KR101870210B1 - Anti-aging composition comprising aster plant extracts - Google Patents
Anti-aging composition comprising aster plant extracts Download PDFInfo
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- KR101870210B1 KR101870210B1 KR1020170142154A KR20170142154A KR101870210B1 KR 101870210 B1 KR101870210 B1 KR 101870210B1 KR 1020170142154 A KR1020170142154 A KR 1020170142154A KR 20170142154 A KR20170142154 A KR 20170142154A KR 101870210 B1 KR101870210 B1 KR 101870210B1
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Abstract
본 명세서에는 개미취속(Aster L.) 식물의 추출물, 이의 분획물 또는 이들로부터 분리한 화합물을 유효성분으로 포함하는 항노화용 조성물이 개시된다. 상기 항노화용 조성물은 노화에 따른 피부 변화를 예방, 지연 또는 개선하는 효과가 있다. 또한, 상기 항노화용 조성물은 콜라겐 분해효소의 발현 또는 활성을 억제하거나, 또는 콜라겐의 발현 또는 활성을 촉진시킴으로써, 피부 주름을 예방 또는 개선하고 피부 탄력을 증진시켜 주는 효과가 있다.In this specification, an anti-aging composition comprising an extract of Aster L. plant, a fraction thereof, or a compound isolated therefrom as an active ingredient is disclosed. The anti-aging composition has an effect of preventing, delaying or improving the skin change caused by aging. In addition, the anti-aging composition inhibits the expression or activity of collagenase or promotes the expression or activity of collagen, thereby preventing or improving wrinkles of the skin and improving skin elasticity.
Description
본 명세서에는 개미취속 식물의 추출물을 유효성분으로 포함하는 항노화용 조성물이 개시된다.The present specification discloses an anti-aging composition comprising an extract of a plant of the genus Anthemis as an active ingredient.
피부는 외부 환경의 자극으로부터 체내의 기관들을 보호해 주며, 체온조절 등의 생체 항상성 유지에 중요한 역할을 한다. 이러한 피부는 여러 가지 내적/외적 요인에 의해서 노화가 발생되며, 크게 유전적 원인에 의한 내인성 노화와 환경적 원인에 의한 외인성 노화로 구분된다. 이 중, 광노화는 자외선(ultraviolet; UV)에 의한 노화를 의미한다. 최근 환경오염으로 인한 오존층 파괴는 자외선의 양을 증가시켰고 이에 따라 광노화에 대한 연구가 주목되고 있다(Wang SQ et al., Dermatol. Ther. 23(1):31-47, 2010). 광노화된 피부에서는 거칠어짐, 탄력 손실, 주름 발생 또는 불규칙한 색소 침착 등과 같은 외관상 특징이 관찰되며, 이 중 광노화의 주된 연구 분야는 피부 주름의 변화에 대한 것이다. 상기 광노화에 의한 피부 주름 형성에 관해 피부의 주요 구성성분인 콜라겐(collagen)의 합성, 분해 및 수분 함유량 등의 기초적인 생리 대사 변화에 대한 연구 결과가 다수 보고되고 있다(Brenneisen et al., Ann. N. Y. Acad. Sci., 973:31-43, 2002).The skin protects the internal organs from stimuli from the external environment, and plays an important role in maintaining biological homeostasis such as body temperature control. Such skin aging occurs due to various internal/external factors, and is largely divided into endogenous aging due to genetic causes and exogenous aging due to environmental causes. Among them, photoaging means aging due to ultraviolet (UV) rays. Recently, the destruction of the ozone layer due to environmental pollution increased the amount of ultraviolet rays, and accordingly, research on photoaging is drawing attention (Wang SQ et al., Dermatol. Ther. 23(1):31-47, 2010). In photoaging skin, appearance features such as roughness, loss of elasticity, occurrence of wrinkles, or irregular pigmentation are observed. Among them, the main research field of photoaging is on changes in skin wrinkles. In relation to the formation of wrinkles in the skin due to photoaging, a number of research results have been reported on basic physiological metabolic changes such as the synthesis, decomposition and moisture content of collagen, which is a major component of the skin (Brenneisen et al., Ann. NY Acad. Sci., 973:31-43, 2002).
피부 진피층에 존재하는 콜라겐은 피부 전체 건조 중량의 약 70~80%를 차지하며, 탄력섬유인 엘라스틴(elastin)과 함께 피부 탄력을 주관하는 것으로 알려져 있다. 특히, 자외선에 의해 활성 산소종(reactive oxygen species) 생성이 증가되고 피부의 효소적/비효소적 항산화 방어체계 붕괴가 유발되어 콜라겐의 분해 증가 및 생합성을 감소시켜 진피층 내의 콜라겐이 현저하게 감소하게 된다(Bickers DR, Athar M, J. Invest. Dermatol., 126(12):2565-2575, 2006). 상기 콜라겐 감소에 중요한 영향을 미치는 것은 콜라겐 분해 효소(MMPs; matrix metalloproteinases)로서, 이는 세포 외 기질(extracellular matrix)과 기저막(basement membrane)의 분해에 관여한다. 상기 효소는 자외선에 의해 활성이 증가되며 이를 억제함으로써 자외선에 의해 유도되는 피부 두께 증가 및 주름 형성이 감소된다는 연구 결과들이 보고된 바 있다(Inomata S et al., J. Invest. Dermatol., 120(1):128-134, 2003). 따라서, 광노화의 예방 및 치료를 위해서는 MMPs를 조절하는 것이 효과적인 방법이다.Collagen present in the dermal layer of the skin accounts for about 70 to 80% of the total dry weight of the skin, and is known to control skin elasticity along with elastin, an elastic fiber. In particular, the generation of reactive oxygen species is increased by ultraviolet rays and the breakdown of the enzymatic/non-enzymatic antioxidant defense system of the skin is caused, thereby increasing the degradation of collagen and reducing biosynthesis, resulting in a remarkable decrease in collagen in the dermal layer. (Bickers DR, Athar M, J. Invest. Dermatol., 126(12):2565-2575, 2006). An important influence on the reduction of collagen is collagen-degrading enzymes (MMPs), which are involved in the decomposition of the extracellular matrix and the basement membrane. Research results have been reported that the activity of the enzyme is increased by ultraviolet light and that by inhibiting it, the increase in skin thickness and wrinkle formation induced by ultraviolet light is reduced (Inomata S et al., J. Invest. Dermatol., 120((Inomata S et al., J. Invest. 1):128-134, 2003). Therefore, for the prevention and treatment of photoaging, controlling MMPs is an effective method.
한편, 피부 진피층의 구성성분인 히알루론산(hyaluronic acid)은 진피층의 콜라겐 사이를 채워 피부의 보습 및 탄력을 유지시키는 성분이다. 특히, 자외선은 히알루론산의 양을 감소시켜 피부 내 수분 함유량을 감소시키고 경피 수분 손실량을 증가시켜 피부 장벽의 손상을 야기한다. 이로 인해 피부가 거칠어지고 탄력성이 감소되어 주름이 생성된다(Baumann L, J. Pathol., 211(2):241-251, 2007). 즉, 피부의 보습력 상실은 피부노화의 주요 원인이 된다.Meanwhile, hyaluronic acid, a constituent of the dermal layer of the skin, is a component that fills the collagens in the dermal layer to maintain moisture and elasticity of the skin. In particular, ultraviolet rays reduce the amount of hyaluronic acid, thereby reducing the moisture content in the skin and increasing the amount of transdermal moisture loss, causing damage to the skin barrier. As a result, the skin becomes rough and the elasticity decreases, resulting in wrinkles (Baumann L, J. Pathol., 211(2):241-251, 2007). In other words, loss of moisturizing power of the skin is a major cause of skin aging.
주름 개선에 대한 전 세계 소비자들의 기대와 관심은 레티놀을 시작으로 하여 2000년대부터 천연물 추출성분, 아데노신, 세포성장인자 등 그 종류와 기능이 다양해지고 있는 추세이다(Lee EJ et al., Journal of the Korean Society of Cosmetology, 17(1):127-133, 2011). 기존의 방법은 레티노이드, 아스코르브산, 토코페롤 및 히알루론산 등을 함유하는 화장료나 의약품을 제조하여 사용하는 것이었다.The expectations and interests of consumers around the world for wrinkle improvement, starting with retinol, have been diversifying their types and functions such as natural extracts, adenosine, and cell growth factors since the 2000s (Lee EJ et al., Journal of the) Korean Society of Cosmetology, 17(1):127-133, 2011). The existing method was to prepare and use cosmetics or pharmaceuticals containing retinoids, ascorbic acid, tocopherol and hyaluronic acid.
하지만, 현재 개발되고 있는 피부 주름 개선 또는 피부 노화 개선을 위한 유효성분들은 일부 화장품 원료로 사용할 수 없거나 매우 불안정하고 피부로의 전달이 용이하지 않아 특별한 안정화 시스템 및 전달 체계가 필요하며, 피부 주름의 개선 효과가 가시적이지 않다는 문제점이 있다. 예컨대, 상기 피부 주름 개선에 유효한 성분인 레티노이드는 콜라겐 분해효소를 저해하고 콜라겐 합성을 증가시킴으로써 주름 형성 및 탄력 감소 등의 광노화 현상을 개선하기 위해 이용되고 있으나, 자외선에 매우 민감하여 쉽게 화학적인 변화를 일으켜 피부 자극 등의 부작용이 발생하고 장기적으로 사용해야 효과가 나타난다는 문제점이 있다(Rabe JH, J. Am. Acad. Dermatol., 55:1-19, 2006).However, active ingredients for improving skin wrinkles or skin aging that are currently being developed cannot be used as raw materials for some cosmetics, or they are very unstable and difficult to deliver to the skin, requiring a special stabilization system and delivery system, and improving skin wrinkles. There is a problem that the effect is not visible. For example, retinoids, which are effective ingredients for skin wrinkle improvement, are used to improve photoaging phenomena such as wrinkle formation and elasticity reduction by inhibiting collagen degradation enzymes and increasing collagen synthesis. It causes side effects such as skin irritation and has a problem that it is effective for long-term use (Rabe JH, J. Am. Acad. Dermatol., 55:1-19, 2006).
일 측면에서, 본 명세서는 개미취속(Aster L.) 식물의 추출물, 이의 분획물 또는 이들로부터 분리한 화합물을 유효성분으로 포함하는 항노화용 조성물을 제공하는 것을 목적으로 한다.In one aspect, the present specification aims to provide an anti-aging composition comprising an extract of a plant of Aster L., a fraction thereof, or a compound isolated therefrom as an active ingredient.
일 측면에서, 본 명세서에 개시된 기술은 개미취속(Aster L.) 식물의 추출물을 유효성분으로 포함하는 항노화용 조성물을 제공한다.In one aspect, the technology disclosed in the present specification provides an anti-aging composition comprising an extract of a plant of Aster L. as an active ingredient.
예시적인 일 구현예에서, 상기 개미취속 식물은 개미취(Aster tataricus L. f.), 갯개미취(Aster tripolium L.), 좀개미취(Aster maakii REGEL) 및 벌개미취(Aster koraiensis NaKai)로 이루어진 군에서 선택되는 1 이상일 수 있다.In an exemplary embodiment, the plant of the genus ants is selected from the group consisting of ant odor (Aster tataricus L. f.), ant ant odor (Aster tripolium L.), ant ant odor (Aster maakii REGEL) and bee ant odor (Aster koraiensis NaKai). It can be 1 or more.
예시적인 일 구현예에서, 상기 개미취속 식물은 벌개미취(Aster koraiensis NaKai)일 수 있다.In an exemplary embodiment, the plant of the genus ants may be a bee ants (Aster koraiensis NaKai).
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 물 및 탄소수 1 내지 6의 알코올로 이루어진 군에서 선택되는 1 이상의 용매로 추출한 것일 수 있다.In an exemplary embodiment, the extract of the genus antacid plant may be extracted with one or more solvents selected from the group consisting of water and an alcohol having 1 to 6 carbon atoms.
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 에탄올 추출물일 수 있다.In an exemplary embodiment, the extract of the plant of the genus Anthemis may be an ethanol extract.
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 조성물 전체 중량을 기준으로 0.001 내지 80 중량%로 포함되는 것일 수 있다.In an exemplary embodiment, the extract of the genus antacid plant may be included in an amount of 0.001 to 80% by weight based on the total weight of the composition.
다른 측면에서, 본 명세서에 개시된 기술은 하기 화학식 1로 표시되는 화합물, 이의 유도체, 이의 염, 이의 수화물, 이의 용매화물, 이의 프로드럭 또는 이의 이성질체를 유효성분으로 포함하는 항노화용 조성물을 제공한다.In another aspect, the technology disclosed in the present specification provides a composition for anti-aging comprising a compound represented by the following
[화학식 1][Formula 1]
상기 식에서, R1 및 R2는 각각 수소, 산소, 히드록시, C1~C4의 알킬에스테르 및 C1~C4의 알콕시로 이루어지는 군으로부터 선택되는 어느 하나이고, R1 및 R2 중 어느 하나가 산소이고 다른 하나가 수소인 경우, 상기 R1 또는 R2는 이들과 인접한 두 개의 탄소와 결합하는 에폭사이드이며, 는 단일 또는 이중결합이다.In the above formula, R 1 and R 2 are each selected from the group consisting of hydrogen, oxygen, hydroxy, C 1 to C 4 alkyl ester and C 1 to C 4 alkoxy, and any of R 1 and R 2 When one is oxygen and the other is hydrogen, R 1 or R 2 is an epoxide bonded to two adjacent carbons thereto, Is a single or double bond.
예시적인 일 구현예에서, 상기 화합물은 하기 화학식 2로 표시되는 화합물일 수 있다.In an exemplary embodiment, the compound may be a compound represented by Formula 2 below.
[화학식 2][Formula 2]
예시적인 일 구현예에서, 상기 화합물은 개미취속(Aster L.) 식물의 추출물 또는 이의 분획물로부터 분리된 것일 수 있다.In an exemplary embodiment, the compound may be isolated from an extract of a plant of Aster L. or a fraction thereof.
예시적인 일 구현예에서, 상기 화합물은 조성물 전체 중량을 기준으로 0.0001 내지 10 중량%로 포함되는 것일 수 있다.In an exemplary embodiment, the compound may be included in an amount of 0.0001 to 10% by weight based on the total weight of the composition.
예시적인 일 구현예에서, 상기 조성물은 광노화에 대한 항노화용일 수 있다.In one exemplary embodiment, the composition may be for anti-aging against photoaging.
예시적인 일 구현예에서, 상기 조성물은 피부 주름 개선용일 수 있다.In an exemplary embodiment, the composition may be for improving skin wrinkles.
예시적인 일 구현예에서, 상기 조성물은 피부 탄력 증진용일 수 있다.In an exemplary embodiment, the composition may be for enhancing skin elasticity.
일 측면에서, 본 명세서에 개시된 기술은 개미취속(Aster L.) 식물의 추출물, 이의 분획물 또는 이들로부터 분리한 화합물을 유효성분으로 포함하는 항노화용 조성물을 제공하는 효과가 있다.In one aspect, the technology disclosed in the present specification has the effect of providing an anti-aging composition comprising an extract of a plant of Aster L., a fraction thereof, or a compound isolated therefrom as an active ingredient.
상기 항노화용 조성물은 노화에 따른 피부 변화를 예방, 지연 또는 개선하는 효과가 있다.The anti-aging composition has an effect of preventing, delaying or improving skin changes due to aging.
상기 항노화용 조성물은 콜라겐 분해효소의 발현 또는 활성을 억제하거나, 또는 콜라겐의 발현 또는 활성을 촉진시킴으로써, 피부 주름을 예방 또는 개선하고 피부 탄력을 증진시켜 주는 효과가 있다.The anti-aging composition has an effect of preventing or improving skin wrinkles and enhancing skin elasticity by inhibiting the expression or activity of collagen-degrading enzyme, or by promoting the expression or activity of collagen.
상기 항노화용 조성물은 천연물 유래의 개미취속(Aster L.) 식물의 추출물, 이의 분획물 또는 이들로부터 분리한 화합물을 유효성분으로 포함함으로써, 부작용 발생 가능성이 현저하게 낮고 사용 안정성이 높은 효과가 있다.The anti-aging composition contains an extract of a natural product-derived Aster L. plant, a fraction thereof, or a compound isolated from these as an active ingredient, so that the possibility of occurrence of side effects is remarkably low and the use stability is high.
도 1은 본 명세서의 일 구현예에 따른 벌개미취 추출물 및 화학식 2의 화합물 각각에 의해 콜라겐 분해효소-1의 분비량이 억제되는 효과를 나타낸 것이다. (*p<0.05, **p<0.01)
도 2는 본 명세서의 일 구현예에 따른 벌개미취 추출물 및 화학식 2의 화합물 각각에 의해 타입-1 프로콜라겐의 분비량이 증가되는 효과를 나타낸 것이다. (*p<0.05, **p<0.01)
도 3은 본 명세서의 일 구현예에 따른 벌개미취 추출물 및 화학식 2의 화합물 각각에 의해 콜라겐 분해효소의 발현량이 감소되는 효과를 나타낸 것이다.
도 4는 본 명세서의 일 구현예에 따른 벌개미취 추출물 및 화학식 2의 화합물 각각에 의해 콜라겐의 발현량이 증가되는 효과를 나타낸 것이다.1 shows the effect of inhibiting the secretion of collagen-degrading enzyme-1 by each of the bee ant odor extract and the compound of
Figure 2 shows the effect of increasing the secretion amount of type-1 procollagen by each of the bee ant odor extract and the compound of
3 shows the effect of reducing the expression level of collagenase by each of the extract of bee gill odor and the compound of
4 is a view showing the effect of increasing the expression amount of collagen by each of the bee ant odor extract and the compound of
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
일 측면에서, 본 명세서는 개미취속(Aster L.) 식물의 추출물을 유효성분으로 포함하는 항노화용 조성물을 제공한다.In one aspect, the present specification provides an anti-aging composition comprising an extract of a plant of Aster L. as an active ingredient.
본 명세서에서 "유효성분"은 단독으로 목적으로 하는 활성을 나타내거나 또는 그 자체는 활성이 없는 담체 등과 함께 목적으로 하는 활성을 나타낼 수 있는 성분을 의미한다.In the present specification, the "active ingredient" refers to an ingredient that can exhibit a desired activity by itself, or that can exhibit a desired activity together with a carrier that is not active by itself.
개미취속(Aster L.) 식물은 쌍떡잎식물 초롱꽃목 국화과의 여러해살이풀서, 한국, 일본, 중국 북부 및 북동부, 몽골, 시베리아 등지의 습지에서 서식한다. Aster L. plant is a dicotyledonous plant, a perennial plant of the Asteraceae family, and lives in wetlands in Korea, Japan, northern and northeastern China, Mongolia, and Siberia.
예시적인 일 구현예에서, 상기 개미취속 식물은 개미취(Aster tataricus L. f.), 갯개미취(Aster tripolium L.), 좀개미취(Aster maakii REGEL) 및 벌개미취(Aster koraiensis NaKai)로 이루어진 군에서 선택되는 1 이상일 수 있다. 상기 벌개미취는 별개미취, 고려쑥부쟁이라고도 불리운다.In an exemplary embodiment, the plant of the genus ants is selected from the group consisting of ant odor (Aster tataricus L. f.), ant ant odor (Aster tripolium L.), ant ant odor (Aster maakii REGEL) and bee ant odor (Aster koraiensis NaKai). It can be 1 or more. The bee ant michwi is also called separate ant michwi and Goryeo wormwood.
상기 개미취속 식물은 추출물의 생성을 위해 그의 지상부 또는 지하부의 일부 또는 전부를 포함하는 식물의 전 범위에 걸쳐 제한이 없이 사용 가능하며, 예를 들어 잎, 줄기 및 뿌리로 이루어진 군에서 선택되는 1 이상을 사용할 수 있다. 또한, 상기 개미취속 식물은 생육 단계 중 모든 시기에 걸쳐 사용이 가능하며, 예를 들어 어린순을 이용할 수 있다. 아울러, 상기 개미취속 식물은 재배한 것 또는 시판되는 것 등의 제한이 없이 사용 가능하다.The anthill plant can be used without limitation over the entire range of plants including some or all of the above-ground or underground portions for the production of extracts, for example, one or more selected from the group consisting of leaves, stems, and roots. Can be used. In addition, the plant of the genus ants can be used throughout all periods of the growth stage, for example, young shoots can be used. In addition, the plants of the genus ants can be used without restrictions such as cultivated or commercially available.
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 조추출물뿐만 아니라 추출물의 가공물, 예를 들어 건조, 농축, 분획, 발효 등 추가적인 가공에 의한 모든 형태를 포함하는 것을 의미한다.In an exemplary embodiment, the extract of the plant of the genus ants is meant to include not only a crude extract, but also a processed product of the extract, for example, drying, concentration, fractionation, fermentation, etc. through additional processing.
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 개미취속 식물 그 자체 또는 이를 분말화하거나 추출공정을 통해 수득한 추출물일 수 있다. 상기 추출공정은 당해 기술분야에서 이용되는 통상의 방법에 따라 실시될 수 있다.In an exemplary embodiment, the extract of the plant of the genus Forte may be the plant itself, or an extract obtained through an extraction process or powdering the plant. The extraction process may be carried out according to a conventional method used in the art.
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 물, 탄소수 1 내지 6의 무수 또는 함수 알코올(예컨대, 메탄올, 에탄올, 프로판올 또는 부탄올), 프로필렌글리콜, 부틸렌글리콜, 디프로필렌글리콜, 글리세린, 아세톤, 에틸아세테이트, 클로로포름, 메틸렌클로라이드, 부틸아세테이트, 디에틸에테르, 디클로로메탄, 헥산, 시클로헥산, 에테르, 석유에테르, 벤젠 및 이들의 혼합물을 포함하는 군에서 선택되는 추출용매, 구체적으로 물, 메탄올 및 에탄올을 포함하는 군에서 선택되는 하나 이상의 추출용매로 추출한 추출물일 수 있다. 추출용매의 경우 상기 나열된 추출용매에 한정하는 것은 아니며, 추출용매의 구체적인 사용량은 추출될 각 시료의 5 내지 100 중량배이다.In an exemplary embodiment, the extract of the forsythia plant is water, an anhydrous or hydrous alcohol having 1 to 6 carbon atoms (eg, methanol, ethanol, propanol or butanol), propylene glycol, butylene glycol, dipropylene glycol, glycerin, Extraction solvent selected from the group containing acetone, ethyl acetate, chloroform, methylene chloride, butyl acetate, diethyl ether, dichloromethane, hexane, cyclohexane, ether, petroleum ether, benzene, and mixtures thereof, specifically water, methanol And it may be an extract extracted with one or more extraction solvents selected from the group containing ethanol. The extraction solvent is not limited to the extraction solvents listed above, and the specific amount of the extraction solvent is 5 to 100 times the weight of each sample to be extracted.
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 초임계 추출, 아임계 추출, 고온 추출, 고압 추출, 초음파 추출, 미생물을 이용한 발효나 자연발효대사 또는 XAD 및 HP-20을 포함하는 흡착 수지를 이용한 방법 등 당업계의 통상적인 추출방법에 따라 제조될 수 있다. 구체적으로, 가온하며 환류 추출 또는 상온에서 추출할 수 있으나, 이에 제한되지 않는다. 아울러, 추출횟수는 1 내지 5회일 수 있으나, 구체적으로 3회 반복하여 추출할 수 있으며, 이에 제한되지 않는다. 추출시간은 2 내지 24시간일 수 있고, 구체적으로 2 내지 12시간, 또는 3 내지 10시간, 또는 3 내지 5시간일 수 있으나, 이에 제한되지 않는다. In an exemplary embodiment, the extract of the ant odor plant is supercritical extraction, subcritical extraction, high temperature extraction, high pressure extraction, ultrasonic extraction, fermentation or natural fermentation metabolism using microorganisms, or adsorption resin containing XAD and HP-20 It can be prepared according to a conventional extraction method in the art, such as a method using. Specifically, it may be heated and extracted at reflux or at room temperature, but is not limited thereto. In addition, the number of extractions may be 1 to 5 times, but specifically, extraction may be repeated 3 times, but is not limited thereto. The extraction time may be 2 to 24 hours, specifically 2 to 12 hours, or 3 to 10 hours, or 3 to 5 hours, but is not limited thereto.
예시적인 일 구현예에서, 상기 개미취속 식물의 추출물은 조성물 전체 중량을 기준으로 0.001 내지 80 중량%로 포함되는 것일 수 있다. 개미취속 식물의 추출물이 조성물 내 상기 범위로 포함됨으로써, 다른 함유 물질들과의 적절한 조성비를 갖고 우수한 항노화 효능을 나타내는 효과가 있으며, 경제성 및 효율성 면에서도 바람직할 수 있다. 구체적으로 상기 개미취속 식물의 추출물은 조성물 전체 중량을 기준으로 0.005 내지 78 중량%, 또는 0.01 내지 76 중량%, 또는 0.05 내지 74 중량%, 또는 0.1 내지 72 중량%, 또는 0.5 내지 70 중량%, 또는 1.0 내지 68 중량%, 또는 1.0 내지 66 중량%, 또는 1.0 내지 64 중량%, 또는 1.0 내지 62 중량%, 또는 1.0 내지 60 중량%, 또는 1.0 내지 50 중량%, 또는 1.0 내지 40 중량%, 또는 1.0 내지 30 중량%, 또는 1.0 내지 20 중량%, 또는 1.0 내지 10 중량%로 포함되는 것일 수 있다.In an exemplary embodiment, the extract of the genus antacid plant may be included in an amount of 0.001 to 80% by weight based on the total weight of the composition. Since the extract of the plant of the genus Anthemis is included in the above range in the composition, it has an effect of showing excellent anti-aging efficacy with an appropriate composition ratio with other containing materials, and may be preferable in terms of economy and efficiency. Specifically, the extract of the plant of the genus Anthemis is 0.005 to 78% by weight, or 0.01 to 76% by weight, or 0.05 to 74% by weight, or 0.1 to 72% by weight, or 0.5 to 70% by weight, based on the total weight of the composition, or 1.0 to 68% by weight, or 1.0 to 66% by weight, or 1.0 to 64% by weight, or 1.0 to 62% by weight, or 1.0 to 60% by weight, or 1.0 to 50% by weight, or 1.0 to 40% by weight, or 1.0 It may be included in to 30% by weight, or 1.0 to 20% by weight, or 1.0 to 10% by weight.
다른 측면에서, 본 명세서는 하기 화학식 1로 표시되는 화합물, 이의 유도체, 이의 염, 이의 수화물, 이의 용매화물, 이의 프로드럭 또는 이의 이성질체를 유효성분으로 포함하는 항노화용 조성물을 제공한다.In another aspect, the present specification provides a composition for anti-aging comprising a compound represented by the following
[화학식 1][Formula 1]
상기 식에서, R1 및 R2는 각각 수소, 산소, 히드록시, C1~C4의 알킬에스테르 및 C1~C4의 알콕시로 이루어지는 군으로부터 선택되는 어느 하나이고, R1 및 R2 중 어느 하나가 산소이고 다른 하나가 수소인 경우, 상기 R1 또는 R2는 이들과 인접한 두 개의 탄소와 결합하는 에폭사이드이며, 는 단일 또는 이중결합이다.In the above formula, R 1 and R 2 are each selected from the group consisting of hydrogen, oxygen, hydroxy, C 1 to C 4 alkyl ester and C 1 to C 4 alkoxy, and any of R 1 and R 2 When one is oxygen and the other is hydrogen, R 1 or R 2 is an epoxide bonded to two adjacent carbons thereto, Is a single or double bond.
예시적인 일 구현예에서, 상기 화학식 1의 화합물은 하기 화학식 2 내지 5로 표시되는 화합물일 수 있다.In an exemplary embodiment, the compound of
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
본 명세서에서 "유도체"는 화합물들의 치환 가능한 위치에서 다른 치환기로 변경되는 모든 화합물들을 의미한다. 이러한 치환기의 종류에는 제한이 없으며, 예컨대 각각 독립적으로 히드록실, 페녹시, 티에닐, 푸릴, 피리딜, 시클로헥실, 알킬알콜, 알킬디알콜 또는 임의 치환된 페닐로 치환될 수 있는 C1-10 비사이클릭 탄화수소기; 히드록실, 히드록시메틸, 메틸 또는 아미노로 치환될 수 있는 C5-6 사이클릭 탄화수소기; 또는 당 잔기를 포함할 수 있다. 본 명세서에서 "당 잔기"라는 용어는 다당류 분자로부터 1개의 수소 원자 제거시의 기를 의미하며, 따라서 예를 들어 단당류 또는 올리고당으로부터 유래된 잔기를 의미할 수 있다.In the present specification, "derivative" refers to all compounds that are changed with other substituents at the positions of the compounds capable of being substituted. There is no limitation on the kind of these substituents, such as C 1-10 which may each independently be substituted with hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl, alkyl alcohol, alkyldialcohol or optionally substituted phenyl. Bicyclic hydrocarbon group; C 5-6 cyclic hydrocarbon group which may be substituted with hydroxyl, hydroxymethyl, methyl or amino; Or it may contain a sugar moiety. In the present specification, the term "sugar moiety" refers to a group when one hydrogen atom is removed from a polysaccharide molecule, and thus may mean, for example, a moiety derived from a monosaccharide or an oligosaccharide.
구체적으로, 본 명세서에서 상기 "화합물의 유도체"는 상기 화학식 1에서 수소 또는 알킬기만을 포함하는 치환기를 직쇄(unbranched) 또는 분지(branched)된 C1 내지 C18의 알킬기(alkyl group), C1 내지 C18의 알콕시기(alkoxy group), C1 내지 C18의 알케닐기(alkenyl group), C1 내지 C18의 알키닐기(alkynyl group) 또는 C3 내지 C6의 사이클릭 알킬기(cyclic alkyl group)로 치환하여 얻어지는 화합물을 모두 포함할 수 있다. Specifically, in the present specification, the "compound derivative" refers to a C 1 to C 18 alkyl group, C 1 to which a substituent including only hydrogen or an alkyl group in
본 명세서에서 "염" 또는 "약학적으로 허용 가능한 염"은 약학적으로 허용 가능하고 모 화합물(parent compound)의 바람직한 약리 활성을 갖는 본 명세서의 일 측면에 따른 염을 의미한다. 무기산 또는 유기산 또는 무기 염기 또는 유기 염기로 형성된 통상적인 염 및 4급 암모늄의 산부가염을 포함한다. 상기 염은 (1) 염산, 브롬화수소산, 황산, 질산, 인산 등과 같은 무기산으로 형성되거나; 또는 아세트산, 프로파이온산, 헥사노산, 시클로펜테인프로피온산, 글라이콜산, 피루브산, 락트산, 말론산, 숙신산, 말산, 말레산, 푸마르산, 타르타르산, 시트르산, 벤조산, 3-(4-히드록시벤조일) 벤조산, 신남산, 만델산, 메테인설폰산, 에테인설폰산, 1,2-에테인-디설폰산, 2-히드록시에테인설폰산, 벤젠설폰산, 4-클로로벤젠설폰산, 2-나프탈렌설폰산, 4-톨루엔설폰산, 캄퍼설폰산, 4-메틸바이시클로 [2,2,2]-oct-2-엔-1-카르복실산, 글루코헵톤산, 3-페닐프로파이온산, 트리메틸아세트산, tert-부틸아세트산, 라우릴 황산, 글루콘산, 글루탐산, 히드록시나프토산, 살리실산, 스테아르산, 뮤콘산과 같은 유기산으로 형성되는 산 부가염(acid addition salt); 또는 (2) 모 화합물에 존재하는 산성 프로톤이 치환될 때 형성되는 염을 포함할 수 있다. 적절한 염기 염의 더욱 특정한 예는 나트륨, 리튬, 칼륨, 마그네슘, 알루미늄, 칼슘, 아연, N,N'-디벤질에틸렌디아민, 클로로프로카인, 콜린, 디에탄올아민, 에틸렌디아민, N-메틸글루코사민 및 프로카인의 염을 포함한다.In the present specification, "salt" or "pharmaceutically acceptable salt" refers to a salt according to one aspect of the present specification, which is pharmaceutically acceptable and has a desirable pharmacological activity of a parent compound. And conventional salts formed with inorganic or organic acids or inorganic or organic bases, and acid addition salts of quaternary ammonium. The salt is (1) formed of an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, or the like; Or acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl) Benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, 4-Toluenesulfonic acid, camphorsulfonic acid, 4-methylbicyclo [2,2,2]-oct-2-ene-1-carboxylic acid, glucoheptonic acid, 3-phenylpropionic acid, trimethylacetic acid, tert -Acid addition salts formed from organic acids such as butyl acetic acid, lauryl sulfuric acid, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, muconic acid; Or (2) a salt formed when an acidic proton present in the parent compound is substituted. More specific examples of suitable base salts are sodium, lithium, potassium, magnesium, aluminum, calcium, zinc, N,N'-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, ethylenediamine, N-methylglucosamine and pro Contains salts of Caine.
본 명세서에서 "약학적으로 허용 가능"이란 통상의 의약적 복용량(medicinal dosage)으로 이용할 때 상당한 독성 효과를 피함으로써, 동물, 더욱 구체적으로는 인간에게 사용할 수 있다는 정부 또는 이에 준하는 규제 기구의 승인을 받을 수 있거나 승인 받거나, 또는 약전에 열거되거나 기타 일반적인 약전으로 인지되는 것을 의미한다.As used herein, "pharmaceutically acceptable" means that it can be used in animals, more specifically in humans, by avoiding significant toxic effects when used in a conventional medicinal dosage. It means available or approved, listed in the pharmacopoeia, or recognized as other general pharmacopoeia.
본 명세서에서 "수화물(hydrate)"은 물이 결합되어 있는 화합물을 의미하며, 물과 화합물 사이에 화학적인 결합력이 없는 내포 화합물을 포함하는 광범위한 개념이다.In the present specification, "hydrate" refers to a compound to which water is bound, and is a broad concept including an inclusion compound having no chemical bonding force between water and the compound.
본 명세서에서 "용매화물"은 용질의 분자나 이온과 용매의 분자나 이온 사이에 생긴 고차의 화합물을 의미한다.In the present specification, "solvate" refers to a high-order compound formed between molecules or ions of a solute and molecules or ions of a solvent.
본 명세서에서 "프로드럭(prodrug)"은 어떤 약물을 화학적으로 변화시켜 물리적, 화학적 성질을 조절한 약물을 의미하며, 그 자체는 생리 활성을 나타내지 않지만 투여 후 체내에서 화학적 혹은 효소의 작용에 의해 원래의 약물로 바뀌어 약효를 발휘할 수 있다. 프로드럭은 투여되면, 대사 과정을 통하여 화학 변환을 통해 활성 약물로 변환된다. 일반적으로, 이러한 프로드럭은 본 명세서에 따른 화합물의 기능적 유도체이고, 생체 내에서 원하는 화합물로 쉽게 변환된다. 예를 들어, 적절한 프로드럭 유도체를 선별하고 제조하는 통상의 방법은 문헌["Design Of Prodrugs", H Bund Saard, Elsevier, 1985]에 기재되어 있다. 이 문헌의 전체 내용은 본원에 참고로 원용된다.In the present specification, "prodrug" refers to a drug in which physical and chemical properties are controlled by chemically changing a drug. It can exert its medicinal effect by changing to a drug of When administered, prodrugs are converted into active drugs through chemical transformation through metabolic processes. In general, these prodrugs are functional derivatives of the compounds according to the present specification, and are easily converted into the desired compounds in vivo. For example, conventional methods for selecting and preparing suitable prodrug derivatives are described in "Design Of Prodrugs", H Bund Saard, Elsevier, 1985. The entire contents of this document are incorporated herein by reference.
"이성질체"란 화학식은 같으나 동일하지는 않은 화합물의 관계를 의미하며, 이러한 이성질체의 종류에는 구조 이성질체, 기하 이성질체, 광학 이성질체 및 입체 이성질체가 있다. 구조 이성질체란, 분자식은 같지만 구조가 달라 다른 성질을 갖는 화합물을 의미하고, 기하 이성질체란, 이중결합으로 연결된 두 원자에 결합된 원자 또는 원자단의 공간적 배치가 다른 이성질체를 의미하고, 입체 이성질체란, 동일한 화학적 구성을 갖지만 공간 중에서 원자 또는 기의 배열의 측면에서 상이한 화합물 의미하고, 광학 이성질체(거울상 이성질체)란, 서로 겹치지 않는 거울상을 갖는 한 화합물의 두 입체이성질체를 의미하며, 부분입체 이성질체란, 둘 이상의 비대칭 중심을 가지고 그것의 분자들이 서로 거울상이 아닌 입체이성질체를 의미한다."Isomer" refers to a relationship between compounds having the same formula but not the same, and types of such isomers include structural isomers, geometric isomers, optical isomers and stereoisomers. Structural isomers refer to compounds having the same molecular formula but different structures and different properties, and geometric isomers refer to isomers having different spatial arrangements of atoms or groups bonded to two atoms connected by double bonds, and stereoisomers refer to the same It refers to compounds having a chemical composition but different in terms of the arrangement of atoms or groups in space, and optical isomers (enantiomers) refer to two stereoisomers of a compound having non-overlapping mirror images, and diastereomers refer to two or more It refers to a stereoisomer that has an asymmetric center and its molecules are not mirror images of each other.
본 명세서에서 "이성질체"는 광학 이성질체(optical isomers)(예를 들면, 본래 순수한 거울상 이성질체(essentially pure enantiomers), 본래 순수한 부분 입체 이성질체(essentially pure diastereomers) 또는 이들의 혼합물)뿐만 아니라, 형태 이성질체(conformation isomers)(즉, 하나 이상의 화학 결합의 그 각도만 다른 이성질체), 위치 이성질체(position isomers)(예컨대, 호변이성체(tautomers)) 또는 기하 이성질체(geometric isomers)(예컨대, 시스-트랜스 이성질체)를 포함한다.As used herein, "isomers" refer to optical isomers (eg, essentially pure enantiomers, essentially pure diastereomers, or mixtures thereof), as well as conformational isomers. isomers) (i.e., isomers that differ only in the angle of one or more chemical bonds), position isomers (e.g. tautomers) or geometric isomers (e.g., cis-trans isomers). .
본 명세서에서 "본래 순수(essentially pure)"란, 예컨대 거울상 이성질체 또는 부분 이성질체와 관련하여 사용한 경우, 거울상 이성질체 또는 부분 이성질체를 예로 들 수 있는 구체적인 화합물이 약 90% 이상, 바람직하게는 약 95% 이상, 보다 바람직하게는 약 97% 이상 또는 약 98% 이상, 보다 더 바람직하게는 약 99% 이상, 보다 더욱 더 바람직하게는 약 99.5% 이상(w/w) 존재하는 것을 의미한다.In the present specification, "essentially pure" means, for example, when used in connection with enantiomers or diaisomers, specific compounds exemplified by enantiomers or diaisomers are at least about 90%, preferably at least about 95%. , More preferably at least about 97% or at least about 98%, even more preferably at least about 99%, and even more preferably at least about 99.5% (w/w).
예시적인 일 구현예에서, 상기 화학식 1의 화합물은 시판되는 것을 이용하거나, 개미취속 식물을 포함하는 천연물로부터 얻어지거나, 또는 유기화학적 합성법으로 합성할 수 있다.In an exemplary embodiment, the compound of
예시적인 일 구현예에서, 상기 화학식 1의 화합물은 개미취속(Aster L.) 식물의 추출물 또는 이의 분획물로부터 분리될 수 있다.In an exemplary embodiment, the compound of
예컨대, 상기 화학식 1의 화합물은 개미취속 식물을 물, 유기용매 또는 이들의 혼합물로 이루어진 추출용매를 가하여 개미취속 식물의 추출물을 수득하는 단계(단계 1); 상기 단계 1에서 수득한 추출물을 분획하여 분획물을 수득하는 단계(단계 2); 및 상기 단계 2에서 수득한 분획물에 대해 실리카겔 크로마토그래피를 수행하여 화학식 1의 화합물을 분리하고 정제하는 단계(단계 3)를 포함하여 제조될 수 있다.For example, the compound of
상기 단계 2에서 분획물은 n-헥산, 에틸아세테이트, n-부탄올 및 물을 이용하여 순차적으로 계통분획하여 얻은 n-헥산 분획물, 에틸아세테이트 분획물, n-부탄올 분획물 및 물 분획물일 수 있다.The fraction in
또한, 상기 단계 2에서 분획물은 헥산, 초산에틸 및 메탄올로 이루어진 군에서 선택되는 1 이상의 유출용매를 이용하여 수득한 분획물일 수 있다.In addition, the fraction in
상기 단계 3에서 실리카겔 크로마토그래피는 크기배제 크로마토그래피용 컬럼을 사용하여 수행될 수 있으며, 바람직하게는 세파덱스 LH-20을 충진한 컬럼을 사용할 수 있다. 상기 단계 2에서 수득한 분획물에 대하여 100% 메탄올을 이동상으로 하여 세파덱스 LH-20 컬럼을 이용한 실리카겔 크로마토그래피를 수행할 수 있다. 이때, 수득한 분획물에 대하여 고속액체 크로마토그래피를 수행하여 화학식 1의 화합물을 분리할 수 있다.In step 3, silica gel chromatography may be performed using a column for size exclusion chromatography, and preferably a column filled with Sephadex LH-20 may be used. The fraction obtained in
상기 고속액체 크로마토그래피는 20 부피%에서 30 부피%, 25 부피%에서 40 부피%, 25 부피% 아세토니트릴로 농도 구배된 물과 아세토니트릴의 혼합용매를 전개용매로 사용하여 수행될 수 있다. 이때, 상기 이동상의 유속은 2 내지 15 ㎖/분인 것이 바람직하고, 수행 시간은 0.5 내지 1 시간인 것이 바람직하다.The high performance liquid chromatography may be performed using a mixed solvent of water and acetonitrile in a concentration gradient from 20% by volume to 30% by volume, from 25% by volume to 40% by volume, and from 25% by volume acetonitrile as a developing solvent. At this time, the flow rate of the mobile phase is preferably 2 to 15 ml/min, and the execution time is preferably 0.5 to 1 hour.
예시적인 일 구현예에서, 상기 화학식 1의 화합물은 조성물 전체 중량을 기준으로 0.0001 내지 10 중량%로 포함되는 것일 수 있다. 화학식 1의 화합물이 조성물 내 상기 범위로 포함됨으로써, 다른 함유 물질들과의 적절한 조성비를 갖고 우수한 항노화 효능을 나타내는 효과가 있으며, 경제성 및 효율성 면에서도 바람직할 수 있다. 구체적으로 상기 화학식 1의 화합물은 조성물 전체 중량을 기준으로 0.0005 내지 10 중량%, 또는 0.001 내지 10 중량%, 또는 0.005 내지 10 중량%, 또는 0.01 내지 10 중량%, 또는 0.01 내지 8 중량%, 또는 0.01 내지 6 중량%, 또는 0.01 내지 4 중량%로 포함되는 것일 수 있다.In an exemplary embodiment, the compound of
본 명세서에서 "항노화용"은 유전적 요인 등을 포함하는 내적 요인과 자외선 등을 포함하는 외적 요인에 의해 발생하는 노화 현상을 예방, 지연 또는 개선하는 용도를 의미한다. 예를 들어, 노화에 따른 피부 변화 현상, 예컨대 피부 탄력 감소, 주름 생성, 주름의 깊이나 수의 증가, 건조함 등의 현상을 예방, 지연시키거나 개선, 완화하는 것을 의미한다.In the present specification, "anti-aging" refers to a use of preventing, delaying, or improving aging caused by internal factors including genetic factors and external factors including ultraviolet rays. For example, it means preventing, delaying, improving, or alleviating phenomena of skin changes caused by aging, such as reduction of skin elasticity, wrinkle formation, increase in the depth or number of wrinkles, and dryness.
예시적인 일 구현예에서, 상기 조성물은 광노화에 대한 항노화용 조성물일 수 있다.In an exemplary embodiment, the composition may be a composition for anti-aging against photoaging.
예시적인 일 구현예에서, 상기 조성물은 피부 주름을 개선하거나, 또는 피부 탄력을 증진시키는 항노화용 조성물일 수 있다. 구체적으로, 상기 조성물은 주름의 생성 시기를 가능한 늦추어 주름 생성을 예방 또는 방지하거나, 이미 생성된 주름을 완화 또는 개선하는 효과가 있다. 또한, 상기 조성물은 피부 탄력 감소를 예방 또는 방지하거나, 피부 탄력을 증진 또는 개선하는 효과가 있다.In an exemplary embodiment, the composition may be an anti-aging composition that improves skin wrinkles or improves skin elasticity. Specifically, the composition has an effect of preventing or preventing wrinkle formation by delaying the generation time of wrinkles as much as possible, or alleviating or improving wrinkles that have already been created. In addition, the composition has an effect of preventing or preventing a decrease in skin elasticity, or promoting or improving skin elasticity.
상기 조성물은 콜라겐 분해효소(Collagenase)의 발현을 억제하거나 또는 본 명세서의 조성물에 의해 미미하게 발현된 콜라겐 분해효소의 활성을 저해할 수 있다. 다른 측면에서, 상기 조성물은 콜라겐 분해효소(Collagenase)의 발현 또는 활성을 저해하는 상위(up-stream)의 효소 또는 단백질과 같은 물질에도 특정 효과를 가져올 수 있다.The composition may inhibit the expression of collagenase or may inhibit the activity of a collagenase that is slightly expressed by the composition of the present specification. In another aspect, the composition may have a specific effect on substances such as up-stream enzymes or proteins that inhibit the expression or activity of collagenase.
상기 조성물은 콜라겐의 발현을 촉진시키거나 이의 활성을 증진시킬 수 있다. 다른 측면에서, 상기 조성물은 콜라겐의 발현 또는 활성을 증가시키는 상위(up-stream)의 효소 또는 단백질과 같은 물질에도 특정 효과를 가져올 수 있다.The composition may promote the expression of collagen or enhance its activity. In another aspect, the composition may have a specific effect on substances such as up-stream enzymes or proteins that increase the expression or activity of collagen.
예시적인 일 구현예에서, 상기 항노화용 조성물은 약학 조성물일 수 있다.In an exemplary embodiment, the anti-aging composition may be a pharmaceutical composition.
본 명세서에서 약학 조성물은 피부 외용제 조성물을 포함하는 것일 수 있다. 약학 조성물의 제형은 용액제, 현탁제, 유액제, 겔제, 점적제, 좌제(坐劑), 크림제, 연고제, 패취제, 패드제 또는 분무제일 수 있으나, 이에 제한되는 것은 아니다. 상기 제형은 당해 분야의 통상적인 방법에 따라 용이하게 제조될 수 있으며, 부형제, 수화제, 유화 촉진제, 현탁제, 삼투압 조절을 위한 염 또는 완충제, 착색제, 향신료, 안정화제, 방부제, 보존제 또는 기타 상용하는 보조제를 적당히 사용할 수 있다.In the present specification, the pharmaceutical composition may include a composition for external application for skin. The formulation of the pharmaceutical composition may be a solution, a suspension, an emulsion, a gel, a drop, a suppository, a cream, an ointment, a patch, a pad, or a spray, but is not limited thereto. The formulation can be easily prepared according to conventional methods in the art, and excipients, hydrating agents, emulsification accelerators, suspending agents, salts or buffers for controlling the osmotic pressure, coloring agents, spices, stabilizers, preservatives, preservatives or other compatible Adjuvants can be used in moderation.
또한, 약학 조성물은 목적하는 방법에 따라 경구, 비경구, 직장, 국소, 경피, 정맥 내, 근육 내, 복강 내, 피하 등으로 투여할 수 있으며, 약학 조성물의 유효성분은 투여받을 대상의 연령, 성별, 체중, 병리 상태 및 그 심각도, 투여 경로 또는 처방자의 판단에 따라 달라질 것이다. 이러한 인자에 기초한 적용량 결정은 당업자의 수준 내에 있으며, 이의 1일 투여 용량은 예를 들어 0.1 mg/g/일 내지 100 mg/g/일, 보다 구체적으로는 5 mg/g/일 내지 50 mg/g/일이 될 수 있으나, 이에 제한되는 것은 아니다.In addition, the pharmaceutical composition may be administered orally, parenteral, rectal, topical, transdermal, intravenous, intramuscular, intraperitoneal, subcutaneous, etc. according to a desired method, and the active ingredient of the pharmaceutical composition is the age of the subject to be administered, It will depend on sex, weight, pathologic condition and severity, route of administration, or the judgment of the prescriber. Determination of the application amount based on these factors is within the level of those skilled in the art, and its daily dose is, for example, 0.1 mg/g/day to 100 mg/g/day, more specifically 5 mg/g/day to 50 mg/day. It may be g/day, but is not limited thereto.
예시적인 일 구현예에서, 상기 항노화용 조성물은 화장료 조성물일 수 있다.In an exemplary embodiment, the anti-aging composition may be a cosmetic composition.
본 명세서에서 화장료 조성물은 제형이 특별히 한정되지 않으며, 목적하는 바에 따라 적절하게 선택할 수 있다. 예를 들어, 용액, 수상에 유상을 분산시켜 얻은 에멀젼, 유상에 수상을 분산시켜 얻은 에멀젼, 현탁액, 고체, 겔, 분말, 페이스트, 포말(foam) 또는 에어로졸 조성물의 제형으로 제조될 수 있으나, 이에 제한되는 것은 아니다.In the present specification, the formulation of the cosmetic composition is not particularly limited, and may be appropriately selected depending on the intended purpose. For example, it may be prepared in the form of a solution, an emulsion obtained by dispersing an oil phase in an aqueous phase, an emulsion obtained by dispersing an aqueous phase in an oil phase, a suspension, a solid, a gel, a powder, a paste, a foam, or an aerosol composition. It is not limited.
또한, 화장료 조성물은 상기한 물질 이외에 주 효과를 손상시키지 않는 범위 내에서, 바람직하게는 주 효과에 상승 효과를 줄 수 있는 다른 성분들을 더 포함할 수 있다. 또한 상기 화장료 조성물은 지방 물질, 유기용매, 용해제, 농축제, 겔화제, 연화제, 항산화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온봉쇄제, 킬레이트화제, 보존제, 비타민, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 지질 소낭 또는 화장품에 통상적으로 사용되는 임의의 다른 성분과 같은 화장품학 또는 피부과학 분야에서 통상적으로 사용되는 보조제를 포함할 수 있다. 상기 성분의 배합량은 본 명세서의 목적 및 효과를 손상시키지 않는 범위 내에서 당업자가 용이하게 선정하여 사용할 수 있으며, 그 배합량은 조성물 전체 중량을 기준으로 0.01 내지 5 중량%, 또는 0.01 내지 3 중량%일 수 있다.In addition, the cosmetic composition may further include other ingredients capable of giving a synergistic effect to the main effect within a range that does not impair the main effect in addition to the above-described substances. In addition, the cosmetic composition is a fatty substance, an organic solvent, a solubilizing agent, a thickening agent, a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, a surfactant, water, an ionic or nonionic emulsifier. , Fillers, sequestrants, chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic actives, lipid vesicles or any other ingredients commonly used in cosmetics, such as cosmetic or It may contain adjuvants commonly used in the field of dermatology. The blending amount of the ingredients can be easily selected and used by a person skilled in the art within a range that does not impair the purpose and effect of the present specification, and the blending amount is 0.01 to 5% by weight, or 0.01 to 3% by weight based on the total weight of the composition. I can.
예시적인 일 구현예에서, 상기 조성물은 식품 조성물일 수 있다.In one exemplary embodiment, the composition may be a food composition.
본 명세서에서 식품 조성물은 다양한 형태의 식품 첨가제 또는 기능성 식품을 제공한다. 구체적으로, 상기 조성물을 포함하는 침출차, 액상차, 음료, 발효유, 치즈, 요구르트, 주스, 생균제제 또는 건강보조식품 등으로 가공될 수 있으며, 그 외 다양한 식품 첨가제의 형태로 사용될 수 있다.In the present specification, the food composition provides various types of food additives or functional foods. Specifically, it may be processed into leached tea, liquid tea, beverages, fermented milk, cheese, yogurt, juice, probiotics, health supplements, etc. including the composition, and may be used in the form of various other food additives.
또한, 식품 조성물은 유효성분이 목적으로 하는 주 효과를 손상시키지 않는 범위 내에서 주 효과에 상승 효과를 줄 수 있는 다른 성분 등을 더 포함할 수 있다. 예를 들어, 물성 개선을 위하여 향료, 색소, 살균제, 산화 방지제, 방부제, 보습제, 점증제, 무기염류, 유화제 및 합성 고분자 물질 등의 첨가제를 더 포함할 수 있다. 그 외에도, 수용성 비타민, 유용성 비타민, 고분자 펩티드, 고분자 다당 및 해초 엑기스 등의 보조성분을 더 포함할 수 있다. 상기 성분들은 제형 또는 사용 목적에 따라 당업자가 어려움 없이 적의 선정하여 배합할 수 있으며, 그 첨가량은 본 명세서의 목적 및 효과를 손상시키지 않는 범위 내에서 선택될 수 있다. 예를 들어, 상기 성분들의 첨가량은 조성물 전체 중량을 기준으로, 0.01 내지 5 중량%, 또는 0.01 내지 3 중량% 범위일 수 있다.In addition, the food composition may further include other ingredients that can give a synergistic effect to the main effect within a range in which the active ingredient does not impair the intended main effect. For example, additives such as fragrances, pigments, disinfectants, antioxidants, preservatives, moisturizers, thickeners, inorganic salts, emulsifiers, and synthetic polymer substances may be further included in order to improve physical properties. In addition, auxiliary components such as water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymer polysaccharides, and seaweed extract may be further included. The above ingredients may be appropriately selected and blended by a person skilled in the art according to the formulation or purpose of use, and the amount added may be selected within a range that does not impair the purpose and effect of the present specification. For example, the amount of the components added may range from 0.01 to 5% by weight, or from 0.01 to 3% by weight, based on the total weight of the composition.
이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 예시하기 위한 것으로서, 본 발명의 범위가 이들 실시예에 의해 제한되는 것으로 해석되지 않는 것은 당업계에서 통상의 지식을 가진 자에게 있어서 자명할 것이다.Hereinafter, the present invention will be described in more detail through examples. These examples are for illustrative purposes only, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not construed as being limited by these examples.
실시예 1. 개미취속(Example 1. Ant odor ( AsterAster L.) 식물의 추출물 및 분획물 제조 L.) Preparation of plant extracts and fractions
본 실시예에서는 개미취속(Aster L.) 식물로 벌개미취(Aster koraiensis NaKai)를 4월 중순(어린순)과 8월 중순(성체)에 강원도 평창 등지에서 채집하여 이용하였다. 건조된 벌개미취를 세절한 후 벌개미취 180 g에 2 L의 에탄올을 가하고 3시간 동안 가온 환류 추출한 후 추출액을 여과하였다. 추출액을 여과한 후 남은 잔사에 다시 2 L의 에탄올을 가하고 3시간 동안 가온 환류 추출하는 방법을 추가로 2회 반복하여 총 추출액 6 L를 수득하였다. 상기 추출액 6 L를 35 ℃에서 감압 농축하여 에탄올 추출물 8.5 g을 수득하였다. In this example, bee ants (Aster koraiensis NaKai) as a plant of the genus Aster L. were collected and used in mid-April (young) and mid-August (adult) in Pyeongchang, Gangwon-do. After the dried bee ant odor was minced, 2 L of ethanol was added to 180 g of bee ant odor, followed by heating under reflux extraction for 3 hours, and the extract was filtered. After filtering the extract, 2 L of ethanol was added to the remaining residue, and the method of heating under reflux extraction for 3 hours was repeated two more times to obtain a total of 6 L of the extract. 6 L of the extract was concentrated under reduced pressure at 35° C. to obtain 8.5 g of an ethanol extract.
또한, 상기 벌개미취 에탄올 추출물을 분별깔때기를 이용하여 n-헥산, 에틸아세테이트, n-부탄올 및 물로 순차적으로 분획하였으며, 그 결과 n-헥산 분획물(0.94g), 에틸아세테이트 분획물(1.74g), n-부탄올 분획물(1.86g) 및 물 분획물(2.2g)을 얻을 수 있었다. In addition, the ethanol extract of beehive odor was sequentially fractionated into n-hexane, ethyl acetate, n-butanol and water using a separatory funnel, and as a result, n-hexane fraction (0.94 g), ethyl acetate fraction (1.74 g), n- A butanol fraction (1.86 g) and a water fraction (2.2 g) were obtained.
상기 제조된 추출물과 분획물은 디메틸설폭사이드(Dimethyl sulfoxide; DMSO)에 녹인 후, 하기 실험에 이용하였다.The prepared extracts and fractions were dissolved in dimethyl sulfoxide (DMSO) and used in the following experiments.
실시예 2. 화합물들의 분리 및 동정Example 2. Isolation and identification of compounds
상기 실시예 1에서 수득한 벌개미취의 에탄올 추출물 5.8 g을 85 g의 C-18 역상 수지로 충진된 감압 컬럼 크로마토그래피를 이용하여 하기 여섯 개의 분획물을 수득하였다. 용리 조건은 헥산, 초산에틸 및 메탄올을 사용하였으며, 헥산/초산에틸(10:1(v/v)) 400 mL로 시작하여 헥산/초산에틸(5:1(v/v)) 400 mL, 헥산/초산에틸(2:1(v/v)) 400 mL, 헥산/초산에틸(1:1(v/v)) 400 mL, 초산에틸 400 mL 및 메탄올 400 mL를 유출용매로 사용하였다. 수득한 분획물들 중 헥산/초산에틸(5:1) 분획물 및 헥산/초산에틸(2:1) 분획물을 합하여 400 mg의 혼합 분획물을 제조하였고, 이 혼합 분획물 중 200 mg으로 65% 아세토니트릴/물을 유출용매로 사용한 고속액체크로마토그래피법을 이용하여(컬럼 21 mm × 250 mm; 유속 10 mL/min) 주성분을 분리한 결과, 화학식 2로 표시되는 짐나스테르코리아인 B(9 mg), 화학식 3로 표시되는 짐나스테르코리아인 C(2 mg), 화학식 4로 표시되는 짐나스테르코리아인 E(0.5 mg) 및 화학식 5로 표시되는 1,8,15-헵타데카트리엔-11,13-디인-10-올(1 mg)을 수득하였다.The following six fractions were obtained by using reduced pressure column chromatography filled with 5.8 g of the ethanol extract of beehive odor obtained in Example 1 with 85 g of C-18 reverse phase resin. Elution conditions were hexane, ethyl acetate and methanol, starting with 400 mL of hexane/ethyl acetate (10:1 (v/v)), 400 mL of hexane/ethyl acetate (5:1 (v/v)), hexane 400 mL of /ethyl acetate (2:1 (v/v)), 400 mL of hexane/ethyl acetate (1:1 (v/v)), 400 mL of ethyl acetate, and 400 mL of methanol were used as effluent solvents. Of the obtained fractions, the hexane/ethyl acetate (5:1) fraction and the hexane/ethyl acetate (2:1) fraction were combined to prepare a mixed fraction of 400 mg, and 200 mg of the mixed fraction was 65% acetonitrile/water. As a result of separating the main component by high-speed liquid chromatography using as the effluent solvent (column 21 mm × 250 mm;
상기 화합물들의 구조 분석을 위하여, 하기와 같이 NMR 분석 및 질량 분석을 실시하였다. 분자량 및 분자식은 Agilent 1100 고속유체크로마토그래피-질량 분광계(HPLC-ESI-MS)를 이용한 MS 측정을 통하여 결정하였으며, 핵자기공명기(Varian 500㎒ NMR)을 이용한 1H, 13C-NMR 스펙트럼(spectrum) 분석을 통하여 그 구조를 하기 화학식 2 내지 5와 같이 동정하였다. 분석 결과는 다음과 같다.For structural analysis of the compounds, NMR analysis and mass spectrometry were performed as follows. Molecular weight and molecular formula were determined through MS measurement using an Agilent 1100 high-speed fluid chromatography-mass spectrometer (HPLC-ESI-MS), and 1 H, 13 C-NMR spectrum using a nuclear magnetic resonance (Varian 500㎒ NMR). ) Through the analysis, the structure was identified as shown in the following
[화학식 2][Formula 2]
짐나스테르코리아인 B :Jim Naster Korean B:
미황색 액상 화합물;Pale yellow liquid compound;
분자식 C17H22O2; UV λmax 200, 237, 251, 266 nm; ESI-MS m/z 281 [M+Na]+;Molecular formula C 17 H 22 O 2 ; UV λmax 200, 237, 251, 266 nm; ESI-MS m/z 281 [M+Na] + ;
1H NMR(500 MHz, CDCl3) δ 5.81 (1H, ddt, J = 17.0, 10.5, 7.0 Hz, H-2), 5.62 (1H, dtd, J = 10.0, 7.5, 1.0 Hz, H-8), 5.51 (1H, ddt, J = 10.0, 8.5, 1.5 Hz, H-9), 5.19 (1H, br d, J = 8.5 Hz, H-10), 5.01 (1H, ddt, J = 17.0, 2.0, 2.0 Hz, H-1trans), 4.95 (1H, ddt, J = 10.5, 2.0, 1.0 Hz, H-1cis), 3.19 (1H, qd, J = 5.0, 2.0 Hz, H-16), 3.13 (1H, d, J = 2.0 Hz, H-15), 2.12 (2H, dtd, J = 7.0, 7.0, 1.0 Hz, H2-7), 2.05 (2H, dt br t J =7.0, 7.0, 1.0 Hz, H2-3), 1.85 (1H, br s, 10-OH), 1.37-1.42 (4H, m, H2-4, H2-6), 1.31-1.35 (2H, m, H2-5), 1.35 (3H, d, J = 5.0 Hz, H-17). 1 H NMR (500 MHz, CDCl 3 ) δ 5.81 (1H, ddt, J = 17.0, 10.5, 7.0 Hz, H-2), 5.62 (1H, dtd, J = 10.0, 7.5, 1.0 Hz, H-8) , 5.51 (1H, ddt, J = 10.0, 8.5, 1.5 Hz, H-9), 5.19 (1H, br d, J = 8.5 Hz, H-10), 5.01 (1H, ddt, J = 17.0, 2.0, 2.0 Hz, H-1 trans ), 4.95 (1H, ddt, J = 10.5, 2.0, 1.0 Hz, H-1 cis ), 3.19 (1H, qd, J = 5.0, 2.0 Hz, H-16), 3.13 ( 1H, d, J = 2.0 Hz, H-15), 2.12 (2H, dtd, J = 7.0, 7.0, 1.0 Hz, H 2 -7), 2.05 (2H, dt br t J =7.0, 7.0, 1.0 Hz , H 2 -3), 1.85 (1H, broad singlet, 10-OH), 1.37-1.42 (4H, m, H 2 -4, H 2 -6), 1.31-1.35 (2H, m, H 2 -5 ), 1.35 (3H, d, J = 5.0 Hz, H-17).
[화학식 3][Formula 3]
짐나스테르코리아인 C :Jim Naster Korean C:
미황색 액상 화합물;Pale yellow liquid compound;
분자식 C19H24O3; UV λmax 200, 235, 248, 260 nm; ESI-MS m/z 323 [M+Na]+;Molecular formula C 19 H 24 O 3 ; UV λmax 200, 235, 248, 260 nm; ESI-MS m/z 323 [M+Na] + ;
1H NMR(500 MHz, CDCl3) δ 5.93 (1H, d, J = 6.0 Hz, H-15), 5.88 (1H, dddd, J = 17.0, 10.0, 6.0, 1.0 Hz, H-16), 5.82 (1H, ddtd, J = 17.0, 10.0, 7.0, 1.0 Hz, H-2), 5.62 (1H, dt br t, J = 10.5, 7.5, 1.0 Hz, H-8), 5.55 (1H, d, J = 17.0 Hz, H2-17trans), 5.23 (1H, dd br t, J = 10.5, 8.5, 1.0 Hz, H-9), 5.36 (1H, d, J = 10.0, H2-17cis), 5.21 (1H, d br d, J = 8.5, 1.0 Hz, H-10), 5.01 (1H, d br dt, J = 17.0, 1.5, 1.0 Hz, H2-1trans), 4.95 (1H, ddt, J = 10.0, 1.0, 1.0 Hz, H2-1cis), 2.12 (2H, dtd, J = 8.5, 7.5, 1.0 Hz, H2-7), 2.11 (3H, s, CH3CO), 2.06 (2H, dtd, J = 7.0, 7.0, 1.0 Hz, H2-3), 1.37-1.44 (4H, m, H2-4, H2-6), 1.31-1.35 (2H, m, H2-5). 1 H NMR (500 MHz, CDCl 3 ) δ 5.93 (1H, d, J = 6.0 Hz, H-15), 5.88 (1H, dddd, J = 17.0, 10.0, 6.0, 1.0 Hz, H-16), 5.82 (1H, ddtd, J = 17.0, 10.0, 7.0, 1.0 Hz, H-2), 5.62 (1H, dt br t, J = 10.5, 7.5, 1.0 Hz, H-8), 5.55 (1H, d, J = 17.0 Hz, H 2 -17 trans ), 5.23 (1H, dd br t, J = 10.5, 8.5, 1.0 Hz, H-9), 5.36 (1H, d, J = 10.0, H 2 -17 cis ), 5.21 (1H, d br d, J = 8.5, 1.0 Hz, H-10), 5.01 (1H, d br dt, J = 17.0, 1.5, 1.0 Hz, H 2 -1 trans ), 4.95 (1H, ddt, J = 10.0, 1.0, 1.0 Hz, H 2 -1 cis ), 2.12 (2H, dtd, J = 8.5, 7.5, 1.0 Hz, H 2 -7), 2.11 (3H, s, CH 3 CO), 2.06 ( 2H, dtd, J = 7.0, 7.0, 1.0 Hz, H 2 -3), 1.37-1.44 (4H, m, H 2 -4, H 2 -6), 1.31-1.35 (2H, m, H 2 -5 ).
[화학식 4][Formula 4]
짐나스테르코리아인 E :Jim Naster Korean E:
미황색 액상 화합물;Pale yellow liquid compound;
분자식 C17H24O3; UV λmax 200, 237, 251, 265 nm; ESI-MS m/z 299 [M+Na]+;Molecular formula C 17 H 24 O 3 ; UV λmax 200, 237, 251, 265 nm; ESI-MS m/z 299 [M+Na] + ;
1H NMR(500 MHz, CDCl3) δ 5.82 (1H, ddt, J = 17.0, 10.5, 7.0 Hz, H-2), 5.63 (1H, dt br d, J = 10.0, 7.0, 1.0 Hz, H-8), 5.53 (1H, ddt, J = 10.0, 8.0, 1.5 Hz, H-9), 5.22 (1H, d br t, J = 8.0, 1.0 Hz, H-10), 5.01 (1H, ddt, J = 17.0, 2.0, 2.0 Hz, H2-1trans), 4.95 (1H, ddt, J = 10.5, 2.0, 1.5 Hz, H2-1cis), 4.62 (1H, dd, J = 4.0, 0.5 Hz, H-15), 4.05 (1H, qdd, J = 6.5, 4.0, 1.5 Hz, H-16), 2.14 (2H, dt, J = 7.0, 6.5 Hz, H2-7), 2.05 (2H, dt, J =7.0, 7.0 Hz, H2-3), 1.32-1.44 (6H, m, H2-4, H2-5, H2-6), 1.35 (3H, d, J = 6.5 Hz, H3-17). 1 H NMR (500 MHz, CDCl 3 ) δ 5.82 (1H, ddt, J = 17.0, 10.5, 7.0 Hz, H-2), 5.63 (1H, dt br d, J = 10.0, 7.0, 1.0 Hz, H- 8), 5.53 (1H, ddt, J = 10.0, 8.0, 1.5 Hz, H-9), 5.22 (1H, d br t, J = 8.0, 1.0 Hz, H-10), 5.01 (1H, ddt, J = 17.0, 2.0, 2.0 Hz, H 2 -1 trans ), 4.95 (1H, ddt, J = 10.5, 2.0, 1.5 Hz, H 2 -1 cis ), 4.62 (1H, dd, J = 4.0, 0.5 Hz, H-15), 4.05 (1H, qdd, J = 6.5, 4.0, 1.5 Hz, H-16), 2.14 (2H, dt, J = 7.0, 6.5 Hz, H 2 -7), 2.05 (2H, dt, J =7.0, 7.0 Hz, H 2 -3), 1.32-1.44 (6H, m, H 2 -4, H 2 -5, H 2 -6), 1.35 (3H, d, J = 6.5 Hz, H 3 -17).
[화학식 5][Formula 5]
1,8,15-헵타데카트리엔-11,13-디인-10-올 :1,8,15-heptadecatrien-11,13-diin-10-ol:
미황색 액상 화합물;Pale yellow liquid compound;
분자식 C17H22O; UV λmax 217, 240, 255, 269, 284 nm; ESI-MS m/z 265 [M+Na]+;Molecular formula C 17 H 22 O; UV λmax 217, 240, 255, 269, 284 nm; ESI-MS m/z 265 [M+Na] + ;
1H NMR(500 MHz, CDCl3) δ 6.34 (1H, dq, J = 15.5, 6.5 Hz, H-16), 5.82 (1H, ddt, J = 17.0, 10.0, 8.0 Hz, H-2), 5.61 (1H, dt, J = 10.5, 7.5 Hz, H-8), 5.54 (1H, br d, J = 15.5 Hz, H-15), 5.54 (1H, dd br t, J = 10.5, 8.5, 1.5 Hz, H-9), 5.24 (1H, d, J = 8.5 Hz, H-10), 5.01 (1H, ddt, J = 17.0, 1.5, 1.5 Hz, H2-1trans), 4.95 (1H, ddt, J = 10.0, 2.0, 1.5 Hz, H2-1cis), 2.13 (2H, dtd, J = 7.5, 7.0, 1.0 Hz, H2-7), 2.06 (2H, dt, J = 7.0, 7.0 Hz, H2-3), 1.83 (3H, dd, J = 6.5, 2.0 Hz, H3-17), 1.34-1.43 (4H, m, H2-4, H2-6), 1.23-1.33 (2H, m, H2-5). 1 H NMR (500 MHz, CDCl 3 ) δ 6.34 (1H, dq, J = 15.5, 6.5 Hz, H-16), 5.82 (1H, ddt, J = 17.0, 10.0, 8.0 Hz, H-2), 5.61 (1H, dt, J = 10.5, 7.5 Hz, H-8), 5.54 (1H, br d, J = 15.5 Hz, H-15), 5.54 (1H, dd br t, J = 10.5, 8.5, 1.5 Hz , H-9), 5.24 (1H, d, J = 8.5 Hz, H-10), 5.01 (1H, ddt, J = 17.0, 1.5, 1.5 Hz, H 2 -1 trans ), 4.95 (1H, ddt, J = 10.0, 2.0, 1.5 Hz, H 2 -1 cis ), 2.13 (2H, dtd, J = 7.5, 7.0, 1.0 Hz, H 2 -7), 2.06 (2H, dt, J = 7.0, 7.0 Hz, H 2 -3), 1.83 (3H, dd, J = 6.5, 2.0 Hz, H 3 -17), 1.34-1.43 (4H, m, H 2 -4, H 2 -6), 1.23-1.33 (2H, m, H 2 -5).
실험예 1. 콜라겐 분해효소-1 분비량 억제 Experimental Example 1. Inhibition of the secretion of collagen-degrading enzyme-1
상기 <실시예 >1 내지 <실시예 2>를 통해 얻은 벌개미취 추출물 및 짐나스테르코리아인 B 각각에 대해 콜라겐 분해효소-1(Matrix Metalloproteinase-1, MMP-1)의 분비량 억제 효능을 측정하였다. 양성 대조군으로는 Epigallocatechin gallate (EGCG, Sigma, USA) 10 μM 농도를 사용하였다.The effect of inhibiting secretion of collagen degrading enzyme-1 (Matrix Metalloproteinase-1, MMP-1) was measured for each of the extracts of bee gill taste and Jimnaster Koreain B obtained through the <Examples> 1 to <Example 2>. Epigallocatechin gallate (EGCG, Sigma, USA) 10 μM concentration was used as a positive control.
먼저, 2.5%의 우태아 혈청이 함유된 DMEM(Dulbecco's Modified Eagle's Media) 배지가 들어 있는 24-공 평판배양기(24-well microtiter plate)에 인간의 섬유아세포를 1×105 세포/공(well)이 되도록 넣고, 90% 정도 자랄 때까지 배양하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>를 통해 얻은 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 1시간 동안 처리한 후, DPBS로 워싱한 다음, UV조사기를 이용하여 15 mJ을 조사하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 추가로 처리하였다. 24시간 경과한 다음 세포배양액을 채취하여 원심분리하고 상등액만 수득하였다. First, 1×10 5 cells/well of human fibroblasts in a 24-well microtiter plate containing DMEM (Dulbecco's Modified Eagle's Media) medium containing 2.5% fetal bovine serum. Put so as to be, and cultured until about 90% growth. Thereafter, 5, 10, 20 μg/ml of the ethanol extract obtained through <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, and 5, 10, 20 μM of Jimnaster Koreain B , And EGCG was treated at a concentration of 10 μM for 1 hour, washed with DPBS, and then irradiated with 15 mJ using a UV irradiator. Thereafter, 5, 10, 20 μg/ml of the ethanol extracts of bee ant odor of <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, 5, 10, 20 μM of Jimnaster Koreain B, and EGCG was further treated at a concentration of 10 μM. After 24 hours, the cell culture solution was collected, centrifuged, and only the supernatant was obtained.
이후, 채취한 상등액으로부터 콜라겐 분해효소-1 측정 키트(QIA55, Merch & Co., 미국)를 이용하여 콜라겐 분해효소-1 생성 정도를 측정하였다. 먼저, 콜라겐 분해효소 1차 항체가 균일하게 도포된 96-공 평판(96-well plate)에 채취된 상기 세포배양액을 넣고 2시간 동안 항원-항체 반응을 상온에서 실시하였다. 2시간 후 발색단이 결합된 1차 콜라겐 항체를 96-공 평판(96-well plate)에 넣고 1시간 동안 반응시켰다. 1시간 후 발색유발물질을 넣어 실온에서 30분간 발색을 유발시킨 후 다시 종결버퍼를 넣어 반응(발색)을 중지시킨 결과, 반응액의 색깔은 노란색을 띄며 반응 진행의 정도에 따라 노란색의 정도가 다르게 나타났다. 노란색을 띠는 96-공 평판(96-well plate)의 흡광도를 흡광계를 이용하여 450/540 nm에서 측정하였다.Thereafter, the degree of collagenase-1 production was measured using a collagenase-1 assay kit (QIA55, Merch & Co., USA) from the collected supernatant. First, the collected cell culture solution was added to a 96-well plate uniformly coated with a primary collagenase antibody, and an antigen-antibody reaction was performed at room temperature for 2 hours. After 2 hours, the primary collagen antibody to which the chromophore was bound was placed in a 96-well plate and reacted for 1 hour. After 1 hour, a color-producing substance was added to induce color development at room temperature for 30 minutes, and then the reaction (color development) was stopped by adding a terminating buffer.As a result, the color of the reaction solution is yellow and the degree of yellow is different depending on the progress of the reaction. appear. The absorbance of a yellow 96-well plate was measured at 450/540 nm using an absorbance meter.
그 결과, 도 1에서 보는 바와 같이 벌개미취 추출물 및 짐나스테르코리아인 B 각각은 농도 의존적으로 콜라겐 분해효소-1의 분비량을 현저하게 억제하는 것을 확인할 수 있었다.As a result, as shown in FIG. 1, it was confirmed that each of the extract of bee ants and jimnaster Koreain B significantly suppressed the secretion of collagen-degrading enzyme-1 in a concentration-dependent manner.
실험예 2. 타입-1 프로콜라겐(Type-1 procollagen) 분비량 증가Experimental Example 2. Increasing the amount of secretion of type-1 procollagen
상기 <실시예 1> 내지 <실시예 2>를 통해 얻은 벌개미취 추출물 및 짐나스테르코리아인 B 각각에 대해 타입-1 프로콜라겐(Type-1 procollagen)의 분비량 증가 효능을 측정하였다. 양성 대조군으로는 EGCG 10 μM 농도를 사용하였다.The effect of increasing the secretion amount of type-1 procollagen was measured for each of the bee ant odor extract and Jim Naster Koreain B obtained through the <Example 1> to <Example 2>.
먼저, 2.5%의 우태아 혈청이 함유된 DMEM(Dulbecco's Modified Eagle's Media) 배지가 들어 있는 24-공 평판배양기(24-well microtiter plate)에 인간의 섬유아세포를 1×105 세포/공(well)이 되도록 넣고, 90% 정도 자랄 때까지 배양하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>를 통해 얻은 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 1시간 동안 처리한 후, DPBS로 워싱한 다음, UV조사기를 이용하여 15 mJ을 조사하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 추가로 처리하였다. 24시간 경과한 다음 세포배양액을 채취하여 원심분리하고 상등액만 수확하여, 콜라겐 합성의 지표가 되는 펩타이드(procollagen type-Ⅰ C-peptide, PIP)를 ELISA 키트(MK101, Takara Bio Ink., 일본)를 이용하여 콜라겐 생성에 미치는 영향을 정량적으로 측정하였다. First, 1×10 5 cells/well of human fibroblasts in a 24-well microtiter plate containing DMEM (Dulbecco's Modified Eagle's Media) medium containing 2.5% fetal bovine serum. Put so as to be, and incubated until about 90% growth. Thereafter, 5, 10, 20 μg/ml of the ethanol extract obtained through <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, and 5, 10, 20 μM of Jimnaster Koreain B , And EGCG was treated at a concentration of 10 μM for 1 hour, washed with DPBS, and then irradiated with 15 mJ using a UV irradiator. Thereafter, 5, 10, 20 μg/ml of the ethanol extracts of bee ant odor of <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, 5, 10, 20 μM of Jimnaster Koreain B, and EGCG was further treated at a concentration of 10 μM. After 24 hours, the cell culture solution was collected, centrifuged, and only the supernatant was harvested. A peptide (procollagen type-I C-peptide, PIP), an indicator of collagen synthesis, was prepared using an ELISA kit (MK101, Takara Bio Ink, Japan) Was used to quantitatively measure the effect on collagen production.
먼저, 프로콜라겐에 대한 마우스 단일클론 항체가 균일하게 도포된 96-공 평판(96-well plate)에 퍼록시다제(peroxidase)로 표지한 항체-PIP 컨쥬게이트를 넣어 반응시켰다. 그 후 채취한 상기 세포배양액을 넣고 37℃ 인큐베이터에서 3시간 동안 반응시키고 기질용액을 넣어 발색시켰다. 실온에서 15분간 방치 후 반응중지용액을 넣어 반응을 중지시키고 흡광계를 이용하여 450 nm에서 흡광도를 측정하였다.First, an antibody-PIP conjugate labeled with peroxidase was added to a 96-well plate uniformly coated with a mouse monoclonal antibody against procollagen and reacted. Then, the collected cell culture solution was added and reacted in an incubator at 37° C. for 3 hours, followed by color development by adding a substrate solution. After allowing to stand at room temperature for 15 minutes, a reaction stopping solution was added to stop the reaction, and absorbance was measured at 450 nm using an absorbance meter.
그 결과, 도 2에서 보는 바와 같이 벌개미취 추출물 및 짐나스테르코리아인 B 각각은 타입-1 프로콜라겐의 생성 및 분비를 촉진시키는 데 뛰어난 효과를 가짐을 알 수 있었다.As a result, as shown in FIG. 2, it was found that each of the bee ant odor extract and Jim Naster Koreain B had excellent effects in promoting the production and secretion of type-1 procollagen.
실험예 3. 콜라겐 분해효소(MMP) 발현량 억제 Experimental Example 3. Inhibition of the expression level of collagen degrading enzyme (MMP)
상기 <실시예 1> 내지 <실시예 2>를 통해 얻은 벌개미취 추출물 및 짐나스테르코리아인 B 각각에 대해 콜라겐 분해효소(Matrix Metalloproteinase, MMP)의 발현량 억제 효능을 측정하였다. 양성 대조군으로는 EGCG 10 μM 농도를 사용하였다.The effect of inhibiting the expression level of collagen-degrading enzyme (Matrix Metalloproteinase, MMP) was measured for each of the extracts of bee gill odor and Jimnaster Koreain B obtained through the <Example 1> to <Example 2>.
먼저, 2.5%의 우태아 혈청이 함유된 DMEM(Dulbecco's Modified Eagle's Media) 배지가 들어 있는 6-공 평판배양기(6-well microtiter plate)에 인간의 각질형성세포를 2×106 세포/공(well)이 되도록 넣고, 90% 정도 자랄 때까지 배양하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>를 통해 얻은 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 1시간 동안 처리한 후, DPBS로 워싱한 다음, UV조사기를 이용하여 15 mJ을 조사하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 추가로 처리하였다. 24시간 경과한 다음 세포로부터 TRIzol 시약(Invitrogen, Carlsbad, CA, USA)을 사용하여 총 RNA를 수확하여 역전사시킨 후, RT-PCR 분석을 다음과 같이 수행하였다. 먼저 cDNA 합성을 위해 상기 RNA를 reverse transcriptase로 역전사시켰다. RT-PCR은 다음의 특정 프라이머로 수행하였다: First, 2×10 6 cells/well of human keratinocytes in a 6-well microtiter plate containing DMEM (Dulbecco's Modified Eagle's Media) medium containing 2.5% fetal bovine serum. ), and incubated until about 90% growth. Thereafter, 5, 10, 20 μg/ml of the ethanol extract obtained through <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, and 5, 10, 20 μM of Jimnaster Koreain B , And EGCG was treated at a concentration of 10 μM for 1 hour, washed with DPBS, and then irradiated with 15 mJ using a UV irradiator. Thereafter, 5, 10, 20 μg/ml of the ethanol extracts of bee ant odor of <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, 5, 10, 20 μM of Jimnaster Koreain B, and EGCG was further treated at a concentration of 10 μM. After 24 hours, total RNA was harvested from the cells using a TRIzol reagent (Invitrogen, Carlsbad, CA, USA) and reverse transcribed, and then RT-PCR analysis was performed as follows. First, for cDNA synthesis, the RNA was reverse transcribed with reverse transcriptase. RT-PCR was performed with the following specific primers:
β-actinβ-actin
Forward primer: 5'-AGCCATGTACGTAGCCATCC-3' (서열번호 1)Forward primer: 5'-AGCCATGTACGTAGCCATCC-3' (SEQ ID NO: 1)
Reverse primer: 5'-CTCTCAGCTGTGGTGGTGAA-3' (서열번호 2)Reverse primer: 5'-CTCTCAGCTGTGGTGGTGAA-3' (SEQ ID NO: 2)
MMP-1MMP-1
Forward primer: 5'-ACAGCTTCCCAGCGACTCTA-3' (서열번호 3)Forward primer: 5'-ACAGCTTCCCAGCGACTCTA-3' (SEQ ID NO: 3)
Reverse primer: 5'-CTCTTGGCAAATCTGGCGTG-3' (서열번호 4)Reverse primer: 5'-CTCTTGGCAAATCTGGCGTG-3' (SEQ ID NO: 4)
MMP-2MMP-2
Forward primer: 5'-CGCATCTGGGGCTTTAAACAT-3' (서열번호 5)Forward primer: 5'-CGCATCTGGGGCTTTAAACAT-3' (SEQ ID NO: 5)
Reverse primer: 5'-CCATTAGCGCCTCCATCGTA-3' (서열번호 6)Reverse primer: 5'-CCATTAGCGCCTCCATCGTA-3' (SEQ ID NO: 6)
MMP-9MMP-9
Forward primer: 5'-CATCCGGCACCTCTATGGTC-3' (서열번호 7)Forward primer: 5'-CATCCGGCACCTCTATGGTC-3' (SEQ ID NO: 7)
Reverse primer: 5'-CATCGTCCACCGGACTCAAA-3' (서열번호 8)Reverse primer: 5'-CATCGTCCACCGGACTCAAA-3' (SEQ ID NO: 8)
각각의 상대적인 mRNA 발현량 값은 β-actin 값으로 표준화하였다.Each relative mRNA expression level value was normalized to the β-actin value.
그 결과, 도 3에서 보는 바와 같이 벌개미취 추출물 및 짐나스테르코리아인 B 각각은 콜라겐 분해효소(MMP-1, MMP-2, MMP-9) 발현량을 현저하게 억제시키는 것을 알 수 있었다.As a result, as shown in Fig. 3, it was found that each of the extract of bee ant gill odor and Jim Naster Koreain B significantly inhibited the expression levels of collagen-degrading enzymes (MMP-1, MMP-2, MMP-9).
실험예 4. 콜라겐 발현량 증가 Experimental Example 4. Increasing the amount of collagen expression
상기 <실시예 1> 내지 <실시예 2>를 통해 얻은 벌개미취 추출물 및 짐나스테르코리아인 B 각각에 대한 콜라겐의 발현량 증가 효능을 측정하였다. 양성 대조군으로는 EGCG 10 μM 농도를 사용하였다.The effect of increasing the expression level of collagen for each of the extract of bee ant odor obtained through the above <Example 1> to <Example 2> and Jim Naster Koreain B was measured.
먼저, 2.5%의 우태아 혈청이 함유된 DMEM(Dulbecco's Modified Eagle's Media) 배지가 들어 있는 6-공 평판배양기(6-well microtiter plate)에 인간의 각질형성세포를 2×106 세포/공(well)이 되도록 넣고, 90% 정도 자랄 때까지 배양하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>를 통해 얻은 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 1시간 동안 처리한 후, DPBS로 워싱한 다음, UV조사기를 이용하여 15 mJ을 조사하였다. 그 후 무혈청 DMEM 배지에 녹여진 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물을 5, 10, 20 μg/ml, 짐나스테르코리아인 B를 5, 10, 20 μM, 그리고 EGCG를 10 μM 농도로 추가로 처리하였다. 24시간 경과한 다음 세포로부터 TRIzol 시약(Invitrogen, Carlsbad, CA, USA)을 사용하여 총 RNA를 수확하여 역전사시킨 후, RT-PCR 분석을 다음과 같이 수행하였다. 먼저 cDNA 합성을 위해 상기 RNA를 reverse transcriptase로 역전사시켰다. RT-PCR은 다음의 특정 프라이머로 수행하였다: First, 2×10 6 cells/well of human keratinocytes in a 6-well microtiter plate containing DMEM (Dulbecco's Modified Eagle's Media) medium containing 2.5% fetal bovine serum. ), and incubated until about 90% growth. Thereafter, 5, 10, 20 μg/ml of the ethanol extract obtained through <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, and 5, 10, 20 μM of Jimnaster Koreain B , And EGCG was treated at a concentration of 10 μM for 1 hour, washed with DPBS, and then irradiated with 15 mJ using a UV irradiator. Thereafter, 5, 10, 20 μg/ml of the ethanol extracts of bee ant odor of <Example 1> to <Example 2> dissolved in a serum-free DMEM medium, 5, 10, 20 μM of Jimnaster Koreain B, and EGCG was further treated at a concentration of 10 μM. After 24 hours, total RNA was harvested from the cells using a TRIzol reagent (Invitrogen, Carlsbad, CA, USA) and reverse transcribed, and then RT-PCR analysis was performed as follows. First, for cDNA synthesis, the RNA was reverse transcribed with reverse transcriptase. RT-PCR was performed with the following specific primers:
β-actinβ-actin
Forward primer: 5'-AGCCATGTACGTAGCCATCC-3' (서열번호 1)Forward primer: 5'-AGCCATGTACGTAGCCATCC-3' (SEQ ID NO: 1)
Reverse primer: 5'-CTCTCAGCTGTGGTGGTGAA-3' (서열번호 2)Reverse primer: 5'-CTCTCAGCTGTGGTGGTGAA-3' (SEQ ID NO: 2)
COL1A1COL1A1
Forward primer: 5'-TGAGCGGACGCTAACCCCCT-3' (서열번호 9)Forward primer: 5'-TGAGCGGACGCTAACCCCCT-3' (SEQ ID NO: 9)
Reverse primer: 5'-CAGACGGGACAGCACTCGCC-3' (서열번호 10)Reverse primer: 5'-CAGACGGGACAGCACTCGCC-3' (SEQ ID NO: 10)
각각의 상대적인 mRNA 발현량 값은 β-actin 값으로 표준화하였다.Each relative mRNA expression level value was normalized to the β-actin value.
그 결과, 도 4에서 보는 바와 같이 벌개미취 추출물 및 짐나스테르코리아인 B 각각은 콜라겐 COL1A1 발현량 증가에 뛰어난 효과를 가짐을 알 수 있었다.As a result, as shown in FIG. 4, it was found that each of the extract of bee ant odor and Jim Naster Koreain B had an excellent effect on increasing the expression level of collagen COL1A1.
본 발명의 일 측면에 따른 조성물의 제형예를 아래에서 설명하나, 다른 여러 가지 제형으로도 응용 가능하며, 이는 본 발명을 한정하고자 함이 아닌 단지 구체적으로 설명하고자 함이다.An example of the formulation of the composition according to an aspect of the present invention is described below, but it can be applied to various other formulations, and this is not intended to limit the present invention, but is intended to be described in detail.
[제형예 1] 영양화장수(밀크로션)[Formulation Example 1] Nutritional lotion (milk lotion)
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B를 하기 표 1의 영양화장수 제형 비율대로 하여 통상적인 방법에 따라 영양화장수를 제조하였다.Nutrient cosmetic water was prepared according to a conventional method by using the ethanol extract of bee ant odor or Jimnaster Koreain B of the <Example 1> to <Example 2> according to the nutritional cosmetic water formulation ratio of Table 1 below.
표 1.Table 1.
[제형예 2] 유연화장수(스킨로션)[Formulation Example 2] Softening lotion (skin lotion)
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B를 하기 표 2의 유연화장수 제형 비율대로 하여 통상적인 방법에 따라 유연화장수를 제조하였다.Softening lotion was prepared according to a conventional method by using the ethanol extract of beehive taste or jimnaster Koreain B of the <Example 1> to <Example 2> according to the ratio of the softening lotion formulation shown in Table 2 below.
표 2.Table 2.
[제형예 3] 영양크림[Formulation Example 3] Nourishing Cream
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B를 하기 표 3의 영양크림 제형 비율대로 하여 통상적인 방법에 따라 영양크림을 제조하였다.A nutrient cream was prepared according to a conventional method by using the ethanol extract of bee ant odor or Jimnaster Koreain B of the <Example 1> to <Example 2> according to the nutritional cream formulation ratio shown in Table 3 below.
표 3.Table 3.
[제형예 4] 마사지크림[Formulation Example 4] Massage Cream
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B를 하기 표 4의 마사지크림 제형 비율대로 하여 통상적인 방법에 따라 마사지크림을 제조하였다.A massage cream was prepared according to a conventional method by using the ethanol extract of bee ant odor or Jim Naster Koreain B of the <Example 1> to <Example 2> according to the ratio of the massage cream formulation shown in Table 4 below.
표 4.Table 4.
[제형예 5] 팩[Formulation Example 5] Pack
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B를 하기 표 5의 팩 제형 비율대로 하여 통상적인 방법에 따라 팩을 제조하였다.A pack was prepared according to a conventional method by using the ethanol extract of bee ant odor or jimnaster Koreain B of the <Example 1> to <Example 2> according to the ratio of the pack formulation shown in Table 5 below.
표 5.Table 5.
[제형예 6] 젤[Formulation Example 6] Gel
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B를 하기 표 6의 젤 제형 비율대로 하여 통상적인 방법에 따라 젤을 제조하였다.A gel was prepared according to a conventional method by using the ethanol extract of beehive odor or jimnaster Koreain B of the <Example 1> to <Example 2> according to the gel formulation ratio shown in Table 6 below.
표 6.Table 6.
[제형예 7] 건강식품[Formulation Example 7] Health Food
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 1000 mg, 비타민 A 아세테이트 70 ㎍, 비타민 E 1.0 mg, 비타민 B1 0.13 mg, 비타민 B2 0.15 mg, 비타민 B6 0.5 mg, 비타민 B12 0.2 ㎍, 비타민 C 10 mg, 비오틴 10 ㎍, 니코틴산아미드 1.7 mg, 엽산 50 ㎍, 판토텐산 칼슘 0.5 mg, 황산제1철 1.75 mg, 산화아연 0.82 mg, 탄산마그네슘 25.3 mg, 제1인산칼륨 15 mg, 제2인산칼슘 55 mg, 구연산칼륨 90 mg, 탄산칼슘 100 mg, 염화마그네슘 24.8 mg를 혼합하여 제조할 수 있으며, 그 배합비를 임의로 변형 실시하여도 무방하며, 통상의 건강식품 제조방법에 따라 상기의 성분을 혼합한 다음 과립을 제조하고, 통상의 방법에 따라 건강식품 조성물 제조에 사용할 수 있다.Ethanol extract of beehive odor of <Example 1> to <Example 2> or Jimnaster Koreain B 1000 mg, vitamin A acetate 70 ㎍, vitamin E 1.0 mg, vitamin B1 0.13 mg, vitamin B2 0.15 mg, vitamin B6 0.5 mg, vitamin B12 0.2 μg,
[제형예 8] 건강음료[Formulation Example 8] Health Drink
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 1000 mg, 구연산 1000 mg, 올리고당 100 g, 매실농축액 2 g, 타우린 1 g에 정제수를 가하여 전체 900 ml로 통상의 건강음료 제조방법에 따라 상기의 성분을 혼합한 다음, 약 1시간 동안 85℃에서 교반 가열한 후 만들어진 용액을 여과하여 멸균된 2 L 용기에 취득하여 밀봉 멸균한 뒤 냉장 보관한 다음 건강음료 조성물 제조에 사용할 수 있다.Purified water was added to the ethanol extract of beehive odor of the <Example 1> to <Example 2> or 1000 mg of Jimnaster Koreain B, 1000 mg of citric acid, 100 g of oligosaccharide, 2 g of plum concentrate, and 1 g of taurine to obtain a total of 900 ml. After mixing the above ingredients according to the normal health drink manufacturing method, the resulting solution is stirred and heated at 85°C for about 1 hour, filtered, obtained in a sterilized 2 L container, sealed and sterilized, and then stored in the refrigerator. It can be used to prepare the composition.
[제형예 9] 츄잉껌[Formulation Example 9] Chewing gum
껌 베이스 20 중량%, 설탕 76.9 중량%, 향료 1 중량% 및 물 2 중량%와 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 0.1 중량%를 배합하여 통상의 방법으로 츄잉껌을 제조하였다.20% by weight of gum base, 76.9% by weight of sugar, 1% by weight of flavor, and 2% by weight of water, and 0.1% by weight of the ethanol extract of beehive odor of <Example 1> to <Example 2> or Jim Naster Korea B Chewing gum was prepared by a conventional method.
[제형예 10] 캔디[Formulation Example 10] Candy
설탕 60 중량%, 물엿 39.8 중량% 및 향료 0.1 중량%와 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 0.1 중량%를 배합하여 통상의 방법으로 캔디를 제조하였다.
[제형예 11] 비스켓[Formulation Example 11] Biscuit
박력 1급 25.59 중량%, 중력 1급 22.22 중량%, 정백당 4.80 중량%, 식염 0.73 중량%, 포도당 0.78 중량%, 팜쇼트닝 11.78 중량%, 암모늄 1.54 중량%, 중조 0.17 중량%, 중아황산나트륨 0.16 중량%, 쌀가루 1.45 중량%, 비타민 B₁0.0001 중량%, 비타민 B₂0.0001 중량%, 밀크향 0.04 중량%, 물 20.6998 중량%, 전지분유 1.16 중량%, 대용분유 0.29 중량%, 제1인산칼슘 0.03 중량%, 살포염 0.29 중량% 및 분무유 7.27 중량%와 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 중량%를 배합하여 통상의 방법으로 비스켓을 제조하였다.
[제형예 12] 산제[Formulation Example 12] Powder
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 50 mg, 결정셀룰로오즈 2 g을 혼합한 후 통상의 산제 제조방법에 따라서 기밀포에 충진하여 산제를 제조하였다.A powder was prepared by mixing the ethanol extract of beehive odor of the above <Example 1> to <Example 2> or 50 mg of Jimnaster Koreain B, and 2 g of crystalline cellulose, and then filled in an airtight cloth according to a conventional powder preparation method. .
[제형예 13] 정제[Formulation Example 13] Tablet
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 50 mg, 결정셀룰로오즈 400 mg, 스테아린산 마그네슘 5 mg을 혼합한 후 통상의 정제 제조방법에 따라서 타정하여 정제를 제조하였다.After mixing the ethanol extract of beehive odor of <Examples 1> to <Example 2> or 50 mg of Zimnaster Koreain B, 400 mg of crystalline cellulose, and 5 mg of magnesium stearate, tablets were prepared by tableting according to a conventional tablet manufacturing method. Was prepared.
[제형예 14] 캡슐제[Formulation Example 14] Capsule
상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 30 mg, 유청단백질 100 mg, 결정셀룰로오즈 400 mg, 스테아린산 마그네슘 6 mg을 혼합한 후 통상의 캡슐제 제조방법에 따라서 젤라틴 캡슐에 충전하여 캡슐제를 제조하였다.A conventional capsule preparation method after mixing the ethanol extract of beehive odor of the <Examples 1> to <Example 2> or 30 mg of Jimnaster Koreain B, 100 mg of whey protein, 400 mg of crystalline cellulose, 6 mg of magnesium stearate According to the following, a gelatin capsule was filled to prepare a capsule.
[제형예 15] 주사제[Formulation Example 15] Injection
통상의 주사제 제조방법에 따라 활성성분을 주사용 증류수에 용해하고 pH를 약 7.5로 조절한 다음 상기 <실시예 1> 내지 <실시예 2>의 벌개미취 에탄올 추출물 또는 짐나스테르코리아인 B 100 mg, 주사용 증류수, pH 조절제를 혼합하여 2 ml 용량의 앰플에 충진하고 멸균시켜 주사제를 제조하였다.According to a conventional injection preparation method, the active ingredient is dissolved in distilled water for injection and the pH is adjusted to about 7.5, and then the ethanol extract of beehive odor of <Examples 1> to <Example 2> or
이상, 본 발명 내용의 특정한 부분을 상세히 기술하였는바, 당업계의 통상의 지식을 가진 자에게 있어서, 이러한 구체적인 기술은 단지 바람직한 실시태양일 뿐이며, 이에 의해 본 발명의 범위가 제한되는 것이 아닌 점은 명백할 것이다. 따라서 본 발명의 실질적인 범위는 첨부된 청구항들과 그것들의 등가물에 의해 정의된다고 할 것이다.As described above, specific parts of the present invention have been described in detail, and for those of ordinary skill in the art, these specific techniques are only preferred embodiments, and the scope of the present invention is not limited thereto. It will be obvious. Therefore, it will be said that the practical scope of the present invention is defined by the appended claims and their equivalents.
<110> KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY <120> ANTI-AGING COMPOSITION COMPRISING ASTER PLANT EXTRACTS <130> 17P612/IND <160> 10 <170> KopatentIn 2.0 <210> 1 <211> 20 <212> DNA <213> beta-actin forward primer <400> 1 agccatgtac gtagccatcc 20 <210> 2 <211> 20 <212> DNA <213> beta-actin reverse primer <400> 2 ctctcagctg tggtggtgaa 20 <210> 3 <211> 20 <212> DNA <213> MMP-1 forward primer <400> 3 acagcttccc agcgactcta 20 <210> 4 <211> 20 <212> DNA <213> MMP-1 reverse primer <400> 4 ctcttggcaa atctggcgtg 20 <210> 5 <211> 21 <212> DNA <213> MMP-2 forward primer <400> 5 cgcatctggg gctttaaaca t 21 <210> 6 <211> 20 <212> DNA <213> MMP-2 reverse primer <400> 6 ccattagcgc ctccatcgta 20 <210> 7 <211> 20 <212> DNA <213> MMP-9 forward primer <400> 7 catccggcac ctctatggtc 20 <210> 8 <211> 20 <212> DNA <213> MMP-9 reverse primer <400> 8 catcgtccac cggactcaaa 20 <210> 9 <211> 20 <212> DNA <213> COL1A1 forward primer <400> 9 tgagcggacg ctaaccccct 20 <210> 10 <211> 20 <212> DNA <213> COL1A1 reverse primer <400> 10 cagacgggac agcactcgcc 20 <110> KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY <120> ANTI-AGING COMPOSITION COMPRISING ASTER PLANT EXTRACTS <130> 17P612/IND <160> 10 <170> KopatentIn 2.0 <210> 1 <211> 20 <212> DNA <213> beta-actin forward primer <400> 1 agccatgtac gtagccatcc 20 <210> 2 <211> 20 <212> DNA <213> beta-actin reverse primer <400> 2 ctctcagctg tggtggtgaa 20 <210> 3 <211> 20 <212> DNA <213> MMP-1 forward primer <400> 3 acagcttccc agcgactcta 20 <210> 4 <211> 20 <212> DNA <213> MMP-1 reverse primer <400> 4 ctcttggcaa atctggcgtg 20 <210> 5 <211> 21 <212> DNA <213> MMP-2 forward primer <400> 5 cgcatctggg gctttaaaca t 21 <210> 6 <211> 20 <212> DNA <213> MMP-2 reverse primer <400> 6 ccattagcgc ctccatcgta 20 <210> 7 <211> 20 <212> DNA <213> MMP-9 forward primer <400> 7 catccggcac ctctatggtc 20 <210> 8 <211> 20 <212> DNA <213> MMP-9 reverse primer <400> 8 catcgtccac cggactcaaa 20 <210> 9 <211> 20 <212> DNA <213> COL1A1 forward primer <400> 9 tgagcggacg ctaaccccct 20 <210> 10 <211> 20 <212> DNA <213> COL1A1 reverse primer <400> 10 cagacgggac agcactcgcc 20
Claims (8)
[화학식 2]
A cosmetic composition for improving skin wrinkles or skin elasticity comprising a compound represented by the following formula (2), a derivative thereof, a salt thereof, a hydrate thereof, a solvate thereof, a prodrug thereof or an isomer thereof as an active ingredient.
(2)
상기 화합물은 개미취속(Aster L.) 식물의 추출물 또는 이의 분획물로부터 분리된 것인, 피부 주름 개선 또는 피부 탄력 증진용 화장료 조성물.
The method according to claim 1,
Wherein the compound is isolated from an extract of Aster L. plant or a fraction thereof.
상기 화합물은 조성물 전체 중량을 기준으로 0.0001 내지 10 중량%로 포함되는, 피부 주름 개선 또는 피부 탄력 증진용 화장료 조성물.
The method according to claim 1,
Wherein the compound is contained in an amount of 0.0001 to 10% by weight based on the total weight of the composition.
[화학식 2]
A food composition for improving skin wrinkles or skin elasticity comprising a compound represented by the following formula (2), a derivative thereof, a salt thereof, a hydrate thereof, a solvate thereof, a prodrug thereof or an isomer thereof as an active ingredient.
(2)
상기 화합물은 개미취속(Aster L.) 식물의 추출물 또는 이의 분획물로부터 분리된 것인, 피부 주름 개선 또는 피부 탄력 증진용 식품 조성물.
6. The method of claim 5,
Wherein the compound is isolated from an extract of Aster L. plant or a fraction thereof, to improve skin wrinkles or skin elasticity.
상기 화합물은 조성물 전체 중량을 기준으로 0.0001 내지 10 중량%로 포함되는, 피부 주름 개선 또는 피부 탄력 증진용 식품 조성물.6. The method of claim 5,
Wherein the compound is contained in an amount of 0.0001 to 10% by weight based on the total weight of the composition.
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