KR20090022928A - Composition for curing sepsis comprising compound k - Google Patents
Composition for curing sepsis comprising compound k Download PDFInfo
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- KR20090022928A KR20090022928A KR1020070088626A KR20070088626A KR20090022928A KR 20090022928 A KR20090022928 A KR 20090022928A KR 1020070088626 A KR1020070088626 A KR 1020070088626A KR 20070088626 A KR20070088626 A KR 20070088626A KR 20090022928 A KR20090022928 A KR 20090022928A
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Abstract
Description
본 발명은 화합물 K를 함유하는 패혈증 치료용 조성물에 관한 것으로, 더욱 구체적으로 하기 화학식 1로 표시되는 화합물 K (Compound K)를 유효성분으로 함유하는 패혈증 치료용 조성물에 관한 것이다.The present invention relates to a composition for treating sepsis containing Compound K, and more particularly, to a composition for treating sepsis containing Compound K (Compound K) represented by Formula 1 as an active ingredient.
그람 음성 균에 의한 패혈증(Gram-negative sepsis)은 병원의 중환자실에서의 주된 사망 원인중의 하나이며, 그 빈도가 세계적으로 계속 증가하는데 이는 침투경로의 빈도증가와 면역억제로 이어지는 치료에 기인된다. 이 증상은 내피세포의 손상, 응고장애, 혈관긴장 소멸, 조직 hypoperfusion, 여러 기관의 기능저하로 특징된다. 이런 현상은 미생물이 생산한 물질에 기인한 조절할 수 없는 거대한 염증 반응의 결과이다. 이들 물질로는 LPS (lipopolysaccharide) 이라 불리는 내 독소를 들 수 있는데 그람 음성 세균의 외막의 구성요소이고, 전 염증성 사이토카인의 생산을 야기한다. 항생제의 투여 외에는 패혈증에 대한 치료는 아주 제한적이다. 그 러므로 패혈증에 걸린 숙주의 생존율을 높이고 전신적인 염증을 억제하는 물질의 발견은 아주 크게 요구되고 있다.Gram-negative sepsis is one of the leading causes of death in the intensive care unit of hospitals, and its frequency continues to increase worldwide due to increased frequency of infiltration pathways and treatments that lead to immunosuppression. . This symptom is characterized by damage to endothelial cells, coagulation disorders, vasospasm, tissue hypoperfusion, and impaired function of various organs. This is the result of a massive, uncontrolled inflammatory response due to the substances produced by the microorganisms. These substances include endotoxins called lipopolysaccharides (LPS), which are components of the outer membrane of Gram-negative bacteria and cause the production of proinflammatory cytokines. Except for the administration of antibiotics, treatment for sepsis is very limited. Therefore, there is a great demand for finding a substance that improves the survival rate of sepsis hosts and suppresses systemic inflammation.
인삼은 오래 전부터 건강을 위해 사용되어 왔다. 인삼의 약리효능을 나타내는 성분은 진세노사이드(ginsenosides)로 여러 가지의 생물학적 효능을 나타내는데, 그 예로 항염증, 항종양 등을 들 수 있다. 이들 진세노사이드 중 진세노사이드 Rb1, Rb2, Rc 및 Rd는 장내세균에 의해 대사되어 화합물 K(compound K, C-K; 도 1)로 전환되어 이용된다.Ginseng has long been used for health. Ingredients that indicate the pharmacological efficacy of ginseng are ginsenosides (ginsenosides), which exhibit various biological effects, such as anti-inflammatory and anti-tumor. Among these ginsenosides, ginsenosides Rb1, Rb2, Rc and Rd are metabolized by enterobacteria and converted to compound K (compound K, C-K; FIG. 1).
화합물 K (20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol)는 프로토파낙사디올 진세노사이드(protopanaxadiol ginsenoside) 대사체로서 생체 내 또는 생체 외에서 여러 가지 다양한 면역관계 약리작용 (Wakabayashi C, 1998, Hasegawa H, 1995, Lee SJ, 1999), 항알러지 효과(Bae EA, Choo MK, 2003, Kim DH, 2003, Lee JH, 2006) 등을 나타낸다. 여러 연구 결과에서 몇몇의 진세노사이드는 글루코코티코이드-유사 활성(glucocorticoid-like activity)을 보이는데, 글루코코티코이드 수용체(glucocorticoid receptor, GR)를 직간접적으로 활성화 시킨다 (Lee YJ, 1997, Lee YN, 1996). 다른 연구에 의하면 toll like receptor 4 (TLR4)와 GR 상호간의 작용에 의하여 항상성과 면역작용간의 조화로운 조절로 염증성 질환의 새로운 치료방법이 제시되고 있다 (Ogawa S, 2005).Compound K (20-O-beta-D-glucopyranosyl-20 (S) -protopanaxadiol) is a metabolite of protopanaxadiol ginsenoside, which acts as a variety of immunological pharmacological agents (Wakabayashi C). , 1998, Hasegawa H, 1995, Lee SJ, 1999), anti-allergic effects (Bae EA, Choo MK, 2003, Kim DH, 2003, Lee JH, 2006). Several studies have shown that some ginsenosides exhibit glucocorticoid-like activity, which directly or indirectly activates the glucocorticoid receptor (GR) (Lee YJ, 1997, Lee YN, 1996). Other studies have suggested a novel treatment for inflammatory diseases by harmonizing control between homeostasis and immune action by interactions between toll like receptor 4 (TLR4) and GR (Ogawa S, 2005).
본 발명은 내독소에 의해 야기된 반응을 화합물 K가 조절하는 사실을 발견하여 치명적인 패혈증을 치료하는 새로운 치료제로서의 가능성을 설명하고자 한다. 화합물 K의 전처리와 후처리가 그람음성 박테리아의 LPS에 의해 야기된 패혈증이 유도된 마우스의 생존을 회복시키는 결과와 이를 통한 생체 내 전신성 염증반응을 화합물 K가 조절한다는 사실을 발견하였다. 따라서 본 발명은 화합물 K가 항염증과 항패혈증의 효과를 나타낸다는 사실을 확인하였다.The present invention seeks to explain the potential of a novel therapeutic agent to treat fatal sepsis by discovering the fact that Compound K modulates the response caused by endotoxin. It was found that pretreatment and posttreatment of Compound K resulted in the recovery of survival of sepsis-induced mice caused by LPS of Gram-negative bacteria, and that Compound K regulates systemic inflammatory responses in vivo. Therefore, the present invention confirmed that the compound K shows the effects of anti-inflammatory and anti-septicemia.
이에, 본 발명자들은 상기 종래기술들의 문제점들을 극복하기 위하여 예의 연구노력한 결과, 홍삼 사포닌 전환체인 화합물 K (Compound K)가 그람 음성균에 의한 패혈증 및 패혈증 쇼크에 있어서, 항패혈증 효과가 우수함을 확인하고, 본 발명을 완성하게 되었다.Accordingly, the present inventors have made intensive studies to overcome the problems of the prior art, and as a result, the compound K (Compound K), which is a red ginseng saponin convertor, confirmed that the antiseptic effect was excellent in sepsis and sepsis shock caused by Gram-negative bacteria, The present invention was completed.
따라서, 본 발명의 주된 목적은 항패혈증 효능을 갖는 홍삼 사포닌 전환체인 화합물 K (Compound K)를 유효성분으로 함유하는 조성물을 제공하는 데 있다.Therefore, the main object of the present invention is to provide a composition containing Compound K (Compound K) which is a red ginseng saponin convertor having antiseptic efficacy as an active ingredient.
본 발명의 한 양태에 따르면, 본 발명은 하기 화학식 1로 표시되는 화합물 K (Compound K)를 유효성분으로 함유하는 패혈증 치료용 조성물을 제공한다. 본 발명에서는 종래 알려져 있는 진사노사이드 대사체로 알려져 있는 화합물 K의 새로운 용도, 즉 화합물 K의 항패혈증 효과를 밝혔다.According to one embodiment of the present invention, the present invention provides a composition for treating sepsis, which contains Compound K (Compound K) represented by the following Chemical Formula 1 as an active ingredient. In the present invention, a novel use of compound K, known as the cinnanoside metabolite, known in the art, namely, the anti-septic effect of compound K was disclosed.
[화학식 1][Formula 1]
본 발명의 조성물에서, 상기 화합물 K는 홍삼 사포닌인 진세노사이드 Rb1, Rb2, Rc 또는 Rd로 부터의 전환체인 것을 특징으로 한다. 본 발명의 화합물 K는 홍삼에는 없는 물질로 홍삼사포닌이 장내세균에 의해 전환되어 소량 생성되는 사포닌 전환체이다. 본 발명의 실시예에서는 화합물 K를 프로토파낙사디올 타입 사포닌들 (진세노사이드 Rb1, Rb2, Rc 및 Rd)과 Aspergillus niger 유래 셀룰라아제를 인큐베이션함으로써 얻을 수 있었다. 기존의 알려진 화합물 K의 효능은 주로 항암 효과인 반면 본 발명에서 확인된 효능은 항패혈증으로, 약제학적 조성물로서의 이용이 가능하다.In the composition of the present invention, the compound K is characterized in that the red ginseng saponin ginsenosides Rb1, Rb2, Rc or a conversion from Rd. Compound K of the present invention is a substance not found in red ginseng, and is a saponin convertor in which red ginseng saponin is converted by enterobacteriaceae. In the examples of the present invention, compound K can be obtained by incubating protophanaxadiol type saponins (ginsenosides Rb1, Rb2, Rc and Rd) with Aspergillus niger derived cellulase. While the efficacy of known compounds K is primarily an anticancer effect, the efficacy identified in the present invention is anti sepsis, which can be used as a pharmaceutical composition.
본 발명의 조성물에서, 상기 패혈증은 바람직하게는 그람 음성균의 LPS에 의해 유발되는 것을 특징으로 한다. 본 발명의 실시예에서는 패혈증의 한 형태인 그람 음성균에 의한 패혈증(Gram-negative sepsis)을 그람 음성균의 LPS로 처리하여유발시킨 뒤, 본 발명의 화합물 K를 투여하여 항패혈증 효과를 확인하였다.In the composition of the present invention, the sepsis is characterized in that it is preferably caused by LPS of Gram-negative bacteria. In an embodiment of the present invention, Gram-negative sepsis caused by Gram-negative bacteria was induced by LPS of Gram-negative bacteria, which is a form of sepsis, and then the compound K of the present invention was administered to confirm the anti-septic effect.
본 발명의 조성물이 약제학적 조성물로 이용되기 위해서는 약제학적 분야에서 공지된 방법에 의해 제조될 수 있으며, 그 자체 또는 약학적으로 허용되는 담체, 부형제, 희석제 등과 혼합하여 분말, 과립, 정제, 캡슐제 또는 주사제 등의 제형으로 제조되어 사용될 수 있다. 또한 이들은 경구 또는 비경구로 투여될 수 있다.In order to use the composition of the present invention as a pharmaceutical composition can be prepared by a method known in the pharmaceutical field, powders, granules, tablets, capsules by themselves or mixed with a pharmaceutically acceptable carrier, excipient, diluent, etc. Or in the form of an injection or the like. They can also be administered orally or parenterally.
본 발명에 따른 화합물 K를 유효성분으로서 투여하는 투여량은 환자의 연령, 성별, 상태, 질병의 증상에 따라 적절히 선택될 수 있으며, 바람직하게는 1일 0.01 내지 100 mg/kg(체중)의 화합물 K가 투여될 수 있다.The dosage for administering Compound K according to the present invention as an active ingredient may be appropriately selected according to the age, sex, condition, and symptoms of the disease of the patient, and preferably 0.01 to 100 mg / kg (body weight) of compound per day. K may be administered.
이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하기로 한다. 이들 실시예는 단지 본 발명을 예시하기 위한 것이므로, 본 발명의 범위가 이들 실시예에 의해 제한되는 것으로 해석되지는 않는다.Hereinafter, the present invention will be described in more detail with reference to Examples. Since these examples are only for illustrating the present invention, the scope of the present invention is not to be construed as being limited by these examples.
이상 설명한 바와 같이, 본 발명에 따르면 홍삼 사포닌인 진사노사이드의 대사체인 화합물 K를 효소를 이용하여 얻을 수 있으며, 이러한 화합물 K는 인체 흡수가 용이하고 안정성이 이미 검증되어 있다. 본 발명은 화합물 K의 새로운 용도로서 패혈증이 유발된 마우스에서 항패혈증 효과가 우수함을 확인하여 패혈증 치료를 위한 약제학적 조성물로서의 활용 가능성을 제시하고 있다.As described above, according to the present invention, compound K, which is a metabolite of ginsanoside, which is red ginseng saponin, can be obtained by using an enzyme, and this compound K is easily absorbed by humans and its stability has already been verified. The present invention confirms the excellent anti-septic effect in sepsis-induced mice as a new use of compound K, suggesting the possibility of use as a pharmaceutical composition for the treatment of sepsis.
실시예 1. 화합물 K의 제조 및 분리Example 1. Preparation and Separation of Compound K
진세노사이드 대사물의 하나인 화합물 K는 다음과 같이 분리하였다. 프로토파낙사디올 타입 사포닌 1g(진세노사이드 Rb1, Rb2, Rc 및 Rd, KT&G 중앙연구원에서 자체분리)을 Aspergillus niger 유래 셀룰라아제(cellulase)와 37℃에서 48시간 동간 인큐베이션하였다. 반응물은 n-부탄올로 추출하고, 부탄올 분획을 농축한 후, 클로로포름-메탄올 (9:1)을 이동상으로 사용하여 실리카 겔 컬럼에서 화합물 K를 분리한 후 다시 ODS(C18) 컬럼을 사용하여 크로마토그래피를 수행하였다. 정제물은 HPLC(Waters HPLC system)로 분석하였다: column, Discovery C18(25× 0.46cm, 5um, Supelco); elution solvent, solvent A(water) and solvent B(acetonitrile)-gradient profile of solvent A to solvent B; from 80: 20 to 10: 90 for 0-90 min.; Detector, UV 203nm. 분리된 화합물 K는 13C-NMR, 1H-NMR, HPLC, FAB-MS를 사용하여 동정하였으며, 화합물 K의 순도는 97% 이상이었다.Compound K, one of the ginsenoside metabolites, was isolated as follows. 1 g of protopanaxadiol-type saponin (ginsenoside Rb1, Rb2, Rc and Rd, self-separated from KT & G Central Research Institute) was incubated with Aspergillus niger derived cellulase (cellulase) for 48 hours at 37 ° C. The reaction was extracted with n-butanol, the butanol fraction was concentrated, the compound K was separated from the silica gel column using chloroform-methanol (9: 1) as the mobile phase and chromatographed again using an ODS (C18) column. Was performed. Purification was analyzed by HPLC (Waters HPLC system): column, Discovery C 18 (25 × 0.46 cm, 5um, Supelco); elution solvent, solvent A (water) and solvent B (acetonitrile) -gradient profile of solvent A to solvent B; from 80: 20 to 10: 90 for 0-90 min .; Detector, UV 203 nm. The separated compound K was identified using 13 C-NMR, 1 H-NMR, HPLC, FAB-MS, the purity of the compound K was more than 97%.
실시예 2. 실험동물 및 재료의 준비Example 2 Preparation of Experimental Animals and Materials
본 발명에 기술된 모든 실험은 C57BL/6 background를 가진 마우스를 사용하여 수행하였다. 모든 동물-관련 절차는 충남대학교의 Institutional Animal Care and Use Committee의 가이드라인에 따라 수행하였다. 마우스는 8-10주령을 LPS 시험에 사용하였다. 시험군을 나이와 성별로 분류하였다. Escherichia coli O26:B6 LPS(Sigma-Aldrich)를 멸균 PBS에서 희석한 뒤, 동물의 복강 내로 주사하였다.All experiments described herein were performed using mice with a C57BL / 6 background. All animal-related procedures were performed in accordance with the guidelines of the Institutional Animal Care and Use Committee of Chungnam National University. Mice were used for the LPS test at 8-10 weeks of age. Test groups were classified by age and gender. Escherichia coli O26: B6 LPS (Sigma-Aldrich) was diluted in sterile PBS and injected into animals intraperitoneally.
실시예 3. 패혈증 마우스 모델을 이용한 화합물 K(C-K)의 효능 분석Example 3 Efficacy Analysis of Compound K (C-K) Using Sepsis Mouse Model
C-K(화합물 K)가 생체 내에서 내 독소에 의한 패혈증에 효과가 있는지를 알기 위해 murine 패혈증 모델을 구축하였다. C57B/L6 마우스(group 당 25 마리씩)에 대하여 CK (10, 30 및 50 mg/kg)를 구강투여 하였다. 1일 후 그람음성균 내독소(LPS)를 복강 내로 40mg/kg(체중) 주사하여 패혈성 쇼크를 유발하였다. 그 후 5일간의 생존율을 조사하였다.To determine whether C-K (Compound K) is effective in endotoxin-induced sepsis in vivo, a murine sepsis model was constructed. CK (10, 30 and 50 mg / kg) was orally administered to C57B / L6 mice (25 per group). One day later, gram-negative bacterial endotoxin (LPS) was injected into the abdominal cavity by 40 mg / kg (body weight) to cause septic shock. The survival rate was then examined for 5 days.
40 mg/kg의 LPS는 대조군을 90% 사망케 하였으나, C-K를 경구투여 할 경우 LPS-주사된 마우스를 농도-의존적으로 생존율을 증가시켰다. 가장 고농도 시험군(50 mg/kg)에서는 85%가 생존하였고, 30 mg/kg에서도 50%가 생존하였다 (P < 0.05) (도 2).LPS at 40 mg / kg caused 90% death of the control group, but LPS-injected mice increased the survival rate concentration-dependently when C-K was orally administered. 85% survived in the highest concentration test group (50 mg / kg) and 50% survived even at 30 mg / kg (P <0.05) (FIG. 2).
실시예 4. C-K의 내독소 유래 치명적인 쇼크(lethal shock)의 억제 효과Example 4 Inhibitory Effects of C-K on Endotoxin-Derived Lethal Shock
C-K가 LPS에 의해 야기된 내독소 쇼크로부터 마우스를 보호할 수 있는 지를 조사하였다. 마우스를 여러 그룹으로 나누고, 40 mg/kg의 LPS농도로 복강내(i.p.)로 주사하였다. LPS가 40 mg/kg body weight로 주사하였을 경우 대조군에서는 40시간 내에 100 %가 사망하였다 (n = 25). 이 때 C-K를 6 시간 후에 투여하였을 경우 100시간 동안 70%가 생존함을 관찰할 수 있었다 (도 3a). 다른 군에서는 LPS를 30 mg/kg body weight로 투여한 경우 대조군에서의 사망률은 70%인데, C-K를 처리하였을 경우 유의하게 생존율이 증가하였다 (도 3b)(P < 0.006). 이런 결과는 C-K가 그람음성균에 의한 패혈증 쇼크(gram-negative septic shock)를 치료하는 새로운 치료제로서의 가능성을 제시하고 있다.It was investigated whether C-K can protect mice from endotoxin shock caused by LPS. Mice were divided into groups and injected intraperitoneally (i.p.) at an LPS concentration of 40 mg / kg. Injecting LPS at 40 mg / kg body weight resulted in 100% death within 40 hours in the control group (n = 25). At this time, when C-K was administered after 6 hours, it was observed that 70% survived for 100 hours (FIG. 3A). In the other group, the LPS administered at 30 mg / kg body weight was 70% mortality in the control group, but significantly increased survival when treated with C-K (FIG. 3B) (P <0.006). These results suggest that C-K may be a novel therapeutic for the treatment of gram-negative septic shock.
도 1은 본 발명의 화합물 K의 화학식이다.1 is a chemical formula of compound K of the present invention.
도 2는 본 발명의 화합물 K가 생체 내에서 내 독소에 의한 패혈증에 대한 효과를 나타낸 것이다.Figure 2 shows the effect of Compound K of the present invention on sepsis caused by endotoxin in vivo.
도 3은 본 발명의 화합물 K의 내독소 유래 치명적인 쇼크(lethal shock)의 억제 효과를 나타낸 것이다.Figure 3 shows the inhibitory effect of endotoxin-derived lethal shock of compound K of the present invention.
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KR101952951B1 (en) | 2018-11-18 | 2019-02-28 | 주식회사 아리바이오 | Production method of black yeast culture liquid containing compound k, functional cosmetic and compound containing compound k |
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KR101401658B1 (en) * | 2011-06-16 | 2014-06-02 | 한국생명공학연구원 | Antibiotic consisting of ginsenoside compound K or derivatives thereof |
KR101300775B1 (en) | 2013-01-30 | 2013-08-29 | 경희대학교 산학협력단 | Composition for preventing and treating of neuropathic pain containing ginsenoside Rb1 and Rg3,Compound K,or saponin extract from Panax ginseng as an effective ingredient |
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