 기질과 효소(15 Unit/㎖) 첨가 또는 무첨가(대조구) 총 90㎕ 반응액을 이용해 효소억제정도를 조사하였다. 억제물질로 1mM 농도의 비타민 C, α-알부틴(α-arbutin), 갈릭산, 갈락산 배당체(GG)에 대한 버섯 유래 티로시나제 효소의 활성을 L-DOPA 기질(1mM)에 따라 흡광도 475nm에서 측정하였다. A total of 90 μl reaction solution was added to 0.33 mM phosphate buffer (pH 7) with or without 3.3 mM L-DOPA (3- (3,4-dihydroxyphenyl) -L-alanine) substrate and enzyme (15 Unit / And the degree of enzyme inhibition was examined. The activity of mushroom-derived tyrosinase enzyme for 1 mM concentration of vitamin C, α-arbutin, galactic acid and galactanic acid glycoside (GG) as inhibitor was measured at 475 nm according to L-DOPA substrate (1 mM) .
멜라닌 생성억제 효과로, 버섯 유래 티로시나제 효소를 가지고 실험한 결과, 비타민 C는 80.2%, 알부틴은 42.2%, 갈릭산은 35.6%, 갈릭산배당체는 50.2%로 티로시나제 억제율을 나타내어, 갈릭산 배당체는 갈릭산이나 알부틴보다 41% 또는 18% 더 높은 미백효과가 있었다(도 8).
As a result of the experiment with mushroom-derived tyrosinase enzyme, it was found that the inhibition rate of tyrosinase was 80.2% for vitamin C, 42.2% for arbutin, 35.6% for gallic acid and 50.2% for gallic acid glycoside, Or 41% or 18% higher than arbutin (Fig. 8).
5) 콜라겐 생성 및 MMP(matrix metalloproteinase)-1 효소 억제 정도 (주름예방효과)5) Collagen production and MMP (matrix metalloproteinase) -1 enzyme inhibition (wrinkle prevention effect)
MMP는 기질금속단백질분해효소(matrix metalloproteinase)로 아연-의존 엔도프로티아제(Zinc dependent endoprotease)로 MMP-1은 간질성 콜라게나제(interstitial collagenase)로 피부에 UV 노출시 증가되어 타입 I 또는 III 콜라겐(collagen)을 분해하는 효소이다.MMP is a matrix metalloproteinase, which is a zinc-dependent endoprotease. MMP-1 is an interstitial collagenase, which is increased by UV exposure to the skin. Type I or III It is an enzyme that breaks down collagen.
인간 피부 상피 세포(Human newborn foreskin fibroblast)인 HS68 세포주(ATCC CRL 1635, USA)를 이용해 세포가 80% confluence에 도달하면 UVB 광(312 nm, Spectroline Model EB-160C, 미국) 조사후 새 배지를 첨가하여 24시간 배양하였다. UVB(100 mJ/cm2) 조사하기 전에 알부틴, 갈릭산 및 갈릭산 배당체(5, 10~100μM)를 미리 처리하였다. 이때 생성된 콜라겐 함량과 MMP-1 효소량은 웨스턴 블롯을 이용해 조사하였다. 콜라겐(type 1 & 3) 함량은 웨스턴 블롯과 RT-PCR을 이용해 조사하였다. RT-PCR에 사용된 프라이머 서열은 Col type 1 정방향 프라이머(cgaaggttcccctggacgagacg; 서열번호 1) 및 역방향 프라이머(ggcacaagggatgacacgcgttc; 서열번호 2), Col type 3 정방향 프라이머(gacgggtgaaccgggtattgc; 서열번호 3) 및 역방향 프라이머(acttctcccttctcgccgttag; 서열번호 4)를 사용하였다.When cells reached 80% confluence using HS68 cell line (human newborn foreskin fibroblast) (ATCC CRL 1635, USA), new medium was added after UVB light (312 nm, Spectroline Model EB-160C, USA) And cultured for 24 hours. Arbutin, gallic acid and gallic acid glycosides (5, 10-100 μM) were pretreated before irradiation with UVB (100 mJ / cm 2 ). The amount of collagen produced and the amount of MMP-1 enzyme were examined by Western blotting. Collagen (
주름예방 효과 조사 결과로, 인간 상피세포주를 이용해 콜라겐(type 1) 생성량 및 주름생성관련 효소 MMP-1(interstitial collagenase) 생성량을 측정하였다. 갈릭산과 그 배당체를 10~100μM 농도범위로 처리한 후 UV 노출된 세포로부터 Total RNA를 추출해 RT-PCR한 결과, 콜라겐 생성량은 갈릭산 배당체> 알부틴> 갈릭산 순으로 갈릭산 배당체가 알부틴이나 갈릭산보다 높았다(도 9A). 또한 이와 유사한 결과를 웨스턴 블롯 분석을 통해 재확인 하였다(도 9B). 또한 이 웨스턴 블롯의 140kDa 크기의 lower band를 NIH densitometry program을 이용해 밴드의 밀도를 정량화 하였다(도 9B). 갈릭산 배당체는 25μM부터 100μM 까지 높은 콜라겐 함량을 나타내 적은 농도에서도 주름방지 효과를 보이는 것을 관찰하였다. 특히 100μM 농도의 시료 처리에서, 콜라겐 생성량은 control을 100%로 간주시, 갈릭산 배당체가 258%로 갈릭산 177%보다 45.7% 콜라겐 생성량이 높았다(도 9B). 또한 UV에 노출 후 주름생성효소인 MMP-1 효소 생성량을 조사한 결과, 100μM 시료 처리시, MMP-1 효소는 무처리 100%, UVB 처리시 200% 대비, 알부틴 170%, 갈릭산 175%와 갈릭산 배당체 153%로 갈락산 배당체가 가장 적게 생겼으며 알부틴보다 주름생성억제 효과가 높게 관찰되었다(도 10).
As a result of the wrinkle prevention effect, collagen (type 1) production and wrinkle-related enzyme MMP-1 (interstitial collagenase) production amount were measured using human epithelial cell line. Total RNA was extracted from UV-exposed cells after treatment with gallic acid and its glycosides in a concentration range of 10 to 100 μM. As a result of RT-PCR, the amount of collagen production was found to be as follows: gallic acid glycosides>arbutin> (Fig. 9A). Similar results were reaffirmed by western blot analysis (Fig. 9B). In addition, the density of the band was quantified using the NIH densitometry program in the lower band of the 140-kDa band of the western blot (Fig. 9B). Galactic acid glycosides showed high collagen content from 25 μM to 100 μM and showed wrinkle preventing effect even at low concentrations. In particular, when 100 μM of the sample was treated with 100 μM of the control, the amount of collagen produced was 258% of galactic acid glycosides and 45.7% of collagen production was higher than that of 177% of galactic acid (FIG. In addition, the amount of MMP-1 enzyme produced after exposure to UV was 100% for MMP-1 enzyme treatment, 200% for UVB treatment, 170% for arbutin, 175% for gallic acid, 153% of the acid glycoside showed the least amount of galactanic acid glycosides and the wrinkle formation inhibitory effect was higher than that of arbutin (FIG. 10).
실시예 6. 관능 시험Example 6. Sensory test
<제조예><Production Example>
반응혼합물(250㎖)은 0.32M 갈릭산(27.2 g), 355mM 수크로스(60.7 g), 덱스트란수크라제(0.65 units/㎖)로 구성되어, 상기 혼합물을 37℃에서 12시간 반응시킨 후, 5분간 가열하여 효소반응을 정지시켜, 갈릭산 당전이 유사체(GG)를 준비하였다.
The reaction mixture (250 ml) consisted of 0.32 M galic acid (27.2 g), 355 mM sucrose (60.7 g) and dextran sucurease (0.65 units / ml) , And the reaction was stopped by heating for 5 minutes to prepare an analogue (GG) of gallic acid.
<비교예><Comparative Example>
0.32M 갈릭산(27.2 g)를 그대로 갈릭산(GA)으로 준비하였다.
0.32 M galactic acid (27.2 g) was prepared as it was as galactic acid (GA).
상기 제조예 및 비교예를 통해서 제조된 GG 및 갈릭산을 80℃ 온수에 녹여 훈련된 관능검사 요원 20명을 대상으로 3회의 반복에 의한 관능 평가를 실시하였다. 관능검사 항목은 용해도, 향, 맛, 전체적인 기호도에 대하여 실시하였으며 5점 척도법에 따라 5점을 만점으로 하여 다음의 평가기준에 의하여 피시험자가 점수를 기록한 후 이들의 평균값을 구하여 기록하였다. GG and gallic acid prepared by the above preparation examples and comparative examples were dissolved in hot water at 80 ° C. and sensory evaluation was carried out by repeating the triple
5: 아주 좋다 ~ 1: 아주 나쁘다 5: Very good ~ 1: Very bad
본 발명의 제조예에 의하여 제조된 GG가 비교예보다 향과 맛에서 높은 관능적 점수를 보였으며, 용해도도 매우 높은(실험적으로 거의 녹지 않았는데 12mM 또는 2.04㎎/㎖ 녹을 수 있게 증가됨) 것으로 나타났다.The GG prepared according to the preparation example of the present invention showed a higher sensory score in flavor and taste than the comparative example, and the solubility was also very high (experimentally, it was almost insoluble but increased to melt 12 mM or 2.04 mg / ml).
<110> INDUSTRY FOUNDATION OF CHONNAM NATIONAL UNIVERSITY <120> Composition for improving skin whitening and wrinkle comprising gallic acid glycoside as effective component <130> PN16289 <160> 4 <170> KopatentIn 2.0 <210> 1 <211> 23 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 1 cgaaggttcc cctggacgag acg 23 <210> 2 <211> 23 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 2 ggcacaaggg atgacacgcg ttc 23 <210> 3 <211> 21 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 3 gacgggtgaa ccgggtattg c 21 <210> 4 <211> 22 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 4 acttctccct tctcgccgtt ag 22 <110> INDUSTRY FOUNDATION OF CHONNAM NATIONAL UNIVERSITY <120> Composition for improving skin whitening and wrinkling gallic acid glycoside as effective component <130> PN16289 <160> 4 <170> Kopatentin 2.0 <210> 1 <211> 23 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 1 cgaaggttcc cctggacgag acg 23 <210> 2 <211> 23 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 2 ggcacaaggg atgacacgcg ttc 23 <210> 3 <211> 21 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 3 gacgggtgaa ccgggtattg c 21 <210> 4 <211> 22 <212> DNA <213> Artificial Sequence <220> <223> primer <400> 4 acttctccct tctcgccgtt ag 22
Claims (8)
a) 수용체 물질로서 0.1~1M 갈릭산, 기질로서 0.1~1M 설탕 및 덱스트란수크라제 효소가 포함된 혼합물을 준비하는 단계;
b) 상기 혼합물을 28~38℃에서 2~24시간 동안 반응시키는 단계; 및
c) 상기 반응시킨 혼합물에 부탄올을 첨가하여 갈릭산 배당체를 분리하는 단계.The cosmetic composition for skin whitening and wrinkling according to claim 1, wherein the galactic acid glycoside is produced through the following steps:
a) preparing a mixture comprising 0.1-1 M galactic acid as a receptor substance, 0.1-1 M sugar as a substrate and dextran sucrose enzyme;
b) reacting the mixture at 28 to 38 DEG C for 2 to 24 hours; And
c) adding butanol to the reaction mixture to separate the gallic acid glycosides.
Y = -158.9 + 0.32X1 + 0.24X2 + 0.63X3 - 0.00047X1 2 - 0.00013X2 2 - 0.00089X3 2 + 0.0000139X1X2 - 0.000011X1X3 - 0.000062X2X3.3. The method according to claim 2, wherein the optimal production of the galactic acid glycosides is carried out by the following regression equation derived from the reaction surface analysis method in which the substrate (X 1 ), the enzyme (X 2 ) and the receptor substance (X 3 ) The cosmetic composition for skin whitening and wrinkle improvement according to claim 1,
Y = -158.9 + 0.32X 1 + 0.24X 2 + 0.63X 3 - 0.00047X 1 2 - 0.00013X 2 2 - 0.00089 X 3 2 + 0.0000139 X 1 X 2 - 0.000011X 1 X 3 - 0.000062X 2 X 3 .
a) 수용체 물질로서 0.1~1M 갈릭산, 기질로서 0.1~1M 설탕 및 덱스트란수크라제 효소가 포함된 혼합물을 준비하는 단계;
b) 상기 혼합물을 28~38℃에서 2~24시간 동안 반응시키는 단계; 및
c) 상기 반응시킨 혼합물에 부탄올을 첨가하여 갈릭산 배당체를 분리하는 단계.The health food composition for skin whitening and wrinkling according to claim 6, wherein the galactic acid glycosides are prepared by the following steps:
a) preparing a mixture comprising 0.1-1 M galactic acid as a receptor substance, 0.1-1 M sugar as a substrate and dextran sucrose enzyme;
b) reacting the mixture at 28 to 38 DEG C for 2 to 24 hours; And
c) adding butanol to the reaction mixture to separate the gallic acid glycosides.
Y = -158.9 + 0.32X1 + 0.24X2 + 0.63X3 - 0.00047X1 2 - 0.00013X2 2 - 0.00089X3 2 + 0.0000139X1X2 - 0.000011X1X3 - 0.000062X2X3.The method of claim 7, wherein the gallic optimal generation of acid glycoside is by the regression equation to be derived by the substrate (X 1), the response surface analysis for the enzyme (X 2), the receptor material (X 3) to the main variable Wherein the composition is prepared under optimized conditions.
Y = -158.9 + 0.32X 1 + 0.24X 2 + 0.63X 3 - 0.00047X 1 2 - 0.00013X 2 2 - 0.00089X 3 2 + 0.0000139X 1 X 2 - 0.000011X 1 X 3 - 0.000062X 2 X 3 .
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| KR20220111340A (en) * | 2021-02-02 | 2022-08-09 | 대구대학교 산학협력단 | Composition for anti-wrinkle comprising compound isolated from gallic acid oxide as effective component |
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| KR20200030346A (en) * | 2018-09-12 | 2020-03-20 | 주식회사 엘지생활건강 | A composition for promoting the proliferation of human adipose derived stem cell |
| KR20220111340A (en) * | 2021-02-02 | 2022-08-09 | 대구대학교 산학협력단 | Composition for anti-wrinkle comprising compound isolated from gallic acid oxide as effective component |
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