KR101309848B1 - A novel manufacturing method of ginsenoside Rh1 by simultaneous co-reaction of hydrolysis and solvent extraction from ginseng powder - Google Patents
A novel manufacturing method of ginsenoside Rh1 by simultaneous co-reaction of hydrolysis and solvent extraction from ginseng powder Download PDFInfo
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
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- A61K2236/15—Preparation or pretreatment of starting material involving mechanical treatment, e.g. chopping up, cutting or grinding
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/17—Preparation or pretreatment of starting material involving drying, e.g. sun-drying or wilting
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
Abstract
본 발명은 인삼 성분중 진세노사이드 Rh1을 염산가수분해 처리와 용매추출반응을 동시에 수행하여 2시간이내에 대량생산할 수 있는 방법을 제공하는 것으로 인삼을 건조하여 분쇄한 인삼분말에 3 N HCl 용액과 n-Butanol을 동시에 동량비로 넣고 핫플레이트상에서 150℃에서 가열 교반하면서 반응을 수행하면서 이 때 용매와 수분의 소실을 방지하기 위하여 반응용기 상부에 냉각관을 설치하고 휘발된 용매와 수분이 다시 냉각되어 낙하되도록 하며. 반응이 완료되면 냉각과 동시에 물층과 n-Butanol층이 분획이 이루어지는데 이를 분획여두로 n-Butanol층만을 모아 건조된 반응산물에 물과 에틸아세테이트를 넣고 분역여두로 2회 반복 추출한 것을 다시 건조하여 Rh 1을 함유한 건조물을 회수하므로써 건조 인삼 1 g당 22.1mg의 인삼 진세노사이드 Rh1을 상기 간단한 조작과 단시간 반응시간내 생산할 수 있는 뛰어난 효과가 있다The present invention provides a method for mass production of ginsenoside Rh1 in ginseng components by hydrochloric acid hydrolysis and solvent extraction at the same time in 2 hours. Put the same amount of Butanol at the same time and conduct the reaction by heating and stirring at 150 ℃ on a hot plate. To make sure. Upon completion of the reaction, the water layer and the n-Butanol layer are partitioned at the same time as cooling. The n-Butanol layer is collected by fractional extraction. Water and ethyl acetate are added to the dried reaction product, and the mixture is repeatedly extracted with a separation filter. By recovering the dried product containing Rh 1, 22.1 mg of ginseng ginsenoside Rh1 per g of dried ginseng can be produced within the above simple operation and short reaction time.
Description
본 발명은 인삼분말을 가수분해와 용매추출의 동시반응법을 이용한 인삼 사포닌 진세노사이드 Rh1의 제조방법에 관한 것으로 인삼성분중 진세노사이드 Rh1이 직접 전환되면서 용매추출되어 추가 가수분해 되는것을 방지하므로써 고농도 Rh1을 단시간 대량 생산할 수 있는 신규한 공정을 제공하는 것에 관한 것이다.The present invention relates to a method for preparing ginseng saponin ginsenoside Rh1 using a simultaneous reaction method of hydrolysis and solvent extraction of ginseng powder, by preventing ginsenoside Rh1 from ginseng components being directly converted to prevent additional hydrolysis. The present invention relates to providing a novel process for mass production of high concentrations of Rh1 in a short time.
인삼사포닌 진세노이드(ginsenoids)는 인삼에 존재하는 다양한 약리효능을 나타내는 성분이다. Ginseng saponin ginsenoids (ginsenoids) is a component that exhibits various pharmacological effects present in ginseng.
인삼(Panax ginseng C.A. Meyer)은 오래 전부터 사용되어 온 가장 중요한 한방약용식물로 동북아시아에서 주로 보기약(氣藥)으로 사용되어 왔으며, 최근 인삼 가공기술의 발달로 소비자들이 섭취가 간편하고, 휴대가 편리한 2차 가공 인삼제품들이 개발되고 있으며, 생활수준의 향상과 함께 건강에 관한 관심이 높아지면서 인삼·홍삼에 관한 관심도 꾸준히 높아지고 있다. 우리나라의 경우, 2004년부터 시행된 건강기능식품법의 시행으로 많은 대기업에서 인삼제품 시장에 신규 진출해 시장규모가 급격히 증가하고 있으며, 인삼업계의 인홍삼시장 규모는 2004년 3,112억 원에서 2006년 6,000억 원, 2010년도에는 1조원대의 거대시장을 형성할 것으로 전망하고 있다.Ginseng (Panax ginseng CA Meyer) is the most important herbal medicine that has been used for a long time. It has been used mainly as a botanical medicine in Northeast Asia. Recently, with the development of ginseng processing technology, consumers can easily consume and carry Convenient secondary processed ginseng products are being developed, and interest in ginseng and red ginseng is steadily increasing as health care interests increase with the improvement of living standards. In Korea, due to the implementation of the Health Functional Food Act since 2004, many large corporations have entered the ginseng product market, and the market size is rapidly increasing.In the ginseng industry, the size of the ginseng market in 2004 was KRW 311.2 billion and 6,000 in 2006. It is expected to form a huge market of KRW 1 trillion in 2010.
한편,인삼 가공제품들은 농축액, 정분, 차류, 타브렛, 캡슐, 분말류, 음료, 환제, 절편삼, 봉밀삼, 과자류, 주류 등이 주류를 이루고 있으나, 인삼이나 홍삼 추출물이나 분말 등 단순 가공에 의한 제품이 대부분으로 진세노사이드 특정성분을 높이는 제조방법은 표준품을 만드는데 그치는 경우가 대부분이고 이러한 제품생산은 제조공정이 복잡하여 고비용이 발생하기 때문에 제품화가 용이하지 않았다. On the other hand, ginseng processed products are mainly composed of concentrates, meals, teas, tablets, capsules, powders, beverages, pills, sliced ginseng, beeswax, confectionary, alcoholic beverages, etc. Most of the manufacturing methods to increase the ginsenoside specific ingredients to make a standard product, and the production of these products was not easy because the production process is complicated and expensive.
홍삼의 특유 사포닌 진세노사이드류는 Rs1, Rs2, Rs3, Rg2, Rg3, Rh1이고 주요 진세노사이드는 Rg2와 Rg3로 각각 0.029%, 0.034% 함유하고 있으며 백삼의 특유 진세노사이드류는 Rb1, Rb2, Rc, Rd이며 주요 성분은 Rb1으로 0.82%를 함유하고 있다(최신고려인삼 성분과 효능편, 한국인삼연초연구원). The unique saponin ginsenosides of red ginseng are Rs1, Rs2, Rs3, Rg2, Rg3 and Rh1, and the major ginsenosides are Rg2 and Rg3, containing 0.029% and 0.034%, respectively. It is Rd and its main component is Rb1, which contains 0.82% (Latest Ginseng and Efficacy, Korea Ginseng and Tobacco Research Institute).
주요 프로사포게닌으로 인삼 사포닌을 50% 초산과 같은 약산으로 가수분해시킬 때 탄소 20번 위치에서 결합된 당류가 선택적으로 가수분해되어 주로 Rg3, Rg2를 고농도로 생산할 수 있다(국내공개특허 공개번호 10-2005-109269). 또한 사포게닌은 인삼 사포닌을 7% 황산용액으로 가수분해하여 3번, 6번, 20번 위치의 탄소에 결합된 당류를 모두 가수분해하여 Panaxadiol과 Panaxatriol을 생산할 수 있었다(인삼성분분석법, 한국인삼연초연구소).Major pro sand paper when the ginsenoside as genin be hydrolyzed with mild acid such as 50% acetic acid and the sugars binding the carbon of 20-position is selectively hydrolyzed primarily to produce Rg3, Rg 2 in a high concentration (in Japan Laid-Open Patent Publication No. 10-2005-109269). Also, saponenin was able to produce Panaxadiol and Panaxatriol by hydrolyzing ginseng saponin with 7% sulfuric acid solution to hydrolyze all the sugars bound to carbon at positions 3, 6 and 20 (Ginseng Component Analysis, Korean Ginseng and Tobacco). laboratory).
국내등록특허 10-0329259는 효소를 이용하여 인삼 사포닌 당기를 변화시켜서 희소 인삼사포닌인 Rh2와 Rh1을 제조하는 방법을 개시하였는데 사포닌 알파-글루코시다제로 Panaxadiol계 진세노사이드로부터 Rh2를 생산하고 알파-람노시다제을 이용하여 Rg2의 당을 분해하여 Rh1을 생산하는 방법을 개시하고 있다.또, 국내공개특허 10-2006-0109189는 루코노스톡속의 미생물을 이용하여 진세노사이드 Rh2, Rg3, F2를 생산하는 방법을 개시하고 있으며 국내공개특허특1999-000458에서는 Panaxadiol계 진세노사이드를 효소 락타제(lactase)와 반응시켜 Rg3를 생산한는 방법을 개시한 바 있다.Korean Patent No. 10-0329259 discloses a method for preparing rare Ginseng saponins Rh 2 and Rh 1 by varying ginseng saponin pull using an enzyme, which produces Rh 2 from Panaxadiol-based ginsenosides with saponin alpha-glucosidase. Disclosed is a method of producing Rh 1 by decomposing a sugar of Rg 2 using alpha-lamnosidase. In addition, Korean Laid-Open Patent Publication No. 10-2006-0109189 discloses ginsenoside Rh 2 , using microorganisms of the genus Lukonostok. A method for producing Rg 3 and F 2 is disclosed, and in Korean Patent Laid-Open No. 1999-000458, a method of producing Rg 3 by reacting Panaxadiol-based ginsenosides with an enzyme lactase (lactase) is disclosed.
상기 기술들은 인삼 진세노사이드 특정 성분을 생산하여 진세노사이드 종류에 따른 생리활성을 극대화하고 권장 섭취량을 사람들이 복용할 수 있게 함으로써 인삼 사포닌의 과용을 막고 사람의 연령과 신체상황에 맞는 섭취량을 결정할 수 있게 한다.홍삼의 주요성분중 하나인 Rg3은 평활근세포를 사멸시키는 기능이 있어 심혈관 질환이 생길 가능성을 높이는 것으로 보고된 바 있으며(Toxicological Science, 2010)따라서,홍삼사포닌 전체 성분을 복용하는 것보다 상기 특정 성분만을 복용하는 것이 인체에 더 유용할 수 있다.진세노이드 Rh1의 주요 작용은 간보호, 항종양 작용, 혈소판 응집억제등이 있으며 세포와 세포간의 유착현상을 억제고 항알러지, 피부염증질환 치료효과, 항암효과 및 여성 호르몬 유사기능 등이 알려져 있다. These technologies produce ginsenoside specific ingredients to maximize the physiological activity according to the ginsenoside type and allow people to take the recommended intake to prevent overdose of ginseng saponin and determine the intake according to the age and physical condition of the person. Rg3, one of the main components of red ginseng, has been reported to increase the likelihood of cardiovascular disease due to its function of killing smooth muscle cells (Toxicological Science, 2010). It may be more useful to the human body to take only certain components. The main actions of ginsenoid Rh1 include hepatoprotective, anti-tumor, and platelet aggregation inhibition, inhibiting cell-to-cell adhesion, anti-allergic and dermatitis diseases. Therapeutic effects, anticancer effects and female hormone-like functions are known.
특히, 상기 등록특허 10-0329259에서 처럼 인삼사포닌 진세노사이드를 효소를 이용하여 Rh2와 Rh1을 생산하는 방법은 고비용과 복잡한 공정이 수반되는 단점이 있었으며 특히 효소를 이용하여 반응추출시간이 장시간 소요되 장시간 효소반응에 따른 고비용과 효소상태에 따른 반복 재현성의 차이로 인하여 품질이 일정하시 못하다는 문제점이 있었다.
In particular, the method of producing Rh2 and Rh1 using ginseng saponin ginsenoside using enzymes, as described in the registered patent 10-0329259, has a disadvantage of high cost and complicated processes, and particularly, the reaction extraction time using enzymes takes a long time. There was a problem that the quality was not constant due to the high cost of the long time enzymatic reaction and the reproducibility difference according to the enzyme state.
따라서, 본 발명의 목적은 인삼분말을 산가수분해와 용매추출을 동시적으로 수행하여 인삼 진세노사이드 Rh1으로 전환됨과 동시에 추출 시켜 Panaxatriol로 추가 가수분해되는것을 억제하여 저비용으로 단시간 고농도의 진세노이드 Rh1을 생산할 수 있는 신규한 제조방법 제공하는 데 있다.Therefore, an object of the present invention is to simultaneously perform the acid hydrolysis and solvent extraction of ginseng powder is converted to ginseng ginsenoside Rh1 and extracted at the same time to inhibit further hydrolysis to Panaxatriol to reduce the high concentration of ginsenoid Rh1 for a short time It is to provide a new manufacturing method that can produce.
발명의 상기 목적은 인삼을 건조하여 분쇄한 인삼분말에 3 N HCl 용액과 n-Butanol을 동시에 넣고 핫플레이트상에서 150℃ 정도의 열을 가하여 교반하면서 반응을 수행하므로써 달성였다. 본 발명의 다른 목적은 첨가한 반응중 용매와 수분의 소실을 방지하기 위하여 반응용기 상부에 냉각관을 설치하여 휘발된 용매와 수분이 다시 냉각되어 반응용기 내부로 낙하되도록 하므로써 달성하였다. 본 발명의 다른 목적은 상기 반응이 완료되면 냉각과 동시에 물층과 n-Butanol층이 분획이 이루어지게 하고 분획여두로 n-Butanol층만을 따로 모아 건조된 반응산물에 물과 에틸아세테이트를 넣고 분역여두로 2회 반복 추출하고 이를 회전농축기로 건조하여 진세노이드 Rh 1 생성물을 획득 함으로써 달성하였다.The object of the present invention was achieved by adding 3 N HCl solution and n-Butanol to the ginseng powder dried and pulverized with ginseng at the same time to perform the reaction while stirring by adding a heat of about 150 ℃ on a hot plate. Another object of the present invention was achieved by installing a cooling tube on the upper part of the reaction vessel to prevent the loss of the solvent and water during the added reaction so that the volatilized solvent and water is cooled again to fall into the reaction vessel. Another object of the present invention is that when the reaction is completed, the water layer and the n-Butanol layer is cooled at the same time as the cooling is completed and the n-Butanol layer is collected separately by putting the water and ethyl acetate in the dried reaction product into Extraction was repeated twice and dried by rotary condenser to achieve the ginsenoid Rh 1 product.
본 발명은 홍삼의 진세노사이드 Rh1 성분을 산가수분해 처리와 유기용매추출반응을 동시적으로 수행하여 2시간의 단시간 내에 저비용으로 생산할 수 있는 신규한 제조방법을 제공하는 뛰어난 효과가 있다.The present invention has an excellent effect of providing a novel manufacturing method that can be produced at a low cost in a short time of 2 hours by simultaneously performing the acid hydrolysis treatment and organic solvent extraction reaction of ginsenoside Rh1 component of red ginseng.
도 1은 본 발명 실시에 따른 가수분해와 용매추출의 동시반응을 위한 용매별 분획특성을 나타낸 사진도이다.
도 2는 본 발명에 따른 산가수분해와 유기용매추출 동시적 처리로 생성된 Rh1 성분과 Rh1 표준물질의 액체크로마토그램
도 3은 본 발명의 실시예에 따른 가수분해와 용매추출의 동시반응를 위한 염산농도에 따른 반응산물 및 분획특성을 나타낸 사진도이다.
도 4는 본 발명의 실시예에 따른 염산농도별 액체크로마토그램 Rh1성분 피크의 면적을 나타낸 그림이다.1 is a photograph showing the fractionation characteristics for each solvent for the simultaneous reaction of hydrolysis and solvent extraction according to the present invention.
Figure 2 is a liquid chromatogram of the Rh1 component and Rh1 standard material produced by simultaneous hydrolysis and organic solvent extraction according to the present invention
Figure 3 is a photograph showing the reaction product and fractionation characteristics according to hydrochloric acid concentration for the simultaneous reaction of hydrolysis and solvent extraction according to an embodiment of the present invention.
4 is a graph showing the area of the liquid chromatogram Rh1 peak by hydrochloric acid concentration according to an embodiment of the present invention.
이하, 건조 인삼분말 1g당 22.1mg 의 Rh1 성분을 생산할 수 있는 신규한 제조방법을 구체적으로 설명한다.Hereinafter, a novel production method capable of producing 22.1 mg of Rh1 component per 1 g of dry ginseng powder will be described in detail.
본 발명자들은 인삼분말을 산가수분해법과 유기용매추출법을 동시에 채용하여 동시적으로 수행함으로써 인삼 Rh1성분을 2 시간 정도의 단시간에 반응과 추출을 완료함으로써 비용을 절감하고 반응과정을 단순화하고 반복재현성이 확실한 인삼 Rh1 성분의 고농도 제조방법을 제시한 것에 그 특징이 있고 반응산물을 동정하고 유기 용매의 종류와 첨가하는 염산 농도의 최적 조건을 규명하였다. The present inventors simultaneously carry out ginseng powder by acid hydrolysis method and organic solvent extraction method to complete the reaction and extraction of ginseng Rh1 components in a short time of about 2 hours to reduce cost, simplify the reaction process and repeat reproducibility. It is characterized by the high concentration method of producing ginseng Rh1 components, and the reaction products were identified and the optimum conditions of the type of organic solvent and the concentration of hydrochloric acid added were identified.
그러나,본 발명의 구체적인 내용을 실시예를 들어 상세히 설명하고자 하지만 본 발명의 권리범위는 이들 실시예에만 한정되는 것은 아니고 첨가하는 산이나 용매의 변경및, 추출방법의 단순한 변경 등에 의하여 당업자가 얼마든지 모방할 수 있으며 그와 같은 기술구성의 단순한 변경은 본 발명의 권리범위에 모두 포함된다 고 할 것이다.
However, the present invention will be described in detail with reference to Examples. However, the scope of the present invention is not limited to these Examples, and the skilled person can change the acid or solvent to be added, and simply change the extraction method. It can be said that a simple change in the configuration of such technology is all included in the scope of the present invention.
실시 예1: 가수분해와 용매추출의 동시적처리에 적합한 용매의 선택Example 1 Selection of Solvent Suitable for Simultaneous Treatment of Hydrolysis and Solvent Extraction
본 발명에 있어서 산가수분해와 동시에 유기용매의 동시추출을 수행하기 위하여 다양한 용매를 사용하여 반응완료 후 분획하고 그 결과 얻은 반응산물의 상태를 확인하였다 (도1). In the present invention, in order to perform simultaneous extraction of the organic solvent at the same time with acid hydrolysis, fractions were completed after completion of the reaction using various solvents to confirm the state of the resulting reaction product (FIG. 1).
여기서사용한, 유기 용매로는 n-Butanol, Acetone, Ethylacetate, Hexane이며 이들을 각각 3 N HCl과 동시에 인삼분말에 넣고 교반 하면서 상기 실시예에서와 같이 150℃에서 2 시간 반응시켰다. 반응결과,Acetone 과 Ethylacetate는 사포닌의 계면활성 반응에 의해 분획(fractionation)이 잘 이루어지지 않았음이 확인되었고 Hexane구에서는 Rh1성분의 추출이 제대로 되지 않았다.본 발명의 상기 실시예에 따르면 산가수분해와 유기용매추출의 동시적 처리에는 n-Butanol이 가장 바람직한 유기 용매로 판단되었다.
The organic solvents used herein were n-Butanol, Acetone, Ethylacetate, and Hexane, which were added to ginseng powder and stirred at the same time with 3 N HCl, respectively. As a result of the reaction, Acetone and Ethylacetate were found to be poorly fractionated by the saponin interfacial reaction, and the Rh1 component was not properly extracted in Hexane sphere. Acid hydrolysis according to the embodiment of the present invention. N-Butanol was considered as the most preferred organic solvent for simultaneous treatment of and organic solvent extraction.
실시예2: 출발물질의 가수분해와 용매추출 동시적처리 및 그 결과 반응산물의 동정 Example 2 Simultaneous Treatment of Hydrolysis and Solvent Extraction of Starting Materials and Identification of Reaction Products
반응용기에 수분함량 18%의 인삼분말 2g에 염산용액 100mL 와 n-Butanol 100mL 을 동시에 넣고 2 시간 동안 핫플레이트로 150℃로 가열하고 교반하면서 가수분해와 추출반응을 동시 수행하여 가수분해에 의해 생성되는 Rh1이 Panaxatriol로 완전히 가수분해되는 것을 억제하였다. 100 ml of hydrochloric acid solution and 100 ml of n-Butanol were added to 2 g of 18% ginseng powder with 18% water content in the reaction vessel. Rh1 was inhibited from being completely hydrolyzed to Panaxatriol.
반응중 상기 반응 용기 상부에 냉각관을 설치하여 휘발되는 용매와 수분을 냉각시키고 이를 반응용기에 다시 낙하하도록 하였고 이와같이 반응이 완료된 반응액은 물층과 n-Butanol층으로 분획되는데 이때 n-Butanol층을 분획여두로 모았다. n-Butanol 추출액 50㎖ 회전농축기에서 건조하여 251㎎의 반응산물을 획득 하였다. 상기 건조된 반응산물 251㎎에 다시 물 50㎖ 과 에틸아세테이트 50㎖를 넣고 분액여두로 2회 반복 추출하고 이 것을 회전농축기에서 건조시켜 메탄올 192㎎ 을 획득하고 메탄올 1㎖에 녹인 것을 Sep-Pak C18 카트리지에 주입하고 10㎖ 메탄올로 추출한 것을 액체크로마토그래피를 사용하여 반응산물을 동정하였다.During the reaction, a cooling tube was installed at the top of the reaction vessel to cool the volatilized solvent and water, which was then dropped back into the reaction vessel. The reaction solution was separated into a water layer and an n-butanol layer. Fractions were collected with a filter. n-Butanol extract was dried in a 50 ml rotary concentrator to obtain 251 mg of reaction product. Respectively. 50 ml of water and 50 ml of ethyl acetate were added to the dried reaction product 251 mg, and the mixture was extracted twice with a separatory filter. The extract was dried in a rotary condenser to obtain 192 mg of methanol, which was dissolved in 1 ml of methanol. Sep-Pak C18 The reaction product was identified using liquid chromatography, which was injected into the cartridge and extracted with 10 ml of methanol.
인삼 Rh1성분 분석은 칼럼 PreavailTM Carbohydrate ES(5 ㎛, 250× 4.6 ㎜)과 칼럼온도 60℃에서 A 용매(CH3CN : H2O : IsoPrOH = 80 : 5 : 15)75%, B 용매(CH3CN : H2O : IsoPrOH = 67 : 21 : 12) 25%의 비율로 시작하여 28분까지 A 용매 15%, B 용매 85%로 gradient를 주면서 분당 0.8mL의 유속으로 액체크로마토그래피를 수행하였고 검출기로는 ELSD(Evaporative light scattering detector)를 사용하였다. 표준 Rh1성분은 ChromaDexTM사에서 구입한 것을 사용하였다.Ginseng Rh1 component analysis was performed by using Preavail TM Carbohydrate ES (5 ㎛, 250 × 4.6 mm) and A solvent (CH 3 CN: H 2 O: IsoPrOH = 80: 5: 15) CH 3 CN: H 2 O: IsoPrOH = 67: 21: 12) Perform liquid chromatography at a flow rate of 0.8 mL per minute with a gradient of 15% A solvent and 85% B solvent starting at 25% and up to 28 minutes. An ELSD (evaporative light scattering detector) was used as a detector. The standard Rh1 component was purchased from ChromaDex ™ .
도 2는 표준 Rh1과 반응산물의 크로마토그램을 중첩시켜 머무름 시간을 비교한 것으로 Rh1 성분 피크를 6.1분에서 6.4분 사이에서 확인하였다.
Figure 2 compares the retention time by overlapping the chromatogram of the standard Rh1 and the reaction product to confirm the Rh1 component peak between 6.1 minutes and 6.4 minutes.
실시 예3: 염산농도와 Rh1 성분생성량Example 3: Hydrochloric Acid Concentration and Rh1 Production
본 발명에 따라 염산의 농도를 3 N 이하의 농도인 0.1 N, 0.5 N, 1 N, 2 N 농도에서 각각 n-Butanol과 혼합하여 인삼분말에 첨가한 다음 상기 실시예에서와 마찬가지로, 교반하면서 가열하여 2시간 반응시킨 다음 냉각시켰다. 0.1 N HCl농도 에서는 분획이 원활히 이루어지지 않았고 염산의 농도가 진해질수록 반응산물의 색이 진해지는 것을 확인할 수 있었다(도3). According to the present invention, the concentration of hydrochloric acid is added to the ginseng powder by mixing with n-Butanol at concentrations of 0.1 N, 0.5 N, 1 N, and 2 N, each having a concentration of 3 N or less, and then heated with stirring as in the above embodiment. Reacted for 2 hours and then cooled. At 0.1 N HCl concentration, the fraction was not made smoothly, and as the concentration of hydrochloric acid increased, the color of the reaction product became darker (FIG. 3).
한편, 본 발명의 실시예에서는 염산농도를 0.5 N, 1 N, 2 N, 3 N, 4 N로 각각 조절하여 가수분해와 용매추출을 동시에 반응시키고 건조한 반응산물에 물과 에틸아세테이트를 넣고 다시 분액여두로 2회 반복 추출한 것을 회전농축기로 건조시키고 메탄올에 녹여 액체크로마토그래피를 수행하여 본 결과, Rh1성분 피크면적이 3 N까지 급격히 올라간 다음에 4 N까지는 차이가 없었는데 이로써 Rh1 생산을 위한 최적 염산농도는 3 N임이 확인되었다(도4). Meanwhile, in the embodiment of the present invention, hydrochloric acid and solvent extraction are simultaneously reacted by adjusting the hydrochloric acid concentration to 0.5 N, 1 N, 2 N, 3 N, and 4 N, and water and ethyl acetate are added to the dried reaction product, and the liquid is separated again. As a result of drying the extract twice with dilution with a rotary concentrator and dissolving it in methanol, liquid chromatography was performed. As a result, the peak peak area of the Rh1 component increased to 3 N, and there was no difference until 4 N. Was found to be 3 N (FIG. 4).
실험결과, 건조한 인삼분말 1g으로부터 가수분해와 용매추출 동시반응을 통해 얻을수 있는 Rh1성분은 22.1 ㎎으로 2.2% 생산수율을 나타냈다.이와 같은 결과는 통상 Rh1성분이 홍삼에서 0.013% 함유되어 있는 것을 감안할 때 매우 높은 고농도의 인삼 Rh1성분을 수득할 수 있는 뛰어난 효과가 확인되었다.
As a result, Rh1 component obtained through simultaneous reaction of hydrolysis and solvent extraction from 1g of dried ginseng powder was 22.1 mg, which yielded 2.2% yield. This result is considered that Rh1 component contains 0.013% in red ginseng. An excellent effect of obtaining a very high concentration of ginseng Rh1 component was confirmed.
이상 설명한 바와 같이, 본 발명은 인삼분말 1 g당 22.1 mg의 Rh1성분을 간단한 조작과 단시간 반응으로 고농도로 생산할 수 있는 뛰어난 효과가 있으므로 식품가공산업상 매우 유용한 발명으로 인삼 Rh1성분을 함유한 다양한 특수식품의 원료로 제공할 수 있다.As described above, the present invention has an excellent effect of producing 22.1 mg of Rh1 component per g of ginseng powder in high concentration by simple operation and short reaction time, and thus is a very useful invention in the food processing industry. Can be used as a raw material for food.
Claims (2)
Method for producing ginsenoside Rh1 characterized in that the solution of hydrochloric acid and n-butanol mixed in the same ratio to the ginseng powder and heat stirring at 150 ℃ for 2 hours to perform acid hydrolysis and solvent extraction reaction.
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