AU2002309856A1 - 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 - Google Patents

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

Info

Publication number
AU2002309856A1
AU2002309856A1 AU2002309856A AU2002309856A AU2002309856A1 AU 2002309856 A1 AU2002309856 A1 AU 2002309856A1 AU 2002309856 A AU2002309856 A AU 2002309856A AU 2002309856 A AU2002309856 A AU 2002309856A AU 2002309856 A1 AU2002309856 A1 AU 2002309856A1
Authority
AU
Australia
Prior art keywords
dpa
epa
dha
ara
eicosatetraenoic acid
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
Application number
AU2002309856A
Other versions
AU2002309856B2 (en
Inventor
Jesus Ruben Abril
Wulf Banzhaf
Gerhard Kohn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Original Assignee
DSM IP Assets BV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Priority claimed from PCT/US2002/015454 external-priority patent/WO2002092540A1/en
Publication of AU2002309856A1 publication Critical patent/AU2002309856A1/en
Assigned to MARTEK BIOSCIENCES CORPORATION reassignment MARTEK BIOSCIENCES CORPORATION Amend patent request/document other than specification (104) Assignors: MARTEK BIOSCIENCES BOULDER CORPORATION
Application granted granted Critical
Publication of AU2002309856B2 publication Critical patent/AU2002309856B2/en
Priority to AU2009200194A priority Critical patent/AU2009200194B2/en
Assigned to DSM IP ASSETS B.V. reassignment DSM IP ASSETS B.V. Request for Assignment Assignors: MARTEK BIOSCIENCES CORPORATION
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Description

PRODUCTION AND USE OF A POLAR LIPID-RICH FRACTION
CONTAINING OMEGA-3 AND/OR OMEGA-6 HIGHLY UNSATURATED
FATTY ACIDS FROM MICROBES, GENETICALLY MODIFEED
PLANT SEEDS AND MARINE ORGANISMS
FIELD OF THE INVENTION
The present invention relates to the fields of production and use, and in particular, the extraction, separation, synthesis and recovery of polar lipid-rich fractions containing eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), docosapentaenoic acid (DPA(n-3) or DPA(n-6)), arachidonic acid (ARA), and eicosatetraenoic acid (C20:4n-3) from microorganisms, genetically modified seeds and marine organisms (including fish and squid) and their use in human food applications, animal feed, pharmaceutical applications and cosmetic applications.
BACKGROUND OF THE INVENTION
Highly unsaturated fatty acids of the omega-6 and omega-3 series represent a special class of bioactive lipids in that they are important structurally in membranes in the body, but also participate directly and indirectly in communication between cells through the eicosanoid pathways and by their influence of these fatty acids on gene expression. Six of these fatty acids, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), docosapentaenoic acid (DPA(n-3) or DPA(n-6)), arachidonic acid (ARA), and eicosatetraenoic acid (C20:4n-3) have been shown to be effective in preventing/treating cardiovascular disease, inflammatory disease, immune function imbalances, fertility and some of these fatty acids (ARA, DHA DPA(n-6) are important structurally in the brain and nervous system. Recent evidence indicates that some highly unsaturated fatty acids may be more bioavailable when supplied in a phospholipid form than in a triglyceride form. EPA, DHA, and ARA have historically been supplied to the nutritional supplement markets in the form of oil extracted from algae or fish. However recent evidence indicates that some polyunsaturated fatty acids may be more bioavailable in a phospholipid form rather than in a triglyceride form. This may be because of the bipolar nature of phospholipids, making them readily solubilizable in the gut and available for digestion and uptake. This same bipolar property of phospholipids additionally would make these fatty acids more functional in topical applications such as creams and lotions or more soluble in aqueous-based applications such as beverages because of there ability to participate in emulsification processes. We propose that there may be important advantages in supplying these omega-3 and omega-6 HUFAs in the form of phospholipids and improved processes for recovering polar lipids enriched in these fatty acids are also needed. Examples of polar lipids include phospholipids (e.g. phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidyl- glycerol, diphosphatidylglycerols), cephalins, sphingolipids (sphingomyelins and glycosphingolipids), and glycoglycerolipids. Phospholipids are composed of the following major structural units: fatty acids, glycerol, phosphoric acid, and amino alcohols. They are generally considered to be structural lipids, playing important roles in the structure of the membranes of plants, microbes and animals. Because of their chemical structure, polar lipids exhibit a bipolar nature, exhibiting solubility or partial solubility in both polar and non-polar solvents. The term polar lipid within the present description is not limited to natural polar lipids but also includes chemically modified polar lipids. Although the term oil has various meanings, as used herein, it will refer to the triacylglycerol fraction.
One of the important characteristics of polar lipids, and especially phospholipids, is that they commonly contain polyunsaturated fatty acids (PUFAs: fatty acids with 2 or more unsaturated bonds). In many plant, microbial and animal systems, they are especially enriched in the highly unsaturated fatty acids (HUFAs: fatty acids with 4 or more unsaturated bonds) of the omega-3 and omega-6 series. Although these highly unsaturated fatty acids are considered unstable in triacylglycerol form, they exhibit enhanced stability when incorporated in phospholipids.
The primary sources of commercial PUFA-rich phospholipids are soybeans and canola seeds. These biomaterials do not contain any appreciable amounts of highly unsaturated fatty acids unless they have been genetically modified. The phospholipids (commonly called lecithins) are routinely recovered from these oilseeds as a by-product of the vegetable oil extraction process. For example, in the production of soybean or canola oil, the beans (seeds) are first heat-treated and then crushed, ground, and/or flaked, followed by extraction with a non-polar solvent such as hexane. Hexane removes the triacylglycerol-rich fraction from the seeds together with a varying amount of polar lipids (lecithins). The extracted oil is then de-gummed (lecithin removal) either physically or chemically as a part of the normal oil refining process and the precipitated lecithins recovered. This process however has two disadvantages: (1) the seeds must be heat- treated before extraction with hexane, increasing the processing cost, and increasing undesirable oxidation reactions and denaturing the protein fraction, thereby decreasing its value as a by-product; and (2) the use of the non-polar solvents such as hexane also presents toxicity and flammability problems that must be dealt with.
The crude lecithin extracted in the "de-gumming" process can contain up to about 33% oil (triacylglycerols) along with sterols and glucosides. One preferred method for separating this oil from the crude lecithin is by extraction with acetone. The oil (triacylglycerols) is soluble in acetone and the lecithin is not. The acetone solution is separated from the precipitate (lecithin) by centrifugation and the precipitate dried under first a fiuidized bed drier and then a vacuum drying oven to recover the residual acetone as the product is dried. Drying temperatures of 50-70°C are commonly used. The resulting dried lecithins contain approximately 2-4% by weight of oil (triacylglycerols). Process temperatures above 70°C can lead to thermal decomposition of the phospholipids. However, even at temperatures below 70°C the presence of acetone leads to the formation of products that can impair the organoleptic quality of the phospholipids. These byproducts can impart musty odors to the product and also a pungent aftertaste.
What is needed is an improved process for effectively recovering polar lipids and phospholipids rich in omega-3 and omega-6 HUFAs from biomaterials that enables the use of these fatty acid in food, nutritional supplement, pharmaceutical and cosmetic applications. Furthermore the fractions are needed as an ingredient in feed for companion animals and in aquaculture.
SUMMARY OF THE INVENTION In accordance with the present invention, an improved process is provided for recovering polar lipids enriched in omega-3 and/or omega-6 HUFAs from native biomaterials such as seeds and microorganisms and the use thereof.
In one embodiment of the present invention, a method is provided for providing a human, animal or aquaculture organism diet supplement enriched with at least one of eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), docosapentaenoic acid (n- 3)(DPAn-3), eicosatetraenoic acid (n-3), docosapentaenoic acid (n-6)(DPAn-6) or arachidonic acid (ARA). The method includes the steps of producing a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from genetically modified seeds or marine animals; and providing the polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA in a form consumable or usable by humans or animals. Preferably, the animal is a companion animal. In another embodiment of the present invention, a method is provided for treating a deficiency in at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA. The method includes the steps of producing a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and providing the polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA to treat the deficiency. The deficiency can result in an inflammatory condition, an immune system imbalance, a cardiovascular disease, a developmental deficit related to nervous system development, a woman's health condition or an infant's health condition. In another embodiment of the present invention, a method is provided for treating a chronic inflammatory disease state of the lung. The method includes the steps of producing a purified phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; blending the phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one of EPA-, GLA- or SDA-rich oils; and producing an aerosol comprising the blend for the treatment of the disease states. The chronic inflammatory disease state of the lung can result in chronic obstructive pulmonary disease (COPD), asthma or cystic fibrosis. In another embodiment of the present invention, a method is provided for the treatment of skin lesions, induced burn, UV-irradiation or other skin disorders. The method includes the steps of producing a purified phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; blending the phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one EPA-, GLA- or SDA-rich oil; and producing a lotion or cream for the treatment of the skin disorders. In another embodiment of the present invention, a method is provided for treating cachexia and severe fat malabsorption. The method includes the steps of producing a purified phospholipid enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA; blending the purified phospholipid enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one other purified phospholipid; blending the purified phospholipid enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one DHA, EPA, GLA- or SDA-rich oil; and producing a liquid or dried dietetic product for the treatment of the disease states. The cachexia or severe fat malabsorption can be a result of cancer or Crohn's disease. Preferably, the at least one other purified phospholipid is obtained from the group consisting of soy, rape seed, evening primrose, safflower, sunflower, canola, peanut, egg and mixtures thereof.
In another embodiment of the present invention, a method is provided for the treatment of H. pylori-infection of gastrointestinal tract. The method includes the steps of producing a purified phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; blending the phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one EPA-, GLA- or SDA-rich oil; and producing a fat emulsion or a dietetic product for the treatment of the disease.
In another embodiment of the present invention, a method is provided for providing a fat blend enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA. The method includes the steps of extracting a polar lipid- rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and mixing the polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with another oil. Preferably, the another oil is selected from the group consisting of fish oil, microbial oil, vegetable oil, GLA-containing oil, SDA-containing oil or mixtures thereof. In another embodiment of the present invention, a method is provided for providing a blend of polar lipids enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA. The method includes the steps of extracting a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and mixing the polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with another polar lipid. Preferably, the another polar lipid is selected from the group consisting of soy polar lipids, rapeseed polar lipids, sunflower polar lipids, safflower polar lipids, canola polar lipids, peanut polar lipids or egg yolk polar lipids and mixtures thereof.
In another embodiment of the present invention, a fat blend is provided enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA. The fat blend includes a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and another oil. Preferably, the another oil is selected from the group consisting of fish oil, microbial oil, vegetable oil, GLA-containing oil, SDA-containing oil and mixtures thereof.
In another embodiment of the present invention, a method is provided for producing a blend of polar lipids enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA. The method includes the steps of extracting an EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA-enriched polar lipid-rich fraction from microbes, seeds or marine animals; and mixing the EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA-enriched polar lipid-rich fraction with another polar lipid. Preferably, the another polar lipid is selected from the group consisting of soy polar lipids, rapeseed polar lipids, sunflower polar lipids, safflower polar lipids, canola polar lipids, peanut polar lipids or egg yolk polar lipids and mixtures thereof.
In another embodiment of the present invention, purified phospholipids enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA derived from polar lipid-rich fraction extracted from genetically modified seeds or marine animals are provided. Preferably, the EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA-enriched phospholipid-fraction is in a form consumable or usable by humans or animals.
In another embodiment of the present invention, a method is provided for providing a human, animal or aquaculture organism diet supplement enriched with at least one of eicosapentaenoic acid (EPA), docosapentaenoic acid (n-3)(DPAn-3), eicosatetraenoic acid (n-3) or docosapentaenoic acid (n-6)(DPAn-6). The method includes the steps of producing a polar lipid-rich fraction enriched with at least one of EPA, DPA(n-3), DPA(n-6) and eicosatetraenoic acid from microbes, genetically modified seeds or marine animals; and providing the polar lipid-rich fraction enriched with at least one of EPA, DPA(n-3), DPA(n-6) and eicosatetraenoic acid in a form consumable or usable by humans or animals. The polar lipid-rich fraction of the methods or products of can be provided as an ingredient of dietetic, pharmaceutical and cosmetic applications.
The fat blend of the methods or products of the present invention can be provided as an ingredient of dietetic, pharmaceutical and cosmetic applications.
The blend of polar lipids of the methods or products of the present invention can be provided as an ingredient of dietetic, pharmaceutical and cosmetic applications.
The purified phospholipids of the methods or products of the present invention can be provided as an ingredient of dietetic, pharmaceutical and cosmetic applications.
Preferably, the marine animals of the methods and products of the present invention are fish, squid, mollusks or shrimp. Preferably, the marine animals are fish or fish eggs from the group including salmon, tuna, haddock, sardines, mackerel, or menhaden.
Preferably, the microbes of the methods and products of the present invention are selected from fungi, microalgae, protozoa or bacteria. More preferably, microbes are selected from the Stramenopiles, Thraustochytriales, Chrysophyceae, Xanthophyceae, Bacillariophyceae, Dinophyceae, Phaeophyceae, Rhodophyceae, Chlorophyceae, Euglenophyceae, Cryptophyceae, Oomycetes, Chytridomycetes, or Zygomycetes. More preferably, the microbes are selected from the group of genera consisting of Mortierella, Mucor, Phycomyces, Rhizopus, Pythium, Ochromonas, Nitzschia, Phaeodactylum, Skeletonema, Fucus, Laminaria, Platymonas, Achyla, Phytophera, Schizochytrium, Thraustochytrium, or Crypthecodinium.
Preferably, the EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid, ARA or mixture thereof employed in the methods and products of the present invention makes up at least two weight percent of the total fatty acids of the polar lipid fraction.
Preferably, the EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid, ARA or mixture thereof employed in the methods and products at the present invention makes up at least five weight percent of the total fatty acids of the polar lipid fraction. Preferably, the plant seeds or microbes employed in the methods and products to the present invention have been genetically modified to increase their n-3 or n-6 HUFA content.
Preferably, the seeds or microbes used in the methods and products of the present invention have been genetically modified to increase the production of at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA.
Preferably, the seeds employed in the methods and products of the present invention are selected from the group consisting of canola, rapeseed, linseed, flaxseed, sunflower, safflower, peanuts, soybeans or corn. Preferably, the polar lipid-rich fraction is extracted from the seeds and microbes using alcohol.
In an alternative embodiment of the present invention, the polar lipid-rich fraction is derived as a by-product (e.g., by de-gumming) of oil extraction from the seeds using hexane and other non-polar solvents.
Preferably, the polar lipid-rich fraction used in the methods and products of the present invention is extracted from the seeds and microbes by use of gravity or centrifugal extraction technology.
DETAILED DESCRIPTION OF THE INVENTION
Because of their bipolar nature, polar lipids (including phospholipids) are of significant commercial interest as wetting and emulsifying agents. These properties may also help make HUFAs in the phospholipids more bioavailable, in addition to enhancing their stability. These properties make phospholipids ideal forms of ingredients for use in nutritional supplements, food, infant formula, pharmaceutical, and cosmetic applications. Dietary benefits of phospholipids include both improved absorption and improved incorporation. Phospholipids also have a broad range of functionality in the body in that they are important cell membrane constituents, they are good emulsifiers, they can act as intestinal surfactants, serve as a choline source and as a source of HUFAs.
EPA, DHA, and ARA are normally produced for the nutritional supplement market and food uses through the extraction (by cooking) of fish (EPA and DHA) such as menhaden, tuna or salmon, or hexane extraction of fungal biomass (ARA) from the genus Mortierella. The phospholipids in both processes are removed in a later degumming step that produces a waste material comprising a complex mixture of neutral lipids, sterols, glucosides and phospholipids. This material is normally sold to the domestic animal feed industry to dispose of it.
Besides fish and fungal biomass, there are microbial sources of DHA and DPA(n-
6). For the present invention, useful microbes can be selected from fungi, microalgae, protozoa or bacteria. These organisms can be selected from the groups including the
Stramenopiles, Thraustochytriales, Chrysophyceae, Xanthophyceae, Bacillariophyceae,
Dinophyceae, Phaeophyceae, Rhodophyceae, Chlorophyceae, Euglenophyceae,
Cryptophyceae, Oomycetes, Chytridomycetes, or Zygomycetes. Useful microbes can also be selected from the group of genera consisting of Mortierella, Mucor, Phycomyces, Rhizopus, Pythium, Ochromonas, Nitzschia, Phaeodactylum, Skeletonema, Fucus,
Platymonas, Achyla, Phytophera, Schizochytrium, Thraustochytrium, or
Crypthecodinium. Microorganisms are good sources of phospholipids because they can be grown in culture in a manner that optimizes phospholipid production and minimizes triglyceride (oil) production. On the other hand the methods used in this invention allow both oil and phospholipids to be recovered separately in forms that can be used directly in food, feed, nutritional supplements, cosmetic or pharmaceutical application.
DHA, EPA and ARA phospholipids can be recovered from fish, microalgae, or fungi through the degumming process described above. However as noted this produces a complex material containing many other compounds including neutral lipids, sterols, glucosides, etc
A preferred embodiment of the present invention is to use alcohol and centrifugation to recover the omega-3 and/or omega-6 HUFA-rich phospholipids. Preferred methods for this recovery are described in the following references, which are incorporated by reference herein in their entirety: i. PCT Application Serial No. PCT/USO 1/12047, entitled "Method for the
Fractionation of Oil and Polar Lipid-Containing Native Raw Materials" filed April 12, 2001; ii. PCT Application Serial No. PCT/USOl/12049, entitled "Method For The Fractionation Of Oil And Polar Lipid-Containing Native Raw Materials Using Water-Soluble Organic Solvent And Centrifugation" filed April 12, 2001.
Once the omega-3 and/omega-6 rich phospholipid fractions have been extracted by these preferred processes, they can be used directly as ingredients or they can be purified further and even separated into phospholipid classes by well-known techniques such as different forms of chromatography, molecular distillation, and special refining techniques. Polar lipid groups phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine, phosphatidylinositol, and sphingolipids. The phospholipid rich polar lipids or the purified phospholipid rich fractions can also be mixed with another lipid or oil such as fish lipids, microbial lipids, vegetable lipids, GLA-containing lipids, SDA-containing lipids and mixtures thereof, or be mixed with another phospholipid fraction (lecithin) such as soy or egg yolk lecithin, sunflower lecithin, peanut lecithin or mixtures thereof prior to use as a nutritional supplement, feed or food ingredient. These mixtures of phospholipids can also be incorporated into creams or lotions for topical applications (e.g. treating of skin conditions) or skin lesions induced by bums, UV- irradiation or other skin damaging processes. The mixtures can also be processed to produce a liquid or spray-dried dietetic product or fat emulsion for treating cachexia and severe fat malabsorption or for treatment of H. pylori infection of the gastrointestinal tract or incorporated into aerosol sprays for treating chronic inflammatory disease states of the lung (e.g., COPD, asthma, cystic fibrosis).
Advantages of the present invention including providing omega-3 and/or omega-6 ΗUFAs in a more bioactive and functional form (phospholipid) than the triglyceride form and include a better process (e.g., a) no need for heat treatment; b) no use of toxic solvents (like hexane) and c) no artifacts and off-flavors due to the use of acetone) for recovering these phospholipids from oilseeds and microbes. The EPA, DΗA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and/or ARA content of the total fatty acids of the polar lipid fractions and comprise at least two weight percent of the total fatty acids of the polar lipid fraction, more preferably greater than 5 weight percent, more preferably greater than 10 weight percent, and most preferably greater than 20 weight percent of total fatty acids in the polar lipid fraction.
EXAMPLE
Example 1
Phospholipids were extracted from salmon, salmon roe, Black tiger prawns, squid, Schizochytrium sp, and the total fatty acid content of the phospholipids was determined by gas chromatography. The results are presented in Table 1. As can be observed the phospholipid fraction of these biomaterials can be used to deliver omega-3 and/or omega- 6 HUFAs and in this form these bioactive fatty acids should be more stable, more bioavailable, and more functional.
Table 1. Total fatty acid content of phospholipids extracted from 4 types marine animal products and forma microbial source.
The present invention, in various embodiments, includes components, methods, processes, systems and/or apparatus substantially as depicted and described herein, including various embodiments, subcombinations, and subsets thereof. Those of skill in the art will understand how to make and use the present invention after understanding the present disclosure. The present invention, in various embodiments, includes providing devices and processes in the absence of items not depicted and/or described herein or in various embodiments hereof, including in the absence of such items as may have been used in previous devices or processes, e.g., for improving performance, achieving ease and/or reducing cost of implementation.
The foregoing discussion of the invention has been presented for purposes of illustration and description. The foregoing is not intended to limit the invention to the form or forms disclosed herein. Although the description of the invention has included description of one or more embodiments and certain variations and modifications, other variations and modifications are within the scope of the invention, e.g., as may be within the skill and knowledge of those in the art, after understanding the present disclosure. It is intended to obtain rights which include alternative embodiments to the extent permitted, including alternate, interchangeable and/or equivalent structures, functions, ranges or steps to those Claimed, whether or not such alternate, interchangeable and/or equivalent structures, functions, ranges or steps are disclosed herein, and without intending to publicly dedicate any patentable subject matter.

Claims (39)

We claim:
1. A method for providing a human, animal or aquaculture organism diet supplement enriched with at least one of eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), docosapentaenoic acid (n-3)(DPAn-3), eicosatetraenoic acid (n-3), docosapentaenoic acid (n-6)(DPAn-6) or arachidonic acid (ARA) comprising the steps:
(a) producing a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from genetically modified seeds or marine animals; and
(b) providing said polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA in a form consumable or usable by humans or animals.
2. The method of Claim 1 , wherein the animal is a companion animal.
3. A method for treating a deficiency in at least one of EPA, DHA, DPA(n- 3), DPA(n-6), eicosatetraenoic acid or ARA comprising the steps: (a) producing a polar lipid-rich fraction enriched with at least one of EPA, DHA,
DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and
(b) providing said polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA to treat said deficiency.
4. The method of Claim 3, wherein said deficiency results in an inflammatory condition, an immune system imbalance, a cardiovascular disease, a developmental deficit related to nervous system development, a woman's health condition or an infant's health condition.
5. A method for treating a chronic inflammatory disease state of the lung comprising the steps:
(a) producing a purified phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals;
(b) blending said phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one of EPA-,
GLA- or SDA-rich oils; and
(c) producing an aerosol comprising the blend of step (b) for the treatment of said disease states.
6. The method of claim 5, wherein the chronic inflammatory disease state of the lung is COPD, asthma or cystic fibrosis.
7. A method for the treatment of skin lesions, induced bu , UV-irradiation or other skin disorders comprising the steps: (a) producing a purified phospholipid fraction enriched with at least one of
EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals;
(b) blending said phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one EPA-, GLA- or SDA-rich oil; and
(c) producing a lotion or cream for the treatment of said skin disorders.
8. A method for treating cachexia or fat malabsorption comprising the steps: (a) producing a purified phospholipid enriched with at least one of EPA,
DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA; (b) blending said purified phospholipid enriched with at least one of EPA,
DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one other purified phospholipid;
(c) blending said purified phospholipid enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one DHA, EPA, GLA- or SDA-rich oil; and
(d) producing a liquid or dried dietetic product for the treatment of said disease states.
9. The method of Claim 8, wherein the cachexia or fat malabsorption is a result of cancer or Crohn's disease.
10. The method of Claim 8, wherein the at least one other purified phospholipid is obtained from the group consisting of soy, rape seed, evening primrose, safflower, sunflower, canola, peanut, egg and mixtures thereof.
11. A method for the treatment of H. ^ /oπ'-infection of gastrointestinal tract comprising the steps: (a) producing a purified phospholipid fraction enriched with at least one of
EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; (b) blending said phospholipid fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with at least one EPA-, GLA- or SDA-rich oil; and
(c) producing a fat emulsion or a dietetic product for the treatment of said disease.
12. A method for providing a fat blend enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA comprising the steps:
(a) extracting a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and
(b) mixing said polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with another oil.
13. The method of Claim 12, wherein said another oil is selected from the group consisting of fish oil, microbial oil, vegetable oil, GLA-containing oil, SDA- containing oil or mixtures thereof.
14. A method for providing a blend of polar lipids enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA comprising the steps:
(a) extracting a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and
(b) mixing said polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid and ARA with another polar lipid.
15. The method of Claim 14, wherein said another polar lipid is selected from the group consisting of soy polar lipids, rape seed polar lipids, sunflower polar lipids, safflower polar lipids, canola polar lipids, peanut polar lipids or egg yolk polar lipids and mixtures thereof.
16. A fat blend enriched with at least one of EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA comprising:
(a) a polar lipid-rich fraction enriched with at least one of EPA, DHA, DPA(n- 3), DPA(n-6), eicosatetraenoic acid and ARA from microbes, genetically modified seeds or marine animals; and
(b) another oil.
17. The oil of Claim 16, wherein said another oil is selected from the group consisting of fish oil, microbial oil, vegetable oil, GLA-containing oil, SDA-containing oil and mixtures thereof.
18. A blend of polar lipids enriched with at least one of EPA, DHA, DPA(n- 3), DPA(n-6), eicosatefraenoic acid or ARA comprising the steps:
(a) extracting a EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA-enriched polar lipid-rich fraction from microbes, seeds or marine animals; and
(b) mixing said EPA, DHA, DPA(n-3), DPA(n-6), eicosatefraenoic acid or ARA-enriched polar lipid-rich fraction with another polar lipid.
19. The method of Claim 18, wherein said another polar lipid is selected from the group consisting of soy polar lipids, rape seed polar lipids, sunflower polar lipids, safflower polar lipids, canola polar lipids, peanut polar lipids or egg yolk polar lipids and mixtures thereof.
20. Purified phospholipids enriched with at least one EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA derived from polar lipid-rich fraction extracted from genetically modified seeds or marine animals.
21. The purified phospholipids of Claim 20, wherein said EPA, DHA, DPA(n- 3), DPA(n-6), eicosatetraenoic acid or ARA-enriched phospholipid-fraction is in a form consumable or usable by humans or animals.
22. A method for providing a human, animal or aquaculture organism diet supplement enriched with at least one of eicosapentaenoic acid (EPA), docosapentaenoic acid (n-3)(DPAn-3), eicosatetraenoic acid (n-3) or docosapentaenoic acid (n-6)(DPAn-6) comprising the steps:
(a) producing a polar lipid-rich fraction enriched with at least one of EPA, DPA(n-3), DPA(n-6) and eicosatetraenoic acid from microbes, genetically modified seeds or marine animals; and
(b) providing the polar lipid-rich fraction enriched with at least one of EPA, DPA(n-3), DPA(n-6) and eicosatetraenoic acid in a form consumable or usable by humans or animals.
23. A polar lipid-rich fraction of the method or product of any preceding
Claim as an ingredient of dietetic, pharmaceutical or cosmetic applications.
24. A fat blend of the method or product of any preceding Claim as an ingredient of dietetic, pharmaceutical or cosmetic applications.
25. A blend of polar lipids of the method or product of any preceding Claim as an ingredient of dietetic, pharmaceutical or cosmetic applications.
26. Purified phospholipids of the method or product of any preceding Claim as an ingredient of dietetic, pharmaceutical or cosmetic applications.
27. The method or product of any preceding Claim, wherein said marine animals are fish, squid, mollusks or shrimp.
28. The method or product of any preceding Claim, wherein said marine animals are fish or fish eggs from the group including salmon, tuna, haddock, sardines, mackerel, or menhaden.
29. The method or product of any preceding Claim, wherein said microbes are selected from fungi, microalgae, protozoa or bacteria.
30. The method or product of any preceding Claim, wherein said microbes are selected from the Stramenopiles, Thraustochytriales, Chrysophyceae, Xanthophyceae, Bacillariophyceae, Dinophyceae, Phaeophyceae, Rhodophyceae, Chlorophyceae, Euglenophyceae, Cryptophyceae, Oomycetes, Chytridomycetes, or Zygomycetes.
31. The method or product of any preceding Claim, wherein said microbes are selected from the group of genera consisting of Mortierella, Mucor, Phycomyces, Rhizopus, Pythium, Ochromonas, Nitzschia, Phaeodactylum, Skeletonema, Fucus, Laminaria, Platymonas, Achyla, Phytophera, Schizochytrium, Thraustochytrium, or Crypthecodinium.
32. The method of or product of any preceding Claim, wherein EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid, ARA or mixture thereof comprises at least two weight percent of the total fatty acids of the polar lipid fraction.
33. The method or product of any preceding Claim, wherein EPA, DHA, DPA(n-3), DPA(n-6), eicosatefraenoic acid, ARA or mixture thereof comprises at least five weight percent of the total fatty acids of the polar lipid fraction.
34. The method or product of any preceding Claim, wherein said plant seeds or microbes have been genetically modified to increase their n-3 or n-6 HUFA content.
35. The method or product of any preceding Claim, wherein said seeds or microbes have been genetically modified to increase the production of at least one of
EPA, DHA, DPA(n-3), DPA(n-6), eicosatetraenoic acid or ARA.
36. The method or product of any preceding Claim, wherein said seeds are selected from the group consisting of canola, rape seed, linseed, flaxseed, sunflower, safflower, peanuts, soybeans or com.
37. The method or product of any preceding Claim, wherein said polar lipid- rich fraction is extracted from said seeds and microbes using alcohol.
38. The method or product of any preceding Claim, wherein said polar lipid- rich fraction is derived as a by-product of oil extraction from said seeds using hexane or other non-polar solvent.
39. The method or product of any preceding Claim, wherein said polar lipid- rich fraction is extracted from said seeds and microbes by use of gravity or cenfrifugal extraction technology.
AU2002309856A 2001-05-14 2002-05-14 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 Ceased AU2002309856B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2009200194A AU2009200194B2 (en) 2001-05-14 2009-01-20 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

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US29089901P 2001-05-14 2001-05-14
US60/290,899 2001-05-14
PCT/US2002/015454 WO2002092540A1 (en) 2001-05-14 2002-05-14 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

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU2009200194A Division AU2009200194B2 (en) 2001-05-14 2009-01-20 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

Publications (2)

Publication Number Publication Date
AU2002309856A1 true AU2002309856A1 (en) 2003-05-01
AU2002309856B2 AU2002309856B2 (en) 2008-10-23

Family

ID=23117970

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2002309856A Ceased AU2002309856B2 (en) 2001-05-14 2002-05-14 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
AU2009200194A Ceased AU2009200194B2 (en) 2001-05-14 2009-01-20 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

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU2009200194A Ceased AU2009200194B2 (en) 2001-05-14 2009-01-20 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

Country Status (8)

Country Link
US (1) US20050129739A1 (en)
EP (2) EP2255668A3 (en)
JP (3) JP2004536059A (en)
AU (2) AU2002309856B2 (en)
CA (1) CA2451116C (en)
HK (1) HK1151439A (en)
MX (1) MX281182B (en)
WO (1) WO2002092540A1 (en)

Families Citing this family (92)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6566583B1 (en) * 1997-06-04 2003-05-20 Daniel Facciotti Schizochytrium PKS genes
WO2002092540A1 (en) * 2001-05-14 2002-11-21 Martek Biosciences Corporation 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
MXPA03010467A (en) * 2001-05-14 2004-12-06 Martek Biosciences Boulder Corp Production and use of a polar lipid-rich fraction containing stearidonic acid and gamma linolenic acid from plant seeds and microbes.
WO2003011873A2 (en) 2001-07-27 2003-02-13 Neptune Technologies & Bioressources Inc. Natural marine source phospholipids comprising flavonoids, polyunsaturated fatty acids and their applications
EP2368445A1 (en) * 2002-06-18 2011-09-28 Martek Biosciences Corporation Stable Emulsions of Oils in Aqueous Solutions and Methods for Producing Same
AU2003283429A1 (en) * 2002-11-26 2004-06-18 Phares Pharmaceutical Research N.V. Marine lipid compositions
CA2518197A1 (en) * 2003-03-07 2004-09-23 Advanced Bionutrition Corporation Feed formulation for terrestrial and aquatic animals
WO2004098311A1 (en) * 2003-05-05 2004-11-18 Denofa As Fish oils with an altered fatty acid profile, method of producing same and their use
US11952581B2 (en) 2003-08-01 2024-04-09 Basf Plant Science Gmbh Process for the production of polyunsaturated fatty acids in transgenic organisms
EP2166069B2 (en) 2003-08-01 2024-01-24 BASF Plant Science GmbH Method for producing polyunsaturated fatty acids in transgenic organisms
US8921422B2 (en) 2003-10-01 2014-12-30 The Iams Company Methods and kits for enhancing ability to learn in a puppy or kitten
AU2005209480B2 (en) 2004-01-30 2010-09-02 Bionovate Limited Solvent extraction of lipids such as essential fatty acids
WO2005083053A2 (en) 2004-02-27 2005-09-09 Basf Plant Science Gmbh Method for producing unsaturated omega-3 fatty acids in transgenic organisms
JP4567047B2 (en) 2004-02-27 2010-10-20 ビーエーエスエフ プラント サイエンス ゲーエムベーハー Process for producing polyunsaturated fatty acids in transgenic plants
BR122019013214B1 (en) 2004-04-22 2022-04-12 Commonwealth Scientific And Industrial Research Organisation Isolated polynucleotide, vector, recombinant cell, method of producing a recombinant cell, method of producing one or more long-chain polyunsaturated fatty acid(s), method of producing a transgenic seed, method of producing oil, method of producing an oilseed, transgenic seed extract, composition comprising said extract, feed and use of said recombinant cell or extract
US7807849B2 (en) * 2004-04-22 2010-10-05 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
EP1656839A1 (en) 2004-11-11 2006-05-17 N.V. Nutricia Nutrition containing lipid blend
WO2006054183A2 (en) * 2004-11-17 2006-05-26 Natural Asa Enzymatically synthesized marine phospholipids
US7884131B2 (en) * 2004-11-19 2011-02-08 Martek Biosciences, Corporation Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same
DE102005003624A1 (en) * 2005-01-26 2006-07-27 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Antioxidative active extract, useful to prepare fatty acid composition, which is useful as e.g. an active agent in pharmaceutical composition, a food supplement and/or food ingredient or an animal feed, comprises Crypthecodinium species
GB0506788D0 (en) * 2005-04-04 2005-05-11 Biosea Man As Process
JP5886511B2 (en) 2005-06-07 2016-03-16 ディーエスエム ニュートリショナル プロダクツ アーゲーDSM Nutritional Products AG Eukaryotic microorganisms for the production of lipids and antioxidants
FR2889957B1 (en) * 2005-09-01 2008-06-27 Gerard Pieroni USE OF PHOSPHOLIPID DHA FOR THE PREPARATION OF A COMPOSITION FOR THE TREATMENT OF RESPIRATORY INSUFFICIENCY.
CA2630173C (en) * 2005-11-18 2018-01-09 Commonwealth Scientific And Industrial Research Organisation Feedstuffs for aquaculture comprising stearidonic acid
JP4344827B2 (en) * 2005-11-28 2009-10-14 国立大学法人九州大学 Method for producing phospholipids containing long-chain highly unsaturated fatty acids using microorganisms of the genus Schizochytrium
US20070213298A1 (en) * 2006-02-07 2007-09-13 Universitetet I Oslo Omega 3
AR059376A1 (en) 2006-02-21 2008-03-26 Basf Plant Science Gmbh PROCEDURE FOR THE PRODUCTION OF POLYINSATURATED FATTY ACIDS
NZ547429A (en) 2006-05-24 2009-09-25 Ind Res Ltd Extraction of highly unsaturated lipids with liquid dimethyl ether
WO2008004900A1 (en) * 2006-07-05 2008-01-10 Photonz Corporation Limited Production of ultrapure epa and polar lipids from largely heterotrophic culture
WO2008129358A2 (en) 2006-08-01 2008-10-30 Ocean Nutrition Canada Ltd. Oil producing microbes and methods of modification thereof
WO2008025068A1 (en) 2006-08-29 2008-03-06 Commonwealth Scientific And Industrial Research Organisation Synthesis of fatty acids
CA2662260C (en) * 2006-08-29 2015-10-27 Martek Biosciences Corporation Use of dpa(n-6) oils in infant formula
EP2120920A4 (en) * 2007-02-20 2011-06-15 Martek Biosciences Corp Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same
US8697138B2 (en) 2007-03-28 2014-04-15 Aker Biomarine As Methods of using krill oil to treat risk factors for cardiovascular, metabolic, and inflammatory disorders
ES2415684T3 (en) 2007-03-28 2013-07-26 Aker Biomarine As Biologically effective krill oil compositions
EP2153736B1 (en) * 2007-05-11 2017-04-19 Bizen Chemical Co., Ltd. Novel leukotriene receptor antagonist from marine sources
AU2008288677A1 (en) * 2007-08-17 2009-02-26 Murray Goulburn Co-Operative Co. Limited Compositions comprising phospholipids
US20090064567A1 (en) 2007-09-12 2009-03-12 Martek Biosciences Corporation Biological oils and production and uses Thereof
CN101909467B (en) 2007-11-01 2013-04-24 恩兹默泰克有限公司 Lipid mixture for infant nutrition
US8343753B2 (en) 2007-11-01 2013-01-01 Wake Forest University School Of Medicine Compositions, methods, and kits for polyunsaturated fatty acids from microalgae
US20090202672A1 (en) * 2008-02-11 2009-08-13 Monsanto Company Aquaculture feed, products, and methods comprising beneficial fatty acids
JP2010079993A (en) * 2008-09-26 2010-04-08 Toshiba Storage Device Corp Storage device and method for adjusting storage device
JP2010090065A (en) * 2008-10-08 2010-04-22 Nihon Kolmar Co Ltd Cosmetic product
CA2743880C (en) * 2008-11-18 2020-08-18 James Robertson Petrie Recombinant cells comprising exogenous a5 elongase and methods for producing docosapentaenoic acid
CN104042600A (en) 2009-02-02 2014-09-17 帝斯曼知识产权资产有限公司 Methods for improving cognitive function and decreasing heart rate
US8372812B2 (en) 2009-02-26 2013-02-12 Aker Biomarine Asa Phospholipid and protein tablets
US8207363B2 (en) 2009-03-19 2012-06-26 Martek Biosciences Corporation Thraustochytrids, fatty acid compositions, and methods of making and uses thereof
CN101812484B (en) * 2009-03-20 2012-04-25 厦门汇盛生物有限公司 Method for producing DHA by Schizochytrium in high-density culture through fermentation
EP2272383A1 (en) 2009-06-22 2011-01-12 SBAE Industries NV Composition Comprising Omega-7 and/or Omega-4 Fatty Acids
US20110177061A1 (en) 2009-07-10 2011-07-21 Martek Biosciences Corporation Methods of treating and preventing neurological disorders using docosahexaenoic acid
US20110082205A1 (en) 2009-10-01 2011-04-07 Panker Cynthia A Docosahexaenoic Acid Gel Caps
US8586567B2 (en) 2009-10-29 2013-11-19 Acasti Pharma, Inc. Concentrated therapeutic phospholipid compositions
KR20150013667A (en) 2010-01-19 2015-02-05 디에스엠 아이피 어셋츠 비.브이. Eicosapentaenoic acid-producing microorganisms, fatty acid compositions, and methods of making and uses thereof
FR2955461B1 (en) * 2010-01-27 2012-04-13 Polaris NUTRITIONAL INGREDIENT RICH IN DHA AND EPA
JP5576699B2 (en) * 2010-04-15 2014-08-20 花王株式会社 GIP elevation inhibitor
MY163938A (en) 2010-06-14 2017-11-15 Io-Mega Holding Corp Method for the production of algae derived oils
ITMI20101666A1 (en) * 2010-09-13 2012-03-14 Dmf Dietetic Metabolic Food S R L COMPOSITION BASED ON DOCOSAESAENOIC ACID (DHA), IN THE TREATMENT OF CYSTIC FIBROSIS AND NON-ALCOHOLIC HEPATIC STEATOSIS
LT2697345T (en) * 2011-04-14 2016-09-12 Polar Omega A/S A process for the isolation of a phospholipid
CA2842272C (en) * 2011-07-21 2020-04-28 Dsm Ip Assets B.V. Fatty acid compositions
WO2013024174A1 (en) 2011-08-18 2013-02-21 Dsm Ip Assets B.V. Dha triglyceride, dha free fatty acid, and dha ethyl ester emulsions, and methods of treating spinal cord injury
DE102011113283A1 (en) 2011-09-06 2013-03-07 Johann Wolfgang Goethe-Universität Increase of lipid content in microalgae by genetic manipulation of a triacylglycerol (TAG) lipase
PE20150269A1 (en) * 2012-01-23 2015-02-19 Restorsea Llc COSMETIC COMPOSITION CONTAINING AN EGG Hatching PROTEIN
MY187101A (en) 2012-06-15 2021-08-31 Commw Scient Ind Res Org Production of long chain polyunsaturated fatty acids in plant cells
US10123986B2 (en) 2012-12-24 2018-11-13 Qualitas Health, Ltd. Eicosapentaenoic acid (EPA) formulations
PT2934505T (en) * 2012-12-24 2021-07-02 Qualitas Health Inc Eicosapentaenoic acid (epa) formulations
US9629820B2 (en) 2012-12-24 2017-04-25 Qualitas Health, Ltd. Eicosapentaenoic acid (EPA) formulations
CN105189740B (en) 2013-03-13 2019-01-15 帝斯曼营养品股份公司 Engineered microorganisms
AU2014203179C1 (en) 2013-06-14 2017-05-04 Aker Biomarine Antarctic As Lipid extraction processes
EP2826384A1 (en) 2013-07-16 2015-01-21 Evonik Industries AG Method for drying biomass
CN105813627A (en) 2013-12-13 2016-07-27 雷斯托尔西有限公司 Exfoliative hair retention-promoting formulation
US11718577B2 (en) 2013-12-18 2023-08-08 Commonwealth Scientific And Industrial Research Organisation Lipid compositions comprising triacylglycerol with long-chain polyunsaturated fatty acids
UA122768C2 (en) 2013-12-18 2021-01-06 Коммонвелз Сайнтіфік Енд Індастріал Рисерч Организейшн Lipid comprising long chain polyunsaturated fatty acids
GB201400431D0 (en) 2014-01-10 2014-02-26 Aker Biomarine As Phospholipid compositions and their preparation
SG11201609241QA (en) 2014-05-16 2016-12-29 Restorsea Llc Biphasic cosmetic
AU2015281791A1 (en) 2014-06-27 2017-01-12 Commonwealth Scientific And Industrial Research Organisation Lipid comprising docosapentaenoic acid
EA037184B1 (en) * 2014-06-27 2021-02-16 Коммонвелт Сайнтифик Энд Индастриэл Рисерч Организэйшн Lipid comprising docosapentaenoic acid
US10619175B2 (en) 2014-10-02 2020-04-14 Evonik Operations Gmbh Process for producing a PUFA-containing feedstuff by extruding a PUFA-containing biomass
EP3200603A1 (en) 2014-10-02 2017-08-09 Evonik Degussa GmbH Feedstuff of high abrasion resistance and good stability in water, containing pufas
CA2958457C (en) 2014-10-02 2022-10-25 Evonik Industries Ag Process for producing a pufa-containing biomass which has high cell stability
EP3200604B1 (en) 2014-10-02 2021-11-03 Evonik Operations GmbH Method for preparing an animal feed
EP3229604A1 (en) * 2014-12-12 2017-10-18 DSM IP Assets B.V. Feed supplement material for use in aquaculture feed
NZ735362A (en) 2015-02-11 2019-01-25 Aker Biomarine Antarctic As Lipid compositions
EP3256003B1 (en) 2015-02-11 2022-11-09 Aker Biomarine Antarctic AS Lipid extraction processes
AR104042A1 (en) 2015-03-26 2017-06-21 Mara Renewables Corp HIGH-DENSITY PRODUCTION OF BIOMASS AND OIL USING GLUCEROL IN GROSS
CN104914207B (en) * 2015-06-29 2017-03-15 通威股份有限公司 The assay method of DHA content in a kind of schizochytrium limacinum algae powder
MX2018000502A (en) 2015-07-13 2018-09-07 Mara Renewables Corp Enhancing microalgal metabolism of xylose.
US20210289817A1 (en) * 2016-06-01 2021-09-23 Cargill, Incorporated Fish feed prepared from oilseed plants producing omega-3 fatty acids
US10851395B2 (en) 2016-06-10 2020-12-01 MARA Renewables Corporation Method of making lipids with improved cold flow properties
CH713170B1 (en) 2017-05-22 2018-05-31 La Prairie Group Ag Cosmetic or dermatological preparation containing an aqueous and a lipophilic fish extract.
CH713169B1 (en) * 2017-05-22 2018-05-31 La Prairie Group Ag Cosmetic or dermatological preparation containing a fish extract.
CN108813634A (en) * 2018-06-01 2018-11-16 中国科学院青岛生物能源与过程研究所 A kind of fast food type yolk oligopeptides-phosphatide type DHA economic benefits and social benefits dietary supplements and preparation method thereof
CN117229848A (en) * 2023-07-20 2023-12-15 青岛和合汇途工程技术有限公司 Wet fractionation method for preparing 2-bit DHA algae oil

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2490631A1 (en) * 1980-09-24 1982-03-26 Roussel Uclaf NOVEL LIPID COMPOSITION FOR USE IN DIETETICS, REANIMATION AND THERAPEUTICS
SU1175486A1 (en) * 1983-08-31 1985-08-30 Ордена Трудового Красного Знамени Институт Биохимии Им.А.В.Палладина Method of obtaining a complex of phospholipides
CH663951A5 (en) * 1984-10-10 1988-01-29 Nestle Sa PROCESS FOR THE SELECTIVE ENRICHMENT OF POLYUNSATURATED FATTY ACIDS IN A MIXTURE CONTAINING ENRICHED FRACTION FATTY ACIDS AND COMPOSITIONS CONTAINING THE SAME.
US4870011A (en) * 1985-01-22 1989-09-26 Director General Of Agency Of Industrial Science And Technology Method for obtaining lipids from fungus bodies
GB8507058D0 (en) * 1985-03-19 1985-04-24 Efamol Ltd Pharmaceutical & dietary compositions
JPS6256497A (en) * 1985-09-05 1987-03-12 Nisshin Oil Mills Ltd:The Production of phospholipid composition containing eicosapentaenoic acid
US4816271A (en) * 1987-01-16 1989-03-28 Adelia Scaffidi Skin lotions and creams
GB8813766D0 (en) * 1988-06-10 1988-07-13 Efamol Holdings Essential fatty acid compositions
JP2909508B2 (en) * 1989-02-14 1999-06-23 マルハ株式会社 Krill phospholipid fractionation method
ZA92452B (en) * 1991-01-24 1992-10-28 Martek Corp Microbial oil mixtures and uses thereof
SE9101642D0 (en) * 1991-05-30 1991-05-30 Kabi Pharmacia Ab phospholipids
PH31293A (en) * 1991-10-10 1998-07-06 Rhone Poulenc Agrochimie Production of y-linolenic acid by a delta6-desaturage.
JPH0765066B2 (en) * 1992-05-28 1995-07-12 工業技術院長 Method for producing eicosapentaenoic acid-containing substance using red alga Fudarac
DE4219360C2 (en) * 1992-06-12 1994-07-28 Milupa Ag Process for the production of lipids with a high proportion of long-chain, highly unsaturated fatty acids
US5583019A (en) * 1995-01-24 1996-12-10 Omegatech Inc. Method for production of arachidonic acid
EP0823475B1 (en) * 1995-04-17 2009-06-17 National Institute of Advanced Industrial Science and Technology Novel microorganisms capable of producing highly unsaturated fatty acids and process for producing highly unsaturated fatty acids by using the microorganisms
JP3985035B2 (en) * 1995-09-14 2007-10-03 独立行政法人産業技術総合研究所 (N-6) Docosapentaenoic Acid-Containing Oil and Fat, Method for Producing the Oil and Use, and Use
JPH09194362A (en) * 1996-01-19 1997-07-29 Bizen Kasei Kk Composition consisting of phospholipid containing docosahexanenoic acid and eicosapentanenoic acid
US5883273A (en) * 1996-01-26 1999-03-16 Abbott Laboratories Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds
US6080787A (en) * 1997-02-21 2000-06-27 Abbott Laboratories Methods for reducing the incidence of necrotizing enterocolitis
US5968809A (en) * 1997-04-11 1999-10-19 Abbot Laboratories Methods and compositions for synthesis of long chain poly-unsaturated fatty acids
US5993221A (en) * 1997-05-01 1999-11-30 Beth Israel Deaconess Medical Center, Inc. Dietary formulation comprising arachidonic acid and methods of use
GB9715203D0 (en) * 1997-07-19 1997-09-24 Piper Edwina M Composition
DE69831674T2 (en) * 1997-08-01 2006-06-22 Martek Biosciences Corp. DHA-CONTAINING NEEDLE COMPOSITIONS AND METHOD FOR THE PRODUCTION THEREOF
PT1250058E (en) * 2000-01-14 2009-04-15 Epax As Marine lipid composition for feeding aquatic organisms
AU783066B2 (en) * 2000-04-12 2005-09-22 Westfalia Separator Ag Method for the fractionation of oil and polar lipid-containing native raw materials
MXPA03010467A (en) * 2001-05-14 2004-12-06 Martek Biosciences Boulder Corp Production and use of a polar lipid-rich fraction containing stearidonic acid and gamma linolenic acid from plant seeds and microbes.
WO2002092540A1 (en) * 2001-05-14 2002-11-21 Martek Biosciences Corporation 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

Similar Documents

Publication Publication Date Title
AU2009200194B2 (en) 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
AU2002309856A1 (en) 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
AU2002318135B2 (en) Production and use of a polar lipid-rich fraction containing stearidonic acid and gamma linolenic acid from plant seeds and microbes
AU2002318135A1 (en) Production and use of a polar lipid-rich fraction containing stearidonic acid and gamma linolenic acid from plant seeds and microbes
JP2004536059A5 (en)
Haq et al. Phospholipids from marine source: Extractions and forthcoming industrial applications
WO2007067207A1 (en) Stabilized form of fish oil
JP2004536801A5 (en)
JP2006507846A (en) Marine phospholipid composition
WO2012139588A2 (en) A process for the isolation of a phospholipid
JP2011530302A (en) Oil containing one or more long-chain polyunsaturated fatty acid phospholipids derived from biomass
AU2019392175B2 (en) Very long chain fatty acid compositions
Showman Utilizing the parts of common food products as functional ingredients Part 1: Separation and concentration of ω-3 PUFA-rich phospholipids by hydration of krill oil Part 2: Functional properties of a concentrated egg yolk protein powder using a one-step organic solvent extraction process
Panpipat et al. Palm Phospholipids
Pokorný et al. Food lipids