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    • 专利摘要:
    rebaudioside-mogroside mixtures v. The present invention relates to a composition comprising the mogroside v and a rebaudioside component in a weight ratio of <242>1:1 and <243>6:1, wherein the rebaudioside component consists of one or more selected compounds from the group consisting of rebaudioside a, rebaudioside b and rebaudioside d. a method of purifying a luo han guo extract includes contacting the luo han guo extract with activated carbon and a macroporous polymeric adsorbent resin, an ion exchange resin, or both. a composition includes an extract of luo han guo, wherein the mogroside v constitutes from 50% by weight to 75% by weight of the extract of luo han guo and the composition comprises from 0 to 13% by weight in total with respect to the mogroside v de aromatic glycosides, and 0 to 15 ppm of semi-volatile organic compounds in relation to mogroside v.
    公开号:BR112013018961B1
    申请号:R112013018961-4
    申请日:2012-01-24
    公开日:2021-08-10
    发明作者:John R. Bridges；Alfred Carlson；Brian Timothy Pohrte；Mary Quinlan；Timothy C. Schunck；Elber F. Tejada；Shelly Yuqing Zhou
    申请人:Tate & Lyle Ingredients Americas Llc；
    IPC主号:
    专利说明:

    Background
    [001] Natural caloric sweeteners, such as sucrose, glucose and fructose, have desirable flavor characteristics, but add to the caloric content of products. Therefore, there is great consumer interest in low-calorie or no-calorie sweeteners that are considered healthier alternatives. High potency natural and non-caloric synthetic sweeteners are known but often have flavor profiles that are not as desirable to consumers as sugars. Therefore, it is desirable to develop non-caloric sweeteners that can be substituted for sugar and that have a more desirable flavor profile.
    [002] The species Stevia rebaudiana (“Stevia”) is the source of certain naturally occurring sweet steviol glycosides. Considerable research and development has been done to evaluate the use of Stevia's steviol sweet glycosides as non-caloric sweeteners. Sweet steviol glycosides that can be extracted from Stevia include the six Rebaudiosides (ie, Rebaudiosides A through F), stevioside (the predominant glycoside in wild Stevia extracts), steviolbioside, rubusoside, and dulcosides.
    Commercial low-calorie or no-calorie sweeteners based on Rebaudioside A and other sweet steviol glycosides tend to have bitter and licorice aftertastes. These characteristics are especially notable at concentrations above approximately 300 ppm. In food applications, preferred usage levels (8-10% sugar equivalence values) are typically approximately 500 ppm to approximately 1,000 ppm, above the range in which off-flavors are first noticed. As such, a need continues to exist for low-calorie, low- and/or no-calorie sweeteners including steviol sweet glycosides that have flavor profiles with little or no bitterness, off-flavours (eg, licorice), or sweetness profiles such as sweeteners. more natural caloric or combinations of such properties. Invention Summary
    [004] In one aspect, the invention provides a composition comprising Mogroside V and a Rebaudioside component in a weight ratio of >1:1 and <6:1, wherein the Rebaudioside component consists of one or more compounds selected to from the group consisting of Rebaudioside A, Rebaudioside B and Rebaudioside D.
    [005] In another aspect, the invention provides a method of purifying an extract of Luo Han Guo which includes contacting the extract of Luo Han Guo with activated carbon and a macroporous polymeric adsorbent resin, an ion exchange resin, or both.
    [006] In yet another aspect, the invention provides a composition including an extract of Luo Han Guo, wherein Mogroside V constitutes from 50% by weight to 75% by weight of the extract of Luo Han Guo and the composition includes from 0 in 13% by weight in total in relation to Mogroside V of aromatic glycosides, and from 0 to 15 ppm of semi-volatile organic compounds in relation to Mogroside V. Brief description of the drawings
    [007] Figure 1 shows the HPLC analysis of an exemplary dry Luo Han Guo extract, and the analysis of the same material that had been treated with carbon according to the invention, in the upper and lower chromatograms respectively.
    [008] Figure 2 shows enlarged views of the chromatograms shown in Figure 1.
    [009] Figure 3 shows gas chromatograms of semi-volatile organic compounds present in a sample of Luo Han Guo, one taken before treatment with activated carbon and one after treatment with activated carbon according to the invention.
    [010] Figure 4 shows an HPLC chromatogram of a Luo Han Guo fraction containing components that produce a musty taste.
    [011] Figure 5 shows an ATR-FTIR spectrum of a Luo Han Guo fraction showing characteristic bands compatible with the presence of an aromatic glycoside.
    [012] Figure 6 shows an accurate Time of Flight (ToF) mass spectrum of the principal component in Figure 4. Detailed description of the invention Definitions
    [013] As used in this application, the phrase "sweet steviol glycoside" means any naturally occurring compound that has the general structure of a steviol diterpene ring system with one or more saccharide residues chemically attached to the ring.
    [014] As used in this application, the phrase “Rebaudioside component” means the total of Rebaudiosides A, B and D present, with the understanding that only one or two of these may actually be present. Sweetener Compositions Including Rebaudioside-Mogroside V Mixtures
    [015] It is now described that mixtures of Mogroside V with Rebaudioside component consisting of one or more of Rebaudiosides A, B and D provide superior flavor characteristics, in many cases superior to the Rebaudioside or Mogroside V component alone, when compared to one equal level of sweetness. In some systems, the improved taste is even more evident by pH values from approximately pH 2 to approximately pH 8.
    [016] Mogroside V can be obtained from extracts of Luo Han Guo, commercially available from several sources. Exemplary methods of producing such extracts are described in U.S. Pat. U.S. No. 5,411,755 and Publn. No. 2006/0003053, both of which are incorporated in this application by reference for all useful purposes. Luo Han Guo is extracted from the fruit of Siraitia grosvenorii, a herbaceous perennial vine native to southern China and northern Thailand. It is one of four species in the genus Siraitia. Botanical synonyms include Momordica grosvenorii and Thladiantha grosvenorii. The extract is approximately 200 to 300 times sweeter than sucrose.
    [017] Typically, Mogroside V is the single most abundant Mogroside component of Luo Han Guo extracts, accompanied by other Mogrosides such as Mogrosides I, II, III, IV and VI as well as other extracted materials such as polyphenols, flavonoids, melanoidins, terpenes, proteins, sugars, aromatic glycosides and semi-volatile organic compounds. In some embodiments of the invention, Mogroside V is provided in the form of a Luo Han Guo extract (crude or purified and/or concentrated to increase the Mogroside V content). In some embodiments, Mogroside V constitutes at least 40% by weight of the extract, or at least 45% by weight or at least 50% by weight. Typically, it will constitute at most 95% by weight of the extract, at most 85% by weight of the extract, at most 75% by weight of the extract, at most 70% by weight of the extract, or at most 65% by weight, or at most 60% by weight.
    [018] In some sweetening compositions according to the invention, the weight ratio of Mogroside V to Rebaudioside component is at least 1:1, or at least 1.3:1 or at least 1.5:1. The weight ratio is typically at most 5:1, or at most 4:1, or at most 3.5:1, or at most 3:1, or at most 2.5:1, or at most 2:1 , or at most 1.9:1, or at most 1.8:1, or at most 1.7:1.
    [019] The Rebaudioside component consists of one or more of Rebaudioside A, B and/or D. The Rebaudioside component typically constitutes at least 65% by weight of total steviol sweet glycosides present, or at least 70% by weight, or at least 75% by weight or at least 80% by weight, or at least 90% by weight or at least 97% by weight. The balance of sweet steviol glycosides, if any, may include one or more of Rebaudiosides C, E and/or F, stevioside, and any other sweet steviol glycoside not part of the Rebaudioside component. Typically, Rebaudioside A will constitute at least 50% by weight of the steviol sweet glycosides present, or at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight or at least 95% by weight. Rebaudioside A, B and D can be obtained from extracts of Stevia rebaudiana, commercially available from several sources. Many different methods of producing such extracts and obtaining relatively pure Rebaudioside A, B or D from the extracts are known and have been described in the literature. In a typical process, stevia plants are dried and subjected to an extraction process in water. This crude extract contains approximately 50% Rebaudioside A. Several glycoside molecules in the extract are separated through crystallization techniques, typically using ethanol or methanol as a solvent, allowing the isolation of pure Rebaudioside A, B and D. The individual purified glycosides then can be used in combination to provide Rebaudioside components useful in the present invention.
    [020] Although the sweetening compositions of the invention may include mixtures of various types of sweeteners in various amounts, in some embodiments the composition consists essentially of an optionally purified Luo Han Guo extract and/or concentrate and an optionally purified Stevia extract and /or concentrate. Removal of undesirable flavor components from Luo Han Guo
    [021] It has now also been found, after extensive studies, that the presence of certain impurities in Luo Han Guo extracts results in an undesirable taste described by some tasters as "musty". In particular, aromatic glycosides and semi-volatile organic compounds have been identified as producers of this off-taste, although additional moldy off-taste components or other components may also be present. A particular aromatic glycoside has a molecular mass of 502 Daltons and appears to be a particularly musty taste producer. This compound is in accordance with the formula C26H30O10, and all compounds in total having this molecular formula are in some limited embodiments in accordance with the invention. Any means of achieving a sufficiently low level of this compound is suitable for the purposes of the invention. A suitable way is to pass an aqueous solution of Mogroside V, for example, in the form of an optionally purified and/or concentrated Luo Han Guo extract, through a column of granular activated carbon. Other forms of activated carbon, eg powders, can also be used. Carbon treatment also typically removes off-taste, moldy or other additional components as well as pesticide residues and other such substances that are generally undesirable in ingredients intended for human consumption. Typically, water is the only vehicle present during the carbon treatment, and no organic solvent is added. In some embodiments, Luo Han Guo extract is treated with a macroporous polymeric adsorbent resin, an ion exchange resin, and activated carbon. Typically, treatments will be in that order, but they don't have to be. An exemplary macroporous polymeric resin is commercially available from Rohm and Haas, Philadelphia, PA under the tradename AMBERLITE® XAD1180N. An exemplary suitable ion exchange resin is an anionic resin that is available under the trade name AMBERLITE® FPA90 CL, also from Rohm and Haas.
    [022] Treatment should employ a sufficient amount of activated carbon and should occur with a sufficiently long contact time to reduce the level of one or more aromatic glycosides and impurities of the semi-volatile organic compound to an acceptable level. In some embodiments of the invention, the sweetener composition comprises from 0 to 13% by weight total aromatic glycosides, or from 0 to 11% by weight, or from 0 to 10% by weight, or from 0 to 9% by weight, all in relation to Mogroside V. The aromatic glycosides can be phenyl glycosides or more specifically phenolic glycosides, or they can be coumarin glycosides or more specifically furanocoumarin glycosides. These same limits may also be appropriate in some embodiments for compounds of molecular weight 502, and more specifically for compounds according to formula C26H30O10, in each case referring to the total amount of all compounds of mass 502 or of formula C26H30O10.
    [023] In some embodiments of the invention, the sweetener composition comprises from 0 to 15 ppm by weight in total semi-volatile organic compounds, or from 0 to 11 ppm by weight, or from 0 to 7 ppm by weight, or from 0 to 3 ppm by weight, all relative to Mogroside V. The term "semi-volatile", as used in this application, means compounds having a molecular weight greater than 120 Daltons and a boiling point at pressure of 1 atm greater than 150°C and up to 350 °C. Such semi-volatile organic compounds may comprise, but are not limited to, the compounds listed in Table 7. Semi-volatile organic compounds, for example, may include aliphatic, unsaturated aliphatic furans, esters, polycyclic hydrocarbons and/or terpenoids.
    [024] Commercially available Luo Han Guo fruit powder extract, typically containing at least 40% Mogroside V (d.s.b), can be treated with activated carbon as follows. The dry extract is dissolved in deionized water at a concentration of at least approximately 1% by weight, and typically at most approximately 70% by weight. The water is heated to a temperature sufficient to favor dissolution of the powdered material, typically in a range between room temperature and 160°F (71.1°C), and optionally filtered using a microfiltration membrane or using filter paper with a non-reactive filter aid. The purpose of microfiltration is to remove insoluble proteins and/or microorganisms that can deteriorate the product. The resulting filtrate is subjected to adsorption with active carbon (also known as activated carbon). Carbon can be any form of available active carbon and, for example, can be derived from wood, bituminous coal, lignite coal, coconut, charred animal bones or any other source. In one embodiment, the active carbon that is used is an active carbon produced by the steam activation of lignite coal. Typically, carbon is in the form of granules, but other physical forms such as activated carbon powders or beads can also be employed. It will generally be advantageous to use an active carbon that is highly porous and that has a high surface area (eg more than 100 m2/g, more than 200 m2/g or more than 300 m2/g). Unwanted components that cause the off-taste (as well as other undesirable substances such as pesticides) are adsorbed onto the carbon, but the flavor-enhanced material is not adsorbed and is continuously eluted. The method allows recovery yields (dry substance basis) between 50% and 99.9%. The amount of active carbon used can range from 0.05% to 150% (as a percentage of the dry substance present in the aqueous solution of Luo Han Guo fruit extract). More typically, to achieve sufficiently low levels of off-taste components, at least 2% by weight or at least 5% by weight of activated carbon relative to Luo Han Guo fruit extract is used on a solids basis. In certain embodiments, at least 6% by weight or at least 10% by weight yield the best results. Typically, a maximum of 15% by weight will be used.
    [025] In a typical process, a column is packed with the desired amount of active carbon (typically in granular form), and deionized water is run through the column from top to bottom or bottom to top (downflow or upflow direction ) at a flow rate ranging from 1 to 10 bed volumes per hour. The amount of water to pass can vary from 2 to 5 bed volumes. Water can be at an elevated temperature (eg (135°F to 185°F)) when contacted with active carbon, which helps to reduce the leaching of unwanted substances such as heavy metals to carbon when the aqueous solution of the Luo Han Guo fruit extract is subsequently passed through the column. Since the water has displaced the remaining air and some fine carbon particulates, the aqueous solution of Luo Han Guo's fruit extract is fed to the column at a flow rate that can range from 1 to 10 bed volumes per hour. The column must be lined and the jacket temperature must be kept at the same temperature as the feed solution, which will typically be in the range of ambient temperature to 71°C. Initially, the feed displaces the water in the column. Once the column effluent shows signs of material present, the effluent is collected as improved flavor material. The presence of solids in the effluent can be evaluated by measuring the refractive index (RI). A correlation between RI and dry substance is typically constructed for this purpose.
    [026] Luo Han Guo fruit extract is fed to the column until the target treatment level has been reached. Once feeding ends, the remaining Luo Han Guo fruit extract still present in the column is expelled with deionized or reverse osmosis water, displacing the Luo Han Guo material. Effluent collection is continued until the refractive index of the effluent is close to that of water only.
    [027] Optionally, the recovered flavor-enhanced material can be concentrated in order to increase the % DS (dry substance) to any suitable level for subsequent drying, if desired. Concentration can be completed by evaporation or membranes, or by any other suitable method. Membrane concentration is possible with the use of a nanofiltration membrane (200 Da. M.W.C.O.) or with a reverse osmosis membrane (with a >98%) salt rejection assay. Both membranes can be used separately without losing a significant amount of mogrosides to the permeate. The material is then dried using a conventional spray drying unit or using a conventional spray agglomeration unit or other means. Or the material can be used as is. In one embodiment, the recovered flavor-enhanced material is combined with one or more components, such as Rebaudioside A, B and/or D or a purified Stevia extract containing sweet steviol glycosides, prior to drying. Use of sweetening compositions including rebaudioside-mogroside V mixtures
    [028] Compositions containing rebaudioside-mogroside V mixtures can be processed using known methods to modify particle size and physical form. Methods such as agglomeration, spray drying, drum drying and other forms of physical processing can be applied to adjust particle size to deliver better flow, hydration or dissolution properties. The compositions can be supplied in liquid forms, optionally containing one or more preservatives and/or processing aids, for ease of use in specific applications. Compositions containing rebaudioside-mogroside V mixtures can be co-processed with bulking agents such as maltodextrins and similar compounds to deliver products with controlled sweetness, dosage, potency and handling properties.
    [029] The sweetening compositions of the present invention are useful as low-calorie, low-calorie, or non-caloric sweeteners in foodstuffs, that is, edible or chewable compositions such as foods, beverages, medicines, candies, chewing gum and the like. It has been found that the sweetening compositions of the present invention can have a sweetness profile that is more like sugar and reduced bitter aftertaste and reduced off flavors (e.g. licorice) than sweeteners including only sweet steviol glycosides. Testing has shown that, in most cases, the sweetening compositions of the present invention are preferred by test subjects over compositions that include 97% Rebaudioside A when tested at a concentration that provides equal sweetness. In particular, sweetening compositions provide both immediate sweetness and delayed sweetness, resulting in more taste satisfaction. By adding the sweetening compositions of the present invention to foods and beverages it is expected to result in more palatable foods and beverages compared to those prepared with the known sweetening composition containing steviol sweet glycosides, such as compositions having 97% Rebaudioside A as the sweetener.
    [030] The sweetening compositions, according to the invention, may include, in addition to the Rebaudioside-Mogroside V mixture, other high potency sweeteners. For example, sweet steviol glycosides may be included. Specific examples of suitable high potency sweeteners include natural high potency sweeteners such as: dulcoside A, dulcoside B (also known as Rebaudioside C), rubusoside, mogroside III, mogroside IV, mogroside VI, siamenoside, monatin and its salts (monatin SS, RR, RS, SR), curculin, glycyrrhizic acid and its salts, thaumatin, monelin, mabinlin, brazein, hernandulcin, phylodulcin, glycyphyllin, and phloridzin; and high potency artificial sweeteners such as: saccharin, aspartame, sucralose, neotame, cyclamate and potassium acesulfame.
    [031] According to the invention, rebaudioside-mogroside V mixtures can also be combined with caloric sweeteners such as sugars (for example, high fructose corn syrup, sucrose, fructose, etc.) and polyols (for example, sorbitol, xylitol, lactitol, etc.) and/or other low calorie sweeteners to produce reduced calorie sweetening compositions.
    [032] In some embodiments, the invention provides foodstuffs including sweetening compositions with high concentrations of rebaudioside-mogroside V mixtures. Essentially any edible or chewable composition can be sweetened according to the invention. Non-limiting examples include foodstuffs, (eg baked goods, soups, sauces, processed meats, canned fruits, canned vegetables, dairy products, frozen confections); beverages (eg, carbonated soft drinks, ready-to-drink teas, sports drinks, dairy drinks, alcoholic drinks, energy drinks, tasty waters, vitamin drinks, fruit drinks, and fruit juices, powdered soft drinks), medicines or pharmaceuticals (eg pills, pills, suspensions, etc.), nutraceutical products (eg supplements, vitamins, etc.) candy or confectionery; bubble gum; tobacco products (for example, chewing tobacco); and the like. The sweetening composition is included in an amount effective to impart the desired amount of sweetness to the sweetened product. In some embodiments, the pH of the sweetened product is at least approximately 2 and no greater than approximately 8.
    [033] In some embodiments, foodstuffs contain a sweetening composition including mixtures of rebaudioside-mogroside V and one or more additional sweet steviol glycosides as described in this application. In some embodiments, the sweetening composition including Rebaudioside components, additional steviol glycoside components and Mogroside V component are present in foodstuffs in a total concentration of at least approximately 50 ppm, or at least approximately 200 ppm, or at least approximately 500 ppm, or at least approximately 1,000 ppm, or at least approximately 1,500 ppm, or at least approximately 3,500 ppm, or at least approximately 5,000 ppm. EXAMPLES Example 1 - Preference Test of Stevia-mogroside V Mixtures against Rebaudioside A
    [034] Mixtures of a solid extract of Luo Han Guo containing Mogroside V 50% by weight with a Stevia product containing mainly Rebaudioside A were compared in sweetness preference test and panel against Rebaudioside 97% by weight. Luo Han Guo extract was a purified version of a commercial product available from Biovittoria (Guilin, People's Republic of China) under the trade name Fruit Sweetness™, where purification was done by treatment with activated carbon as described elsewhere in this application to remove aromatic glycosides and semi-volatile organic compounds, which produce off-flavours. This product is identified below as Sample A. The Stevia product was a commercial product available from GLG Life Tech Corporation of Vancouver, BC, Canada under the trade name BlendSure™ 7.5, consisting of approximately 75% Rebaudioside A and 25% Stevioside 25% by weight. Preference Test
    [035] The paired comparison test was conducted for sweetness and preference of blends of BlendSure 7.5 and Sample A having sweetness equal to 97% Rebaudioside A in a pH 3 citric acid buffer (0.045% citric acid and 0.013% sodium citrate) with a panel of tasters. Tests were conducted as complete block designs with between 24 and 46 ratings. The order of presentation has been rotated. The solutions were served in 2-ounce cups marked with 3-digit codes at room temperature. Participants were instructed to consume at least half of each sample. There was a one-minute forced waiting period between tests to debug the participants' palates. Participants were asked to identify the solution that was sweetest and which they liked the most. Bottled water, 2% sucrose solution and unsalted crackers were available to the participants to cleanse their palates before and during the test. Sweetness results were analyzed as two-tailed tests at an alpha risk of 0.05 with the binomial test, as shown below.
    [036] The results of questions of sweetness and preference were analyzed with the binomial test and calculated Thurstonian d'. The p-value of a one-tailed binomial test is calculated as
    where c is the number of successes, n is the number of tests, and p0 is the probability of odds. A test is considered statistically significant when the p-value is less than the alpha risk of the a priori set. The p-value of two tails is double one-tailed p-value as calculated above.
    [037] The Thurstonian d' is a linear measure of psychophysical difference. A d' = 1 is generally considered to be “only perceptible difference” (JND) where a stimulus will be judged stronger in 75% of tests. Thurstonian's d' is independent of the test method and for the paired comparison the tests are calculated as
    where p is the proportion of successes and Φ (•) is the cumulative distribution function of the standard normal distribution. A complete treatment of these statistical calculations can be found in standard textbooks on the subject (Bi J., “Sensory Discrimination Tests and Measurements”, Blackwell Publishing, 2006, Chapters 2 and 9).
    [038] The results of the combined replicated tests are shown below in Table 1. Table 1

    [039] In citric acid buffer pH 3 and sweetness levels that were not significantly different (p value >0.05 two tails), the above data indicates a preference for mixtures containing proportions of Mogroside V to Rebaudioside A within certain tracks. Specifically, the following can be seen.
    [040] A mixture of 675 ppm of Sample A and 225 of BlendSure 7.5 (75% Sample A, 900 ppm total) was significantly preferred over 900 ppm of 97% Rebaudioside A.
    [041] A mixture of 825 ppm Sample A and 275 BlendSure 7.5 (75% Sample A, 1100 ppm total) was significantly preferred over 1,000 ppm 97% Rebaudioside A.
    [042] A mixture of 444 ppm Sample A and 296 BlendSure 7.5 (Sample A 60%, 740 ppm total) was not significantly different from 605 ppm Rebaudioside A 97%.
    [043] A mixture of 547 ppm of Sample A and 365 of BlendSure 7.5 (Sample A 60%, 912 ppm total) was significantly preferred over 705 ppm Rebaudioside A 97%.
    [044] A mixture of 660 ppm Sample A and 440 BlendSure 7.5 (Sample A 60%, 1100 ppm total) was not significantly different in preference to 1000 ppm Rebaudioside A 97%.
    [045] Mixtures of Sample A and BlendSure 7.5 that contained Sample A 75% performed better than mixes containing Sample A 60% versus Rebaudioside A 97%.
    [046] Mixtures of Sample A and BlendSure 7.5 were more preferred over Rebaudioside A 97% as the sweetness level increased. Example 2 - Preference Test of Stevia-Mogroside V Mixtures against Stevia
    [047] Mixtures of a solid extract of Luo Han Guo containing Mogroside V 50% by weight with a Stevia product containing mainly Rebaudioside A in a pH 3 citric acid buffer (0.045% citric acid and 0.013% sodium citrate) were compared in sweetness panel test and preferably against Stevia's product. The mixtures and the Stevia product were as described in Example 1. Synergy can be detected by constructing isoboles (iso-effect curves) where the concentrations of two substances that have equal effect, in this case sweetness, are plotted in a diagram with the axis being the concentration of substances. Linear isoboles result when there is no synergy between the two substances. An isobole with a downward curvature results when there is synergy between the two substances. A full discussion of isoboles and synergy can be found in Berenbaum, "What is Synergy", Pharmacological Reviews, Vol. 1989, No. 41 pages 93-129. BlendSure 7.5 and Sample A blends having sweetness equal to 500 ppm, 700 ppm and 900 ppm BlendSure 7.5 were predicted to be linear isoboles with no sweetness synergy assumption.
    [048] Paired comparison testing was conducted for sweetness and preference of blends of BlendSure 7.5 and Sample A which are sweet equal to 500 ppm, 700 ppm and 900 BlendSure ppm 7.5 levels with a taster panel. Tests were conducted as a complete block design with between 34 and 44 ratings. The order of presentation has been rotated. The solutions were served in 2-ounce cups marked with 3-digit codes at room temperature. Participants were instructed to consume at least half of each sample. There was a one-minute forced waiting period between tests to compensate for the palates of the roundtable participants. Participants were asked to identify the solution that was sweetest and which they liked the most. Bottled water, 2% sucrose solution and unsalted crackers were available to the participants to cleanse their palates before and during the test. The results were analyzed as in Example 1 and are summarized in Table 2. Table 2


    [049] As can be seen from the above data, there was no evidence of sweetness synergy between BlendSure 7.5 and Sample A. However, the preference of a blend of BlendSure 7.5 and Sample A over BlendSure 7.5 only increased with the proportion of Sample A for BlendSure 7.5 increased, and also as sweetness increased. Example 3 - Removal of Aromatic Glycosides and Semivolatile Organic Compounds from Luo Han Guo Extract
    [050] A coated 3' x ^” ID glass column (embedded Ace glass) of approximately 115 mL capacity was packed with approximately 57 g of virgin granular active carbon (12x40 CAL from Calgon Corporation) which had been freshly washed with water boiling. The column jacket was heated to 60°C and maintained at that temperature for the duration of the experiment. After packing the column, approximately 500 mL of deionized water was passed through the carbon bed at a flow rate of 2.5 mL/min in order to displace and remove fine carbon particulates. A 27 wt% solution of Biovittoria Fruit Sweetness™ (approximately 50 wt% Mogroside V on dry solids (dsb) basis) was prepared by dissolving 1.241 kg of Biovittoria Fruit Sweetness™ in 3.318 kg of Milli-Q water (water supplied by a Milli-Q reverse osmosis water purification system, available from Millipore Corp.). The solution was then heated to 60°C, passed through the Millipore Optiseal Durapore 0.22 µm hydrophilic pleated cartridge filter into a sterile feed bottle and maintained at 60°C during the run.
    [051] The solution was passed through the column at a rate of 2.6 g/min (equivalent to 1.25 Bed volumes per hour) using MASTERFLEX® 13 tubing and a peristaltic pump (MASTERFLEX® pump). The effluent was collected in fractions of 90 minutes, with an average mass of 234 grams per fraction. After fraction 19 (run time elapsed: 28.5 hours), the effluent was sampled and it was informally determined that the effluent tasted significantly better than the feed material. Therefore, an additional 355.5 g of Biovittoria Fruit Sweetness™ was dissolved in 945.3 g of Milli-Q water, brought to 60°C, passed through the 0.22 μm Millipore Optiseal Durapore hydrophilic pleated cartridge filter and added to the feeding bottle. After 37.5 hours, sweetener removal (the term "sweetener removal" is understood as washing the column to remove the remaining Fruit Sweetness™ solution) was started by modifying the column feed to Milli-Q water (60° Ç). The column was left to remove sweetener for 6 hours until the refractive index of the effluent was similar to that of water. The material collected in all fractions corresponded to a total mass yield of approximately 98% by weight of the dry material fed to the apparatus. The treatment level of the total material fed to the apparatus (1241 g + 335 g) was calculated to be 3.61% by weight. A round table of eight experienced tasters compared acceptability with respect to reduced off-taste by comparing aqueous solutions of Fruit Sweetness™, Composite Fractions 1 to 5, Composite Fractions 1 to 10, Composite Fractions 1 to 15, Composite Fractions 1 through 20 and Composite fractions 1 through 25. Composites 1 through 5, 1 through 10 and 1 through 15 were found to exhibit a significant level of flavor improvement over the Fruit Sweetness™ fed material. A Composite of fractions 1 to 15 contained a dry mass of 947 g, thus corresponding to a carbon treatment level of 6.0% by weight. The Composite of fractions 1 through 15 was identified below as SAMPLE A (A 286683).
    [052] HPLC was used to determine the aromatic glycoside composition of the Biovittoria Fruit Sweetness™ feed and the best tasting effluent from Luo Han Guo after carbon treatment. A Waters 2695 Separation Module was equipped with a Waters 2487 Dual À Absorbance detector and a C18 Phenomenex Gemini Column, 5 µm, 150 x 4.6 mm with Security Guard C18 Phenomenex Gemini cartridge, 4 x 3 mm. An acetonitrile/water gradient listed below was used as the mobile phase, at a flow rate of 1.0 mL/min and a column temperature of 40°C. UV detection at 203 nm was used, and injection volume of 40 µL. Mobile phase: Linear segment gradient in % acetonitrile/water volume

    [053] A pure Mogroside V standard (ChomaDex, Inc.) was used for the calibrated quantification of all components detected at 203 nm. Table 3 summarizes the % by weight of components on a dry solids basis (dsb) as Mogroside V. A significant reduction in the elution of aromatic glycosides from the HPLC column in the range of 3.5 to 4.5 minutes under defined conditions above was observed between the Biovittoria Fruit Sweetness™ feed and the carbon effluent and this reduction corresponded to the significant flavor improvement observed. Table 3

    [054] The GC headspace with flame ionization detection (FID) as defined by the following conditions was used to determine the composition of semi-volatile organic compounds in the best tasting Luo Han Guo and Luo Han Guo feed recovered after carbon treatment .

    Multiplier compensation: 0V
    [055] A standard of pure D-limonene (Sigma-Aldrich) was used for calibrated quantification of all components of the semi-volatile organic compound shown in Figure 3. Table 4 summarizes the total semi-volatile organic compounds in ppm by weight of the components in one dry solids base (dsb) as D-limonene. A significant reduction of semi-volatile organic compounds from Biovittoria Fruit Sweetness™ feed (284178) to carbon treated Luo Han Guo (Sample A 286683) is seen, corresponding to the significant improvement in the flavor of Luo Han Guo. Table 4
    Example 4 - Identification of Undesired Flavor Components in Luo Han Guo Extract
    [056] Sensory evaluation found that Luo Han Guo material that has passed through carbon in the aqueous solution tastes better, more acceptable than the Luo Han Guo feed material. HPLC analysis of an exemplary dry Luo Han Guo extract having a Mogroside V content of approximately 50% by weight (Biovittoria Fruit Sweetness™), and analysis of the same material that had been carbon treated and sprayed dry, is shown respectively in the upper and lower chromatograms in Figure 1. The HPLC method parameters were as in Example 3 with the following modified linear segment gradient. Mobile phase: Linear gradient in % by volume of acetonitrile/water

    [057] HPLC analysis showed that the profile of mogroside isomers remained essentially unchanged after carbon treatment. An enlarged view of the more polar region of the chromatograms in Figure 1 is shown in Figure 2, where the treated product shown in the lower chromatogram shows peaks in the vicinity of 21 min (marked with an arrow) much reduced compared to the untreated product in the upper chromatogram . In order to determine the elution rate of component(s) close to 21 min and the reduction in the off-taste “musty”, a series of purification and extraction steps were applied to the spent carbon that had been used to treat Luo Han Guo de in a similar manner to Example 3. After each extraction purification step during this study, a group of expert tasters evaluated the carbon-treated Luo Han Guo samples that had been spiked with ~5 to 10X the original level of the recovered components in order to to identify samples that exhibited the "musty" off-taste characteristic of Fruit Sweetness™.
    [058] To recover the components removed by the carbon treatment of the aqueous Luo Han Guo solution, approximately 500 g of spent carbon that had been used for the Luo Han Guo refining was sequentially extracted with multiple 350 mL aliquots of solvents after washing with water. Ethanol and then acetone were used to wash the carbon. The extracts were filtered through 0.45 µm nylon filters and evaporated to dryness under a stream of nitrogen at room temperature to recover approximately 2.0 g of solid. The aforementioned expert taster group noted that the acetone extract residue contained the significant "musty" off-taste characteristic of Fruit Sweetness™. It was also confirmed that the 21 min HPLC component (Figures 1 and 2) was contained in the acetone fraction and also in all subsequent "musty" off-taste fractions, as described below.
    [059] The liquid-liquid extraction between 50 mL of water and 50 mL of chloroform was applied to the initial fraction extracted from acetone after complete drying. The undesirable “musty” taste remained with the water-soluble fraction (approximately 1.8 g of recovered solid). Subsequently, solid phase extraction (SPE) using four stacked Waters Sep-Pak C18 SPE cartridges (Waters Corp., WAT020515) was applied to further fractionate off-taste residue. Approximately 10 mg/ml of the residue in water was charged to the 10 ml cartridges at once after conditioning the SPEs with 5 ml methanol and 10 ml Milli-Q water. The recovered fractions were then obtained using a 10 ml series of SPE wash as follows; 100% water, 2% acetonitrile (MeCN)/98%water, 5% MeCN, 10% MeCN, 20% MeCN, 25% MeCN, 30% MeCN, 40% MeCN, 50% MeCN and 100% MeCN. All extracts were dried under a stream of nitrogen and evaluated by a sensory panel. This entire spent carbon isolation procedure through SPE fractionation was repeated three times with the same sensory results.
    [060] The "musty" off-taste characteristic was determined to be significantly concentrated at approximately 250 mg of solids recovered from the eluted SPE fraction of 20% MeCN/80% water (288054) as verified by the expert taster group when reinforced in a carbon-treated aqueous solution of Luo Han Guo. HPLC of this fraction again showed the 21 min elution component, Figure 4. Chemical analyzes of the primary components of this isolate, relative to a SPE blank (10 mL water + 10 mL 50% MeCN + 10 mL 100% MeCN ) were conducted using; Antek total nitrogen, Folin-Ciocalteu phenolic colorimetric test, ninhydrin colorimetric test for proteins, amino acid analysis by ion chromatography of an acid digestion, dry solid ATR-FTIR, LC-MS and NMR. The results are summarized in Tables 5 and 6 and are compatible with an aromatic glycoside class of compounds. Table 5

    [061] Figure 5 shows the ATR-FTIR spectrum corrected in the fraction reference 288054. The characteristic bands of OH, CH, aliphatic CO and weak phenyl absorbances can be seen, all compatible with the presence of an aromatic glycoside. No C=O absorbance is observed. Figure 6 shows the accurate Time of Flight (ToF) mass spectrum of the principal component that corresponds to sample 288054 in Figure 4 with a retention time of 21.0 minutes. The table inset in Figure 6 lists the most likely stoichiometric formula for the 503 Dalton mass ion. The most likely exact mass with mass accuracy of 1.6 ppm is shown to be a neutrally charge compound C26H30O10. Table 6

    [062] The distribution and suggested identity of a variety of semi-volatile components were evaluated using the headspace of 5% aqueous solutions by Gas Chromatography with mass spectrometric detection (GC-MS) as defined in Example 3. Figure 3 shows a comparison of the semivolatile component profile of the Fruit Sweetness™ (284178) and Sample A feed. Table 7 shows a listing of the best MS library combinations of 28 semivolatile organic compounds that match those marked in Figure 3. Known organoleptic responses of taste and odor for these compounds are listed for comparison (eg see, Mosciano, G., Perfumer and Flavorist 25, No. 6, 26, (2000). Table 7

    Example 5
    [063] An amount of 40 g of Fruit Sweetness™ was dissolved in 200 g of Milli-Q water in a 500 mL beaker and 30 g of activated carbon (BG-HHM from Calgon Carbon Corporation) was added to the Fruit Sweetness solution. ™. The activated carbon slurry was stirred for 2 hours, taking 50 µL samples of the sterile filtered solution at 0, 5, 15, 30, 60, 90 and 120 minutes. Samples were diluted 20-fold in Milli-Q water and analyzed by HPLC for the relative abundance of mogrosides between time points. After 2 hours, the activated carbon slurry was filtered through Whatman #2 filter paper and the filtrate was strained sterile into a tared freeze drying bottle. Once the sterile filtrate had been freeze-dried, its mass was recorded and analyzed with HPLC for Mogroside V content. The vacuum-frozen material was designated Sample B. A 550 ppm neutral pH water solution of Sample B (Carbon-treated Fruit Sweetness™ slurry) was then tested against 500 ppm Reb A 97 in pH neutral water for taste preference by 48 to 50 participants. For comparison, Fruit Sweetness™ was also tested against 500 ppm Reb A 97 for preference in pH neutral water. Tests were conducted as complete block drawings. The order of presentation has been rotated. The solutions were served in 2-ounce cups at room temperature. Participants were instructed to consume the entire sample. Participants were not allowed to disapprove the samples. Participants were asked to identify which solution was sweetest and which they preferred. Bottled water, 2% sucrose solution and unsalted crackers were available to the participants to cleanse their palates before and during the test.
    [064] Data were analyzed with the binomial test with an alpha risk of 0.05 as a two-tailed test for sweetness and a one-tailed test for preference. Table 8
    Table 9

    [065] Table 8 shows that the commercial Fruit Sweetness™ product was not significantly preferred over Reb A at the level of equi-sweetness. However, Fruit Sweetness™ carbon-treated Sample B slurry was significantly preferred over BlendSure 7.5 at the equi-sweetness level (Table 9).
    [066] Although the invention is illustrated and described in this application with reference to specific embodiments, the invention is not intended to be limited to the details shown. Rather, various modifications can be made to the details within the scope and range of equivalents of the claims without departing from the invention.
    权利要求:
    Claims (21)
    [0001]
    1. Composition, characterized in that it comprises a) Luo Han Guo extract which has been treated with an activated carbon and which is composed of at least 40% by weight of Mogroside V and b) a Rebaudioside component in which the Mogroside V and the Rebaudioside component are present in the composition in a weight ratio of >1:1 and <6:1, and the Rebaudioside component consists of one or more compounds selected from the group consisting of Rebaudioside A, Rebaudioside B and Rebaudioside D.
    [0002]
    2. Composition according to claim 1, characterized in that the weight ratio is > 1.5:1.
    [0003]
    3. Composition according to claim 1, characterized in that the Rebaudioside component is provided as a component of a Stevia extract comprising sweet steviol glycosides, wherein the Rebaudioside component constitutes at least 70% by weight of sweet steviol glycosides.
    [0004]
    4. Composition according to claim 1, characterized by the fact that Mogroside V constitutes a range of 45% by weight to 60% by weight of Luo Han Guo extract.
    [0005]
    5. Composition according to claim 1, characterized in that the composition comprises from 0 to 13% by weight in total aromatic glycosides, in relation to Mogroside V.
    [0006]
    6. Composition according to claim 1, characterized in that the composition comprises from 0 to 13% by weight in the total of compounds that have a molecular mass of 502 Daltons, in relation to Mogroside V.
    [0007]
    7. Composition according to claim 1, characterized in that the composition comprises from 0 to 13% by weight in the total of compounds according to the formula C26H30O10, in relation to Mogroside V.
    [0008]
    8. Composition according to claim 1, characterized in that the composition comprises from 0 to 15 ppm by weight in total semi-volatile organic compounds, in relation to Mogroside V.
    [0009]
    9. Composition according to claim 1, characterized in that it further comprises a caloric sweetener.
    [0010]
    10. Composition according to claim 1, characterized in that it further comprises an additional high potency sweetener.
    [0011]
    11. Drink, characterized in that it comprises the composition as defined in claim 1.
    [0012]
    12. Food, characterized in that it comprises the composition as defined in claim 1.
    [0013]
    13. Oral health product, characterized in that it comprises the composition as defined in claim 1.
    [0014]
    14. Tobacco product, characterized in that it comprises the composition as defined in claim 1.
    [0015]
    15. Pharmaceutical product, characterized in that it comprises the composition as defined in claim 1.
    [0016]
    16. Nutraceutical product, characterized in that it comprises the composition as defined in claim 1.
    [0017]
    17. Composition according to claim 1, characterized in that the Luo Han Guo extract was additionally placed in contact with a macroporous polymeric adsorbent resin, an ion exchange resin or both.
    [0018]
    18. Composition according to claim 1, characterized in that the Luo Han Guo extract was placed in contact with a macroporous polymeric adsorbent resin, an ion exchange resin and activated carbon.
    [0019]
    19. Composition according to claim 1, characterized in that the Luo Han Guo extract was placed in contact with a macroporous polymeric adsorbent resin, an ion exchange resin and activated carbon, in the sequence listed.
    [0020]
    20. Composition according to claim 1, characterized in that the treatment with activated charcoal presents reduced levels of aromatic glycosides and semi-volatile organic compounds in the Luo Han Guo extract.
    [0021]
    21. Composition according to claim 1, characterized in that pesticide residues were removed from the Luo Han Guo extract as a result of treatment with activated charcoal.
    类似技术:
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    同族专利:
    公开号 | 公开日
    AU2012209241A1|2013-09-19|
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    AU2012209241B2|2015-12-17|
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    MX2013008633A|2013-10-03|
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    法律状态:
    2020-09-15| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|
    2020-09-24| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|
    2021-02-09| B15K| Others concerning applications: alteration of classification|Free format text: A CLASSIFICACAO ANTERIOR ERA: A23L 1/236 Ipc: A23L 27/10 (2016.01), A23L 33/105 (2016.01), A23L |
    2021-02-17| B07A| Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]|
    2021-06-22| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|
    2021-08-10| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 24/01/2012, OBSERVADAS AS CONDICOES LEGAIS. |
    优先权:
    申请号 | 申请日 | 专利标题
    US201161437399P| true| 2011-01-28|2011-01-28|
    US61/437,399|2011-01-28|
    PCT/US2012/022339|WO2012103074A2|2011-01-28|2012-01-24|Rebaudioside-mogroside v blends|
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