A type of xanthohumol microcapsule, its preparation method and application

Abstract

This invention, entitled "A Xanthohumulin Microcapsule, Its Preparation Method, and Its Application," belongs to the field of cosmetic technology. The technical problem to be solved is to provide a xanthohumulin microcapsule with higher stability, better encapsulation effect, simpler operation, and higher cost-effectiveness. The key technical points are: a xanthohumulin microcapsule, characterized in that the raw materials for preparing the xanthohumulin microcapsule include: xanthohumulin, component A, component B, and dipropylene glycol; the mass ratio of xanthohumulin to component A and component B is 0.01-1:0.25:0.075-0.5; component A is whey protein or whey protein peptide; and component B is chitosan hydrochloride.

Description

Technical Field

[0001] This invention belongs to the field of cosmetic technology, specifically relating to a xanthohumol microcapsule, its preparation method, and its application. Background Technology

[0002] Xanthohumol (XN) is a small molecule compound extracted from hops (Humulus lupulus L.). It belongs to the chalcone class of flavonoids in polyphenols, and its structural formula is shown in Formula 1.

[0003]

[0004] Formula 1 Xanthumol possesses various biological activities, including antioxidant, anti-inflammatory, antitumor, and neuroprotective effects, and has wide applications in cosmetics and other fields. However, its applications are significantly limited. Xanthumol has extremely low water solubility and bioavailability, and it is prone to isomerization under the influence of light and heat, which restricts the widespread use of this natural active ingredient.

[0005] Microencapsulation technology is an encapsulation technique that uses natural polymer materials as wall materials to encapsulate active substances into fine particles through physical or chemical methods. This technology can isolate sensitive active ingredients from the external environment in an encapsulated form, thereby effectively blocking the influence of adverse factors such as air and light. For example, Chinese invention patent CN109820837A discloses a microcapsule containing natural astaxanthin ester and its preparation method. The microcapsule includes a capsule wall material and an oil phase containing natural astaxanthin ester encapsulated by the capsule wall material. The capsule wall material includes main components and auxiliary components. The main components are one or more of gums, polysaccharides, polysaccharides, proteins, and peptides. The auxiliary components are one or more of sucrose esters, polyol fatty acid esters, ascorbic acid and its salts, isoascorbic acid and its salts, ethylenediaminetetraacetic acid, and natural polyphenols. The oil phase includes natural astaxanthin ester, fat, oil, phospholipids, polyol, and stabilizers. However, stabilizers still need to be added to the oil phase of this microcapsule to improve the stability of the natural astaxanthin ester.

[0006] Furthermore, there are currently no known technologies that utilize microencapsulation to address the stability and water solubility issues of xanthohumol. Existing conventional microencapsulation techniques are also prone to drawbacks such as solvent residue, cumbersome process steps, and insufficient membrane mechanical strength. Therefore, there is an urgent need in this field to provide xanthohumol microcapsules that offer higher stability, better encapsulation performance, simpler operation, and greater cost-effectiveness. Summary of the Invention

[0007] The purpose of this invention is to provide: A method for preparing xanthohumulin microcapsules, and related technologies, to solve technical problems such as providing xanthohumulin microcapsules with higher stability, better encapsulation effect, simpler operation, and higher cost-effectiveness, or combinations thereof.

[0008] Terminology Explanation: Unless otherwise defined, all technical terms in this invention have the same meanings as commonly understood by one of ordinary skill in the art to which the subject matter pertains. Unless otherwise stated, all patents, patent inventions, and disclosures referenced in this invention are incorporated herein by reference in their entirety. If multiple definitions exist for terms in this invention, the definitions in this chapter shall prevail.

[0009] It should be understood that the above brief description and the following detailed description are exemplary and for illustrative purposes only, and do not limit the subject matter of the invention in any way. In this invention, the singular is used in conjunction with the plural unless otherwise specifically stated. It should also be noted that, unless otherwise stated, the use of “or” or “or” means “and / or”. Furthermore, the use of the term “comprising” and other forms such as “including,” “containing,” and “contains” are not limiting.

[0010] The definition of the standard chemical term can be found in the reference "Food Microencapsulation Technology", China Light Industry Press, 2006.

[0011] Unless otherwise stated, conventional methods within the scope of the art, such as encapsulation efficiency and Fourier transform infrared spectroscopy, shall be used for testing.

[0012] Unless specifically defined, the use of various commercially available products in this invention employs standard techniques. For example, it may be carried out using the manufacturer's instructions for use with the reagent kit, or in accordance with methods known in the art or the description of this invention. The techniques and methods described herein can generally be implemented according to conventional methods well known in the art, based on the descriptions in the various summary and more specific documents cited and discussed in this specification.

[0013] The term "microcapsule" as used in this invention refers to a semi-transparent, closed microcapsule on which a solid or liquid drug (referred to as core material) is encapsulated by a polymer or copolymer (referred to as capsule material). The microcapsule has a granular or spherical appearance and a diameter between 5 and 400 μm.

[0014] The term "encapsulation rate" used in this invention refers to the percentage of drug encapsulated in liposomes and nanoparticles relative to the total drug content. It reflects the degree to which the drug is encapsulated by the carrier and is an important indicator for quality control.

[0015] The term "homogenization" as used in this invention refers to the process of micronizing and homogenizing the dispersions in a suspension (or emulsion) system. This process simultaneously reduces the size of the dispersions and improves the uniformity of their distribution. This technology refines materials through actions such as extrusion and impact; for example, a high-pressure homogenizer can break down fat particles in dairy products to improve system stability.

[0016] In a first aspect, the present invention provides: A type of xanthohumulin microcapsule, wherein the raw materials for preparing the xanthohumulin microcapsule include: xanthohumulin, component A, component B and dipropylene glycol; The mass ratio of xanthohumol to component A and component B is 0.01-1:0.25:0.075-0.5; Component A is whey protein or whey protein peptide; component B is chitosan hydrochloride.

[0017] As some specific embodiments of the present invention, the mass ratio of xanthohumol to component A and component B is 0.01-1:0.25:0.075-0.5, including but not limited to 0.01:0.25:0.075, 0.05:0.25:0.075, 0.1:0.25:0.075, 0.01:0.25:0.25, 0.05:0.25:0.25, 0.1:0.25:0.25, 0.01:0.25:0.5, 0.05:0.25:0.5, 0.1:0.25:0, or any ratio within this mass ratio range.

[0018] In some preferred embodiments of the present invention, the mass ratio of the fulvic acid to component A and component B is 1:0.5:0.15, 1:0.5:0.5, or 1:0.5:1. Under these mass ratio conditions, a higher fulvic acid loading effect can be achieved.

[0019] Secondly, the present invention provides: The preparation method of the above-mentioned xanthohumol microcapsules includes the following steps: (1) First, dissolve whey protein or whey protein peptide in water to obtain solution A; dissolve chitosan hydrochloride in water to obtain solution B; dissolve xanthohumol in dipropylene glycol to obtain solution C; (2) Adjust the pH values ​​of solutions A and B to 7.0 ± 0.1; (3) After solution A is stirred and homogenized, solution C and solution B are added in sequence and stirred and homogenized to obtain a mixed solution. After drying, the solution is obtained.

[0020] As some preferred embodiments of the present invention, in step (3), before drying, the microcapsules need to be homogenized 3-5 times under a pressure of 800-1200 bar. The homogenization pressure includes, but is not limited to, 800 bar, 900 bar, 1000 bar, 1100 bar, 1200 bar, or any pressure within this range; the number of homogenization cycles includes, but is not limited to, 3, 4, or 5 times. High-pressure homogenization further reduces the particle size of the microcapsules, thereby improving the transdermal absorption effect.

[0021] As some specific embodiments of the present invention, the mass-to-volume ratio of fulvic acid to dipropylene glycol is 0.04-0.06 g: 5-15 mL, including but not limited to: 0.04 g: 5 mL, 0.04 g: 10 mL, 0.04 g: 15 mL, 0.05 g: 5 mL, 0.05 g: 10 mL, 0.05 g: 15 mL, 0.06 g: 5 mL, 0.06 g: 10 mL, 0.06 g: 15 mL, or any mass-to-volume ratio within this range; preferably 1 g: 200 mL. This preferred ratio can further improve the encapsulation effect of fulvic acid in the microcapsules.

[0022] As some specific embodiments of the present invention, the mass-to-volume ratio of the whey protein or whey protein peptide to water is 0.2-0.3g:40-50mL, including but not limited to: 0.2g:40mL, 0.2g:45mL, 0.2g:50mL, 0.25g:40mL, 0.25g:45mL, 0.25g:50mL, 0.3g:40mL, 0.3g:45mL, 0.3g:50mL, or any mass-to-volume ratio within this range; preferably 1g:180mL. This preferred ratio can further improve the encapsulation effect of fulvic acid in the microcapsules.

[0023] As some specific embodiments of the present invention, the mass-to-volume ratio of chitosan hydrochloride to water is 0.075-0.5g:40-50mL, including but not limited to: 0.075g:40mL, 0.075g:45mL, 0.075g:50mL, 0.25g:40mL, 0.25g:45mL, 0.5g:50mL, 0.5g:40mL, 0.5g:45mL, 0.5g:50mL, or any mass-to-volume ratio within this range; preferably 1g:90mL. This preferred ratio can further improve the encapsulation effect of fulvic acid in the microcapsules.

[0024] As some specific embodiments of the present invention, in step (3), the homogenization conditions of solution A and solution C and solution B after addition are: homogenization at 10000-12000 rpm for 3-6 min; wherein, the homogenization speed includes but is not limited to 10000, 11000, 12000 rpm or any speed within the range of such speed; the homogenization time includes but is not limited to 3, 4, 5, 6 min or any time within such time.

[0025] Thirdly, the present invention provides: Application of the above-mentioned xanthohumol microcapsules or the xanthohumol microcapsules prepared by the above-mentioned preparation method in the preparation of cosmetics.

[0026] The beneficial effects of this invention are as follows: This invention utilizes dipropylene glycol to dissolve xanthohumol. With the aid of whey protein or whey protein peptides and chitosan hydrochloride, effective encapsulation of xanthohumol is achieved, effectively delaying isomerization and improving its stability. Furthermore, by optimizing the amounts of whey protein or whey protein peptides and chitosan hydrochloride, the encapsulation effect is further improved without significantly altering the particle size or particle size distribution.

[0027] This invention further improves the encapsulation effect of xanthohumulin through a high-pressure homogenization preparation process, while the resulting microcapsule xanthohumulin has smaller particle size, higher stability, and better resolubility. Attached Figure Description

[0028] Figure 1 This is the standard curve for xanthohumol.

[0029] Figure 2 Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 1.

[0030] Figure 3 Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 2.

[0031] Figure 4 The Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 3 is shown.

[0032] Figure 5 The Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 4 is shown.

[0033] Figure 6 The Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 5 is shown.

[0034] Figure 7 The Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 6.

[0035] Figure 8The Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 7.

[0036] Figure 9 Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 8.

[0037] Figure 10 Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 9.

[0038] Figure 11 Fourier transform infrared spectrum of the xanthohumol microcapsules prepared in Example 10.

[0039] Figure 12 The image shows a scanning electron microscope image of the xanthohumol microcapsules prepared in Example 3.

[0040] Figure 13 The image shows a scanning electron microscope image of the xanthohumol microcapsules prepared in Example 8.

[0041] Figure 14 The image shows the reconstituted state of the xanthohumol microcapsules prepared in Examples 3 and 8. Detailed Implementation

[0042] The following non-limiting embodiments are intended to enable those skilled in the art to gain a more comprehensive understanding of the present invention, but do not limit the invention in any way. The following content is merely an exemplary description of the scope of protection claimed by the present invention, and those skilled in the art can make various changes and modifications to the present invention based on the disclosed content, and such changes should also fall within the scope of protection claimed by the present invention.

[0043] The present invention will be further described below by way of specific embodiments. Unless otherwise specified, all instruments, devices, equipment, reagents, products, etc., used in the embodiments of the present invention are obtained through conventional commercial means.

[0044] The source information for some of the raw materials is shown in Table 1.

[0045] Table 1 Raw Material Information Table

[0046] Example 1 A method for preparing xanthohumol microcapsules, comprising the following steps: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0047] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0048] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a liquid sample, which is then freeze-dried to obtain the final product.

[0049] Example 2 A method for preparing xanthohumol microcapsules differs from Example 1 only in that: after stirring and homogenizing, a high-pressure homogenization process is added three times. The specific steps are as follows: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0050] (2) Stir solutions A, B and C at 60°C and 500 rpm for 2 hours until completely dissolved. Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0051] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 3 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0052] Example 3 A method for preparing xanthohumol microcapsules differs from Example 1 only in that: after stirring and homogenizing, a high-pressure homogenization process is added five times. The specific steps are as follows: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0053] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0054] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0055] Example 4 A method for preparing xanthohumol microcapsules differs from Example 3 only in the amount of chitosan hydrochloride used. The specific steps are as follows: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.25g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0056] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0057] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a liquid sample, which is then freeze-dried to obtain the final product.

[0058] Example 5 A method for preparing xanthohumol microcapsules differs from Example 3 only in the amount of chitosan hydrochloride used. The specific steps are as follows: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.075g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0059] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0060] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a liquid sample, which is then freeze-dried to obtain the final product.

[0061] Example 6 A method for preparing xanthohumol microcapsules differs from Example 1 only in that whey protein is replaced with an equal amount of whey protein peptides. The specific steps are as follows: (1) Weigh 0.25g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0062] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0063] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a liquid sample, which is then freeze-dried to obtain the final product.

[0064] Example 7 A method for preparing xanthohumol microcapsules differs from Example 6 only in that: after stirring and homogenizing, a high-pressure homogenization process is added three times. The specific steps are as follows: (1) Weigh 0.25g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0065] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0066] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 3 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0067] Example 8 A method for preparing xanthohumol microcapsules differs from Example 6 only in that: after stirring and homogenizing, a high-pressure homogenization process is added five times. The specific steps are as follows: (1) Weigh 0.25g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0068] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0069] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0070] Example 9 A method for preparing xanthohumol microcapsules differs from Example 8 only in the amount of chitosan hydrochloride used. The specific steps are as follows: (1) Weigh 0.25g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.075g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0071] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0072] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0073] Example 10 A method for preparing xanthohumol microcapsules differs from Example 8 only in the amount of chitosan hydrochloride used. The specific steps are as follows: (1) Weigh 0.25g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.25g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0074] (2) Adjust the pH of solutions A and B to 7.0±0.1 (using 0.5 M citric acid or sodium hydroxide).

[0075] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0076] Comparative Example 1 A method for preparing xanthohumol microcapsules differs from Example 9 only in the amount of whey protein peptides used. The specific steps are as follows: (1) Weigh 0.05g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0077] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0078] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0079] Comparative Example 2 A method for preparing xanthohumol microcapsules differs from Example 8 only in the amount of whey protein peptides used. The specific steps are as follows: (1) Weigh 0.05g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0080] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0081] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0082] Comparative Example 3 A method for preparing xanthohumol microcapsules differs from Example 8 only in the amount of chitosan hydrochloride used. The specific steps are as follows: (1) Weigh 0.25g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.025g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0083] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0084] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0085] Comparative Example 4 A method for preparing xanthohumol microcapsules differs from Example 8 only in the amount of chitosan hydrochloride used. The specific steps are as follows: (1) Weigh 0.25g of whey protein peptides and dissolve them in 45mL of deionized water to obtain protein solution A; dissolve 0.6g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0086] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0087] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0088] Comparative Example 5 A method for preparing xanthohumol microcapsules differs from Example 3 only in that whey protein is replaced with an equal amount of gelatin. The specific steps are as follows: (1) Weigh 0.25g of gelatin and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0089] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0090] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0091] Comparative Example 6 A method for preparing xanthohumol microcapsules differs from Example 8 only in that whey protein peptides are replaced with an equal amount of corn peptides. The specific steps are as follows: (1) Weigh 0.25g of corn peptide and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0092] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0093] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0094] Comparative Example 7 A method for preparing xanthohumol microcapsules differs from Example 3 only in that chitosan hydrochloride is replaced with an equal amount of pectin. The specific steps are as follows: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of pectin in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0095] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0096] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0097] Comparative Example 8 A method for preparing xanthohumol microcapsules differs from Example 3 only in that chitosan hydrochloride is replaced with an equal amount of λ-caryopsis. The specific steps are as follows: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of λ-carrageenan in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of dipropylene glycol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0098] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0099] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0100] Comparative Example 9 A method for preparing xanthohumol microcapsules differs from Example 3 only in that dipropylene glycol is replaced with an equal amount of 2-hexyl-1-decyl alcohol. The specific steps are as follows: (1) Weigh 0.25g of whey protein and dissolve it in 45mL of deionized water to obtain protein solution A; dissolve 0.5g of chitosan hydrochloride in 45mL of deionized water to obtain polysaccharide solution B; weigh 0.05g of xanthohumol and dissolve it in 10mL of 2-hexyl-1-decyl alcohol to obtain solution C (wherein, solutions A, B and C are stirred at 60℃ and 500rpm for 2h until completely dissolved).

[0101] (2) Adjust the pH of solutions A and B to 7.0 ± 0.1 (using 0.5 M citric acid or sodium hydroxide).

[0102] (3) First, homogenize solution A at 11000 rpm for 5 min; then slowly add solution C to solution A and homogenize at 11000 rpm for 5 min to obtain a mixture; finally, slowly add solution B to the mixture and continue to homogenize at 11000 rpm for 5 min to obtain a primary sample. Then, homogenize at 1000 bar for 5 times to obtain the final liquid sample. Freeze-dry to obtain the final liquid sample.

[0103] Detection Example 1 The encapsulation efficiency of the xanthohumol microcapsules prepared in Examples 1-10 and Comparative Examples 1-9 was determined using the following methods: (1) Preparation of xanthohumol standard curve: To prepare a 0.1 mg / mL xanthohumol solution: Dissolve 1 mg of xanthohumol powder (pure) in 10 mL of anhydrous ethanol.

[0104] To prepare a 1.25 μg / mL xanthohumol solution: Take 25 μL of a 0.1 mg / mL xanthohumol solution and dilute it to 2 mL with anhydrous ethanol; then take an appropriate amount of the solution and perform a wavelength scan in the 200-800 nm range using a UV spectrophotometer to determine that the wavelength of the maximum absorption peak of xanthohumol is 305 nm.

[0105] The 1.25 μg / mL xanthohumol solution was diluted to obtain xanthohumol solutions of 1 μg / mL, 0.625 μg / mL, 0.3125 μg / mL, and 0.15625 μg / mL. Measurements were taken at the wavelength of the maximum absorption peak of xanthohumol, and a standard curve for xanthohumol was plotted.

[0106] (2) Determination of the encapsulation efficiency of xanthohumol microcapsules: The total xanthohumol content and the free xanthohumol content on the surface of the microcapsules were determined, and the encapsulation efficiency was calculated.

[0107] The determination of total xanthohumol involved dissolving the microcapsules in anhydrous ethanol, sonicating for 20 min, centrifuging at 4500 rpm for 15 min, collecting the supernatant, and measuring the UV absorbance at 305 nm. The total xanthohumol mass (m) was then calculated. 总 (μg).

[0108] Determination of unencapsulated xanthohumol: Microcapsules were immersed in petroleum ether and vortexed for 20 min, then centrifuged at 4500 rpm for 15 min. The upper organic phase was collected, and the petroleum ether was evaporated at 40℃. The microcapsules were then redissolved in ethanol, and the absorbance was measured at 305 nm. The mass of unencapsulated xanthohumol (m³) was calculated. 未 (μg).

[0109] The formula for calculating the encapsulation ratio is as follows: Encapsulation efficiency (%) = (m 总 -m 未 ) / m 总×100% The standard curve of xanthohumol is as follows Figure 1 As shown, the equation of the standard curve is: y = 0.70172x + 0.05728, R0 2 =0.996.

[0110] The encapsulation efficiency results are shown in Table 2.

[0111] Table 2. Encapsulation efficiency of xanthohumol by xanthohumol microcapsules

[0112] As shown in Table 2, the microcapsules prepared in the embodiments of the present invention all achieved an encapsulation rate of over 75% for xanthohumulin. When whey protein was used as the microcapsule wall material, the highest encapsulation rate reached 94.20 ± 0.49%. When whey protein peptides were used as the microcapsule wall material, Example 9 showed the highest encapsulation rate, at 92.22 ± 3.27%. Furthermore, comparisons between Examples 1-3 (whey protein microcapsules) or Examples 6-8 (whey protein peptide microcapsules) show that high-pressure homogenization significantly improves the microcapsule encapsulation rate. Comparisons between Examples 3-5 and Examples 8-10 show that chitosan hydrochloride can achieve comparable encapsulation rates within a certain dosage range.

[0113] Detection Example 2 The particle size, polydispersity index (PDI), and zeta potential of the xanthohumol microcapsules prepared in Examples 1-10 and Comparative Examples 1-9 were determined, respectively, using the following methods: 0.1 g of microcapsules were dissolved in 3.9 g of ultrapure water to obtain an aqueous solution of xanthohumulin microcapsules. 0.5 mL of the prepared xanthohumulin microcapsule sample solution was then added to 1.5 mL of ultrapure water and mixed thoroughly. The mixture was placed in a polystyrene cuvette, and the particle size, polydispersity index, and zeta potential of the xanthohumulin microcapsules were determined using a Malvern Nano-ZS90 laser particle size analyzer. The test results are shown in Table 3.

[0114] Table 3. Particle size, polydispersity index, and zeta potential of xanthohumol microcapsules

[0115] As shown in Table 3, comparing Examples 1-3 and Examples 6-8, the particle size gradually decreases. The difference in their preparation processes lies in increasing the number of high-pressure homogenization cycles. Under the same formulation conditions, Preparation Process 3, which underwent 5 high-pressure homogenization cycles, had the smallest particle size, while Preparation Process 1, which did not undergo high-pressure homogenization, had the largest particle size. This indicates that high-pressure homogenization helps reduce the microcapsule particle size and improves transdermal absorption. Furthermore, under the same preparation process, compared to whey protein, whey protein peptides can form microcapsules with a smaller particle size (300nm-400nm), which helps improve transdermal absorption. While the microcapsules prepared in Comparative Examples 1-9 also have a small particle size, these microcapsules have poor solubility, exhibiting a certain degree of insoluble matter after dissolution, which was detected by analyzing the supernatant.

[0116] Detection Example 3 The Fourier transform infrared (FTIR) spectra of the xanthohumol microcapsules prepared in Examples 1-10 were tested respectively to detect the microcapsule encapsulation effect.

[0117] The test method is as follows: 1-2 mg of xanthohumulin microcapsule powder is mixed with 100-200 mg of dry potassium bromide solid (KBr). The sample is detected and its characteristic chemical groups are analyzed using the potassium bromide pellet method and Fourier transform infrared spectroscopy. The scanning range is 4000-400 cm⁻¹. 1 .

[0118] The Fourier transform infrared spectra of the xanthohumol microcapsules prepared in Examples 1-10 are shown below. Figures 2-11 As shown in the figure. It can be seen that the xanthohumol monomer is located at approximately 1450-1600 cm⁻¹. -1 There are multiple medium-intensity peaks at approximately 1381 cm⁻¹, which is due to the C=C vibration of the aromatic ring of xanthohumol; and at approximately 1381 cm⁻¹... -1 The characteristic peak at this location is attributed to the symmetric bending vibration of the methyl group on the isopentenyl side chain of the xanthohumol molecule.

[0119] Figure 2 , Figure 5 For microcapsules that have not undergone high-pressure homogenization, the microcapsule bands are located at 1450-1600 cm⁻¹. -1 With 1381cm -1 The characteristic peak of xanthohumol with moderate intensity was still present. High-pressure homogenization significantly improved the encapsulation effect, as seen in the bands of microcapsules treated with high-pressure homogenization five times. Figure 4 , Figure 7 ), 1450-600cm -1 With 1381cm -1The typical characteristic peaks of xanthohumol at two locations have basically disappeared, indicating that the absorption peaks of xanthohumol have been covered by the strong absorption bands of the protein amide bonds and polysaccharide backbone of the wall material. This suggests that xanthohumol has been embedded in the composite wall material of whey protein / whey protein peptide and chitosan hydrochloride.

[0120] Detection Example 4 The morphology of the xanthohumol microcapsules prepared in Examples 3 and 8 was observed by scanning electron microscopy (SEM).

[0121] Scanning electron microscope images of the xanthohumol microcapsules prepared in Examples 3 and 8 are shown below. Figures 12-13 As shown in the table, the wall material combination of whey protein and chitosan hydrochloride can aggregate to form larger ellipsoidal microcapsules, while whey protein peptides form smaller spherical microcapsules, consistent with the particle size analysis results in Table 3. Furthermore, although the microcapsules obtained from whey protein peptides have smaller particle sizes and better transdermal absorption, their shells are relatively loose and have lower mechanical strength. Conversely, while the relatively larger whey protein particle size slightly affects scalp absorption, the resulting microcapsules have dense shells and high mechanical strength, making them suitable for different applications.

[0122] Case 5 The xanthohumol microcapsules prepared in Examples 3 and 8 were dissolved in water at a concentration of 25% (m / m), and the reconstitution state was observed. The results are as follows. Figure 14 As shown.

[0123] Depend on Figure 14 As can be seen, the aqueous solution of whey protein peptide microcapsules is a pale yellow transparent liquid (left), and the aqueous solution of whey protein microcapsules is a milky white liquid (right), both showing good rehydration solubility.

[0124] Finally, it should be noted that the above content is only used to illustrate the technical solution of the present invention, and is not intended to limit the scope of protection of the present invention. Simple modifications or equivalent substitutions made by those skilled in the art to the technical solution of the present invention do not depart from the essence and scope of the technical solution of the present invention.

Claims

1. A type of xanthohumol microcapsule, characterized in that, The raw materials for preparing the xanthohumol microcapsules include: xanthohumol, component A, component B, and dipropylene glycol; The mass ratio of xanthohumol to component A and component B is 0.01-1:0.25:0.075-0.5; Component A is whey protein or whey protein peptide; component B is chitosan hydrochloride.

2. The xanthohumol microcapsules according to claim 1, characterized in that, The mass ratio of xanthohumol to component A and component B is 0.5:0.25:0.075-0.

5.

3. The xanthohumol microcapsules according to claim 2, characterized in that, The mass ratio of xanthohumol to component A and component B is 1:0.5:0.15, 1:0.5:0.5, or 1:0.5:

1.

4. The method for preparing xanthohumol microcapsules according to any one of claims 1-3, characterized in that, Includes the following steps: (1) First, dissolve whey protein or whey protein peptide in water to obtain solution A; dissolve chitosan hydrochloride in water to obtain solution B; dissolve xanthohumol in dipropylene glycol to obtain solution C; (2) Adjust the pH values ​​of solutions A and B to 7.0 ± 0.1; (3) After solution A is stirred and homogenized, solution C and solution B are added in sequence and stirred and homogenized to obtain a mixed solution. After drying, the solution is obtained.

5. The preparation method according to claim 4, characterized in that, In step (3), the material needs to be homogenized 3-5 times under a pressure of 800-1200 bar before drying.

6. The preparation method according to claim 1, characterized in that, The mass-to-volume ratio of xanthohumol to dipropylene glycol is 0.04-0.06 g: 5-15 mL; preferably 1 g: 200 mL.

7. The preparation method according to claim 1, characterized in that, The mass-to-volume ratio of the whey protein or whey protein peptide to water is 0.2-0.3g:40-50mL; preferably 1g:180mL.

8. The preparation method according to claim 4, characterized in that, The mass-to-volume ratio of chitosan hydrochloride to water is 0.075-0.5g:40-50mL, preferably 1g:90mL.

9. The preparation method according to claim 4, characterized in that, In step (3), the conditions for homogenization of solution A and solution C and solution B after addition are: homogenization at 10000-12000 rpm for 3-6 min.

10. The use of the xanthohumulin microcapsules according to any one of claims 1-3 or the xanthohumulin microcapsules prepared by the preparation method according to any one of claims 4-9 in the preparation of cosmetics.

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