KR102590647B1 - Composition for preventing, improving or treating obesity comprising fermented product of Momordica charantia or compound isolated therefrom as effective component - Google Patents
Composition for preventing, improving or treating obesity comprising fermented product of Momordica charantia or compound isolated therefrom as effective component Download PDFInfo
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- KR102590647B1 KR102590647B1 KR1020210015495A KR20210015495A KR102590647B1 KR 102590647 B1 KR102590647 B1 KR 102590647B1 KR 1020210015495 A KR1020210015495 A KR 1020210015495A KR 20210015495 A KR20210015495 A KR 20210015495A KR 102590647 B1 KR102590647 B1 KR 102590647B1
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- Prior art keywords
- acid
- compound
- bitter melon
- preventing
- fermented
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- A—HUMAN NECESSITIES
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Abstract
본 발명은 여주 발효물 또는 이로부터 분리된 화합물을 유효성분으로 함유하는 비만의 예방, 개선 또는 치료용 조성물에 관한 것으로, 본 발명의 여주 발효물 또는 이로부터 분리된 신규 화합물은 지방 축적 억제능이 우수하므로, 항비만용 건강기능식품 또는 비만 치료제의 소재로 유용하게 활용될 수 있을 것이다.The present invention relates to a composition for preventing, improving or treating obesity containing a fermented bitter melon or a compound isolated therefrom as an active ingredient. The fermented bitter melon or a new compound isolated therefrom of the present invention has an excellent ability to inhibit fat accumulation. Therefore, it can be useful as a material for anti-obesity health functional food or obesity treatment.
Description
본 발명은 여주 발효물 또는 이로부터 분리된 화합물을 유효성분으로 함유하는 비만의 예방, 개선 또는 치료용 조성물에 관한 것이다.The present invention relates to a composition for preventing, improving or treating obesity containing fermented bitter melon or a compound isolated therefrom as an active ingredient.
비만은 체내에 지방조직이 과다하게 축적된 상태로, 주로 에너지 소비량에 비해 영양소를 과다 섭취할 경우 일어나는 에너지 불균형에 의해 유도되며, 이 외에도 호르몬의 변화, 유전, 정신 건강 문제 및 사회경제적 요인 등에 의해서도 유도된다고 알려져 있다. 비만 인구는 전세계적으로 증가하는 추세로, 최근 성인병을 유발하는 중요한 요인으로 지목받으며 비만의 심각성이 중요한 문제로 대두되고 있다.Obesity is a condition in which excessive adipose tissue is accumulated in the body. It is mainly induced by energy imbalance that occurs when nutrient intake is excessive compared to energy consumption. In addition, it can also be caused by hormonal changes, genetics, mental health problems, and socioeconomic factors. It is known to be induced. The obese population is increasing worldwide, and the severity of obesity has recently emerged as an important issue as it has been pointed out as an important factor causing adult diseases.
현재 비만을 치료하는 치료제로는 세로토닌 신경계를 저해하는 펜플루라민, 노르아드레날린 신경계를 통한 에페드린 및 카페인, 세로토닌 및 노르아드레날린 신경계에 동시에 작용하는 시부트라민 및 췌장에서 생성되는 리파아제를 저해하여 지방의 흡수를 줄여주는 오르리스타트 등의 약물이 있다. 그러나 기존에 사용되어온 약물 중 펜플루라민 등은 원발성 폐고혈압이나 심장 판막 병변과 같은 부작용을 일으켜 사용이 금지되었으며, 다른 약물들도 혈압감소나 유산혈증 등의 문제점이 발생하여 심부전, 신질환 등의 환자에는 사용하지 못하는 문제점이 있다. 따라서 부작용이 적은 비만의 예방, 개선 또는 치료 물질의 개발이 요구된다.Current treatments for obesity include fenfluramine, which inhibits the serotonergic nervous system, ephedrine and caffeine, which act on the noradrenergic nervous system, sibutramine, which acts simultaneously on the serotonin and noradrenergic nervous system, and Orly, which reduces fat absorption by inhibiting lipase produced in the pancreas. There are medications such as Start. However, among the previously used drugs, fenfluramine has been banned due to side effects such as primary pulmonary hypertension and heart valve lesions, and other drugs have also caused problems such as decreased blood pressure and lactic acidemia, so they are not used in patients with heart failure or renal disease. There is a problem that cannot be done. Therefore, the development of substances to prevent, improve, or treat obesity with fewer side effects is required.
한편, 한국공개특허 제2010-0134575호에 '여주로부터 추출한 화합물의 당뇨병과 비만증 예방 및 치료 약품 제조에서의 용도'가 개시되어 있고, 한국등록특허 제1690369호에 '여주 혼합 열수추출물을 유효성분으로 포함하는 항비만용 약학적 조성물 및 이의 제조방법'이 개시되어 있으나, 본 발명의 여주 발효물 또는 이로부터 분리된 화합물을 유효성분으로 함유하는 비만의 예방, 개선 또는 치료용 조성물에 대해서는 기재된 바가 없다.Meanwhile, Korea Patent Publication No. 2010-0134575 discloses the use of compounds extracted from bitter melon in the manufacture of drugs for preventing and treating diabetes and obesity, and Korean Patent No. 1690369 discloses the use of mixed hot water extracts of bitter melon as an active ingredient. 'A pharmaceutical composition for anti-obesity and a method for producing the same' is disclosed, but there is no description of a composition for the prevention, improvement or treatment of obesity containing the fermented product of bitter melon of the present invention or a compound isolated therefrom as an active ingredient. .
본 발명은 상기와 같은 요구에 의해 도출된 것으로서, 본 발명자들은 여주 열수추출물에 양송이 분쇄물의 여과액을 첨가하여 발효시킨 여주 발효물과 상기 여주 발효물의 분획물로부터 분리된 화학식 1의 화합물이 3T3-L1 전지방세포(preadipocyte)에서 지방 축적 억제능이 우수한 것을 확인함으로써, 본 발명을 완성하였다.The present invention was developed in response to the above-mentioned needs, and the present inventors have discovered that the compound of formula 1 isolated from the fermented bitter melon fruit and the fraction of the fermented bitter melon fermented by adding the filtrate of crushed button mushroom to the bitter melon hot water extract is 3T3-L1. The present invention was completed by confirming that it had excellent ability to inhibit fat accumulation in preadipocytes.
상기 과제를 해결하기 위해, 본 발명은 화학식 1의 화합물 또는 이의 허용 가능한 염; 또는 화학식 1의 화합물을 포함하는 여주 발효물;을 유효성분으로 함유하는 비만의 예방 또는 개선용 건강기능식품 조성물을 제공한다.In order to solve the above problems, the present invention provides a compound of Formula 1 or an acceptable salt thereof; Or a fermented bitter melon containing the compound of Chemical Formula 1; provided as a health functional food composition for preventing or improving obesity containing as an active ingredient.
또한, 본 발명은 화학식 1의 화합물 또는 이의 허용 가능한 염; 또는 화학식 1의 화합물을 포함하는 여주 발효물;을 유효성분으로 함유하는 비만의 예방 또는 치료용 약학 조성물을 제공한다.Additionally, the present invention relates to a compound of Formula 1 or an acceptable salt thereof; Or a fermented bitter melon containing the compound of Formula 1; Provided is a pharmaceutical composition for preventing or treating obesity containing as an active ingredient.
본 발명의 여주 발효물 또는 이로부터 분리된 신규 화합물은 지방 축적 억제능이 우수하므로, 항비만용 건강기능식품 또는 비만 치료제의 소재로 유용하게 활용될 수 있을 것으로 기대된다.The fermented bitter melon of the present invention or the new compound isolated therefrom has an excellent ability to inhibit fat accumulation, so it is expected to be useful as a material for anti-obesity health functional food or obesity treatment.
도 1A는 여주 열수추출물과 여주 발효물의 에틸아세테이트 분획물(EtOAc)을 대상으로 HPLC(High Performance Liquid Chromatography)를 수행한 결과이고, 도 1B는 여주 발효물의 에틸아세테이트 분획물로부터 분리된 APM-1 화합물(화학식 1) 및 APM-2 화합물(화학식 2)의 구조식이다. 빨간색 화살표: EtOAc 분획물에서 분리된 APM-1 화합물(tR 9.2 min) 및 APM-2 화합물(tR 11.6 min).
도 2는 여주 열수추출물, 여주 발효물, 여주 발효물의 분획물(n-Hexane layer, EtOAc layer, n-BuOH layer, H2O layer), 이로부터 분리된 APM-1 화합물(화학식 1) 또는 APM-2 화합물(화학식 2)의 세포 독성을 확인한 결과이다.
도 3A는 여주 열수추출물, 여주 발효물 또는 여주 발효물의 분획물(n-Hexane layer, EtOAc layer, n-BuOH layer, H2O layer)의 지방 축적 억제능을 확인한 결과이고, 도 3B는 여주 발효물의 에틸아세테이트 분획물(EtOAc)로부터 분리된 APM-1 화합물(화학식 1) 및 APM-2 화합물(화학식 2)의 지방 축적 억제능을 확인한 결과이다. DMI: 지방 생성 촉진 유도제(1μM Dexamethasone, 0.5mM IBMX, 1μM Insulin), Nor: DMI 무처리군(시료 무처리). Cont: DMI 처리군(시료 무처리), EGCG(양성대조군): (-)-에피갈로카테킨 갈레이트(epigallocatechin gallate).
도 4는 APM-1 화합물(화학식 1)이 처리된 3T3-L1 전지방세포(preadipocyte)의 Oil red O 염색 결과 사진이다. DMI: 지방 생성 촉진 유도제(1μM Dexamethasone, 0.5mM IBMX, 1μM Insulin). Figure 1A shows the results of HPLC (High Performance Liquid Chromatography) on Yeoju hot water extract and the ethyl acetate fraction (EtOAc) of Yeoju fermented product, and Figure 1B shows the APM-1 compound (chemical formula) isolated from the ethyl acetate fraction of Yeoju fermented product. 1) and the structural formula of APM-2 compound (Formula 2). Red arrows: APM-1 compound (t R 9.2 min) and APM-2 compound (t R 11.6 min) isolated from the EtOAc fraction.
Figure 2 shows Yeoju hot water extract, Yeoju fermented product, fractions of Yeoju fermented product (n-Hexane layer, EtOAc layer, n-BuOH layer, HO layer), and APM-1 compound (Formula 1) or APM-2 compound separated therefrom. This is a result of confirming the cytotoxicity of (Formula 2).
Figure 3A shows the results of confirming the fat accumulation inhibition ability of bitter melon hot water extract, bitter melon fermentation, or fractions of bitter melon fermentation (n-Hexane layer, EtOAc layer, n-BuOH layer, H2O layer), and Figure 3B shows the ethyl acetate fraction of bitter melon fermentation. This is the result of confirming the fat accumulation inhibition ability of A PM-1 compound (Formula 1) and APM-2 compound (Formula 2) isolated from (EtOAc). DMI: adipogenesis-promoting inducer (1μM Dexamethasone, 0.5mM IBMX, 1μM Insulin), Nor: DMI untreated group (sample untreated). Cont: DMI treated group (no sample treatment), EGCG (positive control): (-)-epigallocatechin gallate.
Figure 4 is a photograph of Oil red O staining results of 3T3-L1 preadipocytes treated with APM-1 compound (Formula 1). DMI: adipogenic inducer (1μM Dexamethasone, 0.5mM IBMX, 1μM Insulin).
본 발명의 목적을 달성하기 위하여, 본 발명은 하기 화학식 1의 화합물 또는 이의 허용 가능한 염; 또는 하기 화학식 1의 화합물을 포함하는 여주 발효물;을 유효성분으로 함유하는 비만의 예방 또는 개선용 건강기능식품 조성물을 제공한다.In order to achieve the object of the present invention, the present invention is a compound of the following formula (1) or an acceptable salt thereof; Or, it provides a health functional food composition for preventing or improving obesity containing as an active ingredient a fermented bitter melon containing a compound of the following formula (1).
본 발명의 건강기능식품 조성물에 있어서, 상기 화학식 1의 화합물은 여주 발효물로부터 분리된 것일 수 있고, 바람직하게는 여주 발효물의 에틸아세테이트 분획물(Ethly acetate, EtOA)로부터 분리된 것일 수 있으나, 이에 특별히 제한되는 것은 아니며, 다른 천연물로부터 추출하거나 합성하는 것이 얼마든지 가능하다.In the health functional food composition of the present invention, the compound of formula 1 may be separated from the fermented bitter melon, preferably separated from the ethyl acetate fraction (EtOA) of the fermented bitter melon. It is not limited, and it is possible to extract or synthesize it from other natural products.
본 발명의 건강기능식품 조성물에 있어서, 상기 여주 발효물은 여주 열수추출물을 양송이(Agaricus bisporus) 균사체로 발효시킨 것일 수 있으나, 이에 제한되지 않는다. 상기 양송이 균사체는 양송이 분쇄물과 증류수의 혼합물을 여과하여 수득한 여과액을 의미하는 것일 수 있고, 상기 여과액에는 폴리페놀 산화효소(polyphenol oxidase)가 포함되어 있다.In the health functional food composition of the present invention, the fermented product of bitter melon may be obtained by fermenting bitter melon hot water extract with button mushroom ( Agaricus bisporus ) mycelium, but is not limited thereto. The button mushroom mycelium may refer to a filtrate obtained by filtering a mixture of crushed button mushrooms and distilled water, and the filtrate contains polyphenol oxidase.
본 발명의 여주 발효물, 이의 분획물 또는 이로부터 분리된 화합물은 3T3-L1 전지방세포(preadipocyte)에서 지방 축적 억제능이 우수하여 비만 개선에 효과가 있다.The fermented bitter melon of the present invention, its fractions, or compounds isolated therefrom have an excellent ability to inhibit fat accumulation in 3T3-L1 preadipocytes and are effective in improving obesity.
본 명세서에서, 상기 "이의 허용 가능한 염"은 본 발명 화합물의 생물학적 특성을 유지하면서 독성을 나타내지 않거나 제약 용도로 부적절하지 않은 임의의 본 발명 화합물의 염을 나타낸다. 이러한 염은 당업계에 공지된 다양한 유기 및 무기 반대이온으로부터 유래할 수 있으며, 이들을 포함한다. 이러한 염으로는 유기 또는 무기산, 예컨대 염산, 브롬화수소산, 황산, 질산, 인산, 술팜산, 아세트산, 트리플루오로아세트산, 트리클로로아세트산, 프로피온산, 헥산산, 시클로 펜틸프로피온산, 글리콜산, 글루타르산, 피루브산, 락트산, 말론산, 숙신산, 소르브산, 아스코르브산, 말산, 말레산, 푸마르산, 타르타르산, 시트르산, 벤조산, 3-(4-히드록시벤조일)벤조산, 크르산, 신남산, 만델산, 프탈산, 라우르산, 메탄술폰산, 에탄술폰산, 1,2-에탄-디술폰산, 2-히드록시에탄술폰산, 벤젠 술폰산, 4-클로로벤젠술폰산, 2-나프탈렌술폰산, 4-톨루엔술폰산, 캄포르산, 캄포르술폰산, 4-메틸비시클로 [2.2.2]-옥트-2-엔-1-카르복실산, 글루코헵톤산, 3-페닐프로피온산, 트리메틸아세트산, 테르트-부틸아세트산, 라우릴 황산, 글루콘산, 글루탐산, 히드록시나프토산, 살리실산, 스테아르산, 시클로헥실술팜산, 퀸산 또는 뮤콘산 등과 형성된 산 부가염; 또는 모 화합물에 존재하는 산성 양성자가 금속 이온(예를 들면, 알칼리 금속 이온, 알칼리 토금속 이온 또는 알루미늄 이온), 알칼리 금속 또는 알칼리 토금속수산화물(예컨대, 나트륨, 칼륨, 칼슘, 마그네슘, 알루미늄, 리튬, 아연 및 바륨 수산화물), 암모니아로 치환되거나, 또는 유기 염기, 예컨대 지방족, 지환족 또는 방향족 유기 아민, 예를 들면 암모니아, 메틸아민, 디메틸아민, 디에틸아민, 피콜린, 에탄올아민, 디에탄올아민, 트리에탄올아민, 에틸렌디아민, 리신, 아르기닌, 오르니틴, 콜린, N,N'-디벤질에틸렌-디아민, 클로로프로카인, 디에탄올아민, 프로카인, N-벤질페네틸아민, N-메틸글루카민 피페라진, 트리스(히드록시메틸)-아미노메탄 또는 테트라메틸암모늄 히드록시드와 배위 결합한 경우에 형성된 염 등을 포함할 수 있다.As used herein, the term “acceptable salt thereof” refers to any salt of the present compound that retains the biological properties of the present compound and is not toxic or unsuitable for pharmaceutical use. Such salts may be derived from and include a variety of organic and inorganic counterions known in the art. These salts include organic or inorganic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, sulfamic acid, acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, hexanoic acid, cyclopentylpropionic acid, glycolic acid, glutaric acid, Pyruvic acid, lactic acid, malonic acid, succinic acid, sorbic acid, ascorbic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl)benzoic acid, chric acid, cinnamic acid, mandelic acid, phthalic acid, Lauric acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzene sulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, 4-toluenesulfonic acid, camphoric acid, camphor acid. Forsulfonic acid, 4-methylbicyclo [2.2.2]-oct-2-en-1-carboxylic acid, glucoheptonic acid, 3-phenylpropionic acid, trimethylacetic acid, tert-butylacetic acid, lauryl sulfate, gluconic acid. , acid addition salts formed with glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, cyclohexylsulfamic acid, quinic acid or muconic acid, etc.; or the acidic proton present in the parent compound is a metal ion (e.g., an alkali metal ion, an alkaline earth metal ion, or an aluminum ion), an alkali metal, or an alkaline earth metal hydroxide (e.g., sodium, potassium, calcium, magnesium, aluminum, lithium, zinc). and barium hydroxide), ammonia, or substituted with an organic base such as aliphatic, cycloaliphatic or aromatic organic amines such as ammonia, methylamine, dimethylamine, diethylamine, picoline, ethanolamine, diethanolamine, triethanol. Amine, ethylenediamine, lysine, arginine, ornithine, choline, N,N'-dibenzylethylene-diamine, chloroprocaine, diethanolamine, procaine, N-benzylphenethylamine, N-methylglucamine piperazine , tris(hydroxymethyl)-aminomethane, or a salt formed when coordinated with tetramethylammonium hydroxide.
또한, 염의 예로는 나트륨, 칼륨, 칼슘, 마그네슘, 암모늄 또는 테트라알킬암모늄 염 등이 있으며, 화합물이 염기성 관능기를 함유하는 경우에는 비독성유기산 또는 무기산과의 염, 예컨대 히드로할라이드(예를 들면, 히드로클로라이드 또는 히드로브로마이드), 술페이트, 포스페이트, 술파메이트, 니트레이트, 아세테이트, 트리플루오로아세테이트, 트리클로로아세테이트, 프로피오네이트, 헥사노에이트, 시클로펜틸프로피오네이트, 글리콜레이트, 글루타레이트, 루베이트, 락테이트, 말로네이트, 숙시네이트, 소르베이트, 아스코르베이트, 말레이트, 말레에이트, 푸마레이트, 타르타레이트, 시트레이트, 벤조에이트, 3-(4-히드록시벤조일푸마레이트, 타르타레이트, 시트레이트, 벤조에이트, 3-(4-히드록시벤조일)벤조에이트, 피크레이트, 신나메이트, 만델레이트, 프탈레이트, 라우레이트, 메탄술포네이트 메실레이트), 에탄술포네이트, 1,2-에탄-디술포네이트, 2-히드록시에탄술포네이트, 벤젠술포네이트(베실레이트), 4-클로로벤젠술포네이트, 2-나프탈렌술포네이트, 4-톨루엔술포네이트, 캄포레이트, 캄포르술포네이트, 4-메틸비시클로[2.2.2]-옥트-2-엔-1-카르복실레이트, 글루코헵토네이트, 3-페닐프로피오네이트, 트리메틸아세테이트, 테르트-부틸아세테이트, 라우릴 술페이트, 글루코네이트, 벤조에이트, 글루타메이트, 히드록시나프토에이트, 살리실레이트, 스테아레이트, 시클로헥실술파메이트, 퀴네이트 또는 뮤코네이트 염 등을 포함할 수 있다.Additionally, examples of salts include sodium, potassium, calcium, magnesium, ammonium, or tetraalkylammonium salts, and when the compound contains a basic functional group, salts with non-toxic organic acids or inorganic acids, such as hydrohalides (e.g., hydrohalides). chloride or hydrobromide), sulfate, phosphate, sulfamate, nitrate, acetate, trifluoroacetate, trichloroacetate, propionate, hexanoate, cyclopentylpropionate, glycolate, glutarate, lutein Bates, lactate, malonate, succinate, sorbate, ascorbate, maleate, maleate, fumarate, tartarate, citrate, benzoate, 3-(4-hydroxybenzoyl fumarate, tartarate) citrate, benzoate, 3-(4-hydroxybenzoyl)benzoate, picrate, cinnamate, mandelate, phthalate, laurate, methanesulfonate (mesylate), ethanesulfonate, 1,2-ethane -Disulfonate, 2-hydroxyethanesulfonate, benzenesulfonate (besylate), 4-chlorobenzenesulfonate, 2-naphthalenesulfonate, 4-toluenesulfonate, camphorate, camphorsulfonate, 4- Methylbicyclo[2.2.2]-oct-2-en-1-carboxylate, glucoheptonate, 3-phenylpropionate, trimethyl acetate, tert-butylacetate, lauryl sulfate, gluconate, benzoate. It may include ate, glutamate, hydroxynaphthoate, salicylate, stearate, cyclohexylsulfamate, quinate, or muconate salt.
본 발명의 건강기능식품 조성물은 분말, 과립, 환, 정제, 캡슐, 캔디, 시럽 및 음료 중에서 선택된 하나의 제형일 수 있으나, 이에 제한되지 않는다.The health functional food composition of the present invention may be in a formulation selected from powder, granule, pill, tablet, capsule, candy, syrup, and beverage, but is not limited thereto.
본 발명의 화합물 또는 상기 화합물을 포함하는 여주 발효물을 식품첨가물로 사용하는 경우, 상기 본 발명의 화합물 또는 상기 화합물을 포함하는 여주 발효물을 그대로 첨가하거나 다른 식품 또는 식품성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효 성분의 혼합양은 그의 사용 목적(예방 또는 개선)에 따라 적절하게 사용될 수 있다. 일반적으로, 식품 또는 음료의 제조시 본 발명의 건강기능식품 조성물은 원료에 대하여 15 중량부 이하, 바람직하게는 10 중량부 이하의 양으로 첨가된다. 그러나 건강을 목적으로 하는 장기간의 섭취의 경우에는 상기 양은 상기 범위 이하일 수 있다.When using the compound of the present invention or a fermented bitter melon containing the compound as a food additive, the compound of the present invention or a fermented bitter melon containing the compound may be added as is or used together with other foods or food ingredients, It can be used appropriately according to conventional methods. The mixed amount of active ingredients can be appropriately used depending on the purpose of use (prevention or improvement). Generally, when manufacturing a food or beverage, the health functional food composition of the present invention is added in an amount of 15 parts by weight or less, preferably 10 parts by weight or less, based on the raw materials. However, in the case of long-term intake for health purposes, the amount may be below the above range.
상기 식품의 종류에는 특별한 제한은 없다. 상기 건강기능식품 조성물을 첨가할 수 있는 식품의 예로는 육류, 소시지, 빵, 초콜릿, 캔디류, 스낵류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 차 드링크제, 알콜 음료 및 비타민 복합제 등이 있으며, 통상적인 의미에서의 건강식품을 모두 포함한다. 상기 음료는 탄산음료, 기능성이온음료, 쥬스(예를 들어, 사과, 배, 포도, 알로에, 감귤, 복숭아, 당근, 토마토쥬스 등), 식혜 등을 포함한다.There are no special restrictions on the types of foods above. Examples of foods to which the health functional food composition can be added include meat, sausages, bread, chocolate, candies, snacks, confectionery, pizza, ramen, other noodles, gum, dairy products including ice cream, various soups, beverages, and tea. There are drinks, alcoholic beverages, and vitamin complexes, and it includes all health foods in the conventional sense. The beverages include carbonated beverages, functional ion beverages, juices (e.g., apple, pear, grape, aloe, tangerine, peach, carrot, tomato juice, etc.), sikhye, and the like.
본 발명의 기능성 식품은 식품 제조 시에 통상적으로 첨가되는 성분을 포함하며, 예를 들어, 단백질, 탄수화물, 지방, 영양소 및 조미제를 포함한다. 예컨대, 드링크제로 제조되는 경우에는 유효성분 이외에 천연 탄수화물 또는 향미제를 추가 성분으로서 포함시킬 수 있다. 상기 천연 탄수화물은 모노사카라이드(예컨대, 글루코오스, 프럭토오스 등), 디사카라이드(예컨대, 말토스, 수크로오스 등), 올리고당, 폴리사카라이드(예컨대, 덱스트린, 시클로덱스트린 등) 또는 당알코올(예컨대, 자일리톨, 소르비톨, 에리쓰리톨 등)인 것이 바람직하다. 상기 향미제는 천연 향미제(예컨대, 타우마틴, 스테비아 추출물 등)와 합성 향미제(예컨대, 사카린, 아스파르탐 등)를 이용할 수 있다. 상기 건강기능식품 조성물 외에 여러가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산음료에 사용되는 탄산화제 등을 더 함유할 수 있다.The functional food of the present invention includes ingredients commonly added during food production, and includes, for example, proteins, carbohydrates, fats, nutrients and seasonings. For example, when manufacturing a drink, natural carbohydrates or flavoring agents may be included as additional ingredients in addition to the active ingredient. The natural carbohydrates include monosaccharides (e.g., glucose, fructose, etc.), disaccharides (e.g., maltose, sucrose, etc.), oligosaccharides, polysaccharides (e.g., dextrins, cyclodextrins, etc.), or sugar alcohols (e.g., , xylitol, sorbitol, erythritol, etc.) are preferred. The flavoring agent may be a natural flavoring agent (e.g., thaumatin, stevia extract, etc.) or a synthetic flavoring agent (e.g., saccharin, aspartame, etc.). In addition to the above health functional food composition, various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH regulators, stabilizers, preservatives, glycerin, alcohol, carbonated drinks. It may further contain a carbonating agent used for.
상기 건강기능식품 조성물 이외에 여러 가지 영양제, 비타민, 저해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산음료에 사용되는 탄산화제 등을 더 함유할 수 있다. 이러한 상기 첨가되는 성분의 비율은 크게 중요하진 않지만 본 발명의 건강기능식품 조성물 100 중량부에 대하여, 0.01 내지 0.1 중량부의 범위에서 선택되는 것이 일반적이다.In addition to the above health functional food composition, various nutrients, vitamins, inhibitors, flavors, colorants, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol, It may further contain carbonating agents used in carbonated drinks. The ratio of the ingredients added is not very important, but is generally selected in the range of 0.01 to 0.1 parts by weight based on 100 parts by weight of the health functional food composition of the present invention.
본 발명은 또한, 상기 화학식 1의 화합물 또는 이의 허용가능한 염; 또는 상기 화학식 1의 화합물을 포함하는 여주 발효물;을 유효성분으로 함유하는 비만의 예방 또는 치료용 약학 조성물을 제공한다.The present invention also provides a compound of Formula 1 or an acceptable salt thereof; Or it provides a pharmaceutical composition for the prevention or treatment of obesity containing as an active ingredient a fermented bitter melon containing the compound of Formula 1.
본 발명의 약학 조성물에 있어서, 상기 화학식 1의 화합물은 여주 발효물의 분획물에서 분리된 것으로, 여주 발효물 또는 이로부터 분리된 화합물은 상기 전술한 바와 같다.In the pharmaceutical composition of the present invention, the compound of Formula 1 is isolated from a fraction of the fermented bitter melon, and the fermented bitter melon or the compound isolated therefrom is as described above.
본 발명에 따른 상기 약학 조성물은 각각 통상의 방법에 따라 캡슐제, 산제, 과립제, 정제, 현탁액, 에멀젼, 시럽, 에어로졸 등의 경구형 제형, 외용제, 좌제 및 멸균 주사용액의 형태로 제형화하여 사용될 수 있다.The pharmaceutical composition according to the present invention can be formulated and used in the form of oral dosage forms such as capsules, powders, granules, tablets, suspensions, emulsions, syrups, aerosols, external preparations, suppositories, and sterile injection solutions according to conventional methods. You can.
본 발명의 약학 조성물은 유효성분 이외에 약학적으로 허용되는 담체를 포함할 수 있으며, 이러한 담체는 제제 시에 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 조성물은 상기 성분들 이외에 윤활제, 습윤제, 감미제, 향미제, 유화제, 현탁제, 보존제 등을 추가로 포함할 수 있다. 상기 성분 추가 시에는 복합 사용에 따른 피부 안전성, 제형화의 용이성, 유효성분들의 안정성을 고려할 수 있다.The pharmaceutical composition of the present invention may contain a pharmaceutically acceptable carrier in addition to the active ingredient, and such carriers are commonly used in formulations, such as lactose, dextrose, sucrose, sorbitol, mannitol, starch, acacia gum, Calcium phosphate, alginate, gelatin, calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methyl cellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and minerals. Includes, but is not limited to, oil. In addition to the above ingredients, the pharmaceutical composition of the present invention may further include lubricants, wetting agents, sweeteners, flavoring agents, emulsifiers, suspending agents, preservatives, etc. When adding the above ingredients, skin safety due to combined use, ease of formulation, and stability of the active ingredients can be taken into consideration.
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 배출비율, 치료기간, 동시 사용되는 약물을 포함한 요소 및 기타 의학 분야에 잘 알려진 요소에 따라 결정될 수 있다. 본 발명의 약학 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 the disease with a reasonable benefit/risk ratio applicable to medical treatment, and the effective dose level is determined by the type, severity, and activity of the patient's disease. , may be determined based on factors including sensitivity to the drug, time of administration, route of administration and excretion rate, duration of treatment, concurrently used drugs, and other factors well known in the field of medicine. The pharmaceutical composition of the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, may be administered sequentially or simultaneously with conventional therapeutic agents, and may be administered singly or multiple times. Considering all of the above factors, it is important to administer an amount that can achieve the maximum effect with the minimum amount without side effects, and this can be easily determined by a person skilled in the art.
본 발명의 약학 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 다양하게 처방될 수 있다.The appropriate dosage of the pharmaceutical composition of the present invention may be prescribed in various ways depending on factors such as formulation method, administration method, patient's age, weight, sex, pathological condition, food, administration time, administration route, excretion rate, and reaction sensitivity. You can.
본 발명의 약학 조성물은 경구 또는 비경구로 투여할 수 있으며, 비경구 투여의 경우, 피부에 국소적으로 도포, 정맥 내 주입, 피하 주입, 근육 주입, 복강 주입, 경피 투여 등으로 투여할 수 있다. The pharmaceutical composition of the present invention can be administered orally or parenterally, and in the case of parenteral administration, it can be administered topically on the skin, intravenous injection, subcutaneous injection, intramuscular injection, intraperitoneal injection, transdermal administration, etc.
이하, 본 발명을 실시예에 의해 상세히 설명한다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail by examples. However, the following examples only illustrate the present invention, and the content of the present invention is not limited to the following examples.
제조예 1. 여주 발효물 제조Preparation Example 1. Preparation of Yeoju fermented product
(주)두손애약초에서 구입한 건조된 여주 4.5 kg을 물 45 L에 침지하고 90℃에서 3시간 동안 추출한 후 저온감압농축하여 여주 열수추출물 농축액 1.5 kg을 수득하였다. 또한, 여주 열수추출물의 효소 반응을 위해 양송이(Agaricus bisporus) 40 g을 증류수 100 ㎖과 혼합하여 믹서기로 분쇄하고 5겹 거즈로 필터링하여 폴리페놀 산화효소(polyphenol oxidase)가 함유된 효소원을 제조하였다. 상기 제조된 효소원(60 ㎖)의 폴리페놀 산화효소 활성을 측정하기 위해 피로갈롤(pyrogallol)을 기질로 사용하여 산화 반응 후 생성되는 벤조트로폴론(benzotropolone)의 함량을 UV 분광광도계로 360 nm에서 흡광도를 측정하였으며, 흡광도값이 0.78~0.79인 효소원을 여주 열수추출물의 효소 반응에 사용하였다. 흡광도는 효소원 1.5 ㎖을 200 mM 피로갈롤(in 50 mM sodium phosphate buffer, pH 7.2) 1.5 ㎖과 함께 석영셀에 넣고 5분 동안 산화 반응을 유도한 후 측정하였으며, Blank군에는 1.5 ㎖의 기질 용액과 증류수 1.5 ㎖을 첨가하여 측정하였다(Food Chemistry, 88, 2004, 69-77 및 BBRC, 130(2), 1985, 633-639 참고). 4.5 kg of dried Yeoju purchased from Duson Ae Herb Co., Ltd. was immersed in 45 L of water, extracted at 90°C for 3 hours, and then concentrated under low temperature and reduced pressure to obtain 1.5 kg of Yeoju hot water extract concentrate. In addition, for the enzymatic reaction of Yeoju hot water extract, 40 g of button mushroom ( Agaricus bisporus ) was mixed with 100 ml of distilled water, pulverized in a blender, and filtered through 5-layer gauze to prepare an enzyme source containing polyphenol oxidase. . To measure the polyphenol oxidase activity of the prepared enzyme source (60 ml), the content of benzotropolone produced after the oxidation reaction was measured using a UV spectrophotometer at 360 nm using pyrogallol as a substrate. The absorbance was measured, and an enzyme source with an absorbance value of 0.78 to 0.79 was used for the enzyme reaction of the Yeoju hot water extract. Absorbance was measured after placing 1.5 ml of enzyme source in a quartz cell with 1.5 ml of 200 mM pyrogallol (in 50 mM sodium phosphate buffer, pH 7.2) and inducing an oxidation reaction for 5 minutes. The Blank group was given 1.5 ml of substrate solution. and 1.5 ml of distilled water were added (see Food Chemistry, 88, 2004, 69-77 and BBRC, 130(2), 1985, 633-639).
그 다음, 여주 열수추출물 농축액 15 g을 증류수 40 ㎖에 희석하고 효소원 60 ㎖과 함께 500 ㎖의 비커에 담은 후 교반기를 이용하여 상온에서 80분 동안 반응시켜 여주 발효물을 제조하였다.Next, 15 g of Yeoju hot water extract concentrate was diluted in 40 ml of distilled water, placed in a 500 ml beaker along with 60 ml of enzyme source, and reacted at room temperature for 80 minutes using a stirrer to prepare Yeoju fermented product.
실시예 1. 여주 발효물로부터 화학식 1 및 2의 화합물 분리Example 1. Isolation of compounds of formulas 1 and 2 from bitter melon fermentation product
여주의 효소 반응 실험을 36회 반복 수행하였으며, 생산된 여주 발효물 750 g을 10% 메탄올(MeOH) 2 ℓ에 희석한 후 n-헥산(hexane, 2 ℓ×3회), 에틸아세테이트(EtOAc, 2 ℓ×3회) 및 n-부탄올(BuOH, 2 ℓ×3회)를 이용하여 분획하여 추출한 후 상기 각 용매별 분획물을 저온감압농축하고 건조시켜 n-hexane 분획물 0.2 g, EtOAc 분획물 3.3 g, n-BuOH 분획물 17.4 g 및 H2O 분획물 540.9 g을 얻었다. The enzyme reaction experiment of bitter melon was repeated 36 times, and 750 g of the fermented bitter melon produced was diluted in 2 liters of 10% methanol (MeOH) and mixed with n-hexane (2 liters x 3 times), ethyl acetate (EtOAc, After fractionation and extraction using n-butanol (BuOH, 2 ℓ×3 times) and n-butanol (BuOH, 2 ℓ×3 times), the fractions for each solvent above were concentrated under reduced pressure at low temperature and dried to obtain 0.2 g of n-hexane fraction, 3.3 g of EtOAc fraction, 17.4 g of n-BuOH fraction and 540.9 g of H 2 O fraction were obtained.
그 다음, 3T3-L1 전지방세포(preadipocyte)의 분화 억제능이 우수한 EtOAc 분획물의 가용부 2.3 g을 Toyopearl HW-40 column(2.5 cm i.d.×42 cm)을 이용하여 H2O/MeOH의 MeOH 함량을 높이면서 칼럼크로마토그래피를 수행하여 EMC01~EMC06 소분획을 얻었다. YMC Pack ODS A-302 column(4.6 cm i.d.×150 mm, 5 ㎛)을 충진제로 이용한 칼럼크로마토그래피를 수행하여 소분획물 EMC02 171.4 mg으로부터 APM-1(tR 9.2 min, 16.3 mg) 및 APM-2(tR 11.6 min, 19.7 mg) 화합물을 수득하였다(도 1A). 이동상은 0.1% 포름산(formic acid, solvent A)과 아세토나이트릴(acetonitrile, solvent B)을 사용하였으며, 구배 용출(gradient elution)을 100% solvent A로 분석하여 30 min, 0% A; 100% B의 용매 조성으로 물질을 분석하였고, 이동상의 유속은 1.0 ㎖/min을 유지하여 280 nm에서 화합물을 검출하였다(표 1).Next, it has an excellent ability to inhibit the differentiation of 3T3-L1 preadipocytes. 2.3 g of the soluble portion of the EtOAc fraction was subjected to column chromatography using a Toyopearl HW-40 column (2.5 cm id × 42 cm) while increasing the MeOH content of H 2 O/MeOH to obtain subfractions EMC01 to EMC06. APM-1 (t R 9.2 min, 16.3 mg) and APM-2 were obtained from 171.4 mg of small fraction EMC02 by performing column chromatography using YMC Pack ODS A-302 column (4.6 cm id (t R 11.6 min, 19.7 mg) compound was obtained (Figure 1A). The mobile phase used was 0.1% formic acid (solvent A) and acetonitrile (solvent B), and gradient elution was analyzed with 100% solvent A for 30 min, 0% A; The material was analyzed with a solvent composition of 100% B, and the flow rate of the mobile phase was maintained at 1.0 mL/min to detect the compound at 280 nm (Table 1).
실시예 2. 여주 발효물로부터 분리된 화학식 1 및 2 화합물의 구조결정Example 2. Structure determination of compounds of formula 1 and 2 isolated from fermented bitter melon
상기 여주 발효물의 에틸아세테이트 분획물로부터 분리된 화합물은 분광화학적 및 구조 분석을 통해 화학식 1로 표시되는 신규 화합물과 화학식 2로 표시되는 Monaspilosuslin 화합물로 결정하였다(도 1B).The compounds isolated from the ethyl acetate fraction of the fermented bitter melon were determined to be a new compound represented by Formula 1 and a Monaspilosuslin compound represented by Formula 2 through spectrochemical and structural analysis (Figure 1B).
2-1. 화학식 1(New)2-1. Formula 1 (New)
화합물 1은 노란색의 무결정형 분말상 형태로 화합물을 수득하였으며, UV 스펙트럼에서 227 및 291 nm의 최대 흡광도를 나타내어 γ-lactone 골격임을 시사하였다. HRFABMS 스펙트럼에서 m/z 143.0344 [M+H]+의 base peak를 확인하여 분자량을 추정하였으며, 분자식은 C6H7O4로 확인하였다. 1H NMR 스펙트럼에서 한 개의 이중결합에 해당하는 proton 시그널이 δ 7.91 (1H, s, H-6)에서 관찰되었으며, 한 개의 methyl기가 δ 2.27 (3H, s, H-7)에서 관찰되었다. 13C NMR 및 HSQC 스펙트럼에서 한 개의 carbonyl carbon 시그널이 δ 168.5 (C-2)에서 관찰되었으며, 5개의 이중결합 carbon 시그널과 함께 한 개의 methyl기가 δ 13.8 (C-7)에서 관찰되었다. Key HMBC 스펙트럼에서 H-6이 C-4, 5와의 상관관계를 나타내었으며, H-7이 C-2, 3, 4와의 HMBC 상관관계를 나타내었다. 이상의 결과로 화합물 1은 기존에 보고되지 않은 신규 화합물로 확인하였으며, tetronic acid 유도체 화합물로 구조 결정하였다.Compound 1 was obtained in the form of a yellow amorphous powder, and showed maximum absorbance at 227 and 291 nm in the UV spectrum, suggesting that it was a γ-lactone skeleton. The molecular weight was estimated by checking the base peak of m/z 143.0344 [M+H] + in the HRFABMS spectrum, and the molecular formula was confirmed to be C 6 H 7 O 4 . In the 1H NMR spectrum, a proton signal corresponding to one double bond was observed at δ 7.91 (1H, s, H-6), and one methyl group was observed at δ 2.27 (3H, s, H-7). In the 13 C NMR and HSQC spectra, one carbonyl carbon signal was observed at δ 168.5 (C-2), and one methyl group along with five double bond carbon signals were observed at δ 13.8 (C-7). In the key HMBC spectrum, H-6 showed correlation with C-4 and 5, and H-7 showed HMBC correlation with C-2, 3, and 4. As a result of the above results, Compound 1 was confirmed to be a new compound that had not previously been reported, and its structure was determined as a tetronic acid derivative compound.
2-2. 화학식 2(Monaspilosuslin)2-2. Formula 2 (Monaspilosuslin)
화합물 2는 갈색 무결정형 분말상 형태로 화합물을 얻었으며, FABMS 측정 결과 m/z 323 [M+Na]+의 base peak를 확인하여 분자량을 추정하였다. 1H NMR 스펙트럼에서 trans-olefin에 해당하는 시그널이 δ 7.85 (1H, d, J = 15.6 Hz, H-8) 및 6.23 (1H, d, J = 15.6 Hz, H-7)이 측정되었고, 한 개의 이중결합에 해당하는 singlet proton이 δ 5.77 (1H, s, H-10)에서 관찰되었다. 또한 한 개의 oxygenated methine δ 4.09 (1H, m, H-3), 한 개의 hydroxymethyl기 δ 3.70 (1H, d, J = 7.2 Hz, H-13), 3.63 (1H, d, J = 7.2 Hz, H-13), 두 개의 methylene group δ 2.00 (1H, m, H-2), 1.80 (1H, m, H-4), 1.78 (1H, m, H-2), 1.77 (1H, m, H-4)이 관찰되었으며, 3개의 methyl기가 δ 1.96 (3H, s, H-14), 1.08 (3H, s, H-12), 0.86 (3H, s, H-11)에서 관찰되었다. 13C NMR 및 HSQC 스펙트럼에서 한 개의 carbonyl기가 δ 173.3 (C-15)에서 관찰되었고, trans-olefin, oxygenated methine, hydroxymethyl, methyl 등의 시그널이 관찰되었다. 1H-1H COSY, HMBC 및 NOESY 등의 2D NMR 측정결과 화합물 2는 Monascus pilosus 미생물을 이용하여 발효시킨 쌀에서 분리된 sequiterpene 화합물인 monaspilosuslin 화합물으로 구조 결정하였다.Compound 2 was obtained in the form of a brown amorphous powder, and the molecular weight was estimated by confirming the base peak of m/z 323 [M+Na] + as a result of FABMS measurement. In the 1 H NMR spectrum, signals corresponding to trans -olefin were measured at δ 7.85 (1H, d, J = 15.6 Hz, H-8) and 6.23 (1H, d, J = 15.6 Hz, H-7). A singlet proton corresponding to a double bond was observed at δ 5.77 (1H, s, H-10). Also, one oxygenated methine δ 4.09 (1H, m, H-3), one hydroxymethyl group δ 3.70 (1H, d, J = 7.2 Hz, H-13), 3.63 (1H, d, J = 7.2 Hz, H -13), two methylene groups δ 2.00 (1H, m, H-2), 1.80 (1H, m, H-4), 1.78 (1H, m, H-2), 1.77 (1H, m, H- 4) was observed, and three methyl groups were observed at δ 1.96 (3H, s, H-14), 1.08 (3H, s, H-12), and 0.86 (3H, s, H-11). In 13 C NMR and HSQC spectra, one carbonyl group was observed at δ 173.3 (C-15), and signals such as trans -olefin, oxygenated methine, hydroxymethyl, and methyl were observed. As a result of 2D NMR measurements of 1 H- 1 H COSY, HMBC, and NOESY, the structure of compound 2 was determined to be monaspilosuslin, a sequiterpene compound isolated from rice fermented using Monascus pilosus microorganisms.
실시예 3. 세포 독성 확인Example 3. Confirmation of cytotoxicity
3T3-L1 전지방세포(preadipocyte; Korean Cell Line Bank)는 10% FBS(fetal bovine serum)와 1% penicillin/streptomycin(100 U/㎖)을 첨가한 DMEM(Dulbeccos's Modified Eagle's Medium, Gibco, 미국)을 사용하여 37℃, 5% CO2 배양기에 적응시켜 계대 배양하였다. 상기 배양된 3T3-L1 세포(1×105 세포/웰)를 96웰-플레이트에 분주한 후 시료(여주 열수추출물, 여주 발효물, 여주 발효물의 분획물 또는 이로부터 분리된 화합물)를 농도별로 0.02 ㎖ 처리하고 배양한 후 MTT 용액(5 mg/㎖) 0.02 ㎖을 처리하여 반응시켰다. 반응이 끝난 후 540 nm에서 ELISA plate reader(Tecan Austria GmBH, Grodig, Austria)를 이용하여 흡광도를 측정하였다. 3T3-L1 preadipocytes (Korean Cell Line Bank) were grown in DMEM (Dulbeccos's Modified Eagle's Medium, Gibco, USA) supplemented with 10% FBS (fetal bovine serum) and 1% penicillin/streptomycin (100 U/ml). It was subcultured by adapting it to an incubator at 37°C and 5% CO 2 . After dispensing the cultured 3T3-L1 cells (1×10 5 cells/well) into a 96-well plate, samples (Yeoju hot water extract, bitter melon fermentation, fractions of bitter melon fermentation, or compounds isolated therefrom) were added at a concentration of 0.02. After treatment and culture, 0.02 ml of MTT solution (5 mg/ml) was added to react. After the reaction was completed, the absorbance was measured at 540 nm using an ELISA plate reader (Tecan Austria GmBH, Grodig, Austria).
그 결과, 여주 발효물, 여주 발효물의 분획물 또는 이로부터 분리된 화합물 모두 90% 이상의 높은 생존율을 보였고(도 2), 이를 통해 본 발명의 여주 발효물, 여주 발효물의 분획물 또는 이로부터 분리된 화합물은 세포 독성이 없음을 알 수 있었다.As a result, the fermented bitter melon, fractions of the fermented bitter melon, or compounds isolated therefrom all showed a high survival rate of more than 90% (Figure 2), which shows that the fermented bitter melon of the present invention, the fractions of the fermented bitter melon, or the compounds isolated therefrom It was found that there was no cytotoxicity.
실시예 4. 항비만 효능 확인Example 4. Confirmation of anti-obesity efficacy
3T3-L1 세포(1×105 세포/웰)를 플레이트에 분주한 후 각 웰당 세포가 100% 채워지는 시점에 2일간 더 배양하였다. 상기 배양된 세포에 DMI(1μM Dexamethasone, 0.5mM IBMX, 1μM Insulin)를 포함하는 10% FBS(fetal bovine serum) DMEM 배지(Dulbeccos's Modified Eagle's Medium, Gibco, 미국)를 처리하여 2일 동안 지방세포 분화를 유도한 후, 인슐린 2μM이 함유된 10% FBS DMEM로 2일 동안 배양하였다. 그 후 2일 간격으로 총 4일간 10% FBS DMEM 배양액으로 교체하였다. 지방세포 분화를 유도하는 동안 배양액에 시료를 처리하였다. 분화가 완성되는 시점인 8일째에 지방의 축적 정도를 확인하기 위해 triglyceride assay kit(Sigma-Aldrich, 미국)를 사용하여 Oil Red-O 염색을 수행하였으며, 염색된 지방 세포는 Olympus microscope(Olympus Optical Co., Ltd., 일본)를 이용하여 관찰하였다. 3T3-L1 cells (1×10 5 cells/well) were dispensed onto the plate and cultured for an additional 2 days until each well was 100% filled with cells. The cultured cells were treated with 10% FBS (fetal bovine serum) DMEM medium (Dulbeccos's Modified Eagle's Medium, Gibco, USA) containing DMI (1μM Dexamethasone, 0.5mM IBMX, 1μM Insulin) for adipocyte differentiation for 2 days. After induction, the cells were cultured for 2 days in 10% FBS DMEM containing 2 μM insulin. Afterwards, the culture medium was replaced with 10% FBS DMEM at 2-day intervals for a total of 4 days. Samples were treated with culture medium while inducing adipocyte differentiation. To confirm the degree of fat accumulation on day 8, when differentiation was completed, Oil Red-O staining was performed using a triglyceride assay kit (Sigma-Aldrich, USA), and the stained fat cells were analyzed under an Olympus microscope (Olympus Optical Co. ., Ltd., Japan) was used to observe.
먼저, 여주 발효물과 이의 분획물의 지방 축적 정도를 측정한 결과, 지방 생성 촉진 유도제인 DMI 단독 처리군(Cont, 시료 무처리)은 무처리 대조군(DMI 및 시료 무처리)에 비해 지방 축적 정도가 증가하였으나, DMI와 여주 발효물 또는 이의 EtOAc 분획물을 병행 처리하면 지방 축적 정도가 감소하는 것을 확인하였다. 특히, 20 μg/㎖ 농도의 EtOAc 분획물을 처리할 경우 약 46% 수준으로 지방 축적이 억제되었고, 양성대조군(EGCG 처리)과 유사한 지방 축적 억제 효과를 나타내었다(도 3A). First, as a result of measuring the degree of fat accumulation in fermented bitter melon and its fractions, the group treated only with DMI, an inducer for promoting lipogenesis (Cont, sample untreated), had a lower degree of fat accumulation compared to the untreated control group (DMI and sample untreated). However, it was confirmed that the degree of fat accumulation decreased when DMI and fermented bitter melon or its EtOAc fraction were treated in parallel. In particular, when treated with the EtOAc fraction at a concentration of 20 μg/ml, fat accumulation was suppressed by about 46%, showing a similar effect on suppressing fat accumulation as the positive control group (EGCG treatment) (Figure 3A).
또한, 여주 발효물의 에틸아세테이트 분획물에서 분리된 APM-1 및 APM-2 화합물의 지방 축적 정도를 측정한 결과, DMI와 APM-1 화합물을 병행 처리하면 지방 축적 정도가 감소하였고, 특히 10 uM 농도의 APM-1을 처리할 경우 약 60% 수준으로 지방 축적이 억제되어 양성대조군보다 지방 축적 억제 효과가 우수한 것을 확인하였다. 반면, APM-2 화합물은 지방 축적 억제 효과가 거의 없음을 확인하였다(도 3B).In addition, as a result of measuring the degree of fat accumulation of APM-1 and APM-2 compounds isolated from the ethyl acetate fraction of fermented bitter melon, the degree of fat accumulation was reduced when DMI and APM-1 compounds were treated in parallel, especially at a concentration of 10 uM. When treated with APM-1, fat accumulation was suppressed by about 60%, confirming that the effect of suppressing fat accumulation was superior to that of the positive control group. On the other hand, it was confirmed that the APM-2 compound had little effect on suppressing fat accumulation (Figure 3B).
또한, 분화된 3T3-L1 세포에서 지방 축적에 대한 APM-1 화합물의 효과를 확인하기 위해 Oil red O 염색을 수행한 후 현미경으로 관찰한 결과, DMI 단독 처리군에 비해 APM-1 화합물과 DMI를 병행 처리한 실험군에서 붉게 염색된 정도가 적게 관찰되었다(도 4). 이를 통해, 본 발명의 여주 발효물, 여주 발효물의 분획물 또는 이로부터 분리된 화학식 1의 화합물은 지방 축적을 억제시킬 수 있으므로, 비만 개선에 효과가 있을 것으로 예상되었다.In addition, to confirm the effect of the APM-1 compound on fat accumulation in differentiated 3T3-L1 cells, Oil red O staining was performed and observed under a microscope. As a result, the APM-1 compound and DMI compared to the DMI treatment group alone. In the experimental group treated in parallel, less red staining was observed (Figure 4). Through this, it was expected that the fermented bitter melon of the present invention, the fraction of the fermented bitter melon, or the compound of formula 1 isolated therefrom could inhibit fat accumulation and thus be effective in improving obesity.
Claims (5)
[화학식 1]
A health functional food composition for preventing or improving obesity containing a compound of the following formula (1) or an acceptable salt thereof as an active ingredient.
[Formula 1]
[화학식 1]
A pharmaceutical composition for preventing or treating obesity containing a compound of the following formula (1) or an acceptable salt thereof as an active ingredient.
[Formula 1]
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