A supramolecular complex for inhibiting an enzyme and use in cosmetics

Abstract

The application provides an enzyme inhibiting supramolecular complex and application in cosmetics, and relates to the field of cosmetic raw materials.The supramolecular complex is a supramolecular structure formed by hydrogen bond connection of coriander glycoside and sodium phosphatide through high-pressure homogenization treatment and gradient freeze-drying treatment, and can inhibit key enzymes of sebaceous gland secretion, including aminoacylase N, 3beta-hydroxysteroid dehydrogenase and fatty acid synthase.The supramolecular complex can be added into different types of cosmetics, especially cosmetics with oil control and pore shrinking functions, so that the supramolecular complex can not only play a role of the composition itself, but also improve the transdermal rate by using the lipophilicity of phospholipid, and maximizes the cosmetic effect.

Description

Technical Field

[0001] This invention belongs to the field of cosmetic raw materials, and in particular relates to an enzyme activity that inhibits the secretion of sebum by sebaceous glands. Background Technology

[0002] Skin lipids are produced by sebaceous cells, keratinocytes, and the skin microbiome, significantly influencing skin condition through various mechanisms. Lipids are important metabolites with many vital cellular functions, including energy metabolism, signal transduction, enzyme activation, transmembrane transport, cell proliferation, development, differentiation, and apoptosis. Based on the type of linkages between lipid chains, they are classified into classes and subclasses. The classification system provided by the lipid atlas includes eight classes: fatty acids (FA), glycerides (GL), glycerophospholipids (GP), sphingolipids (SP), sterol esters (ST), allyl esters (PR), glycolipids (SL), and polyketides (PK).

[0003] The typical structure of skin lipids consists of three parts. (1) Lipids derived from sebaceous cells are synthesized by sebaceous glands and secreted onto the skin surface. The main components include squalene, triglycerides, fatty acids, wax esters, cholesterol, cholesterol esters, etc.; (2) Lipid precursors derived from keratinocytes are synthesized by keratinocytes and secreted in the form of lamellar structures. Finally, lipid precursors and lipid synthases are released into the extracellular space of stratum corneum cells, and lipid precursors are catalyzed by lipid synthases to generate lipids, mainly including ceramides (CER), fatty acids (FA), and bilirubin (CHOL); (3) The skin microbiota is an important source of skin lipids and cannot be ignored. The skin is colonized by a variety of microorganisms, most of which produce lipids in the skin during metabolism, such as short-chain fatty acids (SCFA). Propionibacterium acnes in the hair follicle duct produces lipases to convert triglycerides into monoglycerides, diglycerides, or free fatty acids; Staphylococcus epidermidis can esterify cholesterol; when sebum reaches the skin surface, squalene is oxidized. Therefore, compared to freshly secreted sebum, the lipids on the skin surface contain less triglycerides and more monoesters, diesters, or free fatty acids. The main source of lipids is sebaceous gland secretion. The lipid composition of sebaceous gland secretion is: triglycerides 41%, wax esters 25%, free fatty acids 16.4%, squalene 12%, cholesterol esters 2.1%, and cholesterol 1.4%. The average sebum production in a healthy adult is approximately 1 mg / 10 cm³. 2 Every 3 hours.

[0004] The key enzymes regulating sebum secretion by sebaceous glands include three parts: 1. Enzymes related to the regulation of sebaceous gland differentiation and proliferation: dipeptidyl peptidase IV and aminopeptidase N; 2. Hormones related to the regulation of sebum secretion, involving key enzymes in the synthesis of squalene, cholesterol, pregnenol, androstenediol, testosterone, and dihydrotestosterone, including cholesterol synthesis rate-limiting enzyme (HMG-CoA), cholesterol side chain cleavage enzyme, 17β-hydroxysteroid dehydrogenase, 3β-hydroxysteroid dehydrogenase, Δ5,Δ4-isomerase, aromatase (CYP19A1), steroid 5α-reductase I (SRD5A1), and steroid 5α-reductase II (SRD5A2). 3. Key enzymes in the synthesis of triglycerides and waxes in sebaceous glands: citrate lyase (ACLY), acetyl-CoA carboxylase (ACC), fatty acid synthase (FAS), stearoyl-CoA (SCD), fatty acid desaturase-2 (FADS2), and fatty acid chain elongation enzyme (ELOVL).

[0005] Active substances in natural products mainly originate from natural organisms such as plants, animals, and microorganisms. They are obtained through extraction, purification, and concentration, exhibiting structural diversity and biological activity, and fall under the category of natural products. Plant-based sources are predominantly numerous. Supermolecules, based on molecular assemblies and intermolecular covalent hydrogen bonds, achieve multi-molecular strength, elongation, and fracture toughness, increasing the permeability of substances. Different types of intermolecular interactions can be distinguished based on their varying strengths, orientations, and dependence on distance and angle.

[0006] Commonly used natural plant extracts in cosmetics for oil control and acne treatment include Scutellaria baicalensis, Forsythia suspensa, Salvia miltiorrhiza, Taraxacum mongolicum, Lonicera japonica, Paeonia suffruticosa, Morus alba root bark, Hedyotis diffusa, Coix lacryma-jobi, Prunella vulgaris, Citrus aurantium, Viola yedoensis, Anemarrhena asphodeloides, Ligusticum chuanxiong, Ligustrum lucidum, Crataegus pinnatifida, Pinellia ternata, and Paeonia lactiflora. However, these extracts are complex in composition, require high dosages, have unclear targeting, and carry potential sensitization risks. Some plant extracts target the type I 5α-reductase pathway to achieve oil control; however, this enzyme is limited to converting testosterone into dihydrotestosterone and does not reduce testosterone production. It also does not consider sebaceous gland differentiation and proliferation, or triglyceride synthesis, thus having certain limitations.

[0007] How to utilize the active substances in natural products to inhibit the enzyme system in the skin that regulates sebum secretion by sebaceous glands, thereby achieving targeted and highly effective skincare product formulations, is a problem that urgently needs to be solved. Summary of the Invention

[0008] The purpose of this invention is to provide a supramolecular complex that inhibits sebum secretion from sebaceous glands. The active ingredient in the supramolecular complex effectively inhibits the enzymes that secrete sebum from sebaceous glands in the skin, thereby reducing skin lipid secretion and solving problems such as inflammation, clogged pores, and enlarged pores caused by excessive sebum secretion.

[0009] To solve the above-mentioned technical problems, the present invention provides a supramolecular complex that can inhibit key enzymes in sebum secretion. The specific technical solution is as follows:

[0010] A supramolecular complex that inhibits the key enzyme in sebum secretion is formed from sodium phosphatidylcholine (PLA) and citronellol.

[0011] Furthermore, the supramolecular complex is composed of the following mixture in the following proportions:

[0012] Mix 50-90 parts of sodium phosphatidylcholine (PLA) and 15-30 parts of coriander glycoside, dissolve them in a 0.025-0.25 mol / L sodium hydroxide aqueous solution to prepare a 1-20% aqueous solution, and perform high-pressure homogenization at a pressure greater than 50-150 MPa, a flow rate of 10-100 ml / min, for 10-60 minutes, followed by freeze drying at a gradient temperature of -80℃ to -4℃.

[0013] Furthermore, sodium phosphatidylcholine is mainly derived from lysophospholipids (LPLs) produced by the sequential reaction of soybeans or egg yolks with phospholipase A1 (PLA1) and phospholipase A2 (PLA2). These LPLs are then converted into phosphatidic acid (LPA) by the reaction of lysophospholipase D (Lyso PLD), and sodium hydroxide is added at a 1:1 mol ratio for saponification.

[0014] Furthermore, piracetamine mainly comes from plants of the Rutaceae family, specifically those in the genus Rutaceae and the genus Citrus.

[0015] Furthermore, the genus *Ruta* includes *Ruta rotundifolia*. Agathosma betulina (PJBergius) Pillans or Buku ( Barosma betulina Bartl. & HLWendl.); Citrus genus includes sour orange (Citrus aurantium Linnaeus) and broadleaf lemon. (Citrus latifolia Tanaka ex Q. Jiménez).

[0016] Furthermore, the whole plant of *Citrus bucrocarpa* or *Citrus leucosus* is dried and dehydrated; pulverized into a fine powder of 40-80 mesh; soaked in an ethanol-water mixture at a material-to-liquid ratio of 1:10 (7:3), with pectinase and cellulase added at 0.1-0.5% of the dry matter weight of *Citrus bucrocarpa* during the soaking process, and stirred for 10 hours; the mixture is then filtered three times using a plate and frame filter to remove enzymes, tannins, fibers, and pigments; the extract is concentrated by molecular distillation to remove solvents and low- and medium-polarity active substances, collecting the high-polarity fraction; the high-polarity fraction is then collected by supercritical carbon dioxide extraction; and finally, the extract is heated to 50°C to remove the solvent and crystallize to obtain piracetaminoside.

[0017] Furthermore, the enzymes that secrete sebum from sebaceous glands include enzymes that regulate sebaceous gland activity, such as the key enzymes 17β-hydroxysteroid dehydrogenase and 3β-hydroxysteroid dehydrogenase in cholesterol-to-testosterone synthesis; key enzymes that enable acetyl-CoA to carboxylate into palmitic acid and triglycerides, such as acetyl-CoA carboxylase (ACC), fatty acid synthase (FAS), stearoyl-CoA (SCD), and fatty acid desaturase-2 (FADS2); and aminopeptidase N (APN), an enzyme involved in sebaceous gland proliferation and differentiation.

[0018] Furthermore, the half-inhibitory concentrations (IC50) of the supermolecules inhibiting 3β-hydroxysteroid dehydrogenase, fatty acid synthase, and aminopeptidase N were 0.05 mg / ml, 0.11 mg / ml, and 0.32 mg / ml, respectively.

[0019] Supramolecular complex components are key enzymes that inhibit sebum secretion from sebaceous glands, serving as natural skincare ingredients and are used in the cosmetics industry for oil control and pore minimization.

[0020] Furthermore, the supramolecular complex component containing the key enzyme that inhibits sebum secretion from sebaceous glands is added to the cosmetic at a mass ratio of 0.01%-10%.

[0021] Furthermore, the cosmetics include various skin care formulations such as toners, masks, gels, lotions, and creams.

[0022] The supramolecular complex of an enzyme that inhibits sebum secretion by sebaceous glands, as described in this invention, has the following advantages:

[0023] This invention provides a supramolecular complex of sodium phosphatidylcholine and citrus succinate obtained by biocatalysis, molecular distillation, supercritical carbon dioxide extraction, and spray drying of citrus succinate and lemon. This complex is then homogenized with sodium phosphatidylcholine under ultra-high pressure and freeze-dried. Compared to mechanically mixed compositions, this complex has smaller particle size, higher permeability, stronger stability, and higher water solubility. The molecules can be linked by hydrogen bonds to form complex, organized aggregates while maintaining a certain degree of integrity and microstructure. It can be added to various types of cosmetics, especially products with oil-controlling and pore-minimizing properties. It can safely and effectively inhibit sebum secretion-related enzymes in the skin, particularly 3β-hydroxysteroid dehydrogenase, fatty acid synthase (FAS), and aminopeptidase N (APN), reducing sebaceous gland proliferation and differentiation, as well as testosterone and fatty acid synthesis, thereby maximizing the targeted efficacy of cosmetics.

[0024] The supramolecular complex is formed by high-pressure homogenization of sodium phosphatidylcholine and citronellol in a dilute alkaline solution. Structural analysis shows that the hydroxyl part of the rutin at the farthest end of the aglycone nucleus of citronellol can share a charge with the sodium salt part of sodium phosphatidylcholine, forming phosphatidylcholine-citronellol. Attached Figure Description

[0025] Figure 1 This is a bar chart showing the inhibitory enzyme activity of a supermolecular complex. Detailed Implementation

[0026] To better understand the purpose, structure, and function of this invention, a supramolecular complex for inhibiting sebaceous secretion enzymes will be described in further detail below with reference to the accompanying drawings.

[0027] Skin pores are tiny openings on the surface of the skin. On one hand, "skin pores" refers to the openings of sweat gland ducts, which are invisible to the naked eye (5–10 micrometers in diameter). On the other hand, "skin pores" also refers to the visible openings of sebaceous gland hair follicles, whose opening diameter is generally 40–80 micrometers.

[0028] Enlarged pores are mainly caused by two factors: increased sebum secretion from the sebaceous glands and loss of collagen around the pores. 1. Excessive sebum secretion makes pores appear larger under light refraction and reflection. Additionally, excess sebum mixes with dead skin cells that haven't shed properly, forming plugs that clog pores and physically enlarge them. Excessive sebum secretion also increases free fatty acid levels, leading to inflammation and a color difference between the pores and the surrounding skin. 2. Due to factors such as light exposure, environment, and age, dermal aging causes skin collapse at the pore area, resulting in a height difference between the pores and the surrounding skin, giving them an oval or teardrop shape. Excessive proliferation of sebaceous gland stem cells leads to an increase in the surface area of ​​the sebaceous glands. Controlled hormone changes cause lipid cells to metabolize rapidly, producing triglycerides.

[0029] Hormone metabolism begins with the formation of cholesterol, which is then converted into testosterone, and finally into dihydrotestosterone. The three molecules of acetyl-CoA from the tricarboxylic acid cycle are catalyzed by thiolytic enzymes and HMG-CoA synthase to generate HMG-CoA. HMG-CoA, under the catalysis of HMG-CoA reductase, consumes two molecules of NADPH and H to generate mevalonate, which is then synthesized into squalene and cholesterol on the endoplasmic reticulum. Cholesterol, as a substrate, consumes NADPH on the inner mitochondrial membrane and, catalyzed by side-chain cleavage enzymes, sequentially yields pregnenolone, 17-α-hydroxypregnenolone, and dehydroepiandrosterone. This is followed by 17β-hydroxysteroid dehydrogenase to generate androstenedione, and then by 3β-hydroxysteroid dehydrogenase and Δ5,Δ4 isomerase to generate testosterone. On one hand, testosterone is metabolized by aromatase (CYP19A1) into 17β-estradiol (E2)—the most potent endogenous estrogen in the human body, which exerts its biological effects through estrogen receptor α (ERα) and estrogen receptor β (ERβ). On the other hand, testosterone is metabolized by steroid 5α-reductase type 1 (SRD5A1) and steroid 5α-reductase type 2 (SRD5A2) into 5α-dihydrotestosterone (DHT)—the most potent endogenous androgen in the human body, which exerts its biological effects through androgen receptor (AR).

[0030] The synthesis of triglycerides begins with citric acid obtained from the tricarboxylic acid cycle as a substrate. The citric acid is then passed through citrate lyase, acetyl-CoA carboxylase, and fatty acid synthase to obtain palmitate. This palmitate is then catalyzed by stearoyl-CoA desaturase to obtain monounsaturated fatty acids, followed by fatty acid desaturase-2 to obtain polyunsaturated fatty acids, and finally phosphatidic acid. 1,2-Diaacylglycerol (DAG) and triglycerides (TAG) are then synthesized from phosphatidic acid as substrates.

[0031] Sebaceous glands and their functions: Sebaceous glands are present in the skin of all mammals except whales and porpoises. One of their prominent functions is the secretion of sebum, a relatively neutral mixture of lipids, most of which is resynthesized by the glands, covering the fur as a hydrophobic protection, preventing excessive moisture and providing insulation. Sebaceous glands endow the skin with independent endocrine functions and play an important role in hormone-induced skin aging (37,38). They express all the enzymes required for steroid production. In addition, in many species, specialized sebaceous gland-like structures, such as the prepuce glands in rodents, are primarily responsible for releasing pheromones for territorial marking and sexual attraction. However, the composition of sebum exhibits significant species specificity, and in humans, the function of these sebaceous glands appears to be of limited importance. Although sebum is the main component of lipids on the surface of human skin, it is suggested that the latter does not form a barrier; sebum was previously thought to have no antibacterial or antifungal properties in vivo. Sebum, a product of active sebaceous glands, transports lipid-soluble antioxidants from the skin surface to the skin surface. Corticotropin-releasing hormone (CRH) is a hypothalamic-pituitary-adrenal (HPA) neurotransmitter that regulates sebaceous cell proliferation, induces neutral lipid synthesis, and enhances the mRNA expression of Δ5-3β-hydroxysteroid dehydrogenase. DP-IV is a homodimeric type II transmembrane glycoprotein (76), belonging to the postproline dipeptidyl aminopeptidase family, which also includes fibroblast activators DP VIII, DP IX, and DP II. DP IV is a serine exopeptidase that preferentially catalyzes the release of n-terminal dipeptides from oligopeptides and polypeptides, with proline in the penultimate position. APN is a 150 kDa type II membrane metalloproteinase primarily expressed in bone marrow mononuclear cell lineages and catalyzes the hydrolysis of neutral amino acids from the n-terminus of oligopeptides (79). This enzyme has been shown to participate in the degradation of several neuropeptides, angiotensin, cytokines, immunomodulatory peptides, and extracellular matrix proteins. The functional role of exopeptidases in sebaceous gland organs, and the use of these exopeptidase inhibitors, alone or in combination, as a novel group of substances, strongly affect sebaceous cell function and may play a therapeutic role in the early stages of acne pathogenesis.

[0032] Piperidin, also known as piperidin and piperidin, found in Bukhu and Lemon succinate has the structure 3',5,7-trihydroxy-4'-methoxyflavonoid 7-rutin. It is a grayish-yellow, hygroscopic powder. In dilute alkaline solutions, the hydroxyl groups of the rutin side chain are free.

[0033] Example

[0034] The entire plant of either *Citrus pulcherrima* or *Citrus aurantiacus* is treated according to the following steps:

[0035] Dehydration: The entire plant of the above-mentioned plants is dried and dehydrated;

[0036] Crushing: The dried material obtained after drying is crushed by a crusher and passed through a 40-80 mesh sieve;

[0037] Alcohol extraction: Mix 70% ethanol with dry matter at a ratio of 10:1 and soak for 10 hours;

[0038] Enzymatic hydrolysis: During the soaking process, add 0.1% pectinase and 0.2% cellulase by weight of the dried plant.

[0039] Sieving: The soaked mixture is passed through a plate and frame filter three times to obtain the filtrate;

[0040] Fractional distillation: Molecular distillation of the filtrate to obtain a highly polar fraction;

[0041] Purification 1: The highly polar extract was subjected to supercritical carbon dioxide extraction to obtain crude coriander glycosides;

[0042] Purification 2: Heat to 50℃ to remove solvent, and crystallize to obtain piracetamine for later use.

[0043] Sodium phosphatidyl acid was obtained by processing egg yolks according to the following steps:

[0044] Enzymatic hydrolysis: 100,000 IU of phospholipase A1, A2, and lysophospholipase were added at 0.01% of the weight of the egg yolk. The mixture was kept in a constant temperature water bath at 35°C and stirred for 30 minutes. The reaction system was prepared into a 50% egg yolk aqueous solution using phosphate buffer solution (pH 6.5).

[0045] Purification: After the reaction is complete, filter through a 0.22-micron membrane;

[0046] Saponification: Phosphatidic acid and sodium hydroxide are added to a reaction vessel in a molar ratio of 1:1, and the mixture is stirred for 1 hour to obtain sodium phosphatidate.

[0047] The three natural product molecules obtained above—bukuroiperidine, broadleaf limoniperidine, and sodium phosphatidylcholine—were used to prepare supramolecular complexes according to the proportions in Table 1 for subsequent experiments.

[0048]

[0049] Preparation of supramolecular complexes.

[0050] 1. Take piracetam and sodium phosphate according to the proportions in Table 1; 2. Prepare a 0.1 mol / L sodium hydroxide aqueous solution, and prepare a 5% (w / w) mixture of piracetam and sodium phosphate in 100 ml; 3. Homogenize under high pressure (100 MPa) at a flow rate of 25 ml / min for 30 minutes; 4. Freeze-dry at -80℃ for 4 hours, increasing the temperature by 10℃ per step, freezing for 1 hour per step, until reaching -20℃, then increasing the temperature by 5℃ per step, freezing for 1 hour per step, until reaching -5℃. Seven sets of freeze-dried powder samples were prepared for later use.

[0051] Detection of supramolecular complexes.

[0052] 1. Detection of maximum absorption wavelength using a UV-Vis spectrophotometer: Comparative Examples 1, 2, and 3 are λ... 344nm , λ 343 nm , λ 345 nm , λ 273 nm Comparative Example 4 is λ 271 nm The second peak is λ 345 nm The ultraviolet absorption peak exhibits a bimodal structure. In Examples 1, 2, and 3, the maximum absorption wavelengths of the obtained supramolecular complexes are, in order, λ. 298 nm , λ 296 nm , λ 305 nm Furthermore, the peak around 273 nm disappeared, while the 345 nm peak was very weak, indicating that the maximum absorption peak of the example was shifted compared to comparative examples 1, 2, and 3. This suggests the formation of a supramolecular complex.

[0053] 2. High-performance liquid chromatography (HPLC) detection of supramolecular complexes: HPLC conditions: column, flow rate 1 ml / min, UV detection wavelength 275 nm, mobile phase acetonitrile / water. Gradient elution was used, starting with 90% water-10% acetonitrile and ending with 10% water-90% acetonitrile. Each gradient was defined as a 10-part decrease in water concentration, with each gradient elution lasting two minutes, for a total of 18 minutes. Comparative Examples 1, 2, and 3 showed single-peak retention times of 13.82, 13.77, and 9.85, respectively; Comparative Example 4 showed retention times of 9.73 and 13.71, exhibiting a bimodal structure. Examples 1, 2, and 3 yielded supramolecular complexes with triple-peak retention times of 9.80, 11.25, and 13.78, respectively. However, the peak area integral at retention time 11.25 accounted for 74.32%, while the other two peaks accounted for 18.54% and 7.14%, respectively. This indicates the formation of supramolecular complexes.

[0054] Establishment of an in vitro inhibition model.

[0055] Add 0.1 mg of the enzyme solution from Table 2, and 0.1 mg of buffer solution from Examples 1-3 / Comparative Examples 1-4, to a water bath at 38°C for 10 minutes. Add 2 ml of androstenediol, malonyl-CoA, and hydrolyzed whey protein to each of the Control Groups 1-3, and incubate at 38°C for 10 minutes. Shake well and let stand for 1 hour. Take 2 ml of the supernatant and centrifuge at 14 kg / min for 5 minutes. Measure the absorbance of the supernatant at 275 nm.

[0056] The test group included supramolecular complexes obtained in Examples 1-3 and mixtures obtained in Comparative Examples 1-4, and the enzyme activities of 3β-hydroxysteroid dehydrogenase, fatty acid synthase, and aminopeptidase N were detected.

[0057]

[0058] Inhibition rate = (OD of test group - OD of supramolecular complex - OD of control group) / OD of control group.

[0059] The inhibition rates of 3β-hydroxysteroid dehydrogenase obtained from in vitro model testing are shown in Table 3. Both the supramolecular complex and the comparative examples showed some inhibitory effect on 3β-hydroxysteroid dehydrogenase, with the supramolecular complex exhibiting a significantly higher inhibition rate than comparative examples 1-4. The composition of Example 2 is preferred.

[0060]

[0061] The results of fatty acid synthase inhibition rate obtained from in vitro model testing are shown in Table 4. All supramolecular complexes in the examples exhibit a certain inhibitory effect on fatty acid synthase, while the comparative examples show weaker inhibitory effects or even promoting effects. The inhibition rate of the supramolecular complexes is significantly higher than that of comparative examples 1-4. The composition of Example 1 is preferred.

[0062]

[0063] The inhibition rates of aminopeptidase N obtained from in vitro model testing are shown in Table 5. All supramolecular complexes in the examples exhibited a certain inhibitory effect on aminopeptidase N, with inhibition rates exceeding 60%. The comparative examples showed weaker inhibitory effects or even promoting effects on aminopeptidase N. The inhibition rates of the supramolecular complexes were significantly higher than those of comparative examples 1-4. The composition of Example 3 is preferred.

[0064]

[0065] Test case

[0066] The extract of the present invention was prepared according to Table 6 and then subjected to subsequent tests.

[0067]

[0068] Fibronectin activity test (1) Evaluation of facial smoothness in human experiments.

[0069] Experimental Methods: Thirty Asian women aged 20-40 years were selected for a half-face comparison test. The test sample was applied to the left cheek, and the control sample to the right cheek, with the entire face applied twice daily. Facial VISIA images were captured for each participant at days 0 and 14. The Image-Pro® Plus Chinese Version 7.0.1 image processing and enhancement analysis system was used to process pore area and number. A Cutometer MPA 580 sebum probe was used to collect oil content data. Pore area, number of pores, and oil content were analyzed for both left and right cheeks, and the percentage change was calculated. A negative (-) indicated a decrease, and a positive (+) indicated an increase. The average value was calculated for all 30 participants. A significance analysis was performed.

[0070] In the test cases, pore area, pore number, and cheek oil volume decreased by an average of -16.33%, -18.78%, and -17.87%, respectively, significantly higher than the average control group. For pore area, 50% of the test cases showed a reduction of 10%-30% in pore area, with only 16.67% showing no reduction. In contrast, 56.67% of the control group showed a reduction of 5%-20%, with 20% showing no reduction in pore area. For pore number, 66.67% of the test cases showed a reduction of 10%-30% in pore number, with only 10% showing no reduction in pore area. In contrast, 46.67% of the control group showed a reduction of 5%-20% in pore number, with 23.33% showing no reduction in pore number. In the test cases of facial oil reduction, 60% of the participants experienced a reduction in oil content of 10%-30%, with only 3.33% showing no reduction. In contrast, 46.67% of the participants in the comparative study experienced a reduction in facial oil content of 5%-20%, and 33.33% reported no reduction in oil content. All three aspects demonstrate that the supramolecular complex used in the test cases is superior to ordinary mechanical mixtures in controlling oil and minimizing pores.

[0071]

[0072] It is understood that the present invention has been described through some embodiments, and those skilled in the art will recognize that various changes or equivalent substitutions can be made to these features and embodiments without departing from the spirit and scope of the invention. Furthermore, under the teachings of the present invention, these features and embodiments can be modified to adapt to specific situations and materials without departing from the spirit and scope of the invention. Therefore, the present invention is not limited to the specific embodiments disclosed herein, and all embodiments falling within the scope of the claims of this application are within the protection scope of the present invention.

Claims

1. A supramolecular complex for inhibiting the enzyme of sebaceous glands that secretes sebum, characterized in that, The supramolecular complex is composed of coriariagenin and sodium phosphatide, sodium phosphatide 50-90 parts, coriariagenin 15-30 parts; coriariagenin is from buchu and ruta graveolens; The preparation method of the supramolecular complex is characterized in that the mixture of coriariagenin and sodium phosphatide is configured into a 1-20% aqueous solution, high-pressure homogenization is carried out, the pressure is greater than 50-150 MPa, the flow rate is 10-100 ml / min, the time is 10-60 minutes, and the freeze-drying is carried out in a gradient temperature of-80℃ to-4℃; The preparation method of coriariagenin in the supramolecular complex is characterized in that, S1 dehydration: drying and dehydration treatment is carried out on buchu and ruta graveolens, and 5 kinds of plants; S2 crushing: the dry matter is crushed by a crusher and sieved through a 40-80 mesh sieve; S3 alcohol extraction: water-alcohol soaking extraction is used, 70% ethanol and dry matter are in a ratio of 10:1; S4 biological lysis: during the soaking process, 0.1-0.5% pectinase and cellulase are added according to the weight of the dry matter of buchu, and stirring and soaking are carried out for 10 hours; S5 purification 1: plate and frame circulation filtration is carried out for 3 times; S6 purification 2: molecular distillation is used to concentrate the extraction solution, and the high-polarity part is collected; S7 purification 3: the high-polarity part is collected through supercritical carbon dioxide extraction; S8 purification 4: heating at 50℃ to remove solvent and crystallize to obtain coriariagenin; The preparation method of sodium phosphatide in the supramolecular complex is characterized in that, S1 enzymatic hydrolysis: the reaction of phospholipase A1 and phospholipase A2 produces lysophosphatidate, which is converted into phosphatidic acid by lysophospholipase D reaction, 0.01% is added, constant temperature water bath at 35℃, stirring for 30 minutes, and the reaction system is configured into a 50% egg yolk aqueous solution with a phosphate buffer solution at pH 6.5; S2 purification: 0.22 micron filter membrane is used after the reaction is completed; S3 saponification: phosphatidic acid and sodium hydroxide are added to the reaction kettle according to a molar ratio of 1:1, stirring reaction is carried out for 1 hour, and sodium phosphatide is obtained.

2. Use of a supramolecular complex inhibiting the enzyme of sebaceous glands that secretes sebum in cosmetics, characterized in that, The cosmetic product includes cosmetic water, facial mask, jelly, emulsion and cream.

3. Use of a supramolecular complex of an enzyme that inhibits the secretion of sebum according to claim 2 in a cosmetic product, characterized in that, The composition is added to the cosmetic product in a mass ratio of 0.01%-10%.

4. The supramolecular complex of claim 1, wherein the enzyme is selected from the group consisting of lipase, phospholipase, and a combination thereof. The enzyme is an enzyme that regulates sebum activity in the skin, an enzyme that metabolizes hormones, and an enzyme that synthesizes triglycerides.

5. An enzyme which inhibits the secretion of sebum according to claim 4, characterized in that, The enzyme is aminopeptidase N, 3β-hydroxysteroid dehydrogenase, and fatty acid synthase.

Images