JPH06212186A - Production of eicosapentaenoic acid from red alga fudaraku - Google Patents
Production of eicosapentaenoic acid from red alga fudarakuInfo
- Publication number
- JPH06212186A JPH06212186A JP4195829A JP19582992A JPH06212186A JP H06212186 A JPH06212186 A JP H06212186A JP 4195829 A JP4195829 A JP 4195829A JP 19582992 A JP19582992 A JP 19582992A JP H06212186 A JPH06212186 A JP H06212186A
- Authority
- JP
- Japan
- Prior art keywords
- extraction
- eicosapentaenoic acid
- fudaraku
- red alga
- organic solvent
- 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
- 235000020673 eicosapentaenoic acid Nutrition 0.000 title claims abstract description 18
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 title claims abstract description 5
- 229960005135 eicosapentaenoic acid Drugs 0.000 title claims abstract description 5
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 3
- 150000003904 phospholipids Chemical group 0.000 claims description 2
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 13
- 239000003960 organic solvent Substances 0.000 abstract description 11
- 208000007536 Thrombosis Diseases 0.000 abstract description 5
- 208000010125 myocardial infarction Diseases 0.000 abstract description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract description 2
- 239000001569 carbon dioxide Substances 0.000 abstract description 2
- 206010008088 Cerebral artery embolism Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 201000010849 intracranial embolism Diseases 0.000 abstract 1
- 238000000194 supercritical-fluid extraction Methods 0.000 abstract 1
- 241001474374 Blennius Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010008118 cerebral infarction Diseases 0.000 description 4
- 208000026106 cerebrovascular disease Diseases 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 150000002632 lipids Chemical group 0.000 description 4
- 239000002028 Biomass Substances 0.000 description 3
- 230000023555 blood coagulation Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- 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、これまであまり返り見
られなかった未利用海藻である紅藻フダラク中より血清
脂質改善作用や血液凝固抑制作用などを有する高機能油
脂エイコサペンタエン酸（以下ＥＰＡと記す）を分離精
製し、健康食品、医療用原料、飼料等の機能性製品分野
に応用展開出来るものである。BACKGROUND OF THE INVENTION The present invention relates to a highly functional oil, eicosapentaenoic acid (hereinafter referred to as EPA), which has serum lipid-improving action and blood coagulation-inhibiting action from the red seaweed Fudarac which is an unused seaweed which has not been returned so far. Can be applied and developed in the field of functional products such as health foods, medical raw materials, and feeds.
【０００２】[0002]
【従来の技術】ＥＰＡ等の高度不飽和の高機能油脂は体
内で形成されない。このＥＰＡは血栓症、脳梗塞、心筋
梗塞等を防止する作用のあることで知られている。この
様な高級高度不飽和脂肪酸の供給源量として肝油など魚
類等がその主なものである。供給原料の拡大と未利用海
洋バイオマス資源の利用技術が求められている現状に於
て海洋に植生する海藻の脂質部は未だその有効利用法が
無く、有効利用法開発が急務の課題となっている。2. Description of the Related Art Highly unsaturated and highly functional fats and oils such as EPA are not formed in the body. This EPA is known to have an action of preventing thrombosis, cerebral infarction, myocardial infarction and the like. The main sources of such higher polyunsaturated fatty acids are fish such as liver oil. In the current situation where expansion of supply materials and utilization technology of unused marine biomass resources are required, the lipid part of seaweed vegetation in the ocean does not yet have an effective utilization method, and the development of an effective utilization method is an urgent issue. There is.
【０００３】[0003]
【発明が解決しようとする課題】未利用海藻より血栓
症、脳梗塞、心筋梗塞等を防止する作用のあることで知
られるＥＰＡを提供することを目的とする。An object of the present invention is to provide an EPA known to have an action of preventing thrombosis, cerebral infarction, myocardial infarction and the like from unused seaweed.
【０００４】[0004]
【課題を解決するための手段】本発明者らはＥＰＡの供
給原料の拡大と未利用海洋バイオマス資源を利用するた
めに鋭意探索研究を重ねた結果、これまで全くこれらの
高級高度不飽和脂肪酸の含有が知られていなかった紅藻
フダラクに、このＥＰＡが主要な構成成分として存在
し、しかも、ＳＣ−ＣＯ2抽出を介在した抽出分離の場
合の好適な材料であることを解明するに至った。[Means for Solving the Problems] As a result of extensive research conducted by the present inventors in order to expand the feedstock of EPA and utilize unused marine biomass resources, as a result, it has hitherto been possible to completely eliminate these higher polyunsaturated fatty acids. It has been clarified that this EPA is present as a main constituent component in the red alga Fudarac, which was not known to be contained, and is a suitable material in the case of extraction and separation mediated by SC-CO 2 extraction. .
【０００５】本発明は多くの海藻を研究対象にして研究
した結果、当該海藻の有機溶剤抽出物の分析ならびに抽
出物の構造面の研究の結果、当該紅藻フダラクの脂質部
が主要成分として高級高度不飽和脂肪酸をリン脂質の主
要構成脂肪酸とする材料であることを明からかにするこ
とによって本発明をなすに至った。The present invention has been conducted on many seaweeds, and as a result of the analysis of the organic solvent extract of the seaweed and the structural study of the extract, the lipid portion of the red alga Fudarac is the major component. The present invention has been accomplished by making it clear that polyunsaturated fatty acids are the main constituent fatty acids of phospholipids.
【０００６】有機溶媒抽出は、全行程を通じて操作は低
温で行なうのが好ましい。例えば最初にクロロホルム・
メタノール抽出し、それより飽和脂肪酸などをＳＣ−Ｃ
Ｏ2抽出法等で除去した形で当該目的物を分離精製す
る。フダラクを凍結乾して直接ＳＣ−ＣＯ2 抽出し、飽
和脂肪酸及び炭化水素等の除去行った後、直接有機溶媒
（有機溶剤等）で抽出し蛋白部および糖部を除去した
後、その物自体からＳＣ−ＣＯ2抽出で飽和脂肪酸及び
炭化水素等の除去抽出しする行程をも含ませることがで
きる。本発明によって得られるＥＰＡは有機溶媒法その
ものだけに比較してパルミチン酸を１０パーセント程度
除去することが出来る。結果としてＥＰＡは約４０パー
セント以上の高濃度を含有する。The organic solvent extraction is preferably carried out at a low temperature throughout the entire process. For example, first chloroform
Extract with methanol and add saturated fatty acid to SC-C
The target product is separated and purified in a form removed by the O 2 extraction method or the like. Fudaraku is freeze-dried and directly subjected to SC-CO 2 extraction to remove saturated fatty acids and hydrocarbons, and then directly extracted with an organic solvent (organic solvent, etc.) to remove protein and sugar moieties, and then the product itself. The process of removing saturated fatty acids and hydrocarbons and extracting by SC-CO 2 extraction can be included. The EPA obtained by the present invention can remove about 10% of palmitic acid as compared with the organic solvent method itself. As a result, EPA contains high concentrations of about 40 percent or more.
【０００７】[0007]
【作用】本発明方法によると血栓症、脳梗塞、心筋梗
塞、血清脂質改善作用や、血液凝固抑制作用などを有す
る高機能油脂ＥＰＡを、これまで発見されなかった紅藻
フダラクを原料としてよりよく製造することができるの
で、本発明方法はＥＰＡの工業的製法として好適であ
る。According to the method of the present invention, a highly functional fat EPA having thrombosis, cerebral infarction, myocardial infarction, serum lipid improving action, blood coagulation inhibiting action, etc. Since it can be produced, the method of the present invention is suitable as an industrial production method of EPA.
【０００８】紅藻フダラク２００〜５００ｇを十分水洗
し低温に保ってブレンダーにかけ、フダラク部の砕片を
得た。この砕片は低温下に凍結乾燥し有機溶媒抽出（ク
ロロホルム・メタノール等）を行い高濃度高級不飽和脂
肪酸部を得た。得られる抽出物の量は約５０ｍｇ／ｇ
（フダラク凍結乾燥試料）であり淡い黄色を呈してい
る。その脂肪酸組成の分析は常法に従いメチルエステル
化したサンプルをガスクロマトグラフイ−によって分析
した。当該抽出物の構成脂肪酸の主な構成は次の通りで
ある。１４：０（２．３％）、１６：０（３４．０
％）、１６：１（４．１％）、１８：１（８．２％）２
０：４（１５．９％）、２０：５（３５．３％）であ
る。200 to 500 g of the red alga Fudarac was thoroughly washed with water, kept at a low temperature, and then subjected to a blender to obtain fragments of the Fudarac part. This crushed piece was freeze-dried at a low temperature and extracted with an organic solvent (chloroform / methanol, etc.) to obtain a high-concentration higher unsaturated fatty acid moiety. The amount of extract obtained is about 50 mg / g
(Fudarak freeze-dried sample) and has a pale yellow color. The fatty acid composition was analyzed by gas chromatography of a methyl esterified sample according to a conventional method. The main constituents of the constituent fatty acids of the extract are as follows. 14: 0 (2.3%), 16: 0 (34.0)
%), 16: 1 (4.1%), 18: 1 (8.2%) 2
It is 0: 4 (15.9%) and 20: 5 (35.3%).
【０００９】有機溶剤抽出物のＳＣ−ＣＯ2抽出除去操
作によるＥＰＡの高濃度化は有機溶剤抽出物をクロロホ
ルム、有機溶剤などの有機溶媒に溶解し１０〜３５メッ
シュの海砂に一様にコーテイングした。抽出除去条件は
液化二酸化炭素を高圧ポンプで流通式の抽出槽（１００
ｍｌ）に送り超臨界状態とした。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
離槽に誘導し除去物を捕手した。又使用ガス量は積算流
量計で測定した。圧力：２５．０ＭＰａ、温度３１３
Ｋ、ＣＯ2流量：１．０５〜３．００ｄｍ3／ｍｉｎ抽出
除去時間１０〜３０時間、抽出試料：１０ｇ。抽出除去
される物の量は約０．１ｇ／ｇであり白色を呈してい
る。除去処理された物質はパルミチン酸の含有量が減少
しＥＰＡの分析値が高くなっている。その結果は１４：
０（２．４％）１６：０（３７．１％）１６：１（１．
７％）１８：１（８．０％）２０：４（７．９％）２
０：５（４０．６％）である。To increase the concentration of EPA by the SC-CO 2 extraction and removal operation of the organic solvent extract, the organic solvent extract is dissolved in an organic solvent such as chloroform or an organic solvent and uniformly coated on 10-35 mesh sea sand. did. Extraction and removal conditions are liquefied carbon dioxide with a high-pressure pump and a flow-type extraction tank (100
ml) and brought to a supercritical state. The inside of the extraction tank was kept at a constant pressure by a pressure regulator, and the gas flushed under atmospheric pressure was guided to the separation tank to catch the removed substance. The amount of gas used was measured with an integrating flow meter. Pressure: 25.0 MPa, temperature 313
K, CO 2 flow rate: 1.05 to 3.00 dm 3 / min extraction removal time 10 to 30 hours, extracted sample: 10 g. The amount of the substance to be extracted and removed is about 0.1 g / g, which is white. The substance subjected to the removal treatment has a reduced content of palmitic acid and an increased EPA analysis value. The result is 14:
0 (2.4%) 16: 0 (37.1%) 16: 1 (1.
7%) 18: 1 (8.0%) 20: 4 (7.9%) 2
It is 0: 5 (40.6%).
【００１０】[0010]
【発明の効果】本発明方法によると血栓症、脳梗塞、心
筋梗塞、血清脂質改善作用や、血液凝固抑制作用などを
有する高機能油脂ＥＰＡが、これまで発見されなかった
紅藻フダラクを原料としてよりよく製造することができ
ることで、海洋未利用バイオマス資源のさらなる利用研
究に本発明方法は寄与することが出来る。EFFECTS OF THE INVENTION According to the method of the present invention, a highly functional fat EPA having thrombosis, cerebral infarction, myocardial infarction, serum lipid improving action, blood coagulation inhibiting action and the like is prepared from the red alga Fudarac, which has not been discovered so far. By being able to be manufactured better, the method of the present invention can contribute to further utilization research of unused marine biomass resources.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ６１Ｋ 31/20 ＡＢＳ ＡＣＢ 9283−4Ｃ Ｃ１１Ｂ 1/10 2115−4Ｈ (72)発明者 後藤富雄 宮城県塩釜市藤倉三丁目17−26─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI Technical display location A61K 31/20 ABS ACB 9283-4C C11B 1/10 2115-4H (72) Inventor Tomio Goto Miyagi Prefecture 3-17-26 Fujikura, Shiogama City
Claims (2)
タエン酸を分離製造する方法。1. A method for separating and producing eicosapentaenoic acid from the red alga Fudarac.
化炭素抽出処理を行い、得られるリン脂質部の処理行程
に超臨界二酸化炭素抽出分離行程を入れエイコサペンタ
エン酸を製造する方法。2. A method for producing eicosapentaenoic acid, wherein the solvent extract of Fudarak is subjected to a supercritical carbon dioxide extraction treatment, and a supercritical carbon dioxide extraction separation step is added to the treatment step of the resulting phospholipid part.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4195829A JPH0765066B2 (en) | 1992-05-28 | 1992-05-28 | Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4195829A JPH0765066B2 (en) | 1992-05-28 | 1992-05-28 | Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06212186A true JPH06212186A (en) | 1994-08-02 |
| JPH0765066B2 JPH0765066B2 (en) | 1995-07-12 |
Family
ID=16347707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4195829A Expired - Lifetime JPH0765066B2 (en) | 1992-05-28 | 1992-05-28 | Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0765066B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004047554A1 (en) * | 2002-11-26 | 2004-06-10 | Phares Pharmaceutical Research N.V. | Marine lipid compositions |
| KR20040057909A (en) * | 2002-12-25 | 2004-07-02 | 시라코 가부시키가이샤 | Health foods having a blood liquidity-improving action |
| JP2004536059A (en) * | 2001-05-14 | 2004-12-02 | マーテック バイオサイエンシズ ボールダー コーポレーション | Generation and use of polar lipid-rich fractions containing ω-3 and / or ω-6 polyunsaturated fatty acids from microorganisms, genetically modified plant seeds and marine organisms |
| KR20150020513A (en) * | 2013-08-13 | 2015-02-26 | (주)다인내추럴 | Method for Microencapsulation of Fat-Soluble Materials and Method for Functional Beverage by Using Microencapsulated Fat-Soluble Materials |
| CN107904016A (en) * | 2017-11-10 | 2018-04-13 | 海南三元星生物科技股份有限公司 | A kind of red algae essential oil and preparation method thereof |
Citations (4)
| 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 |
| 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 |
-
1992
- 1992-05-28 JP JP4195829A patent/JPH0765066B2/en not_active Expired - Lifetime
Patent Citations (4)
| 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 |
| 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 |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004536059A (en) * | 2001-05-14 | 2004-12-02 | マーテック バイオサイエンシズ ボールダー コーポレーション | Generation and use of polar lipid-rich fractions containing ω-3 and / or ω-6 polyunsaturated fatty acids from microorganisms, genetically modified plant seeds and marine organisms |
| EP1392623A4 (en) * | 2001-05-14 | 2005-05-04 | Martek Biosciences Corp | Production and use of a polar lipid-rich fraction containing omega-3 and/or omega-6 highly unsatruated fatty acids from microbes, genetically modified plant seeds and marine organisms |
| JP2008088181A (en) * | 2001-05-14 | 2008-04-17 | Martek Biosciences Corp | PRODUCTION AND USE OF POLAR LIPID-RICH FRACTION CONTAINING omega-3 AND/OR omega-6 HIGHLY UNSATURATED FATTY ACID(S) DERIVED FROM MICROORGANISM, GENETICALLY-MODIFIED PLANT SEED AND MARINE ORGANISM |
| JP2010065048A (en) * | 2001-05-14 | 2010-03-25 | Martek Biosciences Corp | PRODUCTION AND USE OF POLAR LIPID-RICH FRACTION CONTAINING omega-3 AND/OR omega-6 HIGHLY UNSATURATED FATTY ACID FROM MICROBE, GENETICALLY MODIFIED PLANT SEED AND MARINE ORGANISM |
| EP2255668A3 (en) * | 2001-05-14 | 2012-04-04 | Martek Biosciences Corporation | Production and Use of a Polar Lipid-Rich Fraction Containing Omega-3 and/or Omega-6 Highly Unsaturated Fatty Acids from Microbes, Genetically Modified Plant Seeds and Marine Organisms |
| WO2004047554A1 (en) * | 2002-11-26 | 2004-06-10 | Phares Pharmaceutical Research N.V. | Marine lipid compositions |
| KR20040057909A (en) * | 2002-12-25 | 2004-07-02 | 시라코 가부시키가이샤 | Health foods having a blood liquidity-improving action |
| KR20150020513A (en) * | 2013-08-13 | 2015-02-26 | (주)다인내추럴 | Method for Microencapsulation of Fat-Soluble Materials and Method for Functional Beverage by Using Microencapsulated Fat-Soluble Materials |
| CN107904016A (en) * | 2017-11-10 | 2018-04-13 | 海南三元星生物科技股份有限公司 | A kind of red algae essential oil and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0765066B2 (en) | 1995-07-12 |
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