• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    curcumin solubilized the present invention relates to a solubilized, consisting of curcumin with a percentage less than or equal to 10% by weight, preferably less than or equal to 7.5% by weight, preferably special, of 6 % by weight, and at least one emulsifier with a hlb value in the range between 13 and 18, especially polysorbate 80 or polysorbate 20 or a mixture of polysorbate 20 and polysorbate 80, the mean diameter of the micelles being charged with curcumin it is between 5 nm and 40 nm, preferably between 6 nm and 20 nm, preferably between 7 nm and 10 nm.
    公开号:BR112015014654B1
    申请号:R112015014654-6
    申请日:2013-05-15
    公开日:2020-08-18
    发明作者:Dariush Behnam
    申请人:Aquanova Ag；
    IPC主号:
    专利说明:

    [0001] Curcumin is an extract of turmeric and has been used for centuries as a spice, food coloring (E100), but also as a medicine in traditional medicine and in recent decades it has become global and widely known in conventional medicine as an active substance in immunology, osteogenesis, angiogenesis, neurogenesis and carcinogenesis, thanks to the publication of numerous study results.
    [0002] Curcumin is offered in many final products (food supplements), such as, for example, in capsules or in cloudy liquid drinks, in their native form (powder) or combined with excipients such as oil, glycerin, ethanol, phospholipids or lecithin, cyclodextrin, gum arabic, gelatin, pectins, sugar esters of dietary fatty acids or saponins. However, the problem is that these formulations are not transparent, do not produce any clear aqueous solution and have extremely low absorption or bioavailability.
    [0003] To increase bioavailability, it is known to use other components besides curcumin, for the creation of carrier systems, such as, for example, emulsions or liposomes. While in emulsions curcumin is dissolved in a lipophilic phase and is stabilized in the form of drops in an aqueous environment, in liposomes curcumin can be maintained in a layer of phospholipids. This way, in fact, the bioavailability can be increased by up to 50%, however, these formulations as liposomes are extremely mechanically unstable and neither resistant to the environment in the stomach.
    [0004] In conventional medicine, curcumin finds special attention in the context of neurogenesis (among others, Morbus Alzheimer) and carcinogenesis (cancer). In order to be able to preventively tackle these popular diseases, first of all conditioned by age, which have already taken on threatening proportions for economic policy, the optimization of the absorption or bioavailability of curcumin through a respectively appropriate formulation is a task of the present invention. In addition, the present invention has the task of achieving a stable, homogeneous fine distribution of curcumin in the respective final products, such as foodstuffs and food supplements.
    [0005] The present invention provides a micellar curcumin formulation on the basis of which, in the scope of a study in humans, a bioavailability of at least 230 times greater than that of native curcumin has been found. The present invention provides a solubilized product consisting of curcumin with a percentage less than or equal to 10% by weight, preferably less than or equal to 7.5% by weight, preferably special, 6% by weight and at least one emulsifier with an HLB value in the range between 13 and 18, especially polysorbate 80 or polysorbate 20 or a mixture of polysorbate 20 and polysorbate 80, the mean diameter of micelles loaded with curcumin being in the range between 5 nm and 40 nm, preferably between 6 nm and 20 nm, preferably between 7 nm and 10 nm.
    [0006] With this, a large load of the micelles with curcumin can be performed with advantage, without the micelles breaking and the curcumin in the dilution with water being released as sediment.
    [0007] The formulation of transparent and completely stable, water-soluble curcumin according to the present invention presents, without the above mentioned excipients as in soft and hard gelatin capsules, in gelatin-free capsules (hard and / or soft) and in beverages or liquid final products based on water, regardless of pH, a stable transparency and in addition, a considerably improved bioavailability. Products with such transparency and solubility in water, but also especially with such a high bioavailability of the curcumin formulation are urgently sought by the relevant industry for innovative products such as capsule filling and as transparent curcumin drinks. As far as the inventor is aware, a curcumin formulation that meets these requirements does not yet exist.
    [0008] The particularly small size of the micelles in the solubilized according to the present invention generates a clear and permanently transparent product. The narrow particle size distribution also contributes to this, since that of the micelle diameter distribution only reaches about 4 nm to about 30 nm.
    [0009] The particle size distribution of the micelles was measured according to the principle of dynamic light scattering in a 180 ° retrodispersion arrangement with 780 nm wavelength laser light. Due to the small particle sizes, the formation of a transparent liquid is advantageously achieved, especially for perception by the human eye. The solubilized transparency can also be represented by its low turbidity.
    [0010] For this, the following working hypothesis is applied: The more transparent an aqueous dilution of a solubilized or other curcumin formulation is, the better its solubilization. The better the solubilization, the better the bioavailability.
    [0011] The solubilized product according to the present invention also stands out for the fact that the total circuminoid concentration in human blood plasma, measured one hour after oral administration of 500 mg of curcumin in the form of the solubilized product, is approximately 500 nm curcuminoid for each mL of plasma ± 100 ng of circuminoid for each mL of plasma. In comparison to this, in oral consumption of native curcumin in powder form, after one hour, only about 1.3 ng of curcuminoid was obtained for each mL of plasma.
    [0012] The study in humans that is the basis of these values was carried out with 24 healthy people, aged between 19 and 29 years old, who received once, orally, a 500 mg dose of native curcumin or curcumin in the form of the solubilized according to the present invention. At different times, within 24 hours of ingesting curcumin, blood tests were performed. In order to minimize the possible influence of food digested in parallel, the test subjects received standardized meals. One hour after ingesting curcumin natively, less than 1 nmol / L of plasma was measured, eight hours after ingestion, 2.4 nmol / L and 24 hours after ingestion, 2.4 nmol / L. In contrast, in curcumin solubilized according to the present invention, one hour after ingestion, 1.964 nmol / L of blood plasma was measured, eight hours after ingestion 307.1 nmol / L was measured, and 24 hours after intake, 67.7 nmol / L. In that, a solubilized with 66.5% by weight of curcumin (commercially called "6% NovaSol curcumin" of the holder) was used. Therefore, increases in the concentration of curcumin in the blood plasma by a factor between 36 and 2800 appeared through the formulation of the solubilized according to the present invention compared to native curcumin.
    [0013] In the measurement over a 24-hour period, the surface under the curve of the entire concentration of curcumin in the blood plasma (area under the total curcumin plasma concentration time curve AUC) was 42.6 nmopl h / L at administration of native curcumin and 9821.4 nmol h / L in the administration of the solubilized according to the present invention. A little generalizing it can be said that the AUC plasma for 24 hours of the curcumin solubilized according to the present invention is in the range of about 9500 to about 10,000 nmol h / L.
    [0014] Accordingly, the bioavailability of the 66.5% curcumin solubilized product is clearly better than that of the native form. Observed as plasma AUC for 24 hours, the bioavailability increases about 230 times due to the formulation of the solubilized according to the present invention.
    [0015] This can already be registered in the especially small turbidity of the solubilized product that can be understood as a type of characteristic value for bioavailability. The turbidity of the solubilized product according to the present invention is less than 30 FNU, preferably less than 20 FNU, and most preferably in the range between 0.5 FNU and 2 FNU, measured by measuring diffused light with infrared light according to the instructions of ISO 7027 with a dilution of the solubilized to a ratio of 1: 1000 in water.
    [0016] This small turbidity is maintained by the solubilizer according to the present invention also after 24 hours of storage at 21 ° C and pH 7, just as after an hour of storage at 37 ° C and pH 1, 1, that is, on the one hand, under conditions of storage at room temperature in aqueous dilution and, on the other hand, when passing through the stomach. Therefore, curcumin in the solubilized according to the present invention, according to the inventor's current understanding, is also present after passing through the stomach, still in the form of very small stable micelles, and can therefore be very well absorbed in the tract. subsequent digestive tract.
    [0017] For turbidity determination by experiment, turbidity measurement instruments are calibrated with a standard suspension. Therefore, the indication does not occur in the form of the measured light intensity, but as a concentration of the calibration suspension. In the measurement of any suspension, the indication therefore means that the respective liquid causes the same dispersion of light as the standard suspension of the indicated concentration. The internationally agreed turbidity pattern is formazine. The most common units is the indication "FNU", which means "Formazine Nephelometric Units". That is, for example, the unit used in the preparation of water for measuring at 90 ° according to the instructions of ISO 7072. The turbidity of the solubilized according to the present invention is less than 30 FNU, preferably less than 20 FNU, and preferably special, is in the range between 0.5 FNU and 2 FNU, measured by means of measurement of diffused light with infrared light according to the instructions of ISO 7027, with a dilution of the solubilized to a ratio of 1: 1000 in the water.
    [0018] Depending on the application case, the solubilized product according to the present invention may contain up to 5% by weight of water and / or between 12% by weight and 20% by weight of glycerin.
    [0019] With advantage it was evident that the solubilized according to the present invention can be offered in simple form in capsules for oral administration, since it does not harm the capsules. Accordingly, the present invention also provides a capsule filled with the solubilized, the capsule being made as a soft gelatin capsule or a hard gelatin capsule or as a soft capsule without gelatin or as a hard capsule without gelatin.
    [0020] Another way of offering is a fluid containing the solubilized according to the present invention, the fluid being a food, a drink, a cosmetic product such as a cream, a lotion or ointment or a pharmaceutical product. In particular, the fluid may contain an aqueous dilution of the solubilized product. The applicability of the solubilized according to the present invention in a fluid does not depend on its viscosity, likewise the solubilized can be integrated in both hydrophilic and lipophilic media.
    [0021] The following will be explained examples of execution for solubilized according to the present invention.
    [0022] Particle size measurements were performed with the Particle Metrix NANOTRAC backscatter particle analyzer. The measurement principle is based on dynamic light scattering (DLS) in a 180 ° heterodyne back scattering arrangement. In this geometry, a part of the laser beam is mixed with the diffused light. This has the same positive effect, with regard to the signal and noise ratio, as the overlapping of all light wave lengths in a Fourier spectrometer. The color of the sample has no influence on the quality of the measurement. The measurements were carried out in aqueous solution diluted 1000 times. For this, the solubilized was dissolved in water, with stirring. It can be completely dissolved in water. This solution is stable and transparent.
    [0023] Example 1: Curcumin solubilized with polysorbate 80.
    [0024] For the production of the solubilized product, only 930 g of polysorbate 80 and 70 g of 95% curcumin powder are used. These 70 g contain 95% curcumin, that is, 66.5 g.
    [0025] As polysorbate 80 commercially available preparations can be used, such as, for example, TEGO SMO 20 V, InCoPa or Crillet 4 / Tween 80-LQ- (SG), Croda or Lamesorb SMO 80, Cognis. Commercially available preparations can also be used as 95% curcumin powder, for example Oleoresin Turmeric 95% (Curcumin powder), Jupiter Leys or Curcumin BCM-95-SG, Eurochem or Curcumin BCM-95-CG, Eurochem or Curcuma Oleoresin 95%, Henry Lamotte.
    [0026] The polysorbate 80 is heated to about 48 ° C to about 52 ° C. With stirring, curcumin powder is added slowly to polysorbate 80. During the addition of curcumin powder, heating continues to about 87 ° C to about 91 ° C. The solubilized that forms is cooled to below 60 ° C and is then ready to be filled.
    [0027] The solubilized has a yellow-orange to reddish color, very dark, of intense color, and transparent.
    [0028] The percentage of curcumin can be increased at the expense of polysorbate 80 to more or less 10% by weight.
    [0029] Example 2: Solubilized curcumin with polysorbate 20.
    [0030] For the production of the solubilized, only 894 g of polysorbate 20 and 106 g of 95% curcumin powder are used. These 106 g contain 95% curcumin, that is, 100.7 g.
    [0031] As polysorbate 20 commercially available preparations can be used, such as, for example, TEGO SML 20 V, InCoPa or Tween 20, Crillet 1-LQ- (SG), Croda or Lamesorb SML 20, Cognis. Commercially available preparations can also be used as 95% curcumin powder, for example Oleoresin Turmeric 95% (Curcumin powder), Jupiter Leys or Curcumin BCM-95-SG, Eurochem or Curcumin BCM-95-CG, Eurochem or Curcuma Oleoresin 95%, Henry Lamitte.
    [0032] Polysorbate 20 is heated to about 63 ° C to about 67 ° C. Under stirring, curcumin powder is added slowly to polysorbate 20. During the addition of curcumin powder, heating continues to about 83 ° C to about 87 ° C. The solubilized that forms is cooled slowly to below 45 ° C and is then ready to be filled.
    [0033] The solubilized has a yellow-orange to reddish color, very dark, with an intense and transparent color.
    [0034] The percentage of curcumin can be varied at the expense of polysorbate 80. In the attached figure 1 photographs of samples of different curcumin formulations are shown. On the left side of the illustration, samples are shown 24 hours after the addition of water, at a temperature of 21 ° C, under neutral conditions (pH 7). On the right side of the illustration, the samples are shown under physiological conditions, one hour after addition to water, at a temperature of 37 ° C, under conditions such as in the stomach (pH 1.1). Respectively so much water was added to the outlet preparations that the concentration of curcumin in the sample shown was 11.4 g / L. The following formulations were compared in detail:
    [0035] Sample A: Curcumin extract, native form, powder, 95% curcumin (BCM 95). 12 g of the powder was introduced into water.
    [0036] Sample B: Micronized with 17.5% curcumin, powder, Raps. 65.1 g of the powder was placed in a liter of water.
    [0037] Sample C: Formulation of 13% curcumin, powder, Wacker Chemie. 87.7 g of the powder were placed in a liter of water.
    [0038] Sample D: Curcumin solubilized according to the present invention according to Example 1. 200 g of the liquid solubilized were placed in one liter of water.
    [0039] While at room temperature, in neutral conditions and also at 37 ° C and acidic conditions, samples A, B and C show both sedimentation formation and also phase separation, sample D is transparent and homogeneous. The solubilized product according to the present invention also shows, in the entire temperature range of minus 20 ° C to 100 ° C, no phase separation and no sedimentation formation. In addition, sample D shows both room temperature under neutral conditions as well as at 37 ° C and acidic conditions, a more intense red color, due to which the sample in black and white photography appears clearly darker than samples A, B and C that have a yellow-orange color.
    [0040] It is evident to the person skilled in the art that the present invention is not restricted to the execution examples described above, but, on the contrary, it can be varied in many ways. In particular, the characteristics of the various examples of execution can also be combined or replaced by each other.
    权利要求:
    Claims (10)
    [0001]
    1. Micellar curcumin formulation characterized by being composed of curcumin in an amount less than or equal to 10% by weight, preferably less than or equal to 7.5% by weight, particularly preferably 6% by weight, and at least minus an emulsifier with an HLB value in the range between 13 and 18, namely polysorbate 80 or polysorbate 20 or a mixture of polysorbate 20 and polysorbate 80, where the average diameter of micelles loaded with curcumin is between 5 nm and 40 nm, preferably between 6 nm and 20 nm, particularly preferably between 7 nm and 10 nm.
    [0002]
    2. Formulation, according to claim 1, characterized by the fact that the range of the micelle diameter distribution extends from 4 nm to 30 nm.
    [0003]
    3. Formulation according to any of the preceding claims, characterized by the fact that the turbidity of the formulation is less than 30 FNU, preferably less than 20 FNU, and particularly preferably, in the range between 0.5 FNU and 2 FNU , determined by measuring diffused light with infrared light, according to the requirements of the ISO 7027 standard, with a dilution of the formulation in water in the proportion of 1: 1000.
    [0004]
    4. Formulation according to any one of the preceding claims, characterized by the fact that the turbidity of the formulation after 24 hours of storage at 21 ° C and pH 7 is less than 30 FNU, preferably less than 20 FNU, and particularly preferably, in the range between 0.5 FNU and 2 FNU, determined by measuring diffused light with infrared light, according to the requirements of the ISO 7 027 standard, with a dilution of the formulation in water in the proportion of 1: 1000.
    [0005]
    5. Formulation according to any of the preceding claims, characterized by the fact that the turbidity of the formulation after one hour of storage at 37 ° C and pH 1.1 is less than 30 FNU, preferably less than 20 FNU, and particularly preferably, in the range between 0.5 FNU and 2 FNU, determined by measuring diffused light with infrared light, according to the requirements of the ISO 7027 standard, with a dilution of the formulation in water in a ratio of 1: 1000.
    [0006]
    6. Formulation, according to any of the preceding claims, characterized by the fact that the formulation contains up to 5% by weight of water.
    [0007]
    7. Formulation according to any one of the preceding claims, characterized by the fact that the formulation contains between 12% by weight and 20% by weight of glycerin.
    [0008]
    8. Capsule filled with a formulation as defined in any of the preceding claims, characterized by the fact that the capsule is formed as a soft or hard gelatinous capsule or as a soft or hard non-gelatinous capsule.
    [0009]
    9. Fluid containing a formulation as defined in any of claims 1 to 8, characterized by the fact that the fluid is selected from the group comprising food products, beverages, cosmetics and pharmaceutical products.
    [0010]
    10. Fluid according to claim 9, characterized by the fact that the fluid comprises an aqueous dilution of the formulation.
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    法律状态:
    2018-01-16| B07D| Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]|
    2018-05-02| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|
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    优先权:
    申请号 | 申请日 | 专利标题
    DE202012012130.8U|DE202012012130U1|2012-12-19|2012-12-19|Curcuminsolubilisat|
    DE202012012130.8.|2012-12-19|
    PCT/EP2013/001427|WO2014094921A1|2012-12-19|2013-05-15|Curcumin solubilisate|
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