KR20190048493A - Novel compound from plasma-treated phloridzin and anti-obesity composition comprising the same as effective component - Google Patents
Novel compound from plasma-treated phloridzin and anti-obesity composition comprising the same as effective component Download PDFInfo
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- KR20190048493A KR20190048493A KR1020170143488A KR20170143488A KR20190048493A KR 20190048493 A KR20190048493 A KR 20190048493A KR 1020170143488 A KR1020170143488 A KR 1020170143488A KR 20170143488 A KR20170143488 A KR 20170143488A KR 20190048493 A KR20190048493 A KR 20190048493A
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- Prior art keywords
- phloridzin
- plasma
- compound
- obesity
- present
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- A—HUMAN NECESSITIES
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
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Abstract
Description
본 발명은 플라즈마 처리된 플로리진 유래 신규 화합물 및 이를 유효성분으로 함유하는 항비만용 조성물에 관한 것으로, 더욱 상세하게는 플로리진에 플라즈마를 처리하여 생성된 플로리진 이합체 화합물 및 이를 유효성분으로 함유하는 항비만용 조성물에 관한 것이다. The present invention relates to a novel compound derived from plasma-treated florixin and an antiobesity composition containing the compound as an active ingredient, and more particularly to a floririzin dimer compound produced by treating florazin with plasma, To an anti-obesity composition.
비만은 체내에 지방조직이 과다하게 축적된 상태로, 비만인 경우 일반적으로 체중이 많이 나가지만, 비만이 아니더라도 근육이 많은 사람도 체중이 많이 나갈 수 있기 때문에 체내에 지방조직이 과다한 상태를 비만으로 정의한다. 오랜 기간에 걸쳐 에너지 소비량에 비해 영양소를 과다 섭취할 경우 에너지 불균형에 의해 비만이 유도되며, 이 외에도 호르몬의 변화, 유전, 정신 건강 문제 및 사회경제적 요인 등이 복합적으로 관련되어 있다. 전 세계적으로 비만 인구가 증가하는 추세로, 최근 성인병을 유발하는 중요한 요인으로 지목받으며 비만의 심각성이 중요한 문제로 대두되고 있다.Obesity is a state of excessive accumulation of adipose tissue in the body. Obesity usually causes a lot of weight. However, even if not obese, even people with a lot of muscles can lose a lot of weight. do. Excessive intake of nutrients over a long period of time in relation to energy consumption induces obesity by energy imbalance, and in addition is associated with changes in hormones, genetic, mental health problems, and socioeconomic factors. As the global obesity population is increasing, the importance of obesity has become an important issue.
비만을 예방 및 개선하고, 건강 체중을 유지하기 위해서는 균형잡힌 식사와 규칙적인 운동을 통하여 평생 동안 꾸준한 관리가 필요하다. 특히 지방세포는 한번 만들어지면 크기는 줄일 수 있으나, 자연적으로 제거하는 것은 불가능하여 영구적으로 인체에 남아있게 되므로 처음부터 비만이 되지 않도록 예방하는 것이 중요하다. In order to prevent and improve obesity and to maintain a healthy weight, a balanced diet and regular exercise are needed to maintain the lifelong lifetime. In particular, fat cells can be reduced in size once they are made, but it is impossible to remove them naturally and it is left permanently in the human body, so it is important to prevent obesity from the beginning.
비만의 예방, 개선 또는 치료를 위해서 섭취하는 칼로리를 줄이고, 활동 및 운동량을 증가시키는 방법 및 지방흡수를 감소시키는 등의 약물을 복용하는 방법 등이 이용되고 있다. Methods for reducing calories consumed, increasing activity and exercise, and taking medications such as reducing fat absorption for the prevention, improvement, or treatment of obesity have been used.
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 혈압 감소나 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 serotonin nervous system, ephedrine and caffeine through the noradrenergic nervous system, sibutramine, which simultaneously acts on the serotonin and noradrenergic nervous system, and olyrie, which inhibits the lipase produced by the pancreas, There are drugs such as start. However, pfuramilamine has been prohibited because of its side effects such as primary pulmonary hypertension and heart valve lesion, and other drugs have problems such as decreased blood pressure and lactic acidosis, and are used for patients with heart failure and renal disease There is a problem that can not be done. Therefore, there is a need to prevent, ameliorate, or develop a therapeutic substance for obesity with a low side effect.
한편, 플로리진(phloridzin)은 플로레틴(phloretin)에 포도당(glucose)이 결합한 형태의 칼콘(chalcone) 배당체 화합물로서 사과의 과육보다는 비식용부인 껍질이나 씨에 많이 함유되어 있어, 사람들의 직접적인 섭취는 적은 편이다. 따라서 다양한 생물전환 방법을 이용하여 버려지는 비식용부로부터 새로운 천연 생리활성 물질을 개발한다면, 버려지는 원료를 자원화하여 환경문제를 방지할 수 있고, 새로운 소득원이 될 수 있다.On the other hand, phloridzin is a chalcone glycoside compound in which glucose is bound to phloretin, which is contained in shells and seeds of non-edible ginseng rather than apple flesh. It is small. Therefore, if a new natural bioactive substance is developed from abandoned non-edible parts using various bioconversion methods, it is possible to save abandoned raw materials, prevent environmental problems, and become a new source of income.
한편, 전리된 가스 상태인 플라즈마에는 전자, 양이온, 음이온, 자유라디칼 및 광자 등을 포함하는 활성산소종이 존재한다. 최근에는 기존의 식품 살균 기술이 갖고 있는 문제점들을 최소화시키기 위하여 다양한 기술들이 개발되고 있으며, 그중에서도 비열 플라즈마 처리기술이 주목을 끌고 있다. 비열 플라즈마 기술은 식품의 미생물을 저해하는 기술 이외에 환경, 의료 분야에서 살균 및 소독기술로 개발되고 있으나, 식품의 성분에 화학적, 기능적 변화에 대한 연구는 아직 미흡한 상황이다. On the other hand, in the ionized plasma, there exist active oxygen species including electrons, cations, anions, free radicals, and photons. In recent years, various technologies have been developed to minimize the problems of existing food disinfection technology, and non-thermal plasma processing technology has attracted attention. Nonthermal plasma technology is being developed as a disinfection and disinfection technology in environment and medical field besides the technology to inhibit microorganisms of food. However, research on the chemical and functional change of food ingredient is still insufficient.
한편, 한국등록특허 제1492277호에는 나트륨 글루코즈 공-전달체 2의 억제제로서의 플로리진 유사체가 개시되어 있지만, 본 발명의 플라즈마 처리된 플로리진 유래 신규 화합물 및 이를 유효성분으로 함유하는 항비만용 조성물에 관해 개시된 바 없다.On the other hand, Korean Patent No. 1492277 discloses a florigen analogue as an inhibitor of
본 발명은 상기와 같은 요구에 의해 도출된 것으로서, 플로리진에 플라즈마를 처리하여 플라즈마 유래의 이합체 화합물(메틸렌비스플로리진, 디글루코실메틸렌비스플로리진, 메틸렌비스플로레틴)을 제조하고, 상기 플라즈마 유래 신규 화합물을 유효성분으로 함유하는 항비만용 조성물을 제공하며, 상기 조성물이 췌장 리파아제(pancreatic lipase)의 활성을 저해하고, 지방축적을 억제하는 것을 확인함으로써, 본 발명을 완성하였다.Disclosure 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 a method for producing a plasma-derived dimer compound (methylenebisphloridin, diglucosylmethylenebisphloridine, methylenebisfloretin) Which comprises the novel compound as an active ingredient, and that the composition inhibits the activity of pancreatic lipase and inhibits the fat accumulation, thereby completing the present invention.
상기 과제를 해결하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염을 제공한다:In order to solve the above-mentioned problems, the present invention provides a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:
[화학식 1][Chemical Formula 1]
상기 식에서, R1 및 R2는 각각 또는 수소(H)이다.Wherein R < 1 > and R < 2 & Or hydrogen (H).
또한, 본 발명은 상기 화합물을 유효성분으로 함유하는 비만의 예방 또는 치료용 약학 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for preventing or treating obesity containing the above-mentioned compound as an active ingredient.
또한, 본 발명은 상기 화합물을 유효성분으로 함유하는 비만의 예방 또는 개선용 건강기능식품 조성물을 제공한다. The present invention also provides a health functional food composition for preventing or ameliorating obesity containing the above-mentioned compound as an active ingredient.
본 발명은 플라즈마 처리된 플로리진 유래 신규 화합물 및 이를 유효성분으로 함유하는 항비만용 조성물에 관한 것으로, 플로리진에 플라즈마를 처리하여 3종의 플로리진 유래의 이합체 화합물(메틸렌비스플로리진, 디글루코실메틸렌비스플로리진, 메틸렌비스플로레틴)을 제조하였으며, 상기 화합물은 플로리진에 비해 췌장 리파아제(pancreatic lipase)의 활성을 저해하고, 지방세포의 분화 시 지방축적을 억제하는 효과가 증진되며, 특히 플로리진에 당이 제거된 형태인 플로레틴이 메틸기에 의해 이합체를 형성한 본 발명의 메틸렌비스플로레틴은 플로레틴에 비해서도 지방축적 억제효과가 우수하므로, 비만의 예방 또는 치료용 약학 조성물, 비만의 예방 또는 개선용 건강기능식품 조성물로 활용할 수 있다. The present invention relates to a novel compound derived from plasma-treated florixin and an antiobesity composition containing the same as an effective ingredient. The present invention relates to a novel compound derived from plasma-treated floririne and a method of treating the florisin with plasma to prepare a dimeric compound derived from three kinds of florirines (methylene bis- (Methylenebisfloridine, methylenebisflorin, methylenebisfloridine, methylenebisflorin and methylenebisflorethine). These compounds inhibit the activity of pancreatic lipase and inhibit fat accumulation during the differentiation of adipocytes, The methylene bis floretine of the present invention in which floretine, a sugar-removed form of floridin, forms a duplex by a methyl group, is superior to floretin in its effect of inhibiting fat accumulation, and thus is useful as a pharmaceutical composition for preventing or treating obesity, Or as a health functional food composition for prevention or improvement.
도 1은 본 발명의 신규 화합물인 메틸렌비스플로리진(methylenebisphloridzin) 화합물(A), 디글루코실메틸렌비스플로리진(deglucoslymethylenebisphloridzin) 화합물(B), 메틸렌비스플로레틴(methylenebisphloretin) 화합물(C)의 HMBC 수행결과, 수소와 탄소의 상호작용 관계를 나타낸 것이다.
도 2는 본 발명의 신규 화합물에 의한 지방축적 억제효과를 확인한 결과이다. MDI(IBMX(3-isobutyl-1-methylxanthine), 덱사메타손(dexamethasone), 인슐린(insulin)의 혼합물)는 분화 유도 물질로, 지방전구세포인 3T3-L1의 분화를 유도하기 위해 사용하였다. Control은 화합물을 처리하지 않은 음성대조군이고, 1은 플로리진을 처리한 군이고, 2는 메틸렌비스플로리진(methylenebisphloridzin) 화합물을 처리한 군이고, 3은 디글루코실메틸렌비스플로리진(deglucoslymethylenebisphloridzin) 화합물을 처리한 군이고, 4는 메틸렌비스플로레틴(methylenebisphloretin) 화합물을 처리한 군이며, 5는 플로레틴을 처리한 군이다. *은 MDI만 처리한 Control군에 비해 지방세포 분화가 유의미하게 감소하였다는 것으로, p<0.05임을 의미한다.BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a graph showing the results of the HMBC performance of a novel compound of the present invention, methylenebisphloridzin (A), deglucosylmethylenebisphloridzin (B), and methylenebisphloretin (C) As a result, the relationship between hydrogen and carbon is shown.
Fig. 2 shows the result of confirming the fat accumulation inhibitory effect by the novel compound of the present invention. MDI (a mixture of 3-isobutyl-1-methylxanthine, dexamethasone, and insulin) was used as a differentiation inducing substance to induce the differentiation of 3T3-L1 as a lipogenic precursor cell. Control was a negative control without compound treatment, 1 was treated with floridine, 2 was treated with methylenebisphloridzin compound, 3 was treated with
본 발명은 하기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염에 관한 것이다.The present invention relates to a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof.
상기 식에서, R1 및 R2는 각각 또는 수소(H)이다.Wherein R < 1 > and R < 2 & Or hydrogen (H).
본 발명의 일 구현 예에서, 상기 R1 및 R2는 각각 인 메틸렌비스플로리진(methylenebisphloridzin) 화합물일 수 있으나, 이에 제한하지 않는다. In one embodiment of the present invention, R < 1 > and R < 2 & But are not limited to, methylenebisphloridzin compounds.
본 발명의 일 구현 예에서, 상기 R1은 이고, R2는 수소(H)인 디글루코실메틸렌비스플로리진(deglucoslymethylenebisphloridzin) 화합물일 수 있으나, 이에 제한되지 않는다.In one embodiment of the invention, R < 1 > is And R 2 is hydrogen (H), but it is not limited thereto.
본 발명의 일 구현 예에서, 상기 R1 및 R2는 수소(H)인 메틸렌비스플로레틴(methylenebisphloretin) 화합물일 수 있으나, 이에 제한되지 않는다.In one embodiment of the present invention, R < 1 > and R < 2 > may be methylenebisphloretin compounds which are hydrogen (H), but are not limited thereto.
본 발명의 일 구현 예에서, 상기 화합물은 플로리진에 플라즈마를 처리하는 단계를 포함하여 제조할 수 있고, 상기 플라즈마는 유전장벽 방전, 코로나 방전, 마이크로파 방전 또는 아크 방전 플라즈마일 수 있으며, 예를 들면 유전체 장벽 방전의 방식으로 200~300W 전력 및 10~20㎑ 주파수 조건에서 플로리진에 30~80분 동안 처리하는 것이고, 바람직하게는 유전체 장벽 방전의 방식으로 250W 전력 및 15㎑ 주파수 조건에서 플로리진에 40~60분 동안 처리하는 것이고, 가장 바람직하게는 유전체 장벽 방전의 방식으로 250W 전력 및 15㎑ 주파수 조건에서 플로리진에 60분 동안 처리하는 것이지만, 이에 제한되지 않는다.In one embodiment of the present invention, the compound may be prepared by treating the plasma with a floridine, wherein the plasma may be a dielectric barrier discharge, a corona discharge, a microwave discharge or an arc discharge plasma, In the manner of dielectric barrier discharge, for 30 to 80 minutes at a frequency of 200 to 300 W power and 10 to 20 kHz frequency, preferably at a 250 W power and 15 kHz frequency in a manner of dielectric barrier discharge But is not limited to, treating for 40 to 60 minutes, and most preferably for 60 minutes at Floritz in 250 W power and 15 KHz frequency conditions in the manner of dielectric barrier discharge.
또한, 본 발명은 상기 화합물을 유효성분으로 함유하는 비만의 예방 또는 치료용 약학 조성물에 관한 것이다. The present invention also relates to a pharmaceutical composition for preventing or treating obesity, which comprises the above compound as an active ingredient.
상기 플라즈마가 처리된 플로리진 유래 신규 화합물은 췌장 리파아제(pancreatic lipase)의 활성을 저해하고, 지방세포의 분화시 지방축적을 억제하는 것이지만, 이에 제한되지 않는다.The plasma-treated novel compound derived from Florisin inhibits the activity of pancreatic lipase and inhibits fat accumulation upon differentiation of adipocytes, but is not limited thereto.
본 발명의 약학조성물은 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. The pharmaceutical composition of the present invention may contain a pharmaceutically acceptable carrier in addition to the active ingredient. Such a carrier is usually used at the time of formulation, and includes lactose, dextrose, sucrose, sorbitol, mannitol, starch, Calcium carbonate, calcium phosphate, alginate, gelatin, calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methylcellulose, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and minerals Oils, and the like, but are not limited thereto. The pharmaceutical composition of the present invention may further contain a lubricant, a wetting agent, a sweetening agent, a flavoring agent, an emulsifying agent, a suspending agent, a preservative, etc., in addition to the above components.
본 발명에 따른 약학조성물의 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 according to the present invention may vary depending on such factors as the formulation method, the administration method, the patient's age, body weight, sex, pathological condition, food, administration time, administration route, excretion rate, .
본 발명의 약학조성물은 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 may be administered orally or parenterally. In the case of parenteral administration, the composition may be administered topically to the skin, intravenously, subcutaneously, intramuscularly, intraperitoneally, or transdermally.
본 발명의 약학조성물은 비만의 억제 및 치료를 위하여 단독으로, 또는 수술, 방사선치료, 호르몬치료, 화학치료 및 생물학적 반응 조절제를 사용하는 방법들과 병용하여 사용할 수 있다. The pharmaceutical composition of the present invention can be used alone or in combination with methods using surgery, radiation therapy, hormone therapy, chemotherapy and biological response modifiers for the inhibition and treatment of obesity.
본 발명의 조성물에 포함되는 유효성분의 농도는 치료 목적, 환자의 상태, 필요기간 등을 고려하여 결정할 수 있으며 특정 범위의 농도로 한정되지 않는다.The concentration of the active ingredient contained in the composition of the present invention can be determined in consideration of the purpose of treatment, the condition of the patient, the period of time required, and the like, and is not limited to a specific range of concentration.
본 발명의 약학조성물은 당해 발명이 속하는 기술분야에서 통상의 지식을 가진 자가 용이하게 실시할 수 있는 방법에 따라, 약학적으로 허용되는 담체 또는 부형제를 이용하여 제제화함으로써 단위 용량 형태로 제조되거나 또는 다용량 용기 내에 내입시켜 제조될 수 있다. 이때 제형은 주사제, 크림, 패취, 분무제, 연고제, 경고제, 로션제, 리니멘트제, 파스타제 및 카타플라스마제 중에서 선택된 어느 하나의 제형으로 제조될 수도 있으며, 분산제 또는 안정화제를 추가적으로 포함할 수 있다.The pharmaceutical composition of the present invention may be manufactured in a unit dosage form by formulating it using a pharmaceutically acceptable carrier or excipient according to a method which can be easily carried out by those having ordinary skill in the art to which the present invention belongs Into a capacity container. The formulations may be formulated into any one of the formulations selected from injectables, creams, patches, sprays, ointments, alerts, lotions, liniments, pastes and cataplasms, and may additionally contain dispersing or stabilizing agents have.
또한, 본 발명은 상기 화합물을 유효성분으로 함유하는 비만의 예방 또는 개선용 건강기능식품 조성물에 관한 것이다. The present invention also relates to a health functional food composition for preventing or ameliorating obesity containing the above-mentioned compound as an active ingredient.
본 발명의 건강기능식품 조성물을 식품첨가물로 사용하는 경우, 상기 건강기능식품 조성물을 그대로 첨가하거나 다른 식품 또는 식품성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효성분의 양은 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 섭취인 경우에는 상기 양은 상기 범위 이하일 수 있으며, 안전성 면에서 아무런 문제가 없기 때문에 유효성분은 상기 범위 이상의 양으로 사용될 수 있다.When the health functional food composition of the present invention is used as a food additive, the health functional food composition may be added as it is, or may be used together with other food or food ingredients, and suitably used according to a conventional method. The amount of the active ingredient can be suitably used depending on its use purpose (prevention or improvement). Generally, the health functional food composition of the present invention is added in an amount of not more than 15 parts by weight, preferably not more than 10 parts by weight based on the raw material, when the food or beverage is produced. However, in the case of long-term consumption intended for health, the amount may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount of more than the above range.
상기 건강기능식품의 종류에 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.There is no particular limitation on the kind of the health functional food. Examples of the foods to which the health functional food composition can be added include dairy products including meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen and other noodles, gums, ice cream, soups, Drinks, alcoholic beverages, and vitamin complexes, all of which include health foods in a conventional sense.
또한, 본 발명의 건강기능식품 조성물은 식품, 특히 기능성 식품으로 제조될 수 있다. 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 포함할 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.In addition, the health functional food composition of the present invention can be produced as a food, particularly a functional food. The functional food of the present invention includes components that are ordinarily added in food production, and includes, for example, proteins, carbohydrates, fats, nutrients, and seasonings. For example, when it is made of a drink, it may contain, in addition to the active ingredient, a natural carbohydrate or a flavoring agent as an additional ingredient. The natural carbohydrate may be selected from the group consisting of monosaccharides (e.g., glucose, fructose, etc.), disaccharides (e.g., maltose, sucrose etc.), oligosaccharides, polysaccharides (e.g., dextrin, cyclodextrin, , Xylitol, sorbitol, erythritol, etc.). The flavoring agent may be a natural flavoring agent (e.g., tau Martin, stevia extract, etc.) and a synthetic flavoring agent (e.g., saccharin, aspartame, etc.).
상기 건강기능식품 조성물 이외에 여러 가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알코올, 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-mentioned health functional food composition, various nutrients, vitamins, electrolytes, flavors, colorants, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloid thickening agents, pH adjusting agents, stabilizers, preservatives, glycerin, A carbonating agent used in beverages, and the like. Although the ratio of the above-mentioned ingredients is not critical, it is generally selected in the range of 0.01 to 0.1 part by weight based on 100 parts by weight of the health functional food composition of the present invention.
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. 플라즈마가Plasma 처리된 Treated 플로리진Florian 유래 신규 화합물의 제조 및 분리 Preparation and Separation of Derived New Compounds
플라즈마 처리를 위해 유전체 장벽 방전(dielectric barrier discharge, DBD)(250W, 15kHz, ambient air) 플라즈마 기기(240×200×100mm)를 사용하였다. 플로리진 1.0g을 메탄올(MeOH) 7.0ℓ에 녹인 후, DBD 플라즈마 기기에서 20, 40 및 60분 동안 처리하며, 신규 물질의 생성을 역상 HPLC(reversed phase high performance liquid chromatography)를 통하여 모니터링하였다. A dielectric barrier discharge (DBD) (250 W, 15 kHz, ambient air) plasma device (240 × 200 × 100 mm) was used for the plasma treatment. 1.0 g of floridine was dissolved in 7.0 L of methanol (MeOH), treated with DBD plasma apparatus for 20, 40 and 60 minutes, and the formation of the new substance was monitored by reversed phase high performance liquid chromatography (HPLC).
HPLC 분석의 이동상 용매로는 1% 포름산(formic acid, A)과 아세토나이트릴(acetonitrile, B)을 사용하였다. 물질 분석은 0-5분 동안은 95%(v/v)의 A 용매와 5%(v/v)의 B 용매 조성으로, 5-10분 동안은 85%(v/v)의 A 용매와 15%(v/v)의 B 용매 조성으로, 10-15분 동안은 70%(v/v)의 A 용매와 30%(v/v)의 B 용매 조성으로, 15-20분 동안은 50%(v/v)의 A 용매와 50%(v/v)의 B 용매 조성으로, 20-30분 동안은 100%(v/v) B 용매 조성으로 물질 분석을 하였으며, 이동상의 유속은 분당 1.0㎖를 유지하였고, 280nm의 파장에서 화합물을 검출하였다. HPLC 분석용 칼럼은 YMC-Pack ODS A-302 컬럼(4.6mm i.d.×150mm; YMC Co., Ltd., Tokyo, Japan)을 사용하였다. 1% formic acid (A) and acetonitrile (B) were used as mobile phase solvents for HPLC analysis. Material analysis was carried out for 5 to 10 minutes with 85% (v / v) of A solvent and 5% (v / v) With a B solvent composition of 15% (v / v), a solvent composition of 70% (v / v) A solvent and 30% (v / v) B for 10-15 minutes, The solvent was analyzed with a solvent composition of 100% (v / v) A solvent and 50% (v / v) B solvent for 20-30 minutes, 1.0 ml was maintained and the compound was detected at a wavelength of 280 nm. The column for HPLC analysis was a YMC-Pack ODS A-302 column (4.6 mm id x 150 mm; YMC Co., Ltd., Tokyo, Japan).
플라즈마를 60분 동안 처리한 경우, 다양한 신규 물질이 생성됨을 확인한 후, 플라즈마를 60분 동안 처리한 후 생성된 플로리진 반응물을 건조하고, 메탄올(MeOH)에 용해시킨 후, YMC GEL ODS AQ 120-50S 컬럼(2.5㎝ i.d.×40㎝) 상에서 단계적 구배를 통해 화합물 A(100.8㎎, t R 16.6분), 화합물 B(76.1㎎, t R 19.4분), 화합물 C(2.3㎎, t R 22.6분) 및 화합물 D(38.5㎎, t R 16.9분)를 분리하였다. 화합물 D는 이전에 보고된 플로레틴이었다(J Nat Prod(1980), 43, 739-751). When the plasma was treated for 60 minutes, it was confirmed that various new materials were produced. After the plasma was treated for 60 minutes, the produced flurbine reactant was dried and dissolved in methanol (MeOH), and then YMC GEL ODS AQ 120- 50S column (2.5㎝ id × 40㎝) compound a (100.8㎎, t R 16.6 min) through a step-by-step gradient, compound B (76.1㎎, t R 19.4 min) and compound C (2.3㎎, t R 22.6 min) on and the compound D (38.5㎎, t R 16.9 min) was isolated. Compound D was a previously reported floretine (J Nat Prod (1980), 43, 739-751).
실시예Example 2. 2. 플라즈마가Plasma 처리된 Treated 플로리진Florian 유래 신규 화합물의 구조 분석 Structural analysis of the resulting new compounds
실시예 1에서 분리한 화합물 A, B 및 C의 구조를 분석하였다. The structures of the compounds A, B, and C isolated in Example 1 were analyzed.
신규 화합물 A: 황색의 무정형 분말. [α]20 D-18.1°(c0.1, MeOH); UV λmax MeOH㎚(logε): 203(4.10), 226(4.01), 288(3.83); 1H NMR(CD3OD, 600MHz): δ7.04(4H, d, J=8.4Hz, H-2, -2a, -6, -6a), 6.67(4H, d, J=8.4Hz, H-3, -3a, -5, -5a), 6.26(2H, s, H-3', -3a'), 5.03(2H, d, J=7.8Hz, H-1", -1a"), 3.88(2H, dd, J=2.4, 12.0Hz, H-6", -6a"), 3.79(2H, s, H-CH2), 3.68(2H, dd, J=6.0, 12.0Hz, H-6", -6a"), 3.50(4H, t, J=7.8Hz, H-8, -8a), 3.47(2H, m, H-2", -2a"), 3.40(2H, m, H-3", -3a"), 3.38(2H, m, H-4", -4a"), 3.36(2H, m, H-5", -5a"), 2.87(4H, t, J=7.8Hz, H-7, 7a); 13C NMR(CD3OD, 150MHz): δ207.2(C-9, -9a), 164.0(C-4', -4a'), 163.6(C-6', -6a'), 160.4(C-2', -2a'), 156.4(C-4, -4a), 133.8(C-1, -1a), 130.4(C-2, -2a, -6, -6a), 116.1(C-3, -3a, -5, -5a), 109.1(C-5', -5a'), 106.7(C-1', -1a'), 102.1(C-1", -1a"), 96.0(C-3', -3a'), 78.4(C-3", -3a"), 78.3(C-5", -5a"), 74.7(C-2", -2a"), 71.1(C-4", -4a"), 62.4(C-6", -6a"), 47.0(C-8, -8a), 30.8(C-7, -7a), 16.2(C-CH2); FABMS m/z 833[M-H]-, HRFABMS m/z 833.2657[M-H]-(calcd for C43H47O20, 833.2661).New compound A: amorphous amorphous powder. [a] 20 D -18.1 [deg.] ( c 0.1, MeOH); UV? Max MeOH nm (log?): 203 (4.10), 226 (4.01), 288 (3.83); 1 H NMR (CD 3 OD, 600MHz): δ7.04 (4H, d, J = 8.4Hz, H-2, -2a, -6, -6a), 6.67 (4H, d, J = 8.4Hz, H -3, -5, -5a), 6.26 (2H, s, H-3 ', -3a'), 5.03 (2H, d, J = 7.8Hz, H- 3.88 (2H, dd, J = 2.4, 12.0Hz, H-6 ", -6a"), 3.79 (2H, s, H-CH 2), 3.68 (2H, dd, J = 6.0, 12.0Hz, H- (2H, m, H), 3.70 (2H, m, H-2 ", -2a"), 3.50 (4H, t, J = 7.8Hz, , 3.38 (2H, m, H-5 ", -5a"), 2.87 (4H, t, J = 7.8 Hz, H-7, 7a); 13 C NMR (CD 3 OD, 150MHz): δ207.2 (C-9, -9a), 164.0 (C-4 ', -4a'), 163.6 (C-6 ', -6a'), 160.4 (C -2 ', -2a'), 156.4 (C-4, -4a), 133.8 (C-1, -1a), 130.4 , -3a, -5, -5a), 109.1 (C-5 ', -5a'), 106.7 (C-1 ', -1a'), 102.1 -3 ', -3a'), 78.4 (C-3 '', -3a ''), 78.3 (C-5 ', -5a''), 74.7 ", -4a"), 62.4 ( C-6 ", -6a"), 47.0 (C-8, -8a), 30.8 (C-7, -7a), 16.2 (C-CH 2); FABMS m / z 833 [MH] - , HRFABMS m / z 833.2657 [MH] - (calcd for C 43 H 47 O 20 , 833.2661).
상기 결과를 종합하여, 신규 화합물 A는 분자식 C43H47O20의 메틸렌비스플로리진(methylenebisphloridzin)으로 규명하였다.In conclusion, the novel compound A was identified as methylenebisphloridzin of the molecular formula C 43 H 47 O 20 .
신규 화합물 B: 백색의 무정형 분말. [α]20 D-11.2°(c0.1, MeOH); UV λmax MeOH㎚(logε): 205(4.08), 225(4.06), 289(3.81); 1H NMR(CD3OD, 600MHz): δ7.05(2H, d, J=7.8Hz, H-2, -6), 7.01(2H, d, J=8.4Hz, H-2a, -6a), 6.68(2H, d, J=8.4Hz, H-3, -5), 6.67(2H, d, J=8.4Hz, H-3a, -5a), 6.29(1H, s, H-3'), 5.92(1H, s, H-3a'), 5.04(1H, d, J=7.8Hz, H-1"), 3.87(1H, dd, J=2.4, 12.0Hz, H-6"), 3.71(2H, s, H-CH2), 3.68(1H, dd, J=6.0, 12.0Hz, H-6"), 3.49(1H, m, H-2"), 3.45(1H, m, H-3"), 3.44(2H, t, J=7.8Hz, H-8), 3.42(1H, m, H-5"), 3.39(1H, m, H-4"), 3.27(2H, t, J=7.8Hz, H-8a), 2.86(2H, t, J=7.8Hz, H-7), 2.82(2H, t, J=7.8Hz, H-7a); 13C NMR(CD3OD, 150MHz): δ207.3(C-9), 207.1(C-9a), 163.6(C-6a'), 163.5(C-6'), 163.3(C-2a'), 163.2(C-4'), 162.7(C-4a'), 160.6(C-2'), 156.4(C-4), 156.3(C-4a), 133.9(C-1a), 133.7(C-1), 130.4(C-2, -6), 130.3(C-2a, -6a), 116.1(C-3, -5), 116.0(C-3a, -5a), 109.3(C-1'), 106.7(C-1a'), 106.6(C-5'), 106.5(C-5a'), 105.6(C-3a'), 102.0(C-1"), 96.5(C-3'), 78.4(C-5"), 78.3(C-3"), 74.7(C-2"), 71.1(C-4"), 62.4(C-6"), 47.4(C-8a), 46.9(C-8), 31.4(C-7), 30.7(C-7a), 16.2(C-CH2); FABMS m/z 721[M-H]-, HRFABMS m/z 721.2141[M-H]-(calcd for C37H37O15, 721.2132).New compound B: white amorphous powder. [α] 20 D -11.2 ° ( c 0.1, MeOH); UV? Max MeOH nm (log?): 205 (4.08), 225 (4.06), 289 (3.81); 1 H NMR (CD 3 OD, 600MHz): δ7.05 (2H, d, J = 7.8Hz, H-2, -6), 7.01 (2H, d, J = 8.4Hz, H-2a, -6a) , 6.68 (2H, d, J = 8.4 Hz, H-3, -5), 6.67 (2H, d, J = 8.4 Hz, H- , 5.92 (1H, s, H -3a '), 5.04 (1H, d, J = 7.8Hz, H-1 "), 3.87 (1H, dd, J = 2.4, 12.0Hz, H-6"), 3.71 (2H, s, H-CH 2), 3.68 (1H, dd, J = 6.0, 12.0Hz, H-6 "), 3.49 (1H, m, H-2"), 3.45 (1H, m, H- M, H-4 "), 3.27 (2H, t, 3H), 3.44 (2H, t, J = 7.8Hz, H- J = 7.8Hz, H-8a) , 2.86 (2H, t, J = 7.8Hz, H-7), 2.82 (2H, t, J = 7.8Hz, H-7a); 13 C NMR (CD 3 OD, 163.3 (C-6 '), 163.3 (C-2a'), 163.2 (C-4 '), 163.6 , 162.7 (C-4a '), 160.6 (C-2'), 156.4 (C-4), 156.3 , -6.3), 130.3 (C-2a, -6a), 116.1 (C-3, -5), 116.0 , 106.6 (C-5 '), 106.5 (C-5a'), 105.6 (C-3a '), 102.0 (C-3), 74.7 (C-2), 71.1 (C-4), 62.4 ), 30.7 (C-7a) , 16.2 (C-CH 2); FABMS m / z 721 [MH] - , HRFABMS m / z 721.2141 [MH] - (calcd for C 37 H 37 O 15 , 721.2132).
상기 결과를 종합하여, 신규 화합물 B는 분자식 C37H37O15의 디글루코실메틸렌비스플로리진(deglucoslymethylenebisphloridzin)으로 규명하였다.In conclusion, the novel compound B was identified as deglucosylmethylenebisphloridzin of the molecular formula C 37 H 37 O 15 .
신규 화합물 C: 백색의 무정형 분말. UV λmax MeOH㎚(logε): 205(4.12), 227(4.03), 289(3.78); 1H NMR(CD3OD, 600MHz): δ7.04(4H, d, J=9.0Hz, H-2, H-2a, -6, -6a), 6.68(4H, d, J=8.4Hz, H-3, H-3a, -5, -5a), 5.91(2H, s, H-3', H-3a'), 3.69(2H, s, H-CH2), 3.34(4H, t, J=7.8Hz, H-8, H-8a), 2.85(4H, t, J=7.8Hz, H-7, H-7a); 13C NMR(CD3OD, 150MHz): δ206.9(C-9, -9a), 163.4(C-6', -6a'), 163.3(C-2', -2a'), 162.7(C-4', -4a'), 156.5(C-4, -4a), 133.9(C-1, -1a), 130.3(C-2, -2a, -6, -6a), 116.1(C-3, -3a, -5, -5a), 107.1(C-5', -5a'), 105.3(C-1', -1a'), 96.1(C-3', -3a'), 47.4(C-8, -8a), 31.6(C-7, -7a), 14.4(C-CH2); FABMS m/z 559[M-H]-, HRFABMS m/z 559.1599[M-H]-(calcd for C31H27O10, 559.1604).New compound C: White amorphous powder. UV? Max MeOH nm (log?): 205 (4.12), 227 (4.03), 289 (3.78); 1 H NMR (CD 3 OD, 600MHz): δ7.04 (4H, d, J = 9.0Hz, H-2, H-2a, -6, -6a), 6.68 (4H, d, J = 8.4Hz, (2H, s, H-CH 2 ), 3.34 (4H, t, 3H, J = 7.8 Hz, H-8, H-8a), 2.85 (4H, t, J = 7.8 Hz, H-7, H-7a); 13 C NMR (CD 3 OD, 150MHz): δ206.9 (C-9, -9a), 163.4 (C-6 ', -6a'), 163.3 (C-2 ', -2a'), 162.7 (C -4 ', -4a'), 156.5 (C-4, -4a), 133.9 (C-1, -1a), 130.3 , -3a, -5, -5a), 107.1 (C-5 ', -5a'), 105.3 -8, -8a), 31.6 (C -7, -7a), 14.4 (C-CH 2); FABMS m / z 559 [MH] - , HRFABMS m / z 559.1599 [MH] - (calcd for C 31 H 27 O 10 , 559.1604).
상기 결과를 종합하여, 신규 화합물 C는 분자식 C31H27O10의 메틸렌비스플로레틴(methylenebisphloretin)으로 규명하였다.Taking the above results into consideration, the novel compound C was identified as methylenebisphloretin of the molecular formula C 31 H 27 O 10 .
신규 화합물인 메틸렌비스플로리진(methylenebisphloridzin) 화합물(A), 디글루코실메틸렌비스플로리진(deglucoslymethylenebisphloridzin) 화합물(B), 메틸렌비스플로레틴(methylenebisphloretin) 화합물(C)의 HMBC 수행결과, 수소와 탄소의 상호작용 관계는 도 1에 나타낸 바와 같다.As a result of HMBC of the new compounds, methylenebisphloridzin (A), deglucosylmethylenebisphloridzin (B) and methylenebisphloretin (C), hydrogen and carbon The interaction relationship is as shown in Fig.
실시예Example 3. 3. 플라즈마가Plasma 처리된 Treated 플로리진Florian 유래 신규 화합물의 췌장 리파아제 저해 활성 측정 Of pancreatic lipase inhibitory activity of the novel compounds
췌장 리파아제 저해활성 측정은 Kim 등이 행한 방법을 변형하여 실시하였다. 즉 효소 완충용액(10mM MOPS, 1mM EDTA, pH 6.8)에 돼지 췌장 리파아제(porcine pancreatic lipase)를 0.5g/200㎖의 농도로 4℃를 유지하면서 용해하고, 상기 용해물을 4000rpm으로 원심 분리한 후, 상층액에 트리스 완충용액(100mM Tris-HCl, 5mM CaCl2, pH 7.0)과 효소 완충용액(enzyme buffer)을 혼합하였다. 실시예 1에서 분리한 신규 화합물은 DMSO로 용해하여 최종 농도가 3%(w/v)가 되도록 한 후, 37℃에서 15분 동안 상기의 돼지 췌장 리파아제 효소와 함께 교반하였다. 그 후, 10mM이 되게 DMF에 용해한 기질용액 p-NPB(p-nitrophenyl butyrate)를 첨가하여 37℃에서 35분 동안 재반응시켰다. 반응물은 진탕한 후, ELISA 리더를 이용하여 405nm에서 흡광도를 측정하였다. 오르리스타트(orlistat)는 양성대조군으로 사용하였다. 췌장 리파아제 저해활성은 시료용액의 첨가군과 무첨가군의 흡광도 감소율로 나타내었다.The pancreatic lipase inhibitory activity was measured by modifying the method of Kim et al. That is, porcine pancreatic lipase was dissolved in an enzyme buffer solution (10 mM MOPS, 1 mM EDTA, pH 6.8) at a concentration of 0.5 g / 200 ml while being kept at 4 캜, and the lysate was centrifuged at 4000 rpm , And the supernatant was mixed with a Tris buffer solution (100 mM Tris-HCl, 5 mM CaCl 2 , pH 7.0) and an enzyme buffer. The novel compounds isolated in Example 1 were dissolved in DMSO to a final concentration of 3% (w / v) and then stirred with the porcine pancreatic lipase enzyme for 15 min at 37 < 0 > C. Subsequently, the substrate solution p-NPB (p-nitrophenyl butyrate) dissolved in DMF to 10 mM was added and reacted at 37 ° C for 35 minutes. The reaction was shaken and then absorbance was measured at 405 nm using an ELISA reader. Orlistat was used as a positive control. The pancreatic lipase inhibitory activity was expressed as the absorbance reduction rate of the sample solution addition group and the no addition group.
그 결과, 표 1에 나타난 바와 같이 60분 동안 플라즈마 처리한 신규 화합물이 혼합되어 있는 플로리진, 신규화합물인 메틸렌비스플로리진, 디글루코실메틸렌비스플로리진 및 메틸렌비스플로레틴 각각의 췌장 리파아제 저해활성은 종래의 플로리진에 비해 증가하는 것을 확인하였고, 그 중 디글루코실메틸렌비스플로리진 및 메틸렌비스플로레틴은 플로레틴에 비해서도 증진된 췌장 리파아제 저해활성을 나타내었으며, 메틸렌비스플로레틴의 IC50값은 5.2±0.5μM로 가장 우수한 췌장 리파아제 저해활성을 나타내었다. As a result, as shown in Table 1, pancreatic lipase inhibitory activity of each of the novel compounds florisine, methylene bis-flurbine, diglycosyl methylene bis-fluorine and methylene bis- Was increased compared with the conventional floridine, and diglucosylmethylenebisphloridase and methylenebisflorethine exhibited enhanced pancreatic lipase inhibitory activity compared to floretin, and the IC 50 value of methylenebisflorethine Was 5.2 ± 0.5 μM and showed the best pancreatic lipase inhibitory activity.
실시예Example 4. 4. 플라즈마가Plasma 처리된 Treated 플로리진Florian 유래 신규 화합물의 지방축적 억제효과 측정 Measurement of inhibitory effect of new compounds on fat accumulation
플라즈마가 처리된 플로리진 유래 신규 화합물의 항비만 효과를 확인하기 위해, 3T3-L1 지방전구세포를 분화시켜 지방세포 내의 지방축적 정도를 Oil-red-O 염색을 통하여 측정하였다.In order to confirm the anti-obesity effect of plasma-treated novel floririn compounds, 3T3-L1 lipid precursor cells were differentiated and the degree of fat accumulation in adipocytes was measured through Oil-red-O staining.
3T3-L1 세포를 24 웰 플레이트에 웰당 5×104개의 세포 수로 분주한 후, 웰이 세포로 100% 채워지는 시점이 된 이후에, 2일 동안 더 유지시켰다. 세포는 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, 2μM 인슐린이 함유된 10% FBS DMEM으로 이틀 동안 배양하였다. 그 후 2일 마다 4일 동안 10% FBS DMEM 배양액으로 교체하였다. 지방세포 분화를 유도하는 동안 실시예 1에서 분리한 본 발명의 신규 화합물을 25μM, 50μM, 100μM 농도로 각 배양에 처리하였고, 분화가 완성되는 시점인 8일째에 지방의 축적 정도를 확인하기 위해 Oil-red-O 염색을 실시하였다. 3T3-L1 cells were dispensed into 24-well plates at 5 × 10 4 cells per well and then maintained for another 2 days after the well was 100% filled with cells. Cells were induced for 2 days with adipocyte differentiation in 10% FBS DMEM medium containing MDI (0.5 mM 3-isobutyl-1-methylxanthine (IBMX), 1 μM dexamethasone, 1 μM insulin) and after 48 h incubation, 2 μM insulin Containing 10% FBS DMEM for 2 days. Subsequently, the cells were replaced with 10% FBS DMEM medium for 2 days every 4 days. During the induction of adipocyte differentiation, the new compounds of the present invention isolated in Example 1 were treated at 25 μM, 50 μM and 100 μM concentrations, and in order to confirm the degree of accumulation of fat on the 8th day when the differentiation was completed, -red-O staining was performed.
그 결과, 도 2에 나타난 바와 같이 플로리진에 비해 본 발명의 신규 화합물(메틸렌비스플로리진, 디글루코실메틸렌비스플로리진, 메틸렌비스플로레틴)에 의한 지방축적 억제효과가 증가하였으며, 특히 플로리진에 당이 제거된 형태인 플로레틴이 메틸기에 의해 이합체를 형성한 본 발명의 메틸렌비스플로레틴은 플로레틴에 비해서도 더욱 증진된 지방축적 억제효과를 나타내었다.As a result, as shown in FIG. 2, the effect of inhibiting fat accumulation by the novel compounds of the present invention (methylenebisfloridine, diglucosylmethylenebisfloridine, methylenebisfloretin) was increased as compared with florixin, Methylene bisphosphretin of the present invention in which a sugar-removed form of floretine was formed by a methyl group showed a further enhanced fat accumulation inhibitory effect than that of floretin.
Claims (8)
[화학식 1]
상기 식에서, R1 및 R2는 각각 또는 수소(H)이다.1. A compound represented by the following formula (1): < EMI ID =
[Chemical Formula 1]
Wherein R < 1 > and R < 2 & Or hydrogen (H).
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