KR101900244B1 - Composition for anti-obesity comprising novel compound isolated from Ainsliaea acerifolia extract as effective component - Google Patents
Composition for anti-obesity comprising novel compound isolated from Ainsliaea acerifolia extract as effective component Download PDFInfo
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- KR101900244B1 KR101900244B1 KR1020160099136A KR20160099136A KR101900244B1 KR 101900244 B1 KR101900244 B1 KR 101900244B1 KR 1020160099136 A KR1020160099136 A KR 1020160099136A KR 20160099136 A KR20160099136 A KR 20160099136A KR 101900244 B1 KR101900244 B1 KR 101900244B1
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Abstract
본 발명은 단풍취(Ainsliaea acerifolia) 추출물의 에틸아세테이트 분획물 또는 상기 분획물에서 분리한 화학식 1로 표시되는 화합물, 화학식 2로 표시되는 화합물 또는 이들의 혼합물을 유효성분으로 포함하는 항비만용 조성물에 관한 것으로, 본 발명의 화학식 1로 표시되는 화합물은 췌장 리파아제 저해 효과가 우수하며, 본 발명의 화학식 2로 표시되는 화합물은 지방세포 분화 억제 및 지방 축적 억제 효과가 우수하므로, 본 발명의 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물 단독 또는 이들의 혼합물을 비만의 예방 또는 치료용 약학 조성물 및 비만의 예방 또는 개선용 건강기능식품 조성물로서 유용하게 사용할 수 있다.The present invention relates to a process for producing Ainsliaea The present invention relates to an anti-obesity composition comprising an ethyl acetate fraction of an acerifolia extract or a compound represented by the general formula (1), a compound represented by the general formula (2) or a mixture thereof isolated from the fraction as an active ingredient. The compounds to be displayed are excellent in the effect of inhibiting pancreatic lipase, and the compounds represented by the formula (2) of the present invention are excellent in inhibition of adipocyte differentiation and inhibiting lipid accumulation. Therefore, the compound represented by the formula (1) Compounds alone or a mixture thereof can be usefully used as a pharmaceutical composition for preventing or treating obesity and a health functional food composition for preventing or ameliorating obesity.
Description
본 발명은 단풍취 추출물로부터 분리한 신규 화합물을 유효성분으로 포함하는 항비만용 조성물에 관한 것이다.The present invention relates to an anti-obesity composition comprising as an active ingredient a novel compound isolated from a single-puff extract.
비만은 체내에 지방이 필요 이상으로 과도하게 쌓인 경우를 말하며, 국민건강 통계에 따르면, 비만 유병률은 1998년 26.0%에서 2011년 31.4%로, 증가 추이를 보인다. 특히 비만은 다양한 성인병의 합병증과 관련이 있는 것으로 밝혀지고 있다. 예를 들어, 비만환자는 정상 체중인 사람에 비하여 간경변증 질환의 경우 2배, 뇌혈관질환의 경우 1.6배 및 관상동맥질환의 경우 1.8배 정도 사망률이 높은 것으로 보고되어 있다. Obesity is defined as the excess accumulation of fat in the body, and according to national health statistics, the prevalence of obesity is increasing from 26.0% in 1998 to 31.4% in 2011. Obesity has been found to be associated with complications of various adult diseases. For example, obesity patients have been reported to have a higher mortality rate compared to those who have normal weight, twice as much in the case of cirrhosis, 1.6 times in the case of cerebrovascular disease and 1.8 times in the case of coronary artery disease.
현재, 비만에 대한 치료방법으로 식이요법, 운동요법 및 약물요법 등이 시도되고 있으며, 이 중 약물요법으로 사용되는 비만치료제는 식욕의 조절, 지방의 소화·흡수 방해, 에너지 소비의 증가 또는 지질대사의 조절 등을 타겟으로 개발되었으나, 다양한 부작용이 존재한다.Currently, obesity treatment methods such as diet, exercise and drug therapy are being tried. Among them, the therapeutic agents for obesity, which are used as drug therapy, include appetite control, obstruction of digestion and absorption of fat, increase of energy consumption, , But there are various side effects.
제니칼(로슈)은 췌장 및 소화계에서 분리되는 리파아제 억제를 유도하여 지방흡수를 억제하지만, 2~3%의 낮은 체중감량 효과를 보이며, 잦은 설사, 지방변 등의 부작용을 동반한다. Xenical (Roche) induces lipase inhibition in the pancreas and digestive system, which inhibits fat absorption, but has a low weight loss effect of 2 to 3% and often has side effects such as diarrhea and fatty liver.
또한, 리덕틸(애보트)은 세로토닌과 노르아드레날린의 재흡수 억제를 통해 식욕을 억제시킴으로써, 5~10%의 체중감량효과가 있으나 뇌졸증과 심근경색 등 심혈관계 질환의 부작용이 있어, 2010년 유럽 의약품 안전청(EMA)과 미국 식품의약품안전청(FDA)이 처방과 사용중지 및 자발적 회수 권고조치를 내려 시장에서 퇴출되었으며, 국내에서는 2010년 10월경 식품의약품안전청에 의해 판매가 중단되었다. In addition, Reductile (Abbott) inhibits appetite by inhibiting the reuptake of serotonin and noradrenaline, thereby reducing weight loss by 5 to 10%. However, there are side effects of cardiovascular diseases such as stroke and myocardial infarction, (EMA) and the US Food and Drug Administration (FDA) have withdrawn from the market due to prescription and discontinuation and voluntary recall recommendations. In Korea, sales were discontinued by the Food and Drug Administration in October 2010.
이외에도 항비만 약제로 개발된 제품 중에서 심각한 부작용으로 인해 판매가 금지된 것들이 상당수에 이른다. 예로 아미노필린은 탁월한 체지방 분해효과에도 불구하고 정신신경계, 순환기계, 소화기계에 걸쳐 폭넓은 부작용이 보고된 바 있고, 펜프루라민, 덱스펜플루라민, 토피라메이 또는 에피드린 등도 비만치료에 부적합한 약물로 판정되어 판매가 금지되었다. 이와 같이 합성의약품의 부작용과 만성질환의 극복에 서양의학이 한계를 보임에 따라 항비만 효과를 가진 천연물 식·의약품에 대한 가치가 새롭게 부각되고 있다. In addition, many of the products developed as anti-obesity drugs are prohibited from selling due to serious side effects. For example, aminophylline has been reported to have widespread adverse effects on the mental nervous system, circulatory system, and digestive system, despite its excellent body fat degradation, and penfluramine, dexfenfluramine, topiramime, or ephedrine, Sales were banned. As such, the value of natural products and medicines with anti-obesity effect is newly emerging due to the limitations of western medicine due to side effects of synthetic drugs and overcoming of chronic diseases.
한편, 단풍취(Ainsliaea acerifolia)는 국화과(Compositae)에 속하는 다년초로서, 높이 35~80cm이고, 가지가 없으며, 긴 갈색 털이 드문드문 있다. 식용으로는 어린 순을 먹으며, 류마티스 관절염과 식중독을 치료하는데 사용하여 왔다. Ainsliaea acerifolia is a perennial plant belonging to the family Asteraceae (Compositae), 35-80 cm high, without branches, and long brown hairs are sparse. It has been used for the treatment of rheumatoid arthritis and food poisoning.
한국등록특허 제1405429호는 단풍취를 포함하는 야생초 화장품에 대하여 개시하고 있으며, 한국공개특허 제2016-0027401호는 마가목 또는 단풍취 추출물을 포함하는 쌀국수 및 이의 제조방법을 개시하고 있으나, 본 발명의 단풍취 추출물로부터 분리한 신규 화합물을 유효성분으로 포함하는 항비만용 조성물에 대해서는 개시된 바 없다. Korean Patent Publication No. 1405429 discloses a wild grass cosmetic containing a single-pest, Korean Patent Laid-Open Publication No. 2016-0027401 discloses a rice nucifera containing an extract of Ravine or a Pale Breeze and a preparation method thereof, Has not been disclosed for an anti-obesity composition containing a novel compound as an active ingredient.
본 발명은 상기와 같은 요구에 의해 도출된 것으로서, 본 발명은 단풍취 추출물의 에틸아세테이트 분획물에서 분리한 신규 화합물을 유효성분으로 포함하는 항비만용 조성물을 제공하고, 본 발명의 신규 화합물이 췌장 리파아제 활성 저해 효과와 지방세포 분화 억제 및 지방 축적 억제 효과를 나타낸다는 것을 확인함으로써, 본 발명을 완성하였다.SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned needs, and an object of the present invention is to provide an anti-obesity composition comprising as an active ingredient a novel compound isolated from the ethyl acetate fraction of the extract of A. pneumoniae, Inhibitory effect, suppression of adipocyte differentiation and inhibition of fat accumulation, thereby completing the present invention.
상기 목적을 달성하기 위하여, 본 발명은 단풍취(Ainsliaea acerifolia) 추출물의 에틸아세테이트 분획물을 유효성분으로 포함하는 비만의 예방 또는 치료용 약학 조성물을 제공한다.In order to achieve the above object, the present invention relates to a method for producing Ainsliaea The present invention provides a pharmaceutical composition for preventing or treating obesity comprising an ethyl acetate fraction of acerifolia extract as an active ingredient.
또한, 본 발명은 하기 화학식 1로 표시되는 화합물 또는 약제학적으로 허용 가능한 그의 염; 하기 화학식 2로 표시되는 화합물 또는 약제학적으로 허용 가능한 그의 염; 또는 이들의 혼합물;을 유효성분으로 포함하는 것을 특징으로 하는 비만의 예방 또는 치료용 약학 조성물을 제공한다.The present invention also relates to a compound represented by the following general formula (1): or a pharmaceutically acceptable salt thereof; A compound represented by the following formula 2 or a pharmaceutically acceptable salt thereof; Or a mixture thereof, as an active ingredient. The present invention also provides a pharmaceutical composition for preventing or treating obesity.
상기 화학식 1에서,In Formula 1,
R은 쿠마로일기(coumaroyl)를 나타낸다.R represents coumaroyl.
상기 화학식 2에서,In Formula 2,
R1 및 R2는 각각 카페오일기(caffeoyl)를 나타내고;R 1 and R 2 each represent a caffeoyl;
R3는 메틸기를 나타낸다.R 3 represents a methyl group.
또한, 본 발명은 단풍취(Ainsliaea acerifolia) 추출물의 에틸아세테이트 분획물을 유효성분으로 포함하는 비만의 예방 또는 개선용 건강기능식품 조성물을 제공한다.The present invention also relates to a process for the production of Ainsliaea The present invention provides a health functional food composition for preventing or ameliorating obesity comprising an ethyl acetate fraction of an acerifolia extract as an active ingredient.
또한, 본 발명은 화학식 1로 표시되는 화합물 또는 그의 염; 화학식 2로 표시되는 화합물 또는 그의 염; 또는 이들의 혼합물;을 유효성분으로 포함하는 것을 특징으로 하는 비만의 예방 또는 개선용 건강기능식품 조성물을 제공한다.The present invention also relates to a compound represented by the formula (1) or a salt thereof; A compound represented by the formula (2) or a salt thereof; Or a mixture thereof, as an active ingredient. The present invention also provides a health functional food composition for preventing or ameliorating obesity.
본 발명은 단풍취(Ainsliaea acerifolia) 추출물의 에틸아세테이트 분획물 또는 상기 분획물에서 분리한 화학식 1로 표시되는 화합물, 화학식 2로 표시되는 화합물 또는 이들의 혼합물을 유효성분으로 포함하는 항비만용 조성물에 관한 것으로, 본 발명의 화학식 1로 표시되는 화합물은 췌장 리파아제 저해 효과가 우수하며, 본 발명의 화학식 2로 표시되는 화합물은 지방세포 분화 억제 및 지방 축적 억제 효과가 우수하므로, 본 발명의 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물 단독 또는 이들의 혼합물을 비만의 예방 또는 치료용 약학 조성물 및 비만의 예방 또는 개선용 건강기능식품 조성물로서 유용하게 사용할 수있다.The present invention relates to a process for producing Ainsliaea The present invention relates to an anti-obesity composition comprising an ethyl acetate fraction of an acerifolia extract or a compound represented by the general formula (1), a compound represented by the general formula (2) or a mixture thereof isolated from the fraction as an active ingredient. The compounds to be displayed are excellent in the effect of inhibiting pancreatic lipase, and the compounds represented by the formula (2) of the present invention are excellent in inhibition of adipocyte differentiation and inhibiting lipid accumulation. Therefore, the compound represented by the formula (1) Compounds alone or a mixture thereof can be usefully used as a pharmaceutical composition for preventing or treating obesity and a health functional food composition for preventing or ameliorating obesity.
도 1은 화학식 2로 표시되는 신규 화합물의 지방세포 분화 저해효과 및 지방 축적 저해효과를 확인한 결과이다. p value가 0.01 미만이면 유의성이 있는 것으로 평가하였다.Fig. 1 shows the results of confirming the adipocyte differentiation inhibitory effect and the fat accumulation inhibitory effect of the novel compound represented by the formula (2). A p value of less than 0.01 was considered significant.
본 발명은 단풍취(Ainsliaea acerifolia) 추출물의 에틸아세테이트 분획물을 유효성분으로 포함하는 비만의 예방 또는 치료용 약학 조성물에 관한 것이다.The present invention relates to a process for producing Ainsliaea The present invention relates to a pharmaceutical composition for preventing or treating obesity, which comprises an ethyl acetate fraction of an acerifolia extract as an active ingredient.
본 발명의 단풍취는 전체 지상부 및 지하부를 사용할 수 있으며, 바람직하게는 단풍취의 지상부를 사용하는 것이 바람직하다.In the present invention, it is possible to use the entire ground portion and the ground portion, and preferably, the ground portion of the ventilation odor is preferably used.
본 발명의 단풍취 추출물은 당업계에 공지된 통상의 추출방법을 제한 없이 이용하여 제조될 수 있고, 통상의 추출방법은 초음파 추출법, 여과법 및 환류추출법 등을 포함할 수 있으나, 이에 한정되지 않는다. The extract of the present invention may be prepared using any conventional extraction method known in the art without limitation, and conventional extraction methods may include, but are not limited to, ultrasonic extraction, filtration and reflux extraction.
본 발명의 단풍취 추출물은 단풍취 전체 또는 일부(잎, 뿌리 또는 열매)를 물, C1~C4의 저급 알코올 또는 이들의 혼합물을 추출용매로 사용하여 추출하는 것이 바람직하며, 더 바람직하게는 에탄올로 추출하는 것이며, 더욱더 바람직하게는 70%(v/v)의 에탄올을 사용하여 추출하는 것이지만, 이에 한정하는 것은 아니다.The extract of the present invention is preferably extracted with water or a lower alcohol of C 1 -C 4 or a mixture thereof as an extraction solvent, more preferably ethanol And more preferably 70% (v / v) ethanol. However, the present invention is not limited thereto.
본 발명에서, '분획물'은 다양한 구성성분을 포함하는 혼합물로부터 특정 성분 또는 특정 그룹을 분리하는 분획방법에 의하여 얻어진 결과물을 의미한다. 용매 분획, 실리카겔 크로마토그래피, 역상 크로마토그래피, prep-HPLC 등을 이용하여 활성 물질이 농축된 특정 분획물을 제조할 수 있다.In the present invention, 'fraction' means the result obtained by a fractionation method for separating a specific component or a specific group from a mixture containing various constituents. Particular fractions enriched in active material can be prepared using solvent fractions, silica gel chromatography, reverse phase chromatography, prep-HPLC, and the like.
상기 단풍취 추출물의 에틸아세테이트 분획물은 하기 화학식 1로 표시되는 화합물, 하기 화학식 2로 표시되는 화합물 또는 이들의 혼합물을 유효성분으로 포함할 수 있다.The ethylacetate fraction of the single-puff extract may contain, as an active ingredient, a compound represented by the following formula (I), a compound represented by the following formula (II), or a mixture thereof.
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R은 쿠마로일기(coumaroyl)를 나타낸다. R represents coumaroyl.
[화학식 2](2)
상기 화학식 2에서,In Formula 2,
R1 및 R2는 각각 카페오일기(caffeoyl)를 나타내고;R 1 and R 2 each represent a caffeoyl;
R3는 메틸기를 나타낸다.R 3 represents a methyl group.
본 발명은 상기 화학식 1로 표시되는 화합물 또는 약제학적으로 허용 가능한 그의 염; 상기 화학식 2로 표시되는 화합물 또는 약제학적으로 허용 가능한 그의 염; 또는 이들의 혼합물;을 유효성분으로 포함하는 것을 특징으로 하는 비만의 예방 또는 치료용 약학 조성물에 관한 것이다.The present invention relates to a compound represented by the general formula (1) or a pharmaceutically acceptable salt thereof; A compound represented by Formula 2 or a pharmaceutically acceptable salt thereof; Or a mixture thereof, as an active ingredient. The present invention also relates to a pharmaceutical composition for preventing or treating obesity.
본 발명의 상기 화학식 1 및 2로 표시되는 화합물들은 화합물에 따라 약학적으로 허용 가능한 염의 형태로 투여될 수 있다. "약제학적으로 허용 가능한 염"은 독성이 없거나 적은 산 또는 염기로 제조된 염들을 말한다. The compounds represented by formulas (1) and (2) of the present invention may be administered in the form of a pharmaceutically acceptable salt depending on the compound. "Pharmaceutically acceptable salts" refer to salts prepared with little or no acidity or base.
본 발명의 화합물들이 상대적으로 산성일 경우 염기(base) 부가 염들은 충분한 양의 원하는 염기와 적당한 비활성(inert) 용매로 그러한 화합물들의 중성 형태를 접촉하여 얻을 수 있다. When the compounds of the present invention are relatively acidic, base addition salts can be obtained by contacting neutral forms of such compounds with a sufficient amount of the desired base and a suitable inert solvent.
약제학적으로 허용 가능한 염기 부가 염은 나트륨, 칼륨, 칼슘, 암모늄, 마그네슘 또는 유기 아미노로 이루어진 염을 포함하나, 이에 한정되는 것은 아니다. Pharmaceutically acceptable base addition salts include, but are not limited to, salts of sodium, potassium, calcium, ammonium, magnesium or organic amino.
본 발명의 화합물들이 상대적으로 염기성일 경우 산(acid) 부가 염들은 충분한 양의 원하는 산과 적당한 비활성 용매로 그러한 화합물들의 중성 형태를 접촉하여 얻을 수 있다. Where the compounds of the present invention are relatively basic, acid addition salts may be obtained by contacting the neutral form of such compounds with a sufficient amount of the desired acid and a suitable inert solvent.
약제학적으로 허용 가능한 산 부가 염은 프로피온산, 이소부틸산, 옥살산, 사과산, 말론산, 안식향산, 호박산, 수버릭(suberic), 푸마르산, 만데릭산, 프탈릭산, 벤젠설폰산, p-토릴설폰산, 구연산, 주석산, 메탄설폰산, 염산, 브롬산, 질산, 탄산, 일수소탄산(monohydrogencarbonic), 인산, 일수소인산, 이수소인산, 황산, 일수소황산, 요오드화수소 또는 아인산(phosphorous acid)으로 형성된 염을 포함하나, 이에 한정되는 것은 아니다. Pharmaceutically acceptable acid addition salts include those derived from propionic acid, isobutyric acid, oxalic acid, malic acid, malonic acid, benzoic acid, succinic acid, sueric, fumaric acid, mandelic acid, phthalic acid, benzenesulfonic acid, Monohydrogencarbonic acid, phosphoric acid, monohydrogenphosphoric acid, dihydrogenphosphoric acid, sulfuric acid, monohydrogensulfuric acid, hydrogen iodide or phosphorous acid, and the like. ≪ / RTI > but are not limited to, the salts formed with
또한, 알지네이트(arginate) 같은 아미노산의 염 및 글루쿠로닉(glucuronic) 또는 갈락투노릭(galactunoric) 산들과 같은 유기산의 유사체를 포함하나, 이에 한정되는 것은 아니다.It also includes, but is not limited to, salts of amino acids such as arginate and analogs of organic acids such as glucuronic or galactunoric acids.
본 발명의 화합물들은 화합물에 따라 수화물 형태를 포함하여 용매화된 형태뿐만 아니라 비-용매화된(unsolvated) 형태로 존재할 수도 있다. 본 발명의 화합물들은 결정형 또는 무정형 형태로 존재할 수 있으며, 이러한 모든 물리적 형태는 본 발명의 범위에 포함된다. The compounds of the present invention may exist in unsolvated as well as solvated forms, including hydrated forms depending on the compound. The compounds of the present invention may exist in crystalline or amorphous form, and all such physical forms are included within the scope of the present invention.
또한, 본 발명의 화합물들은 화합물에 따라 광학 중심인 비대칭 탄소원자 또는 이중 결합을 가질 수 있어 라세미체, 에난치오머, 디아스테레오머, 기하 이성질체 등이 존재할 수 있으며, 이들 또한 본 발명의 범위에 포함된다.In addition, the compounds of the present invention may have an asymmetric carbon atom or a double bond, which is an optical center depending on the compound, and thus there may exist racemates, enanthiomers, diastereomers, geometric isomers and the like, .
본 발명의 약학 조성물은 경구 또는 비경구의 여러 가지 제형일 수 있다. 제제화할 경우에는 보통 사용하는 충진제, 증량제, 결합제, 습윤제, 붕해제, 계면활성제 등의 희석제 또는 부형제를 사용하여 조제된다. 경구투여를 위한 고형 제제에는 정제, 환제, 산제, 과립제, 캡슐제 등이 포함되며, 이러한 고형 제제는 하나 이상의 화합물에 적어도 하나 이상의 부형제 예를 들면, 전분, 탄산칼슘, 수크로오스(sucrose) 또는 락토오스(lactose), 젤라틴 등을 섞어 조제된다. 또한, 단순한 부형제 이외에 스테아린산 마그네슘, 탈크 등과 같은 윤활제들도 사용된다. The pharmaceutical composition of the present invention may be various oral or parenteral formulations. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid formulations for oral administration include tablets, pills, powders, granules, capsules, and the like, which may contain one or more excipients such as starch, calcium carbonate, sucrose or lactose lactose, gelatin and the like. In addition to simple excipients, lubricants such as magnesium stearate, talc, and the like may also be used.
경구 투여를 위한 액상 제제로는 현탁제, 내용액제, 유제, 시럽제 등이 해당되는데 흔히 사용되는 단순 희석제인 물, 리퀴드 파라핀 이외에 여러 가지 부형제, 예를 들면 습윤제, 감미제, 방향제, 보존제 등이 포함될 수 있다. 비경구 투여를 위한 제제에는 멸균된 수용액, 비수성 용제, 현탁제, 유제, 동결건조제제, 좌제가 포함된다.Liquid preparations for oral administration include suspensions, solutions, emulsions, syrups and the like. Various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like may be included in addition to water and liquid paraffin, which are simple diluents commonly used. have. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, freeze-dried preparations, and suppositories.
비수성 용제 및 현탁 용제로는 프로필렌글리콜(propylene glycol), 폴리에틸렌 글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테르 등이 사용될 수 있다. 좌제의 기제로는 위텝솔(witepsol), 마크로골, 트윈tween) 61, 카카오지, 라우린지, 글리세로 젤라틴 등이 사용될 수 있다.Examples of non-aqueous solvents and suspensions include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, injectable esters such as ethyl oleate, and the like. Examples of suppositories include witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin and the like.
본 발명의 약학 조성물은 경구 또는 비경구로 투여될 수 있으며, 비경구 투여 시 피부 외용 또는 복강 내, 직장, 정맥, 근육, 피하, 자궁 내 경막 또는 뇌혈관 내 주사 방식을 선택하는 것이 바람직하지만, 이에 한정하는 것은 아니다.The pharmaceutical composition of the present invention may be administered orally or parenterally, and it is preferable to select the intravenous, intraperitoneal, rectal, intravenous, intramuscular, subcutaneous, intrauterine or intracerebral injection methods during parenteral administration, But is not limited to.
본 발명에 따른 약학 조성물은 약제학적으로 유효한 양으로 투여한다. 본 발명에 있어서, "약제학적으로 유효한 양"은 의학적 치료에 적용 가능한 합리적인 수혜/위험 비율로 질환을 치료하기에 충분한 양을 의미하며, 유효용량 수준은 환자의 질환의 종류, 중증도, 약물의 활성, 약물에 대한 민감도, 투여 시간, 투여 경로 및 배출 비율, 치료기간, 동시 사용되는 약물을 포함한 요소 및 기타 의학 분야에 잘 알려진 요소에 따라 결정될 수 있다. 본 발명의 조성물은 개별 치료제로 투여하거나 다른 치료제와 병용하여 투여될 수 있고 종래의 치료제와는 순차적 또는 동시에 투여될 수 있으며, 단일 또는 다중 투여될 수 있다. 상기한 요소들을 모두 고려하여 부작용없이 최소한의 양으로 최대 효과를 얻을 수 있는 양을 투여하는 것이 중요하며, 이는 당업자에 의해 용이하게 결정될 수 있다.The pharmaceutical composition according to the present invention is administered in a pharmaceutically effective amount. In the present invention, "pharmaceutically effective amount" means an amount sufficient to treat a disease at a reasonable benefit / risk ratio applicable to medical treatment, and the effective dose level will depend on the type of disease, severity, , Sensitivity to the drug, time of administration, route of administration and rate of release, duration of treatment, factors including co-administered drugs, and other factors well known in the medical arts. The composition of the present invention can be administered as an individual therapeutic agent or in combination with other therapeutic agents, and can be administered sequentially or simultaneously with conventional therapeutic agents, and can be administered singly or in multiple doses. It is important to take into account all of the above factors and to administer the amount in which the maximum effect can be obtained in a minimal amount without side effects, which can be easily determined by those skilled in the art.
본 발명의 조성물의 투여량은 환자의 체중, 연령, 성별, 건강상태, 식이, 투여시간, 투여방법, 배설률 및 질환의 중증도에 따라 그 범위가 다양하게 사용할 수 있다.The dosage of the composition of the present invention may be varied depending on the patient's body weight, age, sex, health condition, diet, administration time, administration method, excretion rate, and severity of disease.
본 발명은 단풍취(Ainsliaea acerifolia) 추출물의 에틸아세테이트 분획물을 유효성분으로 포함하는 비만의 예방 또는 개선용 건강기능식품 조성물에 관한 것이다.The present invention relates to a process for producing Ainsliaea The present invention relates to a health functional food composition for preventing or ameliorating obesity comprising an ethyl acetate fraction of an acerifolia extract as an active ingredient.
본 발명의 단풍취는 전체 지상부 및 지하부를 사용할 수 있으며, 바람직하게는 단풍취의 지상부를 사용하는 것이 바람직하다.In the present invention, it is possible to use the entire ground portion and the ground portion, and preferably, the ground portion of the ventilation odor is preferably used.
본 발명의 단풍취 추출물은 당업계에 공지된 통상의 추출방법을 제한 없이 이용하여 제조될 수 있고, 통상의 추출방법은 초음파 추출법, 여과법 및 환류추출법 등을 포함할 수 있으나, 이에 한정되지 않는다. The extract of the present invention may be prepared using any conventional extraction method known in the art without limitation, and conventional extraction methods may include, but are not limited to, ultrasonic extraction, filtration and reflux extraction.
본 발명의 단풍취 추출물은 단풍취 전체 또는 일부(잎, 뿌리 또는 열매)를 물, C1~C4의 저급 알코올 또는 이들의 혼합물을 추출용매로 사용하여 추출하는 것이 바람직하며, 더 바람직하게는 에탄올로 추출하는 것이며, 더욱더 바람직하게는 70%(v/v)의 에탄올을 사용하여 추출하는 것이지만, 이에 한정하는 것은 아니다.The extract of the present invention is preferably extracted with water or a lower alcohol of C 1 -C 4 or a mixture thereof as an extraction solvent, more preferably ethanol And more preferably 70% (v / v) ethanol. However, the present invention is not limited thereto.
본 발명에서, '분획물'은 다양한 구성성분을 포함하는 혼합물로부터 특정 성분 또는 특정 그룹을 분리하는 분획방법에 의하여 얻어진 결과물을 의미한다. 용매 분획, 실리카겔 크로마토그래피, 역상 크로마토그래피, prep-HPLC 등의 기술을 이용하여 활성물질이 농축된 특정 분획물을 제조할 수 있다.In the present invention, 'fraction' means the result obtained by a fractionation method for separating a specific component or a specific group from a mixture containing various constituents. Specific fractions enriched in active material can be prepared using techniques such as solvent fractions, silica gel chromatography, reverse phase chromatography, prep-HPLC, and the like.
상기 단풍취 추출물의 에틸아세테이트 분획물은 하기 화학식 1로 표시되는 화합물, 하기 화학식 2로 표시되는 화합물 또는 이들의 혼합물을 유효성분으로 포함할 수 있다.The ethylacetate fraction of the single-puff extract may contain, as an active ingredient, a compound represented by the following formula (I), a compound represented by the following formula (II), or a mixture thereof.
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R은 쿠마로일기(coumaroyl)를 나타낸다. R represents coumaroyl.
[화학식 2](2)
상기 화학식 2에서,In Formula 2,
R1 및 R2는 각각 카페오일기(caffeoyl)를 나타내고;R 1 and R 2 each represent a caffeoyl;
R3는 메틸기를 나타낸다.R 3 represents a methyl group.
본 발명은 상기 화학식 1로 표시되는 화합물 또는 그의 염; 상기 화학식 2로 표시되는 화합물 또는 그의 염; 또는 이들의 혼합물;을 유효성분으로 포함하는 것을 특징으로 하는 비만의 예방 또는 개선용 건강기능식품 조성물에 관한 것이다.The present invention relates to a compound represented by the general formula (1) or a salt thereof; A compound represented by the formula (2) or a salt thereof; Or a mixture thereof, as an active ingredient. The present invention also relates to a health functional food composition for preventing or ameliorating obesity.
본 발명의 건강기능식품 조성물은 음료, 환, 정제(tablet), 캡슐제(capsule) 및 산제 중에서 선택된 어느 하나로 제조하거나, 다른 식품 또는 식품의 성분에 첨가하여 제조될 수 있으며, 통상적인 방법에 따라 적절하게 제조될 수 있다.The health functional food composition of the present invention can be prepared by any one selected from beverage, ring, tablet, capsule and acid, or by adding it to other food or ingredients of food, Can be suitably manufactured.
본 발명의 건강기능식품 조성물을 첨가할 수 있는 식품의 일례로는 육류, 소시지, 빵, 초콜릿, 캔디류, 스넥류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차, 드링크제, 알코올 음료 및 비타민 복합제 중에서 선택된 어느 하나의 형태일 수 있으며, 통상적인 의미에서의 건강식품을 모두 포함한다. Examples of foods to which the health functional food composition of the present invention can be added include dairy products including meat, sausage, bread, chocolate, candy, snack, confectionery, pizza, ramen, other noodles, gums, ice cream, Beverage, tea, drink, alcoholic beverage, and vitamin complex, and includes all the health foods in the ordinary sense.
상기 건강기능식품은 여러 가지 영양제, 비타민, 광물(전해질), 합성 및 천연 풍미제, 착색제 및 증진제(치즈, 초콜릿 등), 펙트산 및 그의 염, 알킨산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알코올, 탄산음료에 사용되는 탄산화제 등을 함유할 수 있다. 그 밖에 천연 과일 주스 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 이러한 성분은 독립적으로 또는 조합하여 사용할 수 있다. The health functional foods include various nutrients, vitamins, minerals (electrolytes), synthetic and natural flavors, colorants and enhancers (cheese, chocolate etc.), pectic acid and its salts, alkynic acid and its salts, , pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, carbonating agents used in carbonated drinks, and the like. It may also contain flesh for the production of natural fruit juices and vegetable drinks. These components may be used independently or in combination.
본 발명의 건강기능식품 조성물은 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있다. 상기 천연 탄수화물은 포도당, 과당과 같은 모노사카라이드, 말토스, 슈크로스와 같은 디사카라이드, 및 덱스트린, 사이클로덱스트린과 같은 폴리사카라이드, 자일리톨, 소르비톨, 에리트리톨 등의 당알콜이다. 감미제로서는 타우마틴, 스테비아 추출물과 같은 천연 감미제나, 사카린, 아스파르탐과 같은 합성 감미제 등을 사용할 수 있다. The health functional food composition of the present invention may contain various flavors or natural carbohydrates as an additional ingredient. The natural carbohydrates are sugar saccharides such as monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, xylitol, sorbitol and erythritol. Examples of sweeteners include natural sweeteners such as tau martin and stevia extract, synthetic sweeteners such as saccharin and aspartame, and the like.
이하, 실시예를 이용하여 본 발명을 더욱 상세하게 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로 본 발명의 범위가 이들에 의해 제한되지 않는다는 것은 당해 기술분야에서 통상의 지식을 가진 자에게 있어 자명한 것이다. Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are merely illustrative of the present invention and that the scope of the present invention is not limited thereto.
실시예Example 1. One. 단풍취A single blow 추출물로부터 단일 화합물의 분리 Isolation of a single compound from the extract
1-1. 단풍취 추출물로부터 유기 용매 분획물의 제조1-1. Preparation of organic solvent fractions from sweet algae extract
신선한 단풍취(Ainsliaea acerifolia) 5.0 kg을 적당한 크기로 분쇄한 후, 실온에서 70% 에탄올로 3회 추출한 후 감압 농축하여 70% 에탄올 추출물 (203.3g)을 얻었다. 70% 에탄올 추출물을 4L의 10% 메탄올에 현탁시켜 n-헥산을 4L씩 2회 분획하여, n-헥산 분획물을 얻었다. 이어서 물 분획물에 에틸 아세테이트, 부탄올로 순차적으로 4L씩 2회 용매분획하였고, 나머지를 물 분획물로 하였다. 이에 따란 n-헥산 분획물 73.8g, 에틸 아세테이트 분획물 56.0g, 부탄올 분획물 28.0g 및 물 분획물 186.0g을 얻었다.Fresh breeze ( Ainsliaea acerifolia ) were pulverized to an appropriate size, and then extracted three times with 70% ethanol at room temperature, followed by concentration under reduced pressure to obtain a 70% ethanol extract (203.3 g). The 70% ethanol extract was suspended in 4 L of 10% methanol, and n-hexane was fractionated twice in 4 L portions to obtain n-hexane fractions. Subsequently, the water fraction was fractionated twice with 4 L each of ethyl acetate and butanol sequentially, and the remainder was used as a water fraction. There were obtained 73.8 g of the n-hexane fraction, 56.0 g of the ethyl acetate fraction, 28.0 g of the butanol fraction and 186.0 g of the water fraction.
1-2. 유기 용매 분획물로부터 활성 성분의 분리1-2. Isolation of active ingredient from organic solvent fractions
상기 1-1에서 제조된 단풍취의 에틸 아세테이트 분획물이 췌장 리파아제 저해활성을 나타냄을 확인하였고, 상기 단풍취의 에틸아세테이트 분획물로부터 활성성분을 분리하기 위해서, HW-40 역상컬럼 크로마토그래피(Toyopearl HW-40 column, coarse grade, 2.8 cm×51 cm)를 이용하여 전개용매 H2O, 20%, 40%, 60% 및 100% 메탄올(v/v)로 분취하였다. 상기 분취 순서에 따라 총 5개의 분획으로 나누어 각각의 분획을 농축 건조하였다.It was confirmed that the ethyl acetate fraction obtained from the above-mentioned 1-1 showed the pancreatic lipase inhibitory activity. To isolate the active ingredient from the ethyl acetate fraction of the above-mentioned odor pest, HW-40 reverse phase column chromatography (Toyopearl HW-40 column , 20%, 40%, 60%, and 100% methanol (v / v) using the developed solvent, H2O, coarse grade, 2.8 cm × 51 cm. The fractions were divided into five fractions according to the above sorting order, and the respective fractions were concentrated and dried.
상기 5개의 분획 중 3번째 분획을 40% 메탄올(v/v) 용리액에 대해서 20% 메탄올(v/v) 용매로 하여 컬럼 크로마토그래피(YMC GEL ODS AQ 120-50S column, 1.1 cm×40 cm, YMC Co., Kyoto, Japan) 를 수행한 후 HPLC(20% 아세토니트릴, YMC-Pack ODS A-302 column, 4.6 mm×150 mm, YMC Co., Kyoto, Japan) 로 정제하여 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물을 각각 분리하였다.The third fraction of the five fractions was subjected to column chromatography (YMC GEL ODS AQ 120-50S column, 1.1 cm x 40 cm, elution solvent: 20% methanol (v / v) YMC Co., Kyoto, Japan) and then purified by HPLC (20% acetonitrile, YMC-Pack ODS A-302 column, 4.6 mm x 150 mm, YMC Co., Kyoto, Japan) The compound and the compound represented by the formula (2) were respectively separated.
1-3. 화학식 1로 표시되는 화합물의 구조분석1-3. Structural analysis of the compound represented by formula (1)
상기 실시예 1-2에서 분리한 화학식 1로 표시되는 화합물의 [α]D 값, UV 스펙트럼, IR 스펙트럼, HR-FAB-MS 스펙트럼, 1H-NMR 및 13C-NMR을 측정한 결과는 하기 기재한 바와 같으며, 이에 따라 화학식 1의 화합물을 동정하였다.[Α] D value, UV spectrum, IR spectrum, HR-FAB-MS spectrum, 1 H-NMR and 13 C-NMR of the compound of the formula (1) The compound of formula (1) was identified.
[α]D: +23.0° (c. 0.1, MeOH);[[alpha]] D : +23.0 [deg.] (c 0.1, MeOH);
UV max(MeOH) nm : 207.0, 246.0, 301.0;UV max (MeOH) nm: 207.0, 246.0, 301.0;
IR (nujol) cm- 1 : 3400, 1746, 1705, 1512, 1435, 1255, 1151;IR (nujol) cm - 1 : 3400, 1746, 1705, 1512, 1435, 1255, 1151;
HR-FAB-MS: 577.2093 [M+Na]+ (C30H34O10Na);HR-FAB-MS: 577.2093 [ M + Na] + (C 30 H 34 O 10 Na);
NMR (DMSO-d6): 하기 표 1NMR (DMSO-d6): < EMI ID =
1-4. 화학식 2로 표시되는 화합물의 구조분석1-4. Structural analysis of the compound represented by formula (2)
상기 실시예 1-2에서 분리한 화학식 2로 표시되는 화합물의 [α]D 값, UV 스펙트럼, IR 스펙트럼, HR-FAB-MS 스펙트럼, 1H-NMR 및 13C-NMR을 측정한 결과는 하기 기재한 바와 같으며, 이에 따라 동정하여 화합물 2는 methyl 3,5-di-O-caffeoyl-epi-quinate 로 동정하였다.[Α] D value, UV spectrum, IR spectrum, HR-FAB-MS spectrum, 1 H-NMR and 13 C-NMR of the compound represented by the general formula (2) As described above, compound 2 was identified as methyl 3,5-di-O-caffeoyl-epi-quinate.
[α]D: -120.0° (c. 0.2, MeOH);[[alpha]] D : -120.0 [deg.] (c 0.2, MeOH);
UV max(MeOH) nm : 296, 330;UV max (MeOH) nm: 296, 330;
IR (nujol) cm- 1 : 3410, 1685, 1605, 1520, 1160, 976, 810;IR (nujol) cm < -1 > : 1 3410, 1685, 1605, 1520, 1160, 976, 810;
HR-FAB-MS: 531.1506 [M+H]+ (C26H27O12);HR-FAB-MS: 531.1506 [M + H] < + > (C 26 H 27 O 12 );
1H NMR (CD3OD, 600 MHz) : δ 7.61, 7.54 (each 1H, d, J = 15.6 Hz, H-7', H-7"), 7.07 (1H, d, J = 2.0 Hz, H-2'), 7.06 (1H, d, J = 2.0 Hz, H-2"), 6.97 (1H, dd, J = 8.4, 2.0 Hz, H-6'), 6.96 (1H, dd, J = 8.4, 2.0 Hz, H-6"), 6.78 (1H, d, J = 8.4 Hz, H-5'), 6.77 (1H, d, J = 8.4 Hz, H-5"), 6.34, 6.21 (each 1H, d, J = 15.6 Hz, H-8',H-8"), 5.43 (1H, m, H-3), 5.39 (1H, m, H-5), 3.96 (1H, dd, J = 9.0, 3.0 Hz, H-4), 3.69 (3H, s, OCH3-7), 2.31 (1H, dd, J = 14.4, 3.6 Hz, H-6ax), 2.23 (1H, dd, J = 13.6, 3.0 Hz, H-2eq), 2.11 (1H, dd, J = 13.6, 9.0 Hz, H-2ax), 2.06 (1H, m, H-6eq); 1 H NMR (CD 3 OD, 600 MHz): δ 7.61, 7.54 (each 1H, d, J = 15.6 Hz, H-7 ', H-7 "), 7.07 (1H, d, J = 2.0 Hz, H (1H, dd, J = 8.4 Hz), 7.06 (1H, d, J = 2.0 Hz, H- , 2.0 Hz, H-6 "), 6.78 (1H, d, J = 8.4 Hz, H-5 '), 6.77 (1H, d, J = 8.4 Hz, H- (d, J = 15.6 Hz, H-8 ', H-8''), 5.43 (1H, m, H-3) , 3.0 Hz, H-4) , 3.69 (3H, s, OCH3-7), 2.31 (1H, dd, J = 14.4, 3.6 Hz, H-6 ax), 2.23 (1H, dd, J = 13.6, 3.0 Hz, H-2 eq ), 2.11 (1H, dd, J = 13.6, 9.0 Hz, H-2 ax ), 2.06 (1H, m, H-6 eq );
13C NMR (CD3OD, 150 MHz) : δ 180.1 (C-7), 168.0 (C-9',C-9"), 148.1 (C-4"), 147.9 (C-4'), 145.5 (C-3"), 145.4 (C-3'), 145.3 (C-7', C-7"), 126.7 (C-1"), 126.5 (C- 1'), 121.5 (C-6', C-6"), 111.5 (C-5', C-5"), 114.7 (C-8"), 114.2 (C-8'), 113.8 (C-2' , C-2"), 74.9 (C-1), 73.1 (C-5), 71.8 (C-4), 71.1 (C-3), 52.9 (C-7 MeO), 39.5 (C-2), 36.3 (C-6). 13 C NMR (CD 3 OD, 150 MHz): δ 180.1 (C-7), 168.0 (C-9 ', C-9 "), 148.1 (C-4"), 147.9 (C-4'), 145.5 (C-3 ''), 145.4 (C-3 '), 145.3 (C-7', C-7 ''), 126.7 , C-6 "), 111.5 (C-5 ', C-5"), 114.7 (C-1), 73.1 (C-5), 71.8 (C-4), 71.1 (C-3), 52.9 (C-7 MeO), 39.5 (C-2), 36.3 (C-6).
2. 췌장 리파아제 저해 효과2. Pancreatic lipase inhibitory effect
췌장 리파아제 저해활성 측정 실험은 돼지 췌장 리파아제를 이용하여 측정하였다.Measurement of pancreatic lipase inhibitory activity was measured using porcine pancreatic lipase.
효소완충용액[10 mM MOPS (morpholinepropanesulphonic acid) 및 1 mM EDTA, pH 6.8]에 혼합된 6μL(10 units)의 돼지 췌장 리파아제(porcine pancreatic lipase, Sigma, St. Louis, MO, USA)와 169 μL의 Tris 완충용액(100 mM TrisHC1 and 5 mM CaCl2, pH 7.0)를 혼합하여 준비한다. 여기에 다양한 농도로 준비한 화학식 1로 표시되는 화합물, 화학식 2로 표시되는 화합물과 양성 대조약물로 Orlistat (Roche, Basel, Switzerland)을 사용하여 20 μL를 혼합하여 37℃에서 15분간 인큐베이션한다. 이후 5μL의 기질 용액[10mM p-NPB(p-nitrophenylbutyrate) in dimethylformamide]를 첨가한 다음 15분간 더 인큐베이션한다. 췌장 리파아제 활성은 p-NPB가 췌장 리파아제에 의하여 가수분해되어 나오는 p-니트로페놀(p-nitrophenol)을 ELISA기기(BIO-TEK, Synergy HT, USA)를 이용하여 405nm의 파장에서 흡광도를 측정하였다.(10 units) of porcine pancreatic lipase (Sigma, St. Louis, Mo., USA) and 169 μL of a mixture of 10 μM (10 mM MOPS (morpholinepropanesulphonic acid) and 1 mM EDTA, pH 6.8) Tris buffer solution (100 mM TrisHCl and 5 mM CaCl2, pH 7.0) is prepared by mixing. 20 μL of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 prepared as various concentrations and the positive control drug Orlistat (Roche, Basel, Switzerland) were mixed and incubated at 37 ° C. for 15 minutes. Then, 5 μL of a substrate solution [10 mM p-NPB (p-nitrophenylbutyrate) in dimethylformamide] is added, followed by further incubation for 15 minutes. Pancreatic lipase activity was measured by absorbance of p-nitrophenol (p-nitrophenol) obtained by hydrolysis of p-NPB by pancreatic lipase using an ELISA instrument (BIO-TEK, Synergy HT, USA) at a wavelength of 405 nm.
췌장 리파아제 활성 억제 정도는 화학식 1로 표시되는 화합물, 화학식 2로 표시되는 화합물에 의하여 억제된 흡광도의 비율을 퍼센트 값으로 환산하여 계산하였고, 췌장 리파아제의 활성을 50% 억제하는 농도(IC50)를 계산하였다.The degree of inhibition of pancreatic lipase activity was calculated by converting the ratio of the absorbance suppressed by the compound represented by the formula (1) and the compound represented by the formula (2) to the percentage value, and the concentration (IC 50 ) for inhibiting the activity of the pancreatic lipase by 50% Respectively.
화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물 모두 췌장 리파아제의 활성을 저해하는 효과가 있음을 확인하였다. 따라서 본 발명에 따른 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물은 항비만 효과 및 체지방감소 효과가 있을 것으로 생각된다.It was confirmed that both the compound represented by formula (1) and the compound represented by formula (2) were effective in inhibiting the activity of pancreatic lipase. Therefore, the compound represented by the formula (1) and the compound represented by the formula (2) according to the present invention are thought to have an anti-obesity effect and a body fat reducing effect.
실시예Example 3. 3T3-L1 3. 3T3-L1 지방전구세포를Fat precursor cells 이용한 Used 항비만Anti-obesity 효과 effect
3-1. 3T3-L1 지방전구세포의 준비3-1. Preparation of 3T3-L1 adipose precursor cells
3T3-L1 지방전구세포는 미국세포주은행(ATCC)으로부터 구매하여 실험에 사용하였다. 3T3-L1은 지방세포의 대사과정을 연구하는 데에 널리 이용되는 세포주로서, 상기 세포의 분화가 활발할수록 지방세포 내의 지방 축적이 활발하여 비만을 유도하게 된다. 따라서 항비만 효과를 가질 것으로 생각되는 물질을 상기 세포에 처리하였을 때, 세포의 분화가 적을수록 항비만 효과가 큰 물질인 것으로 볼 수 있다.3T3-L1 adipose precursor cells were purchased from the American Cell Line Bank (ATCC) and used for the experiments. 3T3-L1 is a widely used cell line for studying the metabolic process of adipocytes. As the differentiation of these cells becomes more active, the accumulation of adipocytes in the adipocytes becomes active and induces obesity. Therefore, when a cell suspected of having an anti-obesity effect is treated with the cell, the smaller the cell differentiation, the greater the anti-obesity effect.
3-2. 3T3-L1 지방전구세포의 지방세포로의 분화 유도3-2. Differentiation of 3T3-L1 adipocytes into adipocytes
마우스 전구지방세포인 3T3-L1을 10% 소 태아 혈청(fetal bovine serum, FBS)을 포함한 DMEM 배지를 넣고 37℃, 5% CO2의 조건에서 배양하였다. 3T3-L1 전구지방세포를 24 웰 플레이트에 웰당 5×104개의 세포 수로 분주한 후, 웰이 전구지방세포로 100% 채워지는 시점이 된 이후에, 2일 동안 더 유지시켰다. 전구지방세포는 MDI(0.5mM 3-isobutyl-1-methylxanthine(IBMX), 1μM 덱사메타손, 1μM 인슐린)를 포함하는 10% FBS DMEM 배지로 지방세포 분화를 2일 동안 유도하였고, 배양 48시간 후, 2 μM 인슐린이 함유된 10% FBS DMEM으로 이틀 동안 배양하였다. 그 후 2일 마다 4일 동안 10% FBS DMEM 배양액으로 교체하였다. 지방세포 분화를 유도하는 동안 본 발명에 따른 화학식 2로 표시되는 화합물을 25μM, 50μM, 100μM 농도로 각 배양에 처리하였고, 분화가 완성되는 시점인 8일째에 지방세포 분화 정도를 관찰하였다.3T3-L1 mouse precursor adipocytes were cultured in DMEM medium supplemented with 10% fetal bovine serum (FBS) at 37 ° C and 5% CO 2 . 3T3-L1 precursor adipocytes were dispensed into 24-well plates at 5 x 10 4 cells per well, and then maintained for two more days after the well was 100% filled with precursor adipocytes. The precursor adipocytes were induced for 2 days with 10% FBS DMEM medium containing MDI (0.5 mM 3-isobutyl-1-methylxanthine (IBMX), 1 μM dexamethasone, 1 μM insulin) and cultured for 2 days with 10% FBS DMEM containing [mu] M insulin. Subsequently, the cells were replaced with 10% FBS DMEM medium for 2 days every 4 days. During the induction of adipocyte differentiation, the compounds of formula (2) according to the present invention were treated at 25 μM, 50 μM and 100 μM concentration, and the degree of adipocyte differentiation was observed on the 8th day when the differentiation was completed.
3-3. 오일 레드 O (Oil red O) 염색 및 분석3-3. Oil red O dyeing and analysis
지방의 축적 정도를 확인하기 위해 오일 레드 O 염색을 하였다. 상기 실험에서 유도한 지방세포의 분화 정도를 오일 레드 O 염색을 통해 1차적으로 현미경을 통해 확인하였고, 지방세포 염색 정도는 500nm 흡광도에서 세포의 분화된 지방의 양을 측정하였다.Oil red O was stained to confirm the accumulation of fat. The degree of differentiation of adipocyte derived from the above experiment was firstly confirmed by microscopic examination through oil red O staining and the degree of differentiation of cells in the degree of adipocyte staining was measured at 500 nm absorbance.
그 결과, 도 1에 나타나는 것과 같이, 본 발명에 따른 화학식 2로 표시되는 화합물은 3T3-L1 지방전구세포의 분화를 농도의존적으로 억제하였고, 결과적으로 지방의 양도 감소시킴을 확인하였다(도 1). As a result, as shown in FIG. 1, the compound of Formula 2 according to the present invention inhibited the differentiation of 3T3-L1 adipocyte precursor cells in a concentration-dependent manner, and consequently decreased the amount of fat (FIG. 1) .
따라서 본 발명에 따른 화학식 2로 표시되는 화합물은 항비만 효과 및 체지방감소 효과가 있을 것으로 생각된다.Therefore, the compound of formula (2) according to the present invention is expected to have anti-obesity effect and body fat reduction effect.
Claims (8)
[화학식 1]
상기 화학식 1에서,
R은 쿠마로일기(coumaroyl)를 나타낸다. A pharmaceutical composition for preventing or treating obesity, which comprises a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient:
[Chemical Formula 1]
In Formula 1,
R represents coumaroyl.
[화학식 1]
상기 화학식 1에서,
R은 쿠마로일기(coumaroyl)를 나타낸다. A health functional food composition for preventing or ameliorating obesity, which comprises a compound represented by the following formula (1) or a salt thereof as an active ingredient:
[Chemical Formula 1]
In Formula 1,
R represents coumaroyl.
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KR102377533B1 (en) * | 2020-01-03 | 2022-03-23 | 안동대학교 산학협력단 | Method for producing sunsik using Ainsliaea acerifolia extract powder |
KR102362147B1 (en) * | 2020-01-03 | 2022-02-11 | 안동대학교 산학협력단 | Method for producing low calorie gummy jelly using Ainsliaea acerifolia extract powder |
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KR102397639B1 (en) * | 2020-01-03 | 2022-05-13 | 안동대학교 산학협력단 | Method for producing gum using Ainsliaea acerifolia extract powder |
KR102384552B1 (en) * | 2020-01-03 | 2022-04-15 | 안동대학교 산학협력단 | Method for producing seasoning sauce for chicken using Ainsliaea acerifolia extract powder |
CN113402529B (en) * | 2021-06-23 | 2022-04-15 | 南京中医药大学 | Trimeric guaiane type sesquiterpenoids, preparation method and application thereof |
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KR101405429B1 (en) | 2012-10-29 | 2014-06-11 | 정다운 | Cosmetics containing natural grass |
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KR20220064693A (en) | 2020-11-12 | 2022-05-19 | 중앙대학교 산학협력단 | Composition for Antiobesity Comprising Capmatinib |
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