JPS5857365A - Clithioneine - Google Patents
ClithioneineInfo
- Publication number
- JPS5857365A JPS5857365A JP56155605A JP15560581A JPS5857365A JP S5857365 A JPS5857365 A JP S5857365A JP 56155605 A JP56155605 A JP 56155605A JP 15560581 A JP15560581 A JP 15560581A JP S5857365 A JPS5857365 A JP S5857365A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- ergothioneine
- clithioneine
- present
- chromatography
- 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)
Abstract
Description
【発明の詳細な説明】
本発明はクリチオネイ７に関する０本発明者らは、ドタ
ササコ（０１ｉｔｏａｙｂｅ ａｃｒｏｍｅｌｍｌｇａ
）Ｏ生Ｉ！＠性成分に′）−で検討してきたが、今般
。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to Crithionei 7.
) O student I! We have been considering the @sexual component')-, but this time.
新ａｔ−成分を見出し、本発明に到達した。A new at-component was discovered and the present invention was achieved.
すなわち、本発明は、式（１）
で示されるクリチオネインにめる。以下１本発明の詳細
な説明する。That is, the present invention focuses on critionein represented by formula (1). The present invention will be explained in detail below.
本発明に係るクリチオネインは、上記式中で示されるコ
＜８＞ −ＩＩ −Ｃコ（８）−ヒドロキシ−３（８）
−７１ノーＪ−カルボキシプロピルツーエルゴチオネイ
ンであり、本発明者らの命名によるものである。このク
リチオネインは、ドクササコの子実体より得られる。ド
クササコは、−名ヤブシメジ又はヤケドキンといわれ、
秋季、竹林内に多数群生又は数個叢生する。子実体は高
さＪ ＝ ／ Ｏａｘ０傘は径夕〜１ＯＤ１１％橙褐色
で中央部は〈埋んで漏斗形をなし、周縁は下方Ｋｍれる
。ＸはＪ〜！ａａＸＯ，ｊｚＯ，Ｉａｍで傘とほぼ同色
。分布は日本（本州）である。ドクサナコよりクリチオ
ネインを得るのは１例えは次のような方法による。すな
わち％まず子実体の水抽出物をアセトン又はアルコール
を用いて沈殿処理する０次いで難溶物を透析後、さらに
クロマトグラフィー、イオン交換樹脂、ｔＰ紙電気泳動
等によって精製する。Crithionein according to the present invention is a co<8>-II-C co(8)-hydroxy-3(8) represented by the above formula.
-71 No J-carboxypropyl-to-ergothioneine, named by the present inventors. This clithionein is obtained from the fruiting body of Doxasako. Doxasako is called Yabushimeji or Yakedokin.
In autumn, they grow in large numbers or in clusters in bamboo forests. The fruit body is height J = / Oax0 The cap is orange-brown in diameter, and the central part is buried and funnel-shaped, and the periphery extends Km downward. X is J~! aaXO, jzO, and Iam, almost the same color as the umbrella. Distribution is Japan (Honshu). An example of how to obtain critionein from doxanaco is as follows. That is, first, an aqueous extract of the fruiting body is precipitated using acetone or alcohol. Next, hardly soluble substances are dialyzed, and then further purified by chromatography, ion exchange resin, tP paper electrophoresis, etc.
クロマトグラフィーとしては、カラムクロマトダラフイ
ー、薄層クロマトグラフィー等が用いられる。カラムク
ロ！トゲラフイーＯ充填剤としては、シリカゲル、アル
２す、活性炭等が挙げられる。溶出溶剤は、充填剤に応
じて適宜選択されるが、活性炭を用い良場合には、エタ
ノールが好適である。薄層クロマトグラフィーの吸着剤
としては、シリカゲル、ア＃ミナ、−１ルロースパウダ
ー等が用−られる、展開溶媒としては、メタノール、タ
ロロホルム等が好適である。精製法の一例として、好適
には、透析−イオン交換樹脂処理−Ｆ紙電気泳動−薄層
クロ１トゲラフイー−逆相高速液体クロマトグラフィー
の組合せが挙げられる０本発明に係るクリチオネインは
血圧降下作用を有し、血圧降下剤゛ としての用途が
期待される。As the chromatography, column chromatography, thin layer chromatography, etc. are used. Karamkuro! Examples of the Togelafy O filler include silica gel, aluminum oxide, and activated carbon. The elution solvent is appropriately selected depending on the filler, but if activated carbon is suitable, ethanol is suitable. As the adsorbent for thin layer chromatography, silica gel, aminumina, -1 luulose powder, etc. are used. As the developing solvent, methanol, taloloform, etc. are suitable. As an example of the purification method, a preferable combination of dialysis, ion exchange resin treatment, F paper electrophoresis, thin layer chromatography, reversed phase high performance liquid chromatography, etc. It is expected to be used as a blood pressure lowering agent.
以下実施例により本発明をさらに詳細に説明する。The present invention will be explained in more detail with reference to Examples below.
実施例／
／Ｆ７７年〜ｌり７デ都に新濤県で採取したドクササコ
子冥体１ｔ、Ｉｋｆより２次の工１ＭＫよ）クリチオネ
イン３１ｑを得え。EXAMPLE / Obtain 31 q of clithionein (1 MK of secondary work from Ikf) and 1 t of Doxasako child's body collected in Shinto Prefecture in 1977.
／ｌ、ｌ：ｋｌ ドタナサコ
」
水抽出物
１４１ｆ 外液
Ｉｔ １０％Ｆ！ｔｏＨ
Ｏ，ｆｆ コ、ｔ ｑｋ Ｍ１１４０Ｈθ
／ｊｊｑ ｊａｌ
６１ｑ ＲｆＯ，ＪＩ
得られ九クリチオネインは、ニンヒドリンで黄色を示し
、ボーリー（Ｐａｕｘｙ ）試験（Ｊ、 Ｍｅｌ。/l,l:kl Dotanasako'' Water extract 141f External fluid It 10%F! toH O,ff ko,t qk M1140Hθ /jjq jal 61q RfO,JI The nine-crithionein obtained showed a yellow color with ninhydrin and was tested by the Pauxy test (J, Mel.
Ｏｈｅｍ、、 ／ ／、コｓｒ（ｔｙｇｒ＞）で黄色を
示す。Ohem, / /, shows yellow in cosr (tygr>).
ｏ、ｓｉ、１ｔ４ｏ、ｓ
施光度：〔−〕雷十杯、２＠（ｏ斌０．ｊ、Ｂ宜０）工
Ｒ：Ｊ４００−コ、２００ 、 ／ ４ Ｊ ０ｔｘ−
’ （ｎｕ、１０１）Ｕｖ ：λｐＨ７ａａ４ ｎｍ（
ｔ ／６ｏｏｏ）ａｘ
ｉ ｐＨココｊ４ｃｎｍ （＠／７３００）ｍ＆Ｘ
λｐＨ／、２コＩｌｌｒｕｍ（ｍ／１０００）ＰＬＸ
Ｍム８８ ： ｍ／ｅ Ｊ＃７，１１３１％（Ｍ＋１
）”≦
芳香族水素の’ＨＮＭＲ（＃ｐ、０７ 、０ （ｓ）
）は、式（１）で示されるＳ−（β−アミノ−β−カル
ダキシエチル）−エルゴチオネインと酷似する。クリチ
オネインは、上記式（厘）で示される化合物に類似し九
置換パターンのインダゾール環を有する（ｓ））Ｋ：よ
って支持される。Ｋｌ−Ｍｓスペクトルは、分子状イオ
ンのピークを示さないが、フラグメンテーション・パタ
ーンは式（厘）で示されるエルゴチオネインのそれと完
全Ｋ 一致し九。したがってインダゾール環の！−位の
置換は一〇ＨＩＯＲ（ＮＭｅｓ） ００２である。ＨＭ
ＭＲと”ＯＭＭＢスペクトルはこの部分の存在を明らか
にし良。o, si, 1t4o, s Light intensity: [-] Raijubei, 2@(obin0.j, Bgi0) Engineering R: J400-ko, 200, / 4 J 0tx-
' (nu, 101) Uv: λpH7aa4 nm (
t /6ooo) ax i pH here j4cnm (@/7300) m&X λpH/, 2coIllrum (m/1000) PLX Mmu88: m/e J#7,1131% (M+1
)"≦ 'HNMR of aromatic hydrogen (#p, 07, 0 (s)
) is very similar to S-(β-amino-β-cardaxyethyl)-ergothioneine represented by formula (1). Crithionein is similar to the compound of formula (厘) above and has an indazole ring with a nine-substitution pattern (s)). Although the Kl-Ms spectrum does not show any molecular ion peaks, the fragmentation pattern completely matches that of ergothioneine shown by the formula (9). Hence the indazole ring! The substitution at the - position is 10HIOR(NMes)002. H.M.
MR and OMMB spectra clearly reveal the existence of this part.
’ ＨＩＩＭＲ： ずＤ！０ ３．、ｚ ４’ （ｅ
＊りＨ）”ＯＮＭＲ： ＃ｎ２０７ ｏ、ｏ （ｔ、−
０Ｈｚ−）ｂｚ４１．ｔ （ｑ 、 −）１Ｍｅｓ ）
。'HIIMR: ZuD! 0 3. , z 4' (e
*riH)"ONMR: #n207 o, o (t, -
0Hz-)bz41. t(q, −)1Mes)
.
Ｉ Ｏ９４（６、−０１１２（ＮＭａｌ ） Ｇｏ！″
）、１７参、７（ｔ、−ＢＯＨｉ→、ｔ Ｏ，２（ｄ
、−ＱＨ（１ｍ１３）ＣＯｉ）、７７．４（ａ、 ａ
ｍ−ｏＨ）、 ／７Ｊ、＃（ｍ、−００！″）〕よシ決
定された。なお確認のためクリチオネインをラネーＮ１
で処理すると、ふたつのニンヒドリン陰性の化合物及び
ひとつのボーリー陽性の化合物が得られ友。クロマトグ
ラフィー及び各種スペクトルによればそれらはＬ−スレ
゛オニン、Ｌ−ａ−アミノ−ｎ−酢酸及びＬ−へルシニ
ンであつ良。I O94 (6, -0112 (NMal) Go!''
), 17, 7(t, -BOHi→, t O,2(d
, -QH(1m13)COi), 77.4(a, a
m-oH), /7J, #(m,-00!″)] was determined.For confirmation, crithionein was added to Raney N1.
Two ninhydrin-negative compounds and one Boley-positive compound were obtained. According to chromatography and various spectra, they are L-threonine, La-amino-n-acetic acid, and L-hercynin.
すなわち、本発明のクリチオネインＦｉ１λ（８）−Ｂ
−（Ｊ （８）−ヒドロキシ−Ｊ（８）−アギノー３
−カルボキシプロピル〕−エルゴチオネインであること
が示された。That is, the critionein Fi1λ(8)-B of the present invention
-(J(8)-hydroxy-J(8)-agino3
-carboxypropyl]-ergothioneine.
出 願 人 三菱化成工業株式会社
代 還 人 弁理士 長谷用 −
（ほか１名）
手続補正鳶（砿）
１ 事件の表示
昭和５６年特許願第１５ｇ６０５号
２ 発明の名称
り リ チ オ ネ イ ン３ 補正をす
る省
事件との関係 出願人
（５９６） 三菱化成工業株式会社
４代理人 〒１００
東京都千代田区丸の内二丁目５番２月
三菱化成工業株式会社内
５ 補正命令の日付 昭和５７年２ ／１２３日（発送
日）６ 補正の対象 願 書 および 明 細 書
７ 補正の内容Applicant: Mitsubishi Chemical Industries, Ltd. Representative: Patent attorney: Yo Hase - (1 other person) Procedural amendment (Tobi) 1. Indication of the case 1982 Patent Application No. 15g605 2. Name of the invention: Lithion 3. Relationship with the Ministry case for amendment Applicant (596) Mitsubishi Chemical Industries, Ltd. 4 Agent Address: February 5, 2-5 Marunouchi, Chiyoda-ku, Tokyo 100 Mitsubishi Chemical Industries, Ltd. Date of amendment order February 1982 /123rd (shipment date) 6 Subject of amendment Application and specification 7 Contents of amendment
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56155605A JPS5857365A (en) | 1981-09-30 | 1981-09-30 | Clithioneine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56155605A JPS5857365A (en) | 1981-09-30 | 1981-09-30 | Clithioneine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5857365A true JPS5857365A (en) | 1983-04-05 |
Family
ID=15609672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56155605A Pending JPS5857365A (en) | 1981-09-30 | 1981-09-30 | Clithioneine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5857365A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5399818U (en) * | 1976-06-23 | 1978-08-12 |
-
1981
- 1981-09-30 JP JP56155605A patent/JPS5857365A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5399818U (en) * | 1976-06-23 | 1978-08-12 |
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