KR100948679B1 - A hangover curing composition containings cis???Hexadecenoic acid or 2???2?Aminoethyl?amino?ethanol as an active ingredient - Google Patents
A hangover curing composition containings cis???Hexadecenoic acid or 2???2?Aminoethyl?amino?ethanol as an active ingredient Download PDFInfo
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- KR100948679B1 KR100948679B1 KR1020070121946A KR20070121946A KR100948679B1 KR 100948679 B1 KR100948679 B1 KR 100948679B1 KR 1020070121946 A KR1020070121946 A KR 1020070121946A KR 20070121946 A KR20070121946 A KR 20070121946A KR 100948679 B1 KR100948679 B1 KR 100948679B1
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- Prior art keywords
- formula
- acid
- hangover
- compound represented
- active ingredient
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/045—Organic compounds containing nitrogen as heteroatom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/133—Amines having hydroxy groups, e.g. sphingosine
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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
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/334—Foods, ingredients or supplements having a functional effect on health treating the effects of consuming alcohol, narcotics or other addictive behavior, e.g. treating hangover or reducing blood alcohol levels
Abstract
본 발명은 화학식 1 또는 화학식 2로 표시되는 화합물을 유효성분으로 함유하는 숙취해소용 조성물에 관한 것으로서, 더욱 상세하게는 본 발명의 화학식 1로 표시되는 시스-9-헥사데센산(팔미톨레인산)[cis-9-Hexadecenoic acid(Palmitoleic acid)] 또는 화학식 2로 표시되는 2-[(2-아미노에틸)아미노]에탄올{2-[(2-Aminoethyl)amino]ethanol}은 아세트알데히드 분해 활성 및 알코올 분해 활성을 나타냄으로써 숙취해소에 유용하게 이용될 수 있다. The present invention relates to a hangover composition comprising the compound represented by the formula (1) or (2) as an active ingredient, more specifically cis-9-hexadecenoic acid (palmitoleic acid) represented by the formula (1) of the present invention ) [cis-9-Hexadecenoic acid (Palmitoleic acid)] or 2-[(2-aminoethyl) amino] ethanol represented by the formula (2) is the acetaldehyde degrading activity and It can be usefully used for hangover elimination by exhibiting alcohol degrading activity.
<화학식 1><Formula 1>
<화학식 2><Formula 2>
시스-9-헥사데센산(팔미토레인산), 2-[(2-아미노에틸)아미노]에탄올, 숙취해소, 아세트알데히드 분해활성, 알코올 분해활성 Cis-9-hexadecenoic acid (palmitoreic acid), 2-[(2-aminoethyl) amino] ethanol, hangover elimination, acetaldehyde decomposing activity, alcohol decomposing activity
Description
본 발명은 화학식 1 또는 화학식 2로 표시되는 화합물을 유효성분으로 함유하는 숙취해소용 조성물에 관한 것으로서, 더욱 상세하게는 본 발명의 화학식 1로 표시되는 시스-9-헥사데센산(팔미톨레인산)[cis-9-Hexadecenoic acid(Palmitoleic acid)] 또는 화학식 2로 표시되는 2-[(2-아미노에틸)아미노]에탄올{2-[(2-Aminoethyl)amino]ethanol}을 유효성분으로 함유하는 숙취해소용 조성물에 관한 것이다. The present invention relates to a hangover composition comprising the compound represented by the formula (1) or (2) as an active ingredient, more specifically cis-9-hexadecenoic acid (palmitoleic acid) represented by the formula (1) of the present invention ) [cis-9-Hexadecenoic acid (Palmitoleic acid)] or 2-[(2-aminoethyl) amino] ethanol represented by the formula (2) {2-[(2-Aminoethyl) amino] ethanol} as an active ingredient It relates to a hangover composition.
알코올은 뇌의 억제중추를 마비하여 섭취시 외관상 흥분한 상태를 보여주는데, 의식과 동작을 억제하고 수면 및 마취 효과가 있어 스트레스를 많이 받는 현대인의 주요한 기호식품이다. 우리나라의 음주 문화는 경제성장과 함께 그 소비가 계속 증가하고 있고, 현재 개인당 알코올 소비 수준은 세계에서 최고 수준이다. 그러나, 알코올은 과다 섭취하는 경우에 중독증으로 발전할 수 있고, 뇌 등의 중추신경계 뿐만 아니라 소화기관 및 간 등의 대사기관도 손상시키는 개인 건강을 위협하는 문제가 되고 있다. 또한, 음주운전 등으로 인한 교통사고의 증가는 사회적 문제로 크게 대두하고 있어, 알코올이 인체에 미치는 영향을 최소화할 수 있는 식품이나 의약품 등에 대한 요구도 증가하고 있다.Alcohol paralyzes the restraint of the brain and shows an excited state when ingested. It suppresses consciousness and movement, and has a sleep and anesthetic effect, which is a major favorite food for modern people who are stressed. Korea's drinking culture continues to grow with economic growth, and the current level of alcohol consumption per individual is the highest in the world. However, alcohol can develop into addiction when excessively ingested, and poses a threat to personal health that damages not only the central nervous system such as the brain, but also the metabolic organs such as the digestive system and the liver. In addition, the increase in traffic accidents due to drunk driving, etc. is emerging as a social problem, and the demand for foods or drugs that can minimize the effects of alcohol on the human body is also increasing.
음주 후 숙취 현상은 간세포에 축적된 에틸알코올 또는 아세트알데히드의 독성 작용에 의하여 발생되는 것으로, 상기 독성 작용이 장시간 지속되어 신진대사 등에 장애를 일으켜 발생된다. 구체적으로, 정상적인 에틸알코올 대사과정은 에틸알코올이 체내에 유입되면 위장 또는 소장에서 흡수되어 혈관 속으로 들어가 간장으로 이동하고, 간세포에는 알코올 탈수소효소가 있어 알코올을 아세트알데히드로 산화시키고, 상기 아세트알데히드는 간세포에 있는 아세트알데히드 탈수소효소에 의하여 초산을 분해되어 온몸의 근육이나 지방조직으로 이행되어 최종적으로는 탄산가스와 물로 분해되는 것이다.The hangover phenomenon after drinking alcohol is caused by the toxic action of ethyl alcohol or acetaldehyde accumulated in hepatocytes, and the toxic action lasts for a long time, causing metabolism and the like. Specifically, in normal ethyl alcohol metabolism, when ethyl alcohol enters the body, it is absorbed by the gastrointestinal or small intestine, enters the blood vessels, and moves to the liver, and the liver cells have alcohol dehydrogenase, which oxidizes alcohol to acetaldehyde, and the acetaldehyde Acetic acid dehydrogenase in hepatocytes decomposes acetic acid and transfers it to muscles and adipose tissues throughout the body and finally into carbon dioxide and water.
또한, 상기 아세트알데히드 탈수소효소에는 아세트알데히드가 저농도인 경우에도 기능하는 Ⅱ형과 아세트알데히드가 고농도인 경우에만 작용하는 Ⅰ형이 있으나, 동양인은 일반적으로 Ⅱ형 아세트알데히드 탈수소효소가 결핍 내지 부족하기 때문에 아세트알데히드가 쉽게 분해되지 않는다. 따라서, 산화되지 아니한 아세트알데히드 및 에틸알코올의 유독 작용에 의하여 간세포와 뇌세포의 손상을 야기한다. 아울러, 알코올의 탈수작용으로 인한 체내의 수분 부족과 수분과 함께 여러 가지 전해질이 체외로 배출되어 전해질이 부족해진다. 상기 원인으로 인하여 정상적인 신진대사가 방해받아 구토, 두통, 오한, 복통 등의 다양한 숙취 현상이 발생하게 된다.In addition, the acetaldehyde dehydrogenase has a type II which functions even at low concentrations of acetaldehyde and a type I which functions only at high concentrations of acetaldehyde, but oriental people generally lack or lack an acetaldehyde dehydrogenase of type II. Acetaldehyde is not readily degraded. Therefore, damage of hepatocytes and brain cells is caused by the toxic action of unoxidized acetaldehyde and ethyl alcohol. In addition, various electrolytes are discharged to the outside of the body together with a lack of water and water due to the dehydration of alcohol, and the electrolyte is insufficient. Normal metabolism is disturbed due to the above causes, causing various hangovers such as vomiting, headache, chills and abdominal pain.
이러한 음주 후의 숙취 현상을 해소하기 위하여, 생약 제재 또는 인공 제재를 단독 또는 혼합하여 제조되는 다수의 숙취해소제가 개발되고 있으며, 민간에서는 북어국이나 콩나물국 등이 숙취해소에 자주 이용되고 있으나 보관이나 복용이 불편하여 이용에 한계가 있다. 따라서, 상기의 문제점을 해결하면서 경제적이고 효과가 탁월한 숙취해소제의 개발이 요구되고 있다.In order to solve the hangover phenomenon after drinking, a number of hangover medicinal products are prepared, which are prepared by mixing or using herbal medicines or artificial preparations. This inconvenience is limited to use. Therefore, while solving the above problems, there is a demand for the development of an economic and effective hangover relievers.
이에, 본 발명자들은 시스-9-헥사데센산(팔미토레인산) 및 2-[(2-아미노에틸)아미노]에탄올 화합물의 그 활성 및 기능성을 규명한 결과, 아세트알데히드 분해 활성 및 알코올 분해 활성을 나타냄으로써 숙취해소용으로 유용하게 사용될 수 있음을 발견함으로써 본 발명을 완성하였다.Accordingly, the present inventors have identified the activity and functionality of cis-9-hexadecenoic acid (palmitorenoic acid) and 2-[(2-aminoethyl) amino] ethanol compound, and as a result, acetaldehyde decomposing activity and alcohol decomposing activity The present invention has been completed by discovering that it can be usefully used for hangover relief.
본 발명의 목적은 시스-9-헥사데센산(팔미톨레인산)[cis-9-Hexadecenoic acid(Palmitoleic acid)] 또는 2-[(2-아미노에틸)아미노]에탄올{2-[(2-Aminoethyl)amino]ethanol} 화합물을 유효성분으로 함유하는 숙취해소용 조성물을 제공하는 것이다.An object of the present invention is cis-9-hexadecenoic acid (palmitoleic acid) [cis-9-Hexadecenoic acid (Palmitoleic acid)] or 2-[(2-aminoethyl) amino] ethanol {2-[(2- Aminoethyl) amino] ethanol} It is to provide a hangover composition containing the compound as an active ingredient.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물을 유효성분으로 함유하는 숙취해소제를 제공한다.In order to achieve the above object, the present invention provides a hangover releasing agent containing a compound represented by the following formula (1) as an active ingredient.
또한, 본 발명은 하기 화학식 2로 표시되는 화합물을 유효성분으로 함유하는 숙취해소제를 제공한다.In addition, the present invention provides a hangover releasing agent containing a compound represented by the following formula (2) as an active ingredient.
또한, 본 발명은 하기 화학식 1로 표시되는 화합물을 유효성분으로 함유하는 숙취해소용 건강기능식품을 제공한다.In addition, the present invention provides a health functional food for hangover relief containing the compound represented by the following formula (1) as an active ingredient.
아울러, 본 발명은 하기 화학식 2로 표시되는 화합물을 유효성분으로 함유하는 숙취해소용 건강기능식품을 제공한다.In addition, the present invention provides a dietary supplement for hangover containing the compound represented by the following formula (2) as an active ingredient.
본 발명의 시스-9-헥사데센산(팔미토레익산)[cis-9-Hexadecenoic acid(Palmitoleic acid)] 또는 2-[(2-아미노에틸)아미노]에탄올{2-[(2-Aminoethyl)amino]ethanol} 화합물은 아세트알데히드 분해 활성 및 알코올 분해 활성을 나타냄으로써 숙취해소에 유용하게 이용될 수 있다. Cis-9-hexadecenoic acid (palmitoleic acid) [cis-9-Hexadecenoic acid (Palmitoleic acid)] or 2-[(2-aminoethyl) amino] ethanol {2-[(2-Aminoethyl) amino of the present invention ] ethanol} compound can be useful for hangover elimination by showing acetaldehyde and alcohol degradation activity.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 하기 화학식 1 또는 화학식 2로 표시되는 화합물을 유효성분으로 함유하는 숙취해소제를 제공한다.The present invention provides a hangover resolver containing a compound represented by the following formula (1) or (2) as an active ingredient.
<화학식 1><Formula 1>
<화학식 2><Formula 2>
본 발명의 화학식 1 또는 화학식 2로 표시되는 화합물은 본 발명의 기술분야에서 널리 알려진 방법에 의하여 추출된 것 또는 상업적으로 구입한 것을 적절히 선택하여 사용할 수 있으며, 그 방법 또는 물질은 특별히 한정되지 않는다.Compound represented by the formula (1) or formula (2) of the present invention can be used by appropriately selected or extracted by a method well known in the art of the present invention, the method or material is not particularly limited.
본 발명에서는 상기 화학식 1 및 화학식 2를 하기와 같은 방법으로 제조하였다.In the present invention, Formula 1 and Formula 2 were prepared by the following method.
1) 황태(Theragra chalcogramma)를 메탄올로 추출하는 단계;1) Theragra chalcogramma ) with methanol;
2) 단계 1)의 추출물을 추가로 유기용매를 가하여 유기용매 분획물을 제조하는 단계;2) adding an organic solvent to the extract of step 1) to prepare an organic solvent fraction;
3) 단계 2)의 분획물을 컬럼 크로마토그래피에 흡착시키고 톨루엔(toluene): 아세톤(Aceton) : 메탄올로 구성되는 농도구배를 적용하여 얻을 수 있는 활성 분획물을 수득하는 단계; 및3) adsorbing the fraction of step 2) by column chromatography and obtaining an active fraction obtained by applying a concentration gradient consisting of toluene: acetone: methanol; And
4) 단계 3)의 활성 분획물을 추가로 2차 컬럼 크로마토그래피에 흡착시키고 물 : 메탄올로 구성되는 농도구배를 적용하여 얻을 수 있는 활성 화합물을 수득하는 단계,4) adsorbing the active fraction of step 3) to secondary column chromatography and obtaining an active compound which can be obtained by applying a concentration gradient consisting of water: methanol,
상기 제조방법에 있어서, 단계 1)의 황태는 생산한 것 또는 시판되는 것을 제한 없이 사용할 수 있다. 추출시 메탄올은 황태 분량의 5 내지 15배 첨가하여 추출하는 것이 바람직하며, 10배 첨가하여 추출하는 것이 더욱 바람직하다. 상기 용매를 가한 후 환류 냉각하여 추출하는 것이 바람직하다. 추출시 온도는 0 ~ 40℃인 것이 바람직하며, 40℃인 것이 더욱 바람직하나 이에 한정하지 않는다. 또한, 추출시간은 5 ~ 15 일이 바람직하며, 10 일이 더욱 바람직하나 이에 한정하지 않는다. 아울러, 추출 회수는 1 내지 5회인 것이 바람직하며, 3회 반복 추출하는 것이 더욱 바람직하나 이에 한정되는 것은 아니다. 상기 방법에 의하여 황태를 추출, 여과한 뒤 여과액을 감압 농축하여 황태 추출물을 수득하였다.In the above production method, the yellow of step 1) can be used without limitation to those produced or marketed. During the extraction, methanol is preferably added by adding 5 to 15 times the amount of yellow, and more preferably, extracted 10 times. After adding the solvent, reflux cooling is preferably performed. The temperature at the time of extraction is preferably 0 ~ 40 ℃, more preferably 40 ℃ but not limited thereto. In addition, the extraction time is preferably 5 to 15 days, more preferably 10 days is not limited thereto. In addition, the number of times the extraction is preferably 1 to 5 times, more preferably three times repeated extraction is not limited thereto. After extracting and filtering the yellow matter by the above method, the filtrate was concentrated under reduced pressure to obtain a yellow extract.
상기 제조방법에 있어서, 단계 2)의 유기용매는 n-헥산, 에틸아세테이트 및 부탄올로 계통 분획하는 것이 바람직하며 에틸아세테이트 또는 부탄올을 사용하는 것이 더욱 바람직하다. 본 발명에서는 에틸아세테이트 또는 부탄올 분획물을 감압 농축하였다.In the above production method, the organic solvent of step 2) is preferably fractionated into n-hexane, ethyl acetate and butanol, and more preferably ethyl acetate or butanol is used. In the present invention, ethyl acetate or butanol fractions were concentrated under reduced pressure.
상기 제조방법에 있어서, 단계 3) 및 단계 4)의 컬럼 크로마토그래피는 실리카겔, 세파덱스, LH-20, ODS(octadecylsilica), RP-18, 폴리아미드, 도요펄(Toyopearl) 및 XAD 수지로 이루어진 군으로부터 선택된 충진제를 이용하는 컬럼 크로마토그래피를 수행하여 활성화합물을 분리 및 정제할 수 있다. 컬럼 크로마토그래피는 필요에 따라 적절한 충진제를 선택하여 수차례 실시할 수 있다. 본 발명에서는 상기 황태의 에틸아세테이트 분획물을 실리카겔(silicagel) 컬럼 크로마토그래피에 흡착시키고 이동상으로 톨루엔(toluene): 아세톤(Aceton)을 농도구배(100 : 0 → 0 : 100)를 1차 적용한 후, 아세톤 : 메탄올을 농도구배(100 : 0 → 0 : 100)를 2차 적용하여, 9개의 분획물 E1 ~ E9을 순차적으로 용출하였고, 이 중 아세톤 : 메탄올의 농도(6 : 4)에서 활성분획물(E9)을 얻었다(표 1 참조). 또한, 상기 황태의 부탄올 분획물을 실리카겔 컬럼 크로마토그래피에 흡착시키고 이동상으로 톨루엔(toluene): 아세톤(Aceton)을 농도구배(100 : 0 → 0 : 100)를 1차 적용한 후, 아세톤 : 메탄올을 농도구배(100 : 0 → 0 : 100)를 2차 적용하여, 12개의 분획물 B1 ~ B12를 순차적으로 용출하였고, 이 중 톨루엔 : 아세톤의 농도(10 : 0)에서 활성분획물(B1)을 얻었다(표 2 참조).In the above method, the column chromatography of steps 3) and 4) is composed of silica gel, Sephadex, LH-20, octadecylsilica (ODS), RP-18, polyamide, Toyopearl and XAD resin. Column chromatography using a filler selected from can be performed to isolate and purify the active compound. Column chromatography can be carried out several times by selecting the appropriate filler as required. In the present invention, the ethyl acetate fraction of sulfur is adsorbed on silica gel column chromatography, and toluene: acetone is first applied to a concentration gradient (100: 0 → 0: 100) as a mobile phase, followed by acetone. : Methanol was applied to the concentration gradient (100: 0 → 0: 100) for the second time, and nine fractions E1 to E9 were sequentially eluted, and acetone: methanol (6: 4) was active fraction (E9). Was obtained (see Table 1). In addition, the butanol fraction of the yellow adsorbed on silica gel column chromatography, and toluene: acetone was first applied to the mobile phase with a concentration gradient (100: 0 → 0: 100), and then acetone: methanol was used. (100: 0 → 0: 100) was applied secondly, and 12 fractions B1 to B12 were eluted sequentially, of which active fraction (B1) was obtained at a concentration of toluene: acetone (10: 0) (Table 2). Reference).
상기 활성 분획물들(E9 및 B1)을 각각 2차로 옥타데실실리카(Octadecylsilica) 컬럼 크로마토그래피에 흡착시키고 물 : 메탄올로 구성되는 농도(70 : 30)을 적용하여 활성 분획물(E9)에서는 화합물 1, 활성 분획물(B1)에서 화합물 2를 각각 수득하였다. 상기 분리된 화합물 1 및 화합물 2는 질량분석 기(mass spectrograph, MS) 및 핵자기공명(nuclear magnetic resonance, NMR)을 통해서 각각 화학식 1로 표시되는 시스-9-헥사데센산(팔미톨레인산) 및 화학식 2로 표시되는 2-[(2-아미노에틸)아미노]에탄올{2-[(2-Aminoethyl)amino]ethanol}인 것을 확인하였다. The active fractions (E9 and B1) were respectively adsorbed on octadecylsilica column chromatography in a second step and water (methanol) concentration (70: 30) was applied to the active fraction (E9) to obtain compound 1, activity. Compound 2 was obtained respectively in fraction (B1). The separated compound 1 and compound 2 are cis-9-hexadecenoic acid (palmitoleic acid) represented by Chemical Formula 1 through mass spectrograph (MS) and nuclear magnetic resonance (NMR), respectively. And 2-[(2-aminoethyl) amino] ethanol {2-[(2-Aminoethyl) amino] ethanol} represented by the formula (2).
본 발명에서는 상기 화학식 1 또는 화학식 2로 표시되는 화합물이 아세트알데히드 분해 활성에 미치는 영향을 알아보기 위하여, 아세트알데히드에 상기 화학식 1 또는 화학식 2로 표시되는 화합물을 각각 첨가한 후, 아세트알데히드 디하이드로제나제(Acetaldehyde dehydrogenase, ALDH)를 첨가하여 반응시킨 후 흡광도의 변화를 측정하였다. 그 결과, 화학식 1 또는 화학식 2로 표시되는 화합물은 대조군인 ALDH만 첨가한 것에 비해, ALDH의 활성을 높히는 것을 알 수 있었다. 체내에 과량의 알코올이 섭취된 경우, 알코올의 분해산물로 생성된 아세트알데히드는 뇌로 전해져 많은 유해화합물로 바뀌어 맥박의 증가나 발한, 홍조, 오심, 구토 등의 증상을 초래하고 숙취를 느끼게 된다. ALDH 활성은 간손상을 주지 않으면서 아세트알데히드 분해를 촉진시키는 것이다. 따라서, 본 발명의 화학식 1 또는 화학식 2로 표시되는 화합물은 ALDH의 활성을 증가시켜 아세트알데히드 분해를 촉진시킴으로써 숙취해소제로 이용될 수 있음을 알 수 있다. In the present invention, in order to determine the effect of the compound represented by the formula (1) or formula (2) on the acetaldehyde decomposition activity, after adding the compound represented by the formula (1) or formula (2) to acetaldehyde, respectively, acetaldehyde dehydrogena After the reaction was added (Acetaldehyde dehydrogenase, ALDH) and the change in absorbance was measured. As a result, it was found that the compound represented by the formula (1) or (2) increases the activity of ALDH as compared with the addition of only ALDH as a control. When excess alcohol is ingested in the body, acetaldehyde produced as a breakdown product of alcohol is transmitted to the brain and converted into many harmful compounds, causing symptoms such as increased pulse, sweating, redness, nausea and vomiting, and a hangover. ALDH activity promotes acetaldehyde degradation without causing liver damage. Therefore, it can be seen that the compound represented by Formula 1 or Formula 2 of the present invention can be used as a hangover scavenger by increasing the activity of ALDH to promote acetaldehyde degradation.
본 발명에서는 화학식 1 또는 화학식 2로 표시되는 화합물이 알코올 분해 활성에 미치는 영향을 알아보기 위하여, 알코올에 화학식 1 또는 화학식 2로 표시되는 화합물들을 각각 첨가한 후, 알코올 디하이드로제나제(Alcohol dehydrogenase, ADH)를 첨가하여 반응시킨 후 흡광도의 변화를 측정하였다. 그 결과, 상기 화학식 1 또는 화학식 2로 표시되는 화합물은 대조군인 ADH만 첨가한 것에 비해, ADH의 활성을 높히는 것을 알 수 있었다. 따라서, 본 발명의 화학식 1 또는 화학식 2로 표시되는 화합물은 ADH의 활성을 증가시켜 알코올 분해를 촉진시킴으로써 숙취해소제로 이용될 수 있음을 알 수 있다. In the present invention, in order to determine the effect of the compound represented by the formula (1) or (2) on the alcohol degradation activity, after adding the compounds represented by the formula (1) or (2) to the alcohol, respectively, alcohol dehydrogenase (Alcohol dehydrogenase, After the reaction was added by ADH), the change in absorbance was measured. As a result, it was found that the compound represented by Formula 1 or Formula 2 increases the activity of ADH as compared with the addition of only ADH as a control. Therefore, it can be seen that the compound represented by Formula 1 or Formula 2 of the present invention can be used as a hangover antagonist by increasing the activity of ADH to promote alcohol degradation.
본 발명의 숙취해소제는 화학식 1 또는 화학식 2로 표시되는 화합물에 약학적으로 허용가능한 염을 포함할 수 있다. 상기 약학적으로 허용가능한 염은 유리산(free acid)에 의해 형성된 부가염이 유용하다. 적합한 유리산으로는 유기산과 무기산을 사용할 수 있으며, 무기산으로는 염산, 브롬산, 황산 및 인산 등을 사용할 수 있고 유기산으로는 구연산(citric acid), 초산, 젖산, 주석산(tartariac acid), 말레인산, 푸마르산(fumaric acid), 포름산, 프로피온산(propionic acid), 옥살산, 트리플루오로아세트산, 벤조산, 글루콘산, 메탄술폰산, 글리콜산, 숙신산, 4-톨루엔술폰산, 갈룩투론산, 엠본산, 글루탐산 또는 아스파르트산 등을 사용할 수 있다. 나아가, 약학적으로 허용가능한 염뿐만 아니라, 통상의 방법에 의해 조제될 수 있는 모든 염, 수화물 및 용매화물을 모두 포함할 수 있다.Hangover releasing agent of the present invention may include a pharmaceutically acceptable salt in the compound represented by the formula (1) or formula (2). The pharmaceutically acceptable salts are useful addition salts formed with free acid. Suitable free acids may be organic and inorganic acids, inorganic acids may be hydrochloric acid, bromic acid, sulfuric acid and phosphoric acid, and organic acids may be citric acid, acetic acid, lactic acid, tartariac acid, maleic acid, Fumaric acid, formic acid, propionic acid, oxalic acid, trifluoroacetic acid, benzoic acid, gluconic acid, methanesulfonic acid, glycolic acid, succinic acid, 4-toluenesulfonic acid, galluxuronic acid, embonic acid, glutamic acid or aspartic acid Etc. can be used. Furthermore, not only pharmaceutically acceptable salts, but also all salts, hydrates and solvates that can be prepared by conventional methods may be included.
본 발명의 숙취해소제는 화학식 1 또는 화학식 2로 표시되는 화합물 중에서 하나 이상을 선택적으로 함유할 수 있으며, 상기 성분에 추가로 동일 또는 유사한 기능을 나타내는 유효성분을 1종 이상 함유할 수 있다. Hangover releasing agent of the present invention may optionally contain one or more of the compounds represented by the formula (1) or formula (2), and may further contain one or more active ingredients exhibiting the same or similar functions in addition to the above components.
본 발명의 숙취해소제는 임상 투여 시에 경구 또는 비경구로 투여가 가능하며 일반적인 의약품 제제의 형태로 사용될 수 있다. 즉, 본 발명의 숙취해소제는 실제 임상 투여 시에 경구 및 비경구의 여러 가지 제형으로 투여될 수 있는데, 제제화할 경우에는 보통 사용하는 충진제, 증량제, 결합제, 습윤제, 붕해제 및 계면활성제 등의 희석제 또는 부형제를 사용하여 조제된다. 경구 투여를 위한 고형 제제에는 정제, 환제, 산제, 과립제 및 캡슐제 등이 포함되며, 이러한 고형 제제는 본 발명의 약학적 조성물에 적어도 하나 이상의 부형제 예를 들면, 전분, 탄산칼슘, 수크로스, 락토오스 및 젤라틴 등을 섞어 조제된다. 또한 단순한 부형제 이외에 마그네슘, 스티레이트, 탈크 같은 윤활제들도 사용된다. 경구 투여를 위한 액상 제제로는 현탁제, 내용액제, 유제 및 시럽제 등이 해당되는데 흔히 사용되는 단순 희석제인 물, 리퀴드 파라핀 이외에 여러 가지 부형제, 예를 들면 습윤제, 감미제, 방향제 및 보존제 등이 포함될 수 있다. 비경구 투여를 위한 제제에는 멸균된 수용액, 비수성용제, 현탁제, 유제, 동결건조제제 및 좌제가 포함된다. 비수성용제와 현탁용제로는 프로필렌글리콜, 폴리에틸렌 글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테르 등이 사용될 수 있다. 좌제의 기제로는 위텝솔(witepsol), 마크로골, 트윈(tween) 61, 카카오지, 라우린지, 글리세롤 및 젤라틴 등이 사용될 수 있다. 본 발명의 숙취해소제는 비경구 투여시 피하주사, 정맥주사 또는 근육내 주사를 통할 수 있다. Hangover reliever of the present invention can be administered orally or parenterally during clinical administration and can be used in the form of a general pharmaceutical formulation. That is, the hangover releasing agent of the present invention may be administered in various oral and parenteral formulations during actual clinical administration, and when formulated, diluents such as fillers, extenders, binders, wetting agents, disintegrating agents, and surfactants that are commonly used Or using excipients. Solid preparations for oral administration include tablets, pills, powders, granules and capsules, and the like, which may be used in the pharmaceutical composition of the present invention at least one excipient such as starch, calcium carbonate, sucrose, lactose And gelatin etc. are mixed and prepared. In addition to simple excipients, lubricants such as magnesium, styrate and talc are also used. Liquid preparations for oral administration include suspensions, solutions, emulsions and syrups, and may include various excipients such as wetting agents, sweeteners, fragrances and preservatives, in addition to commonly used simple diluents such as water and liquid paraffin. have. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations and suppositories. As the non-aqueous solvent and the suspension solvent, propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used. As the base of the suppository, witepsol, macrogol, tween 61, cacao butter, laurin butter, glycerol and gelatin may be used. Hangover reliever of the present invention can be via subcutaneous injection, intravenous injection or intramuscular injection during parenteral administration.
본 발명의 숙취해소제의 바람직한 투여량은 환자의 상태 및 체중, 질병의 정도, 약물형태, 투여경로 및 기간에 따라 다르지만, 당업자에 의해 적절하게 선택될 수 있다. Preferred dosages of the hangover resolver of the present invention vary depending on the condition and weight of the patient, the extent of the disease, the form of the drug, the route of administration and the duration, and may be appropriately selected by those skilled in the art.
또한, 본 발명은 화학식 1 또는 화학식 2로 표시되는 화합물을 유효성분으로 함유하는 숙취해소용 건강기능식품을 제공한다.The present invention also provides a health functional food for hangover resolution containing the compound represented by the formula (1) or (2) as an active ingredient.
본 발명의 화학식 1 또는 화학식 2로 표시되는 화합물을 그대로 첨가하거나 다른 식품 또는 식품 성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효 성분의 혼합양은 사용 목적(예방, 건강 또는 치료적 처치)에 따라 적합하게 결정될 수 있다. 일반적으로, 식품 또는 음료의 제조시에 본 발명의 화학식 1 또는 화학식 2로 표시되는 화합물은 원료에 대하여 15 중량부 이하, 바람직하게는 10 중량부 이하의 양으로 첨가된다. 그러나 건강 및 위생을 목적으로 하거나 또는 건강 조절을 목적으로 하는 장기간의 섭취의 경우에는 상기 양은 상기 범위 이하일 수 있으며, 안전성 면에서 아무런 문제가 없기 때문에 유효성분은 상기 범위 이상의 양으로도 사용될 수 있다.The compound represented by the formula (1) or (2) of the present invention may be added as it is or used with other food or food ingredients, and may be appropriately used according to a conventional method. The mixed amount of the active ingredient may be suitably determined depending on the purpose of use (prevention, health or therapeutic treatment). Generally, the compound represented by the formula (1) or (2) 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 material in the manufacture of food or beverage. However, in the case of long-term intake for health and hygiene or health control purposes, the amount may be below the above range, and the active ingredient may be used in an amount above the above range because there is no problem in terms of safety.
상기 식품의 종류에는 특별한 제한은 없다. 상기 물질을 첨가할 수 있는 식품의 예로는 육류, 소세지, 빵, 쵸코렛, 캔디류, 스넥류, 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 food. Examples of the food to which the substance can be added include dairy products including meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gums, ice cream, various soups, drinks, tea, drinks, Alcoholic beverages and vitamin complexes, and the like and include all of the health foods in the conventional sense.
본 발명의 건강음료 조성물은 통상의 음료와 같이 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있다. 상술한 천연 탄수화물은 포도당, 과당과 같은 모노사카라이드, 말토스, 슈크로스와 같은 디사카라이드, 및 덱스 트린, 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 beverage composition of the present invention may contain various flavors or natural carbohydrates, etc. as additional components, as in the general beverage. The above-mentioned natural carbohydrates are glucose, monosaccharides such as fructose, disaccharides such as maltose and sucrose, and polysaccharides such as dextrin and cyclodextrin, sugar alcohols such as xylitol, sorbitol and erythritol. As the sweetening agent, natural sweetening agents such as tautin and stevia extract, synthetic sweetening agents such as saccharin and aspartame, and the like can be used.
상기 외에 본 발명의 조성물은 여러가지 영양제, 비타민, 전해질, 풍미제, 착색제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알콜, 탄산 음료에 사용되는 탄산화제 등을 함유할 수 있다. 그밖에 본 발명의 조성물은 천연 과일쥬스, 과일쥬스 음료 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 이러한 성분은 독립적으로 또는 조합하여 사용할 수 있다. In addition to the above, the composition of the present invention includes various nutrients, vitamins, electrolytes, flavoring agents, coloring agents, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners, pH regulators, stabilizers, preservatives, glycerin, alcohols, carbonic acid. Carbonating agents and the like used in beverages. In addition, the composition of the present invention may contain a flesh for preparing natural fruit juice, fruit juice beverage and vegetable beverage. These components can be used independently or in combination.
이하, 본 발명을 하기 실시예, 실험예 및 제제예에 의하여 상세히 설명한다.Hereinafter, the present invention will be described in detail by the following Examples, Experimental Examples and Formulation Examples.
단, 하기 실시예, 실험예 및 제제예는 본 발명을 구체적으로 예시하는 것이며, 본 발명의 내용이 하기의 실시예, 실험예 및 제제예에 의해 한정되는 것은 아니다.However, the following Examples, Experimental Examples, and Formulation Examples specifically illustrate the present invention, and the contents of the present invention are not limited to the following Examples, Experimental Examples, and Formulation Examples.
<< 실시예Example > 화학식 1 또는 화학식 2로 표시되는 화합물의 제조> Preparation of Compounds Represented by Formula 1 or Formula 2
<1-1> 황태의 메탄올 추출물의 제조<1-1> Preparation of Yellow Methanol Extract
인제 용대리 황태덕장으로부터 용대리 황태를 지원받아 잘게 파쇄하여 시료로 사용하였다. 대상 실험군은 국내에 생산하는 인제 용대리 황태를 대상으로 실험을 진행하였다. 황태 500g을 잘게 파쇄하여 메탄올에 10일간 추출한 후 추출물 을 여과지(filter paper)(185㎜Ø, Whatman NO.2, Cat NO. 1002 185)로 여과시킨 후, 회전식 감압농축기(rotary evaporator)(EYELA NE-2001 5L, Japan)를 이용하여 40℃이하의 중탕에서 감압 농축하였다. 상기 결과, 56.1g(11.22%) 수득하였다. Inje Yong-dae Hwang Tae-deok was supported by the Yong-dae Hwang-tae, finely crushed and used as a sample. The experimental group carried out experiments with the Inje Yong-Dae Tae-Hwang produced in Korea. Finely crushed 500 g of yellow, extracted for 10 days in methanol, and then the extract was filtered with a filter paper (185 mmØ, Whatman NO.2, Cat NO. 1002 185), and then rotary evaporator (EYELA NE) -2001 5L, Japan) was concentrated under reduced pressure in a hot bath of 40 ℃ or less. As a result, 56.1 g (11.22%) was obtained.
<1-2> 활성 <1-2> active 분획물의Fraction 제조 Produce
황태의 메탄올 추출물(54g)을 증류수 1L에 현탁시켜 분별깔때기(separate funnel)에 넣은 후, 헥산(Hexane), 에틸 아세테이트(EtOAc), 부탄올(BuOH), 물(H2O) 순으로 순차적 용매 분획하였다. 동일한 방법으로 3회 반복하였으며, 헥산 분획 10.77g(19.94%), 에틸 아세테이트 분획 4.61g(8.53%), 부탄올 분획 6.9g(12.78%), 수용성 분획 31.4g(58.15%)을 각각 수득하였다.Suspended methanol extract (54g) of sulfur in 1L of distilled water and placed in a separatory funnel, and then sequentially fractionated solvents in the order of hexane (Hexane), ethyl acetate (EtOAc), butanol (BuOH), and water (H 2 O). It was. The same procedure was repeated three times, and 10.77 g (19.94%) of hexane fraction, 4.61 g (8.53%) of ethyl acetate fraction, 6.9 g (12.78%) of butanol fraction, and 31.4 g (58.15%) of water-soluble fraction were obtained, respectively.
상기 분획물 중 에틸 아세테이트 분획층(9.2g)을 이용하여 실리카겔 컬럼 크로마토그래피를 실시하였다. 각 시료를 메탄올로 용해시킨 다음 실리카겔로 충진시키고 유리 컬럼(glass column)(4×70 ㎝, 7734, Merck社)에 충진시킨 시료를 하기 표 1과 같은 톨루엔 : 아세톤 : 메탄올의 농도구배 용매 시스템을 이용하여 9개(E1 ~ E9)의 소분획 각각을 순차적으로 용출하였으며, 아세톤 : 메탄올의 농도(6 : 4)에서 높은 활성을 가지는 분획물(E9)을 수득하였다(표 1 참조). Silica gel column chromatography was performed using an ethyl acetate fraction layer (9.2 g) in the fraction. Each sample was dissolved in methanol, filled with silica gel, and filled in a glass column (4 × 70 cm, 7734, Merck, Inc.). Each of the nine (E1-E9) subfractions was eluted sequentially to obtain a fraction (E9) having high activity at acetone: methanol concentration (6: 4) (see Table 1).
시료무게 : 4g, 컬럼 크기 : 4cm, Merck(社) 실리카겔(7734)Sample weight: 4g, Column size: 4cm, Merck silica gel (7734)
또한, 부탄올 분획층(4g)을 실리카겔 컬럼 크로마토그래피를 실시하였다. 각 시료를 메탄올로 용해시킨 다음 실리카겔로 충진시키고 유리 컬럼(glass column)(4×70 ㎝, 7734, Merck社)에 충진시킨 시료를 하기 표 2와 같은 톨루엔 : 아세톤 : 메탄올의 농도구배 용매 시스템을 이용하여 12개(B1 ~ B12)의 소분획 각각을 순차적으로 용출하였으며, 톨루엔 : 아세톤의 농도(10 : 0)에서 높은 활성을 가지는 분획물(B1)을 수득하였다(표 2 참조).In addition, a butanol fraction layer (4 g) was subjected to silica gel column chromatography. Each sample was dissolved in methanol, filled with silica gel, and filled in a glass column (4 × 70 cm, 7734, Merck, Inc.). Each of the 12 small fractions (B1 to B12) was eluted sequentially to obtain a fraction (B1) having high activity at a concentration of toluene: acetone (10: 0) (see Table 2).
시료무게 : 4g, 컬럼 크기 : 4cm, Merck(社) 실리카겔(7734)Sample weight: 4g, Column size: 4cm, Merck silica gel (7734)
<1-3> 활성 화합물의 제조<1-3> Preparation of Active Compound
상기 활성 분획물들(E9 및 B1)을 각각 옥타데실실리카(Octadecylsilica) 컬럼 크로마토그래피에 흡착시키고 물 : 메탄올로 구성되는 농도(70 : 30)을 적용하여 활성 분획물(E9)에서는 화합물 1, 활성 분획물(B1)에서는 화합물 2를 각각 수득하였다. 상기 분리된 화합물들은 질량분석기(mass spectrograph, Autospec. M363 series), UV 분광기(ultraviolet spectrometer, jasco680), 적외선 분광기(infrared spectrometer, IR, FT-3000, Excalibur) 및 1H- 및 13C- 핵자기공명(nuclear magnetic resonance, Bruker Avance 300)을 통해서 각각 화학식 1로 표시되는 시스-9-헥사데센산(팔미톨레인산) 및 화학식 2로 표시되는 2-[(2-아미노에틸)아미노]에탄올{2-[(2-Aminoethyl)amino]ethanol}인 것을 확인하였다. The active fractions (E9 and B1) were adsorbed on octadecylsilica column chromatography, respectively, and water (methanol) concentrations (70: 30) were applied to the active fraction (E9) to obtain compound 1, the active fraction ( In compound B1, compound 2 was obtained, respectively. The isolated compounds were mass spectrograph (Autospec.M363 series), UV spectrometer (jasco680), infrared spectrometer (IR, FT-3000, Excalibur) and 1 H- and 13 C-nuclear magnetic Cis-9-hexadecenoic acid (palmitolenic acid) represented by the formula (1) and 2-[(2-aminoethyl) amino] ethanol represented by the formula (2) through resonance (nuclear magnetic resonance, Bruker Avance 300) { 2-[(2-Aminoethyl) amino] ethanol}.
<< 실험예Experimental Example 1> 아세트알데히드 1> acetaldehyde 디하이드로제나제Dehydrogenase 활성 측정 Active measurement
아세트 알데히드 0.1 ㎕에 상기 화학식 1 또는 화학식 2로 표시되는 화합물들을 각각 0.1 ㎕ 첨가하고 ALDH를 첨가하여 37℃ 물중탕(water bath)에서 10분간 반응시킨 후 340nm에서 흡광도를 측정하여 1%의 농도에서 ALDH 활성에 미치는 영향을 알아보았다. 음성 대조군은 ALDH에 완충용액을 첨가하였고 양성 대조군은 ALDH 활성을 증가시키는 것으로 알려진 아스파르트산을 첨가하였다. To 0.1 μl of acetaldehyde, 0.1 μl of the compound represented by Chemical Formula 1 or Chemical Formula 2 was added thereto, and ALDH was added thereto to react for 10 minutes in a water bath at 37 ° C., and then absorbance was measured at 340 nm at a concentration of 1%. The effect on ALDH activity was examined. Negative controls added buffer to ALDH and positive controls added aspartic acid, which is known to increase ALDH activity.
하기와 같은 식으로 ALDH 활성을 산출하였다. ALDH activity was calculated by the following formula.
ALDH 활성(%) = (B/A) × 100ALDH Activity (%) = (B / A) × 100
A : 대조구의 최대 흡광도A: maximum absorbance of the control
B : 실험구의 최대 흡광도B: maximum absorbance of the experiment
그 결과, 하기 표 3에서 보는 바와 같이, 본 발명의 화학식 1 또는 화학식 2로 표시되는 화합물은 대조군에 비해 ALDH의 활성을 증가시키는 것을 알 수 있다.As a result, as shown in Table 3, it can be seen that the compound represented by Formula 1 or Formula 2 of the present invention increases the activity of ALDH compared to the control.
<< 실험예Experimental Example 2> 알코올 2> alcohol 디하이드로나제Dehydronase 활성 측정 Active measurement
ADH(Alcohol dehydrogenase) 활성도는 Choi 등과 Racker의 방법을 변용하여 UV/VIS 스펙트로미터(spectrophotometer)(V-530, Jasco社)를 이용하여 340nm에서 형성되는 NADH의 흡광도를 측정함으로써 나타내었다. 시험관에 알코올 0.1 ㎕, NAD수용액(2 ㎍/㎕) 0.5 ㎕, 상기 화합물을 각각 0.1 ㎕를 첨가하고 0.01M glycine-NaOH 완충용액(pH 8.8)를 총부피가 1.8 ㎕가 되게 첨가한 후 25℃ 항온 수조에 10분간 반응시키고 ADH(18 units/㎕) 0.25 ㎕를 가하여 340nm에서 흡광도의 변화를 측정하였다. 이때 대조군은 ADH 대신 0.01M glycine-NaOH 완충용액 0.25 ㎕를 넣은 것으로 하였다. ADH의 활성은 반응 종료시의 최대 흡광도를 대조군의 최대 흡광도에 대한 비율로 나타내었으며 다음과 같은 식으로 계산하였다. Alcohol dehydrogenase (ADH) activity was expressed by measuring the absorbance of NADH formed at 340 nm using a UV / VIS spectrophotometer (V-530, Jasco) using a modified method of Choi et al. 0.1 μl of alcohol, 0.5 μl of NAD solution (2 μg / μl) and 0.1 μl of the compound were added to each test tube, and 0.01 M glycine-NaOH buffer solution (pH 8.8) was added so that the total volume was 1.8 μl. After 10 minutes of reaction in a constant temperature bath, 0.25 μl of ADH (18 units / μl) was added to measure the change in absorbance at 340 nm. In this case, 0.25 μl of 0.01M glycine-NaOH buffer solution was used instead of ADH. The activity of ADH was expressed as the ratio of the maximum absorbance at the end of the reaction to the maximum absorbance of the control group was calculated as follows.
ADH 활성 = (B/A) × 100ADH activity = (B / A) × 100
A: 대조구의 최대 흡광도A: maximum absorbance of the control
B: 실험구의 최대 흡광도B: maximum absorbance of the experiment
그 결과, 하기 표 4에서 보는 바와 같이, 본 발명의 화학식 1 또는 화학식 2로 표시되는 화합물은 대조군에 비해 ADH의 활성을 증가시키는 것을 알 수 있다.As a result, as shown in Table 4, it can be seen that the compound represented by Formula 1 or Formula 2 of the present invention increases the activity of ADH compared to the control.
하기에 본 발명의 조성물을 위한 제제예를 예시한다.Examples of preparations for the compositions of the present invention are illustrated below.
<< 제제예Formulation example 1> 1> 산제의Powder 제조 Produce
화학식 1의 화합물 20 mg20 mg of compound of Formula 1
유당 100 mgLactose 100 mg
탈크 10 mg
상기의 성분들을 혼합하고 기밀포에 충진하여 산제를 제조한다.The above ingredients are mixed and filled in an airtight cloth to prepare a powder.
<제제예 2> 정제의 제조 Formulation Example 2 Preparation of Tablet
화학식 1의 화합물 10 mg10 mg of compound of Formula 1
옥수수전분 100 mgCorn starch 100 mg
유당 100 mgLactose 100 mg
스테아린산 마그네슘 2 mg2 mg magnesium stearate
상기의 성분들을 혼합한 후 통상의 정제의 제조방법에 따라서 타정하여 정제를 제조한다.After mixing the above components, tablets are prepared by tableting according to a conventional method for preparing tablets.
<< 제제예Formulation example 3> 캡슐제의 제조 3> Preparation of capsule
화학식 1의 화합물 10 mg10 mg of compound of Formula 1
결정성 셀룰로오스 3 mg3 mg of crystalline cellulose
락토오스 14.8 mgLactose 14.8 mg
마그네슘 스테아레이트 0.2 mgMagnesium Stearate 0.2 mg
통상의 캡슐제 제조방법에 따라 상기의 성분을 혼합하고 젤라틴 캡슐에 충전하여 캡슐제를 제조한다.According to a conventional capsule preparation method, the above ingredients are mixed and filled into gelatin capsules to prepare capsules.
<< 제제예Formulation example 4> 주사제의 제조 4> Preparation of Injection
화학식 1의 화합물 10 mg10 mg of compound of Formula 1
만니톨 180 mgMannitol 180 mg
주사용 멸균 증류수 2974 mgSterile distilled water for injection 2974 mg
Na2HPO4 ,12H2O 26 mgNa 2 HPO 4 , 12H 2 O 26 mg
통상의 주사제의 제조방법에 따라 1 앰플당(2㎖) 상기의 성분 함량으로 제조한다.According to the conventional method for preparing an injection, the amount of the above ingredient is prepared per ampoule (2 ml).
<< 제제예Formulation example 5> 5> 액제의Liquid 제조 Produce
화학식 2의 화합물 20 mg20 mg of compound of formula 2
이성화당 10 g10 g of isomerized sugar
만니톨 5 g5 g of mannitol
정제수 적량Purified water
통상의 액제의 제조방법에 따라 정제수에 각각의 성분을 가하여 용해시키고 레몬향을 적량 가한 다음 상기의 성분을 혼합한 다음 정제수를 가하여 전체를 정제수를 가하여 전체 100㎖로 조절한 후 갈색병에 충진하여 멸균시켜 액제를 제조한다.According to the conventional method of preparing a liquid solution, each component is added and dissolved in purified water, lemon flavor is added to the mixture, and then the above ingredients are mixed, purified water is added to adjust the total amount to 100 ml, and then filled in a brown bottle. The solution is prepared by sterilization.
<< 제제예Formulation example 6> 건강 식품의 제조 6> Manufacture of healthy food
화학식 2의 화합물 1000 ㎎1000 mg of compound of formula 2
비타민 혼합물 적량Vitamin mixture proper amount
비타민 A 아세테이트 70 ㎍70 μg of Vitamin A Acetate
비타민 E 1.0 ㎎Vitamin E 1.0 mg
비타민 B1 0.13 ㎎Vitamin B1 0.13 mg
비타민 B2 0.15 ㎎Vitamin B2 0.15 mg
비타민 B6 0.5 ㎎Vitamin B6 0.5 mg
비타민 B12 0.2 ㎍0.2 μg of vitamin B12
비타민 C 10 ㎎
비오틴 10 ㎍10 μg biotin
니코틴산아미드 1.7 ㎎Nicotinic Acid 1.7 mg
엽산 50 ㎍50 μg folic acid
판토텐산 칼슘 0.5 ㎎Calcium Pantothenate 0.5mg
무기질 혼합물 적량Mineral mixture
황산제1철 1.75 ㎎Ferrous Sulfate 1.75 mg
산화아연 0.82 ㎎Zinc Oxide 0.82 mg
탄산마그네슘 25.3 ㎎Magnesium carbonate 25.3 mg
제1인산칼륨 15 ㎎Potassium monophosphate 15 mg
제2인산칼슘 55 ㎎Dibasic calcium phosphate 55 mg
구연산칼륨 90 ㎎Potassium Citrate 90 mg
탄산칼슘 100 ㎎Calcium Carbonate 100 mg
염화마그네슘 24.8 ㎎Magnesium chloride 24.8 mg
상기의 비타민 및 미네랄 혼합물의 조성비는 비교적 건강식품에 적합한 성분을 바람직한 실시예로 혼합 조성하였지만, 그 배합비를 임의로 변형 실시하여도 무방하며, 통상의 건강식품 제조방법에 따라 상기의 성분을 혼합한 다음, 과립을 제조하고, 통상의 방법에 따라 건강식품 조성물 제조에 사용할 수 있다.Although the composition ratio of the above-mentioned vitamin and mineral mixtures is mixed with a component suitable for a health food in a preferred embodiment, the compounding ratio may be arbitrarily modified, and the above ingredients are mixed according to a conventional health food manufacturing method. The granules may be prepared and used for preparing a health food composition according to a conventional method.
<< 제제예Formulation example 7> 건강 음료의 제조 7> Manufacture of health drinks
화학식 2의 화합물 1000 ㎎1000 mg of compound of formula 2
구연산 1000 ㎎Citric acid 1000 mg
올리고당 100 g100 g oligosaccharides
매실농축액 2 gPlum concentrate 2 g
타우린 1 g1 g of taurine
정제수 전체 900 ㎖900 ml of purified water
통상의 건강음료 제조방법에 따라 상기의 성분을 혼합한 다음, 약 1시간 동안 85℃에서 교반 가열한 후, 만들어진 용액을 여과하여 멸균된 2ℓ 용기에 취득하여 밀봉 멸균한 뒤 냉장 보관한 다음 본 발명의 건강음료 조성물 제조에 사용한다. After mixing the above components according to a conventional healthy beverage production method, and then stirred and heated at 85 ℃ for about 1 hour, the resulting solution is filtered and obtained in a sterilized 2 L container, sealed sterilization and refrigerated and then stored in the present invention For the preparation of healthy beverage compositions.
상기 조성비는 비교적 기호음료에 적합한 성분을 바람직한 실시예로 혼합 조성하였지만, 수요계층, 수요국가, 사용용도 등 지역적, 민족적 기호도에 따라서 그 배합비를 임의로 변형 실시하여도 무방하다.Although the composition ratio is a composition that is relatively suitable for the preferred beverage in a preferred embodiment, the compounding ratio may be arbitrarily modified according to regional and ethnic preferences such as demand hierarchy, demand country, and usage.
도 1은 황태로부터 화학식 1로 표시되는 화합물을 분리하는 과정을 나타내는 모식도이고,1 is a schematic diagram showing a process of separating the compound represented by the formula (1) from the Emperor,
도 2는 황태로부터 화합물 1 및 화학식 2로 표시되는 화합물을 분리하는 과정을 나타내는 모식도이다.Figure 2 is a schematic diagram showing the process of separating the compound represented by Formula 1 and Formula 2 from the Emperor.
Claims (8)
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US4021572A (en) | 1975-07-23 | 1977-05-03 | Scott Eugene J Van | Prophylactic and therapeutic treatment of acne vulgaris utilizing lactamides and quaternary ammonium lactates |
KR20040005545A (en) * | 2002-07-09 | 2004-01-16 | 김선재 | Preparation of beverage contained de-alcohol activity substance |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US4021572A (en) | 1975-07-23 | 1977-05-03 | Scott Eugene J Van | Prophylactic and therapeutic treatment of acne vulgaris utilizing lactamides and quaternary ammonium lactates |
KR20040005545A (en) * | 2002-07-09 | 2004-01-16 | 김선재 | Preparation of beverage contained de-alcohol activity substance |
Non-Patent Citations (2)
Title |
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논문1:Int J Biochem |
논문3:Vopr.Med.Khim |
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