JPH048038B2 - - Google Patents
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- Publication number
- JPH048038B2 JPH048038B2 JP58048433A JP4843383A JPH048038B2 JP H048038 B2 JPH048038 B2 JP H048038B2 JP 58048433 A JP58048433 A JP 58048433A JP 4843383 A JP4843383 A JP 4843383A JP H048038 B2 JPH048038 B2 JP H048038B2
- Authority
- JP
- Japan
- Prior art keywords
- coenzyme
- extraction
- adsorption
- adsorbent
- extract
- 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
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- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 65
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 47
- 238000000605 extraction Methods 0.000 claims description 47
- 238000001179 sorption measurement Methods 0.000 claims description 32
- 239000003463 adsorbent Substances 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 230000002209 hydrophobic effect Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 230000001580 bacterial effect Effects 0.000 description 11
- 238000011084 recovery Methods 0.000 description 11
- 238000003795 desorption Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 230000000813 microbial effect Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 229910003460 diamond Inorganic materials 0.000 description 3
- 239000010432 diamond Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000586779 Protaminobacter Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 241000589506 Xanthobacter Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 229940110767 coenzyme Q10 Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Description
【発明の詳細な説明】
本発明は補酵素Ｑの製造法に関し、さらに詳し
くは補酵素Ｑ含有物から抽出および吸着の２処理
をくりかえすことによつて補酵素Ｑを得る方法に
係わる。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing coenzyme Q, and more particularly to a method for obtaining coenzyme Q by repeating two processes of extraction and adsorption from a coenzyme Q-containing material.
補酵素Ｑ含有物中の補酵素Ｑは親水性溶媒を用
いて抽出でき、また抽出は無水のときよりも数
wt％程度の含水率となるような水が存在する方
が抽出率が良好なことが知られている。一方、抽
出時の含水率が最適値よりも高くなるに伴い補酵
素Ｑの抽出剤への溶解度が急激に減少し、抽出率
も著しく低下する。従つて、高含水率下での抽出
において、抽出率を上げるには多量の抽出剤を必
要とするようになる。ところで補酵素Ｑ含有物の
濃縮液あるいは懸濁液等には、通常、多量の水が
含まれているが、このような水分を多量に含有す
る物質を原料とする場合には、抽出混合液は高含
水率となり、多量の抽出剤を必要とする。 Coenzyme Q in coenzyme Q-containing materials can be extracted using a hydrophilic solvent, and the extraction
It is known that the extraction rate is better when water is present with a water content of about wt%. On the other hand, as the water content during extraction becomes higher than the optimum value, the solubility of coenzyme Q in the extractant decreases rapidly, and the extraction rate also decreases significantly. Therefore, in extraction under high water content, a large amount of extractant is required to increase the extraction rate. By the way, concentrates or suspensions of coenzyme Q-containing substances usually contain a large amount of water, but when using substances containing a large amount of water as raw materials, the extraction mixture has a high water content and requires a large amount of extractant.
高含水率の物質から少量の溶媒を使用して効率
よく補酵素Ｑを抽出することについては、補酵素
Ｑ含有物に親水性溶媒と吸着剤とを一緒に加えて
撹拌し、補酵素Ｑをその含有物から抽出すると同
時に、これを吸着剤に吸着させるとの方法がすで
に知られている（特開昭55−39701号）。しかしな
がら、この方法において吸着剤から補酵素Ｑを溶
出させるに先立つて通常は吸着剤から抽出残渣を
分離除去しなければならないが、吸着剤および抽
出残渣はいずれも固体であるので抽出残渣を実質
的に完全に分離除去することは、技術的にも困難
でありかつ経済的にも不利である。またこの方法
では、さらに補酵素Ｑの回収率が低くなり、また
吸着剤の使用時間も短い。そこで、本発明者らは
補酵素Ｑの製造法に関し、種々、検討した結果、
抽出原料と吸着剤とは共存させず、まず抽出液を
得てから、次いでこの抽出液と疎水性吸着剤とを
接触させて補酵素Ｑを吸着剤に吸着させたのち、
吸着残液を抽出剤として再使用する本発明を完成
するに到つた。 To efficiently extract coenzyme Q from substances with high water content using a small amount of solvent, coenzyme Q is extracted by adding a hydrophilic solvent and an adsorbent together to a coenzyme Q-containing material and stirring. A method is already known in which the substances contained therein are extracted and at the same time adsorbed onto an adsorbent (Japanese Patent Application Laid-open No. 39701/1983). However, in this method, before coenzyme Q can be eluted from the adsorbent, the extraction residue must usually be separated and removed from the adsorbent, but since both the adsorbent and the extraction residue are solids, it is necessary to remove the extraction residue substantially. It is technically difficult and economically disadvantageous to completely separate and remove them. Furthermore, in this method, the recovery rate of coenzyme Q is further lowered, and the use time of the adsorbent is also shortened. Therefore, the present inventors conducted various studies regarding the method for producing coenzyme Q, and found that
The extraction raw material and the adsorbent are not allowed to coexist; first, an extract is obtained; then, this extract is brought into contact with a hydrophobic adsorbent to adsorb coenzyme Q on the adsorbent;
The present invention has been completed in which the adsorption residue is reused as an extractant.
すなわち、本発明は、補酵素Ｑ含有物からの補
酵素Ｑの製造法において、親水性溶媒と補酵素Ｑ
含有物とを水の存在下で接触させる抽出処理と、
該抽出処理で得られた補酵素Ｑ抽出液中の補酵素
Ｑを疎水性吸着剤に吸着させる吸着処理とをくり
かえし、かつ該吸着処理で得られた吸着残液を抽
出剤として再使用することを特徴とする補酵素Ｑ
の製造法である。 That is, the present invention provides a method for producing coenzyme Q from a coenzyme Q-containing material, in which a hydrophilic solvent and coenzyme Q
an extraction process in which the contained substances are brought into contact with each other in the presence of water;
Repeating the adsorption treatment in which coenzyme Q in the coenzyme Q extract obtained in the extraction treatment is adsorbed onto a hydrophobic adsorbent, and reusing the adsorption residual liquid obtained in the adsorption treatment as an extractant. Coenzyme Q characterized by
This is the manufacturing method.
本発明において、補酵素Ｑ含有物としては動・
植物組織ならびに細菌、酵母および糸状菌等の微
生物菌体などがある。抽出に先立つて、動、植物
組織は通常ホモジナイザー、超音波あるいは酸・
アルカリ等による前処理にかけられる。また、微
生物菌体のうち酵母および糸状菌などの菌体は通
常、前記のような前処理にかけられるが、細菌菌
体は前処理にかける必要はないが、前処理にかけ
てもよい。 In the present invention, coenzyme Q-containing substances include
These include plant tissues and microbial cells such as bacteria, yeast, and filamentous fungi. Prior to extraction, animal and plant tissues are usually processed using a homogenizer, ultrasound, or acid.
It is subjected to pre-treatment with alkali etc. Further, among microorganisms, cells such as yeast and filamentous fungi are usually subjected to the above-mentioned pretreatment, but bacterial cells do not need to be subjected to pretreatment, but may be subjected to pretreatment.
微生物菌体は培養後、集菌したペースト状ある
いは水懸濁状の湿菌体およびこれらを乾燥した乾
燥菌体等が通常使用される。なお、培養液をその
まま使用することを妨げない。 After culturing, microbial cells are usually used in the form of wet microbial cells in the form of a paste or water suspension, and dried microbial cells obtained by drying these. Note that the culture solution may be used as it is.
親水性溶媒としてはメタノール、エタノール、
プロパノールおよびブタノール等のアルコールな
らびにアセトンのような溶媒があげられる。これ
らの溶媒のうち、プロパノール、ブタノール、お
よびアセトンは通常はそれぞれ単独で使用され、
またメタノールおよびエタノールなどは単独でも
使用されるが通常はプロパノール、アセトン、ブ
タノールなどの他の溶媒と併用される。抽出時の
抽出混合液の含水率は100×水分（wt）／水分＋
溶媒（wt）として50wt％以下、好ましくは３〜
50wt％、特に好ましくは５〜40wt％となるよう
な含水率とされる。なお、水が少いときは水を溶
媒とともに、または単独で補充することが必要で
ある。含水率が低くすぎると疎水性吸着剤への補
酵素Ｑの吸着能が低下し、したがつて抽出される
べき補酵素Ｑ当たり多量の吸着剤が必要となる。
また、含水率が高すぎると、補酵素Ｑの溶媒への
溶解度があまりにも小さくなり、抽出率の低下を
もたらす。 Hydrophilic solvents include methanol, ethanol,
Mention may be made of alcohols such as propanol and butanol and solvents such as acetone. Of these solvents, propanol, butanol, and acetone are typically used alone;
Although methanol and ethanol can be used alone, they are usually used in combination with other solvents such as propanol, acetone, and butanol. The moisture content of the extraction mixture during extraction is 100 x moisture (wt)/moisture +
50wt% or less as solvent (wt), preferably 3~
The water content is set to 50 wt%, particularly preferably 5 to 40 wt%. Note that when water is low, it is necessary to replenish water together with the solvent or alone. If the water content is too low, the adsorption capacity of coenzyme Q to the hydrophobic adsorbent will be reduced, and therefore a large amount of adsorbent will be required per coenzyme Q to be extracted.
Furthermore, if the water content is too high, the solubility of coenzyme Q in the solvent will be too low, resulting in a decrease in extraction rate.
抽出温度、時間には特に制限はないが抽出温度
は、常温または室温ないし50℃が好ましい。ま
た、抽出時間は抽出剤の種類、原料の種類、状
態、温度などによつて異り一概にいえないが通常
は20〜30分乃至一夜程度でよい。 The extraction temperature and time are not particularly limited, but the extraction temperature is preferably room temperature or room temperature to 50°C. Further, the extraction time varies depending on the type of extractant, the type of raw material, the condition, the temperature, etc., and cannot be determined unconditionally, but it is usually about 20 to 30 minutes to overnight.
補酵素Ｑ含有物と溶媒との接触は、通常は補酵
素Ｑ含有物と溶媒とを混合した抽出混合液を撹拌
することによつて行なわれる。 Contact between the coenzyme Q-containing material and the solvent is usually carried out by stirring an extraction mixture containing the coenzyme Q-containing material and the solvent.
このようにして撹拌されたのちの抽出混合液か
ら抽出液を分離するには遠心分離、沈降分離およ
び濾過等の通常の固液分離手段が採用される。な
お、微生物菌体は通常は親水性溶媒の存在下では
凝集しているために沈降分離あるいは濾過しやす
くなつており、連続的に容易に抽出液を得ること
ができる。 To separate the extract from the extracted mixture after being stirred in this manner, conventional solid-liquid separation means such as centrifugation, sedimentation, and filtration are employed. In addition, since microbial cells are usually aggregated in the presence of a hydrophilic solvent, they are easily separated by sedimentation or filtered, and an extract can be easily obtained continuously.
次いで抽出液は疎水性吸着剤に接触せしめら
れ、補酵素Ｑは吸着剤に吸着される。 The extract is then brought into contact with a hydrophobic adsorbent, and coenzyme Q is adsorbed onto the adsorbent.
疎水性吸着剤には、特に制限はないが、残存シ
ラノール基を最小限度におさえた化学結合型シリ
カゲルまたはたとえば市販品であるアンバーライ
ト（商品名）およびハイポラース（商品名）など
の多孔性合成樹脂などが好適に使用される。 There are no particular restrictions on the hydrophobic adsorbent, but chemically bonded silica gel with minimal residual silanol groups or porous synthetic resins such as commercially available Amberlite (trade name) and Hyporase (trade name) are examples of hydrophobic adsorbents. etc. are preferably used.
この吸着は、通常はこれら吸着剤をたえばカラ
ムに充填し、このカラムに抽出液を流下させる。
または抽出液と吸着剤とを混合し、撹拌もしくは
揺動させてもよい。工業的には前者が好ましい。
このようにして補酵素Ｑは吸着剤に吸着され、こ
の吸着剤を吸着残液と分離する。 For this adsorption, these adsorbents are usually packed in a column, for example, and the extract is allowed to flow down the column.
Alternatively, the extract and the adsorbent may be mixed and stirred or shaken. The former is preferred industrially.
In this way, coenzyme Q is adsorbed on the adsorbent, and this adsorbent is separated from the adsorption residual liquid.
なお、通常は、抽出液はそのまま吸着処理に付
されるが、抽出等の含水率の好適範囲からづれな
い限りは水もしくは溶媒を添加もしくは除去する
ことを妨げない。 Although the extract is usually subjected to adsorption treatment as it is, it is not prohibited to add or remove water or a solvent as long as the water content does not deviate from the preferred range for extraction.
吸着温度は通常、抽出温度と同一乃至これより
やや高目の一たとえば５〜10℃程度高い−温度と
する。吸着温度を抽出温度より低くすると油状物
等が析出固化し、カラムの閉塞をきたしたり吸着
剤表面が被覆されるおそれがある。 The adsorption temperature is usually the same as or slightly higher than the extraction temperature, for example, about 5 to 10°C higher. If the adsorption temperature is lower than the extraction temperature, oily substances will precipitate and solidify, which may clog the column or coat the surface of the adsorbent.
本発明において、同一の補酵素Ｑ含有物に対し
て、抽出−吸着の一連の操作を複数回加えなけれ
ばならないが、通常は２回以上好ましくは４〜10
回程度繰返えされる。なお、このとき各回に使用
される抽出剤はリサイクルして再使用する。 In the present invention, the same coenzyme Q-containing material must be subjected to a series of extraction-adsorption operations multiple times, but usually two or more times, preferably 4 to 10 times.
It is repeated several times. Note that the extractant used each time is recycled and reused.
吸着後、吸着剤から有機溶媒で補酵素Ｑを脱着
溶出させ、この溶出液より補酵素Ｑを回収精製す
る。脱着は前記の吸着ごとに毎回行なつてもよい
が、好ましくは数回の吸着により、吸着剤がほぼ
補酵素Ｑで飽和吸着された後に行なわれる。この
脱着に使用される有機溶媒は補酵素Ｑをよく溶解
するものであればよく、疎水性有機溶媒たとえば
石油エーテルおよびｎ−ヘキサンなども使用しう
るが、抽出に使用された親水性溶媒と同じ種類の
ものを用いることは溶媒の種類を増やさないこと
からも好ましい。この場合に、脱着用の溶媒は含
水率の低いもの程脱着に要する溶媒量を少なくす
ることができるので好ましい。 After adsorption, coenzyme Q is desorbed and eluted from the adsorbent using an organic solvent, and coenzyme Q is recovered and purified from this eluate. Desorption may be carried out every time the adsorption is performed, but it is preferably carried out after the adsorbent has been adsorbed to almost saturation with coenzyme Q by several adsorptions. The organic solvent used for this desorption may be any organic solvent as long as it dissolves coenzyme Q well, and hydrophobic organic solvents such as petroleum ether and n-hexane may also be used; It is preferable to use different types of solvents because it does not increase the number of types of solvents. In this case, it is preferable to use a solvent for desorption with a lower water content because the amount of solvent required for desorption can be reduced.
なお、必要に応じ、脱着に先立つて、含水親水
性溶媒を吸着剤に接触させることによつて、吸着
している不純物の一部を脱着させることができ、
補酵素Ｑの溶出画分中の純度を向上させることが
できる。 Note that, if necessary, some of the adsorbed impurities can be desorbed by bringing a water-containing hydrophilic solvent into contact with the adsorbent prior to desorption.
The purity of coenzyme Q in the elution fraction can be improved.
吸着で得られた補酵素Ｑを実質的に含有しない
吸着残液は抽出剤として再使用する。 The adsorption residue obtained by adsorption, which does not substantially contain coenzyme Q, is reused as an extractant.
本発明での吸着では、吸着時に比較的高含水率
の抽出液を吸着原料として使用し、脱着時には比
較的低含水率の溶媒を使用することにより、疎水
性吸着剤は、その補酵素Ｑの吸着能は大きくな
り、かつ、脱着によつて補酵素Ｑおよび不純物は
実質的に完全に脱着され、脱着後において補酵素
Ｑの吸着能は実質的に完全に回復し、また、目づ
まりなどがなく、長期間にわたつて繰返えし使用
が可能である。 In the adsorption according to the present invention, an extract with a relatively high water content is used as an adsorption raw material during adsorption, and a solvent with a relatively low water content is used during desorption. The adsorption capacity increases, and coenzyme Q and impurities are substantially completely desorbed by desorption, and after desorption, the coenzyme Q adsorption capacity is substantially completely recovered, and clogging etc. It can be used repeatedly over a long period of time.
また、本発明では、吸着剤と固体の抽出原料お
よび抽出残渣との分離が不要であり、しかも補酵
素Ｑの回収率も高く、また吸着剤の使用時間も長
く、かつ得られる補酵素Ｑの純度が高い。 In addition, the present invention does not require separation of the adsorbent from the solid extraction raw material and extraction residue, has a high recovery rate of coenzyme Q, requires a long use time of the adsorbent, and reduces the amount of coenzyme Q obtained. High purity.
以下実施例により、さらに具体的に本発明を説
明する。しかしながら、本発明はこれらによつて
限定されるものではない。 The present invention will be explained in more detail below with reference to Examples. However, the present invention is not limited thereto.
実施例 １
メタノールを炭素源として培養したプロタミノ
バクター属の細菌の培養液2.0から遠心分離に
より、600gの菌体濃縮液（補酵素Q10含量216mg）
を得た。これに、20wt％含水アセトン1500mlを
加え２容三角フラスコを抽出槽とし35℃で撹拌
した（抽出混合液の含水率は31.5wt％）。この抽
出混合液を吸引濾過して抽出液を得、一方、抽出
残渣を抽出槽に残留させた。この抽出液を、吸着
剤として多孔性合成樹脂ダイヤイオンHp−20（三
菱化成(株)製）30mlが充填され、35℃に保温された
カラムを流下させて、吸着剤に補酵素Q10を吸着
させ、カラムから排出された抽出残液を抽出槽に
リサイクルし再使用した。このようにして抽出−
吸着−リサイクルを17時間続けた。この間抽出−
吸着−リサイクルの一連の操作を約５回繰返し
た。Example 1 600 g of bacterial cell concentrate (Coenzyme Q 10 content: 216 mg) was obtained by centrifugation from culture solution 2.0 of Protaminobacter bacteria cultured using methanol as a carbon source.
I got it. To this was added 1500 ml of 20 wt% aqueous acetone, and the mixture was stirred at 35°C using a 2-volume Erlenmeyer flask as an extraction tank (the water content of the extraction mixture was 31.5 wt%). This extraction mixture was suction-filtered to obtain an extract, while the extraction residue remained in the extraction tank. This extract was passed down a column filled with 30 ml of porous synthetic resin Diaion Hp-20 (manufactured by Mitsubishi Kasei Corporation) as an adsorbent and kept at 35°C, and coenzyme Q 10 was transferred to the adsorbent. After adsorption, the extraction residual liquid discharged from the column was recycled to the extraction tank and reused. Extract in this way -
Adsorption-recycling continued for 17 hours. Extracted during this time
The series of adsorption-recycling operations was repeated about 5 times.
ついで、吸着剤に吸着された補酵素Q10を2wt
％含水アセトン100mlを流下して脱着、溶出した。
溶出液中の補酵素Q10は210mgであつた。これは
回収率97％に相当する。 Next, 2wt of coenzyme Q 10 adsorbed on the adsorbent
Desorption and elution were carried out by flowing down 100 ml of % hydrated acetone.
Coenzyme Q 10 in the eluate was 210 mg. This corresponds to a recovery rate of 97%.
比較例 １
実施例１と同様にして得られた菌体濃縮液
600gに、20wt％含水アセトン1500mlを加え、35
℃で17時間撹拌して抽出した。抽出終了後、遠心
分離して得られた抽出液を、実施例１と同様にし
て、ダイヤイオンHp−20に補酵素Q10を吸着させ
たのち、この抽出・吸着処理を繰り返すことなく
2wt％含水アセトンで実施例１と同様にして溶出
した。この場合の溶出液中の補酵素Q10は98mgで
あつた。これは回収率45％に相当し、極めて低い
値であつた。Comparative Example 1 Bacterial cell concentrate obtained in the same manner as Example 1
Add 1500ml of 20wt% hydrated acetone to 600g,
The mixture was stirred and extracted at ℃ for 17 hours. After the extraction was completed, the extract obtained by centrifugation was adsorbed to Diaion Hp-20 to adsorb coenzyme Q 10 in the same manner as in Example 1, without repeating this extraction and adsorption process.
Elution was carried out in the same manner as in Example 1 using 2wt% aqueous acetone. In this case, the amount of coenzyme Q 10 in the eluate was 98 mg. This corresponded to a recovery rate of 45%, which was an extremely low value.
比較例 ２
実施例１と同様にして得られた菌体濃縮液
600gに20wt％含水アセトン1500mlとダイヤイオ
ンHp−20 30mlとを一緒に加え、35℃で17時間撹
拌した。この抽出混合液を100メツシユ篩にかけ
ダイヤイオンHp−20を篩別しようとしたが、菌
体が凝集状態となつているため菌体がダイヤイオ
ンHp−20と一緒に篩上残り、そのままでは篩別
できなかつた。そこで、この抽出混合液に水を約
６加え、菌体の凝集状態をある程度解いたのち
篩別したが、なお篩上に若干菌体がとどまつてい
るため、篩を水槽に浸しながら揺動してようやく
菌体のみを通過させ、ダイヤイオンHp−20を篩
別できた。Comparative Example 2 Bacterial cell concentrate obtained in the same manner as Example 1
1500 ml of 20 wt% aqueous acetone and 30 ml of Diaion Hp-20 were added to 600 g, and the mixture was stirred at 35°C for 17 hours. I attempted to sieve this extraction mixture through a 100 mesh sieve to remove the Diamond Ion Hp-20, but since the bacterial cells were in an agglomerated state, they remained on the sieve together with the Diamond Ion Hp-20. I couldn't tell them apart. Therefore, approximately 60% of water was added to this extraction mixture to break up the aggregation of the bacterial cells to some extent, and then sieved. However, some bacterial cells still remained on the sieve, so the sieve was immersed in a water tank and shaken. Finally, we were able to pass only the bacterial cells and sieve out the Diamond Ion Hp-20.
このダイヤイオンHp−20をカラムに充填した
のち、2wt％含水アセトンで吸着補酵素Q10を溶
出した。この場合の溶出液中の補酵素Q10は174
mgであつた。これは回収率約81％に相当する。 After filling a column with this Diaion Hp-20, adsorbed coenzyme Q 10 was eluted with 2 wt% aqueous acetone. Coenzyme Q10 in the eluate in this case is 174
It was mg. This corresponds to a recovery rate of approximately 81%.
なお、ダイヤイオンHp−20の使用量を前記の
２倍量の60mlとした場合には、回収率は約90％で
あつた。 Note that when the amount of Diaion Hp-20 used was doubled to 60 ml, the recovery rate was about 90%.
実施例 ２
メタノールを炭素源として培養したキサントバ
クター属の細菌の培養液２を遠心分離し、菌体
濃縮液300g（補酵素Q10含量108mg）を得、これに
12wt％含水イソプロパノール（水との共沸組成
にほぼ相当）750mlを加え、35℃で撹拌した（こ
のときの抽出混合液の含水率は37.5wt％）ほか
は、実施例１と同様にして抽出を行つた。得られ
た抽出液を、シリカゲルにオクタデシル基を共有
結合させたYMCゲルODS（山村化学研究所製）
が15ml充填され、37℃に保たれたカラムを流下さ
せて、補酵素Q10を吸着させた。カラムより流出
した吸着残液は抽出槽にリサイクルされた。この
抽出−吸着−リサイクルの一連の操作を４時間続
けた。この間に、リサイクルさせた液量は抽出−
吸着−リサイクルの一連の操作を約５回繰返した
ことに相当する量であつた。カラムに吸着された
補酵素Q10を2wt％含水イソプロパノール100mlを
流下し、溶出した。溶出液中の補酵素Q10は104
mgであつた。これは回収率96％に相当する。Example 2 Culture solution 2 of Xanthobacter bacteria cultured using methanol as a carbon source was centrifuged to obtain 300 g of bacterial cell concentrate (coenzyme Q 10 content 108 mg).
Extraction was carried out in the same manner as in Example 1, except that 750 ml of 12 wt% hydrous isopropanol (approximately equivalent to the azeotropic composition with water) was added and stirred at 35°C (the water content of the extraction mixture at this time was 37.5 wt%). I went to The obtained extract was converted into YMC gel ODS (manufactured by Yamamura Kagaku Kenkyusho), which is made by covalently bonding octadecyl groups to silica gel.
Coenzyme Q 10 was adsorbed by flowing down a column filled with 15 ml of coenzyme Q10 and kept at 37°C. The adsorption residue that flowed out of the column was recycled to the extraction tank. This series of extraction-adsorption-recycling operations was continued for 4 hours. During this period, the amount of recycled liquid is extracted -
The amount was equivalent to repeating a series of adsorption-recycling operations about 5 times. Coenzyme Q 10 adsorbed on the column was eluted by flowing down 100 ml of 2 wt% aqueous isopropanol. Coenzyme Q 10 in eluate is 104
It was mg. This corresponds to a recovery rate of 96%.
比較例 ３
吸着残液のリサイクルは行なわなかつたほか
は、実施例２と同様にして４時間抽出し、抽出終
了後遠心分離により得られた抽出液を実施例２と
同様にして吸着、脱着した。得られた溶出液中の
補酵素Q10は65mgであつた。これは回収率60％に
しか相当しなかつた。Comparative Example 3 Extraction was carried out in the same manner as in Example 2 for 4 hours, except that the adsorption residual liquid was not recycled, and after the extraction was completed, the extract obtained by centrifugation was adsorbed and desorbed in the same manner as in Example 2. . The amount of coenzyme Q 10 in the obtained eluate was 65 mg. This corresponded to a recovery rate of only 60%.
比較例 ４
実施例２と同様にして得られた菌体濃縮液
300gに12wt％含水イソプロパノール750mlおよび
YMCゲルODS15mlを添加し、35℃で４時間にわ
たつて抽出と吸着とを行なつた。この抽出混合液
にさらに水約３を加えたほかは比較例２と同様
にしてYMCゲルODSを分離し、脱着して補酵素
Q10を溶出した。Comparative Example 4 Bacterial cell concentrate obtained in the same manner as Example 2
300g with 750ml of 12wt% hydrated isopropanol and
15 ml of YMC gel ODS was added, and extraction and adsorption were performed at 35°C for 4 hours. YMC gel ODS was separated in the same manner as in Comparative Example 2, except that about 3 ml of water was further added to this extraction mixture, and the coenzyme was desorbed and
Q10 was eluted.
この場合の溶出液中の補酵素Q10は91mgであつ
た。これは回収率84％に相当する。 In this case, the amount of coenzyme Q 10 in the eluate was 91 mg. This corresponds to a recovery rate of 84%.
実施例 ３
メタノールを炭素源とした培養で得たプロタミ
ノバクター属の細菌の噴霧乾燥菌体100g（補酵素
Q10含量198mg）にアセトン30、メタノール60
および水10よりなる混合溶媒400mlを加え、
40℃で撹拌したほかは実施例１と同様にして、抽
出液を得、この抽出液を実施例２と同様にして吸
着、脱着して補酵素Q10を吸着させ、かつ吸着残
液は抽出槽にリサイクルした。抽出−吸着−リサ
イクルを３時間続けた。この間にリサイクルされ
た吸着残液の液量は、抽出−吸着−リサイクルの
操作を約８回繰返したことに相当する量であつ
た。吸着剤に吸着された補酵素Q10を2wt％含水
アセトン150mlを流下し脱着、溶出した。溶出液
中の補酵素Q10量は195mgであつた。これは回収
率98.5％を相当する。Example 3 100 g of spray-dried bacterial cells of the genus Protaminobacter obtained by culturing using methanol as a carbon source (coenzyme
Q 10 content 198mg) with 30% acetone and 60% methanol
Add 400 ml of a mixed solvent consisting of 10 parts of water and
An extract was obtained in the same manner as in Example 1, except for stirring at 40°C, and this extract was adsorbed and desorbed in the same manner as in Example 2 to adsorb coenzyme Q 10 , and the residual adsorbed liquid was extracted. Recycled into tank. Extraction-adsorption-recycling continued for 3 hours. The amount of adsorption residue recycled during this period was equivalent to repeating the extraction-adsorption-recycling operation about 8 times. Coenzyme Q 10 adsorbed on the adsorbent was desorbed and eluted by flowing 150 ml of 2 wt% aqueous acetone. The amount of coenzyme Q10 in the eluate was 195 mg. This corresponds to a recovery rate of 98.5%.
比較例 ５
吸着残液のリサイクルを行なわなかつた以外は
実施例３と同様にして、補酵素Q10を96mg得た。
これは回収率46％にすぎなかつた。Comparative Example 5 96 mg of coenzyme Q 10 was obtained in the same manner as in Example 3, except that the adsorption residual liquid was not recycled.
This was a recovery rate of only 46%.
Claims (1)
いて、水分３〜50wt％を含有する親水性溶媒と
補酵素Ｑ含有物とを接触させる抽出処理と、該抽
出処理後の固液分離により得られた補酵素Ｑ抽出
液中の補酵素Ｑを疎水性吸着剤に吸着させる吸着
処理とをくりかえし、かつ該吸着処理で得られた
吸着残液を抽出剤としてそのまま再使用すること
を特徴とする補酵素Ｑの製造法。1. In the method for producing coenzyme Q from a coenzyme Q-containing material, an extraction treatment in which a hydrophilic solvent containing 3 to 50 wt% of water is brought into contact with a coenzyme Q-containing material, and solid-liquid separation after the extraction treatment. It is characterized by repeating an adsorption treatment in which coenzyme Q in the obtained coenzyme Q extract is adsorbed on a hydrophobic adsorbent, and reusing the adsorption residual liquid obtained in the adsorption treatment as it is as an extractant. A method for producing coenzyme Q.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4843383A JPS59173088A (en) | 1983-03-23 | 1983-03-23 | Preparation of coenzyme q |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4843383A JPS59173088A (en) | 1983-03-23 | 1983-03-23 | Preparation of coenzyme q |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59173088A JPS59173088A (en) | 1984-09-29 |
| JPH048038B2 true JPH048038B2 (en) | 1992-02-13 |
Family
ID=12803218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4843383A Granted JPS59173088A (en) | 1983-03-23 | 1983-03-23 | Preparation of coenzyme q |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59173088A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018003974A1 (en) | 2016-07-01 | 2018-01-04 | 株式会社カネカ | Method for producing coenzyme q10 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5630941A (en) * | 1979-08-24 | 1981-03-28 | Ajinomoto Co Inc | Purification of coenzyme q |
-
1983
- 1983-03-23 JP JP4843383A patent/JPS59173088A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5630941A (en) * | 1979-08-24 | 1981-03-28 | Ajinomoto Co Inc | Purification of coenzyme q |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59173088A (en) | 1984-09-29 |
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