New use of HMO (s)

By using a combination of lactose-N-trisaccharide and fucosyl lactose, the problem of skin free radical damage is solved, effective free radical scavenging and antioxidant effects are achieved, and skin aging is delayed.

CN119970761APending Publication Date: 2025-05-13HENRUI (QINGDAO) BIOTECH CO LTD
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Patent Information

Application Number
CN202411120620.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-08-15
Publication Date
2025-05-13

AI Technical Summary

Technical Problem

The skin has a series of damage caused by free radical damage, such as dry skin, pigmentation and aging, and it is difficult for the existing technology to effectively eliminate free radicals.

Method used

Lactose-N-trisaccharide (LNT II) is used as the main ingredient, combining fucosyl lactose to form a composition to remove free radicals from the skin.

Benefits of technology

The composition has excellent free radical removal function, can effectively antioxidant, prevent skin aging, and keep the skin soft, smooth and elastic.

✦ Generated by Eureka AI based on patent content.

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Abstract

The invention relates to a novel application of HMO (s) and a composition containing HMO (s), and belongs to the technical field of HMO (s) application and the technical field of skin care products. The invention provides an application of lactose-N-trisaccharide (LNT II) in preparation of a free radical scavenging composition. The composition with free radical scavenging activity can be used as an antioxidant product, and the composition contains lactose-N-trisaccharide (LNT II). Preferably, the composition also contains fucosyllactose. The composition provided by the invention can effectively scavenge free radicals and prevent senescence.
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Description

Technical Field

[0001] The invention relates to a new application of HMO(s) and a composition containing HMO(s), belonging to the technical field of HMO(s) application and skin care product. Background Art

[0002] Free radicals are the product of the body's metabolic process. They are very active and are easily attracted to genetic material in cells, causing chemical reactions, which can lead to cell damage and aging.

[0003] In addition, external factors can also stimulate the body to produce "free radicals". If there is not enough protection, ultraviolet radiation will produce free radicals, which will destroy the normal function of the skin's epidermal cells, reduce the skin's immunity, and then produce spots.

[0004] In summary, if the "free radicals" in the body are not eliminated in time, the skin will produce a series of damage symptoms, such as dry and cracked skin, dark yellow, pigmentation spots, aging and sagging, and even redness, swelling and inflammation. In order to maintain the health of the body, it is necessary to provide a composition that removes free radicals. Summary of the invention

[0005] Purpose of the invention: To explore new applications of HMO(s) and to provide a free radical scavenging composition containing HMO(s).

[0006] Technical solution:

[0007] Human milk oligosaccharides (HMOs) are a unique oligosaccharide mixture found in human milk. They are rich in variety and have been shown to have biological activities such as promoting the rapid development of the brain, intestines and immune system of newborns. The inventors surprisingly found that lactose-N-trisaccharide (LNT II) has excellent free radical scavenging function.

[0008] In a first aspect of the present application, there is provided the use of lactose-N-trisaccharide (LNT II) in preparing a free radical scavenging composition.

[0009] The composition having free radical scavenging activity can be used as an antioxidant product.

[0010] The inventors also found that the reasonable combination of lactose-N-trisaccharide (LNT II) and fucosyllactose can produce a synergistic effect.

[0011] In a second aspect, the present application provides a composition containing lactose-N-trisaccharide (LNT II). The composition has the function of scavenging free radicals.

[0012] The compositions described in the first and second aspects of the present application include, but are not limited to, cosmetics, functional foods, dermatological or pharmaceutical topical compositions.

[0013] The functional food, dermatology or local pharmaceutical composition includes, but is not limited to, granules, tablets, solutions, gels and other dosage forms. These compositions may also be added with other active ingredients or other pharmaceutical excipients as required, without particular limitation. The preparation method of the composition is prepared according to conventional methods in the industry, without particular limitation.

[0014] The cosmetics include, but are not limited to, aerosol sprays, creams, lotions, ointments, powders, patches, pomades, solutions, hand-pump sprays, sticks, masks, etc. Other raw materials and auxiliary materials of these cosmetics can be formulated according to the existing technology without special restrictions, and the production method is also not particularly limited, and can be produced according to conventional methods in the industry.

[0015] Preferably, the amount of lactose-N-trisaccharide in the composition ranges from 0.1% to 1.2%. When the amount of lactose-N-trisaccharide is less than 0.1%, the free radical scavenging ability is not ideal. When the amount of lactose-N-trisaccharide is higher than 1.2%, the free radical scavenging ability and the growth rate become smaller.

[0016] In a third aspect, the present application provides a composition comprising lactose-N-triose and fucosyllactose.

[0017] Preferably, the fucosyllactose is selected from 2'-fucosyllactose (2'-fucosyllactose, 2'-FL), 3-fucosyllactose (3-FL), difucosyllactose (DFL), lactose-N-fucopentaose I (Lacto-N-fucopentaose I, LNFP I), lactose-N-difucosyllactose I

[0018] (Lacto-N-difucohexaose I, LNDFH I) or more thereof.

[0019] Preferably, in the composition, the mass ratio of lactose-N-triose to fucosyllactose is 1:9-15.

[0020] Preferably, in the composition, the mass ratio of lactose-N-triose to fucosyllactose is 1:10-14.

[0021] Preferably, in the composition, the mass ratio of lactose-N-triose to fucosyllactose is 1:12.5.

[0022] The composition of the present invention can be formulated into any suitable product form. Such product forms include, but are not limited to, aerosol sprays, creams, emulsions, solids, liquids, dispersions, foams, gels, lotions, mousses, ointments, powders, patches, pomades, solutions, hand-pump sprays, sticks, facial masks, etc. The composition of the present invention can be conveniently used to prepare or as a cosmetic, dermatological or pharmaceutical topical application product by various methods well known in the art.

[0023] The composition is composed of at least one dosage form selected from the group consisting of lotion, skin softener, toner, astringent, nourishing cream, eye cream, liquid foundation, dry powder, cream, essence, oil, gel, lotion, beauty serum, facial mask, facial mask base liquid, soap, facial cleansing foam and body cleanser.

[0024] Preferably, the composition described in the present application is prepared as a cream product.

[0025] The cream product, optionally, further comprises an adjuvant acceptable in the field of cosmetics. These adjuvants specifically include grease, emulsifier, humectant, thickener, surfactant and preservative. The suitable grease, emulsifier, thickener, humectant and surfactant are well known to those skilled in the art.

[0026] The cream product comprises 5-10% of oil, 8-16% of emulsifier, 10-20% of thickener and 5-15% of moisturizer.

[0027] The oil is not particularly limited and may be one or more of the oils commonly used in the industry, such as caprylic / capric triglyceride, cetyl ethylhexanoate and hydrogenated polyisobutene.

[0028] The emulsifier is not particularly limited and can be one or more of the commonly used emulsifiers in the industry, such as hydrogenated lecithin, glyceryl stearate citrate, glyceryl stearate SE, stearic acid, stearate, polyglycerol-3-methylglucose distearate, polysorbate, phytosterols, and the like.

[0029] The thickener is not particularly limited and can be one or more of the commonly used thickeners in the industry, such as peach gum, fucoidan, myristyl alcohol, and arachidyl alcohol.

[0030] The moisturizing agent is not particularly limited and can be any one or more of the commonly used moisturizing agents in the industry, such as glycerin, butylene glycol, propylene glycol, glyceryl polyether-26, polyethylene glycol-32, and sodium hyaluronate.

[0031] It may also include preservatives, such as any one or more of phenoxyethanol, ethylhexylglycerin, caprylyl glycol, pentylene glycol, glycine, etc. In terms of mass percentage, the HMOs skin care product includes 1-5% preservatives, preferably 2-4%.

[0032] Preferably, the cream contains 5-10% glycerol, 0.5-2% sodium hyaluronate, 4-10% hydroxypropyl-β-cyclodextrin, 0.1-0.2% allantoin, 4-8% caprylic triglyceride, 0.3-2% carbomer, 0.5-3% hydroxyethyl cellulose, 0.5-1.0% lactose-N-triose, and the balance is pure water.

[0033] Further preferably, the cream further contains fucosyllactose, wherein the mass ratio of sugar-N-trisaccharide to fucosyllactose is 1:9-15.

[0034] Preferably, the cream contains 6.5-9% glycerol, 0.8-1.5% sodium hyaluronate, 5.5-8% hydroxypropyl-β-cyclodextrin, 0.15% allantoin, 5-7% caprylic triglyceride, 0.4-1.5% carbomer, 0.7-2.5% hydroxyethyl cellulose, 0.8-1.2% lactose-N-triose, and the balance is pure water.

[0035] Further preferably, the cream further contains fucosyllactose, wherein the mass ratio of lactose-N-triose to fucosyllactose is 1:10-14.

[0036] Preferably, the cream further contains fucosyllactose, wherein the mass ratio of lactose-N-triose to fucosyllactose is 1:12-14.

[0037] Preferably, the cream further contains fucosyllactose, wherein the mass ratio of lactose-N-triose to fucosyllactose is 1:12.5.

[0038] Preferably, the cream contains 7g glycerol, 0.9g sodium hyaluronate, 0.15g allantoin, 7g hydroxypropyl-β-cyclodextrin, 6g caprylic triglyceride, 0.8g carbomer, 1.5g hydroxyethyl cellulose, 1.2g lactose-N-triose, and the remainder is pure water, totaling 100g.

[0039] Preferably, the cream contains 7g glycerol, 0.9g sodium hyaluronate, 0.15g allantoin, 7g hydroxypropyl-β-cyclodextrin, 6g caprylic triglyceride, 0.8g carbomer, 1.5g hydroxyethyl cellulose, 1.2g lactose-N-triose, 10g fucosyllactose, and the balance is pure water, totaling 100g.

[0040] In one embodiment, the skin care product containing HMO(s) of the present application is exemplified as a cream.

[0041] The preparation method of the HMO(s)-containing cream is as follows:

[0042] Step 1: Evenly mix the formulated amounts of glycerin, caprylic triglyceride, allantoin, carbomer, and hydroxypropyl-β-cyclodextrin, and stir and mix for 30-50 minutes at a temperature of 60-80° C. and a stirring rate of 800-1000 r / min to obtain a uniform liquid phase A;

[0043] Step 2: Mix the formulated amount of sodium hyaluronate, hydroxyethyl cellulose, HMO(s) (lactose-N-triose and / or fucosyllactose) with 10-30% by weight of purified water, and stir at 800-1200 r / min for 1-1.5 h at room temperature to obtain liquid phase B;

[0044] Step 3: Under the conditions of 60-80°C and a stirring rate of 800-1000r / min, liquid phase A and liquid phase B are evenly mixed under stirring, and the water in the formula is added, and homogenization is continued. Finally, the mixture is cooled to room temperature, and the pH is adjusted to 6-7 to obtain a cream.

[0045] The cream is suitable for the following skin types, preferably, dry skin, oily skin, sensitive skin, infant skin, mature skin, etc.

[0046] Beneficial effects:

[0047] The present invention provides a composition with a free radical scavenging function. The composition has an excellent free radical scavenging function, is safe and reliable, is non-irritating to the skin, and does not produce allergic reactions. The composition described in the present application can scavenges free radicals generated in the skin, plays an anti-oxidation and anti-aging role, keeps the skin soft, smooth, delicate and elastic, improves the water retention capacity of the skin, and maintains skin health. DETAILED DESCRIPTION

[0048] The experimental methods used in the following examples are conventional methods unless otherwise specified; all materials, reagents, etc., are commercially available unless otherwise specified.

[0049] Unless otherwise defined, all technical terms and scientific terms used in this specification have the same meanings as those commonly understood by those skilled in the art. In general, the nomenclature used in this specification is well known and commonly used in the art.

[0050] It should be noted that the terms used herein are only for describing specific embodiments and are not intended to limit the exemplary embodiments according to the present invention. In addition, it should be understood that when the terms "comprising" and / or "including" are used in this specification, they indicate the presence of features, steps, operations, devices, components and / or combinations thereof. It should be understood that the scope of protection of the present invention is not limited to the specific embodiments described below; it should also be understood that the terms used in the embodiments of the present invention are intended to describe specific embodiments and are not intended to limit the scope of protection of the present invention.

[0051] In the examples, lactose-N-triose (LNT II), 2'-fucosyllactose (2'-FL), 3-fucosyllactose (3-FL), difucosyllactose (DFL), lactose-N-fucopentose I (LNFP I), and lactose-N-difucohexaose I (LNDFHI) were prepared by Shandong Henglu Biotechnology Co., Ltd., and other raw materials were purchased through commercial channels.

[0052] Example 1-24. Preparation of HMO(s) aqueous solution composition and study of its free radical scavenging activity

[0053] 1. According to the concentration indexes described in Table 1, the compositions of Examples 1-24 were prepared, and the solvent was purified water.

[0054] Table 1

[0055]

[0056]

[0057] 2. Study on free radical scavenging activity of the compositions of Examples 1-24

[0058] Test principle:

[0059] 1,1-Diphenyl-2-trinitrophenylhydrazine (DPPH for short) is a stable long-lived free radical. Its ethanol solution is dark purple and has strong absorption near 517nm. When there is a free radical scavenger, the light absorption of DPPH ethanol solution is weakened due to pairing with its single electron. The degree of fading of DPPH ethanol solution is linearly related to the number of electrons it accepts, which can be used to evaluate the ability of the test sample to scavenge free radicals, that is, the size of the antioxidant activity.

[0060] The test reagents are shown in Table 2.

[0061] Table 2

[0062] name brand model DPPH Maclean 100mg / bottle Anhydrous ethanol Wide test 500mL / bottle Purified water Blue Sky 500mL / bottle

[0063] Phosphate buffer (PBS) was prepared according to conventional methods at pH 7.4.

[0064] Hydroxyl radical scavenging test protocol:

[0065] (1) Blank test: 150 μL or 200 μL of distilled water, 200 μL of 1.5 mM FeSO4 solution, 300 μL of 150 mM phosphate (PBS) buffer (pH 7.4), and 200 μL of 0.75 mM phenanthroline solution were added to the reaction system in sequence, mixed evenly, and 200 μL of 0.1% (v / v) H2O2 solution was added, mixed evenly, and reacted at 37°C in the dark for 30 min. The absorbance was measured at a wavelength of 517 nm and recorded as A0;

[0066] (2) Free radical scavenging test: Take 150 μL of each solution of Example 1 to Example 24, add 200 μL of 1.5 mM FeSO4 solution, 300 μL of 150 mM PBS buffer (pH 7.4), and 200 μL of 0.75 mM o-phenanthroline solution, mix well, add 200 μL of 0.1% (v / v) H2O2 solution, mix well, react at 37°C in the dark for 30 min, and measure the absorbance at a wavelength of 517 nm, which is recorded as A. i ;

[0067] (3) Control test: 350 μL or 400 μL of distilled water, 200 μL of 1.5 mM FeSO4 solution, 300 μL of 150 mM PBS buffer (pH 7.4), and 200 μL of 0.75 mM o-phenanthroline solution were added to the reaction system in sequence, mixed evenly, and reacted at 37°C in the dark for 30 min. The absorbance was measured at a wavelength of 517 nm, and the average value of three parallels was calculated and recorded as A. j ;

[0068] The hydroxyl radical scavenging rate was calculated according to the following formula and the results are recorded in Table 3.

[0069]

[0070] Table 3. Free radical scavenging rate

[0071]

[0072]

[0073] Table 3 Data Description:

[0074] (1) The compositions obtained in Examples 1-24 have free radical scavenging activity.

[0075] (2) The free radical scavenging activity of the compound compositions of Examples 15-24 was higher than that of the single composition, indicating that the reasonable combination of lactose-N-trisaccharide and fucosyllactose produced a synergistic effect.

[0076] Examples 25-32. The creams of Examples 25-32 were prepared according to the formulations described in Table 4 and with reference to the preparation method of the cream described in the specification.

[0077] Table 4.

[0078]

[0079] Comparative Examples 1-5. The creams of Comparative Examples 1-5 were prepared according to the formulations described in Table 5 and the preparation method of the cream described in the specification.

[0080] Table 5

[0081]

[0082]

[0083] Example 33. Study on free radical scavenging of the creams obtained in Examples 25-32 and Control Examples 1-5.

[0084] Referring to the free radical (DPPH) scavenging method described in Example 1 and T / SHRH006-2018 "Cosmetics - Free Radical (DPPH) Scavenging Example Method", the free radical scavenging ability of the samples of Examples 25-32 and Comparative Examples 1-5 was determined. The cream was diluted with 95% ethanol, and the results are recorded in Table 6.

[0085] Table 6

[0086] Cream Free radical scavenging rate, % Example 25 Cream 15.67 Example 26 Cream 28.87 Example 27 Cream 38.98 Example 28 Cream 47.61 Example 29 Cream 69.32 Example 30 Cream 68.24 Example 31 Cream 67.63 Example 32 Cream 67.01 Comparative Example 1 Cream 3.32 Comparative Example 2 Cream 22.33 Comparative Example 3 Cream 21.36 Comparative Example 4 Cream 20.18 Comparative Example 5 Cream 20.87

[0087] The data in Table 6 illustrate: The creams described in Examples 25-32 have excellent free radical scavenging activity.

[0088] The above description is only the preferred embodiment of the present application and is not intended to limit the present application. Although the present application is described in detail with reference to the aforementioned embodiments, those skilled in the art can still modify the technical solutions described in the aforementioned embodiments or replace some of the technical features therein by equivalents. Any modification, equivalent replacement, improvement, etc. made within the spirit and principles of the present application shall be included in the protection scope of the present application.

Claims

1. Application of lactose-N-trisaccharide (LNT II) in the preparation of free radical scavenging compositions.

2. A composition, characterized in that Contains lactose-N-triose (LNT II).

3. The composition according to claim 2, characterized in that The amount of lactose-N-triose used ranges from 0.1% to 1.2%.

4. A composition, characterized in that Contains lactose-N-triose and fucosyllactose, Preferably, the fucosyllactose is selected from one or more of 2'-fucosyllactose (2'-fucosyllactose, 2'-FL), 3-fucosyllactose (3-FL), difucosyllactose (DFL), lactose-N-fucopentaose I (Lacto-N-fucopentaose I, LNFP I), and lactose-N-difucohexaose I (Lacto-N-difucohexaose I, LNDFH I), Preferably, in the composition, the mass ratio of lactose-N-triose to fucosyllactose is 1:9-15, Preferably, in the composition, the mass ratio of lactose-N-triose to fucosyllactose is 1:10-14, Preferably, in the composition, the mass ratio of lactose-N-triose to fucosyllactose is 1:12.

5.

5. A cream, characterized in that: Contains 5-10% glycerol, 0.5-2% sodium hyaluronate, 4-10% hydroxypropyl-β-cyclodextrin, 0.1-0.2% allantoin, 4-8% caprylic triglyceride, 0.3-2% carbomer, 0.5-3% hydroxyethyl cellulose, 0.5-1.0% lactose-N-triose, and the balance is pure water.

6. The cream according to claim 5, characterized in that It also contains fucosyllactose, wherein the mass ratio of lactose-N-triose to fucosyllactose is 1:9-15. Preferably, the fucosyllactose is selected from one or more of 2'-fucosyllactose (2'-fucosyllactose, 2'-FL), 3-fucosyllactose (3-FL), difucosyllactose (DFL), lactose-N-fucopentaose I (Lacto-N-fucopentaose I, LNFP I), and lactose-N-difucohexaose I (Lacto-N-difucohexaose I, LNDFH I).

7. The cream according to claim 5, characterized in that Contains 6.5-9% glycerol, 0.8-1.5% sodium hyaluronate, 5.5-8% hydroxypropyl-β-cyclodextrin, 0.15% allantoin, 5-7% caprylic triglyceride, 0.4-1.5% carbomer, 0.7-2.5% hydroxyethyl cellulose, 0.8-1.2% lactose-N-triose, and the balance is pure water. Further preferably, the cream further contains fucosyllactose, wherein the mass ratio of lactose-N-triose to fucosyllactose is 1:10-14. Preferably, the cream further contains fucosyllactose, wherein the mass ratio of lactose-N-triose to fucosyllactose is 1:12-14. Preferably, the cream further contains fucosyllactose, wherein the mass ratio of lactose-N-triose to fucosyllactose is 1:12.

5.

8. The cream according to claim 5, characterized in that Contains 7g of glycerin, 0.9g of sodium hyaluronate, 0.15g of allantoin, 7g of hydroxypropyl-β-cyclodextrin, 6g of caprylic triglyceride, 0.8g of carbomer, 1.5g of hydroxyethyl cellulose, 1.2g of lactose-N-triose, and the balance is pure water, totaling 100g.

9. The cream according to claim 5, characterized in that Contains 7g of glycerin, 0.9g of sodium hyaluronate, 0.15g of allantoin, 7g of hydroxypropyl-β-cyclodextrin, 6g of caprylic triglyceride, 0.8g of carbomer, 1.5g of hydroxyethyl cellulose, 1.2g of lactose-N-triose, 10g of fucosyllactose, and the balance is pure water, a total of 100g.

10. Use of the composition according to claims 2-4 in scavenging free radicals.