Coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion compound and preparation method thereof

Abstract

The invention discloses a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion compound and a preparation method thereof, and particularly relates to the technical field of food raw materials. A preparation form of double-layer inclusion of phospholipid on the inner layer and cyclodextrin on the outer layer is adopted, so that the solubility and bioavailability of the coenzyme Q10 are remarkably improved, and good stability is shown. Meanwhile, the preparation process is simple, the used organic solvent is relatively safe and single, and the method is suitable for industrial mass production.

Description

Technical Field

[0001] The invention belongs to the technical field of food raw materials, and specifically relates to a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion compound and a preparation method thereof. Background Art

[0002] Coenzyme Q10 (coenzyme Q10), also known as decenone and ubiquinone, is orange-yellow in color and is an endogenously synthesized fat-soluble antioxidant. It is mainly present in mitochondria, as well as in all cell membranes, lipoproteins and blood. Coenzyme Q10 can be divided into oxidized form (Q, also known as ubiquinone) and reduced form (QH2, also known as ubiquinol). Reduced coenzyme Q10 on the market is extremely unstable and can be easily converted into oxidized coenzyme Q10. In addition, the price of reduced coenzyme Q10 is much higher than that of oxidized coenzyme Q10.

[0003] As a lipophilic substance, CoQ10 forms micelles with the help of pancreatic and bile secretions and is absorbed by the small intestine. After absorption, the body reduces CoQ10 to ubiquinol and incorporates it into chylomicrons, which are transported to the circulation through lymphatic vessels. In the liver, Coenzyme Q10 will be added to very low density lipoprotein (VLDL) / low density lipoprotein (LDL) particles and released into the circulation again.

[0004] Coenzyme Q10 is mainly involved in the electron transfer process of the cell respiratory chain in the body, and transforms the redox structure in the body, thereby playing an antioxidant role, which is essential for maintaining the energy supply of cells. In addition, Coenzyme Q10 also has anti-inflammatory, free radical scavenging, and cell protection from oxidative damage. It is widely used in health products and medicines for the treatment of cardiovascular diseases, improving immunity, anti-fatigue and anti-aging.

[0005] However, coenzyme Q10 is highly fat-soluble, extremely low in water-solubility, has a large molecular weight, has poor oral bioavailability, and is unstable under conditions such as light, heat, and oxygen, which greatly limits its clinical application effect.

[0006] In the existing technology, in order to improve the bioavailability of coenzyme Q10, researchers have proposed a variety of improvement schemes, from simple oily dispersions to nanotechnology-guided systems, such as nanocrystals, self-nanoemulsifying drug delivery systems, etc., to overcome the solubility problem. There is also water dispersion through microcapsule technology, but the improvement of water solubility is limited; liposome technology is used to improve bioavailability, but the coenzyme Q10 content is low, which is not conducive to large-scale industrial production; although phospholipid complex technology has a certain improvement in bioavailability, the effect is limited, the cost is high, it is easy to absorb moisture, and the application scenarios are limited.

[0007] Patent CN101053556A introduces the use of hydroxypropyl-β-cyclodextrin as cyclodextrin to encapsulate coenzyme Q10, and after drying, a coenzyme Q10 inclusion complex is formed, but the Q10 content is low.

[0008] Patent CN1981750B introduces a water-soluble coenzyme Q10 composition and preparation method, which uses coenzyme Q10, γ-cyclodextrin, sugar alcohol and disintegrant. The coenzyme Q10 composition is prepared by stirring in an aqueous medium with a high-speed homogenizer or ultrasonic oscillation, then passing through a high-pressure homogenizer, and finally freeze-drying to form a solid dispersion, granulating, and granulating. Although the bioavailability is improved to a certain extent, the production cost is relatively high.

[0009] Patent CN117618392A introduces a highly stable and water-soluble coenzyme Q10 microcapsule and a preparation method thereof. The microcapsule is prepared using coenzyme Q10, glyceryl monostearate, acetylated mono- and diglycerides, medium-chain glycerides, caprylic and capric glyceride, wall materials, and water to improve bioavailability.

[0010] Patent CN117204564A provides a water-soluble coenzyme Q10 composite carrier with high bioavailability, a preparation method and its application. A porous material is used to adsorb a gel precursor, i.e., a molten mixture of a dispersed phase, a gelling agent and coenzyme Q10, and the gelation process is controlled to obtain a high-load, high-bioavailability coenzyme Q10 composite carrier.

[0011] Currently, oxidized coenzyme Q10 is widely used in the market. Although the bioavailability of reduced coenzyme Q10 is better than that of the former, it is unstable, easily oxidized, and has a higher price. Many researchers are committed to improving the bioavailability of coenzyme Q10. Currently, most of them are coenzyme Q10 microcapsules, solid dispersions, inclusion compounds, etc.

[0012] Coenzyme Q10 has extremely high fat solubility, extremely poor water solubility, and low bioavailability. Therefore, improving the water solubility of coenzyme Q10 is an important research and development upgrade direction. Its solubility in buffer is a key indicator for evaluating the water solubility of the raw material. The solubility of coenzyme Q10 raw material in PBS7.0 is 0, and the solubility of some coenzyme Q10 microcapsule powders on the market is less than 5%. The solubility of coenzyme Q10 solid dispersions is also about 5%, and the inclusion rate of the inclusion complex is also poor. The solubility of coenzyme Q10 phospholipid complex is also poor, at only 6%.

[0013] The preparation process of the present invention is simple, and the organic solvent used is relatively safe and single, which is suitable for large-scale industrial production. The prior art mostly uses a two-phase solvent, which has both an aqueous phase and an organic phase, and the operation is relatively complicated, and the reaction needs to be very intense, such as introducing preparation methods such as high-pressure homogenization, otherwise Q10 cannot be included and the preparation is difficult to form. Summary of the invention

[0014] The purpose of the present invention is to provide a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion compound in view of the deficiencies of the prior art.

[0015] In a first aspect, the present invention provides a phospholipid-cyclodextrin bilayer inclusion complex of a fat-soluble compound, wherein the fat-soluble compound is specifically coenzyme Q10.

[0016] In some embodiments, the first layer of the phospholipid-cyclodextrin bilayer inclusion complex of the fat-soluble compound is composed of phospholipids complexed with coenzyme Q10 to form a phospholipid complex of coenzyme Q10.

[0017] In some embodiments, the second layer of the phospholipid-cyclodextrin bilayer inclusion complex of the fat-soluble compound is further comprised of a phospholipid complex of coenzyme Q10 included in cyclodextrin, thereby forming a coenzyme Q10 phospholipid-cyclodextrin bilayer inclusion complex.

[0018] In some embodiments, the phospholipids include, but are not limited to, one or more combinations of sunflower lecithin, soybean lecithin, egg yolk lecithin, phosphatidylcholine, cardiolipin, sphingomyelin, glycolipids, gangliosides, cerebrosides, PEG-derivatized lipids, monoglycerides, and diglycerides.

[0019] In some embodiments, the phospholipids include, but are not limited to, one or more combinations of sunflower lecithin, soybean lecithin, and egg yolk lecithin.

[0020] In some embodiments, it is characterized in that the cyclodextrin includes but is not limited to α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin.

[0021] In some embodiments, the mass ratio of phospholipid to cyclodextrin is 5:1-1:50.

[0022] In some embodiments, the mass ratio of phospholipid to cyclodextrin is 3:1-1:50.

[0023] In some embodiments, the mass ratio of phospholipid to cyclodextrin is 1:1-1:50.

[0024] In some embodiments, the mass ratio of phospholipid to cyclodextrin is 1:2-1:50.

[0025] In some embodiments, the mass ratio of phospholipid to cyclodextrin is 1:5-1:50.

[0026] In some embodiments, the mass ratio of Coenzyme Q10 to phospholipid is 20:1-1:10.

[0027] In some embodiments, the mass ratio of Coenzyme Q10 to phospholipid is 15:1-1:5.

[0028] In some embodiments, the mass ratio of Coenzyme Q10 to phospholipid is 12:1-1:1.

[0029] In some embodiments, the mass ratio of Coenzyme Q10 to cyclodextrin is 10:1-1:20.

[0030] In some embodiments, the mass ratio of Coenzyme Q10 to cyclodextrin is 5:1-1:10.

[0031] In some embodiments, the mass ratio of Coenzyme Q10 to cyclodextrin is 2:1-1:10.

[0032] In a second aspect, the present invention provides a method for preparing a phospholipid-cyclodextrin bilayer inclusion complex, wherein coenzyme Q10 is firstly complexed with phospholipid to form a coenzyme Q10 phospholipid complex; and then the complex is included with cyclodextrin to form a coenzyme Q10 phospholipid-cyclodextrin bilayer inclusion complex.

[0033] In some embodiments, only one organic solvent is used in the preparation method.

[0034] In some embodiments, the organic solvent includes but is not limited to ethyl acetate, methanol, ethanol, and acetone.

[0035] In some embodiments, the preparation method comprises the following steps:

[0036] (1) dissolving coenzyme Q10 in an organic solvent to obtain a coenzyme Q10 solution;

[0037] (2) dissolving phospholipids in the above solution and mixing them evenly to obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex;

[0038] (3) adding cyclodextrin to the coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex, and continuing to stir the reaction to form a phospholipid-cyclodextrin double-layer inclusion complex; removing the organic solvent from the inclusion complex solution to obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0039] In some embodiments, the solute ratio of Coenzyme Q10 to the organic solvent is 1 g: 1-1000 mL.

[0040] In some embodiments, the solute ratio of Coenzyme Q10 to the organic solvent is 1 g:3-500 mL.

[0041] In some embodiments, the solute ratio of Coenzyme Q10 to the organic solvent is 1 g:5-300 mL.

[0042] In some embodiments, the solute ratio of Coenzyme Q10 to the organic solvent is 1 g:7-100 mL.

[0043] In some embodiments, the solute ratio of Coenzyme Q10 to the organic solvent is 1 g:10-60 mL.

[0044] In some embodiments, the stirring temperature after adding cyclodextrin is 10-150°C.

[0045] In some embodiments, the stirring temperature after adding cyclodextrin is 20-120°C.

[0046] In some embodiments, the stirring temperature after adding cyclodextrin is 30-90°C.

[0047] In some embodiments, the stirring time is 1-30 hours.

[0048] In some embodiments, the stirring time is 1-20 hours.

[0049] In some embodiments, the stirring time is 1-10 h.

[0050] In a third aspect, the present invention provides a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex, further comprising food-acceptable additives.

[0051] In a fourth aspect, the present invention provides the above-mentioned coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex, and its use in the preparation of health foods, dietary supplements and / or foods for treating cardiovascular diseases, improving immunity, resisting fatigue and delaying aging.

[0052] In some embodiments, the cardiovascular disease is a heart-related disease.

[0053] In some embodiments, the phospholipid-cyclodextrin bilayer inclusion complex is used to power a heart.

[0054] In some embodiments, the double-layer inclusion complex is used to improve symptoms of palpitations, arrhythmias, heart palpitations, and low blood pressure associated with heart disease.

[0055] Beneficial effects:

[0056] 1. The coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex provided by the present invention adopts a preparation form in which the inner layer is phospholipid and the outer layer is cyclodextrin double-layer inclusion, which significantly improves the solubility and bioavailability of coenzyme Q10, the solubility in PBS buffer solution reaches 30%, and shows good stability.

[0057] 2. The preparation process of the present invention is simple, and the organic solvent used is relatively safe and single, which is suitable for large-scale industrial production. The reference document uses a two-phase method, which has both an aqueous phase and an organic phase. The operation is relatively complicated, and the reaction needs to be very intense, such as introducing preparation methods such as high-pressure homogenization, otherwise Q10 cannot be included and the preparation is difficult to form.

[0058] 3. Compared with the inclusion complex formed by coenzyme Q10 alone and phospholipid and the inclusion complex formed by coenzyme Q10 alone and cyclodextrin, the solubility of the double-layer inclusion complex of the present invention is much greater than the complex and inclusion complex formed alone, and has a synergistic effect. DETAILED DESCRIPTION

[0060] In order to facilitate the understanding of those skilled in the art, the present invention is further described below in conjunction with embodiments, and the contents mentioned in the implementation modes are not intended to limit the present invention.

[0061] Example 1

[0062] Dissolve 5 g of coenzyme Q10 in 175 mL of ethanol to obtain a coenzyme Q10 solution; dissolve 2.06 g of soybean lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 22.94 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue stirring the reaction, and react at 90° C. for 1 hour to form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0063] Example 2

[0064] Dissolve 5 g of coenzyme Q10 in 150 mL of ethanol to obtain a coenzyme Q10 solution; dissolve 1.24 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 13.76 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, and react at 70° C. for 2 hours to form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0065] Example 3

[0066] Dissolve 5 g of coenzyme Q10 in 300 mL of ethanol to obtain a coenzyme Q10 solution; dissolve 0.41 g of egg yolk phospholipids in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 4.59 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, and react at 50° C. for 5 hours to form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0067] Example 4

[0068] Dissolve 5 g of coenzyme Q10 in 50 mL of ethanol to obtain a coenzyme Q10 solution; dissolve 1.65 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 18.35 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, and react at 30° C. for 9 hours to form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0069] Example 5

[0070] Dissolve 5 g of coenzyme Q10 in 200 mL of ethanol to obtain a coenzyme Q10 solution; dissolve 1.7 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 28.30 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, react at 70° C. for 7 hours, and form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0071] Example 6

[0072] Dissolve 5 g of coenzyme Q10 in 200 mL of ethanol to obtain a coenzyme Q10 solution; dissolve 2.18 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 12.82 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, and react at 70° C. for 2 hours to form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0073] Example 7

[0074] Dissolve 5 g of coenzyme Q10 in 200 mL of ether to obtain a coenzyme Q10 solution; dissolve 3.3 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 36.70 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, and react at 70° C. for 5 hours to form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0075] Example 8

[0076] Dissolve 5 g of coenzyme Q10 in 200 mL of ethanol to obtain a coenzyme Q10 solution; dissolve 4.13 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 45.87 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, react at 70° C. for 5 hours, and form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0077] Example 9

[0078] Dissolve 5 g of coenzyme Q10 in 200 mL of petroleum ether to obtain a coenzyme Q10 solution; dissolve 4.13 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 45.87 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir and react, react at 70° C. for 5 hours to form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0079] Example 10

[0080] Dissolve 5 g of coenzyme Q10 in 200 mL of methanol to obtain a coenzyme Q10 solution; dissolve 4.13 g of sunflower lecithin in the above solution, mix well, and obtain a coenzyme Q10-phospholipid solution; add 45.87 g of cyclodextrin to the coenzyme Q10-phospholipid solution, continue to stir the reaction, react at 70° C. for 5 hours, and form an inclusion complex solution; evaporate the inclusion complex solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

[0081] Comparative Example 1

[0082] Dissolve 5g of coenzyme Q10 and 2.06g of phospholipids in 175mL of ethanol to obtain a coenzyme Q10 phospholipid solution; dissolve 22.94g of cyclodextrin in an appropriate amount of water to form a cyclodextrin solution; fully mix and stir the coenzyme Q10 solution and cyclodextrin solution, react at 90℃ for 1h, evaporate the reactants under reduced pressure, remove ethanol and water, and obtain the product. However, its properties are poor, the color is uneven, the texture is uneven, and coenzyme Q10 cannot be included.

[0083] Comparative Example 2

[0084] Dissolve 5 g of coenzyme Q10 in 175 mL of ethanol to obtain a coenzyme Q10 solution; add 25 g of cyclodextrin to the coenzyme Q10 solution, continue stirring the reaction, react at 90° C. for 1 hour to form an inclusion solution, evaporate the solution under reduced pressure to remove ethanol, and obtain a coenzyme Q10 inclusion complex.

[0085] Comparative Example 3

[0086] Dissolve 5 g of coenzyme Q10 in 175 mL of ethanol to obtain a coenzyme Q10 ethanol solution; dissolve 25 g of cyclodextrin in an appropriate amount of water to form a cyclodextrin solution; fully mix and stir the coenzyme Q10 solution and the cyclodextrin solution, react at 90° C. for 1 hour, evaporate the reactants under reduced pressure to remove ethanol and water, and obtain the product.

[0087] Comparative Example 4

[0088] 5 g of coenzyme Q10 was dissolved in MCT (medium chain triglycerides), 25 g of phospholipids and vitamin E were dissolved in 175 mL of ethanol, and the two were mixed to obtain a coenzyme Q10 phospholipid alcohol solution, to which a buffer solution was added, and ultrasonic treatment was performed for 30 minutes. The reactants were then evaporated under reduced pressure to remove ethanol, and water and modified starch were slowly added thereto. The mixture was fully mixed and stirred, and high shearing was performed for 5 minutes. The mixture was then spray-dried to obtain coenzyme Q10 liposomes.

[0089] Example 11 Dissolution Test

[0090] The mass ratio of coenzyme Q10 to the total mass of phospholipids and cyclodextrin was kept constant at 1:5, and the corresponding coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complexes were prepared according to different ratios (the ratio of phospholipids to cyclodextrin was 0%, 6%, 9%, 17%, 27%), which were samples 1-5, and dissolution tests were performed.

[0091] Dissolution Test:

[0092] Prepare pH 7.0 phosphate buffer containing 0.5% sodium taurocholate and dispense equal amounts into different dissolution cups at 37°C and 250 rpm;

[0093] Weigh the sample and dissolve it in different dissolution cups according to the coenzyme Q10 content, and start timing;

[0094] Samples were taken at 2 h, filtered and diluted, the liquid phase was taken up, the content of coenzyme Q10 in the aqueous solution was detected, and the dissolution was calculated as shown in Table 1.

[0095] Table 1

[0096] sample The ratio of phospholipids to cyclodextrin Dissolution / % Sample 1 0％ 0％ Sample 2 6％ 29％ Sample 3 9％ 30.8％ Sample 4 17％ 18％ Sample 5 27％ 3.5％

[0097] The principle of this preparation is to first react coenzyme Q10 and phospholipids to form a phospholipid complex through hydrogen bonds, and then add cyclodextrin to encapsulate the complex, first compounding and then encapsulating, so that coenzyme Q10 reaches dissolution, thereby improving bioavailability. Phospholipids are lipids with amphiphilicity. An appropriate amount of phospholipids can link the fat-soluble substance coenzyme Q10 and the water-soluble substance gamma-cyclodextrin through hydrogen bonds, van der Waals forces and other forces, thereby improving solubility and dissolution in water.

[0098] Example 12

[0099] The dissolution rates of two commercially available coenzyme Q10 microcapsules, coenzyme Q10 phospholipid complexes, and samples prepared according to this patent were tested.

[0100] Coenzyme Q10 microcapsule 1: The main excipients are sodium starch octenylsuccinate, maltodextrin, and corn oil;

[0101] Coenzyme Q10 microcapsule 2: The main excipients are sodium starch octenylsuccinate, corn starch, maltodextrin, gum arabic, and MCT oil.

[0102] Prepare pH 7.0 phosphate buffer and dispense equal amounts into different dissolution cups at 37°C and 250 rpm.

[0103] Weigh the coenzyme Q10 sample (in terms of coenzyme Q10 content) and dissolve it in different dissolution cups, and start timing;

[0104] Samples were taken at 2 h, filtered and diluted, the liquid phase was taken, the content of coenzyme Q10 in the aqueous solution was detected, and the dissolution rate was calculated, as shown in Table 2.

[0105] Table 2

[0106]

[0107]

[0108] The above data show that compared with the products obtained by single inclusion with phospholipid or cyclodextrin and reacting under two-phase conditions, the coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex prepared by the present invention has a better solubility effect.

[0109] Embodiment 13

[0110] Solubility test: Take appropriate amounts of coenzyme Q10 preparation and its raw materials, i.e., 2 microcapsule powders, 1 phospholipid complex, the double-layer inclusion compound of Example 1, and coenzyme Q10 raw materials, add 50 ml of aqueous solution, ultrasonically oscillate for 20 minutes, centrifuge and filter, take the filtrate as the test solution, and use high performance liquid chromatography to detect the coenzyme Q10 content in the solution. The results are shown in Table 3, indicating that the phospholipid-cyclodextrin double-layer inclusion compound of coenzyme Q10 of the present invention has better solubility.

[0111] Table 3

[0112]

[0113] It should be understood that the detailed description of the technical solutions of the present invention by means of the preferred embodiments is illustrative rather than restrictive. A person skilled in the art may modify the technical solutions described in the embodiments, or replace some of the technical features by equivalents, based on reading the specification of the present invention; and these modifications or replacements do not deviate the essence of the corresponding technical solutions from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A phospholipid-cyclodextrin bilayer inclusion complex of a fat-soluble compound, characterized in that: The fat-soluble compound is coenzyme Q10.

2. The phospholipid-cyclodextrin bilayer inclusion compound according to claim 1, characterized in that: The first layer is composed of phospholipids complexed with coenzyme Q10 to form a phospholipid complex of coenzyme Q10.

3. The phospholipid-cyclodextrin bilayer inclusion compound according to claim 2, characterized in that: The second layer further includes the phospholipid complex of coenzyme Q10 by cyclodextrin, thereby forming a phospholipid-cyclodextrin double-layer inclusion complex of coenzyme Q10.

4. The phospholipid-cyclodextrin bilayer inclusion compound according to any one of claims 1 to 3, characterized in that: The phospholipids include one or more of sunflower lecithin, soybean lecithin, egg yolk lecithin, phosphatidylcholine, sphingolipids, cardiolipin, sphingomyelin, glycolipids, gangliosides, cerebrosides, PEG-derived lipids, monoglycerides, and diglycerides.

5. The phospholipid-cyclodextrin bilayer inclusion compound according to any one of claims 1 to 4, characterized in that: The mass ratio of phospholipid to cyclodextrin is 5:1-1:

50.

6. The phospholipid-cyclodextrin bilayer inclusion compound according to any one of claims 1 to 4, characterized in that: The mass ratio of coenzyme Q10 to phospholipids is 20:1-1:

10.

7. The phospholipid-cyclodextrin bilayer inclusion compound according to any one of claims 1 to 4, characterized in that: The mass ratio of coenzyme Q10 to cyclodextrin is 10:1-1:

20.

8. The method for preparing the phospholipid-cyclodextrin double-layer inclusion compound according to any one of claims 1 to 7, characterized in that: First, coenzyme Q10 is complexed with phospholipids to form a coenzyme Q10 phospholipid complex; then the complex is included with cyclodextrin to form a phospholipid-cyclodextrin double-layer inclusion complex of coenzyme Q10.

9. The preparation method according to claim 8, characterized in that: Only one organic solvent is used in this preparation method.

10. The preparation method according to claim 9, characterized in that: The organic solvent is selected from ethyl acetate, methanol, ethanol and acetone.

11. The preparation method according to claim 10, characterized in that: The steps include: (1) dissolving coenzyme Q10 in an organic solvent to obtain a coenzyme Q10 solution; (2) dissolving phospholipids in the above solution and mixing them evenly to obtain a coenzyme Q10-phospholipid complex; (3) adding cyclodextrin to the coenzyme Q10-phospholipid complex, continuing to stir the reaction to form a phospholipid-cyclodextrin double-layer inclusion complex; removing the organic solvent from the inclusion complex solution to obtain a coenzyme Q10 phospholipid-cyclodextrin double-layer inclusion complex.

12. The phospholipid-cyclodextrin bilayer inclusion compound according to any one of claims 1 to 7, further comprising a food-acceptable additive.

13. The phospholipid-cyclodextrin bilayer inclusion compound according to any one of claims 1 to 11, wherein the phospholipid-cyclodextrin bilayer inclusion compound is used in the preparation of health food, dietary supplement and / or food for treating cardiovascular diseases, improving immunity, resisting fatigue and delaying aging.

14. The use of the phospholipid-cyclodextrin double-layer inclusion compound according to claim 13, characterized in that: The cardiovascular disease is a heart-related disease.

15. Use of the phospholipid-cyclodextrin double-layer inclusion compound according to claim 14, characterized in that: The phospholipid-cyclodextrin bilayer inclusion complex is used to provide power for the heart.

16. Use of the phospholipid-cyclodextrin double-layer inclusion compound according to claim 14, characterized in that: The double-layer inclusion compound is used to improve the symptoms of palpitations, arrhythmia, heart palpitations and low blood pressure associated with heart disease.

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