US20140274922A1 - Algal omega 7 compositions - Google Patents

Algal omega 7 compositions Download PDF

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US20140274922A1
US20140274922A1 US14/025,766 US201314025766A US2014274922A1 US 20140274922 A1 US20140274922 A1 US 20140274922A1 US 201314025766 A US201314025766 A US 201314025766A US 2014274922 A1 US2014274922 A1 US 2014274922A1
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approximately
algal
composition
fatty acid
acid
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US14/025,766
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Leslie van der Meulen
Daniel Fleischer
Michelle L. Collins
James Astwood
Jeffrey Gerard Hippler
Andrew Thompson
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Aurora Algae Inc
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Aurora Algae Inc
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Priority to US14/025,772 priority Critical patent/US9445619B2/en
Priority to US14/025,766 priority patent/US20140274922A1/en
Assigned to AURORA ALGAE, INC. reassignment AURORA ALGAE, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: VAN DER MEULEN, LESLIE, HIPPLER, Jeffrey Gerard, THOMPSON, ANDREW, ASTWOOD, James, COLLINS, Michelle L., FLEISCHER, DANIEL
Publication of US20140274922A1 publication Critical patent/US20140274922A1/en
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    • 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
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    • C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
    • C—CHEMISTRY; METALLURGY
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Definitions

  • This invention relates to algal biochemistry, and more specifically, to algal omega 7 compositions.
  • algal omega 7 compositions including algal fatty acid compositions comprising by dry weight from about approximately 0.5% to about approximately 99% C16:1 n7 palmitoleic acid (POA).
  • algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 10% saturated fatty acids; from about approximately 0% to about approximately 99% arachidonic acid; from about approximately 0% to about 99% docosahexaenoic acid; and/or from about approximately 0% to about approximately 99% eicosapentaenoic acid.
  • algal omega 7 compositions including algal fatty acid compositions comprising by dry weight from about approximately 0.5% to about approximately 99% C16:1 n7 palmitoleic acid (POA).
  • algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 10% saturated fatty acids; from about approximately 0% to about approximately 10% arachidonic acid; substantially no (i.e. less than approximately 0.5%) docosahexaenoic acid; and/or from about approximately 0% to about approximately 10% eicosapentaenoic acid.
  • algal fatty acid compositions may include by dry weight about approximately 90% palmitoleic acid, less than about approximately 10% saturated fatty acids, less than about approximately 10% arachidonic acid, substantially no docosahexaenoic acid, and less than about approximately 10% eicosapentaenoic acid.
  • the algal palmitoleic acid compositions described herein may be desaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from saturated algal compositions comprising by total weight approximately 50% POA, approximately 50% palmitic acid (PA) and substantially no DHA.
  • the saturated algal compositions may result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 23% PA, less than approximately 10% ARA, and substantially no DHA.
  • the saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, less than approximately 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • the saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight from between approximately 0% EPA and 99% EPA, from between approximately 0% POA and 99% POA, less than approximately 20% saturated fats, from between approximately 0% ARA and 99% ARA, and from between approximately 0% DHA and 99% DHA.
  • FIG. 1 shows an actual fatty acid (in ethyl ester form) profile for an exemplary total algal oil composition.
  • FIG. 2 shows a flow chart for an exemplary method of unsaturating an exemplary saturated fatty acyl moieties (FAMs) rich algal composition.
  • FAMs saturated fatty acyl moieties
  • FIG. 3 shows the actual content of 16:0 ethyl ester (palmitic acid) expressed as mg/g ethyl ester in the liquid phase at each of steps 210 - 250 as described in connection with FIG. 2 .
  • FIG. 4 shows an actual fatty acid profile for an exemplary fatty acid composition comprising mostly C16:1 n7 palmitoleic acid that resulted after processing an exemplary total algal oil composition such as that shown in FIG. 1 by the exemplary method shown and described in connection with FIG. 2 .
  • FIG. 5 is a data table for an actual fatty acid profile for an exemplary total algal oil composition (in ethyl ester form), such as shown in FIG. 1 , an exemplary saturated algal composition (in ethyl ester form), and an exemplary fatty acid composition (in ethyl ester form) comprising mostly C16:1 n7 palmitoleic acid, as shown in FIG. 4 .
  • FIG. 6 is an actual saturated fat profile for an exemplary whole biomass (“WB”) (in a form of a fatty acid methyl ester), an exemplary crude biomass (“Crude”) (in a form of a fatty acid methyl ester), an exemplary algal oil composition (“TAO”) (in ethyl ester form), an exemplary 16 chain fatty acid composition (in ethyl ester form), and an exemplary C16:1 n7 palmitoleic acid (in ethyl ester form).
  • WB whole biomass
  • Crude in a form of a fatty acid methyl ester
  • TEO algal oil composition
  • 16 chain fatty acid composition in ethyl ester form
  • C16:1 n7 palmitoleic acid in ethyl ester form
  • a fatty acid is a carboxylic acid with a long aliphatic tail (chain), which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Saturated fatty acids have no double bonds between carbon atoms. Unsaturated fatty acids have one or more double bonds between carbon atoms. When counting from the terminal methyl carbon toward the carbonyl carbon on an unsaturated fatty acid, the first double bond signifies the omega double bond, such as observed in omega 3, omega 6, or omega 7 fatty acids.
  • Palmitoleic acid is an omega-7 monounsaturated fatty acid with a 16-carbon chain with one double bond, denoted as C16:1 n7. A beneficial fatty acid, it has been shown to suppress inflammation. Dietary sources of omega-7 are found in animal and plant sources, including sea buckthorn berries, macadamia nuts, cold water fish and dairy fat. These sources, however, are not concentrated and/or purified sources of POA and often contain a mixed fatty acid profile of saturated and polyunsaturated fats.
  • Palmitic acid is a saturated fatty acid with a 16-carbon chain and no double bonds, denoted as C16:0. Consumption of saturated fats such as palmitic acid is believed to increase the risk of developing diabetes, obesity, stroke and cardiovascular diseases.
  • Alpha linolenic acid is an omega-3 polyunsaturated fatty acid (PUFA) with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, denoted as C18:3 n3.
  • PUFA polyunsaturated fatty acid
  • Arachidonic acid is an omega-6 PUFA with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end.
  • ARA is also denoted as C20:4 n6.
  • Examples of dietary sources of omega-6 PUFAs include refined vegetable oils, such as corn and soy oil, seeds and nuts and the oils extracted from them. Consumption is therefore sufficient in the average diet.
  • Eicosapentaenoic acid is an omega-3 fatty acid PUFA with the connotation C20:5 n3. It is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end.
  • Docosahexaenoic acid is an omega-3 fatty acid PUFA. It is a carboxylic acid with a 22-carbon chain and six cis double bonds; the first double bond is located at the third carbon from the omega end. DHA is also denoted as C22:6 n3.
  • algal omega 7 compositions including algal fatty acid compositions comprising by dry weight from about approximately 0.5% to about approximately 99% C16:1 n7 palmitoleic acid (POA).
  • algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 20% saturated fatty acids; from about approximately 0% to about approximately 99% arachidonic acid; from about approximately 0% to about 99% docosahexaenoic acid; and/or from about approximately 0% to about approximately 99% eicosapentaenoic acid.
  • the various exemplary algal omega 7 compositions provided herein may comprise by dry weight from about approximately 0.5% to about approximately 99% palmitoleic acid.
  • Such algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 20% saturated fatty acids; from about approximately 0% to about approximately 10% arachidonic acid; substantially no (i.e. less than approximately 0.5%) docosahexaenoic acid; and/or from about approximately 0% to about approximately 10% eicosapentaenoic acid.
  • the various exemplary algal omega 7 compositions provided herein may further be in ethyl ester form.
  • ethyl esters are derived by reacting free fatty acids with ethanol. Called esterification, the resulting ethyl ester allows for the fractional distillation (concentration) of the long chain fatty acids at lower temperatures. This step allows for the selective concentration of the fatty acids to levels greater than found in nature.
  • the ethyl ester forms of the various exemplary algal omega 7 compositions provided herein may be converted to a triglyceride form by performing an enzymatic reaction with the ethyl ester form in the presence of glycerol, heating under a vacuum, and filtering out the enzymes.
  • immobilized lipase enzymes may be those isolated from Candida antarctica and/or commercially supplied by Novozyme or Sigma Aldrich.
  • the algal palmitoleic acid compositions described herein may be desaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from saturated algal compositions comprising by total weight approximately 50% POA, approximately 50% palmitic acid (PA) and substantially no DHA.
  • the saturated algal compositions may result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • the saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, less than approximately 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • the saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight from between approximately 0% EPA and 99% EPA, from between approximately 0% POA and 99% POA, less than approximately 10% saturated fats, from between approximately 0% ARA and 99% ARA, and from between approximately 0% DHA and 99% DHA.
  • Algae are mostly aquatic photosynthetic organisms that range from microscopic flagellate to giant kelp. Algae may be loosely grouped into seven categories: Euglenophyta (euglenoids), Chrysophyta (golden-brown algae), Pyrrophyta (fire algae), Dinoflagellata, Chlorophyta (green algae), Rhodophyta (red algae), Paeophyta (brown algae), and Xanthophyta (yellow-green algae).
  • Lipid extracted from any algae genus may be used in the various embodiments of the present invention, including Amphora, Anabaena, Anikstrodesmis, Botryococcus, Chaetoceros, Chlorella, Chlorococcum, Cyclotella, Cylindrotheca, Dunaliella, Emiliania, Euglena, Glossomastix, Haematococcus, Isochrysis, Monochrysis, Monoraphidium, Nannochloris, Nannochloropsis, Navicula, Nephrochloris, Nephroselmis, Nitzschia, Nodularia, Nostoc, Oochromonas, Oocystis, Oscillatoria, Pavlova, Phaeodactylum, Picochloris, Platymonas, Pleurochrysis, Porphyra, Pseudoanabaena, Pyramimonas, Scenedesmus, Stichococcus, Synecho
  • FIG. 1 shows an actual fatty acid (in ethyl ester form) profile for an exemplary total algal oil composition that was produced and analyzed by the present inventors.
  • exemplary total algal oil compositions may comprise by total weight approximately 30% EPA, approximately 27% palmitoleic acid, approximately approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • An exemplary total algal oil composition such as the exemplary total algal oil composition shown in FIG. 1 , may be processed via high vacuum distillation, resulting in an exemplary algal composition comprising saturated fatty acyl moieties (FAMs) including by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
  • FAMs saturated fatty acyl moieties
  • FIG. 2 shows a flow chart for an exemplary method of unsaturating an exemplary saturated fatty acyl moieties (FAMs) rich algal composition.
  • FAMs saturated fatty acyl moieties
  • 100 milliliters (mls) of the exemplary saturated algal composition is chilled at 4° C. for 24 hours, resulting in formation of transparent crystals as stoutly needles.
  • the mixture comprising the transparent crystals is vacuum-filtered through a whatman #1 paper filter, and the cake is blotted with kimwipes to remove interstitial liquid.
  • the filtered liquid phase is brought to ⁇ 3° C. for 24 hours, and a second crop of crystals is formed as described above.
  • the filtered liquid phase is brought to ⁇ 10° C. for 24 hours, and a third crop of crystals is formed, these crystals being smaller and rounder than earlier crops.
  • the filtered liquid phase is then brought to ⁇ 20° C. for 24 hours, and forms a turbid suspension which is filtered.
  • FIG. 3 shows the actual content of 16:0 ethyl ester (palmitic acid) expressed as mg/g (in ethyl ester form) in the liquid phase at each of steps 210 - 250 as described in connection with FIG. 2 .
  • each diamond represents the actual content of 16:0 ethyl ester (palmitic acid) expressed as mg/g (in ethyl ester form) in the liquid phase, beginning with step 210 for the diamond at the left, and progressing to step 250 for the diamond at the right.
  • FIG. 4 shows an actual fatty acid profile for an exemplary fatty acid composition comprising mostly C16:1 n7 palmitoleic acid that resulted after the present inventors processed an exemplary total algal oil composition such as that shown in FIG. 1 by the exemplary method shown and described in connection with FIG. 2 .
  • exemplary algal omega 7 compositions may comprise approximately 90% palmitoleic acid, less than approximately 10% saturated fatty acids, less than approximately 2% arachidonic acid, substantially no docosahexaenoic acid, and less than approximately 10% eicosapentaenoic acid.
  • FIG. 5 is a data table for an actual fatty acid profile determined by the present inventors for an exemplary total algal oil composition (in ethyl ester form), such as shown in FIG. 1 , an exemplary saturated FAM-rich algal composition (in ethyl ester form), and an exemplary fatty acid composition (in ethyl ester form) comprising mostly C16:1 n7 palmitoleic acid, as shown in FIG. 4 .
  • the data table in FIG. 5 shows fatty acid type by milligrams per gram (mg/g) as found in the ethyl ester forms of the various algal compositions.
  • the exemplary fatty acid composition (in ethyl ester form) comprising mostly C16:1 n7 palmitoleic acid, also comprises only 3.46% saturated fatty acids.
  • FIG. 6 is an actual saturated fat profile for an exemplary whole biomass (“WB”) (in a form of a fatty acid methyl ester), an exemplary crude biomass (“Crude”) (in a form of a fatty acid methyl ester), an exemplary total algal oil composition (“TAO”) (in ethyl ester form), an exemplary 16 chain fatty acid composition (in ethyl ester form), and an exemplary C16:1 n7 palmitoleic acid (in ethyl ester form).
  • WB whole biomass
  • Crude in a form of a fatty acid methyl ester
  • TEO total algal oil composition
  • TEO 16 chain fatty acid composition
  • C16:1 n7 palmitoleic acid in ethyl ester form
  • the exemplary algal composition is less saturated than both the exemplary crude and whole algal biomass compositions.

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Abstract

Provided herein are exemplary algal omega 7 compositions, including algal fatty acid compositions comprising by dry weight from about approximately 0.5% to about approximately 99% C16:1 n7 palmitoleic acid (POA). Such algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 20% saturated fatty acids; from about approximately 0% to about approximately 99% arachidonic acid; from about approximately 0% to about 99% docosahexaenoic acid; and/or from about approximately 0% to about approximately 99% eicosapentaenoic acid. Further exemplary algal fatty acid compositions may include by dry weight about approximately 90% POA, less than about approximately 20% saturated fatty acids, less than about approximately 10% ARA, substantially no DHA, and less than about approximately 10% EPA.

Description

    CROSS-REFERENCE TO RELATED APPLICATIONS
  • The present application claims the benefit and priority of U.S. Provisional Patent Application Ser. No. 61/800,114 filed on Mar. 15, 2013 and titled “(EPA) Algal Biomass and Oil Compositions and Impact on Health,” which is hereby incorporated by reference.
  • The present application claims the benefit and priority of U.S. Provisional Patent Application Ser. No. 61/800,029 filed on Mar. 15, 2013 and titled “Microalga Species and Industrial Applications,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______, filed on ______ concurrently with the present application and titled “Algal Oil Compositions,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______, filed on ______ concurrently with the present application and titled “Conversion of Free Fatty Acids to Ethyl Esters,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______, filed on ______ concurrently with the present application and titled “Algal Omega 7 and Algal Omega 3 Blend Compositions,” which is hereby incorporated by reference.
  • The present application is related to U.S. Non-Provisional patent application Ser. No. ______, filed on ______ concurrently with the present application and titled “Compositions and Methods for Utilization of Algal Compounds,” which is hereby incorporated by reference.
    • BACKGROUND OF THE INVENTION Field of the Invention
  • This invention relates to algal biochemistry, and more specifically, to algal omega 7 compositions.
    • SUMMARY OF THE INVENTION
  • Provided herein are exemplary algal omega 7 compositions, including algal fatty acid compositions comprising by dry weight from about approximately 0.5% to about approximately 99% C16:1 n7 palmitoleic acid (POA). Such algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 10% saturated fatty acids; from about approximately 0% to about approximately 99% arachidonic acid; from about approximately 0% to about 99% docosahexaenoic acid; and/or from about approximately 0% to about approximately 99% eicosapentaenoic acid.
  • Provided herein are also exemplary algal omega 7 compositions, including algal fatty acid compositions comprising by dry weight from about approximately 0.5% to about approximately 99% C16:1 n7 palmitoleic acid (POA). Such algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 10% saturated fatty acids; from about approximately 0% to about approximately 10% arachidonic acid; substantially no (i.e. less than approximately 0.5%) docosahexaenoic acid; and/or from about approximately 0% to about approximately 10% eicosapentaenoic acid.
  • Further exemplary algal fatty acid compositions may include by dry weight about approximately 90% palmitoleic acid, less than about approximately 10% saturated fatty acids, less than about approximately 10% arachidonic acid, substantially no docosahexaenoic acid, and less than about approximately 10% eicosapentaenoic acid.
  • The algal palmitoleic acid compositions described herein may be desaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from saturated algal compositions comprising by total weight approximately 50% POA, approximately 50% palmitic acid (PA) and substantially no DHA. The saturated algal compositions may result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 23% PA, less than approximately 10% ARA, and substantially no DHA.
  • The saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, less than approximately 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • The saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight from between approximately 0% EPA and 99% EPA, from between approximately 0% POA and 99% POA, less than approximately 20% saturated fats, from between approximately 0% ARA and 99% ARA, and from between approximately 0% DHA and 99% DHA.
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 shows an actual fatty acid (in ethyl ester form) profile for an exemplary total algal oil composition.
  • FIG. 2 shows a flow chart for an exemplary method of unsaturating an exemplary saturated fatty acyl moieties (FAMs) rich algal composition.
  • FIG. 3 shows the actual content of 16:0 ethyl ester (palmitic acid) expressed as mg/g ethyl ester in the liquid phase at each of steps 210-250 as described in connection with FIG. 2.
  • FIG. 4 shows an actual fatty acid profile for an exemplary fatty acid composition comprising mostly C16:1 n7 palmitoleic acid that resulted after processing an exemplary total algal oil composition such as that shown in FIG. 1 by the exemplary method shown and described in connection with FIG. 2.
  • FIG. 5 is a data table for an actual fatty acid profile for an exemplary total algal oil composition (in ethyl ester form), such as shown in FIG. 1, an exemplary saturated algal composition (in ethyl ester form), and an exemplary fatty acid composition (in ethyl ester form) comprising mostly C16:1 n7 palmitoleic acid, as shown in FIG. 4.
  • FIG. 6 is an actual saturated fat profile for an exemplary whole biomass (“WB”) (in a form of a fatty acid methyl ester), an exemplary crude biomass (“Crude”) (in a form of a fatty acid methyl ester), an exemplary algal oil composition (“TAO”) (in ethyl ester form), an exemplary 16 chain fatty acid composition (in ethyl ester form), and an exemplary C16:1 n7 palmitoleic acid (in ethyl ester form).
    •  DETAILED DESCRIPTION OF THE INVENTION
  • A fatty acid is a carboxylic acid with a long aliphatic tail (chain), which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Saturated fatty acids have no double bonds between carbon atoms. Unsaturated fatty acids have one or more double bonds between carbon atoms. When counting from the terminal methyl carbon toward the carbonyl carbon on an unsaturated fatty acid, the first double bond signifies the omega double bond, such as observed in omega 3, omega 6, or omega 7 fatty acids.
  • Palmitoleic acid (POA) is an omega-7 monounsaturated fatty acid with a 16-carbon chain with one double bond, denoted as C16:1 n7. A beneficial fatty acid, it has been shown to suppress inflammation. Dietary sources of omega-7 are found in animal and plant sources, including sea buckthorn berries, macadamia nuts, cold water fish and dairy fat. These sources, however, are not concentrated and/or purified sources of POA and often contain a mixed fatty acid profile of saturated and polyunsaturated fats.
  • Palmitic acid (PA) is a saturated fatty acid with a 16-carbon chain and no double bonds, denoted as C16:0. Consumption of saturated fats such as palmitic acid is believed to increase the risk of developing diabetes, obesity, stroke and cardiovascular diseases.
  • Alpha linolenic acid (ALA) is an omega-3 polyunsaturated fatty acid (PUFA) with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, denoted as C18:3 n3.
  • Arachidonic acid (ARA) is an omega-6 PUFA with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end. ARA is also denoted as C20:4 n6. Examples of dietary sources of omega-6 PUFAs include refined vegetable oils, such as corn and soy oil, seeds and nuts and the oils extracted from them. Consumption is therefore sufficient in the average diet.
  • Eicosapentaenoic acid (EPA) is an omega-3 fatty acid PUFA with the connotation C20:5 n3. It is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end.
  • Docosahexaenoic acid (DHA) is an omega-3 fatty acid PUFA. It is a carboxylic acid with a 22-carbon chain and six cis double bonds; the first double bond is located at the third carbon from the omega end. DHA is also denoted as C22:6 n3.
  • Provided herein are exemplary algal omega 7 compositions, including algal fatty acid compositions comprising by dry weight from about approximately 0.5% to about approximately 99% C16:1 n7 palmitoleic acid (POA). Such algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 20% saturated fatty acids; from about approximately 0% to about approximately 99% arachidonic acid; from about approximately 0% to about 99% docosahexaenoic acid; and/or from about approximately 0% to about approximately 99% eicosapentaenoic acid.
  • The various exemplary algal omega 7 compositions provided herein may comprise by dry weight from about approximately 0.5% to about approximately 99% palmitoleic acid. Such algal compositions may also include (either individually or any combination of) by dry weight: from about approximately 0% to about approximately 20% saturated fatty acids; from about approximately 0% to about approximately 10% arachidonic acid; substantially no (i.e. less than approximately 0.5%) docosahexaenoic acid; and/or from about approximately 0% to about approximately 10% eicosapentaenoic acid.
  • Additionally, the various exemplary algal omega 7 compositions provided herein may further be in ethyl ester form. Such ethyl esters are derived by reacting free fatty acids with ethanol. Called esterification, the resulting ethyl ester allows for the fractional distillation (concentration) of the long chain fatty acids at lower temperatures. This step allows for the selective concentration of the fatty acids to levels greater than found in nature.
  • The ethyl ester forms of the various exemplary algal omega 7 compositions provided herein may be converted to a triglyceride form by performing an enzymatic reaction with the ethyl ester form in the presence of glycerol, heating under a vacuum, and filtering out the enzymes. Per some exemplary methods, immobilized lipase enzymes may be those isolated from Candida antarctica and/or commercially supplied by Novozyme or Sigma Aldrich.
  • The algal palmitoleic acid compositions described herein may be desaturated (i.e. removing the saturated fatty acids from the monounsaturated and/or polyunsaturated fatty acids) from saturated algal compositions comprising by total weight approximately 50% POA, approximately 50% palmitic acid (PA) and substantially no DHA. The saturated algal compositions may result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • The saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight approximately 30% EPA, approximately 27% POA, less than approximately 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • The saturated algal compositions may also result from the processing of total algal oil compositions comprising by total weight from between approximately 0% EPA and 99% EPA, from between approximately 0% POA and 99% POA, less than approximately 10% saturated fats, from between approximately 0% ARA and 99% ARA, and from between approximately 0% DHA and 99% DHA.
  • In various embodiments, various algae species may be the source of the compositions provided herein. Algae are mostly aquatic photosynthetic organisms that range from microscopic flagellate to giant kelp. Algae may be loosely grouped into seven categories: Euglenophyta (euglenoids), Chrysophyta (golden-brown algae), Pyrrophyta (fire algae), Dinoflagellata, Chlorophyta (green algae), Rhodophyta (red algae), Paeophyta (brown algae), and Xanthophyta (yellow-green algae). Lipid extracted from any algae genus may be used in the various embodiments of the present invention, including Amphora, Anabaena, Anikstrodesmis, Botryococcus, Chaetoceros, Chlorella, Chlorococcum, Cyclotella, Cylindrotheca, Dunaliella, Emiliania, Euglena, Glossomastix, Haematococcus, Isochrysis, Monochrysis, Monoraphidium, Nannochloris, Nannochloropsis, Navicula, Nephrochloris, Nephroselmis, Nitzschia, Nodularia, Nostoc, Oochromonas, Oocystis, Oscillatoria, Pavlova, Phaeodactylum, Picochloris, Platymonas, Pleurochrysis, Porphyra, Pseudoanabaena, Pyramimonas, Scenedesmus, Stichococcus, Synechococcus, Synechocystis, Tetraselmis, Thalassiosira, and Trichodesmium.
  • FIG. 1 shows an actual fatty acid (in ethyl ester form) profile for an exemplary total algal oil composition that was produced and analyzed by the present inventors. As illustrated by FIG. 1, exemplary total algal oil compositions may comprise by total weight approximately 30% EPA, approximately 27% palmitoleic acid, approximately approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
  • An exemplary total algal oil composition, such as the exemplary total algal oil composition shown in FIG. 1, may be processed via high vacuum distillation, resulting in an exemplary algal composition comprising saturated fatty acyl moieties (FAMs) including by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
  • FIG. 2 shows a flow chart for an exemplary method of unsaturating an exemplary saturated fatty acyl moieties (FAMs) rich algal composition.
  • At step 210, 100 milliliters (mls) of the exemplary saturated algal composition is chilled at 4° C. for 24 hours, resulting in formation of transparent crystals as stoutly needles.
  • At step 220, the mixture comprising the transparent crystals is vacuum-filtered through a whatman #1 paper filter, and the cake is blotted with kimwipes to remove interstitial liquid.
  • At step 230, the filtered liquid phase is brought to −3° C. for 24 hours, and a second crop of crystals is formed as described above.
  • At step 240, the filtered liquid phase is brought to −10° C. for 24 hours, and a third crop of crystals is formed, these crystals being smaller and rounder than earlier crops.
  • At step 250, the filtered liquid phase is then brought to −20° C. for 24 hours, and forms a turbid suspension which is filtered.
  • FIG. 3 shows the actual content of 16:0 ethyl ester (palmitic acid) expressed as mg/g (in ethyl ester form) in the liquid phase at each of steps 210-250 as described in connection with FIG. 2. Referring to FIG. 3, each diamond represents the actual content of 16:0 ethyl ester (palmitic acid) expressed as mg/g (in ethyl ester form) in the liquid phase, beginning with step 210 for the diamond at the left, and progressing to step 250 for the diamond at the right.
  • FIG. 4 shows an actual fatty acid profile for an exemplary fatty acid composition comprising mostly C16:1 n7 palmitoleic acid that resulted after the present inventors processed an exemplary total algal oil composition such as that shown in FIG. 1 by the exemplary method shown and described in connection with FIG. 2.
  • As shown in FIG. 4, exemplary algal omega 7 compositions may comprise approximately 90% palmitoleic acid, less than approximately 10% saturated fatty acids, less than approximately 2% arachidonic acid, substantially no docosahexaenoic acid, and less than approximately 10% eicosapentaenoic acid.
  • FIG. 5 is a data table for an actual fatty acid profile determined by the present inventors for an exemplary total algal oil composition (in ethyl ester form), such as shown in FIG. 1, an exemplary saturated FAM-rich algal composition (in ethyl ester form), and an exemplary fatty acid composition (in ethyl ester form) comprising mostly C16:1 n7 palmitoleic acid, as shown in FIG. 4.
  • The data table in FIG. 5 shows fatty acid type by milligrams per gram (mg/g) as found in the ethyl ester forms of the various algal compositions. Remarkably, as shown in FIG. 5, the exemplary fatty acid composition (in ethyl ester form) comprising mostly C16:1 n7 palmitoleic acid, also comprises only 3.46% saturated fatty acids.
  • FIG. 6 is an actual saturated fat profile for an exemplary whole biomass (“WB”) (in a form of a fatty acid methyl ester), an exemplary crude biomass (“Crude”) (in a form of a fatty acid methyl ester), an exemplary total algal oil composition (“TAO”) (in ethyl ester form), an exemplary 16 chain fatty acid composition (in ethyl ester form), and an exemplary C16:1 n7 palmitoleic acid (in ethyl ester form). The data is reflected as % saturated fats to total saturated and non-saturated fats.
  • As shown in FIG. 6, the exemplary algal composition is less saturated than both the exemplary crude and whole algal biomass compositions.
  • While various embodiments have been described above, it should be understood that they have been presented by way of example only, and not limitation. Thus, the breadth and scope of a preferred embodiment should not be limited by any of the above-described exemplary embodiments.

Claims (25)

What is claimed is:
1. An algal fatty acid composition comprising by dry weight approximately 0.5% to approximately 99% C16:1 n7 palmitoleic acid and less than approximately 20% saturated fatty acids.
2. The algal fatty acid composition of claim 1, further comprising by dry weight less than approximately 10% arachidonic acid.
3. The algal fatty acid composition of claim 1, further comprising by dry weight substantially no docosahexaenoic acid.
4. The algal fatty acid composition of claim 1, further comprising by dry weight less than approximately 10% eicosapentaenoic acid.
5. The algal fatty acid composition of claim 1, as unsaturated from a saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
6. The saturated fatty acyl moiety-rich algal composition of claim 5, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
7. An algal fatty acid composition comprising by dry weight greater than approximately 70% palmitoleic acid and less than approximately 20% saturated fatty acids.
8. The algal fatty acid composition of claim 7, further comprising by dry weight less than approximately 10% arachidonic acid.
9. The algal fatty acid composition of claim 7, further comprising by dry weight substantially no docosahexaenoic acid.
10. The algal fatty acid composition of claim 7, further comprising by dry weight less than approximately 10% eicosapentaenoic acid.
11. The algal fatty acid composition of claim 7, as processed from a saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
12. The saturated fatty acyl moiety-rich algal composition of claim 11, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
13. An algal fatty acid composition comprising by dry weight greater than approximately 80% palmitoleic acid and less than approximately 20% saturated fatty acids.
14. The algal fatty acid composition of claim 13, further comprising by dry weight less than approximately 10% arachidonic acid.
15. The algal fatty acid composition of claim 13, further comprising by dry weight substantially no docosahexaenoic acid.
16. The algal fatty acid composition of claim 13, further comprising by dry weight less than approximately 10% eicosapentaenoic acid.
17. The algal fatty acid composition of claim 13, as processed from a saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
18. The saturated fatty acyl moiety-rich algal composition of claim 17, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
19. An algal fatty acid composition comprising by dry weight approximately 90% palmitoleic acid, less than approximately 20% saturated fatty acids, less than approximately 10% arachidonic acid, substantially no docosahexaenoic acid, and less than approximately 10% eicosapentaenoic acid.
20. The algal fatty acid composition of claim 19, as processed from a saturated fatty acyl moiety-rich algal composition comprising by total weight approximately 50% POA, approximately 50% PA and substantially no DHA.
21. The saturated fatty acyl moiety-rich algal composition of claim 20, as processed from a total algal oil composition comprising by total weight approximately 30% EPA, approximately 27% POA, approximately 0% to 20% saturated fats, less than approximately 10% ARA, and substantially no DHA.
22. The algal fatty acid composition of claim 1, wherein the composition is in a form of an ethyl ester (EE), a mono, di, or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
23. The algal fatty acid composition of claim 7, wherein the composition is in a form of an ethyl ester (EE), a mono, di, or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
24. The algal fatty acid composition of claim 13, wherein the composition is in a form of an ethyl ester (EE), a mono, di, or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
25. The algal fatty acid composition of claim 19, wherein the composition is in a form of an ethyl ester (EE), a mono, di, or triacylglycerol (MAG, DAG, TAG), a phospholipid (PL), a galactolipid (GL), free fatty acid (FFA), or a sulfoquinovosyl diacylglycerol (SQDG).
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