JP2023548424A - Improved omega-3 containing compositions - Google Patents

Abstract

The present disclosure relates to bioavailable oil compositions, wherein at least 20% by weight of the total lipid content comprises polar lipids, such as glycolipids or phospholipids, and at least 30% by weight of the polar lipids comprises glycolipids; Up to 4% by weight of the oil composition is composed of chlorophyll species. Also disclosed are formulations containing said oil compositions and methods of making said oil compositions from algal oils or extracts.

Description

[Related applications]
Not applicable.

[Statement regarding federally sponsored research or development]
Not applicable.

Today, omega-3 oils are in high demand because aquaculture, fishing, and other marine sources alone can supply approximately 800,000 tons of omega-3 fatty acids annually for human consumption. This is below the human nutritional requirement of 1.4 million tonnes needed to supply the world's population with 500 mg of omega-3 fatty acids daily, and is expected to worsen with population growth. Omega-3 fatty acid deficiencies have been observed around the world, particularly affecting people living in North America, Central Europe, the Middle East, India, Brazil, and the United Kingdom, with regional and socio-economic differences within each country. A difference was discovered. Three major omega-3 fatty acids are found in nature. Alpha linoleic acid (ALA), which has 18 carbons and 3 double bonds, is found in, for example, flaxseed, soybean oil, and olives. Docosahexaenoic acid (DHA), which has 22 carbons and 6 double bonds and is important for infant development, is found in the breast milk of mammals (including humans) and fish oil, and is found in aquatic species (algae). only grows. Eicosapentaenoic acid (EPA), which has 20 carbons and 5 double bonds, grows only in aquatic species (algae), like DHA, and can be extracted from krill krill and fish that eat algae, or from the algae itself. .

"Working algae", i.e. algae that grow using sunlight or artificial light and photosynthesis, contain lipids that are polar in nature and are bioavailable, although they also contain other components. These components cause the oil extracted from the algae to have an overall very dark, almost blackish appearance and to be highly viscous, resembling a tar-like black solid.

Highly bioavailable EPA-containing, low viscosity, low chlorophyll content, light amber to dark amber oil for use in nutraceuticals and pharmaceuticals. Although no composition is currently available, it is highly desirable.

The present disclosure relates to EPA-enriched compositions with enhanced bioavailability. The starting material for this composition may be derived from algae, by way of example and without limitation. In one embodiment, a composition is disclosed comprising a polar lipid fraction of a total lipid concentration of at least 20% by weight of the total lipid, wherein the polar lipid fraction is at least 30% by weight of the total lipid concentration. % glycolipids, and the composition contains no more than 4% of the weight percent of the composition as chlorophyll concentrate. In certain embodiments herein, the composition further comprises 4% or less of the weight percent of the composition as a polysaccharide composition. Additional embodiments of EPA-rich compositions with increased bioavailability and improved composition profiles and resulting attributes are also disclosed.

The embodiments described above provide attractive compositions for use in both the nutraceutical and pharmaceutical fields in terms of reduced opacity and viscosity, as well as other beneficial attributes.

A composition as described above, wherein at least 20% by weight of the total lipids is a polar lipid fraction, and at least 30% by weight of said polar lipids is a glycolipid fraction, but the chlorophyll fraction is less than 4% by weight in the composition. The formulation may further include additive non-polar lipids and/or nutraceutical oils such as DHA, or other beneficial additives as described in more detail below, which also improve bioavailability. It helps provide a particular beneficial combination of oils that are higher in color, rich in nutrients, brighter in color, and lower in viscosity.

The present disclosure also provides the steps of obtaining an algal paste, extracting the algal paste with alcohol to form an alcoholic extract of algal lipids, and extracting the resulting alcoholic extract (e.g., with hydrocarbon hexane or separating the non-polar lipid fraction (with an organic solvent such as heptane) and transferring the alcohol layer containing the pigment and polar lipids to an additional processing step; adding water, followed by sequential extraction (e.g., with heptane) to extract the pigment fraction and separating the polar lipid fraction. Subsequently, polar lipids can be obtained by evaporation from said polar lipid-containing fraction, and dyes can also be obtained by evaporation of said dye-containing fraction. Polysaccharides can be obtained from the fractions containing said polysaccharides by subjecting said fractions to a short winterization stage. Chlorophyll can also be removed from the chlorophyll-containing fraction using a suitable bleaching substance.

The present disclosure also provides an alternative method of producing an oil composition with low chlorophyll content that includes obtaining an algae oil or extract that includes both polar and non-polar lipid fractions and also has a chlorophyll concentrate. including. The method includes substantially separating a chlorophyll concentrate along with a non-polar lipid fraction, wherein the polar lipid fraction and the non-polar lipid fraction are separated to separate polar components from non-polar components in the algal oil or extract. further comprising using the polarity characteristics of the component. Additional steps include bleaching substantially all of the chlorophyll concentrate from the non-polar containing fraction and recombining the polar and non-polar lipid fractions to produce an oil composition with low chlorophyll content. Contains steps and.

These and other features of the disclosure are described in more detail in the detailed description below.

1 discloses a schematic diagram of extraction and bleaching process steps for an exemplary method of producing oil of embodiments of the present disclosure. 1 is a photographic depiction of an embodiment of a composition of the present disclosure having the desired target polar lipid, glycolipid and chlorophyll concentrations, bioavailability, color, and viscosity of an oil composition, the embodiment of which is disclosed herein; has been done. For example, a photograph of a powder obtained by a method embodiment of the present disclosure consisting of substantially non-lipid components, including polysaccharides contained in the crude ethanolic algae extract produced by the method embodiments described herein. It is a depiction. 1 is a graph showing spectral characterization for an embodiment of an ethanolic extract of Nannochloropsis and a product after pigment removal, as discussed in Example 1. FIG. 2 is a graph showing UV-visible spectral characterization for an embodiment of algae extraction, as discussed in Example 2. FIG.

The following detailed description is intended to illustrate, by way of example and not limitation, the claimed disclosure. This description clearly enables any person skilled in the art to make and use the claimed disclosure, and provides several embodiments, adaptations, and variations of the claimed disclosure. , alternatives, and uses are explained. Furthermore, it is to be understood that the claimed disclosure is not to be limited in its application only to the details and compositions specifically set forth in the following description or illustrated in the drawings. The claimed disclosure is capable of other embodiments and of being practiced or carried out in various ways. Additionally, it is to be understood that the phrases and terminology used herein are for purposes of explanation and should not be considered limiting.

The term "polar lipid" as used herein refers to an amphipathic lipid having a hydrophilic head and a hydrophobic tail. Examples of polar lipids include phospholipids and glycolipids.

As used herein, the term "non-polar lipid" refers to a fatty molecule in which the charge distribution is approximately uniform and the molecule does not have positively and negatively charged ends. Examples of non-polar lipids include triglycerides of various fatty acids in oils, such as EPA and palmitoleic acid.

To produce the disclosed embodiments of the oil composition, an algae extract can be obtained that is provided as a dark green or even black, highly viscous oil.

The procedure for obtaining the algal biomass extract and the starting algae and extraction procedure for preparing the algal biomass may include the following steps.

Obtaining an algae paste, such as Nannochloropsis or Chlorella algae paste; and extracting the algae paste with an alcohol, such as ethyl alcohol, to form an alcoholic extract of algal lipids with a low water content (e.g., Nannochloropsis or Chlorella algae paste); forming an ethanolic extract of Psis lipids (hereinafter abbreviated as "EEN") and extracting the resulting EEN (e.g. with an organic solvent such as the hydrocarbon hexane or heptane) to extract non-polar lipids ( For example, separating triglycerides, waxes, carotenes) fractions, thereby forming a "non-polar lipid fraction (F#1 in FIG. 1)" in the heptane layer. The alcohol layer contains pigments and polar lipids and can be transferred to additional processing steps (see Figure 1).

The next processing step is to add water to the extracted (e.g. with heptane) alcohol layer and then sequentially extract (e.g. with heptane) the pigment fraction (see Figure 1, heptane layer, F#3 ) and separating the polar lipid fraction (see Figure 1, water-alcoholic layer, F#2). Polar lipids can be obtained from the F#2 fraction by evaporation, and dyes can be obtained by evaporation from the F#3 fraction. The F#1 layer can contain a certain amount of chlorophyll and carotenoids, which can be removed by methods known to those skilled in the art, such as those known for the production of edible oils. Examples of these methods include adsorption-filtration using silica gel, bleaching clays such as B80, T41, activated carbon, and the like. As a result of the selective removal of chlorophyll from the F#1 fraction, this embodiment results in a somewhat liquid to semi-solid oil with an almost clear to deep amber color, including red color.

An alternative method of obtaining algal oil or extract is disclosed in U.S. Pat. No. 8,591,912 B1 (Kiran Kadam and Brian Goodall), the contents of which are all incorporated herein by reference. .

The following examples illustrate the invention.

[Example 1]
2.1 Process protocol for this example (see Figure 1)
1) 100 g of Nannochloropsis algal paste (solid content in water 22-27%) was weighed. (Step 1, Figure 1)
2) The algae paste was placed in a 2L flask and 850ml of alcohol was added. (Step 1, Figure 1)
3) The algae were extracted at a temperature of 70° C. for 45 minutes with vigorous stirring. (Step 1, Figure 1)
4) The solid algae residue was filtered from the ethanol extract (vacuum filtration). (Step 2, Figure 1)
5) Place the ethanol extract from the previous step into a separatory funnel (2 L), add 300 mL of heptane to the resulting extract, stir vigorously for 2 minutes, separate the layers, and carefully sort out the top layer. , into another flask to obtain about 120 mL of green heptane layer. (Step 3, Figure 1)
6) Add another 100 mL of heptane to the ethanol layer, stir vigorously for 2 minutes, separate the layers (ethanol layer - bottom layer, and heptane layer - top layer), carefully sort out the top layer and add the remaining 100 mL of heptane obtained from the previous step. Combined with heptane layer (~200-220 mL of combined green heptane layer was obtained, fraction F#1). (Step 4, Figure 1)
7) Added 1 g of silica gel to the total heptane layer obtained and stirred vigorously for 5 minutes, then filtered the slurry through a 1 g layer of silica gel (instead of silica gel, activated carbon or T41 bleaching earth may be used) . Due to the different properties of various silica gels, activated carbons, and bleaching earths, the actual amount of material should be adjusted in the factory. (Step 8, Figure 1)
8) Remove the bottom layer (ethanol layer) from step 6 of this protocol, add 350 mL of water and 200 mL of heptane, and shake the mixture vigorously for 2 minutes. After allowing the separated phases to stand for approximately 5 minutes, the top layer was carefully filtered into a separate flask (this step yielded ~400 mL of green heptane layer). (Step 5, Figure 1)
9) Repeatedly extract the lower layer in the above step using 200 mL (3 x 200 mL) of heptane. The top layer was carefully sorted and combined with the heptane layer obtained from the previous step (~1000-1020 mL of combined green heptane layer was obtained, fraction F#3). (Step 5, Figure 1)
10) The extracted lower layer contained purified polar lipids (F#2). This fraction is purified, for example, by 3 g of Amaze-N bleach adsorbent or similar adsorbent (if necessary) from Helix Chromatography (15 E. Palantine Rd. #118, Prospect Heights, IL 60070; helixchrom.com). be able to.
11) The obtained fractions were evaporated in vacuo while heating below 45°C.

The above process steps and test results demonstrate a highly efficient liquid-liquid extraction method for removing chlorophyll and carotenoid fractions from algae extracts such as Nannochloropsis or Chlorella lipids. By using the above embodiments of the disclosed method, more than 99% of chlorophylls a and b and pheophytin were removed from the ethanolic extract of Nannochloropsis, as well as approximately 2% of the carotenoids (medium polar carotenoids). /3 was removed. See Tables 2 and 3 below. Table 2: Extract mass balance (composition) and Table 3: Main components of Nannochloropsis ethanol extract for mass and weight % analysis of composition. Refer to FIG. 4 for the spectral characteristics of the Nannochloropsis ethanol extract after pigment removal.

Viscosity measurements can vary depending on factors such as temperature, compositional concentration of the various ingredients in the formulation, but after combining the polar and neutral lipid fractions at 25 °C, as described herein, The viscosity reading measured for an embodiment of the Nannochloropsis extract produced as described in , 165,000 mPa. 's was shown.

In summary, the product shown in Example 1 can be resolved into three fractions of the input Nannochloropsis ethanol extract. 1) fraction (F#1), non-polar lipids, mainly triglycerides; 2) fraction (F#2), polar lipids including glycolipids and phospholipids; 3) fraction (F#3), It can be broken down into a medium polar fraction containing diglycerides and monoglycerides, free fatty acids (FFA's), carotenoids and chlorophyll. The purified F#1 and F#2 fractions can be used as a valuable lipid source rich in palmitoleic acid and eicosapentaenoic acid (EPA). F#3 is a concentrate of natural pigments, including chlorophyll, astaxanthin, and zeaxanthin, and is also valuable as a food additive. Fractions F#1 to F#3 can each be used as food additives and are valuable raw materials with high biological potential.

[Example 2]
Dark green paste samples of algal biomass were generally described in U.S. Patent No. 8,591,912 B1 (see generally column 6, line 62 to column 9, line 3). manufactured by the method. The algal biomass paste was extracted with hot absolute ethanol. Specifically, 66 g of algae paste, 3×250 mL of ethanol, 75° C., 30′ were each stirred at 500 rpm, and centrifuged at 4450 rpm for 10 minutes to obtain an algae extract sample.

As a result of analysis of oil extracts, the main polar lipids in algae samples were 1) glycolipids (monogalactosyl diglyceride (MGDG) and digalactosyl diglyceride (DGDG)) and 2) phospholipids (phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol) (see Table 4 herein).

The bioavailable, low chlorophyll content, polar lipid-rich oil embodiments of the present disclosure quantified herein were produced from the starting materials using the following additional steps.

1) Polar lipids were separated from a mixture of nonpolar lipids, chlorophyll, and other components based on polarity differences.

2) Bleach the chlorophyll from the remaining non-polar lipid components using well-developed protocols for vegetable oil bleaching, as described in Example 1 above, e.g., to obtain 1 g of silica gel. After addition to the heptane layer and vigorous stirring for 5 minutes, the slurry was filtered through a 1 g layer of silica gel (activated carbon or T41 bleaching earth may be used instead of silica gel). Due to the different properties of various silica gels, activated carbons, and bleaching earths, the actual amount of material should usually be adjusted in the factory.

3) The polar lipid fraction from step (1) above was combined with the bleached non-polar lipid from step (2) above.

A low chlorophyll-containing oil composition rich in bioavailable polar lipids with a generally low viscosity, nearly clear to light brown color was obtained. See FIG. 5 for spectral analysis. The composition was a waxy solid at an ambient temperature of about 70 degrees Fahrenheit. The composition melts when heated and exhibits a low viscosity when mixed with other oils such as triglycerides.

Analysis of the oil compositions of the bioavailable oil embodiments of the present disclosure produced using the above processes described herein revealed the following components and characteristics (column 1), as shown in Table 1: ), and a composition range (column 2).

Minor variations in the weight percentages and other properties of the oil components disclosed in this application may be obtained by modifying the processes used as known to those skilled in the art. However, preferably the weight percent of the polar lipid fraction in the total lipid concentrate of the oil produced is greater than 20 percent, preferably greater than 30 percent, more preferably greater than 40 percent, more More preferably, it is greater than 50% by weight, and even more preferably about 70% or more. Also preferably, of the oil product, the weight percent of chlorophyll concentrate is less than 4%, more preferably less than 3.0%, even more preferably less than 2.0% of the total oil product weight; Even more preferably less than 1.0%, even more preferably about 0.1% or less. Also preferably, of the oil product, the weight percent of polysaccharide concentrate is less than or equal to about 4%, more preferably less than 3.0%, and even more preferably less than 2.0% of the total oil product weight. , even more preferably less than 1.0% or lower. Furthermore, the weight percent of glycolipids as a weight percent of total polar lipids is greater than 20%, preferably greater than 30%, more preferably greater than about 40%, even more preferably greater than 50%, and even more. Preferably, it is about 60% or more, and of the total oil composition, the weight percent of glycolipids is more than 10%, more preferably more than 20%, and even more preferably about 25% or more. Furthermore, the weight percent of phospholipids as a weight percent of polar lipids is greater than 20%, more preferably greater than 30%, even more preferably greater than 35%, of the total oil composition. is more than 20%, more preferably more than 30%, even more preferably more than 40%. Without wishing to be bound by any particular theory, Applicants believe that the combination of these properties, including very low chlorophyll concentrations in the oil product, results in an attractive, light-colored, nearly transparent amber color. It is thought that it is produced from to a deeper amber color. Also, the EPA concentration in the total oil product content is at least 20% by weight, more preferably at least 25% by weight, and even more preferably at least about 30% by weight or more is produced. Similarly, the omega-3 content in the oil product is at least 20% by weight, more preferably at least 25% by weight, and even more preferably at least about 30% by weight or more is produced. An increase in the bioavailability of the produced oil was also achieved.

Embodiments of the process of the present disclosure also provide a powder of non-lipid components, such as polysaccharides, in the crude ethanolic algae extract. See FIG. 3.

It should also be noted that for the EPA-containing high polar content oils of the present disclosure, the weight percent of chlorophyll is significantly reduced. 1) Chlorophyll a, 2) Protochlorophyll a, and 3) Methylchlorophyllide. Preferably, the weight percent of chlorophyll in said composition is less than 4%, preferably less than 3%, more preferably less than 2%, even more preferably less than 1%, more preferably less than 3%, more preferably less than 2%, more preferably less than 1%, and more preferably less than 3% of the total weight percent of said composition. More preferably less than 0.5%, even more preferably less than about 0.1%.

In another embodiment of the composition of the present disclosure, the composition comprises carotenoids, such as carotenes (α and β), and zeaxanthin (yellow pigment), and several others including canthaxanthin and zeaxanthin (red pigment). The weight percent of the components is increased, with total carotenoids constituting more than 0.5%, preferably 1% or more of the total weight of the extract.

In other alternative embodiments of the present disclosure, the embodiments disclosed herein of low chlorophyll oil compositions comprising bioavailable highly polar lipids and comprising EPA may contain other useful ingredients. It can be provided as a formulation to which is added. These other useful ingredients can be added alone or in one or more combinations, such as with other essential oils, nutritional supplements, dietary supplements, and the like. Specific examples include, but are not limited to, the following: 1) Other omega-3-containing oils or ingredients, such as DHA and EPA (e.g. in the form of neutral lipids extracted as a product of the invention or supplied externally), lysolipids from the invention ), or externally supplied ethyl esters of DHA or EPA; 2) carotenoids, including astaxanthin, lutein, zeaxanthin, lycopene, carotenes (α and β), cryptoxanthin, and mixtures thereof; 3) vitamins such as vitamins C and D, 4) cannabinoids such as cannabidiol (CBD), and 5) other combinations. Such formulations containing some of these species with less color and/or less viscous compositional profiles include highly polar lipids, high glycolipids produced by embodiments of the methods disclosed herein. , and the overall color profile and viscosity of formulations containing fatty acid compositions having low chlorophyll concentrations. This may therefore be achieved, for example, by including non-polar lipids that are re-added from the original biomass stock or external sources, or by manufacturing formulations that exhibit such attributes.

An example of a nutraceutical formulation comprising a blend of polar EPA fractions and DHA (omega-3) as described above may advantageously be in a ratio of 10-90 to 90-10, where preferred levels of polar EPA formulation The ingredients are mixed at 20-50%. Applications of such formulations include other neutral lipids and ingredients for formulation with essential uses as primary nutraceuticals/dietary supplements for cardiovascular health, mood, anti-depression, etc. Also includes use as a delivery system for. This may be DHA, other neutral forms of EPA, or mixtures thereof. Astaxanthin at 10-60% levels can also be advantageously formulated with pure polar EPA lipids or blends thereof with neutral EPA and/or EPA, preferably at 10-30% levels. Another ingredient that may advantageously be added to such formulations is Coenzyme Q10 at a level of about 1-50%, preferably about 2-20%, relative to polar EPA, either pure or in said formulation.

In addition to other attributes, the formulation blend to which neutral lipids have been added, for example, less than 50,000 mPa·s, preferably less than 10,000 mPa·s, more preferably less than about 2,000 mPa·s, most preferably may be useful for targeting various viscosity levels, such as about 300 mPa·s or less.

In view of the above, it will be seen that certain objects and advantages of the present disclosure have been achieved and other advantageous results obtained.

All matter contained in the above description or shown in the accompanying drawings is to be interpreted as illustrative, as various changes may be made to the configuration described above without departing from the scope of the disclosure. should not be construed in a restrictive sense.

Claims (51)

A composition comprising a total lipid concentration, wherein at least 20% by weight of the total lipid concentration comprises a polar lipid fraction, and more than about 30% by weight of the polar lipid fraction. A composition comprising glycolipids, wherein the composition comprises no more than 4% of its weight percent as chlorophyll concentrate. 2. The composition of claim 1, wherein the composition has a total lipid concentration of at least about 75% by weight of the total composition. 2. The composition of claim 1, wherein the composition has a total lipid concentrate of at least about 90% by weight of the total composition. 2. The composition of claim 1, wherein at least about 50% by weight of the total lipid concentrate comprises a polar lipid fraction. 2. The composition of claim 1, wherein the composition comprises no more than about 1.0% of its total weight percent as chlorophyll concentrate. 2. The composition of claim 1, wherein the composition further comprises at least about 20% total omega-3 by weight. 7. The composition of claim 6, wherein the weight percent of total omega-3 in the composition comprises at least about 30% by weight. 2. The composition of claim 1, wherein the composition further comprises at least about 20% total EPA by weight. 2. The composition of claim 1, wherein the glycolipid comprises at least about 60% by weight of polar lipids. 2. The composition of claim 1, wherein the composition comprises at least about 20% glycolipids by weight. 2. The composition of claim 1, wherein the composition comprises at least about 40% glycolipids by weight. 2. The composition of claim 1, wherein the composition further comprises a phospholipid comprising at least about 40% of the polar lipid by weight, as a weight percent of the polar lipid. 13. The composition of claim 12, wherein the phospholipid comprises at least about 60% of its polar lipids by weight. 2. The composition of claim 1, wherein the composition comprises at least about 20% phospholipids by weight. 15. The composition of claim 14, wherein the composition comprises at least about 40% phospholipids by weight. 2. The composition of claim 1, wherein the composition comprises about 4% or less polysaccharide by weight. 17. The composition of claim 16, wherein the composition comprises about 2% or less polysaccharide by weight. 2. The composition of claim 1, wherein the composition exhibits a clear to deep amber color in ambient light. The composition of claim 1, wherein the composition has a viscous to waxy oil texture at about 21.1°C (70°F). A composition comprising a total lipid concentrate, wherein at least 50% by weight of the total lipid concentrate comprises a polar lipid fraction, the polar lipid fraction being at least 40% by weight of the polar lipid fraction. % of glycolipids, said composition comprising no more than about 1% of said % by weight as chlorophyll concentrate. 21. The composition of claim 20, wherein the total composition comprises at least about 20% glycolipids by weight. 22. The composition of claim 21, wherein the total composition comprises at least about 40% glycolipids by weight. 21. The composition of claim 20, wherein the composition has a total lipid concentration of at least about 75% by weight of the total composition. 24. The composition of claim 23, wherein the composition has a total lipid concentration of at least about 90% by weight of the total composition. 21. The composition of claim 20, wherein at least about 70% by weight of the total lipid concentrate comprises a polar lipid fraction. 21. The composition of claim 20, wherein the composition comprises no more than about 0.1% of its total weight percent as chlorophyll concentrate. 21. The composition of claim 20, wherein the composition further comprises at least about 20% total omega-3 by weight. 28. The composition of claim 27, wherein the weight percent of total omega-3 in the composition comprises at least about 30%. 21. The composition of claim 20, wherein the composition further comprises at least about 20% total EPA by weight. 21. The composition of claim 20, wherein the composition further comprises at least about 40% phospholipid by weight of its polar lipids. 31. The composition of claim 30, wherein the phospholipid comprises at least about 60% by weight of polar lipids. 21. The composition of claim 20, wherein the composition comprises at least about 20% phospholipids by weight. 33. The composition of claim 32, wherein the composition comprises at least about 40% phospholipids by weight. 21. The composition of claim 20, wherein the composition comprises about 4% or less polysaccharide by weight. 35. The composition of claim 34, wherein the composition comprises about 1% or less polysaccharide by weight. 21. The composition of claim 20, wherein the composition exhibits a clear to deep amber color in ambient light. 21. The composition of claim 20, wherein the composition has a viscous to waxy oil texture at about 21.1°C (70°F). A preparation,
A composition comprising a total lipid concentrate, wherein at least 20% by weight of the total lipid concentrate comprises a polar lipid fraction and greater than about 30% by weight of the polar lipid fraction comprises glycolipids. a composition comprising 4% or less of the weight percent of the composition as chlorophyll concentrate;
one or more additives selected from the group consisting of other omega-3-containing oils, antioxidants, vitamins, and cannabinoids;
Preparations, including. 39. The formulation of claim 38, wherein the antioxidant is selected from the group consisting of astaxanthin, lutein, zeaxanthin, lycopene, alpha-carotene, beta-carotene, and cryptoxanthin. A method for producing an oil composition having a low chlorophyll content, the method comprising:
a. obtaining an algal oil or extract containing both polar and non-polar lipid fractions and having a chlorophyll concentrate;
b. using the polar properties of the polar lipid fraction and the non-polar lipid fraction to separate polar components from non-polar components in the algal oil or extract;
c. bleaching substantially all of the chlorophyll concentrate from the non-polar containing fraction;
d. recombining the polar lipid fraction and the non-polar lipid fraction to produce an oil composition with reduced chlorophyll content. A method for producing an oil composition having a low chlorophyll content, the method comprising:
a. obtaining an algae paste;
b. extracting the algal paste with alcohol to form an alcoholic extract of algal lipids with a low water content;
c. substantially removing the non-polar lipid fraction in the organic solvent layer by further extracting the alcoholic extract with an organic solvent to separate the non-polar lipid fraction;
d. separating an alcohol layer containing a pigment and a polar lipid;
e. Adding water to the alcohol layer and sequentially adding the organic solvent for further extraction to substantially remove the pigment fraction and forming a water-alcohol layer containing the polar lipid;
f. separating a polar lipid fraction from the water-alcohol layer by evaporation. 42. The method of claim 41, wherein the organic solvent is hexane or heptane. 42. The method of claim 41, wherein the method further comprises forming a dye concentrate by evaporation of the dye-containing fraction. 44. The method of claim 43, wherein the pigment concentrate comprises carotenoids and chlorophyll. 42. The method of claim 41, wherein the non-polar lipid fraction comprises triglycerides. 42. The method of claim 41, wherein the polar lipid fraction comprises glycolipids and phospholipids. 42. The method of claim 41, wherein the polar lipid fraction comprises EPA. 42. The method of claim 41, wherein the polar lipid fraction comprises palmitoleic acid. 42. The method of claim 41, wherein the polar lipid fraction comprises no more than about 4% chlorophyll by weight. 42. The method of claim 41, wherein the polar lipid fraction comprises about 1% or less chlorophyll by weight. 42. The method of claim 41, wherein the polar lipid fraction comprises about 0.1% or less chlorophyll by weight.

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