KR102664892B1 - Composition for skin improvement containing tenuifoliside A - Google Patents
Composition for skin improvement containing tenuifoliside A Download PDFInfo
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- KR102664892B1 KR102664892B1 KR1020160114540A KR20160114540A KR102664892B1 KR 102664892 B1 KR102664892 B1 KR 102664892B1 KR 1020160114540 A KR1020160114540 A KR 1020160114540A KR 20160114540 A KR20160114540 A KR 20160114540A KR 102664892 B1 KR102664892 B1 KR 102664892B1
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- skin
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- present
- cosmetic composition
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- A61K8/00—Cosmetics or similar toiletry preparations
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- A—HUMAN NECESSITIES
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- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61Q19/00—Preparations for care of the skin
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- 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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Abstract
본 발명은 테뉴폴리사이드 에이(tenuifoliside A)를 포함하는 화장료 조성물에 관한 것으로, 보다 상세하게는 피부 미백, 피부 탄력 증진, 주름 개선, 보습, 항산화 또는 피부 트러블 개선 등의 우수한 효과를 가지는 화장료 조성물에 관한 것이다. 본 발명의 조성물은 저농도에서도 뛰어난 멜라닌 총량 감소 효과를 나타내고 콜라겐 합성 촉진 효과, 엘라스타제 활성 저해 효과가 우수하며, 항산화, 항염증 및 항당화 효과가 우수하여 피부 미백용, 탄력 증진용 또는 주름 개선용, 피부 보습용, 항산화용 및 피부 트러블 개선용 화장료 조성물로서 사용할 수 있다. 또한, 본 발명의 테뉴폴리사이드 에이를 포함하는 조성물은 식품 조성물 및 의약외품 조성물로서 사용할 수 있다.The present invention relates to a cosmetic composition containing tenuifoliside A, and more specifically, to a cosmetic composition having excellent effects such as skin whitening, skin elasticity enhancement, wrinkle improvement, moisturizing, antioxidant or skin trouble improvement. It's about. The composition of the present invention exhibits an excellent effect of reducing the total amount of melanin even at low concentrations, has an excellent effect of promoting collagen synthesis and inhibiting elastase activity, and has excellent antioxidant, anti-inflammatory and anti-glycation effects for skin whitening, enhancing elasticity or improving wrinkles. It can be used as a cosmetic composition for skin moisturizing, antioxidant, and skin trouble improvement. Additionally, the composition containing tenupolyside A of the present invention can be used as a food composition and quasi-drug composition.
Description
본 발명은 테뉴폴리사이드 에이(tenuifoliside A)를 포함하는 화장료 조성물에 관한 것으로서, 보다 상세하게는 피부 미백, 피부 탄력 증진, 주름 개선, 보습, 항산화 또는 피부 트러블 개선 등의 우수한 효과를 가지는 화장료 조성물에 관한 것이다. 또한, 본 발명은 테뉴폴리사이드 에이를 포함하는 식품 조성물 및 의약외품 조성물에 관한 것이다.The present invention relates to a cosmetic composition containing tenuifoliside A, and more specifically, to a cosmetic composition having excellent effects such as skin whitening, skin elasticity enhancement, wrinkle improvement, moisturizing, antioxidant or skin trouble improvement. It's about. Additionally, the present invention relates to a food composition and a quasi-drug composition containing tenupolyside A.
일반적으로 알려진 미백 성분으로서, 코지산(Kojic acid) 또는 알부틴(Arbutin) 등과 같은 티로시나제 효소활성을 억제하는 물질, 하이드로퀴논(Hydroquinone), 비타민 C(L-Ascorbic acid) 또는 이들의 유도체와 각종 식물 추출물이 있다. 이들은 멜라닌 색소의 합성을 저해함으로써, 피부 톤을 밝게 하여 피부 미백을 실현할 수 있을 뿐만 아니라, 자외선, 호르몬 또는 유전에 기인한 기미나 주근깨 등의 피부 과색소 침착증의 개선이 가능하다. 그러나 피부 적용 시, 자극과 발적 등의 안전성의 문제로 사용량의 제한이 있거나, 효과가 미미하여 실질적인 효과를 기대할 수 없는 문제점이 있다.Commonly known whitening ingredients include substances that inhibit tyrosinase enzyme activity such as kojic acid or arbutin, hydroquinone, vitamin C (L-Ascorbic acid) or their derivatives, and various plant extracts. There is. By inhibiting the synthesis of melanin pigment, they can not only brighten skin tone and achieve skin whitening, but also improve skin hyperpigmentation such as spots and freckles caused by ultraviolet rays, hormones, or genetics. However, when applied to the skin, there is a limit to the amount of use due to safety issues such as irritation and redness, or the effect is so small that no practical effect can be expected.
콜라겐은 피부의 섬유아세포(Fibroblast)에서 생성되는 주요 기질 단백질로서 세포 외 간질에 존재하고, 중요한 기능으로는 피부의 기계적 견고성, 결합조직의 저항력과 조직의 결합력, 세포접착의 지탱, 세포 분할과 분화(유기체의 성장 혹은 상처 치유 시)의 유도 등이 알려져 있다. 이러한 콜라겐은 연령 및 자외선 조사에 의한 광 노화에 의해 감소하며, 콜라겐을 분해하는 콜라게나제 효소 활성으로 콜라겐 감소가 촉진된다. 이는 피부의 주름 형성과 밀접한 연관이 있다고 알려져 있다.Collagen is a major matrix protein produced by skin fibroblasts and is present in the extracellular matrix. Its important functions include mechanical rigidity of the skin, connective tissue resistance and tissue adhesion, support for cell adhesion, and cell division and differentiation. Induction (during the growth of organisms or wound healing) is known. Collagen decreases due to age and photoaging caused by ultraviolet irradiation, and collagen reduction is promoted by collagenase enzyme activity that decomposes collagen. This is known to be closely related to the formation of wrinkles on the skin.
또한, 엘라스틴(Elastin) 섬유는 콜라겐과 가교 결합을 형성하며 피부 탄력에 관여하고 있는 주름 생성에 중요한 피부 구성성분이다. 엘라스틴 섬유의 결핍과 응집, 엘라스틴 분해 효소인 엘라스타제(Elastase)의 활성도의 현격한 증가는 피부 주름 생성 요인 중의 하나로 밝혀지고 있다. 엘라스타제는 엘라스틴을 분해할 수 있는 유일한 효소로서 이에 대한 저해는 피부 주름 개선을 근본적으로 줄여줄 수 있다고 알려져 있다.In addition, elastin fibers form cross-links with collagen and are an important skin component in wrinkle formation, which is involved in skin elasticity. Deficiency and aggregation of elastin fibers and a significant increase in the activity of elastase, an elastin decomposing enzyme, have been found to be one of the factors causing skin wrinkles. Elastase is the only enzyme that can decompose elastin, and its inhibition is known to fundamentally reduce the improvement of skin wrinkles.
아울러, 콜라겐 및 엘라스틴 섬유는 진피층 내의 수분 보유에 중요한 역할을 하는 기질 단백질로 이러한 기질 단백질이 수분을 흡착하며, 이들이 이루는 구조 내부에 수분 보유력을 높여 피부가 적정 수분을 함유한 상태를 유지할 수 있도록 해주며, 이를 통해 피부의 탄력을 유지하는데 관여한다고 알려져 있다.In addition, collagen and elastin fibers are matrix proteins that play an important role in retaining moisture in the dermal layer. These matrix proteins absorb moisture and increase the moisture retention capacity within the structure they form, allowing the skin to maintain an appropriate moisture content. It is known to be involved in maintaining skin elasticity.
현재, 피부 탄력 증진 및 주름 개선 화장료로는 레티노이드, 아데노신, 동물태반유래 단백질, 클로렐라 추출물 등이 알려져 있다. 가장 잘 알려져 있는 레티놀은 콜라겐 합성을 촉진하며 엘라스타제 효소를 저해하는 물질이지만 불안정하며, 피부 적용 시 자극, 발적 등의 안전성 문제로 사용량의 제한이 있으며, 클로렐라 추출물 등은 효과가 미미하여 실질적으로 피부 탄력 증진 및 주름 개선 효과를 기대하기가 어렵다고 알려져 있다.Currently, retinoids, adenosine, animal placenta-derived proteins, and chlorella extract are known as cosmetics for improving skin elasticity and improving wrinkles. The most well-known retinol is a substance that promotes collagen synthesis and inhibits the elastase enzyme, but it is unstable and its usage is limited due to safety issues such as irritation and redness when applied to the skin. It is known that it is difficult to expect the effect of improving elasticity and improving wrinkles.
당화(Glycation)는 일반적으로 효소의 관여 없이 일어나는 단백질 또는 지방에 포도당 또는 과당과 같은 단순당이 공유결합을 형성하는 반응을 의미한다. 최종당화산물의 축적은 단백질을 단단하고 더욱 부서지기 쉬운 상태로 변화시키며, 당화된 콜라겐은 진피층의 세포 외 기질에서 콜라겐이 적절한 구조를 형성하지 못하도록 함으로써 피부의 탄력을 잃게 하고 주름 생성을 촉진한다(Dyer, D. G. et al, The Journal of Clinical Investigation., 9, p. 2463, 1993). 또한 당화로 인해 생성된 최종당화산물은 갈색 빛을 띠는 물질로써, 피부 노화가 진행되면서 점차 얼굴빛이 노랗게 변하는 원인 물질로 생각되고 있으며, 특정 최종당화산물이 쌓일수록 피부에서 반사되는 반사 빛이 줄어든다고 알려져 있다(Hiroshi, O. et al, Skin Research and Technology, 15, p. 496, 2009). 당화를 억제하는 물질로 아미노구아니딘(Aminoguanidine), 피리독사민(Pyridoxamine), 아스피린(Aspirin) 등이 알려져 있으나, 이들 물질은 피부에 대한 안전성의 문제로 사용량의 제한이 있거나, 효과가 미미하여 실질적으로 효과를 기대할 수 없는 문제점이 있다.Glycation generally refers to a reaction in which a simple sugar such as glucose or fructose forms a covalent bond with a protein or fat without the involvement of enzymes. Accumulation of advanced glycation end products changes proteins into a hard and more brittle state, and glycated collagen prevents collagen from forming an appropriate structure in the extracellular matrix of the dermal layer, causing skin to lose elasticity and promote the formation of wrinkles. Dyer, D. G. et al, The Journal of Clinical Investigation., 9, 2463, 1993). In addition, the advanced glycation end products produced by glycation are brown-colored substances and are thought to be the cause of the complexion gradually turning yellow as skin aging progresses. As certain advanced glycation end products accumulate, the reflected light reflected from the skin decreases. It is known that (Hiroshi, O. et al, Skin Research and Technology, 15, p. 496, 2009). Aminoguanidine, Pyridoxamine, and Aspirin are known as substances that inhibit glycation, but these substances have limits on the amount of use due to safety issues on the skin, or their effects are so minimal that they are practically effective. There is a problem that cannot be expected.
화장품은 피부를 보호하고 피부의 미화 및 청결을 위해 사용되는 제품이지만, 그 조성으로는 피부 보호 목적과는 상이한 성분들이 제품 형성을 위해 불가피하게 포함된다. 이러한 성분들로는 계면활성제, 방부제, 향료, 자외선 차단제, 색소뿐 아니라, 그 밖의 효능 및 효과를 부여하기 위한 여러 가지 성분들이 여기에 포함된다. 이들 성분은 일반적으로 피부에 염증이나 뾰루지, 부종 등 각종 트러블을 발생시키는 것으로 알려져 있다(Maibach. H. I., Contact Dermatitis, 6. 369-404, 1980). 또한, 체내로부터 배출되는 피지 및 땀, 화장품 성분 중의 지방산, 고급 알코올, 단백질 성분 등이 피부상에 존재하는 피부 상재균에 의해 독성이 강한 물질로 분해되어 이들에 의해 피부 염증이 유발될 수도 있으며, 태양으로부터 나오는 자외선에 의해서도 피부 염증이 유발된다는 것은 잘 알려진 사실이다.Cosmetics are products used to protect the skin and to beautify and clean the skin, but their composition inevitably includes ingredients different from those for the purpose of skin protection. These ingredients include surfactants, preservatives, fragrances, sunscreens, pigments, as well as various other ingredients to provide efficacy and effectiveness. These ingredients are generally known to cause various skin problems such as inflammation, rashes, and edema (Maibach. H. I., Contact Dermatitis, 6. 369-404, 1980). In addition, sebum and sweat discharged from the body, fatty acids, higher alcohols, and protein components in cosmetic ingredients are decomposed into highly toxic substances by skin flora existing on the skin, which may cause skin inflammation. It is a well-known fact that skin inflammation is also caused by ultraviolet rays from the sun.
염증 반응은 붉어짐(feeling of redness), 따끔거림(pricking feeling), 화끈거림(burning hotness), 팽윤(swelling), 조직의 변화와 같은 5가지 현상으로 나타나는데, 이는 해로운 주위 환경, 즉 세균과 같은 외부 물질의 침입과 기계적 손상으로부터 생체를 보호하려는 생리적인 반응이다. 이러한 염증현상은 여러 종류의 다형핵 백혈구(PMNs)와 면역 물질의 많은 증가를 초래하며, 이처럼 증가된 세포들은 염증성 세포 산물인 다양한 종류의 단백질 분해 효소와 사이토카인 등을 분비함으로써 치료 및 방어를 할 수 있게 해준다. 그러나, 이러한 작용은 인접해 있는 조직 세포와 비세포 성분들에 해로운 손상을 일으키기도 한다. 따라서, 적절한 조건 하에서는 염증 초기 상태가 지난 후 정상 기능을 되찾게 되지만, 염증을 자극하는 자극제가 없어지지 않거나 계속해서 만들어질 경우에는 결과적으로 만성 염증이 일어나게 되어 더욱더 심각한 조직의 손상을 가져온다.The inflammatory response is manifested by five phenomena such as feeling of redness, pricking feeling, burning hotness, swelling, and tissue changes, which are caused by harmful environmental factors, such as bacteria. It is a physiological response to protect the living body from intrusion of substances and mechanical damage. This inflammatory phenomenon causes a large increase in various types of polymorphonuclear leukocytes (PMNs) and immune substances, and these increased cells secrete various types of proteolytic enzymes and cytokines, which are inflammatory cell products, to provide treatment and defense. It allows you to However, these actions can also cause detrimental damage to adjacent tissue cells and non-cellular components. Therefore, under appropriate conditions, normal function is restored after the initial state of inflammation has passed, but if the stimulant that stimulates inflammation does not disappear or continues to be produced, chronic inflammation eventually occurs, resulting in more serious tissue damage.
한편, 테뉴폴리사이드 에이(tenuifoliside A)는 분자식 C31H38O17, 분자량 682.63를 가지는 페닐프로파노이드(phenylpropanoid) 계열의 화합물로서, 테뉴폴리사이드 에이(tenuifoliside A) 또는 [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxyoxan-2-yl]methyl 4-hydroxybenzoate로 명명된다. 한편, 테뉴폴리사이드 A는 원지(Polygala tenuifolia Willd., 원지과 Polygalaceae)로부터 분리한 식물성 폴리페놀 화합물로서, 페닐프로파노이드 성분으로 구성되어 있으며, 피리딘, 메탄올, 에탄올 등의 용매에 녹는 것으로 알려져 있다.On the other hand, tenuifoliside A is a compound of the phenylpropanoid series with the molecular formula C 31 H 38 O 17 and molecular weight 682.63. Tenuifoliside A or [(2R, 3S, 4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-3-[(E)-3- It is named (3,4,5-trimethoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxyoxan-2-yl]methyl 4-hydroxybenzoate. Meanwhile, Tenupolyside A is the base ( Polygala It is a plant polyphenol compound isolated from tenuifolia Willd. (Polygalaceae), consists of phenylpropanoid components, and is known to be soluble in solvents such as pyridine, methanol, and ethanol.
이러한 배경하에, 본 발명자들은 피부 미백, 피부 탄력 증진, 주름 개선, 보습, 항산화 및 피부 트러블 개선 효과가 우수한 물질에 관하여 연구를 수행하였으며, 이에 테뉴폴리사이드 에이를 유효성분으로 포함하는 조성물이 멜라닌 총량 감소, 콜라겐 합성 촉진, 엘라스타제 활성 저해, 항산화, 항염증 및 항당화 효과를 나타냄을 규명하여, 이를 활용한 화장료 조성물, 식품 조성물 및 의약외품 조성물을 완성하기에 이르렀다.Against this background, the present inventors conducted research on substances with excellent skin whitening, skin elasticity enhancement, wrinkle improvement, moisturizing, antioxidant, and skin trouble improvement effects, and found that a composition containing tenupolyside A as an active ingredient was found to reduce the total amount of melanin. By discovering that it has a reduction, collagen synthesis promotion, elastase activity inhibition, antioxidant, anti-inflammatory and anti-glycation effects, cosmetic compositions, food compositions and quasi-drug compositions using it were completed.
본 발명의 목적은 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 화장료 조성물을 제공하는 것이다.The purpose of the present invention is to provide a cosmetic composition containing tenupolyside A represented by Formula 1 or a cosmetically acceptable salt thereof as an active ingredient.
구체적으로, 본 발명의 목적은 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 미백용 화장료 조성물을 제공하는 것이다.Specifically, the purpose of the present invention is to provide a cosmetic composition for skin whitening containing tenupolyside A represented by Formula 1 or a cosmetically acceptable salt thereof as an active ingredient.
또한 구체적으로, 본 발명의 목적은 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 탄력 증진 또는 주름 개선용 화장료 조성물을 제공하는 것이다.Additionally, specifically, the purpose of the present invention is to provide a cosmetic composition for promoting skin elasticity or improving wrinkles, which contains tenupolyside A represented by Chemical Formula 1 or a cosmetically acceptable salt thereof as an active ingredient.
또한 구체적으로, 본 발명의 목적은 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 보습용 화장료 조성물을 제공하는 것이다.Additionally, specifically, the purpose of the present invention is to provide a cosmetic composition for moisturizing skin containing tenupolyside A represented by Chemical Formula 1 or a cosmetically acceptable salt thereof as an active ingredient.
또한 구체적으로, 본 발명의 목적은 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 트러블 개선용 화장료 조성물을 제공하는 것이다.Additionally, specifically, the purpose of the present invention is to provide a cosmetic composition for improving skin troubles containing tenupolyside A represented by Chemical Formula 1 or a cosmetically acceptable salt thereof as an active ingredient.
본 발명의 다른 목적은 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 식품학적으로 허용 가능한 염을 유효성분으로 포함하는 식품 조성물을 제공하는 것이다.Another object of the present invention is to provide a food composition containing tenupolyside A represented by Formula 1 or a foodologically acceptable salt thereof as an active ingredient.
본 발명의 또 다른 목적은 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 의약외품 조성물을 제공하는 것이다.Another object of the present invention is to provide a quasi-drug composition containing tenupolyside A represented by Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
본 발명은 상기와 같은 과제들을 해결하고, 본 발명의 목적을 달성하기 위하여 화학식 1로 표시되는 화합물 또는 이의 화장품학적으로 허용 가능한 염을 포함하는 화장료 조성물을 제공한다.In order to solve the above problems and achieve the object of the present invention, the present invention provides a cosmetic composition containing the compound represented by Formula 1 or a cosmetically acceptable salt thereof.
구체적으로, 본 발명의 하나의 양태로서, 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 미백용 화장료 조성물을 제공한다.Specifically, as one aspect of the present invention, a cosmetic composition for skin whitening containing tenupolyside A represented by Formula 1 or a cosmetically acceptable salt thereof as an active ingredient is provided.
본 발명의 다른 양태로서, 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 탄력 증진 또는 주름 개선용 화장료 조성물을 제공한다.In another aspect of the present invention, a cosmetic composition for promoting skin elasticity or improving wrinkles is provided, comprising Tenupolyside A represented by Formula 1 or a cosmetically acceptable salt thereof as an active ingredient.
본 발명의 또 다른 양태로서, 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 보습용 화장료 조성물을 제공한다.In another aspect of the present invention, a cosmetic composition for moisturizing skin containing tenupolyside A represented by Formula 1 or a cosmetically acceptable salt thereof as an active ingredient is provided.
본 발명의 또 다른 양태로서, 화학식 1로 표시되는 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 트러블 개선용 화장료 조성물을 제공한다.In another aspect of the present invention, a cosmetic composition for improving skin troubles is provided, comprising tenupolyside A represented by Chemical Formula 1 or a cosmetically acceptable salt thereof as an active ingredient.
본 발명의 또 다른 양태로서, 테뉴폴리사이드 에이 또는 이의 식품학적으로 허용 가능한 염을 유효성분으로 포함하는 식품 조성물을 제공한다.In another aspect of the present invention, a food composition is provided comprising tenupolyside A or a foodologically acceptable salt thereof as an active ingredient.
본 발명의 또 다른 양태로서, 테뉴폴리사이드 에이 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 의약외품 조성물을 제공한다.In another aspect of the present invention, a quasi-drug composition containing tenupolyside A or a pharmaceutically acceptable salt thereof as an active ingredient is provided.
본 발명에서는 하기 화학식 1로 표시되는 테뉴폴리사이드 에이 화합물 또는 이의 염을 포함하는 조성물을 제공한다.The present invention provides a composition comprising tenupolyside A compound or a salt thereof represented by the following formula (1).
[화학식 1] [Formula 1]
본 발명에 있어서, “테뉴폴리사이드 에이(tenuifoliside A)”는 상기 화학식 1로 표시되고, 분자식 C31H38O17, 분자량 682.63를 가지며, 테뉴폴리사이드 에이(tenuifoliside A) 또는 [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-3-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxyoxan-2-yl]methyl 4-hydroxybenzoate로 명명된다. 한편, 테뉴폴리사이드 A는 원지(Polygala tenuifolia Willd., 원지과 Polygalaceae)로부터 분리한 식물성 폴리페놀 화합물로서, 페닐프로파노이드 성분으로 구성되어 있으며, 피리딘, 메탄올, 에탄올 등의 용매에 녹는 것으로 알려져 있으며, 페닐프로파노이드(phenylpropanoid) 계열의 화합물이다. In the present invention, “tenuifoliside A” is represented by the above formula 1, has a molecular formula C 31 H 38 O 17 , a molecular weight of 682.63, and is composed of tenuifoliside A or [(2R,3S) ,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)-3-[(E)-3 It is named -(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]oxyoxan-2-yl]methyl 4-hydroxybenzoate. Meanwhile, Tenupolyside A is the base ( Polygala It is a plant polyphenol compound isolated from tenuifolia Willd. (Polygalaceae) and is composed of phenylpropanoid components. It is known to be soluble in solvents such as pyridine, methanol, and ethanol, and is a phenylpropanoid series compound. am.
본 발명은 테뉴폴리사이드 에이의 획득 방법에 특별히 한정되지 않으며, 당업계에 공지된 방법으로 화학적으로 합성하거나, 시판되는 물질을 사용할 수 있다.The present invention is not particularly limited to the method of obtaining tenupolyside A, and it can be chemically synthesized by a method known in the art, or a commercially available material can be used.
본 발명의 화학식 1로 표시되는 테뉴폴리사이드 에이는 용매화된 형태뿐만 아니라 비-용매화된(unsolvated) 형태로 존재할 수도 있다. 본 발명의 테뉴폴리사이드 에이는 결정형 또는 무정형 형태로 존재할 수 있으며, 이러한 모든 물리적 형태는 본 발명의 범위에 포함된다.Tenupolyside A represented by Formula 1 of the present invention may exist in an unsolvated form as well as a solvated form. Tenupolyside A of the present invention may exist in crystalline or amorphous form, and all such physical forms are included within the scope of the present invention.
본 발명에 따른 조성물에 있어, 상기 테뉴폴리사이드 에이의 함량은 조성물 전체 중량 대비 0.0001 내지 10 중량% 인 것이 바람직하다.In the composition according to the present invention, the content of tenupolyside A is preferably 0.0001 to 10% by weight based on the total weight of the composition.
본 발명은 상기 화학식 1로 표시되는 화합물 또는 이의 화장품학적으로 허용 가능한 염을 포함하는 화장료 조성물을 제공한다. The present invention provides a cosmetic composition containing the compound represented by Formula 1 or a cosmetically acceptable salt thereof.
또한, 구체적으로, 본 발명은 상기 화학식 1로 표시되는 화합물 또는 이의 화장품학적으로 허용 가능한 염을 포함하는 피부 미백용, 피부 탄력 증진 또는 주름 개선용, 피부 보습용, 항산화용 또는 피부 트러블 개선용 화장료 조성물을 제공할 수 있다.In addition, specifically, the present invention relates to a cosmetic for skin whitening, improving skin elasticity or wrinkles, moisturizing skin, antioxidant or improving skin troubles, comprising the compound represented by Formula 1 or a cosmetically acceptable salt thereof. A composition may be provided.
본 발명에 있어서, “피부 미백”이라 함은 멜라닌 색소의 합성을 저해함으로써 피부 톤을 밝게 할 뿐만 아니라, 자외선, 호르몬 또는 유전에 기인한 기미나 주근깨 등의 피부 과색소 침착을 개선하는 것을 말한다. 본 발명의 일 실시예에서는, 화학식 1로 표시되는 화합물을 쥐의 멜라노마 세포(B-16 mouse melanoma cell)에 첨가한 후 멜라닌 총량을 측정한 결과, 상기 화합물을 첨가한 실험군의 경우 양성대조군에 비하여 상당히 우수한 멜라닌 총량 감소 효과를 나타내어, 화학식 1로 표시되는 화합물을 포함하는 조성물은 피부 미백 용도로 사용될 수 있음을 확인하였다(표 1).In the present invention, “skin whitening” refers to not only brightening skin tone by inhibiting the synthesis of melanin pigment, but also improving skin hyperpigmentation such as spots and freckles caused by ultraviolet rays, hormones, or genetics. In one embodiment of the present invention, the total amount of melanin was measured after adding the compound represented by Formula 1 to mouse melanoma cells (B-16 mouse melanoma cells). As a result, the experimental group to which the compound was added was compared to the positive control group. It was confirmed that the composition containing the compound represented by Formula 1 can be used for skin whitening by showing a significantly superior effect in reducing the total amount of melanin compared to that of the composition (Table 1).
본 발명에 있어서, “피부 탄력 증진”이란 피부가 쳐지거나 늘어지는 정도를 완화시켜주는 것으로, 엘라스틴으로 구성된 탄력섬유가 콜라겐(collagen)이라고 하는 교원섬유와 함께 존재하는데, 엘라스틴과 콜라겐이 충분히 존재하는 상태에서 피부 탄력이 유지되는 것을 말한다. 본 발명에 있어서, “주름 개선”이란 피부에 주름이 생성되는 것을 억제 또는 저해하거나, 이미 생성된 주름을 완화시키는 것을 말한다. In the present invention, “promoting skin elasticity” refers to alleviating the degree of sagging or sagging skin, where elastic fibers composed of elastin exist together with collagen fibers called collagen, and elastin and collagen are sufficiently present. This means that skin elasticity is maintained in this condition. In the present invention, “wrinkle improvement” refers to suppressing or inhibiting the formation of wrinkles on the skin or alleviating wrinkles that have already formed.
본 발명의 일 실시예에서는, 화학식 1로 표시되는 화합물을 인간 유래 섬유아세포의 배양액에 첨가한 후 콜라겐 합성 촉진 효과를 실험한 결과, 상기 화합물을 첨가한 실험군의 경우 양성대조군에 비하여 같은 농도에서 상당히 우수한 콜라겐 합성 효과를 나타내었다(표 2). In one embodiment of the present invention, the effect of promoting collagen synthesis was tested after adding the compound represented by Formula 1 to the culture medium of human-derived fibroblasts. As a result, the experimental group to which the compound was added significantly increased at the same concentration compared to the positive control group. It showed excellent collagen synthesis effect (Table 2).
또한, 본 발명의 일 실시예에서는, 상기 화학식 1로 표시되는 화합물의 엘라스타제 활성 저해 효과를 실험한 결과, 테뉴폴리사이드 에이를 첨가한 실험군의 경우 우수한 엘라스타제 활성 저해 효과를 나타내었다(표 3). 이를 통해, 화학식 1로 표시되는 화합물을 포함하는 조성물은 피부 탄력 증진 또는 주름 개선 용도로 사용될 수 있음을 확인하였다.In addition, in one example of the present invention, as a result of testing the elastase activity inhibition effect of the compound represented by Formula 1, the experimental group to which tenupolyside A was added showed an excellent elastase activity inhibition effect ( Table 3). Through this, it was confirmed that a composition containing the compound represented by Formula 1 can be used for improving skin elasticity or improving wrinkles.
본 발명에 있어서, “피부 보습”이란 피부에 수분감을 증가시켜주고, 촉촉한 상태를 유지시키는 것을 의미한다. 피부 보습 효과는 피부의 주름개선, 탄력도 증가에 도움을 줄 수 있다. 본 발명의 일 실시예에서는, 상기 화학식 1로 표시되는 화합물의 우수한 콜라겐 합성 효과, 엘라스타제 활성 저해 효과를 나타내었는바, 화학식 1로 표시되는 화합물 포함하는 조성물은 피부 보습 용도로 사용될 수 있음을 확인하였다(표 2 내지 3).In the present invention, “skin moisturizing” means increasing moisture in the skin and maintaining a moist state. The skin moisturizing effect can help improve skin wrinkles and increase elasticity. In one embodiment of the present invention, the compound represented by Formula 1 showed excellent collagen synthesis effect and elastase activity inhibition effect, indicating that a composition containing the compound represented by Formula 1 can be used for skin moisturizing purposes. Confirmed (Tables 2 to 3).
본 발명에 있어서, “항산화”란 세포 내 대사 또는 자외선의 영향으로 인한 산화적 스트레스에 따라 반응성이 높은 자유 라디칼(free radical) 또는 활성산소종(reactive oxygen species;ROS)에 의한 세포의 산화를 억제하는 것을 말하며, 자유 라디칼 또는 활성산소종을 제거하여 이로 인한 세포의 손상이 감소되는 것을 포함한다. 본 발명의 일 실시예에서는, 화학식 1로 표시되는 화합물의 자유라디칼 소거 활성을 측정한 결과, 상기 화합물을 첨가한 실험군의 경우 양성대조군에 비하여 더 우수한 항산화 효과를 나타내었다. 이를 통해 화학식 1로 표시되는 화합물을 포함하는 조성물은 항산화 용도로 사용될 수 있으며, 피부 미백, 탄력 증진, 주름 개선 및 피부 보습에 있어, 보조적인 역할로 작용할 수 있음을 확인하였다(표 4).In the present invention, “antioxidation” refers to inhibiting oxidation of cells by highly reactive free radicals or reactive oxygen species (ROS) due to oxidative stress caused by intracellular metabolism or the effects of ultraviolet rays. This refers to removing free radicals or reactive oxygen species and reducing damage to cells caused by them. In one example of the present invention, as a result of measuring the free radical scavenging activity of the compound represented by Formula 1, the experimental group to which the compound was added showed a better antioxidant effect than the positive control group. Through this, it was confirmed that the composition containing the compound represented by Formula 1 can be used for antioxidant purposes and can play an auxiliary role in skin whitening, improving elasticity, improving wrinkles, and moisturizing the skin (Table 4).
본 발명에 있어서, “피부 트러블”이란 대식세포에서의 과도한 일산화질소 생성으로 인하여 유발된 염증에 의해 발생할 수 있는 피부질환을 의미한다. 상기 피부 트러블은 염증과 관련된 피부질환이면 그 종류에 관계없이 모두 포함되며, 상기 염증과 관련된 피부질환의 비제한적인 예로는 아토피 피부염, 건선, 방사선, 화학물질, 화상 등에 의해 촉발되는 홍반성 질환, 산 화상, 수포성 피부병, 태선 모양 종류 질환, 알레르기에 기한 가려움증, 지루성 습진, 장미 여드름, 심상성 천포창, 다형 삼출성 홍반, 결절 홍반, 귀두염, 음문염, 원형 탈모증과 같은 염증성 모발 손실, 피부 T-세포 림프종 등이 있으며, 구체적으로, 피부발진, 여드름, 뾰루지, 주사(빨간 코) 등이 있으나 이에 제한되는 것은 아니다. 또한, 본 발명에서 사용되는 용어, "트러블 개선"이란 피부에 트러블이 생성되는 것을 억제 또는 저해하거나, 이미 생성된 트러블을 완화시키는 것을 말한다. In the present invention, “skin trouble” refers to a skin disease that can be caused by inflammation caused by excessive production of nitric oxide in macrophages. The skin trouble includes any type of skin disease related to inflammation, and non-limiting examples of skin diseases related to inflammation include atopic dermatitis, psoriasis, erythematous disease triggered by radiation, chemicals, burns, etc. Acid burns, bullous dermatoses, lichenoid diseases, itching due to allergies, seborrheic eczema, acne rosacea, pemphigus vulgaris, erythema multiforme exudative, erythema nodosum, balanitis, vulvitis, inflammatory hair loss such as alopecia areata, skin T- Cellular lymphoma, etc. specifically includes, but is not limited to, skin rash, acne, pimples, rosacea (red nose), etc. In addition, the term "trouble improvement" used in the present invention refers to suppressing or inhibiting the formation of skin troubles or relieving already created troubles.
본 발명에 있어서, “항염증”이란 염증을 억제하는 것을 말하며, 상기 염증은 어떤 자극에 대한 생체조직의 방어반응의 하나로, 조직 변질, 순환 장애와 삼출, 조직 증식의 세가지를 병발하는 복잡한 병변을 말한다. 보다 구체적으로 염증은 선천성 면역의 일부이며 다른 동물에서처럼 인간의 선천성 면역은 병원체에 특이적으로 존재하는 세포 표면의 패턴을 인식한다. 식세포는 그런 표면을 가진 세포를 비자기로 인식하고 병원체를 공격한다. 만일 병원균이 신체의 물리적 장벽을 깨고 들어온다면 염증반응이 일어난다. 염증반응은 상처부위에 침입한 미생물들에 대한 적대 환경을 만드는 비특이적인 방어작용이다. 염증반응에서, 상처가 나거나 외부 감염체가 체내로 들어왔을 때, 초기단계 면역반응을 맡고 있는 백혈구들이 몰려들어 사이토카인을 발현한다. 따라서 세포 내 사이토카인의 발현양이 염증반응 활성화의 지표가 된다. 본 발명의 항염증은 피부에서 발병된 염증을 억제하는 것일 수 있다.In the present invention, “anti-inflammation” refers to suppressing inflammation, which is one of the defense responses of living tissue to certain stimuli and causes complex lesions that occur together with three factors: tissue deterioration, circulatory failure and exudation, and tissue proliferation. says More specifically, inflammation is part of innate immunity, and as in other animals, human innate immunity recognizes patterns on the cell surface that are specific to pathogens. Phagocytes recognize cells with such a surface as non-self and attack the pathogen. If pathogens break through the body's physical barriers, an inflammatory response occurs. The inflammatory response is a non-specific defense function that creates a hostile environment for microorganisms invading the wound area. In an inflammatory response, when a wound occurs or an external infectious agent enters the body, white blood cells responsible for the initial immune response flock in and express cytokines. Therefore, the expression level of intracellular cytokines becomes an indicator of inflammatory response activation. The anti-inflammatory of the present invention may suppress inflammation occurring in the skin.
본 발명의 일 실시예에서는, 화학식 1로 표시되는 화합물의 NO 생성 억제력을 측정한 결과, 상기 화합물을 첨가한 실험군의 경우 양성대조군에 상응하는 정도의 항염증 효과를 나타내었다. 이를 통해 화학식 1로 표시되는 화합물을 포함하는 조성물은 피부 트러블 개선 용도로 사용될 수 있으며, 피부 미백, 탄력 증진, 주름 개선 및 피부 보습에 있어, 보조적인 역할로 작용할 수 있음을 확인하였다(표 5).In one example of the present invention, as a result of measuring the NO production inhibition power of the compound represented by Formula 1, the experimental group to which the compound was added showed an anti-inflammatory effect comparable to that of the positive control group. Through this, it was confirmed that the composition containing the compound represented by Formula 1 can be used to improve skin troubles and can play an auxiliary role in skin whitening, improving elasticity, improving wrinkles, and moisturizing the skin (Table 5) .
본 발명에 따른 화장료 조성물은 용액, 외용연고, 크림, 폼, 영양화장수, 유연화장수, 팩, 유연수, 유액, 메이크업베이스, 에센스, 비누, 액체 세정료, 입욕제, 선 스크린크림, 선오일, 현탁액, 유탁액, 페이스트, 겔, 로션, 파우더, 비누, 계면활성제-함유 클린싱, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션, 패취 및 스프레이로 구성된 군으로부터 선택되는 제형으로 제조할 수 있으나, 이에 제한되는 것은 아니다.The cosmetic composition according to the present invention includes solutions, external ointments, creams, foams, nourishing lotions, softening lotions, packs, softening water, emulsions, makeup bases, essences, soaps, liquid cleansers, bath salts, sunscreen creams, sun oils, suspensions, Can be prepared in a formulation selected from the group consisting of emulsions, pastes, gels, lotions, powders, soaps, surfactant-containing cleansers, oils, powder foundations, emulsion foundations, wax foundations, patches and sprays. That is not the case.
또한, 본 발명의 화장료 조성물은 일반 피부 화장료에 배합되는 화장품학적으로 허용 가능한 담체를 1 종 이상 추가로 포함할 수 있으며, 통상의 성분으로 예를 들면 유분, 물, 계면활성제, 보습제, 저급 알콜, 증점제, 킬레이트제, 색소, 방부제, 향료 등을 적절히 배합할 수 있으나, 이에 제한되는 것은 아니다.In addition, the cosmetic composition of the present invention may additionally include one or more cosmetically acceptable carriers that are blended with general skin cosmetics, and common ingredients include, for example, oil, water, surfactant, moisturizer, lower alcohol, Thickeners, chelating agents, pigments, preservatives, fragrances, etc. may be appropriately mixed, but are not limited thereto.
본 발명의 화장료 조성물에 포함되는 화장품학적으로 허용 가능한 담체는 제형에 따라 다양하다.Cosmetically acceptable carriers included in the cosmetic composition of the present invention vary depending on the formulation.
본 발명의 제형이 연고, 페이스트, 크림 또는 젤인 경우에는, 담체 성분으로서 동물성 유, 식물성 유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크, 산화아연 또는 이들의 혼합물이 이용될 수 있다.When the formulation of the present invention is an ointment, paste, cream or gel, the carrier ingredient may be animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide or Mixtures of these can be used.
본 발명의 제형이 파우더 또는 스프레이인 경우에는, 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록사이드, 칼슘 실케이트, 폴리아미드 파우더 또는 이들의 혼합물이 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진제를 포함할 수 있다.When the formulation of the present invention is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silcate, polyamide powder, or mixtures thereof may be used as the carrier ingredient, and especially in the case of a spray, chloro May contain propellants such as fluorohydrocarbons, propane/butane or dimethyl ether.
본 발명의 제형이 용액 또는 유탁액인 경우에는, 담체 성분으로서 용매, 용해화제 또는 유탁화제가 이용되며, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알콜, 벤질 벤조에이트, 프로필렌글리콜, 1,3-부틸글리콜 오일이 이용될 수 있으며, 특히, 목화씨 오일, 땅콩 오일, 옥수수 배종 오일, 올리브오일, 피마자 오일 및 참깨 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 이용될 수 있다.When the formulation of the present invention is a solution or emulsion, a solvent, solubilizing agent or emulsifying agent is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-Butyl glycol oils may be used, in particular cottonseed oil, peanut oil, corn germ oil, olive oil, castor oil and sesame oil, aliphatic esters of glycerol, fatty acid esters of polyethylene glycol or sorbitan. there is.
본 발명의 제형이 현탁액인 경우에는, 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알콜, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다.When the formulation of the present invention is a suspension, the carrier components include water, a liquid diluent such as ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, and miso. Crystalline cellulose, aluminum metahydroxide, bentonite, agar, or tracant may be used.
본 발명의 제형이 비누인 경우에는 담체 성분으로서 지방산의 알칼리 금속 염, 지방산 헤미에스테르 염, 지방산 단백질 히드롤리제이트, 이세티오네이트, 라놀린 유도체, 지방족 알콜, 식물성 유, 글리세롤, 당 등이 이용될 수 있다.When the formulation of the present invention is soap, alkali metal salts of fatty acids, hemiester salts of fatty acids, fatty acid protein hydrolyzates, isethionates, lanolin derivatives, fatty alcohols, vegetable oils, glycerol, sugars, etc. may be used as carrier ingredients. You can.
본 발명의 다른 양태로서, 상기 화학식 1로 표시되는 화합물 또는 이의 식품학적으로 허용 가능한 염을 포함하는 식품 조성물을 제공한다.In another aspect of the present invention, a food composition comprising the compound represented by Formula 1 or a foodologically acceptable salt thereof is provided.
또한, 구체적으로, 본 발명은 상기 화학식 1로 표시되는 화합물 또는 이의 식품학적으로 허용 가능한 염을 포함하는 피부 미백용, 피부 탄력 증진 또는 주름 개선용, 피부 보습용, 항산화용, 또는 피부 트러블 개선용 식품 조성물을 제공할 수 있다. 상기 화학식 1로 표시되는 테뉴폴리사이드 에이 화합물, 피부 미백, 피부 탄력 증진, 주름 개선, 피부 보습, 항산화 및 피부 트러블 개선은 상기에서 설명한 바와 같다. 상기 식품 조성물은 건강기능식품의 형태로 사용될 수 있으나, 이에 제한되는 것은 아니다.In addition, specifically, the present invention relates to a compound containing the compound represented by Formula 1 or a food-acceptable salt thereof for whitening skin, improving skin elasticity or improving wrinkles, moisturizing skin, antioxidant, or improving skin troubles. A food composition can be provided. Tenupolyside A compound represented by Chemical Formula 1, skin whitening, skin elasticity enhancement, wrinkle improvement, skin moisturization, antioxidant and skin trouble improvement are as described above. The food composition may be used in the form of a health functional food, but is not limited thereto.
본 발명의 식품 조성물에 포함된 화학식 1로 표시되는 화합물 또는 이의 식품학적으로 허용 가능한 염은 화학식 1로 표시되는 화합물을 포함하는 동식물, 이의 추출물, 이의 분획물 또는 이의 가공물의 형태로 포함될 수 있다. 또한 상기 조성물은 유효성분 이외에 식품학적으로 허용 가능한 식품보조첨가제를 포함할 수 있다.The compound represented by Formula 1 or a foodologically acceptable salt thereof contained in the food composition of the present invention may be included in the form of animals or plants containing the compound represented by Formula 1, extracts thereof, fractions thereof, or processed products thereof. Additionally, the composition may include food additives that are foodologically acceptable in addition to the active ingredients.
본 발명에 있어서, "식품보조첨가제"란 식품에 보조적으로 첨가될 수 있는 구성요소를 의미하며, 각 제형의 건강기능식품을 제조하는데 첨가되는 것으로서 당업자가 적절히 선택하여 사용할 수 있다. 식품보조첨가제의 예로는 여러 가지 영양제, 비타민, 광물(전해질), 합성 풍미제 및 천연 풍미제 등의 풍미제, 착색제 및 충진제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산음료에 사용되는 탄산화제 등이 포함되지만, 상기 예들에 의해 본 발명의 식품보조첨가제의 종류가 제한되는 것은 아니다.In the present invention, “food supplement” refers to a component that can be added to food as an auxiliary ingredient, and can be appropriately selected and used by a person skilled in the art as it is added to manufacture each type of health functional food. Examples of food supplements include various nutrients, vitamins, minerals (electrolytes), flavoring agents such as synthetic and natural flavors, colorants and fillers, pectic acid and its salts, alginic acid and its salts, organic acids, and protective colloidal thickeners. , pH adjusters, stabilizers, preservatives, glycerin, alcohol, carbonating agents used in carbonated beverages, etc., but the types of food supplements of the present invention are not limited to the above examples.
본 발명의 식품 조성물에는 건강기능식품이 포함될 수 있다. 본 발명에 있어서, "건강기능식품"이란 인체에 유용한 기능성을 가진 원료나 성분을 사용하여 정제, 캅셀, 분말, 과립, 액상 및 환 등의 형태로 제조 및 가공한 식품을 말한다. 여기서 “기능성”이라 함은 인체의 구조 및 기능에 대하여 영양소를 조절하거나 생리학적 작용 등과 같은 보건용도에 유용한 효과를 얻는 것을 의미한다. 본 발명의 건강기능식품은 당업계에서 통상적으로 사용되는 방법에 의하여 제조 가능하며, 상기 제조시에는 당업계에서 통상적으로 첨가하는 원료 및 성분을 첨가하여 제조할 수 있다. 또한 상기 건강기능식품의 제형 또한 건강기능식품으로 인정되는 제형이면 제한 없이 제조될 수 있다. 본 발명의 식품 조성물은 다양한 형태의 제형으로 제조될 수 있으며, 일반 약품과는 달리 식품을 원료로 하여 약품의 장기 복용 시 발생할 수 있는 부작용 등이 없는 장점이 있고, 휴대성이 뛰어나, 본 발명의 건강기능식품은 피부 미백, 피부 탄력 증진 또는 주름 개선, 피부 보습, 항산화 또는 피부 트러블 개선 효과를 증진시키기 위한 보조제로 섭취가 가능하다.The food composition of the present invention may include health functional foods. In the present invention, “health functional food” refers to food manufactured and processed in the form of tablets, capsules, powders, granules, liquids, and pills using raw materials or ingredients with functional properties useful to the human body. Here, “functionality” means controlling nutrients for the structure and function of the human body or obtaining useful effects for health purposes, such as physiological effects. The health functional food of the present invention can be manufactured by a method commonly used in the art, and can be manufactured by adding raw materials and components commonly added in the art. Additionally, the formulation of the health functional food can also be manufactured without limitation as long as it is a formulation recognized as a health functional food. The food composition of the present invention can be manufactured in various types of formulations, and unlike general drugs, it is made from food as a raw material and has the advantage of not having side effects that may occur when taking the drug for a long period of time. It is also excellent in portability and can be used as a pharmaceutical composition according to the present invention. Health functional foods can be consumed as supplements to improve skin whitening, skin elasticity, wrinkle improvement, skin moisturization, antioxidant or skin trouble improvement effects.
본 발명의 건강기능식품이 취할 수 있는 형태에는 제한이 없으며, 통상적인 의미의 식품을 모두 포함할 수 있고, 기능성 식품 등 당업계에 알려진 용어와 혼용 가능하다. 아울러 본 발명의 건강기능식품은 당업자의 선택에 따라 식품에 포함될 수 있는 적절한 기타 보조성분과 공지의 첨가제를 혼합하여 제조할 수 있다. 첨가할 수 있는 식품의 예로는 육류, 소세지, 빵, 쵸코렛, 캔디류, 스낵류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차, 드링크제, 알콜 음료 및 비타민 복합제 등이 있으며, 본 발명에 따른 화학식 1로 표시되는 화합물을 주성분으로 하여 제조한 즙, 차, 젤리 및 주스 등에 첨가하여 제조할 수 있다. 또한 동물을 위한 사료로 이용되는 식품도 포함한다.There is no limit to the form that the health functional food of the present invention can take, and it can include all foods in the conventional sense, and can be used interchangeably with terms known in the art, such as functional food. In addition, the health functional food of the present invention can be manufactured by mixing known additives with other appropriate auxiliary ingredients that can be included in the food according to the selection of a person skilled in the art. Examples of foods that can be added include meat, sausages, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gum, dairy products including ice cream, various soups, beverages, tea, drinks, alcoholic beverages, and There are vitamin complexes, etc., and they can be prepared by adding the compound represented by Chemical Formula 1 according to the present invention to juices, teas, jellies, etc. prepared as main ingredients. It also includes foods used as feed for animals.
본 발명의 또 다른 양태로서, 상기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염을 포함하는 의약외품 조성물을 제공한다.In another aspect of the present invention, a quasi-drug composition containing the compound represented by Formula 1 or a pharmaceutically acceptable salt thereof is provided.
또한, 구체적으로, 본 발명은 상기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염을 포함하는 피부 미백용, 피부 탄력 증진 또는 주름 개선용, 피부 보습용, 항산화용, 또는 피부 트러블 개선용 의약외품 조성물을 제공할 수 있다. 상기 화학식 1로 표시되는 테뉴폴리사이드 에이 화합물, 피부 미백, 피부 탄력 증진, 주름 개선, 피부 보습, 항산화 및 피부 트러블 개선은 상기에서 설명한 바와 같다.In addition, specifically, the present invention relates to a compound containing the compound represented by Formula 1 or a pharmaceutically acceptable salt thereof for whitening skin, improving skin elasticity or improving wrinkles, moisturizing skin, antioxidant, or improving skin troubles. A quasi-drug composition can be provided. Tenupolyside A compound represented by Chemical Formula 1, skin whitening, skin elasticity enhancement, wrinkle improvement, skin moisturization, antioxidant and skin trouble improvement are as described above.
본 발명의 의약외품 조성물에는 상기 성분 외에 필요에 따라 약학적으로 허용 가능한 담체, 부형제 또는 희석제를 더욱 포함할 수 있다. 상기 약학적으로 허용 가능한 담체, 부형제 또는 희석제는 본 발명의 효과를 해하지 않는 한 제한되지 않으며, 예를 들어 충진제, 증량제, 결합제, 습윤제, 붕해제, 계면활성제, 윤활제, 감미제, 방향제, 보존제 등을 포함할 수 있다.In addition to the above ingredients, the quasi-drug composition of the present invention may further include pharmaceutically acceptable carriers, excipients, or diluents as needed. The pharmaceutically acceptable carrier, excipient, or diluent is not limited as long as it does not impair the effect of the present invention, and includes, for example, fillers, extenders, binders, wetting agents, disintegrants, surfactants, lubricants, sweeteners, fragrances, preservatives, etc. It can be included.
본 발명의 약학적으로 허용 가능한 담체, 부형제 또는 희석제의 대표적인 예로는, 락토즈, 덱스트로스, 슈크로스, 솔비톨, 만니톨, 자일리톨, 말티톨, 전분, 젤라틴, 글리세린, 아카시아 고무, 알지네이트, 칼슘포스페이트, 칼슘카보네이트, 칼슘실리케이트, 셀룰로즈, 메틸 셀룰로즈, 미정질 셀룰로즈, 폴리비닐 피롤리돈, 물, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 탈크, 마그네슘 스테아레이트, 광물유, 프로필렌글리콜, 폴리에틸렌글리콜, 식물성 오일, 주사가능한 에스테르, 위텝솔, 마크로골, 트윈 61, 카카오지, 라우리지 등을 들 수 있다.Representative examples of pharmaceutically acceptable carriers, excipients or diluents of the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, maltitol, starch, gelatin, glycerin, gum acacia, alginate, calcium phosphate, calcium. Carbonate, calcium silicate, cellulose, methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methyl hydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, mineral oil, propylene glycol, polyethylene glycol, vegetable oil. , injectable esters, Wethepsol, Macrogol, Tween 61, Kakaoji, Lauridge, etc.
또한, 본 발명의 화학식 1로 표시되는 화합물을 의약외품으로 사용하는 경우, 추가로 동일 또는 유사한 기능을 나타내는 유효성분을 1종 이상 함유할 수 있다. 예컨대, 공지의 피부 미백, 탄력 증진, 주름 개선, 보습, 항산화 또는 항염증 성분을 포함할 수 있을 것이다. 추가적인 피부 미백, 탄력 증진, 주름 개선, 보습, 항산화 또는 항염증 성분을 포함하게 되면 본 발명의 조성물의 피부 미백, 탄력 증진, 주름 개선, 보습, 항산화 또는 피부 트러블 개선 효과는 더욱 증가될 수 있을 것이다. 상기 성분 추가 시에는 복합 사용에 따른 피부 안전성, 제형화의 용이성, 유효성분들의 안정성을 고려할 수 있다. 상기 의약외품 조성물은 당업계에 공지된 미백 성분으로서, 코즈산(Kojic acid), 알부틴(Arbutin) 등과 같은 티로시나제 효소활성을 억제하는 물질, 하이드로퀴논(Hydroquinone), 비타민-C(L-Ascorbic acid); 당업계에 공지된 피부 탄력, 주름 개선 또는 보습 성분으로서, 레티노산, TGF, 동물 태반 유래의 단백질, 베툴린산 및 클로렐라 추출물; 당업계에 공지된 항산화 성분으로서, 페놀성 화합물, 플라보노이드, 토코페롤, 비타민 C, 셀레늄; 당업계에 공지된 항염증 성분으로서, 비스테로이드계로 플루페남산, 이부프로펜, 벤지다민, 인도메타신, 프레드니솔론, 덱사메타손, 알란토인, 아즈엔, 하이드로코티손; 및 이들의 유도체와 각종 식물 추출물로 구성되는 군으로부터 선택되는 1종 또는 2종 이상의 성분을 추가로 포함할 수 있다. 추가 성분은 전체 조성물 중량에 대하여 0.0001 중량% 내지 10 중량%로 포함될 수 있을 것이며, 상기 함량 범위는 피부 안전성, 상기 화학식 1로 표시되는 화합물의 제형화 시의 용이성 등의 요건에 따라 조절될 수 있을 것이다.In addition, when the compound represented by Formula 1 of the present invention is used as a quasi-drug, it may additionally contain one or more active ingredients showing the same or similar functions. For example, it may include known skin whitening, elasticity enhancement, wrinkle improvement, moisturizing, antioxidant or anti-inflammatory ingredients. If additional skin whitening, elasticity enhancement, wrinkle improvement, moisturizing, antioxidant or anti-inflammatory ingredients are included, the skin whitening, elasticity enhancement, wrinkle improvement, moisturizing, antioxidant or skin trouble improvement effects of the composition of the present invention can be further increased. . When adding the above ingredients, skin safety due to combined use, ease of formulation, and stability of the active ingredients can be taken into consideration. The quasi-drug composition includes whitening ingredients known in the art, such as substances that inhibit tyrosinase enzyme activity such as Kojic acid and Arbutin, Hydroquinone, Vitamin-C (L-Ascorbic acid); Skin elasticity, wrinkle improvement or moisturizing ingredients known in the art include retinoic acid, TGF, protein from animal placenta, betulinic acid and chlorella extract; Antioxidant ingredients known in the art include phenolic compounds, flavonoids, tocopherol, vitamin C, selenium; Anti-inflammatory ingredients known in the art include non-steroidal flufenamic acid, ibuprofen, benzydamine, indomethacin, prednisolone, dexamethasone, allantoin, Azn, hydrocortisone; and one or two or more ingredients selected from the group consisting of their derivatives and various plant extracts. Additional ingredients may be included in an amount of 0.0001% to 10% by weight based on the total weight of the composition, and the content range may be adjusted according to requirements such as skin safety and ease of formulation of the compound represented by Formula 1. will be.
본 발명의 의약외품 조성물은 소독 청결제, 샤워폼, 연고액, 물티슈, 코팅제 등을 예시할 수 있으나 이에 제한되는 것이 아니며, 의약외품의 제제화 방법, 용량, 이용방법, 구성성분 등은 기술분야에 공지된 통상의 기술로부터 적절히 선택될 수 있다.The quasi-drug composition of the present invention may include, but is not limited to, disinfectant cleaners, shower foams, ointments, wet tissues, coating agents, etc., and the formulation method, dosage, usage method, components, etc. of the quasi-drugs are commonly known in the technical field. It can be appropriately selected from the techniques.
또한, 본 발명의 상기 화학식 1로 표시되는 화합물은 개체의 피부에 도포하는 단계를 포함하는, 피부 미백, 피부 탄력 증진 또는 주름 개선, 피부 보습, 항산화 또는 피부 트러블 개선 방법에 사용될 수 있다. 상기 개체는 쥐, 가축, 인간 등을 포함하는 포유동물을 제한 없이 포함한다.In addition, the compound represented by Formula 1 of the present invention can be used in a method for skin whitening, improving skin elasticity or wrinkle improvement, skin moisturizing, antioxidant, or improving skin troubles, which includes the step of applying it to the skin of an individual. The subject includes mammals, including rats, livestock, humans, etc., without limitation.
본 발명의 테뉴폴리사이드 에이 또는 이의 화장품학적으로 허용 가능한 염을 유효성분으로 포함하는 화장료 조성물은 피부 미백, 탄력 증진 또는 주름 개선, 피부 보습, 항산화, 피부 트러블 개선 효능이 우수하다. 구체적으로 본 발명의 조성물은 저농도에서도 뛰어난 멜라닌 총량 감소 효과를 나타내고 콜라겐 합성 촉진 효과, 엘라스타제 활성 저해 효과가 우수하며, 항산화, 항염증 및 항당화 효과가 우수하여 피부 미백용, 탄력 증진용 또는 주름 개선용, 피부 보습용, 항산화용 및 피부 트러블 개선용 화장료 조성물로서의 활용도가 높다. 또한, 본 발명의 테뉴폴리사이드 에이를 포함하는 조성물은 식품 조성물 및 의약외품 조성물로서 사용할 수 있다.The cosmetic composition containing Tenupolyside A or a cosmetically acceptable salt thereof of the present invention as an active ingredient has excellent skin whitening, elasticity improvement or wrinkle improvement, skin moisturizing, antioxidant, and skin trouble improvement effects. Specifically, the composition of the present invention exhibits an excellent effect of reducing the total amount of melanin even at low concentrations, has an excellent effect of promoting collagen synthesis and inhibiting elastase activity, and has excellent antioxidant, anti-inflammatory and anti-glycation effects, so that it is used for skin whitening, improving elasticity or It has high utility as a cosmetic composition for wrinkle improvement, skin moisturizing, antioxidant use, and skin trouble improvement. Additionally, the composition containing tenupolyside A of the present invention can be used as a food composition and quasi-drug composition.
이하, 실시예를 통하여 본 발명의 구성 및 효과를 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 예시하기 위한 것일 뿐 본 발명의 범위가 이들 실시예에 의해 제한되는 것은 아니다.Hereinafter, the configuration and effects of the present invention will be described in more detail through examples. These examples are only for illustrating the present invention and the scope of the present invention is not limited by these examples.
참조예Reference example 1 : One : 테뉴폴리사이드tenupoliside 에이( no way( tenuifolisidetenuifoliside A) 물질 정보 A) Material information
[화학식 1][Formula 1]
물질명 : Tenuifoliside ASubstance name: Tenuifoliside A
CAS No. : 139726-35-5CAS No. : 139726-35-5
분자식 : C31H38O17 Molecular formula: C 31 H 38 O 17
분자량 : 682.63Molecular Weight: 682.63
구입처 : CHENGDU MUST BIO-TECHNOLOGY CO., LTD. Where to buy: CHENGDU MUST BIO-TECHNOLOGY CO., LTD.
실험예Experiment example 1 : 세포 수준에서의 멜라닌 총량 감소 효과에 따른 미백 효과 1: Whitening effect due to the effect of reducing the total amount of melanin at the cellular level
상기 화학식 1의 화합물을 쥐의 멜라노마 세포(B-16 mouse melanoma cell)의 배양액에 첨가하여 세포 수준에서의 멜라닌 총량을 측정함으로써 미백 효과를 확인하였다(Lotan R., Lotan D. Cancer Res. 40:3345-3350, 1980). 실험 전 쥐의 멜라노마 세포에 대하여 독성을 평가하여 독성이 없는 농도를 선정하여 미백 평가를 수행하였다.The compound of Formula 1 was added to the culture medium of B-16 mouse melanoma cells, and the whitening effect was confirmed by measuring the total amount of melanin at the cellular level (Lotan R., Lotan D. Cancer Res . 40 :3345-3350, 1980). Before the experiment, toxicity was evaluated for rat melanoma cells, a non-toxic concentration was selected, and whitening evaluation was performed.
화학식 1의 화합물을 배양액에 최종 농도가 1 ppm 또는 20 ppm이 되도록 하였으며, 대조군인 셀리나는 20 ppm이 되도록 첨가하여 각각 B-16 멜라노마 세포에 처리한 후 3일간 배양하였다.The compound of Formula 1 was added to the culture medium to a final concentration of 1 ppm or 20 ppm, and Selina, a control, was added to 20 ppm, treated with B-16 melanoma cells, and cultured for 3 days.
이후, 세포들을 트립신(trypsin) 처리하여 배양용기로부터 떼어내 원심분리한 후, 멜라닌을 추출하였다. 떼어낸 세포는 수산화나트륨 용액(1N 농도) 1 ml를 가하여 10 분간 끓여 멜라닌을 녹이고 분광 광도계를 이용하여 400 nm에서 흡광도를 측정함으로써 생성된 멜라닌의 양을 측정하였다.Afterwards, the cells were treated with trypsin, removed from the culture vessel, centrifuged, and melanin was extracted. To the removed cells, 1 ml of sodium hydroxide solution (1N concentration) was added and boiled for 10 minutes to dissolve the melanin. The amount of melanin produced was measured by measuring the absorbance at 400 nm using a spectrophotometer.
상기 멜라닌 양은 단위 세포수당(1×106 cell)의 흡광도로 나타내는 방법으로 측정하였으며, 음성대조군에 대한 상대적인 멜라닌 총량을 저해율(%)로 계산하고 결과를 하기 표 1에 정리하였다.The amount of melanin was measured by expressing the absorbance per unit cell (1 × 10 6 cell), and the total amount of melanin relative to the negative control group was calculated as an inhibition rate (%), and the results are summarized in Table 1 below.
상기 표 1의 결과에서 볼 수 있듯이, 화학식 1의 화합물은 양성대조군인 셀리나와 비교했을 때, 같은 농도인 20 ppm에서도 상당히 우수한 멜라닌 총량 감소 효과를 나타내어, 피부 미백 용도로 사용할 수 있음을 알 수 있었다.As can be seen from the results in Table 1, the compound of Chemical Formula 1 showed a significantly superior effect of reducing the total amount of melanin even at the same concentration of 20 ppm compared to Selina, a positive control, and could be used for skin whitening. .
실험예Experiment example 2 : 인체 유래의 섬유아세포에서 제1형 콜라겐(type Ⅰ collagen) 합성 촉진 효과 2: Effect of promoting type 1 collagen synthesis in human-derived fibroblasts
화학식 1의 화합물을 인간 유래 섬유아세포의 배양액에 첨가하여 세포 수준에서 제1형 콜라겐 합성 촉진 효과를 확인하였다. 합성된 콜라겐의 측정은 PICP EIA kit(Procollagen Type Ⅰ C-Peptide Enzyme Immuno Assay KIT)를 이용하여 정량하였다. 콜라겐 합성량을 측정하기 위해 화학식 1의 화합물을 섬유아세포의 배양배지(DMEM 배지)에 첨가하여 48 시간 배양한 후 배양액을 취하여 PICP EIA 키트로 저농도에서 제1형 콜라겐 합성 정도를 분광광도계를 이용하여 450 nm에서 측정하였다.The compound of Formula 1 was added to the culture medium of human-derived fibroblasts, and the effect of promoting type 1 collagen synthesis was confirmed at the cellular level. The synthesized collagen was quantified using the PICP EIA kit (Procollagen Type Ⅰ C-Peptide Enzyme Immuno Assay KIT). To measure the amount of collagen synthesis, the compound of formula 1 was added to the culture medium (DMEM medium) of fibroblasts and cultured for 48 hours, then the culture medium was taken and the degree of type 1 collagen synthesis was measured at low concentration using a PICP EIA kit using a spectrophotometer. Measured at 450 nm.
효과의 비교를 위하여 시료를 처리하지 않은 섬유아세포의 배양배지(음성대조군)와 비타민 C(양성대조군)를 최종농도 52.85 μg/ml 가 되도록 첨가한 시료에 대하여 동일한 방법으로 콜라겐 합성 정도를 측정하였다. 콜라겐 생성 증가율은 대조군에 대한 상대적인 콜라겐 생성량의 비율로 계산하고 결과를 하기 표 2에 나타내었다.To compare the effects, the degree of collagen synthesis was measured using the same method for samples to which untreated fibroblast culture medium (negative control) and vitamin C (positive control) were added to a final concentration of 52.85 μg/ml. The rate of increase in collagen production was calculated as the ratio of collagen production relative to the control group, and the results are shown in Table 2 below.
상기 표 2의 결과에서 볼 수 있듯이, 화학식 1의 화합물을 처리한 경우, 농도 의존적으로 콜라겐 합성이 증가되었고, 일반적으로 콜라겐 합성을 유도하는 것으로 잘 알려진 비타민 C를 적용한 경우에 비해 같은 농도인 50 ppm에서 우수한 콜라겐 합성 효과를 나타내었다. 따라서, 화학식 1의 화합물은 피부 탄력 증진, 주름 개선 또는 피부 보습 용도로 사용할 수 있음을 알 수 있었다. As can be seen from the results in Table 2, when treated with the compound of Formula 1, collagen synthesis increased in a concentration-dependent manner, and compared to the case where vitamin C, which is generally known to induce collagen synthesis, was applied, the same concentration of 50 ppm showed excellent collagen synthesis effect. Accordingly, it was found that the compound of Formula 1 can be used to improve skin elasticity, improve wrinkles, or moisturize the skin.
실험예Experiment example 3 : 3: 엘라스타제elastase 활성 저해 효과 ( Active inhibitory effect ( 반복수number of repetitions = 3) = 3)
엘라스틴(elastin)을 분해하는 효소인 엘라스타제(elastase)의 활성 저해 효과를 다음과 같이 확인하였다.The effect of inhibiting the activity of elastase, an enzyme that decomposes elastin, was confirmed as follows.
엘라스타제(elastase)는 사람의 백혈구 세포로부터 유래한 것을 사용하였고, 엘라스타제의 기질로 합성 기질인 MeOSuc-Ala-Ala-Pro-Val-pNA를 사용하였다. 완충용액은 100 mM의 Tris (pH 7.5) 용액을 사용하였다. 엘라스타제는 완충용액을 이용하여 최종적으로 0.2 mU 을 사용하였다. 또한 엘라스타제의 합성 기질은 DMSO를 이용하여 100 mM 용액을 만든 후 최종 농도가 0.5 mM이 되도록 완충용액을 이용하여 희석하였다. 이 때, 양성 대조군은 엘라스테이즈 저해 물질로 알려진 퀘르세틴(Quercetin)을 10 ppm 농도로 넣은 것으로 설정하였다. 엘라스타제 저해 후보인 화학식 1의 화합물은 최종농도가 10, 20 ppm이 되도록 첨가하였다. 반응은 96-웰 플레이트에서 진행하였으며, 상온에서 20 분간 반응시켰다. 분광 광도계를 이용하여 1 분 간격으로 405 nm에서 흡광도를 측정하여, 시간 대비 흡광도의 기울기를 구하여 효소의 활성도를 측정하였다. 엘라스타제 저해율은 다음과 같이 계산하였으며, 그 결과는 하기 표 3에 나타내었다.Elastase derived from human white blood cells was used, and the synthetic substrate MeOSuc-Ala-Ala-Pro-Val-pNA was used as the elastase substrate. A 100mM Tris (pH 7.5) solution was used as the buffer solution. Finally, 0.2 mU of elastase was used using a buffer solution. In addition, the synthetic substrate of elastase was made into a 100mM solution using DMSO and then diluted with a buffer solution to reach a final concentration of 0.5mM. At this time, the positive control was set to contain quercetin, known as an elastase inhibitor, at a concentration of 10 ppm. The compound of Formula 1, a candidate for elastase inhibition, was added to a final concentration of 10 and 20 ppm. The reaction was carried out in a 96-well plate and reacted at room temperature for 20 minutes. Absorbance was measured at 405 nm at 1 minute intervals using a spectrophotometer, and the slope of absorbance versus time was obtained to measure enzyme activity. The elastase inhibition rate was calculated as follows, and the results are shown in Table 3 below.
상기 표 3의 결과에서 볼 수 있듯이, 화학식 1의 화합물은 양성대조군과 비교해 대등한 효과를 보이며, 대조군과 대비해서 엘라스타제 활성 저해 효과가 우수함을 확인하였다. 따라서, 화학식 1의 화합물은 피부 탄력 증진, 주름 개선 또는 피부 보습 용도로 사용할 수 있음을 알 수 있었다. As can be seen from the results in Table 3, the compound of Formula 1 showed an equivalent effect compared to the positive control group, and was confirmed to have an excellent elastase activity inhibition effect compared to the control group. Accordingly, it was found that the compound of Formula 1 can be used to improve skin elasticity, improve wrinkles, or moisturize the skin.
실험예Experiment example 4 : 항산화 효과 - 자유라디칼 소거율 4: Antioxidant effect - free radical scavenging rate
화학식 1의 화합물의 항산화 작용을 확인하기 위해 자유라디칼 소거 활성을 측정하였다. 자유라디칼 소거 활성은 DPPH를 이용하여 측정하였다. DPPH는 시그마사(Sigma Co., Ltd, 미국)에서 구입하여 사용하였다. 먼저, 1.5 mM (0.06 mg/ml)의 표준 DPPH 에탄올 용액을 만들었다. 그리고, 3차 증류수를 이용하여 1000 μg/ml 비타민 C 용액을 만든 다음 1/2씩 연속 희석하여 1000, 500, 250, 125, 62.5, 31.25, 15.625, 7.8125, 3.90625, 1.953125, 0.9765625, 0.48828125 μg/ml 농도의 비타민 C 시료를 만들었다. 또한 비타민 C와 동일한 농도로 화학식 1의 화합물의 희석액을 준비하였다. 그 다음, 상기 시료와 표준 DPPH 용액을 같은 비율로 첨가하여 잘 교반한 후, 37 ℃에서 30 분간 반응시키고 520 ㎚에서 흡광도를 측정하였다. 이때, 상기 시료 대신 에탄올을 첨가한 것을 대조군으로 하였다. 자유라디칼 소거능은 half maximal inhibitory concentration(억제 중간 값)인 IC50을 구하여 그 결과를 하기 표 4에 나타내었다. IC50은 무첨가 대조군의 자유라디칼을 50% 제거하는데 필요한 비타민 C 및 화학식 1의 화합물의 농도로써 자유라디칼 소거능을 표현하는 일반적인 방법이다.To confirm the antioxidant activity of the compound of Formula 1, free radical scavenging activity was measured. Free radical scavenging activity was measured using DPPH. DPPH was purchased and used from Sigma Co., Ltd (USA). First, a standard DPPH ethanol solution of 1.5 mM (0.06 mg/ml) was prepared. Then, make a 1000 μg/ml vitamin C solution using distilled water and then serially dilute it by 1/2 to obtain 1000, 500, 250, 125, 62.5, 31.25, 15.625, 7.8125, 3.90625, 1.953125, 0.9765625, 0.4882812. 5 μg/ A sample of vitamin C at a concentration of ml was prepared. Additionally, a diluted solution of the compound of Formula 1 was prepared at the same concentration as vitamin C. Next, the sample and the standard DPPH solution were added in equal proportions, stirred well, reacted at 37°C for 30 minutes, and absorbance was measured at 520 nm. At this time, ethanol was added instead of the above sample as a control. The free radical scavenging ability was calculated as IC 50 , which is the half maximal inhibitory concentration (median inhibition value), and the results are shown in Table 4 below. IC 50 is a general method of expressing free radical scavenging ability as the concentration of vitamin C and the compound of formula 1 required to remove 50% of free radicals in the no-added control group.
상기 표 4의 결과에서 볼 수 있듯이, 화학식 1의 화합물은 일반적으로 항산화 물질로 알려진 비타민 C를 적용한 경우보다 더 낮은 IC50 값을 지님을 알 수 있었다. 따라서, 화학식 1의 화합물은 우수한 항산화 효과를 나타내어, 항산화 용도로 사용할 수 있으며, 피부 미백, 탄력 증진, 주름 개선 및 피부 보습에 있어, 보조적인 역할로 작용하여 상승효과를 기대할 수 있음을 알 수 있었다.As can be seen from the results in Table 4, the compound of Chemical Formula 1 had a lower IC 50 value than when vitamin C, which is generally known as an antioxidant, was applied. Therefore, it was found that the compound of Formula 1 exhibits excellent antioxidant effects and can be used for antioxidant purposes, and that a synergistic effect can be expected by acting as an auxiliary role in skin whitening, elasticity enhancement, wrinkle improvement, and skin moisturization. .
실험예Experiment example 5 : 항염증 효과 - NO 생성 억제 효과 5: Anti-inflammatory effect - NO production inhibition effect
화학식 1의 화합물의 항염증 효과 및 피부 트러블 개선 효과를 확인하기 위하여 RAW264.7 세포주 (ATCC number: CRL-2278)를 이용한 GRIESS 법으로 일산화질소(NO) 형성 억제 실험을 실시하였다.To confirm the anti-inflammatory effect and skin trouble improvement effect of the compound of Formula 1, a nitric oxide (NO) formation inhibition experiment was conducted using the GRISESS method using RAW264.7 cell line (ATCC number: CRL-2278).
구체적으로, 생쥐의 대식세포인 RAW264.7 세포를 수차례 계대 배양하고, 상기 배양된 세포를 웰 하나에 3×105 개씩 들어가도록 24-웰 플레이트에 넣은 후, 24 시간 동안 배양시켰다. 이어서, 하기 표 5에 나타난 농도로 희석된 화학식 1의 화합물을 함유한 세포 배지로 교체하였다. 이 때, NO-생성 억제물질인 L-NMMA(L-NG-모노메틸아르기닌, L-NG-Monomethylarginine)을 양성대조군으로 함께 처리하여 30분 동안 배양하였고, 자극원으로 LPS(Lipopolysaccharide)를 1 ㎍씩 처리하여 24시간 동안 배양하였다. 상층액을 100 ㎕씩 취해 96-웰 프레이트에 옮기고, GRIESS 용액을 100 ㎕씩 가해 상온에서 10분간 반응시킨 후, 540 nm에서의 흡광도를 측정함으로써 화학식 1의 화합물의 NO 억제 효과를 판단하고, 그 결과를 하기 표 5에 나타내었다.Specifically, RAW264.7 cells, which are mouse macrophages, were subcultured several times, and the cultured cells were placed in a 24-well plate at 3×10 5 cells per well and cultured for 24 hours. Then, the cell medium was replaced with cell medium containing the compound of Formula 1 diluted to the concentration shown in Table 5 below. At this time, L-NMMA (L-NG-Monomethylarginine), an NO-production inhibitor, was treated as a positive control and cultured for 30 minutes, and 1 μg of LPS (Lipopolysaccharide) was added as a stimulus. treated and cultured for 24 hours. Take 100 ㎕ of the supernatant and transfer it to a 96-well plate, add 100 ㎕ of GRIESS solution each, react at room temperature for 10 minutes, and measure the absorbance at 540 nm to determine the NO inhibition effect of the compound of Formula 1. The results are shown in Table 5 below.
상기 표 5의 결과에서 볼 수 있듯이, 화학식 1의 화합물은 대표적인 항염 물질인 L-NMMA에 상응하는 정도의 NO 생성 억제율을 나타내며, 대조군과 비교했을 때 우수한 항염증 효과가 있음을 알 수 있었다. 따라서, 화학식 1의 화합물은 피부 트러블 개선 용도로 사용할 수 있으며, 피부 미백, 탄력 증진, 주름 개선 및 피부 보습에 있어, 보조적인 역할로 작용하여 상승효과를 기대할 수 있음을 알 수 있었다.As can be seen from the results in Table 5, the compound of Formula 1 exhibits a NO production inhibition rate comparable to that of L-NMMA, a representative anti-inflammatory substance, and has an excellent anti-inflammatory effect compared to the control group. Therefore, it was found that the compound of Formula 1 can be used to improve skin troubles, and that a synergistic effect can be expected by playing an auxiliary role in skin whitening, improving elasticity, improving wrinkles, and moisturizing the skin.
실험예Experiment example 6 : 6: 항당화antiglycation (anti-(anti- glycationglycation ) 효과) effect
항당화(anti-glycation) 효능을 확인하기 위하여, L-아르기닌(arginine)과 포도당을 이용하여 항당화 활성을 측정하였다.To confirm the anti-glycation effect, the anti-glycation activity was measured using L-arginine and glucose.
먼저, 1M 인산 완충용액(pH 7.4)을 이용하여 1M L-아르기닌(arginine), 1M 포도당을 녹여 준비하고 1M 인산 완충용액을 이용하여 시료를 25, 50 ppm이 되도록 희석해서 준비하였다. 1M L-아르기닌과 1M 인산 완충용액을 1 대 4의 비율로 섞은 다음 96-웰 플레이트에 80 μl씩 분주하였다. 여기에 각각 25, 50 ppm으로 희석한 시료와 양성 대조군으로 사용될 0.01M 아미노구아니딘(aminoguanidin)을 100 μl씩 첨가하였다. 이 시료들을 잘 섞어준 다음, 마지막으로 포도당의 최종 농도가 0.1M이 되도록 1M 인산 완충용액으로 희석한 포도당을 넣은 후, 70 ℃에서 4 시간 동안 반응시켰다. 96-웰 플레이트를 분광 광도계를 이용하여 420 nm에서 흡광도를 측정하여 당화 정도를 측정하였다.First, 1M L-arginine and 1M glucose were prepared by dissolving them in 1M phosphate buffer solution (pH 7.4), and the sample was diluted to 25 and 50 ppm using 1M phosphate buffer solution. 1M L-arginine and 1M phosphate buffer solution were mixed at a ratio of 1 to 4, and then 80 μl each was dispensed into a 96-well plate. Here, 100 μl of samples diluted to 25 and 50 ppm, respectively, and 0.01M aminoguanidin to be used as a positive control were added. These samples were mixed well, and finally, glucose diluted with 1M phosphate buffer solution was added so that the final concentration of glucose was 0.1M, and then reacted at 70°C for 4 hours. The degree of glycosylation was measured by measuring the absorbance of the 96-well plate at 420 nm using a spectrophotometer.
하기 식의 당화(glycation) 실험군은 1M L-아르기닌과 1M 포도당을 넣어 당화를 유발시킨 실험군이며, 시료 자체의 흡광도를 측정하기 위해서 포도당을 넣지 않고 1M L-아르기닌과 시료만을 넣어 420 nm에서 흡광도를 측정하였다. 당화 저해 활성은 다음과 같은 식으로 구하였으며, 그 결과는 하기 표 6에 나타내었다.The glycation experimental group shown below is an experimental group in which 1M L-arginine and 1M glucose were added to induce glycation. To measure the absorbance of the sample itself, only 1M L-arginine and the sample were added without adding glucose and the absorbance was measured at 420 nm. Measured. The glycation inhibition activity was calculated as follows, and the results are shown in Table 6 below.
상기 표 6의 결과에서 볼 수 있듯이, 화학식 1의 화합물은 항당화 물질로 알려진 아미노구아니딘과 비교할 때, 항당화 효과가 더욱 뛰어남을 알 수 있었다. 따라서, 화학식 1의 화합물은 우수한 항당화 효과를 나타내어, 피부 미백, 탄력 증진, 주름 개선 및 피부 보습에 있어, 보조적인 역할로 작용하여 상승효과를 기대할 수 있음을 알 수 있었다.As can be seen from the results in Table 6, the compound of Formula 1 was found to have a more excellent anti-glycation effect compared to aminoguanidine, a known anti-glycation substance. Therefore, it was found that the compound of Formula 1 exhibits an excellent anti-glycation effect and acts as an auxiliary agent in skin whitening, improving elasticity, improving wrinkles, and moisturizing the skin, so a synergistic effect can be expected.
Claims (11)
상기 화장료 조성물은 피부 미백용; 피부 탄력 증진 또는 주름 개선용; 피부 보습용인 것인, 화장료 조성물.
[화학식 1]
A cosmetic composition containing a compound represented by the following formula (1) or a cosmetically acceptable salt thereof as an active ingredient,
The cosmetic composition is for skin whitening; For improving skin elasticity or wrinkles; A cosmetic composition for moisturizing the skin.
[Formula 1]
The cosmetic composition of claim 1, wherein the composition has the effects of reducing the total amount of melanin, promoting collagen synthesis, inhibiting elastase activity, antioxidant, or anti-glycation.
The method of claim 1, wherein the composition includes a solution, cream, foam, nourishing lotion, softening lotion, pack, softening water, emulsion, makeup base, essence, liquid cleanser, bath agent, sunscreen cream, sun oil, suspension, emulsion, A cosmetic composition, characterized in that it has a formulation selected from the group consisting of paste, gel, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation, patch and spray.
상기 식품 조성물은 피부 미백용; 피부 탄력 증진 또는 주름 개선용; 피부 보습용인 것인, 식품 조성물.
[화학식 1]
A food composition containing a compound represented by the following formula (1) or a foodologically acceptable salt thereof as an active ingredient,
The food composition is for skin whitening; For improving skin elasticity or wrinkles; A food composition for moisturizing skin.
[Formula 1]
상기 의약외품 조성물은 피부 미백용; 피부 탄력 증진 또는 주름 개선용; 피부 보습용인 것인, 의약외품 조성물.
[화학식 1]
A quasi-drug composition containing a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient,
The quasi-drug composition is for skin whitening; For improving skin elasticity or wrinkles; A quasi-drug composition for moisturizing the skin.
[Formula 1]
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| CN104840527A (en) | 2015-05-02 | 2015-08-19 | 浙江大学 | Composition containing tenuifoliside and ginsenoside |
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| CN104975066A (en) | 2014-04-04 | 2015-10-14 | 中国人民解放军总医院 | Specificity probe substrate of cytochrome P450-3A4 enzyme and application thereof |
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