JPS633862B2 - - Google Patents
Info
- Publication number
- JPS633862B2 JPS633862B2 JP3288479A JP3288479A JPS633862B2 JP S633862 B2 JPS633862 B2 JP S633862B2 JP 3288479 A JP3288479 A JP 3288479A JP 3288479 A JP3288479 A JP 3288479A JP S633862 B2 JPS633862 B2 JP S633862B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorophyll
- resin
- solution
- column
- polar
- 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
Links
- 229930002875 chlorophyll Natural products 0.000 claims description 49
- 235000019804 chlorophyll Nutrition 0.000 claims description 49
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 48
- 239000002952 polymeric resin Substances 0.000 claims description 17
- 229920003002 synthetic resin Polymers 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 3
- 239000011648 beta-carotene Substances 0.000 description 3
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 3
- 235000013734 beta-carotene Nutrition 0.000 description 3
- 229960002747 betacarotene Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000243 photosynthetic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 235000016425 Arthrospira platensis Nutrition 0.000 description 1
- 240000002900 Arthrospira platensis Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 240000002299 Symphytum officinale Species 0.000 description 1
- 235000005865 Symphytum officinale Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000001752 chlorophylls and chlorophyllins Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229940082787 spirulina Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003735 xanthophylls Chemical class 0.000 description 1
- 235000008210 xanthophylls Nutrition 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
本発明は、多孔性重合樹脂を用いる吸着法によ
りクロロフイルを分離精製する方法に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for separating and purifying chlorophyll by an adsorption method using a porous polymer resin.
光合成物体を有機溶媒で抽出したクロロフイル
含有溶液には、クロロフイル以外にカロチノイド
類、キサントフイル類、脂質類等が多量に含まれ
ているため、クロロフイルを分離精製するにはク
ロロフイルを劣化させることなくこれらクロロフ
イル以外の物質を除去することが必要である。 The chlorophyll-containing solution obtained by extracting photosynthetic substances with an organic solvent contains large amounts of carotenoids, xanthophylls, lipids, etc. in addition to chlorophyll, so in order to separate and purify chlorophyll, these chlorophylls can be extracted without deteriorating the chlorophyll. It is necessary to remove other substances.
従来からのクロロフイル分離精製方法として
は、ジオキサン処理法、シリカゲルカラムクロマ
トグラフイー法、シヨ糖カラムクロマトグラフイ
ー法、種々の有機溶媒を用いる精製法等がある
が、いずれも実験室的規模で行なわれているに過
ぎず、使用溶媒、ロ過、大量処理等の面で工業的
規模で実施するのは困難である。また、ただ１つ
工業的に行なわれた活性炭クロマトグラフイー法
は、装置が非常に大規模でかつ多量の溶媒を用い
るため能率が悪く操作も煩雑であり、さらには活
性炭を使用するため繰返し使用が困難である等の
欠点があつて必ずしも満足すべき方法ではない。 Conventional methods for separating and purifying chlorophyll include dioxane treatment, silica gel column chromatography, sucrose column chromatography, and purification methods using various organic solvents, but all of them are carried out on a laboratory scale. However, it is difficult to implement it on an industrial scale due to the solvent used, filtration, large-scale processing, etc. Additionally, activated carbon chromatography, the only method that has been used industrially, requires very large scale equipment and uses a large amount of solvent, making it inefficient and complicated to operate.Furthermore, since it uses activated carbon, it has to be used repeatedly. However, it is not always a satisfactory method as it has drawbacks such as difficulty.
そこで本発明は、大量かつ高純度のクロロフイ
ルを簡単な操作でしかも効率よく分離精製するこ
とを目的としてなされたものである。 Therefore, the present invention has been made with the object of separating and purifying a large amount of highly pure chlorophyll with simple operations and efficiently.
すなわち本発明によるクロロフイルの分離精製
方法は、クロロフイル含有溶液を高極性の多孔性
重合樹脂で処理することによつてクロロフイルよ
りも高極性の物質をこの高極性多孔性重合樹脂に
吸着させてクロロフイルを溶液中に残し、次にか
くして処理したクロロフイル含有溶液を中極性の
多孔性重合樹脂で処理することによつてクロロフ
イルをこの中極性多孔性重合樹脂に吸着させるこ
とを特徴とするものである。 That is, the method for separating and purifying chlorophyll according to the present invention involves treating a chlorophyll-containing solution with a highly polar porous polymeric resin, thereby adsorbing a substance that is more polar than chlorophyll onto the highly polar porous polymeric resin, thereby removing chlorophyll. The method is characterized in that chlorophyll is left in the solution and then treated with a medium polar porous polymer resin to adsorb chlorophyll onto the medium polar porous polymer resin.
本発明の実施に当つては、先ず光合成物体を80
％含水アセトン等で抽出したのちｎ−ヘキサンに
転溶させたクロロフイル含有溶液、あるいは抽出
したのち濃縮して得られたペーストをｎ−ヘキサ
ンに溶解したクロロフイル含有溶液を調製する。
このクロロフイル含有溶液を先ず最初に高極性の
多孔性重合樹脂で処理し、次いで中極性の多孔性
重合樹脂で処理する。処理方法としては樹脂をカ
ラムに充填してクロロフイル含有溶液を通液する
方法が好ましく使用できる。 In carrying out the present invention, first, a photosynthetic object is
A chlorophyll-containing solution is prepared by extracting with % aqueous acetone or the like and then dissolving in n-hexane, or by dissolving a paste obtained by extraction and concentration in n-hexane.
This chlorophyll-containing solution is first treated with a porous polymeric resin of high polarity and then with a porous polymeric resin of medium polarity. As a treatment method, a method of filling a column with resin and passing a chlorophyll-containing solution through the column can be preferably used.
すなわち、高極性の多孔性重合樹脂を充填した
カラムにクロロフイル含有ｎ−ヘキサン溶液を通
液して、クロロフイルよりも高極性の物質を樹脂
に吸着させ、クロロフイルはカラム通過液中に残
す。通液を終了した樹脂を必要に応じて適当量の
ｎ−ヘキサンで洗浄することによつてカラム中に
多少保持されたクロロフイルを洗い流す。このよ
うにして得られたカラム通過液と洗浄液とを合体
して中極性の多孔性重合樹脂を充填したカラムに
そのまま通液する。これによつてクロロフイルは
この中極性樹脂に吸着されるが、β−カロチン等
の低極性物質は非吸着物として流出する。最後
に、樹脂に吸着したクロロフイルをアセトンで溶
出し、溶出液を減圧下低温で濃縮することによつ
て、金属様青紫色の光沢ある結晶性粉末の高純度
クロロフイルを得ることができる。 That is, a chlorophyll-containing n-hexane solution is passed through a column packed with a highly polar porous polymeric resin, and a substance more polar than chlorophyll is adsorbed onto the resin, leaving the chlorophyll in the liquid passing through the column. After the resin has passed through, the resin is washed with an appropriate amount of n-hexane as needed to wash away some chlorophyll retained in the column. The column-passing liquid and washing liquid obtained in this manner are combined and directly passed through a column filled with a medium-polar porous polymer resin. As a result, chlorophyll is adsorbed to this medium polar resin, but low polar substances such as β-carotene flow out as non-adsorbed substances. Finally, by eluting the chlorophyll adsorbed on the resin with acetone and concentrating the eluate under reduced pressure at a low temperature, high purity chlorophyll in the form of a metallic blue-purple shiny crystalline powder can be obtained.
使用済の２種類の樹脂はいずれも、酸や塩基に
よる再生を必要とせず。単にメタノール等の極性
溶媒を用いて再生するだけで繰返し使用すること
ができる。 Both used resins do not require regeneration with acids or bases. It can be used repeatedly by simply regenerating it using a polar solvent such as methanol.
なお、樹脂に吸着したクロロフイルをアセトン
で溶出する前に、クロロフイル吸着樹脂を適当量
のトルエン等で洗浄することによつてフエオフイ
チンを容易に除去できることも本発明の１つの利
点である。このフエオフイチンは、通常の原料乾
燥処理方法によるときは原料中のクロロフイルの
相当量が変化して生成されるもので、一旦クロロ
フイル中に混入したフエオフイチンは従来の製精
方法では除去することが極めて困難であつたが、
本発明によれば容易に効果的に除去することがで
きるのである。このフエオフイチンの洗浄除去の
目的で使用する溶媒は、使用樹脂の種類、特にそ
の極性により適当な有機溶媒を選択使用する。 Another advantage of the present invention is that pheophytin can be easily removed by washing the chlorophyll-adsorbing resin with an appropriate amount of toluene or the like before eluting the chlorophyll adsorbed on the resin with acetone. This pheophytin is produced by changing a considerable amount of chlorophyll in the raw material when using normal raw material drying processing methods, and once it is mixed into chlorophyll, it is extremely difficult to remove using conventional refining methods. It was hot, but
According to the present invention, it can be easily and effectively removed. As the solvent used for the purpose of washing and removing the pheophytin, an appropriate organic solvent is selected depending on the type of resin used, especially its polarity.
本発明で使用する高極性の多孔性重合樹脂とし
ては、アンバーライトIR−118B（ローム・アン
ド・ハース・カンパニー社製）、ダイヤイオン
WK−11（三菱化成(株)製）のごとき酸性陽イオン
交換樹脂、およびアンバーライトXAD−11、同
XAD−12のごとき高極性吸着樹脂が好ましく使
用できる。一方、中極性の多孔性重合樹脂として
は、ダイヤイオンPA−306、同WA−20のごとき
塩基性陰イオン交換樹脂、およびアンバーライト
XAD−７、同XAD−８、デユオライトＳ−761
（ケミカル・プロセス・カンパニー社製）のごと
き中極性吸着樹脂が好ましく使用できる。 Highly polar porous polymer resins used in the present invention include Amberlite IR-118B (manufactured by Rohm and Haas Company) and Diaion.
Acidic cation exchange resins such as WK-11 (manufactured by Mitsubishi Kasei Corporation) and Amberlite XAD-11,
Highly polar adsorption resins such as XAD-12 are preferably used. On the other hand, as medium polar porous polymer resins, basic anion exchange resins such as Diaion PA-306 and Diaion WA-20, and Amberlite
XAD-7, XAD-8, Duolite S-761
(manufactured by Chemical Process Company) can be preferably used.
以下に実施例を挙げて本発明をさらに説明す
る。 The present invention will be further explained below with reference to Examples.
実施例 １
スピルリナ粉末100ｇを80％含水アセトン１
で２時間撹拌抽出し、得られた抽出液をロ過した
のち400mlのｎ−ヘキサンに転溶する。このｎ−
ヘキサン溶液を等量の水で水洗したのち、ダイヤ
イオンWK−11の200mlを充填したカラムに通液
して溶液中の極性物質を樹脂に吸着させて除去
し、クロロフイル等はｎ−ヘキサン溶液中に非吸
着物として残留させて通過させる。通液終了後、
200mlのｎ−ヘキサンをカラムに流して樹脂を洗
浄する。通過液と洗浄液を合わせてデユオライト
Ｓ−761の50mlを充填したカラムに通液し、クロ
ロフイル等を樹脂に吸着させ、β−カロチン等の
低極性物質を非吸着物として通過させる。通液終
了後、トルエン200mlをカラムに流してフエオフ
イチンを溶出洗浄したのち、最後にアセトン200
mlを流して樹脂に吸着したクロロフイルを溶出す
る。Example 1 100g of Spirulina powder mixed with 80% hydrated acetone 1
After stirring for 2 hours, the resulting extract was filtered and then dissolved in 400 ml of n-hexane. This n-
After washing the hexane solution with an equal amount of water, the solution is passed through a column packed with 200 ml of Diaion WK-11 to remove polar substances in the solution by adsorption to the resin, and chlorophyll etc. are removed from the n-hexane solution. It remains as a non-adsorbent and passes through. After passing the liquid,
Wash the resin by flowing 200 ml of n-hexane through the column. The combined solution and washing solution are passed through a column packed with 50 ml of Duolite S-761, so that chlorophyll and the like are adsorbed onto the resin, while low polar substances such as β-carotene are allowed to pass through as non-adsorbed substances. After passing through the column, pour 200 ml of toluene into the column to elute and wash the pheophytin, and finally add 200 ml of acetone to the column.
ml to elute the chlorophyll adsorbed to the resin.
かくして得られたクロロフイル含有アセトン溶
液を減圧下低温で濃縮し、含量86.19％（A.O.A.
C法による）のクロロフイル結晶0.78ｇを得た。 The thus obtained chlorophyll-containing acetone solution was concentrated at low temperature under reduced pressure to a content of 86.19% (AOA
0.78 g of chlorophyll crystals (by method C) were obtained.
実施例 ２
コンフリーより抽出したクロロフイルペースト
３ｇ（クロロフイル含量16.44％）をｎ−ヘキサ
ン100mlに溶解した溶液を、ダイヤイオンWK−
11の200mlを充填したカラムに通液して溶液中の
極性物質を樹脂に吸着させて除去し、クロロフイ
ル等はｎ−ヘキサン溶液中に非吸着物として残留
させて通過させる。通液終了後、200mlのｎ−ヘ
キサンをカラムに流して樹脂を洗浄する。通過液
と洗浄液を合わせて、アンバーライトXAD−７
の50mlを充填したカラムに通液し、クロロフイル
等を樹脂に吸着させ、β−カロチン等の低極性物
質を非吸着物として通過させる。通液終了後、ベ
ンゼン−ｎ−ヘキサン（１：１）混液200mlをカ
ラムに流してフエオフイチンを溶出洗浄したの
ち、最後にアセトン200mlを流して樹脂に吸着し
たクロロフイルを溶出する。Example 2 A solution prepared by dissolving 3 g of chlorophyll paste extracted from comfrey (chlorophyll content 16.44%) in 100 ml of n-hexane was mixed with Diaion WK-
Polar substances in the solution are adsorbed onto the resin and removed by passing the solution through a column packed with 200 ml of No. 11, while chlorophyll and the like remain as non-adsorbed substances in the n-hexane solution and are passed through. After the liquid passage is completed, 200 ml of n-hexane is poured into the column to wash the resin. Combine the passing liquid and washing liquid, and add Amberlite XAD-7.
The solution is passed through a column packed with 50 ml of the solution, and chlorophyll etc. are adsorbed on the resin, while low polar substances such as β-carotene are allowed to pass through as non-adsorbed substances. After passing through the column, 200 ml of a benzene-n-hexane (1:1) mixture was run through the column to elute and wash pheophytin, and finally 200 ml of acetone was run through the column to elute the chlorophyll adsorbed to the resin.
かくして得られたクロロフイル含有アセトン溶
液を減圧下低温で濃縮し、含量74.78％のクロロ
フイル結晶0.53ｇを得た。 The chlorophyll-containing acetone solution thus obtained was concentrated under reduced pressure at low temperature to obtain 0.53 g of chlorophyll crystals with a content of 74.78%.
以上の説明から明らかなように本発明によれ
ば、クロロフイル含有溶液を高極性多孔性重合樹
脂で処理し、引き続き中極性多孔性重合樹脂で処
理するという極めて簡単な操作で、工業的規模で
クロロフイル濃縮物中のクロロフイル含量を一挙
に80％前後にまで高めることができる。従つて医
薬用等のさらに高純度のクロロフイルへの精製も
非常に容易に行なうことができる。 As is clear from the above description, according to the present invention, chlorophyll can be produced on an industrial scale by an extremely simple operation in which a chlorophyll-containing solution is treated with a highly polar porous polymer resin and then treated with a medium polar porous polymer resin. The chlorophyll content in the concentrate can be increased to around 80% at once. Therefore, purification to even higher purity chlorophyll for pharmaceutical use etc. can be carried out very easily.
Claims (1)
樹脂で処理することによつてクロロフイルよりも
高極性の物質をこの高極性多孔性重合樹脂に吸着
させてクロロフイルを溶液中に残し、次にかくし
て処理したクロロフイル含有溶液を中極性の多孔
性重合樹脂で処理することによつてクロロフイル
をこの中極性多孔性重合樹脂に吸着させることを
特徴とするクロロフイルの分離精製方法。1. By treating a chlorophyll-containing solution with a highly polar porous polymeric resin, a substance more polar than chlorophyll is adsorbed onto the highly polar porous polymeric resin, leaving the chlorophyll in the solution, and then treated in this way. 1. A method for separating and purifying chlorophyll, which comprises treating a chlorophyll-containing solution with a porous polymeric resin having medium polarity, thereby adsorbing chlorophyll onto the porous polymeric resin having medium polarity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3288479A JPS55124785A (en) | 1979-03-20 | 1979-03-20 | Separation and purification of chlorophyll |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3288479A JPS55124785A (en) | 1979-03-20 | 1979-03-20 | Separation and purification of chlorophyll |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55124785A JPS55124785A (en) | 1980-09-26 |
| JPS633862B2 true JPS633862B2 (en) | 1988-01-26 |
Family
ID=12371292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3288479A Granted JPS55124785A (en) | 1979-03-20 | 1979-03-20 | Separation and purification of chlorophyll |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55124785A (en) |
-
1979
- 1979-03-20 JP JP3288479A patent/JPS55124785A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55124785A (en) | 1980-09-26 |
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