JPH0753560A - Production of 3'(r),4'(r)-3'-epoxyangeloyloxy-4'-acetoxy-3',4'-dihydroseselin - Google Patents
Production of 3'(r),4'(r)-3'-epoxyangeloyloxy-4'-acetoxy-3',4'-dihydroseselinInfo
- Publication number
- JPH0753560A JPH0753560A JP5220535A JP22053593A JPH0753560A JP H0753560 A JPH0753560 A JP H0753560A JP 5220535 A JP5220535 A JP 5220535A JP 22053593 A JP22053593 A JP 22053593A JP H0753560 A JPH0753560 A JP H0753560A
- Authority
- JP
- Japan
- Prior art keywords
- buterixin
- isoepoxy
- compound
- leaf
- inutouki
- 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.)
- Granted
Links
Landscapes
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、医薬品、化粧品、健康
食品等の製造に有用な、3′(R),4′(R)-3′-エポキシア
ンゲロイルオキシ-4′-アセトキシ-3′,4′-ジヒドロセ
セリンを取得する方法に関するものである。FIELD OF THE INVENTION The present invention relates to 3 '(R), 4' (R) -3'-epoxyangeloyloxy-4'-acetoxy-3, which is useful in the production of pharmaceuticals, cosmetics, health foods and the like. The present invention relates to a method for obtaining ′, 4′-dihydroceserine.
【０００２】[0002]
【従来の技術】3′(R),4′(R)-3′-エポキシアンゲロイ
ルオキシ-4′-アセトキシ-3′,4′-ジヒドロセセリン
〔3′(R),4′(R)-3′-epoxyangeloyloxy-4′-acetoxy-
3′,4′-dihydroseselin〕は下記化１の構造式を有し、
アレルギーや炎症、特に気管支喘息、皮膚アレルギー等
の治療に有効であることが知られている（特開昭６３−
１５０２８７号公報）。2. Description of the Related Art 3 '(R), 4' (R) -3'-epoxyangeloyloxy-4'-acetoxy-3 ', 4'-dihydroseserine [3' (R), 4 '(R ) -3′-epoxyangeloyloxy-4′-acetoxy-
3 ′, 4′-dihydroseselin] has the following structural formula:
It is known to be effective for treating allergies and inflammations, especially bronchial asthma, skin allergies, etc. (JP-A-63-63).
150287).
【０００３】[0003]
【化１】 [Chemical 1]
【０００４】3′(R),4′(R)-3′-エポキシアンゲロイル
オキシ-4′-アセトキシ-3′,4′-ジヒドロセセリンは、
これを日本山人参の根茎部から初めて単離した奥田らに
よりイソエポキシ−ブテリキシンという慣用名が与えら
れており、この明細書においても、以下この慣用名を採
用する。3 '(R), 4' (R) -3'-epoxyangeloyloxy-4'-acetoxy-3 ', 4'-dihydroseserine is
Okuda et al., Who first isolated this from the rhizome of Japanese ginseng, gave the trivial name of isoepoxy-buterixin, and this trivial name will be used in this specification as well.
【０００５】イソエポキシ−ブテリキシンは、日本山人
参の根茎部を酢酸エチルで抽出処理すると抽出されて来
るので、得られた抽出物を必要に応じて精製すれば純粋
なイソエポキシ−ブテリキシンを得ることができる（前
記特許出願公開公報）。従来、これ以外のイソエポキシ
−ブテリキシン取得法は知られていない。[0005] Isoepoxy-buterixin is extracted when the rhizome of Japanese ginseng is subjected to extraction treatment with ethyl acetate, and thus the obtained extract can be purified as necessary to obtain pure isoepoxy-buterixin. (The above-mentioned patent application publication). Heretofore, no other isoepoxy-buterixin acquisition method has been known.
【０００６】なお、“日本山人参”は、セリ科の多年植
物であるイヌトウキ(学名：Angelica shikokiana）に属
する栽培品種に付された慣用名と認められ、栽培されて
入手容易であることにより原料とされているが、イヌト
ウキと明確に区別されるものではない。[0006] "Nihonsan ginseng" is recognized as a common name given to a cultivar belonging to a perennial plant of the Apiaceae (scientific name: Angelica shikokiana). However, it is not clearly distinguished from Inuuki.
【０００７】[0007]
【発明が解決しようとする課題】イソエポキシ−ブテリ
キシンは上述の薬理作用を示すことにより各種薬品、化
粧品、健康食品等への利用が期待される。しかしなが
ら、日本山人参根茎部に含まれている量は僅かであり、
根茎部抽出物における含有率もきわめて低いから、前述
の薬理作用を期待する場合、抽出物のまま利用しても効
果はあまり期待できず、精製するにしてもコストが嵩む
という問題点があった。そこで本発明は、上記従来の方
法よりも効率よくイソエポキシ−ブテリキシンを得る方
法を提供することを目的とする。Isoepoxy-buterixin is expected to be used in various chemicals, cosmetics, health foods, etc. due to the above-mentioned pharmacological action. However, the amount contained in the Japanese ginseng rhizome is small,
Since the content rate in the rhizome extract is also extremely low, when expecting the above-mentioned pharmacological action, there is a problem that the effect cannot be expected even if it is used as the extract as it is, and the cost increases even if it is purified. . Therefore, it is an object of the present invention to provide a method for obtaining isoepoxy-buterixin more efficiently than the above conventional method.
【０００８】[0008]
【課題を解決するための手段】本発明によるイソエポキ
シ−ブテリキシン取得方法は、水、有機溶媒、またはこ
れらの混合物を抽出溶媒として日本山人参の葉部を抽出
処理し抽出物を採取することを特徴とするものである。The method for obtaining isoepoxy-buterixin according to the present invention comprises the steps of extracting leaves of Japanese ginseng using water, an organic solvent, or a mixture thereof as an extraction solvent to extract the extract. It is a feature.
【０００９】この発明は、従来薬効なしとして廃棄され
ていた日本山人参の葉部が意外にもイソエポキシ−ブテ
リキシンを多量に含有することを本発明者らが見いだし
たことに基づく。すなわち、日本山人参の葉部は、根茎
部と比べると少なくとも２倍以上、通常３倍以上のイソ
エポキシ−ブテリキシンを含有することが確認された。
The present invention is based on the finding by the present inventors that the leaves of Japanese ginseng, which had been conventionally discarded as having no medicinal effect, unexpectedly contained a large amount of isoepoxy-buterixin. That is, it was confirmed that the leaves of Japanese ginseng contained at least 2 times or more, and usually 3 times or more, isoepoxy-buterixin as compared with the rhizomes.
【００１０】この日本山人参葉部のイソエポキシ−ブテ
リキシンは、水、有機溶媒、またはこれらの混合物によ
り容易に抽出されるので、根茎部からイソエポキシ−ブ
テリキシンを抽出するよりも簡単にイソエポキシ−ブテ
リキシン含有率の高い抽出物を得ることができる。ま
た、抽出物からイソエポキシ−ブテリキシンを単離また
は濃縮する精製操作も簡単で済む。Since the isoepoxy-buterixin of Japanese ginseng leaf is easily extracted with water, an organic solvent or a mixture thereof, it is easier to extract the isoepoxy-buterixin from the rhizome. An extract having a high buterixin content can be obtained. Further, the purification operation for isolating or concentrating the isoepoxy-buterixin from the extract can be simply performed.
【００１１】日本山人参葉部からイソエポキシ−ブテリ
キシンを抽出するためには、水；メタノール、エタノー
ル、プロパノール等の低級アルコール；1,3-ブチレング
リコール、プロピレングリコール、グリセリン等の多価
アルコール；アセトン、メチルエチルケトン等の低級脂
肪族ケトン；酢酸エチル等の低級脂肪酸エステル；ベン
ゼン、ヘキサン等の炭化水素；塩化メチレン、クロロホ
ルム等のハロゲン化炭化水素；ジオキサン、メチルエチ
ルエーテル等の低級脂肪族エーテル等；およびこれらの
混合物等を使用することができる。In order to extract isoepoxy-buterixin from the leaves of Japanese ginseng, water; lower alcohols such as methanol, ethanol and propanol; polyhydric alcohols such as 1,3-butylene glycol, propylene glycol and glycerin; acetone. , Lower aliphatic ketones such as methyl ethyl ketone; lower fatty acid esters such as ethyl acetate; hydrocarbons such as benzene and hexane; halogenated hydrocarbons such as methylene chloride and chloroform; lower aliphatic ethers such as dioxane and methyl ethyl ether; and A mixture of these and the like can be used.
【００１２】原料の日本山人参葉部は、生のままでよい
が、乾燥した保存葉でもよい。葉の採取時期としては秋
が、イソエポキシ−ブテリキシン含有率が高く好まし
い。これを適当に粉砕して抽出処理に付する。The raw material of Japanese ginseng leaf, which is the raw material, may be raw or may be dried preserved leaves. Autumn is preferable as the time for collecting leaves because of its high content of isoepoxy-buterixin. This is appropriately crushed and subjected to extraction treatment.
【００１３】抽出方法には特に制限がなく、簡単には、
常温ないし沸点付近の温度に維持した溶媒中に日本山人
参葉部を浸漬すればよい。抽出液から溶媒を留去すれ
ば、イソエポキシ−ブテリキシンを含有する抽出物が得
られる。必要に応じて活性炭等による脱臭、脱色処理を
施せば、食品、化粧品等に添加しても支障のない粗イソ
エポキシ−ブテリキシンが得られる。There is no particular limitation on the extraction method.
The Japanese ginseng leaf part may be immersed in a solvent maintained at room temperature or a temperature around the boiling point. The solvent is distilled off from the extract to obtain an extract containing isoepoxy-buterixin. If necessary, deodorization and decolorization treatment with activated carbon or the like can be carried out to obtain crude isoepoxy-buterixin which does not interfere with addition to foods, cosmetics and the like.
【００１４】純度の高いイソエポキシ−ブテリキシンを
得るためには、液−液分配抽出、各種クロマトグラフィ
ー、イオン交換、膜分離等の精製手段を適宜採用して精
製する。In order to obtain high-purity isoepoxy-buterixin, purification is carried out by appropriately adopting purification means such as liquid-liquid partition extraction, various chromatography, ion exchange, membrane separation and the like.
【００１５】イソエポキシ−ブテリキシンについては、
アドレナリン、ノルアドレナリン、およびカテコールア
ミンの作用の抑制作用、ＬＴＢ4およびＬＴＣ4の抑制作
用等を有することが確認されている。したがって、本発
明の方法により得られたイソエポキシ−ブテリキシン
も、血管拡張作用、末梢循環の改善、糖尿病症状の改
善、肝の脂肪蓄積防止、アレルギー症状の改善、皮膚炎
等の症状軽快のために、医薬品、医薬部外品、化粧品、
飲食品等に含有させることができる。For isoepoxy-buterixin,
It has been confirmed to have an action of suppressing the actions of adrenaline, noradrenaline, and catecholamine, an action of suppressing LTB 4 and LTC 4 , and the like. Therefore, the isoepoxy-buterixin obtained by the method of the present invention is also for vasodilatory action, improvement of peripheral circulation, improvement of diabetic symptoms, prevention of fat accumulation in liver, improvement of allergic symptoms, improvement of symptoms such as dermatitis. , Pharmaceuticals, quasi drugs, cosmetics,
It can be contained in foods and drinks.
【００１６】[0016]
実施例１ 日本山人参の生葉粉砕物５００ｇに３リットルの酢酸エ
チルを加え、２時間還流下に加熱してイソエポキシ−ブ
テリキシンを抽出した。抽出残渣はさらに２リットルの
酢酸エチルで２回、還流下に加熱して抽出した。抽出液
を合わせて減圧濃縮すると、抽出物５５ｇが得られた。Example 1 To 500 g of freshly ground leaves of Japanese ginseng, 3 liters of ethyl acetate was added and heated under reflux for 2 hours to extract isoepoxy-buterixin. The extraction residue was further extracted twice with 2 liters of ethyl acetate by heating under reflux. The extracts were combined and concentrated under reduced pressure to obtain 55 g of an extract.
【００１７】次いで抽出物５４ｇをシリカゲルカラムク
ロマトグラフィーに付し、下記 n-ヘキサン-酢酸エチル
混合溶媒で順次溶出処理を行なった。 n-ヘキサン-酢酸エチル容積比 混合溶媒使用量（リットル） ２：１ ３ ３：２ ３ １：１ １ １：２ ３ １：４ ２.５Next, 54 g of the extract was subjected to silica gel column chromatography and sequentially eluted with the following n-hexane-ethyl acetate mixed solvent. n-hexane-ethyl acetate volume ratio mixed solvent usage (liter) 2: 1 3 3: 2 3 1: 1 1 1: 2 3 3 1: 4 2.5
【００１８】イソエポキシ−ブテリキシンを含む分画を
セファデックスＬＨ−２０によるカラムクロマトグラフ
ィー（溶媒：酢酸エチル）、次いでシリカゲルクロマト
グラフィー（溶媒：ベンゼン−アセトン＝１０：１）で
精製し、イソエポキシ−ブテリキシン７.２ｇを得た。The fraction containing isoepoxy-buterixin was purified by column chromatography on Sephadex LH-20 (solvent: ethyl acetate) and then on silica gel chromatography (solvent: benzene-acetone = 10: 1) to give an isoepoxy- 7.2 g of buterixin were obtained.
【００１９】実施例２ 日本山人参の葉部と根部を４月および１０月に採取し、
それらの粉砕物（葉部は１ｇ、根部は３ｇ）を酢酸エチ
ル２０mlで３回、それぞれ１時間、還流抽出した。抽出
液を合わせて濃縮乾固し、乾燥抽出物を得た。次いでこ
の抽出物に９０％アセトニトリル５０mlを加えて撹拌
し、不溶物を濾別した。不溶物は９０％アセトニトリル
５mlで洗浄した。濾液と洗浄液を合わせ、９０％アセト
ニトリルを加えて全量を１００mlとし、高速液体クロマ
トグラフィー（ＨＰＬＣ）によるイソエポキシ−ブテリ
キシン定量の試料とした。標品としては、実施例１で得
たイソエポキシ−ブテリキシン１１.１０mgを９０％ア
セトニトリルに溶解し、全量を１００mlにしたものを用
いた。Example 2 The leaves and roots of Japanese ginseng were collected in April and October,
The ground products (1 g for leaves and 3 g for roots) were extracted with 20 ml of ethyl acetate three times under reflux for 1 hour. The extracts were combined and concentrated to dryness to obtain a dry extract. Next, 50 ml of 90% acetonitrile was added to this extract and the mixture was stirred, and the insoluble matter was filtered off. The insoluble matter was washed with 5 ml of 90% acetonitrile. The filtrate and the washing solution were combined and 90% acetonitrile was added to bring the total amount to 100 ml, which was used as a sample for isoepoxy-buterixin quantification by high performance liquid chromatography (HPLC). As the standard, 11.10 mg of isoepoxy-buterixin obtained in Example 1 was dissolved in 90% acetonitrile to make the total amount 100 ml.
【００２０】ＨＰＬＣの条件は次のとおりである。 カラム：ＴＳＫgel ＯＤＳ−１２０ＴM（４.６mm×２
５cm） 溶媒：５０％→９０％アセトニトリル（トリフルオロ酢
酸０.１％含有） ０→２５minグラジエント溶出 流速：１.０ml／min カラム温度：４０℃ 検出：ＵＶ ３４０nm 検体量：２０μl ＨＰＬＣの面積比から、日本山人参の葉部および根部に
おけるイソエポキシ−ブテリキシンの含有率を算出した
結果は表１のとおりであって、葉部は根部よりも顕著に
高率でイソエポキシ−ブテリキシンを含有することが確
認された。The conditions of HPLC are as follows. Column: TSKgel ODS-120T M (4.6mm × 2
5 cm) Solvent: 50% → 90% acetonitrile (containing 0.1% trifluoroacetic acid) 0 → 25 min gradient elution Flow rate: 1.0 ml / min Column temperature: 40 ° C. Detection: UV 340 nm Specimen amount: 20 μl From the area ratio of HPLC The results of calculating the content of isoepoxy-buterixin in the leaves and roots of Japanese ginseng are shown in Table 1, and the leaves may contain isoepoxy-buterixin at a significantly higher rate than the roots. confirmed.
【００２１】[0021]
【表１】 イソエポキシ−ブテリキシン含有率（％） ４月採取葉部 １.６９ 10月採取葉部 ２.９４ ４月採取根部 ０.５５ 10月採取根部 ０.９６[Table 1] Isoepoxy-Buterixin content (%) April collected leaves 1.69 October collected leaves 2.94 April collected roots 0.55 October collected roots 0.96
【００２２】[0022]
【発明の効果】根茎部よりもイソエポキシ−ブテリキシ
ン含有率が著しく高い葉部を用いる本発明によれば、同
じ抽出方法を採用してもイソエポキシ−ブテリキシン含
有率の高い抽出物が得られ、抽出物のまま、粗イソエポ
キシ−ブテリキシンとして使用するときより顕著な使用
効果が奏されるのは勿論、精製して利用する場合にも精
製が容易になり、イソエポキシ−ブテリキシンを安価に
提供することができる。さらに、葉部を利用する本発明
は、根茎部を利用する従来の方法と違って多年植物であ
る日本山人参の株を繰り返し利用することができ、原料
採取がはるかに容易であるから、原料費も低いという利
点がある。EFFECTS OF THE INVENTION According to the present invention, which uses leaves having a significantly higher isoepoxy-buterixin content than the rhizome, an extract having a high isoepoxy-buterixin content can be obtained even if the same extraction method is adopted. As the extract as it is, not only a more remarkable use effect is exhibited when it is used as a crude isoepoxy-buterixin, but also when it is used after purification, the purification becomes easy, and the isoepoxy-buterixin is provided at a low cost. be able to. Furthermore, the present invention utilizing the leaf portion, unlike the conventional method utilizing the rhizome portion, can repeatedly use the strain of Japanese mountain ginseng, which is a perennial plant, and the raw material is much easier to collect. It has the advantage of low cost.
フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ６１Ｋ 31/365 ＡＤＰ 9454−4Ｃ Continuation of the front page (51) Int.Cl. 6 Identification number Office reference number FI technical display location A61K 31/365 ADP 9454-4C
Claims (1)
抽出溶媒として日本山人参(イヌトウキ）の葉部を抽出
処理し抽出物を採取することを特徴とする、3′(R),4′
(R)-3′-エポキシアンゲロイルオキシ-4′-アセトキシ-
3′,4′-ジヒドロセセリンの取得方法。1. 3 '(R), 4', characterized in that the leaves of Japanese ginseng (Inutouki) are subjected to extraction treatment using water, an organic solvent, or a mixture thereof as an extraction solvent.
(R) -3'-Epoxyangeloyloxy-4'-acetoxy-
A method for obtaining 3 ', 4'-dihydroceserine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05220535A JP3122564B2 (en) | 1993-08-13 | 1993-08-13 | Method for obtaining 3 '(R), 4' (R) -3'-epoxyangeloyloxy-4'-acetoxy-3 ', 4'-dihydroseserin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05220535A JP3122564B2 (en) | 1993-08-13 | 1993-08-13 | Method for obtaining 3 '(R), 4' (R) -3'-epoxyangeloyloxy-4'-acetoxy-3 ', 4'-dihydroseserin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0753560A true JPH0753560A (en) | 1995-02-28 |
| JP3122564B2 JP3122564B2 (en) | 2001-01-09 |
Family
ID=16752523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05220535A Expired - Fee Related JP3122564B2 (en) | 1993-08-13 | 1993-08-13 | Method for obtaining 3 '(R), 4' (R) -3'-epoxyangeloyloxy-4'-acetoxy-3 ', 4'-dihydroseserin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3122564B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08256724A (en) * | 1995-03-28 | 1996-10-08 | Hisao Takasaki | Health food |
| JP2014237635A (en) * | 2013-05-09 | 2014-12-18 | 国立大学法人九州大学 | Production method and nerval protective agent |
| JP2016172711A (en) * | 2015-03-16 | 2016-09-29 | 国立大学法人九州大学 | Blood clotting inhibitor and production method of blood clotting inhibitor |
| JP2017066145A (en) * | 2016-10-07 | 2017-04-06 | 国立大学法人九州大学 | Hair matrix cell-proliferation enhancer, dermal papilla cell-proliferation enhancer, alopecic topical agent and production method of alopecic topical agent |
| JP2018024687A (en) * | 2017-09-13 | 2018-02-15 | 国立大学法人九州大学 | Method for producing hair care product, hair matrix cell proliferation promoter, dermal papilla cell proliferation promoter and melanin production promoter |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103120304B (en) * | 2012-06-21 | 2017-04-12 | 刘跃魁 | Planting method for Japanese mountain ginseng |
-
1993
- 1993-08-13 JP JP05220535A patent/JP3122564B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08256724A (en) * | 1995-03-28 | 1996-10-08 | Hisao Takasaki | Health food |
| JP2014237635A (en) * | 2013-05-09 | 2014-12-18 | 国立大学法人九州大学 | Production method and nerval protective agent |
| JP2016172711A (en) * | 2015-03-16 | 2016-09-29 | 国立大学法人九州大学 | Blood clotting inhibitor and production method of blood clotting inhibitor |
| JP2017066145A (en) * | 2016-10-07 | 2017-04-06 | 国立大学法人九州大学 | Hair matrix cell-proliferation enhancer, dermal papilla cell-proliferation enhancer, alopecic topical agent and production method of alopecic topical agent |
| JP2018024687A (en) * | 2017-09-13 | 2018-02-15 | 国立大学法人九州大学 | Method for producing hair care product, hair matrix cell proliferation promoter, dermal papilla cell proliferation promoter and melanin production promoter |
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| JP3122564B2 (en) | 2001-01-09 |
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