KR101276306B1 - Skin whitening composition containing dehydroglyasperin c, dehydroglyasperin d or isoangustone a - Google Patents
Skin whitening composition containing dehydroglyasperin c, dehydroglyasperin d or isoangustone a Download PDFInfo
- Publication number
- KR101276306B1 KR101276306B1 KR1020120087736A KR20120087736A KR101276306B1 KR 101276306 B1 KR101276306 B1 KR 101276306B1 KR 1020120087736 A KR1020120087736 A KR 1020120087736A KR 20120087736 A KR20120087736 A KR 20120087736A KR 101276306 B1 KR101276306 B1 KR 101276306B1
- Authority
- KR
- South Korea
- Prior art keywords
- dihydrogliasperin
- dehydroglyasperin
- skin whitening
- isoangustone
- active ingredient
- Prior art date
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
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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
- 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
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
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- Polymers & Plastics (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
본 발명은 피부 미백용 조성물에 대한 것으로, 더욱 상세하게는 디하이드로글리아스페린(dehydroglyasperin) C 또는 디하이드로글리아스페린(dehydroglyasperin) D 또는 이소앙구스톤(isoangustone) A를 함유하는 피부 미백용 조성물에 관한 것이다.
The present invention relates to a composition for skin whitening, and more particularly to a composition for skin whitening containing dehydroglyasperin C or dehydroglyasperin D or isoangustone A. It is about.
최근 삶의 질이 향상되고 평균 수명이 늘어나면서 아름답게 나이를 먹는 것에 대한 욕구가 강해졌으며, 외적 요인이 사회생활의 중요한 경쟁력으로 인식되면서 피부에 대한 관심도 증대되었다. 이러한 추세에 부응하여 기능성 화장품 분야의 시장 규모도 확대되고 있는데, 특히 천연물을 활용한 기능성 화장품 연구가 급속히 진행되고 있다.Recently, as the quality of life has improved and the average life expectancy has increased, the desire to age beautifully has become stronger, and as external factors are recognized as an important competitiveness of social life, interest in the skin has also increased. In response to this trend, the market scale of functional cosmetics is also expanding. In particular, research on functional cosmetics using natural products is rapidly progressing.
동서고금을 막론하고 백옥같은 얼굴은 오래전부터 미의 기준으로 간주되어 왔으며, 피부 미용에 있어 '미백'은 많은 여성들이 가장 신경 쓰는 부분 중 하나이다. Regardless of east and west, white jade face has long been regarded as a standard of beauty, and 'whitening' is one of the most caring parts of women in skin care.
인체의 피부색은 일반적으로 멜라닌, 산화-환원 헤모글로빈, 카로틴, 멜라노이드에 의해 결정되는데, 이 중에서 가장 큰 영향을 미치는 것은 멜라닌이다. 멜라닌은 표피의 기저층에 존재하는 멜라노사이트(melanocyte) 내 멜라노좀(melanosome)에서 만들어진다. 피부가 자외선을 받게 되면 티로신(tyrosine)이 티로시나아제(tyrosinase)라는 효소에 의해 산화되어 도파(DOPA, 3,4-dihydro xyphenylalanine)가 생성된다. 이것이 다시 산화되어 도파퀴논(dopaquinone)으로 전환되고, 도파퀴논은 비효소적인 산화반응을 거쳐 피부색소 침착 현상의 원인이 되는 멜라닌을 형성한다. The skin color of the human body is generally determined by melanin, redox hemoglobin, carotene and melanoids, of which melanin has the greatest effect. Melanin is made from melanosomes in melanocytes present in the basal layer of the epidermis. When the skin is exposed to ultraviolet rays, tyrosine is oxidized by an enzyme called tyrosinase to produce dopa (DOPA, 3,4-dihydro xyphenylalanine). It is oxidized again and converted to dopaquinone, and dopaquinone undergoes nonenzymatic oxidation to form melanin which causes skin pigmentation.
멜라닌은 자외선을 차단하여 진피 이하의 피부 기관을 보호해 주는 동시에, 피부 생체 내에 생겨난 자유 라디칼 등에 의한 피부 내 단백질과 유전자들의 손상을 보호해 주는 유용한 역할을 한다. 하지만, 멜라닌이 필요 이상으로 많이 생기게 되면 피부 노화나 기미, 주근깨 등과 같은 과색소침착증을 유발하며 피부암의 원인이 되기도 한다. 따라서, 미용욕구 충족뿐만 아니라 피부 건강 유지 및 피부 질환 치료를 위해서도 과도한 멜라닌의 생성은 억제되어야 한다. Melanin protects skin organs under the dermis by blocking UV rays, and also plays a useful role in protecting proteins and genes in the skin from free radicals generated in the skin. However, when more melanin is produced than necessary, it causes skin pigmentation such as skin aging, blemishes, and freckles. Therefore, excessive melanin production should be suppressed not only for satisfying beauty needs but also for maintaining skin health and treating skin diseases.
멜라닌의 합성을 억제하는 방법으로는 적절한 자외선 차단제를 함유한 화장료를 사용하여 자외선에 대한 노출을 방지 또는 감소시키거나, 멜라닌 합성 세포인 멜라노사이트의 세포활성을 저해시키는 방법, 티로시나아제의 활성을 억제하여 멜라닌 합성을 억제하는 방법 등이 있다. 하지만, 현재 티로시나아제의 억제제로 개발되어 있는 알부틴(arbutin), 코직산(5-hydroxy-2-hydormethyl-v-pyrone), 하이드로퀴논(hydroquinone) 등의 물질들은 낮은 저해활성 및 물질 자체의 불안정성, 그리고 피부에 대한 독성의 문제점을 가지고 있다. 따라서, 피부 독성이 없고 안정하며 멜라닌 생성억제효과가 높은 천연의 저해물질이 필요한 실정이다.Examples of the method for inhibiting the synthesis of melanin include a method of preventing or reducing exposure to ultraviolet rays using a cosmetic agent containing a suitable ultraviolet screening agent, a method of inhibiting melanocyte cytosine activity of melanocyte synthesis cells, a method of inhibiting tyrosinase activity And inhibiting the synthesis of melanin. However, materials such as arbutin, 5-hydroxy-2-hydormethyl-v-pyrone, and hydroquinone, which are currently developed as inhibitors of tyrosinase, have low inhibitory activity and instability of the material itself, And it has a problem of toxicity to the skin. Therefore, there is a need for a natural inhibitor that is not toxic to skin and stable and has a high melanin inhibitory effect.
최근에는 천연물, 특히 식물 중에서 미백 활성 성분을 찾기 위한 연구가 활발하며, 다수의 식물 추출물 및 생약재 추출물 등이 티로시나제에 작용하여 멜라닌의 생성을 억제한다는 사실이 밝혀졌다. 그러나, 이들 역시 안전성, 변색 가능성 등의 측면에서 화장품 또는 의약품에 유효 농도 이상으로 첨가하는데에는 많은 문제점이 있다. 또한, 활성 유효 성분 및 이들의 효능이 명확히 규명되어 있지 못한 문제점도 있다.Recently, research has been actively conducted to find a whitening active ingredient among natural products, especially plants, and it has been found that many plant extracts and herbal extracts act on tyrosinase to inhibit melanin production. However, these also have many problems in addition to the effective concentration in cosmetics or pharmaceuticals in terms of safety, discoloration potential. In addition, there are problems that the active active ingredients and their efficacy are not clearly identified.
이에 본 발명자들은 감초 추출물의 유효 성분에 대해 연구하던 중, 감초 추출물에서 분리한 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A가 티로시나아제의 활성을 억제하고 멜라닌 생성을 저해한다는 사실을 규명함으로써 본 발명을 완성하였다.
Therefore, while the present inventors studied the active ingredient of licorice extract, dihydrogliasperin C or dihydrogliasperin D or isoangustone A isolated from licorice extract inhibits the activity of tyrosinase and inhibits melanin production. The present invention has been completed by identifying the fact of inhibition.
본 발명은 피부 미백 효과가 있는 천연활성물질을 새롭게 발굴하여, 이를 유효성분을 함유하는 피부 미백용 조성물로 개발하여 제공하고자 한다.
The present invention is to newly discover a natural active substance having a skin whitening effect, to develop and provide a composition for skin whitening containing the active ingredient.
본 발명은 제1형태로, 하기 화학식 1의 구조를 갖는 디하이드로글리아스페린 C를 유효성분으로 함유하는 피부 미백용 조성물을 제공한다.The present invention provides, in a first aspect, a composition for skin whitening containing dihydrogliasperin C having a structure of formula (1) as an active ingredient.
[화학식 1][Formula 1]
또한, 본 발명은 제2형태로, 하기 화학식 2의 구조를 갖는 디하이드로글리아스페린 D를 유효성분으로 함유하는 피부 미백용 조성물을 제공한다. In another aspect, the present invention provides a composition for skin whitening containing dihydrogliasperin D having the structure of formula (2) as an active ingredient.
[화학식 2][Formula 2]
또한, 본 발명은 제3형태로, 하기 화학식 3의 구조를 갖는 이소앙구스톤 A를 유효성분으로 함유하는 피부 미백용 조성물을 제공한다. In another aspect, the present invention provides a composition for skin whitening containing isoangustone A having a structure of formula (3) as an active ingredient.
[화학식 3](3)
한편, 상기 본 발명의 제1형태 내지 제3형태에 있어서, 상기 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A는, 일 예로 감초 유래인 것을 사용할 수 있다. In the first to third aspects of the present invention, the dihydrogliasperin C, the dihydrogliasperin D or the isoangustone A can be used, for example, from licorice.
한편, 상기 본 발명의 제1형태 내지 제3형태에 있어서, 상기 조성물은, 바람직하게 화장료 조성물 또는 식품 조성물일 수 있다.In the first to third aspects of the present invention, the composition may preferably be a cosmetic composition or a food composition.
이하, 본 발명에 대해 더욱 상세히 설명하고자 한다.
Hereinafter, the present invention will be described in more detail.
본 발명자들은 피부 미백 효과가 있는 생리활성물질을 탐색하는 과정에서 감초에 함유되어 있는 파이토케미칼(phytochemical)인 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A에 주목하게 되었다. The present inventors came to pay attention to the phytochemical dihydrogliasperin C or dihydrogliasperin D or isogustone A, which is a phytochemical contained in licorice, in the search for a bioactive substance having a skin whitening effect.
플라보노이드(flavonoid)는 꽃, 잎, 줄기 또는 과실 등 식물의 여러 부위에 함유되어 있는 천연의 항균 물질로서, 외부 자극으로부터 식물을 보호하고 색소를 형성하게 하는 등의 기능을 할 뿐만 아니라, 사람에게 있어 항산화성, 항균성, 항바이러스성, 항암성과 같은 생리 활성을 나타낸다(Havsteen,B.H. (2002) The biochemistry and medical significance of the flavonoids. Parmacol Ther 96, 67-202.). 감초는 이러한 플라보노이드(flavonoid)계 화합물을 다량 함유하고 있는데, 그 함량은 약 5.5% 정도이고(Kim,E.Y. et al . (2004) Screening of the antioxidant activity of some medicinal plants. Korean J Food Sci. Technol 36, 333-338.), 감초에 존재하는 디하이드로글리아스페린 C, 디하이드로글리아스페린 D, 이소앙구스톤 A는 프레닐화된 플라보노이드(prenylated flavonoid)로, 플라보노이드의 하위에 속한다. 이소프렌(isopren) 구조를 포함한 프레닐화된 플라보노이드는 식물성 에스트로젠으로 작용하거나 항산화성을 나타낸다고 알려져 있다(Dufall,K.G. et al . (2003) Antioxidant activity of prenylated flavonoids from the West African medicinal plant Dorstenia mannii. J Ethnopharmacol. 67-72.). Flavonoids are natural antibacterial substances contained in various parts of plants such as flowers, leaves, stems, or fruits, which not only function to protect plants from external stimuli and to form pigments, but also to humans. It exhibits physiological activities such as antioxidant, antimicrobial, antiviral and anticancer properties (Havsteen, BH (2002) The biochemistry and medical significance of the flavonoids. Parmacol Ther 96, 67-202.). Licorice contains a large amount of these flavonoid compounds, which are about 5.5% (Kim, EY et al . (2004) Screening of the antioxidant activity of some medicinal plants. Korean J Food Sci. Technol 36, 333-338.), Dihydrogliasperin C, dihydrogliasperin D, isoangustone A present in licorice are prenylated flavonoids, belonging to the lower flavonoids. Prenylated flavonoids containing isopren structures are known to act as phytoestrogens or exhibit antioxidant properties (Dufall, KG et al.). al . (2003) Antioxidant activity of prenylated flavonoids from the West African medicinal plant Dorstenia mannii. J Ethnopharmacol. 67-72.).
디하이드로글리아스페린 C, 디하이드로글리아스페린 D, 이소앙구스톤 A는 건조된 감초 뿌리를 메틸렌 클로라이드(methylene chloride) 또는 에틸 아세테이트(ethyl acetate)를 용매로 하여 추출한 후, 실리카겔 컬럼 크로마토그래피(silica gel column chromatography)를 통해 분리 및 정제할 수 있다. Dihydrogliasperin C, dihydrogliasperin D and isoangustone A were extracted from dried licorice roots using methylene chloride or ethyl acetate as a solvent, followed by silica gel column chromatography. It can be separated and purified by gel column chromatography.
현재까지 알려진 디하이드로글리아스페린 C, 디하이드로글리아스페린 D, 이소앙구스톤 A의 주된 생리기능은 항당뇨작용으로, 마우스에서 PPAR-(peroxisome proliferation activated receptor)의 경로를 활성화하여 내당능을 향상시키고 혈당 수치를 낮추는 작용을 하는 것으로 알려져 있다(Kuroda,M. et al . (2003) Phenolics with PPAR-gamma ligand-binding activity obtained from licorice (Glycyrrhiza uralensis roots) and ameliorative effects of glycyrin on genetically diabetic KK-A(y) mice. Bioorg Med Chem Lett. 4267-72.). 하지만, 이 등의 논문에서는, 혈액 중의 포도당(glucose)을 솔비톨(sorbitol)로 전환하는 효소인 알도스 리덕타제(aldose reductase)를 저해하는 데에는 낮은 효과를 나타내는 것으로 보고되었다(Lee,Y.S. et al . (2010) Aldose Reductase Inhibitory Compounds from Glycyrrhiza uralensis. Biol. Pharm. Bull. 917-921.). The main physiological functions of dihydrogliasperin C, dihydrogliasperin D, and isoangustone A, which are known to date, are antidiabetic, which activates the pathway of peroxisome proliferation activated receptor (PPAR-) in mice to enhance glucose tolerance. It is known to lower blood sugar levels (Kuroda, M. et . al . (2003) Phenolics with PPAR-gamma ligand-binding activity obtained from licorice (Glycyrrhiza uralensis roots) and ameliorative effects of glycyrin on genetically diabetic KK-A (y) mice. Bioorg Med Chem Lett. 4267-72.). However, in this paper, it has been reported to have a low effect on the inhibition of aldose reductase, an enzyme that converts glucose in the blood to sorbitol (Lee, YS et. al . (2010) Aldose Reductase Inhibitory Compounds from Glycyrrhiza uralensis. Biol. Pharm. Bull. 917-921.).
한편, 이소앙구스톤 A의 경우, 전립선 암세포인 DU145와 유방암 세포인 4T1의 세포주기를 차단하고 세포자가사멸(apoptosis)의 특징적인 현상인 DNA 응축을 증가시키며, 세포자가사멸(apoptosis) 관련 단백질인 Fas, TRAIL, Mel-1S와 카스파라아제(Caspase)-8, -9, -3, -7, 폴리(ADP-리보오스) 폴리머라아제(PARP)의 발현을 증가시키는 것으로 보고되었다. 또한, 세포주기 관련 단백질인 CDK2, CDK4, 사이클린(cyclin) A, 사이클린(cyclin) D1의 발현과 CDK2의 활성을 감소시켜 암세포의 증식을 억제하는 효과를 나타내는 것으로 보고되었다(Seon,M.R, et al . (2012) Hexane/ethanol extract of Glycyrrhiza uralensis and its active compound isoangustone A induce G1 cycle arrest in DU145 human prostate and 4T1 murine mammary cancer cells, J Nutr Biochem. 85-92.).On the other hand, isoanguston A blocks the cell cycle of DU145, a prostate cancer cell, and 4T1, a breast cancer cell, increases DNA condensation, a characteristic phenomenon of apoptosis, and is associated with apoptosis-related protein. It has been reported to increase the expression of Fas, TRAIL, Mel-1S and caspase-8, -9, -3, -7, poly (ADP-ribose) polymerase (PARP). In addition, it has been reported to reduce the expression of CDK2, CDK4, cyclin A, cyclin D1 and the activity of CDK2, which inhibits the proliferation of cancer cells (Seon, MR, et. al . (2012) Hexane / ethanol extract of Glycyrrhiza uralensis and its active compound isoangustone A induce G1 cycle arrest in DU145 human prostate and 4T1 murine mammary cancer cells, J Nutr Biochem. 85-92.).
한편, 본 발명에서는 디하이드로글리아스페린 C, 디하이드로글리아스페린 D, 이소앙구스톤 A의 티로시나아제 활성 억제 효과와 멜라닌 생성 저해 효과를 측정하였는데, 천연 티로시나아제 억제제인 알부틴과 비교했을 때, 더 낮은 농도에서 티로시나아제의 활성을 억제하고, 멜라닌 생성 세포에서 멜라닌 생성을 저해하는 것으로 나타났다. Meanwhile, in the present invention, the inhibitory effect on tyrosinase activity and melanin production of dihydrogliasperin C, dihydrogliasperin D and isoanguston A was measured, compared with arbutin, a natural tyrosinase inhibitor. Inhibitors of tyrosinase activity at lower concentrations and melanogenesis in melanogenesis cells.
한편, 본 발명은 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A를 미백능 발휘를 위한 유효성분으로 포함하는 것을 특징으로 하는 식품 조성물을 제공한다. 최근 먹는 화장품이 크게 유행하고 있는데, 먹는 화장품이란 기존에 피부에 바르는 화장품 형태를 넓게 확장시켜 새롭게 정립한 용어으로서, 피부에 좋은 기능성 성분을 피부에 바르는 것에 만족하지 않고, 음식처럼 먹음으로써, 피부에 특정 기능성을 발휘하게 하는 식품을 의미한다. On the other hand, the present invention provides a food composition comprising dihydrogliasperin C or dihydrogliasperin D or isoanguston A as an active ingredient for exhibiting whitening ability. In recent years, the cosmetics to be eaten are in great popularity, and the term cosmetics to be eaten is a newly established term that has been widely extended in the form of cosmetics applied to the skin, and is not satisfied with applying functional ingredients that are good for the skin to the skin, and by eating like food, It means a food to exhibit a specific functionality.
본 발명의 식품 조성물은 바람직하게 육류, 곡류, 카페인 음료, 일반음료, 초콜렛, 빵류, 스넥류, 과자류, 피자, 젤리, 면류, 껌류, 아이스크림류, 알코올성 음료, 술, 비타민 복합제 및 그 밖의 건강보조식품류 중 선택되는 어느 하나인 것인 것일 수 있으나, 반드시 이에 한정되는 것은 아니다. 식품 중에 첨가되는 양은 미백능 발휘를 위해 첨가되는 통상의 정도이면 좋다. The food composition of the present invention is preferably meat, grains, caffeine drinks, general beverages, chocolate, breads, snacks, confectionery, pizza, jelly, noodles, gums, ice creams, alcoholic beverages, alcohol, vitamin complexes and other health supplements It may be any one selected from, but is not necessarily limited thereto. The amount added in the food may be a normal degree added to exhibit the whitening ability.
한편, 본 발명은 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A를 미백능 발휘를 위한 유효성분으로 포함하는 것을 특징으로 하는 화장료 조성물을 제공한다. 화장료 조성물은 특정의 제형으로 반드시 국한되어야 하는 것이 아니고, 화장품으로 사용될 수 있는 모든 형태의 제형을 다 포함하는데, 그 예로는 화장수, 젤, 수용성 리퀴드, 크림, 에센스, 수중유(O/W)형 및 유중수(W/O)형으로 이루어진 기초화장료 제형, 수중유형 또는 유중수형의 메이크업베이스, 파운데이션, 스킨커버, 립스틱, 립그로스, 페이스파우더, 투웨이케익, 아이새도, 치크칼라 및 아이브로우펜슬류로 이루어진 색조화장료 제형 등이 있다. 화장품 중에 첨가되는 양은 미백능을 발휘하기 위해 첨가되는 통상의 정도이면 좋다.
On the other hand, the present invention provides a cosmetic composition comprising dihydrogliasperin C or dihydrogliasperin D or isoanguston A as an active ingredient for exhibiting whitening ability. Cosmetic compositions are not necessarily limited to particular formulations, and include all forms of formulations that can be used in cosmetics, such as lotion, gel, water soluble liquid, cream, essence, oil-in-water (O / W) type And W / O foundation cosmetic formulation, oil-in-water or water-in-oil makeup base, foundation, skin cover, lipstick, lip gloss, face powder, two-way cake, eye shadow, cheek color and eyebrow pencil Color cosmetic formulations and the like. The quantity added in cosmetics should just be a normal grade added in order to exhibit whitening ability.
상기에서 살펴본 바와 같이, 본 발명의 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A을 유효성분으로 함유하는 조성물은, 멜라닌 생성에 중요한 역할을 하는 효소인 티로시나아제의 활성을 억제하며, 특히 디하이드로글리아스페린 D의 경우, 티로시나아제 억제제인 천연 미백원료 알부틴에 비해 200배 이상의 효능을 나타내므로 피부 미백 조성물로 유용하게 사용할 수 있다. 또한, 멜라닌 생성 세포에서 멜라닌 생성을 저해하므로 우수한 피부 미백 효과를 발휘한다.
As described above, the composition containing the dihydrogliasperin C or the dihydrogliasperin D or isoangustone A of the present invention as an active ingredient, the activity of tyrosinase, an enzyme that plays an important role in the production of melanin In particular, in the case of dihydrogliasperin D, since it exhibits 200 times more efficacy than the natural whitening material arbutin, a tyrosinase inhibitor, it can be usefully used as a skin whitening composition. In addition, it inhibits melanin production in melanogenesis cells, thereby exerting an excellent skin whitening effect.
도 1은 티로시나아제 활성 억제 효과를 나타낸 것으로, 레인 1은 무처리 대조군, 레인 2는 알부틴 200 μM 처리군, 레인 3은 디하이드로글리아스페린 C 0.5 μM 처리군, 레인 4는 디하이드로글리아스페린 C 1 μM 처리군, 레인 5는 디하이드로글리아스페린 D 0.5 μM 처리군, 레인 6은 디하이드로글리아스페린 D 1 μM 처리군, 레인 7은 이소앙구스톤 A 0.5 μM 처리군, 레인 8은 이소앙구스톤 A 1 μM 처리군이다.
도 2는 멜라닌 생성 저해 효과를 나타낸 것으로, a는 무처리 대조군, b는 α-MSH 처리군, c는 α-MSH와 디하이드로글리아스페린 C 0.5 μM 처리군, d는 α-MSH와 디하이드로글리아스페린 C 1 μM 처리군, e는 α-MSH와 디하이드로글리아스페린 D 0.5 μM 처리군, f는 α-MSH와 디하이드로글리아스페린 D 1 μM 처리군, g는 α-MSH와 이소앙구스톤 A 0.5 μM 처리군, i는 α-MSH와 알부틴 200 μM 처리군이다.1 shows the effect of inhibiting tyrosinase activity,
Figure 2 shows melanin production inhibitory effect, a is a non-treated control group, b is α-MSH treated group, c is α-MSH and dihydrogliasperin C 0.5 μM treated group, d is α-MSH and
이하, 본 발명의 내용에 대해 하기 실험예 및 실시예를 통해 더욱 상세히 설명하고자 한다. 다만, 본 발명의 권리범위가 하기 실시예에만 한정되는 것은 아니고, 그와 등가의 기술적 사상의 변형까지를 포함한다.
Hereinafter, the content of the present invention will be described in more detail through the following experimental examples and examples. However, the scope of the present invention is not limited to the following embodiments, and includes modifications of equivalent technical ideas.
[[ 실험예Experimental Example 1: 티로시나아제 활성 억제 효과 측정] 1: Determination of Tyrosinase Activity Inhibition Effect]
실험예 1에서는 멜라닌 생합성에 관여하는 효소인 티로시나아제를 이용하여 본 발명 디하이드로글리아스페린 C, 디하이드로글리아스페린 D 및 이소앙구스톤 A의 티로시나아제 활성 억제 효과 측정하였다. 본 실험에서 사용하는 디하이드로글리아스페린 C, 디하이드로글리아스페린 D, 이소앙구스톤 A는 건조된 감초의 뿌리로부터 추출한 것을 사용하였다. In Experimental Example 1, the tyrosinase activity inhibitory effect of the present invention dehydrogliasperin C, dihydrogliasperin D and isoanguston A was measured using tyrosinase, an enzyme involved in melanin biosynthesis. Dihydrogliasperin C, dihydrogliasperin D, and isoangustone A used in this experiment were extracted from the root of dried licorice.
먼저, 티로시나아제 활성 억제 효과를 측정하기 위하여 제1인산칼륨(potassium phosphate monobasic)과 제2인산칼륨(potassium phosphate dibasic)을 증류수(D.W.)에 녹여 0.1 M 인산 칼륨 완충용액(potassium phosphate buffer, pH 6.8)를 제조하였다. 티로시나아제에 대한 반응기질로 사용하기 위하여 L-티로신(tyrosine, Sigma, USA)을 증류수(D.W.)에 녹여 1 mM L-티로신 용액을 제조하였고, 반응 효소로 작용하는 티로시나아제(Sigma, USA)는 0.1 M 인산 칼륨 완충용액에 녹여 2,000 Unit/mL로 준비하였다.First, to measure the inhibitory effect of tyrosinase activity, potassium phosphate monobasic and potassium phosphate dibasic were dissolved in distilled water (DW) and 0.1 M potassium phosphate buffer (PH). 6.8). L-tyrosine (Styma, Sigma, USA) was dissolved in distilled water (DW) to prepare a 1 mM L-tyrosine solution for use as a reactor for tyrosinase, tyrosinase (Sigma, USA) ) Was dissolved in 0.1 M potassium phosphate buffer and prepared at 2,000 Unit / mL.
550 μL 기준, 0.1 M 인산 칼륨 완충용액 250 μL, 티로시나아제 25 μL, 시료 25 μL, 증류수(D.W.) 225 μL를 24-웰 프레이트(well plate)에 넣고 25℃에서 10분간 혼합한 후, 1 mM L-티로신 용액을 250 μL을 첨가하여 25℃에서 10분간 반응시켰다. 반응을 정지시킨 후 반응혼합물을 96-웰 프레이트(well plate)에 150 μL씩 옮겨 마이크로플레이트 리더(microplate reader, Sunrise-Basic Tecan, Austria)를 이용하여 475 nm에서 흡광도를 측정하였다. 무처리 대조군의 경우, 시료 대신 증류수를 넣어주었다. 티로시나아제 활성은 다음과 같은 수학식 1로부터 계산하였다.250 μL of 0.1 M potassium phosphate buffer, 250 μL of tyrosinase, 25 μL of sample, 225 μL of distilled water (DW) in a 24-well plate and mixed for 10 minutes at 25 ° C. 250 μL of the mM L-tyrosine solution was added and reacted at 25 ° C. for 10 minutes. After stopping the reaction, the reaction mixture was transferred to a 96-well plate by 150 μL and absorbance was measured at 475 nm using a microplate reader (Sunrise-Basic Tecan, Austria). In the untreated control group, distilled water was added instead of the sample. Tyrosinase activity was calculated from the following equation (1).
[수학식 1][Equation 1]
측정결과 (도1), 디하이드로글리아스페린 C와 디하이드로글리아스페린 D가 티로시나아제의 활성을 농도 의존적으로 가장 잘 억제함을 확인할 수 있었고, 이소앙구스톤 A 또한 티로시나아제의 활성을 억제함을 확인할 수 있었다. 특히, 디하이드로글리아스페린 D의 경우, 티로시나아제 억제제인 천연 미백원료 알부틴에 비해 200배 이상의 효능을 가지는 것을 확인할 수 있었다.
As a result (Fig. 1), it was confirmed that dihydrogliasperin C and dihydrogliasperin D best inhibit the activity of tyrosinase in a concentration-dependent manner, and isoanguston A also inhibited the activity of tyrosinase. Inhibition was confirmed. In particular, in the case of dihydrogliasperin D, it was confirmed that the tyrosinase inhibitor has a 200-fold or more efficacy compared to the natural whitening material arbutin.
[[ 실험예Experimental Example 2: 멜라닌 생성 저해 효과 측정] 2: measurement of melanin production inhibitory effect]
실험예 2에서는 본 발명 디하이드로글리아스페린 C, 디하이드로글리아스페린 D 및 이소앙구스톤 A의 멜라닌 생성 저해 효과를 측정하기 위하여 사람 유래 멜라닌 생성 세포를 이용하여 폰타나-마손 스테이닝(Fontana-Masson staining)을 수행하였다. In Experimental Example 2, Fontana-Masson staining using human-derived melanocytes to measure the melanogenesis inhibitory effects of the present invention dihydrogliasperin C, dihydrogliasperin D and isoangustone A staining).
감초 추출물 조성물이 α-MSH에 의한 멜라닌 생성에 미치는 영향을 평가하기 위해 사람 유래 멜라닌 생성 세포인 HEM-MP세포(Cascade Biologics Inc., USA)를 24-웰 프레이트(well plate)에 시딩(seeding)하고, 사람 유래 멜라닌 생성 세포 성장 보충제(Human Melanocyte Growth Supplement) 5 mL이 첨가된 미디움(Medium) 254 배지를 사용하여, 37℃, 5% CO2의 조건하에서 24시간 배양하였다. To evaluate the effect of licorice extract composition on melanin production by α-MSH, HEM-MP cells (Cascade Biologics Inc., USA), which are human-derived melanin producing cells, were seeded on a 24-well plate. Then, the culture was incubated for 24 hours under 37 ° C. and 5% CO 2 using Medium 254 medium to which 5 mL of human-derived melanin-producing cell growth supplement (Human Melanocyte Growth Supplement) was added.
24시간 후 배지를 제거하고 0.5, 1 μM의 디하이드로글리아스페린 C, 디하이드로글리아스페린 D, 이소앙구스톤 A과 200 μM의 알부틴을 함유한 배지로 교체하였고, 1시간 후 α-MSH(Sigma, USA)를 최종 농도가 100 nM이 되도록 하여 세포 배양배지에 첨가하였다. 그리고 나서 동일한 조건하에서 세포가 웰의 바닥에 약 80% 이상 찰 때까지 배양하였다. 이때, 시료와 α-MSH를 처리하지 않은 세포를 무처리 대조군, α-MSH만 처리한 세포를 양성 대조군, α-MSH와 알부틴을 처리한 세포를 음성 대조군으로 하였다.After 24 hours the medium was removed and replaced with medium containing 0.5, 1 μM of dihydrogliasperin C, dihydrogliasperin D, isoanguston A and 200 μM of arbutin, and after 1 hour α-MSH ( Sigma, USA) was added to the cell culture medium to a final concentration of 100 nM. The cells were then incubated under the same conditions until at least about 80% of the cells were at the bottom of the wells. At this time, the sample and the cells not treated with α-MSH were treated as untreated control, cells treated with α-MSH only as positive control, and cells treated with α-MSH and arbutin as negative controls.
총 4일간 배양하여 멜라닌 생성이 완료된 시점에 배양액을 제거하고 HEM-MP세포에 함유된 멜라닌을 염색하였다. 이를 위해 PBS로 1번 세척한 후, 무수 에탄올(absolute ethanol)을 500 μL 넣어 30분간 고정시킨 다음 무수 에탄올을 제거하고 암모니아성 은 용액(ammoiacal silver solution)을 넣었다. 이를 60℃에서 30분간 염색시킨 다음, 용액을 제거하고 증류수(D.W.)로 1번 세척하였다. 0.1% 염화금(gold chloride)과 5% 티오황산나트륨(sodium thiosulfate), 핵 고속 적색 염색(nuclear fast red stain) 용액을 이용하여 한 번씩 헹궈준 후 무수 에탄올을 이용하여 탈수하였다. 탈수과정을 거친 후 현미경용 슬라이드와 커버글라스, 봉입제로 표본을 제작하였고 현미경을 이용하여 사진을 찍었다. After the incubation for 4 days, when the melanin production was completed, the culture solution was removed and the melanin contained in the HEM-MP cells was stained. After washing with PBS, 500 μL of absolute ethanol was added and fixed for 30 minutes. Anhydrous ethanol was removed and ammoiacal silver solution was added. It was stained at 60 DEG C for 30 minutes, then the solution was removed and washed once with distilled water (D.W.). After rinsing once with 0.1% gold chloride, 5% sodium thiosulfate and nuclear fast red stain solution, dehydrated with anhydrous ethanol. After the dehydration process, specimens were prepared with microscope slides, cover glasses, and encapsulants, and photographed using a microscope.
측정결과(도 2), 사람 유래 멜라닌 생성 세포에서, 디하이드로글리아스페린 C, 디하이드로글리아스페린 D, 이소앙구스톤 A에 의해, 멜라닌 생성이 저해됨을 확인할 수 있었다.
As a result of the measurement (FIG. 2), it was confirmed that melanin production was inhibited by dehydrogliasperin C, dihydrogliasperin D, and isoangustone A in human-derived melanocytes.
[[ 실시예Example 1: 피부 미백용 식품 조성물 제조] 1: Manufacture food composition for skin whitening]
실시예 1에서는 하기와 같이 피부 미백용 식품 조성물을 제조하였다. In Example 1, a food composition for skin whitening was prepared as follows.
(1) 선식 제조 (1) Manufacturing of wire
현미, 보리, 찹쌀, 율무를 공지의 방법으로 알파화시켜 건조시킨 것을 배전한 후 분쇄기로 입도 60메쉬의 분말로 준비하였다. 검정콩, 검정깨 및 들깨 각각을 공지의 방법으로 쪄서 건조시킨 후 배전 및 분쇄하여 입도 60메쉬의 분말로 준비하였다. 이후, 현미 30중량%, 율무 15중량%, 보리 20중량%, 찹쌀 9중량%, 들깨 7중량%, 검정콩 8중량%, 검정깨 7중량%, 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A 3중량%, 영지 0.5중량% 및 지황 0.5중량%을 혼합하여 선식을 제조하였다.Brown rice, barley, glutinous rice, and yulmu were alphad by a known method, and then dried and roasted. Black beans, black sesame seeds and perilla were each steamed and dried in a known manner, then roasted and ground to prepare a powder having a particle size of 60 mesh. Then, 30% by weight brown rice, 15% by weight barley, 20% by weight barley, 9% by weight glutinous rice, 7% by weight perilla, 8% by weight black soybean, 7% by weight black sesame, dihydrogliasperin C or dihydrogliasperin A wire was prepared by mixing 3% by weight of D or isoanguston A, 0.5% by weight of Ganoderma lucidum and 0.5% by weight of Sulfur.
(2) 츄잉껌 제조(2) Production of chewing gum
껌 베이스 20중량%, 설탕 76.9중량%, 향료 1중량%, 물 2중량%, 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A 0.1중량%를 배합하여 통상의 방법으로 츄잉껌을 제조하였다.Chewing gum in a conventional manner by combining 20% by weight of gum base, 76.9% by weight of sugar, 1% by weight of perfume, 2% by weight of water, 0.1% by weight of dihydrogliasperin C or dihydrogliasperin D or isoanguston A. Was prepared.
(3) 캔디 제조(3) Candy manufacturing
설탕 60중량%, 물엿 39.8중량%, 향료 0.1중량%, 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A 0.1중량%를 배합하여 통상의 방법으로 캔디를 제조하였다.Candy was prepared in a conventional manner by combining 60% by weight of sugar, 39.8% by weight of starch syrup, 0.1% by weight of fragrance, dihydrogliasperin C or dihydrogliasperin D or 0.1% by weight of isoangustone A.
(4) 비스킷 제조(4) Manufacturing of biscuits
박력 1급 25.59중량%, 중력 1급 22.22중량%, 정백당 4.80중량%, 식염 0.73중량%, 포도당 0.78중량%, 팜쇼트닝 11.78중량%, 암모니움 1.54중량%, 중조 0.17중량%, 중아황산나트륨 0.16중량%, 쌀가루 1.45중량%, 비타민 B₁0.0001중량%, 비타민 B₂0.0001중량%, 밀크향 0.04중량%, 물 20.6998중량%, 전지분유 1.16중량%, 대용분유 0.29중량%, 제일인산칼슘 0.03중량%, 살포염 0.29중량%, 분무유 7.27중량%와 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A 1중량%를 배합하여 통상의 방법으로 비스킷을 제조하였다. Force 1st class 25.59 wt%, gravity 1st class 22.22 wt%, white sugar 4.80 wt%, salt 0.73 wt%, glucose 0.78 wt%, palm shortening 11.78 wt%, ammonium 1.54 wt%, sodium bicarbonate 0.17 wt%, sodium bisulfite 0.16 wt% %, Rice flour 1.45 wt%, Vitamin B₁0.0001 wt%, Vitamin B₂0.0001 wt%, Milk flavor 0.04 wt%, Water 20.6998 wt%, Whole milk powder 1.16 wt%, Substitute milk powder 0.29 wt%, 0.01 wt% calcium phosphate , Biscuits were prepared in a conventional manner by combining 0.29% by weight of spraying salt, 7.27% by weight of spray oil, and 1% by weight of dihydrogliasperin C or dihydrogliasperin D or isoanguston A.
(5) 건강음료 제조(5) health drink manufacturing
꿀 0.26중량%, 치옥토산아미드 0.0002중량%, 니코틴산아미드 0.0004중량%, 염산리보플라빈나트륨 0.0001중량%, 염산피리독신 0.0001중량%, 이노시톨 0.001중량%, 오르트산 0.002중량%, 물 98.7362중량%, 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A 1중량%를 배합하여 통상의 방법으로 건강 음료를 제조하였다.Honey 0.26%, Chioctosanamide 0.0002%, Nicotinamide amide 0.0004%, Riboflavin sodium hydrochloride 0.0001%, Pyridoxine hydrochloride 0.0001%, Inositol 0.001%, Orteic acid 0.002%, Water 98.7362%, Dihydro A health beverage was prepared by a conventional method by combining gliasperin C or dihydrogliasperin D or 1% by weight of isoanguston A.
[[ 실시예Example 2: 피부 미백용 2: skin whitening 화장료Cosmetics 조성물 제조] Composition preparation]
실시예 2에서는 하기와 같이 피부 미백용 화장료 조성물을 제조하였다. In Example 2, a cosmetic composition for skin whitening was prepared as follows.
(1) 화장수의 제조(1) Preparation of the lotion
95% 에탄올 8 kg에 폴리피로리돈 0.05 kg, 올리엘알콜 0.1 kg, 폴리옥시에틸렌모노올레이트 0.2 kg, 향료 0.2 kg, 파라옥시안식향산메틸에스테르 0.1 kg, 소량의 산화방지제, 소량의 색소를 혼합 용해하였다. 8 kg of 95% ethanol, 0.05 kg polypyrrolidone, 0.1 kg oleic alcohol, 0.2 kg polyoxyethylene monooleate, 0.2 kg fragrance, 0.1 kg paraoxybenzoate methyl ester, a small amount of antioxidant, a small amount of pigment It was.
한편, 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A 0.05 kg, 글리세린 5 kg을 정제수 85.33 kg에 용해한 후, 상기에서 제조한 혼합액을 첨가한 후, 교반하여 화장수를 제조하였다.Meanwhile, 0.05 kg of dihydrogliasperin C or dihydrogliasperin D or isoangustone A and 5 kg of glycerin were dissolved in 85.33 kg of purified water, and then the mixed solution prepared above was added, followed by stirring to prepare a lotion. .
(2) 에센스의 제조(2) Preparation of Essence
정제수 적당량에 산탄검 0.1 kg과 카르복시비닐폴리머 0.17 kg를 가하고 충분히 분산시켜 완전히 용해시킨 후, 여기에 글리세린 10.0 kg, 1,3-부틸렌글리콜 3.5 kg, 알란토인 0.05 kg, DL-판테놀 0.15 kg, 세로마틴 0.05 kg, 벤조페논-9 0.05 kg, 세라마이드 0.02 kg, 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A 0.03 kg을 혼합하여 수상을 만들었다. 0.1 kg of xanthan gum and 0.17 kg of carboxyvinyl polymer are added to the appropriate amount of purified water and fully dispersed, and then completely dissolved. 10.0 kg of glycerin, 3.5 kg of 1,3-butylene glycol, 0.05 kg of allantoin, 0.15 kg of DL-panthenol, and lengthwise A water phase was made by mixing 0.05 kg martin, 0.05 kg benzophenone-9, 0.02 kg ceramide, dihydrogliasperin C or dihydrogliasperin D or 0.03 kg isoanguston A.
한편, 에탄올(95%) 9.0 kg에 파라옥시안식향산메칠 0.1 kg, 폴리옥시에틸렌경화피마자유 0.45 kg, 초산토코페롤 0.2 kg, 메칠페닐폴리실록산 0.2 kg, 트리에탄올아민 0.17 kg, 향 0.08 kg, 색소 0.0002 kg을 모두 혼합하고 용해시켜서 알코올상을 만들었다. 상기에서 제조한 수상에 알코올상을 서서히 가하면서 아지믹서로 균일하게 교반하여 에센스를 제조하였다. On the other hand, in 9.0 kg of ethanol (95%), 0.1 kg of paraoxybenzoic acid methyl, 0.45 kg of polyoxyethylene hardened castor oil, 0.2 kg of tocopherol acetate, 0.2 kg of methyl phenylpolysiloxane, 0.17 kg of triethanolamine, 0.08 kg of flavor, and 0.0002 kg of pigment All were mixed and dissolved to form an alcohol phase. Essence was prepared by uniformly stirring with an azimixer while gradually adding an alcohol phase to the aqueous phase prepared above.
Claims (8)
[화학식 1]
A cosmetic composition for skin whitening containing dihydrogliasperin C having the structure of Formula 1 as an active ingredient.
[Formula 1]
[화학식 2]
A cosmetic composition for skin whitening containing dihydrogliasperin D having the structure of Formula 2 as an active ingredient.
(2)
[화학식 3]
A cosmetic composition for skin whitening containing isoangustone A having a structure of Formula 3 as an active ingredient.
(3)
상기 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A는,
감초 유래인 것을 특징으로 하는 피부 미백용 화장료 조성물.
The method according to any one of claims 1 to 3,
The dihydrogliasperin C or dihydrogliasperin D or isoangustone A,
A cosmetic composition for skin whitening, which is derived from licorice.
[화학식 1]
A food composition for skin whitening containing dihydrogliasperin C having the structure of Formula 1 as an active ingredient.
[Formula 1]
[화학식 2]
A food composition for skin whitening containing dihydrogliasperin D having the structure of Formula 2 as an active ingredient.
(2)
[화학식 3]
A food composition for skin whitening containing isoangustone A having a structure of Formula 3 as an active ingredient.
(3)
상기 디하이드로글리아스페린 C 또는 디하이드로글리아스페린 D 또는 이소앙구스톤 A는,
감초 유래인 것을 특징으로 하는 피부 미백용 식품 조성물.The method according to any one of claims 5 to 7,
The dihydrogliasperin C or dihydrogliasperin D or isoangustone A,
A food composition for skin whitening, characterized in that it is derived from licorice.
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| KR20100050767A (en) * | 2008-11-06 | 2010-05-14 | 경북대학교 산학협력단 | Composition containing the dehydroglyasperin derivatives for inducing nad(p)h:quinone oxidoreductase and the use thereof |
| KR101101296B1 (en) | 2009-11-09 | 2012-01-04 | 한림대학교 산학협력단 | A method for isolation of antioxidant from glycyrrhiza uralensis |
| KR20120092474A (en) * | 2011-02-11 | 2012-08-21 | 서울대학교산학협력단 | Composition for prevention or treatment of skin diseases containing dehydroglyasperin d |
-
2012
- 2012-08-10 KR KR1020120087736A patent/KR101276306B1/en active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100050767A (en) * | 2008-11-06 | 2010-05-14 | 경북대학교 산학협력단 | Composition containing the dehydroglyasperin derivatives for inducing nad(p)h:quinone oxidoreductase and the use thereof |
| KR101101296B1 (en) | 2009-11-09 | 2012-01-04 | 한림대학교 산학협력단 | A method for isolation of antioxidant from glycyrrhiza uralensis |
| KR20120092474A (en) * | 2011-02-11 | 2012-08-21 | 서울대학교산학협력단 | Composition for prevention or treatment of skin diseases containing dehydroglyasperin d |
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| Journal of Separation Science, Vol. 33(4-5), pp. 664-671 (2010.1.28) * |
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