Composition containing a polyketide pigment

Abstract

The present invention provides a food coloring composition. In particular, the present invention provides a composition or coloring composition comprising at least one polyphenol pigment (i) and one or more of the following compounds (ii): carotenoids (such as lycopene, bixin and / or norbixin), rosmarinic acid, chlorogenic acid, rutin glucoside, (gamma) cyclodextrin and / or tocopherol.

Description

Technical Field

[0001] Technical Field of the Invention The present invention relates to food coloring compositions and, in particular, the present invention provides a composition or coloring composition comprising (i) a polyphenol dye and (ii) a carotenoid (such as lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol, and a method for producing said stabilized coloring composition.

[0002] The present invention also relates to the use of the food coloring compositions described herein in the coloring of food products, and to food products comprising the food coloring compositions described herein.

Background Art

[0003] Background of the Invention Synthetic red dyes, especially azo dyes such as Allura Red AC (Red Dye 40), are commonly used in food coloring due to their attractive cost, bright red color, and excellent stability to light, heat, oxygen, pH, and low microbial contamination. However, these dyes have some side effects on health due to their toxicity.

[0004] This major limitation has increased the pressure to find alternatives to these dyes. Currently, the most popular red food colorants are anthocyanins (E163), red beetroot (E162), and carmine (E120). However, these dyes suffer from a number of drawbacks.

[0005] Anthocyanins are unstable at pH>3, which limits their use in dairy products, bakery, and meat applications where the pH ranges from 5.5 to 6.5. Beetroot extract has poor stability due to several decomposition reactions against heat stress such as hydrolysis, decarboxylation, oxidation and photodegradation of betacyanin molecules (Herbach, K.M., Stintzing, F.C. and Carle, R. (2006), Betalain Stability and Degradation - Structural and Chromatic Aspects. Journal of Food Science, 71: R41 - R50).

[0006] Carmine is a bright red - pink pigment obtained from an aluminum complex derived from carminic acid. Since this pigment is very stable against light and heating, it has become an attractive product in the food industry. However, since this pigment is extracted from an animal source (cochineal insects), it is not a vegan - friendly product. In addition, since this pigment is chemically modified (complexed with aluminum), it is not completely natural.

[0007] Faced with these constraints, manufacturers are compelled to find alternatives that satisfy natural, vegan, halal and kosher consumers. Therefore, the search for new food dyes based on natural compounds with a high stability profile is currently extremely active.

[0008] As a natural red solution, Monascus pigments have been used as natural colorants and natural food additives in East Asia. This odorless and tasteless pigment is produced by various types of Monascus (M. purpureus i) through fermentation, is known to be stable in the pH range of 2 - 10, and is stable to heat, making it an attractive sustainable product. Monascus purpureus is preserved at the general microbial centre of the China Committee for Culture Collection of Microorganisms, and the preservation number of Monascus purpureus is CGMCC No.11317.T.

[0009] However, Monascus pigments have poor stability against light; several papers have reported their sensitivity to sunlight, and more specifically, their sensitivity to ultraviolet irradiation. Under light irradiation, it has been reported that the Monascus side chain is cleaved, generating superoxide anions, hydroxyl radicals, and other radicals. These radicals further react with the double bonds in the pigment structure, which disrupts the double bond conjugation in the Monascus pigment, thus causing loss of color characteristics and fading. Several attempts have been made to improve the stability of Monascus and its pigments such as Monascus during, for example, the fermentation process.

[0010] CN201410118907 reports a fermentation method for preparing a highly light-stable Monascus red pigment. Yang Yijin et al. reported stabilization using rutin and quercetin in Microbiology Journal (2021, volume 12, DOI = 10.3389 / fmicb.2021.678903), but these molecules have poor solubility in aqueous conditions, restricting their use to alcoholic beverages. Chinese Patent CN102702780A discloses a method for preventing the fading of Monascus red pigment, which essentially involves dissolving the Monascus red pigment in a 0.1 percent solution of tryptophan, histidine, tyrosine, or methionine.

[0011] Chinese Patent CN103589189A discloses the application of retrograded starch in reducing the photo-fading of Monascus red pigment, which involves adding retrograded starch to an aqueous solution of Monascus red pigment to completely adsorb the aqueous solution of Monascus red pigment onto the retrograded starch, thereby obtaining a Monascus red pigment product with a function of resisting light radiation.

[0012] Chinese Patent CN101530190B discloses a food Monascus red pigment fixing agent composed of 5 - 10% catechin, 10 - 25% vitamin C, 30 - 40% glucose, and the remaining rutin.

[0013] Despite these numerous tests, the stabilization of polyketide pigments (such as azaphilones) has not been successfully achieved, and there is still a need to find an efficient solution to improve their stability.

Summary of the Invention

[0014] Summary of the Invention In the present invention, we have introduced a novel stabilization method using natural water-soluble or dispersible components to enhance the photo-stability of polyketide pigments such as azaphilones.

[0015] The applicant has surprisingly and unexpectedly found that the use of carotenoids (such as lycopene) and / or other water-soluble compounds, such as rosmarinic acid, chlorogenic acid, rutin glucoside and / or tocopherol, etc., can provide protection against the fading of polyketide pigments such as azaphilones when exposed to light. Without being bound by theory, polyketide pigments such as azaphilones are protected due to the reduction of UV light absorption, which is a major factor leading to this photo-damage.

[0016] This improvement helps to stabilize polyketide pigments such as azaphilones in beverages and confectionery, etc., thus presenting a bright and stable red color. With the solution described in this application, benefits such as its clean and non-GMO label, good nutritional value, and neutral taste without off-notes in the end-use can be obtained.

[0017] Accordingly, the present invention provides a method for stabilizing the color of a polyketide pigment, comprising contacting (i) a polyketide pigment with (ii) a carotenoid (such as lycopene), rosmarinic acid, rutin glucoside, cyclodextrin and / or tocopherol, wherein the resulting polyketide pigment is photo-stable.

[0018] In another aspect, the present invention provides a stabilized pigment obtained according to the stabilization method of the present invention. In another aspect, the present invention provides a coloring composition comprising a stabilized dye and, in addition, a suitable carrier or excipient. In another aspect, the present invention provides a foodstuff, a pharmaceutical, a dietary supplement, a fragrance or a cosmetic product comprising a stabilized dye according to the invention or a coloring composition according to the invention, which has optionally been exposed to light.

[0019] In another aspect, the present invention provides a method for manufacturing a foodstuff, a pharmaceutical, a dietary supplement, a fragrance or a cosmetic product, comprising the step of incorporating a stabilized dye according to the invention or a coloring composition according to the invention into the foodstuff, the pharmaceutical, the dietary supplement, the fragrance or the cosmetic product.

[0020] In another aspect, the present invention provides a method for manufacturing a foodstuff, a pharmaceutical, a dietary supplement, a fragrance or a cosmetic product, comprising the step of incorporating component (i) and component (ii) as defined in any one of the preceding claims, especially when the product is liquid or semi-solid, where component (i) is added directly to the product and as a result product (ii) is also added to the product, or component (ii) is added directly to the product and as a result product (i) is also added to the product. BRIEF DESCRIPTION OF THE DRAWINGS

[0021]

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[0022]

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[0023] Definition As used herein, the term "pigment" refers to a substance that imparts color by absorbing or scattering light of different wavelengths. The term "coloring composition" refers to any pigment formulated with one or more other products, such as a carrier and the like.

[0024] The term "color" refers to color characteristics such as hue, chroma, purity, saturation, intensity, vividness, color value, lightness, brightness and darkness, and the parameters of color model systems used to describe these characteristics, such as the Commission Internationale de l’Eclairage CIE 1976 CIELAB colour space L * a * b * values. The term "hue" refers to the color characteristic that gives a name to a color, such as red, blue and brown.

[0025] Detailed description The terms "comprises", "comprising", "has", "includes", "including", "contains", "containing", or any other variation thereof are in an open-ended form and are intended to cover non-exclusive inclusion of elements. Thus, an article, device, compound, composition, combination, method, or process described as "comprising", "having", "including", or "containing" a list of elements may include not only those elements but also other elements not expressly listed, described, or depicted in the specification or claims. An element or feature preceded by the words "...comprising a", "...containing a", "...having a", or "...including a" does not, in the absence of further limitations, exclude the presence or inclusion of additional elements or features in the article, device, compound, composition, combination, method, or process comprising, containing, having, or including that element or feature.

[0026] The terms "a" and "an" are defined as one or more terms, unless otherwise clearly defined or restricted by other words in this specification. An element or feature starting with "a" or "an" may be interpreted as one of the described elements or features or one or more elements or features. By way of example, CGA may be interpreted as one chlorogenic acid or one or more chlorogenic acids.

[0027] Terms such as "about," "approximately," "essentially," "substantially," their other versions, or other similar relative terms, or similar approximation terms, are defined as being as close as understood by those skilled in the art. These terms are defined, by way of non-limiting, exemplary embodiments, to be within 20% of the recited value, or within 10% of the recited value, or within 5% of the recited value, or within 4% of the recited value, or within 3% of the recited value, or within 2% of the recited value, or within 1% of the recited value, or within 0.5% of the recited value, or within 0.25% of the recited value, or within 0.1% of the recited value.

[0028] In the present disclosure, when an amount is described in weight percent, it should be understood that any and all amounts within the range including the endpoints are intended to be considered as clearly disclosed. For example, the disclosure of "a range of about 1 to about 10" is to be read as indicating every possible number along the continuum between about 1 and about 10. The inventors recognize and understand that every data point within the range is considered to be specified, and that the inventors own the entire range and all points within the range.

[0029] To avoid doubt, preferences, options, specific features, etc. shown for a particular aspect, feature or parameter of the present invention are to be considered as disclosed in combination with all other preferences, options, specific features, etc. shown for the same or other aspects, features and parameters of the present invention, unless otherwise stated in the context.

[0030] The following text defines a broad description of numerous different aspects of the present disclosure. The description should be construed as illustrative, and since it is impracticable, if not impossible, to describe every possible aspect, it does not describe every possible aspect. The features, characteristics, components, compositions, elements, products, steps, or methodologies described herein are understood to be capable of deleting, combining, or substituting all or part of the other features, properties, components, compositions, elements, products, steps, or methodologies described herein. Numerous alternative aspects can be accomplished using either the prior art included within the scope of the claims or technologies developed after the filing date of this patent.

[0031] Preferred features and / or any features of the present invention will now be defined. Unless the context otherwise requires, any aspect of the invention may be combined with any other aspect of the invention. Any preferred or any feature of any aspect may, unless the context otherwise requires, be used alone or in combination with any aspect of the invention and any other preferred or any feature.

[0032] Method for stabilizing a polyketide pigment Surprisingly, by combining a polyketide pigment (such as azaphilone), more specifically a Monascus pigment, with one or more of carotenoids (such as lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, and / or tocopherol, a Monascus pigment with improved stability against light exposure is obtained compared to the polyketide pigment (such as azaphilone), more specifically the polyketide pigment (such as azaphilone), more specifically the Monascus pigment alone.

[0033] Accordingly, the present invention provides a method for stabilizing the color of a polyketide pigment (such as azaphilone), which comprises contacting (i) the polyketide pigment with (ii) a carotenoid (such as lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol, wherein the resulting polyketide pigment (such as azaphilone) is light-stable.

[0034] The present invention also provides a method for producing a light-stable polyketide pigment (such as azaphilone), which comprises the step of contacting (i) the polyketide pigment with (ii) a carotenoid (such as lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol, and optionally the step of mixing (i) and (ii).

[0035] Thus, there is also provided a "stabilized polyketide pigment" or a "light-stable polyketide pigment" obtained by using the method of the present invention. Both terms, "stabilized polyketide pigment" and "light-stable polyketide pigment", are interchangeable in this description.

[0036] Without wishing to be bound by theory, it is believed that the polyketide pigment (such as azaphilone) and lycopene form a complex that provides a stabilized coloring composition having a color such as red, orange or yellow that is stable to light exposure (i.e., the hue does not fade when exposed to light).

[0037] As used herein, "contacting" may correspond to a physical interaction between the polyketide pigment (such as azaphilone) and the compound (ii) described herein, a carotenoid (such as lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, (γ) cyclodextrin and / or tocopherol, and promotes the stabilization (light stabilization) of the polyketide pigment.

[0038] "Contacting with the compound (ii)" may correspond to contacting with a single compound (such as lycopene) or a mixture of compounds (e.g., lycopene and CHA (singular or plural)). Optionally, the method of the present invention may further include the step of mixing (i) and (ii) to obtain a homogeneous mixture.

[0039] Polyketide pigment The polyketides forming part of the present invention include, but are not limited to, azaphilones, anthraquinones, hydroxyanthraquinones and naphthaquinones. For the avoidance of doubt, "a Polyketides pigment" or "the Polyketide pigment" in the present invention is defined as one or more polyketide pigments, i.e., it may refer to only one type of polyketide (such as purified azaphilone), or it may refer to a combination of several pigments (for example, a mixture of atrorosein-type azaphilone pigments obtained from Talaromyces atroroseus disclosed in EP3622081 A1).

[0040] In a preferred embodiment, mycotoxins are excluded. In a preferred embodiment, the polyketide pigment is essentially free of mycotoxins such as citrinin and its derivatives, spiciferinone, cochliospicin A, austdiol and its derivatives.

[0041] The azaphilones that form part of the present invention may be any compound obtainable from fungal genera, including but not limited to those obtainable from one or more of the genera Aspergillus, Chaetomium, Hypoxylon, Monascus, Muycopron, Penicillium, Phomopsis, Pleosporales, Talaromyces, Pestalotiopsis, Phomopsis, Emericella, Epicoccum, Hypoxylon (Jin-Ming Gao et al. Azaphilones: Chemistry and Biology Chem. Rev. 2013, 113, 7, 4755-4811).

[0042] Certain classes of azaphilones include, but are not limited to, nitrogenated azaphilones, austdiols, specificellin and derivatives, deflectins, helotialins, bulgarialactones, spiroazaphilones, O-substituted azaphilones (especially O-containing Monascus pigments), lactone azaphilones, hydrogenated azaphilones, chaetoviridins and chaetomugilins, sequoiatones, tricoflectin and sassafrin azaphilones, pulvillonic acid type azaphilones, sclerothiorins, multiformins and cohelins, ascohiichin, chrysodine type azaphilones, hydrogenated spiroazaphilones, chlorofusins and atrolosins.

[0043] Even more specifically, the azaphilone pigments include the atrorosin-type azaphilone pigments described in EP3622081 A1 and Rasmussen K.B et al. (「Talaromyces atroroseus - Genome sequencing, Monascus pigments and azaphilone gene cluster evolution」Retrieved from the Internet in 2015: https: / / orbit.dtu.dk / en / publications / italaromyces-atroroseusi-genome-sequencing-monascus-pigments-and-), which are incorporated herein by reference.

[0044] This atrorosin-type azaphilone pigment described in EP3622081 A1 and Rasmussen K.B et al. is a "Monascus" like a pigment, biosynthesized by Talaromyces atroroseus, and incorporated herein by reference. Those "Monascus" like pigments have an azaphilone skeleton similar to the orange Monascus pigment PP-O and have a carboxylic acid group C-l, but are unique due to their incorporation of amino acids into the isochromene system. The atrocin described in EP3622081 A1 and Rasmussen K.B et al. are mostly red pigments, and their production is mycotoxin-free. The pigments described in EP3622081 A1 and Rasmussen K.B et al. are biosynthesized by Talaromyces atroroseus using organic (such as one or more amino acids, peptides, amino sugars and / or primary amines) and / or inorganic compounds as nitrogen sources.

[0045] Azaphilone pigments are further presented by Jin-Ming Gao et al. (Azaphilones: Chemistry and Biology Chem. Rev. 2013, 113, 7, 4755-4811) and include azaphilone pigments, which include, but are not limited to, monascuxanthone B (isolated from a yellow mutant of Monascus kaoliang cultivated in rice), monascuspirone and monascusazaphilol (metabolites of two different strains of Monascus pilosus), secoisoaustin C (isolated from the endophyte A. parasiticus of redwood), monalbrin and rubropunctatin (identified from Monascus pigments and from the culture broth of Monascus ruber), monaphyllone A and B (isolated from red mold rice fermented by the mutant strain M. pureus NTU 568), biscoziazaphilone A and B (obtained from the endophyte Biscognia formosana BCRC 33718).

[0046] Azaphilone pigments include Monascus-type azaphilones, which include, but are not limited to, the yellow pigments monascin (C21H26O5) and ankaflavin (C23H30O5), the orange pigments monascorubrin (C23H26O5) and rubropunctatin (C21H22O5), the red pigments monascorubramine (C23H27NO4) and rubropunctamine (C21H23NO4) (Jin-Ming Gao et al. Azaphilones: Chemistry and Biology Chem. Rev. 2013, 113, 7, 4755-4811), all their derivatives and monascorubraminic acid (the compound represented by formula (I)).

[0047]

Chemical formula

[0048] The double bond adjacent to the carboxyl group of the compound represented by formula (I) can have either an E- or Z-configuration, or the compound exists as a mixture. For example, the amino acids are selected from the group consisting of alanine, arginine, asparagine, aspartate (aspartic acid), cysteine, glutamate (glutamic acid), glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, serine, threonine, tyrosine, valine and ornithine. (The amino acids can be in the L or D configuration, or a mixture thereof.)

[0049] For example, the amino sugars are selected from the group consisting of glucosamine and galactosamine. For example, the primary amines are selected from the group consisting of anthranilic acid, aniline, p-phenylenediamine, and ethanolamine.

[0050] The "derivatives" in the present text refer to the basic structure having a different amino acid chain at position 10 (such as the above-mentioned monascus-type azaphilones as examples). For example, when both M. ruber and M. purpureus A are cultured in a chemically defined medium using glutamic acid as a nitrogen source, two pigments, N-glutaryl rubropunctamine and N-glutaryl monascorubramine, are produced, and these have been reported to be linked to glutamic acid by an amino group. Similarly, the liquid-cultured fungus M. ruber produced two water-soluble red pigments, N-glucosyl rubropunctamine and N-glucosyl monascorubramine.

[0051] Monascus pigments containing N generally consist of an isoquinoline skeleton having an n-octanoyl or n-hexanoyl side chain, a 1-propenyl chain, and a γ-lactone ring. Most pigments are various amino acid derivatives of monascorubrin and rubropunctatin (rubropunctamine and monascorubramine).

[0052] Depending on the supplementation to the fermentation medium, different Monascus such as pigments can be obtained (for example, aspartate derivatives of alanine or monascorubrin, and rubropunctatin, Monascus pigment threonine derivatives, arginine derivatives, culturing M. pureus resting cells with glycine results in dark red substances, unnatural amino acids (for example, derivatives containing penicillamine (H-Pen,), cyclohexylalanine (H-Cha,), butylglycine (L-t-Bg,), norleucine (H-Nle,) have been found to be obtained.)

[0053] Also included herein are cavernamine pigments as described in WO202094830. The aforementioned pigments can be obtained by extraction from natural sources or may otherwise be derived from natural sources such as plants, fungi, bacteria or algae. The pigments may be natural, i.e., extracted in their unmodified form from their natural state, or may be obtained from the natural state and even purified or chemically modified.

[0054] They may be provided as a mixture or they may be prepared or isolated individually. When the compounds are prepared individually, they may be extracted from natural sources and purified or they may be prepared via chemical synthesis or by fermentation.

[0055] Carotenoids Carotenoids or tetraterpenoids are yellow, orange, and red organic pigments produced by plants and algae, as well as some bacteria and fungi. In one aspect, the carotenoid may be selected from (i) pure hydrocarbons called carotenes, which include compounds such as, but are not limited to, β-carotene, α-carotene, γ-carotene, or lycopene, (ii) molecules called xanthophylls that contain various forms of oxygen (hydroxyl groups, epoxy groups, etc.), which include, but are not limited to, astaxanthin, zeaxanthin, capsanthin, canthaxanthin, lutein, etc., and (iii) molecules called apocarotenoids such as bixin and norbixin and any mixtures thereof.

[0056] In a specific case, the carotenoid composition of the present invention can be mixed with an oil that forms an oily solution of the carotenoid composition so that the final carotenoid content is 30% w / w or more. In a preferred aspect, the final carotenoid content in the oily solution is at least 31%, at least 32%, at least 33%, at least 34%, at least 35%, at least 36%, at least 37%, at least 38%, at least 39%, at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, or at least 75% (w / w).

[0057] This oily solution of carotenoid can optionally be emulsified as a water-in-oil emulsion containing 1 to 20% oil (preferably olive oil, sunflower oil, oil containing medium-chain triglycerides, or a mix thereof). In a specific aspect, the final concentration of carotenoid in the water-in-oil emulsion is 0.1 to 10%, more preferably 0.5 to 8%. In a preferred aspect, the carotenoid is lycopene.

[0058] Lycopene (CAS number: 502 - 65 - 8) is a symmetric tetraterpene, i.e., it is constructed from eight isoprene units. It is a member of the carotenoid family of compounds and, since it consists entirely of carbon and hydrogen, it is also classified as a carotene. Lycopene (C40H56) is an intermediate in the biosynthetic pathways of β - carotene and xanthophyll. It has a molecular weight of 536.85 and the following molecular formula:

Chem.

[0059] Lycopene exists in different forms and has different colors and intensities, but in all cases the term "lycopene" is used to refer to the chemical substance. However, it should be noted that crystalline lycopene has a strong red color, which is different from dissolved lycopene or dispersed lycopene or solubilized lycopene, which has a yellow - orange color. Furthermore, lycopene that occurs naturally in fruits exists in crystalline form in chromoplasts and can thus retain its red color, as in tomatoes.

[0060] As described, the intense red color of lycopene is due to its crystalline form and is affected by its particle size distribution. Lycopene loses its staining power in the red color range when the crystals dissolve and readily occurs in various organic solvents, such as oils. When lycopene oleoresin is solubilized in an aqueous solution, it exhibits a yellowish - orange color depending on the concentration.

[0061] In one aspect, the lycopene used in the present invention is in its crystalline form. In one aspect, the lycopene used in the present invention may be obtained from natural sources or may be obtainable, or may have a synthetic origin. In one aspect, lycopene may be obtained from plants, photosynthetic bacteria, fungi and / or algae or may be obtainable.

[0062] As will be apparent to those skilled in the art, as used herein, the term "obtainable from" means that lycopene may be obtained directly from plants / algae / animals / prokaryotes, or may be isolated from plants, photosynthetic bacteria, fungi and / or algae, or may be obtained from alternative sources, such as chemical synthesis or enzyme production. As used herein, the term "obtained" means that the extract is directly derived from a plant, photosynthetic bacteria, fungal and / or algal source.

[0063] In certain embodiments, lycopene may be obtained from or obtainable from plant products such as tomatoes, carrots, peppers, vegetable oils, autumn olives, goji berries, watermelons, pink grapefruits, pink guavas, papayas, sea buckthorn, wolfberries (goji, a berry related to tomatoes), rose hips, and any mixtures thereof.

[0064] The lycopene used in the present invention may be produced from plant products using any type of process, such as those described in patent WO 97 / 48287, which describes a method for preparing an oleoresin rich in lycopene from tomatoes, which involves squeezing the tomatoes until pulp is obtained, extracting the lycopene from the pulp with an organic solvent, and subsequently removing the solvent by evaporation to yield an oleoresin having a lycopene content of 2 to 10%.

[0065] Similar methods for obtaining oleoresins rich in carotenoids, especially lycopene, from plants and oils are described, for example, in U.S. Patent 5,245,095 and European Patent 580745, which precipitate with calcium salts, U.S. Patent 5,019,668, which uses a method of distillation after transesterification with oil, WO 95 / 16363, which describes fractionating tomatoes into various fractions containing carotenoid-rich oleoresins, and PCT WO 90 / 08584, which describes extracting lycopene using a supercritical fluid, but the resulting extracts are mixtures of various carotenoids and the extraction yields are extremely low due to their low solubility, as described in various patents. All of these methods are hereby incorporated by reference into this specification.

[0066] In certain embodiments, lycopene is in the form of natural oleoresins such as paprika oleoresin, tomato oleoresin, and the like. Lycopene preparations of biological origin can also be obtained by the fermentation of phycomycete fungi of the genera Phycomyces, Blakeslea, and Choanephora [GB 1008469, U.S. Pat. Nos. 3,097,146, 3,369,974, JP 73016189, JP 73016190, RU 2102416, WO 00 / 77234], which are hereby incorporated by reference into this specification, and lycopene can also be obtained from the fungus B. trispora as described in WO03 / 056028 A1, which is hereby incorporated by reference into this specification.

[0067] Certain carotenoid-rich microalgae of the Dunaliella type are also another important source of lycopene. There are various methods for extracting carotenoids, and in particular lycopene, from these organisms, by extraction with organic solvents (chlorocarbons, hydrocarbons, etc.) or edible oils (DE 4342798), as also reflected in US Patent Nos. 5,378,369, 4,713,398 and 4,680,314. Different processes are described in PCT WO 98 / 08584, where lycopene extracts are obtained using CO2 in the supercritical state, but the extracts obtained are of low purity with respect to lycopene. All of those methods are hereby incorporated herein by reference.

[0068] In the present invention, oleoresins containing lycopene of different purities may be used. In certain embodiments, the oleoresin may contain at least 2% lycopene, such as at least 5%, at least 10%, at least 50%, or at least 99% lycopene, etc.

[0069] In certain embodiments, the lycopene is tomato oleoresin in the form of a free-flowing powder containing about 40% to 100% lycopene. In certain embodiments, the lycopene is trans-lycopene, cis-lycopene, or a mixture thereof.

[0070] In certain embodiments, the lycopene is in crystalline form, characterized by having a crystalline purity of more than 10%, more than 20%, etc., more than 50%, more than 95%, etc. In certain embodiments, the crystals have a cis-lycopene content of less than 3% and an other carotenoid content of less than 3%. In certain embodiments, the lycopene crystals may be mixed with other carotenoids as described herein.

[0071] In one aspect, lycopene is prepared according to the patent application US5965183A, which is incorporated herein by reference. This patent application describes a process for the preparation of a stable lycopene concentrate, which includes reducing the size of lycopene crystals in a food-compatible liquid medium that does not essentially dissolve lycopene. This patent application describes a process for preparing a crystalline lycopene composition, which process includes treating a lycopene-containing oleoresin with a solvent or solvent mixture (such as an acetone / ethyl acetate solvent mixture) that dissolves the lipid phase of the oleoresin and does not substantially dissolve lycopene to remove most of the oleoresin lipids.

[0072] In one aspect, it is preferable to mill the lycopene crystals to an average particle size of less than about 5 μm, such as an average particle size of about 1 - 3 μm. In one aspect, lycopene is dissolved in a food-compatible liquid selected from the group consisting of glycerol, propylene glycol, and ethanol, or a mixture thereof, or a mixture thereof with other food-compatible liquids. In one aspect, the lycopene solution additionally contains lecithin and / or sucrose esters.

[0073] In one aspect, lycopene is extracted from tomatoes using ethyl acetate and ethanol, and after purification and concentration, the final product is formulated with glycerol, lecithin, sucrose esters, and water.

[0074] In another preferred aspect, the carotenoid is bixin and / or norbixin. In one aspect, bixin or norbixin may be obtained or can be obtained from plant products such as the seeds of the achiote tree (Bixa Orellana). The oil of the seeds of the achiote tree is generally known as annatto or annatto coloring. In the European Union, it is identified as Annatto, E number E160b.

[0075] In one aspect, in the present invention, anatto coloring agents obtained from, or obtainable from, the seeds of achiote trees containing bixin and / or norbixin are used. In other aspects, bixin or norbixin is of synthetic origin. In other aspects, the carotenoid is a mixture of lycopene, bixin and / or norbixin. Rosmarinic acid may be of natural or synthetic origin. In one aspect, rosmarinic acid is in the form of a natural product, such as a Lamiaceae extract.

[0076] As used herein, the term "Lamiaceae extract" may refer to an extract from plants of the Lamiaceae family, which includes, but is not limited to, rosemary, sage, oregano, thyme, mint, and the following genera: Melissa (Melissa officinalis or Lemon balm), Salvia (such as Salvia Apiana and Salvia officinalis), Rosmarinus (such as Rosmarinus officinalis), Lepechinia, Origanum, Saimus, Hyssopus, and any mixture thereof.

[0077] The Lamiaceae material used to extract the Lamiaceae extract rich in rosmarinic acid can be any part of the plant, such as leaves, roots, flowers, stems, etc. In a preferred aspect, the plant part is leaves and / or stems.

[0078] The Lamiaceae material may be processed prior to extraction, such as washed, dried, powdered or ground, etc.

[0079] The Lamiaceae extract (such as rosemary and / or Melissa extract) may be obtained, or obtainable, by extracting the aerial parts of the Lamiaceae extract (such as rosemary and / or Melissa extract) with a solvent, followed by any purification depending on the concentration of rosmarinic acid required in the final extract.

[0080] Specific solvents that may be used in the extraction process include water, alcohols (such as methanol, ethanol, etc.), acetone, ethyl acetate, hexane, dichloromethane, and any mixtures thereof, such as alcohol / water mixtures (such as methanol and water mixtures). For example, the extraction solvent can be water, a water-alcohol mixture (about 1% to about 99% alcohol in water). For example, about 30% to about 75% alcohol in water, or about 30% to 50% in water (such as about 35% or about 40% alcohol in water, etc.), or alcohol. Specific alcohols that may be mentioned include ethanol (EtOH) and methanol (MeOH).

[0081] In certain embodiments, extracts of the Lamiaceae family (such as rosemary and / or Melissa extracts) contain at least 1% w / w, at least 3%, etc. of rosmarinic acid. In certain embodiments, extracts of the Lamiaceae family (such as rosemary and / or Melissa extracts) contain 1% to 99% of rosmarinic acid.

[0082] Chlorogenic acids (CGAs) Hereinafter, the term "CGA (singular or plural)" or "chlorogenic acid (singular or plural)" means one or more chlorogenic acids (singular or plural) and their derivatives, including but not limited to neo-chlorogenic acid (neo-CGA; 5-O-caffeoylquinic acid or 5-CQA), cryptochlorogenic acid (crypto-CGA; 4-O-caffeoylquinic acid or 4-CQA), n-chlorogenic acid (n-CGA; 3-O-caffeoylquinic acid or 3-CQA), isochlorogenic acid A (iso-CGA A; 3,5-dicaffeoylquinic acid), isochlorogenic acid B (iso-CGA B; 3,4-dicaffeoylquinic acid), isochlorogenic acid C (iso-CGA C; 4,5-dicaffeoylquinic acid), other chlorogenic acids and isochlorogenic acids known in the art, and combinations thereof.

[0083] The CGA(s) may be of natural origin or of synthetic origin. The CGA(s) may be extracted from various natural sources. Thus, in a preferred embodiment, the chlorogenic acid(s) is / are extracted from a biological material containing chlorogenic acid(s), such as a plant, an animal or a prokaryote.

[0084] The CGA(s) containing the biological material is preferably a plant biological material. The plant biological material may be obtained from or can be obtained from the roots and / or the aerial parts of the plant, such as leaves, flowers, stems, barks, fruits and / or seeds, their tissues (such as the peel of the fruit) or mixtures thereof. For example, the plant biological material may be the leaves of the plant.

[0085] As will be apparent to those skilled in the art, as used herein, the term "can be obtained from" means that the biological material of the plant and / or animal and / or prokaryote may be directly obtained from the plant / algae / animal / prokaryote, may be isolated from the plant / algae / animal / prokaryote, or may be obtained from alternative sources, such as chemical synthesis or enzymatic production. On the other hand, as used herein, the term "obtained" means that the extract is directly derived from a plant / algae / animal / prokaryote source.

[0086] Non-limiting examples of CGA(s) containing biological material of plants are green coffee beans from any species of the genus Coffea such as Coffea arabica, Coffea canephora, Coffea liberica, leaves of Ilex paraguariensis, pomaceous fruits (e.g., apples and pears), stone fruits (e.g., cherries and plums), berries, citrus fruits, cruciferous vegetables (e.g., kale, cabbage and Brussels sprouts), Solanaceae (e.g., tubers of potatoes, tomatoes, and eggplants), Asteraceae (e.g., chicory roots and artichokes), and various other hybrid vegetables. It may also be included in cereals (e.g., oats, barley, rye, rice, corn and wheat). The amount and various types of chlorogenic acids present vary depending on the source. Chlorogenic acids may be extracted from one or more plant sources and / or synthetic chlorogenic acids may be used.

[0087] In a preferred embodiment, CGA(s) are obtained from, or can be obtained from, Arabica, Robusta and / or Liberica green coffee beans and are defined herein as "green coffee extract".

[0088] Naturally-occurring CGA can be present in the compositions of the present invention as purified CGA or as a natural extract obtained from or obtainable from the aforementioned Arabica, Robusta and / or Liberica green coffee beans.

[0089] To obtain CGA, various extraction methods known in the art may be used. For example, solvents that can be used for extraction include, but are not limited to, water, alcohols (such as ethanol), acetone and any mixtures thereof.

[0090] Rutin glucoside The polyglycosylated rutin forming part of the present invention has the following formula:

Chemical formula

[0091] The glycosylation of rutin, a polyphenol flavonoid, is well known in the art, for example, from Journal of Microbiology and Biotechnology Volume 26 Issue 11, pp.1845 - 1854 (2016) and US Patent 5145781. Glycosylated rutin is known for its better water solubility than rutin, and thus rutin can be easily obtained. The glycosylation of rutin occurs at the fourth carbon of the glucose unit. This process always results in an expansion of the values of n in the range from 1 upwards. In the present disclosure, n > 2 includes a majority, higher than 50%, more specifically higher than 60% molar concentration of glycosylated rutin. In a specific embodiment, the average value of n is from 2 - 11, specifically at least 3, more specifically from 3 - 4.

[0092] Tocopherol In the present disclosure, tocopherol (or vitamin E) may include four tocopherols and four tocotrienols. In one aspect, tocopherol is selected from alpha, beta, gamma, and delta tocopherol or mixtures thereof. As a food additive, tocopherol has the E numbers: E306 (tocopherol), E307 (α - tocopherol), E308 (γ - tocopherol), E309 (δ - tocopherol).

[0093] In one aspect, the tocopherol used in the present invention may be obtained from a natural source or may be obtainable. In one aspect, it may have a synthetic origin. In one aspect, tocopherol may be obtained from or may be obtainable from plants, photosynthetic bacteria, fungi, and / or algae.

[0094] In certain embodiments, tocopherol may be obtained from, or may be obtainable from, crude vegetable oils such as soybean, sunflower, canola, rapeseed, cottonseed, safflower, corn, palm, palm kernel and rice bran oil.

[0095] Water-soluble vitamin E (α-tocopherol, αT), such as its esters having acetate (αTA), succinate (αTS), or phosphate (αTP), etc., have increased solubility in water and stability towards reaction with free radicals. In certain embodiments, the tocopherol is a water-dispersible tocopherol.

[0096] Gamma-cyclodextrin: Cyclodextrin is a family of cyclic oligosaccharides and consists of a macrocyclic ring of glucose subunits linked by α-1,4 glycosidic bonds. Cyclodextrin is produced by enzymatic conversion from starch. In the present invention, alpha, beta and / or gamma cyclodextrin may be used.

[0097] In a preferred embodiment, gamma cyclodextrin is used. The Cas number of gamma cyclodextrin is 17465-86-0. Gamma-cyclodextrin is a cycloamylose composed of 8 alpha-(1->4) linked D-glucopyranose units. The molecular weight is 1297.1.

[0098] In the method of the present invention, a second product (ii) selected from the list of carotenoids (such as lycopene), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol is mixed with a polyketide dye (such as azaphilone as referred to herein).

[0099] In a preferred embodiment, the azaphilone is an atrocin-type azaphilone dye, such as those disclosed in EP3622081 A1 or Rasmussen K.B et al. In another preferred embodiment, azaphilone is the dye described by Jin-Ming Gao et al.

[0100] In another preferred embodiment, azaphilone is a Monascus pigment, such as monascin (C21H26O5), ankaflavin (C23H30O5), monascorubin (C23H26O5), rubropunctatin, monascorubramine (C23H27NO4) and / or rubropunctamine (C21H23NO4), one or more thereof.

[0101] In another preferred embodiment, azaphilone is obtained from, or can be obtained from, the genus Aspergillus, Chaetomium, Hypoxylon, Monascus, Muycopron, Penicillium, Phomopsis, Pleosporales, Talaromyces (such as Talaromyces atroroseus), Pestalotiopsis, Phomopsis, Emericella, Epicoccum, Hypoxylon.

[0102] Polyketide pigments (such as azaphilones referred to herein) can be present in solid form (such as powder) or in a liquid solution. Thus, in one embodiment, the polyketide pigment (such as azaphilone) is an aqueous solution. In one embodiment, the aqueous solution may contain at least 50% water, at least 70% water, such as at least 90% water.

[0103] The product(s) (ii) can be in the form of a solid (such as a powder) or present in a liquid solution. As used herein, "liquid solution" includes, without limitation, a solution, emulsion, or dispersion of the components of the mix in a liquid solvent. The liquid solvent can be water, glycerol, or other liquid or a mixture of any solvents suitable for dissolving or dispersing the components of the mix (such as polyketide pigments (such as azaphilones mentioned herein) and component (ii)). In certain embodiments, the aqueous solution may contain at least 50% water, at least 70% water, etc., such as at least 90% water.

[0104] In certain embodiments, the polyketide pigment (such as azaphilone) is present in an aqueous solution. In certain embodiments, both products, both the polyketide pigment and product (ii), can be in the form of a powder or mixed in the form of a powder. Optionally, the resulting mixed powder is then added to a suitable solvent such as water and, optionally, mixed until a uniform solution is obtained.

[0105] In other embodiments, the polyketide pigment is in the form of a powder that is added to the second component (ii) in liquid form. In other embodiments, the polyketide pigment is in liquid form and component (ii) is in the form of a powder that is added to the liquid polyketide pigment.

[0106] Optionally, the polyketide pigment and component (ii) may be further mixed until a uniform mixture is obtained. The mixing of both components may be carried out for at least 5 minutes, at least 10 minutes, etc., such as at least 30 minutes, at least 1 hour, etc. Any method known in the art for mixing the components may be used in the present invention.

[0107] In a preferred embodiment, lycopene is used. Lycopene, as described above, forms crystals that are usually provided as an emulsion in solvents in which lycopene does not dissolve, such as glycerol, water, and mixtures thereof. Thus, in certain embodiments, a suspension of lycopene crystals is used in the method of the present invention. In certain embodiments, lycopene is in the form of an emulsion.

[0108] In certain embodiments, the carotenoid is selected from lycopene, bixin and / or norbixin In certain embodiments, the method of the invention further comprises an additional filtration step to remove the insoluble fraction.

[0109] In certain embodiments of the method of the invention, it further comprises a step of concentrating the stabilized polyketide pigment obtained using the method described herein. In certain embodiments, the method of the invention further comprises a drying step such as spray drying.

[0110] The obtained stabilized polyketide pigments (such as azaphyllon) obtained using the method described herein, as already mentioned, are polyketide pigments (such as azaphyllon), and carotenoids (such as lycopene, bixin and / or norbixin), rosmarinic acid, chlorogenic acid, rutin glucoside or tocopherol, and contain one or more compounds selected from the group consisting of, and have improved stability to light exposure.

[0111] As those skilled in the art will recognize, carotenoids (such as lycopene, bixin and / or norbixin) may be used alone to stabilize the polyketide pigment (such as azaphyllon), or it may be used in combination with one or more of rosmarinic acid, chlorogenic acid(s), rutin glucoside, cyclodextrin, or tocopherol. When multiple components are used to stabilize the polyketide pigment (such as azaphyllon), they can be used together or added sequentially to the polyketide pigment.

[0112] As described above, rosmarinic acid, rutin glucoside, cyclodextrin and / or tocopherol can be provided in solid or liquid form. Thus, in one aspect, they are provided in solid form such as a powder that can be directly added to a solution of a polyketide dye (such as azaphilone). In the case where it is provided as a solution, both solutions (the polyketide dye (such as azaphilone) and rosmarinic acid, etc.) can be brought into contact and optionally mixed (step b).

[0113] The ratio of the polyketide dye (such as azaphilone) to compound (ii) may be 10:90 or more, or about 10:90. In some aspects, the ratio is 20:80 or more or about 20:80. In some aspects, the ratio is 30:70 or more or about 30:70. In some aspects, the ratio is 40:60 or more or about 40:60. In some aspects, the ratio is 50:50 or more or about 50:50. In some aspects, the ratio is 60:40 or more or about 60:40. In some aspects, the ratio is 70:30 or more or about 70:30. In some aspects, the ratio is 80:20 or more or about 80:20. In some aspects, the ratio is 85:15 or more or about 85:15. In some aspects, the ratio is 90:10 or more or about 90:10. In some aspects, the ratio is 95:5 or more or about 95:5. In some aspects, the ratio is 99:1 or more or about 99:1.

[0114] The ratio of the polyketide pigment (such as azaphilone) to compound (ii) may be 99:1 or less, or about 99:1. In some embodiments, the ratio is 95:5 or less, or about 95:5. In some embodiments, the ratio is 90:10 or less, or about 90:10. In some embodiments, the ratio is 85:15 or less, or about 85:15. In some embodiments, the ratio is 80:20 or less, or about 80:20. In some embodiments, the ratio is 70:30 or less, or about 70:30. In some embodiments, the ratio is 60:40 or less, or about 60:40. In some embodiments, the ratio is 50:50 or less, or about 50:50. In some embodiments, the ratio is 40:60 or less, or about 40:60. In some embodiments, the ratio is 30:70 or less, or about 30:70. In some embodiments, the ratio is 20:80 or less, or about 20:80. In some embodiments, the ratio is 10:90 or less, or about 10:90.

[0115] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to compound (ii) may be from 10:90 to 99:1, or about 10:90 to about 99:1, from 10:90 to 90:1, or about 10:90 to about 90:1, from 20:80 to 80:20, or about 20:80 to about 80:20, from 50:50 to 80:20, or about 50:50 to about 80:20, or from 60:40 to 80:20, or about 60:40 to about 80:20.

[0116] In certain embodiments, the polyketide pigment (such as azaphilone) is contacted with a carotenoid such as lycopene, bixin and / or norbixin in a weight ratio of 99:1 to 75:25. In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to the carotenoids such as lycopene, bixin and / or norbixin can be 99:1 or less, or about 99:1. In some embodiments, the ratio is 95:5 or less or about 95:5. In some embodiments, the ratio is 90:10 or less or about 90:10. In some embodiments, the ratio is 85:15 or less or about 85:15. In some embodiments, the ratio is 80:20 or less or about 80:20. In some embodiments, the ratio is 70:30 or less or about 70:30. In some embodiments, the ratio is 60:40 or less or about 60:40. In some embodiments, the ratio is 50:50 or less or about 50:50. In some embodiments, the ratio is 40:60 or less or about 40:60. In some embodiments, the ratio is 30:70 or less or about 30:70. In some embodiments, the ratio is 20:80 or less or about 20:80. In some embodiments, the ratio is 10:90 or less or about 10:90.

[0117] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to the carotenoids such as lycopene, bixin and / or norbixin can be from 10:90 to 99:1 or about 10:90 to about 99:1, from 10:90 to 90:1 or about 10:90 to about 90:1, from 20:80 to 80:20 or about 20:80 to about 80:20, from 50:50 to 80:20 or about 50:50 to about 80:20, or from 60:40 to 80:20 or about 60:40 to about 80:20.

[0118] In certain embodiments, the ratio of the polyketide dye (such as azaphilone) to the carotenoids such as lycopene, bixin and / or norbixin can be 10:90 or more, or about 10:90. In some embodiments, the ratio is 20:80 or more or about 20:80. In some embodiments, the ratio is 30:70 or more or about 30:70. In some embodiments, the ratio is 40:60 or more or about 40:60. In some embodiments, the ratio is 50:50 or more or about 50:50. In some embodiments, the ratio is 60:40 or more or about 60:40. In some embodiments, the ratio is 70:30 or more or about 70:30. In some embodiments, the ratio is 80:20 or more or about 80:20. In some embodiments, the ratio is 85:15 or more or about 85:15. In some embodiments, the ratio is 90:10 or more or about 90:10. In some embodiments, the ratio is 95:5 or more or about 95:5. In some embodiments, the ratio is 99:1 or more or about 99:1.

[0119] In certain embodiments, the polyketide dye (such as azaphilone) is contacted with rosmarinic acid at a weight ratio of 75:25. In a preferred embodiment, the rosmarinic acid is obtained or can be obtained from Lamiaceae such as rosemary or lemon balm. In a preferred embodiment, a Lamiaceae extract such as a rosemary and / or lemon balm extract containing rosmarinic acid is used. As known to those skilled in the art, natural extracts can have variable concentrations of rosmarinic acid, and the Lamiaceae extracts will be used at concentrations that provide the ratio of the polyketide dye (such as azaphilone) to rosmarinic acid as defined herein.

[0120] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to rosmarinic acid can be 99:1 or less, or about 99:1. In some embodiments, the ratio is 95:5 or less, or about 95:5. In some embodiments, the ratio is 90:10 or less, or about 90:10. In some embodiments, the ratio is 85:15 or less, or about 85:15. In some embodiments, the ratio is 80:20 or less, or about 80:20. In some embodiments, the ratio is 70:30 or less, or about 70:30. In some embodiments, the ratio is 60:40 or less, or about 60:40. In some embodiments, the ratio is 50:50 or less, or about 50:50. In some embodiments, the ratio is 40:60 or less, or about 40:60. In some embodiments, the ratio is 30:70 or less, or about 30:70. In some embodiments, the ratio is 20:80 or less, or about 20:80. In some embodiments, the ratio is 10:90 or less, or about 10:90. In a preferred embodiment, the polyketide pigment (such as azaphilone) is contacted with rosmarinic acid at a weight ratio of 75:25.

[0121] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to rosmarinic acid can be from 10:90 to 99:1, or about 10:90 to about 99:1; from 10:90 to 90:1, or about 10:90 to about 90:1; from 20:80 to 80:20, or about 20:80 to about 80:20; from 50:50 to 80:20, or about 50:50 to about 80:20; or from 60:40 to 80:20, or about 60:40 to about 80:20.

[0122] In certain embodiments, the ratio of the polyketide dye (such as azaphilone) to rosmarinic acid can be 10:90 or more, or about 10:90. In some embodiments, the ratio is 20:80 or more or about 20:80. In some embodiments, the ratio is 30:70 or more or about 30:70. In some embodiments, the ratio is 40:60 or more or about 40:60. In some embodiments, the ratio is 50:50 or more or about 50:50. In some embodiments, the ratio is 60:40 or more or about 60:40. In some embodiments, the ratio is 70:30 or more or about 70:30. In some embodiments, the ratio is 80:20 or more or about 80:20. In some embodiments, the ratio is 85:15 or more or about 85:15. In some embodiments, the ratio is 90:10 or more or about 90:10. In some embodiments, the ratio is 95:5 or more or about 95:5. In some embodiments, the ratio is 99:1 or more or about 99:1.

[0123] In certain embodiments, the polyketide dye (such as azaphilone) is contacted with CGA(s) in a weight ratio of 95:5 to 80:20. In a preferred embodiment, the CGA(s) is provided by a green coffee extract obtainable or obtained from one or more species of the genus Coffea such as Coffea arabica, Coffea canephora, Coffea liberica. In a preferred embodiment, the CGA(s) is provided by a natural extract containing CGA(s). As will be appreciated by those skilled in the art, natural extracts containing CGA(s) such as green coffee extract can have variable concentrations of CGA(s), and thus natural extracts containing CGA(s) such as green coffee extract will be used in the present invention at a concentration such that the ratio of the polyketide dye (such as azaphilone) as defined herein to CGA(s) is provided.

[0124] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to CGA(s) can be 99:1 or less, or about 99:1. In some embodiments, the ratio is 95:5 or less, or about 95:5. In some embodiments, the ratio is 90:10 or less, or about 90:10. In some embodiments, the ratio is 85:15 or less, or about 85:15. In some embodiments, the ratio is 80:20 or less, or about 80:20. In some embodiments, the ratio is 70:30 or less, or about 70:30. In some embodiments, the ratio is 60:40 or less, or about 60:40. In some embodiments, the ratio is 50:50 or less, or about 50:50. In some embodiments, the ratio is 40:60 or less, or about 40:60. In some embodiments, the ratio is 30:70 or less, or about 30:70. In some embodiments, the ratio is 20:80 or less, or about 20:80. In some embodiments, the ratio is 10:90 or less, or about 10:90.

[0125] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to CGA(s) can be from 10:90 to 99:1, or about from 10:90 to about 99:1, from 10:90 to 90:1, or about from 10:90 to about 90:1, from 20:80 to 80:20, or about from 20:80 to about 80:20, from 50:50 to 80:20, or about from 50:50 to about 80:20, or from 60:40 to 80:20, or about from 60:40 to about 80:20.

[0126] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to CGA (singular or plural) can be 10:90 or more, or about 10:90. In some embodiments, the ratio is 20:80 or more, or about 20:80. In some embodiments, the ratio is 30:70 or more, or about 30:70. In some embodiments, the ratio is 40:60 or more, or about 40:60. In some embodiments, the ratio is 50:50 or more, or about 50:50. In some embodiments, the ratio is 60:40 or more, or about 60:40. In some embodiments, the ratio is 70:30 or more, or about 70:30. In some embodiments, the ratio is 80:20 or more, or about 80:20. In some embodiments, the ratio is 85:15 or more, or about 85:15. In some embodiments, the ratio is 90:10 or more, or about 90:10. In some embodiments, the ratio is 95:5 or more, or about 95:5. In some embodiments, the ratio is 99:1 or more, or about 99:1.

[0127] In certain embodiments, the polyketide pigment (such as azaphilone) is brought into contact with rutin glucoside at a weight ratio of 80:20 to 50:50, 75:25, etc. In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to rutin glucoside can be 99:1 or less, or about 99:1. In some embodiments, the ratio is 95:5 or less, or about 95:5. In some embodiments, the ratio is 90:10 or less, or about 90:10. In some embodiments, the ratio is 85:15 or less, or about 85:15. In some embodiments, the ratio is 80:20 or less, or about 80:20. In some embodiments, the ratio is 70:30 or less, or about 70:30. In some embodiments, the ratio is 60:40 or less, or about 60:40. In some embodiments, the ratio is 50:50 or less, or about 50:50. In some embodiments, the ratio is 40:60 or less, or about 40:60. In some embodiments, the ratio is 30:70 or less, or about 30:70. In some embodiments, the ratio is 20:80 or less, or about 20:80. In some embodiments, the ratio is 10:90 or less, or about 10:90.

[0128] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to rutin glucoside can be from 10:90 to 99:1, or about 10:90 to about 99:1; from 10:90 to 90:1, or about 10:90 to about 90:1; from 20:80 to 80:20, or about 20:80 to about 80:20; from 50:50 to 80:20, or about 50:50 to about 80:20; or from 60:40 to 80:20, or about 60:40 to about 80:20.

[0129] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to rutin glucoside can be 10:90 or more, or about 10:90. In some embodiments, the ratio is 20:80 or more or about 20:80. In some embodiments, the ratio is 30:70 or more or about 30:70. In some embodiments, the ratio is 40:60 or more or about 40:60. In some embodiments, the ratio is 50:50 or more or about 50:50. In some embodiments, the ratio is 60:40 or more or about 60:40. In some embodiments, the ratio is 70:30 or more or about 70:30. In some embodiments, the ratio is 80:20 or more or about 80:20. In some embodiments, the ratio is 85:15 or more or about 85:15. In some embodiments, the ratio is 90:10 or more or about 90:10. In some embodiments, the ratio is 95:5 or more or about 95:5. In some embodiments, the ratio is 99:1 or more or about 99:1.

[0130] In certain embodiments, the polyketide pigment (such as azaphilone) is contacted with cyclodextrin, particularly gamma-cyclodextrin, in a weight ratio of 80:20 to 50:50. In some embodiments, the ratio of the polyketide dye (such as azaphilone) to cyclodextrin, particularly gamma-cyclodextrin, can be 99:1 or less, or about 99:1. In some embodiments, the ratio is 95:5 or less, or about 95:5. In some embodiments, the ratio is 90:10 or less, or about 90:10. In some embodiments, the ratio is 85:15 or less, or about 85:15. In some embodiments, the ratio is 80:20 or less, or about 80:20. In some embodiments, the ratio is 70:30 or less, or about 70:30. In some embodiments, the ratio is 60:40 or less, or about 60:40. In some embodiments, the ratio is 50:50 or less, or about 50:50. In some embodiments, the ratio is 40:60 or less, or about 40:60. In some embodiments, the ratio is 30:70 or less, or about 30:70. In some embodiments, the ratio is 20:80 or less, or about 20:80. In some embodiments, the ratio is 10:90 or less, or about 10:90.

[0131] In some embodiments, the ratio of the polyketide dye (such as azaphilone) to cyclodextrin, particularly gamma-cyclodextrin, can be from 10:90 to 99:1, or about 10:90 to about 99:1; from 10:90 to 90:1, or about 10:90 to about 90:1; from 20:80 to 80:20, or about 20:80 to about 80:20; from 50:50 to 80:20, or about 50:50 to about 80:20; or from 60:40 to 80:20, or about 60:40 to about 80:20.

[0132] In some embodiments, the ratio of the polyketide pigment (such as azaphilone) to cyclodextrin, particularly gamma-cyclodextrin, can be 10:90 or more, or about 10:90. In some embodiments, the ratio is 20:80 or more, or about 20:80. In some embodiments, the ratio is 30:70 or more, or about 30:70. In some embodiments, the ratio is 40:60 or more, or about 40:60. In some embodiments, the ratio is 50:50 or more, or about 50:50. In some embodiments, the ratio is 60:40 or more, or about 60:40. In some embodiments, the ratio is 70:30 or more, or about 70:30. In some embodiments, the ratio is 80:20 or more, or about 80:20. In some embodiments, the ratio is 85:15 or more, or about 85:15. In some embodiments, the ratio is 90:10 or more, or about 90:10. In some embodiments, the ratio is 95:5 or more, or about 95:5. In some embodiments, the ratio is 99:1 or more, or about 99:1.

[0133] In some embodiments, the polyketide pigment (such as azaphilone) is contacted with tocopherol, particularly soluble or dispersible tocopherol, in a weight ratio of 99:1 to 90:10. In some embodiments, the ratio of the polyketide pigment (such as azaphilone) to tocopherol (especially soluble tocopherol) can be 99:1 or less, or about 99:1. In some embodiments, the ratio is 95:5 or less, or about 95:5. In some embodiments, the ratio is 90:10 or less, or about 90:10. In some embodiments, the ratio is 85:15 or less, or about 85:15. In some embodiments, the ratio is 80:20 or less, or about 80:20. In some embodiments, the ratio is 70:30 or less, or about 70:30. In some embodiments, the ratio is 60:40 or less, or about 60:40. In some embodiments, the ratio is 50:50 or less, or about 50:50. In some embodiments, the ratio is 40:60 or less, or about 40:60. In some embodiments, the ratio is 30:70 or less, or about 30:70. In some embodiments, the ratio is 20:80 or less, or about 20:80. In some embodiments, the ratio is 10:90 or less, or about 10:90.

[0134] In some embodiments, the ratio of the polyketide pigment (such as azaphilone) to tocopherol (especially soluble tocopherol) can be from 10:90 to 99:1, or about 10:90 to about 99:1; from 10:90 to 90:1, or about 10:90 to about 90:1; from 20:80 to 80:20, or about 20:80 to about 80:20; from 50:50 to 80:20, or about 50:50 to about 80:20; or from 60:40 to 80:20, or about 60:40 to about 80:20.

[0135] In certain embodiments, the ratio of the polyketide pigment (such as azaphilone) to the soluble or dispersible tocopherol can be 10:90 or greater, or about 10:90. In some embodiments, the ratio is 20:80 or greater, or about 20:80. In some embodiments, the ratio is 30:70 or greater, or about 30:70. In some embodiments, the ratio is 40:60 or greater, or about 40:60. In some embodiments, the ratio is 50:50 or greater, or about 50:50. In some embodiments, the ratio is 60:40 or greater, or about 60:40. In some embodiments, the ratio is 70:30 or greater, or about 70:30. In some embodiments, the ratio is 80:20 or greater, or about 80:20. In some embodiments, the ratio is 85:15 or greater, or about 85:15. In some embodiments, the ratio is 90:10 or greater, or about 90:10. In some embodiments, the ratio is 95:5 or greater, or about 95:5. In some embodiments, the ratio is 99:1 or greater, or about 99:1.

[0136] In certain embodiments, the polyketide pigment (such as azaphilone) is contacted with two or more products (ii). The inventors of the present invention have demonstrated a synergistic effect of tocopherol and rosmarinic acid (such as lemon balm extract) in protecting and stabilizing polyketide pigments (such as azaphilone) against light exposure.

[0137] Accordingly, the present invention provides a method for stabilizing the color of a polyketide pigment (such as azaphilone), comprising contacting (i) a polyketide pigment (such as azaphilone) with (ii) rosmarinic acid and / or tocopherol, wherein the resulting polyketide pigment (such as azaphilone) is light-stable.

[0138] The present invention also provides a method for producing a light-stable polyketide pigment (such as azaphilone), comprising the steps of contacting (i) a polyketide pigment with (ii) rosmarinic acid and / or tocopherol, and optionally mixing (i) and (ii).

[0139] The resulting coloring composition contains a polyketide pigment and rosmarinic acid and / or tocopherol. In a preferred embodiment, the tocopherol is water-dispersible. The ratio of rosmarinic acid to tocopherol can be 15:1 or more, or about 15:1. In some embodiments, the ratio is 10:1 or more or about 10:1. In some embodiments, the ratio is 20:1 or more or about 20:1. In some embodiments, the ratio is 30:1 or more or about 30:1. In some embodiments, the ratio is 50:50 or more or about 50:50. In some embodiments, the ratio is 60:40 or more or about 60:40. In some embodiments, the ratio is 70:30 or more or about 70:30. In some embodiments, the ratio is 80:20 or more or about 80:20. In some embodiments, the ratio is 85:15 or more or about 85:15. In some embodiments, the ratio is 90:10 or more or about 90:10. In some embodiments, the ratio is 95:5 or more or about 95:5. In some embodiments, the ratio is 99:1 or more or about 99:1.

[0140] Synergistic effect of gamma-cyclodextrin and lemon balm The inventors of the present invention have demonstrated the synergistic effect of gamma-cyclodextrin and rosmarinic acid (such as lemon balm extract) in protecting and stabilizing polyketide pigments (such as azaphyllon) against light exposure.

[0141] Accordingly, the present invention provides a method for stabilizing the color of a polyketide pigment (such as azaphyllon), which includes contacting (i) a polyketide pigment with (ii) rosmarinic acid and / or cyclodextrin, particularly gamma-cyclodextrin, wherein the resulting polyketide pigment (such as azaphyllon) is light-stable.

[0142] The present invention also provides a method for producing a photo-stable polyketide pigment (such as azaphilone), which comprises the steps of: (i) contacting a polyketide pigment with (ii) rosmarinic acid and / or cyclodextrin, particularly gamma-cyclodextrin, and optionally mixing (i) and (ii).

[0143] The resulting colored composition contains a polyketide pigment and rosmarinic acid and / or cyclodextrin, particularly gamma-cyclodextrin. In a preferred embodiment, the tocopherol is water-soluble.

[0144] The ratio of rosmarinic acid to cyclodextrin, particularly gamma-cyclodextrin, can be 15:1 or more, or about 15:1. In some embodiments, the ratio is 10:1 or more, or about 10:1. In some embodiments, the ratio is 20:1 or more, or about 20:1. In some embodiments, the ratio is 30:1 or more, or about 30:1. In some embodiments, the ratio is 50:50 or more, or about 50:50. In some embodiments, the ratio is 60:40 or more, or about 60:40. In some embodiments, the ratio is 70:30 or more, or about 70:30. In some embodiments, the ratio is 80:20 or more, or about 80:20. In some embodiments, the ratio is 85:15 or more, or about 85:15. In some embodiments, the ratio is 90:10 or more, or about 90:10. In some embodiments, the ratio is 95:5 or more, or about 95:5. In some embodiments, the ratio is 99:1 or more, or about 99:1.

[0145] In a further aspect, the present invention relates to a colored composition comprising a stabilized polyketide pigment (such as azaphilone) obtained using the method of the present invention. The colored composition of the present invention may further contain a carrier.

[0146] Suitable carriers include inert solid diluents or fillers, sterile aqueous solutions, and various organic solvents. Examples of solid carriers include lactose, terra alba, sucrose, cyclodextrin, maltodextrin, dextrin, talc, gelatin, agar, pectin, acacia, magnesium stearate, magnesium hydroxide, stearic acid, gum arabic, modified starch, and lower alkyl ethers of cellulose, sucrose, silicon dioxide. Examples of liquid carriers are syrup, vegetable oil, phospholipids, fatty acids, fatty acid amines, polyoxyethylene, and water. Moreover, the carrier or diluent may include alone or in admixture with wax any sustained release material known in the art, such as glyceryl monostearate or glyceryl distearate.

[0147] In a further aspect, the invention relates to a stabilized coloring composition comprising a mixture of a polyketide pigment (such as azaphilone) and at least one product (ii) selected from carotenoids (such as lycopene, bixin and / or norbixin), rosmarinic acid, chlorogenic acid, rutin glucoside, (gamma) cyclodextrin and / or tocopherol. The stabilized pigment of the invention may be obtained using the method of the invention. As previously mentioned, the polyketide pigment (such as azaphilone) and the carotenoid (such as lycopene, bixin and / or norbixin), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin (such as gamma cyclodextrin) and / or tocopherol, at least one product (ii) may be in solid form, then these may be mixed and thereafter dissolved in a suitable solvent. Also, as previously mentioned, both components of the stabilized coloring composition of the invention may be provided in liquid form and thus may be mixed directly in liquid form. Any method known in the art may be used to mix the two components of the stabilized composition of the invention.

[0148] In one embodiment, the stabilized polyketide pigment (such as azaphilone) of the invention has a color with a maximum absorption band at 480 nm ± 5 nm. In one embodiment, the stabilized polyketide pigments (such as azaphilones) of the present invention have a color with a maximum absorption band of 300 + / - 5 nm to 450 nm + / - 5 nm (yellow pigment). In one embodiment, the stabilized polyketide pigments (such as azaphilones) of the present invention have a color with a maximum absorption band of 350 + / - 5 nm to 500 nm + / - 5 nm (orange pigment). In one embodiment, the stabilized polyketide pigments (such as azaphilones) of the present invention have a color with a maximum absorption band of 450 + / - 5 nm to 600 nm + / - 5 nm (red pigment).

[0149] All embodiments regarding the polyketide pigments defined so far for the method of the present invention are also applicable to the stabilized polyketide pigments (such as azaphilones) and the stabilized coloring compositions of the present invention. Also, all embodiments regarding product (ii) defined so far regarding the method of the present invention are applicable to the stabilized polyketide pigments (such as azaphilones) and the stabilized coloring compositions of the present invention.

[0150] In a preferred embodiment, the stabilized polyketide pigments (such as azaphilones) and the stabilized coloring compositions of the present invention comprise one or more of the azaphilone pigments monascin, ankaflavin, monascorubrin, rubropunctatin, monascorubramine, rubropuntamine, atrorosein (singular or plural) and their derivatives.

[0151] In one embodiment, the stabilized coloring composition of the present invention has a color with a maximum absorption band at 380 nm +- 5 nm. In one embodiment, the stabilized coloring composition of the present invention has a color with a maximum absorption band at 450 nm + / - 5 nm. In one embodiment, the stabilized coloring composition of the present invention has a color with a maximum absorption band at 500 nm + / - 5 nm. In one embodiment, the stabilized coloring composition of the present invention has a color with a maximum absorption band at 520 nm + / - 5 nm. The stabilized coloring composition of the present invention may further contain other pigments.

[0152] Foodstuff, dietary supplement, functional food, flavor or cosmetic composition and method for producing same The stabilized coloring composition of the present invention can be used to provide color to any consumer product where a stable red, orange or yellow is desired. Accordingly, in a further aspect, the present invention relates to a method for manufacturing a foodstuff, a pharmaceutical, a dietary supplement, a fragrance or a cosmetic product, comprising the step of incorporating into the foodstuff, the pharmaceutical, the dietary supplement, the fragrance or the cosmetic product a stabilized pigment according to the invention or a coloring composition according to the invention. In a preferred embodiment, the color is stable against light exposure. Components (i) and (ii) may be blended together and incorporated into the product at any stage of the manufacture of the product.

[0153] The inventors have observed that in order to deliver a more stable colorant, it is necessary to premix both components (i) and (ii). Without being bound by theory, polyketide pigments (such as Monascus or Monascus-like pigments) are stabilized by the second component (ii), and in order to obtain this stabilization, premixing of the components is considered necessary before mixing the stabilized colorant with the product (food, cosmetics, etc.). As can be seen from Example 7, when both components are added individually to the product matrix (without premixing to cause stabilization), polyketide pigments (such as Monascus or Monascus-like pigments) are not stable. However, some matrices that are liquid may allow for the mixing and complex formation of both components (i) and (ii) "in situ" (i.e., directly in the matrix) without the need for a further step of blending them together.

[0154] Accordingly, in one embodiment, where the product is in liquid or semi-solid form (such as beverages, milk, dairy products such as yogurt, cream, etc.), both components (i) and (ii) may be added sequentially individually, i.e., without forming a blend or premix. Accordingly, in a further aspect, the present invention comprises the step of incorporating components (i) and (ii) as defined in any one of the preceding claims, particularly when the product is liquid or semi-solid, where component (i) is added directly to the product, and as a result, product (ii) is also added to the product, or component (ii) is added directly to the product, and as a result, product (i) is also added to the product, relating to a method for manufacturing foodstuffs, pharmaceuticals, nutraceuticals, flavorings or cosmetic products. All aspects already mentioned with respect to the dye or coloring composition of the present invention also apply to the method of the present invention.

[0155] In another aspect, the present invention relates to a stabilized dye or stabilized coloring composition as defined herein, comprising a mixture of a polyketide dye (such as azaphyllon) and at least one product (ii) selected from carotenoids (such as lycopene, bixin and / or norbixin), rosmarinic acid, chlorogenic acid, rutin glucoside, cyclodextrin and / or tocopherol, and optionally a vehicle suitable for formulating foodstuffs, pharmaceuticals, nutraceuticals, nutraceutical foods, flavorings or cosmetic products, relating to foodstuffs, pharmaceuticals, nutraceuticals, nutraceutical foods, flavorings or cosmetic products.

[0156] Thus, the present invention relates to foodstuffs, pharmaceuticals, nutraceuticals, nutraceutical foods, flavorings or cosmetic products comprising a stabilized dye or stabilized coloring composition as defined herein, and the color of the foodstuffs, pharmaceuticals, nutraceuticals, nutraceutical foods, flavorings or cosmetic products is stable to light exposure. In a preferred embodiment, the dye or coloring composition of the present invention is obtained using the method of the present invention. In one embodiment, a foodstuff, pharmaceutical, nutraceutical food, flavoring or cosmetic product obtained using the method of the present invention, characterized in having a red, orange or yellow color stable to light.

[0157] In the present invention, the terms "stable to light" or "stable to light exposure" mean that the hue provided by the stabilizing dye of the present invention or the stabilizing coloring composition of the present invention does not change, or has a change of less than 30% with respect to the hue measured under dark conditions. Thus, in certain embodiments, the color provided by the coloring composition of the present invention is stable after light exposure for more than 5 minutes, for example more than 30 minutes, for example more than 1 hour, such as 2 hours, 5 hours, 10 hours, 12 hours, 24 hours, 2 days, 10 days, for example more than 30 days, or for example more than 60 days, or more than 6 months.

[0158] Foods or foodstuffs encompass the following general food categories as defined by the Food and Drug Administration (FDA): Bakery products and baking mixes, which include all ready-to-eat products and products that can be baked immediately, including flour and mixes that require preparation before serving; beverages, alcoholic beverages, which include malt beverages, and cocktail mixes; beverages and beverage bases, non-alcoholic, which include only special or spiced teas, soft drinks, coffee substitutes, and fruit and vegetable flavored gelatin beverages; cheeses, which include cottage cheese, whey cheese, cream, natural, powdered, processed, spreads, dips and various cheeses; chewing gums, which include all forms; coffee and tea, which include regular, decaffeinated and instant types; seasonings and condiments, which include plain-flavored sauces and spreads, olives, pickles, and condiments, but do not include spices or herbs;

[0159] Confectionery and frosting, which includes candy and flavored frosting, marshmallows, baking chocolate, and black, lumps, rock, maple, powder and brown sugar; Toppings, other non-dairy products. Egg products, which include liquid, frozen or dried eggs and egg dishes made therefrom, namely, egg rolls, egg foo young, egg salad and frozen multi-course egg meals, but does not include fresh eggs; Fats and oils, which include margarine, salad dressings, butter, salad oil, shortening and cooking oil; Fish products, which include all cooked main dishes, salads, appetizers, frozen multi-course meals and spreads containing fish, shellfish, and other aquatic animals, but does not include fresh fish; Fresh eggs, which include cooked eggs and egg dishes made only from fresh shelled eggs; Fresh fish, which includes only fresh and frozen fish, shellfish, other aquatic animals;

[0160] Fresh meat, which includes fresh or home-frozen beef or veal, pork, lamb or mutton and home-made raw meat-containing dishes, salads, appetizers, or sandwich spreads made therefrom; Fresh poultry, which includes fresh or home-frozen poultry and game birds, and only home-made fresh poultry-containing dishes, salads, appetizers, or sandwich spreads made therefrom; Pasta, which includes macaroni and noodle products, rice dishes, and frozen multi-course meals without meat or vegetables; Gravy sauce and sauces, which include all meat sauces and gravies, and tomato, milk, butter and special sauces;

[0161] Herbs, seeds, spices, seasonings, blends, extracts, and flavorants, which include all natural and artificial spices, blends, and flavors; meat products, which include all commercially processed or home-cooked commercially processed meat and meat-containing dishes, salads, appetizers, frozen multi-course meat meals, and sandwich ingredients; milk, whole and skim milk, which includes only whole milk, low-fat milk, and non-fat dry milk; dairy products, which include flavored milk and milk beverages, dry milk, toppings, snack dips, spreads, weight management milk beverages, and other milk-derived products; plant protein products, which include the "reconstituted plant protein" category of the United States Academy of Sciences / National Research Council, and meat, poultry, and fish alternatives, analogs, and extender products made from plant protein;

[0162] Poultry products, which include all commercially processed or home-cooked commercially processed poultry and poultry-containing dishes, salads, appetizers, frozen multi-course poultry meals, and sandwich ingredients; all commercially processed vegetables, vegetable dishes, frozen multi-course vegetable meals, and vegetable juices and blends; snack foods, which include chips, pretzels, and other novelty snacks; soups, homemade soups, which include meat, fish, poultry, vegetable, and homemade combination soups; soups and soup mixes, which include commercially prepared meat, fish, poultry, vegetable, and combination soups and soup mixes.

[0163] As used herein, the term "nutritional supplement" relates to compounds that have a beneficial effect on one or more functions of the body in order to provide better health and wellness. Thus, such nutritional agents can be aimed at the prevention and / or treatment of diseases or disease-causing factors. Accordingly, the term "nutritional composition" of the present invention can be used as a synonym for functional foods or foods for specific nutritional purposes, or medical foods. Nutritional compositions are similar to conventional foods and are consumed as part of the normal diet. In a preferred embodiment, the nutritional supplement is a nutritional agent.

[0164] As used herein, the term "nutritional agent or nutritional product" refers to a product suitable for use in humans or animals that contains one or more natural products that provide a health benefit or have a therapeutic effect related to the prevention or reduction of disease, and it is presented in a non-food matrix (such as capsules, powders, etc.) of concentrated natural bioactive products that are present (or not present) in normal foods, and when taken in a dose greater than that present in those foods, it exhibits a health-preferred effect greater than that which normal foods can have. Accordingly, the term "nutritional product" includes, in addition to isolated or purified food products, dosage forms commonly used orally, such as capsules, tablets, sachets, drinkable vials, etc., and generally presented additives or food supplements, and such products provide a physiological benefit or protection against diseases, generally chronic diseases.

[0165] As used herein, the term "pharmaceutical product" relates to compositions and molecular entities that have physiological tolerance. Preferably, the term "pharmaceutically acceptable" means that it has been approved by state or federal government regulatory authorities or is included in the United States Pharmacopeia or other generally recognized pharmacopeias for use in animals, more specifically humans. As used herein, "cosmetic product" refers to a composition suitable for enhancing natural beauty or altering the appearance of the body, without affecting the personal hygiene of humans or animals, or the structure or function of the human or animal body, and includes one or more products that provide such effects. If desired, the cosmetic composition provided by the present invention, in addition to the composition of the present invention, may include one or more cosmetics or cosmetic products, i.e., substances or mixtures intended for exclusive or primary purposes of cleansing, perfuming, altering the appearance of, protecting, keeping in good condition, or correcting body odor of the external parts of the human or animal body (e.g., epidermis, hair system, nails, lips, etc.) and / or the teeth and oral mucosa. Examples useful in the description of cosmetically acceptable vehicles include products contained in the INCI (International Nomenclature of Cosmetic Ingredients) list. The composition of the present invention may be added to a wide variety of products for cosmetic use, which include creams for makeup, skin cleansing, protection, treatment, or care, especially for the face, hands, and feet (e.g., day and night creams, makeup removal creams, foundation creams, sunscreens), liquid foundations, makeup removal lotions, protective or skin care body lotions, sunscreen lotions, skin care lotions, gels, or foams, e.g., cleansing, sunscreen, and self-tanning lotions, bath preparations, deodorant compositions, aftershave lotions or balms, depilatory creams, and compositions used for insect stings and pain. The composition of the present invention may take any of a wide variety of forms and may include, for example, dressings, lotions, solutions, sprays, creams, gels, ointments, or the like.

[0166] The stabilized pigment or coloring composition of the present invention can be added in an effective amount to increase, enhance, and / or modify the color characteristics of a product (such as a foodstuff) or a part thereof. In certain embodiments, the stabilized pigment or coloring composition of the present invention can be added in an effective amount to achieve a desired effect such as imparting a specific red, orange, or yellow color that is stable to light irradiation.

[0167] For example, as described herein, the food coloring composition can be used to impart a red color similar to that obtained when carmine or artificial color is used in food products, such as dairy products, confectionery, beverages, sauces / gravies, and the like. Dairy products can refer to yogurt, custard, milk smoothies, milkshakes, and dairy ice cream.

[0168] Confectionery products can refer to sweet or candy food products, such as chewing gum or hard and soft confectionery products. Non-limiting examples of confectionery products include cakes, cookies, pies, chocolates, chewing gum, gelatin, ice cream, pudding confections, jams, jellies, gummies, hard-boiled candies, chewy candies, cereals and other breakfast foods, canned fruits, and fruit sauces.

[0169] Beverage products can refer to beverages, beverage mixes, and concentrates, which include, but are not limited to, alcoholic and non-alcoholic ready-to-drink beverages and dry powder beverages. Non-limiting examples of beverages can include carbonated and non-carbonated beverages, such as soda, fruit or vegetable juices.

[0170] Sauce products can refer to sweet or flavorful semi-solid compositions used to add flavor, moisture, and / or visual appeal to dishes. Non-limiting examples of sauces include gravy and barbecue sauce.

[0171] Alternative meat products can refer to foods made from vegetarian ingredients that approximate certain types of meat in terms of aesthetic qualities (texture, flavor, appearance, etc.) or chemical characteristics. Non-limiting examples of alternative meat include plant-based (veggie) burgers.

[0172] One of ordinary skill in the art will recognize that the optimal amount of a food coloring composition present in a given food product is determined by factors such as the overall desired color, solubility, regulatory approval, and the like. Based on those factors, one of ordinary skill in the art can readily determine the optimal amount of color for a given product.

[0173] In one aspect, the product (food ingredient, pharmaceutical, dietary supplement, functional food, flavor or cosmetic product) is packaged in a transparent or translucent package.

[0174] Kit The present invention also relates to kits comprising different elements of the coloring compositions of the present invention and optionally instructions regarding the mixing, preparation and / or use of said ingredients. In one aspect, the kit comprises elements that are already mixed and ready for use (e.g., as a blend) and optionally instructions for the use of said ingredients. In one aspect, the kit comprises other colors such as yellow or red.

[0175] Color evaluation The coloring compositions and products containing the coloring compositions of the present disclosure can be analyzed with a spectrophotometer and, as will be described in more detail below, CIELAB L * a * b * values can be calculated from the spectral data. The L * a * b * values represent the characteristics of the color and provide a means for assessing the magnitude of the difference between two colors. The L * a * b * values represent the characteristics of the color and also provide a means for assessing the magnitude of the difference between two colors not only for solutions but also for products. The measurement of the color compositions and products in solid form is accomplished using reflectance measurements from the surface of the product.

[0176] For example, the L * a * b * values consist of a set of coordinate values defined in a three-dimensional Cartesian coordinate system. The L *is the lightness coordinate, with a scale of lightness from black (0 L * units) to white (100 L * units) provided on the vertical axis, and a * and b * are coordinates related to both hue and chroma. a* provides a scale from greenness (-a * units) to redness (+a * units) on the horizontal axis, with an intermediate color at the center point (0 a * units); b * is on the second horizontal axis perpendicular to the first horizontal axis, providing a scale from blueness (-b * units) to yellowness (+b * units), with an intermediate color (0 b * units) at the center point. L * has a value of 50, and the three axes where both a * and b * are zero intersect.

[0177] ΔE is a measure of the magnitude of the total color difference between two colors represented in the CIELAB L * a * b * color space. Skilled color observers have reported that they cannot distinguish the difference between two colors when ΔE is about 2.3 or less. L * a * b * values, L * 1a * 1b * 1 and L * 2a * 2b * 2 for two different colors are calculated using Equation 1.

Equation

[0178] Example Materials and methods Materials and Methods: - Monascus extract: The pigment was purchased from CNJ Nature. According to the supplier, the red pigment was obtained from fermented rice, extracted with ethanol, purified, then blended with maltodextrin, and finally spray-dried. The pigment content is approximately 71%. - Water-soluble rutin: Sophora japonica extract was enzymatically glycosylated. This reaction added sugar to the rutin backbone to make it water-soluble (Figure 2). The final product contains 4.5% rutin glucoside formulated in a water-glycerol carrier.

Chemical formula

[0179] - Lemon balm (4 - 7%): Melissa Officinalis was extracted twice with ethanol (70%), purified using charcoal, and after concentration, the product was blended with monopropylene glycol to obtain 4 - 7% rosmarinic acid. - Water-dispersible tocopherol: Tocopherol was formulated using water and gum arabic, and then spray-dried to form a dry emulsion. The final concentration of tocopherol is 15%.

[0180] - Lycopene suspension: Lycopene was purchased from Lycored. Lycopene was extracted from tomatoes using ethyl acetate and ethanol, purified and concentrated, and the final product was formulated in glycerol, lecithin, sucrose ester, and water. The final pigment content is 2%. - Green bean coffee: Chlorogenic acid was extracted using a mixture of water and ethanol, purified, and then formulated in maltodextrin. The final concentration of chlorogenic acid was 4.5%. - Gamma-cyclodextrin: The product was purchased from Sigma-Aldrich and has a purity >98%. Cas number 17465-86-0

[0181] Example 1: Improvement of Monascus photo-stability using lycopene Solution 1A: 0.03 g of Monascus extract powder (71% pigment) was mixed with 0.015 g of lycopene suspension (2% lycopene), and the blend was introduced into 99.95 g of DI water (Solution 1A). (1A) The solution was measured with a spectrophotometer (Konica Minolta) for the evaluation of the initial L, a, b parameters and set as the standard. The initial absorption at 490 nm was also recorded for the calculation of the pigment retention rate. Subsequently, the samples were subjected to light stress using a SUNTEST cps+ (350 w / m2, 4 °C for 26 h), and the degradation rate was measured by displaying the pigment retention rate R and dE2000. As a control, together with the solution (1A), the solutions of Monascus alone (1B) and lycopene alone (1C) were irradiated simultaneously. Composition of 1B: 0.03% Monascus extract, 99.97% water Composition of 1C: 0.015% lycopene suspension, 99.98% water

[0182] As described so far, the rate of Monascus degradation was explained by the change in the color variation DE2000 and the pigment retention rate at 490 nm.

Number

[0183] Results. As seen in Figures 1 and 2, the photo-stability of Solution 1A (mixture of Monascus and lycopene) increases. Figure 1 shows that light irradiation induced a dramatic decomposition of Monascus molecules, and surprisingly, when mixed with lycopene, a protective effect on Monascus was introduced, which is reflected by an enhancement in the color retention rate from 6% (control) to 55% in the mixture, resulting in a smaller color change (dE2000) (Figure 2). Without being bound by any theory, we presume that lycopene exerts a protective effect on Monascus (sacrificial chromophore).

[0184] Example 2: Screening of polyphenols for photo-stabilization 0.03 g of Monascus extract powder (71% pigment) was mixed with 0.15 g to 1 g of water-soluble polyphenol, and the blend was introduced into DI water to reach a final concentration of 0.03% of Monascus extract. The solution was measured with a spectrophotometer (Konica Minolta) for the evaluation of the initial L, a, b parameters and set as the standard. The initial Abs at the maximum wavelength (490 nm) was also recorded for the calculation of the pigment retention rate. Subsequently, the samples were subjected to light stress for 20 h using SUNTEST cps+ (350 w / m2, T4 °C), and the rate of decomposition was measured by displaying the pigment retention rate R and DE2000 during irradiation. These 20 h in this state correspond to approximately 20 days in the normal light store state of a supermarket.

[0185] - Composition 2A: 0.03% Monascus extract + 99.97% water - Composition 2B: 0.03% Monascus + 0.15% lemon balm extract (eluted with ethanol) + 1% water-soluble rutin (4% rutin glucoside) + 98.82% water. - Composition 2C: 0.03% Monascus + 0.15% lemon balm extract (extracted with ethanol) + 99.82% water. - Composition 2D: 0.03% Monascus + 0.15% green bean coffee extract + 99.82% water. - Composition 2E: 0.03% Monascus + 0.15% green bean coffee extract + 1% water-soluble rutin (4% rutin glucoside) + 98.82% water. - Composition 2F: 0.03% Monascus + 1% water-soluble rutin (4% rutin glucoside) + 98.97% water.

[0186] Results: As found in Example 1, Figure 3 shows that light irradiation induced dramatic decomposition of Monascus molecules. Surprisingly, when mixed with rutin glucoside, a protective effect was introduced to Monascus, which was reflected by the enhancement of the color retention rate from 10% (control) to 57% in the mixture. When lemon balm extract (ethanol extract) was used, the retention rate of Monascus increased by up to 56%, and a stabilizing effect that brought about a smaller color change (dE2000) (Figure 4) was also confirmed.

[0187] Example 3: Screening of different ratios of lemon balm 0.03 g of Monascus extract powder (71% pigment) was mixed with 0.1 - 0.4 g of lemon balm extract, and the blend was introduced into DI water to reach a final concentration of 0.03% of the Monascus extract. The solution was measured with a spectrophotometer (Konica Minolta) for the evaluation of the initial L, a, b parameters and set as the standard. The initial Abs at the maximum wavelength (490 nm) was also recorded for the calculation of the pigment retention rate. Subsequently, the samples were subjected to light stress using SUNTEST cps+ (350 w / m2, T4℃), and the rate of decomposition was measured by displaying the pigment retention rate R and DE00 during irradiation (25 h).

[0188] - 3A composition: 0.03% Monascus extract + 99.97% water. - 3B composition: 0.03% Monascus + 0.1% lemon balm extract (7 - 15% rosmarinic acid) + 99.87% water. - 3C composition: 0.03% Monascus + 0.2% lemon balm extract (7 - 15% rosmarinic acid) + 99.77% water. - 3D composition: 0.03% Monascus + 0.4% lemon balm extract (7 - 15% rosmarinic acid) + 99.57% water.

[0189] Results: As seen in Figure 6, by increasing the dosage of lemon balm extract, the pigment retention rate improved by up to 70% at 0.4% of lemon balm, resulting in a smaller color change (dE2000) Figure 5.

[0190] Example 4: Screening of different ratios of water-dispersible tocopherol 0.03 g of Monascus extract powder (71% pigment) was mixed with 0.01 g to 0.1 g of tocopherol powder (15% tocopherol), and the blend was introduced into DI water to reach a final concentration of 0.03% of Monascus extract. The solution was measured with a spectrophotometer (Konica Minolta) for the evaluation of the initial L, a, b parameters and set as the standard. The initial Abs at the maximum wavelength (490 nm) was also recorded for the calculation of the pigment retention rate. Subsequently, the samples were subjected to light stress using SUNTEST cps+ (350 w / m^2, T4 °C), and the degradation rate was measured by displaying the pigment retention rate R and DE00 during irradiation. - Composition 4A: 0.03% Monascus extract + 99.97% water. - Composition 4B: 0.03% Monascus + 0.01% water-dispersible tocopherol (tocopherol content 15%) + 99.96% water. - Composition 4C: 0.03% Monascus + 0.05% water-dispersible tocopherol (15%) + 99.92% water. - Composition 4D: 0.03% Monascus + 0.1% water-dispersible tocopherol (15%) + 99.87% water. Results: As shown in Figure 7, as the dosage of tocopherol increases, the pigment retention rate improves by up to 60% at 0.1% tocopherol, resulting in a smaller color change (dE2000) (Figure 8).

[0191] Example 5: Synergistic effect of tocopherol and lemon balm 0.03 g of Monascus extract powder (71% pigment) was mixed with 0.25 g of lemon balm extract and different ratios of water-dispersible tocopherol, and the blend was introduced into DI water to reach a final concentration of 0.03% of Monascus extract. The solution was measured with a spectrophotometer (Konica Minolta) for the evaluation of the initial L, a, b parameters and set as the standard. Subsequently, the samples were subjected to light stress using SUNTEST cps+ (350 w / m^2, T4 °), and DE2000 was measured after 20 h of light irradiation.

[0192] - Composition 5A: 0.03% Monascus extract + 99.97% water - Composition 5B:: 0.03% Monascus + 0.25% lemon balm (7 - 14% rosmarinic acid) + 99.96% water. - Composition 5C: 0.03% Monascus + 0.25% lemon balm (7 - 14% rosmarinic acid) + 0.02% water - dispersible tocopherol (15%) + 99.70% water. - Composition 5D: 0.03% Monascus + 0.25% lemon balm (7 - 14% rosmarinic acid) + 0.05% water - dispersible tocopherol (15%) + 99.70% water. Results: As shown in Figure 10, when tocopherol and lemon balm were mixed, the pigment retention rate was improved by up to 84% with 0.025% and 0.05% tocopherol and 0.25% lemon balm, resulting in a smaller color change (dE2000) in Figure 9. This result suggests that there is a synergistic effect of protection against light between lemon balm and tocopherol

[0193] Example 6: Synergistic effect of gamma-cyclodextrin and lemon balm 0.03 g of Monascus extract powder (71% pigment) was mixed with 0.2 g of lemon balm extract (ethanol extract (4 - 7% rosmarinic acid)) or 0.2 g of gamma - cyclodextrin (purchased from sigma, purity 98%), and the mixture of lemon balm extract and gamma - cyclodextrin was also tested (the above composition). The blend was introduced into DI water to reach a final concentration of 0.03% of Monascus extract. The solution was measured with a spectrophotometer (Konica Minolta) for the evaluation of the initial L, a, b parameters and set as the standard. Then, the samples were subjected to light stress using SUNTEST cps+ (350 w / m2, T4C), and DE2000 was measured 15 h after light irradiation.

[0194] - Composition 6A: 0.03% Monascus extract + 99.97% water. - Composition 6B: 0.03% Monascus + 0.2% lemon balm (4 - 7% rosmarinic acid) + 99.95% water. - 6C composition: 0.03% Monascus + 0.20% gamma-cyclodextrin + 99.95% water. - 5D composition: 0.03% Monascus + 0.2% lemon balm (4 - 7% rosmarinic acid) + 0.2% gamma-cyclodextrin + 99.57% water.

[0195] Results: As can be seen in Figure 11, cyclodextrin can improve the stability of pigments. Surprisingly, when lemon balm was mixed with gamma-cyclodextrin pigments, the stability was improved, resulting in a smaller color change (dE2000). This result suggests the possibility of a synergistic effect of protection against light between lemon balm and cyclodextrin.

[0196] Without being bound by any theory, we believe that lemon balm protects against oxygen elimination and photodegradation during ultraviolet filtering, and on the other hand, gamma-cyclodextrin provides a protective effect when hosting the partial carbon chain of Monascus in the hydrophobic cavity of cyclodextrin.

[0197] Example 7: Stabilization using lycopene in a sugar paste matrix Example 7 was carried out to investigate the important components of the mixture for the stabilization of Monascus. - Sample 7A: 0.03 g of Monascus extract powder (71% pigment) was mixed with 0.015 g of lycopene suspension (2% lycopene), mixed with 300 uL of DI water, and the blend was introduced into 99.95 g of sugar paste water (Sample 7A). - Samples were measured with a spectrophotometer (Konica Minolta), and the initial L, a, b parameters were evaluated and set as the standard. Subsequently, the samples were subjected to light stress using SUNTEST cps+ (350 w / m2, 4 °C for 8 h), and the degradation rate was measured by displaying the pigment retention rate R and dE2000. As a control, samples of Monascus alone (7B) and lycopene alone (7C) and unmixed Monascus and lycopene (7D) were irradiated simultaneously with the solution (7A).

[0198] Composition 7B: 0.03% Monascus extract, 99.97% sugar paste Composition 7C: 0.015% lycopene suspension, 99.98% sugar paste Composition 7D: 0.03% Monascus extract was first incorporated into the sugar paste, and then 0.015% of lycopene was added to 99.98% sugar paste without pre - mixing as in 7A As can be seen in Graph 11, pre - mixing lycopene and Monascus gives better retention against light stress.

Claims

1. A method for stabilizing the color of a polyketide dye, comprising (i) contacting the polyketide dye with (ii) a carotenoid, rosmarinic acid, ruting glucoside, cyclodextrin and / or tocopherol, wherein the resulting polyketide dye is photostable.

2. The method according to claim 1, wherein the polyketide is selected from azaphylones, anthraquinones, hydroxyanthraquinones and / or naphthaquinones.

3. The method according to claim 1, wherein the azafilone is selected from one or more of the following: nitrogenated azafilones, austodiols, spiciferinone and derivatives, deflectins, helothialins, bulgarylactones, spiroazafilones, O-substituted azafilones (especially O-containing monascus dyes), lactone azafilones, hydrogenated azafilones, chaetobiridines and chaetomgirines, sequoiatons, trichoflectin and sassafrin azafilones, pulvilonate-type azafilones, sclerothiolins, multiformins and cohelins, ascochitine, chrysodine-type azafilones, hydrogenated spiroazafilones, chlorofucins, atrolosins, N-containing monascus dyes, and atrocin-type azafilones.

4. Azafilone is selected from monasin, ankaflavin, monascorburin, rubropuntatin, monascorbramin, rubropuntamine and / or monascorbramic acid (compounds represented by formula (I)) and any derivative thereof. 【Chemistry 1】 The method according to claim 3, wherein in monascolbramin (C23H27NO4), rubropunctamin (C21H23NO4), and monascolbramic acid, NR is selected from the group consisting of amino acids, peptides, amino sugars, and primary amines, and the waveform bond indicates an unspecified arrangement of adjacent double bonds between carbon 2 and carbon 3.

5. The method according to any one of claims 1 to 4, wherein the polyketide is obtained or can be obtained from one or more of the fungal genera Aspergillus, Chaetomium, Hypoxylon, Monascus, Muycopron, Penicillium, Phomopsis, Pleosporales, Talaromyces, Pestalotiopsis, Phomopsis, Emericella, Epicoccum, and / or Hypoxylon.

6. The method according to claim 5, wherein Talaromyces is Talaromyces atroroseus.

7. The method according to claim 1, wherein the pigments are extracted from their natural state in an unmodified form, or obtained from their natural state and purified or chemically modified.

8. The method according to claim 1, wherein the dye is a mixture or a single compound.

9. The method according to claim 1, wherein the carotenoid is selected from lycopene, bixin, norbixin, or a mixture thereof.

10. The method according to claim 9, wherein lycopene is in crystalline form.

11. The method according to claim 9, wherein in addition to lycopene, bixin and / or norbixin, one or more of rosmarinic acid, ruting glucoside, cyclodextrin and / or tocopherol are used.

12. (ii) is tocopherol and rosmarinic acid, or (ii) is cyclodextrin and rosmarinic acid, The method according to claim 1, wherein chlorogenic acid is optionally used additionally, and the chlorogenic acid is obtained or can be obtained from green beans of any species of the genus Coffea, such as Coffea arabica, Coffea canephora, or Coffea liberica.

13. A stabilized dye obtained by the method of Claim 1, characterized in that it has a color that is stable to light exposure.

14. A coloring composition comprising the stabilizing dye described in claim 13.

15. Food ingredients, pharmaceuticals, nutritional supplements, fragrances, or cosmetic products comprising the stabilized dye according to claim 13, or the coloring composition according to claim 14, which are optionally exposed to light.

16. A method for producing food ingredients, pharmaceuticals, nutritional supplements, fragrances or cosmetic products, comprising the step of incorporating component (i) and component (ii) as defined in claim 1, particularly when the product is liquid or semi-solid, wherein component (i) is directly added to the product and as a result product (ii) is also added to the product, or component (ii) is directly added to the product and as a result product (i) is also added to the product.

17. Food ingredients, pharmaceuticals, nutritional supplements, fragrances, or cosmetic products obtained by the method of claim 16, characterized by having a light-stable red, orange, or yellow color.

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