Masking preparations and compounds from daemonorops draco (dragon blood)

Abstract

The present invention primarily relates to a use of a compound according to formula (I) or a mixture comprising a compound according to formula (I) for reducing, modifying and / or masking a bitter taste impression of one or more bitter tasting substances. The invention furthermore relates to an extract comprising a compound as defined above and to a food or feed composition comprising one or more bitter tasting substances and a compound as defined above.

Description

[0001] Masking preparations and compounds from Daemonorops draco (Dragon Blood)

[0002] The present invention primarily relates to a use of a compound according to formula (I) or a mixture comprising a compound according to formula (I) for reducing, modifying and / or masking a bitter taste impression of one or more bitter tasting substances. The invention furthermore relates to an extract comprising a compound according to formula (I) and to a food or feed composition comprising one or more bitter tasting substances and a compound according to formula (I) or an extract according to the present invention.

[0003] Further aspects of the present invention will arise from the description below, in particular from the examples, as well as from the attached patent claims.

[0004] Bitter taste is in general an unpleasant taste perception. Nevertheless, bitter tasting substances are known to elicit pleasant effects on the human organism, especially on physiological processes. Bitter substances act agonistic on bitter taste receptors (TAS2Rs), whereby bitter-masking substances antagonise TAS2Rs. In the oral cavity TAS2Rs are known for the detection of bitter tasting substances in food and other stimuli from the environment.

[0005] In research, the identification of new agonists and antagonists is a very topical target, pursued by the food industry and also by the pharmaceutical industry focussing on new substances which can be used as an alternative to treat diseases in the airway system and the digestive system. The big advantage of bitter masking substances acting as GPCR or TAS2R (a nt-) agonists is that they can reduce the bitter taste of the pharmaceuticals and with that also the unwanted side effects of the pharmaceuticals. Therefore, it is important to provide substances that can reduce the bitter taste of a substance in a mixture or preparation. Preferably, such substances are obtainable based on natural resources (e.g. plants). In general, the bitter taste perception is mediated via bitter taste receptors, the TAS2Rs, which are G-protein coupled receptors (GPCR) occurring in taste buds on the tongue in the oral cavity, mediating the receptor activation via nerve pathway to the brain, whereby the taste sensation bitter is recognized. So far, 26 different TAS2Rs are known, which are distinguished into three different groups, the broadly tuned, the narrowly tuned and the intermediate ones. TAS2R14 is a broadly tuned receptor, on which quinine, caffeine, and quercetin are acting agonistic among many others. Bitter maskers as 6-methoxyflavanone or 3’,6-dimethoxyflavanon, both phenolic compounds, have antagonistic properties on TAS2R14.

[0006] The primary object of the present invention was to provide a compound suitable for masking bitter taste impressions in mixtures, extracts or food / feed compositions, preferably for masking the bitter taste impression of quinine and / or proteins or protein comprising products. Furthermore, it was an object of the present invention to provide a compound which is cost-effective, easily available, and of biological origin. Another object of the present invention was to improve the quality of protein preparations, preferably for alternative protein products.

[0007] Further objects underlying the present invention follow from the description below and the present patent claims.

[0008] According to a first aspect of the present invention, the stated object is achieved by a use of a compound according to formula (I) or a mixture comprising a compound according to formula (I) for reducing, modifying and / or masking a bitter taste impression of one or more bitter tasting substances. Surprisingly it was found that the compound according to formula (I) is suitable for reducing, modifying and / or masking a bitter taste impression of one or more bitter tasting substances. Furthermore, in the context of the own studies underlying the present invention, it was found that among the various isolated fractions and substances from the extract of the resin of the plant Daemonorops draco, the compound according to formula (I) and extracts containing a compound according to formula (I) are particularly advantageous for the purpose as defined above.

[0009] For the investigation of potentially bitter masking-properties of a specific compound of a plant, usually extracts are fractioned via chromatographic methods and then applied in subsequent sensory analysis and cell-based assays. In the context of the present invention, extracts of, inter alia, the plant Daemonorops draco were investigated in the above mentioned manner. Various fractions have been obtained and several substances have been isolated from an extract of the resin of the plant Daemonorops draco, which is also known as Dragon Blood.

[0010] The phytochemistry of Damaenerops draco was described in various publications (Novel Flavonoids in Dragon's Blood of Daemonorops draco, K.-l. Nakashima, N. Abe, F. Kamiya, T. Ito, M. Oyama and M. linuma, Helv. Chim. Acta 2009 Vol. 92 Issue 10 Pages 1999-2008; DRAGON'S BLOOD FROM DRACACENAE DRACO, STRUCTURE OF NOVEL HOMOISOFLA VANOIDS, L. Camarda, L. Merlini and G. Nasini, Heterocycles 1983 Vol. 20 Issue 1 Pages 39-43; Retro-dihydrochalcones from the resin of Daemonorops draco and their inhibitory activities against renal fibrosis, B.-L. Zhang, C.-T. Tao, L.-S. Zhang and Y.- X. Cheng Fitoterapia 2023 Vol. 168 Pages 105515 DOI: https: / / doi.Org / 10.1016 / j.fitote.2023.105515).

[0011] The well-established HGT-1 cell system was used to identify the cellular bitter response of extracts, fractions and substances. Hereby, a low IPX value is associated with bitter tasting substances, and a high IPX value is correlating with a less intense bitter taste. (Liszt, K. I.; Ley, J. P.; Lieder, B.; Behrens, M.; Stoger, V.; Reiner, A.; Hochkogler, C. M.; Kock, E.; Marchiori, A.; Hans, J.; et al. Caffeine induces gastric acid secretion via bitter taste signaling in gastric parietal cells. Proc Natl Acad Sci U SA 2017, 114 (30), E6260-E6269. DOI: 10.1073 / pnas.1703728114.) Moreover, this cell line was modified via a CRISPR-Cas9 knock-out approach. According to a preferred embodiment of the present invention, the mixture is an extract, preferably wherein the extract is an extract as defined herein below or, respectively, in the patent claims.

[0012] A preferred embodiment of the present invention is a use as defined above, wherein the bitter tasting substance(s) is / are selected from the group consisting of TAS2R receptor modulating substances, preferably TAS2R1 , TAS2R4, TAS2R3, TAS2R5, TAS2R7, TAS2R8, TAS2R9, TAS2R10, TAS2R13, TAS2R14, TAS2R16, TAS2R38, TAS2R39, TAS2R40, TAS2R41 , TAS2R42, TAS2R43, TAS2R44, TAS2R45, TAS2R46, TAS2R47, TAS2R48, TAS2R49, TAS2R50, and / or TAS2R60, more preferably TAS2R4, TAS2R7, TAS2R10, TAS2R14, TAS2R39, TAS2R40, TAS2R43, TAS2R44, and / or TAS2R46, receptor modulating substances.

[0013] Surprisingly, inter alia, the involvement of the TAS2R14 receptor in the cellular bitter response experiments was shown.

[0014] The use of a compound as defined above is particularly advantageous as preferably more than one receptor can be modulated by the TAS2R receptor modulating substances.

[0015] The TAS2R modulating substances are preferably able to modulate one or more TAS2R receptors. In the context of the present invention, modulating preferably is to be understood as activating. Furthermore, the receptors preferably relate to human TAS2R receptors and / or relate to homologues that actually occur in the species.

[0016] A preferred embodiment of the present invention is a use as defined above, wherein the bitter tasting substance(s) is / are selected from the group consisting of flavonoid(s), preferably naringin, neohesperidin, quercitrin, quercetin glycosides, kaempferol glycosides, kaempferol glycosidester(s), preferably kempferol 3-0-(2"'-0-sinapoyl-beta-sophoroside), hydroxy fatty acid(s), saponin(s), preferably soysaponins, glycoalkaloid(s), preferably solanin, bitter amino acid(s), preferably L-leucine, L-isoleucine, L-valin, L-phenylalanine, L- arginine, L-tryptophane, bitter peptide(s), quinine, caffeine, humulone isomere, cucurbita- cin E, absinthin, acesulfame K, acetaminophen, acetylthiourea, aloin, allylisothiocyanate, amarogentin, D-amygdalin, andrographolide, arborescin, arbutin, arglabin, aristolochic acid, artemorin, azathioprine, benzamide, benzoin, brucine, campher, caprolactam, carisoprodol, cascarillin, chloramphenicol, chlorhexidine, chlorpheniramine, chloroquine, cnicin, colchicine, coumarin, crispolide, cromolyn, cucurbitacin B, cycloheximid, dapsone, denatonium benzoate, dextromethorphan, dimethylformamide, diphenylhydramine, diphenidol, diphenylthiourea, divinylsulfoxid, erythromycin, ethylpyrazine, N-ethylthiourea, N,N’- ethylene thiourea, falcarindiol, famotidine, flufenamic acid, grossheimin, haloperidol, helicin, hydrocortisone, 4-hydroxyanisol, limonin, methimazole, 4(6)-methyl-2-thiouracil, methylthiourea, noscapine, orphenadrine, papaverine, parthenolide, picrotoxinin, 1 ,10- phenanthroline, phenylethyl isothiocyanate, PTC, PROP, quassin, saccharin, D-salicin, si- nigrin, sodium benzoate, sodium cyclamate, sodium thiocyanate, strychnine, tatridin B, thiamine, thujon (-)-a, and yohimbine.

[0017] The use of a compound as defined above is particularly advantageous as preferably the bitterness of a broad range of various bitter substances can be reduced, modified, and / or masked.

[0018] A preferred embodiment of the present invention is a use as defined above, wherein the bitter taste impression of proteins and / or protein comprising products is reduced, modified and / or masked.

[0019] The use of a compound as defined above is particularly advantageous for reducing, modifying and / or masking a bitter taste impression of proteins.

[0020] Protein is preferably to be understood as native protein or protein mixture prepared or isolated from a natural source or processed product from such a native protein or protein mixture including partial or full hydrolysis. Therefore, protein in the context of this publication is preferably also to be understood such that it can also contain bitter concomitant or non-covalently bound secondary metabolites from the source, peptides and / or amino acids from nonenzymatic or enzymatic partial or full hydrolysis.

[0021] A preferred embodiment of the present invention is a use as defined above, wherein the bitter taste impression of quinine and / or quinine comprising products is reduced, modified and / or masked.

[0022] The use of a compound as defined above is particularly advantageous for reducing, modifying and / or masking a bitter taste impression of quinine.

[0023] According to a second aspect of the present invention, the stated object is achieved by an extract comprising a compound according to formula (I) wherein the amount of the compound according to formula (I) in the extract is sufficient for reducing, modifying and / or masking a bitter taste impression, of a or, respectively, one or more bitter tasting substance(s), and / or wherein the amount is in a range of from 0.5 to 80 wt.%, preferably in a range of from 1 to 65 wt.%, in each case based on the total amount of the extract.

[0024] According to a preferred embodiment of the present invention an extract as defined above, wherein the compound according to formula (I) is present in a total amount sufficient to reduce the degree of bitterness at least by 10 %, preferably 15 %, preferably with a level of significance of 0.05 %, in comparison to a corresponding extract without a compound according to formula (I), is particularly preferred.

[0025] Typically, bitterness can be determined by using various test concentrations of a bitter compound, e.g. quinine (2, 4, 6, 8, 10, and 12 mg / kg water) or caffeine (300, 400, 500, 600, 700, and 800 mg / kg water). Panellists are rating the bitterness on an unstructured scale of 1 - 100 %. Typically, panellists are rating 10 mg / kg quinine at about 50 + / -10 % of the scale. Similar results are obtained for 500 mg / kg caffeine.

[0026] A preferred embodiment of the present invention is an extract as defined above, wherein the bitter tasting substance(s) is / are selected from the group consisting of TAS2R receptor modulating substances, preferably TAS2R1 , TAS2R4, TAS2R3, TAS2R5, TAS2R7, TAS2R8, TAS2R9, TAS2R10, TAS2R13, TAS2R14, TAS2R16, TAS2R38, TAS2R39, TAS2R40, TAS2R41 , TAS2R42, TAS2R43, TAS2R44, TAS2R45, TAS2R46, TAS2R47, TAS2R48, TAS2R49, TAS2R50, and / or TAS2R60, more preferably TAS2R4, TAS2R7, TAS2R10, TAS2R14, TAS2R39, TAS2R40, TAS2R43, TAS2R44, and / or TAS2R46, receptor modulating substances.

[0027] The extract as defined above is particularly advantageous as preferably more than one receptor can be modulated by the TAS2R receptor modulating substances. A preferred embodiment of the present invention is an extract as defined above, wherein the bitter tasting substance(s) is / are selected from the group consisting of flavonoid(s), preferably naringin, neohesperidin, quercitrin, quercetin glycosides, kaempferol glycosides, kaempferol glycosidester(s), preferably kempferol 3-0-(2"'-0-sinapoyl-beta-sophoroside), hydroxy fatty acid(s), saponin(s), preferably soysaponins, glycoalkaloid(s), preferably solanin, bitter amino acid(s), preferably L-leucine, L-isoleucine, L-valin, L-phenylalanine, L- arginine, L-tryptophane, bitter peptide(s), quinine, caffeine, humulone isomere, cucurbita- cin E, absinthin, acesulfame K, acetaminophen, acetylthiourea, aloin, allylisothiocyanate, amarogentin, D-amygdalin, andrographolide, arborescin, arbutin, arglabin, aristolochic acid, artemorin, azathioprine, benzamide, benzoin, brucine, campher, caprolactam, carisoprodol, cascarillin, chloramphenicol, chlorhexidine, chlorpheniramine, chloroquine, cnicin, colchicine, coumarin, crispolide, cromolyn, cucurbitacin B, cycloheximid, dapsone, denatonium benzoate, dextromethorphan, dimethylformamide, diphenylhydramine, diphenidol, diphenylthiourea, divinylsulfoxid, erythromycin, ethylpyrazine, N-ethylthiourea, N,N’- ethylene thiourea, falcarindiol, famotidine, flufenamic acid, grossheimin, haloperidol, helicin, hydrocortisone, 4-hydroxyanisol, limonin, methimazole, 4(6)-methyl-2-thiouracil, methylthiourea, noscapine, orphenadrine, papaverine, parthenolide, picrotoxinin, 1 ,10- phenanthroline, phenylethyl isothiocyanate, PTC, PROP, quassin, saccharin, D-salicin, si- nigrin, sodium benzoate, sodium cyclamate, sodium thiocyanate, strychnine, tatridin B, thiamine, thujon (-)-a, and yohimbine.

[0028] The extract as defined above is particularly advantageous as preferably the bitterness of a broad range of various bitter substances can be reduced, modified, and / or masked.

[0029] A preferred embodiment of the present invention is an extract as defined above, wherein the amount of the compound according to formula (I) in the extract is sufficient for reducing, modifying and / or masking the bitter taste impression of proteins and / or protein comprising products.

[0030] The extract as defined above is advantageous, since particularly bitter taste impression(s) of proteins is reduced, modified and / or masked.

[0031] A preferred embodiment of the present invention is an extract as defined above, wherein the amount of the compound according to formula (I) in the extract is sufficient for reducing, modifying and / or masking the bitter taste impression of quinine and / or quinine comprising products. The extract as defined above is advantageous, since particularly a bitter taste impression of quinine is reduced, modified and / or masked.

[0032] A preferred embodiment of the present invention is an extract as defined above, wherein the extract is an extract of the plant Daemonorops draco, preferably an extract of the resin of the plant Daemonorops draco.

[0033] Preferred is an extract as defined above, wherein the extract is a crude extract prepared with ethanol (absolute ethanol 100 % or azeotropic ethanol 96 % or diluted ethanol 70 up to 95 %) or with ethyl acetate and, preferably, wherein the resin is treated with hexane or another unipolar solvent (e.g. pentane, but also liquid or supercritical propane, butane or CO2) prior to the extraction in order to remove lipophilic compounds such as fats and, preferably, wherein the crude extract is dried and furthermore separated or enriched, preferably by liquid-solid or liquid-liquid chromatographic methods, more preferably with liquid-solid reversed phase chromatography using usual solvent systems, preferably water, ethanol, methanol, acetonitrile, ethyl acetate, aceton, methyl-tert-butyl ether, formic acid, acetic acid, buffer salts and, preferably, wherein a secondary enriched or purified extract can be again dried and, optionally, wherein the extracts can be recrystallized at every stage.

[0034] An extract as defined above, preferably as obtained above, is advantageous, since extracts of the plant Daemonorops draco have particularly suitable properties to reduce, modify and / or mask bitter taste impression(s) in the sense of the present invention.

[0035] According to another aspect of the present invention, the stated object is achieved by a food or feed composition comprising one or more bitter tasting substances and a compound according to formula (I) or a mixture, preferably an extract as defined above, comprising a compound according to formula (I) wherein the amount of the compound according to formula (I) in the food or feed composition is sufficient for reducing, modifying and / or masking a bitter taste impression, of a or, respectively, one or more bitter tasting substance(s), and / or wherein the amount is in a range of from 5 to 250 mg / kg, more preferably in a range of from 25 to 150 mg / kg, based on the total amount of the composition.

[0036] According to a preferred embodiment of the present invention a composition as defined above, wherein the compound according to formula (I) is present in a total amount sufficient to reduce the degree of bitterness at least by 10 %, preferably 15 %, preferably with a level of significance of 0.05 %, in comparison to a corresponding composition without a compound according to formula (I), is particularly preferred.

[0037] A preferred embodiment of the present invention is a composition as defined above, wherein a or, respectively, the bitter tasting substance(s) is / are selected from the group consisting of TAS2R receptor modulating substances, preferably TAS2R1 , TAS2R4, TAS2R3, TAS2R5, TAS2R7, TAS2R8, TAS2R9, TAS2R10, TAS2R13, TAS2R14, TAS2R16, TAS2R38, TAS2R39, TAS2R40, TAS2R41 , TAS2R42, TAS2R43, TAS2R44, TAS2R45, TAS2R46, TAS2R47, TAS2R48, TAS2R49, TAS2R50, and / or TAS2R60, more preferably TAS2R4, TAS2R7, TAS2R10, TAS2R14, TAS2R39, TAS2R40, TAS2R43, TAS2R44, and / or TAS2R46, receptor modulating substances.

[0038] The composition as defined above is particularly advantageous as preferably more than one receptor can be modulated by the TAS2R receptor modulating substances.

[0039] A preferred embodiment of the present invention is a composition as defined above, wherein the bitter tasting substance(s) is / are selected from the group consisting of flavonoid^), preferably naringin, neohesperidin, quercitrin, quercetin glycosides, kaempferol glycosides, kaempferol glycosidester(s), preferably kempferol 3-0-(2"'-0-sinapoyl-beta- sophoroside), hydroxy fatty acid(s), saponin(s), preferably soysaponins, glycoalkaloid(s), preferably solanin, bitter amino acid(s), preferably L-leucine, L-isoleucine, L-valin, L-phe- nylalanine, L-arginine, L-tryptophane, bitter peptide(s), quinine, caffeine, humulone iso- mere, cucurbitacin E, absinthin, acesulfame K, acetaminophen, acetylthiourea, aloin, allylisothiocyanate, amarogentin, D-amygdalin, andrographolide, arborescin, arbutin, arglabin, aristolochic acid, artemorin, azathioprine, benzamide, benzoin, brucine, campher, caprolactam, carisoprodol, cascarillin, chloramphenicol, chlorhexidine, chlorpheniramine, chloroquine, cnicin, colchicine, coumarin, crispolide, cromolyn, cucurbitacin B, cycloheximid, dapsone, denatonium benzoate, dextromethorphan, dimethylformamide, diphenylhydramine, diphenidol, diphenylthiourea, divinylsulfoxid, erythromycin, ethylpyrazine, N-ethylthi- ourea, N,N’-ethylene thiourea, falcarindiol, famotidine, flufenamic acid, grossheimin, haloperidol, helicin, hydrocortisone, 4-hydroxyanisol, limonin, methimazole, 4(6)-methyl-2- thiouracil, methylthiourea, noscapine, orphenadrine, papaverine, parthenolide, picrotoxinin, 1 ,10-phenanthroline, phenylethyl isothiocyanate, PTC, PROP, quassin, saccharin, D- salicin, sinigrin, sodium benzoate, sodium cyclamate, sodium thiocyanate, strychnine, ta- tridin B, thiamine, thujon (-)-a, and yohimbine.

[0040] The composition as defined above is particularly advantageous as preferably the bitterness of a broad range of various bitter substances is reduced, modified, and / or masked.

[0041] A preferred embodiment of the present invention is a composition as defined above, wherein the composition is a protein comprising product and / or a quinine containing product, preferably, wherein the protein is selected from the group consisting of proteins from whey, soy, pea, faba bean, lentil, canola, lupine, potato, wheat, chickpea, quinoa, mil- let / shorgum, beans, other legumes, algae, fungi, yeasts, and bacteria.

[0042] The composition as defined above is advantageous, since particularly bitter taste impression^) of proteins and / or quinine is reduced, modified and / or masked.

[0043] According to another aspect of the present invention, the stated object is achieved by a method of producing a bitterness reduced product comprising a compound according to formula (I)

[0044] (I), preferably a compound as defined above, or an extract comprising a compound according to formula (I) preferably an extract as defined above, or a composition comprising a compound according to formula (I) preferably a composition as defined above, comprising the following steps:

[0045] (a) providing a compound according to formula (I), a mixture (e.g. extract) or, re- spectively, a composition, as defined above,

[0046] (b) adding the component provided in step (a) to a product, the bitterness of which is to be reduced, preferably in an amount sufficient for reducing, modifying and / or masking a bitter taste impression, of a or, respectively, one or more bitter tasting substance(s) in the product. Preferably, such a method additionally comprises the step of assessing a suitable amount of component (a) for the purpose of the present invention, i.e., for reducing, modifying and / or masking a bitter taste impression, of a or, respectively, one or more bitter tasting substance(s) in the product, before adding component (a) to the product. Further preferred embodiments of such a method become apparent in view of the above described preferred embodiments in connection with the other aspects of the present invention.

[0047] The invention will now be described in more detail hereinafter with references to the examples. Further aspects of the present invention are disclosed in the accompanying claims.

[0048] Description of the Figures:

[0049] Figure 1 shows the impact of quinine [10 ppm] and ethyl acetate extract of Daemonorops draco (DD) [100 ppm] on proton secretion in HGT-1 wild-type cells. The significance was tested with Student’s t-test, **** ... p < 0.001. Quinine [10 ppm] induced proton secretion (p < 0.05) compared to control treated cells (KRHB). Data shown as mean ± SEM, n=4, t.r.= 4-6. AUC was calculated from Intracellular Proton Index (IPX) and compared to quinine treated cells (C (control) = 0.00).

[0050] Figure 2 shows the impact of quinine [10 ppm] and compound according to formula (I) (DMDHE) [100 ppm] on proton secretion in HGT-1 wild-type (wf) cells and TAS2R14 knockout cells. Both incubations are significant different to the control treated cells, tested by ANOVA, moreover significant differences between the incubations are indicated by (*) (p < 0.05). Data shown as mean ± SEM, n=3, t.r.=4-6. AUC was calculated from Intracellular Proton Index (IPX) and compared to control (= Quinine).

[0051] Examples to formula (I) from

[0052] The resinous secretion of the fruit of Daemonorops draco was solubilized in pure ethanol and filtrated to remove particles. Ethanol was removed and the resin was solubilized in dichloromethane, loaded onto a solid phase material and consecutively eluted with n-hex- ane, ethyl acetate (Ethyl acetate extract of Daemonorops draco) and finally with ethanol 95% (Ethanol extract of Daemonorops draco).

[0053] Preparative column chromatography of ethyl acetate extract of Daemonorops draco: Preparative column chromatography of 2.5 g ethyl acetate extract of Daemonorops draco dissolved in 2 g methanol was performed on a C18 5 pm 100 A 250x21 .2 mm (Luna, AXIA Pack First, Phenomenex) column using a HPLC system (P2.1 L, Knauer) with column oven at 20°C (Jetstream), fraction collector (Foxy R1) and UV detector (S2600, Knauer). The column was loaded with 250 pL sample volume and separation was performed using a water / acetonitrile gradient 60 / 40 for 2 minutes then to 35 / 65 over 18 minutes, afterwards to 30 / 70 over 25 minutes and finally to 5 / 95 over 28 minutes. Acetonitrile was removed by rotary evaporation and the remaining aqueous phase was freeze dried. Subfractionation has been performed with the same system equipped with a silica 5 pm 100 A 250x21 .2 mm (Luna, AXIA, Phenomenex) column using a hexane / ethyl acetate gradient: hexane concentration was decreased within 18 minutes from 55% to 50%, further decreased to 40% within another ? minutes, further decreased to 5% within another 3 minutes and hold for 6 minutes at 5% hexane / 95% ethyl acetate and overall 172 mg of a fraction could be isolated. The main component with 65 area percent and molecular mass 286 according to GC-MS was further characterized by NMR and assigned as a compound according to formula (I).

[0054] Spectroscopic and spectrometric data of compound according to formula (I):

[0055] 2,3-dihydro-5,7-dihydroxy-3-[(4-hydroxyphenyl)methyl]-4H-1 -Benzopyran-4-one ( mass 286, C16H14O5, trivial name 4'-demethyl-3,9-dihydroeucomin):1H NMR (600 MHz, DMSO) 6 12.17 (s, 1 H), 7.05 - 7.00 (m, 2H), 6.72 - 6.67 (m, 2H), 5.88 (d, J = 2.2 Hz, 1 H), 5.86 (d, J = 2.1 Hz, 1 H), 4.25 (dd, J = 11 .4, 4.5 Hz, 1 H), 4.07 (dd, J = 1 1 .4, 8.1 Hz, 1 H), 3.00 (dd, J = 13.9, 5.0 Hz, 1 H), 2.95 (ddt, J = 9.5, 8.1 , 4.7 Hz, 1 H), 2.58 (dd, J = 13.9, 9.5 Hz, 1 H);13C NMR (151 MHz, DMSO) 6 197.83, 166.56, 163.79, 162.82, 155.89, 129.93, 128.04, 115.26, 101.26, 95.91 , 94.73, 68.85, 45.59, 39.94, 39.80, 39.66, 39.52, 39.38, 39.24, 39.10, 31 .16.

[0056] 2) Human sensory trial

[0057] A trained panel was given two samples per test with the bitter tasting substance quinine (10 mg / kg in water) on the one hand and potential bitter-masking substance or mixture on the other hand. During the tests, the panellists wear nose-clips to exclude any olfactory impressions. Samples were served with 3-digit code in a sensory room with yellow-red light. Panellists were asked to rate the bitter intensity on a scale of 0-100 %. Data were recorded and statistically elaborated with Eyequestion 4, Logic8 B.V. A pairwise comparison sensory test showed significant bitter masking properties of ethyl acetate extract of Daemonorops draco (500 ppm) on the bitter taste of quinine. A reduction of -33.0% was reached (p < 0.000). Moreover, for the fraction of the extract of ethylene acetate of Daemonorops draco, wherein a compound according to formula (I) was present, bitter masking activity of 27.1% (p < 0.000) was detected (Table 1).

[0058] Table 1 : Sensory study. Pairwise comparison sensory test of selected dragon blood constituents on the bitterness of quinine (10 ppm).

[0059] ‘Reference substances

[0060] Further experiments were conducted with caffeine as bitter substance and showed reduc- tion of the bitter taste by application of compound of formula (I) (Table 2).

[0061] Table 2: Sensory study. Pairwise comparison sensory test of caffeine with and without compound according to formula (I)

[0062] 3) in vitro cell assay

[0063] The impact of quinine [10 ppm] and ethyl acetate extract of Daemonorops draco [100 ppm] on proton secretion in HGT-1 wild-type cells was tested (Figure 1). Cell based studies show an altered response after co-incubation of quinine [10 ppm] with the ethyl acetate extract of the resin of Daemonorops draco [100 ppm] (AUC 0-30 min: 2.26 ± 0.62) compared to quinine [10 ppm] (AUC 0-30 min: -0.22 ± 0.20) (p < 0.001). An anti-secretory effects indicates a bitter-masking ability of the extract of Daemonorops draco on quinine.

[0064] The impact of quinine [10 ppm] and compound according to formula (I) (DMDHE) [100 ppm] on proton secretion in HGT-1 wild-type (wf) cells and TAS2R14 knock-out cells was further investigated (Figure 2). The compound according to formula (I) [100ppm] in combination with quinine [10 ppm] (AUC 0-30 min: 58.82 ± 1.77) reduced the cellular response compared to quinine alone (AUC 0-30 min: -0.36 ± 0.60). Furthermore, an involvement of the bitter taste receptor TAS2R14 in the DMDHE mediated cellular response was shown by a changed response in the HGT-1 TAS2R14ko cells (AUC 0-30 min: 46.36 ± 3.88) compared to the HGT- 1 wt cells (AUC 0-30 min: 58.82 ± 1 .77, p < 0.01). These data are in line with the sensory data shown above, depicting DMDHE as a bitter-masking compound.

[0065] 4) Food or feed compositions

[0066] Taste improvement of a vegan patty: A vegan patty has been produced containing the following ingredients: water, leguminose protein isolate, sun flower oil, leguminose protein concentrate, coconut oil, methylcellulose, fiber, salt, starch, lactic acid and sodium diacetate. Water, thickener and starch are mixed with water, pH is adjusted, proteins are added next followed by fibre and oil ingredients. Finally, a taste masking ingredient according to Table 3 is added. The ingredients are thoroughly mixed and the dough is formed to patties. The patties where baked in an oven at 200°C. After cooling the patties, patties were sliced and samples were coded for a blind tasting with a panel.

[0067] Table 3: Sensory profile of vegan patties with a compound according to formula (I) in comparison to control without bitter masking agent

Claims

Claims1. Use of a compound according to formula (I) or a mixture comprising a compound according to formula (I)for reducing, modifying and / or masking a bitter taste impression of one or more bitter tasting substances.

2. Use according to claim 1 , wherein the bittertasting substance(s) is / are selected from the group consisting of TAS2R receptor modulating substances, preferably TAS2R1 , TAS2R4, TAS2R3, TAS2R5, TAS2R7, TAS2R8, TAS2R9, TAS2R10, TAS2R13, TAS2R14, TAS2R16, TAS2R38, TAS2R39, TAS2R40, TAS2R41 , TAS2R42, TAS2R43, TAS2R44, TAS2R45, TAS2R46, TAS2R47, TAS2R48, TAS2R49, TAS2R50, and / or TAS2R60, more preferably TAS2R4, TAS2R7, TAS2R10, TAS2R14, TAS2R39, TAS2R40, TAS2R43, TAS2R44, and / or TAS2R46, receptor modulating substances.

3. Use according to claim 1 or 2, wherein the bitter tasting substance(s) is / are selected from the group consisting of flavonoid(s), preferably naringin, neohesperidin, quercitrin, quercetin glycosides, kaempferol glycosides, kaempferol glycosidester(s), preferably kempferol 3-0-(2"'-0-sinapoyl-beta-sophoroside), hydroxy fatty acid(s), saponin(s), preferably soysaponins, glycoalkaloid(s), preferably solanin, bitter amino acid(s), preferably L- leucine, L-isoleucine, L-valin, L-phenylalanine, L-arginine, L-tryptophane, bitter peptide(s), quinine, caffeine, humulone isomere, cucurbitacin E, absinthin, acesulfame K, acetaminophen, acetylthiourea, aloin, allylisothiocyanate, amarogentin, D-amygdalin, andro- grapholide, arborescin, arbutin, arglabin, aristolochic acid, artemorin, azathioprine, benzamide, benzoin, brucine, campher, caprolactam, carisoprodol, cascarillin, chloramphenicol, chlorhexidine, chlorpheniramine, chloroquine, cnicin, colchicine, coumarin, crispolide, cromolyn, cucurbitacin B, cycloheximid, dapsone, denatonium benzoate, dextrome-thorphan, dimethylformamide, diphenylhydramine, diphenidol, diphenylthiourea, divinyl- sulfoxid, erythromycin, ethylpyrazine, N-ethylthiourea, N,N’-ethylene thiourea, falcarindiol, famotidine, flufenamic acid, grossheimin, haloperidol, helicin, hydrocortisone, 4-hydroxy- anisol, limonin, methimazole, 4(6)-methyl-2-thiouracil, methylthiourea, noscapine, orphen- adrine, papaverine, parthenolide, picrotoxinin, 1 ,10-phenanthroline, phenylethyl isothiocyanate, PTC, PROP, quassin, saccharin, D-salicin, sinigrin, sodium benzoate, sodium cyclamate, sodium thiocyanate, strychnine, tatridin B, thiamine, thujon (-)-a, and yohimbine.

4. Use according to any of claims 1 to 3, wherein the bitter taste impression of proteins and / or protein comprising products is reduced, modified and / or masked.

5. Use according to any of claims 1 to 4, wherein the bitter taste impression of quinine and / or quinine comprising products is reduced, modified and / or masked.

6. Extract comprising a compound according to formula (I)wherein the amount of the compound according to formula (I) in the extract is sufficient for reducing, modifying and / or masking a bitter taste impression, of a or, respectively, one or more bitter tasting substance(s), and / or wherein the amount is in a range of from 0.5 to 80 wt.%, preferably in a range of from 1 to 65 wt.%, in each case based on the total amount of the extract.

7. Extract according to claim 6, wherein the bitter tasting substance(s) is / are selected from the group consisting of TAS2R receptor modulating substances, preferably TAS2R1 , TAS2R4, TAS2R3, TAS2R5, TAS2R7, TAS2R8, TAS2R9, TAS2R10, TAS2R13, TAS2R14, TAS2R16, TAS2R38, TAS2R39, TAS2R40, TAS2R41 , TAS2R42, TAS2R43, TAS2R44, TAS2R45, TAS2R46, TAS2R47, TAS2R48, TAS2R49, TAS2R50, and / or TAS2R60, more preferably TAS2R4, TAS2R7, TAS2R10, TAS2R14, TAS2R39, TAS2R40, TAS2R43, TAS2R44, and / or TAS2R46, receptor modulating substances.

8. Extract according to claim 6 or 7, wherein the bitter tasting substance(s) is / are selected from the group consisting of flavonoid (s), preferably naringin, neohesperidin, quercitrin, quercetin glycosides, kaempferol glycosides, kaempferol glycosidester(s), preferably kempferol 3-0-(2"'-0-sinapoyl-beta-sophoroside), hydroxy fatty acid(s), saponin(s), preferably soysaponins, glycoalkaloid(s), preferably solanin, bitter amino acid(s), preferably L- leucine, L-isoleucine, L-valin, L-phenylalanine, L-arginine, L-tryptophane, bitter peptide(s), quinine, caffeine, humulone isomere, cucurbitacin E, absinthin, acesulfame K, acetaminophen, acetylthiourea, aloin, allylisothiocyanate, amarogentin, D-amygdalin, andro- grapholide, arborescin, arbutin, arglabin, aristolochic acid, artemorin, azathioprine, benzamide, benzoin, brucine, campher, caprolactam, carisoprodol, cascarillin, chloramphenicol, chlorhexidine, chlorpheniramine, chloroquine, cnicin, colchicine, coumarin, crispolide, cromolyn, cucurbitacin B, cycloheximid, dapsone, denatonium benzoate, dextromethorphan, dimethylformamide, diphenylhydramine, diphenidol, diphenylthiourea, divinyl- sulfoxid, erythromycin, ethylpyrazine, N-ethylthiourea, N,N’-ethylene thiourea, falcarindiol, famotidine, flufenamic acid, grossheimin, haloperidol, helicin, hydrocortisone, 4-hydroxy- anisol, limonin, methimazole, 4(6)-methyl-2-thiouracil, methylthiourea, noscapine, orphen- adrine, papaverine, parthenolide, picrotoxinin, 1 ,10-phenanthroline, phenylethyl isothiocyanate, PTC, PROP, quassin, saccharin, D-salicin, sinigrin, sodium benzoate, sodium cyclamate, sodium thiocyanate, strychnine, tatridin B, thiamine, thujon (-)-a, and yohimbine.

9. Extract according to any one of claims 6 to 8, wherein the amount of the compound according to formula (I) in the extract is sufficient for reducing, modifying and / or masking the bitter taste impression of proteins and / or protein comprising products.

10. Extract according to any one of claims 6 to 9, wherein the amount of the compound according to formula (I) in the extract is sufficient for reducing, modifying and / or masking the bitter taste impression of quinine and / or quinine comprising products.11 . Extract according to any one of claims 6 to 10, wherein the extract is an extract of the plant Daemonorops draco, preferably an extract of the resin of the plant Daemonorops draco.

12. Food or feed composition comprising one or more bitter tasting substances and a compound according to formula (I) or a mixture, preferably an extract as defined in any one of claims 6 to 11 , comprising a compound according to formula (I)wherein the amount of the compound according to formula (I) in the food or feed composition is sufficient for reducing, modifying and / or masking a bitter taste impression, of a or, respectively, one or more bitter tasting substance(s), and / or wherein the amount is in a range of from 5 to 250mg / kg, more preferably in a range of from 25 to 150 mg / kg, based on the total amount of the composition.

13. Composition according to claim 12, wherein a or, respectively, the bitter tasting substance^) is / are selected from the group consisting of TAS2R receptor modulating substances, preferably TAS2R1 , TAS2R4, TAS2R3, TAS2R5, TAS2R7, TAS2R8, TAS2R9, TAS2R10, TAS2R13, TAS2R14, TAS2R16, TAS2R38, TAS2R39, TAS2R40, TAS2R41 , TAS2R42, TAS2R43, TAS2R44, TAS2R45, TAS2R46, TAS2R47, TAS2R48, TAS2R49, TAS2R50, and / or TAS2R60, more preferably TAS2R4, TAS2R7, TAS2R10, TAS2R14, TAS2R39, TAS2R40, TAS2R43, TAS2R44, and / or TAS2R46, receptor modulating substances.

14. Composition according to claim 12 or 13, wherein the bitter tasting substance(s) is / are selected from the group consisting of flavonoid(s), preferably naringin, neohesperi- din, quercitrin, quercetin glycosides, kaempferol glycosides, kaempferol glycosidester(s), preferably kempferol 3-0-(2"'-0-sinapoyl-beta-sophoroside), hydroxy fatty acid(s), sapo- nin(s), preferably soysaponins, glycoalkaloid(s), preferably solanin, bitter amino acid(s), preferably L-leucine, L-isoleucine, L-valin, L-phenylalanine, L-arginine, L-tryptophane, bitter peptide(s), quinine, caffeine, humulone isomere, cucurbitacin E, absinthin, acesulfame K, acetaminophen, acetylthiourea, aloin, allylisothiocyanate, amarogentin, D-amygdalin, andrographolide, arborescin, arbutin, arglabin, aristolochic acid, artemorin, azathioprine, benzamide, benzoin, brucine, campher, caprolactam, carisoprodol, cascarillin, chloramphenicol, chlorhexidine, chlorpheniramine, chloroquine, cnicin, colchicine, coumarin, crispolide, cromolyn, cucurbitacin B, cycloheximid, dapsone, denatonium benzoate, dextromethorphan, dimethylformamide, diphenylhydramine, diphenidol, diphenylthiourea, divi-nylsulfoxid, erythromycin, ethylpyrazine, N-ethylthiourea, N,N’-ethylene thiourea, falca- rindiol, famotidine, flufenamic acid, grossheimin, haloperidol, helicin, hydrocortisone, 4-hy- droxyanisol, limonin, methimazole, 4(6)-methyl-2-thiouracil, methylthiourea, noscapine, or- phenadrine, papaverine, parthenolide, picrotoxinin, 1 ,10-phenanthroline, phenylethyl isothiocyanate, PTC, PROP, quassin, saccharin, D-salicin, sinigrin, sodium benzoate, sodium cyclamate, sodium thiocyanate, strychnine, tatridin B, thiamine, thujon (-)-a, and yohimbine.

15. Composition according to any one of claims 12 to 14, wherein the composition is a protein comprising product and / or a quinine containing product, preferably, wherein the protein is selected from the group consisting of proteins from whey, soy, pea, faba bean, lentil, canola, lupine, potato, wheat, chickpea, quinoa, millet / shorgum, beans, other legumes, algae, fungi, yeasts, and bacteria.

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