`
`APPLICATION
`NUMBER
`60/975,058
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
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`UNITED STATES DEPARTMENT OF COMMERCE
`United States Patent and Trademark Office
`A,
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`Address: COMMISSIONER FOR PATENTS
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`www.uspto.gov
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`FILING or
`371(c) DATE
`09/25/2007
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`GRP ART
`UNIT
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`FIL
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`FEE REC'D
`200
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`ATTY.DOCKET.NO
`NATNUT-30185
`
`ITOT CLAIMSIND CLAIMS
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`CONFIRMATIONNO. 7678
`
`FILING RECEIPT
`
`04009040909)
`
`Date Mailed: 12/14/2007
`
`72960
`Casimir Jones, S.C.
`
`440 Science Drive
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`It will not be examined for patentability and will
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`become abandonednotlater than twelve monthsafter its filing date. Any correspondence concerning the application
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`Applicant(s)
`
`Inge Bruheim, Volda, NORWAY;
`Asgeir Saebo, Eidsnes, NORWAY;
`Snorre Tilseth, Bergen, NORWAY;
`Mikko Griinari, Espoo, FINLAND;
`Powerof Attorney: The patent practitioners associated with Customer Number 72960
`
`If Required, Foreign Filing License Granted: 12/11/2007
`The country code and number of your priority application, to be usedfor filing abroad under the Paris Convention,
`is US 60/975,058
`Projected Publication Date: None, application is not eligible for pre-grant publication
`Non-Publication Request: No
`Early Publication Request: No
`Title
`
`Bioeffective Krill Oil Compositions
`
`PROTECTING YOUR INVENTION OUTSIDE THE UNITED STATES
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`application under the Patent Cooperation Treaty (PCT). An international (PCT) application generally has the same
`effect as a regular national patent application in each PCT-member country. The PCT process simplifies the filing
`of patent applications on the same invention in member countries, but does notresult in a grantof "an international
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`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0001
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`page 0001
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`Security, Department of Commerce (15 CFR parts 730-774); the Office of Foreign AssetsControl, Department of
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`page 3 of 3
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`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0003
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`page 0003
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`Bioeffective krill oil compositions
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`Inventors: Inge Bruheim (Volda, Norway), Asgeir Seebe (Eidsnes, Norway), Snorre Tilseth
`
`(Bergen , Norway) and Mikko Griinari (Espoo, Finland).
`
`FIELD OF THE INVENTION
`
`This invention relates to extracts from Antarctic krill that comprise bioactive fatty acids.
`
`BACKGROUNDOF THE INVENTION
`
`In the Southern Ocean, off the coast of Antarctica, Antarctic krill (Euphausia superba) can be
`
`found in large quantities, ranging from 300-500 million metric tons of biomass. It feeds on
`
`phytoplankton during the short Antarctic summer. During winter, however, its food supply is
`
`limited to ice algae, bacteria, marine detritus as well as depleting body protein for energy [1].
`
`In order to isolate the krill oil from the krill, solvent extraction methods have been used [7-8].
`
`Krill lipids have been extracted by placing the material in a ketone solvent (e.g. acetone) in
`
`order to extract the lipid soluble fraction. This method involves separating the liquid and solid
`
`contents and recovering a lipid rich fraction from the liquid fraction by evaporation. Further
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`processing steps include extracting and recovering by evaporation the remaining soluble lipid
`
`fraction from the solid contents by using a solvent such as ethanol [8]. The compositions
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`produced by these methods are characterized by containing at least 75 ug/g astaxanthin,
`
`preferably 90 ug/g astaxanthin. Another krill lipid extract disclosed contained at least 250
`
`ug/g canastaxanthin [8], preferably 270 ug/g canastaxanthin.
`
`Krill oil compositions have been described as being effective for decreasing cholesterol,
`
`inhibiting platelet adhesion,
`
`inhibiting artery plaque formation, preventing hypertension,
`
`controlling athritis symptoms, preventing skin cancer, enhancing transdermal
`
`transport,
`
`reducing the symptoms of premenstrual symptoms or controlling blood glucose levels in a
`
`patient.
`
`[9] In yet another application, a krill oil composition has been disclosed [4]
`
`comprising a phospholipid and/or a flavanoid. The phospholipid content in the krill lipid
`
`extract could be as high as 60% w/w and the EPA/DHAcontent as high as 35% (w/w).
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`RIMFROST EXHIBIT 1004 page 0004
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`page 0004
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`Furthermore, nutraceuticals, pharmaceuticals and cosmetics comprising the phospholipid
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`extract were disclosed. Previously, it was also shown that supercritical fluid extraction using
`
`neat CO» could be used to prevent the extraction of phospholipids in order to extract the
`
`neutral lipid fraction from krill, which comprised of esterified and free astaxanthin [10].
`
`Supercritical fluid extraction with solvent modifier has previously been used to extract marine
`
`phospholipids
`
`from salmon roe [11], but has not been previously used to extract
`
`phospholipids from krill meal.
`
`The methods described above rely on the processing of frozen krill that are transported from
`
`the Southern Ocean to the processing site. This transportation is both expensive and can
`
`result in degradation of the krill starting material. Data in the literature showing a rapid
`
`decomposition of the oil in krill explains why somekrill oil currently offered as an omega-3
`
`supplement
`
`in the marketplace contains very high amounts of partly decomposed
`
`phosphatidylcholine and also partly decomposed glycerides. Saether et al., Comp. Biochem
`
`Phys. B 83B(1): 51-55 (1986). The products offered also contain high levels of free fatty
`
`acids.
`
`What is needed in the art are methods for processing krill that do not require transport of
`
`frozen krill material over long distances and the products produced by those methods.
`
`SUMMARYOF THE INVENTION
`
`In a first aspect of the invention is a composition characterized by comprising at least 65%
`
`(w/w) phospholipids.
`
`In another aspect of the invention is a composition obtained from aquatic or marine sources,
`
`characterized by comprising 65% (w/w) phospholipids.
`
`In yet another aspect of the invention is a composition obtained from krill, characterized by
`
`comprising at least 65% (w/w) phospholipids.
`
`In another aspect of the invention is a composition obtained from krill, characterized by
`
`comprising at least 65% (w/w) phospholipids and at least 39% omega-3 fatty acids (w/w).
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`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0005
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`page 0005
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`
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`In yet another aspect of the invention is a composition obtained from krill, characterized by
`
`comprising at least 65% (w/w) phospholipids, at least 39% omega-3 fatty acids (w/w) and at
`
`least 580 mg/kg astaxanthin esters.
`
`In another aspect of the invention is a composition obtained from krill, characterized by
`
`comprising at least 39% omega-3 fatty acids (w/w) andat least 580 mg/kg astaxanthin esters.
`
`In yet another aspect of the invention is a composition obtained from krill, characterized by
`
`comprising at least 65% (w/w) phospholipids and at least 5830mg/kg astaxanthin esters.
`
`In yet another aspect is a krill oil effective for reducing insulin resistance, improving blood
`
`lipid profile, reducing inflammation or reducing oxidativestress.
`
`In some embodiments, the present invention provides a composition comprising at least 65%
`
`(w/w) of phospholipids, said phospholipids characterized in containing at least 35% omega-3
`
`fatty acid residues. In some preferred embodiments, the composition is derived from a marine
`
`or aquatic biomass.
`
`In some further preferred embodiments, the composition is derived from
`
`krill.
`
`In some embodiments, the composition comprises less than 2% free fatty acids.
`
`In
`
`some embodiments, composition comprises less than 10% triglycerides.
`
`In some preferred
`
`embodiments, the phospholipids comprise greater than 50% phosphatidylcholine.
`
`In some
`
`embodiments, the composition comprises at least 500 mg/kg astaxanthin esters.
`
`In some
`
`embodiments,
`
`the composition comprises at least 500 mg/kg astaxanthin esters and at least
`
`36% (w/w) omega-3 fatty acids.
`
`In some embodiments, the composition comprises less than
`
`about 0.5g/100g total cholesterol. In some embodiments, the composition comprises less than
`
`about 0.45% arachidonic acid (w/w).
`
`In some embodiments, the present invention provides a krill lipid extract comprising at least
`
`500 mg/kg astaxanthin esters and at
`
`least 36% (w/w) omega-3 fatty acids.
`
`In further
`
`embodiments, the present invention provides a krill
`
`lipid extract comprising at least 100
`
`mg/kg astaxanthin esters, at least 20% (w/w) omega-3 fatty acids, and less than about 0.45%
`
`arachidonic acid (w/w).
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`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0006
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`page 0006
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`In some embodiments, the present invention provides methods comprising administering the
`
`foregoing compositions to a subject in an amount effective for reducing insulin resistance,
`
`reducing inflammation, improving bloodlipid profile and reducing oxidativestress.
`
`In some embodiments, the present invention provides a krill lipid extract comprising greater
`
`than about 80% triglycerides and greater than about 90 mg/kg astaxanthin esters.
`
`In some
`
`embodiments, the krill lipid extract is characterized in containing from about 5% to about
`
`15% omega-3 fatty acid residues.
`
`In some embodiments,
`
`the krill
`
`lipid extract
`
`is
`
`characterized in containing less than about 5% phospholipids.
`
`In some embodiments,, the
`
`krill lipid extract ischaracterized in comprising from about 5% to about 10% cholesterol.
`
`In some embodiments, the present invention provides a krill meal composition comprising
`
`less than about 50g/kg total fat.
`
`In some embodiments, the krill meal composition comprises
`
`from about 5 to about 20 mg/kg astaxanthin esters.
`
`In some embodiments, the krill meal
`
`composition comprises greater than about 65% protein.
`
`In some embodiments, the krill meal
`
`composition of comprises greater than about 70% protein.
`
`In some further embodiments, the
`
`present invention provides an animal feed comprising the krill meal of Claim 21.
`
`In some embodiments, the present invention provides methods of increasing flesh coloration
`
`in an aquatic species comprising feeding said aquatic species a composition comprising the
`
`krill meal described above.
`
`In some embodiments, the present invention provides methods of
`
`increasing growth and overall survival rate of aquatic species by feeding the krill meal
`
`described above.
`
`In some embodiments,
`
`the present
`
`invention provides methods of producing krill oil
`
`comprising: a) providing krill meal; and b) extracting oil from said krill meal. In some
`
`embodiments, the krill meal is produced by heat-treating krill. In some embodiments,the krill
`
`meal
`
`is stored prior to said extraction step.
`
`In some embodiments,
`
`the extracting step
`
`comprises extraction by supercritical fluid extraction. In some embodiments, the supercritical
`
`fluid extraction is a two step process comprising an extraction with carbon dioxide and an
`
`extraction including ethanol as an entrainer.
`
`In some embodiments, the present invention
`
`provides an oil produced by the foregoing method.
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`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0007
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`page 0007
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`In some embodiments, the present invention provides methods of production of krill oil
`
`comprising: a) providing fresh krill; b) treating said fresh krill
`
`to denature lipases and
`
`phospholipases in said fresh krill to provide a denatured krill product; and c)extracting oil
`
`from said denatured krill product.
`
`In some embodiments, the denaturation step comprises
`
`heating of said fresh krill.
`
`In some embodiments, the denaturation step comprises heating
`
`said fresh krill after grinding.
`
`In some embodiments, the methods further comprise storing
`
`said denatured krill product at room temperature or below between the denaturation step and
`
`the extraction step.
`
`In some embodiments, the enzyme denaturation step is achieved by
`
`application of heat.
`
`In some embodiments, the extraction step comprises use of supercritical
`
`carbon dioxide, with or without use of a polar modifier. In some embodiments, the extraction
`
`step comprises use of ethanol.
`
`In some embodiments, the extraction step is comprises ethanol
`
`extraction followed by acetone to precipitation of phospholipids.
`
`In some embodiments, the
`
`denatured krill product is a meal. In some embodiments, the present invention provides an oil
`
`produced by the foregoing method.
`
`In some embodiments,
`
`the present
`
`invention provides a composition comprising an oil
`
`extracted from krill having a phosphatidylcholine content of greater then about 50% (w/w).
`
`In some embodiments, the oil has a phosphatidylcholine content of greater then about 70%
`
`(w/w). In some embodiments, the oil has a phosphatidylcholine content of greater then about
`
`80% (w/w).
`
`In some embodiments, the composition comprises less than 2% free fatty acids.
`
`In some embodiments,
`
`the composition comprises less than 10% triglycerides.
`
`In some
`
`embodiments, the composition comprises at least 500 mg/kg astaxanthin esters.
`
`In some
`
`embodiments, the composition comprises less than about 0.45% arachidonic acid (w/w).
`
`In some embodiments, the present invention provides composition comprising odorless krill
`
`oil.
`
`In some embodiments, the odorless krill oil comprises less than about 10 mg/kg (w/w)
`
`trimethylamine.
`
`In some further embodiments, the present invention provides an odorless
`
`krill 011 produced by the method comprising: extracting a neutral krill oil from a krill oil
`
`containing material by supercritical fluid extraction to provide a deodorized krill material,
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`wherein said neutral krill oil contains odor causing compoundsand extracting a polarkrill oil
`
`from said deodorized krill material by supercritical fluid extraction with a polar entrainer to
`
`provide an essentially odorless krill oil.
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`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0008
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`page 0008
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`
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`In some embodiments, the present invention provides a composition comprising krill oil
`
`containing less than about 70 micrograms/kilogram (w/w) astaxanthin esters.
`
`In some
`
`embodiments,
`
`the compositions comprise less than about 50 micrograms/kilogram (w/w)
`
`astaxanthin esters.
`
`In some embodiments, the compositions comprise less than about 20
`
`micrograms/kilogram (w/w) astaxanthin esters.
`
`In some embodiments,
`
`the compositions
`
`comprise less than about 5 micrograms/kilogram (w/w)astaxanthinesters.
`
`In some embodiments, the present invention provides a krill oil produced by the process
`
`comprising: pumping fresh krill from a trawl onto a ship, heating the krill to provide a krill
`
`material, and extracting oil from the krill material.
`
`In further embodiments,
`
`the present
`
`invention provides a blended krill oil composition
`
`comprising: from about 45% to 55% w/w phospholipids; from about 35% to 45% w/w
`
`triglycerides; and from about 400 to about 1500 ppm astaxanthin.
`
`In some embodiments, the
`
`blended krill oil product comprises a blend of lipid fractions obtained from Euphausia
`
`superba. In some embodiments, the composition comprises from about 25% to 30% omega-3
`
`fatty acids as a percentage of total fatty acids and wherein from about 80% to 90% of said
`
`omega-3 fatty acids are attached to said phospholipids.
`
`In still other embodiments,
`
`the present
`
`invention provides a Euphausia superba krill oil
`
`composition comprising: from about 30% to 60% w/w phospholipids; from about 30% to
`
`50% triglycerides; from about 400 to about 1500 ppm astaxanthin; and from about 20% to
`
`35% omega-3 fatty acids as a percentage of total fatty acids in said composition, wherein
`
`from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.
`
`In still further embodiments, the present invention provides a dietary supplement comprising
`
`encapsulated Euphausia superba krill oil comprising from about 30% to 60% w/w
`
`phospholipids; from about 30% to 50% triglycerides; from about 400 to about 1500 ppm
`
`astaxanthin; and from about 20% to 35% omega-3 fatty acids as a percentage oftotal fatty
`
`acids in said composition, wherein from about 70% to 95% of said omega-3 fatty acids are
`
`attached to said phospholipids.
`
`In some embodiments,
`
`the present
`
`invention provides methods of making a Euphausia
`
`superba krill oil composition comprising: contacting Euphausia superba with a polar solvent
`
`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0009
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`page 0009
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`
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`to provide an polar extract comprising phospholipids; contacting Equphasia superba with a
`
`neutral solvent
`
`to provide a neutral extract comprising triglycerides and astaxanthin;
`
`combining said polar extract and said neutral extract to provide Euphausia superbakrill oil
`
`comprising from about 30% to 60% w/w phospholipids;
`
`from about 30% to 50%
`
`triglycerides; from about 400 to about 1500 ppm astaxanthin; and from about 20% to 35%
`
`omega-3 fatty acids as a percentage of total fatty acids in said composition, wherein from
`
`about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.
`
`In some
`
`embodiments, the methods further comprise the step of encapsulating the Euphausia superba
`
`krill oil.
`
`In some embodiments, the present invention provides a Euphausia superbakrill oil
`
`produced by the methods described above.
`
`In some embodiments,
`
`the present
`
`invention provides methods of producing a dietary
`
`supplement comprising; contacting Euphausia superba with a polar solvent to provide an
`
`polar extract comprising phospholipids; contacting Equphasia superba with a neutral solvent
`
`to provide a neutral extract comprising triglycerides and astaxanthin; combining said polar
`
`extract and said neutral extract to provide Euphausia superba krill oil comprising from about
`
`30% to 60% w/w phospholipids; from about 30% to 50% triglycerides; from about 400 to
`
`about 1500 ppm astaxanthin; and from about 20% to 35% omega-3 fatty acids as a percentage
`
`of total fatty acids in said composition, wherein from about 70% to 95% of said omega-3 fatty
`
`acids are attached to said phospholipids; and encapsulating said Euphausia superbakrill oil.
`
`DEFINITIONS
`
`As used herein, "phospholipid" refers to an organic compound having the following general
`
`structure:
`
`i
`
`O——C—R'
`
`i
`
`—Oo——C—R?
`
`O
`
`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0010
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`page 0010
`
`
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`wherein R1 is a fatty acid residue, R2 is a fatty acid residue or -OH, and R3 is a —H or
`nitrogen
`containing
`compound
`choline
`(HOCH,CH,N’(CH;);30H),
`ethanolamine
`
`(HOCH2CH2NHz), inositol or serine. RI and R2 cannot simultaneously be OH. When R3 is
`
`an —OH,the compoundis a diacylglycerophosphate, while when R3 is a nitrogen-containing
`
`compound, the compound is a phosphatide such as lecithin, cephalin, phosphatidyl serine or
`
`plasmalogen.
`
`Asused herein, the term 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).
`
`Asused herein, astaxanthin refers to the following chemicalstructure:
`
`
`
`Asused herein, astaxanthin esters refer to the fatty acids esterified to OH groupin the
`
`astaxanthin molecule.
`
`DETAILED DESCRIPTION OF THE INVENTION
`
`This invention discloses novel krill oil compositions characterized by containing high levels
`
`of astaxanthin, phospholipids and omega-3 fatty acids. The krill oils compositions are
`
`extracted from krill meal using supercritical fluid extraction (SFE) with a solvent modifier.
`
`The krill meal has been processed on board a ship in Antarctica using live krill as starting
`
`material in order to ensure the highest possible quality of the krill meal. The krill oils are
`
`extracted from the krill meal in two stages, in step 1 the neutral fraction is extracted using
`
`neat supercritical CO2. The neutral fraction consisted mostly of triglycerides and cholesterol.
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`RIMFROST EXHIBIT 1004
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`RIMFROST EXHIBIT 1004 page 0011
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`page 0011
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`
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`In stage 2,
`
`the polar lipids (phospholipids) are extracted by adding 20% ethanol to the
`
`supercritical CO extraction medium. Thepolar krill oil extracted where found to contain 94%
`
`phospholipids (w/w), 46% omega-3 fatty acids (w/w) and 580 mg/kg astaxanthin esters.
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`The present
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`invention provides methods
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`to avoid decomposition of glycerides and
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`phospholipids in krill oil and compositions produced by those methods. The product obtained
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`by these new methodsis virtually free of enzymatically decomposed oil constituents. The
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`solution to the problem is to incorporate a protein denaturation step on fresh krill prior to use
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`of any extraction technology. Denaturation can be achieved by thermal stress or by other
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`means. After denaturation, the oil can be extracted by an optional selection of nonpolar and
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`polar solvents including use of supercritical carbon dioxide. Krill is adapted to a very efficient
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`nutrient digestion at very low temperatures. Therefore the enzymes are sensitive to heat and
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`the step of applying thermal denaturation of lipases and phospholipases does not imply use of
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`very high temperatures. Suprisingly,
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`it has been found that the use of mild denaturation
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`conditions can greatly enhance the quality of krill oil.
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`Additionally, a major obstacle of several processes of extraction is the cost of removing
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`water. This is particularly true for methods feasible for extraction of highly unsaturated lipids
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`where freeze drying has been regarded as the method of choice to avoid oxidative breakdown
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`of lipids. However, the lipids in krill are surprisingly stable against oxidative deterioration.
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`Therefore, a process including moderate use of heat in the water removing process is feasible
`
`provided that the enzymeshave beeninactivated.
`
`A.
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`Krill Processing
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`The present invention provides methods for processing freshly caught krill at the site of
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`capture and preferably on board a ship. After processing on board, the krill can be further
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`subjected to extraction processes on board the ship or at a remote location away from the ship.
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`The processing steps described herein also also allow for the storage of krill material,
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`preferably a krill meal for from about 1,2, 3, 4, 5, 6, 8, 9, 10, 11, or 12 months to about 24 to
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`36 monthsprior to processing.
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`In some preferred embodiments, freshly caught is first subjected to a protein denaturation
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`step. The present invention is not limited to any particular method of protein dentatuation. In
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`some embodiments, the denaturation is accomplished by application of chemicals, heat, or
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`combinations thereof.
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`In some embodiments, freshly caught krill is wet pressed to obtain oil
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`and meal. In some embodiments, the meal is then heated to a temperature of about 50 degrees
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`Celsius to about 100 degrees Celsius for about 20 minutes to about an hour, preferably about
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`40 minutes to coagulate the proteins.
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`In some embodiments, this material is then pressed to
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`yield a press cake. When this method is used on krill, only a small amountofoil is released.
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`Mostof the oil is still present in the denaturated meal.
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`In some embodiments, antioxidants
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`such as ethoxyquin or Vitamin E are added to the meal. However, as shown in the examples,
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`the resulting meal
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`is surprisingly stable. The stability can only partly be explained by
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`addition of an antioxidant to the meal. This antioxidant can after extraction of the oil from
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`denaturated meal be removed by further processing steps. Alternatively the oil can be
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`extracted rather shortly after production of the meal without any addition of antioxidant in the
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`process. Further, storage conditions at a low to very low temperature can be applied if
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`addition of antioxidantis not desired.
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`Krill oil extracted from denaturated krill meal by supercritical fluid extraction even 19 months
`
`after the production of the meal contained virtually no decomposed phospholipids. This
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`product turned out to be substantially different from samples of krill oil available in the
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`market today. Previously described commercial krill processing proceduresutilize krill that
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`has been frozen immediately after catching followed by freeze drying and extraction at low
`
`temperatures. However, these processes only yield a suitable product if the time the krill is
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`kept frozen is very short or the temperature is extremely low (-60-80 C). However, data
`
`provided herein clearly showsthat if a step of denaturation of the proteins is added in front of
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`an optional extraction method, an excellent krill oil can be produced even after a long time of
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`storage. This methodology also opens up for use of alternative methods to remove waterprior
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`to extraction, which in turn has a great impact on costs in full scale operation. If a long time of
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`storage is desired, the denaturated material should preferably be stored at low temperature
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`preferably at -20 C.
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`In some embodiments, krill oil
`
`is extracted from the denatured krill meal.
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`In some
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`embodiments, the krill oil is extracted by contacting the krill meal with ethanol.
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`In some
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`embodiments, krill
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`is then extracted with a ketone solvent such as ethanol.
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`In other
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`embodiments, the krill oil is extracted by one or two step supercritical fluid extraction.
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`In
`
`some embodiments, the supercritical fluid extraction uses carbon dioxide and neutral krill oil
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`is produced. In some embodiments, the supercritical fluid extraction uses carbon dioxide with
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`the addition of a polar entrainer, such as ethanol,
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`to produce a polar krill oil.
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`In some
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`embodiments, the krill mealis first extracted with carbon dioxide followed by carbon dioxide
`
`with a polar entrainer, or vice versa.
`
`The krill oil extracted by the methods of the present invention contains few enzymatic
`
`breakdown products. Examples of the krill oil compositions of the present invention are
`
`provided in Tables 6-17.
`
`In some embodiments, the present invention provides a polar krill
`
`oil comprising at
`
`least 65% (w/w) of phospholipids, wherein the phospholipids are
`
`characterized in containing at least 35% omega-3 fatty acid residues. The present inventionis
`
`not limited to the presence of any particular omega-3 fatty acid residues in the krill oil
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`composition. In some preferred embodiments, the krill oil comprises EPA and DHAresidues.
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`In some embodiments, the krill oil compositions comprise less than about 5%, 4%, 3% or
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`preferably 2% free fatty acids on a weight/weight (w/w) basis.
`
`In some embodiments, the
`
`krill oil compositions comprise less than about 25%, 20%, 15%, 10% or 5% triglycerides
`
`(w/w).
`
`In some embodiments, the krill oil compositions comprise greater than about 30%,
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`40%, 45%, 50%, 55%, 60%, or 65% phosphatidyl choline (w/w).
`
`In some embodiments, the
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`krill oil compositions comprise greater than about 100, 200, 300, 400, or 500 mg/kg
`
`astaxanthin esters and up to about 700 mg/kg astaxanthin esters.
`
`In some embodiments, the
`
`present invention provides krill oil compositions comprising at least 500 mg/kg astaxanthin
`
`esters and at least 36% (w/w) omega-3 fatty acids.
`
`In some embodiments, the krill oil
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`compositions of the present
`
`invention comprise less than about 1.0g/100g, 0.5g/100g,
`
`0.