WO2010097701A1 - Compositions phospholipidiques à faible viscosité - Google Patents

Compositions phospholipidiques à faible viscosité Download PDF

Info

Publication number
WO2010097701A1
WO2010097701A1 PCT/IB2010/000512 IB2010000512W WO2010097701A1 WO 2010097701 A1 WO2010097701 A1 WO 2010097701A1 IB 2010000512 W IB2010000512 W IB 2010000512W WO 2010097701 A1 WO2010097701 A1 WO 2010097701A1
Authority
WO
WIPO (PCT)
Prior art keywords
krill
oil
phospholipids
coagulum
protein
Prior art date
Application number
PCT/IB2010/000512
Other languages
English (en)
Inventor
Snorre Tilseth
Original Assignee
Aker Biomarine Asa
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 Aker Biomarine Asa filed Critical Aker Biomarine Asa
Publication of WO2010097701A1 publication Critical patent/WO2010097701A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56—Materials from animals other than mammals
    • A61K35/612—Crustaceans, e.g. crabs, lobsters, shrimps, krill or crayfish; Barnacles
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting

Definitions

  • the invention relates to processing crustaceans such as krill to oils comprising phospholipids that are Newtonian fluids and/or and have low viscosity, and in particular to the production of oils containing astaxanthin and high levels of phospholipids that show Newtonian fluidity and have a low viscosity.
  • Krill is a small crustacean which lives in all the major oceans world-wide. For example, it can be found in the Pacific Ocean (Euphausia pacified), in the Northern Atlantic (Meganyctiphanes norvegic ⁇ ) and in the Southern Ocean off the coast of Antarctica (Euphausia superba). Krill is a key species in the ocean as it is the food source for many animals such as fish, birds, sharks and whales. Krill can be found in large quantities in the ocean and the total biomass of Antarctic krill (E. superba) is estimated to be in the range of 300-500 million metric tons. Antarctic krill feeds on phytoplankton during the short Antarctic summer.
  • This autoproteolysis is highly efficient also post mortem, making it a challenge to catch and store the krill in a way that preserves the nutritional quality of the krill. Therefore, in order to prevent the degradation of krill the enzymatic activity is either reduced by storing the krill at low temperatures or the krill is made into a krill meal.
  • krill meal process the krill is cooked so that all the active enzymes are denatured in order to eliminate all enzymatic activity.
  • Krill is rich in phospholipids which act as emulsifiers. Thus it is more difficult to separate water, fat and proteins using mechanical separation methods than it is in a regular fish meal production line.
  • krill becomes solid, gains weight and loose liquid more easily when mixed with hot water. Eventually this may lead to a gradual build up of coagulated krill proteins in the cooker and a non-continuous operation due to severe clogging problems. In order to alleviate this, hot steam must be added directly into the cooker.
  • This operation is energy demanding and may also result in a degradation of unstable bioactive components in the krill such as omega-3 fatty acids, phospholipids and astaxanthin.
  • the presence of these compounds, make krill oil an attractive source as a food supplement, a functional food products and a pharmaceutical for the animal and human applications.
  • Omega-3 fatty acids have recently been shown to have potential effect of preventing cardiovascular disease, cognitive disorders, joint disease and inflammation related diseases such as rheumatoid arthritis. Astaxanthin is a strong antioxidant and may therefore assist in promoting optimal health. Hence, there is a need for a method of processing krill into a krill meal at more gentle conditions which prevents the degradation of these valuable bioactive compounds.
  • the invention relates to processing crustaceans such as krill to oils comprising phospholipids that are Newtonian fluids and/or and have low viscosity, and in particular to the production of oils containing astaxanthin and high levels of phospholipids that show Newtonian fluidity and have a low viscosity.
  • the present invention provides compositions comprising less than about 150, 100, 10, 5, 2 or 1 mg/kg astaxanthin or from about 0.1 to about 1, 2, 5, 10 or 200 mg/kg astaxanthin, preferably endogenous, naturally occurring astaxanthin, from about 20% to about 50%, 15% to 45%, or 25% to 35% phospholipids on a w/w basis, and about 15% to 60%, about 20% to 50%, or about 25% to 40% protein on a w/w basis, wherein said phospholipids comprise omega-3 fatty acid residues.
  • the composition comprises a lipid fraction having an omega-3 fatty acid content of from about 5% to about 30%, from 10% to about 30%, or from about 12% to about 18% on a w/w basis.
  • the phospholipids comprise greater than about 60%, 65%, 80%, 85% or 90% phosphatidylcholine on a w/w basis. In some embodiments, the phospholipids comprise less than about 15%, 10%, 8% or 5% ethanolamine on a w/w basis. In some embodiments, the compositions comprise from about 1% to 10%, preferably 2% to 8%, and most preferably about 2% to 6% alkylacylphosphatidylcholine. In some embodiments, the compositions comprise from about 40% to about 70% triacylglycerol on a w/w basis. In further embodiments, the compositions comprise less than about 1% cholesterol. In some embodiments, the protein comprises from about 8% to about 14% leucine on a w/w basis and from about 5% to 11% isoleucine on a w/w basis.
  • the present invention comprises an aqueous phase and a solid phase, said solid phase comprising from about 20% to about 40% phospholipids on a w/w basis, and about 20% to 50% protein on a w/w basis, wherein said phospholipids comprise from about 10% to about 20% omega-3 fatty acid residues.
  • the present invention provides krill compositions comprising astaxanthin, a protein fraction, and a lipid fraction, wherein said lipid fraction comprises less than about 10%, 5% or 3% phospholipids on a w/w basis.
  • the phospholipids comprise less than about 15%, 10% or 5% phosphatidylcholine on a w/w basis.
  • the present invention provides a krill meal comprising astaxanthin and from about 8 % to about 31 % lipids, preferably from about 8% to about 10 or 18 % lipids, wherein said lipids comprises greater than about 80% neutral lipids on a w/w basis.
  • the krill meal comprises less than about 15%, 10%, 5%, 3% or 1% phospholipids.
  • the phospholipids comprise less than about 15%, 10% or 5% phosphatidylcholine on a w/w basis.
  • the present invention provides methods of preparing a phospholipid composition from biological material or biomass comprising: mixing said biological material or biomass with water at a suitable temperature to form a solid phase and an aqueous phase comprising phospholipids and proteins; separating said solid phase from said aqueous phase; heating said aqueous phase at a temperature sufficient to form a phospholipid-protein precipitate; and separating said phospholipid-protein precipitate from said aqueous phase.
  • the present invention provides a phospholipid- protein precipitate obtained by using the foregoing method.
  • the biological material or biomass is krill.
  • the biological material or biomass is selected from crabs, shrimp, calanus, plankton, crayfish, eggs or other phospholipid containing biological materials or biomass.
  • the methods further comprise the step of forming a meal from said solid phase.
  • the step of forming a meal comprises: heating the solid phase in the presence of water; separating fat and protein in said solid phase; and drying said protein to form a meal.
  • the processes further comprise the steps of pressing and drying the coagulum to form a coagulum meal.
  • the drying is by hot air or steam.
  • the present invention provides a phospholipid-protein precipitate obtained by using the foregoing method.
  • the present invention provides a composition comprising a krill solid phase according to the foregoing methods.
  • the present invention provides a krill meal obtained by the foregoing methods.
  • the present invention provides processes comprising: extracting a first lipid fraction from a krill biomass; extracting a second lipid fraction from a krill biomass; and blending said first lipid fraction and said second lipid fraction to provide a krill lipid composition having a desired composition.
  • the one or more of the extracting steps are performed in the absence of substantial amounts of organic solvents.
  • the first lipid fraction is extracted by: mixing krill with water at a suitable temperature to form a solid phase and an aqueous phase comprising phospholipids and protein; separating said solid phase from said aqueous phase; heating said aqueous phase at a temperature sufficient to form a phospholipid-protein precipitate; separating said phospholipid-protein precipitate from said aqueous phase; and separating said phospholipids from said protein.
  • the second lipid fraction is extracted by: heating the solid phase in the presence of water; and separating fat and protein in said solid phase.
  • the first lipid fraction comprises a phospholipid fraction comprising greater than about 90% phosphatidylcholine on a w/w basis.
  • the second lipid fraction comprises greater than about 80% neutral lipids on a w/w basis.
  • the present invention provides processes of producing a phospholipid composition from biological material or biomass comprising: mixing said biological material or biomass with water to increase the temperature of said biological material to about 25 to 80 0 C , preferably to about 50 to 75 0 C, and most preferably to about 60 to 75 0 C to form a first solid phase and a first aqueous phase comprising phospholipids and proteins; separating said first solid phase from said first aqueous phase; and separating a protein and phospholipid fraction from said first aqueous phase.
  • the biomass is heated to the first temperature for at least 3 minutes, preferably from about 3 minutes to 60 minutes, more preferably from about 3 minutes to 20 minutes, and most preferably from about 3 minutes to 10 minutes.
  • the biological material is a marine biomass.
  • the biological material or biomass comprises krill crabs, shrimp, calanus, plankton, crayfish, eggs or other phospholipid containing biological materials or biomass.
  • the present invention is not limited to the use of any particular type of krill.
  • the krill is fresh, while in other embodiments, the krill is frozen.
  • the krill is of the species Euphausia superba.
  • the step of separating a protein and phospholipid fraction from said first aqueous phase comprises heating said first aqueous phase at a temperature sufficient to form a phospholipid-protein coagulate and separating said phospholipid-protein coagulate from said aqueous phase.
  • the processes utilize a second heating step.
  • the first aqueous phase is heated to over 80 0 C, preferably to about 80 to 120 0 C, and most preferably to about 90 to 100 0 C.
  • the krill milk is held at these temperatures for from about 1 minute to about 60 minutes, preferably about 1 minute to about 10 minutes, and most preferably for about 2 minutes to 8 minutes.
  • the heating is at atmospheric pressure, while in other embodiments, the pressure is greater than atmospheric pressure.
  • the processes further comprise the step of pressing said phospholipid-protein coagulate to form a coagulate liquid phase and a coagulate press cake.
  • the processes further comprise drying said coagulate press cake to form a coagulate meal.
  • the processes further comprise extracting a coagulate oil from said coagulate meal.
  • the processes further comprise the steps of pressing and drying the coagulum to form a coagulum meal. In some embodiments, the drying is by hot air or steam.
  • the step of separating a protein and phospholipid fraction from said first aqueous phase comprises filtration of said aqueous phase to provide a phospholipid- protein retentate comprising proteins and phospholipids.
  • filtration is via membrane filtration.
  • the filtration comprises filtering said aqueous phase through a microfilter with a pore size of from about 50 to 500 nm.
  • the processes further comprise the step of dewatering said phospholipid-protein retentate to form a retentate liquid phase and a retentate concentrate.
  • the processes further comprise the step of removing water from said retentate concentrate so that said retentate concentrate is microbially stable.
  • the processes further comprise the step of extracting a retentate oil from said retentate concentrate. In some embodiments, the processes further comprise the step of heating said first solid phase and then pressing said first solid phase to form a first press cake and a second liquid phase. In some embodiments, the processes further comprise the step of drying said first press cake to provide a first krill meal. In some embodiments, the processes further comprise the steps of heating said second liquid phase and then separating said second liquid phase to provide a first krill oil and stickwater. In some embodiments, the stickwater is evaporated and added to said first press cake, and a meal is formed from said evaporated stickwater and said first press cake to provide a second krill meal.
  • the second liquid phase is heated to over 80 0 C, preferably to about 80 to 120 0 C, and most preferably to about 90 to 100 0 C prior to said separation.
  • the processes further comprise the step of combining the previously described coagulate oil or the retentate oil and the first krill oil to provide a blended oil.
  • the coagulate oil, retentate oil, or oil pressed from the first solid phase are combined with the coagulate meal or retentate.
  • the processes of the present invention comprise the further step of supplementing the meals or oils produced as described above with additional proteins, phospholipids, triglycerides, fatty acids, and/or astaxanthin to produce an oil or meal with a desired defined composition.
  • additional proteins, phospholipids, triglycerides, fatty acids, and/or astaxanthin serve as a starting point for producing compositions that are further supplemented in subsequent process steps to produce a desired composition, such a composition containing elevated levels of proteins, lipids or astaxanthin.
  • the present invention provides the lipid- protein composition produced by the foregoing processes.
  • the present invention provides the coagulate meal produced by the foregoing processes.
  • the present invention provides the coagulate oil produced by the foregoing processes. In some embodiments, the present invention provides the retentate meal produced by the foregoing processes. In some embodiments, the present invention provides the retentate oil produced by the foregoing processes. In some embodiments, the present invention provides the krill meal produced by the foregoing processes. In some embodiments, the present invention provides a krill oil produced by the foregoing processes. In some embodiments, the present invention provides a blended oil produced by the foregoing processes. In some embodiments, the compositions of the present invention are supplemented with additional proteins, phospholipids, triglycerides, fatty acids, and/or astaxanthin to produce an oil or meal with a desired defined composition.
  • compositions described above serve as a starting point for producing compositions that are further supplemented in subsequent process steps to produce a desired composition, such a composition containing elevated levels of proteins, lipids or astaxanthin.
  • the present invention provides processes comprising: heating a krill biomass to about 25 to 80 0 C, preferably to about 50 to 75 0 C, and most preferably to about 60 to 75 0 C; separating said krill biomass into solid and liquid phases; extracting a first lipid fraction from said solid phase; extracting a second lipid fraction from said liquid phases; and blending said first lipid fraction and said second lipid fraction to provide a krill lipid composition having a desired composition.
  • the extracting steps are performed in the absence of substantial amounts of organic solvents.
  • the first lipid fraction comprises a phospholipid fraction comprising greater than about 90% phosphatidylcholine on a w/w basis.
  • the second lipid fraction comprises greater than about 80% neutral lipids on a w/w basis.
  • the present invention provides krill compositions comprising from about 0.01 to about 200 mg/kg astaxanthin, from about 45% to about 65% fat w/w, and about 20% to 50% protein w/w, wherein said fat comprises omega-3 fatty acid residues.
  • the fat has an omega-3 fatty acid content of from about 10% to 30 %, preferably 15% to about 25% on a w/w basis.
  • the fat comprises from about 20% to about 50% phospholipids w/w, wherein said phospholipids comprise greater than about 65% phosphatidylcholine w/w and from about 1% to about 10% alkylacylphosphatidylcholine. In some embodiments, the phospholipids comprise less than about 10% ethanolamine on a w/w basis. In some embodiments, the fat comprises from about 40% to about 70% triacylglycerol w/w. In some embodiments, the compositions further comprise less than about 1% cholesterol. In some embodiments, the protein comprises from about 8% to about 14% leucine on a w/w basis and from about 5% to 11% isoleucine on a w/w basis.
  • the present invention provides krill compositions comprising from about 10% to about 20% protein w/w, about 15% to about 30% fat w/w, and from about 0.01 to about 200 mg/kg astaxanthin.
  • the fat has an omega-3 fatty acid content of from about 10% to about 30% on a w/w basis.
  • the fat comprises from about 30% to about 50% phospholipids w/w.
  • the phospholipids comprise greater than about 65% phosphatidylcholine w/w.
  • the phospholipids comprise less than about 10% ethanolamine on a w/w basis.
  • the fat comprises from about 40% to about 70% triacylglycerol w/w.
  • compositions comprise less than about 1% cholesterol.
  • the protein comprises from about 7% to about 13% leucine on a w/w basis and from about 4% to 10% isoleucine on a w/w basis.
  • the present invention provides krill meal press cakes comprising from about 65% to about 75% protein w/w (dry matter) , from about 10% to about 25% fat w/w (dry matter), and from about 1 to about 200 mg/kg astaxanthin (wet base).
  • the fat comprises greater than about 30% neutral lipids and greater than about 30% phospholipids on a w/w basis.
  • the fat comprises from about 50 to about 60% neutral lipids w/w and from about 40% to about 55% polar lipids w/w.
  • the protein comprises from about 5% to about 11% leucine w/w and from about 3% to about 7% isoleucine w/w.
  • the present invention provides krill meals comprising from about 65% to about 75% protein w/w (dry matter) , from about 10% to about 25% fat w/w (dry matter), and from about 1 to about 200 mg/kg astaxanthin (wet base).
  • the fat comprises greater than about 30% neutral lipids and greater than about 30% phospholipids on a w/w basis.
  • the fat comprises from about 50 to about 60% neutral lipids w/w and from about 40% to about 55% polar lipids w/w.
  • the polar lipids comprise greater than about 90% phosphatidyl choline w/w.
  • the polar lipids comprise less than about 10% phosphatidyl ethanolamine w/w.
  • the protein comprises from about 5% to about 11% leucine w/w and from about 3% to about 7% isoleucine w/w.
  • the present invention provides krill oil compositions comprising greater than about 1500 mg/kg total esterified astaxanthin, wherein said esterified astaxanthin comprises from about 25 to 35% astaxanthin monoester on a w/w basis and from about 50 to 70% astaxanthin diester on a w/w basis, and greater than about 20 mg/kg free astaxanthin.
  • the present invention provides krill compositions comprising from about 3% to about 10% protein w/w, about 8% to about 20% dry matter w/w, and about 4% to about 10% fat w/w.
  • the fat comprises from about 50% to about 70% triacylglycerol w/w.
  • the fat comprises from about 30% to about 50% phospholipids w/w.
  • the phospholipids comprise greater than about 90% phosphatidyl choline w/w.
  • the fat comprises from about 10% to about 25% n-3 fatty acids.
  • the fat comprises from about 10% to about 20% EPA and DHA.
  • the krill compositions of the present invention are supplemented with additional proteins, phospholipids, triglycerides, fatty acids, and/or astaxanthin to produce an oil or meal with a desired defined composition.
  • additional proteins phospholipids, triglycerides, fatty acids, and/or astaxanthin
  • the krill compositions described above serve as a starting point for producing compositions that are further supplemented in subsequent process steps to produce a desired composition, such a composition containing elevated levels of proteins, lipids or astaxanthin.
  • the meal and oil compositions of the present invention described above are characterized in containing low levels, or being substantially free of many volatile compounds that are commonly found in products derived from marine biomass.
  • the meals and oils of the present invention are characterized as being substantially free of one or more of the following volatile compounds: acetone, acetic acid, methyl vinyl ketone, 1- penten-3-one, n-heptane, 2-ethyl furan, ethyl propionate, 2-methyl-2-pentenal, pyridine, acetamide, toluene, N,N-dimethyl formamide, ethyl butyrate, butyl acetate, 3 -methyl- 1,4- heptadiene, isovaleric acid, methyl pyrazine, ethyl isovalerate, N,N-dimethyl acetamide, 2- heptanone, 2-ethyl pyridine, butyrolactone, 2,5-dimethyl pyrazine, e
  • the meals and oils of the present invention are characterized in containing less than 1000, 100, 10, 1 or 0.1 ppm (alternatively less than 10 mg/lOOg, preferably less than 1 mg/100 g and most preferably less than 0.1 mg/100 g) of one or more of the following volatile compounds: acetone, acetic acid, methyl vinyl ketone, l-penten-3-one, n-heptane, 2-ethyl furan, ethyl propionate, 2-methyl-2-pentenal, pyridine, acetamide, toluene, N,N-dimethyl formamide, ethyl butyrate, butyl acetate, 3- methyl- 1 ,4-heptadiene, isovaleric acid, methyl pyrazine, ethyl isovalerate, N,N-dimethyl acetamide, 2-heptanone, 2-ethyl pyridine, butyrolactone, 2,5-
  • compositions of the present invention are characterized in comprising less than 10 mg/100g, and preferably less than lmg/100 g (dry weight) of trimethylamine (TMA), trimethylamine oxide (TMAO) and/or lysophosphatidylcholine.
  • TMA trimethylamine
  • TMAO trimethylamine oxide
  • lysophosphatidylcholine lysophosphatidylcholine
  • the present invention provides systems for processing of marine biomass comprising: a mixer for mixing marine biomass and water to form a mixture having a defined temperature, wherein said mixture has a first solid phase and a first liquid phase.
  • the water is heated and said defined temperature of said mixture is from about 25 to 80 0 C, preferably to about 50 to 75 0 C, and most preferably to about 60 to 75 0 C.
  • the systems further comprise a separator in fluid communication with said mixer for separating said first solid phase and said first liquid phase.
  • the first separator is a filter.
  • the systems further comprise a first heater unit in fluid communication with said first separator, wherein said first heater unit heats said first liquid phase to a defined temperature.
  • the defined temperature is about 80 0 C to about 100 0 C, preferably 90 0 C to about 100 0 C, most preferably 95°C to about 100 0 C.
  • the systems further comprise a microfilter in fluid communication with said mixer, wherein said liquid phase is separated into a retentate phase and a permeate phase by said microfilter.
  • the systems further comprise a prefilter in line with said microfilter.
  • the prefilter is a sieve
  • the water is heated and said defined temperature of said mixture is from about 25 to 80 0 C, preferably to about 50 to 75 0 C, and most preferably to about 60 to 75 0 C.
  • the systems further comprise a first separator in fluid communication with said mixer for separating said first solid phase and said first liquid phase.
  • the first separator is a filter.
  • the present invention provides krill compositions comprising from about 10% to about 20% protein w/w, about 15% to about 30% fat w/w, from about 0.01% to about 200 mg/kg astaxanthin, and less than about 1 mg/100g trimethyl amine, trimethyl amine, volatile nitrogen, or lg/100g lysophosphatidylcholine or combinations thereof.
  • the fat has an omega-3 fatty acid content of from about 10% to about 25% on a w/w basis.
  • the fat comprises from about 35% to about 50% phospholipids w/w.
  • the phospholipids comprise greater than about 90% phosphatidylcholine w/w.
  • the phospholipids comprise less than about 10% ethanolamine on a w/w basis.
  • the fat comprises from about 40% to about 60% triacylglycerol w/w.
  • the compositions further comprise less than about 1% cholesterol.
  • the protein comprises from about 7% to about 13% leucine on a w/w basis and from about 4% to 10% isoleucine on a w/w basis.
  • the present invention provides processes for processing of marine biomass comprising: providing a marine biomass and a mixer for mixing marine biomass and water to form a mixture having a defined temperature, wherein said mixture comprises a first solid phase and a first liquid phase.
  • the defined temperature of said mixture is from about 25 to 80 0 C, preferably to about 50 to 75 0 C, and most preferably to about 60 to 75 0 C.
  • the processes further comprise the steps of separating said liquid phase from said solid phase, and heating said liquid phase to about 80 0 C to about 100 0 C, preferably 90 0 C to about 100 0 C, most preferably 95°C to about 100 0 C, to produce a coagulate.
  • the coagulate comprises proteins and lipids.
  • the coagulate is separated from residual liquid by filtering.
  • the present invention provides systems for processing of marine biomass comprising: a ship; a trawl net towable from said ship, said trawl net configured to catch the marine biomass; and a mixer for mixing said marine biomass and water to form a mixture having a defined temperature, wherein said mixture has a first solid phase and a first liquid phase.
  • the marine biomass is krill.
  • the krill is fresh krill and the trawl and ship are configured to deliver the fresh krill to the mixer.
  • system comprises a pump to transfer the biomass from the krill to the ship.
  • the system comprises a microfilter in fluid communication with said mixer, wherein said microfilter separates said first solid phase and said first liquid phase.
  • the marine biomass is krill.
  • the krill is fresh krill.
  • the present invention provides an oil extracted from krill comprising from about 40% to about 60% phospholipids by weight of the oil and about 1 to about 1500 mg/1 astaxanthin, said oil having Newtonian fluidity at 25°C.
  • the oil has a viscosity of about 400 to about 1200 microPascals/sec at 25°C.
  • the oil comprises about 35% to about 55% w/w triglycerides.
  • the oil further comprises about 10% to about 35% w/w omega-3 fatty acid residues.
  • the phospholipids comprise about greater than 90% phosphatidyl choline by weight of the phospholipids.
  • the oil has a viscosity of about 800 to about 1100 microPascals/sec at 25°C.
  • the krill is Euphausia superba.
  • the present invention provides a capsule containing the previous oil compositions.
  • the capsule is a gel capsule.
  • the present invention provides an oral dosage form comprising an oil extracted from krill comprising from about 40% to about 60% phospholipids by weight of said oil and about 1 to about 1500 mg/1 astaxanthin, the oil having a viscosity of about 700 to about 1200 microPascals/sec at 25°C.
  • the oral dosage form is a gel capsule.
  • the oral dosage form is a free flowing oil.
  • the present invention provides an oil extracted from krill comprising from about 40% to about 60% phospholipids by weight of the oil and about 1 to about 1500 mg/1 astaxanthin, said oil having a viscosity of about 400 to about 1200 microPascals/sec at 25°C. In some embodiments, the oil has Newtonian fluidity at 25°C.
  • the present invention provides processes for producing a krill oil having Newtonian fluidity comprising: mixing said krill with water to increase the temperature of the krill to about 25 to 80 0 C to form a first solid phase and a first aqueous phase comprising said phospholipids and proteins; separating said first solid phase from said first aqueous phase; heating said first aqueous phase to produce a phospholipid and protein concentrate; and extracting an oil from the phospholipid and protein concentrate.
  • the oil is extracted with ethanol.
  • the ethanol is removed by evaporation under reduced pressure.
  • the present invention provides krill oils produced by the foregoing processes.
  • the present invention provides a pharmaceutical composition comprising one or more of the compositions described above in combination with a pharmaceutically acceptable carrier.
  • the present invention provides a food product comprising one or of the foregoing compositions.
  • the present invention provides a dietary supplement comprising one or more of the foregoing compositions.
  • the present invention provides an animal feed comprising one or more of the foregoing compositions.
  • Figure 1 shows an overview of the process of making krill meal with a two stage cooking process.
  • Figure 2 is a graph of the Permeate flux as function of dry matter of the retentate (%) (°Brix).
  • Figure 3 is a graph of Average Flux as function of dry matter in retentate.
  • Figure 4 is a GC of the neutral fraction extracted from krill coagulate.
  • Figure 5 is a GC analysis of the neutral fraction extracted from krill coagulate.
  • Figure 6 is a GC of the polar fraction extracted from krill coagulate.
  • Figure 7 is a GC analysis of the polar fraction extracted from krill coagulate.
  • Figures 8a, 8b, and 8c provides graphs depicting Newtonian fluidity at 15°C, 25°C, and 35°C, respectively.
  • phospholipid refers to an organic compound having the following general structure:
  • Rl is a fatty acid residue
  • R2 is a fatty acid residue or -OH
  • R3 is a -H or nitrogen containing compound choline (HOCH 2 CH 2 N + (CH 3 ) 3 ⁇ H ), ethanolamine (HOCH 2 CH 2 NH 2 ), inositol or serine.
  • Rl and R2 cannot simultaneously be OH.
  • R3 is an -OH
  • the compound is a diacylglycerophosphate
  • R3 is a nitrogen-containing compound
  • the compound is a phosphatide such as lecithin, cephalin, phosphatidyl serine or plasmalogen.
  • ether phospholipid refers to a phospholipid having an ether bond at position 1 the glycerol backbone.
  • ether phospholipids include, but are not limited to, alkylacylphosphatidylcholine (AAPC), lyso-alkylacylphosphatidylcholine (LAAPC), and alkylacylphosphatidylethanolamine (AAPE).
  • a "non-ether phospholipid” is a phospholipid that does not have an ether bond at position 1 of the glycerol backbone.
  • omega-3 fatty acid refers to polyunsaturated fatty acids that have the final double bond in the hydrocarbon chain between the third and fourth carbon atoms from the methyl end of the molecule.
  • Non-limiting examples of omega-3 fatty acids include, 5,8,11,14,17-eicosapentaenoic acid (EPA), 4,7,10,13,16,19-docosahexanoic acid (DHA) and 7,10,13,16,19-docosapentanoic acid (DPA).
  • astaxanthin refers to the following chemical structure:
  • astaxanthin esters refer to the fatty acids esterified to OH group in the astaxanthin molecule.
  • w/w refers to the amount of a given substance in a composition on weight basis.
  • a composition comprising 50% w/w phospholipids means that the mass of the phospholipids is 50% of the total mass of the composition (i.e., 50 grams of phospholipids in 100 grams of the composition, such as an oil).
  • fresh krill refers to krill that is has been harvested less than about 12, 6, 4, 2 or preferably 1 hour prior to processing.
  • fresh krill is characterized in that products made from the fresh krill such as coagulum comprise less than 1 mg/lOOg TMA, volatile nitrogen or Trimetylamine oxide-N, alone or in combination, and less than lg/100 g lysophosphatidylcholine.
  • Newtonian fluid refers to a fluid whose stress versus strain rate curve is linear and passes through the origin.
  • the constant of proportionality is known as the "viscosity.”
  • the term “having Newtonian fluidity” is used in reference to a fluid, for example an oil containing phospholipids, that exhibits fluidity properties that are substantially Newtonian fluid-like, i.e., the stress versus strain rate curve is substantially linear and passes approximately through the origin.
  • the invention relates to processing crustaceans such as krill to oils comprising phospholipids that are Newtonian fluids and/or and have low viscosity, and in particular to the production of oils containing astaxanthin and high levels of phospholipids that show Newtonian fluidity and have a low viscosity.
  • the present invention provides systems and methods for the continuous processing of fresh or frozen krill into useful products, including krill oil, krill meal, and a krill protein/phospholipid coagulum.
  • compositions of the present invention are further distinguished from other krill oil supplements marketed for human use in that the described compositions are, in some embodiments, provided as solids or powders comprising a combination of krill lipids, including krill phospholipids and krill triglycerides, and krill- derived protein.
  • These solids/powders may preferably be provided in capsules, gel capsules, or as tablets or caplets.
  • the present invention provides solvent-free methods to produce a phospholipid-containing composition from a biomass such as krill, crabs, Calanus, plankton, eggs, crayfish, shrimp and the like without using organic solvents.
  • a biomass such as krill, crabs, Calanus, plankton, eggs, crayfish, shrimp and the like
  • the biomass preferably krill, freshly harvested or frozen
  • the biomass is heated to a temperature in the range of 25 to 80 0 C, preferably 40 to 75°C, and most preferably 60 to 75°C in order to dissolve/disperse lipids and proteins from the krill into the water phase, which is called krill milk.
  • the biomass is heated to and held at this first temperature for at least 3 minutes, preferably from about 3 minutes to 60 minutes, more preferably from about 3 minutes to 20 minutes, and most preferably from about 3 minutes to 10 minutes.
  • the processes then utilize a second heating step.
  • the proteins and phospholipids are precipitated out of the water phase produced from the first heating step by heating the krill milk (after removal of the krill solids) to a temperature of greater than about 80 0 C, preferably 80 to 120 0 C, most preferably 95 to 100 0 C.
  • the krill milk is held at these temperatures for from about 1 minute to about 60 minutes, preferably about 1 minute to about 10 minutes, and most preferably for about 2 minutes to 8 minutes.
  • the water phase may be heated at atmospheric pressure, or the water phase may be heated in a closed system at an elevated pressure so that the temperature can be increased above 100 0 C. Accordingly, in some embodiments, the heating is at atmospheric pressure, while in other embodiments, the pressure is greater than atmospheric pressure.
  • the precipitate formed (hereafter called a coagulum) can be isolated and characterized.
  • the processes further comprise the steps of pressing and drying the coagulum to form a coagulum meal. In some embodiments, the drying is by hot air or steam.
  • the solid phase (e.g., krill solids) is preferably used to make a krill meal which also has a novel composition.
  • the krill milk is microfiltrated.
  • the solid phase produced by microfiltration (called the retentate) is similar to that of the coagulum. Data show that the coagulum and retentate are low in cholesterol. In some embodiments, the retentate and coagulum are substantially free of cholesterol. In some embodiments, the retentate and coagulum comprise less than 1% cholesterol, preferably less than 0.1% cholesterol. This is a novel method to remove at least a portion of the lipids, such as phospholipids, from the krill.
  • the present invention provides systems and processes for processing a marine biomass.
  • the marine biomass is krill, preferably the Antarctic krill Euphausia superba.
  • Other krill species may also be processed using the systems and processes of the present invention.
  • the krill is processed in a fresh state as defined herein.
  • the krill is processed on board a ship as described below within 12, 10, 8, 6, 4, or preferably 2 hours of catching the krill.
  • the krill is processed on board a ship within 1 or preferably 0.5 hours of catching the krill.
  • the ship tows a trawl that is configured to catch krill.
  • the trawl comprises a pump system to pump the freshly caught krill from the trawl to the ship so that the krill can be processed in a fresh state.
  • the pump system comprises a tube that extends below the water the trawl and a pumping action is provided by injecting air into the tube below the waterline so that the krill is continuously drawn or pumped from the trawl, through the tube and on board the ship.
  • Preferred trawling systems with pumps are described in PCT Applications WO 07/108702 and WO 05/004593, incorporated herein by reference.
  • FIG. 1 As shown in Figure 1, fresh or frozen is krill is mixed in mixer with a sufficient amount of hot water from water heater to increase the temperature of the krill mass to approximately 40 to 75°C, preferably 50 to 75 0 C, more preferably 60 to 75 0 C, and most preferably about 60 to 70 0 C.
  • the water heater is a steam heated kettle, while in other embodiments, the water heater is a scraped surface heat exchanger.
  • the heated mass is then separated into liquid (krill milk) and krill solid fractions in a filter. In some embodiments, the separation is performed by sieving through a metal sieve.
  • the krill milk is heated to approximately 90 0 C to 100 0 C, preferably to about 95°C to 100 0 C in a heater.
  • a heater Any type of suitable water or liquid heater may be used.
  • the heater is a scraped surface heat exchanger. This heating step produced a solid fraction (the coagulum described above) and a liquid fraction.
  • the separator utilizes a filter as previously described. The present invention is not limited to the use of any particular type of filter.
  • the filter is a woven filter.
  • the filter comprises polymeric fibers.
  • the coagulum is introduced into a dewaterer.
  • the dewaterer is a press such as screw press.
  • Pressing produces a liquid fraction and a press cake.
  • the press cake is dried in a drier to produce coagulum meal.
  • the solid krill fraction is introduced into a dewaterer for dewatering.
  • the dewaterer is a press such as screw press. Pressing produces a press cake and a liquid fraction.
  • the press cake is dried in a drier, such as an air drier or steam drier, to provide krill meal.
  • the liquid fraction is centrifuged to produce a neutral krill oil containing high levels of astaxanthin and stickwater.
  • the stick water is added back into the krill press cake to make a full meal, including the various components of the stick water such as soluble proteins, amino acids, etc.
  • the krill milk can be treated by microfiltration instead of by heating to form a coagulum.
  • the krill milk is introduced into a microfilter.
  • Microfiltration produces a fraction called a retentate and a liquid permeate.
  • the retentate is concentrated by evaporation under vacuum to stability, water activity ⁇ 0.5 Aw.
  • Membrane filtration of cooking liquid is preferably performed at about 70 0 C with a filter having a pore size of about
  • the liquid fraction is prefiltered prior to microfiltration.
  • the prefilter is a roto-fluid sieve (air opening 100 ⁇ m).
  • the krill meal process is less susceptible to clogging problems and the use of hot steam in the cooker can be avoided.
  • the data disclosed show the coagulum contains a high percentage of phospholipids, hence the separation of the fat in the new krill meal process can be obtained using mechanical methods as in standard fish meal processes. In fact, the separation of fat from the meal is important.
  • the krill meal should have a low fat value in order to have satisfactory technical properties. Mechanically separating the fat from the meal will result in a neutral oil rich in astaxanthin. If the neutral
  • the present invention provides a krill coagulate and retentate compositions.
  • the compositions are characterized in containing a combination of protein and lipids, especially phospholipids.
  • the compositions are solids or powders (also referred to as a meal).
  • the compositions comprise from about 20% to about 50% protein w/w, preferably about 30% to 40% protein w/w, and about 40% to 70% lipids w/w, preferably about 50% to 65% lipids w/w, so that the total amount of proteins and lipids in the compositions of from 90 to 100%.
  • the lipid fraction contains from about 10 g to 30 g omega-3 fatty acid residues per 100 g of lipid, preferably about 15 g to 25 g omega-3 fatty acids residues per 100 g lipids (i.e., from 10 to 30% or preferably from 15 to 25% omega-3 residues expressed w/w as a percentage of total lipids in the composition).
  • the lipid fraction of the composition comprises from about 25 to 50 g polar lipids per 100 g lipids (25 to 50% w/w expressed as percentage of total lipids), preferably about 30 to 45 g polar lipids per 100 g total lipids (30 to 45% w/w expressed as percentage of total lipids), and about 50 to 70 g nonpolar lipids per 100 g lipids (50 to 70% w/w expressed as percentage of total lipids), so that the total amount of polar and nonpolar lipids is 90 to 100% of the lipid fraction.
  • the phospholipids comprise greater than about 60% phosphatidylcholine on a w/w basis.
  • the phospholipids comprise less than about 10% ethanolamine on a w/w basis. In some embodiments, the compositions comprise from about 20% to about 50% triacylglycerol on a w/w basis. In some embodiments, the compositions comprise less than about 1% cholesterol. In some embodiments, the protein fraction comprises from about 8% to about 14% leucine on a w/w basis and from about 5% to 11% isoleucine on a w/w basis. In some embodiments, the compositions comprise less than about 200, 10, 5 or 1 mg/kg naturally occurring or endogenous astaxanthin. In some embodiments, the compositions comprise from about 0.01 to about 200 mg/kg naturally-occurring astaxanthin.
  • the astaxanthin content of the composition can be increased by adding in astaxanthin from other (exogenous) sources, both natural and non-natural.
  • the compositions can be supplemented with exogenous proteins, triglycerides, phospholipids and fatty acids such as omega-3 fatty acids to produce a desired composition.
  • a pre-heated krill composition is a pre-heated krill composition.
  • Non- limiting examples of the pre-heated krill composition is a krill composition comprising lipids with less than 10% or 5% phospholipids, and in particular phosphatidylcholine.
  • krill meal product produced from the solid phase left after the first heating step (i.e., the heating step at below 80 C).
  • the krill meal has good nutritional and technical qualities such as a high protein content, low fat content and has a high flow number.
  • the ratios of polar lipids to neutral lipids and EPA to DHA is substantially enhanced as compared to normal krill meal.
  • the krill meals comprise from about 60% to about 80% protein on a w/w basis, preferably from about 70% to 80% protein on a w/w basis, from about 5% to about 20% fat on a w/w basis, and from about 1 to about 200 mg/kg astaxanthin, preferably from about 50 to about 200 mg/kg astaxanthin.
  • the fat comprises from about 20 to 40% total neutral lipids and from about 50 to 70% total polar lipids on a w/w basis (total lipids).
  • the ratio of polar to neutral lipids in the meal is from about 1.5: 1 to 3: 1, preferably about 1.8: 1 to 2.5:1, and most preferably from about 1.8: 1 to 2.2: 1.
  • the fat comprises from about 20% to 40% omega-3 fatty acids, preferably about 20% to 30% omega-3 fatty acids.
  • the ratio of EPA:DHA is from about 1.8: 1 to 1 :0.9, preferably from about 1.4: 1 to 1 : 1.
  • the present invention provides oil produced by the processes described above.
  • the oils comprise greater than about 1800 mg/kg total esterified astaxanthin, wherein said esterified astaxanthin comprises from about 25 to 35% astaxanthin monoester on a w/w basis and from about 50 to 70% astaxanthin diester on a w/w basis, and less than about 40 mg/kg free astaxanthin.
  • the present invention provides oils extracted from the coagulum powder (meal) described above.
  • the coagulum powder is extracted with ethanol.
  • the coagulum powder may be extracted with a suitable quantity of 96% ethanol for for about one hour at about 15 to 30 0 C.
  • the mixture of ethanol and coagulum powder is then filtered and the ethanol is removed evaporation, preferably at reduced pressure.
  • the coagulum powder is extracted by super critical fluid extraction.
  • the oils comprise from about 40% to about 60% phospholipids by weight of said oil, about 1 to about 1500 mg/1 astaxanthin, and have a viscosity of about 700 to about 1200 microPascals/sec ( ⁇ P/sec) at 25°C. In some embodiments, the oils have oil have a viscosity of about 800 to about 1100 ⁇ P/sec at 25°C. In some embodiments, the oils comprise about 35% to about 55% w/w triglycerides. In some embodiments, the oils comprise about 10% to about 35% w/w omega-3 fatty acid residues. In some embodiments, the phospholipids comprise about greater than 90% phosphatidyl choline by weight of the phospholipids.
  • the krill is Euphausia superba.
  • the oil is provided in a capsule, preferably a gel capsule.
  • the compositions of the present invention are highly palatable humans and other animals.
  • the oil and meal compositions of the present invention are characterized as containing low levels of undesirable volatile compounds or being substantially free of many volatile compounds that are commonly found in products derived from marine biomass.
  • the meals and oils of the present invention are characterized as being substantially free of one or more of the following volatile compounds: acetone, acetic acid, methyl vinyl ketone, l-penten-3-one, n-heptane, 2-ethyl furan, ethyl propionate, 2-methyl-2- pentenal, pyridine, acetamide, toluene, N,N-dimethyl formamide, ethyl butyrate, butyl acetate, 3 -methyl- 1 ,4-heptadiene, isovaleric acid, methyl pyrazine, ethyl isovalerate, N,N-dimethyl acetamide, 2-heptanone, 2-ethyl pyridine, butyrolactone, 2,5-dimethyl pyrazine, ethyl pyrazine, N,N-dimethyl propanamide, benzaldehyde, 2-octanone, ⁇ -my
  • the meals and oils of the present invention are characterized in containing less than 1000, 100, 10, 1 or 0.1 ppm (alternatively less than 10 mg/100g, preferably less than 1 mg/100 g and most preferably less than 0.1 mg/100 g) of one or more of the following volatile compounds: acetone, acetic acid, methyl vinyl ketone, l-penten-3-one, n-heptane, 2-ethyl furan, ethyl propionate, 2- methyl-2-pentenal, pyridine, acetamide, toluene, N,N-dimethyl formamide, ethyl butyrate, butyl acetate, 3 -methyl- 1 ,4-heptadiene, isovaleric acid, methyl pyrazine, ethyl isovalerate, N,N-dimethyl acetamide, 2-heptanone, 2-ethyl pyridine, butyrolactone, 2,5
  • compositions of the present invention are characterized in comprising less than 10 mg/100g, and preferably less than lmg/100 g (dry weight) of trimethylamine (TMA), trimethylamine oxide (TMAO) and/or lysophosphatidylcholine.
  • TMA trimethylamine
  • TMAO trimethylamine oxide
  • the present invention provides an oral dosage form comprising an oil extracted from krill comprising from about 40% to about 60% phospholipids by weight of said oil and about 1 to about 1500 mg/1 astaxanthin, wherein the oil has Newtonian fluidity and/or a viscosity of about 700 to about 1200 microPascals/sec at 25°C.
  • compositions of this invention are contained in acceptable excipients and/or carriers for oral consumption.
  • the present invention provides a pharmaceutical compositions one or more of the foregoing compositions in combination with a pharmaceutically acceptable carrier.
  • the actual form of the carrier, and thus, the composition itself, is not critical.
  • the carrier may be a liquid, gel, gelcap, capsule, powder, solid tablet (coated caplet or non-coated), tea, or the like.
  • the composition is preferably in the form of a tablet or capsule and most preferably in the form of a soft gel capsule.
  • Suitable excipient and/or carriers include maltodextrin, calcium carbonate, dicalcium phosphate, tricalcium phosphate, microcrystalline cellulose, dextrose, rice flour, magnesium stearate, stearic acid, croscarmellose sodium, sodium starch glycolate, crospovidone, sucrose, vegetable gums, lactose, methylcellulose, povidone, carboxymethylcellulose, corn starch, and the like (including mixtures thereof).
  • Preferred carriers include calcium carbonate, magnesium stearate, maltodextrin, and mixtures thereof.
  • the various ingredients and the excipient and/or carrier are mixed and formed into the desired form using conventional techniques.
  • the tablet or capsule of the present invention may be coated with an enteric coating that dissolves at a pH of about 6.0 to 7.0.
  • a suitable enteric coating that dissolves in the small intestine but not in the stomach is cellulose acetate phthalate. Further details on techniques for formulation for and administration may be found in the latest edition of Remington's Pharmaceutical Sciences (Maack Publishing Co., Easton, PA).
  • the dietary supplement may comprise one or more inert ingredients, especially if it is desirable to limit the number of calories added to the diet by the dietary supplement.
  • the dietary supplement of the present invention may also contain optional ingredients including, for example, herbs, vitamins, minerals, enhancers, colorants, sweeteners, flavorants, inert ingredients, and the like.
  • the dietary supplement of the present invention may contain one or more of the following: ascorbates (ascorbic acid, mineral ascorbate salts, rose hips, acerola, and the like), dehydroepiandosterone (DHEA), Fo- Ti or Ho Shu Wu (herb common to traditional Asian treatments), Cat's Claw ( ancient herbal ingredient), green tea (polyphenols), inositol, kelp, dulse, bioflavinoids, maltodextrin, nettles, niacin, niacinamide, rosemary, selenium, silica (silicon dioxide, silica gel, horsetail, shavegrass, and the like), spirulina, zinc, and the like.
  • Such optional ingredients may be either naturally occurring or concentrated forms.
  • the dietary supplements further comprise vitamins and minerals including, but not limited to, calcium phosphate or acetate, tribasic; potassium phosphate, dibasic; magnesium sulfate or oxide; salt (sodium chloride); potassium chloride or acetate; ascorbic acid; ferric orthophosphate; niacinamide; zinc sulfate or oxide; calcium pantothenate; copper gluconate; riboflavin; beta-carotene; pyridoxine hydrochloride; thiamin mononitrate; folic acid; biotin; chromium chloride or picolonate; potassium iodide; sodium selenate; sodium molybdate; phylloquinone; vitamin D3; cyanocobalamin; sodium selenite; copper sulfate; vitamin A; vitamin C; inositol; potassium iodide.
  • vitamins and minerals including, but not limited to, calcium phosphate or acetate, tribasic; potassium
  • compositions comprise at least one food flavoring such as acetaldehyde (ethanal), acetoin (acetyl methylcarbinol), anethole (parapropenyl anisole), benzaldehyde (benzoic aldehyde), N butyric acid (butanoic acid), d or 1 carvone (carvol), cinnamaldehyde (cinnamic aldehyde), citral (2,6 dimethyloctadien 2,6 al 8, gera nial, neral), decanal (N decylaldehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C 10), ethyl acetate, ethyl butyrate, 3 methyl 3 phenyl glycidic acid ethyl ester (ethyl methyl phenyl glycidate, strawberry aldehyde,
  • compositions comprise at least one synthetic or natural food coloring (e.g., annatto extract, astaxanthin, beet powder, ultramarine blue, canthaxanthin, caramel, carotenal, beta carotene, carmine, toasted cottonseed flour, ferrous gluconate, ferrous lactate, grape color extract, grape skin extract, iron oxide, fruit juice, vegetable juice, dried algae meal, tagetes meal, carrot oil, corn endosperm oil, paprika, paprika oleoresin, riboflavin, saffron, tumeric, tumeric and oleoresin).
  • synthetic or natural food coloring e.g., annatto extract, astaxanthin, beet powder, ultramarine blue, canthaxanthin, caramel, carotenal, beta carotene, carmine, toasted cottonseed flour, ferrous gluconate, ferrous lactate, grape color extract, grape skin extract, iron oxide, fruit juice, vegetable juice, dried algae
  • compositions comprise at least one phytonutrient (e.g., soy isoflavonoids, oligomeric proanthcyanidins, indol 3 carbinol, sulforaphone, fibrous ligands, plant phytosterols, ferulic acid, anthocyanocides, triterpenes, omega 3/6 fatty acids, conjugated fatty acids such as conjugated linoleic acid and conjugated linolenic acid, polyacetylene, quinones, terpenes, cathechins, gallates, and quercitin).
  • phytonutrient e.g., soy isoflavonoids, oligomeric proanthcyanidins, indol 3 carbinol, sulforaphone, fibrous ligands, plant phytosterols, ferulic acid, anthocyanocides, triterpenes, omega 3/6 fatty acids, conjugated fatty acids such as conjugated linoleic acid
  • Sources of plant phytonutrients include, but are not limited to, soy lecithin, soy isoflavones, brown rice germ, royal jelly, bee propolis, acerola berry juice powder, Japanese green tea, grape seed extract, grape skin extract, carrot juice, bilberry, flaxseed meal, bee pollen, ginkgo biloba, primrose (evening primrose oil), red clover, burdock root, dandelion, parsley, rose hips, milk thistle, ginger, Siberian ginseng, rosemary, curcumin, garlic, lycopene, grapefruit seed extract, spinach, and broccoli.
  • the compositions comprise at least one vitamin (e.g., vitamin A, thiamin (Bl), riboflavin (B2), pyridoxine (B6), cyanocobalamin (B 12), biotin, ascorbic acid (vitamin C), retinoic acid (vitamin D), vitamin E, folic acid and other folates, vitamin K, niacin, and pantothenic acid).
  • the particles comprise at least one mineral (e.g., sodium, potassium, magnesium, calcium, phosphorus, chlorine, iron, zinc, manganese, flourine, copper, molybdenum, chromium, selenium, and iodine).
  • a dosage of a plurality of particles includes vitamins or minerals in the range of the recommended daily allowance (RDA) as specified by the United States Department of Agriculture.
  • the particles comprise an amino acid supplement formula in which at least one amino acid is included (e.g., 1-carnitine or tryptophan).
  • the present invention provide animal feeds comprising one or more the compositions described in detail above.
  • the animal feeds preferably form a ration for the desired animal and is balanced to meet the animals nutritional needs.
  • the compositions may be used in the formulation of feed or as feed for animals such as fish, including fish fry, poultry, cattle, pigs, sheep, shrimp and the like.
  • a novel method for preparing krill meal was investigated. 800 g of preheated water (95-100 0 C) and 20Og of frozen krill (0 0 C) were mixed in a cooker (cooker 1) at a temperature of 75 0 C for 6 minutes. Next, the heated krill and the hot water were separated by filtration. The preheated krill was further cooked (cooker 2) by mixing with 300 g hot water (95 0 C) in a kitchen pan and kept at 90 0 C for 2 minutes before separation over a sieve (1,0 ⁇ 1,5 mm opening). The heated krill was separated from the liquid and transferred to a food mixer and cut for 10 seconds.
  • the total volatile nitrogen (TVN), trimethylamine (TMA) and trimethylamine oxide (TMAO) content were determined in the four products from the cooking test in example 2 (Table 2).
  • the krill was fresh when frozen, so no TMA was detected in the products.
  • the results show that TMAO is evenly distributed in the water phase during cooking of krill.
  • Table 2 Distribution of total volatile nitrogen (TVN), trimethylamine (TMA) and trimethylamine oxide (TMAO) in the products from the cooking procedure.
  • TVN total volatile nitrogen
  • TMA trimethylamine
  • TMAO trimethylamine oxide
  • fat, dry matter and astaxanthin were determined in the products (Table 3). It was observed that the major part of the astaxanthin in the krill was found in the press cake (Table 3). Only a minor part is found in the coagulum which contains more than 60 % of the lipid in the krill raw material. The cooking procedure with leaching of a protein-lipid emulsion increases the concentration of astaxanthin in the remaining fat. The results also show that the water free coagulum contains approximately 40% dry matter and 60% fat. The dry matter consist of mostly protein.
  • Astaxanthin esters input 100 % 2 % 81 83 %
  • the coagulum from the cooking experiment in Example 2 were analysed for lipid classes.
  • the coagulum lipid was dominated by triacylglycerol and phosphatidyl choline with a small quantity of phosphatidyl ethanolamine (Table 4).
  • Table 4 Distribution of lipid classes in the coagulum from cooking experiments.
  • the proportion of phosphatidyl choline increased from 33 % in krill to 42 - 46 % in the coagulum.
  • the free fatty acids were almost absent in the coagulum.
  • the amino acid composition of the coagulum is not much different the amino acid composition in krill. There seems to be a slight increase in the apolar amino acids in the coagulum compared to krill (Table 5). For a protein to have good emulsion properties it is the distribution of amino acids within the protein that is of importance more than the amino acid composition. Table 5. Amino acids in coagulum from cooking Example 2.
  • Hydroxiproline protein ⁇ 0,10 ⁇ 0,10 ⁇ 0,10 g/100g
  • the fatty acid profile of the coagulum is presented in Table 6.
  • the content of EPA (20:5) is about 12.4 g/100 g extracted fat and the content of DHA (22:6) is about 5.0 g/100 g extracted fat.
  • Frozen krill were obtained by Aker Biomarine and 10 tons were stored at Norway Pelagic, Bergen, and retrieved as required.
  • the krill was packed in plastic bags in cardboard boxes with 2* 12.5 kg krill.
  • the boxes with krill were placed in a single layer on the floor of the process plant the day before processing. By the time of processing the krill varied from + 3 0 C to -3 0 C. Analytical methods.
  • Protein, KjeldahFs method Nitrogen in the sample is transformed to ammonium by dissolution in concentrated sulfuric acid with cupper as catalyst. The ammonia is liberated in a basic distillation and determined by titration, (ISO 5983:1997(E), Method A 01). Uncertainty: 1 %. Protein, Combustion: Liberation of nitrogen by burning the sample at high temperature in pure oxygen. Detection by thermal conductivity. Percent protein in the sample is calculated by a multiplication of analysed percent nitrogen and a given protein factor, (AOAC Official Method 990.03, 16th ed. 1996, Method A 25).
  • Ash Combustion of organic matter at 550 0 C. The residue remaining after combustion is defined as the ash content of the sample. (ISO 5984:2002. Method A 02). Uncertainty: 3 %. Fat, Ethyl acetate extraction: Absorption of moisture in wet sample by sodium sulphate, followed by extraction of fat by ethyl acetate (NS 9402, 1994 (modified calculation). Method A 29).
  • Fat, Soxhlet Extraction of fat by petroleum ether. Mainly the content of triglycerides is determined, (AOCS Official Method Ba 3-38 Reapproved 1993. Method A 03).
  • Fat, Bligh and Dyer Extraction of fat by a mixture of chloroform, methanol, and water in the proportion 1:2:0.8 which build a single phase system. Addition of chloroform and water gives a chloroform phase with the lipids and a water/methanol phase. The lipids are determined in an aliquot of the chloroform phase after evaporation and weighing. The extraction includes both triglycerides and phospholipids. (E.G. Bligh & WJ. Dyer: A rapid method of total lipid extraction and purification. Can.J.Biochem.Physiol. VoI 37 (1959). Metode A 56). Astaxanthin: Extraction with ethanol and di-chloromethane.
  • Moisture in oil Determination of actual water content of fats and oils by titration with Karl Fischer reagent, which reacts quantitatively with water, (AOCS Official Method CA 2e-84. Reapproved 1993. Method A 13).
  • TVB-N, TMA- N and TMAO-N were determined in a 6% trichloro-acetic acid extract by micro diffusion and titration.
  • Fatty acids were determined by esterifying the fatty acids to methyl esters, separate the esters by GLC, and quantify by use of C23:0 fatty acid methyl ester as internal standard.( AOCS Official Method Ce lb-89, Method A 68). Lipids were separated by HPLC and detected with a Charged Aerosol Detector. Vitamins A, D and E were analysed at AnalyCen, Kambo.
  • Raw material of krill Table 7 gives the results of analysis of the raw material of the krill that was used in the pilot trials. Besides the first trial, the same shipment of krill was used for all trials. The dry matter was about 21-22 %, fat 6 %, protein 13-14 %, salt 1 % pH, total volatile nitrogen (TVN) 18 mgN/lOOg, trimethylamine (TMA) 4 mg N/100g and trimethylamineoxide (TMAO) 135 mg N/100g. Compared to fish pH, TMAO and salt (Cl -) is high for krill. Table 7. Analysis of raw krill on wet base (wb)
  • Table 8 gives the analysis of raw krill on dry base. If these figures are multiplied with 0.93 it will give the figures on meal base with 7 % water.
  • Tables 9 and 10 provide an analysis of cooked krill after first cooking step on wet base and dry base.
  • Membrane filtration Another way to collect the lipids from the krill milk is to separate by membrane filtration. For this to be possible the milk must not coagulate, but be brought to the membrane filter from the sieve (heating step no. 1).
  • the milk is pre-filtrated, which was done by the sieve (100 ⁇ m).
  • the opening of the micro-filter was 100 nm.
  • 80 kg krill was processed by starting by 80 kg water (95 0 C) and 20 kg krill into the kettle as described. For the first 2 batches of krill clean water was used (160 kg), but for the last 2 batches permeate from the membrane filter was used instead of water.
  • the membrane filtration was followed with a refract meter calibrated for sugar solution (°Brix). The Brix-value is near the dry matter concentration in the process liquids.
  • the flux value for the filter at about 60 0 C was 350 l/m2/h for retentate with 7.8 °Brix (refract meter) and reduced to 290 l/m2/h when the Brix value increased to 9.9 °.
  • the Brix value for the permeate was only 1 ° due to high dilution when the amount to be filtered is small. See Figures 2 and 3.
  • the permeate was golden and transparent.
  • Press cake and press liquid Tables 16 and 17 provide an analysis of press cake on wet and dry base from the different trials.
  • the average amount of press cake per kg raw krill was found to be 0.23 kg.
  • the dry matter of the press cake was between 44 and 48 %.
  • the fat content in dry matter was reduced from 21 % before to 15-20 % after pressing. This will give a press cake meal from 14 to 18.5 % fat, about 67 % protein and 7 % moisture.
  • TMAO was reduced from about 500 mg N/100g dry matter in cooked krill to 95mg N/100g dry matter in the press cake.
  • Oil was produced from the krill solids by centrifugation. Table 18. The oil was almost free for water and the content of astaxanthin was quite high (1.8 g/kg).
  • the yield of coagulum press cake was about 5 % of raw krill.
  • the compositions of coagulum and retentate from micro filtration is compared in Table 20. There was hardly any difference between the products from the two process alternatives.
  • Press cake of coagulum was dried, and Table 21 gives the analysis of the coagulum and final coagulum meal.
  • the proximate composition based on dry matter did not change during drying, and the amino acid composition and fatty acid composition is near identical. There was some loss of phospholipids during drying. This is most probable caused by oxidation of fatty acids, but other chemical modification of the phospholipids may also be of consequence.
  • Table 21 Analysis of Coagulum press cake and meal dried in a Rotadisc dryer on wet and dry base Krill meal. Final krill meal was produced. Press cake and press cake with stick water concentrate were dried in a hot air dryer or steam drier. Table 22. Table 22 Analysis of krill meal from
  • Coagulum meal produced as described in Example 4 was extracted using lab scale SFE. 4,885g of coagulum (freeze dried over night) via a two step extraction: 1) SFE: CO 2 , 500 Bar, 6O 0 C, 70min at a medium flow rate of l,8ml/min of CO 2 ; 2) SFE: CO 2 +15%EtOH, 500 Bar, 6O 0 C, 70min at a medium flow rate of 2,5ml/min of CO 2 +EtOH.
  • the first step extracted l,576g of extracted neutral fraction (NF). As shown in Figures 4 and 5, the analysis at HPLC show lower than the detectable limit content on PL in the NF. It was extracted about 32.25% of the total material. Table 29 provides the peak areas of the components of the neutral fraction as determined by GC.
  • the second step extracted a polar fraction of l,023g corresponding to 20,95% of the total material.
  • the polar fraction consisted mostly of PL and just less than 1% TG. See Figures 6 and 7.
  • Table 30 provides the peak areas of the components of the polar fraction as determined by GC.
  • the coagulate was dried over night with a weight loss of about 5,53% w/w.
  • the total extracted was about 53,2% of the starting weight of the dried material.
  • Freshly harvested krill were processed into coagulum on board the ship either 10 minutes or six hours post harvest.
  • the coagulum produced from both the 10 minute post harvest krill and the 6 hour post harvest krill contained less than lmg/lOOg volatile nitrogen, less than 1 mg/100 g trimethylamine (TMA), and less than lg/100g lysophosphatidylcholine. This can be compared to the coagulum produced from frozen krill in Example 4 above, which contained higher levels of volatile nitrogen, and lysophosphatidylcholine.
  • the methods of the invention which utilize freshly harvested krill provide krill products that are characterized in being essentially free of TMA, volatile nitrogen, and lysophosphatidylcholine.
  • Coagulum meal, 250 g, and krill oil were mixed in a kitchen mixer.
  • the aim was to add 300 - 500 mg astaxanthin/kg coagulum meal. If the oil contains 1500 mg astaxanthin/kg krill oil, at least 200 g oil should be added to one kg of coagulum meal.
  • the flow of the meal was markedly reduced by addition of 10 % oil, and the oil came off on the packaging when the addition of oil was increased to 14 and 20 %.
  • 3.5 kg coagulum from was thawed and milled on a Retsch ZMl with a 2 mm sieve. The quantity of milled powder was 2.96 kg.
  • the 2.96 kg dried coagulum was added 300 g krill oil in three portions.
  • the knives in the mixer were to far from the bottom to give a good mixing, so the mixture was mixed by hand and mixer intermittently.
  • the astaxanthin content in the final mixture was 40 % lower than calculated.
  • New analyses of astaxanthin were performed on the oil and on the fortified meal.
  • the krill oil had been stored in a cold room at 3 0 C for 4 months, and the astaxanthin content in the oil did not change during this storage .
  • a new sample were drawn from the fortified meal after 4 weeks frozen storage, and the astaxanthin content was the same in both samples (Table 31).
  • Table 31 Composition of steam dried coagulum fortified with 10 % krill oil.
  • Astaxanthin Esters mg/kg lipid 328 556
  • the astaxanthin content in fortified coagulum meal is 58 % of the amount in the ingredients. This reduction in astaxanthin takes place during mixing of dried coagulum and krill oil, and indicate that dried coagulum is easily oxidized.
  • the dried coagulum meal was extracted by supercritical fluid extraction.
  • the extracted oil was analyzed as presented in Tables 32-34.
  • Coagulum meal prepared as described above was administered to two human subjects and absorption of the product was determined by measuring omega-3 fatty acids in total lipids and in phospholipids in plasma.
  • Subject 1 consumed 8g of coagulum in combination with yoghurt, whereas subject 2 consumed 8g of krill oil without yoghurt.
  • the data is presented in Tables 35 (Subject 1) and 36 (Subject 2).
  • This example provides an analysis of the volatile compounds in oil extracted from krill meal and oil extracted from coagulum meal.
  • Table 38 oil was extracted by SFE from regular krill meal or meal prepared from coagulum as described above.
  • the oil prepared from coagulum meal had substantially reduced amounts of volatile compounds as compared to the oil prepared from regular krill meal.
  • l-penten-3-one was detected in oil prepared from regular krill meal and was absent in oil prepared from coagulum meal.
  • 1- pentene-3-one have previously been identified has a key marker of fishy and metallic off- flavor in fish oil and fish oil enriched food products (Jacobsen et al, J. Agric Food Chem, 2004, 52, 1635-1641).
  • Dried coagulum meal or powder produced as described above was extracted with ethanol. Samples were heated to 15°C, 25°C, and 35°C in a Grafnt waterbath. The viscosity was determined in a rotational viscosimeter (Rheomat 30, Contraves AG, Zurich). The viscosity in the sample is measured with cup C. The measuring cup with sample and spindle is placed in a water bath and when the temperature of the sample has reached the required temperature the measurement is started. The rotational velocity of the spindle increases from 0 to 340 min 1 during 1 minute, and then the speed decreases to 0 min 1 during 1 minute. For calculating viscosity the output signal from the sample is compared to the signal from the viscosity standard.
  • the shear rates at 340 min “1 are for cup A: 647 s “1 , cup B: 133 s “1 , cup C: 74 s “1 , and cup D: 36 s “1 .
  • a series of measurements starts with a viscosity standard.
  • the C cup and 5000 mPa-s standard were used (Brookfield viscosity standards). When the curve is linear, as for this sample, the viscosity is independent of the shear rate, it has a Newtonian flow. The results are shown in Figures 8 a, b, and c.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Animal Behavior & Ethology (AREA)
  • Zoology (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Insects & Arthropods (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Mycology (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Meat, Egg Or Seafood Products (AREA)

Abstract

La présente invention concerne le traitement de crustacés, notamment du krill, pour obtenir des huiles qui contiennent des phospholipides et sont des fluides newtoniens et/ou possèdent une faible viscosité ; l'invention porte en particulier sur la production d'huiles contenant de l'astaxanthine et des phospholipides et qui montrent une fluidité newtonienne et possèdent une faible viscosité.
PCT/IB2010/000512 2009-02-26 2010-02-25 Compositions phospholipidiques à faible viscosité WO2010097701A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15576709P 2009-02-26 2009-02-26
US61/155,767 2009-02-26

Publications (1)

Publication Number Publication Date
WO2010097701A1 true WO2010097701A1 (fr) 2010-09-02

Family

ID=42244612

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/000512 WO2010097701A1 (fr) 2009-02-26 2010-02-25 Compositions phospholipidiques à faible viscosité

Country Status (1)

Country Link
WO (1) WO2010097701A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102749240A (zh) * 2012-07-18 2012-10-24 山东师范大学 一种从南极磷虾中提取虾青素的方法及检测方法
WO2011124895A3 (fr) * 2010-04-09 2012-11-22 Ayanda Group As Compositions pharmaceutiques et nutraceutiques contenant des phospholipides
US8609157B2 (en) 2009-10-30 2013-12-17 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
CN103501623A (zh) * 2011-02-11 2014-01-08 大德Frd有限公司 用于生产磷虾油的方法以及由所述方法生产的磷虾油
WO2015121378A1 (fr) * 2014-02-12 2015-08-20 Aker Biomarine Antarctic As Compositions contenant des phospholipides liquides pour la préparation de produits pharmaceutiques
WO2015121381A1 (fr) * 2014-02-12 2015-08-20 Aker Biomarine Antarctic As Gelules contenant des doses elevees de phospholipides e krill
WO2016128838A2 (fr) 2015-02-11 2016-08-18 Aker Biomarine Antarctic As Compositions lipidiques
WO2016128830A1 (fr) 2015-02-11 2016-08-18 Aker Biomarine Antarctic As Procédés d'extraction de lipides
WO2016190748A1 (fr) * 2015-05-27 2016-12-01 Rimfrost As Composition d'huile de krill fluide concentrée en phospholipides
US9644169B2 (en) 2007-03-28 2017-05-09 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US9730966B2 (en) 2007-03-28 2017-08-15 Aker Biomarine Antartic As Method of reducing appetite in a human subject comprising administering krill oil composition
EP3218456A1 (fr) * 2014-11-14 2017-09-20 Tharos Ltd. Procédé sans solvant d'obtention d'huiles de krill enrichies en phospholipides et en lipides neutres par fusion et par évaporation
US9867856B2 (en) 2014-01-10 2018-01-16 Aker Biomarine Antarctic As Phospholipid compositions and their preparation
US10080803B2 (en) 2014-04-25 2018-09-25 Aker Biomarine Antartic As Emulsified krill phospholipid compositions
US10704011B2 (en) 2013-06-14 2020-07-07 Aker Biomarine Antarctic As Lipid extraction processes
WO2021156407A1 (fr) * 2020-02-07 2021-08-12 Aker Biomarine Antarctic As Composition dérivée de krill
US11147841B2 (en) 2014-12-19 2021-10-19 Aker Biomarine Antarctic As Enhanced omega-3 formulations
WO2023198752A1 (fr) * 2022-04-12 2023-10-19 Aker Biomarine Antarctic As Farine de krill supplémentée et ses utilisations

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005004593A1 (fr) 2003-07-15 2005-01-20 Aker Seafoods Holding As Dispositif de chalutage
WO2007080515A1 (fr) * 2006-01-13 2007-07-19 Aker Biomarine Asa Extrait de krill prevenant la thrombose
WO2007108702A1 (fr) 2006-03-23 2007-09-27 Aker Seafoods Holding As Appareil pour chalut
WO2008117062A1 (fr) * 2007-03-28 2008-10-02 Aker Biomarine Asa Compositions d'huile de krill biologiquement efficaces
WO2009027692A2 (fr) * 2007-08-29 2009-03-05 Aker Biomarine Asa Procédé inédit de fabrication de farine de krill

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005004593A1 (fr) 2003-07-15 2005-01-20 Aker Seafoods Holding As Dispositif de chalutage
WO2007080515A1 (fr) * 2006-01-13 2007-07-19 Aker Biomarine Asa Extrait de krill prevenant la thrombose
WO2007108702A1 (fr) 2006-03-23 2007-09-27 Aker Seafoods Holding As Appareil pour chalut
WO2008117062A1 (fr) * 2007-03-28 2008-10-02 Aker Biomarine Asa Compositions d'huile de krill biologiquement efficaces
WO2009027692A2 (fr) * 2007-08-29 2009-03-05 Aker Biomarine Asa Procédé inédit de fabrication de farine de krill

Non-Patent Citations (18)

* Cited by examiner, † Cited by third party
Title
"AOAC Official Method 990.03", vol. 25, 1996
"Remington's Pharmaceutical Sciences", 1990, MACK PUBLISHING, pages: 1288 - 1300
"Remington's Pharmaceutical Sciences", MAACK PUBLISHING CO.
AOCS OFFICIAL METHOD BA 3-38 REAPPROVED, 1993
AOCS OFFICIAL METHOD CA 2E-84, 1993
COHEN S. A.; MICHAUD D. P.: "Synthesis of a Fluorescent Derivatizing Reagent, 6-Aminoquinolyl-N-Hydroxysuccinimidyl Carbamate, and Its Application for the Analysis of Hydrolysate Amino Acids via High-Performance Liquid Chromatography", ANALYTICAL BIOCHEMISTRY, vol. 211, 1993, pages 279 - 287
CONWAY, E. I.; A. BYRNE: "An absorption apparatus for the micro determination of certain volatile substances", BIOCHEM. J., vol. 27, 1933, pages 419 - 429
E.G. BLIGH; W.J. DYER: "A rapid method of total lipid extraction and purification", CAN.J.BIOCHEM.PHYSIOL., vol. 37, 1959
ELLINGSEN ET AL., BIOCHEM. J., vol. 246, 1987, pages 295 - 305
FURIA; PELLANCA: "Fenaroli's Handbook of Flavor Ingredients", 1971, THE CHEMICAL RUBBER COMPANY
GULYAEV; BUGROVA: "Removing fats from the protein paste "Okean"", KONSERVNAYA I OVOSHCHESUSHIL'NAYA PROMYSHLENNOST, 1976, pages 37 - 8
JACOBSEN ET AL., J. AGRIC FOOD CHEM, vol. 52, 2004, pages 1635 - 1641
LARSEN, T, SSF RAPPORT NR. A-152, 1991
NIKOLAEVA: "Amino acid composition of protein- coagulate in krill", VNIRO, vol. 63, 1967, pages 161 - 4
PHLEGER ET AL., COMP. BIOCHEM. PHYSIOL., vol. 131B, 2002, pages 733
TAKAICHI S ET AL: "Fatty acids of astaxanthin esteres in krill determined by mild mass spectrometry", COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY. PART B, BIOCHEMISTRYAND MOLECULAR BIOLOGY, ELSEVIER,OXFORD, GB LNKD- DOI:10.1016/S1096-4959(03)00209-4, vol. 136, 1 January 2003 (2003-01-01), pages 317 - 322, XP008110880, ISSN: 1096-4959 *
VIRTUE ET AL., MAR. BIOL., vol. 126, pages 521 - 527
YAMAGUCHI K ET AL: "SUPERCRITICAL CARBON DIOXIDE EXTRACTION OF OILS FROM ANTARCTIC KRILL", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US LNKD- DOI:10.1021/JF00071A034, vol. 34, no. 5, 1 January 1986 (1986-01-01), pages 904 - 907, XP001183110, ISSN: 0021-8561 *

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10543237B2 (en) 2007-03-28 2020-01-28 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US11865143B2 (en) 2007-03-28 2024-01-09 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US10010567B2 (en) 2007-03-28 2018-07-03 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US9730966B2 (en) 2007-03-28 2017-08-15 Aker Biomarine Antartic As Method of reducing appetite in a human subject comprising administering krill oil composition
US9644170B2 (en) 2007-03-28 2017-05-09 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US9644169B2 (en) 2007-03-28 2017-05-09 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US9889163B2 (en) 2007-03-28 2018-02-13 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US9816046B2 (en) 2007-03-28 2017-11-14 Aker Biomarine Antarctic As Bioeffective krill oil compositions
US8865236B2 (en) 2009-10-30 2014-10-21 Tharos Ltd. Solvent-Free Process for Obtaining Phospholipids and Neutral Enriched Krill Oils
US9150815B2 (en) 2009-10-30 2015-10-06 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US9011942B2 (en) 2009-10-30 2015-04-21 Tharos, Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US8772516B2 (en) 2009-10-30 2014-07-08 Tharos. Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US8609157B2 (en) 2009-10-30 2013-12-17 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
WO2011124895A3 (fr) * 2010-04-09 2012-11-22 Ayanda Group As Compositions pharmaceutiques et nutraceutiques contenant des phospholipides
CN103501623A (zh) * 2011-02-11 2014-01-08 大德Frd有限公司 用于生产磷虾油的方法以及由所述方法生产的磷虾油
CN102749240A (zh) * 2012-07-18 2012-10-24 山东师范大学 一种从南极磷虾中提取虾青素的方法及检测方法
US10704011B2 (en) 2013-06-14 2020-07-07 Aker Biomarine Antarctic As Lipid extraction processes
US9867856B2 (en) 2014-01-10 2018-01-16 Aker Biomarine Antarctic As Phospholipid compositions and their preparation
WO2015121378A1 (fr) * 2014-02-12 2015-08-20 Aker Biomarine Antarctic As Compositions contenant des phospholipides liquides pour la préparation de produits pharmaceutiques
US10960016B2 (en) 2014-02-12 2021-03-30 Aker Biomarine Antarctic As Capsules containing high doses of krill phospholipids
US10806742B2 (en) 2014-02-12 2020-10-20 Aker Biomarine Antarctic As Liquid phospholipid-containing compositions for the preparation of pharmaceuticals
WO2015121381A1 (fr) * 2014-02-12 2015-08-20 Aker Biomarine Antarctic As Gelules contenant des doses elevees de phospholipides e krill
US10080803B2 (en) 2014-04-25 2018-09-25 Aker Biomarine Antartic As Emulsified krill phospholipid compositions
EP3218456A1 (fr) * 2014-11-14 2017-09-20 Tharos Ltd. Procédé sans solvant d'obtention d'huiles de krill enrichies en phospholipides et en lipides neutres par fusion et par évaporation
US11147841B2 (en) 2014-12-19 2021-10-19 Aker Biomarine Antarctic As Enhanced omega-3 formulations
WO2016128838A2 (fr) 2015-02-11 2016-08-18 Aker Biomarine Antarctic As Compositions lipidiques
US11819509B2 (en) 2015-02-11 2023-11-21 Aker Biomarine Antarctic As Lipid compositions
US10456412B2 (en) 2015-02-11 2019-10-29 Aker Biomarine Antarctic As Lipid extraction processes
RU2718983C2 (ru) * 2015-02-11 2020-04-15 Акер Биомарин Антарктик Ас Композиции липидов
WO2016128830A1 (fr) 2015-02-11 2016-08-18 Aker Biomarine Antarctic As Procédés d'extraction de lipides
AU2016217566B2 (en) * 2015-02-11 2019-02-14 Aker Biomarine Human Ingredients As Lipid compositions
US10864223B2 (en) 2015-02-11 2020-12-15 Aker Biomarine Antarctic As Lipid compositions
AU2019203314B2 (en) * 2015-02-11 2020-12-24 Aker Biomarine Human Ingredients As Lipid compositions
WO2016128838A3 (fr) * 2015-02-11 2016-10-13 Aker Biomarine Antarctic As Compositions lipidiques
US10525087B2 (en) 2015-05-27 2020-01-07 Rimfrost Technologies As Flowable concentrated phospholipid krill oil composition
WO2016190748A1 (fr) * 2015-05-27 2016-12-01 Rimfrost As Composition d'huile de krill fluide concentrée en phospholipides
US10328105B2 (en) 2015-05-27 2019-06-25 Rimfrost Technologies As Flowable concentrated phospholipid krill oil composition
WO2021156407A1 (fr) * 2020-02-07 2021-08-12 Aker Biomarine Antarctic As Composition dérivée de krill
WO2023198752A1 (fr) * 2022-04-12 2023-10-19 Aker Biomarine Antarctic As Farine de krill supplémentée et ses utilisations

Similar Documents

Publication Publication Date Title
AU2008291978B2 (en) A new method for making krill meal
US20100226977A1 (en) Low viscosity phospholipid compositions
WO2010097701A1 (fr) Compositions phospholipidiques à faible viscosité
AU2008231570B2 (en) Bioeffective krill oil compositions
AU2010217296B2 (en) Phospholipid and protein tablets
AU2014256341C1 (en) A new method for making krill meal
AU2012244229B2 (en) A new method for making krill meal
AU2013227998C1 (en) Bioeffective krill oil compositions
AU2013202260A1 (en) A new method for making krill meal
AU2013206138A1 (en) Phospholipid and protein tablets

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10713704

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10713704

Country of ref document: EP

Kind code of ref document: A1