KR20100041020A - A method for preparing the derivative of rhein which have a boosting anticancer activity from sennoside a using irradiation - Google Patents
A method for preparing the derivative of rhein which have a boosting anticancer activity from sennoside a using irradiation Download PDFInfo
- Publication number
- KR20100041020A KR20100041020A KR1020080099996A KR20080099996A KR20100041020A KR 20100041020 A KR20100041020 A KR 20100041020A KR 1020080099996 A KR1020080099996 A KR 1020080099996A KR 20080099996 A KR20080099996 A KR 20080099996A KR 20100041020 A KR20100041020 A KR 20100041020A
- Authority
- KR
- South Korea
- Prior art keywords
- cancer
- sennoside
- carcinoma
- derivative
- solution
- Prior art date
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Abstract
Description
본 발명은 방사선을 이용한 센노사이드 A로부터 항암효과 증진된 레인 유도체의 제조방법에 관한 것이다.The present invention relates to a method for preparing an anti-cancer effect-enhanced derivative from sennoside A using radiation.
식품의 방사선 조사기술은 국내에서 일반적으로 살균목적으로 많이 사용되고 있는데 이외에도 물성개선, 불순물제거 등의 다양한 효과가 검증되고 있다. 감마선 조사는 코발트-60 방사성 동위원소에서 나오는 단파장 빛인 감마선을 식품이나 의료용품 등에 쬐어 치명적인 전염병 세균들이나 기생충 및 해충들을 완전히 사멸시킬 수 있는 유익하고 효과적인 기술이다. 감마선은 수 센티미터의 콘크리트를 투과할 정도로 고(高) 침투력을 가진 파장이기 때문에 식품 및 보건의료제품을 완전 밀봉한 상태로 조사 처리하여도 무균제품을 생산할 수 있다. 코발트-60에서 방출되는 감마선은 전자와 같은 하전입자에 비하면 투과력이 강하기 때문에 액체나 고체의 내부까지 조사하는 데 적합하다. 의료기구 살균이나 식품조사 목적에는 코발트-60 선원이 이용되고 있다.Food irradiation technology is commonly used in Korea for sterilization purposes, and various effects such as physical property improvement and impurities removal have been verified. Gamma-irradiation is a beneficial and effective technique that can completely kill deadly infectious diseases, parasites and pests by irradiating gamma rays, short-wavelength light from cobalt-60 radioisotopes, on food and medical supplies. Gamma rays are wavelengths that have a high penetration enough to penetrate a few centimeters of concrete, so that sterile products can be produced even when the food and health care products are completely sealed. Gamma rays emitted from cobalt-60 are more permeable to charged particles, such as electrons, and thus are suitable for irradiation inside liquids or solids. Cobalt-60 sources are used for medical device sterilization and food research purposes.
대황(Rheum palmatum L.)의 성분에 대한 연구는 최근까지 계속되고 있는바, 센노사이드 A(sennoside A)에 의한 사하작용(瀉下作用), 소화기 점막손상방지, 알로에-에모딘(aloe-emodin), 에모딘(emodin) 및 레인(rhein)의 항균작용 등이 보고되어 있다(中華本草編纂委: 中華本草, 上海科學技術出版社, 제2권, pp.710, 715-716, 1999). 그 중, 센노사이드 A는 대황 및 센나잎의 주성분으로써 장내세균에 의해서 대사되어 사하작용 및 항암효과를 나타내는 안트라퀴논(anthraquinone) 계열의 화합물이다. 센노사이드 A는 Streptococcus 등의 β-글루코시다아제에 의해 두 개의 글루코오즈가 센노사이드 A 배당체로부터 절단되어 생성되며, 계속해서 Peptostreptococcus 등의 NAD(P)H-의존성 플라빈 효소(환원제)에 의해 생성된 환원형 플라빈이 C-C결합을 비효소적으로 분리시켜 레인안스론(rheinanthrone)이 생성된다. 레인안스론은 산화되기 쉬워서 호기적 조건에서 레인이 된다. 이렇게 생성된 화합물질이 암세포에서 글루코오스의 섭취를 저해시켜 암세포 증식을 억제하게 되고 세포막의 기능을 변화시켜 항암효과를 유발한다. 효소 및 장내미생물을 이용하여 센노사이드 A로부터 레인이 생성되는 과정을 도 1에 나타내었다. 이러한 방법은 수율이 높지 않고, 방법이 복잡하며, 비용이 많이 드는 단점이 있다.Studies on the components of Rheum palmatum L. have been conducted until recently, and the effects of sennoside A on lowering action, prevention of gastrointestinal mucosal damage, and aloe-emodin , Antibacterial effects of emodin and rhein have been reported (中華 本草 編纂 委, 上海 科學 技術 出版社, Vol. 2, pp.710, 715-716, 1999). Among them, sennoside A is an anthraquinone-based compound that is metabolized by enterobacteriaceae as a main component of rhubarb and senna leaves and has a lowering action and anticancer effect. Sennoside A is produced by cleaving two glucoses from sennoside A glycosides by β-glucosidase such as Streptococcus , followed by NAD (P) H-dependent flavin enzymes (reducing agents) such as Peptostreptococcus. Reduced flavin is non-enzymatically separated from the CC bonds to produce rheinanthrone. Lane anthrone is easy to oxidize, and becomes lane in aerobic conditions. Thus produced compound inhibits the ingestion of glucose in cancer cells to inhibit cancer cell proliferation and to change the function of the cell membrane to induce anti-cancer effect. 1 shows a process of generating a lane from sennoside A using an enzyme and an intestinal microorganism. This method is disadvantageous in that the yield is not high, the method is complicated, and expensive.
이에, 본 발명자들은 메탄올에 녹인 센노사이드 A에 과산화수소를 첨가하고 방사선을 조사하여 레인-8-β-D-글루코시드 구조로 전환을 유도한 결과, 높은 수율 로 레인 유도체를 생성할 수 있었고, 기존에 알려진 레인이나 알로에-에모딘에 비하여 항암효과가 더 높은 것을 확인함으로써 본 발명을 완성하였다.Accordingly, the present inventors added hydrogen peroxide to sennoside A dissolved in methanol, and irradiated with radiation to induce the conversion to the lane-8-β-D-glucoside structure, thereby generating a lane derivative in a high yield. The present invention was completed by confirming that the anticancer effect is higher than that of Lane or Aloe-Emodine.
본 발명의 목적은 센노사이드 A에 방사선을 조사하여 항암효과가 증진된 레인 유도체의 함유용액을 제조하는 방법을 제공하는 것이다.It is an object of the present invention to provide a method for preparing a solution containing a lane derivative having enhanced anticancer effect by irradiating sennoside A with radiation.
본 발명의 다른 목적은 상기 방법에 의해 제조되는 항암효과가 증진된 레인 유도체 함유용액을 제공하는 것이다.Another object of the present invention is to provide a rain derivative-containing solution having improved anticancer effect prepared by the above method.
본 발명의 다른 목적은 상기 항암효과가 증진된 레인 유도체 함유용액을 유효성분으로 함유하는 암 예방 및 치료용 약학적 조성물을 제공하는 것이다.It is another object of the present invention to provide a pharmaceutical composition for preventing and treating cancer, which contains a lane derivative-containing solution having an enhanced anticancer effect as an active ingredient.
본 발명의 다른 목적은 항암효과가 증진된 레인 유도체 함유용액을 유효성분으로 함유하는 암 예방 및 개선용 건강기능식품을 제공하는 것이다.Another object of the present invention to provide a health functional food for cancer prevention and improvement containing the rain derivative-containing solution with enhanced anticancer effect as an active ingredient.
상기 목적을 달성하기 위하여, 본 발명은 In order to achieve the above object, the present invention
1) 센노사이드 A를 포함하는 용액에 라디칼 생성제를 첨가하는 단계; 및,1) adding a radical generator to a solution comprising sennoside A; And,
2) 단계 1)의 처리 용액에 방사선을 조사하는 단계를 포함하는 항암효과가 증진된 레인 유도체 함유용액의 제조방법을 제공한다.2) It provides a method for producing a rain derivative-containing solution enhanced anticancer effect comprising the step of irradiating the treatment solution of step 1).
또한, 본 발명은 상기 방법에 의해 제조된, 항암효과가 증진된 레인 유도체 함유용액을 제공한다.In addition, the present invention provides a rain derivative-containing solution prepared by the above method, the anticancer effect enhanced.
또한, 본 발명은 상기 방법에 의해 제조된, 항암효과가 증진된 레인 유도체 함유용액을 유효성분으로 함유하는 암 예방 및 치료용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for preventing and treating cancer, which comprises a rain derivative-containing solution having an anticancer effect enhanced by the above method as an active ingredient.
아울러, 본 발명은 상기 방법에 의해 제조된, 항암효과가 증진된 레인 유도체 함유용액을 유효성분으로 함유하는 암 예방 및 개선용 건강기능식품을 제공한다.In addition, the present invention provides a health functional food for cancer prevention and improvement, which is prepared by the above method, containing an anti-cancer effect-enhanced rain derivative-containing solution as an active ingredient.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 The present invention
1) 센노사이드 A를 포함하는 용액에 라디칼 생성제를 첨가하는 단계; 및,1) adding a radical generator to a solution comprising sennoside A; And,
2) 단계 1)의 처리 용액에 방사선을 조사하는 단계를 포함하는 항암효과가 증진된 레인 유도체 함유용액의 제조방법을 제공한다.2) It provides a method for producing a rain derivative-containing solution enhanced anticancer effect comprising the step of irradiating the treatment solution of step 1).
본 발명의 구체적인 실시예에서는 50% 메탄올에 녹인 센노사이드 A 용액에 0.05%의 농도로 과산화수소를 첨가하여 방사선을 조사한 결과, 레인 유도체의 함량이 증가하는 것을 확인하였다(도 3 참조). 또한, 상기 센노사이드 A 자체에는 항암효과가 없으나, 본 발명에 의해 센노사이드 A가 전환되어 생성된 레인 유도체에서는 확연한 항암효과가 나타났으며(도 4 참조), 기존의 레인 유도체 표준물질보다 항암효과가 증가한 것을 확인하였다(도 5 참조). 이에 본 발명의 방법은 센노사이드 A로부터 항암효과가 증진된 레인 유도체의 제조에 유용하게 이용될 수 있다.In a specific embodiment of the present invention, as a result of irradiation with hydrogen peroxide at a concentration of 0.05% to the sennoside A solution dissolved in 50% methanol, the content of the lane derivative was increased (see FIG. 3). In addition, the sennoside A itself has no anti-cancer effect, but in the lane derivative produced by converting the sennoside A by the present invention showed a clear anti-cancer effect (see Figure 4), the anti-cancer effect than the conventional lane derivative standard It was confirmed that increased (see FIG. 5). Therefore, the method of the present invention can be usefully used for the preparation of a lane derivative having enhanced anticancer effect from sennoside A.
상기 방법에 있어서, 단계 1)의 센노사이드 A를 포함하는 용액은 센노사이드 A 단일물질을 용매에 녹인 것 또는 센노사이드 A를 주성분으로 포함하는 것으로 알 려진 식물, 예를 들면 대황 또는 센나잎의 분쇄액 또는 추출액 등이 있다. 상기 분쇄액은 건조된 대황 또는 센나잎의 분말을 물로 추출한 것을 나타내며, 추출액은 건조된 대황 또는 센나잎의 분말을 알코올 및 알코올 수용액으로 이루어진 군으로부터 선택된 용매를 이용하여 추출한 것을 의미한다. 상기 알코올은 C1 내지 C4 저급 알코올을 이용하는 것이 바람직하며, 저급 알코올로는 에탄올 또는 메탄올을 이용하는 것이 바람직하고, 가장 바람직하게는 상기 용매는 50% 메탄올 수용액이다.In the above method, the solution comprising sennoside A in step 1) is a pulverized plant, for example rhubarb or senna leaf, which is known to have dissolved the sennoside A single substance in a solvent or contains sennoside A as a main component. Liquids or extracts. The pulverized liquid indicates that the powder of dried rhubarb or senna leaves is extracted with water, and the extract liquid means that the powder of dried rhubarb or senna leaves is extracted using a solvent selected from the group consisting of alcohol and aqueous alcohol solution. The alcohol is preferably C 1 to C 4 lower alcohols, it is preferable to use ethanol or methanol as the lower alcohol, most preferably the solvent is a 50% methanol aqueous solution.
단계 1)의 라디칼 생성제에는 과산화수소, 과초산 또는 아스코르브산 등이 있다. 상기 센노사이드 A 용액에 대하여 0.02 내지 0.1 중량부로 첨가되는 것이 바람직하며, 가장 바람직하게는 0.05 중량부로 첨가된다.Radical generators of step 1) include hydrogen peroxide, peracetic acid or ascorbic acid and the like. It is preferably added in an amount of 0.02 to 0.1 parts by weight based on the Sennoside A solution, and most preferably 0.05 part by weight.
단계 2)의 방사선은 감마선, 전자선 또는 X-선을 모두 사용할 수 있으며, 감마선을 사용하는 것이 바람직하다.The radiation of step 2) may use either gamma rays, electron beams or X-rays, preferably gamma rays.
상기 감마선은 코발트(Co)-60, 크립톤(Kr)-85, 스트론튬(Sr)-90 또는 세슘(Cs)-137 등의 방사성 동위원소로부터 방출되는 감마선을 사용하여 조사는 것이 바람직하며, 코발트(Co)-60 방사선 동위원소로부터 방출되는 것이 더 바람직하나 이에 한정되지 않는다. 상기 방사선 조사 선량은 1-10 kGy인 것이 바람직하며, 1-5 kGy인 것이 더욱 바람직하고, 1 kGy인 것이 가장 바람직하다. 상기 방사선 조사 선량의 범위는 센노사이드 A로부터 생성된 레인 유도체가 모두 분해되어 없어질 정도보다 적고, 상기 진세노사이드가 변화되어 증강된 항암효과를 나타낼 수 있음을 기준으로 설정하였다.The gamma rays are preferably irradiated using gamma rays emitted from radioactive isotopes such as cobalt (Co) -60, krypton (Kr) -85, strontium (Sr) -90, or cesium (Cs) -137. More preferably, but not limited to, emission from Co) -60 radioisotopes. The irradiation dose is preferably 1-10 kGy, more preferably 1-5 kGy, and most preferably 1 kGy. The range of the radiation dose was set on the basis that the lane derivatives generated from Senosides A were less than decomposed and disappeared, and the ginsenosides could be changed to show an enhanced anticancer effect.
또한, 본 발명은 상기 방법에 의해 제조된, 항암효과가 증진된 레인 유도체 함유용액을 제공한다.In addition, the present invention provides a rain derivative-containing solution prepared by the above method, the anticancer effect enhanced.
본 발명의 구체적인 실시예에서 본 발명의 방법에 따라 센노사이드 A로부터 생성된 레인 유도체를 고효율로 생성할 수 있었다(도 3 참조). 또한 상기 센노사이드 A 자체에는 항암효과가 없으나, 본 발명에 의해 센노사이드 A가 전환되어 생성된 레인 유도체에서는 확연한 항암효과가 나타났으며(도 4 참조), 기존의 레인 유도체 표준물질보다 항암효과가 증가한 것을 확인하였다(도 5 참조). 이에 본 발명의 센노사이드 A로부터 항암효과가 증진된 레인 유도체를 고효율로 생성할 수 있고, 상기 레인 유도체의 항암 효과가 기존의 레인 표준물질보다 뛰어난 것을 확인하였다.In a specific embodiment of the present invention according to the method of the present invention it was possible to produce a lane derivative generated from sennoside A with high efficiency (see Figure 3). In addition, the sennoside A itself has no anticancer effect, but in the lane derivative produced by converting the sennoside A by the present invention showed a clear anticancer effect (see Figure 4), the anticancer effect than the conventional lane derivative standard It was confirmed that the increase (see Fig. 5). Accordingly, it was confirmed that the lane derivative having enhanced anticancer effect from the sennoside A of the present invention can be produced with high efficiency, and the anticancer effect of the lane derivative is superior to the existing lane standard.
또한, 본 발명은 상기 방법에 의해 제조된, 항암효과가 증진된 레인 유도체 함유용액을 유효성분으로 함유하는 암 예방 및 치료용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for preventing and treating cancer, which comprises a rain derivative-containing solution having an anticancer effect enhanced by the above method as an active ingredient.
본 발명의 구체적인 실시예에서 본 발명의 방법에 따라 센노사이드 A로부터 생성된 레인 유도체를 고효율로 생성할 수 있었다(도 3 참조). 또한 상기 센노사이드 A 자체에는 항암효과가 없으나, 본 발명에 의해 센노사이드 A가 전환되어 생성된 레인 유도체에서는 확연한 항암효과가 나타났으며(도 4 참조), 기존의 레인 유도체 표준물질보다 항암효과가 증가한 것을 확인하였다(도 5 참조). 이에 본 발명의 센노사이드 A로부터 생성된 항암효과가 증진된 레인 유도체의 함유용액은 암 예방 및 치료용 약학적 조성물로 유용하게 이용될 수 있다.In a specific embodiment of the present invention according to the method of the present invention it was possible to produce a lane derivative generated from sennoside A with high efficiency (see Figure 3). In addition, the sennoside A itself has no anticancer effect, but in the lane derivative produced by converting the sennoside A by the present invention showed a clear anticancer effect (see Figure 4), the anticancer effect than the conventional lane derivative standard It was confirmed that the increase (see Fig. 5). Accordingly, the solution containing the lane derivative having enhanced anticancer effect generated from sennoside A of the present invention may be usefully used as a pharmaceutical composition for preventing and treating cancer.
본 발명의 약학적 조성물은 아폽토시스에 의한 세포독성을 나타내며, ROS를 생성하므로, 간암, 위암, 유방암, 결장암, 골암, 췌장암, 두부 또는 경부암, 자궁암, 난소암, 직장암, 식도암, 소장암, 항문부근암, 결장암, 나팔관암종, 자궁내막암종, 자궁경부암종, 질암종, 음문암종, 호지킨병, 전립선암, 방광암, 신장암, 수뇨관암, 신장세포암종, 신장골반암종 및 중추신경계 종양 등의 다양한 암 질환의 예방 및 치료에 사용될 수 있다.The pharmaceutical composition of the present invention exhibits cytotoxicity due to apoptosis and produces ROS, and therefore, liver cancer, gastric cancer, breast cancer, colon cancer, bone cancer, pancreatic cancer, head or neck cancer, uterine cancer, ovarian cancer, rectal cancer, esophageal cancer, small intestine cancer, anal muscle Cancer, colon cancer, fallopian tube carcinoma, endometrial carcinoma, cervical carcinoma, vaginal carcinoma, vulvar carcinoma, Hodgkin's disease, prostate cancer, bladder cancer, kidney cancer, ureter cancer, renal cell carcinoma, renal pelvic carcinoma and central nervous system tumor It can be used for the prevention and treatment of cancer diseases.
본 발명의 약학적 조성물은 본 발명의 레인 유도체 함유용액 외에 추가로 동일 또는 유사한 기능을 나타내는 유효성분을 1종 이상 함유할 수 있다.The pharmaceutical composition of the present invention may further contain one or more active ingredients exhibiting the same or similar functions in addition to the lane derivative-containing solution of the present invention.
본 발명의 약학적 조성물은, 조성물 총 중량에 대하여 상기 항암효과가 증진된 레인 유도체 함유용액을 0.0001 내지 10 중량부로, 바람직하게는 0.001 내지 1 중량부를 포함한다.The pharmaceutical composition of the present invention comprises 0.0001 to 10 parts by weight, preferably 0.001 to 1 part by weight, of the rain derivative-containing solution having enhanced anticancer effect relative to the total weight of the composition.
본 발명에 따른 약학적 조성물은 통상적으로 사용되는 담체, 부형제, 붕해제, 감미제, 활택제, 향미제 및 희석제등을 추가로 포함할 수 있다. 상기 담체, 부형제 및 희석제로는 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 들 수 있다. 상기 붕해제로는 전분글리콜산나트륨, 크로스포비돈, 크로스카멜로스나트륨, 알긴산, 카르복시메틸셀룰로오스 칼슘, 카르복시 메틸 셀룰로오스 나트륨, 키토산, 구아검, 저치환도히드록시프로필셀룰로오스, 마그네슘 알루미늄 실리케이트, 폴라크릴린 칼륨 등이 있다. 또한, 본 발명에 따른 약학적 조성물은 약제학적으로 허용가능한 첨가제를 더 포함할 수 있으며, 이때 약제학적으로 허용가능한 첨가제로는 전분, 젤라틴화 전분, 미결정셀룰로오스, 유당, 포비돈, 콜로이달실리콘디옥사이드, 인산수소칼슘, 락토스, 만니톨, 엿, 아라비아고무, 전호화전분, 옥수수전분, 분말셀룰로오스, 히드록시프로필셀룰로오스, 오파드라이, 전분글리콜산나트륨, 카르나우바 납, 합성규산알루미늄, 스테아린산, 스테아린산마그네슘, 스테아린산알루미늄, 스테아린산칼슘, 백당, 덱스트로스, 소르비톨, 탈크 등이 사용될 수 있다. 본 발명에 따른 약제학적으로 허용가능한 첨가제는 상기 약학적 조성물에 대해 0.1~90 중량부 포함되는 것이 바람직하다. The pharmaceutical composition according to the present invention may further include conventionally used carriers, excipients, disintegrants, sweeteners, lubricants, flavoring agents and diluents. The carriers, excipients and diluents include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline Cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. The disintegrants include sodium starch glycolate, crospovidone, croscarmellose sodium, alginic acid, calcium carboxymethyl cellulose, sodium carboxymethyl cellulose, chitosan, guar gum, low-substituted hydroxypropyl cellulose, magnesium aluminum silicate, and polyacryline Potassium and the like. In addition, the pharmaceutical composition according to the present invention may further include a pharmaceutically acceptable additive, wherein the pharmaceutically acceptable additives include starch, gelatinized starch, microcrystalline cellulose, lactose, povidone, colloidal silicon dioxide, Calcium hydrogen phosphate, lactose, mannitol, malt, gum arabic, pregelatinized starch, corn starch, powdered cellulose, hydroxypropyl cellulose, opadry, sodium starch glycolate, carnauba lead, synthetic aluminum silicate, stearic acid, magnesium stearate, Aluminum stearate, calcium stearate, sucrose, dextrose, sorbitol, talc and the like can be used. The pharmaceutically acceptable additive according to the present invention is preferably included 0.1 to 90 parts by weight based on the pharmaceutical composition.
또한, 본 발명의 약학적 조성물이 적용될 수 있는 개체는 척추동물이고 바람직하게는 포유동물이며, 그보다 바람직하게는 쥐, 토끼, 기니아피크, 햄스터, 개, 고양이와 같은 실험동물이고, 가장 바람직하게는 침팬지, 고릴라와 같은 유인원류 동물이다. 또한, 본 발명의 약학적 조성물은 경구 또는 비경구 투여할 수 있으며, 비경구 투여시 복강내주사, 직장내주사, 피하주사, 정맥주사, 근육내 주사, 자궁내 경막 주사, 뇌혈관내(intracerebroventricular) 주사 또는 흉부내 주사에 의해 투여될 수 있다. 또한, 상기 약학적 조성물은 암의 예방 및 치료를 위하여 상기 개체에 단독으로, 또는 수술, 호르몬 치료, 약물 치료 및 생물학적 반응 조절제를 사용하는 방법들과 병용하여 사용할 수 있다.In addition, the subject to which the pharmaceutical composition of the present invention can be applied is a vertebrate and preferably a mammal, more preferably an experimental animal such as a rat, rabbit, guinea pig, hamster, dog, cat, and most preferably It is ape-like, such as chimpanzees and gorillas. In addition, the pharmaceutical composition of the present invention can be administered orally or parenterally, and intraperitoneal injection, rectal injection, subcutaneous injection, intravenous injection, intramuscular injection, intrauterine epidural injection, cerebrovascular (intracerebroventricular) ) Or by intrathoracic injection. In addition, the pharmaceutical composition may be used alone or in combination with methods using surgery, hormonal therapy, drug treatment and biological response modifiers for the subject for the prevention and treatment of cancer.
본 발명의 약학적 조성물의 바람직한 투여량은 환자의 상태 및 체중, 질병의 정도, 약물형태, 투여경로 및 기간에 따라 다르지만, 당업자에 의해 적절하게 선택될 수 있다. 그러나, 바람직한 효과를 위해서, 본 발명의 약학적 조성물은 1일 0.0001 내지 100 ㎎/㎏으로, 바람직하게는 0.001 내지 100 ㎎/㎏으로 투여하는 것이 좋다. 투여는 하루에 한번 투여할 수도 있고, 수회 나누어 투여할 수도 있다.The preferred dosage of the pharmaceutical composition of the present invention depends 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. However, for the desired effect, the pharmaceutical composition of the present invention is preferably administered at 0.0001 to 100 mg / kg, preferably at 0.001 to 100 mg / kg. Administration may be administered once a day or may be divided several times.
아울러, 본 발명은 상기 방법에 의해 제조된, 항암효과가 증진된 레인 유도체 함유용액을 유효성분으로 함유하는 암 예방 및 개선용 건강기능식품을 제공한다.In addition, the present invention provides a health functional food for cancer prevention and improvement, which is prepared by the above method, containing an anti-cancer effect-enhanced rain derivative-containing solution as an active ingredient.
본 발명의 레인 유도체 함유용액은 식품에 그대로 첨가하거나 다른 식품 또는 식품 성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효 성분의 혼합양은 그의 사용 목적(예방 또는 개선용)에 따라 적합하게 결정될 수 있다. 일반적으로, 식품 또는 음료의 제조시에는 본 발명의 조성물이 원료에 대하여 0.2 내지 20 중량부, 바람직하게는 0.24 내지 10 중량부로 첨가한다. 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 rain derivative-containing solution of the present invention may be added to a food as it is or used with other food or food ingredients, and may be appropriately used according to a conventional method. The mixing amount of the active ingredient can be suitably determined according to the purpose of use (prevention or improvement). Generally, in the preparation of food or beverages, the composition of the present invention is added in an amount of 0.2 to 20 parts by weight, preferably 0.24 to 10 parts by weight, based on the raw materials. 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.
본 발명의 건강식품은 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있다. 상술한 천연 탄수화물은 포도당, 과당과 같은 모노사카라이드, 말토스, 슈크로스와 같은 디사카라이드, 및 덱스트린, 사이클로덱스트린과 같은 폴리사카라이드, 자일리톨, 소르비톨, 에리트리톨 등의 당알콜이다. 감미제 로서는 타우마틴, 스테비아 추출물과 같은 천연 감미제나, 사카린, 아스파르탐과 같은 합성 감미제 등을 사용할 수 있다. 상기 천연 탄수화물의 비율은 본 발명의 건강식품 100 중량부당 0.01~0.04 중량부, 바람직하게는 약 0.02~0.03 중량부 범위에서 선택하는 것이 바람직하다.The health food of the present invention may contain various flavors or natural carbohydrates as additional ingredients. Such natural carbohydrates are monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, and polysaccharides such as dextrin and cyclodextrin, and 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, aspartame, and the like can be used. The ratio of the natural carbohydrate is preferably selected in the range of 0.01 to 0.04 parts by weight, preferably about 0.02 to 0.03 parts by weight, per 100 parts by weight of the health food of the present invention.
상기 식품의 종류에는 특별한 제한은 없다. 상기 물질을 첨가할 수 있는 식품의 예로는 드링크제, 소세지, 비스켓, 쵸코렛, 캔디류, 스넥류, 과자류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 알콜 음료 및 비타민 복합제 등이 있으며, 통상적인 의미에서의 건강 식품을 모두 포함한다.There is no particular limitation on the kind of food. Examples of foods to which the substance may be added include drinks, sausages, biscuits, chocolates, candy, snacks, sweets, gums, dairy products including ice cream, various soups, beverages, alcoholic beverages, and vitamin complexes. It includes all of the health foods in the sense.
상기 외에 본 발명의 건강식품은 여러 가지 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 건강식품은 천연 과일쥬스, 과일쥬스 음료 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 이러한 성분은 독립적으로 또는 조합하여 사용할 수 있다. 이러한 첨가제의 비율은 크게 중요하진 않지만 본 발명의 건강식품 100 중량부당 0.01~0.1 중량부의 범위에서 선택되는 것이 일반적이다.In addition to the above, the health food of the present invention includes various nutrients, vitamins, electrolytes, flavors, coloring agents, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloid thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols. And carbonation agents used in carbonated beverages. In addition, the health food of the present invention may contain a flesh for producing natural fruit juice, fruit juice beverage and vegetable beverage. These components can be used independently or in combination. Although the ratio of such an additive is not critical, it is generally selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the health food of the present invention.
본 발명의 방법에 따라 복잡한 처리 과정 없이 방사선 조사기술을 이용하여 높은 수율로 레인 유도체를 생성할 수 있었고, 아폽토시스에 의해 유발된 항암효과 가 증진되어, 항암제로 유용하게 사용될 수 있다.According to the method of the present invention, it is possible to produce a lane derivative in a high yield using a radiation technique without a complicated treatment process, and the anticancer effect caused by apoptosis is enhanced, it can be usefully used as an anticancer agent.
이하, 본 발명을 실시예, 실험예 및 제조예에 의해 상세히 설명한다.Hereinafter, the present invention will be described in detail by Examples, Experimental Examples and Preparation Examples.
단, 하기 실시예, 실험예 및 제조예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예에 의해 한정되는 것은 아니다.However, the following Examples, Experimental Examples and Preparation Examples are merely illustrative of the present invention, and the content of the present invention is not limited by the following Examples.
<< 실시예Example 1> 1> 센노사이드Sennoside A 처리 A treatment
시중에서 구입한 센노사이드 A(Sigma Aldrich, 미국) 1 ㎎/㎖를 50% 메탄올에 1000 ppm의 농도로 녹인 후, 0.05%의 농도로 과산화수소를 첨가하여 용기에 담은 후, 한국원자력연구원 정읍방사선과학연구소 내에 비치되어 있는 선원 10만 Ci의 코발트(Cobalt)-60 감마선 조사 시설(Point source AECL, IR-79, MDS Nordion International Co. Ltd., Ottawa, ON, Canada)을 이용하여 실온에서 1-5 KGy를 조사하였으며 총 흡수선량의 오차는 ±0.2 Gy였다.Dissolve 1 mg / ml of commercially available Senoside A (Sigma Aldrich, USA) in 50% methanol at a concentration of 1000 ppm, add hydrogen peroxide at a concentration of 0.05%, and place it in a container. Korea Atomic Energy Research Institute 1-5 at room temperature using a 100,000 source cobalt-60 gamma irradiation facility (Point source AECL, IR-79, MDS Nordion International Co. Ltd., Ottawa, ON, Canada) KGy was investigated and the error of total absorbed dose was ± 0.2 Gy.
<< 실험예Experimental Example 1> 1> 센노사이드Sennoside A 용액 내 레인 함량 측정 Determination of Rain Content in Solution A
하기 조건으로 상기 실시예 1에서 처리된 센노사이드 A 용액을 크로마토그래피로 분석하였다:The sennoside A solution treated in Example 1 under the following conditions was analyzed by chromatography:
1) 기기: Agillent HPLC system;1) Instrument: Agillent HPLC system;
2) 컬럼: C18;2) column: C18;
3) UV: 203 ㎚;3) UV: 203 nm;
4) 주입량: 10 ㎕;4) injection amount: 10 μl;
5) Oven 온도: 35℃; 및,5) Oven temperature: 35 ° C .; And,
6) 유동속도: 1.00 ㎖/min.6) Flow rate: 1.00 ml / min.
도 2의 센노사이드 A 및 레인 표준 물질의 크로마토그래피 그래프를 바탕으로 분석한 결과, 도 3에서 나타난 바와 같이 본 발명의 방법에 따른 처리에 의해 레인 유도체의 함량이 증가하는 것을 확인하였다.As a result of analyzing the chromatograph of the sennoside A and the lane standard of FIG. 2, it was confirmed that the content of the lane derivative was increased by the treatment according to the method of the present invention as shown in FIG.
<< 실험예Experimental Example 2> 증진된 항암효과 측정 2> Measured enhanced anticancer effect
인간 전립선암세포인 PC-3 세포(한국세포주은행) 또는 간암세포인 HepG2 세포(한국세포주은행)를 24웰 배양판에 1 × 104 세포/웰로 배양한 후, 레인 표준물질(시그마, 미국), 센노사이드 A, 실시예 1에서 제조한 레인 유도체 및 과산화수소를 첨가하지 않은 채로 실시예 1의 방법대로 방사선에 노출된 센노사이드 A를 0 내지 24 μM의 농도로 처리한 후, 10% FBS를 첨가한 RPMI1640 배지에서 5% CO2, 37℃ 배양기에서 배양하였다. 48시간 후에 배지를 버리고 MTT가 100 ㎍/㎖ 함유되어있는 RPMI 배지로 채운 후, 추가로 3시간 배양시킨 후 배지를 제거하고 이소프로판올을 각 웰 당 500 ㎕씩 분주하고 570 ㎚에서 흡광도를 측정하였다.PC-3 cells (Korea Cell Line Bank) or HepG2 cells (Korea Cell Line Bank), which are human prostate cancer cells, were cultured at 1 × 10 4 cells / well in a 24-well plate, followed by Lane standard (Sigma, USA), Senoside A, the lane derivatives prepared in Example 1, and sennoside A exposed to the radiation according to the method of Example 1 without the addition of the hydrogen peroxide and the concentration of 0 to 24 μM and then 10% FBS was added Incubated in a 37% incubator, 5% CO 2 in RPMI1640 medium. After 48 hours, the medium was discarded and filled with RPMI medium containing 100 μg / ml of MTT, followed by incubation for another 3 hours, the medium was removed, and 500 μl of isopropanol was dispensed in each well, and the absorbance was measured at 570 nm.
그 결과, 도 4에서 나타난 바와 같이 센노사이드 A 및 상기 센노사이드 A에 방사선만 조사된 물질에는 세포독성이 거의 없었으나, 본 발명의 방법으로 센노사 이드 A로부터 제조된 레인 유도체에서는 확연한 항암효과를 확인할 수 있었다.As a result, as shown in Figure 4, the sennoside A and the material irradiated only to the sennoside A had little cytotoxicity, but in the rain derivative prepared from sennoside A by the method of the present invention has a pronounced anticancer effect I could confirm it.
또한, 도 5에서 나타난 바와 같이 본 발명의 방법으로 제조된 레인 유도체는 레인 표준물질에 비해서도 더 높은 세포독성을 나타내었다.In addition, as shown in Figure 5 lane derivatives prepared by the method of the present invention showed a higher cytotoxicity compared to the lane standard.
<제조예 1> 약학적 제제의 제조Preparation Example 1 Preparation of Pharmaceutical Formulation
1. 산제의 제조1. Preparation of powder
본 발명의 레인 유도체 함유용액 2 g2 g of a lane derivative-containing solution of the present invention
유당 1 g1 g lactose
상기의 성분을 혼합하고 기밀포에 충진하여 산제를 제조하였다.The above components were mixed and packed in airtight bags to prepare powders.
2. 정제의 제조2. Preparation of Tablets
본 발명의 레인 유도체 함유용액 100 ㎎100 mg of a lane derivative-containing solution of the present invention
옥수수전분 100 ㎎
유 당 100 ㎎
스테아린산 마그네슘 2 ㎎2 mg magnesium stearate
상기의 성분을 혼합한 후, 통상의 정제의 제조방법에 따라서 타정하여 정제를 제조하였다.After mixing the above components, tablets were prepared by tableting according to a conventional method for producing tablets.
3. 캡슐제의 제조3. Preparation of Capsule
본 발명의 레인 유도체 함유용액 100 ㎎100 mg of a lane derivative-containing solution of the present invention
옥수수전분 100 ㎎
유 당 100 ㎎
스테아린산 마그네슘 2 ㎎2 mg magnesium stearate
상기의 성분을 혼합한 후, 통상의 캡슐제의 제조방법에 따라서 젤라틴 캡슐에 충전하여 캡슐제를 제조하였다.After mixing the above components, the capsule was prepared by filling in gelatin capsules according to the conventional method for producing a capsule.
4. 환의 제조4. Manufacture of rings
본 발명의 레인 유도체 함유용액 1 g1 g of a lane derivative-containing solution of the present invention
유당 1.5 gLactose 1.5 g
글리세린 1 gGlycerin 1 g
자일리톨 0.5 g0.5 g of xylitol
상기의 성분을 혼합한 후, 통상의 방법에 따라 1 환 당 4 g이 되도록 제조하였다.After mixing the above components, it was prepared to be 4 g per ring in a conventional manner.
5. 과립의 제조5. Manufacture of granules
본 발명의 레인 유도체 함유용액 150 ㎎150 mg of a lane derivative-containing solution of the present invention
대두 추출물 50 ㎎Soybean Extract 50mg
포도당 200 ㎎Glucose 200 mg
전분 600 ㎎Starch 600 mg
상기의 성분을 혼합한 후, 30% 에탄올 100 ㎎을 첨가하여 60℃에서 건조하여 과립을 형성한 후 포에 충진하였다.After mixing the above components, 100 mg of 30% ethanol was added and dried at 60 ° C. to form granules, and then filled in fabric.
<제조예 2> 식품의 제조 Preparation Example 2 Preparation of Food
본 발명의 레인 유도체 함유용액을 포함하는 식품들을 다음과 같이 제조하였다.Foods containing the lane derivative-containing solution of the present invention were prepared as follows.
1. 밀가루 식품의 제조1. Preparation of flour food
본 발명의 레인 유도체 함유용액 0.5~5.0 중량부를 밀가루에 첨가하고, 이 혼합물을 이용하여 빵, 케이크, 쿠키, 크래커 및 면류를 제조하여 건강 증진용 식품을 제조하였다.0.5 to 5.0 parts by weight of the lane derivative-containing solution of the present invention was added to flour, and bread, cake, cookies, crackers and noodles were prepared using the mixture to prepare foods for health promotion.
2. 유제품(dairy products)의 제조2. Manufacturing of Dairy Products
본 발명의 레인 유도체 함유용액 5~10 중량부를 우유에 첨가하고, 상기 우유를 이용하여 버터 및 아이스크림과 같은 다양한 유제품을 제조하였다.5-10 parts by weight of the lane derivative-containing solution of the present invention was added to milk, and various dairy products such as butter and ice cream were prepared using the milk.
<제조예 3> 음료의 제조Preparation Example 3 Preparation of Beverage
본 발명의 레인 유도체 함유용액 1000 ㎎1000 mg of a lane derivative-containing solution of the present invention
구연산 1000 ㎎ Citric acid 1000 mg
올리고당 100 g 100 g oligosaccharides
매실농축액 2 g Plum concentrate 2 g
타우린 1 g 1 g of taurine
정제수를 가하여 전체 900 ㎖ Add 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 2 ℓ용기에 취득하여 밀봉 멸균한 뒤 냉장 보관한 다음 본 발명의 건강음료 조성물 제조에 사용한다. After mixing the above components according to the conventional healthy beverage manufacturing method, and stirred and heated at 85 ℃ for about 1 hour, the resulting solution is filtered and obtained in a sterilized 2 L container, sealed sterilized and stored in the refrigerator after Used to prepare the healthy beverage composition of the invention.
상기 조성비는 비교적 기호 음료에 적합한 성분을 바람직한 실시예로 혼합 조성하였지만, 수요계층, 수요국가, 사용 용도 등 지역적, 민족적 기호도에 따라서 그 배합비를 임의로 변형 실시하여도 무방하다.Although the composition ratio is a composition suitable for a preferred beverage in a preferred embodiment, the composition ratio may be arbitrarily modified according to regional and ethnic preferences such as demand hierarchy, demand country, and intended use.
도 1은 센노사이드 A로부터 레인 유도체로 전환되는 과정을 나타낸 도이다.1 is a diagram showing a process of conversion from sennoside A to a lane derivative.
도 2는 센노사이드 A 및 레인 표준물질의 크로마토그래피 그래프를 나타낸 도이다(Junko Koyama et al., Journal of Chromatography A 1145:183-189, 2007):FIG. 2 is a chromatograph of sennoside A and lane standards (Junko Koyama et al ., Journal of Chromatography A 1145: 183-189, 2007):
a: 크로마토그래피 그래프; 및,a: chromatography graph; And,
b: 피크 별 표준물질의 명칭.b: Name of standard by peak.
도 3은 센노사이드 A로부터 방사선 처리에 의해 레인 유도체로 전환된 결과를 나타낸 도이다:3 is a diagram showing the results of conversion from sennoside A to lane derivatives by radiation treatment:
a: 방사선 처리 전; 및,a: before radiation treatment; And,
b: 방사선 처리 후.b: after radiation treatment.
도 4는 간암세포 및 전립선암세포에서 센노사이드 A 표준물질과 본 발명의 방법으로 제조된 레인 유도체의 항암효과를 나타낸 도이다(IRSH: 센노사이드 A + 0.05% 과산화수소 + 1 kGy, IRS: 센노사이드 A + 1 kGy):Figure 4 is a diagram showing the anticancer effect of the sennoside A standard and the lane derivative prepared by the method of the present invention in liver cancer cells and prostate cancer cells (IRSH: sennoside A + 0.05% hydrogen peroxide + 1 kGy, IRS: sennoside A + 1 kGy):
a: 간암세포; 및,a: liver cancer cell; And,
b: 전립선암세포.b: prostate cancer cells.
도 5는 본 발명의 레인 유도체와 기존 레인 표준 물질의 항암효과를 비교한 도이다.5 is a diagram comparing the anticancer effect of the lane derivative of the present invention and the existing lane standard.
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CN103408613A (en) * | 2013-07-22 | 2013-11-27 | 中国科学院西北高原生物研究所 | Preparation method for chemical reference substances of anthraquinone glucoside and stibene glucoside in rheum officinale medicinal material |
CN103505448A (en) * | 2012-06-04 | 2014-01-15 | 香港浸会大学 | Method of using rhein for treating fibrotic conditions and tumors |
CN103585647A (en) * | 2013-11-27 | 2014-02-19 | 江苏省中医药研究院 | Application of isotope labeled dianthrone compound in preparation of antineoplastic drugs |
CN112022866A (en) * | 2020-10-16 | 2020-12-04 | 上海健康医学院 | Application of sennoside A in preparation of medicine for treating liver cancer |
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CN103505448A (en) * | 2012-06-04 | 2014-01-15 | 香港浸会大学 | Method of using rhein for treating fibrotic conditions and tumors |
CN103505448B (en) * | 2012-06-04 | 2016-03-02 | 香港浸会大学 | The application of chrysophanic acid in preparation treatment pancreatic gland fibrosis medicine |
CN103408613A (en) * | 2013-07-22 | 2013-11-27 | 中国科学院西北高原生物研究所 | Preparation method for chemical reference substances of anthraquinone glucoside and stibene glucoside in rheum officinale medicinal material |
CN103408613B (en) * | 2013-07-22 | 2016-01-20 | 中国科学院西北高原生物研究所 | The preparation method of anthraquinone glycoside and stilbene glucoside chemical reference substance in rhubarb medicinal material |
CN103585647A (en) * | 2013-11-27 | 2014-02-19 | 江苏省中医药研究院 | Application of isotope labeled dianthrone compound in preparation of antineoplastic drugs |
CN103585647B (en) * | 2013-11-27 | 2018-04-13 | 江苏省中医药研究院 | Application of the dianthrone compound of isotope marks in antitumor drug is prepared |
CN112022866A (en) * | 2020-10-16 | 2020-12-04 | 上海健康医学院 | Application of sennoside A in preparation of medicine for treating liver cancer |
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