KR100424438B1 - Enzymatic producing method of ginsenoside rd - Google Patents
Enzymatic producing method of ginsenoside rd Download PDFInfo
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- KR100424438B1 KR100424438B1 KR1019980016212A KR19980016212A KR100424438B1 KR 100424438 B1 KR100424438 B1 KR 100424438B1 KR 1019980016212 A KR1019980016212 A KR 1019980016212A KR 19980016212 A KR19980016212 A KR 19980016212A KR 100424438 B1 KR100424438 B1 KR 100424438B1
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Abstract
Description
본 발명의 목적은 인삼에 미량 함유되어 있고, 분리하기가 용이한 주요 다이올형 사포닌을 구조전환시켜 인삼중에 미량 함유되어 있는 진세노사이드 Rd를 간단하게 다량 제조하는 방법에 관한 것이다.An object of the present invention relates to a method for producing a simple amount of ginsenoside Rd contained in trace amounts in ginseng by restructuring major diol-type saponins contained in trace amounts and easy to separate.
본 발명은 다이올형 사포닌으로 부터 효소적방법에 의하여 다음 일반식( I )으로 표시되는 20(S)-프로토파낙사다이올-3-0-베타-디-글루코피라노실(1→2)-베타-디-글루코피라노사이드 [이하 진세노사이드 Rd라 함] 를 제조하는 방법에 관한 것이다.In the present invention, 20 (S) -protopanaxadiol-3-0-beta-di-glucopyranosyl (1 → 2)-represented by the following general formula (I) by enzymatic method from diol-type saponin: A method for producing beta-di-glucopyranoside (hereinafter referred to as ginsenoside Rd).
상기 일반식( I )의 진세노사이드 Rd는 부신피질 호르몬 분비 촉진작용, 코스테론 분비 촉진작용, mesenchyme 세포증식 억제(신장 사구체 비대 억제작용) 등이 있는 성분으로 이미 알려져 있다.Ginsenoside Rd of the general formula (I) is already known as a component having an adrenal cortex hormone secretion promoting effect, a hormone promoting corticosteroid secretion, and a mesenchyme cell proliferation inhibitory effect (extension suppression of renal glomeruli).
인삼 특유의 약리활성 사포닌인 진세노사이드 유도체들은 다마란계의 트리테르페노이드인 프로토파낙사다이올과 프로토파낙사트라이올에 글루코스, 람노스, 아라비노스 또는 자일로스와 같은 당류가 결합한 화합물들로서 현재까지 고려인삼에서 약 30여종의 유도체들이 밝혀져 있다. 또한 인삼 사포닌은 아글리콘에 결합되어 있는 당의 종류나 결합된 당류의 수 또는 결합위치에 따라 약리효능이 각각 다르다는 것이 이미 밝혀져 있으며, 인삼중 함량이 많고 분리하기가 용이한 주요 사포닌의 약리효능에 대해서는 많은 연구가 수행되었으나, 미량사포닌의 약리효능에 관한 연구는 상대적으로 적은 편이다.Ginsenoside derivatives, which are the pharmacologically active saponins unique to ginseng, are compounds in which saccharides such as glucose, rhamnose, arabinose or xylose are combined with protoparanaxadiol, a protoparanaxadiol, and a diteran triterpenoid. To date, about 30 derivatives of Korean ginseng have been identified. In addition, ginseng saponins have already been shown to have different pharmacological effects depending on the type of sugars bound to aglycone, the number of saccharides bound, or the binding position. Although many studies have been conducted, relatively little research has been conducted on the pharmacological effects of microsaponins.
본 발명은 인삼의 사포닌성분중 진세노사이드 Rd의 새로운 제조방법에 관한 것으로 진세노사이드 Rd는 효능실험을 통하여 여러 가지 유효한 효능이 있는 것으로 밝혀지고 있으나 인삼중에는 미량 함유하고 있어 다량의 시료를 얻기가 어려운 실정이다. 한편 인삼사포닌중 진세노사이드 Rb1. Rb2, Rc 등은 파낙사다이올 사포닌 성분으로 함량이 높고 진세노사이드 Rd로 구조전환될 수 있는 기본구조를 갖고 있다. 즉 파낙사다이올 사포게닌의 C3위치에 결합된 포도당 2분자는 같고 다만 C20위치에 결합된 포도당 한분자의 탄소 6번째 위치에 결합된 당류만이 상이하다는 점에 착안하여 본 연구를 수행하게 되었다. 진세노사이드 Rd의 제조에 관한 종래의 방법에서는 진세노사이드 Rb1순품 혹은 지페노사이드 V를 효소 글루코시다제나 람노시다제로 가수분해시켜 제조한 바 있다(영국특허 GB 2179042 A, 하루지 오시오 등, 1987).The present invention relates to a new method for preparing ginsenoside Rd among saponin components of ginseng, and ginsenoside Rd has been found to have various effective effects through efficacy experiments. It is difficult. Ginsenoside Rb 1 . Rb 2 , Rc and the like are high contents of panaxadiol saponin and have a basic structure that can be structurally converted to ginsenoside Rd. In other words, the two glucose molecules bound to the C 3 position of panaxadiol sapogenin are the same, but only the sugars bound to the carbon 6 position of one molecule of glucose bound to the C 20 position are different. It became. Conventional methods for the preparation of ginsenoside Rd have been prepared by hydrolyzing ginsenoside Rb 1 pure or zipenoside V with enzyme glucosidase or rhamnosidase (British GB GB 2179042 A, Haruji Ohio et al., 1987).
본 발명에서는 인삼에 함량이 높고 분리하기가 용이한 진세노사이드 Rb1,Rb2, Rc 및 프로토파낙사다이올계 사포닌 혼합물을 수종의 효소와 반응시켜 그중 진세노사이드 Rd로 구조전환이 우수했던 효소를 선별하였으며 제조수율은 70% 이상으로 간편하게 다량의 시료를 분리 정제할 수 있었다.In the present invention, the ginsenosides Rb 1, Rb 2 , Rc and protopananaxadiol-based saponin mixtures having high content in ginseng and easy to separate are reacted with several enzymes, and among them, enzymes having excellent structural conversion to ginsenoside Rd. And the production yield was more than 70% was able to easily separate and purified a large amount of samples.
본 발명은 인삼에 다량 함유되어 있는 주요 다이올형 사포닌인 진세노사이드 Rb1, Rb2, Rc 또는 다이올계 사포닌 혼합물을 효소적방법으로 구조전환시켜 인삼속에 미량 함유하고 있는 진세노사이드 Rd를 간단하게 다량 제조하기 위한 것이다.The present invention simply converts ginsenosides Rb 1 , Rb 2 , Rc or a diol-based saponin mixture, which is a major diol-type saponin, contained in a large amount of ginseng by enzymatic method, to simplify the ginsenoside Rd contained in traces of ginseng. It is to manufacture much.
본 발명에서는 인삼의 주요 다이올형 사포닌인 진세노사이드 Rb1, Rb2, Rc 또는 다이올계 사포닌 혼합물을 물, 완충용액과 같은 수성용매 또는 수성용매와 유기용매의 혼합액 중에서 미생물에서 분리한 락타제 또는 베타-갈락토시다제와 함께 반응시키면 단기간 내에 C20위치의 글루코스에 결합된 배당체결합이 선택적으로 절단되어 진세노사이드 Rd가 고수율로 생성된다.In the present invention, the ginsenoside Rb 1 , Rb 2 , Rc or diol-based saponin mixture, which is the main diol-type saponin of ginseng, is isolated from microorganisms in an aqueous solvent such as water, a buffer solution, or a mixture of an aqueous solvent and an organic solvent. beta-reacted with a-galactosidase a glycoside bond bonded to the glucose in the C 20 position in a short period of time is selectively cut is produced by ginsenosides Rd is a high yield.
본 발명에 사용되는 용매로는 물, 완충용액과 같은 효소의 활성을 저하시키지 않는 수성용매를 사용하는 것이 좋다. 바람직한 수성용매로는 pH 4~8 범위의 완충용액이 바람직하다. 전술한 수성용매는 단독으로 사용할 수도 있으나 다른 수성용매 및 유기용매와 혼합하여 사용할 수도 있는데, 혼합하여 사용할 수 있는 유기용매는 물과 혼화되면서 효소의 활성을 저하시키지 않는 것이어야 한다. 바람직한 유기용매로는 아세토니트릴, 디옥산, 디메틸 설폭사이드, 메탄올, 에탄올, 1-프로판올, 2-프로판올 등이 있으며, 유기용매의 사용량은 사용한 기질을 기준으로 1∼50% 농도가 되도록 하는 것이 바람직하다.As the solvent used in the present invention, it is preferable to use an aqueous solvent which does not lower the activity of enzymes such as water and a buffer solution. Preferred aqueous solvents are preferably buffer solutions in the range of pH 4-8. The above-mentioned aqueous solvent may be used alone, or may be used in combination with other aqueous solvents and organic solvents. The organic solvents that may be used in admixture should not be degrading the activity of the enzyme while being mixed with water. Preferred organic solvents include acetonitrile, dioxane, dimethyl sulfoxide, methanol, ethanol, 1-propanol, 2-propanol, and the like. The amount of the organic solvent is preferably 1 to 50% based on the substrate used. Do.
본 발명에 사용되는 효소로는 아스퍼질러스 또는 페니실리움속에서 분리한 락타제와 아스퍼질러스속에서 분리한 베타-갈락토시다제가 있으며, 이러한 효소의 첨가방법은 효소의 불활성화가 일어나지 않는 방법이라면 특별히 제한을 받지 않는다.The enzymes used in the present invention include lactase isolated from Aspergillus or penicillium and beta-galactosidase isolated from Aspergillus, and the addition of these enzymes is a method in which enzyme inactivation does not occur. Is not particularly limited.
반응온도는 효소의 불활성화가 일어나지 않는 온도조건이어야 하는데, 수성용매만을 사용하는 경우는 60℃이하가 바람직하고, 수성용매와 유기용매의 혼합액을 사용하는 경우는 40℃이하가 바람직하다. 본 발명에 사용되는 반응시간 역시 효소의 활성이 유지되는 기간이라면 특별히 제한을 받지 않으나 1∼72시간이 적당하다.The reaction temperature should be a temperature condition at which enzyme inactivation does not occur. When only an aqueous solvent is used, 60 ° C. or less is preferable, and when a mixed solution of an aqueous solvent and an organic solvent is used, 40 ° C. or less is preferable. The reaction time used in the present invention is not particularly limited as long as the activity of the enzyme is maintained, but 1 to 72 hours is appropriate.
본 발명에 의한 진세노사이드-Rd 제조방법을 구체적으로 설명하면 다음과 같다. 진세노사이드 Rb1, Rb2, Rc 또는 다이올계사포닌 혼합물을 수성용매 또는 수성용매와 유기용매의 혼합액에 용해시키고 미생물 유래의 락타제 또는 베타-갈락토시다제를 가하고 20∼60℃에서 1∼72시간 반응시킨 후 비등 수욕조에서 10분간 가열하여 효소를 불활성화시켜 진세노사이드 Rd가 다량 함유된 반응액을 얻는다. 이와 같은 효소적방법에 의하면 종래에는 진세노사이드 Rb1을 분리한 다음 효소적방법으로 Rd를 제조하였으나 본 방법에서는 Rb1을 분리하는 어려운 과정을 거치지 않고 사포닌혼합물을 효소와 반응시키면 단기간내에 진세노사이드 Rd만이 주로 생성되기 때문에 분리하기가 용이하다. 본 발명에 의해 제조된 생성물은 다음과 같은 물리화학적 성상을 나타내어 이를 진세노사이드 Rd로 동정하였다.Referring to the ginsenoside-Rd production method according to the present invention in detail. Ginsenosides Rb 1 , Rb 2 , Rc or diol-based saponin mixtures are dissolved in an aqueous solvent or a mixture of an aqueous solvent and an organic solvent, and lactose or beta-galactosidase derived from a microorganism is added to the mixture at 20 to 60 ° C. After the reaction for 72 hours, the reaction mixture was heated for 10 minutes in a boiling water bath to inactivate the enzyme to obtain a reaction solution containing a large amount of ginsenoside Rd. According to the enzymatic method, in the past, ginsenoside Rb 1 was isolated and then Rd was prepared by enzymatic method. However, in this method, if a saponin mixture is reacted with an enzyme without undergoing a difficult process of separating Rb 1 , the ginsenoside is reacted in a short time. Since only the side Rd is mainly produced, it is easy to separate. The product prepared by the present invention exhibited the following physical and chemical properties and was identified as ginsenoside Rd.
이하 본 발명을 실시 예에 의하여 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in detail with reference to Examples.
실시예 1Example 1
진세노사이드 Rb11g을 0.1M 초산완충용액(pH 4.5)에 용해시켜 전체를 50㎖로 정용한 다음 여기에 아스퍼질러스속에서 분리한 락타제 3g을 첨가하여 37℃ 수욕조상에서 교반하면서 48시간 반응시킨다. 박층크로마토그래피에 의해 주기적으로 확인하여 기질이 완전히 소실되면 열수중에서 10분간 가열하여 반응을 종료시킨 다음, 반응액은 수포화부탄올로 추출, 농축하여 진세노사이드 Rd가 9O% 이상 함유된 분말상 반응생성물을 얻었다. 1 g of ginsenoside Rb 1 was dissolved in 0.1 M acetic acid buffer solution (pH 4.5), and the whole was basified to 50 ml. Then, 3 g of lactase isolated from Aspergillus was added thereto and reacted for 48 hours while stirring in a 37 ° C. water bath. Let's do it. After periodic confirmation by thin layer chromatography, when the substrate is completely lost, the reaction is completed by heating in hot water for 10 minutes to terminate the reaction.The reaction solution is extracted with saturated butanol and concentrated to give a powdered reaction product containing more than 9O% of ginsenoside Rd. Got.
실시예 2Example 2
진세노사이드 Rb21g을 초산완충용액 (pH 4.8)에 용해시켜 전체를 5O㎖로 정용한 다음 아스퍼질러스속에서 분리한 베타-갈락토시다제 5g을 첨가하여 37℃ 수욕조상에서 교반하면서 72시간 반응시킨다. 반응액은 열수중 에서 10분간 가열하여 반응을 종료시킨 다음 수포화 부탄올로 추출, 농축하여 진세노사이드 Rd가 80%이상 함유된 반응생성물을 얻었다.1 g of ginsenoside Rb 2 was dissolved in acetic acid buffer solution (pH 4.8), and the whole was basified to 50 ml, followed by addition of 5 g of beta-galactosidase isolated from Aspergillus, followed by 72 hours stirring in a 37 ° C. water bath. Let's do it. The reaction solution was heated in hot water for 10 minutes to complete the reaction, followed by extraction with saturated butanol and concentration to obtain a reaction product containing more than 80% of ginsenoside Rd.
실시예 3Example 3
진세노사이드 Rc 1g을 초산완충용액 (pH 5.0)에 용해시켜 전체를 50㎖로 정용한 다음 여기에 페니실리움속에서 분리한 락타제 5g을 첨가하여 5O℃ 수욕조상에서 교반하면서 72시간 반응시킨다. 반응액은 열수중 에서 10분간 가열하여 반응을 종료시킨 다음 수포화 부탄올로 추출, 농축하여 분말상의 반응생성물 825㎎을 얻었다. 농축액은 실리카겔 컬럼크로마토그래피(클로로포름-메탄올-물=65:35 :10)에 의해 진세노사이드 Rd 678mg을 얻었다.1 g of ginsenoside Rc was dissolved in acetic acid buffer solution (pH 5.0), and the whole was subjected to 50 mL, and 5 g of lactase separated in penicillium was added thereto, followed by 72 hours of stirring in a 50 ° C. water bath. The reaction solution was heated in hot water for 10 minutes to complete the reaction, followed by extraction with saturated butanol to give 825 mg of powdered reaction product. The concentrate was purified by silica gel column chromatography (chloroform-methanol-water = 65:35:10) to obtain 678 mg of ginsenoside Rd.
실시예 4Example 4
진세노사이드 Rc 1g을 시트레이트 완충용액(pH 5.0)에 용해시켜 전체를 50㎖로 정용한 다음 아스퍼질러스속에서 분리한 베타-갈락토시다제 4g을 첨가하여 50℃ 수욕조상에서 교반하면서 72시간 반응시킨다. 반응액은 열수중에서 10분간 가열하여 반응을 종료시킨 다음 수포화 부탄올로 추출, 농축한다. 농축액은 실리카겔 컬럼 크로마토그래피(클로로포름-메탄올-물=65:35:10)에 의해 진세노사이드 Rd 594mg을 얻었다.1 g of ginsenoside Rc was dissolved in citrate buffer (pH 5.0), and the whole solution was passed to 50 ml, followed by addition of 4 g of beta-galactosidase isolated from Aspergillus, followed by 72 hours of stirring in a 50 ° C. water bath. Let's do it. The reaction solution is heated in hot water for 10 minutes to complete the reaction, followed by extraction with saturated butanol and concentration. The concentrate was purified by silica gel column chromatography (chloroform-methanol-water = 65:35:10) to give 594 mg of ginsenoside Rd.
실시예 5Example 5
진세노사이드 Rb1, Rb2, Rc 동량 혼합물 1g을 초산완충용액(pH 5.0)에 용해시켜 전체를 50㎖로 정용한 다음 페니실리움속에서 분리한 락타제 5g을 첨가하여 50℃수욕조상에서 교반하면서 72시간 반응시킨다. 반응액은 열수중에서 가열하여 반응을 종료시킨 다음 다이아이온 HP-20 수지를 충진한 컬럼에 흡착시킨 후 당류와 효소는 증류수로 세척하여 제거하고 반응생성물은 메탄올로 용출시켜 농축한다. 농축액은 실리카겔 컬럼 크로마토그래피(클로로포름-메탄올-물= 65:35:10, 하층)에 의해 진세노사이드 Rd 610mg을 얻었다. 1 g of ginsenosides Rb 1 , Rb 2 , Rc equivalent mixture was dissolved in acetic acid buffer solution (pH 5.0), the whole was basified to 50 ml, and 5 g of lactase separated in penicillium was added and stirred in a 50 ° C. water bath. The reaction is carried out for 72 hours. The reaction solution is heated in hot water to terminate the reaction. The reaction solution is adsorbed onto a column filled with DIION HP-20 resin, and sugars and enzymes are washed off with distilled water. The reaction product is eluted with methanol and concentrated. The concentrate was subjected to silica gel column chromatography (chloroform-methanol-water = 65:35:10, lower layer) to obtain 610 mg of ginsenoside Rd.
실시예 6Example 6
다이올계 사포닌이 주로 함유된 인삼근에서 분리한 조사포닌 분획 1g에 초산완충용액 (pH 5.0)에 용해시켜 전체를 50㎖로 정용한 다음 여기에 아스퍼질러스속에서 분리한 락타제 2g을 첨가하여 37℃의 수욕조상에서 교반하면서 48시간 반응시킨다. 반응액은 열수중 에서 가열하여 반응을 종료시킨 다음 수포화 부탄올로 추출후, 감압 농축한다. 농축액은 실리카겔 컬럼 크로마토그래피(클로로포름-메탄올-물=65:35:10, 하층)에 의해 진세노사이드 Rd 556mg을 얻었다.1 g of irradiated saponin was isolated from ginseng root containing mainly diol-based saponin, dissolved in acetic acid buffer solution (pH 5.0), and the whole was basified to 50 ml, and 2 g of lactase isolated from Aspergillus was added thereto at 37 ° C. The reaction is carried out for 48 hours while stirring in a water bath. The reaction solution is heated in hot water to terminate the reaction, extracted with saturated butanol and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (chloroform-methanol-water = 65:35:10, lower layer) to obtain 556 mg of ginsenoside Rd.
실시예 7Example 7
인삼 추출엑스 1g을 물에 용해시켜 전체를 50㎖로 정용한 다음 여기에 페니실리움속에서 분리한 락타제 3g을 첨가하여 37℃에서 48시간 반응시킨다. 반응액은 열수중 에서 가열하여 효소를 불활성화시킨 다음 수포화 부탄올로 추출, 농축한다. 농축액은 실리카겔 컬럼 크로마토그래피(클로로포름-메탄올-물=65:35:10, 하층)로 분리하여 진세노사이드 Rd가 40%이상 함유된 분말상 반응생성물을 얻었다.1 g of ginseng extract extract was dissolved in water, and the whole was applied to 50 ml. Then, 3 g of lactase separated in penicillium was added thereto and reacted at 37 ° C. for 48 hours. The reaction solution is heated in hot water to inactivate the enzyme, followed by extraction with saturated butanol and concentration. The concentrate was separated by silica gel column chromatography (chloroform-methanol-water = 65: 35: 10, lower layer) to obtain a powdery reaction product containing 40% or more of ginsenoside Rd.
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| KR100997441B1 (en) | 2010-05-24 | 2010-11-30 | 주식회사 한국천연물사이언스 | Method for preparing high purity ginsenoside rd using lactobacillus casei and cosmetic composition for anti-wrinkle comprising the high purity ginsenoside rd |
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| KR20020029138A (en) * | 2000-10-11 | 2002-04-18 | 복성해 | Recombinant enzyme from Thermus caldophilus GK24 strain and process for preparation of ginsenoside Rd using the same |
| KR100403570B1 (en) * | 2000-12-29 | 2003-10-30 | 주식회사 케이티앤지 | Method for the Production of Ginsenoside F2 by Enzymatic Process |
| KR100418604B1 (en) * | 2001-11-01 | 2004-02-11 | 주식회사 태평양 | Manufacturing method of Compound K and Ginsenoside F1 from ginseng ginsenosides |
| KR100420451B1 (en) * | 2001-11-27 | 2004-03-02 | 주식회사 케이티앤지 | The manufacturing method for ginsenoside compound k with cellulase or lactase composition y-ao |
| JP3678362B2 (en) * | 2002-07-23 | 2005-08-03 | 長谷川 秀夫 | Method for producing fermented carrot containing saponin degradation products |
| KR100618171B1 (en) * | 2003-04-30 | 2006-08-29 | 김재백 | Fermented red ginseng containing ginseng saponin degradate and its manufacturing method |
| KR100671291B1 (en) * | 2004-01-27 | 2007-01-18 | 주식회사 비티진 | A manufacturing method of ginsenoside F1 using beta-galactosidase |
| KR100689745B1 (en) * | 2005-05-23 | 2007-03-08 | 주식회사 비티진 | A preparation method for ginsenosides using ?-galactosidase |
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| JPS56127098A (en) * | 1980-05-08 | 1981-10-05 | Tsunematsu Takemoto | Preparation of saponin by enzymatic hydrolysis |
| JPS59163393A (en) * | 1983-03-08 | 1984-09-14 | Takuo Kosuge | Novel saponin derivative, its preparation, drug for promoting function of digestive and inspiratory opgans and enhancing physical strength, containing it |
| JPS6312300A (en) * | 1985-07-22 | 1988-01-19 | Takeda Chem Ind Ltd | Production of ginsenoside-rd |
| JPH0648946A (en) * | 1991-06-21 | 1994-02-22 | Takuo Kosuge | Tonic agent containing saponin derivative |
| KR19980027404A (en) * | 1996-10-16 | 1998-07-15 | 박명규 | Preparation of 20 (S) -ginsenoside Rh₁ and 20 (S) -protopyranthracene |
| KR19990000458A (en) * | 1997-06-05 | 1999-01-15 | 박명규 | Method for preparing Rg3 of ginsenosides |
| KR19990000457A (en) * | 1997-06-05 | 1999-01-15 | 박명규 | Method for preparing trace ginsenosides |
| KR19990074669A (en) * | 1998-03-13 | 1999-10-05 | 박명규 | Ginsenoside AL-beta-di-xyloxide and its preparation method by enzymatic method |
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| JPS56127098A (en) * | 1980-05-08 | 1981-10-05 | Tsunematsu Takemoto | Preparation of saponin by enzymatic hydrolysis |
| JPS59163393A (en) * | 1983-03-08 | 1984-09-14 | Takuo Kosuge | Novel saponin derivative, its preparation, drug for promoting function of digestive and inspiratory opgans and enhancing physical strength, containing it |
| JPS6312300A (en) * | 1985-07-22 | 1988-01-19 | Takeda Chem Ind Ltd | Production of ginsenoside-rd |
| JPH0648946A (en) * | 1991-06-21 | 1994-02-22 | Takuo Kosuge | Tonic agent containing saponin derivative |
| KR19980027404A (en) * | 1996-10-16 | 1998-07-15 | 박명규 | Preparation of 20 (S) -ginsenoside Rh₁ and 20 (S) -protopyranthracene |
| KR19990000458A (en) * | 1997-06-05 | 1999-01-15 | 박명규 | Method for preparing Rg3 of ginsenosides |
| KR19990000457A (en) * | 1997-06-05 | 1999-01-15 | 박명규 | Method for preparing trace ginsenosides |
| KR19990074669A (en) * | 1998-03-13 | 1999-10-05 | 박명규 | Ginsenoside AL-beta-di-xyloxide and its preparation method by enzymatic method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100997441B1 (en) | 2010-05-24 | 2010-11-30 | 주식회사 한국천연물사이언스 | Method for preparing high purity ginsenoside rd using lactobacillus casei and cosmetic composition for anti-wrinkle comprising the high purity ginsenoside rd |
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