US20180110252A1 - Preparations with dehydroabietic acid - Google Patents

Preparations with dehydroabietic acid Download PDF

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Publication number
US20180110252A1
US20180110252A1 US15/567,524 US201615567524A US2018110252A1 US 20180110252 A1 US20180110252 A1 US 20180110252A1 US 201615567524 A US201615567524 A US 201615567524A US 2018110252 A1 US2018110252 A1 US 2018110252A1
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Prior art keywords
dehydroabietic acid
preparation
taste
acid
salt
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US15/567,524
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English (en)
Inventor
Karsten Siems
Grit Kluge
Michael Krohn
Katja RIEDEL
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Analyticon Discovery GmbH
BRAIN Biotech AG
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BRAIN Biotechnology Research and Information Network AG
Analyticon Discovery GmbH
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Assigned to B.R.A.I.N. AG, ANALYTICON DISCOVERY GMBH reassignment B.R.A.I.N. AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Riedel, Katja, KLUGE, Grit, KROHN, MICHAEL, SIEMS, KARSTEN
Publication of US20180110252A1 publication Critical patent/US20180110252A1/en
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/40—Tea flavour; Tea oil; Flavouring of tea or tea extract
    • A23F3/405—Flavouring with flavours other than natural tea flavour or tea oil
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2028—Carboxy compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/40—Table salts; Dietetic salt substitutes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/86—Addition of bitterness inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay

Definitions

  • the invention is in the food sector and relates to new preparations containing dehydroabietic acid, substances containing these, processes for taste modulation and corresponding uses of these substances.
  • Teas but also many fruit juice preparations, contain large amounts of flavonoids, specifically catechins and similar flavonoids, and other secondary phytonutrients such as terpenes or polyphenols, which are said to be beneficial for the human health and are therefore certainly desirable as ingredients, but which convey an intensely bitter, astringent and metallic taste, depending on their amount.
  • flavonoids specifically catechins and similar flavonoids
  • other secondary phytonutrients such as terpenes or polyphenols
  • the state of the art sufficiently describes the use of natural substances, specifically of terpene derivatives, to counteract, cover, or change undesired taste properties.
  • the disadvantages of the compositions mentioned are that they require high quantities, and that they only have very specific effects, particularly with respect to synthetic sweeteners and flavonoids.
  • these substances also exhibit a taste of their own which adulterates the desired taste experience, usually with a deteriorating effect.
  • the effectiveness of these active agents strongly depends on the matrix in which they are used. For producers of foods it is, therefore, of great importance to be able to select from a large number of alternative active agents in order to be able to determine the optimal substance for the particular purpose of application.
  • the object of the present invention was, therefore, to provide a natural substance which is capable of covering, neutralising, or advantageously changing unpleasant taste impressions both of sweeteners, specifically of saccharin and acesulfame-K, as well as of secondary phytonutrients such as inorganic salts, flavonoids, polyphenols, alkaloids and terpenes, specifically those which are present in various tea varieties, particularly fruit teas and herbal teas and beverages made of citrus fruit, even when present in very small quantities.
  • sweeteners specifically of saccharin and acesulfame-K
  • secondary phytonutrients such as inorganic salts, flavonoids, polyphenols, alkaloids and terpenes, specifically those which are present in various tea varieties, particularly fruit teas and herbal teas and beverages made of citrus fruit, even when present in very small quantities.
  • a first subject-matter of the invention relates to preparations, comprising or consisting of
  • dehydroabietic acid fully meets the complex profile of requirements described in the beginning. It improves the taste impression in a wide range of different species of both synthetic and natural sweeteners, and also of various tea varieties and other products where unpleasant, bitter, or astringent taste impressions are caused by flavonoids, the alkaloid caffeine and the monoterpene menthol. It is a purely plant-based product which is fully effective also in very small concentrations of, for example, 25 ⁇ M (7.5 mg/l), and which thus proves to be superior to alternative prior-art substances.
  • Taste impressions particularly unpleasant taste impressions which are intended to be improved within the meaning of the invention are understood as bitter and astringent taste sensations, as are other types of tastes which are, for example, described as similar to licorice. The latter are particularly found in the context of the use of stevia extracts.
  • the diterpene dehydroabietic acid (component (a)) is present both in the needles and the bark, root and particularly the resin of many conifers (among others, in the plant families of Pinaceae and Juniperaceae, and here, in particular, in the genera Pinus, Abies, Larix, Juniperus ). It is a byproduct of paper production and contained in what is referred to as tall oil.
  • Dehydroabietic acid has also been isolated from other plant families (e.g., from the genera Illicium, Liquidambar, Styrax, Callicarpa, Rosmarinus, Salvia, Commiphora, Boswellia ). Dehydroabietic acid is most frequently found in resins (e.g., Liquidambar, Styrax, Boswellia, Commiphora, Colophony, but also in amber).
  • the content of dehydroabietic acid in pine resin is mostly below 10%, but it may also be increased to a content of >50%, using a method that is known by the skilled person as disproportionation (e.g., according to the process described by Song et al in JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, 5(4), 535-542 (1985)).
  • dehydroabietic acid Both enantiomers of dehydroabietic acid are known (CAS 1740-19-8 and CAS 6980-63-8).
  • dehydroabietic acid is understood as meaning the isomers and any optional enantiomeric mixtures within the meaning of the present invention.
  • extracts containing dehydroabietic acid as well as the commercially available technical dehydroabietic acid having a purity of about 85% can be used, the use of high-purity products is preferred, which have a content of dehydroabietic acid of at least 90% by weight, preferably at least 95% by weight, and particularly preferably from about 95 to about 99% by weight.
  • high-purity products are obtainable by the typical work-up procedures of preparative organic chemistry so that the skilled person is not required to make an inventive step. In the following, a corresponding process is described, by way of example, in example 1.
  • dehydroabietic acid instead of using dehydroabietic acid itself, it is also possible to use its salts, specifically its alkali and ammonium salts, particularly the sodium salt.
  • the invention also comprises the use of extracts containing dehydroabietic acid, the production of which also forms part of the skilled person's tools, and which is described, by way of example, in example 2 below.
  • these extracts contain at least 20% by weight, more preferably at least 30% by weight, and particularly preferably from about 40 to about 60% by weight dehydroabietic acid.
  • Suitable sweeteners or sweet-tasting additives forming group (b) are, firstly, carbohydrates such as, for example, trehalose, lactose, maltose, melizitose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D-mannose, D-tagatose, D-arabinose, L-arabinose, D-ribose, D-glyceraldehyde or maltodextrin.
  • carbohydrates such as, for example, trehalose, lactose, maltose, melizitose, raffinose, palatinose, lactulose, D-fructose, D-glucose, D-galactose, L-rhamnose, D-sorbose, D-mannose, D-tagatose, D-ar
  • Plant-based preparations containing these substances are also suitable, for example, on the basis of sugarbeet ( Beta vulgaris ssp., sugar fractions, sugar syrup, molasses), sugar cane ( Saccharum officinarum ssp., molasses, sugar cane syrup), maple syrup ( Acer ssp.) or agave (agave syrup).
  • sugarbeet Beta vulgaris ssp., sugar fractions, sugar syrup, molasses
  • sugar cane Saccharum officinarum ssp., molasses, sugar cane syrup
  • maple syrup Acer ssp.
  • agave syrup agave syrup
  • Suitable are also synthetic, i.e. usually enzymatically produced starch or sugar hydrolysates (invert sugar, fructose syrup) as well as natural or synthetic sweet-tasting substances, such as
  • the sweeteners may also be plant extracts, as is described by way of example in the following.
  • Rebaudiosides are among the steviosides, which are the main components of the plant Stevia rebaudiana, which is also referred to as sweet weed or honey weed.
  • 10% of the dry matter of the leaves are constituted by the diterpene glycoside stevioside, followed by rebaudioside A (2 to 4% by weight) as well as by more than ten other steviol glycosides such as dulcoside.
  • rebaudiosides and stevia extracts for use as sweeteners; a daily uptake of up to 4 mg stevioside per kilogramme of bodyweight is considered harmless.
  • individual rebaudiosides or the extracts of the stevia plant may be used.
  • the substance mixtures according to the invention may contain components (a) and (b) in a weight ratio from about 1:99 to about 99:1, preferably from about 25:75 to about 75:25, and particularly preferably from about 40:60 to about 60:40.
  • dihydrochalcones represent flavonoids, in which particularly the two representatives naringenin dihydrochalcone and neohesperidin dihydrochalcone must be highlighted, which are known as synthetic sweeteners:
  • mogrosides A group of cucurbitane glycosides is referred to as mogrosides, which are known as a component of the natural sweetener Luo Han Guo. Mogroside-V, which is 400 times sweeter than sugar, is highlighted herein.
  • suitable sweeteners also include extracts of the plants which are selected from the group consisting of Rubus allegheniensis, Rubus arcticu, Rubus strigosus, Rubus armeniacus, Rubus caesius, Rubus chamaemorus, Rubus corylifolius agg., Rubus fruticosus agg., Rubus geoides, Rubus glaucus, Rubus gunnianus, Rubus idaeus, Rubus illecebrosus, Rubus laciniatus, Rubus leucodermis, Rubus loganobaccus, Rubus loxensis, Rubus nepalensis, Rubus nessensis, Rubus nivalis, Rubus odoratus, Rubus pentalobus, Rubus phoenicolasius, Rubus saxatilis, Rubus setchuenensis, Rubus spectabilis and Rubus ulmifolius and their mixtures. These are
  • a further active agent in this group is glycyrrhetinic acid, or a corresponding salt, or an extract containing this substance.
  • the acid itself its salts—for example, sodium, potassium, or ammonium salt—or the extracts of the plant Glycyrrhiza glabra.
  • Mono ammonium glycyrrhizinate is particularly preferred.
  • Preferred sweeteners are selected from the group consisting of saccharin, acesulfame-K, steviol glycosides, particularly rebaudioside A, and stevia extracts.
  • the flavonoids forming component (1b) are mostly catechins, which are mainly contained in tea in varying quantities and compositions, and which are among the most powerful bitter principles.
  • catechins which are mainly contained in tea in varying quantities and compositions, and which are among the most powerful bitter principles.
  • the most important representatives are:
  • the alkaloid caffeine contributes to the bitter taste of green and black tea.
  • the bitter or astringent taste is mainly caused by polymethoxylated flavones such as sinensetin and nobiletin, glycosylated flavonoids, e.g., naringin, and by terpenes of the limonoid type, e.g., limonene.
  • Magnesium is an important mineral substance. Under-supply with magnesium is often not diagnosed, but it may appear as a side effect in many diseases (e.g., diabetes, hypertension). Senior citizens and pregnant women frequently have an increased demand for magnesium. An increased demand for magnesium may be balanced by mineral supplements or by adding magnesium to foods, e.g., bread that is specifically produced for senior citizens. Magnesium may be taken in the form of various salts, e.g., as magnesium chloride or magnesium sulfate. Magnesium-containing salts taste bitter, particularly magnesium sulfate, which is also referred to as epsomite.
  • Potassium is also added to foods, but usually not with the intention to balance a potassium deficiency, but as a substitute for salt in order to reduce the sodium content in foods while maintaining the taste of salt.
  • potassium chloride has a bitter taste, only part of the sodium may be substituted by potassium.
  • ascorbic acid, fumaric acid and citric acid, or various sugars (lactose, dextrose), or yeast extract may be added (cf. DE3035518C2).
  • these solutions are only suitable for some foods, as they are not neutral with regard to their taste or may lead to an increased uptake of calories, which is not desired in sodium-chloride reduced foods which are, therefore, healthier.
  • Preparations of the present invention may contain components (a), based on component (b), in concentrations of about 1 to about 500 ⁇ M, preferably, about 10 to about 250 ⁇ M, particularly preferably, about 20 to about 100 ⁇ M.
  • a form of preparation which is intended for commercial distribution and which is particularly suitable, for example, in form of a sweetener tablet typically contains 1 to 40 mg sweetener(s), e.g., saccharin or acesulfame-K, and 1 to 30 mg dehydroabietic acid, based on a total weight of the tablet of 60 mg where the difference in quantity is represented by tableting additives, particularly binders.
  • sweetener(s) e.g., saccharin or acesulfame-K
  • dehydroabietic acid based on a total weight of the tablet of 60 mg where the difference in quantity is represented by tableting additives, particularly binders.
  • One of these tablets corresponds to the sweetening power of one sugar cube and is completely sufficient to sweeten, for example, a common cup of tea, completely masking the unpleasant taste that is linked with the addition of a sweetener in the process.
  • a further subject-matter of the present invention relates to foods which contain the preparations according to the invention.
  • the components individually or together, where the addition of the mixture is preferred.
  • component (a) can be used alone or as a mixture of (a) and (b).
  • Examples for foods comprise baked goods, e.g. bread, dry biscuits, cakes, other baked products, confectionery (e.g. chocolates, chocolate bar products, other bar products, fruit gum, hard and soft caramels, chewing gum), alcoholic or nonalcoholic beverages (for example, coffee, tea, iced tea, wine, wine-containing beverages, beer, beer-containing beverages, liqueurs, schnapps, brandies, fruit-containing (carbonated) beverages, isotonic (carbonated) beverages, refreshing (carbonated) beverages, nectars, spritzers, fruit and vegetable juices, fruit or vegetable juice formulations), instant beverages (for example, instant cocoa beverages, instant tea beverages, instant coffee beverages, instant fruit beverages), meat products (for example, ham, fresh sausage or uncooked sausage formulations, seasoned or marinated fresh or salted meat products), eggs or egg products (dried egg, egg white, egg yolk), cereal products (for example, breakfast cereals, muesli bars, precooked ready-made rice products), dairy products (for example, milk beverages, butter
  • soft drinks or hot drinks or instant drinks such as, for example, teas or fruit juices.
  • a further subject-matter of the invention also relates to pharmaceutical preparations, containing the preparations according to the invention. Also in this case, it is preferred to add component (a) and (b) as a mixture.
  • the pharmaceutical preparations are liquid products, particularly cough syrup, antipyretic agents, or antibiotics. Liquid forms of medication are particularly used in children and where the masking of the bitter taste of the active agent is technologically impossible, for example, when applying capsules, tablets or other solid forms of pharmaceuticals.
  • Both the foods and the pharmaceutical preparations may contain dehydroabietic acid or a salt of dehydroabietic acid in concentrations from about 1 to about 500 ⁇ M, preferably, about 10 to about 250 ⁇ M, particularly preferably about 20 to about 100 ⁇ M.
  • a further subject-matter of the invention relates to a process for masking unpleasant taste impressions of sweeteners and/or flavonoids and/or terpenes and/or alkaloids and/or mineral salts as well as foods or pharmaceutical preparations containing these substances, characterised in that a quantity of a dehydroabietic acid, a salt of dehydroabietic acid and/or an extract containing dehydroabietic acid is added to them.
  • dehydroabietic acid a salt of dehydroabietic acid and/or an extract containing dehydroabietic acid is added in quantities such that the concentration of dehydroabietic acid in the product is from about 1 to about 500 ⁇ M, preferably about 10 to about 250 ⁇ M, more preferably about 20 to about 150 ⁇ M and particularly preferably about 50 to about 100 ⁇ M.
  • dehydroabietic acid a salt of dehydroabietic acid and/or an extract of dehydroabietic acid is also claimed for masking unpleasant taste impressions of sweeteners and/or flavonoids and/or terpenes and/or alkaloids and/or mineral salts as well as foods or pharmaceutical preparations containing these substances, in the process of which dehydroabietic acid, a salt of dehydroabietic acid and/or an extract containing dehydroabietic acid is added to these such that the concentration of dehydroabietic acid in the product is from about 1 to about 500 ⁇ M, preferably about 10 to about 250 ⁇ M, particularly preferably about 20 to about 100 ⁇ M.
  • Human bitter receptor cells were established, and the activation of these cells was quantified in order to detect, by means of a cell-based test system, natural substances which reduce the bitterness of bitter principles.
  • the change of the intracellular potassium level was measured for quantitation of the activation of bitter receptor cells.
  • a human bitter receptor cell line having endogeneous bitter receptors was used for a screening for antagonists in a high-throughput format.
  • the modulation of the intracellular potassium level of the bitter receptor cells was quantitated by means of the potassium-sensitive fluorescence dye Fluo-4 AM in a microplate reader.
  • the activation of the bitter receptor cells by an agonist leads to an increase of the intracellular potassium level.
  • the quantity of mobilised calcium may be quantitated by means of fluorescence, which increases in proportion with the concentration of calcium. In case of inhibition by an antagonist, the quantity of mobilised calcium is significantly lower, as is the change of fluorescence induced by an agonist.
  • the mobilisation of calcium was quantitated as the change of fluorescence (dF) after the addition of the substance, taking into account the basal fluorescence (F0) as dF/F0.
  • the relative fluorescence units (dF/F0) measured after stimulation with agonist and antagonist, were compared with the sole stimulation by the agonist (positive control). In doing so, active substances that are lowering the calcium level were identified. Potential antagonists were repeatedly tested for their activity. Data processing and analysis was performed with a software program of the microplate reader (SoftMax®Pro Software, Molecular Devices).
  • IC50 average inhibitory concentration
  • human bitter taste receptors were stimulated with 0.1-25 ⁇ M of the substance in the presence of the agonist.
  • a representative dose-effect relationship is illustrated in FIG. 1 . It indicates the dose-effect relationship of dehydroabietic acid (BRA-C-0000131) in human taste cells when stimulated with 1 mM saccharin (fluorometric detection) IC50 1.7+/ ⁇ 0.5 ⁇ M.
  • the sensory evaluation of the samples was performed by a panel of five experienced assessors. The sensory tests were performed descriptively, randomized, blinded, and by means of a “sip and spit” method. To this end, the sample is moved within the mouth for a few seconds to evaluate its taste, and it is not swallowed but expectorated. The results may be taken from the following Table 2a:

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US15/567,524 2015-04-22 2016-04-16 Preparations with dehydroabietic acid Abandoned US20180110252A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EPPCT/EP2015/058741 2015-04-22
EP2015058741 2015-04-22
EP15166154.3A EP3085248B1 (fr) 2015-04-22 2015-05-03 Compositions contenant acide dehydro abietique
EP15166154.3 2015-05-03
PCT/EP2016/058472 WO2016169869A1 (fr) 2015-04-22 2016-04-16 Préparations avec acide déhydroabiétique

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EP3085248B1 (fr) 2020-07-01
WO2016169869A1 (fr) 2016-10-27
US20190364945A1 (en) 2019-12-05
JP2018512870A (ja) 2018-05-24
US10653173B2 (en) 2020-05-19

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