Edible pongamia compositions and methods for preparing and using the same

Abstract

Provided herein is a composition obtained by processing pongamia oilseeds. The resulting pongamia composition may be in the form of a meal. The pongamia composition may comprise an optimized nutritional composition obtained by subjecting pongamia oilseeds to a specific processing step. The resulting pongamia composition may also have reduced concentrations of karanjin, pongamol, and tannins. Such pongamia compositions may be suitable as foods or food ingredients for humans and other animals.

Description

Detailed Description of the Invention

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to U.S. Provisional Patent Application No. 62 / 910,315, filed October 3, 2019, which is incorporated herein by reference in its entirety.

[0002] [Technical Field] The present disclosure generally relates to compositions obtained from pongamia oilseeds. More specifically, the present disclosure relates to pongamia compositions with optimized nutritional composition obtained by subjecting pongamia oilseeds to specific processing steps. Such pongamia compositions may be suitable as foods or food ingredients for humans and other non-ruminant animals (e.g., poultry, pigs, dogs, cats, etc.).

[0003] 〔background〕 Growing concerns about population growth, climate change, and the sustainability of existing agricultural practices over the coming decades have led to a surge in research and development into alternative food sources to ensure future global food security. Renewable, plant-based food sources have spurred significant interest as an environmentally friendly and sustainable means to reduce pressure on the global food supply by providing nutrient- and protein-rich alternatives to animal-derived proteins in the human diet.

[0004] Millettia pinnata (also known as Pongamia pinnata or Pongamia glabra, or more colloquially as pongamia or karanja) is a common tree throughout Asia. It may provide a major source of plant-based protein in the future. Pongamia trees use one-tenth the land required by soybeans to produce the same amount of beans. Pongamia trees can grow on degraded soils, avoiding the deforestation problems caused by soybeans. Pongamia also produces significantly more protein and vegetable oil per acre than soybeans. Pongamia seed cake, a by-product of oil extraction from pongamia oilseeds, offers a potentially renewable source of protein, carbohydrates, and dietary fiber for food use, comparable to soybeans. However, pongamia oilseeds also have other components known in the art to have unpleasant tastes and odors, including karanjin and pongamol, and to be used as a viable food source, it is desirable to minimize the amount of karanjin and pongamol in the seed cake.

[0005] No method exists for preparing a pongamia composition with low concentrations of karanjin and pongamol while maintaining the high nutritional content (protein, carbohydrates, etc.) inherent in oilseeds. This currently prevents widespread use of pongamia-derived foods. Existing methods for removing these undesirable components in pongamia seed cake often require harsh, disruptive conditions that reduce and degrade nutrients to the extent that the nutritional value of the pongamia is seriously affected. No method exists for producing a pongamia composition with the critical balance of preserved nutritional content and sufficiently low concentrations of anti-nutrients. This prevents the incorporation of pongamia-derived proteins as an alternative food source on a scale large enough to maintain economic viability.

[0006] Therefore, there is a need in the art for a commercially viable method to obtain an edible composition from pongamia oilseed that maintains an optimum nutritional balance while minimizing components such as karanjin and pongamol.

[0007] 〔overview〕 Provided herein are compositions obtained by processing pongamia oilseeds under specific conditions to obtain compositions suitable for consumption by humans and other animals.

[0008] In some aspects, a pongamia composition is provided that includes karanjin, pongamol, or both; tannins; digestible protein; carbohydrates; antioxidants; and minerals. In some embodiments, the composition has the following (i) to (iii): (i) if present, the karanjin content is 100 ppm or less; (ii) if present, the pongamol content is 100 ppm or less; and (iii) the tannin content is 0.5% w / w or less. In some other aspects, the composition is in the form of a meal. In certain other aspects, the composition is in the form of a flour.

[0009] In other aspects, methods for preparing such pongamia compositions are provided. In some embodiments, the methods include: heating pongamia oilseeds at a temperature between 25°C and 200°C for a suitable time to prepare treated oilseeds; peeling the treated oilseeds to produce dehulled oilseeds; mechanically pressing the dehulled oilseeds to produce a de-oiled seed cake; combining the de-oiled seed cake with a solvent to prepare an extraction mixture, wherein the solvent comprises an alkyl alkanoate, an alcohol, or any combination thereof; and separating the extraction mixture into miscella and the pongamia composition. In some other aspects, the mechanical pressing is performed by an expeller or expander.

[0010] In yet other aspects, the pongamia compositions provided herein are formulated into food compositions suitable for feeding to humans and other non-ruminant animals. In some embodiments, methods are provided that include feeding any of the pongamia compositions described herein to a non-ruminant animal.

[0011] In yet another aspect, a food composition is provided comprising the pongamia composition provided herein. In one aspect, a poultry food is provided comprising a base food; and any of the pongamia compositions described herein. In another aspect, a poultry food is provided comprising corn; a soybean supplement; and any of the pongamia compositions described herein.

[0012] In yet other aspects, food compositions are provided comprising the pongamia compositions provided herein. In some other aspects, food compositions are provided, wherein the food composition is a confectionery, a condiment, a cereal composition, a baked product, a baking product, a cooking aid, a dairy product, a dietary supplement, a tabletop sweetened beverage, or other beverage product.

[0013] DESCRIPTION OF THE DRAWINGS The present application can be best understood by referring to the following description taken in conjunction with the accompanying drawings, in which like parts are referred to by like numerals, and in which:

[0014] FIG. 1 shows an exemplary method for preparing an edible pongamia composition.

[0015] Detailed Description The following description sets forth example methods, parameters, etc. However, it should be recognized that such description is not intended to limit the scope of the present disclosure, but is instead provided as a description of example embodiments.

[0016] [Pongamia composition] In some aspects, provided herein are edible compositions obtained from a process of processing pongamia oilseeds to maximize the removal of certain anti-nutritional components contained therein (e.g., karanjin, pongamol, and tannins, etc.), while optimizing the nutritional balance of other components contained therein (e.g., digestible proteins, carbohydrates, antioxidants, and minerals, etc.).

[0017] As used herein, the components of the pongamia compositions described herein (e.g., karanjin, pongamol, tannins, digestible proteins, carbohydrates, antioxidants, and minerals) refer to components endogenous to the pongamia oilseed from which the compositions are obtained.

[0018] Pongamia oilseeds are known to contain high concentrations of flavonoids containing a furan ring (known as furanoflavonoids), most notably karanjin and pongamol. Furanoflavonoids can be further identified by subclasses, such as flavones, flavonols (e.g., karanjin), and dibenzoylmethanes (e.g., pongamol). Karanjin (left) and pongamol (right) have the following structures, respectively:

[0019] [ka]

[0020] In certain aspects, an edible pongamia composition is provided that includes karanjin or pongamol, or both; tannins; digestible protein; carbohydrates; antioxidants; and minerals. In some embodiments, the composition has the following: (i) if present, the karanjin content is 100 ppm or less; (ii) if present, the pongamol content is 100 ppm or less; and (iii) the tannin content is 0.5% w / w or less.

[0021] In some other aspects, the karanjin and / or pongamol content (if present) is independently 90 ppm or less, 80 ppm or less, 70 ppm or less, 60 ppm or less, 50 ppm or less, 40 ppm or less, 30 ppm or less, 20 ppm or less, 10 ppm or less, 5 ppm or less, 2 ppm or less, 1 ppm or less, 0.5 ppm or less, or 0.1 ppm or less. In certain embodiments, the pongamia composition has a karanjin and / or pongamol concentration on the order of single digit parts per million, or fractional amounts thereof. In some embodiments, the pongamia composition has a karanjin and / or pongamol concentration of at least 0.001 ppm, at least 0.01 ppm, or at least 0.1 ppm.In certain other embodiments, the pongamia composition has a karanjin content and / or a pongamol content of 0.001 ppm to 100 ppm, 0.001 ppm to 90 ppm, 0.001 ppm to 80 ppm, 0.001 ppm to 70 ppm, 0.001 ppm to 60 ppm, 0.001 ppm to 50 ppm, 0.001 ppm to 40 ppm, 0.001 ppm to 30 ppm, 0.001 ppm to 2 ... .001ppm~10ppm, 0.001ppm~5ppm, 0.001ppm~2ppm, 0.001ppm~1ppm, 0.001ppm~0.5ppm, 0.001ppm~0.1ppm, 0.0 1ppm~100ppm, 0.01ppm~90ppm, 0.01ppm~80ppm, 0.01ppm~70ppm, 0.01ppm~60ppm, 0.01ppm~50ppm, 0.01ppm~40 ppm, 0.01ppm~30ppm, 0.01ppm~20ppm, 0.01ppm~10ppm, 0.01ppm~5ppm, 0.01ppm~2ppm, 0.01ppm~1ppm, 0.01pp m~0.5ppm, 0.01ppm~0.1ppm, 0.1ppm~100ppm, 0.1ppm~90ppm, 0.1ppm~80ppm, 0.1ppm~70ppm, 0.1ppm~60ppm, 0. The karanjin and / or pongamol concentrations are typically between 1 ppm and 50 ppm, 0.1 ppm and 40 ppm, 0.1 ppm and 30 ppm, 0.1 ppm and 20 ppm, 0.1 ppm and 10 ppm, 0.1 ppm and 5 ppm, 0.1 ppm and 2 ppm, 0.1 ppm and 1 ppm, 0.1 ppm and 0.5 ppm, 1 ppm and 100 ppm, 1 ppm and 50 ppm, 1 ppm and 20 ppm, 1 ppm and 10 ppm, 1 ppm and 5 ppm, or 1 ppm and 2 ppm. In some embodiments, the pongamia composition may have a karanjin and / or pongamol concentration of less than 100 ppm. These concentrations are undetectable by traditional hexane- and methanol-based analytical methods. In further embodiments, the pongamia composition may have a trace karanjin and / or pongamol concentration on the order of parts per billion (ppb) or parts per trillion (ppt).In some embodiments, the pongamia compositions described herein may contain trace amounts of karanjin and / or pongamol that are undetectable by the alkyl alkanoate-based microwave-assisted solvent extraction analytical methods described herein.

[0022] Similarly, the pongamia compositions of the present disclosure may have very low, undetectable levels of tannin content.

[0023] In some other aspects, the tannin content is 0.4% w / w or less, or 0.3% w / w or less. In still other aspects, the tannin content is 0.2% w / w or less, 0.1% w / w or less, 0.01% w / w or less, or 0.001% w / w or less. In some embodiments, the pongamia composition has a detectable tannin content, and the tannin content of the pongamia composition is at least 0.001% w / w, at least 0.01% w / w, or at least 0.01% w / w. In certain other embodiments, the tannin content is between 0.001% w / w and 0.4% w / w, between 0.001% w / w and 0.3% w / w, between 0.001% w / w and 0.2% w / w, between 0.001% w / w and 0.1% w / w, between 0.001% w / w and 0.01% w / w, between 0.01% w / w and 0.4% w / w, between 0.01% w / w and 0.3% w / w, 0.01%w / w~0.2%w / w, 0.01%w / w~0.1%w / w, 0.1%w / w~0.4%w / w, 0.1%w / w~0.3%w / w, 0.1%w / w~0.2%w / w, 0.2%w / w~0.4%w / w, 0.2%w / w~0.3%w / w, or 0.3%w / w~0.4%w / w.

[0024] In other embodiments, the composition further comprises other furanoflavonoids that may be present in the Pongamia oilseed from which the Pongamia composition is obtained, such as lanceolatin, candione, pongaglabrone, pongaglavon, pongaglabol, ovalifoline, sanaganone, pinatin, gamatin, pongon, glabone, carandiol, pongapine, pachycalin, pongaglavon methyl ether, isopongaglavon, methoxyisopongaglabol, pongol methyl ether, miltocalyxin, 6-methoxyisopongaglabol, pongamoside A, pongamoside B, ponganone XI, pongamoside C, glabra I, ovalitenone, ponganone IX, and pongarotene.

[0025] In some other aspects of the foregoing, the Pongamia composition has a balance of digestible protein, carbohydrates, antioxidants, and minerals to enhance bioavailability in humans and other non-ruminant animals.

[0026] In some other of the foregoing aspects, the pongamia composition is in the form of a meal. In other of the foregoing aspects, the pongamia composition is in the form of a powder.

[0027] In some embodiments, the pongamia compositions of the present disclosure may have the following (i)-(iii): (i) if present, the karanjin content is 100 ppm or less; (ii) if present, the pongamol content is 100 ppm or less; and (iii) the tannin content is 0.5% w / w or less. In other embodiments, the pongamia compositions of the present disclosure may have the following (i)-(iii): (i) if present, the karanjin content is 100 ppm or less, 90 ppm or less, 80 ppm or less, 70 ppm or less, 60 ppm or less, 50 ppm or less, 40 ppm or less, 30 ppm or less, 20 ppm or less, 10 ppm or less, 5 ppm or less, 2 ppm or less, 1 ppm or less, 0.5 ppm or less, or 0.1 ppm or less; (ii) if present, the tannin content is 0.5% w / w or less. and (iii) the tannin content is 0.5% w / w or less, 0.4% w / w or less, or 0.3% w / w or less. In still other embodiments, the tannin content is 0.2% w / w or less, 0.1% w / w or less, 0.01% w / w or less, or 0.001% w / w or less.

[0028] In some of the foregoing embodiments, the pongamia compositions disclosed herein have the following: (i) a karanjin content, if present, of 100 ppm or less; (ii) a pongamol content, if present, of 100 ppm or less; and (iii) a tannin content of 0.5% w / w or less. The pongamia compositions may be further characterized by various organoleptic properties (e.g., taste, palatability, and sensory acceptability).

[0029] For example, color can be an indication or proxy for tannin content in the pongamia composition. In further embodiments, the pongamia compositions described herein can be combined with any of the preceding embodiments. The pongamia composition can have color characteristics determined by its ultraviolet-visible spectral absorption profile or by visual comparison with an appropriate color standard (card) (e.g., USDA color standard). In certain embodiments, the pongamia composition is white.

[0030] [Method for preparing Pongamia composition] The pongamia compositions described herein are obtained from pongamia oilseeds. The pongamia oilseeds are subjected to specific heat and mechanical treatment steps. With reference to FIG. 1 , process 100 is an exemplary process for preparing a pongamia composition. In step 102, pongamia oilseeds are provided. In some embodiments, providing the oilseeds may further comprise removing and / or separating the oilseeds from the pods or shells. Removing the oilseeds from the pods or shells may comprise manual removal or mechanical crushing to open the pods. In certain embodiments, separating the oilseeds from the pods or shells may comprise manual separation, sieving / sorting, or aerodynamic separation (e.g., weight sorting by suction).

[0031] Referring again to Figure 1, the pongamia oilseeds are heated at a suitable temperature for a suitable time in step 104, thereby providing processed pongamia oilseeds. The heat treatment can help promote the breakdown of membranes that bind the oilseeds to the oilseed husk, thereby facilitating downstream processing to remove the husk from the processed oilseeds. In some embodiments, the temperature and duration of the heat treatment can affect the compatibility of the dehulled oilseeds with downstream mechanical pressing processes.

[0032] In some embodiments, the oilseeds are heated to a temperature of at least 25° C., at least 30° C., at least 35° C., at least 40° C., at least 50° C., at least 60° C., at least 70° C., at least 75° C., at least 80° C., at least 90° C., at least 100° C., at least 110° C., at least 120° C., at least 125° C., at least 130° C., at least 140° C., at least 150° C., at least 160° C., at least 170° C., at least 175° C., at least 180° C., or at least 190° C. In other embodiments, the oilseeds are heated to a temperature of 200° C. or less, 190° C. or less, 180° C. or less, 170° C. or less, 160° C. or less, 150° C. or less, 140° C. or less, 130° C. or less, 125° C. or less, 120° C. or less, 110° C. or less, 100° C. or less, 90° C. or less, 80° C. or less, or 75° C. or less. In some variations, the oilseeds are heated at a temperature of 25°C to 200°C, 30°C to 200°C, 60°C to 200°C, 60°C to 180°C, 60°C to 150°C, 60°C to 120°C, 80°C to 200°C, 80°C to 180°C, 80°C to 150°C, 80°C to 120°C, 100°C to 200°C, 100°C to 180°C, 100°C to 150°C, 100°C to 120°C, 120°C to 200°C, 120°C to 180°C, 120°C to 150°C, 150 to 200°C, 150 to 180°C, or 180°C to 200°C.

[0033] In some embodiments, the oilseeds are heated for a period of at least 5 minutes, at least 10 minutes, at least 15 minutes, at least 20 minutes, at least 25 minutes, at least 30 minutes, at least 45 minutes, at least 1 hour, at least 90 minutes, at least 120 minutes, at least 150 minutes, or at least 180 minutes. In other embodiments, the oilseeds are heated for a period of 1 day or less, 20 hours or less, 15 hours or less, 10 hours or less, 5 hours or less, 4 hours or less, 180 minutes or less, 120 minutes or less, 90 minutes or less, 60 minutes or less, 45 minutes or less, 30 minutes or less, 25 minutes or less, 20 minutes or less, 15 minutes or less, or 10 minutes or less. In other embodiments, the oilseeds are heated for a time period of 5 minutes to 3 hours, 5 minutes to 2 hours, 5 minutes to 90 minutes, 5 minutes to 1 hour, 5 minutes to 30 minutes, 5 minutes to 15 minutes, 15 minutes to 3 hours, 15 minutes to 2 hours, 15 minutes to 90 minutes, 15 minutes to 1 hour, 15 minutes to 30 minutes, 30 minutes to 3 hours, 30 minutes to 2 hours, 30 minutes to 90 minutes, 30 minutes to 1 hour, or 30 minutes to 45 minutes. Suitable temperatures and / or residence times for heat treatment may include any combination of times and temperatures described herein. For example, in one embodiment, the oilseeds are heated at 25°C to 200°C for 5 minutes to 3 hours. In some embodiments, the oilseeds are heated for a time period of 5 minutes to 3 hours, 5 minutes to 2 hours, 5 minutes to 90 minutes, 5 minutes to 1 hour, 5 minutes to 30 minutes, 5 minutes to 15 minutes, 15 minutes to 3 hours, 15 minutes to 2 hours, 15 minutes to 90 minutes, 15 minutes to 1 hour, 15 minutes to 30 minutes, 30 minutes to 3 hours, 30 minutes to 2 hours, 30 minutes to 90 minutes, 30 minutes to 1 hour, or 30 minutes to 45 minutes, and at temperatures between 25°C and 200°C, 30°C and 20°C. It is heated to temperatures of 0°C, 60°C to 200°C, 60°C to 180°C, 60°C to 150°C, 60°C to 120°C, 80°C to 200°C, 80°C to 180°C, 80°C to 150°C, 80°C to 120°C, 100°C to 200°C, 100°C to 180°C, 100°C to 150°C, 100°C to 120°C, 120°C to 200°C, 120°C to 180°C, 120°C to 150°C, 150°C to 200°C, 150°C to 180°C, or 180°C to 200°C.

[0034] Referring again to FIG. 1 , the processed oilseeds are then dehulled at step 106. Any suitable technique known in the art for removing the hulls from oilseeds can be used. For example, in some aspects, the processed oilseeds are subjected to an abrasive force to remove the hulls. In certain aspects, dehulling may be performed using an attrition mill or impeller, or mechanical equivalent. In one aspect, the dehulling process does not utilize a wet removal method (e.g., blanching, alkaline and / or aqueous dissolution, etc.). In certain aspects, the pongamia oilseeds undergo a heat treatment prior to dehulling. In some aspects, such a heat treatment is a dry dehulling process. Such a dry dehulling process is distinct from a wet dehulling process, which may include, for example, blanching. In certain embodiments, the pongamia oilseeds that undergo heat treatment, as well as the oilseeds and pongamia compositions obtained from the methods described herein, can be characterized by their moisture content. In some embodiments, the treated oilseeds resulting from the heat treatment have a moisture content of 20% w / w or less, 17% w / w or less, 15% w / w or less, 12% w / w or less, 10% w / w or less, or 8% w / w or less without a further drying step. In other embodiments, the treated oilseeds resulting from the heat treatment have a moisture content of 5% w / w to 20% w / w, 5% w / w to 17% w / w, 5% w / w to 15% w / w, 5% w / w to 12% w / w, 5% w / w to 10% w / w, 5% w / w to 8% w / w, 8% w / w to 20% w / w, 8% w / w to 17% w / w, 8% w / w to 15% w / w, 8% w / w to 12% w / w, In yet another aspect, the treated oilseeds obtained from the thermal treatment may have a moisture content of 8% to 10% w / w, 10% to 20% w / w, 10% to 17% w / w, 10% to 15% w / w, 10% to 12% w / w, 12% to 20% w / w, 12% to 17% w / w, 12% to 15% w / w, 15% to 20% w / w, 15% to 17% w / w, or 17% to 20% w / w. In yet another aspect, the treated oilseeds obtained from the thermal treatment may be dried to adjust the moisture content before a mechanical treatment step to remove oil and obtain a de-oiled seed cake (or press cake).

[0035] Dehulled oilseeds can be described by many characteristics, including, for example, the weight percentage of dehulled oilseeds, tannin content, moisture content, or particle size distribution. In some embodiments, the percentage of dehulled oilseeds can be quantified by visual inspection of the coated and uncoated surface area of ​​the oilseeds. In certain aspects, the dehulled oilseeds have 40% w / w to 100% w / w, 40% w / w to 80% w / w, or 40% w / w to 70% w / w of the oilseeds having less than 50% of their total surface area covered by the husk. In certain aspects, the dehulled oilseeds have an average tannin content of 0.5% w / w or less, 0.4% w / w or less, or 0.3% w / w or less. In still other embodiments, the dehulled oilseeds have an average tannin content of 0.2% w / w or less, 0.1% w / w or less, 0.01% w / w or less, or 0.001% w / w or less. In some embodiments, the dehulled oilseeds have an average tannin content of at least 0.001% w / w, at least 0.01% w / w, or at least 0.01% w / w. In certain embodiments, the tannin content is between 0.001% w / w and 0.4% w / w, between 0.001% w / w and 0.3% w / w, between 0.001% w / w and 0.2% w / w, between 0.001% w / w and 0.1% w / w, between 0.001% w / w and 0.01% w / w, between 0.01% w / w and 0.4% w / w, between 0.01% w / w and 0.3% w / w. / w, 0.01% w / w to 0.2% w / w, 0.01% w / w to 0.1% w / w, 0.1% w / w to 0.4% w / w, 0.1% w / w to 0.3% w / w, 0.1% w / w to 0.2% w / w, 0.2% w / w to 0.4% w / w, 0.2% w / w to 0.3% w / w, or 0.3% w / w to 0.4% w / w.

[0036] In some aspects, removing the hulls from the processed pongamia oilseeds results in a mixture comprising dehulled oilseeds and separated hulls. As such, the method may further comprise separating the separated hulls from the dehulled oilseeds. In some embodiments, the method further comprises separating the dehulled oilseeds from the separated hulls by manual separation, sieving or screening, or aerodynamic separation (i.e., weight sorting by suction).

[0037] Referring again to FIG. 1 , in step 108, the dehulled oilseeds are mechanically pressed to remove oil and provide a de-oiled seed cake (or press cake). In some aspects, the dehulled oilseeds are mechanically pressed using an expeller. In other aspects, the dehulled oilseeds are mechanically pressed using an expander. In yet other aspects, the dehulled oilseeds are mechanically pressed using an extruder. One or more iterations of the mechanical pressing step can be applied to the dehulled oilseeds and / or the resulting de-oiled seed cake to provide a final de-oiled seed cake for use in the subsequent solvent extraction step. In other embodiments, the de-oiled seed cake may be further crushed prior to solvent extraction to provide a de-oiled seed cake having a particular particle size distribution.

[0038] The de-oiled seed cake may be described by other characteristics, such as karanjin concentration, oil content, moisture content, and particle size distribution. For example, in some embodiments, the de-oiled seed cake has a karanjin concentration of at least 200 ppm, or at least 500 ppm. In some embodiments, the de-oiled seed cake has 8-40% by weight, 10-35% by weight, or 8-30% by weight oil.

[0039] Referring again to FIG. 1 , in step 110, the de-oiled seed cake undergoes solvent extraction. In some embodiments, the de-oiled seed cake is combined with the solvent in an extractor. In certain embodiments, the de-oiled seed cake and solvent are mixed, stirred, or agitated in the extractor. In some embodiments, heat may be used in the solvent extraction step. It is noted that the foregoing method may include variations in other parameters that may be part of the combining step, including, for example, residence time of the extraction mixture in the extractor, extractor temperature and pressure, extractor chain speed, particle size distribution of the de-oiled seed cake, ratio of de-oiled seed cake to solvent, and feed rates of the de-oiled seed cake and solvent into the extractor.

[0040] In some embodiments, the solvent comprises an alkyl alkanoate or an alcohol, or any combination thereof. In one embodiment, the solvent comprises an alcohol. Alcohol solvents can include, for example, methanol, propanol, ethanol, butanol, or pentanol.

[0041] In another embodiment, the solvent comprises an alkyl alkanoate. In certain embodiments, the alkyl of the alkyl alkanoate is methyl, ethyl, propyl, or butyl. In certain embodiments, the solvent comprises methyl alkanoate, ethyl alkanoate, propyl alkanoate, or butyl alkanoate, or any combination thereof. In other embodiments, the alkanoate of the alkyl alkanoate is methanoate, ethanoate, propionate, butanoate, or pentanoate. In other embodiments, the solvent comprises alkyl methanoate, alkyl ethanoate, alkyl propionate, alkyl butanoate, alkyl pentanoate, or any combination thereof. In certain embodiments, the solvent comprises alkyl ethanoate. In certain embodiments, the solvent comprises ethyl acetate. Alkyl alkanoate solvents may include, for example, methyl methanoate, methyl ethanoate, methyl propanoate, methyl butanoate, methyl pentanoate, ethyl methanoate, ethyl ethanoate, ethyl propanoate, ethyl butanoate, ethyl pentanoate, propyl methanoate, propyl ethanoate, propyl propanoate, propyl butanoate, propyl pentanoate, butyl methanoate, butyl ethanoate, butyl propanoate, butyl butanoate, and butyl pentanoate, and any combination thereof. In certain embodiments, the solvent comprises an alkyl alkanoate solvent selected from the group consisting of methyl ethanoate, methyl propanoate, methyl butanoate, ethyl methanoate, ethyl ethanoate, ethyl propanoate, ethyl butanoate, propyl methanoate, propyl ethanoate, propyl propanoate, propyl butanoate, butyl methanoate, butyl ethanoate, butyl propanoate, and butyl butanoate.

[0042] In one embodiment, the solvent comprises an alkyl alkanoate of formula (I):

[0043] [ka]

[0044] where: R 1 is C1-C4 alkyl; and R 2 is hydrogen or C1-C4 alkyl.

[0045] In some embodiments, R 1 is C1-C4 alkyl. In other embodiments, R 2 is hydrogen or C1-C4 alkyl. In certain embodiments, R 1 and R 2 is independently C1-C4 alkyl. In certain other embodiments, R 1 is C1-C4 alkyl, and R 2 is hydrogen. R 1 In some embodiments, R is C1-C4 alkyl. 1 is CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2-, CH3CH2(CH3)CH-, (CH3)2CHCH2-, or (CH3)3C-. In some embodiments, R 2 is hydrogen. In other embodiments, R 2 is C1-C4 alkyl. 2 In certain embodiments, where R is C1-C4 alkyl, 2 is CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2-, CH3CH2(CH3)CH-, (CH3)2CHCH2-, or (CH3)3C-. 2 is hydrogen, CH3-, CH3CH2-, or CH3CH2CH2-. In still other embodiments, R 1 is CH3CH2- and R 2 is CH3-. In some embodiments, R 1 is CH3CH2- or CH3CH2CH2CH2-, and R 2 is hydrogen. In other embodiments, R 1 is CH3CH2CH2- and R 2 is CH3CH2CH2- or CH3CH2CH2CH2-. In other embodiments, R1 is C1-C3 alkyl. In still other embodiments, R 1 is methyl, ethyl, n-propyl, or isopropyl. 1 is ethyl. In some embodiments, R 1 is C2-C4 alkyl. In certain embodiments, R 1 is ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or t-butyl. 2 is hydrogen or C1-C3 alkyl. In certain embodiments, R 2 is methyl, ethyl, n-propyl, or isopropyl. 2 is methyl. In yet another embodiment, R 1 is ethyl, and R 2 is methyl. In yet another embodiment, R 2 is hydrogen, ethyl, or n-propyl. 1 is ethyl, n-propyl, or n-butyl, and R 2 is hydrogen, methyl, ethyl, or n-propyl. 2 is methyl. In yet another embodiment, R 1 is ethyl, and R 2 is methyl.

[0046] In some embodiments, the solvent is prepared in situ. For example, an alkyl alkanoate can be prepared by mixing the corresponding alcohol with the corresponding carboxylic acid. In some embodiments, the alkyl alkanoate of formula (I) is prepared by mixing the alcohol R 1 -OH to carboxylic acid R 2 -COOH, where R 1 and R 2is as defined above. In certain embodiments where the alkyl alkanoate is ethyl acetate, the ethyl acetate is prepared in situ by mixing ethanol with acetic acid. In some embodiments, the alkyl alkanoate is prepared in situ prior to combining the alkyl alkanoate solvent with the de-oiled seed cake. In other embodiments, the alkyl alkanoate is prepared in situ using the de-oiled seed cake. For example, in some aspects, the method comprises combining the de-oiled seed cake with a solvent comprising ethyl acetate, wherein the ethyl acetate is prepared in situ. The method comprises mixing the de-oiled seed cake with ethanol and acetic acid.

[0047] Any combination of the extraction solvents described herein may also be used.

[0048] The solvent extraction process produces an extraction mixture, which is then separated in step 120 to produce the miscella and pongamia compositions described herein. In some embodiments, the miscella comprises the liquid fraction of the extraction mixture (e.g., oil, solvent, and any soluble compounds), while the pongamia composition is primarily composed of the residual insoluble solid material (or meal) remaining in the deoiled seed cake. Any suitable solid-liquid separation method can be used in this separation process, including, for example, filtration and decanting.

[0049] In some embodiments, the miscella comprises a mixture of extracted oil, karanjin, pongamol, other furanoflavonoids, and a solvent. In other embodiments, the miscella has a karanjin concentration of 4000 ppm or more. In certain embodiments, the miscella has a karanjin concentration of 4000 ppm or more as measured by the methods described above. In certain embodiments, the miscella may be characterized by oil content, water content, moisture content, solids content, or other properties known in the art.

[0050] It should be understood that in other embodiments, process 100 may include one or more additional steps. For example, the resulting pongamia composition may contain residual levels of solvent. Thus, in some embodiments, the method may include a dry-heating or baking step to reduce the level of residual solvent. In other embodiments, the extraction mixture is subjected to microwave irradiation after the combining step and before the separating step.

[0051] [Analytical measurement] Determination of the concentrations of karanjin, pongamol, and other furanoflavanoids in pongamia compositions after processing (hulling, de-oiling, solvent extraction) or at any stage of the processing process (intact oilseeds, de-hulled oilseeds, de-oiled seed cake) can be carried out by microwave-assisted solvent extraction using appropriate alkyl alkanoate solvents to obtain alkyl alkanoate extracts. The alkyl alkanoate extracts can then be subjected to various liquid chromatography and / or mass spectrometry techniques (e.g., HPLC / MS) to quantify the concentrations of karanjin, pongamol, and other furanoflavanoids in the extracts that represent pongamia compositions. Suitable alkyl alkanoate solvents include those alkyl alkanoate solvents described above, such as alkyl alkanoate solvents selected from the group consisting of methyl methanoate, methyl ethanoate, methyl propanoate, methyl butanoate, methyl pentanoate, ethyl methanoate, ethyl ethanoate, ethyl propanoate, ethyl butanoate, ethyl pentanoate, propyl methanoate, propyl ethanoate, propyl propanoate, propyl butanoate, propyl pentanoate, butyl methanoate, butyl ethanoate, butyl propanoate, butyl butanoate, butyl pentanoate, and any combination thereof.

[0052] In some embodiments, following separation of the irradiated mixture into an extracted pongamia composition and a solvent extract, the method further comprises analyzing the solvent extract. As described herein, analyzing the solvent extract comprises measuring the concentrations of karanjin and pongamol in the solvent extract. The concentrations of karanjin and pongamol in the solvent extract serve as surrogate measurements of the concentrations of karanjin and pongamol originally present in the pongamia composition. In some embodiments, the method comprises measuring the concentrations of karanjin and pongamol in the solvent extract. In some embodiments, the method comprises measuring the individual concentrations of one or more furanoflavonoids in the solvent extract. In certain embodiments, the method comprises measuring the concentration of karanjin in the solvent extract. In other embodiments, the method comprises measuring the concentration of pongamol in the solvent extract.

[0053] The concentration of karanjin, pongamol, and other furanoflavonoids in the solvent extract can be measured using analytical separation and detection techniques known in the art. In some embodiments, the concentration of karanjin, pongamol, and other furanoflavonoids is determined by high-performance liquid chromatography (HPLC). In other embodiments, the concentration of karanjin, pongamol, and other furanoflavonoids is determined by HPLC-mass spectrometry (HPLC-MS). In certain embodiments, the concentration of karanjin, pongamol, and other furanoflavonoids is determined by HPLC-tandem mass spectrometry (HPLC-MS / MS). In some embodiments, the concentration of karanjin, pongamol, and other furanoflavonoids is determined by HPLC-ultraviolet-visible spectrophotometry (HPLC-UV-vis).

[0054] In some aspects, the analytical methods described herein can be referred to as "microwave-assisted alkyl alkanoate solvent extraction analytical methods." In certain embodiments where a specific alkyl alkanoate is used as the alkyl alkanoate solvent, the extraction method can be more specifically referred to by the specific alkyl alkanoate used. For example, in certain embodiments of the aforementioned method, where the alkyl alkanoate solvent comprises ethyl acetate, the analytical method can be referred to as "microwave-assisted ethyl acetate extraction analytical method."

[0055] It should be appreciated that a "microwave-assisted alkyl alkanoate solvent extraction analytical method" includes embodiments in which the alkyl alkanoate solvent contains at least one alkyl alkanoate solvent and, optionally, one or more non-alkyl alkanoate co-solvents. For example, a "microwave-assisted ethyl acetate extraction analytical method" can refer to the use of an alkyl alkanoate solvent containing ethyl acetate and, optionally, one or more co-solvents.

[0056] Use of Pongamia Composition The pongamia compositions described herein (including compositions produced according to any of the methods described herein) can be used as foods or food ingredients suitable for feeding humans and other animals. In some embodiments, methods are provided for feeding any of the pongamia compositions described herein to animals.

[0057] In some embodiments, the animal is a human. In other embodiments, the animal is a non-ruminant animal. As used herein, "non-ruminant animal" should be understood to include animals with a single-chamber stomach (i.e., monogastric). Examples of non-ruminant animals include, for example, poultry, pigs, non-ruminant cattle, dogs, cats, mice, and fish. In certain embodiments, the animal is poultry. In one embodiment, the animal is a chicken.

[0058] In one aspect, the pongamia compositions described herein may be used as a stand-alone food or food product, or in another aspect, the pongamia compositions described herein may be utilized as a food or food ingredient within a larger food or food composition.

[0059] In one aspect, provided herein is a food composition comprising any of the pongamia compositions described herein. In some embodiments, the food composition is a food product (e.g., a confectionery, a condiment, a cereal composition, a baked product, a baking product, a cooking aid, a dairy product, a dietary supplement, and a tabletop sweetener formulation), a beverage, or other beverage product (e.g., a beverage mix or concentrate). In certain other embodiments, the food composition is a grain product or pasta (e.g., a health bar, a grain-based bar), a meat product (e.g., a meat patty comprising the pongamia composition), a dairy product (e.g., a flavored milk drink, a milkshake, a protein shake, a milk-based meal replacement, a yogurt), a plant-based protein product (e.g., an egg product or analog, a meat substitute or analog), processed fruits and fruit juices (e.g., fruit juices, fruit juices, fruit-flavored drinks, fruit smoothies), processed vegetables and vegetable juices (e.g., vegetable juices and smoothies), soups and soup mixes (e.g., prepared soups, dry soup mixes, concentrated soups), or snack foods (e.g., chips, popcorn, extruded snacks).

[0060] In some aspects, provided herein is an animal food comprising any of the pongamia compositions described herein.

[0061] In certain aspects, a poultry food is provided that includes a base diet and any of the pongamia compositions described herein. A suitable base diet for the food compositions described herein may be any non-pongamia-derived material known in the art as forage or fodder. Examples of such materials include hay, straw, silage, grains, legumes, food scraps, and food by-products that have been processed to be suitable for certain non-ruminant animals. In certain embodiments, the base diet may include one or more foods selected from the group consisting of wheat meal, corn meal, barley meal, oat meal, soybean meal, cottonseed meal, safflower seed meal, sunflower seed meal, peanut meal, groundnut meal, and hay. In certain embodiments, the base diet includes wheat meal, corn meal, soybean meal, or any combination thereof.

[0062] In some embodiments, a poultry food is provided that includes corn, a soybean supplement, and any of the pongamia compositions described herein. The pongamia composition is incorporated as a pongamia supplement. In some embodiments, the pongamia supplement and the soybean supplement are present in a weight ratio of 1:1 to 1:25.

[0063] In other aspects, there is provided a container comprising a pongamia composition described herein, or an article of manufacture, such as a foodstuff, comprising a pongamia composition described herein; and a label comprising instructions for using such a pongamia composition or foodstuff.

[0064] In yet another aspect, there is provided a kit comprising a pongamia composition as described herein, or a foodstuff comprising a pongamia composition as described herein; and a package insert comprising instructions for using such pongamia composition or foodstuff.

[0065] [Example] The subject matter of the present disclosure may be better understood by reference to the following examples, which are provided by way of illustration of the present invention and not by way of limitation.

[0066] Example A - Measurement Protocol Example A1: Microwave-assisted extraction (MAE) method for determining the concentration of karanjin, pongamol, and other furanoflavonoids The following example describes a general protocol for determining the concentrations of karanjin and pongamol in Pongamia samples.

[0067] Microwave-assisted extraction of karanjin and pongamol. 0.5 g of pongamia seed cake is added to a microwave extraction tube. 15 mL of either ethyl acetate is then added to the sample tube and vortexed to mix. The sample is then extracted using a microwave extractor under the following conditions: 1) ramp to 70°C for 15 minutes, 2) hold at 70°C for 10 minutes. Once cooled, the supernatant is filtered using filter paper in a Buchner funnel under vacuum.

[0068] HPLC Standard Solutions. Commercially available karanjin and pongamol were mixed with methanol to prepare the following HPLC standard solutions: 0.05, 0.1, 0.2, 0.5, 1.0, 5.0, and 20.0 μg / mL.

[0069] HPLC Instrumentation. HPLC analysis is performed using a mobile phase consisting of solvent A (0.1% formic acid in HPLC water) and solvent B (0.1% formic acid in acetonitrile). The injection volume is 2 μL, and the flow rate is 0.75 mL / min. The column is a C18 5 μm, 50 × 2 mm HPLC column. All HPLC analyses are performed in negative ion mode. MS parameters are: curtain gas, 30 psi; collision gas, 4 psi; nebulizer gas (GS1), 50 psi; drying gas (GS2), 50 psi; ion spray voltage, 5000; temperature, 500 °C; declustering potential (DP), 51 V; entrance potential, 10 V; collision energy (CE), 60 eV for karanjin and 30 eV for pongamol.

[0070] MS / MS quantification of karanjin and pongamol in extracts. Multiple reaction monitoring (MRM) ion transitions are monitored for both karanjin and pongamol. The levels of karanjin and pongamol present in the extracted samples are calculated using Analyst version 1.6.3. Briefly, the peak areas of karanjin and pongamol in the extracted samples are compared to the peak areas of calibration standards to determine the parts per million of karanjin and pongamol.

[0071] Example A2: Determination of shedding rate and tannin content in Pongamia samples The following example describes a general protocol for determining the percentage of husk present and the tannin content in a pongamia sample.

[0072] Dehulling rate. A representative sample of oilseeds is taken to be assessed for dehulling rate. The oilseeds and fragments are sorted into two different groups based on a visual assessment of whether each oilseed or fragment retains more than 50% of its original husk coating. The two groups of oilseeds are weighed separately. The percentage of successful dehulling is calculated as the weight of oilseeds with less than 50% of their original husk intact multiplied by 100% over the sum of the weights of the oilseeds in both groups.

[0073] Tannin Content. The protocol for measuring tannin content in pongamia oilseeds and downstream pongamia products (e.g., deoiled seed cake) was carried out according to the ISO standard protocol for measuring tannin content in sorghum (ISO 9648, ultraviolet spectrophotometry). The sample to be tested was shaken with dimethylformamide. The dimethylformamide mixture was centrifuged and the supernatant was isolated. Ferric ammonium citrate and ammonia were added to an aliquot of the supernatant. The absorbance of the solution was determined by UV spectrophotometry at 525 nm. The tannin content was measured using a calibration curve prepared using tannic acid.

[0074] Example A3: Measurement of composition profile The example below describes a general protocol for analyzing the compositional profile of Pongamia samples for amino acid and other macronutrient content.

[0075] Total Protein. Total protein content is determined by placing a pongamia seed cake sample in the combustion chamber of a protein analyzer, measuring the total nitrogen content of the gas produced by combustion, and calculating protein from the observed nitrogen content using the standard nitrogen conversion factor (protein content = 6.25 x nitrogen content).

[0076] Total Ash: The total ash content is determined by placing a seed cake sample (2 g) in a crucible, dyeing the sample in an oven, ashing the sample in a muffle furnace at 600°C, and weighing the ash (AOAC 942.05 Reference Method).

[0077] Total Moisture Content: Total moisture content is determined by heating a weighed sample in a forced air oven at 130°C for 2 hours and measuring the difference in sample weight, with the percentage difference calculated as moisture content (AOCS BA 2A-38 reference method).

[0078] Total Fat Content. Total fat content was determined by solvent extraction with petroleum ether under reflux (AOCS BA3-38 reference method, modified).

[0079] Total Carbohydrates. Total carbohydrate content is calculated as a percentage of pongamia seed cake (100%) minus the sum of the total ash content (%), total protein content (%), total moisture content (%), and total fat content (%).

[0080] Example B - Large-Scale Extraction Example B1: Preparation of dehulled, deoiled pongamia composition <Thermo-mechanical treatment> Pongamia pods were harvested and the oilseeds were removed from the pods. The isolated oilseeds were then subjected to various heat treatments at different temperatures (60°C, 120°C, 150°C, and 180°C) for different times (5 to 180 minutes). The heat treatments were carried out by placing the pongamia oilseeds in an aluminum baking tray (49.7 cm x 29.5 cm x 8.1 cm) with a perforated base at 75% capacity and placing the filled tray in a forced convection oven preheated to the indicated temperature.

[0081] Fourteen separate combinations of temperature and time were evaluated for heat treatment, as shown in Table 8 below. In addition to the 14 trials, a 100 kilogram scale trial was also conducted under the same conditions as trial number 013. As a control, pongamia oilseed obtained from the same harvest group as the oilseed evaluated in the 14 trials was kept under ambient conditions without any thermo-mechanical treatment.

[0082] After heat treatment, the heat-treated oilseeds were immediately transferred into and passed through an impact huller (Codema VSH 2096, 5 hp motor, rotating impeller) to remove the hulls. Oilseeds from each of the 14 trials were passed through the impact huller. After dehulling, the oilseeds were removed from the impact huller and placed into a multi-aspirator (Kice 6E-6 aspirator, 5 hp fan, cyclone, rotating airlock, 6 inch duct) to separate the hulls from the dehulled oilseeds.

[0083] The percentage of dehulled oilseeds obtained from this method was evaluated according to the protocol described in Example A2 above. The tannin content of the dehulled test samples was also determined according to the protocol described in Example A2 above.

[0084] Table 1 shows the results of measuring the percentage of dehulled Pongamia oilseeds and the tannin content of dehulled seeds for the 14 trials and large-scale trials carried out.

[0085] [Table 1]

[0086] Mechanical pressing and solvent extraction After removing the hulls from the oilseeds, the dehulled oilseeds were mechanically pressed to remove the pongamia oil. The dehulled oilseeds were passed through a small-scale mechanical expeller press (Taby Model 40A Expeller Press). Dehulled oilseeds processed under the above conditions were found to be compatible with the small-scale mechanical expeller press, producing an oil stream and a separate solid de-oiled seed cake. Table 2 below shows the mass percentage of oil removed from the dehulled oilseed samples processed in Table 1 above.

[0087] [Table 2]

[0088] The dehulled and deoiled seed cake (Test No. 013) was extracted with ethyl acetate in an immersion extractor (3 hour residence time, 5:1 solvent:feed ratio). After solvent extraction and miscella removal, the resulting ethyl acetate extracted pongamia meal was analyzed for karanjin concentration, pongamol concentration, and oil content as described in the protocols of Examples A1 and A3 above. The resulting ethyl acetate extracted pongamia meal was determined to have 17 ppm karanjin, 10 ppm pongamol, and 0.80% residual oil. [Brief explanation of the drawings]

[0089] [Figure 1] FIG. 1 shows an exemplary method for preparing an edible pongamia composition.

Claims

1. 1. A pongamia composition comprising: Karanjin, Pongamor, or both; tannins; Digestible protein; carbohydrates; an antioxidant; and mineral, The composition comprises a Pongamia composition comprising: (i) a Pongamia extract; (i) if present, the karanjin content is not more than 100 ppm; (ii) if present, the pongamol content is 100 ppm or less; and (iii) the tannin content is less than or equal to 0.5% w / w;

2. 10. The composition of claim 1, wherein the composition has a tannin content of 0.3% w / w or less.

3. 3. The composition of claim 1, wherein the composition is in the form of a meal.

4. 3. The composition of claim 1, wherein the composition is in the form of a powder.

5. A method for preparing the Pongamia composition according to any one of claims 1 to 4, comprising: heating the pongamia oilseeds at a temperature of 60°C to 180°C for at least 5 minutes to provide treated oilseeds; dehulling the treated oilseeds to produce dehulled oilseeds; mechanically pressing the dehulled oilseeds to produce a de-oiled seed cake; combining the de-oiled seed cake with a solvent to prepare an extraction mixture, the solvent comprising an alkyl alkanoate; and separating the extraction mixture into miscella and the pongamia composition.

6. 6. The method of claim 5, wherein the mechanical pressing step is performed by a press.

7. The method of claim 5 , wherein the mechanical pressing step is performed by an expander.

8. A method comprising the step of feeding a non-human non-ruminant animal the Pongamia composition of any one of claims 1 to 4 as food.

9. The method of claim 8, wherein the non-ruminant animal is poultry.

10. 10. The method of claim 9, wherein the poultry is a chicken.

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