JPH0610156B2 - Method for producing oleanoic acid - Google Patents
Method for producing oleanoic acidInfo
- Publication number
- JPH0610156B2 JPH0610156B2 JP60268189A JP26818985A JPH0610156B2 JP H0610156 B2 JPH0610156 B2 JP H0610156B2 JP 60268189 A JP60268189 A JP 60268189A JP 26818985 A JP26818985 A JP 26818985A JP H0610156 B2 JPH0610156 B2 JP H0610156B2
- Authority
- JP
- Japan
- Prior art keywords
- oleanolic acid
- acid
- sugar beet
- saponin
- sugar
- 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.)
- Expired - Fee Related
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 「産業上の利用分野」 本発明は、テンサイ（甜菜）からオレアノール酸を製造
する方法に関するものである。TECHNICAL FIELD The present invention relates to a method for producing oleanolic acid from sugar beet.
「従来技術」と「発明が解決しようとする問題点」 テンサイはアカザ科の植物でビートと通称され、この菜
根より砂糖を製造するため大量に栽培されている。テン
サイは起泡性の強いサポニンを含有し、これは砂糖製造
工程では生産能率の低下をきたし、製品に混入すると水
溶液は泡立ちが多くなり、数日後には絮状沈殿を生成し
て商品価値を低下する。このためフアンデルハール（Va
n der Harr 1927年）が、テンサイのサポニンは、オレ
アノール酸の配糖体であることを確認して以来、長きに
亘るにもかかわらず、その有効利用についての報告は皆
無である。"Prior Art" and "Problems to be Solved by the Invention" Sugar beet is a plant of the family Rhinoceros family, commonly called "beet," which is cultivated in large quantities to produce sugar from this rape root. Sugar beet contains saponin, which has a strong foaming property, which causes a decrease in production efficiency in the sugar manufacturing process, and when it is mixed in the product, the aqueous solution becomes frothy, and a few days later, a wavy precipitate is formed to increase the commercial value. descend. For this reason Juan der Haar (Va
(n der Harr 1927) confirmed that sugar beet saponin is a glycoside of oleanolic acid, but there has been no report on its effective use for a long time.
本発明者は、上記状況に鑑みテンサイのサポニンの有効
利用をはかるべくイサポニンを加水分解して得られるオ
レアノール酸の薬効ロテンサイにおけるオレアノール酸
の含量及びハテンサイ以外からのオレアノール酸入手の
可能性等につき研究を重ねた。In view of the above situation, the present inventor studied the effectiveness of oleanolic acid obtained by hydrolyzing isaponin in order to effectively utilize saponin of sugar beet. Layered.
その結果イについては；テンサイから得たオレアノール
酸の肝障害に対する有効性を確認し、ロについては；砂
糖製造に利用されている根及び砂糖製造に利用されるこ
とのない葉、更には砂糖製造の過程で不用物として生ず
る糖抽出残滓にもオレアノール酸を確認した。尚、テン
サイにおけるオレアノール酸の含量を、後記の定量法に
より測定した結果を次表に示す。As for the result a, the effectiveness of oleanolic acid obtained from sugar beet for liver damage was confirmed, and for b; the roots used for sugar production and leaves not used for sugar production, and further sugar production. Oleanolic acid was also confirmed in the sugar extraction residue produced as a waste material during the process. The following table shows the results of measuring the content of oleanolic acid in sugar beet by the quantitative method described below.
また、前述ハについては；オレアノール酸は五環性のト
リテルペノイドの一種で次の化学構造式を有しており、
これを合成によつて得ることは困難であり、一方チヨウ
ジノキの蕾、タラノキの樹皮又はトチバニンジンの根茎
等に遊離型や配糖体として含まれているとはいうもの
の、その含量は少なく、これらからの大量入手は期待し
えない、との結論に到つた。 Regarding the above-mentioned C, oleanolic acid is a kind of pentacyclic triterpenoid and has the following chemical structural formula:
It is difficult to obtain this by synthesis, on the other hand, although it is said that it is contained as a free form or glycoside in the buds of Japanese cedar, the bark of cod, or the rhizome of Ginseng, its content is low, but from these It was concluded that the mass acquisition of is not expected.
本発明者は、以上の結果を総合し、テンサイからのオレ
アノール酸の製造が極めて適切であるとの知見に達し、
更にテンサイからのオレアノール酸の製造方法につき、
具体的に研究を進め本発明に到達した。 The present inventors have combined the above results, and have found that the production of oleanolic acid from sugar beet is extremely suitable,
Furthermore, regarding the method of producing oleanolic acid from sugar beet,
The present invention has been achieved by proceeding with specific research.
「問題点を解決するための手段」と「作用」 即ち、本発明は、 テンサイ粉砕物を有機溶媒で抽出処理してサポニンの
抽出物を得、該抽出物を鉱酸で処理してサポニンを加水
分解によりオレアノール酸に変換し、得た粗オレアノー
ル酸を陰イオン交換樹脂で精製することを特徴とするオ
レアノール酸の製造法； 及び テンサイ粉砕物を鉱酸で処理してテンサイ粉砕物中の
サポニンを加水分解によりオレアノール酸に変換した
後、該テンサイ粉砕物の鉱酸処理物を有機溶媒で抽出
し、得た粗オレアノール酸を陰イオン交換樹脂で精製す
ることを特徴とするオレアノール酸の製造法； を提供するものである。“Means for Solving Problems” and “Action” That is, the present invention is to extract saponin by extracting the ground beet extract with an organic solvent to obtain an extract of saponin, and treating the extract with a mineral acid to obtain saponin. A method for producing oleanolic acid, which comprises converting the oleanolic acid by hydrolysis and purifying the obtained crude oleanolic acid with an anion exchange resin; and treating the ground beet with mineral acid to saponin in the ground beet. Is converted to oleanolic acid by hydrolysis, the mineral acid-treated product of the crushed sugar beet is extracted with an organic solvent, and the obtained crude oleanolic acid is purified with an anion exchange resin. ; Is provided.
ここにおいて、テンサイの葉及び糖抽出残滓は、これを
粉砕してそのままテンサイ粉砕物として本発明又は
の処理を施せばよい。Here, the sugar beet leaves and the sugar extraction residue may be crushed and directly subjected to the treatment of the present invention as a crushed sugar beet product.
しかしながら根は、粉砕後水又は温水を加えて撹拌ろ過
して糖質等の水溶性物質を除去し、これをテンサイ粉砕
物として本発明の処理を施すことが望ましい。本発明者
の実験によれば、根はその粉砕物をそのまま処理するよ
りも、粉砕物に含まれる水溶性物質を除去した方が純度
のよいオレアノール酸が効率よく得られるからである。
尚、粉砕したテンサイの根を３倍量の温水（60℃）で１
時間浸漬して水溶性物質を除去しても、これによるサポ
ニンの損失は元のサポニン含量の２％にも満たない程度
であり、殆んど影響はない。However, it is desirable to remove water-soluble substances such as sugars by adding water or warm water to the roots, stirring and filtering the roots, and subjecting the roots to a crushed sugar beet product for the treatment of the present invention. According to the experiments conducted by the present inventor, oleanolic acid having a higher purity can be obtained more efficiently by removing the water-soluble substance contained in the ground product than by treating the ground product as it is.
In addition, 1 crushed sugar beet root with 3 times the amount of warm water (60 ℃)
Even if the water-soluble substance is removed by immersion for a long time, the loss of saponin due to this is less than 2% of the original saponin content, and there is almost no effect.
尤も、先にも述べた如く製糖工場においては、テンサイ
の根は砂糖製造の過程で糖質等の水溶性物質をとり除い
た糖抽出残滓となるため、この糖抽出残滓を粉砕し、本
発明のテンサイ粉砕物として利用すれば、上記した水溶
性物質の除去操作を別途施す必要はない。However, as described above, in sugar production plants, sugar beet roots become sugar extraction residues from which water-soluble substances such as sugars have been removed in the process of sugar production. If it is used as a sugar beet crushed product, it is not necessary to separately perform the above-mentioned water-soluble substance removing operation.
また、根から水溶性物質を除去して得たテンサイ粉砕物
（製糖過程で生ずる糖抽出残滓の粉砕物を含む）は、
の発明にあつては望ましくは、これを乾燥処理すること
なく、含水物のまま、出発原料として使用する。根から
水溶性物質を除去して得たテンサイ粉砕物は、これを乾
燥するとテンサイに含まれている粘着物質が乾燥により
サポニンを固着し、後に抽出処理を施してもサポニンの
抽出効率が極端に低下するからである。In addition, the sugar beet crushed product obtained by removing the water-soluble substance from the root (including the crushed product of the sugar extraction residue generated in the sugar making process)
In the invention described above, it is desirable to use the hydrated product as a starting material without drying it. The sugar beet crushed product obtained by removing the water-soluble substance from the roots, when dried, the sticky substance contained in the sugar beet fixes the saponin due to the drying, and the extraction efficiency of saponin becomes extremely high even if the extraction process is performed later. Because it will decrease.
更に、の発明にあつては、粉砕したテンサイをpH４以
下の水に浸漬後ろ過し、このろ過残留物を出発原料とし
て使用することが望ましい。この酸性溶液での前処理を
施した場合には、前処理を施さなかつた場合のサポニン
の抽出率、約60％が、抽出率90％以上に向上したものと
なるからである。この様に前処理を施さない場合に抽出
率が低下するのは、テンサイに含まれているサポニンの
一部がカルシウムまたはマグネシウム等の金属塩として
存在しており、抽出処理のみではこれらが容易に抽出さ
れないためと考えられる。Further, in the present invention, it is preferable that the crushed sugar beet is immersed in water having a pH of 4 or less and then filtered, and the filtration residue is used as a starting material. This is because when the pretreatment with this acidic solution is performed, the extraction rate of saponin when the pretreatment is not performed, which is about 60%, is improved to 90% or more. The reason why the extraction rate decreases without pretreatment is that some of the saponins contained in sugar beet are present as metal salts such as calcium or magnesium. It is thought that it is not extracted.
抽出処理用の有機溶媒としては、の発明にあつては、
メタノール、エタノール、iso−プロパノール又はｎ−
ブタノール等のアルコール類を使用することができ、
の発明にあつては、これらアルコール類の他、アセト
ン、酢酸エチル、クロロホルム、塩化メチレン、二塩化
エチレン又はベンゼン等を使用することができる。これ
ら有機溶媒を使用しての抽出処理は、の発明にあつて
は、サポニンを抽出物として得るためにおこなうもので
あり、の発明にあつては、サポニンの加水分解物であ
るオレアノール酸を抽出物として得るためにおこなうも
のである。As the organic solvent for the extraction treatment, in the invention of
Methanol, ethanol, iso-propanol or n-
Alcohols such as butanol can be used,
In addition to these alcohols, acetone, ethyl acetate, chloroform, methylene chloride, ethylene dichloride, benzene and the like can be used in the invention. The extraction treatment using these organic solvents is carried out in order to obtain saponin as an extract in the invention of, and in the invention of, oleanolic acid, which is a hydrolyzate of saponin, is extracted. This is done to obtain it as a thing.
上記、有機溶媒を用いての抽出処理は、いずれの発明の
場合とも、熱抽出する方が抽出効率が良い。In any of the inventions, the extraction treatment using the organic solvent described above is more efficient in extraction by heat extraction.
鉱酸での処理は、サポニンを加水分解してオレアノール
酸とするためのものであり、の発明は、この加水分解
を抽出処理の後におこない、の発明は、抽出処理の前
におこなうものである。この加水分解用の鉱酸として
は、例えば、10〜20％の塩酸、硫酸等を使用することが
できる。The treatment with a mineral acid is for hydrolyzing saponin to oleanolic acid, the invention of is performed after the extraction treatment, and the invention of is performed before the extraction treatment. . As the mineral acid for hydrolysis, for example, 10 to 20% hydrochloric acid, sulfuric acid or the like can be used.
の発明において加水分解により得た固形物、及びの
発明において抽出液を留去して得た固形物は、それぞれ
約10％のオレアノール酸を含有する粗オレアノール酸で
ある。The solid obtained by hydrolysis in the invention of 1) and the solid obtained by distilling the extract in the invention of 3 are crude oleanolic acids each containing about 10% of oleanolic acid.
この粗オレアノール酸の精製は、陰イオン交換樹脂に粗
オレアノール酸を通して、陰イオン交換樹脂にオレアノ
ール酸を吸着させ、後に、吸着したオレアノール酸をア
ルカリ液（例えば水酸化ナトリウムのメタノール若しく
はエタノール溶液又はこれらの含水溶液）で溶離させ、
この溶離液を中和した後、溶媒を留去し、残留物を水
洗、乾燥し、最後にメタノール又はエタノール等で再結
晶させておこなうことができる。Purification of this crude oleanolic acid is carried out by passing crude oleanolic acid through an anion exchange resin to adsorb oleanolic acid on the anion exchange resin, and then adsorbing the adsorbed oleanolic acid with an alkaline solution (for example, a solution of sodium hydroxide in methanol or ethanol or Water solution),
After the eluate is neutralized, the solvent is distilled off, the residue is washed with water, dried, and finally recrystallized with methanol or ethanol.
上記した、陰イオン交換樹脂での粗オレアノール酸の処
理にあたつては、陰イオン交換樹脂の負荷を減少させる
べく、粗オレアノール酸をあらかじめアルカリ性溶媒
（例えば水酸化ナトリウムのメタノール若しくはエタノ
ール溶液）に溶解して不溶物をろ過によつて除去し、ろ
液の溶媒を留去し、残留物に水を加えてpH8〜10の液と
なし、ろ過後残留物を水洗して、更に水を加え、中和後
ろ過し、残留物をアルコール類、ジオキサン又はこれら
の含水溶液に溶かして、陰イオン交換樹脂に通すとよ
い。In the above treatment of the crude oleanolic acid with the anion exchange resin, in order to reduce the load of the anion exchange resin, the crude oleanolic acid was previously added to an alkaline solvent (for example, a solution of sodium hydroxide in methanol or ethanol). Dissolve and insoluble matter is removed by filtration, the solvent of the filtrate is distilled off, and water is added to the residue to form a solution having a pH of 8 to 10.After filtration, the residue is washed with water and further water is added. After neutralization and filtration, the residue may be dissolved in alcohols, dioxane or an aqueous solution of these, and passed through an anion exchange resin.
また、オレアノール酸は、弱塩基性陰イオン交換樹脂に
吸着されず、強塩基性陰イオン交換樹脂に吸着されるた
め、この性質を利用して粗オレアノール酸溶液を先ず弱
塩基性陰イオン交換樹脂に流して不純物を吸着させ、次
にこの通過液を強塩基性陰イオン交換樹脂に通すとよ
い。Further, oleanolic acid is not adsorbed on the weakly basic anion exchange resin but is adsorbed on the strongly basic anion exchange resin. Therefore, the crude oleanolic acid solution is first used for the weakly basic anion exchange resin by utilizing this property. It is advisable to let the solution pass through the column to adsorb the impurities, and then pass this passing solution through a strongly basic anion exchange resin.
「実施例等」 以下実施例等により更に具体的に本発明を説明する。"Examples and the like" The present invention will be described more specifically with reference to Examples and the like below.
実施例１＜粗オレアノール酸の製造＞ テンサイの根１kg（オレアノール酸としての含量982m
g）を粉砕し、水１を加え塩酸でpH１とし室温で30分
間撹拌後ろ過した。残留物にメタノール１を加え１時
間還流し、この操作を２回行い、抽出液のメタノールを
減圧留去した。残留物に10％塩酸メタノール50mlを加え
て室温で10時間放置した後減圧乾固し、これを水洗した
後80℃で乾燥して固形物9.8ｇ（オレアノール酸の含量9
01mg、純度9.2％）を得た。本例によるオレアノール酸
の回収率は91.8％であつた。Example 1 <Production of crude oleanolic acid> 1 kg of sugar beet root (content as oleanolic acid 982 m
g) was crushed, water 1 was added, the pH was adjusted to 1 with hydrochloric acid, the mixture was stirred at room temperature for 30 minutes and then filtered. Methanol 1 was added to the residue and refluxed for 1 hour. This operation was repeated twice, and the methanol of the extract was distilled off under reduced pressure. To the residue was added 10% hydrochloric acid methanol (50 ml), the mixture was allowed to stand at room temperature for 10 hours, dried under reduced pressure, washed with water, and dried at 80 ° C to obtain a solid product (9.8 g, oleanolic acid content 9%).
01 mg, purity 9.2%) was obtained. The recovery rate of oleanolic acid according to this example was 91.8%.
実施例２＜粗オレアノール酸の製造＞ テンサイの葉１kg（オレアノール酸としての含量1214m
g）を粉砕し、10％硫酸１を加えて90〜95℃で４時間
加熱し冷後ろ過した。残留物を水洗した後、これに塩化
メチレン１を加えて１時間還流し、この操作を２回お
こなつた。抽出液の塩化メチレンを留去し、残留物を80
℃で乾燥して固形物7.2ｇ（オレアノール酸の含量1126m
g、純度15.6％）を得た。本例によるオレアノール酸の
回収率は92.8％であつた。Example 2 <Production of crude oleanolic acid> Leaves of sugar beet 1 kg (content as oleanolic acid 1214 m
g) was crushed, 10% sulfuric acid 1 was added, the mixture was heated at 90 to 95 ° C. for 4 hours, cooled, and then filtered. After washing the residue with water, methylene chloride 1 was added thereto and refluxed for 1 hour, and this operation was performed twice. Distill off the methylene chloride from the extract and remove the residue to 80
After drying at ℃ 7.2g solids (oleanolic acid content 1126m
g, purity 15.6%). The recovery rate of oleanolic acid according to this example was 92.8%.
実施例３＜粗オレアノール酸の精製＞ 粗オレアノール酸100ｇ（オレアノール酸の含量9.2ｇ）
をメタノール700mlに加熱溶解し、冷後これに１Ｎ水酸
化ナトリウム・メタノール液300mlを加えて室温で１時
間放置後ろ過し、ろ液のメタノールを減圧留去し残留物
に水200mlを加えて（pH8）撹拌後ろ過し水洗した。次に
残留物に水100mlを加えて塩酸で中和した後ろ過し、残
留物を水洗、乾燥して固形物26.3ｇを得た。固形物をメ
タノール700mlに溶解した後ろ過し、ろ液をメタノール
で飽和した弱塩基性陰イオン交換樹脂のアンバーライト
IRA-93 OH型（オルガノ株式会社）150mlを充填したカラ
ム（2.5cm×50cm）にSV=3で流し、更にメタノール450ml
を流してカラム内のオレアノール酸を流出させた。次に
通過液をメタノールで飽和した強塩基性陰イオン交換樹
脂のアンバーライトIRA-411 OH型150mlを充填したカラ
ム（2.5cm×50cm）にSV=3で流してオレアノール酸を吸
着させ、ついでメタノール300mlで洗浄した後、１Ｎ水
酸化ナトリウム・メタノール液600mlをSV=3で流してオ
レアノール酸を溶離した。溶離液を塩酸で中和した後メ
タノールを留去し、残留物を水洗、乾燥して固形物9.8
ｇ（オレアノール酸の含量6.7ｇ、純度68.4％）を得
た。本例によるオレアノール酸の回収率は72.8％であつ
た。これをエタノールから再結晶して白色結晶のオレア
ノール酸6.1ｇ（回収率66.3％）を得た。このものの薄
層クロマトグラフイー〔シリカゲル，ベンゼン−エタノ
ール（85:15）〕はRf値0.4を示した。Example 3 <Purification of crude oleanolic acid> 100 g of crude oleanolic acid (content of oleanolic acid: 9.2 g)
Was dissolved in 700 ml of methanol by heating, and after cooling, 300 ml of 1N sodium hydroxide / methanol solution was added, and the mixture was allowed to stand at room temperature for 1 hour and then filtered. The methanol in the filtrate was distilled off under reduced pressure, and 200 ml of water was added to the residue ( (pH8) After stirring, it was filtered and washed with water. Next, 100 ml of water was added to the residue, which was neutralized with hydrochloric acid and then filtered, and the residue was washed with water and dried to obtain 26.3 g of a solid product. Amberlite, a weakly basic anion exchange resin, was prepared by dissolving solids in 700 ml of methanol and then filtering, and the filtrate was saturated with methanol.
IRA-93 OH type (Organo Co., Ltd.) Flowed in a column (2.5 cm x 50 cm) packed with 150 ml at SV = 3, and further 450 ml of methanol
Oleanolic acid in the column was allowed to flow out. Next, the flow-through was passed through a column (2.5 cm x 50 cm) packed with 150 ml of strong basic anion exchange resin, Amberlite IRA-411 OH type, at SV = 3 to adsorb oleanolic acid and then methanol. After washing with 300 ml, 600 ml of 1N sodium hydroxide / methanol solution was passed at SV = 3 to elute oleanolic acid. After neutralizing the eluent with hydrochloric acid, the methanol was distilled off, and the residue was washed with water and dried to give a solid 9.8.
g (oleanolic acid content 6.7 g, purity 68.4%) was obtained. The recovery rate of oleanolic acid according to this example was 72.8%. This was recrystallized from ethanol to obtain 6.1 g of white crystals of oleanolic acid (recovery rate 66.3%). Thin layer chromatography [silica gel, benzene-ethanol (85:15)] of this product showed an Rf value of 0.4.
融点：301〜303℃ 元素分析値：C30H48O3 理論値(%)C:78.89,H:10.59 実験値(%)C:79.13,H:10.78 オレアノール酸の定量法 粉砕したテンサイ約10ｇを精密に量り、１％塩酸メタノ
ール30mlを加えて１時間還流してサポニンを抽出し、こ
の操作を４回行い、抽出液を減圧留去する。残留物に10
％塩酸ジオキサン10mlを加えて３時間還流してサポニン
を加水分解した後溶媒を減圧留去し、残留物にエーテル
−メタノール(8:2)混液を加えて正確に100mlとしろ過す
る。ろ液の一定量を正確に量り、これにジアゾメタンを
約20分間導入後、溶媒を減圧留去し、残留物にスチグマ
ステロール−ｎ−ブタノール溶液（500μg/ml）１mlを
正確に加えて試料溶液とする。別に標準オレアノール酸
のエーテル−メタノール(8:2)溶液（500μg/ml）１mlを
同様に操作して標準溶液とする。試料溶液及び標準溶液
５μを正確に量り、次の条件でガスクロマトグラフ法
によつて測定し、次式よりオレアノール酸の含量を求め
る。Melting point: 301-303 ° C Elemental analysis value: C 30 H 48 O 3 Theoretical value (%) C: 78.89, H: 10.59 Experimental value (%) C: 79.13, H: 10.78 Quantitative method for oleanolic acid Ground beet approximately 10 g Is weighed accurately, 30 ml of 1% hydrochloric acid methanol is added, refluxed for 1 hour to extract saponin, this operation is repeated 4 times, and the extract is distilled off under reduced pressure. 10 to residue
% Dioxane (10 ml) was added and the mixture was refluxed for 3 hours to hydrolyze saponin, the solvent was distilled off under reduced pressure, and an ether-methanol (8: 2) mixture was added to the residue to make exactly 100 ml, followed by filtration. A certain amount of the filtrate was accurately measured, diazomethane was introduced into this for about 20 minutes, the solvent was distilled off under reduced pressure, and 1 ml of stigmasterol-n-butanol solution (500 μg / ml) was accurately added to the residue to give a sample. Use as a solution. Separately, 1 ml of a standard oleanolic acid ether-methanol (8: 2) solution (500 μg / ml) was similarly processed to prepare a standard solution. A sample solution and 5 μm of a standard solution are accurately weighed and measured by gas chromatography under the following conditions, and the content of oleanolic acid is obtained from the following formula.
Ａ：試料溶液のオレアノール酸のピーク面積に対するス
チグマステロールのピーク面積比 Ｂ：標準溶液のオレアノール酸のピーク面積に対するス
チグマステロールのピーク面積比 オレアノール酸抽出物の定量には、サポニンの加水分解
の操作を省略する。 A: Peak area ratio of stigmasterol to the peak area of oleanolic acid in the sample solution B: Peak area ratio of stigmasterol to the peak area of oleanolic acid in the standard solution The oleanolic acid extract was quantified by hydrolysis of saponin. Omit the operation.
操作条件 カラム：２ｍ×３mmのカラムに３％Silicon Gum SE-30/
Chromosorb W AW DMCS(80〜100メツシユ)を充填 キヤリアーガス及び流量：窒素，毎分60ml付近の一定量 カラム温度：270℃付近の一定温度 注入温度：310℃付近の一定温度 検 出 器：水素炎イオン化検出器(FID) オレアノール酸の四塩化炭素肝障害に対する試験 ddk系雄性マウス（体重18〜20ｇ）１群10匹を用い、被
検薬をアラビアゴム末にて懸濁し、１日２回、３日間連
日経口投与する。３日目の最終投与１時間後に、１％四
塩化炭素（v/vオリーブ油）を後背部皮下に２ml/kg注射
する。注射後、19時間目に最終回の被検薬を経口投与
し、投与後１時間目に、エーテル麻酔下、腹部下行性大
動脈より採血し、得られた血液は、3000r.p.m.にて、15
分間遠心分離をおこない、血清中のグルタミン酸オキザ
ロ酢酸トランスアミナーゼ(GOT)、グルタミン酸ピルビ
ン酸トランスアミナーゼ(GPT)の酵素活性をS・TA-Test w
ako（和光純薬株式会社）を用いて測定する。Operating conditions Column: 3% Silicon Gum SE-30 / on a 2m x 3mm column
Filled with Chromosorb W AW DMCS (80-100 mesh) Carrier gas and flow rate: nitrogen, a fixed amount near 60 ml / min Column temperature: constant temperature around 270 ° C injection temperature: constant temperature around 310 ° C Detector: hydrogen flame Ionization detector (FID) Test of oleanolic acid for carbon tetrachloride liver injury Using 10 ddk male mice (body weight 18 to 20 g) per group, suspending the test drug with gum arabic powder, twice a day, Orally administered for 3 days every day. One hour after the final administration on the 3rd day, 2 ml / kg of 1% carbon tetrachloride (v / v olive oil) is subcutaneously injected into the back of the back. The final test drug was orally administered 19 hours after the injection, and 1 hour after the administration, blood was collected from the abdominal descending aorta under ether anesthesia, and the obtained blood was collected at 3000 rpm for 15 minutes.
Centrifuge for minutes to confirm the enzyme activity of glutamate oxaloacetate transaminase (GOT) and glutamate pyruvate transaminase (GPT) in serum by S ・ TA-Test w.
It is measured using ako (Wako Pure Chemical Industries, Ltd.).
テンサイから抽出したオレアノール酸について試験した
結果は次表の様であつた。The results of testing oleanolic acid extracted from sugar beet are shown in the following table.
テンサイから抽出したオレアノール酸は四塩化炭素肝障
害に対し50mg/kgの投与量で、四塩化炭素処置群に対し
有意な血清中GOT、GPT値の低下がみられ、四塩化炭素肝
障害の予防効果が認められた。また、投与量100mg/kg、5
00mg/kgにおいてもGOT、GPT値の低下がみられ、用量依存
的に効果を持つていることが認められた。 Oleanolic acid extracted from sugar beet at a dose of 50 mg / kg for carbon tetrachloride liver injury showed a significant decrease in serum GOT and GPT values for the carbon tetrachloride treated group, and prevention of carbon tetrachloride liver injury The effect was recognized. Also, the dose 100 mg / kg, 5
Even at 00 mg / kg, GOT and GPT levels decreased, and it was confirmed that the effect was dose-dependent.
「発明の効果」 以上の本発明によれば、製糖工場において多量に廃出さ
れるテンサイの糖抽出残滓等を利用して、合成等によつ
ては製造困難なオレアノール酸を製造することが可能で
ある。[Advantages of the Invention] According to the present invention described above, it is possible to produce oleanolic acid, which is difficult to produce by synthesis or the like, by utilizing sugar extract residue of sugar beet that is largely discharged in a sugar production plant. is there.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 Ｐｈａｒｍａｚｉｅ39〔５〕, （1984），Ｕ．ＷｒａｅｃｉｏｎｏｉＬ. Ｚａｐｒｕｔｋｏ，“Ｉｓｏｌｉｅｒｕｎ ｇ ｄｅｒ Ｏｌｅａｎｏｌａｕｒｅ ａ ｕｓ Ｎｅｂｅｎｐｒｏｄｕｋｔｅｎ ｄ ｅｒ Ｚｕｃｋｅｒｒｕｂｅｎｖｅｒａｒ ｂｅｉｔｕｎｇ（Ｄｅｆａｋａｔｉｏｎｓ ｓｃｈｌａｍｎ）”，Ｐ．350−351 ─────────────────────────────────────────────────── ─── Continuation of the front page (56) References Pharmazie 39 [5], (1984), U.S.S. Wraecionoi L. Zaprutko, "Isolierung der Oleanolaure a us Nebenprodukten der Zuckerrubbernberbeitung (Defakations schlamn)", P.P. 350-351
Claims (2)
サポニンの抽出物を得、該抽出物を鉱酸で処理してサポ
ニンを加水分解によりオレアノール酸に変換し、得た粗
オレアノール酸を陰イオン交換樹脂で精製することを特
徴とするオレアノール酸の製造法。1. A crushed product of sugar beet is subjected to an extraction treatment with an organic solvent to obtain an extract of saponin, and the extract is treated with a mineral acid to convert saponin into oleanolic acid by hydrolysis to obtain the crude oleanolic acid. A method for producing oleanolic acid, which comprises refining with an anion exchange resin.
粉砕物中のサポニンを加水分解によりオレアノール酸に
変換した後、該テンサイ粉砕物の鉱酸処理物を有機溶媒
で抽出し、得た粗オレアノール酸を陰イオン交換樹脂で
精製することを特徴とするオレアノール酸の製造法2. A crushed product of sugar beet is treated with a mineral acid to convert saponin in the crushed product of sugar beet into oleanolic acid by hydrolysis, and then a mineral acid-treated product of the crushed product of sugar beet is extracted with an organic solvent. Method for producing oleanolic acid, characterized by purifying crude oleanolic acid with anion exchange resin
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60268189A JPH0610156B2 (en) | 1985-11-27 | 1985-11-27 | Method for producing oleanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60268189A JPH0610156B2 (en) | 1985-11-27 | 1985-11-27 | Method for producing oleanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62126149A JPS62126149A (en) | 1987-06-08 |
| JPH0610156B2 true JPH0610156B2 (en) | 1994-02-09 |
Family
ID=17455153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60268189A Expired - Fee Related JPH0610156B2 (en) | 1985-11-27 | 1985-11-27 | Method for producing oleanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0610156B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2226346C (en) * | 1995-07-07 | 2007-08-28 | Meiji Seika Kaisha, Ltd. | Triterpene derivatives and pharmaceuticals for treating hepatic disorders |
| KR100490682B1 (en) * | 2002-05-27 | 2005-05-19 | 학교법인 현동학원 | A process for isolating epi-oleanolic acid from Viscum album coloratum |
-
1985
- 1985-11-27 JP JP60268189A patent/JPH0610156B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Ｐｈａｒｍａｚｉｅ３９〔５〕，（１９８４），Ｕ．ＷｒａｅｃｉｏｎｏｉＬ．Ｚａｐｒｕｔｋｏ，"ＩｓｏｌｉｅｒｕｎｇｄｅｒＯｌｅａｎｏｌａｕｒｅａｕｓＮｅｂｅｎｐｒｏｄｕｋｔｅｎｄｅｒＺｕｃｋｅｒｒｕｂｅｎｖｅｒａｒｂｅｉｔｕｎｇ（Ｄｅｆａｋａｔｉｏｎｓｓｃｈｌａｍｎ）"，Ｐ．３５０−３５１ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62126149A (en) | 1987-06-08 |
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