KR102232928B1 - Cosmetic or pharmaceutical composition for skin whitening, elasticity, anti-wrinkle, or skin moisturizing comprising synephrine or a pharmaceutically acceptable salt thereof - Google Patents
Cosmetic or pharmaceutical composition for skin whitening, elasticity, anti-wrinkle, or skin moisturizing comprising synephrine or a pharmaceutically acceptable salt thereof Download PDFInfo
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- KR102232928B1 KR102232928B1 KR1020140104509A KR20140104509A KR102232928B1 KR 102232928 B1 KR102232928 B1 KR 102232928B1 KR 1020140104509 A KR1020140104509 A KR 1020140104509A KR 20140104509 A KR20140104509 A KR 20140104509A KR 102232928 B1 KR102232928 B1 KR 102232928B1
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- South Korea
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- skin
- formula
- present
- elasticity
- pharmaceutically acceptable
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- A—HUMAN NECESSITIES
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- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
본 발명은 하기 화학식 1로 표현되는 화합물 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 미백, 탄력, 주름개선, 또는 보습용 조성물, 특히 화장료 조성물, 약학 조성물 및 건강식품을 제공한다. 본 발명의 화장료 또는 약학 조성물은 부작용이 적어 인체에 안전하면서도 우수한 피부 미백, 탄력, 주름개선, 피부 보습 효과 등을 가진다.
[화학식 1]
The present invention provides a composition for skin whitening, elasticity, wrinkle improvement, or moisturizing, in particular a cosmetic composition, a pharmaceutical composition, and a health food comprising a compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient. The cosmetic or pharmaceutical composition of the present invention has few side effects, so it is safe for the human body and has excellent skin whitening, elasticity, wrinkle improvement, skin moisturizing effects, and the like.
[Formula 1]
Description
본 발명은 피부 미백, 탄력, 주름개선, 또는 보습 등의 우수한 효과를 가지는, 특히 피부와 관련된 우수한 효과를 가지는 화장료 조성물, 약학 조성물 및 건강식품에 관한 것이다. 본 발명은 또한 적은 양으로도 위와 같은 효과를 발휘할 수 있는 화장료 조성물, 약학 조성물 및 건강식품에 관한 것이다. The present invention relates to a cosmetic composition, a pharmaceutical composition, and a health food having excellent effects such as skin whitening, elasticity, wrinkle improvement, or moisturizing, and particularly having excellent effects related to the skin. The present invention also relates to a cosmetic composition, a pharmaceutical composition and a health food that can exert the above effect even in a small amount.
희고 고운 피부를 갖고자 하는 것은 일반적인 소망이다. 피부의 색깔 또는 밝기는 사람의 피부 내 멜라닌(Melanin)의 농도와 분포에 따라 유전적으로 결정되나, 태양 자외선, 피로 또는 스트레스 등의 환경적 또는 생리적 조건에 의해서도 영향을 받는다. 멜라닌은 아미노산의 일종인 티로신(Tyrosine)에 티로시나제(Tyrosinase)라는 효소가 촉매로 작용하여 도파(DOPA) 및 도파퀴논(Dopaquinone)으로 순차적으로 바뀐 후, 비효소적인 산화반응을 거쳐 만들어진다. 이와 같이 멜라닌이 만들어지는 경로는 알려져 있으나, 멜라닌 합성을 유도하는 메커니즘에서 티로시나제가 촉발되는 원인이 무엇인지에 대해서는 아직도 자세히 밝혀지지 않고 있다. It is a common desire to have white and fair skin. The color or brightness of the skin is genetically determined according to the concentration and distribution of melanin in human skin, but is also affected by environmental or physiological conditions such as solar ultraviolet rays, fatigue or stress. Melanin is produced through a non-enzymatic oxidation reaction after being sequentially converted into dopa and dopaquinone by an enzyme called tyrosinase acting as a catalyst in tyrosine, a kind of amino acid. As such, the pathway by which melanin is produced is known, but the cause of the triggering of tyrosinase in the mechanism that induces melanin synthesis is still not elucidated in detail.
한편, 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.Meanwhile, as a commonly known whitening component, substances that inhibit tyrosinase enzyme activity such as Kojic acid or arbutin, hydroquinone, vitamin C (L-Ascorbic acid), or derivatives thereof, and various There are plant extracts. By inhibiting the synthesis of melanin pigments, they can not only realize skin whitening by brightening skin tone, 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 problem in that the amount of use is limited due to safety problems such as irritation and redness, or the effect is insignificant and thus no practical effect can be expected.
콜라겐은 피부의 섬유아세포(Fibroblast)에서 생성되는 주요 기질 단백질로서 세포외 간질에 존재하고, 중요한 기능으로는 피부의 기계적 견고성, 결합조직의 저항력과 조직의 결합력, 세포접착의 지탱, 세포분할과 분화(유기체의 성장 혹은 상처 치유시)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 fibroblasts of the skin and is present in the extracellular interstitial. Its important functions include skin mechanical firmness, connective tissue resistance and tissue bonding, support for cell adhesion, cell division and differentiation. (At the time of growth of organisms or wound healing), the induction and the like are known. Such collagen is reduced by age and photoaging due to ultraviolet irradiation, and collagen reduction is promoted by the activity of collagenase enzymes that degrade collagen. It is known that this is closely related to the formation of wrinkles in 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 엘라스테이즈(Elastase)의 활성도의 현격한 증가는 피부 주름생성 요인 중의 하나로 밝혀지고 있다. 엘라스테이즈는 엘라스틴을 분해할 수 있는 유일한 효소로서 이에 대한 저해는 피부 주름 개선을 근본적으로 줄여 줄 수 있다고 알려져 있다.In addition, elastin fibers form cross-links with collagen and are an important skin component for wrinkle formation, which is involved in skin elasticity. Deficiency and aggregation of elastin fibers, and a marked increase in the activity of elastin-degrading enzyme, Elastase, have been found to be one of the factors of skin wrinkles. Elastase is the only enzyme that can break down elastin, and its inhibition is known to fundamentally reduce the improvement of skin wrinkles.
한편, 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.On the other hand, collagen and elastin fibers are matrix proteins that play an important role in water retention in the dermal layer, and these matrix proteins adsorb moisture and increase moisture retention within the structures that make up the skin so that the skin can maintain a state containing adequate moisture. It is known to be involved in maintaining the elasticity of the skin through this.
현재, 주름개선 화장료로는 레티노이드, 아데노신, 동물태반유래 단백질, 클로렐라 추출물 등이 알려져 있다. 가장 잘 알려져 있는 레티놀은 콜라겐 합성을 촉진하며 엘라스테이즈 효소를 저해하는 물질이지만 불안정하며, 피부 적용시 자극, 발적 등의 안전성 문제로 사용량의 제한이 있으며, 클로렐라 추출물 등은 효과가 미미하여 실질적으로 피부주름 개선효과를 기대하기가 어렵다고 알려져 있다.Currently, retinoids, adenosine, animal placenta-derived proteins, and chlorella extracts are known as wrinkle-improving cosmetics. Retinol, the most well-known substance, promotes collagen synthesis and inhibits elastase enzyme, but it is unstable. When applied to the skin, the amount of use is limited due to safety issues such as irritation and redness. It is known that it is difficult to expect a wrinkle improvement effect.
당화(Glycation)는 일반적으로 효소의 관여 없이 일어나는 단백질 또는 지방에 포도당 또는 과당과 같은 단순당이 공유결합을 형성하는 반응을 의미한다. 당화는 일련의 아마도리 반응, 마이야르 반응으로 알려진 복잡한 화학적 반응을 거쳐 일어나게 되며 그 결과 최종당화산물(AGEs: Advanced glycation endproducts)이 생성된다.Glycation refers to a reaction in which simple sugars such as glucose or fructose form covalent bonds to proteins or fats that generally occur without the involvement of enzymes. Saccharification takes place through a series of complex chemical reactions known as Amadori reactions and Maiyar reactions, resulting in the formation of advanced glycation endproducts (AGEs).
한편 단백질의 당화 과정은 효소 작용이 관여하지 않아 천천히 일어나게 되고 그 결과 콜라겐과 같이 반감기가 긴 단백질에서 더욱 많은 영향을 끼치게 된다. 최종당화산물을 분석한 결과 나이가 많을수록 당화된 콜라겐이 축적되는 양상을 보였으며, 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).On the other hand, the glycosylation process of protein occurs slowly because enzyme action is not involved, and as a result, it has more influence on proteins with a long half-life such as collagen. As a result of analysis of the final glycated product, glycated collagen was accumulated with age, and the accumulation of the final glycated product changed the protein into a hard and brittle state, and glycated collagen was found in the extracellular matrix of the dermal layer. By preventing collagen from forming an appropriate structure, it loses the elasticity of the skin and promotes wrinkle formation (Dyer, DG et al, The Journal of Clinical Investigation., 9, p. 2463, 1993).
또한 당화로 인해 생성된 최종당화산물은 갈색 빛을 띠는 물질로써 피부 노화가 진행됨에 따라 진피층 상부에 쌓이는 것으로 알려져 있다. 피부 노화가 진행되면서 점차 얼굴빛이 노랗게 변하는 원인 물질로 생각되고 있으며, 특정 최종당화산물이 쌓일수록 피부에서 반사되는 반사 빛이 줄어든다고 알려져 있다. 피부 속 멜라닌 색소의 양은 피부 노화와 관계가 약한 반면, 피부 진피층에 쌓이는 최종당화산물은 피부 노화가 진행됨에 따라 점차 그 양이 늘어나게 되고 얼굴빛을 칙칙하게 만들 수 있다(Hiroshi, O. et al, Skin Research and Technology, 15, p. 496, 2009).In addition, the final saccharification product produced by saccharification is known to accumulate on the dermal layer as skin aging progresses as a brownish-colored substance. As skin aging progresses, it is thought to be the causative agent that gradually turns yellowish, and it is known that the reflected light reflected from the skin decreases as a specific final glycated product accumulates. While the amount of melanin pigment in the skin is weakly related to skin aging, the amount of the final glycated product accumulated in the dermal layer of the skin gradually increases as skin aging progresses and can make the face look dull (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.As substances that inhibit saccharification, aminoguanidine, pyridoxamine, and aspirin are known, but these substances have limited amounts of use due to safety issues on the skin, or are insignificant, so they are practically effective. There is a problem that can not be expected.
따라서, 생체에 안전하고, 유효성분이 안정하며, 무엇보다도 기존의 피부 미백, 탄력, 주름개선, 또는 보습 효과가 있는 물질보다 효과가 우수한 미백, 탄력, 주름개선, 또는 보습 효과를 지닌 성분의 개발이 절실히 요망되고 있다.Therefore, it is necessary to develop a component that is safe for the living body and has a stable active ingredient, and above all, has a whitening, elasticity, wrinkle improvement, or moisturizing effect that is superior to the existing skin whitening, elasticity, wrinkle improvement, or moisturizing substances. It is desperately desired.
따라서 본 발명은 위와 같은 문제점을 해결하고, 부작용이 적고 인체에 안전하면서도 미백, 탄력, 주름개선, 또는 보습 효과가 우수한 새로운 활성 성분, 즉, 활성 성분의 이러한 유용한 용도를 제공하는 것이다.Accordingly, the present invention solves the above problems, has few side effects, is safe for the human body, and provides a new active ingredient excellent in whitening, elasticity, wrinkle improvement, or moisturizing effect, that is, such a useful use of the active ingredient.
다시 말해, 본 발명이 해결하고자 하는 과제는 상기 효능이 우수한 활성 성분을 유효성분으로 포함하는 조성물을 제공하고자 한다. In other words, the problem to be solved by the present invention is to provide a composition comprising an active ingredient having excellent efficacy as an active ingredient.
상기 과제를 해결하기 위하여, 본 발명은 시네프린(Synephrine) 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 피부 미백용, 탄력 증진용, 주름개선용, 또는 보습용 조성물, 바람직하게는 화장료 조성물, 약학 조성물 또는 건강식품을 제공한다. In order to solve the above problems, the present invention is a composition for skin whitening, elasticity enhancement, wrinkle improvement, or moisturizing composition, preferably cosmetic, comprising as an active ingredient Synephrine or a pharmaceutically acceptable salt thereof It provides a composition, a pharmaceutical composition, or a health food.
즉, 본 발명은 시네프린 또는 이의 약학적으로 허용 가능한 염의 피부 미백용, 탄력 증진용, 주름개선용, 보습용이라는 새로운 용도를 제공한다.That is, the present invention provides a new use of synephrine or a pharmaceutically acceptable salt thereof for skin whitening, elasticity enhancement, wrinkle improvement, and moisturizing.
본 발명의 발명자들은 시네프린이 피부의 콜라게나제 및 엘라스타제 활성을 저해하고, 항당화 효과를 나타냄으로써 피부의 재생을 촉진하며, 보습, 피부 탄력 및 주름개선 효과가 있다는 사실을 확인하고 본 발명을 완성하게 되었다. 또한 상기 시네프린은 멜라닌 합성을 억제하여 미백 효과를 나타내는 것을 확인하고 본 발명을 완성하게 되었다.The inventors of the present invention confirmed that synephrine inhibits the collagenase and elastase activity of the skin, promotes skin regeneration by exhibiting an anti-glycosylation effect, and has moisturizing, skin elasticity, and wrinkle improvement effects. The invention was completed. In addition, it was confirmed that synephrine exhibits a whitening effect by inhibiting melanin synthesis, thereby completing the present invention.
본 발명에 있어서, ‘미백 효과’라 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.In the present invention, the "whitening effect" 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.
본 발명에 있어서, ‘탄력 또는 피부 탄력 개선’이라 함은 피부가 쳐지거나 늘어지는 정도를 완화시켜주는 것을 의미한다. 또한, 상기 탄력은 엘라스틴과 콜라겐이 충분이 존재하는 상태에서 피부의 탄력성을 유지시켜 주는 것을 의미한다.In the present invention, "improving elasticity or skin elasticity" means reducing the degree of sagging or sagging of the skin. In addition, the elasticity means maintaining the elasticity of the skin in the presence of sufficient elastin and collagen.
본 발명에 있어서, ‘주름개선 효과’라 함은 피부에 주름이 생성되는 것을 억제 또는 저해하거나, 이미 생성된 주름을 완화시키는 것을 말한다. In the present invention, the term "wrinkle improvement effect" refers to suppressing or inhibiting the formation of wrinkles on the skin, or alleviating wrinkles that have already been created.
본 발명에 있어서, ‘보습 또는 피부 보습’이라 함은 피부에 수분감을 증가시켜주고, 촉촉한 상태를 유지시키는 것을 의미한다. 피부 보습 효과는 피부의 주름개선, 탄력도 증가에 도움을 줄 수 있다.In the present invention, the term “moisturizing or moisturizing the skin” refers to increasing the feeling of moisture on the skin and maintaining a moist state. The skin moisturizing effect can help improve skin wrinkles and increase elasticity.
본 발명은 상기와 같은 문제점들을 해결하고, 본 발명의 목적을 달성하기 위하여 하기 화학식 1로 대표되는 화합물 또는 이의 약학적으로 허용 가능한 염을 포함하는 조성물을 제공한다. The present invention provides a composition comprising a compound represented by Formula 1 or a pharmaceutically acceptable salt thereof in order to solve the above problems and achieve the object of the present invention.
[화학식 1][Formula 1]
상기 화학식 1로 대표되는 화합물은 분자식 C9H13NO2 , 분자량 167.21을 가지며, 시네프린(Synephrine), N-Methyloctopamine, Oxedrine 등으로 명명된다. The compound represented by Chemical Formula 1 has a molecular formula of C 9 H 13 NO 2 , a molecular weight of 167.21, and is named as Synephrine, N-Methyloctopamine, Oxedrine, and the like.
본 발명은 상기 시네프린의 획득 방법에 특별히 한정되지 않으며, 당 업계에 공지된 방법으로 화학적으로 합성하거나, 시판되는 물질을 사용할 수 있다. The present invention is not particularly limited to the method for obtaining synephrine, and chemically synthesized by a method known in the art, or a commercially available material may be used.
본 발명에 따른 화장료 조성물, 약학 조성물 및 건강식품에 있어, 상기 시네프린의 함량은 화장료 조성물, 약학 조성물 및 건강식품 전체 중량 대비 0.00001 내지 10 중량%인 것이 바람직하다.In the cosmetic composition, pharmaceutical composition and health food according to the present invention, the content of synephrine is preferably 0.00001 to 10% by weight based on the total weight of the cosmetic composition, pharmaceutical composition and health food.
본 발명의 "약학적으로 허용 가능한 염"은 바람직하게는 염기 부가 염을 포함하며, 상기 염기 부가 염은 나트륨, 칼륨, 칼슘, 암모늄, 마그네슘 또는 유기 아미노로 이루어진 염을 포함하나, 이에 한정되는 것은 아니다.The "pharmaceutically acceptable salt" of the present invention preferably includes a base addition salt, and the base addition salt includes a salt consisting of sodium, potassium, calcium, ammonium, magnesium or organic amino, but is limited thereto. no.
본 발명의 시네프린은 수화물, 에탄올화물 등의 형태를 포함하는 용매화된 형태뿐만 아니라 비-용매화된(unsolvated) 형태로 존재할 수도 있다. 본 발명의 시네프린은 결정형 또는 무정형 형태로 존재할 수 있으며, 이러한 모든 물리적 형태는 본 발명의 범위에 포함된다.Synephrine of the present invention may exist in a non-solvated form as well as a solvated form including a form such as a hydrate, an ethanolate, and the like. Synephrine of the present invention may exist in a crystalline or amorphous form, and all such physical forms are included in the scope of the present invention.
본 발명에 따른 피부 미백, 탄력 증진, 주름개선, 및 피부 보습용 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 for skin whitening, elasticity enhancement, wrinkle improvement, and skin moisturization according to the present invention is a solution, external ointment, cream, foam, nutritional lotion, softening lotion, pack, softening water, emulsion, makeup base, essence, soap, liquid cleaning. Group consisting of cosmetics, bath products, sunscreen cream, sun oil, suspension, emulsion, paste, gel, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation, patch and spray It can be prepared in a formulation selected from, but is not limited thereto.
또한, 본 발명의 화장료 조성물은 일반 피부 화장료에 배합되는 화장품학적으로 허용 가능한 담체를 1종 이상 추가로 포함할 수 있으며, 통상의 성분으로 예를 들면 유분, 물, 계면활성제, 보습제, 저급 알코올, 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 blended in general skin cosmetics, and as common ingredients, for example, oil, water, surfactants, moisturizers, lower alcohols, A thickener, a chelating agent, a colorant, a preservative, a fragrance, and the like may be appropriately blended, but are not limited thereto.
본 발명의 화장료 조성물에 포함되는 화장품학적으로 허용 가능한 담체는 제형에 따라 다양하다. 본 발명의 제형이 연고, 페이스트, 크림 또는 젤인 경우에는, 담체성분으로서 동물성 유, 식물성 유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크, 산화아연 또는 이들의 혼합물이 이용될 수 있다.The cosmetically acceptable carrier included in the cosmetic composition of the present invention varies depending on the formulation. When the formulation of the present invention is an ointment, paste, cream or gel, 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 a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, polyamide powder, or mixtures thereof may be used as a carrier component. In particular, in the case of a spray, additional chloro Propellants such as fluorohydrocarbon, propane/butane or dimethyl ether.
본 발명의 제형이 용액 또는 유탁액인 경우에는, 담체 성분으로서 용매, 용해화제, 또는 유탁화제가 이용되고 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 벤조에이트, 프로필렌 글리콜, 1,3-브틸글리콜 오일이 있으며, 특히, 목화씨 오일, 땅콩 오일, 옥수수 배종 오일, 올리브 오일, 피마자 오일 및 참깨 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다.When the formulation of the present invention is a solution or emulsion, a solvent, a solubilizing agent, or an emulsifying agent is used as a carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl benzoate, propylene glycol, 1,3 -Butylglycol oil, in particular cottonseed oil, peanut oil, corn germ oil, olive oil, castor oil and sesame oil, glycerol aliphatic ester, polyethylene glycol or fatty acid ester of sorbitan.
본 발명의 제형이 현탁액인 경우에는, 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리 옥시에틸렌 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, as a carrier component, a liquid diluent such as water, ethanol or propylene glycol, an ethoxylated isostearyl alcohol, a suspending agent such as polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, micro Crystalline cellulose, aluminum metahydroxide, bentonite, agar or tracant, and the like may be used.
본 발명의 제형이 비누인 경우에는 담체 성분으로서 지방산의 알칼리 금속 염, 지방산 헤미에스테르 염, 지방산 단백질 히드롤리제이트, 이세티오네이트, 라놀린 유도체, 지방족 알코올, 식물성 유, 글리세롤, 당 등이 이용될 수 있다.When the formulation of the present invention is a soap, an alkali metal salt of a fatty acid, a fatty acid hemiester salt, a fatty acid protein hydrolyzate, isethionate, a lanolin derivative, an aliphatic alcohol, vegetable oil, glycerol, sugar, etc. may be used as a carrier component. I can.
본 발명은 또한 상기 화학식 1로 대표되는 화합물을 개체의 피부에 도포하는 단계를 포함하는, 피부 미백, 탄력 증진, 주름개선, 및 피부 보습 방법을 제공한다. 상기 개체는 쥐, 가축, 인간 등을 포함하는 포유동물을 제한 없이 포함한다. The present invention also provides a skin whitening, elasticity enhancement, wrinkle improvement, and skin moisturizing method comprising the step of applying the compound represented by Formula 1 to the skin of an individual. The subject includes, without limitation, mammals including mice, livestock, humans, and the like.
본 발명의 또 다른 실시예에 따르면, 본 발명은 상기 화학식 1의 화합물을 유효성분으로 함유하는 피부 미백, 탄력 증진, 주름개선, 또는 피부 보습용 약학적 조성물을 제공한다. According to another embodiment of the present invention, the present invention provides a pharmaceutical composition for skin whitening, elasticity enhancement, wrinkle improvement, or skin moisturizing, containing the compound of Formula 1 as an active ingredient.
본 발명의 화합물을 포함하는 조성물은 경구 또는 비경구의 여러 가지 제형일 수 있으나, 바람직하게는 비경구 제제일 수 있다. 제제화할 경우에는 보통 사용하는 충진제, 증량제, 결합제, 습윤제, 붕해제, 계면활성제 등의 희석제 또는 부형제를 사용하여 조제된다. 경구투여를 위한 고형제제에는 정제, 환제, 산제, 과립제, 캡슐제 등이 포함되며, 이러한 고형제제는 하나 이상의 화합물에 적어도 하나 이상의 부형제 예를 들면, 전분, 탄산칼슘, 수크로오스(sucrose) 또는 락토오스(lactose), 젤라틴 등을 섞어 조제된다. 또한 단순한 부형제 이외에 스테아린산 마그네슘, 탈크 등과 같은 윤활제들도 사용된다. 경구투여를 위한 액상제제로는 현탁제, 내용액제, 유제, 시럽제 등이 해당되는데 흔히 사용되는 단순 희석제인 물, 리퀴드 파라핀 이외에 여러 가지 부형제, 예를 들면 습윤제, 감미제, 방향제, 보존제 등이 포함될 수 있다. 비경구투여를 위한 제제에는 멸균된 수용액, 비수성용제, 현탁제, 유제가 포함된다. 비수성용제, 현탁용제로는 프로필렌글리콜(propylene glycol), 폴리에틸렌 글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테로 등이 사용될 수 있다.The composition containing the compound of the present invention may be in various oral or parenteral formulations, but preferably may be a parenteral formulation. When formulated, it is prepared by using diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrants, and surfactants that are usually used. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and these solid preparations include at least one excipient in one or more compounds, such as starch, calcium carbonate, sucrose, or lactose ( lactose), gelatin, etc. In addition to simple excipients, lubricants such as magnesium stearate and talc are also used. Liquid preparations for oral administration include suspensions, liquid solutions, emulsions, syrups, etc., but may include various excipients, such as wetting agents, sweeteners, fragrances, and preservatives, in addition to water and liquid paraffin, which are commonly used simple diluents. have. Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, and emulsions. As the non-aqueous solvent and the suspension solvent, propylene glycol, polyethylene glycol, vegetable oil such as olive oil, and injectable ester such as ethyl oleate may be used.
본 발명은 또한 상기 화학식 1의 화합물을 유효성분으로 포함하는 피부 미백, 탄력 증진, 주름개선, 및 피부보습 효과를 위한 피부 외용제의 제형으로 제공할 수 있다.The present invention may also be provided as a formulation of a skin external preparation for skin whitening, elasticity enhancement, wrinkle improvement, and skin moisturizing effect, including the compound of Formula 1 as an active ingredient.
상기 화학식 1의 화합물을 피부외용제로 사용하는 경우, 추가로 지방 물질, 유기 용매, 용해제, 농축제 및 겔화제, 연화제, 항산화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온봉쇄제 및 킬레이트화제, 보존제, 비타민, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 지질 소낭 또는 피부용 외용제에 통상적으로 사용되는 임의의 다른 성분과 같은 피부 과학 분야에서 통상적으로 사용되는 보조제를 함유할 수 있다. 또한 상기 성분들은 피부 과학 분야에서 일반적으로 사용되는 양으로 도입될 수 있다. When the compound of Formula 1 is used for external skin, additionally fatty substances, organic solvents, solubilizers, thickening and gelling agents, emollients, antioxidants, suspending agents, stabilizers, foaming agents, fragrances, surfactants , Water, ionic or nonionic emulsifiers, fillers, sequestering and chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic activators, lipid vesicles or external preparations for skin It may contain adjuvants commonly used in the field of dermatology, such as any other ingredients used as. In addition, the above ingredients may be introduced in an amount generally used in the field of dermatology.
상기 화학식 1의 화합물이 피부 외용제 제형으로 제공될 경우, 이에 제한되는 것은 아니나, 연고, 패취, 겔, 크림 또는 분무제와 같은 제형을 가질 수 있다.When the compound of Formula 1 is provided in a formulation for external application for skin, it is not limited thereto, but may have a formulation such as an ointment, patch, gel, cream, or spray.
본 발명의 약학적 조성물은 특히 바람직하게 비경구용 제제로 이용될 수 있으며, 예를 들어, 피부외용제는 바세린, 스테아릴알콜 등의 약제학적으로 허용되는 적당한 기제; 폴리소르베이트, 솔르비탄 세스퀴올레이트 등의 약제학적으로 허용되는 적당한 계면활성제; 글리세린 등의 약제학적으로 허용되는 적당한 보습제; 약제학적으로 허용되는 적당한 용제; 및 착향제, 착색제, 안정화제, 점성화제 등을 균질하게 혼합하는 통상의 피부외용제 제조방법에 의해서 제조될 수 있다.The pharmaceutical composition of the present invention may be particularly preferably used as a parenteral preparation. For example, the external preparation for skin may include a suitable pharmaceutically acceptable base such as petrolatum and stearyl alcohol; Suitable pharmaceutically acceptable surfactants such as polysorbate and sorbitan sesquioleate; Suitable pharmaceutically acceptable moisturizers such as glycerin; Suitable pharmaceutically acceptable solvents; And a flavoring agent, a colorant, a stabilizer, a viscous agent, and the like are homogeneously mixed.
또한, 본 발명의 상기 화학식 1의 화합물을 의약품으로 사용하는 경우, 추가로 동일 또는 유사한 기능을 나타내는 유효성분을 1종 이상 함유할 수 있다. 예컨대, 공지의 피부 미백, 탄력 증진, 주름개선, 및 보습 성분을 포함할 수 있을 것이다. 추가적인 피부 미백, 탄력 증진, 주름개선, 및 보습 성분을 포함하게 되면 본 발명의 조성물의 피부 미백, 탄력 증진, 주름개선, 및 보습 효과는 더욱 증진될 수 있을 것이다. 상기 성분 추가 시에는 복합 사용에 따른 피부 안전성, 제형화의 용이성, 유효성분들의 안정성을 고려할 수 있다. 본 발명의 한 구체예에서, 상기 조성물은 당업계에 공지된 피부 탄력 또는 주름 개선 성분으로서, 레티노산, TGF, 동물 태반 유래의 단백질, 베툴린산 및 클로렐라 추출물; 당업계에 공지된 미백 성분으로서, 코즈산(Kojic acid), 알부틴(Arbutin) 등과 같은 티로시나제 효소활성을 억제하는 물질, 하이드로퀴논(Hydroquinone), 비타민-C(L-Ascorbic acid); 및 이들의 유도체와 각종 식물 추출물로 구성되는 군으로부터 선택되는 1종 또는 2종 이상의 성분을 추가로 포함할 수 있다. 추가의 성분은 전체 조성물 중량에 대하여 0.0001 중량% 내지 10 중량%로 포함될 수 있을 것이며, 상기 함량 범위는 피부 안전성, 상기 화학식 1의 화합물의 제형화 시의 용이성 등의 요건에 따라 조절될 수 있을 것이다.In addition, when the compound of Formula 1 of the present invention is used as a pharmaceutical, it may further contain one or more active ingredients exhibiting the same or similar function. For example, it may include known skin whitening, elasticity enhancement, wrinkle improvement, and moisturizing ingredients. If additional skin whitening, elasticity enhancement, wrinkle improvement, and moisturizing ingredients are included, the skin whitening, elasticity enhancement, wrinkle improvement, and moisturizing effects of the composition of the present invention may be further enhanced. When the above ingredients are added, skin safety, ease of formulation, and stability of active ingredients can be considered in combination with use. In one embodiment of the present invention, the composition is a skin elasticity or wrinkle-improving component known in the art, including retinoic acid, TGF, protein derived from animal placenta, betulinic acid and chlorella extract; As whitening ingredients known in the art, substances that inhibit tyrosinase enzyme activity such as Kojic acid and arbutin, hydroquinone, vitamin-C (L-Ascorbic acid); And it may further include one or two or more components selected from the group consisting of derivatives thereof 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 of Formula 1 .
본 발명의 약학적 조성물은 유효량의 상기 화학식 1의 화합물을 포함할 때 바람직한 피부 미백 효과, 탄력 증진 효과, 주름개선 효과, 및 보습 효과 효과를 제공할 수 있다. 본 발명에 있어서, ‘유효량’이라 함은 피부 미백 효과를 나타내거나, 탄력 증진 및 주름 개선 효과를 나타내거나, 보습 효과를 나타낼 수 있는 화합물의 양을 의미한다. When the pharmaceutical composition of the present invention contains an effective amount of the compound of Formula 1, it may provide a skin whitening effect, an elasticity enhancing effect, an anti-wrinkle effect, and a moisturizing effect. In the present invention, the term "effective amount" means an amount of a compound capable of exhibiting a skin whitening effect, enhancing elasticity and improving wrinkles, or exhibiting a moisturizing effect.
본 발명의 조성물에 포함되는 상기 화학식 1의 화합물의 유효량은 조성물이 제품화되는 형태, 상기 화합물이 피부에 적용되는 방법 및 피부에 머무르는 시간 등에 따라 달라질 것이다. 예컨대, 상기 조성물이 의약품으로 제품화되는 경우에는 일상적으로 피부에 적용하게 되는 화장품으로 제품화되는 경우에 비해 높은 농도로 상기 화학식 1의 화합물을 포함할 수 있을 것이다. 따라서, 일일 투여량은 상기 화학식 1의 화합물의 양을 기준으로 0.1 내지 100 ㎎/㎏이고, 바람직하게는 30 내지 80 ㎎/㎏이고, 더욱 바람직하게는 50 내지 60 mg/kg이며, 하루 1 ∼ 6 회 투여될 수 있다. The effective amount of the compound of Formula 1 included in the composition of the present invention will vary depending on the form in which the composition is commercialized, the method in which the compound is applied to the skin, and the time it stays on the skin. For example, when the composition is commercialized as a pharmaceutical product, it may contain the compound of Formula 1 at a higher concentration than when it is commercialized as a cosmetic product that is routinely applied to the skin. Therefore, the daily dosage is 0.1 to 100 mg/kg, preferably 30 to 80 mg/kg, more preferably 50 to 60 mg/kg, based on the amount of the compound of Formula 1, and 1 to It can be administered 6 times.
본 발명의 또 다른 실시예에 따르면 상기 화학식 1의 화합물을 포함하는 피부 미백 효과, 탄력 증진 효과, 주름개선 효과 및 보습 효과를 위한 건강식품을 제공한다.According to another embodiment of the present invention, a health food containing the compound of Formula 1 is provided for a skin whitening effect, an elasticity enhancing effect, an anti-wrinkle effect, and a moisturizing effect.
본 명세서에서 '건강식품'이란, 상기 화학식 1의 화합물을 음료, 차류, 향신료, 껌, 과자류 등의 식품소재에 첨가하거나, 캡슐화, 분말화, 현탁액 등으로 제조한 식품으로, 이를 섭취할 경우 건강상 특정한 효과를 가져오는 것을 의미하나, 일반 약품과는 달리 식품을 원료로 하여 약품의 장기 복용 시 발생할 수 있는 부작용 등이 없는 장점이 있다. 이와 같이 하여 얻어지는 본 발명의 건강식품은, 일상적으로 섭취하는 것이 가능하기 때문에 높은 피부 미백 효과, 탄력 증진 효과, 주름개선 효과, 및 보습 효과를 기대할 수 있어 매우 유용하다.In the present specification, the term'health food' refers to a food prepared by adding the compound of Formula 1 to food materials such as beverages, teas, spices, gums, confectionery, or encapsulating, powdering, and suspending. It means that it brings a specific effect, but unlike general drugs, it has the advantage of not having side effects that may occur when taking drugs for a long time by using food as a raw material. Since the health food of the present invention obtained in this way can be consumed on a daily basis, high skin whitening effect, elasticity enhancing effect, wrinkle improvement effect, and moisturizing effect can be expected, and thus it is very useful.
상기 화학식 1의 화합물을 식품첨가물로 사용하는 경우, 상기 화학식 1의 화합물을 그대로 첨가하거나 다른 식품 또는 식품 성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효성분의 혼합양은 그의 사용 목적(예방, 건강 또는 치료적 처치)에 따라 적합하게 결정될 수 있다. 일반적으로, 식품 또는 음료의 제조시에 본 발명의 조성물은 원료에 대하여 15 중량부 이하, 바람직하게는 10 중량부 이하의 양으로 첨가된다. 그러나, 건강 및 위생을 목적으로 하거나 또는 건강 조절을 목적으로 하는 장기간의 섭취의 경우에는 상기 양은 상기 범위 이하일 수 있으며, 안전성 면에서 아무런 문제가 없기 때문에 유효성분은 상기 범위 이상의 양으로도 사용될 수 있다. 상기 식품의 종류에는 특별한 제한은 없다. 상기 물질을 첨가할 수 있는 식품의 예로는 육류, 소세지, 빵, 초콜릿, 캔디류, 스넥류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차, 드링크제, 알콜 음료 및 비타민 복합제 등이 있으며, 통상적인 의미에서의 건강식품을 모두 포함한다. 본 발명의 건강음료 조성물은 통상의 음료와 같이 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있다. 상술한 천연 탄수화물은 포도당, 과당과 같은 모노사카라이드, 말토스, 슈크로스와 같은 디사카라이드, 및 덱스트린, 사이클로덱스트린과 같은 폴리사카라이드, 자일리톨, 소르비톨, 에리트리톨 등의 당알콜이다. 감미제로서는 타우마틴, 스테비아 추출물과 같은 천연 감미제나, 사카린, 아스파르탐과 같은 합성 감미제 등을 사용할 수 있다. 상기 천연 탄수화물의 비율은 본 발명의 조성물 100 mL 당 일반적으로 약 0.01 ∼ 0.04 g, 바람직하게는 약 0.02 ∼ 0.03 g 이다. 상기 외에 본 발명의 건강식품은 여러 가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산 음료에 사용되는 탄산화제 등을 함유할 수 있다. 그 밖에 본 발명의 건강식품은 천연 과일주스, 과일주스 음료 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 이러한 성분은 독립적으로 또는 혼합하여 사용할 수 있다. 이러한 첨가제의 비율은 크게 중요하진 않지만 본 발명의 조성물 100 중량부당 0.01 ~ 0.1 중량부의 범위에서 선택되는 것이 일반적이다.When the compound of Formula 1 is used as a food additive, the compound of Formula 1 may be added as it is or may be used with other foods or food ingredients, and may be appropriately used according to a conventional method. The mixing amount of the active ingredient may be appropriately determined according to the purpose of use (prevention, health or therapeutic treatment). In general, when preparing food or beverage, the composition of the present invention is added in an amount of 15 parts by weight or less, preferably 10 parts by weight or less based on the raw material. However, in the case of long-term intake for the purpose of health and hygiene or for the purpose of health control, the amount may be less than the above range, and there is no problem in terms of safety, so the active ingredient may be used in an amount above the above range. . There is no particular limitation on the type of the food. Examples of foods to which the above substances can be added include meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gum, dairy products including ice cream, various soups, beverages, tea, drinks, There are alcoholic beverages and vitamin complexes, and all health foods in the usual sense are included. The health beverage composition of the present invention may contain various flavoring agents or natural carbohydrates as an additional component, like a conventional beverage. The natural carbohydrates described above are monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, and polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol. As the sweetener, natural sweeteners such as taumatin and stevia extract, and synthetic sweeteners such as saccharin and aspartame can be used. The proportion of the natural carbohydrate is generally about 0.01 to 0.04 g, preferably about 0.02 to 0.03 g per 100 mL of the composition of the present invention. In addition to the above, the health food of the present invention includes various nutrients, vitamins, electrolytes, flavoring agents, coloring agents, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols. , Carbonated beverages, and the like. In addition, the health food of the present invention may contain pulp for the manufacture of natural fruit juice, fruit juice beverage, and vegetable beverage. These ingredients may be used independently or in combination. Although the proportion of these additives is not very important, it is generally selected from 0.01 to 0.1 parts by weight per 100 parts by weight of the composition of the present invention.
이에 제한되는 것은 아니나, 본 발명의 한 구체예에서, 상기 조성물은 상기 화학식 1의 화합물을 전체 조성물 중량에 대하여 0.00001 중량% 내지 10 중량%로 포함할 수 있다. Although not limited thereto, in one embodiment of the present invention, the composition may include the compound of Formula 1 in an amount of 0.00001% to 10% by weight based on the total weight of the composition.
본 발명의 시네프린 또는 이의 약학적으로 허용 가능한 염을 함유하는 조성물은 피부 미백 효과를 나타낸다.The composition containing synephrine or a pharmaceutically acceptable salt thereof of the present invention exhibits a skin whitening effect.
본 발명의 시네프린 또는 이의 약학적으로 허용 가능한 염을 함유하는 조성물은 피부 탄력 증진 또는 주름 개선 효과를 나타낸다. The composition containing synephrine or a pharmaceutically acceptable salt thereof of the present invention exhibits an effect of improving skin elasticity or wrinkles.
본 발명의 시네프린 또는 이의 약학적으로 허용 가능한 염을 함유하는 조성물은 피부 보습 효과를 나타낸다. The composition containing synephrine or a pharmaceutically acceptable salt thereof of the present invention exhibits a skin moisturizing effect.
본 발명의 시네프린 또는 이의 약학적으로 허용 가능한 염을 함유하는 조성물은 안전하면서도 우수한 화장품 원료, 약학 성분으로 이용될 수 있다. The composition containing synephrine or a pharmaceutically acceptable salt thereof of the present invention can be used as a safe and excellent cosmetic raw material and pharmaceutical ingredient.
이하, 본 발명을 보다 구체적으로 설명하기 위하여 하기 실시예 등을 들어 설명한다. 그러나, 본 발명에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며 본 발명의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되어서는 안 된다. 본 발명의 실시예들은 본 발명의 구체적 이해를 돕기 위해 예시적으로 제공되는 것이다.
Hereinafter, in order to describe the present invention in more detail, it will be described with reference to the following examples. However, the embodiments according to the present invention may be modified into various other forms, and the scope of the present invention should not be construed as being limited to the embodiments described below. Embodiments of the present invention are provided by way of example to aid in a specific understanding of the present invention.
참조예Reference example 1: One: 시네프린Synephrine (( SynephrineSynephrine ) 물질 정보) Substance information
[화학식 1][Formula 1]
물질명 : SynephrineName of substance: Synephrine
CAS No. : 94-07-5CAS No. : 94-07-5
분자식 : C9H13NO2 Molecular Formula: C 9 H 13 NO 2
분자량 : 167.21Molecular Weight: 167.21
구입처 : Forever Biotech; Nature Standard; Tauto Biotech (중국)
Where to buy: Forever Biotech; Nature Standard; Tauto Biotech (China)
실시예Example 1: One: 콜라게네이즈Collagenase 활성 억제 효과 Inhibitory effect
콜라겐(Collagen)을 분해하는 효소인 콜라게나제의 활성 저해 효과를 다음과 같이 확인하였다. The inhibitory effect on the activity of collagenase, an enzyme that degrades collagen, was confirmed as follows.
콜라게나제는 쥐의 이자에서 유래한 콜라게나제를 사용하였고, 콜라게나제의 기질로 합성 기질인 N-(3-[2-Furyl]acryloyl)-Leu-Gly-Pro-Ala을 사용하였다. 완충용액은 50mM Tricine, 10mM CaCl2·H2O, 400mM NaCl(pH 7.5)이 녹아 있는 용액을 사용하였다. 합성 기질은 완충용액을 이용하여 10mM의 농도로 녹인 후 최종적으로 75μM이 되도록 희석하였다. 콜라게나제는 4도의 차가운 3차 증류수를 이용하여 1unit/ml 농도로 녹인 후 최종적으로 0.05unit/ml이 되도록 완충용액을 이용하여 희석하였다. 콜라게나제 저해 후보는 최종농도 25, 50ppm에서 실험하였다. 이 때, 양성 대조군은 콜라게나제 저해 효과가 알려진 에피갈로카테킨 갈레이트(EGCG)를 최종농도 50ppm이 되도록 설정하였다. 반응은 96-웰플레이트에서 진행하였으며, 상온에서 10분간 반응시켰다. 분광 광도계를 이용하여 1분 간격으로 345 nm에서 흡광도를 측정하여 시간 대비 흡광도의 최대 기울기를 구하여 효소의 활성으로 정하였다. 콜라게나제 저해율은 다음과 같이 계산하였다.Collagenase was used as a collagenase derived from rat interest, and a synthetic substrate, N-(3-[2-Furyl]acryloyl)-Leu-Gly-Pro-Ala, was used as a substrate for collagenase. As a buffer solution, a solution in which 50mM Tricine, 10mM CaCl 2 ·H 2 O, and 400mM NaCl (pH 7.5) was dissolved was used. The synthetic substrate was dissolved in a buffer solution to a concentration of 10 mM and then diluted to a final concentration of 75 μM. Collagenase was dissolved at a concentration of 1 unit/ml in 4 degrees of cold, tertiary distilled water, and finally diluted to 0.05 unit/ml using a buffer solution. Collagenase inhibitory candidates were tested at final concentrations of 25 and 50 ppm. At this time, the positive control group was set to have a final concentration of 50 ppm epigallocatechin gallate (EGCG), which has a known collagenase inhibitory effect. The reaction was carried out in a 96-well plate, and the reaction was performed at room temperature for 10 minutes. The absorbance was measured at 345 nm at 1 minute intervals using a spectrophotometer, and the maximum slope of the absorbance versus time was determined as the activity of the enzyme. The collagenase inhibition rate was calculated as follows.
화학식 1의 화합물의 콜라게나제 활성 저해 효과 (반복수 =3)Inhibitory effect of the compound of formula 1 on collagenase activity (repeat number = 3)
상기 표 1의 결과에서 볼 수 있듯이, 화학식 1의 화합물은 양성대조군인 EGCG 보다 콜라게나제 활성 저해 효과가 뛰어남을 알 수 있다. 즉, 화학식 1의 화합물은 우수한 콜라게나제 활성 저해효과를 발휘하였다. 따라서, 화학식 1의 화합물은 피부재생, 주름개선을 위한 용도로 사용할 수 있음을 알 수 있었다.
As can be seen from the results of Table 1, it can be seen that the compound of Formula 1 has a better inhibitory effect on collagenase activity than the positive control EGCG. That is, the compound of Formula 1 exhibited an excellent inhibitory effect on collagenase activity. Therefore, it was found that the compound of Formula 1 can be used for skin regeneration and wrinkle improvement.
실시예Example 2: 2: 엘라스타제Elastase 활성 저해 효과 Activity inhibitory effect
엘라스틴(Elastin)을 분해하는 효소인 엘라스테이즈(Elastase)의 활성 저해 효과를 다음과 같이 확인하였다. The inhibitory effect of the activity of Elastase, an enzyme that degrades elastin, was confirmed as follows.
엘라스테이즈(Elastase)는 사람의 백혈구 세포로부터 유래한 엘라스테이즈를 사용하였고, 엘라스테이즈의 기질로 합성 기질인 MeOSuc-Ala-Ala-Pro-Val-pNA를 사용하였다. 완충용액은 100mM의 Tris(pH 7.5) 용액을 사용하였다. 엘라스테이즈는 완충용액을 이용하여 최종적으로 0.2 mU을 사용하였다. 또한 엘라스테이즈의 합성 기질은 DMSO를 이용하여 100mM 용액을 만든 후 최종 농도가 0.5mM이 되도록 완충용액을 이용하여 희석하였다. 이 때, 양성 대조군은 엘라스테이즈 저해 물질로 알려진 퀘르세틴(Quercetin)을 10ppm 농도로 넣은 것으로 설정하였다. 엘라스테이즈 저해 후보는 최종농도가 10, 20ppm이 되도록 첨가하였다. 반응은 96-웰플레이트에서 진행하였으며, 상온에서 20분간 반응시켰다. 분광 광도계를 이용하여 1분 간격으로 405 nm에서 흡광도를 측정하여 시간 대비 흡광도의 기울기를 구하여 효소의 활성도로 정하였다. 엘라스테이즈 저해율은 다음과 같이 계산하였다. For Elastase, Elastase derived from human leukocytes was used, and MeOSuc-Ala-Ala-Pro-Val-pNA, a synthetic substrate, was used as a substrate for Elastase. As the buffer solution, a 100 mM Tris (pH 7.5) solution was used. Elastase was finally used as 0.2 mU using a buffer solution. In addition, the synthetic substrate of Elastase was diluted with a buffer solution to a final concentration of 0.5 mM after making a 100 mM solution using DMSO. At this time, the positive control was set to contain quercetin, known as an elastase inhibitor, at a concentration of 10 ppm. Elastase inhibition candidates were added so that the final concentrations were 10 and 20 ppm. The reaction was carried out in a 96-well plate, and the reaction was performed at room temperature for 20 minutes. The absorbance was measured at 405 nm at 1 minute intervals using a spectrophotometer, and the slope of the absorbance against time was determined, and the activity of the enzyme was determined. Elastase inhibition rate was calculated as follows.
화학식 1의 화합물의 엘라스타제 활성 저해 효과 (반복수 =3)Inhibitory effect of the compound of formula 1 on elastase activity (repeat number = 3)
상기 표 2의 결과에서 볼 수 있듯이, 화학식 1의 화합물을 처리한 경우, 양성대조군 보다 효과는 적으나, 엘라스타제 활성 저해가 뛰어남을 알 수 있다. 즉, 화학식 1의 화합물은 우수한 엘라스타제 활성 저해효과를 발휘하였다. 따라서, 화학식 1의 화합물은 피부재생, 주름개선을 위한 용도로 사용할 수 있음을 알 수 있었다.
As can be seen from the results of Table 2, when the compound of Formula 1 is treated, the effect is less than that of the positive control group, but it can be seen that the inhibition of elastase activity is excellent. That is, the compound of Formula 1 exhibited an excellent inhibitory effect on elastase activity. Therefore, it was found that the compound of Formula 1 can be used for skin regeneration and wrinkle improvement.
실시예Example 3: 미백효과-멜라닌 총량 감소 효과 3: whitening effect-reducing the total amount of melanin
화학식1의 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 미백평가를 수행하였다. The whitening effect was confirmed by measuring the total amount of melanin at the cell level by adding the compound of Formula 1 to the culture medium of mouse melanoma cells (B-16 mouse melanoma cells) (Lotan R., Lotan D. Cancer) Res . 40:3345-3350, 1980). Before the experiment, toxicity was evaluated for the melanoma cells of mice, and a non-toxic concentration was selected to perform whitening evaluation.
화학식 1의 화합물을 배양액에 최종 농도가 1 ppm, 10 ppm이 되도록 하였으며, 대조군인 알부틴은 100 ppm이 되도록 배지에 첨가하여 각각 B-16 멜라노마 세포에 처리하여 3일간 배양하였다. The final concentration of the compound of Formula 1 was 1 ppm and 10 ppm in the culture solution, and arbutin, a control, was added to the medium so that it became 100 ppm, and each of the B-16 melanoma cells was treated for 3 days.
이후, 세포들을 트립신(trypsin) 처리하여 배양용기로부터 떼어내 원심분리한 후, 멜라닌을 추출하였다. 떼어낸 세포는 수산화나트륨 용액(1N 농도) 1 ml를 가하여 10분간 끓여 멜라닌을 녹이고 분광 광도계를 이용하여, 400 nm에서 흡광도를 측정하여 생성된 멜라닌의 양을 측정하였다. Thereafter, the cells were treated with trypsin, removed from the culture vessel, centrifuged, and melanin was extracted. The detached cells were boiled for 10 minutes by adding 1 ml of sodium hydroxide solution (1N concentration) to dissolve melanin, and the absorbance was measured at 400 nm using a spectrophotometer to measure the amount of melanin produced.
상기 멜라닌 양은 단위 세포수당(1×106 cell)의 흡광도로 나타내는 방법으로 측정하였으며, 대조군에 대한 상대적인 멜라닌 총량을 저해율(%)로 계산하고 결과를 표 3에 정리하였다.
The amount of melanin was measured by a method expressed by absorbance per unit cell count (1×10 6 cells), and the total amount of melanin relative to the control was calculated as an inhibition rate (%), and the results are summarized in Table 3.
농도에 따른 세포수준에서의 멜라닌 총량의 감소 효과The effect of reducing the total amount of melanin at the cellular level according to the concentration
(abs)Melanin production
(abs)
상기 표 3의 결과에서 볼 수 있듯이, 화학식1의 화합물은 미백 물질로 알려진 알부틴(arbutin)과 비교할 때, 배양된 쥐의 멜라노마 세포에 대하여 더 적은 농도를 적용하여도 멜라닌 생성저해율이 더 우수하고, 더 적은 멜라닌 총량을 나타내는 것을 확인할 수 있었다. As can be seen from the results of Table 3, when compared to arbutin, which is known as a whitening substance, the compound of Formula 1 exhibits better melanin production inhibition even when a lower concentration is applied to the melanoma cells of the cultured mouse. , It was confirmed that the total amount of melanin was less.
따라서, 화학식 1의 화합물을 이용하여 미백 용도로 사용할 수 있음을 알 수 있었다.
Therefore, it was found that the compound of Formula 1 can be used for whitening purposes.
실시예Example 4: 4: 항당화Anti-glycosylation 효과 effect
당화 저해(anti-glycation) 효능을 확인하기 위하여, L-arginine과 포도당을 이용하여 당화 저해 활성을 측정하였다. In order to confirm the anti-glycation effect, the glycosylation inhibitory activity was measured using L-arginine and glucose.
먼저, 1M 인산 완충용액(pH 7.4)을 이용하여 1M L-아지닌(arginine), 1M 포도당을 녹여 준비하고 1M 인산 완충용액을 이용하여 시료를 50, 100ppm이 되도록 희석해서 준비한다. 1M L-아지닌과 1M 인산 완충용액을 1대 4의 비율로 섞은 다음 96-웰플레이트에 80 μl씩 분주한다. 여기에 각각 50, 100ppm으로 희석한 시료와 양성 대조군으로 사용될 0.01M aminoguanidin을 100 μl씩 첨가한다. 이 시료들을 잘 섞어준 다음, 마지막으로 포도당의 최종 농도가 0.1M이 되도록 1M 인산 완충용액으로 희석한 포도당을 넣어 준다. 70℃에서 4시간 동안 반응 시킨다. 96-웰플레이트를 분광 광도계를 이용하여 420 nm에서 흡광도를 측정하여 당화 정도를 측정하였다. First, prepare by dissolving 1M L-arginine and 1M glucose using 1M phosphate buffer solution (pH 7.4), and dilute the sample to 50 or 100ppm using 1M phosphate buffer solution. Mix 1M L-azinine and 1M phosphate buffer in a ratio of 1 to 4, and then dispense 80 μl into a 96-well plate. Add 100 μl of the sample diluted to 50 and 100 ppm and 0.01M aminoguanidin to be used as a positive control, respectively. After mixing these samples well, add glucose diluted with 1M phosphate buffer so that the final concentration of glucose is 0.1M. It was reacted at 70° C. for 4 hours. The degree of saccharification was measured by measuring the absorbance at 420 nm on a 96-well plate using a spectrophotometer.
하기 식의 Glycation 실험군은 1M L-아지닌과 1M 포도당을 넣어 당화를 유발시킨 실험군이며, 시료 자체의 흡광도를 측정하기 위해서 포도당을 넣지 않고 1M L-아지닌과 시료만을 넣어 420 nm에서 흡광도를 측정하였다. 당화 저해 활성은 다음과 같은 식으로 구할 수 있다. The Glycation experiment group of the following formula is an experimental group in which 1M L-azinine and 1M glucose were added to induce saccharification.In order to measure the absorbance of the sample itself, 1M L-Aginine and only the sample were added without glucose to measure the absorbance at 420 nm. I did. The glycosylation inhibitory activity can be calculated as follows.
화학식 1의 화합물의 항당화 효과Anti-glycosylation effect of the compound of formula 1
상기 표 4의 결과에서 볼 수 있듯이, 화학식1의 화합물은 우수한 항당화 효과를 나타내어 미백 또는 주름 개선 효과를 가질 수 있을 것으로 생각된다.As can be seen from the results of Table 4, it is believed that the compound of Formula 1 exhibits an excellent anti-glycosylation effect and thus may have a whitening or wrinkle improvement effect.
Claims (8)
[화학식 1]
A cosmetic composition for improving skin elasticity or wrinkles comprising a compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
[Formula 1]
[화학식 1]
A cosmetic composition for improving dull skin through inhibition of saccharification comprising a compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
[Formula 1]
[화학식 1]
A health food composition for improving skin elasticity or wrinkles comprising a compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
[Formula 1]
[화학식 1]
A health food composition for anti-glycosylation comprising a compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
[Formula 1]
[화학식 1]
A pharmaceutical composition for improving skin wrinkles comprising a compound represented by the following Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
[Formula 1]
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