KR101105344B1 - Novel Ginsenoside and Use Thereof - Google Patents
Novel Ginsenoside and Use Thereof Download PDFInfo
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- KR101105344B1 KR101105344B1 KR1020100048283A KR20100048283A KR101105344B1 KR 101105344 B1 KR101105344 B1 KR 101105344B1 KR 1020100048283 A KR1020100048283 A KR 1020100048283A KR 20100048283 A KR20100048283 A KR 20100048283A KR 101105344 B1 KR101105344 B1 KR 101105344B1
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- South Korea
- Prior art keywords
- ginsenoside
- treatment
- pharmaceutical composition
- prevention
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Abstract
본 발명은 화학식 1의 구조를 갖는 진세노사이드를 유효성분으로 포함하는 의약, 식품 또는 화장료 조성물에 관한 것이다.
본 발명에 따른 화학식 1의 구조를 갖는 진세노사이드는 인터루킨-12 (Interleukin-12), 인터루킨-6 (Interleukin-6) 및 TNF(Tumor necrosis factor)-α 생산 저해 효과가 우수하여, 이들로 인해 유발되는 자가 면역 질환과 패혈증 등의 치료에 유용하게 활용될 수 있다. The present invention relates to a pharmaceutical, food or cosmetic composition comprising ginsenoside having the structure of Formula 1 as an active ingredient.
Ginsenosides having the structure of Formula 1 according to the present invention is excellent in inhibiting the production of Interleukin-12, Interleukin-6, and Tumor necrosis factor (TNF), It can be usefully used for the treatment of induced autoimmune diseases and sepsis.
Description
본 발명은 신규한 진세노사이드 및 이의 자가 면역 질환 또는 패혈증의 예방 및 치료 용도에 관한 것이다.The present invention relates to novel ginsenosides and their use in the prophylaxis and treatment of autoimmune diseases or sepsis.
진세노사이드(ginsenoside)란 인삼(ginseng)과 배당체(glycoside)의 합성어로 인삼에서 발견되는 특이한 구조의 사포닌을 의미한다. Ginsenoside (ginsenoside) is a compound word of ginseng (ginseng) and glycoside (glycoside) refers to the unique structure of saponin found in ginseng.
인삼은 오랫동안 동아시아 여러 나라에서 건강 증진 및 질병 치료를 위해 사용되어 왔다. 일반적으로 상기 진세노사이드 및 이의 대사 물질이 인삼 추출물의 주 약리 효과를 나타내는 것으로 생각되고 있으며, 지금까지 밝혀진 인삼의 작용은 면역력 증진, 항염 효과, 진통 효과, 지혈 작용 또는 심혈관계 개선 등으로 다양하다. 특히 항염 효과에 대해서는 진세노사이드 Rh1에 의한 항염 및 항알러지 기능, 진세노사이드 Rb1에 의한 TNF-α의 감소, 진세노사이드 Rg1에 의한 면역기능 증대 등이 보고 된 바 있다. Ginseng has long been used in various countries in East Asia for health promotion and disease treatment. In general, the ginsenosides and their metabolites are believed to exhibit the main pharmacological effect of ginseng extract, the action of ginseng that has been found so far vary in immunity enhancement, anti-inflammatory effect, analgesic effect, hemostatic action or cardiovascular improvement . In particular, anti-inflammatory effects have been reported for anti-inflammatory and anti-allergic function by ginsenoside Rh1, reduction of TNF-α by ginsenoside Rb1, and enhancement of immune function by ginsenoside Rg1.
자가 면역 질환은 우리 몸의 면역 기능이 자신을 공격함으로써 일어나는 질병으로 오랜 기간에 걸쳐 형성되고 증상이 만성적으로 지속되며 대체로 장기의 영구손상을 초래하는 것이 일반적이며, 완치할 수 있는 방법이 거의 없는 것이 현실이다. Autoimmune disease is a disease caused by the body's immune function attacking itself, which is formed over a long period of time, the symptoms persist chronically, and usually cause permanent damage to organs, and there is little to be cured. It is a reality.
자가 면역 질환의 예로는 ⅰ) 면역계가 각종 관절의 조직을 공격하는 류마티스관절염(Rheumatoid Arthritis), ⅱ) T 세포에 의하여 유도되는 중추신경계의 자가면역증으로 대부분은 비교적 정상적인 생활이 가능하나, 심한 경우 실명, 마비, 조기사망(premature death)으로 이어질 수 있는 다발성 경화증(MS, Multiple Sclerosis), ⅲ) 췌장의 인슐린 생산 세포를 면역세포가 파괴하여 생기며 MHC 유전자가 중요한 역할을 수행하는 면역매개, 또는 제 Ⅰ 형 당뇨병(Immune-Mediated or Type Ⅰ Diabetes Mellitus), ⅳ) 면역계가 장을 공격하여 나타나는 질환인 염증성 장질환(Inflammatory Bowel Diseases), ⅴ) 피부나 혈관의 경화(thickening)를 유도하는 피부경화증(Scleroderma), ⅵ) 전신성 자가면역증으로 깊은 피로감, 발진, 관절통 등의 증세를 수반하며, 심한 경우 면역계가 신장, 뇌, 폐 등에 손상을 끼칠 수 있는 전신성 루프스(Systemic Lupus Erythematosus, SLE) 등이 있다.Examples of autoimmune diseases include i) Rheumatoid Arthritis in which the immune system attacks tissues of various joints, and ii) autoimmunity of the central nervous system induced by T cells. Multiple Sclerosis (MS), which can lead to blindness, paralysis, and premature death, i.e., immune mediators that destroy the insulin-producing cells of the pancreas and play an important role in the MHC gene Immune-Mediated or Type I Diabetes Mellitus (ⅳ) Inflammatory Bowel Diseases, a disease caused by the immune system attacking the intestine (ⅴ), scleroderma, which induces thickening of the skin or blood vessels (() Scleroderma), ⅵ) Systemic autoimmunity, accompanied by symptoms such as deep fatigue, rash, joint pain, and in severe cases, damage to the kidneys, brain, lungs, etc. Systemic lupus and the like that can hit (Systemic Lupus Erythematosus, SLE).
인터루킨-12는 항원 자극에 의해 수지상세포, 마크로파지 등의 항원제공세포에서 제조되는 인터루킨의 한 종류로, T세포를 자극하여 1형 헬퍼 T 세포로 분화시키는 역할을 수행하며, NK(natural killer) 세포, T림포사이트의 활성도에 중요한 역할을 한다. 이는 IL-12A(p35)와 IL-12B(p40)의 헤테로다이머 형태이며, IL-12A(p35)의 발현은 항상적(constitutive)이어서, 인터루킨-12의 생물학적 기능은 주로 IL-12B(p40)의 발현에 좌우되는데, 이러한 인터루킨-12의 억제가 인체 내 세포에 대한 과잉 면역반응인 자가 면역 질환의 치료에 도움이 될 수 있다는 연구결과가 보고되고 있다. Interleukin-12 is a kind of interleukin produced in antigen-providing cells such as dendritic cells and macrophages by antigen stimulation. It acts to stimulate T cells to differentiate into
패혈증(sepsis)은 미생물에 감염되어 전신에 심각한 염증 반응이 나타나는 상태를 말한다. 보다 구체적으로는 체온이 38도 이상으로 올라가는 발열 증상 혹은 36도 이하로 내려가는 저체온증, 호흡수가 분당 24회 이상으로 증가(빈호흡), 분당 90회 이상의 심박수(빈맥), 혈액 검사상 백혈구 수의 증가 혹은 현저한 감소 중 두 가지 이상의 증상을 보이는 경우, 이를 전신성 염증 반응 증후군(systemic inflammatory response syndrome; SIRS)이라고 부르는데, 이러한 전신성 염증 반응 증후군이 미생물의 감염에 의한 것일 때 패혈증이라고 한다.Sepsis is a condition in which a microbial infection causes a severe inflammatory response throughout the body. More specifically, fever symptoms that rise above 38 degrees, or hypothermia falling below 36 degrees, respiratory rate increases to more than 24 times per minute (empty breathing), heart rate of 90 or more times per minute (tachycardia), or an increase in white blood cell counts on blood tests, or If there is more than one symptom of a significant decrease, it is called systemic inflammatory response syndrome (SIRS), which is called sepsis when the systemic inflammatory response syndrome is caused by a microbial infection.
리포폴리사카라이드(LPS)는 그람 음성 세균의 세포벽을 구성하는 성분으로 인체에 과도하게 노출될 경우 패혈증 쇼크를 유발한다. 이는 숙주 대식세포나 수지상세포와 같은 항원제공세포를 자극하여 숙주 유발 염증과정을 일으키는데, 이때 과량 생성된 인터루킨-6와 TNF-α가 패혈증의 주된 사망원인인 내독소 쇼크(endotoxic shock)를 일으킨다고 알려져 있다. Lipopolysaccharide (LPS) is a component of the cell wall of Gram-negative bacteria and causes excessive sepsis shock when exposed to the human body. It stimulates antigen-providing cells, such as host macrophages and dendritic cells, to cause host-induced inflammatory processes, in which overproduced interleukin-6 and TNF-α cause endotoxic shock, the leading cause of sepsis. Known.
따라서 본 발명의 발명자들은 상기 염증 반응을 일으키는 염증성 사이토카인의 억제 물질들을 연구하던 중, 인삼 추출물 중 잎과 꽃에서 추출된 신규한 진세노이드 화합물이 인터루킨-12 (Interleukin-12), 인터루킨-6 (Interleukin-6) 및 TNF(Tumor Necrosis Factor)-α 생산 억제 활성이 있음을 알아냄으로써 본 발명을 완성하였다.
Therefore, the inventors of the present invention while studying the inhibitory substances of the inflammatory cytokines causing the inflammatory response, the novel ginsenoid compounds extracted from the leaves and flowers of the ginseng extract Interleukin-12, Interleukin-6 ( The present invention was completed by finding out that they have inhibitory activity against Interleukin-6) and Tumor Necrosis Factor (TNF) -α production.
본 발명은 자가 면역 질환 또는 패혈증의 예방 및 치료 효과를 갖는 신규한 진세노사이드 및 이를 포함하는 의약, 식품 및 화장료 조성물을 제공하고자 한다. The present invention is to provide a novel ginsenoside having a prophylactic and therapeutic effect of autoimmune diseases or sepsis and a pharmaceutical, food and cosmetic composition comprising the same.
상기 과제의 해결을 위하여, 본 발명은 화학식 1의 구조를 갖는 진세노사이드를 제공한다. In order to solve the above problems, the present invention provides a ginsenoside having a structure of formula (1).
또한 본 발명은 상기 진세노사이드를 포함하는 자가 면역 질환 또는 패혈증의 예방 및 치료용 의약 조성물을 제공한다. The present invention also provides a pharmaceutical composition for the prevention and treatment of autoimmune diseases or sepsis comprising the ginsenoside.
본 발명에 따른 신규 진세노사이드는 인터루킨-12 (Interleukin-12), 인터루킨-6 (Interleukin-6) 및 TNF(Tumor Necrosis Factor)-α 생산 저해 효과가 우수하여, 이들로 인해 유발되는 자가 면역 질환과 패혈증 등의 치료에 유용하게 활용될 수 있다.
The novel ginsenosides according to the present invention have an excellent inhibitory effect on the production of Interleukin-12, Interleukin-6 and Tumor Necrosis Factor (TNF), and are caused by autoimmune diseases. It can be usefully used for the treatment of sepsis.
도 1은 LPS로 자극한 골수유래 수지상세포의 인터루킨 12 (IL-12) 생산에 미치는 본 발명의 진세노사이드의 저해 효과를 측정한 실시예 2의 실험 결과 그래프이다.
도 2는 LPS로 자극한 골수유래 수지상세포의 인터루킨 12 (IL-12) 생산에 미치는 다른 공지의 진세노사이드의 저해 효과를 측정한 비교예 1의 실험 결과 그래프이다.
도 3는 LPS로 자극한 골수유래 수지상세포의 인터루킨-6 (IL-6) 생산에 미치는 본 발명의 진세노사이드의 저해 효과를 측정한 실시예 3의 실험 결과 그래프이다.
도 4은 LPS로 자극한 골수유래 수지상세포의 TNF-α 생산에 미치는 본 발명의 진세노사이드의 저해 효과를 측정한 실시예 4의 실험 결과 그래프이다.1 is a graph of the experimental results of Example 2 measuring the inhibitory effect of ginsenosides of the present invention on the production of interleukin 12 (IL-12) in LPS-stimulated myeloid-derived dendritic cells.
Figure 2 is a graph of the results of the experiment of Comparative Example 1 measuring the inhibitory effect of other known ginsenosides on the production of interleukin 12 (IL-12) in LPS-stimulated bone marrow-derived dendritic cells.
Figure 3 is a graph of the experimental results of Example 3 measuring the inhibitory effect of ginsenosides of the present invention on the production of interleukin-6 (IL-6) in LPS-stimulated myeloid-derived dendritic cells.
Figure 4 is a graph of the experimental results of Example 4 measuring the inhibitory effect of ginsenosides of the present invention on TNF-α production of LPS-stimulated myeloid-derived dendritic cells.
본 발명은 하기 화학식 1의 구조를 갖는 진세노사이드를 제공한다. The present invention provides ginsenosides having the structure of Formula 1.
[화학식 1][Formula 1]
본 발명의 한 구체예에 따르면, 상기 진세노사이드는 인삼에서 추출하여 사용할 수 있다. 본 발명의 발명자들은, 인삼으로부터 상기 진세노사이드 계열의 신규 화합물을 추출하여 구조를 규명하였고, 이들이 인터루킨-12 (Interleukin-12), 인터루킨-6 (Interleukin-6) 및 TNF(Tumor Necrosis Factor)-α 생산 저해 효과가 있음을 확인하였다. According to one embodiment of the present invention, the ginsenoside may be extracted and used in ginseng. The inventors of the present invention, by extracting the ginsenoside family of novel compounds from ginseng to determine the structure, they are interleukin-12, Interleukin-6 and TNF (Tumor Necrosis Factor)- It was confirmed that the α production inhibitory effect.
상기 인삼이란 고려삼(Panax ginseng), 회기삼(P. quiquefolius), 전칠삼(P. notoginseng), 죽절삼(P. japonicus), 삼엽삼(P. trifolium), 히말라야삼(P. pseudoginseng), 베트남삼(P. vietnamensis) 또는 미국삼(Panax quinquefolium) 등을 의미하나, 이에 제한되는 것은 아니다. 바람직하게는 고려삼(Panax ginseng)을 사용할 수 있고, 특히 잎, 꽃 또는 뿌리 부분에서 추출하여 사용할 수 있다. 이외에도 상기 진세노사이드는 일반적인 화학적 합성 방법에 의해서 합성할 수도 있다. The ginseng is Korean ginseng ( Panax ginseng ), P. quiquefolius , P. notoginseng , P. japonicus , P. trifolium , P. pseudoginseng , P. vietnamensis , or Vietnamese ginseng American Panax quinquefolium ) and the like, but is not limited thereto. Preferably, Panax ginseng may be used, and particularly, extract may be used from a leaf, a flower, or a root part. In addition, the ginsenoside may be synthesized by a general chemical synthesis method.
또한 본 발명은 인삼을 물, 알코올 또는 물과 알코올의 혼합용매로 추출한 후 감압 농축하여 인삼 추출물을 얻는 단계; 이에 극성 용매를 가하고 비극성 용매로 분획하여 극성 용매층을 분리하는 단계; 상기 극성 용매층으로 컬럼 크로마토그라피를 실시하는 단계를 포함하는 인삼으로부터 상기 진세노사이드를 추출하는 방법을 제공한다. In another aspect, the present invention is to extract the ginseng with water, alcohol or a mixed solvent of water and alcohol and then concentrated under reduced pressure to obtain a ginseng extract; Adding a polar solvent and fractionating the non-polar solvent to separate the polar solvent layer; It provides a method for extracting the ginsenoside from ginseng comprising the step of performing column chromatography with the polar solvent layer.
상기 인삼 추출물을 얻는 단계에서 사용되는 알코올은 이에 한정되는 것은 아니지만 메탄올, 에탄올, 부탄올 또는 주정일 수 있으며, 바람직하게는 메탄올일 수 있다. 여기서 '주정'이란 전분질 원료 또는 당질 원료를 발효시킨 후 증류하여 만든 에탄올을 의미한다. 또한 상기 물과 알코올의 혼합용매는 이에 한정되는 것은 아니지만 물과 알코올은 임의 적량 비율대로 혼합하여 사용할 수 있다. The alcohol used in the step of obtaining the ginseng extract may be, but is not limited to, methanol, ethanol, butanol or alcohol, preferably methanol. Here, 'alcohol' refers to ethanol made by distilling fermented starch raw material or sugar raw material. In addition, the mixed solvent of water and alcohol is not limited thereto, and water and alcohol may be mixed and used in any suitable ratio.
상기 극성 용매층을 분리하는 단계에서 사용되는 극성 용매는 이에 한정되는 것은 아니지만 물, 탄소수 1 내지 4의 저급 알코올 및 이들의 혼합용매일 수 있으며, 바람직하게는 물일 수 있다. The polar solvent used in the step of separating the polar solvent layer may be, but is not limited to, water, a lower alcohol having 1 to 4 carbon atoms, and a mixed solvent thereof, preferably water.
또한 상기 극성 용매층을 분리하는 단계에서 사용되는 비극성 용매는 이에 한정되는 것은 아니지만 아세톤, 에틸아세테이트, 에테르, 클로로포름, 이염화메탄, 펜탄, 핵산, 헵탄, 노난, 데칸, 벤젠, 톨루엔, 자이렌 등을 사용할 수 있으며, 바람직하게는 핵산(n-Hexane) 또는 이염화메탄일 수 있다. In addition, the non-polar solvent used in the step of separating the polar solvent layer is not limited to acetone, ethyl acetate, ether, chloroform, methane dichloride, pentane, nucleic acid, heptane, nonane, decane, benzene, toluene, xylene and the like. It may be used, preferably may be a nucleic acid ( n- Hexane) or methane dichloride.
상기 컬럼 크로마토그래피는 이에 한정되는 것은 아니지만 흡착제로서 실리카겔, 역상실리카겔, 세파덱스류, 다이아이온 레진류, 알루미나, 활성탄, 규산마그네슘, 탄산칼슘, 인산칼슘, 인산마그네슘, 마그네시아 또는 수산화칼륨 등을 사용할 수 있으며, 바람직하게는 실리카겔을 사용할 수 있다.The column chromatography may be, but is not limited to, silica gel, reversed phase silica gel, Sephadex, diion resins, alumina, activated carbon, magnesium silicate, calcium carbonate, calcium phosphate, magnesium phosphate, magnesia or potassium hydroxide. And, preferably, silica gel can be used.
그러나 본 발명에 따른 진세노사이드를 제조하는 방법은 이에 제한되는 것은 아니며, 일반적인 화학적 합성 방법에 의해서 제조할 수 있음은 당업자에게 자명하다.
However, the method for preparing ginsenosides according to the present invention is not limited thereto, and it is apparent to those skilled in the art that they can be prepared by a general chemical synthesis method.
또한 본 발명은 상기 진세노사이드를 유효성분으로 포함하는 자가 면역 질환의 예방 및 치료용 의약 조성물을 제공한다. 하기 실시예를 통하여 알 수 있듯이, 본 발명에 따른 진세노사이드는 우수한 인터루킨-12 생산 저해 효과를 갖는다. 이러한 효과를 통해 자가 면역 질환을 예방 및 치료할 수 있으며, 구체적으로 다발성 경화증(MS, multiple sclerosis), 건선, 류마티스 관절염, 크론병(Chrohn's disease), 궤양성 대장염, 제 I 형 당뇨병(diabetes mellitus), 염증성 장질환, 또는 전신성 루프스 등의 자가 면역 질환의 예방 및 치료에 적용될 수 있으나 이에 제한되는 것은 아니다.The present invention also provides a pharmaceutical composition for the prevention and treatment of autoimmune diseases comprising the ginsenoside as an active ingredient. As can be seen through the following examples, ginsenosides according to the present invention has an excellent interleukin-12 production inhibitory effect. These effects can prevent and treat autoimmune diseases, and in particular, multiple sclerosis (MS), psoriasis, rheumatoid arthritis, Crohn's disease, ulcerative colitis, type I diabetes (diabetes mellitus), It may be applied to the prevention and treatment of inflammatory bowel disease or autoimmune diseases such as systemic lupus, but is not limited thereto.
본 발명에 따른 진세노사이드를 유효성분으로 포함하는 자가 면역 질환의 예방 및 치료용 의약 조성물은 자가 면역 질환의 치료에 사용될 수 있다. 따라서 본 발명은 진세노사이드를 유효성분으로 포함하는 자가 면역 질환의 예방 및 치료용 의약 조성물, 자가 면역 질환 치료제의 제조를 위한 진세노사이드의 용도, 그리고 치료상 유효량의 진세노사이드를 대상체에 투여하는 단계를 포함하는 자가 면역 질환의 치료 방법을 제공한다.
Pharmaceutical composition for the prevention and treatment of autoimmune diseases comprising ginsenosides according to the present invention can be used for the treatment of autoimmune diseases. Therefore, the present invention provides a pharmaceutical composition for the prevention and treatment of autoimmune diseases comprising ginsenosides, the use of ginsenosides for the preparation of autoimmune diseases, and a therapeutically effective amount of ginsenosides to a subject. It provides a method of treating an autoimmune disease comprising the steps of.
또한 본 발명은 상기 진세노사이드를 유효성분으로 포함하는 패혈증의 예방 및 치료용 의약 조성물을 제공한다. 하기 실시예를 통하여 알 수 있듯이, 본 발명에 따른 진세노사이드는 패혈증 쇼크를 일으키는 인터루킨-6 (Interleukin-6) 및 TNF(Tumor Necrosis Factor)-α 의 생산 저해 효과가 우수하여, 패혈증 예방 및 치료를 위해 사용될 수 있다. 따라서 본 발명은 진세노사이드를 유효성분으로 포함하는 패혈증의 예방 및 치료용 의약 조성물, 패혈증 치료제의 제조를 위한 진세노사이드의 용도, 그리고 치료상 유효량의 진세노사이드를 대상체에 투여하는 단계를 포함하는 패혈증의 치료 방법을 제공한다.
The present invention also provides a pharmaceutical composition for the prevention and treatment of sepsis comprising the ginsenoside as an active ingredient. As can be seen through the following examples, ginsenosides according to the present invention is excellent in inhibiting the production of Interleukin-6 and TNF (Tumor Necrosis Factor) -α, which cause sepsis shock, prevention and treatment of sepsis Can be used for Accordingly, the present invention includes a pharmaceutical composition for the prevention and treatment of sepsis comprising ginsenoside as an active ingredient, the use of ginsenoside for the preparation of a septic agent, and administering to the subject a therapeutically effective amount of ginsenoside. It provides a method of treating sepsis.
본 발명의 한 구체예에서, 상기 진세노사이드를 유효성분으로 포함하는 자가 면역 질환 또는 패혈증의 예방 및 치료용 의약 조성물은 약학 조성물의 제조에 통상적으로 사용하는 적절한 담체, 부형제, 붕해제, 감미제, 피복제, 팽창제, 윤활제, 활택제, 향미제, 항산화제, 완충액, 정균제, 희석제, 분산제, 계면활성제, 결합제 및 윤활제로 이루어진 군에서 선택되는 하나 이상의 보조제를 추가로 포함할 수 있다.In one embodiment of the present invention, the pharmaceutical composition for the prevention and treatment of autoimmune diseases or sepsis comprising the ginsenoside as an active ingredient is a suitable carrier, excipient, disintegrant, sweetener, commonly used in the manufacture of pharmaceutical compositions, It may further comprise one or more adjuvants selected from the group consisting of coatings, swelling agents, lubricants, glidants, flavors, antioxidants, buffers, bacteriostatics, diluents, dispersants, surfactants, binders and lubricants.
구체적으로 담체, 부형제 및 희석제는 락토즈, 덱스트로즈, 수크로스, 솔비톨, 만니톨, 자일리톨, 에리스리톨, 말티톨, 전분, 아카시아 고무, 알지네이트, 젤라틴, 칼슘 포스페이트, 칼슘 실리케이트, 셀룰로즈, 메틸 셀룰로즈, 미정질 셀룰로스, 폴리비닐 피롤리돈, 물, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 탈크, 마그네슘 스테아레이트 및 광물유를 사용할 수 있으며, 경구투여를 위한 고형제제에는 정제, 환제, 산제, 과립제, 캡슐제 등이 포함되며, 이러한 고형제제는 상기 조성물에 적어도 하나 이상의 부형제, 예를 들면, 전분, 칼슘카보네이트, 수크로스 또는 락토오스, 젤라틴 등을 섞어 조제할 수 있다. 또한 단순한 부형제 이외에 마그네슘 스티레이트, 탈크 같은 윤활제들도 사용할 수 있다. 경구를 위한 액상제제로는 현탁제, 내용액제, 유제, 시럽제 등이 있으며 흔히 사용되는 단순 희석제인 물, 리퀴드 파라핀 이외에 여러 가지 부형제, 예를 들면 습윤제, 감미제, 방향제, 보존제 등이 포함될 수 있다. 비경구 투여를 위한 제제에는 멸균된 수용액, 비수성용제, 현탁제, 유제, 동결건조제제, 좌제 등이 포함된다. 비수성용제, 현탁제로는 프로필렌글리콜, 폴리에틸렌 글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테르 등이 사용될 수 있다. 좌제의 기재로는 위텝솔(witepsol), 마크로골, 트윈(tween) 61, 카카오지, 라우린지, 글리세로제라틴 등이 사용될 수 있다. Specifically, the carriers, excipients and diluents are lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline Cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil can be used, and solid preparations for oral administration include tablets, pills, powders, granules, capsules. And the like, and such solid preparations may be prepared by mixing at least one excipient such as starch, calcium carbonate, sucrose or lactose, gelatin and the like in the composition. In addition to simple excipients, lubricants such as magnesium styrate and talc may also be used. Oral liquid preparations include suspensions, solvents, emulsions, syrups, and the like, 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. Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories, and the like. Examples of the suspending agent include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like. Witsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like may be used as the base material of the suppository.
본 발명의 다른 구체예에서, 상기 진세노사이드를 유효성분으로 포함하는 자가 면역 질환 또는 패혈증의 예방 및 치료용 의약 조성물은 통상적인 방법에 따라 과립제, 산제, 피복정, 정제, 환제, 캡슐제, 좌제, 겔, 시럽, 즙, 현탁제, 유제, 점적제 또는 액제로 제형화하여 사용할 수 있다.In another embodiment of the present invention, the pharmaceutical composition for the prevention and treatment of autoimmune diseases or sepsis comprising the ginsenoside as an active ingredient, granules, powders, coated tablets, tablets, pills, capsules, It may be formulated into suppositories, gels, syrups, juices, suspensions, emulsions, drops or solutions.
본 발명의 일실시예에 따르면 상기 의약 조성물은 정맥내, 동맥내, 복강내, 근육내, 동맥내, 복강내, 흉골내, 경피, 비측내, 흡입, 국소, 직장, 경구, 안구내 또는 피내 경로를 통해 통상적인 방식으로 대상체로 투여할 수 있다.According to one embodiment of the invention the pharmaceutical composition is intravenous, intraarterial, intraperitoneal, intramuscular, intraarterial, intraperitoneal, intrasternal, transdermal, nasal, inhaled, topical, rectal, oral, intraocular or intradermal Via the route can be administered to the subject in a conventional manner.
상기 진세노사이드의 바람직한 투여량은 대상체의 상태 및 체중, 질환의 종류 및 정도, 약물 형태, 투여경로 및 기간에 따라 달라질 수 있으며 당업자에 의해 적절하게 선택될 수 있다. 본 발명의 일실시예에 따르면 이에 제한되는 것은 아니지만 1일 투여량이 0.01 내지 200 mg/kg, 구체적으로는 0.1 내지 200 mg/kg, 보다 구체적으로는 0.1 내지 100 mg/kg 일 수 있다. 투여는 하루에 한 번 투여할 수도 있고 수회로 나누어 투여할 수도 있으며, 이에 의해 본 발명의 범위가 제한되는 것은 아니다.The preferred dosage of ginsenoside may vary depending on the condition and weight of the subject, the type and 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. According to one embodiment of the present invention, but not limited thereto, the daily dosage may be 0.01 to 200 mg / kg, specifically 0.1 to 200 mg / kg, more specifically 0.1 to 100 mg / kg. Administration may be administered once a day or divided into several times, thereby not limiting the scope of the invention.
본 발명에 있어서, 상기 '대상체'는 인간을 포함하는 포유동물일 수 있으나, 이들 예에 한정되는 것은 아니다.
In the present invention, the 'subject' may be a mammal including a human, but is not limited thereto.
또한 본 발명은 상기 화학식 1의 구조를 갖는 진세노사이드를 유효성분으로 포함하는 식품 조성물을 제공한다. 상기 식품 조성물은 인터루킨-12 (Interleukin-12), 인터루킨-6 (Interleukin-6) 및 TNF(Tumor Necrosis Factor)-α 생산 저해 효과가 있어, 특히 자가 면역 질환 및 패혈증의 예방 및 치료 효과를 나타낼 수 있는 건강기능식품 및 일반 식품의 제조에 유용하게 사용될 수 있다. In another aspect, the present invention provides a food composition comprising ginsenoside having the structure of
본 발명의 한 구체예에서, 상기 진세노사이드를 유효성분으로 포함하는 식품 조성물은, 전체 식품 조성물 100 중량부에 대하여 상기 진세노사이드를 0.01 내지 90 중량부, 0.1 내지 90 중량부, 1 내지 90 중량부, 또는 10 내지 90 중량부로 포함할 수 있으나 이에 한정되는 것은 아니다.In one embodiment of the present invention, the food composition comprising the ginsenoside as an active ingredient, 0.01 to 90 parts by weight, 0.1 to 90 parts by weight, 1 to 90 parts by weight of the ginsenoside relative to 100 parts by weight of the total food composition It may include by weight, or 10 to 90 parts by weight, but is not limited thereto.
본 발명의 다른 구체예에서, 상기 식품 조성물은 유기산, 인산염, 항산화제, 유당 카제인, 덱스트린, 포도당, 설탕 및 솔비톨로 이루어진 군에서 선택되는 하나 이상의 첨가제를 추가로 포함할 수 있다. 유기산은 이에 제한되는 것은 아니지만 구연산, 후말산, 아디픽산, 젖산 또는 사과산일 수 있으며, 인산염은 이에 제한되는 것은 아니지만 인산나트륨, 인산칼륨, 산성피로인산염 또는 폴리인산염(중합인산염)일 수 있으며, 항산화제는 이에 제한되는 것은 아니지만 폴리페놀, 카테킨, 알파-토코페롤, 로즈마리 추출물, 감초 추출물, 키토산, 탄닌산 또는 피틴산 등의 천연 항산화제일 수 있다.In another embodiment of the present invention, the food composition may further include one or more additives selected from the group consisting of organic acids, phosphates, antioxidants, lactose casein, dextrin, glucose, sugar and sorbitol. The organic acid may be, but is not limited to, citric acid, fumaric acid, adipic acid, lactic acid or malic acid, and the phosphate may be, but is not limited to, sodium phosphate, potassium phosphate, acid pyrophosphate or polyphosphate (polymeric phosphate), antioxidant The agent may be a natural antioxidant such as, but not limited to, polyphenols, catechins, alpha-tocopherols, rosemary extracts, licorice extracts, chitosan, tannic acid or phytic acid.
본 발명의 또 다른 구체예에서, 상기 진세노사이드를 유효성분으로 포함하는 식품 조성물은 진세노사이드 이외에도 여러 가지 영양제, 비타민, 광물(전해질), 합성 풍미제 및 천연 풍미제 등의 풍미제, 착색제 및 중진제(치즈, 초콜릿 등), 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. 또한 본 발명의 일실시예에 따른 자가 면역 질환의 예방 및 치료용 식품 조성물은 천연 과일 주스, 과일 쥬스 음료 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 이러한 첨가제의 비율은 이에 제한되는 것은 아니지만 본 발명의 조성물 100 중량부당 0 내지 약 20 중량부, 5 내지 20 중량부, 또는 5 내지 15중량부의 범위에서 선택되는 것이 일반적이다.In another embodiment of the present invention, the food composition comprising the ginsenoside as an active ingredient, in addition to ginsenoside, various nutrients, vitamins, minerals (electrolytes), synthetic flavors, such as natural flavors, colorants And neutralizers (cheese, chocolate, etc.), pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols, carbonation agents used in carbonated drinks, and the like. can do. In addition, the food composition for preventing and treating autoimmune diseases according to an embodiment of the present invention may contain a flesh for preparing natural fruit juice, fruit juice beverage and vegetable beverage. The proportion of such additives is generally not limited to, but is selected from the range of 0 to about 20 parts by weight, 5 to 20 parts by weight, or 5 to 15 parts by weight per 100 parts by weight of the composition of the present invention.
본 발명의 일실시예에 따르면, 상기 식품 조성물의 제형은 이에 제한되는 것은 아니지만 고형, 분말, 과립, 정제, 캡슐, 액상 또는 음료 형태일 수 있다.According to one embodiment of the invention, the formulation of the food composition may be in the form of a solid, powder, granules, tablets, capsules, liquids or beverages, but is not limited thereto.
또한 상기 식품 조성물은 이에 제한되는 것은 아니지만 과자류, 당류, 아이스크림 제품류, 유가공품, 식육제품, 어육제품, 두부류 또는 묵류, 식용유지류, 면류, 다류, 음료류, 특수영양식품, 건강보조식품, 조미식품, 얼음, 인삼제품류, 김치절임식품, 건포류, 과일, 야채, 과일 또는 야채의 건조제품, 절단제품, 과일쥬스, 야채쥬스, 이들의 혼합쥬스, 칩류, 면류, 축산가공식품, 수산가공식품, 유가공식품, 발효유식품, 두류식품, 곡류식품, 미생물발효식품, 제과제빵, 양념류, 육가공류, 산성음료수, 감초류, 허브류 등의 식품의 제조에 사용될 수 있다. In addition, the food composition is not limited thereto, but confections, sugars, ice cream products, dairy products, meat products, fish products, tofu or jelly, edible oils, noodles, teas, beverages, special nutrition products, health supplements, seasoned foods, ice , Ginseng products, pickled kimchi, raisins, fruits, vegetables, dried products of fruits or vegetables, cut products, fruit juices, vegetable juices, mixed juices, chips, noodles, livestock processed foods, fish processed foods, dairy products , Fermented milk food, legume food, cereal food, microbial fermented food, bakery, condiments, meat processing, acidic beverages, licorice, herbs and the like can be used in the manufacture of food.
본 발명의 일실시예에 따르면, 상기 진세노사이드를 유효성분으로 포함하는 식품 조성물을 건강기능식품의 제조에 사용할 경우에는 전체 식품 중량의 0.01 내지 15 중량%, 또는 0.1 내지 10 중량%로 사용할 수 있으며, 음료의 제조에 사용할 경우에는 전체 음료 중량의 0.02 내지 10 중량%, 또는 0.3 내지 1 중량%로 사용할 수 있다.
According to one embodiment of the invention, when using a food composition comprising the ginsenoside as an active ingredient in the manufacture of health functional food can be used as 0.01 to 15% by weight, or 0.1 to 10% by weight of the total food weight When used in the manufacture of a beverage, it can be used as 0.02 to 10% by weight, or 0.3 to 1% by weight of the total beverage weight.
또한 본 발명은 화학식 1의 구조를 갖는 진세노사이드(ginsenoside)를 유효성분으로 포함하는 화장료 조성물을 제공한다.In another aspect, the present invention provides a cosmetic composition comprising ginsenoside (ginsenoside) having a structure of formula (1) as an active ingredient.
화학식 1의 구조를 갖는 진세노사이드(ginsenoside)는 하기 실시예를 통하여 알 수 있듯이, 인터루킨-12 (Interleukin-12), 인터루킨-6 (Interleukin-6) 및 TNF(Tumor Necrosis Factor)-α 생산 저해 효과가 우수하여, 아토피성 피부염 등과 같은 피부 염증 반응을 예방 및 치료하기 위한 화장료 조성물로 사용될 수 있다.Ginsenosides having the structure of
본 발명의 한 구체예에서, 상기 화장료 조성물은 화학식 1의 구조를 갖는 진세노사이드와 더불어 화장품에 통상 사용되는 첨가제, 예를 들어, 비타민, 계면활성제, 유화제, 향료, 색소, 안정제, 방부제, 항산화제, 자외선 차단제, pH 조정제 및 킬레이트제로 이루어진 군에서 선택되는 하나 이상의 첨가제를 추가로 포함할 수 있다.In one embodiment of the present invention, the cosmetic composition is a ginsenoside having a structure of formula (1) and additives commonly used in cosmetics, for example, vitamins, surfactants, emulsifiers, flavors, pigments, stabilizers, preservatives, antioxidants And may further include one or more additives selected from the group consisting of sunscreens, pH adjusters and chelating agents.
본 발명의 일실시예에 따르면, 상기 화장료 조성물이 사용되는 화장품은 그 제형에 있어서 이에 한정되는 것은 아니지만 예를 들어 유연화장수, 영양화장수, 마사지크림, 영양크림, 팩, 젤, 에센스, 립스틱, 메이크업 베이스, 파운데이션, 로션, 연고, 겔, 크림, 클렌징, 세안제, 비누, 샴푸, 린스, 트리트먼트 및 미용액일 수 있다. 이러한 화장품은 수성 비타민, 유성 비타민, 고분자 펩티드, 고분자 다당, 스핑고 지질 등의 통상의 성분들을 포함할 수 있으며, 당업자에게 널리 공지된 기술에 따라 용이하게 제조될 수 있다. According to one embodiment of the present invention, the cosmetic composition is used in the formulation is not limited to this, for example, supple cosmetics, nourishing cosmetics, massage cream, nutrition cream, pack, gel, essence, lipstick, makeup Base, foundation, lotion, ointment, gel, cream, cleansing, face wash, soap, shampoo, rinse, treatment and essence. Such cosmetics may include conventional ingredients such as aqueous vitamins, oily vitamins, polymer peptides, polymer polysaccharides, sphingolipids, and the like, and may be readily prepared according to techniques well known to those skilled in the art.
본 발명의 일실시예에 따르면 상기 진세노사이드 성분의 함량은 이에 한정되는 것은 아니지만 화장료 조성물 총 중량에 대하여 0.001 내지 20 중량 %, 0.001 내지 5 중량 %, 또는 0.001 내지 1 중량 % 일 수 있다.
According to one embodiment of the present invention, the content of the ginsenoside component is not limited thereto, but may be 0.001 to 20% by weight, 0.001 to 5% by weight, or 0.001 to 1% by weight based on the total weight of the cosmetic composition.
<실시예><Examples>
이하, 본 발명의 이해를 돕기 위하여 실시예를 들어 상세하게 설명하기로 한다. 다만 하기의 실시예는 본 발명의 내용을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다. 본 발명의 실시예는 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해 제공되는 것이다.
Hereinafter, examples will be described in detail to help understand the present invention. However, the following examples are merely to illustrate the content of the present invention is not limited to the scope of the present invention. The embodiments of the present invention are provided to more completely explain the present invention to those skilled in the art.
<< 실시예Example 1> 1> 진세노사이드의Ginsenoside 제조 Produce
건조된 고려삼(Panax ginseng)의 꽃봉오리 1.2 kg을 메탄올(3L*3, 50℃)로 추출한 후 감압 농축하였다. 추출물(204 g)에 물(H2O) 2.5 L를 가한 후, n-핵산(n-Hexane)과 CH2Cl2(각각 2.5 L*3)로 차례로 분획하였다. n-핵산 및 CH2Cl2분획물의 양은 각각 29.4 g, 15.2 g이었고, 물층의 분획물을 대상으로 Diaion HP-20 컬럼 크로마토그래피를 실시하여 네 개의 분획(Fr. 1.1, 10.8 g; Fr. 1.2, 30.4 g; Fr. 1.3, 29.0 g; Fr. 1.4, 20.0 g)을 얻었다 (이동상: 메탄올과 물의 혼합물; 25, 50, 75, 100% 메탄올; v/v). 그 후 네 번째 분획(Fr. 1.4)을 대상으로 CH2Cl2: 메탄올(20:1→1:1)을 이동상으로 하여 실리카겔 컬럼 크로마토그래피를 실시하여 열한개의 분획을 얻은 후, 열한번째 분획 260 mg을 대상으로 메탄올과 물 9:5 비율 혼합물을 이동상으로 하여 역상 컬럼 크로마토그래피를 실시하여 본 발명의 화합물인 진세노사이드(floralginsenoside Kc) 5.8 mg을 얻었다.
1.2 kg of dried Panax ginseng buds were extracted with methanol (3L * 3, 50 ° C) and concentrated under reduced pressure. 2.5 L of water (H 2 O) was added to the extract (204 g), followed by fractionation with n -nucleic acid (n-Hexane) and CH 2 Cl 2 (2.5 L * 3 each). The amounts of n -nucleic acid and CH 2 Cl 2 fractions were 29.4 g and 15.2 g, respectively. Four fractions (Fr. 1.1, 10.8 g; Fr. 1.2, 30.4 g; Fr. 1.3, 29.0 g; Fr. 1.4, 20.0 g) (mobile phase: mixture of methanol and water; 25, 50, 75, 100% methanol; v / v). The fourth fraction (Fr. 1.4) was then subjected to silica gel column chromatography using CH 2 Cl 2 : methanol (20: 1 → 1: 1) as a mobile phase to obtain eleven fractions. The eleventh fraction 260 mg Reverse phase column chromatography was carried out using methanol and water in a ratio of 9: 5 as a mobile phase, to obtain 5.8 mg of ginsenoside (floralginsenoside Kc) as a compound of the present invention.
하기의 데이터와 표 1 내지 표3은 본 발명의 진세노사이드의 13C NMR(Pyridine-d5, 125 MHz) 및 1H NMR (Pyridine-d5, 500 MHz)결과를 보여준다.The following data and Tables 1 to 3 show 13 C NMR (Pyridine-d 5 , 125 MHz) and 1 H NMR (Pyridine-d 5 , 500 MHz) results of ginsenosides of the present invention.
화학식 1의 Of
무정형의 백색분말; + 11 (c 0.10, MeOH); IR (KBr)νmax 3452, 2918, 1743, 1262 및 1058 cm-1; 1H 및 13C NMR 결과는 표 1 내지 표 3 에 있다; ESI-MS(negative-ion mode) m/z 917 [M - H2O - H]-, 755 [M - H2O - C6H10O5 - H]-; HRESITOFMS(negative-ion mode) m/z 917.4734 [(M - H2O) - H]- (calcd for C45H73O19, 917.4746).
Amorphous white powder; + 11 ( c 0.10, MeOH); IR (KBr) ν max 3452, 2918, 1743, 1262 and 1058 cm −1 ; 1 H and 13 C NMR results are in Tables 1 to 3; Negative-ion mode (ESI-MS) m / z 917 [M-H 2 O-H] - , 755 [M-H 2 O-C 6 H 10 O 5 -H] - ; Negative-ion mode (HRESITOFMS) m / z 917.4734 [(M−H 2 O) −H] − (calcd for C 45 H 73 O 19 , 917.4746).
상기 데이터를 통해, 본 발명의 진세노사이드가 3-O-[β-Dglucopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosyl-3β,12β,20β,23ξ-tetrahydroxy-25,26,27-trinordammar-24-al 이며, 화학식 1의 구조로 나타낼 수 있음을 알 수 있었고, 이를 플로랄진세노사이드(floralginsenoside) Kc 로 명명하였다.
On the data, the ginsenoside of the present invention 3- O - [β -Dglucopyranosyl- (1 → 2) - β -D-glucopyranosyl] -20- O - β -D-glucopyranosyl-3 β, 12 β, 20 β , 23 ξ- tetrahydroxy-25,26,27-trinordammar-24-al, and it can be seen that it can be represented by the structure of
<< 실시예Example 2> 인터루킨-12 생산 저해 활성 평가 2> Evaluation of inhibitory activity of interleukin-12 production
시험에 사용한 진세노사이드 화합물은 DMSO에 녹여서 사용하였다. 골수유래 수지상 세포는 야생형 C57BL/6 마우스 (Taconic Farm, Inc)로부터 회수하여 사용하였다. The ginsenoside compound used for the test was dissolved in DMSO. Bone marrow-derived dendritic cells were recovered from wild-type C57BL / 6 mice (Taconic Farm, Inc) and used.
마우스의 정강이뼈(tibia)와 대퇴골(femur)로부터 DMEM (Invitrogen) 배지로 분사하여 골수를 회수한 후, 골수세포를 GM-CSF를 포함하는 3% J558L 림프잡종세포종 세포배양 상청액(hybridoma cell culture supernatant)이 함유된 RPMI 1640 medium (10% heat-inactivated FBS, 50 μM의 2-ME, 및 2 mM의 글루타민)에 세포배양을 실시하였다. GM-CSF 가 포함된 위 배양배지로 이틀에 한 번씩 배지를 교환하였다. 6일 후 비부착세포와 느슨하게 부착된(loosely adherent) 수지상세포를 회수하여 RPMI 1640 (5% FBS)에 현탁하였다. 수지상세포(DCs)를 48-well plates에 1×105 cells/mL로 분주한 후 본 발명의 화학식 1의 구조를 갖는 진세노사이드를 5 에서 50 μM 농도로 1 시간 전처리한 후 Salmonella minnesota 유래 LPS(Alexis, 10 ng/mL)를 추가 처리하였다. 18시간 후에 세포배양 상청액을 회수하여 마우스 인터루킨-12 중 IL-12B(p40)의 양을 ELISA (BD PharMingen)법으로 측정하였다. 모든 실험은 3번 반복실험하였고 데이터는 3번 반복실험으로부터 얻어진 측정값의 평균 ± 표준편차 (standard deviation)로 나타내었다. After bone marrow was recovered by spraying the tibia and femur from the mouse with DMEM (Invitrogen) medium, the bone marrow cells were harvested from a 3% J558L lymphoma cell tumor supernatant containing GM-CSF. RPMI 1640 medium (10% heat-inactivated) FBS, 50 μM 2-ME, and 2 mM glutamine) were cultured. GM-CSF With Medium was changed every two days with the above culture medium. Six days later, non-adherent cells and loosely adherent dendritic cells were recovered and suspended in RPMI 1640 (5% FBS). After dispensing dendritic cells (DCs) in 48-well plates at 1 × 10 5 cells / mL, Salmonella after pretreatment of ginsenosides having the structure of
결과를 도 1에 나타내었다. 0.1% DMSO로 처리한 수지상세포의 IL-12B(p40) 생산량을 100%로 표시하였다.The results are shown in Fig. IL-12B (p40) production of dendritic cells treated with 0.1% DMSO was expressed as 100%.
도 1을 참조하면, 본 발명의 진세노사이드가 LPS 로 자극한 수지상세포의 IL-12 생산을 상당한 수준으로 저해하는 효과를 가짐을 알 수 있다(IC50 = 16.3).
Referring to Figure 1, it can be seen that the ginsenoside of the present invention has an effect of inhibiting the IL-12 production of LPS-stimulated dendritic cells to a significant level (IC 50 = 16.3).
<< 비교예Comparative example 1> 인터루킨-12 생산 저해 활성 평가 1> Evaluation of inhibitory activity of interleukin-12 production
비교예 1에서는 본 발명의 진세노사이드를 사용하지 않고, 공지의 화합물인 20 μM의 진세노사이드(ginsenoside) Rg1, 진세노사이드(ginsenoside) Km, 진세노사이드(ginsenoside) Ⅱ, 플로랄진세노사이드(floralginsenoside) Kd 및 플로랄진세노사이드(floralginsenoside) Ke를 사용하였다. 그 외에는 실시예 1과 동일하게 실험하였다.
In Comparative Example 1, without using the ginsenoside of the present invention, 20 μM of the known compound ginsenoside Rg1, ginsenoside Km, ginsenoside II, floral ginsenoside (floralginsenoside) Kd and floralginsenoside Ke were used. Other experiments were carried out in the same manner as in Example 1.
비교예의 결과를 도 2에 나타내었다. 0.1% DMSO로 처리한 수지상세포의 IL-12B(p40) 생산량을 100%로 표시하였다.The result of the comparative example is shown in FIG. IL-12B (p40) production of dendritic cells treated with 0.1% DMSO was expressed as 100%.
도2를 참조하면, 20 μM 의 공지의 화합물인 진세노사이드(ginsenoside) Rg1, 진세노사이드(ginsenoside) Km, 진세노사이드(ginsenoside) Ⅱ, 플로랄진세노사이드(floralginsenoside) Kd 및 플로랄진세노사이드(floralginsenoside) Ke는 LPS로 자극한 수지상세포의 IL-12 생산을 저해하지 못하는 것을 알 수 있었다.
Referring to Figure 2, 20 μM of known compounds ginsenoside Rg1, ginsenoside Km, ginsenoside II, floralginsenoside Kd and floral ginsenosides Ke (floralginsenoside) did not inhibit IL-12 production of LPS-stimulated dendritic cells.
<< 실시예Example 3> 인터루킨-6 생산 저해 활성 평가 3> Evaluation of inhibitory activity of interleukin-6 production
실시예 3에서는 IL-12B(p40)를 대상으로 하지 않고, 인터루킨-6을 대상으로 ELISA(BD PharMingen)법을 수행한 것 외에는 실시예 2와 동일하게 실험하였다. 또한 본 발명의 진세노사이드 외에 공지의 화합물인 플로랄진세노사이드(floralginsenoside) J를 대상으로 비교 실험을 수행하였다. In Example 3, the test was carried out in the same manner as in Example 2, except that ELISA (BD PharMingen) was performed on interleukin-6 without targeting IL-12B (p40). In addition to the ginsenoside of the present invention, a comparative experiment was performed on a known compound, floralginsenoside J.
결과를 도 3에 나타내었다. 0.1% DMSO로 처리한 수지상세포의 인터루킨-6 생산량을 100%로 표시하였다.The results are shown in FIG. Interleukin-6 production of dendritic cells treated with 0.1% DMSO was expressed as 100%.
도 3을 참조하면, 본 발명의 진세노사이드가 LPS 로 자극한 수지상세포의 IL-6 생산을 상당한 수준으로 저해하는 효과를 가짐을 알 수 있다.
3, it can be seen that the ginsenoside of the present invention has an effect of inhibiting IL-6 production of LPS-stimulated dendritic cells to a significant level.
<< 실시예Example 4> 4> TNFTNF -α 생산 저해 활성 평가-α production inhibitory activity evaluation
실시예 4에서는 IL-12B(p40)를 대상으로 하지 않고, TNF-α 을 대상으로 ELISA(BD PharMingen)법을 수행한 것 외에는 실시예 2와 동일하게 실험하였다. 또한 본 발명의 진세노사이드 외에 공지의 화합물인 플로랄진세노사이드(floralginsenoside) J를 대상으로 비교 실험을 수행하였다. In Example 4, the test was performed in the same manner as in Example 2, except that ELISA (BD PharMingen) was performed on TNF-α without targeting IL-12B (p40). In addition to the ginsenoside of the present invention, a comparative experiment was performed on a known compound, floralginsenoside J.
결과를 도4에 나타내었다. 0.1% DMSO로 처리한 수지상세포의 TNF-α 생산량을 100%로 표시하였다.The results are shown in FIG. TNF-α production of dendritic cells treated with 0.1% DMSO was expressed as 100%.
도 4를 참조하면, 본 발명의 진세노사이드가 LPS 로 자극한 수지상세포의 TNF-α 생산을 상당한 수준으로 저해하는 효과를 가짐을 알 수 있다.
4, it can be seen that the ginsenoside of the present invention has an effect of inhibiting TNF-α production of LPS-stimulated dendritic cells to a significant level.
이상으로 본 발명의 특정한 부분을 상세히 기술하였는 바, 당업계의 통상의 지식을 가진 자에게 있어서, 이러한 구체적 기술은 단지 바람직한 실시예일 뿐이며, 이에 의해 본 발명의 범위가 제한되는 것이 아닌 점은 명백할 것이다. 따라서, 본 발명의 실질적인 범위는 첨부된 청구항들과 그것들의 등가물에 의하여 정의된다고 할 것이다.
Having described the specific parts of the present invention in detail, it will be apparent to those skilled in the art that such specific descriptions are merely preferred embodiments, and thus the scope of the present invention is not limited thereto. will be. Thus, the substantial scope of the present invention will be defined by the appended claims and their equivalents.
Claims (14)
[화학식 1]
Ginsenosides having the structure of Formula I:
[Formula 1]
상기 인삼 추출물에 극성 용매를 가하고 비극성 용매로 분획하여 극성 용매층을 분리하는 단계; 및
상기 극성 용매층으로 컬럼 크로마토그라피를 실시하는 단계를 포함하는 인삼으로부터 제1항의 진세노사이드를 추출하는 방법.
Extracting ginseng with water, alcohol or a mixed solvent of water and alcohol and concentrating under reduced pressure to obtain a ginseng extract;
Adding a polar solvent to the ginseng extract and fractionating the non-polar solvent to separate the polar solvent layer; And
The method of extracting ginsenoside of claim 1 from ginseng comprising the step of performing column chromatography with the polar solvent layer.
A pharmaceutical composition for preventing and treating autoimmune diseases comprising the ginsenoside of claim 1 as an active ingredient.
담체, 부형제, 붕해제, 감미제, 피복제, 팽창제, 윤활제, 활택제, 향미제, 항산화제, 완충액, 정균제, 희석제, 분산제, 계면활성제, 결합제 및 윤활제로 이루어진 군에서 선택되는 하나 이상의 첨가제를 추가로 포함하는 자가 면역 질환의 예방 및 치료용 의약 조성물.
The method of claim 3,
Add one or more additives selected from the group consisting of carriers, excipients, disintegrants, sweeteners, coatings, swelling agents, lubricants, lubricants, flavoring agents, antioxidants, buffers, bacteriostatic agents, diluents, dispersants, surfactants, binders and lubricants Pharmaceutical composition for the prevention and treatment of autoimmune diseases, including.
상기 자가 면역 질환의 예방 및 치료용 의약 조성물의 제형은 과립제, 산제, 피복정, 정제, 환제, 캡슐제, 좌제, 겔, 시럽, 즙, 현탁제, 유제, 점적제 또는 액제로 이루어진 군에서 선택되는 것인 자가 면역 질환의 예방 및 치료용 의약 조성물.
The method according to claim 3 or 4,
Formulation of the pharmaceutical composition for the prevention and treatment of autoimmune diseases is selected from the group consisting of granules, powders, coated tablets, tablets, pills, capsules, suppositories, gels, syrups, juices, suspensions, emulsions, drops or solutions. Pharmaceutical composition for the prevention and treatment of autoimmune diseases.
상기 자가 면역 질환은 다발성 경화증(MS, multiple sclerosis), 건선, 류마티스 관절염, 크론병(Chrohn's disease), 궤양성 대장염, 제 I 형 당뇨병(diabetes mellitus), 염증성 장질환, 또는 전신성 루프스인 자가 면역 질환의 예방 및 치료용 의약 조성물.
The method of claim 3,
The autoimmune disease is MS, multiple sclerosis, psoriasis, rheumatoid arthritis, Crohn's disease, ulcerative colitis, type I diabetes, diabetes mellitus, inflammatory bowel disease, or systemic lupus autoimmune disease Pharmaceutical composition for prophylaxis and treatment.
A pharmaceutical composition for the prevention and treatment of sepsis comprising the ginsenoside of claim 1 as an active ingredient.
담체, 부형제, 붕해제, 감미제, 피복제, 팽창제, 윤활제, 활택제, 향미제, 항산화제, 완충액, 정균제, 희석제, 분산제, 계면활성제, 결합제 및 윤활제로 이루어진 군에서 선택되는 하나 이상의 첨가제를 추가로 포함하는 패혈증의 예방 및 치료용 의약 조성물.
The method of claim 7, wherein
Add one or more additives selected from the group consisting of carriers, excipients, disintegrants, sweeteners, coatings, swelling agents, lubricants, lubricants, flavoring agents, antioxidants, buffers, bacteriostatic agents, diluents, dispersants, surfactants, binders and lubricants Pharmaceutical composition for the prevention and treatment of sepsis, including.
상기 패혈증의 예방 및 치료용 의약 조성물의 제형은 과립제, 산제, 피복정, 정제, 환제, 캡슐제, 좌제, 겔, 시럽, 즙, 현탁제, 유제, 점적제 또는 액제로 이루어진 군에서 선택되는 것인 패혈증의 예방 및 치료용 의약 조성물.
The method according to claim 7 or 8,
The formulation of the pharmaceutical composition for the prevention and treatment of sepsis is selected from the group consisting of granules, powders, coated tablets, tablets, pills, capsules, suppositories, gels, syrups, juices, suspensions, emulsions, drops or solutions. Pharmaceutical composition for the prevention and treatment of phosphorus sepsis.
A food composition comprising the ginsenoside of claim 1 as an active ingredient.
유기산, 인산염, 항산화제, 유당 카제인, 덱스트린, 포도당, 설탕 및 솔비톨로 이루어진 군에서 선택되는 하나 이상의 첨가제를 추가로 포함하는 식품 조성물.
The method of claim 10,
A food composition further comprising at least one additive selected from the group consisting of organic acids, phosphates, antioxidants, lactose casein, dextrins, glucose, sugars and sorbitol.
상기 식품 조성물의 제형은 분말, 과립, 정제, 캡슐 또는 음료 형태인 식품 조성물.
The method according to claim 10 or 11, wherein
The formulation of the food composition is a food composition in the form of a powder, granules, tablets, capsules or beverages.
Cosmetic composition comprising the ginsenoside of claim 1 as an active ingredient.
비타민, 계면활성제, 유화제, 향료, 색소, 안정제, 방부제, 항산화제, 자외선 차단제, pH 조정제 및 킬레이트제로 이루어진 군에서 선택되는 하나 이상의 첨가제를 추가로 포함하는 화장료 조성물.
The method of claim 13,
Cosmetic composition further comprising at least one additive selected from the group consisting of vitamins, surfactants, emulsifiers, perfumes, pigments, stabilizers, preservatives, antioxidants, sunscreens, pH adjusters and chelating agents.
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