KR950005738B1 - Separation and purification of polysaccharide with nitrogen from taraxaci radix - Google Patents

Separation and purification of polysaccharide with nitrogen from taraxaci radix Download PDF

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KR950005738B1
KR950005738B1 KR1019910025473A KR910025473A KR950005738B1 KR 950005738 B1 KR950005738 B1 KR 950005738B1 KR 1019910025473 A KR1019910025473 A KR 1019910025473A KR 910025473 A KR910025473 A KR 910025473A KR 950005738 B1 KR950005738 B1 KR 950005738B1
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distilled water
polysaccharides
precipitate
nitrogen
dissolved
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KR930012803A (en
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김상준
곽의종
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주식회사선경인더스트리
이승동
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A61K36/288—Taraxacum (dandelion)

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Abstract

The dried herb powder was mixed with 80-100% lower alcohol to removc the melted compounds and the residue was reflux-extracted with adding the distilled water then the solution was centrifugal-separated to remove the residue. The remained upper solution was concentrated under the reduced pressure to precipitate and then the precipitate was melted in the distilled water and ultrafiltrated to give nitrogen-containing polysaccharoid.

Description

황화지정으로부터 질소함유 다당류의 분리 정제방법Separation and Purification Method of Nitrogen-Containing Polysaccharides from Sulfide Specified

본 발명은 황화지정으로부터 질소함유 다당을 분리 정제하는 방법에 관한 것으로서, 더욱 상세하게는 한약재로 사용되는 황화지정 (일명 포공영)으로부터 유효생체활성물질을 질소함유 다당을 고순도, 고수율로 분리, 정제하는 방법에 관한 것이다.The present invention relates to a method for separating and purifying a nitrogen-containing polysaccharide from a sulfide designation, and more particularly, to separate and purify a nitrogen-containing polysaccharide with high purity and high yield from an sulfide designation (aka pogongyoung) used as a herbal medicine. It is about how to.

황화지정은 국화과 식물의 전초로서 한의학적 약리작용으로는 청열해독, 이담, 이뇨, 각종 염증치료, 건위작용이 있는 것으로 알려져 있다. 그 주요성분으로는 타락사신(Taraxacin), 타락사롤(Taraxarol), 타락 사코사이드 (Taraxacoside), 여러지 방산, 이눌린 (Inulin) 베타-시토스테롤 (β- Sitosterol), β-아미린 (β-Amyrin), 다당류 등이 알려져 있다.Sulfurization designation is an outpost of asteraceae plants, and it is known that oriental medicine pharmacological action has clear heat detoxification, edema, diuresis, various inflammatory treatments, and health. Its main ingredients are Taraxacin, Taraxalol, Taraxacoxide, various acids, Inulin Beta-Sitosterol, β-Amyrin , Polysaccharides and the like are known.

일반적으로 다당류 등은 면역촉진작용(Immuno stimulant effect)을 갖고 있는 것으로 알려져 있는 바 본 발명은 황화지정으로부터 생체활성을 갖는 질소함유다당을 고순도, 고수율로 분리, 정제하는 방법의 개발과 이 물질의 면역촉진작용의 연구에서 이루어진 것이다.In general, polysaccharides and the like are known to have an immunostimulating effect. The present invention provides a method for separating and purifying nitrogen-containing polysaccharides having high activity and high purity from the sulfidation method and the purification of these substances. This was done in the study of immunostimulating action.

한편, 일본 약학잡지 (101(6), 538∼543, 1981)에서는 이와 같은 생체활성을 갖는 질소함유 다당을 황화지정으로부터 분리하여 in vivo로 생체활성을 입증하였는바, 이 문헌에 따르면, 황화지정을 85%에탄올로 추출하여 유기용매에 녹는 물질을 제거한 후 증류수로 환류, 추출하고 한외여과법으로 저분자 물질이 제거된 열수추출물을 암세포가 이식된 ddY계 마우스에 복강 투여하여 종양 무게를 관찰하였다. 그 결과 20일간 투여후 대조군과의 비교 결과 종양무게가 상당히 감소되었음을 나타내었다. 따라서 이 열수추출물이 제암활성을 갖는 것으로 발로되었다.On the other hand, Japanese pharmacy magazine (101 (6), 538 to 543, 1981) has demonstrated the bioactivity in vivo by separating nitrogen-containing polysaccharides having such bioactivity from the sulfidation specification, according to this document. Was extracted with 85% ethanol to remove the substance dissolved in the organic solvent, refluxed with distilled water, and extracted by ultrafiltration, the hot water extract from which the low molecular weight material was removed was intraperitoneally administered to ddY mice implanted with cancer cells to observe the tumor weight. As a result, the tumor weight was significantly decreased after 20 days of administration compared with the control group. Therefore, this hot water extract was found to have anticancer activity.

본 발명자들은 열수추출물에서 생체활성을 갖는 고분자물질을 분리 정제함에 있어서 세파텍스 또는 이온 교환수지 컬럼을 이용하지 않고도 고순도, 고수율로 정제하는 아주 효율적이고 간단한 방법을 개발하였고 이렇게하여 얻어진 질소함유 다당의 in vivo 또는 in vitro 실험을 통하여 생체활성도를 입증함으로서 본 발명을 완성하게 되었다.The present inventors have developed a very efficient and simple method for purifying high purity and high yield without separating Sephatex or ion exchange resin column in separating and purifying bioactive polymers from hot water extract. The present invention has been completed by proving bioactivity through in vivo or in vitro experiments.

따라서, 본 발명의 목적은 황화지정으로부터 생체활성을 갖는 질소함유 다당을 분리 정제하는 방법 및 그 활용방안을 제공하는데 그 목적이 있다.Accordingly, an object of the present invention is to provide a method for separating and purifying a nitrogen-containing polysaccharide having bioactivity from a sulfidation designation and a method of using the same.

이하, 본 발명을 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in detail.

본 발명은 황화지정으로부터 생체활성을 갖는 질소함유 다당류를 분리, 정제함에 있어서, 다음 (가) 내지 (라) 공정을 통하여 분리 정제하는 것을 특징으로한다.The present invention is characterized in that the separation and purification of nitrogen-containing polysaccharides having bioactivity from the designated sulfides are separated and purified through the following steps (a) to (d).

(가) 마쇄한 황화지정 건조분말에 80∼100% 저급알콜을 가하여 유기용매에 녹는 물질들을 추출 제거하고 남은 황화지정 잔체에 증류수를 가하여 환류 추출한 다음, 이를 원심분리하여 잔사를 제거하고 상등액을 감압농축한 후, 저급알콜을 가하여 생성된 침전물을 증류수에 녹인 다음 증류수에 대하여 한외여과법으로 여과하여 조엑기스를 분리하는 공정.(A) Add 80-100% lower alcohol to the ground sulfided dry powder, extract and remove the soluble substances in the organic solvent, add distilled water to the remaining sulfided residue, reflux and extract it, and centrifuge to remove the residue and depressurize the supernatant. After concentration, the lower alcohol is added to dissolve the precipitate produced in distilled water and then filtered by ultrafiltration for distilled water to separate the crude extract.

(나) 이 조엑기스를 수용액으로 만든후 여기에 헥사데실트리메틸 암모늄브로마이드(Hexadecyltrimethyl ammonium bomide, 이하 CTA-Br이라 함) 수용액을 가하여 산성다당류는 침전물로, 중성다당류는 상등액으로 각각 분리하는 공정.(B) Making this crude extract into an aqueous solution, and adding an aqueous solution of hexadecyltrimethyl ammonium bomide (hereinafter referred to as CTA-Br) to acidic polysaccharide as a precipitate, and neutral polysaccharide as a supernatant.

(다) 침전으로 형성된 산성다당류를 디메틸설폭사이드 또는 무기염류수용액에 녹인 후 여과하고 그 여액에 저급알콜을 가한후, 원심분리하여 얻은 침전 물을 증류수에 녹인 다음 한외여과법으로 질소함유 다당류를 정제하는 공정.(C) The acid polysaccharides formed by precipitation are dissolved in dimethylsulfoxide or inorganic salt aqueous solution, filtered, low alcohol is added to the filtrate, and the precipitate obtained by centrifugation is dissolved in distilled water and purified by nitrogen filtration. fair.

(라) 중성다당류가 존재하는 상등액에 무기염류수용액을 가하여 수소이온농도를 11∼13으로 조정한 후 원심분리하고, 여기서 생긴 침전물을 디메틸설폭사이드 또는 무기염류 수용액에 녹인 후 여과하고 그 여액에 저급알콜을 가한 후 원심분리하여 얻은 침전물을 증류수에 녹인 다음 한외여과법으로 여과하여 질소함유 다당류를 정제하는 공정.(D) Add an aqueous inorganic salt solution to the supernatant containing neutral polysaccharides, adjust the hydrogen ion concentration to 11-13, and centrifuge. The precipitate is dissolved in dimethyl sulfoxide or an aqueous inorganic salt solution and filtered. A process of purifying nitrogen-containing polysaccharides by dissolving the precipitate obtained by adding alcohol to centrifugation in distilled water and then filtering by ultrafiltration.

이와 같은 본 발명을 하나의 구현예로서 더욱 상세히 설명하면 다음과 같다.If the present invention is described in more detail as an embodiment as follows.

마쇄한 황화지정 건조분말 1kg에 80∼10% 저급알콜을 가하여 유기용매에 녹는 물질들을 추출 제거하고 남은 식물잔체에 증류수 3∼5ℓ를 가하여 12∼24시간 환류 추출한 다음, 이를 원신분리하여 잔사를 제거하고 상등액을 1/4부피로 감압농축한 후 저급알콜을 4∼5배의 부피비로 가한후 생성된 침전물을 증류수에 녹인 다음 증류수에 대하여 한외여과법으로 저분자물질이 제거된 조엑기스를 제조한다.80 kg to 10% lower alcohol was added to 1 kg of the ground sulfide-specified dry powder, and the substances dissolved in the organic solvent were extracted and removed. 3-5 L of distilled water was added to the remaining plant residue, and the mixture was extracted under reflux for 12 to 24 hours. Then, the supernatant was concentrated under reduced pressure to 1/4 volume, low alcohol was added at a volume ratio of 4 to 5 times, and then the resulting precipitate was dissolved in distilled water to prepare a crude extract from which low molecular weight material was removed by ultrafiltration.

조엑기스를 0.5∼2%수용액으로 만든 후 4∼8% CTA-Br수용액을 더이상의 침전이 생성되지 않을때까지 가한후 원심분리하여 침전물과 상등액을 분리한다. 분리된 침전물을 디메틸설폭사이드 또는 3∼5M 무기염류 수용액 500∼1000ml에 녹인후 여과하고 그 여액에 저급알콜을 4∼5배의 부피비로 가한후, 원심분리하여 얻은 침전물을 증류수에 녹인다음 증류수에 대하여 한외여과법으로 저분자 물질을 제거하고 농축하여 생체 활성을 갖는 질소함유다당 2.5∼3.5g을 얻는다.The crude extract is made into 0.5-2% aqueous solution, 4-8% CTA-Br aqueous solution is added until no precipitate is formed, and then the precipitate and the supernatant are separated by centrifugation. The separated precipitate was dissolved in 500-1000 ml of dimethyl sulfoxide or 3-5 M inorganic salt solution, filtered and the lower alcohol was added to the filtrate at a volume ratio of 4-5 times. The precipitate obtained by centrifugation was dissolved in distilled water and then distilled water. The low molecular weight material was removed by ultrafiltration and concentrated to obtain 2.5-3.5 g of nitrogen-containing polysaccharide having biological activity.

조엑기스를 CTA-Br수용액으로 처리한 상등액에 0.5∼2N 수산화나트륨 수용액을 가하여 수소이온농도를 11∼13으로 조정한후 원심분리하고, 여기서 생긴 침전물을 디메틸설폭사이드 또는 3∼5M 무기염류 수용액 250∼500ml에 녹인 후 여과하고 그 여액에 저급알콜을 4∼5배의 부피비로 가한후, 원심분리하여 얻은 침전물을 증류수에 녹인다음 증류수에 대하여 한외여과법으로 저분자 물질을 제거하고 농축하여 생체활성을 갖는 질소함유 다당 0.5∼1.5g을 얻는다.To the supernatant treated with the crude extract with CTA-Br aqueous solution, 0.5-2 N aqueous sodium hydroxide solution was added to adjust the hydrogen ion concentration to 11-13, followed by centrifugation. The precipitate formed therefrom was diluted with dimethyl sulfoxide or 3-5 M inorganic salt aqueous solution 250-. After dissolving in 500ml and filtering, the lower alcohol was added to the filtrate at a volume ratio of 4 to 5 times, and the precipitate obtained by centrifugation was dissolved in distilled water. 0.5-1.5 g of polysaccharides are obtained.

본 발명에서 사용된 상기 저급알콜로서는 예컨대 에탄올이 사용되며, 3-5M의 무기염류수용액은 염화나트륨수용액이 사용된다.As the lower alcohol used in the present invention, for example, ethanol is used, and an aqueous sodium chloride solution of 3-5 M is used as an aqueous sodium chloride solution.

이와 같이, 본 발명에 따라 분리 정제된 상기의 두종류의 질소함유 다당들의 평균분자량은 표준시료로서 단백질을 기준으로 하였을때 각각 500,000∼1,200,000이며 면역증강 효과가 있음은 쥐에 대한 실험을 통하여 확인하였는바이로써 두물질이 항암효과가 있는 것으로 판단된다.As such, the average molecular weights of the two types of nitrogen-containing polysaccharides separated and purified according to the present invention were 500,000 to 1,200,000, respectively, based on protein as a standard sample, and the immuno-boosting effect was confirmed through experiments in mice. By virtue, the two substances are thought to have anticancer effects.

이하, 본 발명을 실시예에 의거하여 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in detail with reference to Examples.

[실시예 1]Example 1

마쇄한 황화지정 건조분말 1kg에 80% 메탄올을 가하여 녹는 물질을 추출 제거하고 남은 황화지정 잔체에 증류수 4ℓ를 가하여 12시간 환류 추출한 다음 이를 원심분리하여 잔사를 제거하고 상등액을 1ℓ로 감압 농축한후 에탄올 4ℓ을 가한후 생성된 침전물을 증류수 1000ml에 녹인다음 증류수에 대하여 한외여과법으로 저분자 물질을 제거하고 농축하여 조엑기스 32g을 얻는다.Extract 80% methanol to 1kg of the ground sulfide-designated dry powder, remove the dissolved substance, add 4 liters of distilled water to the remaining sulfide residue, reflux for 12 hours, remove the residue by centrifugation, and concentrate the supernatant under reduced pressure to 1ℓ. After adding 4 L, the resulting precipitate is dissolved in 1000 ml of distilled water, and then the low molecular weight material is removed by ultrafiltration with distilled water and concentrated to obtain 32 g of crude extract.

조엑기스를 증류수에 녹여서 0.1% 수용액으로 만든후 7% CTA-Br수용액을 침전이 생성되지 않을때까지 가한후 원심분리하여 침전물과 상등액을 분리한다. 분리된 침전물을 4M염화나트륨 수용액 700ml에 녹인후 여과하고 그 여액에 에탄올 2800ml을 가한후 원심분리하여 얻은 침전물을 증류수 100ml에 녹인후 증류수에 대하여 한외여과법으로 저분자 물질을 제거한다음 농축하여 생체활성을 갖는 질소함유 다당류 3.2g을 얻는다(수율 0.32%).Dissolve the crude extract in distilled water to make 0.1% aqueous solution, add 7% CTA-Br aqueous solution until no precipitate is formed, and centrifuge to separate the precipitate and the supernatant. The separated precipitate was dissolved in 700 ml of 4M aqueous sodium chloride solution, filtered, 2800 ml of ethanol was added to the filtrate, and the precipitate obtained by centrifugation was dissolved in 100 ml of distilled water. 3.2 g of containing polysaccharides are obtained (yield 0.32%).

조엑기스를 CTA-Br수용액으로 처리한 상등액에 1N수산화나트륨 수용액을 가하여 수소이온 농도를 13으로 조정한후 원심분리하고 생긴 침전물을 4M염화나트륨 수용액 400m1에 녹인후 여과하고 그 여액에 에탄올 1600ml을 가한후 원신분리하여 얻은 침전물을 증류수 100ml 녹인다음 증류수에 대하여 한외여과법으로 저분자 물질을 제거하고 농축하여 생체활성을 갖는 질소함유 다당 1.2g을 얻는다(수율 0.12%).The supernatant treated with crude extract with CTA-Br aqueous solution was added with 1N aqueous sodium hydroxide solution, the hydrogen ion concentration was adjusted to 13, and then centrifuged. The precipitate obtained by the new separation is dissolved in 100 ml of distilled water, and then the low molecular weight material is removed by ultrafiltration with distilled water and concentrated to obtain 1.2 g of nitrogen-containing polysaccharide having bioactivity (yield 0.12%).

[실시예 2]Example 2

실시예 1과 동일한 방법으로 제조한 조엑기스를 0.1% 수용액으로 만든후 7% CTA-Br수용액을 침전이 생성되지 않을때까지 가한후 원심분리하여 침전물과 상등액을 분리한다.The crude extract prepared in the same manner as in Example 1 was made into 0.1% aqueous solution, and 7% CTA-Br aqueous solution was added until no precipitate was formed, and then the precipitate and the supernatant were separated by centrifugation.

분리된 침전물을 디메틸설폭사이드 1000ml에 녹인후 여과하고 그 여액에 에탄올 4ℓ을 가한후 원심분리하여 얻은 침전물을 증류수 100ml에 녹인후 증류수에 대하여 한외여과법으로 저분자 물질을 제거한다음 농축하여 생체활성을 갖는 질소함유 다당류 2.6g을 얻는다(수율 0.26%).The separated precipitate was dissolved in 1000 ml of dimethyl sulfoxide, filtered, and 4 liters of ethanol was added to the filtrate. The precipitate obtained by centrifugation was dissolved in 100 ml of distilled water, and the low molecular weight was removed by ultrafiltration. 2.6 g of containing polysaccharides are obtained (yield 0.26%).

조엑기스를 CTA-Br수용액으로 처리한 상등액에 1.5N 수산화나트륨 수용액을 가하여 수소이온 농도를 12.5로 조정한후 원심분리하고 생긴 침전물을 디메틸설폭사이드 500ml에 녹인후 여과하고 그 여액에 에탄올 2000ml을 가한후 원심 분리하여 얻은 침전물을 증류수 100ml에 녹인다음 증류수에 대하여 한외여과법으로 저분자 물질을 제거하고 농축하여 생체활성을 갖는 질소함유 다당 0.7g을 얻는다(수율 0.07%).1.5N sodium hydroxide solution was added to the supernatant treated with the crude extract with CTA-Br aqueous solution, the hydrogen ion concentration was adjusted to 12.5, centrifuged and the resulting precipitate was dissolved in 500ml of dimethyl sulfoxide and filtered. The precipitate obtained by centrifugation was dissolved in 100 ml of distilled water, and then the low molecular weight material was removed by ultrafiltration with distilled water and concentrated to obtain 0.7 g of a polysaccharide having a bioactivity (yield 0.07%).

상기 실시예 1에서 얻은 두종류의 질소함유 다당의 화학적 분석자료를 다음 표 1, 2에 나타내었다.Chemical analysis data of two types of nitrogen-containing polysaccharides obtained in Example 1 are shown in Tables 1 and 2 below.

시료 1 : 조엑기스를 CTA-Br 수용액으로 처리한후 원심분리하여 얻은 침전물로 부터 얻은 질소함유 다당.Sample 1: Nitrogen-containing polysaccharide obtained from the precipitate obtained by treating crude extract with CTA-Br aqueous solution and centrifuging.

시료 2 : 조엑기스를 CTA-Br 수용액으로 처리한후 원심분리하여 얻은 상등액으로 부터 얻은 질소함유 다당.Sample 2: Nitrogen-containing polysaccharide obtained from the supernatant obtained by treating crude extract with CTA-Br aqueous solution and centrifuging.

[표 1]TABLE 1

[정색반응][Color reaction]

[표 2]TABLE 2

[성분조성][Composition]

1. 당정량 : 페놀-황산법1. Sugar equivalent: phenol-sulfuric acid method

2. 단백질 : 로우리법(Lowry et al., J. Biol. Chem. 193 : 265, 1951)2. Protein: Lowry et al., J. Biol. Chem. 193: 265, 1951

3. 수분 : 열천칭 TSG를 사용한 표준열 무게 측정3. Moisture: Standard heat weight measurement using thermobalance TSG

상기 실시예 1에서 얻은 시료 1과 2에 대한 면역증강 효과에 의한 항암작용을 다음 표 3에 나타내었는바 이 실험은 무균실에서 사육한 ICR계 마우스를 가지고 일반적 항암실험과 동일하게 실시하였다.The anticancer action by the immuno-enhancing effect on the samples 1 and 2 obtained in Example 1 is shown in the following Table 3. This experiment was carried out in the same manner as the general anticancer test with ICR mice bred in clean room.

[표 3]TABLE 3

Claims (1)

황화지정으로부터 생체활성을 갖는 질소함유 다당류를 분리 정제함에 있어서, 다음 (가) 내지 (라) 공정을 통하여 이루어지는 것을 특징으로 하는 분리 정제방법.Separation and purification of nitrogen-containing polysaccharides having bioactivity from designated sulfides, comprising the following steps (a) to (d). (가) 마쇄한 황화지정 건조분말에 80∼100%저급알콜을 가하여 유기용매에 녹는 물질들을 추출 제거하고 남은 황화지정 잔체에 증류수를 가하여 환류 추출한 다음, 이를 원심분리하여 잔사를 제거하고 상등액을 감압 농축한 후, 저급알콜을 가하여 생성된 침전물을 증류수에 녹인 다음 증류수에 대하여 한여과법으로 여과하여 조엑기스를 분리하는 공정.(A) Add 80-100% lower alcohol to the ground sulfided dry powder, extract and remove the soluble substances in the organic solvent, add distilled water to the remaining sulfided residue, reflux and extract it, and centrifuge to remove the residue and depressurize the supernatant. After concentration, the lower alcohol is added to dissolve the precipitate produced in distilled water and then filtered through distilled water by ultrafiltration to separate the crude extract. (나) 이 조엑기스를 수용액으로 만든후 여기에 헥사데실트리메틸 암모늄브로마이드(Hexadecyltrimethyl ammonium bromide) 수용액을 가하여 산성다당류는 침전물로, 중성다당류는 상등액으로 각각 분리하는 공정.(B) This crude extract is made into an aqueous solution, and hexadecyltrimethyl ammonium bromide is added thereto to separate acidic polysaccharides as precipitates and neutral polysaccharides as supernatants. (다) 침전으로 형성된 산성다당류를 디메틸설폭사이드 또는 무기염류수용액에 녹인 후 여과하고 그 여액에 저급알콜을 가한후, 원심분리하여 얻은 침전물을 증류수에 녹인 다음 한외여과법으로 여과하여 질소함유 다당류를 정제하는 공정.(C) The acid polysaccharides formed by precipitation are dissolved in dimethylsulfoxide or inorganic salt aqueous solution, filtered and lower alcohol is added to the filtrate. The precipitate obtained by centrifugation is dissolved in distilled water and filtered by ultrafiltration to purify nitrogen-containing polysaccharides. Process. (라) 중성다당류가 존재하는 상등액에 무기염류수용액을 가하여 수소이온농도를 11∼13으로 조정한 후 원심분리하고, 여기서 생긴 침전물을 디메틸설폭사이드 또는 무기염류 수용액에 녹인 후 여과하고 그 여액에 저급알콜을 가한후 원심분리하여 얻은 침전물을 증류수에 녹인 다음 한외여과법으로 여과하여 질소함류 다당류를 정제하는 공정.(D) Add an aqueous inorganic salt solution to the supernatant containing neutral polysaccharides, adjust the hydrogen ion concentration to 11-13, and centrifuge. The precipitate is dissolved in dimethyl sulfoxide or an aqueous inorganic salt solution and filtered. A process of purifying nitrogen-containing polysaccharides by dissolving the precipitate obtained by adding alcohol to distilled water and filtering by ultrafiltration.
KR1019910025473A 1991-12-30 1991-12-30 Separation and purification of polysaccharide with nitrogen from taraxaci radix KR950005738B1 (en)

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