JPH1192492A - Method for separating 3-o-glucopyranosyl-gamma-butyrolactone - Google Patents
Method for separating 3-o-glucopyranosyl-gamma-butyrolactoneInfo
- Publication number
- JPH1192492A JPH1192492A JP9273498A JP27349897A JPH1192492A JP H1192492 A JPH1192492 A JP H1192492A JP 9273498 A JP9273498 A JP 9273498A JP 27349897 A JP27349897 A JP 27349897A JP H1192492 A JPH1192492 A JP H1192492A
- Authority
- JP
- Japan
- Prior art keywords
- genus
- glucopyranosyl
- butyrolactone
- water
- chloroform
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、3-0-グルコピラノ
シル-γ-ブチロラクトンの分離方法に関する。更に詳し
くは、アネクトキルス属植物またはシュスラン属植物の
抽出エキスから3-0-グルコピラノシル-γ-ブチロラクト
ンを分離する方法に関する。[0001] The present invention relates to a method for separating 3-0-glucopyranosyl-γ-butyrolactone. More specifically, the present invention relates to a method for separating 3-0-glucopyranosyl-γ-butyrolactone from an extract of a plant belonging to the genus Anectocillus or the plant belonging to the genus Suslan.
【０００２】[0002]
【従来の技術】3-0-グルコピラノシル-γ-ブチロラクト
ンは、台湾を原産地とするラン科アネクトキルス属植物
の金線蓮(Anoectochillus formosanus Hay., A. koshun
ensis,A. roxiburghii)より単離される配糖体化合物で
ある(Phytochemistry第33巻第1133〜7頁、1993)。 2. Description of the Related Art 3-0-Glucopyranosyl-γ-butyrolactone is a genus of Anoectochillus formosanus Hay.
ensis, A. roxiburghii) (Phytochemistry Vol. 33, pp. 1133-7, 1993).
【０００３】この配糖体化合物は、血中の糖濃度を低下
させる作用に対してすぐれた効果を示すので、糖尿病の
予防および治療に対して有効であり、また血中総コレス
テロール値を低下させる作用および血中トリグリセリド
値を低下させる作用に対してもすぐれた効果を示すの
で、コレステロールの過剰摂取によってひき起される様
々な疾患の予防および治療に対しても有効な生理活性物
質である。[0003] The glycoside compound has an excellent effect on the action of lowering the blood sugar concentration, so that it is effective for the prevention and treatment of diabetes and also lowers the total blood cholesterol level. Since it has an excellent effect on the action and the action of lowering the blood triglyceride level, it is a bioactive substance which is also effective for the prevention and treatment of various diseases caused by excessive intake of cholesterol.
【０００４】しかしながら、この化合物を金線蓮等の抽
出エキスから従来法によって単離および精製しようとす
ると、その精製過程で目的化合物が分解し易いため、収
率を低下させるばかりではなく、精製自体をも困難なも
のとしている。However, if this compound is to be isolated and purified from an extract such as gold wire lotus by a conventional method, the target compound is easily decomposed in the purification process. Is also difficult.
【０００５】因みに、前記先行文献では、Anoectochill
us koshunensisの場合、新鮮な全草6Kgから目的化合物
が83mgしか得られず、その収率は0.01%以下にとどまっ
ている。また、これの精製過程で3-0-グルコピラノシル
-γ-ブチロラクトンの加溶媒反応が進み、結果的に殆ん
どがその分解産物しか得られないこともある。[0005] Incidentally, in the above-mentioned prior art, Anoectochill
In the case of us koshunensis, only 83 mg of the target compound is obtained from 6 kg of fresh whole plant, and the yield is less than 0.01%. In addition, 3-0-glucopyranosyl
In some cases, the solvolysis reaction of -γ-butyrolactone proceeds, and as a result, almost all of the decomposition products are obtained.
【０００６】[0006]
【発明が解決しようとする課題】本発明の目的は、アネ
クトキルス属植物またはシュスラン属植物の抽出エキス
から、従来法よりも著しく好収率で3-0-グルコピラノシ
ル-γ-ブチロラクトンを分離する方法を提供することに
ある。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for separating 3-0-glucopyranosyl-γ-butyrolactone from an extract of a plant belonging to the genus Anectocillus or the plant belonging to the genus Suslan in a significantly higher yield than the conventional method. To provide.
【０００７】[0007]
【課題を解決するための手段】かかる本発明の目的は、
アネクトキルス属植物からの有機溶媒抽出エキスをクロ
ロホルムと水とで溶媒間分配し、その水層部分をn-ブタ
ノールとの間で溶媒間分配した後、得られた水溶性フラ
クションをスチレン-ジビニルベンゼン共重合樹脂系吸
着剤を用いたカラムクロマトグラフィーに付し、その水
溶出フラクションをシリカゲルを用いたカラムクロマト
グラフィーに付し、クロロホルム-エタノール混合溶媒
で溶出し、3-0-グルコピラノシル-γ-ブチロラクトンを
分離する方法によって達成される。なお、シュスラン属
植物の場合には、n-ブタノールによる溶媒間分配および
スチレン−ジビニルベンゼン共重合樹脂系吸着剤を用い
たクロマトグラフィーを必要としない。SUMMARY OF THE INVENTION The object of the present invention is as follows.
After extracting the organic solvent extract from the plant of the genus Anectocillus with chloroform and water, the aqueous layer was partitioned between n-butanol and the solvent, and the resulting water-soluble fraction was combined with styrene-divinylbenzene. It was subjected to column chromatography using a polymerized resin-based adsorbent, the water-eluting fraction was subjected to column chromatography using silica gel, and eluted with a chloroform-ethanol mixed solvent to give 3-0-glucopyranosyl-γ-butyrolactone. Achieved by the method of separation. In the case of a plant of the genus Suslan, partition between solvents by n-butanol and chromatography using a styrene-divinylbenzene copolymer resin-based adsorbent are not required.
【０００８】[0008]
【発明の実施の形態】金線蓮等のアネクトキルス属植物
またはその近縁植物であるカゴメラン、ミヤマウズラ等
のシュスラン属植物は、生のままあるいは乾燥した全草
をそのままの状態であるいは粉末状にして、有機溶媒に
よる室温あるいは加熱抽出に付される。有機溶媒として
は、メタノール、エタノール、アセトン等が用いられ、
これらは水との混合溶媒としても用いられる。BEST MODE FOR CARRYING OUT THE INVENTION Plants of the genus Anectocirus, such as a gold wire lotus, or plants of the genus Suslan, such as kagomelan and mountain quail, which are closely related plants, are raw or dried whole plants as they are or in powder form. The mixture is subjected to extraction with an organic solvent at room temperature or by heating. As the organic solvent, methanol, ethanol, acetone or the like is used,
These are also used as a mixed solvent with water.
【０００９】有機溶媒によって抽出され、溶媒を留去し
て得られた抽出エキスは、まずクロロホルムと水とで溶
媒間分配した後、アネクトキルス属植物の場合には、そ
の水層部分がn-ブタノールとの間で好ましくは5回以上
溶媒間分配され、これによって脂溶性部分および色素が
除去される。得られた水溶性フラクションは、スチレン
-ジビニルベンゼン共重合樹脂系吸着剤を用いたカラム
クロマトグラフィーに付し、その後水溶出フラクション
をシリカゲルを用いたカラムクロマトグラフィーに付
し、クロロホルム-エタノール混合溶媒で溶出する。シ
ュスラン属植物の場合には、夾雑する色素が少ないの
で、n-ブタノールによる溶媒間分配およびスチレン−ジ
ビニルベンゼン共重合樹脂系吸着剤による粗精製工程を
格別必要としない。The extracted extract obtained by extracting with an organic solvent and distilling off the solvent is firstly partitioned between chloroform and water, and then, in the case of Anectocillus plants, the aqueous layer is n-butanol. And preferably 5 or more times between the solvent, thereby removing the fat-soluble portion and the dye. The water-soluble fraction obtained is styrene
-Column chromatography using a divinylbenzene copolymer resin-based adsorbent, and then water-eluting fraction is subjected to column chromatography using silica gel, and eluted with a chloroform-ethanol mixed solvent. In the case of a plant of the genus Suslan, since the amount of contaminating pigment is small, a partitioning between solvents using n-butanol and a crude purification step using a styrene-divinylbenzene copolymer resin-based adsorbent are not particularly required.
【００１０】このシリカゲルを用いたカラムからの溶出
に際し、水およびメタノールを含まない溶出溶媒を使用
することが絶対に必要である。ここで、水およびメタノ
ールを含む溶出溶媒を使用すると、3-0-グルコピラノシ
ル-γ-ブチロラクトンの加溶媒分解が起り、収率を低下
させるばかりではなく、分解産物によって3-0-グルコピ
ラノシル-γ-ブチロラクトン自体の精製を困難とさせ
る。また、このような溶出溶媒をくり返し使用した場合
には、3-0-グルコピラノシル-γ-ブチロラクトンがどん
どん分解され、殆んどが分解産物となってしまう。For elution from the column using silica gel, it is absolutely necessary to use an elution solvent free of water and methanol. Here, when an elution solvent containing water and methanol is used, solvolysis of 3-0-glucopyranosyl-γ-butyrolactone occurs, not only reducing the yield, but also decomposing products to 3-0-glucopyranosyl-γ-. This makes purification of butyrolactone itself difficult. In addition, when such an elution solvent is used repeatedly, 3-0-glucopyranosyl-γ-butyrolactone is rapidly decomposed, and almost all are decomposed products.
【００１１】そのために、本発明においては、クロロホ
ルム-エタノール混合溶媒が溶出溶媒として用いられ、
その際エタノールが混合溶媒中重量で約20〜50%、好ま
しくは約30〜35%を占めるような混合溶媒が用いられ
る。For this purpose, in the present invention, a mixed solvent of chloroform and ethanol is used as an elution solvent,
In this case, a mixed solvent in which ethanol occupies about 20 to 50%, preferably about 30 to 35% by weight in the mixed solvent is used.
【００１２】[0012]
【発明の効果】本発明方法により、金線蓮等の抽出エキ
スから3-0-グルコピラノシル-γ-ブチロラクトンを分解
させることなく爽雑物を除去することができ、その収量
は乾燥金線蓮全草12gから1.23gと10%以上の高収率であ
る。しかも、得られた3-0-グルコピラノシル-γ-ブチロ
ラクトンは、粉末状結晶となる程の高純度のものであ
り、従って良好な保存性を示している。また、一連の分
離操作時に3-0-グルコピラノシル-γ-ブチロラクトンの
分解を伴わないため、単離精製工程の操作も簡単で、容
易であるという特徴を有している。Industrial Applicability According to the method of the present invention, exudates can be removed from an extract such as a gold wire lotus without decomposing 3-0-glucopyranosyl-γ-butyrolactone. The yield is as high as 12% to 1.23g and more than 10%. In addition, the obtained 3-0-glucopyranosyl-γ-butyrolactone has such a high purity as to become powdery crystals, and thus shows good storage stability. In addition, since a series of separation operations does not involve the decomposition of 3-0-glucopyranosyl-γ-butyrolactone, the isolation and purification steps are simple and easy.
【００１３】[0013]
【実施例】次に、実施例について本発明を説明する。Next, the present invention will be described by way of examples.
【００１４】実施例1 新鮮な乾燥金線蓮の全草12gを、室温条件下で80%エタノ
ールによる抽出を行ない、4.81gのエキスを得た。この
エキスを、クロロホルムと水とで溶媒分配し、脂溶性部
分を除去した。引続き、水層部分をブタノールとの間で
5回溶媒間分配し、色素を除去したところ、水溶性フラ
クションが1.7g得られた。Example 1 A fresh dried gold wire lotus plant (12 g) was extracted with 80% ethanol at room temperature to obtain 4.81 g of an extract. This extract was subjected to solvent partitioning between chloroform and water to remove fat-soluble portions. Subsequently, the aqueous layer was
When the solvent was distributed five times to remove the dye, 1.7 g of a water-soluble fraction was obtained.
【００１５】この水溶性フラクションを、スチレン−ジ
ビニルベンゼン共重合樹脂系吸着剤(三菱化学製品ダイ
ヤイオンHP-20)を用いた逆相カラムに付し、その水溶出
フラクションを更にシリカゲルを用いた順相カラムに付
し、クロロホルム-エタノール(容量比7：3)混合溶媒で
溶出して3-0-グルコピラノシル-γ-ブチロラクトン1.23
gを粉末状の結晶として得た。 The water-soluble fraction was applied to a reversed-phase column using a styrene-divinylbenzene copolymer resin-based adsorbent (Mitsubishi Chemical's Diaion HP-20), and the water-eluted fraction was further processed using silica gel. 3-0-glucopyranosyl-γ-butyrolactone 1.23 eluted with a chloroform-ethanol (7: 3 volume ratio) mixed solvent
g were obtained as powdery crystals.
【００１６】実施例2 シュスラン属カゴメランの生の全草8.7gを、室温条件下
でメタノールによる抽出を行ない、0.49gのエキスを得
た。このエキスを、クロロホルムと水とで溶媒間分配
し、脂溶性部分を除去し、水層部分より0.45gの水溶性
画分を得た。この画分を、シリカゲルカラムクロマトグ
ラフィーに付し、クロロホルム-エタノール(容量比8:2
→7：3)で溶出し、3-0-グルコピラノシル-γ-ブチロラ
クトン72mgを得た。Example 2 8.7 g of a raw whole plant of Kagomeran of the genus Suslan was extracted with methanol at room temperature to obtain 0.49 g of an extract. This extract was partitioned between chloroform and water, and the fat-soluble portion was removed, to obtain 0.45 g of a water-soluble fraction from the aqueous layer portion. This fraction was subjected to silica gel column chromatography, and chloroform-ethanol (volume ratio: 8: 2
→ Elution at 7: 3) yielded 72 mg of 3-0-glucopyranosyl-γ-butyrolactone.
【００１７】実施例3 シュスラン属ミヤマウズラの生の全草12.6gを還流条件
下でメタノールによる抽出を行ない、1.05gのエキスを
得た。このエキスを、クロロホルムと水とで溶媒間分配
し、脂溶性部分を除去し、水層部分より0.96gの水溶性
画分を得た。この画分を、シリカゲルカラムクロマトグ
ラフィーに付し、クロロホルム-エタノール(容量比8:2
→7：3)で溶出し、3-0-グルコピラノシル-γ-ブチロラ
クトン72mgを得た。Example 3 12.6 g of a raw whole plant of the genus Perilla was extracted with methanol under reflux conditions to obtain 1.05 g of an extract. This extract was partitioned between chloroform and water, and the fat-soluble portion was removed to obtain 0.96 g of a water-soluble fraction from the aqueous layer portion. This fraction was subjected to silica gel column chromatography, and chloroform-ethanol (volume ratio: 8: 2
→ Elution at 7: 3) yielded 72 mg of 3-0-glucopyranosyl-γ-butyrolactone.
Claims (2)
出エキスをクロロホルムと水とで溶媒間分配し、その水
層部分をn-ブタノールとの間で溶媒間分配した後、得ら
れた水溶性フラクションをスチレン-ジビニルベンゼン
共重合樹脂系吸着剤を用いたカラムクロマトグラフィー
に付し、その水溶出フラクションをシリカゲルを用いた
カラムクロマトグラフィーに付し、クロロホルム-エタ
ノール混合溶媒で溶出することを特徴とする3-0-グルコ
ピラノシル-γ-ブチロラクトンの分離方法。1. An organic solvent-extracted extract from a plant of the genus Anectocillus is partitioned between chloroform and water between solvents, and the aqueous layer is partitioned between n-butanol and the solvent. It is characterized in that it is subjected to column chromatography using a styrene-divinylbenzene copolymer resin-based adsorbent, the water-eluting fraction is subjected to column chromatography using silica gel, and eluted with a chloroform-ethanol mixed solvent. A method for separating 0-glucopyranosyl-γ-butyrolactone.
キスをクロロホルムと水とで溶媒間分配し、その水層部
分をシリカゲルを用いたカラムクロマトグラフィーに付
し、クロロホルム-エタノール混合溶媒で溶出すること
を特徴とする3-0-グルコピラノシル-γ-ブチロラクトン
の分離方法。2. An organic solvent-extracted extract from a plant of the genus Suslan is partitioned between chloroform and water, and the aqueous layer is subjected to column chromatography using silica gel and eluted with a chloroform-ethanol mixed solvent. A method for separating 3-0-glucopyranosyl-γ-butyrolactone, comprising the steps of:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9273498A JPH1192492A (en) | 1997-09-19 | 1997-09-19 | Method for separating 3-o-glucopyranosyl-gamma-butyrolactone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9273498A JPH1192492A (en) | 1997-09-19 | 1997-09-19 | Method for separating 3-o-glucopyranosyl-gamma-butyrolactone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH1192492A true JPH1192492A (en) | 1999-04-06 |
Family
ID=17528744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9273498A Pending JPH1192492A (en) | 1997-09-19 | 1997-09-19 | Method for separating 3-o-glucopyranosyl-gamma-butyrolactone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH1192492A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7033617B2 (en) | 2002-07-12 | 2006-04-25 | Academia Sinica | Use of Anoectochilus formosanus plant extracts and their derived fractions as herbal medicines or nutraceutical supplements for chemoprevention or treatment of human malignancies |
| JP2010155821A (en) * | 2008-12-31 | 2010-07-15 | China Medical Univ | Pharmaceutical composition-containing kinsenoside and extract usable for inhibiting formation of osteoclast, inhibiting function of osteoclast, and/or activating osteoblast |
| JP2015080477A (en) * | 2013-10-24 | 2015-04-27 | 東海大学Ｔｕｎｇｈａｉ Ｕｎｉｖｅｒｓｉｔｙ | Anoectochilus spp. fermented product, manufacturing method and application of the same |
-
1997
- 1997-09-19 JP JP9273498A patent/JPH1192492A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7033617B2 (en) | 2002-07-12 | 2006-04-25 | Academia Sinica | Use of Anoectochilus formosanus plant extracts and their derived fractions as herbal medicines or nutraceutical supplements for chemoprevention or treatment of human malignancies |
| SG120937A1 (en) * | 2002-07-12 | 2006-04-26 | Academia Sinica | Use of anoectochilus formosanus plant extracts andtheir derived fractions as herbal medicines or nu traceutical supplements for chemoprevention or treatment of human malignancies |
| JP2010155821A (en) * | 2008-12-31 | 2010-07-15 | China Medical Univ | Pharmaceutical composition-containing kinsenoside and extract usable for inhibiting formation of osteoclast, inhibiting function of osteoclast, and/or activating osteoblast |
| JP2015080477A (en) * | 2013-10-24 | 2015-04-27 | 東海大学Ｔｕｎｇｈａｉ Ｕｎｉｖｅｒｓｉｔｙ | Anoectochilus spp. fermented product, manufacturing method and application of the same |
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