JPH04202176A - Purification of abscisic acid - Google Patents
Purification of abscisic acidInfo
- Publication number
- JPH04202176A JPH04202176A JP33489690A JP33489690A JPH04202176A JP H04202176 A JPH04202176 A JP H04202176A JP 33489690 A JP33489690 A JP 33489690A JP 33489690 A JP33489690 A JP 33489690A JP H04202176 A JPH04202176 A JP H04202176A
- Authority
- JP
- Japan
- Prior art keywords
- abscisic acid
- organic solvent
- cis
- acid
- trans
- 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
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 title claims abstract description 104
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000000746 purification Methods 0.000 title description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 abstract description 13
- 241000123650 Botrytis cinerea Species 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 3
- 239000011707 mineral Substances 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 cultured product Chemical compound 0.000 abstract 1
- 230000000813 microbial effect Effects 0.000 abstract 1
- 229930195732 phytohormone Natural products 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003375 plant hormone Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は植物ホルモンである、（＋）シス−トランス型
アブシジン酸（以下、アブシジン酸と略記する）の精製
法に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for purifying (+) cis-trans type abscisic acid (hereinafter abbreviated as abscisic acid), which is a plant hormone.
〈従来の技術〉
アブシジン酸は天然型植物ホルモンとして重要なもので
あり、広い用途が期待されている。<Prior Art> Abscisic acid is important as a natural plant hormone and is expected to have a wide range of uses.
従来醗酵法によるアブシジン酸の生成については、セル
コスポラ−ｏシコラ（Ｃｅ＋ｃｏｓｐｏ＋ａ ＋ｏｓｉ
ｃｏｌａ） （特開昭５８−３６３９３号公報、特開
昭５６−１６０９９６号公報）およびボトリチス・シネ
レア（ＢｏｌＢ）ｉｓ ｃｉｎｅ＋ｅａ） （特開昭５
８−５１８９５号公報、特開昭６３−２９６６９６号公
報、特開昭６３−２９６６９７号公報、特開平２．−６
０５９０号公報）による液体培養および固体培養が知ら
れている。アブシジン酸の一般的な精製法としては有機
溶媒を用いた抽出法、シリカゲルおよび活性炭などを用
いたクロマトグラフィーを組合せる方法などが挙げられ
、ボトリチス・シネレアの培養物・培養液がらもこの方
法でアブシジン酸を精製単離が可能である。培養物から
のアブシジン酸の精製単離は溶媒抽出を主とした方法で
行われてきたが、溶媒抽出は多量の溶媒を使用する難点
があった。Regarding the production of abscisic acid by conventional fermentation method, Cercospora-o-Cicola (Ce+cospo+a+osi
cola) (JP-A-58-36393, JP-A-56-160996) and Botrytis cinerea (BolB) is cine+ea) (JP-A-58-160996)
No. 8-51895, JP-A-63-296696, JP-A-63-296697, JP-A-Hei 2. -6
Liquid culture and solid culture according to Japanese Patent No. 0590 are known. Common purification methods for abscisic acid include extraction methods using organic solvents and methods that combine chromatography using silica gel and activated carbon, etc. Cultures and culture fluids of Botrytis cinerea are also purified using this method. It is possible to purify and isolate abscisic acid. Purification and isolation of abscisic acid from cultures has been carried out mainly by solvent extraction, but solvent extraction has the disadvantage of using a large amount of solvent.
そこで、強塩基性陰イオン交換樹脂およびポリスチレン
系多孔性吸着樹脂を用いる方法が提案された（特開昭５
？−８２，３４０号公報）。Therefore, a method using a strongly basic anion exchange resin and a polystyrene-based porous adsorption resin was proposed (Japanese Patent Application Laid-open No.
? -82,340).
〈発明が解決しようとする課題〉
特開昭５９−８２３４０号公報の方法により、アブシジ
ン酸の精製がかなり容易になったが、回収率および精製
純度が不十分であった。<Problems to be Solved by the Invention> Although the method disclosed in JP-A-59-82340 made purification of abscisic acid considerably easier, the recovery rate and purification purity were insufficient.
〈課題を解決するための手段〉
そこで本発明者らは鋭意検討の結果、弱塩基性陰イオン
交換樹脂にアブシジン酸を含む培養抽出液を接触させる
ことにより、樹脂にアブシジン酸を吸着させ、アセトン
、メタノールなとの水溶性有機溶媒を７０％以下含んだ
酸またはアルカリにより、収率よくかつ高純度にアブシ
ジン酸を回収できることを見出し、本発明を完成するに
至った。<Means for Solving the Problems> As a result of intensive studies, the present inventors found that by contacting a weakly basic anion exchange resin with a culture extract containing abscisic acid, the resin adsorbed abscisic acid, and acetone The present inventors have discovered that abscisic acid can be recovered in good yield and with high purity using an acid or alkali containing 70% or less of a water-soluble organic solvent such as methanol, and have completed the present invention.
すなわち、本発明は、アブシジン酸を含む溶液を弱塩基
性陰イオン交換樹脂と接触させることにより前記アブシ
ジン酸を前記樹脂に吸着させた後、前記アブシジン酸を
７０％以下の水溶性有機溶媒を含む溶出剤で溶出させる
ことを特徴とするアブシジン酸の精製法である。That is, the present invention allows the abscisic acid to be adsorbed onto the resin by contacting a solution containing abscisic acid with a weakly basic anion exchange resin, and then absorbs the abscisic acid into a solution containing 70% or less of a water-soluble organic solvent. This is a method for purifying abscisic acid characterized by elution using an eluent.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
本発明によれば、アブシジン酸を含む溶液を弱塩基性陰
イオン交換樹脂と接触させることにより、アブシジン酸
を該樹脂に吸着させ、しかるのちに溶出剤により溶出す
ることによりアブシジン酸を精製することができる。According to the present invention, abscisic acid is purified by contacting a solution containing abscisic acid with a weakly basic anion exchange resin to adsorb abscisic acid to the resin, and then eluting it with an eluent. I can do it.
本発明において用いるアブシジン酸を含む溶液は、たと
えばボトリチス・シネレアなどのアブシジン酸生産菌株
の培養物、培養液ならびにそれらの処理物などが挙げら
れる。ボトリチス・シネレアによるアブシジン酸の生産
については、特開昭５８−５１８９５号公報、特開昭６
３−２９６６９６号公報、特開昭６３−２９６６９７号
公報、特開平２−６０５９０号公報に記載されている。Examples of the abscisic acid-containing solution used in the present invention include cultures of abscisic acid-producing bacterial strains such as Botrytis cinerea, culture solutions, and processed products thereof. Regarding the production of abscisic acid by Botrytis cinerea, JP-A No. 58-51895 and JP-A No. 6
It is described in JP-A No. 3-296696, JP-A-63-296697, and JP-A-2-60590.
本発明において用いる弱塩基性陰イオン交換樹脂として
は、″ダイヤイオン”ＷＫＩＯ，同一 ３ −
ＷＫＩＩ、同ＷＫ２０、同ＷＡＩＯ，同ＷＡ１１、同Ｗ
Ａ２０、同ＷＡ２１、同ＷＡ３０（以上、三菱化成社商
品名）、″１アンバーライト″ＩＲ−４Ｂ１同ＩＲ−４
５（以上、ロームアンドハース社商品名）、″ダウエッ
クス″３、同ＭＷＡ−１、同ＷＧ、ＲＡ（以上、ダウケ
ミカル社商品名）などが用いられる。Examples of the weakly basic anion exchange resins used in the present invention include "Diaion" WKIO, "Diaion" 3-WKII, "Diaion" WK20, "Diaion" WAIO, "Diaion" WAIO, "Diaion" WA11, and "Diaion" WKIO.
A20, WA21, WA30 (all Mitsubishi Chemical product names), "1 Amberlight" IR-4B1 IR-4
5 (all trade names of Rohm and Haas), "Dowex" 3, MWA-1, WG, RA (all trade names of Dow Chemical), etc. are used.
本発明において用いる溶出剤としては鉱酸（硫酸、塩酸
など）、アルカリ（苛性ソーダ、苛性カリ、アンモニア
など）の水溶液にメタノール、エタノール、プロパノー
ル、イソプロパノール、アセトンなどの水溶性有機溶媒
を加えた液が用いられる。添加する水溶性有機溶媒の量
が増えるにしたがって、アブシジン酸の溶出率は高まる
が７０％を超えると溶出液中のアブシジン酸の純度は著
しく低下する。有機溶媒の種類あるいはアブシジン酸の
吸着量によっても左右されるが、水溶性有機溶媒の使用
範囲は１０〜７０％（Ｖ／Ｖ）が好適である。鉱酸０．
ＩＮ〜２Ｎ、アルカリ０．１ Ｎ〜２Ｎなどの一般的溶
出−４＝
剤を用いると、溶出されるアブシジン酸の量は１０〜３
０％と回収率が低く実用的でないが、水溶性有機溶媒を
添加することによって回収率を大幅に向上させることが
可能となる。The eluent used in the present invention is a solution prepared by adding a water-soluble organic solvent such as methanol, ethanol, propanol, isopropanol, or acetone to an aqueous solution of mineral acid (sulfuric acid, hydrochloric acid, etc.) or alkali (caustic soda, caustic potash, ammonia, etc.). It will be done. As the amount of water-soluble organic solvent added increases, the elution rate of abscisic acid increases, but when it exceeds 70%, the purity of abscisic acid in the eluate decreases significantly. Although it depends on the type of organic solvent or the amount of abscisic acid adsorbed, the range of use of the water-soluble organic solvent is preferably 10 to 70% (V/V). Mineral acid 0.
Using common elution agents such as IN~2N and alkaline 0.1N~2N, the amount of abscisic acid eluted is 10~3
Although the recovery rate is as low as 0% and is not practical, it is possible to significantly improve the recovery rate by adding a water-soluble organic solvent.
アブシジン酸を含む溶出液からのアブシジン酸の回収は
以下のとおり行う。溶出液を減圧濃縮し、有機溶媒を除
去した後、培養物中に含まれるアミノ酸、タンパク質を
含むカチオン成分を除去するため強酸性陽イオン交換樹
脂を素通りさせ、素通りした液を減圧濃縮しアブシジン
酸を結晶化させる。あるいは溶出液から同様に有機溶媒
を除去した後、ｐ’ Ｈ２〜３に調整し、培養物中に含
まれる中性あるいは塩基性水溶性物質および金属イオン
などを除去するため、酢酸エチルなどの水に溶けにくい
有機溶媒で抽出する。抽出液を無水硫酸ナトリウムなど
を加えて脱水し、炉液を減圧濃縮しアブシジン酸を結晶
化させる。結晶を分離後、真空乾燥してアブシジン酸の
白色結晶を得る。必要があれば、減圧濃縮前に活性炭で
脱色処理する操作を加える。Recovery of abscisic acid from the eluate containing abscisic acid is performed as follows. After concentrating the eluate under reduced pressure to remove the organic solvent, it is passed through a strongly acidic cation exchange resin to remove cationic components including amino acids and proteins contained in the culture, and the passed-through liquid is concentrated under reduced pressure to absorb abscisic acid. crystallize. Alternatively, after removing the organic solvent from the eluate in the same way, adjust the pH to 2 to 3, and add water such as ethyl acetate to remove neutral or basic water-soluble substances and metal ions contained in the culture. Extract with an organic solvent that is poorly soluble. The extract is dehydrated by adding anhydrous sodium sulfate, etc., and the furnace liquid is concentrated under reduced pressure to crystallize abscisic acid. After separating the crystals, they are vacuum dried to obtain white crystals of abscisic acid. If necessary, add decolorization treatment with activated carbon before concentration under reduced pressure.
〈実施例〉 以下本発明の実施例を示す。<Example> Examples of the present invention will be shown below.
実施例１
フスマ７ｇ１ミ力ン乾燥果皮３ｇ１炭酸カルシウムＩｇ
、水１０ｍ１を５００ ｍｌ容三角スラスコに分注し１
２０℃、２０分加圧減菌した培地にボトリチス・シネレ
アＦＥＲＭＰ’−６１５６の胞子または菌糸体の濃厚懸
濁液を培地１ｇあたり１×１０２個細胞以上接種し、２
５°Ｃで７日間静置培養した。培養終了後、２０倍量の
熱水で抽出し、そのが液を２，５分の１に濃縮した。Example 1 7g of wheat bran 3g of dried pericarp 1g of calcium carbonate Ig
Dispense 10 ml of water into a 500 ml Erlenmeyer flask.
A concentrated suspension of Botrytis cinerea FERMP'-6156 spores or mycelium is inoculated into a medium that has been sterilized under pressure at 20°C for 20 minutes, at least 1 x 10 cells per 1 g of the medium, and 2
It was statically cultured at 5°C for 7 days. After the culture was completed, extraction was carried out with 20 times the amount of hot water, and the extract was concentrated to 1/2.5.
この濃縮液をカラムにつめた弱塩基性陰イオン交換樹脂
“ダイヤイオン” ＷＡ ３０ （ＯＨ型）５０ ｍｌ
に通塔し、吸着させた後水洗し、０．２ＮＨＣ１−メタ
ノール（１：１容量比）溶液３００ ｍｌでアブシジン
酸を溶出した。This concentrated solution was packed in a column of weakly basic anion exchange resin "Diaion" WA 30 (OH type) 50 ml
After adsorption, the mixture was washed with water, and abscisic acid was eluted with 300 ml of 0.2N HCl-methanol (1:1 volume ratio) solution.
一方、比較例として同様の培養抽出液を強塩基性陰イオ
ン交換樹脂１″ダイヤイオンＩＩ ｐ Ａ３１６に通塔
し、水洗後０．２ＮＨＣＩ−メタノール（１：１容量比
）溶液５００ ｍｌでアブシジン酸を溶出した。さらに
比較例として、同様の培養抽出液を弱塩基性イオン交換
樹脂“ダイヤイオン”ＷＡ３０に通塔し、水洗後０．２
Ｎ 、ＨＣｎ−メタノール（１：４容量比）溶液３０
０ ｍｌでアブシジン酸を溶出した。On the other hand, as a comparative example, the same culture extract was passed through a strongly basic anion exchange resin 1'' Diaion II p A316, washed with water, and then treated with abscisic acid using 500 ml of 0.2N HCI-methanol (1:1 volume ratio) solution. Furthermore, as a comparative example, a similar culture extract was passed through a weakly basic ion exchange resin "Diaion" WA30, and after washing with water, 0.2
N, HCn-methanol (1:4 volume ratio) solution 30
Abscisic acid was eluted at 0 ml.
これらの方法の精製度を各々表１に示す。The purification degrees of these methods are shown in Table 1.
また”ダイヤイオン”ＷＡ３０の溶出液を濃縮し、酢酸
エチル５０ｍ１を加えて、酢酸エチル層にアブシジン酸
を抽出した。酢酸エチル分層後、無水硫酸ナトリウム２
ｇを加えて脱水した後硫酸す） ＩＪウムを炉別し炉液
を減圧濃縮し、ｎ−へキサンを加え、アブシジン酸を晶
出させた。結晶を分離後、５０℃で真空乾燥し、アブシ
ジン酸の白色結晶１０２ｍｇを得た。Further, the eluate of "Diaion" WA30 was concentrated, 50 ml of ethyl acetate was added, and abscisic acid was extracted into the ethyl acetate layer. After ethyl acetate separation, anhydrous sodium sulfate 2
After dehydration by adding 100 g of sulfuric acid, the IJum was separated in a furnace, the furnace liquid was concentrated under reduced pressure, and n-hexane was added to crystallize abscisic acid. After separating the crystals, they were vacuum dried at 50°C to obtain 102 mg of white crystals of abscisic acid.
実施例２
実施例１と同様の方法で培養して得た培養抽出液の濃縮
液５０ｍ１をカラムにつめたゝゝアンバーライト”ＩＲ
−４５の通塔した後、水洗した。Example 2 "Amberlight" IR in which 50 ml of concentrated culture extract obtained by culturing in the same manner as in Example 1 was packed in a column.
-45 and then washed with water.
次に２ＮＨＣ１−イソプロパノール（３・１容量比）溶
液２５０ ｍｌでアブシジン酸を溶出した。Next, abscisic acid was eluted with 250 ml of 2N HCl-isopropanol (3.1 volume ratio) solution.
溶出液を実施例１−と同様に、濃縮、酢酸エチル抽出、
結晶化を行い、アブシジン酸の白色結晶１０５ ｍｇを
得た。The eluate was concentrated, extracted with ethyl acetate, and
Crystallization was performed to obtain 105 mg of white crystals of abscisic acid.
〈発明の効果〉
本発明の方法によれば、１操作で一挙にアブシジン酸の
純度を向上させることかでき、高純度の精製品を得るこ
とができる。また、その後の精製の負荷を下げ、工業的
に、安価のアブシジン酸を精製することが可能となる。<Effects of the Invention> According to the method of the present invention, the purity of abscisic acid can be improved all at once in one operation, and a highly purified purified product can be obtained. Furthermore, it becomes possible to reduce the burden of subsequent purification and to industrially purify abscisic acid at low cost.
さらに、本発明によればアブシジン酸を高回収率でかつ
高純度に精製することが可能となる。Furthermore, according to the present invention, abscisic acid can be purified with high recovery rate and high purity.
Claims (2)
を弱塩基性陰イオン交換樹脂と接触させることにより前
記アブシジン酸を前記樹脂に吸着させた後、前記アブシ
ジン酸を７０％以下の水溶性有機溶媒を含む溶出剤で溶
出させることを特徴とする（＋）シス−トランス型アブ
シジン酸の精製法。(1) After adsorbing the abscisic acid to the resin by contacting a solution containing (+) cis-trans abscisic acid with a weakly basic anion exchange resin, the abscisic acid is made to have a water solubility of 70% or less. A method for purifying (+) cis-trans type abscisic acid, which comprises elution with an eluent containing an organic solvent.
ル、イソプロパノール、アセトンから選ばれる請求項１
記載のアブシジン酸の精製法。(2) Claim 1 in which the organic solvent is selected from methanol, ethanol, propanol, isopropanol, and acetone.
The described method for purifying abscisic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33489690A JPH04202176A (en) | 1990-11-29 | 1990-11-29 | Purification of abscisic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33489690A JPH04202176A (en) | 1990-11-29 | 1990-11-29 | Purification of abscisic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04202176A true JPH04202176A (en) | 1992-07-22 |
Family
ID=18282446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33489690A Pending JPH04202176A (en) | 1990-11-29 | 1990-11-29 | Purification of abscisic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04202176A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1306035C (en) * | 2004-09-14 | 2007-03-21 | 中国科学院成都生物研究所 | Method for extracting natural abscisic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5982340A (en) * | 1982-11-02 | 1984-05-12 | Kyowa Hakko Kogyo Co Ltd | Purification of abscisic acid |
-
1990
- 1990-11-29 JP JP33489690A patent/JPH04202176A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5982340A (en) * | 1982-11-02 | 1984-05-12 | Kyowa Hakko Kogyo Co Ltd | Purification of abscisic acid |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1306035C (en) * | 2004-09-14 | 2007-03-21 | 中国科学院成都生物研究所 | Method for extracting natural abscisic acid |
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