Sorghum-derived food coloring and antioxidant supplement compositions

Abstract

The present disclosure relates to a composition derived from an extract of a proprietary variety of sorghum that provides excellent natural color antioxidant and functional ingredient properties. The composition can be used in product coloring applications such as food, consumables, clothing, fabrics, polymers, beverages, dietary supplements, etc. Due to its good properties, the composition can be included in products where a red dye or colorant is required, either alone or with other colorants to create different colors, hues, or shades.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to U.S. Provisional Patent Application No. 63 / 305,928, filed February 2, 2022, the entire contents of which are incorporated herein by reference.

[0002]

[0002] This disclosure relates to compositions derived from extracts of proprietary varieties of sorghum that provide superior natural color, antioxidant and other functional ingredient properties. [Background technology]

[0003]

[0003] Identifying resources for degradable and safe compositions is increasingly desirable to eliminate complex manufacturing and toxic by-products as well as to reduce risks to users. Natural resources may be particularly promising due to the ease of decomposition and regeneration of resources and their understood safety for human application. Thus, there is a need to create useful products from natural resources. Summary of the Invention [Means for solving the problem]

[0004] A first aspect of the present disclosure relates to a composition comprising luteolinidin, apigeninidin and a polymer, either alone or in combination with any other aspect herein.

[0005] A second aspect of the present disclosure relates to the composition of the first aspect, wherein the polymer comprises luteloin and luteolin-7-glycoside, either alone or in combination with any other aspect herein.

[0005]

[0006] A third aspect of the present disclosure relates to the composition of the second aspect, wherein the polymer further comprises luteolinidin and apigeninidin, either alone or in combination with any other aspect herein.

[0006]

[0007] A fourth aspect of the present disclosure relates to the composition of the first aspect, further comprising luteolin monomer, either alone or in combination with any other aspect herein.

[0008] A fifth aspect of the present disclosure relates to the composition of the first aspect, further comprising luteolin-7-glucoside monomer, either alone or in combination with any other aspect herein.

[0007]

[0009] A sixth aspect of the present disclosure relates to the composition of the first aspect, further comprising a quercetin monomer or an ether thereof, either alone or in combination with any other aspect herein.

[0008]

[0010] A seventh aspect of the present disclosure relates to the composition of the first aspect, further comprising a benzletin monomer, either alone or in combination with any other aspect herein.

[0011] An eighth aspect of the present disclosure relates to the composition of the first aspect, further comprising a methoxyluteolinidin monomer, either alone or in combination with any other aspect herein.

[0009]

[0012] A ninth aspect of the present disclosure relates to the composition of the first aspect, further comprising one or more isoschaftosides, either alone or in combination with any other aspect herein.

[0010]

[0013] A tenth aspect of the present disclosure relates to the composition of the first aspect, further comprising ferulic acid, either alone or in combination with any other aspect herein.

[0014] An eleventh aspect of the present disclosure relates to the composition of the first aspect, further comprising p-coumaric acid, either alone or in combination with any other aspect herein.

[0011]

[0015] A twelfth aspect of the present disclosure relates to the composition of the first aspect, either alone or in combination with any other aspect herein, for use as a dietary supplement, food colorant, cosmetic ingredient, antioxidant, or dye.

[0012]

[0016] A thirteenth aspect of the present disclosure, either alone or in combination with any other aspect herein, relates to a composition comprising luteolin monomer, luteolin-7-glucoside monomer, and quercetin monomer or ethers thereof.

[0013]

[0017] A fourteenth aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising an apigeninidin monomer, either alone or in combination with any other aspect herein.

[0018] A fifteenth aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising luteolinidin monomer, either alone or in combination with any other aspect herein.

[0014]

[0019] A sixteenth aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising a polyphenol polymer, wherein the polyphenol polymer comprises luteolin and apigeninidin, either alone or in combination with any other aspect herein.

[0015]

[0020] A seventeenth aspect of the present disclosure relates to the composition of the sixteenth aspect, wherein the polyphenol polymer further comprises a dimethyl ether of quercetin, either alone or in combination with any other aspect herein.

[0016]

[0021] An eighteenth aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising a benzletin monomer, either alone or in combination with any other aspect herein.

[0022] A nineteenth aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising an apigeninidin monomer, either alone or in combination with any other aspect herein.

[0017]

[0023] A twentieth aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising a methoxyluteolinidin monomer, either alone or in combination with any other aspect herein.

[0018]

[0024] A twenty-first aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising one or more isoschaftosides, either alone or in combination with any other aspect herein.

[0019]

[0025] A twenty-second aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising ferulic acid, either alone or in combination with any other aspect herein.

[0026] A twenty-third aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising p-coumaric acid, either alone or in combination with any other aspect herein.

[0020]

[0027] A twenty-fourth aspect of the present disclosure relates to the composition of the thirteenth aspect, further comprising one or more polymers composed of linked luteolinidin, luteolin, and quercetin or ethers thereof, either alone or in combination with any other aspect herein.

[0021]

[0028] A twenty-fifth aspect of the present disclosure relates to the composition of any preceding aspect, either alone or in combination with any other aspect herein, derived from the leaves of sorghum cultivar Red Natural.

[0022]

[0029] A twenty-sixth aspect of the present disclosure relates to a food colorant comprising the dry composition of the first or thirteenth aspect, either alone or in combination with any other aspect herein.

[0030] A twenty-seventh aspect of the present disclosure relates to a food colorant comprising the composition of the first or thirteenth aspect and a diluent, either alone or in combination with any other aspect herein.

[0023]

[0031] A twenty-eighth aspect of the present disclosure relates to a food colorant comprising the composition of the first or thirteenth aspect and a preservative, either alone or in combination with any other aspect herein.

[0032] A twenty-ninth aspect of the present disclosure relates to an edible antioxidant comprising the dry composition of the first or thirteenth aspects, either alone or in combination with any other aspect herein.

[0024]

[0033] A thirtieth aspect of the present disclosure relates to an edible antioxidant comprising the composition of the first or thirteenth aspects and a diluent, either alone or in combination with any other aspect herein.

[0025]

[0034] A thirty-first aspect of the present disclosure relates to an edible antioxidant comprising the composition of the first or thirteenth aspect and a preservative, either alone or in combination with any other aspect herein.

[0026]

[0035] A thirty-second aspect of the present disclosure, either alone or in combination with any other aspect herein, relates to a method for preparing the composition of the first or thirteenth aspects, comprising solubilizing Red Natural sorghum leaves and obtaining an extract therefrom.

[0027]

[0036] A thirty-third aspect of the present disclosure relates to the method of the twenty-eighth aspect, further comprising the step of drying the extract, either alone or in combination with any other aspect herein.

[0037] A thirty-fourth aspect of the present disclosure, either alone or in combination with any other aspect herein, relates to the method of the twenty-eighth aspect, further comprising the steps of obtaining a polymer fraction within the extract, hydrolyzing the polymer fraction to prepare monomer units, and adding the monomer units to the composition. [Brief description of the drawings]

[0028] [Figure 1A]

[0038] FIG. 1 shows the absorbance at 475 to 550 nm of an extract from Red Natural leaves. [Figure 1B]

[0039] FIG. 1 shows the absorbance at 475 to 550 nm of an extract from sorghum Triple Trust Feed Milo leaves. [Diagram 2]

[0040] FIG. 13 shows HPLC-PDA-ESI-MS / MS analysis of standardized leaf extracts from the RedNatural cultivar, where the absorbance of the eluate was measured from 260 to 700 nm in addition to the absorbance from 475 to 550 nm. [Diagram 3]

[0041] FIG. 1 shows an annotated HPLC chromatogram of Red Natural leaf extract. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0029]

[0042] The present disclosure relates to a composition of compounds obtained from an extract of sorghum, particularly sorghum cultivar RedNatural. In some embodiments, the extract is obtained from the leaves of sorghum cultivar RedNatural. Certain cultivars of sorghum may accumulate deoxyanthocyanidins and other compounds in specialized tissues (e.g., leaf sheaths) or potentially in specific infection sites. In some embodiments, the compositions of the present disclosure are in aqueous or hydrophilic solutions. In other embodiments, the compositions of the present disclosure may be compatible with hydrophobic or organic solutions. In some embodiments, the compositions or portions thereof may be dissolved in the solution. In some embodiments, the compositions or portions thereof may be suspended or immiscible in the solution. In further embodiments, the compositions of the present disclosure may be in the form of a powder or other dry or semi-dry form, such as a paste. It is a further embodiment that the compositions of the present disclosure may be incorporated into many products, such as food for consumption, beverages, cosmetics, creams, tablets, emulsions, supplements, and many more human consumer products.

[0030]

[0043] It is an aspect of the present disclosure that some compositions of the present disclosure have strong dyeing ability so that the compositions of the present disclosure can be utilized as dyes and / or colorants. As specified herein, the compositions of the present disclosure are extracted from sorghum, particularly sorghum cultivar RedNatural. Thus, the compositions are distinct from plants, but all of the compounds therein are non-toxic and / or safe for human application or consumption. It is a further aspect of the present disclosure that some compositions of the present disclosure have strong antioxidant activity. In some aspects, the compositions can be used in applications for coloring products such as food, consumables, clothing, fabrics, polymers, beverages, dietary supplements, etc. Due to the good properties, the compositions may be included in products where a red dye or red colorant is required, alone or with other colorants to form different colors, hues, or shades.

[0031]

[0044] In some embodiments, the present disclosure relates to a composition of compounds obtained from an extract of sorghum cultivar RedNatural. In some embodiments, the composition comprises a compound extracted from the leaves of sorghum cultivar RedNatural. For the sake of brevity, reference to RedNatural should be understood to refer to the plant sorghum cultivar RedNatural or a part thereof.

[0032]

[0045] In some embodiments, the compounds of the composition are obtained from a series of steps of concentration and isolation from processed RedNatural leaves. However, it is clear that RedNatural does not have to be the actual source of all the compounds of the composition of the present disclosure. For example, as discussed below, in some embodiments of the present disclosure, the composition includes luteolin-7-glucoside and / or luteolin. Although such compounds may be obtained from RedNatural, the composition of the present disclosure does not require that it is extracted therefrom or that all the compounds included in the composition are from RedNatural.

[0033]

[0046] In some embodiments of the present disclosure, the composition of the present disclosure comprises one or more of luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin (7-O-methyl and / or 5-O-methyl), dimethoxyluteolinidin, p-coumaric acid, ferulic acid, and any combination thereof. In some embodiments, the composition may comprise one or more deoxyanthocyanins selected from luteolinidin, apigeninidin, methoxyluteolinidin, and combinations thereof. In some embodiments, the composition may comprise one or more schaftside isomers (including schaftside 1 and schaftside 2) and / or quercetin dimethyl ether (DME) (including quercetin DME1 and quercetin DME2).

[0034]

[0047] In some embodiments, the composition of the present disclosure may comprise a polymer. In some embodiments, the polymer may comprise one or more of the polyphenols and / or flavonoids described herein. In some embodiments, the polymer may comprise cross-linked or covalently bonded compounds comprising at least one of luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftside isomers, one or more quercetin DME, or any combination thereof. In some embodiments, the polymer may comprise at least one deoxyanthocyanin of luteolinidin, apigeninidin, methoxyluteolinidin, and / or dimethoxyluteolinidin. In some embodiments, the polymer may further comprise at least one or more amino acids, peptides, proteins, carbohydrates, lignins, tannins, additional phenols and / or flavonoids, or any combination thereof. It is understood that the polymers of the present disclosure need not be limited or restricted to polymers of only polyphenol or flavonoid compounds.

[0035]

[0048] In some embodiments, the compositions may comprise one or more of the individual compounds luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftside isomers (including schaftside 1 and schaftside 2), quercetin, and / or one or more quercetin DME, or any combination thereof. In some embodiments, the compositions may comprise one or more or polymeric compounds of crosslinked or covalently bonded compounds comprising luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftside isomers, quercetin DME, or any combination thereof. In some embodiments, compositions of the present disclosure may include one or more of luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftside isomers, quercetin and / or quercetin DME, or any combination thereof, as well as polymeric compounds comprising one or more of luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftside isomers, quercetin DME, or any combination thereof.

[0036]

[0049] In some aspects, the present disclosure relates to compositions of deoxyanthocyanins of luteolinidin, apigeninidin, methoxyluteolinidin (and / or dimethoxyluteolinidin), luteolinidin and apigeninidin, luteolinidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), or luteolinidin, apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin). In some aspects, the present disclosure relates to compositions comprising a polymer at least partially comprised of deoxyanthocyanins of luteolinidin, apigeninidin, methoxyluteolinidin (and / or dimethoxyluteolinidin), luteolinidin and apigeninidin, luteolinidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), or luteolinidin, apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin). In a further aspect, the present disclosure provides deoxyanthocyanins of luteolinidin, apigeninidin, methoxyluteolinidin (and / or dimethoxyluteolinidin), luteolinidin and apigeninidin, luteolinidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), or luteolinidin, apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), and luteolinidin, apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin). The present invention relates to a composition of polymers at least partially comprising the deoxyanthocyanins luteolinidin, apigeninidin, methoxyluteolinidin (and / or dimethoxyluteolinidin), luteolinidin and apigeninidin, luteolinidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin), or luteolinidin, apigeninidin and methoxyluteolinidin (and / or dimethoxyluteolinidin).

[0037]

[0050] In some embodiments, the composition may comprise 0.1-70% by weight of the composition of at least one of luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftosid isomers, quercetin, and / or quercetin DME, and may comprise about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68 and 69% w / w.

[0038]

[0051] In some embodiments, the compositions of the present disclosure include one or more polyphenol and / or flavonoid compounds as described herein. In some embodiments, the polyphenol and / or flavonoid content of the composition may be about 0.1 to about 50% by weight of the composition, including about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, and 49% w / w.

[0039]

[0052] In some embodiments, the composition may comprise 0.1-30% by weight of a polymer, the polymer being a crosslinked or covalently bonded compound comprising at least in part one or more of luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftosid isomers, quercetin and / or quercetin DME, comprising about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, and 29% w / w by weight of the composition.

[0040]

[0053] In some embodiments, the composition may comprise about 0.1 to about 20% w / w apigeninidin, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0 , 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0041]

[0054] In some embodiments, the composition may comprise about 0.1 to about 20% w / w luteolinidin, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0 , 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0042]

[0055] In some embodiments, the composition may comprise about 0.1 to about 20% w / w luteolin, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0043]

[0056] In some embodiments, the composition may comprise about 0.1 to about 20% w / w methoxyluteolinidin and / or dimethoxyluteolinidin, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0044]

[0057] In some embodiments, the composition may comprise about 0.1 to about 20% w / w luteolin-7-glycoside, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0045]

[0058] In some embodiments, the composition may comprise about 0.1 to about 20% w / w benzletin, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0046]

[0059] In some embodiments, the composition may contain about 0.1 to about 20% w / w quercetin DME1 and / or quercetin DME2, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5 8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0047]

[0060] In some embodiments, the composition may comprise about 0.1 to about 20% w / w of shaftside 1 and / or shaftside 2, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0048]

[0061] In some embodiments, the composition may comprise about 0.1 to about 20% w / w p-coumaric acid, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0049]

[0062] In some embodiments, the composition may comprise about 0.1 to about 20% w / w ferulic acid, and may be about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2.0, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 30.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7.0, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8, 7.9, 8.0, 8.1, 8.2, 8.3, 8.4, 8.5, 8.6, 8.7, 8.8, 8.9, 9.0, 9.1, 9.2, 9.3, 9.4, 9.5, 9.6, 9.7, 9.8, 9.9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 19% w / w.

[0050]

[0063] In some embodiments, the composition of the present disclosure may further comprise any additional components necessary to adapt the composition to the intended final product.For example, the composition may further comprise additional dyes to achieve different hues.In some embodiments, the composition may comprise lipids, emulsifiers, surfactants and / or creams to provide a topical composition.

[0051]

[0064] In some embodiments, the composition of the present disclosure comprises luteolinidin, apigeninidin, and a polymer as described herein. In some embodiments, the polymer may at least partially comprise luteolinidin and / or apigeninidin. In some embodiments, the polymer may at least partially comprise luteolin and / or luteolin-7-glycoside. In some embodiments, the polymer may at least partially comprise luteolin, luteolin-7-glycoside, luteolinidin, and apigeninidin.

[0052]

[0065] In some embodiments, the composition may comprise luteolinidin, apigeninidin, luteolin, and a polymer described herein.In some embodiments, the composition may comprise luteolinidin, apigeninidin, luteolin luteolin-7-glycoside, and a polymer described herein.

[0053]

[0066] In some embodiments, the compositions of the present disclosure may include luteolinidin, apigeninidin, quercetin and / or ethers thereof, and polymers described herein. In some embodiments, the compositions may include luteolinidin, apigeninidin, luteolin, luteolin-7-glycoside, quercetin and / or ethers thereof, and polymers described herein.

[0054]

[0067] In some embodiments, the compositions of the present disclosure may comprise luteolinidin, apigeninidin, benzletin, and a polymer as described herein. In some embodiments, the compositions may further comprise luteolin and / or luteolin-7-glycoside and / or quercetin and / or ethers thereof.

[0055]

[0068] In some embodiments, the compositions of the present disclosure may comprise luteolinidin, apigeninidin, methoxyluteolinidin (and / or dimethoxyluteolinidin), and a polymer as described herein. In some embodiments, the compositions may further comprise luteolin and / or benzletin and / or luteolin-7-glycoside and / or quercetin and / or ethers thereof.

[0056]

[0069] In some embodiments, the compositions of the present disclosure may comprise luteolinidin, apigeninidin, one or more schaftosides, and a polymer as described herein. In some embodiments, the compositions may further comprise luteolin and / or benzletin and / or methoxyluteolinidin (and / or dimethoxyluteolinidin) and / or luteolin-7-glycoside and / or quercetin and / or ethers thereof.

[0057]

[0070] In some embodiments, the compositions of the present disclosure may comprise luteolinidin, apigeninidin, ferulic acid, and a polymer as described herein. In some embodiments, the compositions may further comprise luteolin and / or benzletin and / or methoxyluteolinidin (and / or dimethoxyluteolinidin) and / or luteolin-7-glycoside and / or one or more schaftosides and / or quercetin and / or ethers thereof.

[0058]

[0071] In some embodiments, the compositions of the present disclosure may comprise luteolinidin, apigeninidin, p-coumaric acid, and a polymer as described herein. In some embodiments, the compositions may further comprise luteolin and / or benzletin and / or ferulic acid and / or methoxyluteolinidin (and / or dimethoxyluteolinidin) and / or luteolin-7-glycoside and / or one or more schaftosides and / or quercetin and / or ethers thereof.

[0059]

[0072] In some embodiments, the compositions of the present disclosure may include luteolin, luteolin-7-glycoside, and quercetin and / or its ethers. In some embodiments, the compositions of the present disclosure may include luteolin, luteolin-7-glycoside, quercetin and / or its ethers, and a polymer as described herein.

[0060]

[0073] In some embodiments, the compositions of the present disclosure may include luteolin, luteolin-7-glycoside, apigeninidin, and quercetin and / or ethers thereof. In some embodiments, the compositions of the present disclosure may include luteolin, luteolin-7-glycoside, apigeninidin, quercetin and / or ethers thereof, and a polymer as described herein.

[0061]

[0074] In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, luteolinidin, and quercetin and / or its ethers. In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, luteolinidin, quercetin and / or its ethers, and a polymer as described herein. In some embodiments, the composition of the present disclosure may further comprise apigeninidin.

[0062]

[0075] In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, and quercetin and / or its dimethyl ether. In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, quercetin and / or its dimethyl ether, and a polymer as described herein. In some embodiments, the composition of the present disclosure may further comprise apigeninidin and / or luteolinidin.

[0063]

[0076] In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, benzletin, and quercetin and / or its ethers. In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, benzletin, quercetin and / or its ethers, and a polymer as described herein. In some embodiments, the composition of the present disclosure may further comprise apigeninidin and / or luteolinidin and / or dimethylquercetin ether.

[0064]

[0077] In some embodiments, the compositions of the present disclosure may include luteolin, luteolin-7-glycoside, methoxyluteolinidin (and / or dimethoxyluteolinidin), and quercetin and / or its ethers. In some embodiments, the compositions of the present disclosure may include luteolin, luteolin-7-glycoside, methoxyluteolinidin (and / or dimethoxyluteolinidin), quercetin and / or its ethers, and a polymer as described herein. In some embodiments, the compositions of the present disclosure may further include apigeninidin and / or luteolinidin and / or benzletin and / or dimethylquercetin ether.

[0065]

[0078] In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, one or more schaftsides, and quercetin and / or its ethers. In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, one or more schaftsides, quercetin and / or its ethers, and a polymer as described herein. In some embodiments, the composition of the present disclosure may further comprise apigeninidin and / or luteolinidin and / or benzletin and / or methoxyluteolinidin (and / or dimethoxyluteolinidin) and / or dimethylquercetin ether.

[0066]

[0079] In some embodiments, the compositions of the present disclosure may comprise luteolin, luteolin-7-glycoside, ferulic acid, and quercetin and / or its ethers. In some embodiments, the compositions of the present disclosure may comprise luteolin, luteolin-7-glycoside, ferulic acid, quercetin and / or its ethers, and a polymer as described herein. In some embodiments, the compositions of the present disclosure may further comprise apigeninidin and / or luteolinidin and / or benzletin and / or methoxyluteolinidin (and / or dimethoxyluteolinidin) and / or one or more schaftosides and / or dimethylquercetin ethers.

[0067]

[0080] In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, p-coumaric acid, and quercetin and / or its ethers. In some embodiments, the composition of the present disclosure may comprise luteolin, luteolin-7-glycoside, p-coumaric acid, quercetin and / or its ethers, and a polymer as described herein. In some embodiments, the composition of the present disclosure may further comprise apigeninidin and / or luteolinidin and / or benzletin and / or methoxyluteolinidin (and / or dimethoxyluteolinidin) and / or ferulic acid and / or one or more schaftosides and / or dimethylquercetin ether.

[0068]

[0081] In some embodiments, the compositions of the present disclosure may include one or more phenolic and / or flavonoid compounds obtained from sorghum cultivar Red Natural. In some embodiments, the compounds may be obtained from the leaves of sorghum cultivar Red Natural. In some embodiments, the compounds are extracted by solubilizing the compounds within the leaves, followed by a series of filtration and concentration steps to obtain a solution or slurry of the desired compounds. In some embodiments, additional compounds may be removed by changing the pH and / or temperature, followed by filtration of the remaining compounds.

[0069]

[0082] Below, an analysis of the compounds identified in RedNatural is described, but it is clear that the compositions described herein can include additional isolated compounds from RedNatural, and also include the addition of additional compounds such as additional amino acids, peptides, vitamins, antioxidants, surfactants, polymers, emulsifiers, water, flavonoids, and the like. In some embodiments, the compositions may include food colorants and / or antioxidants. Such may include dry compositions, as well as the presence of preservatives. Such may also include diluents.

[0070]

[0083] Also contemplated is a method for preparing the composition described herein. In an embodiment, such a method may include solubilizing Red Natural sorghum leaves and obtaining an extract therefrom. Such a method may further include drying the extract. Such a method may include obtaining a polymer fraction in the extract, hydrolyzing the polymer fraction to prepare monomer units, and adding the monomer units to the composition. EXAMPLES

[0071]

[0084] A concentrated solution of compounds obtained after solubilization and pH adjustment of RedNatural leaves was monitored at 475-550 nm and compared to an extract from the sorghum cultivar Triple Trust Feed Milo. Figure 1A shows the spectrum obtained from RedNatural and Figure 1B shows the spectrum from the control (Triple Trust Feed Milo). RedNatural contains red compounds that are not obtained in appreciable amounts from the leaves of commonly used sorghum cultivars.

[0072]

[0085] HPLC-PDA-ESI-MS / MS analysis was performed, in which the absorbance of the eluate was measured from 260 to 700 nm in addition to that from 475 to 550 nm. The data obtained are shown in Figure 2. The identity of the various peaks was determined by mass spectrometry according to standard methods in analytical chemistry, and the presence of significant amounts of luteolin and glycosides was notable.

[0073]

[0086] The three dried extracts from RedNatural leaves were then evaluated for their total phenolic, flavonoid and pigment content using spectrophotometric and chromatographic techniques. The samples belonged to three different production batches, identified as B30, B31 and B34. The powders were dissolved in deionized water, followed by spectrophotometric and chromatographic analysis. The composition was evaluated using ultra-high performance liquid chromatography coupled with photodiode array detection and electrospray ionization with tandem mass spectrometry (uHPLC-PDA-ESI-MS / MS). The total phenolic content of the extracts was 410.9 ± 18.8 mg gallic acid equivalents per gram of sample (about 41% by weight). Of which, flavonoids accounted for 144.9 ± 4.0 mg catechin equivalents per gram of sample (about 15%) and total pigments were 86.3 ± 1.6 mg luteolinidin equivalents per gram of sample (about 8%). The main compounds identified were p-coumaric acid, ferulic acid, two schaftosid isomers, luteolin-7-glucoside, luteolin, quercetin dimethyl ether, benzletin, and the deoxyanthocyanins (luteolinidin, apigeninidin, and methoxyluteolinidin). These compounds accounted for approximately 45% of the degradation peaks in the chromatogram. In addition, the analysis also revealed the presence of polymeric compounds, evidenced by a rise in the baseline of the chromatogram, which accounted for approximately 79% of the total area under the PDA max plot. Acid hydrolysis of the powder resulted in a decrease in the polymeric compounds and an increase in the peak areas of the main phenols previously identified, suggesting that the polymers are at least partially composed of the same compounds found as free components in the extract. Acid hydrolysis of the polymer-enriched fraction obtained using size-exclusion chromatography released luteolin, previously identified in the free state, and a further compound tentatively identified as tyramine. Overall, monomeric compounds accounted for approximately 21% of the uHPLC-PDA signal, whereas polymeric compounds accounted for approximately 79%. The amount of variation in composition can be assessed by the variance of the three measurements. Figure 3 shows the annotated HPLC diagram of the leaf extract.

[0074]

[0087] Various modifications of the present disclosure in addition to those shown and described herein will be apparent to those skilled in the art, and such modifications are also intended to fall within the scope of the appended claims.

[0075]

[0088] It is understood that all reagents are available from sources known in the art unless otherwise specified.

[0089] Of course, it is also to be understood that the disclosure is not limited to the specific embodiments and methods described herein, since the specific components and / or conditions may vary. Moreover, the terms used herein are used only for the purpose of describing the specific embodiments of the disclosure, and are not intended to be limiting in any way. Also, it is understood that, although terms such as "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or sections, these elements, components, regions, layers and / or sections should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a "first element", "component", "region", "layer" or "section" discussed below may be referred to as a second (or other) element, component, region, layer or section without departing from the teachings of the present specification. Similarly, as used herein, the singular forms "a", "an" and "the" are intended to include the plural forms including "at least one" unless the content clearly indicates otherwise. "Or" means "and / or." As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. As used herein, the terms "comprises" and / or "comprising," or "includes" and / or "including" specify the presence of stated features, regions, integers, steps, operations, elements, and / or components, but are further understood to not exclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and / or groups thereof. The term "or combinations thereof" refers to combinations including at least one of the foregoing elements.

[0076]

[0090] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by those skilled in the art to which this disclosure belongs. Terms such as those defined in commonly used dictionaries should be interpreted to have a meaning consistent with the meaning in the context of the relevant art and this disclosure, and it is further understood that they are not interpreted in an idealized or overly formal sense unless expressly defined in this specification.

[0077]

[0091] Reference will be made in detail to exemplary compositions, embodiments and methods of the present disclosure, which constitute the best mode of carrying out the present disclosure currently known to the inventors. The figures are not necessarily to scale. However, it should be understood that the disclosed embodiments are merely illustrative of the present disclosure, which may be embodied in various alternative forms. Therefore, the specific details disclosed herein should not be interpreted as limiting, but merely as representative basis for any embodiment of the present disclosure and / or as representative basis for teaching those skilled in the art how to utilize the present disclosure in various ways.

[0078]

[0092] The patents, publications, and applications mentioned in this specification are indicative of the level of those skilled in the art to which this disclosure pertains, and are herein incorporated by reference to the same extent as if each individual patent, publication, or application was specifically and individually indicated to be incorporated by reference.

[0079]

[0093] The foregoing description is illustrative of particular embodiments of the present disclosure but is not intended to limit its practice. The following claims, including all equivalents thereof, are intended to define the scope of the present disclosure.

Claims

1. 1. A composition for use in dye or antioxidant applications, comprising a concentrate of deoxyanthocyanidins, said concentrate comprising luteolinidin and apigeninidin.

2. The composition of claim 1 further comprising methoxyluteolinidin.

3. 10. The composition of claim 1, further comprising benzletine.

4. 10. The composition of claim 1, further comprising a polymer, wherein the polymer comprises at least one monomer of luteolin, luteolin-7-glucoside, luteolinidin, apigeninidin, benzletin, methoxyluteolinidin, dimethoxyluteolinidin, p-coumaric acid, ferulic acid, one or more schaftosid isomers, one or more quercetin DME, or any combination thereof.

5. The composition of claim 4, wherein the polymer comprises luteoin and luteolin-7-glycoside.

6. 6. The composition of claim 5, wherein the polymer further comprises luteolinidin and apigeninidin.

7. The composition of claim 1 further comprising luteolin monomer.

8. 10. The composition of claim 1, further comprising a quercetin monomer or an ether thereof.

9. 10. The composition of claim 1, further comprising a methoxyluteolinidin monomer.

10. 10. The composition of claim 1, wherein the composition is derived in part from sorghum leaves.

11. A colorant comprising the dry composition of claim 1.

12. An antioxidant comprising the dry composition of claim 1.

13. 10. A method for preparing the composition of claim 1, comprising solubilizing sorghum tissue and obtaining an extract therefrom.

14. 14. The method of claim 13, further comprising drying the extract.

15. 14. The method of claim 13, further comprising obtaining a polymer fraction within the extract.

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