WO2017208058A1 - Produits à base de poudre de cacao à haute teneur en polyphénols, utilisations et procédés de fabrication associés - Google Patents

Produits à base de poudre de cacao à haute teneur en polyphénols, utilisations et procédés de fabrication associés Download PDF

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Publication number
WO2017208058A1
WO2017208058A1 PCT/IB2016/053277 IB2016053277W WO2017208058A1 WO 2017208058 A1 WO2017208058 A1 WO 2017208058A1 IB 2016053277 W IB2016053277 W IB 2016053277W WO 2017208058 A1 WO2017208058 A1 WO 2017208058A1
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Prior art keywords
cocoa
beans
based product
epicatechin
powder
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PCT/IB2016/053277
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English (en)
Inventor
Hector Hugo OLARTE NORENA
Maria José CHICA
Giovanni Scapagnini
Armando ZARRELLI
Antonio PISANTI
Sergio DAVINELLI
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Casaluker S.A.
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Priority to PCT/IB2016/053277 priority Critical patent/WO2017208058A1/fr
Publication of WO2017208058A1 publication Critical patent/WO2017208058A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/0003—Processes of manufacture not relating to composition or compounding ingredients
    • A23G1/0006—Processes specially adapted for manufacture or treatment of cocoa or cocoa products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/0003—Processes of manufacture not relating to composition or compounding ingredients
    • A23G1/002—Processes for preparing or treating cocoa beans or nibs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin

Definitions

  • the present invention relates to cocoa powder based products with a high content in polyphenols and uses and method for the manufacture thereof.
  • the present invention origins in the field of food industry and of nutritional products.
  • the present invention concerns with a process for the production of cocoa based food products, especially cocoa powder, and healthy food products having a high polyphenol contents and with nutritional, nutraceutical, medical or cosmetics uses of these cocoa based products.
  • Edible products containing cocoa derivatives such as chocolate, cocoa butter, cocoa liquor and other cocoa solids are widely consumed for their taste and mouthfeel.
  • cocoa powder is used in the food industry for the preparation of a variety of food products, amongst which chocolate, bakery products, desserts and beverages.
  • cocoa contains certain naturally occurring antioxidant substances such as flavonoids and flavanols, especially catechins and epicatechins and other nutritional substances such as theobromine, theophylline and minerals whose consumption has been associated with certain health benefits, has increased the potential applications of cocoa-based food products.
  • the consumption of chocolate has been associated with the certain health benefits such as improvement in the endothelial vascular function, including regulation of blood pressure and with certain anti-inflammatory activities.
  • One of the general objects of the present invention is to provide a cocoa powder and cocoa based products having a high content of antioxidant substances especially polyphenols such as epicatechins and catechins.
  • Another object of the invention is to provide a method for the preparation of a cocoa powder with a high content in selected polyphenols.
  • Yet another object of the invention is the provision of nutritional or healthy products such as chocolate, beverages or chocolate derivatives with a high content of a selected polyphenol having antioxidant properties.
  • the present invention originates from the finding that a cocoa powder or cocoa- based product highly rich in selected polyphenols can be obtained by using certain specific conditions in the industrial production of cocoa powder.
  • the inventors found that the amount of selected naturally occurring polyphenolic components contained in the starting cocoa beans is retained or only partially affected, if certain specific treatments, which are typical of the traditional methods for producing cocoa powder, are avoided or substantially changed.
  • certain polyphenols contained in the cocoa- based products/powders obtained by the process of the invention may have a bioavailability in the human body which is increased with respect to the naturally occurring polyphenols contained in the starting cocoa beans.
  • the denaturation or oxidation of polyphenols that occurs during processing of cocoa beans is substantially avoided or reduced and selected polyphenolic monomeric components having an improved bioavailability are made available.
  • the present invention provides cocoa components, especially cocoa powder, having high levels of selected cocoa polyphenols.
  • the present invention provides a cocoa-based product, especially a cocoa powder, having an epicatechin content greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg.
  • the present invention concerns with a composition
  • a composition comprising the cocoa-based product of the invention, especially in the form of cocoa powder, having an epicatechin content greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg.
  • the cocoa-based product of the invention is a chocolate.
  • the composition may be a nutritional composition, a food supplement, a medicament or medicine useful for ameliorating or maintaining the health of a human being.
  • the cocoa-based product or a composition containing the cocoa- based product of the invention are useful in the treatment and/or prevention of oxidative stress of the human body.
  • the present invention concerns with a cocoa- based product, especially a cocoa powder or an extract thereof having an epicatechin content greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg for use in the treatments of an inflammatory disease, a metabolic disorder or a cardiovascular disease.
  • the present invention provides a process for the production of a cocoa-based product, especially cocoa powder, having an epicatechin content greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg, the process comprising providing unfermented or underfermented cocoa beans having a moisture or water content of less than 15% by weight and heating the cocoa beans at a temperature of 70 to 130 °C for a period of time of 1 to 30 minutes.
  • the process of the invention excludes a roasting step of the cocoa beans or nibs.
  • roasting step it is intended a conventional heating treatment different from an IR heating.
  • the degree of fermentation of the cocoa beans is determined by changing of the colour grains and may be measured by applying the so-called cutting test according to ISO International Standard No. 1 1 14. 30.
  • a cocoa powder rich in certain selected polyphenols especially epicatechins finds application in the preparation of either a nutritional or medical product which is useful in the prevention and/or treatment of certain conditions or affections of the human organisms.
  • Fig. 1 shows a bar graph illustrating the results of a NF-kB p65 DNA binding activity assay (O.D.) carried out in cultured macrophages with LPS (Lipopolysaccharide), LPS + CE (commercial cocoa powder), LPS + CCP (Colombian Cocoa Powder of the invention) stimulation according to Example 2A.
  • LPS Lipopolysaccharide
  • CE commercial cocoa powder
  • LPS + CCP Cold-Coa Powder of the invention
  • Fig. 2 shows comparative bar graphs illustrating the cytokines IL-1 b, IL-6 and TNF-a expression on macrophages pre-treated with CE (commercial cocoa powder), CCP (Colombian Cocoa Powder of the invention) and exposed to LPS.
  • the blank bars refer to the basal conditions of the macrophages (i.e. untreated cells), according to Example 2A.
  • the exposure of macrophages to LPS induces maximal secretion of cytokines whereas the exposure to CCP the minimal.
  • Fig. 3 shows graphs summarizing the results of a heme oxygenase activity assay by real time PCR determinations carried out according the Example 2D of the present application.
  • the graphs show the ability of CCP of the invention to activate HO-1 gene expression in a more efficient way compared to traditional CE.
  • Fig. 4 shows the results of a Western blot for Nrf2 as illustrated in Example 2E.
  • the bar graphs prove that the treatment with CCP of the invention provides a greater time-dependent increase in Nrf2 protein expression in the nuclear extracts compared to conventional CE.
  • Fig. 5 shows bar graphs illustrating the effects of CCP of the invention in inducing NO production using cultured human umbilical vein endothelial cells (HUVEC) according to Example 2F.
  • HAVEC human umbilical vein endothelial cells
  • Fig. 6 shows a diagram with peaks of (-)-Epicatechin, and of 3'-O-methyl-(-)- epicatechin, and 4'-O-methyl-(-)-epicatechin which are derived from the metabolism of epicatechin, as evidenced in Example 3.
  • Fig. 7 shows a graph reporting the variation of the level of (-)-Epicatechin in plasma (nM) vs. the time (h) after administration in subjects undergoing the protocol according Example 4.
  • Fig. 8 shows a graph reporting the variation in the level of 3'-O-methyl-(-)- epicatechin in plasma (nM) vs. the time (h) after administration in subjects of the protocol according Example 4.
  • Fig. 9 shows a graph reporting the variation in the level of 4'-O-methyl-(-)- epicatechin in plasma (nM) vs. the time (h) after administration in subjects undergoing the protocol according Example 4.
  • Fig. 10 shows three bars reporting the changes of total cholesterol in the subjects treated with cocoa according to the Protocol of Example 6.
  • White, grey and black circle are the different dosages of cocoa group during the treatment.
  • the graph shows a significant differences between the curves of 8 pills/day group and the other two groups (p 0.04).
  • Fig. 1 1 shows the changes of LDL-cholesterol in the subjects treated with cocoa according to the Protocol of Example 6. White, grey and black circle are shown in cocoa group. P ⁇ 0.05 for the comparison with the baseline.
  • Fig. 12 shows graph bars illustrating the plasma HDL concentrations in subjects of the Protocol of Example 6 who showed an increase in total amount of epicatechin metabolites in the urine. P ⁇ 0.05 compared to their counterparts.
  • Fig. 13 shows graph bars illustrating the change of oxidized LDL (Ox-LDL) values within each group after 4 weeks of intervention of the Protocol of Example 6
  • Fig. 14 shows bar graphs illustrating the variation in the ratio omega6/omega3
  • the inventors have found that the amount of (-)epicatechin available in the naturally occurring cocoa beans is retained or preserved during cocoa beans processing for producing cocoa based products such as cocoa powder, if certain specific process conditions are met and combined.
  • the invention concerns with isolated cocoa based products, especially isolated cocoa powder having an (-)epicatechin content which is far close to the amount available in the starting material represented by unfermented or underfermented cocoa beans.
  • isolated cocoa powder having an (-)epicatechin content which is far close to the amount available in the starting material represented by unfermented or underfermented cocoa beans.
  • the inventors have also ascertained that (-) epicatechin contained in the cocoa based product of the invention, when administered by the oral route, has a greater bioavailability with respect to the other polyphenols available in the naturally occurring cocoa beans.
  • the invention provides a cocoa based product which is rich in (-) epicatechin, a selected polyphenol, and which finds application in the food, nutritional and medical field by virtue of its antioxidative activity and bioavailability.
  • the present invention provides an cocoa-based product, especially an cocoa powder, having an epicatechin content greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg.
  • epicathechin is (-) -epicatechin.
  • epicathechin should be intended (-)epicatechin.
  • the cocoa-based product of the invention has an epicatechin or (-) -epicatechin content from 15 to 45 g/Kg, from 18 to 36 g/Kg, preferably from 21 to 33 g/Kg, from 28 to 31 g/kg.
  • the (-) epicatechin contained therein in contrast with most of the polyphenols contained in the cocoa beans, are monomers which having a bioavailability greater that polyphenols available from traditional cocoa product and for this reason may be easily absorbed in the gastrointestinal tract of a subject.
  • the cocoa products of the invention has an amount of (-) epicatechin which is from 5 to 60%, preferably from 10 to 40% by weight greater than the content of (-)epicatechin contained in naturally occurring cocoa beans.
  • cocoa-based products of the invention may be in solid form or in liquid or semi-liquid form.
  • cocoa-based product in solid form or cocoa solids examples include cocoa powder, cocoa bean or portions thereof, cocoa nibs, or solid products obtained by processing cocoa beans with the method of the present invention.
  • the cocoa-based product of the invention is solid and more preferably is a cocoa powder.
  • the present invention provides a composition
  • a composition comprising the cocoa-based product of the invention, especially in the form of cocoa powder, having an (-)epicatechin content > 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg.
  • composition of the invention may be a food product, a nutritional product a dietetic product or a composition certain activity influencing certain activities or metabolism of the human body.
  • compositions of the invention may be solid, semi-solid or liquid.
  • the composition of the invention comprises a chocolate based product.
  • chocolate based product as used herein means a composition containing cocoa solids dispersed in a fat phase.
  • chocolate based products in solid form include sweet semisweet or bittersweet-chocolates, chocolate flavoured products, chocolate flavoured confections, chocolate sweetens, chocolate bars, chocolate fat coatings, low fat chocolate.
  • chocolate based products in liquid form include chocolate muss, milk or buttermilk chocolate, chocolate based beverages or drinks.
  • the fat phase of the chocolate includes cocoa butter, milkfat, vegetable or substituted fats, replacer-equivalent fats and in general conventional fats used in the confectionary industry.
  • the chocolate based product contains sweeteners such as natural sugars such as sucrose, fructose, dextrose, maltose, glucose syrup, honey, invert sugar or artificial sweeteners and its blends such as saccharine, aspartame, acesulphame-k cyclamates or natural sweetener such as stevia or polyalcohols such as mannitol, xylitol, sorbitol, maltitol.
  • sweeteners such as natural sugars such as sucrose, fructose, dextrose, maltose, glucose syrup, honey, invert sugar or artificial sweeteners and its blends such as saccharine, aspartame, acesulphame-k cyclamates or natural sweetener such as stevia or polyalcohols such as mannitol
  • the chocolate based product contain edible emulsifiers such as lecithin, mono and dyglycerides, sorbitan monostearate, polyglycerol esters of fatty acids.
  • edible emulsifiers such as lecithin, mono and dyglycerides, sorbitan monostearate, polyglycerol esters of fatty acids.
  • the composition of the invention is a nutritional composition.
  • the nutritional composition contains cocoa solids of the invention or an extract thereof having an epicatechin content greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg and optional nutrients or micronutrients such as a source of carbohydrates, a source of lipids, and optionally other nutrients or micronutrients.
  • the invention provides a non-therapeutical or therapeutical uses of the cocoa-based product or cocoa powder for reducing the cellular oxidative stress in an organism, especially a human being.
  • oxidative stress is understood herein to refer to an imbalance between oxidizing substances formed in the body by the action of breathing or sunlight and other factors and natural antioxidants produced by the body or in other words, an imbalance between the production of free radicals and the ability of the body to counteract or detoxify their harmful effects through neutralization by antioxidants.
  • the cocoa-based products of the invention find application in the prevention or treatment of the above conditions.
  • the present invention provides a process for the production of a cocoa-based product, especially cocoa powder, having a (-) epicatechin content greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg, said process comprising a heating treatment of unfermented or underfermented cocoa beans wherein said heating treatment comprises or consist essentially of an infrared treatment.
  • the process of the invention exclude a roasting step of the beans for example including a heating at a temperature of 120 to 150 °C, 125 to 145 °C for a time of 1 to 120 minutes.
  • roasting step means a conventional heating which is different from a heating treatment by infrared.
  • the infrared heating of the unfermented or underfermented cocoa beans rapidly heat and expand the shell of the beans facilitating the elimination or removal of the shell of the beans limiting or avoiding damages or denaturalization of polyphenol substances, which occurs when the beans or nibs are roasted in accordance with conventional processes.
  • the process of the invention excludes a roasting step wherein the beans or nibs contained in the shell are roasted.
  • the process excludes a roasting step wherein the
  • the unfermented or underfermented cocoa beans before the heat treatment by infrared have a moisture level or water content of less than 20% by weight of the weight, typically from 5 to 12%, especially from 7 to 8% by weight.
  • the infrared heating treatment is carried out at a temperature of 90 to 1 18 °C, of 105 to 1 15 °C for a time of 1 to 5 minutes, preferably of 2 to 4 minutes.
  • the heating step is carried out by infrared heating at a temperature of 80 to 95 °C for a time of 2 to 10 minutes, typically from 2 to 5 minutes.
  • the heating treatment of the invention is made by a commercial infrared equipment such as that commercialized by the Barth company.
  • the infrared heating treatment is carried out by exposing the beans to an infrared radiation having a wavelength of 2 to 6 microns, which means a frequency from 0.7 to 1 .2x10 8 megacycles/sec.
  • the process of the invention comprises grinding or milling the cocoa nibs into a fluid dark brown cocoa liquor containing the ground/milled particles of cocoa solids suspended in a cocoa butter and
  • the starting material of the process of the invention comprises freshly harvested unfermented or underfermented cocoa beans which are obtained from the pods derived from cocoa trees which typically belong to species of Theobroma cacao.
  • the cocoa trees are selected clones of cocoa trees of Colombian origins having a high polyphenol content.
  • the unfermented cocoa beans have a fermentation degree from 35 to 45% of grains.
  • the grains are extracted by the pod and processed according to the invention without carrying out a fermentation step.
  • cocoa bean In cases where the cocoa bean are not subjected to a fermentation step and nevertheless they have a degree of fermentation from 3 to 8% as grain well fermented, this is the consequence of a naturally occurring fermentation between harvesting of pods and processing of cocoa beans contained in the pods.
  • the underfermented cocoa beans have a fermentation degree from 55 to 65% of grain with violet or purple colour.
  • underfermented cocoa beans are obtained subjecting the extracted cocoa beans to a partial fermentation step (during the draining process) which for example is carried out for a period of time of 20 minutes to 5 hours, of 30 minutes to one hour.
  • the degree of fermentation of the cocoa bean or the change of the colour of the beans is determined by applying the so-called cut test a method in accordance with the International standard ISO cut test No. 1 1 14. 300.
  • this test method cocoa beans are opened or cut lengthwise through the middle, so as to expose the maximum cut surface of cotyledons. Both halves of visually examine each bean in full daylight or equivalent artificial light. Count the number of cocoa bean that shows a violet or purple colored on at least half of the surface of the cotyledons exposed by the cut test.
  • the beans may be divided in four different typologies: 1 . fully fermented beans wherein the predominant colour is brown/dark brown, 2. partially fermented beans wherein the predominant colour is brown-purple, 3. underfermented beans wherein the predominant colour is purple- violet and 4. unfermented bean wherein the predominant colour is slaty-grey. Tipically, 1 and 2 are added.
  • fermentation degree is a numerical value of percentage (%) of the degree of fermentation of a batch of cocoa beans. In certain embodiments, the fermentation degree may vary from 100 to 400 where lower values represents unfermented beans and upper represents fully fermented beans.
  • the "fermentation degree” may be calculated by using a grading scale in % for characterizing the fermentation degree of the 300 grains analysed (divided in 3 groups of 100 grains each one) taken from the sample (about one kilogram) of General batch.
  • the slaty/grey coloration means completely unfermented cocoa beans and, purple-violet coloration means under fermented cocoa beans.
  • the starting material of the process of the invention comprises or consists essentially of underfermented or unfermented beans or mixtures thereof.
  • the beans are extracted from pods from cocoa trees.
  • a fermentation step of the cocoa beans according to the conventional processes of production of cocoa powder/product is not carried out, which means that is absent.
  • the starting unfermented or underfermented cocoa beans may be wet.
  • the available unfermented or underfermented cocoa beans are drained.
  • the draining step b) comprises the removal of the free water within the cocoa beans to delay the start of the fermentation and to reduce the rate of reduction of flavanols contained in the beans by oxidase enzymes action.
  • step b) takes from 5 to 12 or from 12 to 20 hours, for example 14 to 18 hours.
  • the leached water is in an amount of 12 to 16% by weight in respect of the total weight of the beans.
  • Step c) of the process comprises drying the beans to reduce the water content.
  • the total content of the moisture of the beans is reduced to an amount of 7 to 8% by weight to prevent mold growth during storage of cocoa beans, thereby preventing damage to the cocoa butter and the appearance of unusual flavors or odors.
  • the drying step may be carried out gradually in order to prevent the closure of the small holes placed on the surface of the cocoa bean thereby allowing moisture and volatile substances such as acetic acid to outflow while the amount of polyphenols remain unchanged.
  • the drying step comprises the following drying times: (i) First day 3 hours; (ii) Second day: 3-4 hours; (iii) Third day 4-5 hours (iv) Fourth day 5-6 hours and (iv) Fifth day: all day.
  • cocoa beans may be cleaned to remove extraneous non-cocoa materials such as dust particles, metals and nonmetals, rocks, stem, cluster beans, broken beans and other parts of the tree.
  • the average of impurities may be 1 % by weight of the total weight after cleaning.
  • the cleaning step may be carried out using one or more of the following apparatuses: densimetric table, metal detector, dust extractor.
  • step d) the heating treatment of step d) is carried out by infrared.
  • the shell is removed by contacting with boiling water in spray way during the IR process, which makes a swell of the shell and facilitate the separation between the nib and the shell.
  • Another advantage of some embodiments of the process is represented by the fact that the cocoa butter doesn ' t go from the kernel to coat seed.
  • the heating temperature of step is lower than traditional roasting with the whole bean, the lower temperature and time 3 min at 1 10-120 °C reduce possible impairment in the polyphenolics content of the beans.
  • step d) One of the aim of step d) is the preparation of the cocoa beans to make easy take off the shell.
  • the outer portion of the bean referred as shell is separated by the inner portion referred as nib.
  • nibs refers to small pieces of cocoa beans of different sizes without shell obtained in the winnowing process.
  • the beans are cracked and carry to a vibrating screening where the shell is removed for the air action and is graduated depending on the size of the bean.
  • the sieve of the sieving apparatus has holes with different diameters: (i) 8,5 mm, the biggest; (ii) 6,0 mm, flow 44%; 4,0 mm, flow 30,6%; (iv) 2,2 mm, flow 18,1 %; (v) 1 ,0 mm flow 4,9 %.
  • the difference in holes and flow allow to make a classification of the nib by the size.
  • the range admitted is 0, 3 to 0, 6 % nibs in shells, and 1 ,5 -1 ,8 % of shell in nibs.
  • the nibs are passed through sieves and over magnets to remove non-cocoa materials such as metal materials.
  • the nibs undergo to grinding step f) of the process.
  • the grinding step may consist of or comprises a milling step.
  • the grinding step may include a pre-milling step carried out in pre-mills for example in an apparatus with blades wherein the ribs are ground.
  • milling the grinding step carried out with a mill.
  • the milling step comprises the milling of cocoa nibs into a liquefied product which is referred to as cocoa liquor which typically is a fluid dark brown liquor.
  • cocoa liquor typically is a fluid dark brown liquor.
  • the cocoa nibs reach a temperature of 70 to 90 °C for example 80 °C. In these conditions the nibs are liquefied to a cocoa liquor.
  • the fat content of the cocoa liquor is from 50 to 60% for example about 54% and the particle size may be 1 .2% retained on 200 microns mesh.
  • the cocoa liquor produced by the milling step is collected and in certain embodiments is stored in a tank for preconditioning for example at a temperature of 100 -1 10 °C.
  • the resulting mass is pumped to a tank, for example having a capacity of 180- 200kg, and the temperature may be arranged in the range of 105 to 1 15, for example of about 1 10 "C.
  • step g) the cocoa solids are separated from cocoa butter. Typically, the cocoa solids are partially defatted.
  • the separation step comprises or consists of a pressing step h) of the cocoa liquor containing both cocoa solids and cocoa butter.
  • the liquor is pressed in a press, for example under a pressure of 1 1 ,000 psi with a cycle time from 8 to 12 min or 16 min, depending on the fat content.
  • cocoa solids according to the invention typically are in form of a cocoa cake
  • a cocoa butter in liquid or semifluid form typically is a high-fat extract from the cocoa liquor obtained by grilling or milling the nibs.
  • the cocoa cake obtained by the pressing step may be crushed and or a milled to yields a cocoa powder with a high content of polyphenols according to the invention.
  • cocoa butter may be purified for example by filtering and crystalizing.
  • cocoa solids refers to the extract of cocoa beans which contains flavonoids, flavanols such as catechins and epicatechins. Cocoa solids may also refer to the cocoa powder.
  • the invention provides, chocolate liquor and/or cocoa solids or powder and/or cocoa butter obtained by the process according to one or more of the embodiments herein described.
  • the cocoa powder or chocolate liquor or cocoa butter obtained by the process of the invention has a epicatechin content of greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg.
  • the inventors also founds quite unexpectedly that the epicatechin amount of the cocoa powder obtained in accordance with one or more embodiments of the invention is greater than the epicatechin amount contained in the starting cocoa beans.
  • the invention provides a chocolate comprising a cocoa based product or a cocoa powder according to anyone of the above referred embodiments.
  • the chocolates may be prepared starting from the suitable cocoa- based product of the invention using conventional techniques.
  • the chocolate of the invention has a content of cocoa powder of greater than 20%, 30%, 40%, 50%, 60%, 70% 80%, 90%.
  • the present invention provides food or nutritional products containing a cocoa powder or cocoa solids having an epicatechin or (-) - epicatechin content of greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg.
  • the food product is chocolates comprising a cocoa powder and/or cocoa solids and/or chocolate liquor according to anyone of the above referred embodiments.
  • the food product is a chocolate flavoured product comprising a cocoa component referred hereinabove.
  • the invention provides the use of the cocoa based product of the invention, including cocoa powder, cocoa liquor, cocoa solids referred hereinabove for ameliorating or maintaining the health conditions of a mammal, typically a human being, by administering a nutritionally effective amount of cocoa based product having an epicatechin content of from greater or equal than 15 g/kg, typically in the range from 15 to 45 g/Kg, from 18 to 36 g/Kg, from 21 to 33 g/Kg of the product.
  • the following examples are illustrative of the cocoa-based products of the invention and of a process for its production.
  • bioactive compounds available in cocoa were measured by HPLC method: theobromine, caffeine, (-)epicatechin, procyanidin B2, gallic acid, theophylline by. A simultaneous determination of these compounds by adding known amounts of reference standard was carried out.
  • cocoa powder batch according to the invention has a content of procyandin B2, gallic acid, teofillin, polyphenols and especially (-) epicathechin, higher than the batches of the products available in the market.
  • REPORT Cellular experimental models to assess biological activities of a Colombian Cocoa Powder with high polyphenols concentration.
  • cytokines such as IL-1 ⁇ , IL-6 and TNF-a.
  • NF-kB p65 DNA Binging Activity Assay by TransAM p65 transcription factor ELISA kit (Active Motif, Carlsbad, CA). Immortalized cell line of macrophages were stimulated with 500 ng/ml LPS. Cells were pretreated or not for 1 h with CCP 10 ⁇ or a commercial cocoa powder (CE) 10 ⁇ , for 12 hours. Then, DNA binding activity of NF-kB p65 was determined. 12 hours after, LPS stimulation markedly promoted NF-kB p65 DNA binding activity and expression of proinflammatory cytokines IL-1 ⁇ , IL-6 and TNF-a.
  • ATCC human immortalized macrophages were exposed for 6 h to different concentrations of CCP (1 , 10, 25, and 50 ⁇ ). Treatment resulted in a significant (p ⁇ 0.05) increase of HO-1 imRNA, measured by quantitative real-time PCR, with a maximal value at 25 ⁇ .
  • CCP elicits a dose-dependent increase of HO-1 imRNA, measured with respect to the not-inducible HO-2 paralog gene, which reaches the maximum (about 6 fold) at 25 ⁇ , and decreases subsequently at 50 ⁇ .
  • CE is instead much less active in inducing HO-1 gene expression at the same concentrations, and reaches the maximum again at 25 ⁇ (figure 3).
  • the pattern of increase of activity was comparable to the results obtained looking at the cellular imRNAs, confirming the functional significance of the data obtained by the real time PCR determinations (figure 3).
  • Results highlight the ability of CCP to activate HO-1 gene expression, in a more efficient way compared to CE.
  • Nrf2 Activation of Nrf2 expression in different cells.
  • the homogenate was then centrifuged at 3000 rpm for 3 min at 4 Q C and the nuclear pellet was resuspended in 30 ⁇ of cold buffer consisting of 20 mM HEPES (pH 7.9), 0.4 M NaCI, 1 mM EDTA, 1 mM EGTA, 1 ⁇ /W DTT, and protease inhibitors.
  • the pellet was then incubated on ice for 15 min and vortexed for 10-15 s every 2 min.
  • the nuclear extract was finally centrifuged at 13,000 rpm for 5 min at 4 Q C.
  • the supernatant containing the nuclear proteins was resolved by SDS-polyacrylamide gel and submitted to immunoblot analysis using anti-Nrf2 (1 :500 dilution) and anti-Sp1 (1 :500 dilution) antibodies
  • Nrf2 protein expression As shown in figure 4, treatment with CCP caused a significant time-dependent increase in Nrf2 protein expression in the nuclear extracts. Quantification of three independent western blots showed that after 1 h exposure to 25 ⁇ CCP, Nrf2 expression significantly increased and remained up-regulated till 12h, whereas the levels of the housekeeping transcription factor Sp1 were stable. CE induced a lower increment of nuclear Nrf2.
  • NO nitric oxide
  • eNOS endothelial nitric oxide synthase
  • NO regulates vascular tone, proliferation of vascular smooth muscle cells, and hemostasis, among other important functions.
  • Disruptions in the physiological production of NO triggers endothelial cell dysfunction, resulting in an increased susceptibility to CVD. Therefore, strategies aimed at "physiologically" increasing NO bioavailability are promising for the prevention and therapy of CVD, such as of others diseases related to vascular disfunctions.
  • HAVEC human umbilical vein endothelial cells
  • the amount of nitrites was determined spectrophotometrically by the Griess reaction adapted for a 96- well plate reader (Quattrone S et al., Molecular Human Reproduction 2004), by conversion of nitrates to nitrites by a 30 min incubation at 37°C with 100 mlU/ml nitrate reductase (Sigma) and 20 pg/ml NADPH (Sigma). In brief, 100 ⁇ of sample was added to 100 ⁇ of Griess reagent (1 % sulphanilamide and 0.1 % N-[1 -naphtylethylendiamine in 5% phosphoric acid).
  • the optical density at a wavelength of 546 nm was measured with a Bio Rad 550 micro plate reader.
  • Nitrite concentrations in the supernatants were calculated by comparison with standard concentrations of NaNO2 dissolved in culture medium and expressed as nmol/mg of proteins, the latter measured spectrophotometrically by the bicinchoninic acid method. The reported values are the mean (6 SEM) of three separate experiments, each performed in duplicate. CCP added to the culture medium for 12 h caused significant increase of nitrites at all the concentration used with maximal activity at 10, 25 and 50 ⁇ .
  • the product tested in this analysis is a Colombian cocoa sample according to the invention. Firstly, the starting product was subjected to a qualitative and quantitative analyses of its key components. The results are shown in Tables 1 and 2.
  • the sample preparation method was adapted from Unno et al. [1 ]. Two milliliters of plasma were spiked with 100 ⁇ _ of a solution containing 10 ⁇ of 3'-O-Methyl-(-)- epicatechin and 10 ⁇ of 4'-O-Methyl-(-)-epicatechin (internal standards) and diluted with 4 imL of 3.4% (w/v) phosphoric acid. Thereafter, samples were loaded onto solid-phase extraction (SPE) cartridges (Water, 60 mg, 3 cc) previously conditioned with 1 mL of ⁇ , ⁇ -dimethyl formamide (DMF) : methanol (7 : 3) and 0.5% (v/v) acetic acid in water.
  • SPE solid-phase extraction
  • the washing steps consisted of 5 mL of 0.5% (v/v) acetic acid in water, 2 mL of water : methanol : acetic acid (80 : 20 : 0.5), and 2 mL of 0.5% (v/v) acetic acid in acetonitrile.
  • (-)-epicatechinis After absorption in the intestinal tract, (-)-epicatechinis rapidly metabolized into structurally related (-)-epicatechin metabolites by O-glucuronidation, O- sulfonation, O-methylation, and combinations thereof catalyzed by uridine-50- diphosphate glucuronosyl-transferases, sulfo-transferases, and catechol-O- methyltransferases, respectively.
  • the net result of the extensive first-pass metabolism is the presence of glucuronides, sulfates, and/or methyl conjugates in the blood stream. These metabolites chemically different from the aglycone forms originally present in foods, are the compounds that reach the target organs.
  • Solvent A was composed of water with 0.1 % acetic acid and solvent B of acetonitrile with 0.1 % acetic acid. Gradient conditions were as follows: time 0 min, 8% solvent B; time 0.5 min, 33% solvent B; time 5 min, 40% solvent B; time 5.1 min, 100% solvent B; time 6 min, 100% solvent B; time 6.1 min, 33% solvent B; time 8 min, 33% solvent B.
  • the injection volume was 10 imL and the flow rate was 0.5 imL/min.
  • the best signal and resolution in the MS system were achieved using negative-ion mode under the following conditions: capillary 2.00 kV, source temperature 150 °C, desolvation temperature 500 °C, and desolvation gas flow 1000 L/h.
  • (-)-epicatechin metabolites was conducted with the following m/z transition: 305 ⁇ 109 (O-Methylepicatechins), and 289 ⁇ 109 (Epicatechin).
  • the ion spray and orifice voltages, temperature, and collision energy were set at -4200 V, -65 V, 500 °C, and -36 V, respectively.
  • the collision gas (nitrogen) was maintained at the medium setting.
  • Data acquisition was conducted using multiple- reaction monitoring with a 75-ms dwell time per transition.
  • polyphenols contained in the cocoa based products of the invention can be divided into three groups:
  • the main catechin is the epicatechin (up to 35% of the total phenolic content), followed by catechin, gallocatechin, epigallocatechin.
  • Anthocyanins are represented essentially by cianidin-3-a-L-arabinoside and cianidin-3-p-D- galactoside.
  • the most represented in the cocoa procyanidins are the flavan-3,4- diols which, through links condense to form dimers, trimers or oligomers with high molecular weight.
  • Cocoa also contains hydroxybenzoic and hydroxycinnamic acids, whose concentrations are influenced by roasting.
  • polyphenols diffuse pigmented cells and oxidize, giving rise to compounds with high molecular weight, largely insoluble.
  • the hydrolysable tannins are essentially made gallotannins.
  • the processing technology of cocoa during the production of chocolate (roasting, grinding, refining, conching, %) affect decreasing the polyphenol content.
  • Blood samples were collected using EDTA-containing Vacutainers (?) at 0 h (before intake) and 1 , 2, and 4 h after the ingestion. Immediately after collection, the blood samples were placed on ice and centrifuged for 10 min at 3000 g at 4 °C. After centrifugation, the plasma was separated into aliquots, spiked with ascorbic acid (final concentration: 1 img/mL), and stored at -80 °C until analysis. Calibration curves
  • Two calibration standards were prepared by adding appropriate amounts of standards stock solutions to plasma. Blank plasma was collected and pooled from healthy volunteers who followed a diet free of polyphenols for 2 days.
  • a volume of 3 mL of blood was taken to the two volunteers 1 , 2 3, and 4 hours after the administration of one gram of cocoa, under the conditions previously described.
  • Acetonitrile, dioxane, n-hexane, methanol, methyl-t-butyl ether HPLC plus grade were from Sigma-Aldrich. Water was treated in a milliQ water purification system (TGI Pure Water Systems, USA). All other chemicals and solvents were of analytical grade and purchased from common sources.
  • Example 5 Process for the preparation of cocoa powder having a polyphenolic high content
  • a preliminary step included harvesting of cocoa pod from blend of cocoa clones of Colombian cocoa plants, gathering of the pods in the field and bean extraction from the pods.
  • the wet cocoa beans obtained from the preliminary step were unfermented beans having a predominant colouration slaty-grey with some beans having a colour prurple violet.
  • the degree of fermentation of the beans was in the range of 1 10 to 130 calculated by applying the cut test in accordance with ISO cut test No. 1 1 14.
  • the wet beans were subjected to a draining step having a duration of around 15 hours.
  • cocoa pods of around 650g each one where obtained around 1 kg of fresh cocoa bean plus pulp containing 0,12 to 0,16 kg of leachates and 0,84 to 086 kg of fresh cocoa beans with a moisture content of around 60% which after draining gave from 0,50 to 0,516 kg of partially dried cocoa beans.
  • the dried cocoa beans were then transported and stored in a factory for further processing.
  • the cocoa bean were cleaned to remove the impurities or extraneous material such as dust particles, metals and nonmetallic byproducts, rocks, stem, cluster bean and other remaining part of the tree.
  • the average weight of the impurity was around 1 % of the starting weight of beans.
  • densimetric table, metal detector, and duty extractors were used densimetric table, metal detector, and duty extractors.
  • the dried beans were subjected to a winnowing treatment to separate the shell from nibs.
  • the cocoa beans are cracked and carry on a vibrating screening of a sieving apparatus and the shell is removed by air action.
  • the sieve of the apparatus had different holes: (i) 8,5 mm, the biggest; (ii) 6,0 mm flow 44%; 4,0 mm flow 30,6%; (iv) 2,2 mm flow 18,1 %; (v) 1 ,0 mm flow 4,9 %.
  • the difference in holes and flow allow to make a classification of nib by size.
  • the range admitted is 0, 3 and 0, 6 % nibs in shells, and 1 ,5 - 1 ,8 % of shell in nibs. In the fine cocoa least 1 mm, they are approximate 1 ,8%.
  • the nibs were subjected to a milling step. After the winnowing process, the nibs ride to the pre-mills where they are ground.
  • the mills was an apparatus provided with a blade, and the nib were passed through sieves and over strong magnets to remove. In this step the nibs are liquefied and became cocoa liquor, for the temperature and fat content (52%).
  • the content of polyphenols (g/kg) was 40 catechins equivalent.
  • the cocoa liquor was store in a big tank for preconditioning at a temperature of 100 -1 10 °C. Aftertaht the mass was pumped to a small tank with a capacity 180-200kg, and the temperature should be1 10 °C. This liquor went to the press.
  • the press pressure was 1 1 ,000 psi with a cycle time between 8 and 12 min ( depending of the fat content).
  • the machine was opened and the final products were:
  • cocoa powder 68 kg with a moisture of 1 ,9%, cocoa butter 20,6 and a polyphenol content g/kg of 68.9 catechins equivalent, flavanol 34 g/kg catechin equivalent
  • the health status of the participants was assessed and they were selected according to the following inclusion criteria: inclusive age 25-50 years, good general health, and body mass index between 22 and 30 kg/m 2 .
  • Table 1 shows the baseline characteristics of the participants. None of the subjects had a history of chronic diseases. Exclusion criteria included individuals who were taking anti-inflammatory drugs, cardiovascular medications, lipid-altering drugs, and hormone replacement therapy. We also excluded individuals engaged in vigorous exercise, vegetarians, and people who routinely took multivitamins or herbal supplements. From the initial 20 subjects enrolled in the study, 18 met the inclusion criteria, and were divided into 3 groups of 6: the first group took 2 tablets (500 mg) of cocoa/day (1 grams of cocoa/day), the second group took four pills/day (2 grams in total) and the last group took 8 pills/day (4 grams total). The samples were collected at baseline, at 2 hours after the first pills ingestion, at 2 weeks and at the end of the intervention period (figure 1 ).
  • OxLDL oxidized LDL

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Abstract

La présente invention concerne un procédé de production d'un produit à base de cacao, en particulier de la poudre de cacao, comprenant un traitement de chauffage aux infrarouges de fèves de cacao non fermentées ou sous-fermentées. La poudre de cacao obtenue peut être formulée sous forme de chocolat ou de produits alimentaires santé à haute teneur en polyphénols.
PCT/IB2016/053277 2016-06-03 2016-06-03 Produits à base de poudre de cacao à haute teneur en polyphénols, utilisations et procédés de fabrication associés WO2017208058A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022096444A1 (fr) * 2020-11-06 2022-05-12 Société des Produits Nestlé S.A. Produit cacaoté et son procédé de préparation

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WO1998009533A1 (fr) * 1996-09-06 1998-03-12 Mars, Incorporated Constituants du cacao, produits comestibles presentant une teneur accrue en polyphenols, leurs procedes de production et utilisations et utilisations medicales
US6207702B1 (en) * 1999-11-17 2001-03-27 Mars, Incorporated Method for reducing postprandial oxidative stress using cocoa procyanidins
EP1346640A1 (fr) * 2002-03-20 2003-09-24 Société des Produits Nestlé S.A. Extrait de cacao à faible teneur en graisses
US6905715B1 (en) * 1996-09-06 2005-06-14 Mars, Incorporated Cocoa solids having a high cocoa procyanidin content
WO2007002851A2 (fr) * 2005-06-29 2007-01-04 Mars, Incorporated Produits a base de cacao thermiquement traites utilises dans l'amelioration de la sante vasculaire
WO2007002883A1 (fr) * 2005-06-29 2007-01-04 Mars, Incorporated Produits polyphenoles
AU2003236474B2 (en) * 1998-03-12 2007-03-08 Mars, Incorporated Food products having enhanced cocoa polyphenol content and processes for producing same
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US6905715B1 (en) * 1996-09-06 2005-06-14 Mars, Incorporated Cocoa solids having a high cocoa procyanidin content
AU2003236474B2 (en) * 1998-03-12 2007-03-08 Mars, Incorporated Food products having enhanced cocoa polyphenol content and processes for producing same
US6207702B1 (en) * 1999-11-17 2001-03-27 Mars, Incorporated Method for reducing postprandial oxidative stress using cocoa procyanidins
EP1346640A1 (fr) * 2002-03-20 2003-09-24 Société des Produits Nestlé S.A. Extrait de cacao à faible teneur en graisses
WO2007002851A2 (fr) * 2005-06-29 2007-01-04 Mars, Incorporated Produits a base de cacao thermiquement traites utilises dans l'amelioration de la sante vasculaire
WO2007002883A1 (fr) * 2005-06-29 2007-01-04 Mars, Incorporated Produits polyphenoles
GB2452972A (en) * 2007-09-21 2009-03-25 Albert Zumbe Chocolate incorporating cryogenically milled cocoa beans
WO2009092606A2 (fr) * 2008-01-25 2009-07-30 Barry Callebaut Ag Composition
WO2009138418A2 (fr) * 2008-05-15 2009-11-19 Barry Callebaut Ag Procédé de traitement de fèves de cacao

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022096444A1 (fr) * 2020-11-06 2022-05-12 Société des Produits Nestlé S.A. Produit cacaoté et son procédé de préparation

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