JPH0348189B2 - - Google Patents
Info
- Publication number
- JPH0348189B2 JPH0348189B2 JP57036864A JP3686482A JPH0348189B2 JP H0348189 B2 JPH0348189 B2 JP H0348189B2 JP 57036864 A JP57036864 A JP 57036864A JP 3686482 A JP3686482 A JP 3686482A JP H0348189 B2 JPH0348189 B2 JP H0348189B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- chromatography
- acid
- salts
- esters
- 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 - Lifetime
Links
- CWXNEBSQRIECMV-UHFFFAOYSA-N Acromelic acid A Natural products OC(=O)CC1C(NCC1C1=CC=C(NC1=O)C(O)=O)C(O)=O CWXNEBSQRIECMV-UHFFFAOYSA-N 0.000 claims description 8
- 229930183027 acromelic acid Natural products 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001142 circular dichroism spectrum Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- 241000502280 Clitocybe Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- VLSMHEGGTFMBBZ-UHFFFAOYSA-N alpha-Kainic acid Natural products CC(=C)C1CNC(C(O)=O)C1CC(O)=O VLSMHEGGTFMBBZ-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 208000012601 choreatic disease Diseases 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- VLSMHEGGTFMBBZ-OOZYFLPDSA-N kainic acid Chemical compound CC(=C)[C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O VLSMHEGGTFMBBZ-OOZYFLPDSA-N 0.000 description 1
- 229950006874 kainic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Description
本発明はアクロメリン酸並びにその塩もしくは
エステル類に関する。
本発明者らはドクササコ（Clitocybe
acromelealga）の生理活性成分について検討し
てきたが、今般、新規な成分を見出し、本発明に
到達した。
すなわち、本発明は、式（）
で示されるアクロメリン酸並びにその塩もしくは
エステル類にある。
以下、本発明を詳細に説明する。
本発明に係るアクロメリン酸
（acromelicacid）は、本発明者らの命名による
ものであり、ドクササコの子実体より得られた。
ドクササコは、一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３〜10cmである。傘は径５〜
10cm、橙褐色で中央部はくぼんで漏斗形をなし、
周縁は下方に垂れる。茎は３〜５cm×0.5〜0.8cm
で傘とほぼ同色。分布は日本（本州）である。
本発明において、ドクササコよりアクロメリン
酸を得るのは、たとえば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澱処理する。
次いで、難溶物を透析後、2.5〜５％のエタノ
ールを用いてカラムクロマトグラフイーで処理
し、さらにクロマトグラフイー、イオン交換樹
脂、紙電気泳動等によつて精製する。
クロマトグラフイーとしては、カラムクロマト
グラフイー、薄層クロマトグラフイー等が用いら
れる。カラムクロマトグラフイーの充填剤として
は、シリカゲル、アルミナ、活性炭等が挙げられ
る。溶出溶剤は、充填剤に応じて適宜決定される
が、活性炭を用いた場合には、エタノールが好適
である。薄層クロマトグラフイーの吸着剤として
は、シリカゲル、アルミナ、セルロースパウダー
等が用いられる。展開溶媒としては、メタノー
ル、ク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、
(A) 透析−カラムクロマトグラフイー−イオン交
換樹脂−紙電気泳動−薄層クロマトグラフイ
ー−逆相クロマトグラフイー−薄層クロマトグ
ラフイー−紙電気泳動−ゲルクロマトグラフ
イー、
(B) 透析−カラムクロマトグラフイー−イオン交
換樹脂−紙電気泳動−薄層クロマトグラフイ
ー−紙電気泳動−ゲルクロマトグラフイー、
の組合せが挙げられる。
得られるアクロメリン酸は、薬剤的に許容しう
る塩又はエステル類とすることができる。塩とし
ては、たとえばアルカリ金属塩、有機塩基塩、エ
ステルとしては、たとえば、低級アルキルエステ
ルが挙げられる。
本発明に係るアクロメリン酸並びにその塩もし
くはエステル類は、遺伝性進行性（ハンチングト
ン）舞踏病、パーキンソン病、その他神経伝達物
質に関連する病気の治療への適用が期待される。
以下、実施例により本発明をさらに詳細に説明
する。
実施例 １
1977年〜1979年に新潟県で採取したドクササコ
子実体16.8Kgより、次の工程によりアクロメリン
酸（′）及び（″）をそれぞれ110μｇ、40μｇ
得た。
The present invention relates to acromelic acid and its salts or esters. The present inventors have discovered that Clitocybe
acromerealga), and have recently discovered a new component and arrived at the present invention. That is, the present invention provides the formula () This includes acromelic acid and its salts or esters. The present invention will be explained in detail below. Acromelic acid according to the present invention was named by the present inventors and was obtained from the fruiting body of Doxasako. Dokusasako, also known as Yabushimeji or Yakedokin, grows in large numbers or in clusters in bamboo forests in autumn. The fruiting body is 3-10 cm in height. Umbrella diameter 5~
10cm long, orange-brown in color with a concave, funnel-shaped center.
The rim hangs downward. Stem is 3-5cm x 0.5-0.8cm
Almost the same color as the umbrella. Distribution is Japan (Honshu). In the present invention, acromelic acid is obtained from doxasaco, for example, by the following method. That is, first, an aqueous extract of the fruiting body is subjected to a precipitation treatment using acetone or alcohol. Next, the poorly soluble material is dialyzed, treated with column chromatography using 2.5 to 5% ethanol, and further purified by chromatography, ion exchange resin, paper electrophoresis, etc. As the chromatography, column chromatography, thin layer chromatography, etc. are used. Examples of packing materials for column chromatography include silica gel, alumina, and activated carbon. The elution solvent is appropriately determined depending on the filler, but when activated carbon is used, ethanol is suitable. Silica gel, alumina, cellulose powder, etc. are used as adsorbents for thin layer chromatography. As the developing solvent, methanol, chloroform, etc. are suitable. As an example of the purification method, preferably, (A) dialysis - column chromatography - ion exchange resin - paper electrophoresis - thin layer chromatography - reversed phase chromatography - thin layer chromatography - paper electrophoresis - Examples include a combination of (B) dialysis-column chromatography-ion exchange resin-paper electrophoresis-thin layer chromatography-paper electrophoresis-gel chromatography. The resulting acromelic acid can be made into pharmaceutically acceptable salts or esters. Examples of the salt include alkali metal salts and organic base salts, and examples of the ester include lower alkyl esters. Acromelic acid and its salts or esters according to the present invention are expected to be applied to the treatment of hereditary progressive (Huntington's) chorea, Parkinson's disease, and other diseases related to neurotransmitters. Hereinafter, the present invention will be explained in more detail with reference to Examples. Example 1 From 16.8 kg of Doxasako fruiting bodies collected in Niigata Prefecture from 1977 to 1979, 110 μg and 40 μg of acromelic acid (′) and (″), respectively, were obtained through the following steps.
Obtained.
【表】
↓ ↓
[Table] ↓ ↓
【表】
↓
単離物A(110μg)
（単離物Ａ及びＢの物性・構造）
360MHz・NMR、UVおよびCDスペクトル等
を種々の類似化合物と比較し、単離化合物Ａ及び
Ｂがそれぞれ前記（′）及び（″）であること
を決定した。
() NMRスペクトル（360MHz、D2O、DSS）
[Table] ↓
Isolate A (110μg)
(Physical properties and structures of isolated compounds A and B) Comparing the 360MHz NMR, UV and CD spectra with various similar compounds, it was confirmed that isolated compounds A and B have the above (') and (''), respectively. () NMR spectrum (360MHz, D 2 O, DSS)
【表】
〜
【table】 ~
【表】
〜
【table】 ~
() UVスペクトル 単離物Ａ 単離物Ｂ PH７ 240313 ｎｍ PH７ 239310 ｎｍ PH２ 242317 PH２ 242313 PH１ 2241312 PH１ 2235302 () 紙電気泳動 （PH4.6600V、２時間） 単離物Ａ ９cm 〃 Ｂ ９cm カイニン酸 ５cm グルタミン酸 ６cm () CDスペクトル 単離物Ａ （−）205cm 〃 Ｂ （＋）206cm () UV spectrum Isolate A Isolate B PH7 240313 nm PH7 239310 nm PH2 242317 PH2 242313 PH1 2241312 PH1 2235302 () Paper electrophoresis (PH4.6600V, 2 hours) Isolate A 9cm B 9cm Kainic acid 5cm Glutamic acid 6cm () CD spectrum isolate A (-) 205cm 〃 B (+) 206cm
Claims (1)
エステル類。[Claims] 1 Formula () Acromelic acid and its salts or esters.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57036864A JPS58154578A (en) | 1982-03-09 | 1982-03-09 | Acromelic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57036864A JPS58154578A (en) | 1982-03-09 | 1982-03-09 | Acromelic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58154578A JPS58154578A (en) | 1983-09-14 |
| JPH0348189B2 true JPH0348189B2 (en) | 1991-07-23 |
Family
ID=12481645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57036864A Granted JPS58154578A (en) | 1982-03-09 | 1982-03-09 | Acromelic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58154578A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04125706U (en) * | 1991-05-09 | 1992-11-17 | ミドリ安全工業株式会社 | tip of shoe upper |
-
1982
- 1982-03-09 JP JP57036864A patent/JPS58154578A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58154578A (en) | 1983-09-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0578723B1 (en) | PROCESS FOR PURIFICATION OF HMG-CoA REDUCTASE INHIBITORS | |
| JPS6059237B2 (en) | Active substances from Lamiaceae plants | |
| JP2511558B2 (en) | Method for separating and purifying Ginkgolide from strawberry leaf | |
| EP0036663B1 (en) | Oxiranebutanoic acid derivatives, their preparation and use, and medicaments containing them | |
| JPH0348189B2 (en) | ||
| DE69532878T2 (en) | A process for purifying viral hepatitis B surface antigen containing a preS2 peptide | |
| CN110003198B (en) | Purification method of penehyclidine | |
| JPS617285A (en) | Extraction of purified saponin | |
| JPH09502707A (en) | Method for producing 9- (2-hydroxy) ethoxymethylguanine | |
| EP1446397B1 (en) | Novel mandelate salts of substituted tetracyclic tetrahydrofuran derivatives | |
| JPS6267025A (en) | Pharmaceutical composition and production thereof | |
| CA1083589A (en) | Effective substance from plants belonging to the labiatae family | |
| Peet et al. | Xanthines with C8 chiral substituents as potent and selective adenosine A1 antagonists | |
| JPH0578384A (en) | Flavonol derivative | |
| JP2809573B2 (en) | New lysophosphatidylinositol and its production method | |
| JPH0386824A (en) | Diterpene compound and antiinflammoatory drug containing the same as active ingredient | |
| CN108948047A (en) | A kind of purification process of tesirolimus | |
| US2480991A (en) | Method of producing penicillin preparations | |
| CH483397A (en) | Process for the preparation of phenylalanine derivatives | |
| SU1168254A1 (en) | Method of obtaining rosavine | |
| JP2000511878A (en) | Purification method of 11β-21-dihydroxy-2′-methyl-5′βH-pregn-1,4-dieno [17,16-D] oxazole-3,20-dione | |
| CN105924409A (en) | Resolution method of (R)-1-((2-chlorphenyl)-(phenyl)-methyl)-piperazine | |
| JPH0149152B2 (en) | ||
| JPS5929700A (en) | Purification of s-adenosyl-l-methionine | |
| JPH1192492A (en) | Method for separating 3-o-glucopyranosyl-gamma-butyrolactone |