KR102249037B1 - Composition for Improving, Preventing or Treating Male Pattern Alopecia Comprising Catechin 7-O-β-D-apiofuranoside As Active Ingredient - Google Patents
Composition for Improving, Preventing or Treating Male Pattern Alopecia Comprising Catechin 7-O-β-D-apiofuranoside As Active Ingredient Download PDFInfo
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- KR102249037B1 KR102249037B1 KR1020200114893A KR20200114893A KR102249037B1 KR 102249037 B1 KR102249037 B1 KR 102249037B1 KR 1020200114893 A KR1020200114893 A KR 1020200114893A KR 20200114893 A KR20200114893 A KR 20200114893A KR 102249037 B1 KR102249037 B1 KR 102249037B1
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- South Korea
- Prior art keywords
- catechin
- apiofuranoside
- present
- composition
- compound
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- A61K31/00—Medicinal preparations containing organic active ingredients
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Abstract
Description
본 발명은 카테킨 7-O-β-D-아피오푸란노사이드를 유효성분으로 포함하는 남성형 탈모증의 개선, 예방 또는 치료용 조성물에 관한 것이다. The present invention relates to a composition for improving, preventing or treating android type alopecia comprising catechin 7-O-β-D-apiofuranoside as an active ingredient.
탈모는 다른 병리적 질환에 비해 병리 장애적 문제는 없지만, 외모에 영향을 미쳐 사회적, 심리적 문제로서 탈모를 겪는 사람에게 큰 영향을 끼친다. 과거에 탈모는 노화현상으로 인식되어 왔으나, 최근에는 유전적 요인과 함께 스트레스, 영양불균형, 사회활동의 변화, 질병, 출산, 식생활의 변화, 불규칙한 생활, 과도한 화학 정발제 사용 등 다양한 요인으로 인해 나타나고 있다. 탈모의 유형은 크게 남성형 탈모, 여성형 탈모, 원형 탈모, 산후 탈모, 지루성 두피염에 의한 탈모로 분류되며, 그 중에서 비율이 가장 높은 탈모의 유형은 남성형 탈모이다. Hair loss does not have a pathological disorder problem compared to other pathological diseases, but it affects the appearance and greatly affects the person who suffers hair loss as a social and psychological problem. In the past, hair loss has been recognized as an aging phenomenon, but recently, it appears due to various factors such as stress, nutritional imbalance, changes in social activities, diseases, childbirth, changes in diet, irregular life, and excessive use of chemical hairdressing agents along with genetic factors. have. The types of hair loss are largely classified into male-type hair loss, female-type hair loss, circular hair loss, postpartum hair loss, and hair loss due to seborrheic scalp infection, and among them, the type of hair loss with the highest rate is male-type hair loss.
남성형 탈모는 유전적인 원인에 의하여 발생되고 탈모가 빨리 시작되면 탈모의 정도도 더 심해지는 경향이 있다. 반면, 유전적 원인 이외에 남성호르몬인 테스토스테론(Testosterone)이 5알파-환원효소(5α-reductase)에 의해 디하이드로테스토스테론(Dihydrotestosterone, DHT)으로 변화되어 생생된 DHT가 모유두세포를 위축시키고 세포분열을 둔화시켜 모발이 가늘어지거나 탈모가 진행된다. Male pattern hair loss is caused by a genetic cause, and when hair loss begins quickly, the degree of hair loss tends to become more severe. On the other hand, in addition to the genetic cause, testosterone, a male hormone, is converted into dihydrotestosterone (DHT) by 5α-reductase, and the resulting DHT atrophys the dermal papilla cells and slows cell division As a result, the hair becomes thinner or hair loss progresses.
미녹시딜(minoxidil)은 1970년대 초에 고혈압치료를 위한 혈관확장제로 개발되었으나, 부작용으로 다모증이 보고되면서 발모 촉진제로 사용되었다. 발모효과에 대한 기전은 정확하게 밝혀져 있지 않지만, 혈관 확장으로 인한 영양공급 증가로 모발성장을 유도한다고 보고되었다. 그러나, 미녹시딜은 이미 대머리가 되어버린 두피의 앞쪽에서는 효과가 없으며, 6-12개월간 하루 두 차례씩 꾸준히 두피에 도포하지 않으면 효과를 볼 수 없다. 미녹시딜의 부작용으로는 부종, 빈맥, 국소박리, 피부염, 투여 부위에 대한 쓰라림, 홍반, 피부 벗겨짐, 가려움증, 건조증, 피부낙설, 접촉피부염 등이 보고되었고, 다모증이 유발될 수 있다고 보고된 바가 있다. 또한, 미녹시딜이 모발 주기에 영향을 주어 휴지기 모발탈락(shedding)의 증가로 인해 탈모가 더 심해지는 현상이 있을 수 있으며, 투역을 중지하는 경우 치료 전의 상태로 환원되는 기간이 짧은 단점이 있다. Minoxidil was developed as a vasodilator for the treatment of hypertension in the early 1970s, but was used as a hair growth promoting agent as hirsutism was reported as a side effect. Although the mechanism for the hair growth effect is not accurately identified, it has been reported that hair growth is induced by increasing nutrient supply due to vasodilation. However, minoxidil is not effective in the front of the scalp, which has already become bald, and if it is not steadily applied to the scalp twice a day for 6-12 months, the effect cannot be seen. Side effects of minoxidil include edema, tachycardia, local peeling, dermatitis, soreness at the site of administration, erythema, peeling of the skin, itchiness, dryness, skin dropping, and contact dermatitis, and it has been reported that hirsutism can be induced. In addition, since minoxidil affects the hair cycle, there may be a phenomenon in which hair loss becomes more severe due to an increase in shedding during the resting period, and there is a shortcoming in that the period of returning to the state before treatment is short when the dialysis is stopped.
본 명세서에서 언급된 특허문헌 및 참고문헌은 각각의 문헌이 참조에 의해 개별적이고 명확하게 특정된 것과 동일한 정도로 본 명세서에 참조로 삽입된다. The patent documents and references mentioned in this specification are incorporated herein by reference to the same extent as if each document was individually and clearly specified by reference.
본 발명자들은 보다 안전하고 부작용 없는 천연물 유래의 탈모 방지제를 개발하기 위해 연구 노력하였다. 그 결과, 느릅나무속 식물의 초임계 추출박의 추출물로부터 단일 화합물로서 분리한 카테킨 7-O-β-D-아피오푸란노사이드(catechin 7-O-β-D-apiofuranoside) 화합물이 인간 모유듀 세포에서 테스토스테론 유래의 디하이드로테스토스테론(DHT)의 생성을 억제함을 실험적으로 증명함으로써 남성형 탈모증의 치료제로 개발될 수 있음을 확인하여 본 발명을 완성하였다. The present inventors have made research efforts to develop a natural product-derived anti-hair loss agent that is safer and has no side effects. As a result, the catechin 7-O-β-D-apiofuranoside (catechin 7-O-β-D-apiofuranoside) compound isolated as a single compound from the extract of the supercritical extract of the elm plant The present invention was completed by confirming that it can be developed as a therapeutic agent for android type alopecia by experimentally demonstrating that it inhibits the production of testosterone-derived dihydrotestosterone (DHT) in cells.
따라서, 본 발명의 목적은 남성형 탈모증의 개선, 예방 또는 치료용 조성물을 제공하는 것에 있다. Accordingly, an object of the present invention is to provide a composition for improving, preventing or treating android type alopecia.
본 발명의 다른 목적 및 기술적 특징은 이하의 발명의 상세한 설명, 청구의 범위 및 도면에 의해 보다 구체적으로 제시된다. Other objects and technical features of the present invention are presented in more detail by the following detailed description, claims, and drawings.
본 발명의 일 양태에 따르면, 본 발명은 카테킨 7-O-β-D-아피오푸란노사이드(catechin 7-O-β-D-apiofuranoside) 화합물을 유효성분으로 포함하는 남성형 탈모증의 예방, 개선 또는 치료용 조성물을 제공한다. According to one aspect of the present invention, the present invention is the prevention and improvement of androgenetic alopecia comprising a catechin 7-O-β-D-apiofuranoside compound as an active ingredient Or it provides a composition for treatment.
본 발명 조성물의 유효성분인 카테킨 7-O-β-D-아피오푸란노사이드는 아래의 화학식 1로 표시되는 카테킨 배당체 화합물이다. Catechin 7-O-β-D-apiofuranoside, an active ingredient of the composition of the present invention, is a catechin glycoside compound represented by the following formula (1).
[화학식 1] [Formula 1]
본 발명 조성물의 유효성분인 카테킨 7-O-β-D-아피오푸란노사이드(catechin 7-O-β-D-apiofuranoside)는 천연물로부터 분리된 것을 사용할 수 있으나, 화학적으로 합성된 것도 추출된 것과 동일한 효과를 나타낸다는 것은 통상의 기술자에게 자명하다. Catechin 7-O-β-D-apiofuranoside, the active ingredient of the composition of the present invention, can be used isolated from natural products, but chemically synthesized ones are also extracted. It is obvious to a person skilled in the art that it exhibits the same effect as that.
본 발명의 카테킨 7-O-β-D-아피오푸란노사이드 화합물은 천연물 추출물인 느릅나무속 식물의 초임계 추출박의 용매 추출물에 다량 포함되어 있으며, 이 추출물로부터 통상의 단일 화합물 분리 방법에 의해 얻을 수 있다. The catechin 7-O-β-D-apiofuranoside compound of the present invention is contained in a large amount in the solvent extract of the supercritical extract of the elm plant, which is a natural product extract, from this extract by a conventional single compound separation method. You can get it.
본 발명에서 느릅나무속 식물의 초임계 추출박(supercritical extract residue)은 느릅나무속 식물을 초임계 추출방법에 의해 추출하고 남은 잔여물(residue)을 의미한다. In the present invention, the supercritical extract residue of the Elm genus refers to a residue left after extracting the Elm genus plant by the supercritical extraction method.
본 발명의 초임계 추출박 제조에 사용되는 느릅나무속(Ulmus) 식물은 장미목 느릅나무과의 식물을 포함하며, 예를 들어 당느릅나무(Ulmus davidiana), 느릅나무(Ulmus davidiana var. japonica), 혹느릅나무(Ulmus davidiana var. japonica for. Suberosa), 참느릅나무(Ulmus parvifolia), 비술나무(Ulmus pumila), 난티나무(Ulmus laciniata), 왕느릅나무(Ulmus macrocarpa) 등을 포함한다. 가장 대표적으로는 당느릅나무(Ulmus davidiana), 느릅나무(Ulmus davidiana var. japonica)를 사용할 수 있다. The Elm genus (Ulmus) plant used in the production of the supercritical extract of the present invention includes a plant of the Rosaceae elm family, for example, Ulmus davidiana, Elm tree (Ulmus davidiana var. japonica), and lump elm. Trees (Ulmus davidiana var.japonica for.Suberosa), Ulmus parvifolia, Ulmus pumila, Ulmus laciniata, and Ulmus macrocarpa. Most representatively, the elm tree (Ulmus davidiana), the elm tree (Ulmus davidiana var. japonica) can be used.
본 발명에서 초임계 추출에 사용되는 느릅나무속 식물은 느릅나무속 식물의 전체; 또는 줄기, 뿌리, 잎, 꽃, 열매, 및 씨앗으로 구성된 군에서 선택된 느릅나무속 식물의 일부를 사용할 수 있다. 바람직하게는 느릅나무속 식물의 줄기, 가지 또는 뿌리를 사용할 수 있다. 본 발명에서 초임계 추출 전에 상기 느릅무나무속 식물 전체 또는 일부를 건조 및/또는 분쇄할 수 있다. The elm plant used for supercritical extraction in the present invention is the whole of the elm plant; Alternatively, a part of an Elm genus plant selected from the group consisting of stems, roots, leaves, flowers, fruits, and seeds may be used. Preferably, a stem, branch or root of an Elm genus plant may be used. In the present invention, before the supercritical extraction, the whole or part of the elm plant may be dried and/or pulverized.
본 발명에서 초임계 추출(supercritical extraction) 방법은 초임계 상태의 유체를 사용하여 천연물에 함유된 향, 색소, 유지류 또는 기능성 물질을 변성 없이 추출하는 방법을 의미한다. In the present invention, the supercritical extraction method refers to a method of extracting flavors, pigments, oils, or functional substances contained in natural products without denaturation by using a fluid in a supercritical state.
상기 초임계 상태의 유체는 임계점(supercritical point)의 일정한 고온 고압의 한계점을 넘어 기체와 액체의 구별이 되지 않는 상태의 유체를 의미한다. 상기 초임계 유체는 초임계이산화탄소(supercritical carbon dioxide)를 예로 들 수 있다. 상기 초임계이산화탄소는 임계온도(31℃) 및 임계압력(7.5 MPa)을 초과한 상태의 이산화탄소로서 기체와 액체의 성질을 동시에 가진 유체이다. The fluid in the supercritical state refers to a fluid in a state in which gas and liquid cannot be distinguished beyond a limit point of a constant high temperature and high pressure at a supercritical point. The supercritical fluid may be, for example, supercritical carbon dioxide. The supercritical carbon dioxide is carbon dioxide in a state exceeding a critical temperature (31° C.) and a critical pressure (7.5 MPa), and is a fluid having both gas and liquid properties.
본 발명에서의 초임계 추출법은 예를 들어 초임계 유체와 용질의 혼합물을 추출온도와 같은 온도에서 감압하여 팽창시켜 초임계 유체의 용해력이 감소되면서 용질이 분리되는 압력변화법 방식; 또는 초임계 유체의 온도를 높여서 용해력을 감소시킴으로서 초임계 유체와 용질을 분리하는 온도 변화법 방식으로 행해질 수 있으나, 이에 한정되지 않는다. The supercritical extraction method in the present invention includes, for example, a pressure change method in which a mixture of a supercritical fluid and a solute is decompressed and expanded at a temperature equal to the extraction temperature to reduce the dissolving power of the supercritical fluid and the solute is separated; Alternatively, the temperature of the supercritical fluid may be increased to decrease the dissolving power, and thus, the supercritical fluid may be separated from the solute, but the method is not limited thereto.
본 발명에서 상기 초임계유체와 함께 보조용매를 사용할 수 있으며, 보조용매는 당업계에서 통상적으로 이용되는 극성 용매를 포함하며, 바람직하게는 알코올, 물, 에틸렌 글라이콜, 폴리에틸렌글라이콜, 프로필렌카보네이트, 포름산, 아세트산, 아세토니트릴, 클로로디프루오로메탄 또는 이의 혼합물로 구성된 군으로부터 선택하여 사용할 수 있다. In the present invention, a co-solvent may be used with the supercritical fluid, and the co-solvent includes a polar solvent commonly used in the art, and preferably alcohol, water, ethylene glycol, polyethylene glycol, and propylene It can be used by selecting from the group consisting of carbonate, formic acid, acetic acid, acetonitrile, chlorodifluoromethane, or mixtures thereof.
본 발명에서 초임계 추출용 용기는 온도와 압력이 조절될 수 있으며, 추출원료와 초임계 유체가 접촉하도록 구성된 용기이면 특별히 한정되지 않는다. In the present invention, the container for supercritical extraction may be controlled in temperature and pressure, and it is not particularly limited as long as it is a container configured to contact the extraction raw material and the supercritical fluid.
본 발명에서 초임계 추출에서의 압력은 100-600 bar 범위일 수 있고, 초임계 추출에서의 온도는 10-100℃ 범위일 수 있으며, 초임계 추출에서의 초임계 유체 및 보조용매의 유속은 10-100 g/분일 수 있다. 당업계의 통상의 기술자는 초임계 추출에서 압력, 온도, 유체 및 보조용매의 유속을 상기 범위 내에서 적절하게 조절하여 사용할 수 있다. In the present invention, the pressure in the supercritical extraction may be in the range of 100-600 bar, the temperature in the supercritical extraction may be in the range of 10-100°C, and the flow rate of the supercritical fluid and the auxiliary solvent in the supercritical extraction may be 10 May be -100 g/min. Those of ordinary skill in the art may use the pressure, temperature, fluid and co-solvent flow rates in the supercritical extraction to be appropriately adjusted within the above range.
상기 초임계 추출방법을 행한 후에 얻어진 느릅나무속 식물의 초임계 추출박에 대해 용매를 사용한 추출을 통해 추출물을 얻는다. 바람직하게는 상기 용매 추출은 느릅나무의 초임계 추출박을 추출용매와 접촉시키는 공정을 통해 수행된다. 용매 추출 단계 전에 상기 느릅나무의 초임계 추출박을 건조 및/또는 분쇄할 수 있다. 본 발명에서 상기 추출 용매는 바람직하게는 알코올을 사용할 수 있으며, 상기 알코올은 탄소수 1-4의 무수 또는 함수 저급 알코올, 예를 들어 메탄올, 에탄올, 프로판올, 부탄올, 노말-프로판올, 이소-프로판올 및 노말-부탄올을 들 수 있다. The supercritical extract of the elm plant obtained after performing the supercritical extraction method is subjected to extraction using a solvent to obtain an extract. Preferably, the solvent extraction is performed through a process of contacting the supercritical extract foil of elm with an extraction solvent. Before the solvent extraction step, the supercritical extract foil of the elm tree may be dried and/or pulverized. In the present invention, the extraction solvent may preferably use an alcohol, and the alcohol is an anhydrous or water-containing lower alcohol having 1-4 carbon atoms, such as methanol, ethanol, propanol, butanol, normal-propanol, iso-propanol, and normal -Butanol is mentioned.
본 발명에서 상기 느릅나무 초임계 추출박의 용매 추출물에 대해 추가적인 분획을 실시하여 분획물을 얻을 수 있다. In the present invention, a fraction can be obtained by performing an additional fractionation on the solvent extract of the supercritical extract of the elm tree.
상기 분획은 추출과 마찬가지로 분획 용매를 상기 추출물과 접촉시켜 행한다. 상기 분획에 사용되는 용매는 (a) 물, (b) 알코올, (c) 상기 저급 알코올과 물과의 혼합용매, (d) 아세톤, (e) 에틸아세테이트, (f) 클로로포름, (g) 부틸아세테이트, (h) 1,3-부틸렌글리콜, (i) 헥산 및 (j) 디에틸에테르를 포함한다. 바람직하게는 에틸아세테이트를 사용하여 얻은 분획물일 수 있다. The fractionation is carried out by contacting the fractionation solvent with the extract, similarly to extraction. The solvent used for the fractionation is (a) water, (b) alcohol, (c) a mixed solvent of the lower alcohol and water, (d) acetone, (e) ethyl acetate, (f) chloroform, (g) butyl Acetate, (h) 1,3-butylene glycol, (i) hexane and (j) diethyl ether. Preferably, it may be a fraction obtained using ethyl acetate.
상기 분획물로부터 크로마토그래피(chromatography)와 같은 당업계에서 공지된 통상적인 단일 화합물의 분리 방법을 사용하여 카테킨 7-O-β-D-아피오푸란노사이드를 분리할 수 있다. 본 발명에서 사용될 수 있는 단일 화합물의 분리 정제 방법은 예컨대 TLC (Thin Layer Chromatography) 또는 HPLC (High Performance Liquid Chromatography)의 방법을 사용할 수 있다. From the fraction, catechin 7-O-β-D-apiofuranoside can be separated using a conventional single compound separation method known in the art, such as chromatography. A method of separating and purifying a single compound that can be used in the present invention may use, for example, a method of thin layer chromatography (TLC) or high performance liquid chromatography (HPLC).
본 명세서 구체적인 일 실시예에서 입증되는 바와 같이, 본 발명의 활성 화합물인 카테킨 7-O-β-D-아피오푸란노사이드는 인간 유래 모유두세포(HFDPC)에서 테스토스테론이 5알파-환원효소(5α-reductase)에 의해 디하이드로테스토스테론(DHT, Dihydrotestosterone)으로 변환되는 것을 저해함으로써, 남성형 탈모의 예방, 치료, 개선 효과를 발휘할 수 있다. As demonstrated in one specific example of the present specification, the active compound of the present invention, catechin 7-O-β-D-apiofurannoside, is a testosterone in human-derived dermal papilla cells (HFDPC). -reductase) by inhibiting the conversion to dihydrotestosterone (DHT), it can exhibit the effect of preventing, treating, and improving male pattern hair loss.
본 명세서에서 용어 “유효성분으로 포함하는”이란 본 발명의 카테킨 7-O-β-D-아피오푸란노사이드 화합물이 남성형 탈모증의 예방, 개선 또는 치료의 효능을 달성하는 데 충분한 양을 포함하는 것을 의미한다. In the present specification, the term "comprised as an active ingredient" means that the catechin 7-O-β-D-apiofuranoside compound of the present invention contains an amount sufficient to achieve the effect of preventing, ameliorating or treating android type alopecia. Means that.
본 명세서에서 용어 “탈모”는 비정상적인 모발의 유실로 인해 정상적으로 모발이 존재해야할 부위에 모발이 없는 상태를 의미하며, 용어 “탈모증”은 상기와 같은 탈모로 인하여 야기되는 상태(condition)를 의미한다. In the present specification, the term “hair loss” refers to a state in which there is no hair in a region where hair should normally exist due to the loss of abnormal hair, and the term “alopecia” refers to a condition caused by the aforementioned hair loss.
본 발명에서 “남성형 탈모증”은 안드로겐성 탈모증이라고도 하며, 유전적 원인과 남성호르몬의 영향 또는 노화가 원인인 탈모증을 의미한다. In the present invention, "androgenic alopecia" is also referred to as androgenetic alopecia, and refers to alopecia caused by genetic causes and effects of male hormones or aging.
구체적으로, 본 발명에서 “남성형 탈모증”은 남성 호르몬인 테스토스테론이 5알파-환원효소 작용에 의해 변환되어 생성되는 디하이드로테스토스테론(DHT)에 의해 유발되는 탈모증일 수 있다. Specifically, in the present invention, "androgenic alopecia" may be alopecia caused by dihydrotestosterone (DHT) produced by converting testosterone, a male hormone, through a 5-alpha-reductase action.
본 발명의 조성물은 남성형 탈모증의 예방 또는 치료용 약학적 조성물 형태로 제공될 수 있으며, 약학적 조성물은 약학적으로 허용되는 담체를 포함할 수 있다. The composition of the present invention may be provided in the form of a pharmaceutical composition for preventing or treating android type alopecia, and the pharmaceutical composition may include a pharmaceutically acceptable carrier.
본 명세서에서 용어 “예방”은 탈모로 인한 증상 또는 탈모의 합병증으로 인한 증상의 발생의 억제를 의미하며, 용어 “치료”는 이미 발생된 탈모로 인한 증상 또는 탈모의 합병증으로 인한 증상의 경감 또는 제거를 의미한다. In the present specification, the term “prevention” refers to the suppression of the occurrence of symptoms due to hair loss or complications of hair loss, and the term “treatment” means reduction or elimination of symptoms due to already occurring hair loss or symptoms due to hair loss complications Means.
본 발명의 조성물에서 약학적으로 허용되는 담체는 제제시에 통상적으로 이용되는 것으로서, 락토스, 덱스트로스, 수크로스, 솔비톨, 만니톨, 전분, 아카시아 고무, 인산 칼슘, 알기네이트, 젤라틴, 규산 칼슘, 미세결정성 셀룰로스, 폴리비닐피롤리돈, 셀룰로스, 물, 시럽, 메틸 셀룰로스, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 활석, 스테아르산 마그네슘 및 미네랄 오일 등을 포함하나, 이에 한정되는 것은 아니다. 본 발명의 약학적 조성물 은 상기 성분들 이외에 윤활제, 습윤제, 감미제, 향미제, 유화제, 현탁제, 보존제 등을 추가로 포함할 수 있다. 적합한 약학적으로 허용되는 담체 및 제제는 Remington's Pharmaceutical Sciences (19th ed., 1995)에 상세히 기재되어 있다. Pharmaceutically acceptable carriers in the composition of the present invention are commonly used at the time of formulation, and are lactose, dextrose, sucrose, sorbitol, mannitol, starch, gum acacia, calcium phosphate, alginate, gelatin, calcium silicate, fine Crystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methyl cellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, mineral oil, and the like, but are not limited thereto. The pharmaceutical composition of the present invention may further include a lubricant, a wetting agent, a sweetening agent, a flavoring agent, an emulsifying agent, a suspending agent, a preservative, and the like in addition to the above components. Suitable pharmaceutically acceptable carriers and formulations are described in detail in Remington's Pharmaceutical Sciences (19th ed., 1995).
본 발명의 약학적 조성물은 경구 또는 비경구로 투여할 수 있고, 비경구 투여인 경우에는 정맥내 주입, 피하 주입, 근육내 주입, 복강내 주입, 경피 투여 등으로 투여할 수 있다. The pharmaceutical composition of the present invention may be administered orally or parenterally, and in the case of parenteral administration, it may be administered by intravenous injection, subcutaneous injection, intramuscular injection, intraperitoneal injection, transdermal administration, or the like.
본 발명의 약학적 조성물의 적합한 투여량은 제제화 방법, 투여 방식, 환자의 연령, 체중, 성, 병적 상태, 음식, 투여 시간, 투여 경로, 배설 속도 및 반응 감응성과 같은 요인들에 의해 다양하며, 보통으로 숙련된 의사는 소망하는 치료 또는 예방에 효과적인 투여량을 용이하게 결정 및 처방할 수 있다. A suitable dosage of the pharmaceutical composition of the present invention varies depending on factors such as formulation method, mode of administration, age, weight, sex, pathological condition, food, administration time, route of administration, excretion rate and response sensitivity of the patient, Usually the skilled practitioner can readily determine and prescribe a dosage effective for the desired treatment or prophylaxis.
본 발명의 약학적 조성물의 1일 투여량은 0.001-10,000 ㎎/㎏이다. The daily dosage of the pharmaceutical composition of the present invention is 0.001-10,000 mg/kg.
본 발명의 약학적 조성물은 당해 발명이 속하는 기술분야에서 통상의 지식을 가진 자가 용이하게 실시할 수 있는 방법에 따라, 약제학적으로 허용되는 담체 및/또는 부형제를 이용하여 제제화함으로써 단위 용량 형태로 제조되거나 또는 다용량 용기 내에 내입시켜 제조될 수 있다. 이 때 제형은 오일 또는 수성 매질중의 용액, 현탁액 또는 유화액 형태이거나 엑스제, 분말제, 과립제, 정제 또는 캅셀제 형태일 수도 있으며, 분산제 또는 안정화제를 추가적으로 포함할 수 있다. The pharmaceutical composition of the present invention is prepared in unit dosage form by formulating using a pharmaceutically acceptable carrier and/or excipient according to a method that can be easily carried out by a person having ordinary knowledge in the art. Or it can be prepared by incorporating it into a multi-dose container. In this case, the formulation may be in the form of a solution, suspension, or emulsion in an oil or aqueous medium, or may be in the form of an extract, powder, granule, tablet or capsule, and may additionally include a dispersant or a stabilizer.
본 발명의 다른 양태에 따르면, 카테킨 7-O-β-D-아피오푸란노사이드를 유효성분으로 포함하는 남성형 탈모증의 예방 또는 개선용 기능성 화장품 조성물을 제공한다. According to another aspect of the present invention, there is provided a functional cosmetic composition for preventing or improving android type alopecia comprising catechin 7-O-β-D-apiofuranoside as an active ingredient.
본 명세서에서 용어 “개선”은 탈모로 인한 증상 또는 탈모의 합병증으로 인한 증상의 경감 또는 완화를 의미한다. In the present specification, the term “improvement” means alleviation or alleviation of symptoms due to hair loss or symptoms due to complications of hair loss.
본 발명의 기능성 화장품 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클린싱, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 유연 화장수, 영양 화장수, 영양 크림, 마사지 크림, 에센스, 아이 크림, 클렌징 크림, 클렌징 포옴, 클렌징 워터, 팩, 스프레이 또는 파우더의 제형으로 제조될 수 있다. The functional cosmetic composition of the present invention may be prepared in any formulation conventionally prepared in the art, for example, solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing It may be formulated as a cleansing, oil, powder foundation, emulsion foundation, wax foundation, and spray, but is not limited thereto. In more detail, it may be prepared in the form of a flexible lotion, nutritional lotion, nutritional cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
본 발명의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물성유, 식물성유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다. When the formulation of the present invention is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc, or zinc oxide may be used as a carrier component. I can.
본 발명의 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로 플루오로히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진체를 포함할 수 있다. When the formulation of the present invention is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate, or polyamide powder may be used as a carrier component. In particular, in the case of a spray, additionally chlorofluorohydrocarbon, propane / May contain propellants such as 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 알코올, 벤질 벤조에이트, 프로필렌글리콜, 1,3-부틸글리콜 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 alcohol, benzyl benzoate, propylene glycol, 1 ,3-butylglycol 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 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다. When the formulation of the present invention is a suspension, 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, and crystallites Sex cellulose, aluminum metahydroxide, bentonite, agar or tracanth, and the like can be used.
본 발명의 제형이 계면-활성제 함유 클린징인 경우에는 담체 성분으로서 지방족 알코올 설페이트, 지방족 알코올 에테르 설페이트, 설포숙신산 모노에스테르, 이세티오네이트, 이미다졸리늄 유도체, 메틸타우레이트, 사르코시네이트, 지방산 아미드 에테르 설페이트, 알킬아미도베타인, 지방족 알코올, 지방산 글리세리드, 지방산 디에탄올아미드, 식물성 유, 라놀린 유도체 또는 에톡실화 글리세롤 지방산 에스테르 등이 이용될 수 있다. When the formulation of the present invention is a surfactant containing cleansing, as a carrier component, aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide Ether sulfates, alkylamidobetaines, fatty alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters may be used.
본 발명의 기능성 화장품 조성물에 포함되는 성분은 유효성분과 담체 성분 이외에, 화장품 조성물에 통상적으로 이용되는 성분들을 포함하며, 예컨대 항산화제, 안정화제, 용해화제, 비타민, 안료 및 향료와 같은 통상적인 보조제를 포함할 수 있다. The ingredients included in the functional cosmetic composition of the present invention include ingredients commonly used in cosmetic compositions in addition to the active ingredient and the carrier ingredient, and include conventional adjuvants such as antioxidants, stabilizers, solubilizers, vitamins, pigments, and fragrances. Can include.
본 발명의 카테킨 7-O-β-D-아피오푸란노사이드 화합물은 인간 유래 모유두 세포에서 테스토스테론으로부터 5알파-환원효소에 의해 변환되는 디하이드로테스토스테론(DHT)의 생성을 억제하여, 남성형 탈모증의 치료, 예방 또는 개선 용도의 활성물질로 이용될 수 있다. The catechin 7-O-β-D-apiofuranoside compound of the present invention inhibits the production of dihydrotestosterone (DHT), which is converted by 5 alpha-reductase from testosterone in human-derived dermal papilla cells, to prevent androgenetic alopecia. It can be used as an active substance for treatment, prevention or improvement purposes.
도 1a에는 본 발명의 화합물의 분리 공정을 요약한 공정 흐름도이다.
도 1b에는 느릅나무 가지 초임계 추출박의 에탄올 추출물내에서 카테킨 7-O-β-D-아피오푸란노사이드를 확인한 크로마토그래피 결과를 보여준다.
도 1c는 느릅나무 가지 초임계 추출박의 에탄올 추출물에 대해 에틸아세테이트로 분획한 분획물내에서 카테킨 7-O-β-D-아피오푸란노사이드를 확인한 크로마토그래피 결과를 보여준다.
도 1d는 느릅나무 가지 초임계 추출박의 에탄올 추출물에 대해 에틸아세테이트로 분획한 분획물을 Prep-LC으로 분리하여 얻은 카테킨 7-O-β-D-아피오푸란노사이드 화합물을 확인한 결과이다.
도 2a는 카테킨 7-O-β-D-아피오푸란노사이드 화합물의 TOF-MS의 분석결과이다.
도 2b는 카테킨 7-O-β-D-아피오푸란노사이드 화합물의 13C-NMR 데이터이다.
도 2c는 카테킨 7-O-β-D-아피오푸란노사이드 화합물의 1H-NMR 데이터이다.
도 2d는 카테킨 7-O-β-D-아피오푸란노사이드 화합물의 구조 분석 결과이다.
도 3는 카테킨 7-O-β-D-아피오푸란노사이드 화합물의 인간 유래 모유두 세포에서 디하이드로테스토스테론(Dihydrotestosterone, DHT)의 생성에 미치는 영향을 측정한 결과이다. *P<0.001 vs blank group. #P<0.001 and †P<0.05 vs testosterone group. Figure 1a is a process flow diagram summarizing the separation process of the compound of the present invention.
Figure 1b shows the chromatographic results confirming catechin 7-O-β-D-apiofuranoside in the ethanol extract of the supercritical extract of elm branches.
Figure 1c shows the chromatographic results confirming the catechin 7-O-β-D-apiofuranoside in the fraction fractionated with ethyl acetate for the ethanol extract of the supercritical extract of elm branches.
Figure 1d is a result of confirming the catechin 7-O-β-D-appiofuranoside compound obtained by separating the fraction fractionated with ethyl acetate for the ethanol extract of the supercritical extract of elm branches by Prep-LC.
Figure 2a is a TOF-MS analysis result of the catechin 7-O-β-D- apiofuranoside compound.
2B is 13C-NMR data of a catechin 7-O-β-D-apiofuranoside compound.
2C is 1H-NMR data of a catechin 7-O-β-D-apiofuranoside compound.
Figure 2d is the result of structural analysis of the catechin 7-O-β-D-apiofuranoside compound.
3 is a result of measuring the effect of a catechin 7-O-β-D-apiofuranoside compound on the production of dihydrotestosterone (DHT) in human-derived dermal papilla cells. *P<0.001 vs blank group. #P<0.001 and †P<0.05 vs testosterone group.
하기 본 명세서에서 설명된 구체적인 실시예는 본 발명의 바람직한 구현예 또는 예시를 대표하는 의미이며, 이에 의해 본 발명의 범위가 한정되지는 않는다. 본 발명의 변형과 다른 용도가 본 명세서 특허청구범위에 기재된 발명의 범위로부터 벗어나지 않는다는 것은 당업자에게 명백하다. The specific examples described in the present specification below are meant to represent preferred embodiments or examples of the present invention, and the scope of the present invention is not limited thereto. It will be apparent to those skilled in the art that variations and other uses of the invention do not depart from the scope of the invention described in the claims of this specification.
실시예 Example
1. 실험 재료 및 방법 1. Experimental materials and methods
(1) 카테킨 7-O-β-D-아피오푸란노사이드 화합물의 분리 (1) Isolation of Catechin 7-O-β-D-Apiofuranoside Compound
본 실험에서 느릅나무(Ulmus) 가지의 초임계 추출은 초임계유체 추출 생산용 장비(SCFE-P400, Ilsin Autoclave, Daejeon, Korea)를 사용하여 행하였다. In this experiment, supercritical extraction of Ulmus branches was performed using a supercritical fluid extraction production equipment (SCFE-P400, Ilsin Autoclave, Daejeon, Korea).
느릅나무 가지를 서울약령시장에서 구입하여 이물질을 제거하고 세척한 후, 음건하여 실험재료로 사용하였다. 건조된 시료 100kg을 200 메쉬(mesh)의 분쇄망을 통과하도록 분쇄하고, 분쇄된 느릅나무 가지를 추출조의 온도를 50℃로 조절하여 온도를 유지시켰다. 온도가 안정화되면 느릅나무 가지 시료를 넣고 CO2 가스를 등압으로 유지시킨 후, 고압펌프를 이용하여 라인(line)을 통해 실험압력 조건인 400 bar에 도달할 때까지 컨트롤 밸브(Control valve)를 조절하여 주입하였다. 설정 압력에 도달 후 추출조 하부로 에탄올(주정: 식용 알콜)을 분당 0.5~0.6L씩 160분 동안 총 60~80L를 투입하여 추출을 진행하였으며, 시료에 남아있는 잔존 에탄올을 제거하기 위해 설정된 압력과 온도로 60~120분동안 고압펌프를 이용하여 CO2를 흘려보내며 추출을 완료하였다. Elm branches were purchased at Seoul Yangnyeong Market, foreign substances were removed, washed, and then shaded to be used as an experimental material. 100 kg of the dried sample was pulverized so as to pass through a crushing net of 200 mesh, and the temperature of the pulverized elm branch was adjusted to 50° C. to maintain the temperature. When the temperature is stabilized, insert an elm branch sample and maintain the CO 2 gas at isostatic pressure, and then adjust the control valve through a line using a high-pressure pump until the experimental pressure condition reaches 400 bar. And injected. After reaching the set pressure, ethanol (alcohol: edible alcohol) was added to the bottom of the extraction tank at 0.5~0.6L per minute for a total of 60~80L for 160 minutes, and the pressure was set to remove the residual ethanol remaining in the sample. The extraction was completed by flowing CO 2 using a high-pressure pump at over temperature for 60 to 120 minutes.
위와 같이 느릅나무 가지를 초임계 추출을 하고 난 후에 얻어진 느릅나무 초임계 추출박 시료 100kg을 음건하여 60% 에탄올로 실온에서 1회 추출하여 여과하였다. 그 추출액을 감압농축 및 동결건조를 실시해 최종 4.81 kg을 확보하였다. After supercritical extraction of elm branches as described above, 100 kg of supercritical extract sample of elm tree obtained was dried in the shade, extracted once at room temperature with 60% ethanol, and filtered. The extract was concentrated under reduced pressure and freeze-dried to obtain a final 4.81 kg.
확보된 느릅나무 초임계 추출박의 에탄올 추출물(“USCFR”)을 1 kg 정량하여 분별깔때기를 이용하여 에틸아세테이트 용매분획을 실시하여 에틸아세테이트 용매 분획물(“USCFREA”) 185.2 g을 확보하였다. 1 kg of ethanol extract (“USCFR”) of the obtained elm supercritical extract was quantified, and ethyl acetate solvent fractionation was performed using a separatory funnel to obtain 185.2 g of an ethyl acetate solvent fraction (“USCFREA”).
확보한 에틸아세테이트 용매 분획물(“USCFREA”)으로부터 Prep-LC(Waters, 미국)를 이용하여, 실리카겔 레진을 활용할 때는 이동상인 용매를 Chloroform:Methanol:Water(70:30:4)를 사용하여 분리를 하였으며, C18 컬럼 레진을 활용할 때는 MeOH:Water(0 - 100%) 이동상 조건을 활용하여 단일 화합물을 정제 하였다(도 1a 내지 도 1d 참조). Using Prep-LC (Waters, USA) from the obtained ethyl acetate solvent fraction (“USCFREA”), and when using silica gel resin, use Chloroform:Methanol:Water (70:30:4) as a mobile phase solvent. And, when using a C18 column resin, a single compound was purified using MeOH:Water (0-100%) mobile phase conditions (see FIGS. 1A to 1D).
(2) TOF-MS를 활용한 추출물내의 지표 화합물의 분석 (2) Analysis of indicator compounds in extracts using TOF-MS
TMP를 통한 고진공과 고감도 검출기를 이용한 고분해능의 비행시간형 질량분석기(TOF-MS)로 Direct Probe를 이용하여 느릅나무 가지 초임계박 에탄올 추출물내의 주성분인 카테킨 7-O-β-D-아피오푸란노사이드의 분자량 및 분자구조를 확인하였다. A high-resolution time-of-flight mass spectrometer (TOF-MS) using a high vacuum and high sensitivity detector through TMP. The catechin 7-O-β-D-Apiofuranno, the main component in the ethanol extract of elm branch supercritical gourd using a direct probe. The molecular weight and molecular structure of the side were confirmed.
아래 표 1에 시료 정보 및 분석 조건을 기재하였다. Sample information and analysis conditions are described in Table 1 below.
TOF-MS의 분석결과는 도 2a에 나타내었고, 13C-NMR 데이터는 도 2b에 나타내었고, 1H-NMR 데이터는 도 2c에 나타내었다. 본 발명의 카테킨 7-O-β-D-아피오푸란노사이드 화합물의 구조 분석 결과는 도 2d에 나타내었다. The analysis results of TOF-MS are shown in Fig. 2A, 13C-NMR data are shown in Fig. 2B, and 1H-NMR data are shown in Fig. 2C. The results of structural analysis of the catechin 7-O-β-D-apiofuranoside compound of the present invention are shown in FIG. 2D.
(3) 세포 배양 (3) cell culture
본 실시예에서 사용한 인간 유래 모유두 세포(hair follicle dermal papilla cells, HFDPC)는 모발의 성장 및 유지의 특성을 나타내는 세포로써 PromoCell (Heidelberg, Germany)에서 구입하여 사용하였다. HDFPC 세포는 공급처에서 추천하는 papilla cell 전용 배지(PromoCell, Heidelberg, Germany or Cell biologics Inc, IL, USA)에 접종하여 37℃, 5% CO2 조건에서 24 - 48시간 계대 배양하여 실험에 사용하였다. Human-derived dermal papilla cells (HFDPC) used in this example were purchased and used from PromoCell (Heidelberg, Germany) as cells exhibiting the characteristics of hair growth and maintenance. HDFPC cells were inoculated in a papilla cell-only medium recommended by the supplier (PromoCell, Heidelberg, Germany or Cell biologics Inc, IL, USA) and subcultured for 24 to 48 hours under conditions of 37°C and 5% CO 2 and used in the experiment.
(4) 디하이드로테스토스테론 생성 억제 활성 분석 (4) Dihydrotestosterone production inhibitory activity assay
카테킨 7-O-β-D-아피오푸란노사이드(catechin 7-O-β-D-apiofuranoside)이 모유두 세포에서 테스토스테론으로부터 디하이드로테스토스테론을 생성하는 과정을 억제하는지를 실험하였다. 디하이드로테스토스테론(dihydrotestosterone, DHT) 정량 분석은 ELISA 키트 사용한 면역화학정량분석에 의해 실시하였다. DHT 분석 ELISA 키트는 Alpco (NH, USA)에서 구입하여 사용하였다. 키트를 사용한 실험은 제조사 제공의 지침서에 따라 실시하였으며, 세포 용해물(cell lysate) 부피(ml) 당 항원의 양(pg/μg)을 농도 단위로 환산하여 결과를 도출하였다. It was tested whether catechin 7-O-β-D-apiofuranoside inhibits the production of dihydrotestosterone from testosterone in dermal papilla cells. Quantitative analysis of dihydrotestosterone (DHT) was performed by immunochemical quantitative analysis using an ELISA kit. The DHT assay ELISA kit was purchased and used from Alpco (NH, USA). The experiment using the kit was conducted according to the manufacturer's instructions, and the result was derived by converting the amount of antigen (pg/μg) per volume (ml) of cell lysate into a concentration unit.
(5) 통계 처리 (5) statistical processing
모든 실험은 3회 반복 실시하여 평균값과 표준편차를 제시하였다. 또한 SPSS(Statistical Package for Social Science, ver. 18, IBM, Chicago IL. USA)를 이용하여 P<0.05 수준에서 실험군과 대조군의 평균치를 Student’s t-test로 유의성을 검증하였다. All experiments were repeated three times to present the mean value and standard deviation. In addition, using SPSS (Statistical Package for Social Science, ver. 18, IBM, Chicago IL. USA), the significance of the mean values of the experimental group and the control group at the P<0.05 level was verified with Student's t-test.
2. 실험결과 2. Experiment result
(1) 카테킨 7-O-β-D-아피오푸란노사이드의 디하이드로테스토스테론(DHT) 저해 활성 측정 결과 (1) Measurement result of dihydrotestosterone (DHT) inhibitory activity of catechin 7-O-β-D-apiofuranoside
모유두세포에 20nM 테스토스테론(Testosterone)을 처리 한 결과 디하이드로테스토스테론(dihydrotestosterone, DHT)의 생성량이 통계적으로 유의성 있게 높아짐을 확인하였다. As a result of treating dermal papilla cells with 20nM testosterone, it was confirmed that the production of dihydrotestosterone (DHT) was statistically significantly increased.
이어서, 카테킨 7-O-β-D-아피오푸란노사이드의 DHT 생성 억제능을 확인하기 위해 양성대조군으로서 남성형 탈모 방지 약품으로 잘 알려진 미녹시딜을 사용하여 비교 실험을 행하였다. 미녹시딜(10 μM)을 처리한 양성대조군에서는 DHT의 생성이 유의성 있게 억제됨을 확인하였다. 카테킨 7-O-β-D-아피오푸란노사이드(125 ㎍/㎖, 150 ㎍/㎖, 1100 ㎍/㎖)을 처리한 경우 미녹시딜 보다 강력하지는 않지만 농도 의존적으로 통계적으로 유의성 있게 DHT 생성을 억제하는 효과를 확인할 수 있었다. 음성대조군과 비교하였을 때에도 통계적으로 유의성 있게 DHT 생성을 억제하였다(도 3). Subsequently, in order to confirm the ability of catechin 7-O-β-D-afiofuranoside to inhibit DHT production, a comparative experiment was conducted using minoxidil, which is well known as an androgenic anti-hair loss drug, as a positive control. It was confirmed that the production of DHT was significantly suppressed in the positive control group treated with minoxidil (10 μM). Treatment with catechin 7-O-β-D-apiofuranoside (125 µg/ml, 150 µg/ml, 1100 µg/ml) inhibits DHT production in a statistically significant concentration-dependent manner, although it is not stronger than minoxidil. I could see the effect. Even when compared with the negative control group, DHT generation was statistically significantly suppressed (FIG. 3).
이상으로 본 발명의 특정한 부분을 상세히 기술하였는 바, 당업계의 통상의 지식을 가진 자에게 있어서 이러한 구체적인 기술은 단지 바람직한 구현 예일 뿐이며, 이에 본 발명의 범위가 제한되는 것이 아닌 점은 명백하다. 따라서, 본 발명의 실질적인 범위는 첨부된 청구항과 그의 등가물에 의하여 정의된다고 할 것이다.As described above, specific parts of the present invention have been described in detail, and it is clear that these specific techniques are only preferred embodiments for those of ordinary skill in the art, and the scope of the present invention is not limited thereto. Accordingly, it will be said that the substantial scope of the present invention is defined by the appended claims and their equivalents.
Claims (7)
A composition for the prevention or treatment of android type alopecia comprising a catechin 7-O-β-D-apiofuranoside compound as an active ingredient.
The method according to claim 1, wherein the catechin 7-O-β-D-apiofuranoside compound is one having an activity to inhibit the production of dihydrotestosterone (DHT) from testosterone, and composition for the prevention or treatment of androgenetic alopecia.
The method according to claim 1, wherein the android type alopecia is induced by dihydrotestosterone (DHT), a composition for preventing or treating android type alopecia.
The method according to claim 1, wherein the composition is a pharmaceutical composition, a composition for preventing or treating androgenetic alopecia.
Functional cosmetic composition for the prevention or improvement of android type alopecia comprising a catechin 7-O-β-D-apiofuranoside compound as an active ingredient.
The functional cosmetic composition of claim 5, wherein the catechin 7-O-β-D-apiofuranoside compound has an activity of inhibiting the production of dihydrotestosterone (DHT) from testosterone. .
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KR1020200114893A KR102249037B1 (en) | 2020-09-08 | 2020-09-08 | Composition for Improving, Preventing or Treating Male Pattern Alopecia Comprising Catechin 7-O-β-D-apiofuranoside As Active Ingredient |
US17/927,894 US20230201232A1 (en) | 2020-09-08 | 2021-04-29 | COMPOSITION FOR AMELIORATION, PREVENTION OR TREATMENT OF HAIR LOSS, COMPRISING CATECHIN 7-O-beta-D-APIOFURANOSIDE AS ACTIVE INGREDIENT |
EP21866938.0A EP4140490A4 (en) | 2020-09-08 | 2021-04-29 | Composition for amelioration, prevention or treatment of hair loss, comprising catechin 7-o-?-d-apiofuranoside as active ingredient |
PCT/KR2021/005465 WO2022055067A1 (en) | 2020-09-08 | 2021-04-29 | Composition for amelioration, prevention or treatment of hair loss, comprising catechin 7-o-β-d-apiofuranoside as active ingredient |
CN202180054968.0A CN116209451A (en) | 2020-09-08 | 2021-04-29 | Composition for improving, preventing or treating alopecia comprising catechin 7-O-beta-D-apioside as active ingredient |
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KR20060095062A (en) * | 2005-02-25 | 2006-08-30 | 주식회사 엘지생활건강 | Hair growth agent composition |
KR20130123626A (en) | 2012-05-03 | 2013-11-13 | 임용택 | Sea cucumber composition capable of preventing alopecia and skin-aging and environment-friendly cosmetic products using the same |
KR101659516B1 (en) | 2014-08-01 | 2016-09-23 | 전창진 | Hair growth natural composition for coating of head skin |
KR102016002B1 (en) | 2019-05-02 | 2019-08-29 | 주식회사 아이엘바이오 | Cosmetic composition for improving skin-whitening, anti-wrinkle and head skin |
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KR20060095062A (en) * | 2005-02-25 | 2006-08-30 | 주식회사 엘지생활건강 | Hair growth agent composition |
KR20130123626A (en) | 2012-05-03 | 2013-11-13 | 임용택 | Sea cucumber composition capable of preventing alopecia and skin-aging and environment-friendly cosmetic products using the same |
KR101659516B1 (en) | 2014-08-01 | 2016-09-23 | 전창진 | Hair growth natural composition for coating of head skin |
KR102016002B1 (en) | 2019-05-02 | 2019-08-29 | 주식회사 아이엘바이오 | Cosmetic composition for improving skin-whitening, anti-wrinkle and head skin |
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