JPH06247893A - Production of octadecatetraenoic acid - Google Patents
Production of octadecatetraenoic acidInfo
- Publication number
- JPH06247893A JPH06247893A JP5059537A JP5953793A JPH06247893A JP H06247893 A JPH06247893 A JP H06247893A JP 5059537 A JP5059537 A JP 5059537A JP 5953793 A JP5953793 A JP 5953793A JP H06247893 A JPH06247893 A JP H06247893A
- Authority
- JP
- Japan
- Prior art keywords
- octadecatetraenoic acid
- acid
- extraction treatment
- carbon dioxide
- octadecatetraenoic
- 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.)
- Granted
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はオクタデカテトラエン酸
の新規な製造方法に関するものである。さらに詳しくい
えば、本発明は、未利用海藻である褐藻コモングサか
ら、種々の生理活性を有する高機能油脂の重要な前駆体
であるオクタデカテトラエン酸を効率よく分離精製する
方法に関するものである。FIELD OF THE INVENTION The present invention relates to a novel process for producing octadecatetraenoic acid. More specifically, the present invention relates to a method for efficiently separating and purifying octadecatetraenoic acid, which is an important precursor of highly functional fats and oils having various physiological activities, from brown seaweed Common Alga, which is an unused seaweed. .
【０００２】[0002]
【従来の技術】従来、オクタデカテトラエン酸は、血栓
症、脳梗塞、心筋梗塞などを防止する作用のあるエイコ
サペンタエン酸（ＥＰＡ）の前駆体として、また海藻胞
子発芽阻止、海藻の成長抑制作用などを有する特異な生
理活性物質として知られている。2. Description of the Related Art Conventionally, octadecatetraenoic acid has been used as a precursor of eicosapentaenoic acid (EPA), which has an action of preventing thrombosis, cerebral infarction, myocardial infarction, etc., and also inhibits seaweed spore germination and seaweed growth inhibition. It is known as a unique physiologically active substance having actions.
【０００３】ＥＰＡは魚油にかなりの高濃度で含まれて
いるが、この魚油にはオクタデカテトラエン酸はほとん
ど含まれていない。海藻にはオクタデカテトラエン酸を
含むものがあるが、その含有量は非常に低く、これまで
まとまった量のオクタデカテトラエン酸を得ることは容
易ではなかった。近年、未利用海洋バイオマス資源の利
用技術が求められているが、海洋に植生する海藻の脂質
部についてはまだその有効利用法がなく、有効利用法の
開発が急務となっている。Although EPA is contained in a considerably high concentration in fish oil, this fish oil contains almost no octadecatetraenoic acid. Some seaweeds contain octadecatetraenoic acid, but the content is very low, and it has not been easy to obtain a large amount of octadecatetraenoic acid. Recently, there has been a demand for utilization technology of unused marine biomass resources, but there is no effective utilization method for the lipid portion of seaweed vegetation in the ocean, and development of an effective utilization method is urgently needed.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、未利用海藻
を原料とし、ＥＰＡの前駆体として、また、海藻胞子発
芽阻止、海藻の成長抑制作用を有する特異な生理活性物
質として知られているオクタデカテトラエン酸を効率よ
く製造する方法を提供することを目的としてなされたも
のである。The present invention is based on unused seaweed as a raw material, is known as a precursor of EPA, and is also known as a unique physiologically active substance having a seaweed spore germination inhibition and seaweed growth inhibitory action. The object of the present invention is to provide a method for efficiently producing octadecatetraenoic acid.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、未利用海
藻からオクタデカテトラエン酸を製造する方法を開発す
るために鋭意研究を重ねた結果、これまで全く高級高度
不飽和脂肪酸の含有が知られていなかった褐藻コモング
サに、該オクタデカテトラエン酸が主要な構成成分とし
て存在していること、そしてこのものを、有機溶媒抽出
法と超臨界二酸化炭素抽出法とを組み合わせることによ
り、効率よく分離精製することを見出し、この知見に基
づいて本発明を完成するに至った。[Means for Solving the Problems] As a result of intensive studies conducted by the present inventors to develop a method for producing octadecatetraenoic acid from unused seaweed, it has hitherto been possible to contain completely higher unsaturated fatty acids. Was not known in the brown alga common gutta, the octadecatetraenoic acid is present as a major constituent, and by combining this with an organic solvent extraction method and a supercritical carbon dioxide extraction method, The inventors have found that they can be efficiently separated and purified, and have completed the present invention based on this finding.
【０００６】すなわち、本発明は、褐藻コモングサに、
有機溶媒抽出処理及び超臨界二酸化炭素抽出処理を施
し、オクタデカテトラエン酸を分離精製することを特徴
とするオクタデカテトラエン酸の製造方法を提供するも
のである。That is, the present invention provides a common brown alga,
It is intended to provide a method for producing octadecatetraenoic acid, which comprises performing an organic solvent extraction treatment and a supercritical carbon dioxide extraction treatment to separate and purify octadecatetraenoic acid.
【０００７】本発明方法においては、褐藻コモングサに
有機溶媒抽出処理と超臨界二酸化炭素抽出処理を組み合
わせて施すが、有機溶媒抽出操作は全工程を通じて低
温、例えば−２〜１０℃の範囲の温度で行うのが好まし
い。この抽出操作に用いられる有機溶媒としては、海藻
脂質部抽出に適した溶媒であればよく、例えばｎ−ヘキ
サン、酢酸エチル、クロロホルム／メタノール混合溶媒
などが好ましく挙げられる。また、このようにして得た
抽出物を次いで超臨界二酸化炭素抽出処理に付す。この
超臨界抽出処理は、例えば流通式の超臨界抽出装置によ
って行われる。In the method of the present invention, common algae of brown algae are subjected to a combination of an organic solvent extraction treatment and a supercritical carbon dioxide extraction treatment. The organic solvent extraction operation is carried out at a low temperature throughout the entire process, for example, at a temperature in the range of −2 to 10 ° C. It is preferable to carry out. The organic solvent used in this extraction operation may be any solvent suitable for extracting the seaweed lipid portion, and for example, n-hexane, ethyl acetate, a chloroform / methanol mixed solvent and the like are preferable. The extract thus obtained is then subjected to a supercritical carbon dioxide extraction treatment. This supercritical extraction process is performed by, for example, a flow-type supercritical extraction device.
【０００８】本発明方法を好適に実施するには、まず、
原料の褐藻コモングサを風乾や凍結乾燥したのち、又は
そのまま０℃付近の低温に保ってミキサーにかけ、乳状
とし、あるいは破片状にする。乳状にする場合は海水濃
度の塩水を加えて行ってもよい。次いで適当な溶媒を用
いて有機溶媒抽出処理を行ったのち、その抽出物から飽
和脂肪酸などを超臨界二酸化炭素抽出処理により除去す
ることによって、所望のオクタデカテトラエン酸を分離
精製することができる。In order to preferably carry out the method of the present invention, first,
The raw brown alga Common guttata is air-dried or freeze-dried, or is kept as it is at a low temperature of around 0 ° C. and is mixed into a milky or broken piece. When emulsified, salt water having a seawater concentration may be added. Then, after conducting an organic solvent extraction treatment using a suitable solvent, the desired octadecatetraenoic acid can be separated and purified by removing saturated fatty acid and the like from the extract by supercritical carbon dioxide extraction treatment. .
【０００９】また、他の方法として、凍結乾燥したコモ
ングサを直接超臨界二酸化炭素抽出処理し、飽和脂肪酸
及び炭化水素などを除去したのち、直接有機溶媒抽出処
理してタンパク質部及び糖部を除去し、次いでそのもの
自体から超臨界二酸化炭素抽出処理により飽和脂肪酸及
び炭化水素などを除去することによって、所望のオクタ
デカテトラエン酸を分離精製してもよい。As another method, freeze-dried common grass is directly subjected to supercritical carbon dioxide extraction treatment to remove saturated fatty acids and hydrocarbons, and then directly subjected to organic solvent extraction treatment to remove protein portion and sugar portion. Then, the desired octadecatetraenoic acid may be separated and purified by removing saturated fatty acids, hydrocarbons and the like from itself by a supercritical carbon dioxide extraction treatment.
【００１０】本発明方法によって得られるオクタデカテ
トラエン酸油は、有機溶媒抽出法のみによる方法に比較
して、パルミチン酸を１０重量％程度除去することがで
き、その結果、オクタデカテトラエン酸を約２５重量％
以上の高濃度で含有する。The octadecatetraenoic acid oil obtained by the method of the present invention can remove about 10% by weight of palmitic acid as compared with the method using only the organic solvent extraction method. As a result, octadecatetraenoic acid is obtained. About 25% by weight
It is contained at the above high concentration.
【００１１】[0011]
【発明の効果】本発明方法によると、ＥＰＡの前駆体と
して、また海藻胞子発芽阻止、海藻の成長抑制作用など
を有する特異な生理活性物質として知られているオクタ
デカテトラエン酸を、これまで注目されなかった褐藻コ
モングサを原料として容易に製造することができるの
で、本発明方法はオクタデカテトラエン酸の工業的製法
として好適である。EFFECT OF THE INVENTION According to the method of the present invention, octadecatetraenoic acid, which is known as a precursor of EPA and a unique physiologically active substance having a seaweed spore germination inhibitory action, a seaweed growth inhibitory action, etc. The method of the present invention is suitable as an industrial method for producing octadecatetraenoic acid, since it can be easily produced using brown alga common corn that has not received attention as a raw material.
【００１２】[0012]
【実施例】次に実施例により本発明をさらに詳細に説明
する。EXAMPLES The present invention will be described in more detail with reference to examples.
【００１３】実施例 褐藻コモングサ５００ｇを凍結乾燥し、破片状としたの
ち、クロロホルム／メタノール混合溶媒にて５℃で抽出
処理し、抽出物１１０ｍｇ／ｇ（コモングサ凍結乾燥試
料）を得た。この抽出物は濃い黒緑色を呈していた。抽
出脂質部は塩基性水溶液及び酸性水溶液で振り分け、さ
らに活性炭を用いてクロロフイルなどを除去したのち、
飽和脂肪酸エステルや炭化水素などを超臨界二酸化炭素
抽出処理により除去した。この抽出物中に含有する脂肪
酸の構成は次のとおりである。EXAMPLE 500 g of brown alga Common guttata was lyophilized to form fragments, and then extracted with a mixed solvent of chloroform / methanol at 5 ° C. to obtain 110 mg / g of an extract (common gutta lyophilized sample). This extract had a dark black-green color. The extracted lipid part is sorted with a basic aqueous solution and an acidic aqueous solution, and chlorophyll and the like are removed using activated carbon.
Saturated fatty acid esters and hydrocarbons were removed by supercritical carbon dioxide extraction treatment. The composition of fatty acids contained in this extract is as follows.
【００１４】 テトラデカン酸 ： ６．５重量％ ヘキサデカン酸 ：２０．０重量％ ヘキサデカモノエン酸 ： ４．２重量％ オクタデカン酸 ： １．１重量％ オクタデカモノエン酸 ：１７．９重量％ オクタデカジエン酸 ： ７．８重量％ オクタデカトリエン酸 ：１０．４重量％ オクタデカテトラエン酸 ：１８．２重量％ エイコサテトラエン酸 ： ７．４重量％ エイコサペンタエン酸 ： ０．９重量％Tetradecanoic acid: 6.5% by weight Hexadecanoic acid: 20.0% by weight Hexadecamonoenoic acid: 4.2% by weight Octadecanoic acid: 1.1% by weight Octadecamonoenoic acid: 17.9% by weight Octadecadiene Acid: 7.8 wt% octadecatrienoic acid: 10.4 wt% Octadecatetraenoic acid: 18.2 wt% Eicosatetraenoic acid: 7.4 wt% Eicosapentaenoic acid: 0.9 wt%
【００１５】次に、オクタテトラエン酸の高濃度化を、
前記抽出物をエステル化し、クロロホルムを用い、硝酸
銀担持シリカゲルカラムで展開し、精製することにより
行った。Next, increasing the concentration of octatetraenoic acid
The extract was esterified, developed with silica gel column supporting silver nitrate using chloroform, and purified.
【００１６】一方、超臨界二酸化炭素抽出分離におい
て、抽出分離ラインに硝酸銀担持シリカゲルカラムを付
設し、エステル化物をクロロホルムに溶解し、１０〜３
５メッシュの海砂にコーティングし、抽出分離した。こ
の抽出処理については、液化二酸化炭素を高圧ポンプで
流通式の抽出槽（１００ｍｌ）に送り、超臨界状態と
し、抽出槽内は圧力調整器で一定圧に保ち、大気圧下に
フラッシュされたガスを分離器に誘導して抽出物を得
た。抽出条件は圧力：２５．０ＭＰａ、温度３１３Ｋ、
ＣＯ2流量：１．０５〜３．００ｄｍ3／分、抽出時間１
０〜３０時間、抽出試料：２８ｇである。On the other hand, in supercritical carbon dioxide extraction separation, a silver nitrate-supporting silica gel column is attached to the extraction separation line, and the esterified product is dissolved in chloroform to give 10-3.
It was coated on 5 mesh sea sand and extracted and separated. Regarding this extraction process, liquefied carbon dioxide was sent to a flow-type extraction tank (100 ml) with a high-pressure pump to bring it into a supercritical state, and the inside of the extraction tank was kept at a constant pressure with a pressure regulator and was flushed under atmospheric pressure. Was introduced into a separator to obtain an extract. The extraction conditions are pressure: 25.0 MPa, temperature 313 K,
CO 2 flow rate: 1.05 to 3.00 dm 3 / min, extraction time 1
0 to 30 hours, extracted sample: 28 g.
【００１７】このような操作により、パルミチン酸の含
有量が減少し、オクタデカテトラエン酸の含有量が増加
し、前者では６０重量％以上、後者では７５重量％以上
となった。By such an operation, the content of palmitic acid was decreased and the content of octadecatetraenoic acid was increased to 60% by weight or more in the former and 75% by weight or more in the latter.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 生島 豊 宮城県仙台市青葉区中山５丁目18−１− 506 (72)発明者 後藤 富雄 宮城県塩釜市藤倉三丁目17−26 (72)発明者 佐藤 修 秋田県横手市横手町字下飛瀬133 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yutaka Ikushima 5-18-1-506 Nakayama, Aoba-ku, Sendai-shi, Miyagi Prefecture (72) Inventor Tomio Goto 3-chome 17-26 Fujikura, Shiogama-shi, Miyagi Prefecture (72) Inventor Osamu Sato 133 Shimohise, Yokote-cho, Yokote-shi, Akita
Claims (1)
び超臨界二酸化炭素抽出処理を施し、オクタデカテトラ
エン酸を分離精製することを特徴とするオクタデカテト
ラエン酸の製造方法。1. A method for producing octadecatetraenoic acid, which comprises subjecting brown alga common gussa to organic solvent extraction treatment and supercritical carbon dioxide extraction treatment to separate and purify octadecatetraenoic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5059537A JPH07122071B2 (en) | 1993-02-23 | 1993-02-23 | Method for producing substance containing octadecatetraenoic acid as constituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5059537A JPH07122071B2 (en) | 1993-02-23 | 1993-02-23 | Method for producing substance containing octadecatetraenoic acid as constituent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06247893A true JPH06247893A (en) | 1994-09-06 |
| JPH07122071B2 JPH07122071B2 (en) | 1995-12-25 |
Family
ID=13116122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5059537A Expired - Lifetime JPH07122071B2 (en) | 1993-02-23 | 1993-02-23 | Method for producing substance containing octadecatetraenoic acid as constituent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07122071B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100415335C (en) * | 2004-03-11 | 2008-09-03 | 南京农业大学 | Preparation method of seaweed antioxidation active component |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6055096A (en) * | 1983-09-06 | 1985-03-29 | 岩谷産業株式会社 | Manufacture of neutral lipid from fishes and shells |
| JPS6272793A (en) * | 1985-09-26 | 1987-04-03 | バブコツク日立株式会社 | Method for concentrating and separating eicosapentaenic acidfrom fish oil |
| JPS6422819A (en) * | 1987-06-24 | 1989-01-25 | Efamol Ltd | Amnesia treating or preventing composition |
| JPS6479191A (en) * | 1987-09-22 | 1989-03-24 | Ishikawajima Harima Heavy Ind | Production of fat-soluble component by mass cultivation of order laminariales |
| JPH01294649A (en) * | 1988-05-21 | 1989-11-28 | Agency Of Ind Science & Technol | Method for extracting docosahexaenoic acid and eicosapentaenoic acid in high concentration from spermary of walleye pollack |
| JPH028298A (en) * | 1988-06-17 | 1990-01-11 | Agency Of Ind Science & Technol | Selective separation and purification of docosahexaenoic acid and eicosapentaenoic acid from internal organs of cuttlefish |
-
1993
- 1993-02-23 JP JP5059537A patent/JPH07122071B2/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6055096A (en) * | 1983-09-06 | 1985-03-29 | 岩谷産業株式会社 | Manufacture of neutral lipid from fishes and shells |
| JPS6272793A (en) * | 1985-09-26 | 1987-04-03 | バブコツク日立株式会社 | Method for concentrating and separating eicosapentaenic acidfrom fish oil |
| JPS6422819A (en) * | 1987-06-24 | 1989-01-25 | Efamol Ltd | Amnesia treating or preventing composition |
| JPS6479191A (en) * | 1987-09-22 | 1989-03-24 | Ishikawajima Harima Heavy Ind | Production of fat-soluble component by mass cultivation of order laminariales |
| JPH01294649A (en) * | 1988-05-21 | 1989-11-28 | Agency Of Ind Science & Technol | Method for extracting docosahexaenoic acid and eicosapentaenoic acid in high concentration from spermary of walleye pollack |
| JPH028298A (en) * | 1988-06-17 | 1990-01-11 | Agency Of Ind Science & Technol | Selective separation and purification of docosahexaenoic acid and eicosapentaenoic acid from internal organs of cuttlefish |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100415335C (en) * | 2004-03-11 | 2008-09-03 | 南京农业大学 | Preparation method of seaweed antioxidation active component |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07122071B2 (en) | 1995-12-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |