WO2021017317A1 - Procédé d'inhibition de la photodégradation d'ergothionéine et son application - Google Patents

Procédé d'inhibition de la photodégradation d'ergothionéine et son application Download PDF

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WO2021017317A1
WO2021017317A1 PCT/CN2019/118950 CN2019118950W WO2021017317A1 WO 2021017317 A1 WO2021017317 A1 WO 2021017317A1 CN 2019118950 W CN2019118950 W CN 2019118950W WO 2021017317 A1 WO2021017317 A1 WO 2021017317A1
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composition
hyaluronate
ergothioine
molecular weight
ergothioneine
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PCT/CN2019/118950
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English (en)
Chinese (zh)
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魏玉洁
陆震
贾玉倩
陈雯雯
毛华
孙元军
郭文逸
石艳丽
郭学平
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华熙生物科技股份有限公司
山东华熙海御生物医药有限公司
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Publication of WO2021017317A1 publication Critical patent/WO2021017317A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/38—Other non-alcoholic beverages
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the invention belongs to the field of biochemical industry, and relates to a method for inhibiting the photodegradation of ergothioine, in particular to a composition containing ergothioine and its application.
  • Ergothioneine is a rare natural amino acid discovered in a fungus Claviceps purpurea in 1909.
  • ergothioneine exists in many animals and plants, and has important physiological activities in the body. Studies have shown that it can eliminate free radicals, anti-inflammatory, maintain DNA biosynthesis, normal cell growth, and cellular immunity. kind of physiological function.
  • patent CN103181933B discloses a method for preparing a functional oral preparation rich in thioneine, which will be rich in thioneine edible The mycelium is mixed with water, stirred and leached at high temperature, and then concentrated and added with food additives to make a liquid oral preparation.
  • Patent CN109939027A discloses a method for preparing ergothioine-containing cosmetic stock solution by fermentation of Hericium erinaceus. The stock solution has strong anti-oxidation, anti-radiation and anti-inflammatory effects, and can be used as a raw material to be added to water, milk, cream and other cosmetics in.
  • ergothioine has the disadvantages of being easy to decompose when exposed to light and poor stability. The degradation of ergothioine will reduce or even disappear the efficacy. Therefore, it is necessary to find a method that can inhibit the photodegradation of ergothioneine and develop a product with stable efficacy that can be used in food, health products and cosmetics.
  • the present invention provides a method that can effectively inhibit the photodegradation of thiothione.
  • the invention also provides an ergothioine-containing composition which has stable efficacy and can be used in food, health care products and cosmetics.
  • the present invention adopts the following technical solutions.
  • a method for inhibiting the degradation of ergothioine includes the following steps: adding hyaluronate into a solution containing ergothioine.
  • An ergothioine-containing composition includes ergothioine and hyaluronate.
  • the content of the ergothioine in the solution or composition is 0.0005 to 0.01 wt%.
  • the content of the hyaluronic acid salt is not less than 0.1 wt%; more preferably not less than 0.5 wt%; even more preferably 0.5-1.2 wt%.
  • the ergothioine source may be ergothioine extract or ergothioine powder.
  • the ergothioneine extract is liquid or solid.
  • the ergothioine content in the liquid ergothioine extract is 50-500 mg/L; the ergothioine content in the solid ergothioine extract is 0.1-0.5 mg/g.
  • the hyaluronic acid salt is selected from salts that are conventionally used for skin or food, such as at least one of sodium salt, potassium salt, magnesium salt, zinc salt, calcium salt or quaternary ammonium salt.
  • the molecular weight of the hyaluronate is 3kDa-1800kDa.
  • the molecular weight of the hyaluronate can be in a single range, or a mixture of several different molecular weight ranges; such as high molecular weight hyaluronate (1000kDa-1800kDa), medium molecular weight hyaluronate (500kDa-1000kDa) ), a mix of low molecular weight hyaluronate (10kDa-500kDa) and ultra-low molecular weight hyaluronate (3kDa-10kDa).
  • the hyaluronate is 1-3 parts by weight of hyaluronate with a molecular weight of 1200kDa-1600kDa, 2-4 parts by weight of hyaluronate with a molecular weight of 300kDa-800kDa, and hyaluronate with a molecular weight of 3kDa-10kDa Mix of 2-5 parts by weight of acid salt.
  • the above composition can be prepared by conventional methods. For example, it is formulated into a mother liquor with a certain concentration after dissolution, or the raw material powders are uniformly mixed.
  • composition also contains auxiliary materials acceptable in the field of food and health food, such as at least one of solvents, preservatives, thickeners, flavoring agents, flavors and pigments.
  • the composition also contains auxiliary materials acceptable in the cosmetics field, such as solvents, solubilizers, surfactants, preservatives, antioxidants, pH regulators, penetration enhancers, liposomes, moisturizers, thickeners, chelating agents At least one of a mixture, a skin feel modifier, a surfactant, an emulsifier, a propellant/propellant, a fragrance, a coloring agent, and a sunscreen agent.
  • solvents solubilizers, surfactants, preservatives, antioxidants, pH regulators, penetration enhancers, liposomes, moisturizers, thickeners, chelating agents
  • solvents such as solvents, solubilizers, surfactants, preservatives, antioxidants, pH regulators, penetration enhancers, liposomes, moisturizers, thickeners, chelating agents
  • solvents such as solvents, solubilizers, surfactants, preservatives, antioxidants, pH regulators, penetration enhancers, liposome
  • composition also contains other effective ingredients, such as anti-oxidation, anti-ultraviolet, promoting cell proliferation, whitening, anti-inflammatory and other functional ingredients.
  • the use of the above composition in the preparation of food health products can be directly used for moisturizing and anti-aging, and can also be added to food health products as an active ingredient.
  • a food and health product containing the above composition containing the above composition.
  • the content of the composition in the food and health product is 0.1-100wt%; preferably 1-20wt%; more preferably 2-10wt%.
  • the function of the food health product can be a food health product that is moisturizing and anti-aging, anti-inflammatory, joint maintenance or repair, and intestinal and stomach clearing.
  • the food and health product can be in the form of at least one of beverages, powders, oral liquids, tablets, capsules, and granular solid powders.
  • compositions in the preparation of cosmetics can be directly used for skin moisturizing and anti-aging, and can also be added to cosmetics as an active ingredient.
  • a cosmetic comprising the above composition.
  • the content of the composition in cosmetics is 0.1-100% by weight; preferably 1-20% by weight; more preferably 2-10% by weight.
  • the cosmetic function can be moisturizing, anti-aging, anti-inflammatory, whitening, sunscreen or isolation cosmetics.
  • the cosmetic form may be at least one of sunscreen, release cream, skin lotion, toner, skin care gel, skin care lotion, skin cream, essence, eye cream, facial mask or spray.
  • the present invention combines hyaluronate and ergothioine, which can effectively inhibit the photodecomposition of ergothioine.
  • the composition is used in food health products and cosmetics, and has good moisture retention and functional stability.
  • Figure 1 is the influence of sodium hyaluronate concentration and molecular weight on the content of thioneine before and after light exposure;
  • Figure 2 shows the cell morphology of UV damaged cells treated with 5% of the sample
  • Figure 3 shows the morphology of the cells after 5% sample treatment and then UV damage.
  • Example 1 The inhibitory effect of hyaluronic acid on the photodegradation of thioneine
  • the light conditions 1000 Lux were used to simulate the degradation of thioneine-containing products during use to determine the inhibitory effect of hyaluronic acid on the photodegradation of thioneine.
  • Ergothioine is determined by high performance liquid chromatography, HPLC conditions: Column: Hypersil ODS C18 column (250mm ⁇ 4.6mm, particle size 5 ⁇ m); column temperature: 30°C; mobile phase: acetonitrile-water (3:97) ; Flow rate: 1.0mL/min; Detection wavelength: 254nm; Injection volume: 20 ⁇ L.
  • the initial thioneine content was 145.4 mg/L. After 5 days of light, the results of the change of thioneine content are shown in Table 1. From the results, when the addition amount of sodium hyaluronate is 0.5%, it can effectively inhibit the photodegradation of ergothioneine, and this inhibitory effect has nothing to do with the molecular weight of hyaluronic acid.
  • hyaluronic acid salts of various molecular weights have inhibitory effects on the degradation of thioneine.
  • the inhibitory effect of hyaluronic acid on the photodegradation of ergothione is directly proportional to the concentration. As the concentration increases, the inhibitory effect increases; when the concentration of hyaluronate reaches 0.6%, the slope of the curve becomes smaller and increases The amplitude tends to be flat.
  • sample S4 Take the sodium hyaluronate and thioneine extracts with a molecular weight of 3kDa-10kDa, add water and stir evenly to dissolve, to obtain sample S4;
  • the ratio of S1 take sodium hyaluronate with a molecular weight of 1200kDa-1600kDa and sodium hyaluronate with a molecular weight of 300kDa-800kDa, add water and heat to 85°C and stir to dissolve the sodium hyaluronate. After the sodium hyaluronate is completely dissolved, the temperature is reduced to 45 °C, then add the formula amount of sodium hyaluronate with a molecular weight of 3kDa-10kDa and stir evenly to obtain sample C2.
  • the samples S1-4 and C1 and C2 prepared in Example 2 were placed in transparent plastic bottles, and were placed in a light incubator (1000 Lux) at 25° C. for 5 days, or stored in the dark for 5 days before use.
  • a light incubator 1000 Lux
  • the illuminated samples S1-4, C1, C2 and non-illuminated S1, C1, C2 prepared in Example 2 were respectively dissolved in water to prepare solutions with the final concentrations of the above samples of 2.0%, 4.0%, 6.0%, and 8.0% spare. Precisely measure 5.0 mL of the DPPH solution and 5.0 mL of the sample solution prepared in Example 2 with different concentrations, respectively, and place them in a test tube with a stopper, and mix them evenly. Adjust zero with an equal volume of 95% ethanol-water mixed solution.
  • sample solution Prepare 5% concentration of the C1, C2, S1-4 and non-illuminated C1, C2, S1 sample solutions of Example 2 with serum-free DMEM culture solution, and filter them through a 0.22 ⁇ m filter. bacteria.
  • DCFH-DA probe solution Dilute DCFH-DA with PBS solution (0.1M, pH 7.4), and add 1mL PBS to 0.375 ⁇ L.
  • HaCaT cells in the logarithmic growth phase were seeded in a 12-well culture plate at a density of 5 ⁇ 10 4 cells/mL, 2 mL of cell suspension per well, and routinely cultured in a carbon dioxide incubator at 37° C. and 5% CO 2 for 24 hours.
  • Group operations as follows:
  • the level of ROS in the cells was significantly increased compared to the normal cultured cells. Compared with the damage model group, some ROS can be removed after exposure to the sample after UV damage. It can be seen from the data in Table 6 that the sample C2 prepared in Example 2 has a low ROS clearance rate, while C1 and S1-4 have a certain clearance effect on the generated ROS. However, ergothione is cleared of ROS after exposure to light. However, after adding hyaluronic acid to ergothioneine, the ROS clearance rate of the composition before and after light is relatively stable.
  • Example 4 The effect of the composition on the repair of UV-induced cell damage and the cell's defense against UV damage
  • sample solution The illuminated and non-illuminated samples S1, C1, C2 prepared in Example 2 were respectively dissolved in serum-free medium to prepare S1 and C1, C2 with final concentrations of 2.0%, 3.0%, 4.0%, and 5.0% The solution is filtered and sterilized with a 0.22 ⁇ m filter membrane for later use.
  • HaCaT cells Take the HaCaT cells in the logarithmic growth phase, after trypsinization, adjust the cell density to 1 ⁇ 10 5 /mL, inoculate in a flat-bottomed 96-well cell culture plate, 100 ⁇ L of cell suspension per well, and place in a carbon dioxide incubator at 37°C, 5% CO 2 routine culture overnight.
  • 7.2J/cm 2 UVA plus 126mJ/cm 2 UVB were used to irradiate HaCaT cells, and the test groups are as follows:
  • the culture medium was discarded, and 100 ⁇ L of the sample solution with a concentration of 2.0%, 3.0%, 4.0%, and 5.0% was added to each well.
  • the old culture medium was discarded in the normal group and the model group, and 100 ⁇ L of fresh culture medium was added. Enter the incubator and continue to cultivate for 24h.
  • Relative proliferation rate (%) absorbance of test group/absorbance of normal group ⁇ 100%
  • the ultraviolet damage repair ability of the ergothione extract after illumination is much lower than that of the non-illuminated ergothione extract, while the ultraviolet damage repair ability of the composition of the ergothione extract and hyaluronic acid before and after illumination is not significantly different. . It shows that hyaluronic acid can effectively inhibit the reduction of ergothione damage repairing ability after exposure to ultraviolet light.
  • UVA+UVB combined irradiation the HaCaT cell boundary is unclear, the membrane structure is damaged, and there are many apoptotic cells. After the irradiation, after the sample solution is processed, the HaCaT morphology partly returns to normal, and the apoptotic cells are significantly reduced.
  • Figure 2 shows the UV Cell morphology of damaged cells treated with 5% sample S1.
  • test groups were as follows. Each well of the test group was added with 100 ⁇ L of sample solution with a concentration of 2.0%, 3.0%, 4.0%, and 5%. The normal group and the model group were added with equal amounts of serum-free medium and placed in the incubator Continue to culture for 24h.
  • Human skin fibroblasts were irradiated with 7.2J/cm 2 UVA plus 126mJ/cm 2 UVB. After irradiation, discard the old culture medium, add serum-free culture medium, and continue culturing for 24 hours, add 10 ⁇ L WST-1 to each well, and place it in the cell culture incubator to continue incubating for 4 hours. Measure the light absorption value with a microplate reader at a wavelength of 450nm, and calculate the relative proliferation rate (%) according to the following formula:
  • Relative proliferation rate (%) absorbance of test group/absorbance of normal group ⁇ 100%
  • a beautifying, intestinal and stomachic beverage containing ergothioine composition which is composed of the following components:
  • thioneine composition 10, sodium citrate 0.2, honey 0.7, deionized water 89.1; thioneine composition: containing 1.2% potassium hyaluronate with a molecular weight of 1600kDa-1800kDa, thioneine extract 1 % (The content of ergothioneine is 200mg/L), supplemented with water;
  • Technological process mixing ergothioine composition, sodium citrate, honey and deionized water, compounding and sterilizing to obtain beverage.
  • a powder containing ergothioine composition for beauty, nourishing and joint maintenance which is composed of the following components:
  • thioneine composition 5 chondroitin sulfate 0.5, maltodextrin 10, honey 0.5, deionized water 84
  • thioneine composition containing 0.7% calcium hyaluronate with a molecular weight of 300kDa-800kDa, ergot Thiine extract 1.5% (ergothioine content is 150mg/L), supplemented with water;
  • a moisturizing and anti-aging sunscreen lotion containing ergothioine composition which is composed of the following components:
  • Ingredient wt% Phase A: sodium stearoyl glutamate 1.0, pentaerythritol distearate 2.0, dioctyl carbonate 5.0, dimethyl silicone oil 2.0, ethoxyethyl p-methoxycinnamate 7.5, paraben Ketone 5.0, Homosalicylate 5.0, Homosalate 5.0, Dimerized Linoleyl Alcohol/Dimethyl Carbonate Copolymer 1.0, Sodium Polyacrylate 0.6; Phase B: Ergothioine Composition 10.0, Deionized Water 55.9 , Flavor and preservative 0.1; thioneine composition: containing 0.1% sodium hyaluronate with a molecular weight of 1200kDa-1600kDa, 0.3% sodium hyaluronate with a molecular weight of 300kDa-800kDa, and sodium hyaluronate with a molecular weight of 3kDa-10kDa 0.5%, thioneine
  • Process Heating phase A and phase B to 80-85°C respectively. Add phase B to phase A with stirring. Homogenize at 55-60°C, stir and cool to below 30°C.
  • a moisturizing and anti-aging emulsion containing ergothioine composition consisting of the following components:
  • Phase A appropriate amount of deionized water, Carbo 934 NF 0.30
  • Phase B triethanolamine 0.10, deionized water 1.00
  • Phase C monoglyceride 5.00, cetyl alcohol 2.00, natural canola oil 2.00, simethicone 1.00
  • Phase D Ergothioine composition 15.0, Jimei II 0.30, flavor and preservative 0.1
  • Ergothioine composition containing 0.2% of sodium hyaluronate with a molecular weight of 1200kDa-1600kDa, 0.4% of sodium hyaluronate with a molecular weight of 300kDa-800kDa, 0.3% of sodium hyaluronate with a molecular weight of 3kDa-10kDa, thioneine extract 0.5% (ergothioine content is 400mg/L), 1,3-butanediol 2%, 1,2-pentanediol 3%, water supplement.
  • a moisturizing and anti-aging toner containing ergothioine composition which is composed of the following components:
  • Phase A glycerin 5.0, propylene glycol 3.0, oat extract 2.0, benzophenone-4/benzophenone-5 0.5, containing ergothioine composition 9.4, deionized water to 100
  • Thioine composition containing 0.1% sodium hyaluronate with a molecular weight of 1200kDa-1600kDa, 0.4% sodium hyaluronate with a molecular weight of 300kDa-800kDa, 0.4% sodium hyaluronate with a molecular weight of 3kDa-10kDa, thionin extract Liquid 1% (the content of ergothioneine is 200mg/L), 1,3-butanediol 2%, 1,2-pentanediol 3%, water supplement.
  • Phase B Azone/PEG40 hydrogenated castor oil 1.0, hydrolyzed protein 0.5, triethanolamine 0.25.

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  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Gerontology & Geriatric Medicine (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un procédé d'inhibition de la photodégradation d'ergothionéine, et une application associée, consistant à ajouter du hyaluronate à une solution contenant de l'ergothionéine, la teneur en ergothionéine étant de 0,0005 % à 0,01 % en poids, et la teneur en hyaluronate étant supérieure à 0,1 % en poids. La combinaison de hyaluronate et d'ergothionéine peut inhiber efficacement la photodégradation d'ergothionéine, et la composition peut être utilisée dans des produits alimentaires et de soins de santé ou des cosmétiques, ayant un bon effet de rétention d'humidité et une efficacité stable.
PCT/CN2019/118950 2019-07-29 2019-11-15 Procédé d'inhibition de la photodégradation d'ergothionéine et son application WO2021017317A1 (fr)

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CN111568918B (zh) * 2020-06-24 2021-11-16 华熙生物科技股份有限公司 一种治疗炎性痤疮的凝胶组合物及其制备方法
CN111803397B (zh) * 2020-07-07 2022-12-02 华熙生物科技股份有限公司 一种头皮护理产品及其制备方法
CN114681451B (zh) * 2020-11-10 2023-11-03 华熙生物科技股份有限公司 透明质酸或其盐和/或海藻糖的组合物及其在稳定麦角硫因中的用途
CN115944548A (zh) * 2023-02-03 2023-04-11 山东福瑞达生物股份有限公司 一种提高麦角硫因光稳定性的控油组合物及其应用
CN116158988A (zh) * 2023-03-21 2023-05-26 江苏仅三生物科技有限公司 一种具有美白、抗衰功效的护肤组合物及其应用

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