Compounds

Abstract

The present invention relates to a composition having a synergistic anti-oxidation effect, the components of which are obtained from plant extracts, and the composition can be used for the preparation of food products.

Description

[0001] Technical field of the invention

[0002] The present invention relates to the use of plant extracts for obtaining antioxidants, which can be used in the preparation of foods, cosmetics and nutraceuticals. Background of the Invention

[0004] Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals and chain reactions that can damage biological cells. Antioxidants are widely used in agroindustries, such as meat and poultry, beverages, salad dressings, condiments, snacks, etc., to preserve food by delaying its spoilage, rancidity, or discoloration. Furthermore, antioxidants have also been used in various cosmetics and toiletry products to prevent oxidation, as well as in pharmaceutical compositions. Finally, antioxidants are also commonly used as nutritional supplements. Therefore, the main use of antioxidants is to prevent the degradation of product properties by preventing oxidative damage and cell damage caused by oxygen free radicals.

[0005] The use of synthetic antioxidants in commercial food preparation has been largely replaced by antioxidants of natural origin, such as those found in spices (e.g., rosemary and sage). Antioxidants obtained from natural sources have been shown to be stable at high temperatures, readily soluble in oils, and are considered safer than synthetic antioxidants. Most natural antioxidants are derived from plant materials, such as fruits, vegetables, herbs, and spices.

[0006] Antioxidants are primarily obtained from liquid extracts in solvents containing the natural source of the antioxidant. Minor variations in the process of obtaining the plant and / or the treatments leading to the extraction process can result in significant differences in the yield and antioxidant activity of the extract. Furthermore, scale-up of such extractions is not always easy and can result in increased production of byproducts. Therefore, to facilitate the antioxidant extraction process and help reduce the amount of byproducts from the extraction process, alternative antioxidants with higher antioxidant capacity are needed. SUMMARY OF THE INVENTION

[0008] The present inventors have discovered that certain combinations of antioxidant extracts result in a synergistic effect in the antioxidant activity of the extract composition.

[0009] Therefore, a first aspect of the present invention relates to an antioxidant composition comprising chlorogenic acid and one or more additional components or combinations of components selected from the group consisting of:

[0010] (i) rosmarinic acid; and

[0011] (ii) phenolic diterpenes,

[0012] wherein the ratio of the chlorogenic acid to the one or more additional components or combination of components is from about 100:1 to about 1:100.

[0013] Another aspect of the present invention relates to the use of a composition according to the invention for the preparation of a food or beverage product for humans or animals, a nutritional supplement, a nutraceutical formulation, a fragrance or flavoring, a pharmaceutical or veterinary formulation, an oenological or cosmetic formulation.

[0014] Another aspect of the present invention relates to the use of a composition according to the invention as an antioxidant.

[0015] Another aspect of the present invention relates to a method for preventing and / or inhibiting oxidation in a food or beverage product for human or animal use, a nutritional supplement, a nutraceutical preparation, a fragrance or flavoring, a pharmaceutical or veterinary preparation, an oenological or cosmetic preparation, comprising the step of contacting the food with a composition according to the invention.

[0016] Another aspect of the present invention relates to a food or beverage product for human or animal use, a nutritional supplement, a nutraceutical preparation, a spice or flavoring, a pharmaceutical or veterinary preparation, a brewing or cosmetic preparation comprising the antioxidant composition according to the present invention, or a nutraceutical or dietary supplement comprising a composition according to the present invention and an adjuvant acceptable to a food or beverage product for human or animal use, a nutritional supplement, a nutraceutical preparation, a spice or flavoring, a pharmaceutical or veterinary preparation, a brewing or cosmetic preparation. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1 ORAC-CAT values ​​for a blend containing rosemary and green coffee beans.

[0019] Figure 2 .CAT value of a blend containing sage and green coffee beans.

[0020] Figure 3 .TSL in pork = TBArs value during 10 days. Detailed Description of the Invention

[0022] As mentioned above, the present invention discloses a composition of extracts with antioxidant effects, which exhibits synergistic antioxidant activity compared to the antioxidant activity of individual extracts. These compositions are obtained by mixing antioxidant extracts from different plant sources in a certain ratio.

[0023] Composition of the present invention

[0024] Therefore, a first aspect of the present invention relates to an antioxidant composition, from this point onwards, to a composition of the invention comprising chlorogenic acid and one or more additional components or combinations of components selected from the group consisting of:

[0025] (i) rosmarinic acid; and

[0026] (ii) phenolic diterpenes,

[0027] wherein the ratio of the chlorogenic acid to the one or more additional components or combination of components is from about 100:1 to about 1:100.

[0028] As used herein, the term "antioxidant" refers to a compound that is capable of inhibiting reactions promoted by oxygen or reactions induced by the presence of metals such as iron (Fenton reaction), thereby preventing oxidation and rancidity of the composition. Thus, an antioxidant reduces the amount of oxidation over a given period of time when compared to the oxidation that would occur in the absence of the antioxidant. Methods for determining the antioxidant capacity of a compound in a composition are well known in the art and are exemplified in the Examples section of the specification under the "In Vitro ORAC Test" and "In Vitro CAT Test" sections.

[0029] As used herein, the term "chlorogenic acid" refers to esters of caffeic acid and (-)-quinic acid. Chlorogenic acid occurs naturally in coffee, primarily as monoesters and diesters of quinic acid and phenolic groups (e.g., caffeic acid, ferulic acid, coumaric acid, methoxycinnamic acid) attached to various positions. Chlorogenic acid is defined in the CAS Registry Database entry numbered 202650-88-2 and structurally represented by formula (iii):

[0030]

[0031] The ratio of chlorogenic acid can be associated with one additional component of the composition of the present invention, such as rosmarinic acid or a phenolic diterpene, or it can be associated with two additional components of the composition of the present invention, namely rosmarinic acid and a phenolic diterpene. In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to the one or more additional components or combination of components is about 95:5, 97:7, about 90:10, about 85:15, about 80:20, about 75:25, about 70:30, about 65:35, about 60:40, about 55:45, about 50:50, about 45:55, about 40:60, about 35:65, about 30:70, about 25:75, about 20:80, about 15:85, about 10:90, about 7:97, about 5:95. In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to the one or more additional components or combination of components is from 50:1 to 1:50, preferably from 25:1 to 1:25. In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to the one or more additional components or combination of components is from about 50:1 to about 1:50, for example from about 25:1 to about 1:25, for example from about 10:1 to about 1:10, for example from about 5:1 to about 1:5.

[0032] In preferred embodiments of the compositions of the present invention, the concentration of chlorogenic acid is from about 0.1% w / v to 55% w / w, from about 0.5% to about 25%, from about 1% to about 10%, from about 2.0% to about 3.0%, from about 2.1% w / w to 2.9% w / w, from about 2.15% w / w to 2.85% w / w, from about 2.2% w / w to 2.8% w / w, from about 2.25% w / w to 2.75% w / w. In a more preferred embodiment of the composition of the present invention, the concentration of chlorogenic acid is from about 4% to about 5%, from about 2% w / w to about 3% w / w.

[0033] The composition of the present invention further comprises one or more additional components selected from rosmarinic acid and phenolic diterpenes.

[0034] As used herein, the term "diterpenes" refers to a class of compounds composed of four isoprene units, generally having 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 that include, among others, carnosic acid, carnosol, rosmanol, epirosmanol and methoxyepirosmanol. These components are, at least to some extent, the result of carnosic acid degradation, but they still have antioxidant activity. "Phenolic diterpenes" are intended to include carnosic acid, carnosol and their derivatives. Therefore, when "phenolic diterpenes" are mentioned in the present invention, all carnosic acids, carnosols and their derivatives are included.

[0035] In preferred embodiments of the composition of the present invention, the ratio of chlorogenic acid to phenolic diterpenes is from about 25:1 to about 1:25, from about 10:1 to about 1:10, from about 5:1 to about 1:5, preferably from about 0.9:1 to about 1:0.9.

[0036] 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 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.

[0037] The phenolic diterpenes of the present composition can be obtained in the form of an extract of the aboveground parts of sage (Salvia). In a preferred embodiment of the present composition, the phenolic diterpenes are provided in the form of an extract of the aboveground parts of sage (preferably leaves). "Aerial parts of sage" refers to stems, leaves, petioles, flowers, fruits and seeds, preferably leaves, from the genus Salviaceae, which is composed of shrubs, perennial herbs and annual plants. In a preferred embodiment of the present composition, the aerial parts of sage, preferably leaves, are from the plant Salvia officinalis or the plant Salvia apiana.

[0038] Those skilled in the art will be aware of known methods for providing an extract of the aerial parts of sage, as these methods are well known in the art. For example, the method described in document WO 96 / 34534, which is incorporated herein by reference, can be used in the present invention. In a preferred embodiment of the composition of the present invention, an extract of the aerial parts (preferably leaves) of sage is obtained by the following steps:

[0039] (i) extracting the aerial parts (preferably leaves) of sage with acetone and activated carbon; and optionally

[0040] (ii) further purifying the extract.

[0041] In step (i) of the process for obtaining an extract of aerial parts, preferably leaves, of sage, the extraction is carried out with a combination of an organic solvent, namely acetone, and activated carbon.

[0042] Several methods for extracting plant parts are known in the art. One such method is solvent extraction, a method for separating compounds based on their relative solubility in two different immiscible liquids, typically water (polar) and an organic solvent (non-polar). There is a net transfer of one or more species from one liquid phase to another, typically from an aqueous phase to an organic phase. The transfer is driven by chemical potential, meaning that once the transfer is complete, the overall system of chemical components comprising the solute and solvent is in a more stable configuration (lower free energy). In a preferred embodiment of the composition of the present invention, the extract of green coffee beans is obtained by extraction with an alcoholic solvent.

[0043] In the context of the present invention, the term "solvent" refers to a substance that dissolves a solute, thereby producing a solution. The solvent is typically a liquid, but can also be a solid, a gas, or a supercritical fluid.

[0044] As used herein, the term "alcohol solvent" refers to a solvent comprising an ethyl group attached to a hydroxyl group. Examples of alcohol solvents include, but are not limited to, ethanol, ethylene glycol, isopropyl alcohol, methanol, isobutyl alcohol, diethylene glycol, and the like. In a preferred embodiment of the present composition, the green coffee bean extraction is performed with ethanol, preferably at a ratio of 75% to 25% solvent to water.

[0045] As used herein, the term "activated carbon" (also known as activated charcoal) refers to a form of carbon commonly used for filtering pollutants from water and air, as well as for many other uses. It is processed to have small, low-volume pores, which increase the surface area available for adsorption or chemical reactions. In a preferred embodiment of the composition of the present invention, the extraction of the aerial parts of sage (preferably leaves) is carried out with an activated carbon 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, about 10% w / w.

[0046] In order to obtain better results during the extraction of the aerial parts (preferably leaves) of sage, in a preferred embodiment of the composition of the present invention, the extraction of the aerial parts (preferably leaves) of sage is carried out at a temperature of about 50°C to about 60°C, preferably 56.4°C, under stirring for about 1 hour to about 3 hours, preferably about 2 hours.

[0047] Once the extraction step has been performed and the resulting plant residues removed, the extract can be further purified to obtain higher concentrations of the active substances by methods known in the art, such as those described in WO 96 / 34534, which is incorporated herein by reference.

[0048] 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 the one or more additional components or combinations of components is from 50:1 to 1:50, for example, from 25:1 to 1:25, for example, from 10:1 to 1:10, for example, from 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 from 50:1 to about 1:50, for example, from about 25:1 to about 1:25, for example, from about 10:1 to about 1:10, for example, from about 6:1 to about 1:6, preferably from about 5:1 to about 1:5.

[0049] 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. As used herein, the term "rosmarinic acid" refers to a 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 by the esterification of caffeic acid with 3,4-dihydroxyphenyllactic acid. Rosmarinic acid is defined in the CAS registry database as entry number 20283-92-5 and is structurally defined by formula (vii)

[0050]

[0051] 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, the rosmarinic acid is provided in the form of 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 from the plant species Rosemary (Salvia rosmarinus).

[0052] In a preferred embodiment, the rosemary leaf extract is obtained by extraction with water or an alcoholic solvent. The term "alcoholic solvent" was previously defined, and the definition also applies to the current embodiment. In a preferred embodiment of the composition of the present invention, the rosemary leaf extraction is carried out with water.

[0053] Aqueous extractions are well known in the art and their use is part of the expert's general knowledge. In a preferred embodiment of the composition according to the invention, the extraction of the 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.

[0054] In a preferred embodiment of the composition of the present invention, the obtained rosemary leaf extract is further filtered and concentrated, preferably by membrane filtration.

[0055] Once the concentration step has been performed, 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.

[0056] As previously mentioned, 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, preferably leaves or seeds of Melissa officinalis. 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 with ethanol and activated carbon, wherein the ethanol is used at a concentration of about 70% v / v solvent to water, and the 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, about 10% w / v.

[0057] 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.

[0058] In preferred embodiments, the compositions of the present invention further comprise caffeine in a concentration of about 0.01% w / w to about 15% w / w, 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, about 4% w / v to 5% w / v. In preferred embodiments, the compositions of the present invention further comprise a concentration of about 0.01% w / w to about 1.5% w / v, about 0.25% w / v to 1.5% w / v, about 0.3% w / v to 1.45% w / v, about 0.35% w / v to 1.4% w / v, about 0.4% w / v to 1.35% w / v, about 0.45% w / v to 1.3% w / v, about 0.5% w / v to 1.25 % w / v, 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, about 0.9% w / v to 1% w / v of caffeine.

[0059] As used herein, the term "caffeine" refers to a bitter, white, crystalline purine, a methylxanthine alkaloid, which is defined in the CAS Registry database as entry number 58-08-2 and is structurally defined by formula (iv)

[0060]

[0061] Since coffee beans are a source of both chlorogenic acid and caffeine, preparing the present composition starting with 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), winter bark (Drimys winteri), green tea (Camellia sinensis), elderflower (Sambucus nigra), and Boehmeria caudate. In a preferred embodiment of the present composition, chlorogenic acid and caffeine are provided in the form of an extract of green coffee beans. As used herein, the expression "green coffee beans" refers to unroasted coffee beans. In another preferred embodiment of the present composition, the coffee beans are from the plant species Coffea Arabica or Coffea Robusta.

[0062] Methods for obtaining chlorogenic acid and caffeine from coffee beans are well known in the art and examples are provided in this specification (see Examples).

[0063] In a preferred embodiment of the composition of the present invention, the green coffee bean extract obtained is further filtered and concentrated. In another preferred embodiment, the concentrated extract is supplemented with an organic strong or weak acid.

[0064] As used herein, the term "organic acid" refers to an organic compound with acidic properties. The most common organic acid is carboxylic acid, whose acidity is related to its carboxyl group -COOH. Sulfonic acids containing the group -SO2OH are relatively strong acids. Alcohols with -OH can act as acids, but they are generally very weak. The relative stability of the conjugate base of the acid determines its acidity. Other groups can also impart acidity, usually weak: thiol groups -SH, enol groups, and phenolic groups. In biological systems, organic compounds containing these groups are generally referred to as organic acids. Examples of organic acids are, but are not limited to, lactic acid, acetic acid, formic acid, citric acid, oxalic acid, uric acid, malic acid, and tartaric acid.

[0065] In preferred embodiments of the compositions of the present invention, the concentration of the phenolic diterpene carnosic acid is from about 0.1% w / v to 5% w / v, from about 0.25% w / v to 4.75% w / v, from about 0.5% w / v to 4.5% w / v, from about 0.75% w / v to 4.25% w / v, from about 1% w / v to 4% w / v, from about 1.25% w / v to 3.75% w / v, from about 1.5% w / v to 3.5% w / v, from about 1.75% w / v to 3.25% w / v, from about 2% w / v to 3% w / v, from about 2.25% w / v to 3% w / v, from about 2.5% w / v to 3% w / v.

[0066] In the context of this specification, the term "carnosic acid" refers to a benzylabietan diterpene, which is present in rosemary, sage, etc. Carnosic acid is defined in the CAS registry database as accession number 3650-09-7 and is structurally defined by formula (v):

[0067]

[0068] In a preferred embodiment of the composition of the present invention, the ratio of chlorogenic acid to the phenolic diterpenoid carnosic acid is from about 50:1 to 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 5:1 to about 1:5. In a more preferred embodiment of the composition of the present invention, 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. In preferred embodiments of the compositions of the present invention, 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 4.4% w / v, from about 1% w / v to 4.6% w / v. / v to 3.9% w / v, about 1.2% w / v to 3.8% w / v, about 1.3% w / v to 3.7% w / v, about 1.4% w / v to 3.6% w / v, about 1.5% w / v to 3.5% w / v, about 1.6% w / v to 3.4% w / v, about 1.7% w / v to 3.3% w / v, about 1.8% w / v to 3.2% w / v, about 1.9% w / v to 3.1% w / v, about 2% w / v to 3% w / v, about 2.1% w / v to 3% w / v, about 2.2% w / v to 3% w / v, about 2.3% w / v to 3% w / v, about 2.4% w / v to 3% w / v, about 2.5% w / v to 3% w / v.

[0069] As used herein, the term "carnosol," e.g., carnosic acid, refers to a phenolic diterpenoid found in rosemary, salvia officinalis, etc. Carnosol is defined in the CAS registry database as Accession No. 5957-80-2 and is structurally defined by formula (vi):

[0070]

[0071] Carnosic acid and carnosol can be obtained from an extract of rosemary leaves. In a preferred embodiment of the composition of the present invention, the phenolic diterpenes carnosic acid and / or carnosol, as appropriate, are provided in the form of a rosemary leaf extract. In another preferred embodiment of the composition of the present invention, the rosemary leaves are from the plant species Salvia officinalis.

[0072] Several methods for obtaining extracts of the aerial parts of rosemary are available in the literature, for example in document WO 96 / 34534, which is incorporated herein by reference. In a preferred embodiment of the composition of the present invention, the extract of the aerial parts of rosemary is obtained by a process comprising the following steps:

[0073] (i) extracting the aerial parts with an organic solvent, and optionally

[0074] (ii) further purifying the extract.

[0075] As used herein, the term "organic solvent" refers to a carbon-based substance that is 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, glycerol, and the like. In a preferred embodiment of the present composition, the organic solvent used in the rosemary leaf extract is acetone.

[0076] Once the extraction step has been performed and the resulting plant residues removed, the extract can be further purified by methods known in the art to achieve higher concentrations of the active substances, such as those described in WO 96 / 34534, which is incorporated herein by reference.

[0077] Once obtained, the extracts mentioned herein for use in the compositions of the present invention may be filtered, dried, further purified, concentrated, etc. Techniques for applying these methods to extracts are well known in the art, and the expert will know these methods and be able to select the optimal parameters for performing these techniques. In a preferred embodiment, the composition of the extract is processed by a technique selected from the group consisting of filtration, drying, concentration, grinding, filtration and drying, filtration and concentration, filtration and concentration and drying, filtration and drying and grinding, or concentration and 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.

[0078] The extract mentioned herein can be further formulated in a liquid or solid carrier. The extract obtained in order to form the synergistic composition of the present invention can further comprise a suitable carrier. In a preferred embodiment, the present composition also comprises a carrier. As used herein, the term "carrier" refers to any type of material compatible with the intended use, and molecules, compounds, substances (such as plant extracts) or compositions can be loaded thereon by physical interactions or chemical interactions with the carrier material. As an example of a carrier material interacting with a plant extract or composition, interaction must not prevent the plant extract or composition from exerting its desired effect, i.e., reducing its antioxidant activity. In a preferred embodiment of the present composition, the carrier is a liquid or solid. In another preferred embodiment of the present composition, the carrier is selected from ethanol, maltodextrin and monopropylene glycol (MPG).

[0079] Methods and uses of the present invention

[0080] As mentioned above, substances with antioxidant properties have several uses, in particular in the agri-food industry. One aspect of the present invention therefore relates to the use of a composition according to the invention as an antioxidant, from this point onwards relating to use I according to the invention.

[0081] Another aspect of the present invention relates to a method for preventing and / or inhibiting oxidation of a food product, said method comprising the step of contacting said food product with a composition according to the present invention, from this point onwards relating to the method of the present invention.

[0082] A further aspect of the present invention relates to the use of a composition according to the invention for preventing and / or inhibiting oxidation of foods, from this point onwards relating to use II according to the invention.

[0083] All previous embodiments and definitions described in relation to the previous aspect are equally valid for the current aspect and its embodiments.

[0084] Thus, in certain embodiments, the present invention relates to a method for preventing and / or inhibiting oxidation of a food or beverage product for human or animal use, a nutritional supplement, a nutraceutical formulation, a spice or flavoring, a pharmaceutical or veterinary formulation, an oenological or cosmetic formulation, said method comprising the step of contacting the food or beverage product for human or animal use, the nutritional supplement, the nutraceutical formulation, the spice or flavoring, the pharmaceutical or veterinary formulation, the oenological or cosmetic formulation with a composition comprising chlorogenic acid and one or more additional components or combinations of components selected from the group consisting of:

[0085] (i) rosmarinic acid; and

[0086] (ii) phenolic diterpenes,

[0087] wherein the ratio of the chlorogenic acid to the one or more additional components or combination of components is from about 100:1 to about 1:100.

[0088] Thus, in certain embodiments, the present invention relates to the use of a composition comprising chlorogenic acid and one or more additional components or combinations of components selected from the group consisting of:

[0089] (i) rosmarinic acid; and

[0090] (ii) phenolic diterpenes,

[0091] wherein the ratio of the chlorogenic acid to the one or more additional components or combination of components is from about 100:1 to about 1:100.

[0092] Therefore, in certain embodiments, the present invention relates to a method for preventing and / or inhibiting oxidation of a food or beverage product for human or animal use, a nutritional supplement, a nutraceutical formulation, a spice or flavoring, a pharmaceutical or veterinary formulation, an oenological or cosmetic formulation, comprising the step of contacting the food or beverage product for human or animal use, the nutritional supplement, the nutraceutical formulation, the spice or flavoring, the pharmaceutical or veterinary formulation, the oenological or cosmetic formulation with a composition comprising chlorogenic acid and one or more additional components or a combination of components selected from the group consisting of:

[0093] (i) rosmarinic acid; and

[0094] (ii) phenolic diterpenes,

[0095] wherein the ratio of the chlorogenic acid to the one or more additional components or combination of components is from about 100:1 to about 1:100.

[0096] In certain embodiments of the uses and methods of the present invention, the ratio of chlorogenic acid to the one or more additional components or combination of components is about 95:5, 97:7, about 90:10, about 85:15, about 80:20, about 75:25, about 70:30, about 65:35, about 60:40, about 55:45, about 50:50, about 45:55, about 40:60, about 35:65, about 30:70, about 25:75, about 20:80, about 15:85, about 10:90, about 7:97, about 5:95. In certain embodiments, the ratio of chlorogenic acid to the one or more additional components or combination of components is 50:1 to 1:50, preferably 25:1 to 1:25. In certain embodiments, the ratio of chlorogenic acid to the one or more additional components or combination 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.

[0097] In certain embodiments of the uses and methods 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.

[0098] In certain embodiments of the uses and methods of the present invention, the ratio of chlorogenic acid to the phenolic diterpenoid carnosic acid is from about 50:1 to 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 5:1 to about 1:5. In certain embodiments, 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. 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, from about 1% w / v to 4. 3.9% w / v, about 1.2% w / v to 3.8% w / v, about 1.3% w / v to 3.7% w / v, about 1.4% w / v to 3.6% w / v, about 1.5% w / v to 3.5% w / v, about 1.6% w / v to 3.4% w / v, about 1.7% w / v to 3.3% w / v, about 1.8% w / v to 3.2% w / v, about 1.9% w / v to 3.1% w / v, about 2% w / v to 3% w / v, about 2.1% w / v to 3% w / v, about 2.2% w / v to 3% w / v, about 2.3% w / v to 3% w / v, about 2.4% w / v to 3% w / v, about 2.5% w / v to 3% w / v.

[0099] As used herein, the term "oxidation" refers to exposure of a composition and / or food to conditions sufficient to cause it to be significantly oxidized (e.g., an amount of atmospheric oxygen). Oxidation will occur through reactions including, but not limited to, reactions promoted by oxygen or reactions induced by the presence of metals such as iron (Fenton reactions). As used herein, the expression "preventing and / or inhibiting oxidation of a food" refers to a reduction in the oxidation that occurs in the presence of the composition of the present invention compared to the oxidation that occurs in the absence of the composition. The term "preventing" refers to the complete absence of oxidation in the food when the food comprises the composition of the present invention. The term "inhibiting" refers to a reduction in the level of oxidation that occurs in the food when oxygen is present. In a specific embodiment of the method of the present invention, the oxidation of the food 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 to the oxidation level of the food in the absence of the composition. Methods for measuring food oxidation are well known in the art and literature, for example, Barriuso et al, 2013 (European Food Research and Technology volume 236, pages 1-15).

[0100] In a particular embodiment, the method according to the invention or the use I or II according to the invention is in the production of an agri-food product.

[0101] The term "agri-food" as used herein refers to products used in the manufacture, processing and preparation of food products for animal consumption, preferably human consumption.

[0102] In a particular embodiment, the method according to the invention or the use I or II according to the invention is in the manufacture of a food product.

[0103] The term "food" as used herein is intended to mean a substance suitable for human or animal consumption. In addition, the term food as used herein is also intended to include beverages and food materials used to prepare food. The term food as used herein includes, but is not limited to, beverages, eggs, egg-based products, including, but not limited to, mayonnaise, salad dressings, sauces, ice cream, egg powder, modified egg yolks, and products made therefrom; baked goods, including bread, cakes, sweet dough products, laminated dough, liquid batter, muffins, donuts, biscuits, crackers, and cookies; confectionery, including chocolate, candy, caramel, halawa, chewing gum, including sugar-free and sugar-sweetened chewing gum, bubble gum, soft bubble gum, chewing gum, and pudding; frozen products, including sorbet, preferably frozen Dairy products, including ice cream and iced milk; dairy products, including cheese, butter, milk, coffee cream, whipping cream, custard, milk drinks and yogurt; mousse, whipped vegetable cream, meat products, including processed meat products; edible oils and fats, aerated and non-aerated whipping products, oil-in-water emulsions, water-in-oil emulsions, margarine, shortening and spreads, including low-fat and very low-fat spreads; dressings, mayonnaise, dips, cream-based sauces, cream-based soups, beverages, spice emulsions, sauces, drinks, pastry, oils, baked goods, fillings and edible inks.

[0104] In a preferred embodiment of the method according to the invention or of uses I or II according to the invention, the food is a product selected from the group consisting of eggs, mayonnaise, salad dressings, sauces, ice cream, powdered eggs, modified egg yolks, bread, cakes, sweet dough products, laminated dough, liquid batter, muffins, donuts, biscuits, crackers, cookies, chocolate, candy, caramel, halawa, chewing gum, bubble gum, soft bubble gum, chewing gum, pudding, sorbet, ice cream, ice milk, cheese, butter, milk, coffee cream, whipping cream, custard, milk 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, pastries, dairy products, oils, baked goods, fillings and edible inks.

[0105] In another preferred embodiment of the method according to the invention or uses I or II according to the invention, the food is a meat product. The term "meat product" as used herein refers to products obtained from poultry, fish, cattle, pork, sheep, etc., with or without fat, in the form of cut or minced meat, processed or unprocessed ground meat, frozen meat, semi-frozen meat, or chilled meat. In another preferred embodiment of the method according to the invention or uses I or II according to the invention, the food is a pork product.

[0106] In another preferred embodiment of the method according to the invention or of uses I or II according to the invention, the food is a beverage, preferably a lemon-flavored beverage with natural and / or artificial flavoring.

[0107] The amount of the composition of the present invention used in the manufacture of a food product will depend on the type of food product and the intended use of this product.

[0108] Foods, nutritional supplements or dietary supplements and other products of the present invention

[0109] The use of the present invention allows the production of food or beverage products for humans or animals, nutritional supplements, nutraceutical preparations, spices or flavorings, pharmaceutical or veterinary preparations, winemaking or cosmetic preparations with an extended shelf life (i.e., reduced oxidation of the product). Therefore, another aspect of the present invention relates to a product (e.g., a food or beverage product for humans or animals, nutritional supplements, nutraceutical preparations, spices or flavorings, pharmaceutical or veterinary preparations, winemaking or cosmetic preparations) comprising the composition of the present invention, and from this point on, to a food of the present invention, or a nutraceutical or dietary supplement of the present invention, etc., comprising the composition of the present invention and a food or dietary acceptable adjuvant.

[0110] All previous embodiments and definitions described in relation to the previous aspect are equally valid for the current aspect and its embodiments.

[0111] As used herein, the term "nutraceutical" refers to a substance that can be used in the fields of nutrition and pharmaceutical applications. Thus, nutraceutical compositions can be used as supplements to food and beverages, as well as as pharmaceutical preparations for enteral or parenteral use, which can be solid preparations, such as capsules or tablets, or liquid preparations, such as solutions or suspensions.

[0112] The expression "food or dietary acceptable adjuvant" used herein refers to any food material that can be used together with a main food material to enhance, preserve and improve the properties of the main food material. Adjuvants can also be used as fillers, diluents, viscosity modifiers, etc.

[0113] In a preferred embodiment of the food of the present invention, the food is a meat product. In another preferred embodiment of the food of the present invention, the food is a pork product.

[0114] The expert will know how to adjust the amount of the composition in the food. In a preferred embodiment of the product of the invention (e.g. a food or beverage product for humans or animals, a nutritional supplement, a nutraceutical formulation, a spice or flavoring, a pharmaceutical or veterinary formulation, an oenological or cosmetic formulation), the composition in the product (e.g. a food, etc.) comprises a ratio of chlorogenic acid to phenolic diterpenes of about 0.1:1 to about 1:0.1, preferably about 0.8:1 to about 1:0.8.

[0115] In another preferred embodiment of the product (such as food, etc.) of the present invention, the composition in the product (such as food, etc.) comprises:

[0116] - about 0.1% w / w to about 55.0% w / w, preferably about 2.0% w / w to 25% w / w chlorogenic acid;

[0117] - from about 0.1% w / w to about 10.0 w / w, preferably from 0.2% w / w to about 5% w / w caffeine; and

[0118] - at least about 0.1% w / w phenolic diterpenes.

[0119] In another preferred embodiment of the product (e.g., food, etc.) of the present invention, the composition in the product (e.g., food, etc.) comprises about 2.25% w / w to about 2.4% w / w of chlorogenic acid, about 0.25% w / w to about 1.5% w / w of caffeine and more than 2.5% w / w of phenolic diterpenes.

[0120] In another preferred embodiment of the product (eg, food, etc.) of the present invention, the concentration in the product (eg, food, etc.) is from about 0.5 parts per million (ppm) to about 1000 ppm, preferably from about 400 ppm to about 600 ppm.

[0121] In another preferred embodiment, the product of the present invention (e.g., food, etc.) comprises from about 1 ppm to about 1000 ppm of chlorogenic acid, for example, from 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, 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, 700 ppm, 600 ppm, 500 ppm, 400 ppm, 30 ppm, 20 ppm, 100 ppm, 90 ppm, 80 ppm, 70 In certain embodiments, the product (e.g., food, etc.) comprises 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, relative to the final weight of the product.

[0122] In another preferred embodiment, the product of the present invention (e.g., food, etc.) contains from about 1 ppm to about 1000 ppm of phenolic diterpenes, for example, from 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, 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, 700 ppm, 600 ppm, 500 ppm, 400 ppm, 30 ppm, 20 ppm, 100 ppm, In certain embodiments, the product comprises, relative to the final weight of the product, 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, even more preferably about 10 ppm to about 15 ppm.

[0123] In another preferred embodiment, the product of the present invention (e.g., food, etc.) contains from about 1 ppm to about 50 ppm of phenolic diterpenes, preferably from about 1 ppm to about 40 ppm of phenolic diterpenes, more preferably from about 1 ppm to about 30 ppm of phenolic diterpenes, even more preferably from about 10 ppm to about 15 ppm, relative to the final weight of the product.

[0124] In another preferred embodiment, the product of the present invention (e.g., food, etc.) is a meat product, and the concentration of the composition in the food is about 5 ppm to about 20 ppm of chlorogenic acid and about 5 ppm to about 25 ppm of phenolic diterpenes, relative to the final weight of the product.

[0125] In another preferred embodiment, the product (eg, food) of the present invention is a meat product, and the concentration of the composition in the food is about 13.5 ppm of chlorogenic acid and about 15 ppm of phenolic diterpenes relative to the final weight of the product.

[0126] In another preferred embodiment, the product (eg, food) of the present invention is a pork product, and the concentration of the composition in the food is about 9 ppm of chlorogenic acid and about 10 ppm of phenolic diterpenes relative to the final weight of the product.

[0127] In another embodiment of the food product of the present invention, the food product is a meat product, and the concentration of the composition in the food product is about 13.5 ppm of chlorogenic acid and about 15 ppm of phenolic diterpenes.

[0128] In another embodiment of the food of the present invention, the food is a meat product, and wherein the concentration of the composition in the food is from about 5 ppm to about 15 ppm, for example, about 9 ppm, of chlorogenic acid and from about 5 ppm to about 20 ppm, for example, about 10 ppm or about 15 ppm, of phenolic diterpenes.

[0129] In another preferred embodiment of the food product of the present invention, the food product is a pork product, and the concentration of the composition in the food product is about 9 ppm of chlorogenic acid and about 10 ppm of phenolic diterpenes, relative to the final weight of the product.

[0130] In another preferred embodiment, the product (e.g., food, etc.) of the present invention comprises from about 1 ppm to about 1000 ppm of rosmarinic acid, for example, from 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, 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, 700 ppm, 600 ppm, 500 ppm, 400 ppm, 30 ppm, 20 ppm, 100 ppm, or to 5 ppm. In certain embodiments, the product comprises 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, even more preferably about 10 ppm to about 15 ppm of rosmarinic acid, relative to the final weight of the product.

[0131] In another embodiment, the product of the present invention (e.g., food, etc.) comprises from about 1 ppm to about 50 ppm of rosmarinic acid, preferably from about 1 ppm to about 40 ppm of rosmarinic acid, more preferably from about 1 ppm to about 30 ppm of rosmarinic acid, even more preferably from about 10 ppm to about 15 ppm, relative to the final weight of the product.

[0132] In another preferred embodiment, the product of the present invention (e.g., food, etc.) is a beverage product, and the concentration of the composition in the food is from about 5 ppm to about 20 ppm of chlorogenic acid and from about 5 ppm to about 25 ppm of rosmarinic acid, relative to the final weight of the product.

[0133] In another preferred embodiment, the product (eg, food) of the present invention is a beverage product, and the concentration of the composition in the food is about 13.5 ppm of chlorogenic acid and about 15 ppm of rosmarinic acid relative to the final weight of the product.

[0134] In another preferred embodiment, the product (eg, food) of the present invention is a beverage product, and the concentration of the composition in the food is about 9 ppm of chlorogenic acid and about 10 ppm of rosmarinic acid, relative to the final weight of the product.

[0135] In another preferred embodiment, the food product of the present invention is a beverage product, and the concentration of the composition in the food product is about 9 ppm of chlorogenic acid and about 10 ppm of rosmarinic acid, relative to the final weight of the product.

[0136] In another preferred embodiment, the food product of the present invention is a beverage product, and the concentration of the composition in the food product is about 9 ppm of chlorogenic acid and about 1.5 ppm of rosmarinic acid, relative to the final weight of the product.

[0137] In another preferred embodiment, food of the present invention is a beverage. As used herein, term "beverage" refers to any drinkable or edible liquid. In another preferred embodiment of food, beverage is a lemon-flavored beverage, and local flavor is natural and / or artificial.

[0138] The expert will know how to adjust the amount of the composition in the beverage.In another preferred embodiment of the food product of the present invention, the composition comprises from about 4% to about 5% chlorogenic acid, from about 0.3% to about 3% caffeine and from about 0.5% to about 1% rosmarinic acid.

[0139] In a preferred embodiment of the food product of the present invention, the composition is present in the beverage in a concentration of about 50 to 500 ppm, preferably about 100 ppm to about 300 ppm.

[0140] In another preferred embodiment of the food of the present invention, the food is a beverage, preferably a lemon-flavored beverage, wherein the concentration of the composition in the food is from about 1 ppm to about 500 ppm of chlorogenic acid, such as 200 ppm to 500 ppm of chlorogenic acid, such as 400 ppm of chlorogenic acid, and from about 0.5 ppm to about 50 ppm of rosmarinic acid, such as 20 to 40 ppm, such as 30 ppm of rosmarinic acid.

[0141] In another preferred embodiment of the food of the present invention, the food is a beverage, preferably a lemon-flavored beverage, wherein the concentration of the composition in the food is about 9 ppm of chlorogenic acid and about 1.5 ppm of rosmarinic acid, relative to the final weight of the product.

[0142] ***

[0143] The present invention will be described by the following examples, which are to be considered as illustrative only and not limiting of the scope of the invention. Example

[0144] Example 1: Product Description

[0145] Table 1: Overview of the obtained extract products

[0146]

[0147] *Natural Extract = Natural Extract, P80: Polysorbate 80, MPG = PG = Propylene Glycol, Malto = Maltodextrin

[0148] 1. Rosemary CA WS (Table 1, Extract A)

[0149] A detailed process for preparing a composition of rosemary extract is described in U.S. Patent No. 5,859,293 (PCT WO96 / 34534), which is incorporated herein by reference in its entirety. A brief overview of the process is as follows: Rosemary leaves are extracted with acetone at room temperature. After extraction, the acetone extract is filtered to separate the solution from the rosemary leaves and concentrated under reduced pressure to produce a concentrated natural extract. An aqueous sodium carbonate (Na2CO3) solution is added to the concentrated natural extract to dissolve carnosic acid and other organic acids while precipitating alkali-insoluble substances. The solution is filtered to separate the solids, and the filtrate is further concentrated under reduced pressure. Once concentration is complete, phosphoric acid (H3PO4) is added, and acid-insoluble substances (including carnosic acid, carnosol, and sage derivatives) are precipitated from the concentrated solution. The precipitated solid is then separated from the liquid by filtration and rinsed with water to remove impurities. Finally, the solid is dried in a vacuum oven and then ground into a powder.

[0150] The product can then be formulated on different carriers (solid or liquid) to adjust its physical properties (physical form, solubility, color...).

[0151] 2. Green coffee bean extract (Table 1, extracts B and C)

[0152] Green coffee beans of Arabica or Robusta coffee are ground and extracted using an alcohol extraction method. Any other plant or organism comprising chlorogenic acid, or any other method providing or producing chlorogenic acid, may be used.

[0153] Here, the extraction solvent consisted of 75% ethanol and 25% water.

[0154] The extract thus obtained is filtered and concentrated. The concentrated extract is supplemented with an organic acid, either a weak or strong acid, in this case citric acid. The obtained extract is further filtered and concentrated with or without a liquid carrier such as propylene glycol. To obtain Extract C, the concentrated natural extract is spray-dried on maltodextrin.

[0155] 3. Sage extract (Table 1, extracts D and E)

[0156] The aerial parts (leaves and stems) of Salvia officinalis or Sage alba were extracted with 2-5% activated charcoal and acetone under mechanical stirring at reflux (56.4°C) for 2 hours. After extraction, 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 WO96 / 34534. Extract D.

[0157] The product can then be formulated on different carriers (solid or liquid) (extract E) to adjust its physical properties (physical form, solubility, color...).

[0158] 4. Rosemary RA extract (Table 1, extract F)

[0159] Rosemary leaves were extracted by percolation with water at 90° C. for 1 hour and 30 minutes. After the extraction was complete, the water extract was concentrated by filtration through a membrane.

[0160] Once the concentration step has been performed, the extract is purified on a polymeric adsorption resin and the purified extract is spray dried over maltodextrin.

[0161] Example 2. Method

[0162] 2.1-In vitro ORAC assay

[0163] Antioxidant activity was determined by oxygen radical absorbance capacity on a Tecan Infinite fluorescence microplate reader according to the procedure of Ou et al. 2013 (AOAC Official Method 2012.23 Total Antioxidant Activity). This method describes how to perform the analysis of lipophilic and hydrophilic samples.

[0164] The ORAC assay measures a sample's ability to bind oxygen free radicals. A reactive oxygen species generator (AAPH) is added to parallel reactions containing equal amounts of a fluorescent probe (fluorescein sodium salt). Reactions contain either a buffer blank or an antioxidant sample and a standard (Trolox). The antioxidant capacity of a sample is the net difference between the area under the curve (AUC) of the sample and blank. This net AUC for the sample is compared to the net AUC for a standard concentration of Trolox to express the ORAC value of the sample as μmol Trolox equivalents / gram (μmol TE / g).

[0165] The result obtained is proportional to the amount of extract. A blend of products will give an ORAC value proportional to the ORAC of each extract weighted by its proportion in the blend.

[0166] ORAC(blend) = ∑(ORAC of individual extracts * ratio of extracts in blend)

[0167] Example: For a blend of 30% extract 1 with ORAC = 2000 μmol TE / g and 70% extract 2 with ORAC = 700 μmol TE / g, we would expect the ORAC value of the blend to be:

[0168] (2000x 0.3)+(700x 0.7)=1090μmol TE / g

[0169] 2.2. In vitro CAT assay

[0170] The antioxidant capacity was determined by conjugating autooxidizable trienes on a Tecan Infinite microplate reader according to the procedure of Laguerre et al. (Analytical Biochemistry 380 (2008) 282-290).

[0171] As an ORAC assay, the CAT assay measures a sample's ability to bind oxygen free radicals. A reactive oxygen species generator (AAPH) is added to parallel reactions containing equal amounts of an absorbance probe (emulsion). Reactions contain a buffer blank or an antioxidant sample and a standard (Trolox). The antioxidant capacity of a sample is the net difference between the area under the curve (AUC) for the sample and blank. This net AUC for the sample is compared to the net AUC for a standard concentration of Trolox to express the sample's CAT value as μmol Trolox equivalents / gram (μmol TE / g).

[0172] As ORAC, the result obtained is proportional to the amount of extract. A blend of products will give a CAT value proportional to the CAT of each extract weighted by its proportion in the blend.

[0173] CAT(blend) = ∑(CAT of individual extracts * ratio of extracts in blend)

[0174] 2.3. Testing in meat applications (pork)

[0175] For each form, meat (composition see Table 2) was mixed by hand with the amount of extract described in Table 3 until fully incorporated.

[0176] Table 2: Composition of pork used

[0177] Element ％ Pork shoulder 81.00 Pork back fat 13.00 Salt 1.80 black pepper 0.15 Sodium lactate (60%) 4.20

[0178] Table 3: Dosage of extracts in pork applications

[0179]

[0180] Patties were formed and stored in a modified atmosphere (MAP) at 4°C in the dark for 10 days. Samples were analyzed by TBars assay after 3, 6 and 10 days of storage.

[0181] TBA-RS (thiobarbituric acid-reactive substances) is a common analytical method for the degree of oxidation in meat and fish products. The three-carbon compound malondialdehyde (MDA) is the primary carbonyl-degrading molecule of auto-oxidized polyunsaturated substances during secondary oxidation. The basic principle of this method is that one molecule of MDA reacts with two molecules of TBA to form a pink pigment, the MDA-TBA complex, which can be spectrophotometrically quantified at 509, 532, and 580 nm.

[0182] For each approach, a 150 g quantity of ground pork was mixed by hand with a sufficient level of extract until fully incorporated. Patties were formed and cooked in an oven (170°C) until the temperature at the core reached 70°C.

[0183] The patties were stored at 4°C in a light box without any packaging (simply placed on plates to maximize oxygen contact to accelerate the oxidation process).

[0184] TBars measurements were performed as previously described in Zhang et al, Food Science and Human Wellness, 5, 39-48 (2016)).

[0185] Two series were conducted at different times and with different batches of meat, using a sage / green coffee bean blend.

[0186] 2.4. Beverage testing

[0187] Lemon flavor + 12 ppm citral was added to a standard beverage matrix (acidified and sugar water) with or without the addition of our antioxidant extract (dosages are 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.

[0188] Sensory analysis was conducted on "fresh" and "aged" samples, both with and without antioxidants, to understand how well the solution was working. Flavor impression analysis involved quantifying the sensory characteristics of the products through open group discussions. Trained expert panelists tasted the complete product set and generated descriptors specifically for the samples being evaluated. They individually rated the intensity scores for each of these descriptors, then discussed their ratings for each descriptor as a group and agreed on a final consensus profiling. Testing was conducted in a discussion room, with the panel leader collecting the results.

[0189] Table 4: Dosage of extracts and active ingredients in beverage applications

[0190]

[0191]

[0192] Example 3: Results

[0193] 1. In vitro ORAC and CAT antioxidant tests

[0194] 1. Contains a blend of rosemary extract and green coffee bean extract

[0195] From Table 4 and Figure 1 As can be seen in Figure 2, when extract A is blended with extract B, the expected ORAC value can be determined as follows:

[0196] Theoretical ORAC value of the blend = 0.5 × ORAC (A) + 0.5 × ORAC (B) = 0.5 × 541.5 + 0.5 × 913.94

[0197] Theoretical ORAC value of the blend = 727.72

[0198] After analyzing a blend containing 50% Extract A and 50% Extract B, the ORAC value was 2.7 times higher than expected, indicating a synergistic effect due to the blending of these products.

[0199] Table 4: ORAC Measurement

[0200] Extract Description ORAC A 541,5 B 913,94 A+B (50 / 50) Theory 727,72 A+B(50 / 50) actual 1966,53

[0201] 2. Blend of sage extract and green coffee bean extract

[0202] From Table 5 and Figure 2 As can be seen from the graph, when extract C is blended with extract D, the expected CAT value obtained is:

[0203] Theoretical CAT value of blend = 0.5×CAT(C)+0.5×CAT(D)

[0204] Theoretical CAT value of the blend = 0.5 × 1031.82 + 0.5 × 795.7

[0205] Theoretical CAT value of the blend = 913.76

[0206] After analyzing the blend containing 50% Extract A and 50% Extract B, the CAT value was 1.4 times higher than expected. This clearly shows that there is a synergistic antioxidant effect as a result of the blend of these products.

[0207] Table 5: CAT measurements

[0208] Extract Description CAT D 1031,82 C 795,7 C+D theory 913,76 C+D actual 1313,1

[0209] 3. Results in meat applications (pork)

[0210] like Figure 3 As shown in Table 6, the TBArs values ​​of the negative controls were observed to increase significantly over time, reaching almost 3 meqMDA / kg in the first series and exceeding 4.5 meqMDA / kg in the second series after a 10-day shelf life of the meat. In contrast, the meat containing the blend of green coffee bean and sage extract at different doses remained below 0.8 meqMDA / kg after the shelf life.

[0211] The use of natural antioxidant solutions appears to prevent lipid oxidation mechanisms.

[0212] Table 6: TBArs results in pork

[0213]

[0214] 4. Results in beverage applications

[0215] Sensory analysis was conducted on fresh and aged samples with and without antioxidants to understand how well the solution was working.

[0216] As can be seen in Table 7, rosemary alone at 30 ppm and green coffee beans alone at 440 ppm protected the lemon flavor from oxidation. The effects on flavor and balance properties were partially protected (20%). Lemon candy notes and citrus fresh notes were also partially protected (27% and 67% for rosemary and 27% and 33% for green coffee beans). However, the citrus notes were not protected. In addition, the formation of oxidized notes was limited. 30 ppm of rosemary only limited the formation of oxidized citral cherry notes and lime distillate notes (67% and 17%), but could not limit the formation of oxidized citral animal notes and oxidized terpene notes. 440 ppm of 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%.

[0217] Surprisingly, combining the two extracts at half the dose, we observed an important synergistic effect. The citrus notes were not protected by the individual extracts, while we observed 50% protection with the combination. In addition, the combination better protected the lemon candy and lemon fresh notes (47% and 67% versus the expected only 27% and 50%). Finally, the oxidized note formation was better limited than expected. We expected an 8% limit for the oxidized citral animal note, and we obtained a 17% limit. We expected a 67% limit for the oxidized citral cherry note, and we obtained an 83% limit. We expected an 8% limit for the oxidized terpene note, and we obtained a 17% limit. Finally, we expected a 17% limit for the lime distillate note, and we obtained a 33% limit.

[0218] Based on these results, we expected to observe the same synergistic effect between green coffee and another botanical rich in rosmarinic acid, such as lemon balm.

[0219]

Claims

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

100.

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

25.

3. The composition according to claim 1 or 2, 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. The composition according to any one of claims 1 to 3, wherein the ratio of chlorogenic acid to phenolic diterpenes is from about 5:1 to about 1:5, preferably from about 0.9:1 to about 1:0.

9.

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

6. The composition according to any one of claims 1 to 5, wherein the rosmarinic acid is provided in the form of an extract of aerial parts of Rosemary and / or an extract of aerial parts of Melissa officinalis.

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

8. A method for preventing and / or inhibiting oxidation of a food or beverage product for human or animal use, a nutritional supplement, a nutraceutical preparation, a spice or flavoring, a pharmaceutical or veterinary preparation, a brewing or cosmetic preparation, said method comprising the step of contacting the food or beverage product for human or animal use, the nutritional supplement, the nutraceutical preparation, the spice or flavoring, the pharmaceutical or veterinary preparation, the brewing or cosmetic preparation with a composition according to any one of claims 1 to 6.

9. Use of a composition according to any one of claims 1 to 6 for preventing and / or inhibiting oxidation in food or beverage products, nutritional supplements, nutraceutical preparations, spices or flavorings, pharmaceutical or veterinary preparations, brewing or cosmetic preparations for humans or animals.

10. The use according to claim 9, for the production of food or beverage products for humans or animals, nutritional supplements, nutraceutical preparations, spices or flavorings, pharmaceutical or veterinary preparations, winemaking or cosmetic preparations.

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

12. A food or beverage product for human or animal use, a nutritional supplement, a nutraceutical preparation, a spice or flavoring, a pharmaceutical or veterinary preparation, a brewing or cosmetic preparation, comprising the antioxidant composition according to any one of claims 1 to 6 and an adjuvant acceptable to the food or beverage product for human or animal use, the nutritional supplement, the nutraceutical preparation, a spice or flavoring, a pharmaceutical or veterinary preparation, a brewing or cosmetic preparation.

13. The food or beverage product for human or animal use, nutritional supplement, nutraceutical formulation, spice or flavoring, pharmaceutical or veterinary formulation, brewing or cosmetic formulation according to any one of claims 11 to 12, wherein the composition in the food comprises chlorogenic acid to phenolic diterpenes in a ratio of about 0.1:1 to about 1:0.1, preferably about 0.8:1 to about 1:0.

8.

14. The food or beverage product for human or animal use, nutritional supplement, nutraceutical preparation, spice or flavoring, pharmaceutical or veterinary preparation, brewing or cosmetic preparation according to any one of claims 11 to 13, wherein the composition in the food comprises: - about 0.1% w / w to about 55.0% w / w, preferably about 2.0% w / v to 25% w / w 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 caffeine; and - at least about 0.1% w / w phenolic diterpenes.

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

16. The product (e.g., a food or beverage product) according to claim 15, wherein the concentration of the composition in the product (e.g., a food or beverage product) is about 5 to 50 ppm relative to the final weight of the product.

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

18. The product (eg, a food or beverage product) according to any one of claims 11 to 16, wherein the concentration of phenolic diterpenes is from about 5 ppm to about 1000 ppm relative to the final weight of the product.

19. The product (eg, 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 relative to the final weight of the product.

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

21. The product (e.g., a food or beverage product) according to claim 20, wherein the food is a meat product and wherein the concentration of the composition in the food is about 13.5 ppm of chlorogenic acid and about 15 ppm of phenolic diterpenes relative to the final weight of the product.

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

23. The product (e.g., a food or beverage product) according to claim 19, wherein the product is a beverage, preferably a lemon-flavored beverage, wherein the concentration of the composition in the food product is from about 1 ppm to about 100 ppm of chlorogenic acid and from about 0.1 ppm to about 50 ppm of rosmarinic acid, relative to the final weight of the product.

24. The product (e.g., a food or beverage product) according to claim 23, wherein the product is a beverage, preferably a lemon-flavored beverage, wherein the concentration of the composition in the food product is about 9 ppm of chlorogenic acid and about 1.5 ppm of rosmarinic acid relative to the final weight of the product.

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