compound

Abstract

The present invention relates to compositions having synergistic antioxidant properties whose components are derived from plant extracts, wherein the compositions are useful in food preparations.

Description

[Technical Field]

[0001] FIELD OF THE INVENTION The present invention relates to the use of plant extracts to obtain antioxidants useful in the production of foodstuffs, cosmetics and functional foods. [Background technology]

[0002] Background of the Invention Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals and chain reactions that can damage living cells. Antioxidants are widely used in the agricultural industry, such as meat and poultry, beverages, salad dressings, seasonings, and snacks, to preserve and slow food deterioration, rancidity, and discoloration. In addition, antioxidants have also been used in various cosmetic and toiletry products, as well as pharmaceutical compositions, to prevent oxidation. Finally, antioxidants are also commonly used as nutraceuticals. Therefore, the primary use of antioxidants is to prevent the deterioration of product characteristics by preventing oxidative damage as well as cellular damage caused by oxygen radicals.

[0003] The use of synthetic antioxidants in commercial food preparations has been largely replaced by antioxidants from natural sources, such as those found in spices such as rosemary and sage. Antioxidants from natural sources have been found to be stable at high temperatures, are readily soluble in oil, and are considered safer than synthetic antioxidants. Most natural antioxidants are derived from plant materials such as fruits, vegetables, herbs, and spices.

[0004] Antioxidants are mainly obtained from liquid extracts in solvents from natural sources where antioxidants exist. Small changes in the process of obtaining plants and the processing leading up to the extraction process can result in large differences in yield and in the antioxidant activity of the extract. Furthermore, scaling up such extractions is not always easy and results in increased production of by-products. Therefore, alternative antioxidants with higher antioxidant capacity are needed to facilitate the antioxidant extraction process and help reduce the amount of by-products from the extraction process. Summary of the Invention

[0005] Summary of the Invention The inventors have discovered that certain combinations of antioxidant extracts provide a synergistic effect on the antioxidant activity of the extract composition. Thus, a first aspect of the present invention is a composition comprising chlorogenic acid and: (i) rosmarinic acid; and (ii) Phenolic diterpenes and one or more additional components or combinations of components selected from the group consisting of: wherein the ratio of chlorogenic acid to one or more additional components or combination of components is from about 100:1 to about 1:100.

[0006] Another aspect of the invention relates to the use of a composition according to the invention in the manufacture of a human or animal food or beverage product, a nutritional supplement, a nutraceutical formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a vinification formulation or a cosmetic formulation. Another aspect of the present invention relates to the use of the composition according to the invention as an antioxidant.

[0007] Another aspect of the present invention relates to a process for preventing and / or inhibiting oxidation of a human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking formulation or a cosmetic formulation, the process comprising the step of contacting a foodstuff with a composition according to the present invention.

[0008] Another aspect of the present invention relates to a human or animal food or beverage product, nutraceutical, functional food formulation, fragrance or flavoring agent, pharmaceutical or veterinary formulation, vinification or cosmetic formulation comprising an antioxidant composition according to the present invention, or a nutraceutical or dietary supplement comprising a composition according to the present invention, as well as an acceptable adjuvant for the human or animal food or beverage product, nutraceutical, functional food formulation, fragrance or flavoring agent, pharmaceutical or veterinary formulation, vinification or cosmetic formulation. [Brief explanation of the drawings]

[0009] [Figure 1] ORAC-CAT values ​​for formulas containing rosemary and green coffee beans. [Figure 2] CAT values ​​for formulas containing sage and green coffee beans. [Figure 3] TSL in pork = TBArs value for a 10-day period. DETAILED DESCRIPTION OF THE INVENTION

[0010] Detailed Description of the Invention As mentioned above, the present invention discloses compositions of extracts with antioxidant effects that exhibit synergistic antioxidant activity compared to the antioxidant activity of the individual extracts. These compositions are obtained by mixing antioxidant extracts from different plant sources in certain proportions.

[0011] Compositions of the Invention Therefore, a first aspect of the present invention is a composition comprising chlorogenic acid and: (i) rosmarinic acid; and (ii) Phenolic diterpenes and one or more additional components or combinations of components selected from the group consisting of: wherein the ratio of chlorogenic acid to one or more additional components or combination of components is from about 100:1 to about 1:100.

[0012] The term " antioxidant " as used herein refers to a compound that can inhibit the reaction promoted by oxygen or the reaction induced by the presence of metals such as iron (Fenton reaction), thereby preventing the oxidation and rancidity of composition.Therefore, antioxidant reduces the amount of oxidation over a given period of time compared with the oxidation that would occur in its absence.The method for determining the antioxidant capacity of a compound in a composition is well known in the art, and is exemplified in the examples section of this specification under the section " In vitro ORAC test " and " In vitro CAT test ".

[0013] The term "chlorogenic acid" as used herein refers to an ester of caffeic acid and (-)-quinic acid. Chlorogenic acid naturally occurs in coffee primarily as monoesters and diesters of quinic acid with phenolic groups (such as caffeic acid, ferulic acid, coumaric acid, and methoxycinnamic acid) attached at various positions. Chlorogenic acid is identified in the CAS Registry Database entry by number 202650-88-2 and structurally by the formula (iii): [ka] It is defined by

[0014] The ratio of chlorogenic acid may be relative to one additional component of the compositions of the present invention (such as rosmarinic acid or a phenolic diterpene) or may be relative to both additional components of the compositions of the present invention, i.e., rosmarinic acid and a phenolic diterpene. In preferred embodiments of the compositions of the present invention, the ratio of chlorogenic acid to one or more additional components or combinations of components is about 95:5, 97:7, 90:10, 85:15, 80:20, 75:25, 70:30, 65:35, 60:40, 55:45, 50:50, 45:55, 40:60, 35:65, 30:70, 25:75, 20:80, 15:85, 10:90, 7:97, or 5:95. In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to one or more additional components or combinations of components is 50:1 to 1:50, preferably 25:1 to 1:25. In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to one or more additional components or combinations of components is about 50:1 to about 1:50, such as about 25:1 to about 1:25, for example about 10:1 to about 1:10, for example about 5:1 to about 1:5.

[0015] In a preferred embodiment of the composition of the present invention, the concentration of chlorogenic acid is about 0.1% w / v to 55% w / w, about 0.5% to about 25%, about 1% to about 10%, about 2.0% to about 3.0%, about 2.1% w / w to 2.9% w / w, about 2.15% w / w to 2.85% w / w, about 2.2% w / w to 2.8% w / w, about 2.25% w / w to 2.75% w / w, about 2.3% w / w to 2.7% w / w, about 2.3% w / w to 2.65% w / w, about 2.3% w / w to 2.6 ... In a more preferred embodiment of the composition of the present invention, the concentration of chlorogenic acid is about 4% to about 5%, or about 2% to about 3% w / w.

[0016] The compositions of the present invention further comprise one or more additional components selected from rosmarinic acid and phenolic diterpenes. The term "diterpene," as used herein, refers to a class of chemical compounds composed of four isoprene units and often has the molecular formula C 20 H 32 They are biosynthesized by plants, animals, and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being the main intermediate. "Phenolic diterpenes" are a subgroup of diterpenes, including, among others, carnosic acid, carnosol, rosmanol, epirosmanol, and methoxyepirosmanol. These components are, at least to some extent, the result of the degradation of carnosic acid, but they still possess antioxidant properties. "Phenolic diterpenes" are intended to encompass carnosic acid, carnosol, and their derivatives. Therefore, when "phenolic diterpenes" are referred to in this invention, carnosic acid, carnosol, and all of their derivatives are included.

[0017] In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to phenolic diterpene is about 25:1 to about 1:25, about 10:1 to about 1:10, about 5:1 to about 1:5, preferably about 0.9:1 to about 1:0.9.

[0018] In preferred embodiments of the compositions of the present invention, the concentration of phenolic diterpenes is at least about 0.5% w / w, at least about 1.7% w / w, at least about 1.8% w / w, at least about 1.9% w / w, at least about 2.0% w / w, at least about 2.1% w / w, at least about 2.2% w / w, at least about 2.3% w / w, at least about 2.4% w / w, preferably at least about 2.5% w / w, at least about 3.0% w / w, at least about 5.0% w / w, at least about 10% w / w, at least about 25% w / w, at least 50% w / w, at least 90% w / w.

[0019] The phenolic diterpene of the composition of the present invention can be obtained as an extract of the aerial parts of Salvia.In a preferred embodiment of the composition of the present invention, the phenolic diterpene is provided as an extract of the aerial parts of Salvia, preferably leaves.The term "aerial parts of Salvia" refers to the stems, leaves, petioles, flowers, fruits and seeds, preferably leaves, of plants of the genus Salvia, which belong to the family Lamiaceae and are composed of shrubs, perennial herbs and annual herbs.In a preferred embodiment of the composition of the present invention, the aerial parts of Salvia, preferably leaves, are derived from the plant Salvia officinalis or the plant Salvia apiana.

[0020] Those skilled in the art will recognize that there are known methods for obtaining the extract of the aerial parts of Salvia, as they are well known in the art.For example, the method described in the document WO96 / 34534, which is incorporated herein by reference, may be used in the present invention.In a preferred embodiment of the composition of the present invention, the extract of the aerial parts of Salvia, preferably the leaves, is prepared by the following method: (i) extracting the aerial parts of Salvia, preferably the leaves, with acetone and activated carbon; and, optionally, (ii) further purifying the extract is obtained by In step (i) of the method for obtaining an extract of the aerial parts, preferably the leaves, of Salvia, the extraction is carried out using a composition of an organic solvent (i.e., acetone) and activated carbon.

[0021] Several methods for extracting plant parts are known in the art. One such method is solvent extraction, which separates compounds based on their relative solubility in two different immiscible liquids, usually water (polar) and organic solvent (non-polar). There is a net transfer of one or more species from one liquid to another liquid phase (generally from an aqueous phase to an organic phase). The transfer is driven by chemical potential. That is, once the transfer is complete, the overall system of chemical components that make up the solute and solvent assumes a more stable conformation (lower free energy). In a preferred embodiment of the composition of the present invention, an extract of green coffee beans is obtained by extraction with an alcoholic solvent.

[0022] In the context of this invention, a "solvent" refers to a substance that dissolves a solute to produce a solution. Solvents are usually liquids, but can also be solids, gases, or supercritical fluids.

[0023] The term "alcoholic solvent," as used herein, refers to a solvent containing an ethyl group bonded to a hydroxyl group. Examples of alcoholic solvents include, but are not limited to, ethanol, ethylene glycol, isopropanol, methanol, isobutanol, diethylene glycol, etc. In a preferred embodiment of the composition of the present invention, the extraction of green coffee beans is carried out with ethanol, preferably at a solvent to water ratio of 75% to 25%.

[0024] The term "activated carbon," also known as activated charcoal, as used herein refers to a form of carbon commonly used to filter contaminants from water and air, among many other uses. It is engineered to have small, low-volume pores to increase the surface area available for adsorption or chemical reaction. In a preferred embodiment of the composition of the present invention, the aerial parts of Salvia, preferably the leaves, are extracted with activated carbon at a concentration of about 1% w / w to about 15% w / w, preferably about 3.5% w / w, about 4% w / w, about 5% w / w, or about 10% w / w.

[0025] In order to obtain better results in the extraction process of the aerial parts of Salvia, preferably the leaves, in a preferred embodiment of the composition of the present invention, the extraction of the aerial parts of Salvia, preferably the leaves, is carried out at a temperature of about 50°C to about 60°C, preferably 56.4°C, for about 1 hour to about 3 hours, preferably about 2 hours, with stirring.

[0026] After the extraction step has been carried out and the resulting plant residues removed, the extract is further purified by methods already known in the art to achieve higher concentrations of active ingredients, such as the methods described in WO 96 / 34534, which is incorporated herein by reference.

[0027] Another possible component of the composition of the present invention is rosmarinic acid. In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to one or more additional components or combinations of components is 50:1 to 1:50, such as 25:1 to 1:25, such as 10:1 to 1:10, such as 5:1 to 1:5. In a more preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to rosmarinic acid is about 50:1 to about 1:50, such as about 25:1 to about 1:25, such as about 10:1 to about 1:10, such as about 6:1 to about 1:6, preferably about 5:1 to about 1:5.

[0028] In a preferred embodiment of the method of the present invention, the concentration of rosmarinic acid is at least 0.1% w / w, preferably at least about 0.5% w / w, more preferably at least about 1% w / w. The term "rosmarinic acid" as used herein refers to the polyphenolic component of many culinary herbs, including rosemary (Salvia rosmarinus), lemon balm (Melissa officinalis L.), perilla (Perilla frutescens L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). Rosmarinic acid is an ester formed through the esterification of caffeic acid with 3,4-dihydroxyphenyllactic acid. Rosmarinic acid is identified in the CAS Registry Database entry by number 20283-92-5 and structurally by the formula (vii): [ka] It is defined by

[0029] Rosmarinic acid can be obtained from an extract of the aerial parts of rosemary or an extract of the aerial parts of Melissa officinalis. In a preferred embodiment of the composition of the present invention, rosmarinic acid is provided as an extract of rosemary leaves or an extract of the aerial parts of Melissa officinalis. In another preferred embodiment of the composition of the present invention, the rosemary leaves are derived from the plant species Salvia rosmarinus.

[0030] In a preferred embodiment, the rosemary leaf extract is obtained by extraction with water or an alcoholic solvent. The term "alcoholic solvent" has been defined above, and said definition is equally applicable to the present embodiment. In a preferred embodiment of the composition of the present invention, the rosemary leaf extraction is carried out with water.

[0031] Water extractions are well known in the art and their application is part of the general knowledge of experts. In a preferred embodiment of the composition of the present invention, the extraction of rosemary leaves is carried out by percolation at a temperature of about 80°C to about 100°C, preferably 90°C, for about 1 hour to about 3 hours, preferably about 1.5 hours.

[0032] In a preferred embodiment of the composition of the present invention, the rosemary leaf extract obtained is further filtered and concentrated, preferably by membrane filtration.

[0033] After the concentration step is carried out, the extract is purified on a polymeric adsorption resin, and the purified extract is spray-dried on maltodextrin or formulated on ethanol or propylene glycol.

[0034] As mentioned above, rosmarinic acid can be obtained from an extract of the aerial parts of Melissa officinalis. The term "aerial parts" as used herein refers to, but is not limited to, buds, leaves, stems, flowers, fruits, and seeds, with Melissa officinalis leaves or seeds being preferred. In a preferred embodiment of the composition of the present invention, the extract of the aerial parts of Melissa officinalis is obtained by extraction with ethanol and activated carbon. In another preferred embodiment of the composition of the present invention, the extract of the aerial parts of Melissa officinalis is obtained by extraction with ethanol and activated carbon, wherein ethanol is used at a solvent concentration of about 70% v / v relative to water, and activated carbon is used at a concentration of about 1% w / v to about 15% w / v, preferably about 3% w / v, about 4% w / v, about 5% w / v, about 6% w / v, about 7% w / v, about 8% w / v, or about 10% w / v.

[0035] In a preferred embodiment, the composition of the present invention further comprises caffeine, wherein the ratio of chlorogenic acid to caffeine is from about 15:1 to about 1:15, such as from 10.1 to about 1.10, such as from about 1.5:1 to about 10:1, such as from about 1.5.1 to about 1:1.5.

[0036] In preferred embodiments, the compositions of the present invention further comprise caffeine at a concentration of about 0.01% w / v to about 15% w / v, about 0.25% w / v to 12% w / v, about 0.5% w / v to 10% w / v, about 1% w / v to 9% w / v, about 2% w / v to 8% w / v, about 2% w / v to 7% w / v, about 3% w / v to 6% w / v, or about 4% w / v to 5% w / v. In a preferred embodiment, the composition of the present invention comprises from about 0.01% w / w to about 1.5% w / v, from about 0.25% w / v to 1.5% w / v, from about 0.3% w / v to 1.45% w / v, from about 0.35% w / v to 1.4% w / v, from about 0.4% w / v to 1.35% w / v, from about 0.45% w / v to 1.3% w / v, from about 0.5% w / v to 1.25% w / v, or from about Further containing caffeine at concentrations of about 0.55% w / v to 1.2% w / v, about 0.6% w / v to 1.15% w / v, about 0.65% w / v to 1.1% w / v, about 0.7% w / v to 1.05% w / v, about 0.75% w / v to 1% w / v, about 0.8% w / v to 1% w / v, about 0.85% w / v to 1% w / v, and about 0.9% w / v to 1% w / v.

[0037] The term "caffeine," as used herein, refers to a bitter-tasting, white crystalline purine methylxanthine alkaloid, which is identified in the CAS Registry Database entry by the number 58-08-2 and structurally by the formula (iv): [ka] It is defined by

[0038] Since coffee beans are a source of both chlorogenic acid and caffeine, preparing the composition of the present invention starting from coffee beans will result in a composition containing both chlorogenic acid and caffeine. However, for the purposes of the present invention, any plant containing chlorogenic acid and / or caffeine may be used, such as yerba mate (Ilex paraguariensis), white tea (Camellia sinensis), wintersbark (Drimys winteri), green tea (Camellia sinensis), elderflower (Sambucus nigra), and Boehmeria caudate. In a preferred embodiment of the composition of the present invention, chlorogenic acid and caffeine are provided as an extract of green coffee beans. As used herein, the term "green coffee beans" refers to unroasted coffee beans. In another preferred embodiment of the composition of the present invention, the coffee beans are derived from the plant species Coffea Arabica or Coffea robusta.

[0039] Methods for obtaining chlorogenic acids and caffeine from coffee beans are widely known in the art and examples are provided in the present description (see Examples). In a preferred embodiment of the composition of the present invention, the obtained green coffee bean extract is further filtered and concentrated. In another preferred embodiment, the concentrated extract is supplemented with an organic strong or weak acid.

[0040] The term "organic acid," as used herein, refers to an organic compound with acidic properties. The most common organic acids are carboxylic acids, whose acidity is related to their carboxyl group, -COOH. Sulfonic acids, containing the -SO2OH group, are relatively strong acids. Alcohols with -OH can act as acids, but are usually very weak. The relative stability of an acid's conjugate base determines its acidity. Other groups can also impart acidity, but these are usually weak: thiol groups, -SH, enol groups, and phenolic groups. In biological systems, organic compounds containing these groups are commonly referred to as organic acids. Examples of organic acids include, but are not limited to, lactic acid, acetic acid, formic acid, citric acid, oxalic acid, uric acid, malic acid, and tartaric acid.

[0041] In a preferred embodiment of the composition of the present invention, the concentration of the phenolic diterpene carnosic acid is 0.1% w / v to 5% w / v, about 0.25% w / v to 4.75% w / v, about 0.5% w / v to 4.5% w / v, about 0.75% w / v to 4.25% w / v, about 1% w / v to 4% w / v, about 1.25% w / v to 3.75% w / v, about 1.5% w / v to 3.5% w / v, about 1.75% w / v to 3.25% w / v, about 2% w / v to 3% w / v, about 2.25% w / v to 3% w / v, or about 2.5% w / v to 3% w / v.

[0042] The term "carnosic acid" in the context of this specification refers to a benzenediol abietane diterpene found in Salvia rosmarinus, Salvia officinalis, etc. Carnosic acid is identified in the CAS Registry Database entry by accession number 3650-09-7 and structurally by the formula (v): [ka] It is defined by

[0043] In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to the phenolic diterpene carnosolic acid is about 50:1 to 1:50, for example, about 25:1 to 1:25, for example, about 10:1 to 1:10, for example, about 5:1 to 1:5. In a more preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to rosmarinic acid is about 6:1 to 1:6, preferably about 5:1 to 1:5. In a preferred embodiment of the composition of the present invention, the concentration of the phenolic diterpene carnosol is about 0.001% w / v to about 5% w / v, about 0.01% w / v to 5.0% w / v, about 0.1% w / v to 5.0% w / v, about 0.2% w / v to 4.8% w / v, about 0.3% w / v to 4.7% w / v, about 0.4% w / v to 4.6% w / v, about 0.5% w / v to 4.5% w / v, about 0.6% w / v to 4.4% w / v, about 0.7% w / v to 4.3% w / v, about 0.8% w / v to 4.2% w / v, about 0.9% w / v to 4.1% w / v, about 1% w / v to 4% w / v, Approximately 1.1% w / v to 3.9% w / v, approximately 1.2% w / v to 3.8% w / v, approximately 1.3% w / v to 3.7% w / v, approximately 1.4% w / v to 3.6% w / v, approximately 1.5% w / v to 3.5% w / v, approximately 1.6% w / v to 3.4% w / v, approximately 1.7% w / v to 3.3% w / v, approximately 1.8% w / v to 3.2% w / v, approximately 1.9% w / v to 3.1% w / v, approximately 2% w / v to 3% w / v, approximately 2.1% w / v to 3% w / v, approximately 2.2% w / v to 3% w / v, approximately 2.3% w / v to 3% w / v, approximately 2.4% w / v to 3% w / v, and approximately 2.5% w / v to 3% w / v.

[0044] The term "carnosol," such as carnosic acid, as used herein refers to a phenolic diterpene found in Salvia rosmarinus, Salvia officinalis, etc. Carnosol is identified in the CAS Registry Database entry by accession number 5957-80-2 and structurally by the formula (vi): [ka] It is defined by

[0045] Carnosic acid and carnosol can be obtained from rosemary leaf extract.In a preferred embodiment of the composition of the present invention, the phenolic diterpene carnosic acid and / or carnosol are optionally provided as rosemary leaf extract.In another preferred embodiment of the composition of the present invention, rosemary leaf is derived from the plant species Salvia rosmarinus.

[0046] Several procedures for obtaining an extract of the aerial parts of rosemary are available in the literature, such as in document WO 96 / 34534, which is incorporated herein by reference. In a preferred embodiment of the composition of the present invention, an extract of the aerial parts of rosemary is obtained by the following steps: (i) extracting the aerial parts with an organic solvent, and optionally (ii) further purifying the extract The compound is obtained by a method comprising the steps of:

[0047] The term "organic solvent" as used herein refers to a carbon-based substance capable of dissolving or dispersing one or more other substances. Examples of organic solvents include, but are not limited to, acetic acid, acetone, acetonitrile, benzene, 1-butanol, 2-butanol, chloroform, ethanol, glycerin, etc. In a preferred embodiment of the composition of the present invention, the organic solvent used in the rosemary leaf extract is acetone.

[0048] After the extraction step has been carried out and the resulting plant residues removed, the extract is further purified by methods already known in the art to achieve higher concentrations of active ingredients, such as the methods described in WO 96 / 34534, which is incorporated herein by reference.

[0049] The extracts referred to herein for use in the compositions of the present invention may be filtered, dried, and further purified, concentrated, etc. after they are obtained. Techniques for applying such processes to extracts are well known in the art, and experts will be aware of such methods and be able to select the best parameters for carrying out such techniques. In a preferred embodiment of the composition, the extract is processed by a technique selected from filtration, drying, concentration, grinding, filtration and drying, filtration and concentration, filtration, concentration and drying, filtration, drying and grinding, or concentration, drying, and grinding. In another preferred embodiment of the composition of the present invention, the extract is dried in a vacuum oven at a temperature of about 50°C to about 100°C, preferably about 75°C, and more preferably about 85°C.

[0050] The extracts referred to herein can be further formulated in either a liquid or solid carrier. The extract obtained to form the synergistic composition of the present invention can further comprise a suitable carrier. In a preferred embodiment, the composition of the present invention further comprises a carrier. As used herein, the term "carrier" refers to any type of material suitable for the intended use, capable of supporting molecules, compounds, substances (such as plant extracts), or compositions through physical or chemical interaction with the carrier material. As an example of the interaction between the carrier material and the plant extract or composition, the interaction should not prevent the plant extract or composition from exerting its desired effect, i.e., should not reduce its antioxidant activity. In a preferred embodiment of the composition of the present invention, the carrier is liquid or solid. In another preferred embodiment of the composition of the present invention, the carrier is selected from the group consisting of ethanol, maltodextrin, and monopropylene glycol (MPG).

[0051] Processes and Uses of the Invention As mentioned above, substances with antioxidant properties find several uses, particularly in the agricultural and food industries. Thus, one aspect of the present invention relates to the use of the composition of the present invention as an antioxidant (hereinafter, Use I of the present invention).

[0052] Another aspect of the present invention relates to a process for preventing and / or inhibiting oxidation of foodstuffs, the process comprising the step of contacting the foodstuff with a composition of the present invention (hereinafter the process of the present invention). A further aspect of the present invention relates to the use of the composition of the present invention for preventing and / or inhibiting oxidation of foodstuffs (hereinafter Use II of the present invention). All previous embodiments and definitions set forth with respect to the previous aspects are equally valid for the present aspect and its embodiments.

[0053] Thus, in one aspect, the present invention relates to a process for preventing and / or inhibiting oxidation of a human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking or cosmetic formulation, comprising treating the human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking or cosmetic formulation with chlorogenic acid and one of the following: (i) rosmarinic acid; and (ii) Phenolic diterpenes and one or more additional components or combinations of components selected from the group consisting of: wherein the ratio of chlorogenic acid to one or more additional components or combination of components is from about 100:1 to about 1:100.

[0054] Thus, in one aspect, the present invention provides a composition comprising chlorogenic acid and: (i) rosmarinic acid; and (ii) Phenolic diterpenes and one or more additional components or combinations of components selected from the group consisting of: Here, the ratio of chlorogenic acid to one or more additional components or combinations of components as antioxidants is from about 100:1 to about 1:100.

[0055] Thus, in one aspect, the present invention relates to a process for preventing and / or inhibiting oxidation of a human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking or cosmetic formulation, comprising treating the human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking or cosmetic formulation with chlorogenic acid and one of the following: (i) rosmarinic acid; and (ii) Phenolic diterpenes and one or more additional components or combinations of components selected from the group consisting of: wherein the ratio of chlorogenic acid to one or more additional components or combination of components is from about 100:1 to about 1:100.

[0056] In some embodiments of the uses and processes of the present invention, the ratio of chlorogenic acid to one or more additional components or combinations of components is about 95:5, 97:7, 90:10, 85:15, 80:20, 75:25, 70:30, 65:35, 60:40, 55:45, 50:50, 45:55, 40:60, 35:65, 30:70, 25:75, 20:80, 15:85, 10:90, 7:97, or 5:95. In some embodiments, the ratio of chlorogenic acid to one or more additional components or combinations of components is 50:1 to 1:50, preferably 25:1 to 1:25. In some embodiments, the ratio of chlorogenic acid to one or more additional components or combinations of components is from about 50:1 to about 1:50, e.g., from about 25:1 to about 1:25, e.g., from about 10:1 to about 1:10, e.g., from about 5:1 to about 1:5.

[0057] In certain embodiments of the uses and processes of the present invention, the ratio of chlorogenic acid to rosmarinic acid is from about 50:1 to about 1:50, such as from about 25:1 to about 1:25, such as from about 10:1 to about 1:10, such as from about 6:1 to about 1:6, preferably from about 5:1 to about 1:5.

[0058] In some embodiments of the uses and processes of the present invention, the ratio of chlorogenic acid to the phenolic diterpene carnosolic acid is about 50:1 to 1:50, such as about 25:1 to about 1:25, such as about 10:1 to about 1:10, such as about 5:1 to about 1:5. In some embodiments, the ratio of chlorogenic acid to rosmarinic acid is about 6:1 to about 1:6, preferably about 5:1 to about 1:5. In certain embodiments, the concentration of the phenolic diterpene carnosol is from about 0.001% w / v to about 5% w / v, from about 0.01% w / v to 5.0% w / v, from about 0.1% w / v to 5.0% w / v, from about 0.2% w / v to 4.8% w / v, from about 0.3% w / v to 4.7% w / v, from about 0.4% w / v to 4.6% w / v, from about 0.5% w / v to 4.5% w / v, from about 0.6% w / v to 4.4% w / v, from about 0.7% w / v to 4.3% w / v, from about 0.8% w / v to 4.2% w / v, from about 0.9% w / v to 4.1% w / v, from about 1% w / v to 4% w / v, or from about 1.1% w / v. Approximately 1.2% w / v to 3.8% w / v, approximately 1.3% w / v to 3.7% w / v, approximately 1.4% w / v to 3.6% w / v, approximately 1.5% w / v to 3.5% w / v, approximately 1.6% w / v to 3.4% w / v, approximately 1.7% w / v to 3.3% w / v, approximately 1.8% w / v to 3.2% w / v, approximately 1.9% w / v to 3.1% w / v, approximately 2% w / v to 3% w / v, approximately 2.1% w / v to 3% w / v, approximately 2.2% w / v to 3% w / v, approximately 2.3% w / v to 3% w / v, approximately 2.4% w / v to 3% w / v, and approximately 2.5% w / v to 3% w / v.

[0059] As used herein, the term "oxidation" refers to the exposure of a composition and / or food material to conditions (such as a certain amount of atmospheric oxygen) sufficient to significantly oxidize it. Oxidation may occur through, but is not limited to, reactions promoted by oxygen or reactions induced by the presence of metals such as iron (Fenton's reaction). As used herein, the phrase "preventing and / or inhibiting food material oxidation" refers to a reduction in the oxidation that occurs to food materials in the presence of a composition of the present invention compared to oxidation that occurs in the absence of the composition. The term "prevention" refers to the complete absence of oxidation of food materials when the food material comprises a composition of the present invention. The term "inhibit" refers to a reduction in the level of oxidation that occurs to food materials. In certain embodiments of the process of the present invention, the oxidation of food material is inhibited by at least 1%, at least 5%, at least 10%, at least 15%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 91%, at least 92%, at least 93%, at least 94%, at least 95%, at least 96%, at least 97%, at least 98%, at least 99%, compared with the oxidation level of food material without the composition of the present invention.Methods for measuring food oxidation are well known in the art and in literature, for example, Barriuso et al., 2013 (European Food Research and Technology, Vol. 236, pp. 1-15).

[0060] In a particular embodiment, the process of the invention or the use I or II of the invention is in the manufacture of agro-alimentary products. The term "agro-alimentary", as used herein, refers to products used in manufacturing, processing and preparing food products for animal consumption, preferably human consumption. In a particular embodiment, the process of the invention or the use I or II of the invention is in the manufacture of a foodstuff.

[0061] The term "foodstuff," as used herein, is intended to mean a substance that is suitable for human or animal consumption. Furthermore, the term foodstuff, as used herein, is intended to encompass beverages and food ingredients used in the preparation of the foodstuff. As used herein, the term foodstuff includes, without limitation: beverages, eggs, egg-based products (including but not limited to mayonnaise, salad dressings, sauces, ice cream, egg powder, processed egg yolks and products made therefrom); baked products (breads, cakes, sweet doughs, etc.); dough products, laminated dough, liquid batters, muffins, donuts, biscuits, crackers and cookies); confectionery (including chocolate, candy, caramel, halawa, gums including unsweetened and sweetened gums, bubble gum, soft bubble gum, chewing gum, and puddings); frozen products (frozen dairy products including sorbet, preferably ice cream and ice milk); dairy products (including cheese, butter, milk, coffee creamer, whipped cream, custard cream, dairy drinks and yogurt); mousse, whipped vegetable cream, meat products (including processed meat products); edible oils and fats, carbonated and non-carbonated whipped products, oil-in-water emulsions, water-in-oil emulsions, margarine, shortening, and spreads including low-fat and extra-low-fat spreads; dressings, mayonnaise, dips, cream-based sauces, cream-based soups, beverages, spice emulsions, sauces, beverages, patisserie, oils, bakery products, fillings and edible inks.

[0062] In a preferred embodiment of the inventive process or the inventive use I or II, the foodstuff is a product selected from the group consisting of eggs, mayonnaise, salad dressing, sauces, ice cream, egg powder, modified egg yolks, bread, cake, sweet dough products, laminated dough, liquid batter, muffins, donuts, biscuits, crackers, cookies, chocolate, candy, caramel, halva, gum, bubble gum, soft bubble gum, chewing gum, pudding, sherbet, ice cream, ice milk, cheese, butter, milk, coffee creamer, whipped cream, custard cream, dairy drinks, yogurt, mousse, whipped vegetable cream, meat, processed meat products, oil, edible oil, fat, oil-in-water emulsion, water-in-oil emulsion, margarine, mayonnaise, dips, cream-based sauces, cream-based soups, beverages, spice emulsions, sauces, patisserie, dairy products, oils, bakery products, fillings and edible inks.

[0063] In a further preferred embodiment of the process of the present invention or the use I or II of the present invention, the food material is a meat product.The term "meat product" is used herein to mean a product extracted from poultry, fish, cattle, pigs, sheep, etc., which may be fatty or lean, and may be in the form of cut or shredded meat, minced meat, frozen meat, semi-frozen meat, or chilled meat, and may be processed or unprocessed.In a further preferred embodiment of the process of the present invention or the use I or II of the present invention, the food material is a pork product.

[0064] In a further preferred embodiment of the process of the invention or the use I or II of the invention, the foodstuff is a beverage, preferably a lemon-flavored beverage, the flavor of which may be natural and / or artificial. The content of the composition for the preparation of the foodstuff of the present invention will depend on the type of foodstuff as well as the intended use of such product.

[0065] Foodstuffs, functional foods, dietary supplements and other products of the present invention Use of the present invention allows the production of human or animal food or beverage products, dietary supplements, functional food formulations, fragrances or flavoring agents, pharmaceutical or veterinary preparations, oenological or cosmetic preparations with extended shelf life (i.e., reduced oxidation of said products).Accordingly, another aspect of the present invention relates to products (such as human or animal food or beverage products, dietary supplements, functional food formulations, fragrances or flavoring agents, pharmaceutical or veterinary preparations, oenological or cosmetic preparations) comprising the composition of the present invention, hereinafter referred to as foodstuffs of the present invention, or functional food or dietary supplements of the present invention, comprising the composition of the present invention and a food or dietary acceptable supplement.

[0066] All previous embodiments and definitions set forth with respect to the previous aspects are equally valid for the present aspect and its embodiments. The term "nutraceutical" as used herein refers to substances that are useful in both the nutritional and pharmaceutical fields. Thus, functional food compositions can be used as supplements to food and beverages, as well as pharmaceutical preparations for enteral or parenteral administration (which may be solid preparations such as capsules or tablets, or liquid preparations such as solutions or suspensions).

[0067] The expression "food or dietarily acceptable adjuvant," as used herein, refers to any food ingredient that can be used with a main ingredient to enhance, preserve, and improve the characteristics of the main ingredient. Adjuvants can also function as fillers, diluents, viscosity adjusters, etc.

[0068] In a preferred embodiment of the foodstuff of the present invention, the foodstuff is a meat product. In another preferred embodiment of the foodstuff of the present invention, the foodstuff is a pork product. A specialist will know how to adjust the amount of the composition in the foodstuff. In a preferred embodiment of the product of the present invention (such as a human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking or cosmetic formulation, etc.), the composition in the product (such as a foodstuff) comprises chlorogenic acid and phenolic diterpene in a ratio of about 0.1:1 to about 1:0.1, preferably about 0.8:1 to about 1:0.8.

[0069] In another preferred embodiment of the product (e.g., foodstuff, etc.) of the present invention, the composition in the product (e.g., foodstuff, etc.) comprises: - from about 0.1% w / w to about 55.0% w / w, preferably from about 2.0% w / w to 25% w / w, of chlorogenic acid; - from about 0.1% w / w to about 10.0 w / w, preferably from 0.2% w / w to about 5% w / w of caffeine; and at least about 0.1% w / w of phenolic diterpenes Includes.

[0070] In another preferred embodiment of the product (e.g., foodstuff, etc.) of the present invention, the composition in the product (e.g., foodstuff, etc.) comprises from about 2.25% w / w to about 2.4% w / w of chlorogenic acid, from about 0.25% w / w to about 1.5% w / w of caffeine, and greater than 2.5% w / w of phenolic diterpenes. In another preferred embodiment of the product (eg, foodstuff) of the present invention, the concentration in the product (eg, foodstuff) is about 0.5 parts per million (ppm) to about 1000 ppm, preferably about 400 ppm to about 600 ppm.

[0071] In another preferred embodiment, the product (e.g., foodstuff, etc.) of the present invention has a saturation concentration of about 1 ppm to about 1000 ppm, for example, about 5 ppm, 10 ppm, 20 ppm, 30 ppm, 40 ppm, 50 ppm, 60 ppm, 70 ppm, 80 ppm, 90 ppm, 100 ppm, 200 ppm, 300 ppm, 400 ppm, 500 ppm, 600 ppm, 700 ppm, 800 ppm, The chlorogenic acid content may be from about 1000 ppm, 900 ppm, 800 ppm, 700 ppm, 600 ppm, 500 ppm, 400 ppm, 300 ppm, 200 ppm, 100 ppm, 90 ppm, 80 ppm, 70 ppm, 60 ppm, 50 ppm, 40 ppm, 30 ppm, 20 ppm, 10 ppm, or up to 5 ppm. In one embodiment, the product (e.g., foodstuff) contains about 50 ppm of chlorogenic acid, preferably about 1 ppm to about 40 ppm of chlorogenic acid, more preferably about 1 ppm to about 30 ppm of chlorogenic acid, and even more preferably about 9 ppm to about 13.5 ppm of chlorogenic acid, based on the final weight of the product.

[0072] In another preferred embodiment, the product (e.g., foodstuff, etc.) of the present invention has an α-tocopherol content of about 1 ppm to about 1000 ppm, for example, about 5 ppm, 10 ppm, 20 ppm, 30 ppm, 40 ppm, 50 ppm, 60 ppm, 70 ppm, 80 ppm, 90 ppm, 100 ppm, 200 ppm, 300 ppm, 400 ppm, 500 ppm, 600 ppm, 700 ppm, 800 ppm The product contains from about 900 ppm to about 1000 ppm, 900 ppm, 800 ppm, 700 ppm, 600 ppm, 500 ppm, 400 ppm, 300 ppm, 200 ppm, 100 ppm, 90 ppm, 80 ppm, 70 ppm, 60 ppm, 50 ppm, 40 ppm, 30 ppm, 20 ppm, 10 ppm, or up to 5 ppm of phenolic diterpenes. In one embodiment, the product contains about 50 ppm of phenolic diterpenes, preferably 1 ppm to about 50 ppm of phenolic diterpenes, preferably about 1 ppm to about 40 ppm of phenolic diterpenes, more preferably about 1 ppm to about 30 ppm of phenolic diterpenes, and even more preferably about 10 ppm to about 15 ppm of phenolic diterpenes, based on the final weight of the product.

[0073] In another preferred embodiment, the product (e.g., foodstuff) of the present invention contains, based on the final weight of the product, about 1 ppm to about 50 ppm of phenolic diterpenes, preferably about 1 ppm to about 40 ppm of phenolic diterpenes, more preferably about 1 ppm to about 30 ppm of phenolic diterpenes, and even more preferably about 10 ppm to about 15 ppm of phenolic diterpenes.

[0074] In another preferred embodiment, the product (e.g., foodstuff) of the present invention is a meat product, and the concentration of the composition in the foodstuff is about 5 ppm to about 20 ppm for chlorogenic acid and about 5 ppm to about 25 ppm for phenolic diterpene, based on the final weight of the product. In another preferred embodiment, the product (e.g., foodstuff) of the present invention is a meat product, and the concentration of the composition in the foodstuff is about 13.5 ppm chlorogenic acid and about 15 ppm phenolic diterpene, based on the final weight of the product. In another preferred embodiment, the product (e.g., foodstuff) of the present invention is a pork product, and the concentration of the composition in the foodstuff is about 9 ppm chlorogenic acid and about 10 ppm phenolic diterpene, based on the final weight of the product.

[0075] In another embodiment of the foodstuff of the present invention, the foodstuff is a meat product and the concentration of the composition in the foodstuff is about 13.5 ppm chlorogenic acid and about 15 ppm phenolic diterpene. In another embodiment of the food material of the present invention, the food material is a meat product, and wherein the concentration of the composition in the food material is about 5 ppm to about 15 ppm, for example, about 9 ppm, for chlorogenic acid and about 5 ppm to about 20 ppm, for example, about 10 ppm or about 15 ppm, for phenolic diterpene. In another preferred embodiment, the foodstuff of the present invention is a pork product, and the concentration of the composition in the foodstuff is about 9 ppm chlorogenic acid and about 10 ppm phenolic diterpene, based on the final weight of the product.

[0076] In another preferred embodiment, the product (e.g., foodstuff, etc.) of the present invention has a saturation concentration of about 1 ppm to about 1000 ppm, for example, about 5 ppm, 10 ppm, 20 ppm, 30 ppm, 40 ppm, 50 ppm, 60 ppm, 70 ppm, 80 ppm, 90 ppm, 100 ppm, 200 ppm, 300 ppm, 400 ppm, 500 ppm, 600 ppm, 700 ppm, 800 ppm, The product may contain from about 1000 ppm, 900 ppm, 800 ppm, 700 ppm, 600 ppm, 500 ppm, 400 ppm, 300 ppm, 200 ppm, 100 ppm, 90 ppm, 80 ppm, 70 ppm, 60 ppm, 50 ppm, 40 ppm, 30 ppm, 20 ppm, 10 ppm, or up to 5 ppm of rosmarinic acid. In one embodiment, the product contains about 50 ppm of rosmarinic acid, preferably about 1 ppm to about 50 ppm of rosmarinic acid, preferably about 1 ppm to about 40 ppm of rosmarinic acid, more preferably about 1 ppm to about 30 ppm of rosmarinic acid, and even more preferably about 10 ppm to about 15 ppm of rosmarinic acid, based on the final weight of the product.

[0077] In another aspect, the product (e.g., foodstuff) of the present invention contains, based on the final weight of the product, about 1 ppm to about 50 ppm of rosmarinic acid, preferably about 1 ppm to about 40 ppm of rosmarinic acid, more preferably about 1 ppm to about 30 ppm of rosmarinic acid, and even more preferably about 10 ppm to about 15 ppm of rosmarinic acid.

[0078] In another preferred embodiment, the product (e.g., food material) of the present invention is a beverage product, and the concentration of the composition in the food material is about 5 ppm to about 20 ppm for chlorogenic acid and about 5 ppm to about 25 ppm for rosmarinic acid, based on the final weight of the product. In another preferred embodiment, the product (e.g., foodstuff) of the present invention is a beverage product, and the concentration of the composition in the foodstuff is about 13.5 ppm chlorogenic acid and about 15 ppm rosmarinic acid, based on the final weight of the product. In another preferred embodiment, the product (e.g., foodstuff) of the present invention is a beverage product, and the concentration of the composition in the foodstuff is about 9 ppm chlorogenic acid and about 10 ppm rosmarinic acid, based on the final weight of the product.

[0079] In another preferred embodiment, the foodstuff of the present invention is a beverage product, and the concentration of the compositions in the foodstuff is about 9 ppm chlorogenic acid and about 10 ppm rosmarinic acid, based on the final weight of the product. In another preferred embodiment, the foodstuff of the present invention is a beverage product, and the concentrations of the compositions in the foodstuff are about 9 ppm chlorogenic acid and about 1.5 ppm rosmarinic acid, based on the final weight of the product.

[0080] In another preferred embodiment, the foodstuff of the present invention is a beverage. The term "beverage" as used herein refers to any drinkable or edible liquid. In another preferred embodiment of the foodstuff, the beverage is a lemon-flavored beverage, and the flavor is natural and / or artificial.

[0081] A specialist would know how to adjust the amounts of the compositions in the beverage. In another preferred embodiment of the foodstuff of the present invention, the composition comprises about 4% to about 5% chlorogenic acid, about 0.3% to about 3% caffeine, and about 0.5% to about 1% rosmarinic acid.

[0082] In a preferred embodiment of the foodstuff of the present invention, the composition is present in the beverage at a concentration of about 50 to 500 ppm, preferably about 100 ppm to about 300 ppm. In another preferred embodiment of the food material of the present invention, the food material is a beverage, preferably a lemon-flavored beverage, and the concentration of the composition in the food material is about 1 ppm to about 500 ppm of chlorogenic acid, for example, 200 ppm to 500 ppm of chlorogenic acid, for example, 400 ppm of chlorogenic acid, and about 0.5 ppm to about 50 ppm of rosmarinic acid, for example, 20 to 40 ppm of rosmarinic acid, for example, 30 ppm of rosmarinic acid.

[0083] In another preferred embodiment of the foodstuff of the present invention, the foodstuff is a beverage, preferably a lemon-flavored beverage, wherein the concentrations of the compositions in the foodstuff are about 9 ppm chlorogenic acid and about 1.5 ppm rosmarinic acid, based on the final weight of the product. ***

[0084] The present invention will now be described by the following examples, which should be regarded as merely illustrative and not as limiting the scope of the invention.

[0085] example Example 1: Product Description Table 1: Summary of the extracted products obtained [Table 1] * Nat extract = natural extract, P80: Polysorbate 80, MPG = PG = propylene glycol, Malto = maltodextrin

[0086] 1. Rosemary CA WS (Table 1, Extract A) Detailed procedures for preparing rosemary extract compositions are described in U.S. Patent No. 5,859,293 (PCT WO96 / 34534), which is incorporated herein by reference in its entirety. Briefly, the procedures are summarized as follows: rosemary leaves were extracted with acetone at room temperature. After the extraction was completed, the acetone extract was filtered to separate the solution from the rosemary leaves and concentrated under reduced pressure to produce a concentrated natural extract. Aqueous sodium carbonate (Na2Co3) was added to the concentrated natural extract to precipitate base-insoluble substances while dissolving carnosic acid and other organic acids. The solution was filtered to separate the solids, and the filtrate was further concentrated under reduced pressure. After final concentration was achieved, phosphoric acid (H3PO4) was added, and acid-insoluble substances (including carnosic acid, carnosol, and carnosine derivatives) precipitated from the concentrated solution. The precipitated solids were then separated from the liquid through filtration and rinsed with water to remove impurities. Finally, the solid was dried in a vacuum oven and then ground into a powder.

[0087] The product can then be formulated on a variety of solid or liquid carriers to adjust its physical properties (physical form, solubility, color, etc.).

[0088] 2. Green coffee bean extracts (Table 1, extracts B and C) Green coffee beans of Coffea arabica or Coffea robusta were ground and extracted using alcohol extraction. Any other plant or organism that contains chlorogenic acid, or any other process that provides or yields chlorogenic acid, may also be used. Here, the extraction solvent consisted of 75% ethanol and 25% water.

[0089] The extract thus obtained was filtered and concentrated. The concentrated extract was supplemented with an organic acid, a weak acid, or a strong acid, in this case, citric acid. The obtained extract was further filtered and concentrated with or without a liquid carrier such as propylene glycol. To obtain Extract C, the concentrated natural extract was spray-dried on maltodextrin.

[0090] 3. Salvia extracts (Table 1, extracts D and E) The aerial parts (leaves and stems) of Salvia officinalis or Salvia apiana were extracted with 2-5% activated carbon with acetone at reflux (56.4°C) under mechanical stirring for 2 hours. After extraction was complete, the acetone extract was filtered to remove plant residues. The resulting acetone extract was concentrated under reduced pressure. Further purification was performed as described in WO 96 / 34534. Extract D. The product can then be formulated on various carriers, solid or liquid (extract E), to adjust its physical properties (physical form, solubility, color, etc.).

[0091] 4. Rosemary RA extract (Table 1, extract F) Rosemary leaves were extracted by percolation with water at 90° C. for 1 hour and 30 minutes. After the extraction was completed, the water extract was concentrated by membrane filtration. After carrying out the concentration step, the extract is purified on a polymeric adsorption resin and the purified extract is spray dried on maltodextrin.

[0092] Example 2. Method 2.1-In vitro Test ORAC Determination of antioxidant capacity by oxygen radical absorbance capacity was performed on a fluorescence microplate reader Tecan Infinite according to the procedure of Ou et al., 2013 (AOAC Official Method 2012.23 Total Antioxidant Activity). The method describes how to perform the analysis on lipophilic and hydrophilic samples.

[0093] The ORAC assay measures the ability of a sample to bind oxygen radicals. A reactive oxygen species generator (AAPH) is added in parallel reactions containing an equal amount of a fluorescent probe (fluorescein sodium salt). Reactions contain either a buffer blank or an antioxidant sample and standard (Trolox). The antioxidant capacity of a sample is the net difference in area under the curve (AUC) between the sample and the blank. To express the ORAC value of a sample as μmol of Trolox equivalents per gram (μmol TE / g), the net AUC of the sample is compared to the net AUC of the Trolox standard concentration.

[0094] The results obtained are proportional to the amount of extract: the product blend will produce an ORAC value proportional to the ORAC of each extract weighted by its proportion in the blend.

number

[0095] 2.2.In vitro test CAT Measurement of antioxidant capacity by conjugated autoxidizable trienes was carried out in a microplate reader Tecan Infinite according to the procedure of Laguerre et al. (Analytical Biochemistry 380 (2008) 282-290).

[0096] Similar to the ORAC assay, the CAT assay measures the ability of a sample to bind oxygen radicals. A reactive oxygen species generator (AAPH) is added in parallel reactions containing an equal amount of absorbance probe (emulsion). Reactions contain either a buffer blank or an antioxidant sample and standard (Trolox). The antioxidant capacity of a sample is the net difference in area under the curve (AUC) between the sample and the blank. To express the sample's CAT value as equivalents in TE / g of Trolox per gram (TE / g TE / g), the net AUC of the sample is compared to the net AUC of the Trolox standard concentration.

[0097] As with ORAC, the results obtained are proportional to the amount of extract: a product blend will produce a CAT value proportional to the CAT of each extract weighted by its proportion in the blend.

number

[0098] 2.3. Testing in meat applications (pork) For each modality, meat (composition is precisely described in Table 2): [Table 2] was mixed by hand with the exact amount of extract listed in Table 3 until blended.

[0099] [Table 3]

[0100] Patties were formed and stored for 10 days under modified atmosphere (MAP) in the dark at 4° C. Samples were analyzed by the TBars assay after 3, 6 and 10 days of storage.

[0101] TBA-RS (thiobarbituric acid reactive substances) is a common assay for the degree of oxidation in meat and fish products. Malonaldehyde (MDA), a three-carbon compound, is the primary carbonyl decomposition molecule of autoxidized, secondary-oxidized polyunsaturated materials. The basic principle of the method is that the reaction of one molecule of malonaldehyde with two molecules of TBA forms a pink pigment, the malonaldehyde-TBA complex, which can be quantified spectrophotometrically at 509, 532, and 580 nm.

[0102] For each modality, a 150g quantity of minced pork was mixed by hand with the appropriate amount of extract until thoroughly mixed. Patties were formed and cooked in an oven (170°C) until the temperature at the core reached 70°C. The patties were stored unwrapped in a light box at 4°C (simply placed on a plate to maximize oxygen contact and accelerate the oxidation process).

[0103] TBars measurements were performed as previously described in Zhang et al., Food Science and Human Wellness, 5, 39-48 (2016). Two series were launched at different times, with different batches of meat and a sage / green coffee bean blend.

[0104] 2.4. Testing in beverages Lemon flavor + 12 ppm citral was spiked in a standard beverage matrix (acidified sweetened water) with or without our antioxidant extract (dosages in Table 4). The "aged" samples were then subjected to an accelerated aging process at 40°C for 4 weeks, and the "fresh" samples were stored at 4°C.

[0105] To understand how well the solutions performed, sensory profiling was performed on "fresh" and "aged" samples with and without antioxidants. Flavor impression profiling consists of quantifying the sensory attributes of a product through an open group discussion. Expert-trained panelists taste the complete product set and generate descriptors specifically for the sample being evaluated. They individually rate an intensity score for each of these descriptors, then, as a group, discuss their individual ratings and agree on a final consensus profile. Testing is performed in a discussion room, and results are collected by the panel leader.

[0106] Table 4: Dosage of extracts and active ingredients for beverage applications [Table 4-1]

[0107] Example 3: Results 1. In vitro ORAC and CAT antioxidant tests 1. Formulation containing rosemary extract and green coffee bean extract As can be seen in Table 4 and Figure 1, when extract A is combined with extract B, the predicted ORAC value can be determined as follows:

number

[0108] 2. Sage extract and green coffee bean extract blend As can be seen in Table 5 and Figure 2, when extract C is combined with extract D, the CAT values ​​that are expected to be obtained are as follows:

number

[0109] After analysis of a combination containing 50% Extract A and 50% Extract B, the CAT value was 1.4 times higher than expected, clearly indicating the presence of a synergistic antioxidant effect as a result of the combination of these products. [Table 5]

[0110] 3. Results of application to meat (pork) As can be seen in Figure 3 and Table 6, a clear increase in TBArs values ​​was observed over time for the negative controls, reaching nearly 3 meqMDA / kg for the first series and over 4.5 meqMDA / kg for the second series after 10 days of the meat's shelf life. In comparison, meat containing different dosages of the green coffee bean and sage extract blend remains below 0.8 meqMDA / kg even after shelf life. The use of natural antioxidant solutions is believed to prevent lipid oxidation mechanisms. [Table 6]

[0111] 4. Results of application to beverages To understand how well the solutions worked, sensory profiling was performed on fresh and aged samples with and without antioxidants.

[0112] As can be seen in Table 7, rosemary alone at 30 ppm and green coffee beans alone at 440 ppm protected lemon flavor from oxidation. The flavor and balanced profile impact were partially protected (20%). Lemon candy notes and citrus fresh notes were also partially protected (27% and 67% for rosemary, 27% and 33% for green coffee beans). However, citrus notes were not protected. Furthermore, the formation of oxidized notes was limited. At 30 ppm, rosemary only limited the formation of oxidized citral cherry notes and lime distillate notes (67% and 17%), but was unable to limit the formation of oxidized citral animal notes and oxidized terpene notes. At 440 ppm, green coffee beans limited the formation of oxidized citral animal notes, oxidized terpene notes, and lime distillate notes by 17%, and the formation of oxidized citral cherry notes by 67%.

[0113] Surprisingly, significant synergistic effects were observed by combining both extracts at half the dosage. Citrus notes were not protected by the extracts alone, whereas 50% protection was observed with the combination. Furthermore, lemon candy notes and lemon fresh notes were better protected by the combination (47% and 67%, compared to the predicted 27% and 50%). Finally, the formation of oxidized notes was better limited than expected. We predicted an 8% oxidized citral animal note limitation and observed a 17% limitation. We predicted a 67% oxidized citral cherry note limitation and observed an 83% limitation. We predicted an 8% oxidized terpene note limitation and observed a 17% limitation. Finally, we predicted a 17% oxidized lime distillate note limitation and observed a 33% limitation.

[0114] Considering these results, we predict that the same synergistic effect can be observed between green coffee beans and other plants rich in rosmarinic acid, such as lemon balm. Table 7

Claims

1. Chlorogenic acid and: (i) rosmarinic acid; and (ii) phenolic diterpenes, and one or more additional components or combinations of components selected from the group consisting of: wherein the ratio of chlorogenic acid to one or more additional components or combinations of components is from about 100:1 to about 1:100; The antioxidant composition.

2. 2. The composition of claim 1, wherein the ratio of chlorogenic acid to one or more additional components or ingredients is from 50:1 to 1:50, preferably from 25:1 to 1:

25.

3. 3. The composition according to claim 1, wherein the ratio of chlorogenic acid to rosmarinic acid is from about 6:1 to about 1:6, preferably from about 5:1 to about 1:

5.

4. 4. The composition according to any one of claims 1 to 3, wherein the ratio of chlorogenic acid to phenolic diterpene is from about 5:1 to about 1:5, preferably from about 0.9:1 to about 1:0.

9.

5. The composition of any one of claims 1 to 4, wherein the chlorogenic acid is provided as an extract of green coffee beans.

6. A composition according to any one of claims 1 to 5, wherein rosmarinic acid is provided as an extract of the aerial parts of rosemary and / or an extract of the aerial parts of Melissa officinalis.

7. Use of a composition according to any one of claims 1 to 6 as an antioxidant.

8. 10. A process for preventing and / or inhibiting oxidation of a human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking or cosmetic formulation, said process comprising the step of contacting the human or animal food or beverage product, a dietary supplement, a functional food formulation, a fragrance or flavoring agent, a pharmaceutical or veterinary formulation, a winemaking or cosmetic formulation with a composition according to any one of claims 1 to 6.

9. 7. Use of a composition according to any one of claims 1 to 6 for preventing and / or inhibiting oxidation of human or animal food or beverage products, dietary supplements, functional food formulations, fragrances or flavouring agents, pharmaceutical or veterinary formulations, oenological or cosmetic formulations.

10. 10. Use according to claim 9 in the manufacture of a food or drink product for humans or animals, a dietary supplement, a functional food formulation, a fragrance or flavouring agent, a pharmaceutical or veterinary formulation, a vinification formulation or a cosmetic formulation.

11. 11. The process according to claim 8 or the use according to claim 9 or 10, wherein the food product is a product selected from the group consisting of meat, beverages, sauces, patisserie, dairy products, oils, bakery, fillings and edible inks, preferably a meat or beverage product, preferably a lemon-flavored beverage.

12. 10. A human or animal food or drink product, dietary supplement, functional food formulation, fragrance or flavoring agent, pharmaceutical or veterinary formulation, vinification or cosmetic formulation comprising the antioxidant composition of any one of claims 1 to 6 and an adjuvant acceptable to the human or animal food or drink product, dietary supplement, functional food formulation, fragrance or flavoring agent, pharmaceutical or veterinary formulation, vinification or cosmetic formulation.

13. 13. The human or animal food or beverage product, dietary supplement, functional food formulation, fragrance or flavoring agent, pharmaceutical or veterinary formulation, vinification formulation or cosmetic formulation according to claim 11 or 12, wherein the composition in the foodstuff comprises chlorogenic acid and phenolic diterpene in a ratio of about 0.1:1 to about 1:0.1, preferably about 0.8:1 to about 1:0.

8.

14. 14. A human or animal food or beverage product, dietary supplement, functional food formulation, fragrance or flavoring agent, pharmaceutical or veterinary formulation, oenological formulation or cosmetic formulation according to any one of claims 11 to 13, wherein the composition in the foodstuff comprises: - from about 0.1% w / w to about 55.0% w / w, preferably from about 2.0% w / v to 25% w / w of chlorogenic acid; from about 0.1% w / w to about 10.0% w / w, preferably from 0.2% w / w to about 5% w / w of caffeine; and at least about 0.1% w / w of phenolic diterpenes Including, Said human or animal food or drink product, dietary supplement, functional food formulation, fragrance or flavoring agent, pharmaceutical or veterinary formulation, oenological formulation or cosmetic formulation.

15. 15. The product (such as a food or beverage product) of any one of claims 11 to 14, wherein the concentration of the composition in the product (such as a food or beverage product) is from about 1 to about 10,000 ppm.

16. 16. The product (such as a food or beverage product) of claim 15, wherein the concentration of the composition in the product (such as a food or beverage product) is about 5 to 50 ppm based on the final weight of the product.

17. 17. The product (such as a food or beverage product) of any one of claims 11 to 16, wherein the concentration of chlorogenic acid is from about 5 ppm to about 1000 ppm based on the final weight of the product.

18. 17. The product (such as a food or beverage product) of any one of claims 11 to 16, wherein the concentration of the phenolic diterpene is from about 5 ppm to about 1000 ppm based on the final weight of the product.

19. 17. The product (such as a food or beverage product) according to any one of claims 11 to 16, wherein the concentration of rosmarinic acid is from about 5 ppm to about 1000 ppm based on the final weight of the product.

20. 20. The product (e.g., a food or beverage product) of claim 18, wherein the foodstuff is a meat product and the concentration of the composition in the foodstuff is from 5 ppm to about 20 ppm of chlorogenic acid and from about 5 ppm to about 25 ppm of phenolic diterpene, based on the final weight of the product.

21. 21. The product (such as a food or beverage product) of claim 20, wherein the food product is a meat product and the concentration of the composition in the food product is about 13.5 ppm chlorogenic acid and about 15 ppm phenolic diterpene, based on the final weight of the product.

22. 22. The product (e.g., a food or beverage product) of claim 21, wherein the product is a meat product and the concentration of the composition in the food product is about 5 ppm to about 15 ppm (e.g., about 9 ppm) of chlorogenic acid and about 5 ppm to about 20 ppm (e.g., about 10 ppm) of phenolic diterpenes, based on the final weight of the product.

23. 20. The product (such as a food or beverage product) of claim 19, wherein the product is a beverage, preferably a lemon-flavored beverage, and the concentrations of the compositions in the food product are from about 1 ppm to about 100 ppm for chlorogenic acid and from about 0.1 ppm to about 50 ppm for rosmarinic acid, based on the final weight of the product.

24. 24. The product (such as a food or beverage product) of claim 23, wherein the product is a beverage, preferably a lemon-flavored beverage, and the concentration of the composition in the food product is about 9 ppm chlorogenic acid and about 1.5 ppm rosmarinic acid, based on the final weight of the product.

Images