Biomass Extracts for Skin Applications

Abstract

The present invention relates to a composition having prebiotic and antipathogenic properties and its use for dermocosmetic purposes, such as skin regeneration and protection.

Description

[Technical field]

[0001] The present invention relates to a composition having prebiotic and antimicrobial properties and its use for dermocosmetic purposes, such as skin regeneration and protection. [Background technology]

[0002] Mammalian skin is considered to be one of the largest organs in the body, especially the one with the largest surface area. The skin forms the first line of defense against microorganisms that may enter the body through air, water, food or materials that come into contact with the body. When the body becomes infected on the skin or throughout the body, the traditional approach to such hygiene problems has been to treat the skin / body with antibacterial actives that reduce or kill the bacteria. Recent studies show that many bacteria that are permanently present on the skin (called skin commensal bacteria) do not actually cause infection, but rather they are beneficial bacteria that protect the skin from disease-causing pathogens. Thus, there is a trend away from treating the skin with broad spectrum antibacterial actives to kill all microorganisms present on the skin (or any other part of the body) as a means of treating infections. Rather, this approach is more geared towards targeted or selective inhibition / killing of desired microorganisms, excluding skin commensals, and / or increasing the number and functionality of skin commensal bacteria through the use of prebiotics.

[0003] The health and beauty benefits of providing a healthy and balanced skin microbiome have only recently become better understood.As a result, only a limited number of suitable prebiotic agents have been identified for use on skin.In addition, conventional prebiotic agents are typically administered orally, for example as part of a nutritional supplementation regimen.Although oral intake may be suitable for delivering prebiotic agents to the digestive tract, it may not be the best way to deliver prebiotic agents to the microbiome found on skin.

[0004] Thus, there is a need to improve the health and / or appearance of human skin by providing compositions that exhibit prebiotic activity towards one or more commensal skin microorganisms, while at the same time controlling undesirable microbial activity. Summary of the Invention [Means for solving the problem]

[0005] One aspect of the present invention is a method for producing a prebiotic composition, comprising the steps of: a) providing a biomass; b) optionally determining the lipid, protein and / or carbohydrate content in said biomass; c) optionally pretreating the biomass, the optional pretreatment being a hydrothermal pretreatment at about 90° C.; d) optionally removing lipids and / or proteins from the biomass; e) contacting the biomass with a catalyst in the presence of water and / or an organic solvent to form a reaction mixture, the catalyst being an ionic polymer or a combination of ionic polymers, an ionic polypolymer network, an ionic polymer supported on a solid support, and / or a polymer membrane incorporating an ionic polymer; f) heating the reaction mixture at 100°C to 150°C to decompose the biomass in the reaction mixture to produce a liquid phase and a solid phase, the liquid phase comprising the prebiotic composition and the solid phase comprising residual biomass; g) cooling the reaction mixture to room temperature; h) isolating at least a portion of said liquid phase from said solid phase; i) optionally adding one or more compounds selected from bentonite, charcoal, zeolite, amorphous silica and / or ion exchange solvents to the isolated liquid phase; j) recovering the prebiotic composition from the isolated liquid phase; Including, The ionic polymer (IP) is composed of monomers of formula I, [ka] or a first monomer of formula I [ka] and, [ka] and at least one second monomer selected from the group consisting of: During the ceremony, n and m are independently selected from 1, 2, 3, 4, 5, and 6; z and w are independently selected from 0, 1, 2, and 3; Z1, Z2 and Z3 each independently represent [ka] is a cation selected from the group comprising: R1, R2, R3, R4, R5, R6 and R7 each independently represent a bond, H, C1-C6 alkyl, C1-C6 allyl, -CH2-(CH2) p -O-(CH2) q -CH3, C1-C6 alkoxy, C1-C6 alkoxyalkyl, benzyl, -SO3H, -(CH2) q -SO3H, provided that two of R1, R2, R3, R4, R5, R6 and R7 are each a bond; p and q are independently selected from 0, 1, 2, 3, 4, 5, and 6; L is an optional linker, and if present, each occurrence of L is independently H, substituted or unsubstituted C1-C 20 Alkylene, C1-C 20 Alkenylene, C1-C 20 Alkynylene and substituted or unsubstituted C5-C 10aryl, the substituents being selected from the group comprising H, -SOH, -COOH, -[P(=O)(OH)2], -O-SOH, -O-COOH, -O-[P(=O)(OH)2]; A is an optional acidic group, and if present, each occurrence of A is independently selected from the group consisting of H, -SOH, -COOH, -[P(=O)(OH)2], -O-SOH, -O-COOH, -O-[P(=O)(OH)2], -CH2-COOH, with the proviso that when z and w are 0, A is present in formula IV; X - F - , Cl - , Br - , I - , ClO4 - , BF4 - , PF6 - , AsF6 - , SbF6 - , NO2 - , NO3 - , HSO4 - , SO4 2- , PO4 3- , HPO4 2- , CF3CO2 - , CF3CO3 - , CO3 2- , CF3SO3 - , C1-C6 carboxylate, CN - , SCN - , OCN - , CNO - , N3 - , tosylate, mesylate, trifluoromethanesulfonate, trifluoroethanesulfonate, ditrifluoromethanesulfonylamino, docusate, xylenesulfonate; Ra is C1~C 24 is alkyl, Rb and Rc are each independently selected from the group consisting of H and CH3, or absent; Rd is C1~C 24 C1-C, optionally substituted with alkyl 24 Alkylene or C1-C 24 is alkyl, Re and Rf each independently represent C1 to C 24 is alkyl, Y is N or O, with the proviso that when Y is O, Rc is absent; R is C1~C 24 Alkyl and C5-C 10 aryl or absent; the ionic polypolymer network comprises one or more ionic polymers (IPs) crosslinked; the solid support has at least one surface comprising the one or more ionic polymers (IPs) or the ionic polypolymer network; The polymer membrane incorporates one or more ionic polymers (IPs) or an ionic polypolymer network. A method is provided.

[0006] Another aspect of the invention provides a prebiotic composition obtainable by the method of the invention.

[0007] Another aspect of the present invention is a method for producing a an effective amount of a prebiotic composition of the present invention; At least one dermatologically acceptable carrier; The present invention provides a topical cosmetic composition comprising:

[0008] Another aspect of the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention for the non-therapeutic treatment of the skin.

[0009] Another aspect of the present invention provides a use of the prebiotic composition of the present invention or the topical composition of the present invention for regulating the growth of at least one probiotic bacterium on the skin, comprising a step of applying an effective amount of the prebiotic composition of the present invention or the topical composition of the present invention to said skin.

[0010] Another aspect of the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention for preventing dysbiosis (imbalance of the microflora, dysbiosis) on the external surface of the human or animal body.

[0011] Another aspect of the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention for stimulating the skin immune system. [Brief description of the drawings]

[0012] [Figure 1] FIG. 1 shows gene expression by qRT-PCR: inhibition test against S. aureus. [Diagram 2] FIG. 2 shows gene expression after 2 days of prebiotic testing against S. epidermidis. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. The publications and applications mentioned herein are provided solely for their disclosure prior to the filing date of the present application. Nothing herein is to be construed as an admission that the invention is not entitled to antedate such publication by virtue of prior invention. In addition, the materials, methods, and examples are illustrative only and are not intended to be limiting.

[0014] In case of conflict, the present specification, including definitions, will control. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the subject matter of this specification belongs. The following definitions are provided herein to facilitate understanding of the present invention.

[0015] The term "comprise" is used generally in the sense of include, i.e. permitting the presence of one or more features or components. Also, as used in the specification and claims, the word "comprising" can include similar embodiments described with the terms "consisting of" and / or "consisting essentially of."

[0016] As used in this specification and claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise.

[0017] As used in this specification and the claims, the term "and / or" as used in phrases such as "A and / or B" is intended to include "A and B," "A or B," "A" and "B."

[0018] "Cosmetic composition" means a composition suitable for external (topical) application to the skin and / or other keratinous tissue, such as hair and nails, of a mammal, preferably a human, and intended to improve the condition and / or appearance of the skin or keratinous tissue, or otherwise provide a skin care benefit. External means the surface of the skin or other keratinous tissue. Cosmetic compositions include any color cosmetics, nail care products, or skin care products. "Skin care" means regulating and / or improving skin condition. Some non-limiting examples of skin care benefits and improvements in skin condition and / or appearance include improving the appearance and / or feel of skin by providing a smoother and more uniform appearance and / or feel, increasing the thickness of one or more layers of skin, improving the elasticity or resilience of skin, improving skin firmness, reducing the oily, shiny, and / or dull appearance of skin, improving skin hydration or moisturization, improving the appearance of fine lines and / or wrinkles, improving skin texture or smoothness, improving skin peeling or scaling, plumping skin, improving skin barrier properties, improving skin tone, reducing the appearance of redness or skin blemishes, and / or improving skin luminosity, luster, or translucency.Some non-limiting examples of cosmetic compositions include products that leave color on the face, such as foundations, mascaras, concealers, eyeliners, brow colors, eyeshadows, blushers, lipsticks, lip balms, face powders, solid emulsion compacts, etc. "Skin care products" include, but are not limited to, skin creams, moisturizers, lotions, and body washes.

[0019] "Dermatologically acceptable carrier" means a carrier that may be applied topically to the skin or keratinous tissue. Dermatologically acceptable carriers may be in a wide variety of forms, such as, for example, simple solutions (water-based or oil-based), solid forms (gels or sticks), and emulsions (water-in-oil or oil-in-water).

[0020] "Effective amount" refers to a sufficient amount of a particular component / composition to have a particular property under a particular condition. For example, an effective amount of a prebiotic composition refers to an amount sufficient to cause a desired increase in metabolic product levels and / or bacterial numbers of one or more selected microorganisms in vitro and / or in vivo.

[0021] "Prebiotic" refers to any substance or combination of substances that can be utilized as nutrients by a selected microorganism (e.g., a skin commensal microorganism), can induce the growth and / or activity of the selected microorganism, can induce the replication of the selected microorganism, can be utilized as an energy source by the selected microorganism, and / or can be utilized by the selected microorganism for the production of biological molecules (i.e., RNA, DNA, and proteins). Non-limiting examples of prebiotics include mucopolysaccharides, oligosaccharides such as galactooligosaccharides ("GOS"), polysaccharides, amino acids, vitamins, nutrient precursors, organism harvested metabolic products, lipids, and proteins.

[0022] "Replication" refers to the division of a microorganism into daughter cells (eg, by mitosis or binary fission).

[0023] "Skin" refers to one or more of the epidermis, dermis and hypodermis (i.e., subcutaneous tissue), hair follicle, hair root, hair bulb, ventral epithelial layer of the nail bed, sebaceous glands and sweat glands (eccrine and apocrine). The skin is mammalian skin, preferably human skin. In some embodiments, the skin is the external surface of a human or animal body.

[0024] "Skin commensal microorganisms" or "skin commensal bacteria" or "probiotic bacteria" refer to prokaryotic and eukaryotic organisms that can colonize (i.e., live and grow on) or temporarily reside on human skin in vitro and / or in vivo. Probiotic bacteria act on the host's immune system to induce a defense response that prevents colonization and invasion by pathogens.

[0025] "Topical" and variations thereof refer to compositions that are intended to be applied directly to the exterior surface of the skin or other keratinous tissue.

[0026] Unless otherwise indicated, the terms "microbiota" and "microbiome" refer to the collective genome of microorganisms (composed of bacteria, bacteriophages, fungi, protozoa, and viruses) that live in and on the human body.

[0027] An "aryl" group is a substituent having the structural formula H2C=CH-CH2R, where R is the remainder of the molecule.

[0028] The term "monomer" refers to a molecule that can undergo polymerization or copolymerization, thereby contributing a building block to the requisite structure of a macromolecule (polymer).

[0029] As used herein, "crosslinking" refers to the bonding of two or more monomers, oligomers, or longer polymer chains by crosslinking of a crosslinking agent such as an element, a molecular group, a compound, or another oligomer or polymer. Crosslinking can result in a polymer network (which may be two-dimensional or three-dimensional) in which polymer subunits are interconnected with multiple crosslinkers and without free ends. Crosslinking may occur upon exposure to a stimulus such as heat or light. As a result, some crosslinking processes occur at elevated temperatures and some may occur at room temperature or even lower temperatures. As the crosslink density increases, the properties of the material can change from thermoplastic to thermosetting.

[0030] As used herein, "phenolic compounds" are a class of small molecules characterized by a structure having at least one phenolic unit.

[0031] One aspect of the present invention provides a method for biomass hydrolysis into a prebiotic composition that has excellent antibacterial and prebiotic properties.

[0032] In one embodiment, the present invention provides a method for producing a prebiotic composition from biomass, comprising the steps of: a) providing a biomass; b) optionally determining the lipid, protein and / or carbohydrate content in said biomass; c) optionally pretreating the biomass, the optional pretreatment being a hydrothermal pretreatment at about 90° C.; d) optionally removing lipids and / or proteins from the biomass; e) contacting the biomass with a catalyst in the presence of water and / or an organic solvent to form a reaction mixture, the catalyst being an ionic polymer or a combination of ionic polymers, an ionic polypolymer network, an ionic polymer supported on a solid support, and / or a polymer membrane incorporating an ionic polymer; f) heating the reaction mixture at 100°C to 150°C to decompose the biomass in the reaction mixture to produce a liquid phase and a solid phase, the liquid phase comprising the prebiotic composition and the solid phase comprising residual biomass; g) cooling the reaction mixture to room temperature; h) isolating at least a portion of said liquid phase from said solid phase; i) optionally adding one or more compounds selected from bentonite, charcoal, zeolite, amorphous silica and / or ion exchange solvents to the isolated liquid phase; j) recovering the prebiotic composition from the isolated liquid phase; The present invention provides a method comprising:

[0033] In one embodiment, contacting the biomass with a catalyst in step e) to form a reaction mixture comprises adding water and / or a suitable organic solvent and an effective amount of a catalyst to the biomass to form a reaction mixture, said catalyst being an ionic polymer of the invention or a combination of ionic polymers of the invention, an ionic polymer network of the invention, a membrane incorporating an ionic polymer of the invention and / or a solid support supported ionic polymer of the invention, and decomposition step f) comprises heating the reaction mixture of step e) for a suitable period of time followed by cooling to room temperature (typically 20-25° C.).

[0034] In some embodiments of the method for producing a prebiotic composition from biomass, the method further comprises applying N2 or CO2 pressure during the decomposition step f), the pressure may be in the range of 20 bar to 300 bar, preferably 20 bar to 150 bar.

[0035] In some embodiments of the method for producing a prebiotic composition from biomass, step i) is performed, i.e., step i) is not optional.

[0036] The term "biomass" as used herein refers to living or dead biological material that can be used in the method for producing the prebiotic composition of the present invention. In some embodiments, the biomass is selected from the group including spent yeast slurry, spent barley, brewer's spent grain, pellets, nuts or solid feed (for cattle); crops or crop residues: corn, soybean, sorghum, oats, barley, copra, chaff, husk or husk, sugar beet waste; peeling products; fish meal; meat and bone meal; molasses; oil cake and pomace; oligosaccharides; preserved feed plants: silage; seaweed; seeds and grains, either whole or prepared by crushing, grinding, etc.; germinated cereals and legumes; yeast extract. Preferably, the biomass is yeast slurry or brewer's spent grain. Most preferably, the biomass is brewer's spent grain. The term "brewery spent grains (BSG)" is a by-product of the brewing industry and a food waste product obtained as a mostly solid residue after wort production in the brewing process. The term "yeast slurry" is typically used in the brewing industry to describe a pasty mixture of yeast and liquid.

[0037] Optionally, before any use, the carbohydrate and / or lipid content is determined in the biomass based on standard methods. Lipids can be determined / extracted using the Folch method (Folch J, Lees M, Stanley, GHS, 1957, 226, 497-509) with a mixture of methanol, chloroform and water (2:1:0.8, v / v / v) and subsequent phase separation. Carbohydrate determination is performed, for example, according to the NREL protocol "Determination of Structural Carbohydrates and Lignin in Biomass". For example, 1 ml of 72% sulfuric acid was added to 100 mg of biomass. The slurry was stirred for 1 hour at 30°C, followed by the addition of 28 ml of deionized water. The mixture was autoclaved for 1 hour at 120°C, cooled to room temperature and used for sugar analysis by HPLC and acid-soluble lignin measurement using UV spectrophotometry at 205 nm wavelength. The same hydrolysates were used for protein analysis by Bradford protein assay. The residue from the acid hydrolysis was washed with 100 mL of water and then dried at 105° C. for Klason lignin determination.

[0038] The optional pretreatment of the biomass used in the methods described herein uses one or more methods selected from the group consisting of washing, solvent extraction, solvent swelling, crushing, grinding, steam pretreatment, explosive steam pretreatment, dilute acid pretreatment, hot water pretreatment (about 90°C), alkaline pretreatment, lime pretreatment, wet oxidation, wet explosion, ammonia fibre explosion, organic solvent pretreatment, biological pretreatment, ammonia percolation, ultrasound, electroporation, microwave, supercritical CO2, supercritical H2O, ozone and gamma irradiation. The optional pretreatment of the biomass includes, for example, grinding of the biomass. To overcome the bottleneck of reaction rate limited by surface reaction and mass transfer, a pretreatment process of the biomass by ball mill grinding is highly recommended, which leads to a decrease in crystallinity and an increase in the specific surface area of ​​the cellulosic material. Depending on the mechanical ball milling performed on the biomass, there is a decrease in the structural particle size, a decrease in the degree of polymerization of the cellulose, and an increase in the amorphous content of the cellulose.

[0039] In one embodiment of the method for producing the prebiotic composition of the invention, the optional pretreatment of the biomass (step c) consists of hydrothermal pretreatment of the biomass at about 90° C. for 30 min to 2 h, preferably 1 h, followed by cooling to room temperature (20° C. to 25° C.) and filtration, to obtain a solid phase (i.e., pretreated biomass) used in step e).

[0040] Optional removal of lipids and / or proteins from the biomass used in the methods described herein provides a biomass richer in fiber products for further degradation by step f). Lipid removal is performed by methods known in the art, such as mechanical pressing, organic solvents, or supercritical CO2. Protein removal is performed by methods known in the art, such as water containing enzymes, alcohols, salts and / or detergents, or extrusion.

[0041] Some ionic polymers used in the present invention methods of producing a prebiotic composition from biomass consist of a polymer backbone containing anions and cations, as disclosed in International Publication WO 2019 / 058270 A1, which is incorporated by reference in its entirety. Specifically, the ionic polymers (IPs) used in the present invention methods of producing a prebiotic composition from biomass consist of monomers of formula I or [ka] or a first monomer of formula I [ka] and, [ka] and at least one second monomer selected from the group consisting of: During the ceremony, n and m are independently selected from 1, 2, 3, 4, 5, 6; preferably n and m are independently selected from 1, 2, 3; most preferably n is 2 and m is 1 or 2. z and w are independently selected from 0, 1, 2, 3; preferably z and w are independently selected from 0 and 1; most preferably z and w are 0 or 1.

[0042] Z1, Z2 and Z3 each independently represent [ka] and preferably Z1, Z2 and Z3 are each independently a cation selected from the group consisting of: [ka] and most preferably, Z1, Z2 and Z3 are each independently a cation selected from the group consisting of: [ka] is a cation selected from the group comprising: R1, R2, R3, R4, R5, R6 and R7 each independently represent a bond, H, C1-C6 alkyl, C1-C6 allyl, -CH2-(CH2) p -O-(CH2) q -CH3, C1-C6 alkoxy, C1-C6 alkoxyalkyl, benzyl, -SO3H, -(CH2) q R1, R2, R3, R4, R5, R6 and R7 are each independently selected from the group comprising: —SO3H with the proviso that two of R1, R2, R3, R4, R5, R6 and R7 are each a bond; preferably R1, R2, R3, R4, R5, R6 and R7 are each independently selected from the group comprising: a bond, H, C1-C6 alkyl with the proviso that two of R1, R2, R3, R4, R5, R6 and R7 are each a bond; most preferably R1, R2, R3, R4, R5, R6 and R7 are each independently selected from the group comprising: a bond and H with the proviso that two of R1, R2, R3, R4, R5, R6 and R7 are each a bond; p and q are independently selected from 0, 1, 2, 3, 4, 5, and 6; L is an optional linker, and if present, each occurrence of L is independently H, substituted or unsubstituted C1-C 20 Alkylene, C1-C 20 Alkenylene, C1-C 20 Alkynylene and substituted or unsubstituted C5-C 10 aryl, the substituents being selected from the group comprising H, -SOH, -COOH, -[P(=O)(OH)2], -O-SOH, -O-COOH, -O-[P(=O)(OH)2], preferably L is absent; A is an optional acidic group, and when present, each occurrence of A is independently selected from the group comprising: H, -SOH, -COOH, -[P(=O)(OH)2], -O-SOH, -O-COOH, -O-[P(=O)(OH)2], -CH-COOH, with the proviso that when z and w are 0, A is present in formula IV; preferably, when present, each occurrence of A is independently selected from the group comprising: H, -SOH, -COOH, -O-COOH, -CH-COOH, with the proviso that when z and w are 0, A is present in formula IV; most preferably, A is not present or, when present, each occurrence of A is independently selected from the group comprising: H, -COOH, -CH-COOH, with the proviso that when z and w are 0, A is present in formula IV; X - F - , Cl - , Br - , I - , ClO4 - , BF4 - , PF6 - , AsF6 - , SbF6 - , NO2 - , NO3 - , HSO4 - , SO4 2- , PO4 3- , HPO4 2- , CF3CO2 - , CF3CO3 - , CO3 2- , CF3SO3 - , C1-C6 carboxylate, CN - , SCN - , OCN - , CNO - , N3 - , tosylate, mesylate, trifluoromethanesulfonate, trifluoroethanesulfonate, ditrifluoromethanesulfonylamino, docusate, xylenesulfonate, preferably X - F - , Cl - , HSO4 - , SO4 2- , PO4 3- , HPO4 2- , CF3CO2- , CF3CO3 - , CF3SO3 - and most preferably selected from the group comprising X - is Cl - , HSO4 - , SO4 2- , CF3SO3 - The compound is selected from the group consisting of: Ra is C1~C 24 is alkyl, Rb and Rc are each independently selected from the group consisting of H and CH3 or absent, preferably Rc is absent; Rd is C1~C 24 C1-C, optionally substituted with alkyl 24 Alkylene or C1-C 24 alkyl, preferably Rd is C1-C2 alkylene or C1-C2 alkyl or C1-C3 alkyl; Re and Rf each independently represent C1 to C 24 alkyl, preferably CH3; Y is N or O, with the proviso that when Y is O, Rc is absent; R is C1~C 24 Alkyl and C5-C 10 Preferably R is selected from the group including aryl or absent, and preferably R is CH3.

[0043] In the context of the present invention, the feature "A is an optional acidic group" means that A is an optional group, preferably an acidic group, i.e. A is either present or absent.

[0044] In some embodiments of the method, the second monomer of formula VI of the ionic polymer (IP) is [ka] It is.

[0045] In some embodiments of the method, the second monomer of formula VI of the ionic polymer (IP) is [ka] It is.

[0046] In some embodiments of the method, the (first) monomer of formula I of the ionic polymer (IP) is [ka] It is.

[0047] In some embodiments of the ionic polymer of the present method, Z1 and Z2 are the same (identical). In other embodiments, Z1 and Z2 are different.

[0048] In some embodiments of the ionic polymer of the method of the present invention, Z1 and Z2 are [ka] R2 and R5 are bonds, R1, R3 and R4 are H, and n is not 4.

[0049] In another embodiment of the ionic polymer of the present invention, Z1 and Z2 are [ka] wherein R2 and R5 are bonds, n is 4, and at least one of R1, R3, and R4 is not H.

[0050] In some preferred embodiments of the ionic polymer of the method of the present invention, the C1-C6 carboxylate is selected from the group including formate, acetate, propionate, butyrate, hexanoate, maleate, fumarate, oxalate, lactate, pyruvate.

[0051] The ratio between different monomers in the ionic polymer of the present invention, including the first monomer and the second monomer, can be any suitable ratio and may vary depending on the biomass to be treated. In some embodiments, the first and second monomers are present in a ratio of 1:1 or 4:1. In some other embodiments, the ratio of the first monomer to the second monomer used in the methods described herein ranges from 4:1 to 1:4.

[0052] According to some embodiments of the method of the present invention, the monomer according to formula I is [ka] The compound is selected from the group consisting of:

[0053] According to a further embodiment of the process of the invention, the monomer according to formula I is [ka] is selected from.

[0054] According to some embodiments of the method of the present invention, the monomer according to formula II is [ka] It is.

[0055] According to some embodiments, the method of the present invention comprises: [ka] [ka] The present invention provides an ionic polymer selected from the group comprising: x and y each independently represent an integer selected within the range of 1 to 1000, preferably 1 to 500 or 1 to 200, and more preferably 1 to 100 or 1 to 50.

[0056] According to some embodiments, the method of the present invention comprises: [ka] The present invention provides an ionic polymer selected from the group comprising: x and y each independently represent an integer selected within the range of 1 to 1000, preferably 1 to 500 or 1 to 200, and more preferably 1 to 100 or 1 to 50.

[0057] According to one embodiment of the method of the present invention, the ionic polymer is [ka] It is.

[0058] According to another embodiment of the method of the present invention, the ionic polymer (IP-A5) consists of a monomer of formula (I) and a monomer of formula VI below: [ka]

[0059] According to another embodiment of the method of the present invention, the ionic polymer (IP-A6) consists of a monomer of formula (I) and a monomer of formula (VI) below: [ka]

[0060] In some embodiments of the method for producing a prebiotic composition, the organic solvent is selected from the group including alcohols (e.g., methanol, ethanol, butanol, ethylene glycol, etc., preferably ethanol), ethers (e.g., dimethoxyethane, diglyme, butyl methyl ether, etc.), ketones (e.g., methyl isobutyl ketone, N-methyl-2-pyrrolidone, etc.), eutectic solvents (e.g., glycerol, choline chloride, octanoic acid, tetrabutylammonium chloride, poly(ethylene glycol), choline chloride, lactic acid, glycine).

[0061] In some embodiments of the methods of the present invention, recovery of the prebiotic composition can be by any technique known in the art, such as filtration, centrifugation, or gravity settling. After recovery, the prebiotic composition can be used in liquid form, or it can be concentrated, or it can be dried into a powder form.

[0062] The effective amount of the ionic polymer or combinations thereof of the present invention used in the methods described herein may depend on several factors, including, for example, the type of biomass, the amount of biomass, the protein, carbohydrate and / or lipid content in the biomass, the type and number of pretreatments applied to the biomass, and the reaction conditions (such as temperature and time). The effective amount of the ionic polymer of the present invention refers to an amount sufficient to degrade the biomass into the prebiotic composition of the present invention. In some embodiments, the effective amount of the ionic polymer of the present invention is typically 0.005:1 w / w to 10:1 w / w, 0.05:1 w / w to 10:1 w / w, 0.5:1 w / w to 10:1 w / w, 1:1 w / w to 1:5 w / w, preferably 0.1:1 w / w to 1:5 w / w, and most preferably 0.005:1 w / w to 0.5:1 w / w, compared to the biomass load.

[0063] The biomass to water ratio used in the methods described herein can depend on several factors, including, for example, the type of biomass and the amount of biomass. In some embodiments, the biomass to water and / or organic solvent (alcohols, ethers, ketones, eutectic solvents, etc.) ratio used in the methods described herein ranges from 1:100 w / v to 1:1 w / v, preferably 1:50 w / v to 1:10 w / v, or preferably 0.5:10 w / v to 1.5:10 w / v.

[0064] The preferred temperature profile for heating used in the methods described herein also depends on the biomass starting material used and the intended monomer and oligomer mixture to be produced. The heating temperature should preferably be kept at a maximum of 170° C., in some embodiments at a maximum of 150° C. In some embodiments, the heating temperature is between 50° C. and 170° C., or between 80° C. and 170° C., preferably between 100° C. and 150° C., or between 100° C. and 130° C. Preferably, when applied on a small scale, the heating is carried out in a high pressure autoclave reactor, which is sealed and then heated for the appropriate reaction time and temperature.

[0065] In some embodiments, suitable reaction times in the methods described herein are, for example, 10 minutes to 10 hours, preferably 0.5 hours to 5 hours, or 0.5 hours to 3 hours, or 1 hour to 3 hours, depending on the type and amount of biomass.

[0066] The method for producing the prebiotic composition operates at moderate temperatures, typically below 150° C., whereas prior art methods require temperatures in excess of 150° C. In addition, the method for producing the prebiotic composition of the present invention provides fewer by-products, which allows for easier recovery of the desired product.

[0067] Another aspect of the present invention provides a prebiotic composition obtainable by the method for producing a prebiotic composition of the present invention.

[0068] In various embodiments, the prebiotic composition of the present invention comprises at least one carbohydrate compound. Such carbohydrate compounds may be bio-based compounds. The benefit of the carbohydrate compounds may be to improve the balance of the body region symbiotic flora by providing an energy source to promote beneficial microbial growth in the body region. In some embodiments, the at least one carbohydrate compound comprises inulin, α-glucan oligosaccharides, fructooligosaccharides, isomaltooligosaccharides, xylooligosaccharides, arabinoxylooligosaccharides, β-glucans, transgalactooligosaccharides, mannan-oligosaccharides, lactulose, xylitol, lactitol, trehalose, or combinations thereof. The prebiotic composition of the present invention may further comprise hydrolyzed proteins and phenolics (such as ferulic acid).

[0069] In some embodiments, the prebiotic composition of the present invention comprises (by weight %). Total oligosaccharides: 50%~70% Protein and / or protein hydrolysates: 20% to 40% Phenolic compounds (phenols): <1% Minerals: <8% Moisture: <10% In the above, the oligosaccharide is Glucose: 1% to 20% by weight of total oligosaccharides Xylose: 20% to 40% by weight of total oligosaccharides Arabinose: 5% to 30% by weight of total oligosaccharides and the distribution of the degree of polymerization (DP) of said oligosaccharides is as follows: DP1: 0%~10% DP2~DP30:>80%

[0070] Certain embodiments provide prebiotic compositions of the invention in which the oligosaccharides comprise β-(1,4) linked xylose units, α-(1,2) arabinose, or α-(1,3) arabinose, or β-(1,4) linked xylose units substituted with α-(1,2) arabinose, or α-(1,3) arabinose, or both α-(1,2) arabinose and α-(1,3) arabinose, and linked glucose units to form a (1,3)-(1,4)-β-D-glucan molecule.

[0071] Another particular embodiment provides a prebiotic composition of the invention, in which the oligosaccharides are both linear and branched in structure, preferably comprising arabinoxylooligosaccharides in which at least one arabinose or xylose is located at the reducing end of the oligosaccharide backbone. The ratio of arabinose units to xylose units in the oligosaccharides varies depending on the reaction conditions and the ionic polymer applied. Thus, in one embodiment, in the prebiotic composition of the invention, the branched oligosaccharides comprise arabinose units and xylose units, preferably with an arabinose / xylose ratio of 0.4 to 1.2, preferably with a ratio of 0.4 to 1.0, preferably with a ratio of 0.45 to 1.0, preferably with a ratio of 0.5 to 0.9. In one embodiment of the prebiotic composition, the branched or linear oligosaccharides comprise xylose units and are substantially free of arabinosyl groups.

[0072] In one embodiment of the prebiotic composition of the invention, the oligosaccharide comprises at least two β(1-4) glucose units linked together.

[0073] In one embodiment of the prebiotic composition of the invention, the oligosaccharide comprises at least two β(1-4) linked xylose units linked to each other.

[0074] In one embodiment of the prebiotic composition of the invention, the oligosaccharides comprise at least one branch consisting of an α(1-3) linked arabinose unit or a β(1-3) linked xylose unit attached to the backbone.

[0075] In one embodiment of the prebiotic composition of the invention, the oligosaccharides comprise a β(1-4) linked xylose unit linked to at least one α(1-2) arabinose unit.

[0076] In one embodiment of the prebiotic composition of the invention, the oligosaccharides comprise a β(1-4) linked xylose unit in which a mono-substituted xylose is linked to at least one α(1-2) arabinose unit and one α(1-3) arabinose unit.

[0077] In one embodiment of the prebiotic composition of the invention, the oligosaccharides comprise β(1-4) linked xylose units in which at least one disubstituted xylose is linked to one α(1-2) arabinose unit and one α(1-3) arabinose unit.

[0078] In one embodiment of the prebiotic composition of the invention, the oligosaccharides comprise β(1-4) linked xylose units in which there is at least one mono-substituted xylose with an α(1-3) arabinose unit and a di-substituted xylose with one α(1-2) arabinose unit and one α(1-3) arabinose unit.

[0079] In one embodiment of the prebiotic composition of the invention, the oligosaccharide comprises at least one trisaccharide in which a xylose is linked by a (1-4) bond between two glucose units (Glc α(1-4) Xyl α(1-4) Glc) or between one arabinose and a xylose unit (Ara α(1-6) [Xyl β(1-4)] Glc).

[0080] In one embodiment of the prebiotic composition of the invention, the oligosaccharides comprise at least one branch consisting of an α(1-3) linked arabinose unit or a β(1-2) linked xylose unit attached to the backbone.

[0081] In one embodiment of the prebiotic composition of the invention, the oligosaccharide comprises at least one trisaccharide in which a xylose is linked by a (1-4) bond between two glucose units (Glc α(1-4) Xyl α(1-4) Glc) or between one arabinose and a xylose unit (Ara α(1-6) [Xyl β(1-4)] Glc).

[0082] In some embodiments, the backbone of the prebiotic compositions of the present invention is composed of β-(1,4) linked xylose residues, which can be substituted with arabinose residues, and hydroxycinnamic acid, ferulic acid, and p-coumaric acid can be esterified onto the arabinose residues.

[0083] In some embodiments, the backbone of the prebiotic compositions of the invention is composed of β-(1,4) linked xylose residues, which may be substituted with arabinose residues, and additional uronic acids or methylated uronic acids may be present thereon.

[0084] In some embodiments, the oligosaccharides and / or proteins in the prebiotic compositions of the invention have an average molecular weight of less than 10 kDa, preferably less than 7.5 kDa, preferably less than 5 kDa, preferably less than 4 kDa, preferably less than 2 kDa.

[0085] One advantage of the prebiotic composition of the present invention is that it does not cause turbidity when used in a cosmetic composition.Another advantage of the prebiotic composition of the present invention is that it has little or very light color, and therefore does not color the cosmetic composition.

[0086] Another aspect of the present invention is a topical cosmetic composition comprising: an effective amount of a prebiotic composition of the present invention; At least one dermatologically acceptable carrier; The present invention provides a cosmetic composition for topical application comprising:

[0087] The topical cosmetic composition herein comprises an effective amount of the prebiotic composition of the present invention. The prebiotic composition may be present in an amount of more than 0.001%, more than 0.01%, more than 0.05%, more than 0.1%, more than 0.5%, more than 1%, more than 2%, more than 3%, more than 4%, or even more than 5% by weight of the topical cosmetic composition. To avoid cosmetically undesirable properties (e.g., stickiness or poor spreadability), it may be desirable to limit the amount of prebiotic composition in the topical cosmetic composition to less than 25%, less than 20%, less than 15%, less than 10%, or even less than 5% by weight of the composition. In certain embodiments, the prebiotic composition may be present in an amount of 0.1% to 10% by weight of the topical cosmetic composition, preferably 0.5% to 5% by weight, and most preferably 0.001% to 5% by weight of the topical cosmetic composition.

[0088] In certain embodiments, the prebiotic composition may be present in an amount sufficient to increase the bacterial count of at least one skin commensal microorganism by at least 10% in vitro (e.g., 10-200% or more, 50-175%, 100-150%, or any value within these ranges). Additionally or alternatively, the prebiotic composition may be present in an amount sufficient to increase the bacterial count of at least two skin commensal microorganisms by at least 10% in vitro (e.g., 10-200%, 20-180%, 30-160%, 40-150%, 50-120%, or any value within these ranges). Further, the prebiotic composition may be present in an amount sufficient to increase the bacterial count of at least three skin commensal microorganisms by at least 10% in vitro (e.g., 10-200% or more, or any value within this range). In vitro bacterial counts may be determined according to a plate count test, described in more detail below.

[0089] The topical cosmetic composition of the present invention comprises one or more dermatologically acceptable carriers. Such carriers may be selected from the group comprising: Water and / or water-miscible solvents. Suitable water-miscible solvents include monohydric alcohols, dihydric alcohols, polyhydric alcohols, glycerol, glycols, polyalkylene glycols such as polyethylene glycols, and mixtures thereof. When the topical cosmetic composition is in the form of an emulsion, the water and / or water-miscible solvents typically combine with the aqueous phase of the emulsion. · One or more suitable oils. The oil may be a volatile oil or a non-volatile oil. Volatile oils suitable for use in the present invention may have a viscosity in the range of 0.5 to 5 centistokes (cSt) at 25°C. Volatile oils may be used to promote more rapid drying of the skin care composition after it has been applied to the skin. Non-volatile oils may be included to provide emolliency and protective benefits to the skin. one or more suitable silicone oils, such as one or more polysiloxanes, and / or hydrocarbon oils (e.g. linear, branched, or cyclic alkanes and alkenes) and / or amides (suitable amides include N-acetyl-N-butylaminopropionate, N-lauroyl isopropyl sarcosine, and N,N-diethyltoluamide), and / or ethers (suitable examples of these ethers include PPG-14 butyl ether, PPG-15 stearyl ether, dioctyl ether, dodecyl octyl ether, and mixtures thereof). Emulsifiers. Emulsifiers may be desirable when the composition is provided in the form of an emulsion or when immiscible materials are combined. Structuring agents may be used to increase the viscosity of the topical cosmetic composition, thicken, solidify, or provide a solid or crystalline structure to the topical cosmetic composition. Structuring agents are typically classified based on solubility, dispersibility, or compatibility. Examples of aqueous or water structuring agents include polymeric agents, natural or synthetic gums, polysaccharides, and the like. Other exemplary types of polymeric structuring agents include, but are not limited to, carboxylic acid polymers, polyacrylamide polymers, sulfonated polymers, high molecular weight polyalkyl glycols or polyglycerins, copolymers thereof, hydrophobically modified derivatives thereof, and mixtures thereof.

[0090] The topical cosmetic compositions of the present invention may optionally contain ingredients useful for regulating and / or improving the condition of mammalian skin. Some non-limiting examples of such optional ingredients include vitamins (one or more water-soluble vitamins, such as vitamin B, vitamin C, vitamin D, vitamin K, etc.); peptides and peptide derivatives; sugar amines, sunscreen actives (or sunscreens) and / or UV absorbers, humectants, moisturizers, skin conditioners, colorants (pigments, dyes, lakes, combinations thereof, etc.), film-forming compositions, phytosterols, salicylic acid compounds, hexamidines, dialkanoyl hydroxyproline compounds, flavonoids, retinoid compounds, botanicals, N-acyl amino acid compounds, derivatives thereof, and combinations thereof.

[0091] The topical cosmetic composition of the present invention may be in any one of a variety of forms known in the art, including, for example, emulsions, lotions, milks, liquids, solids, creams, gels, micelles, ointments, pastes, serums, sticks, sprays, tonics, aerosols, foams, pencils, and the like. The cosmetic composition may be incorporated into shaving preparation products, including, for example, gels, foams, lotions, and creams, including both aerosol and non-aerosol versions. Other cosmetic compositions include antiperspirants, deodorants, and personal cleaning compositions such as soaps and shampoos.

[0092] The topical cosmetic composition of the present invention may be prepared according to conventional methods known in the art for making such compositions. Such methods may include mixing the ingredients in one or more steps to achieve a relatively homogeneous state, with or without heating, cooling, application of vacuum, etc. For example, emulsions may be prepared by first mixing the aqueous phase materials separately from the fatty phase materials, and then combining the two phases as necessary to obtain the desired continuous phase. In certain embodiments, the composition may be prepared to provide suitable stability (physical stability, chemical stability, photostability, etc.) and / or delivery of the active agent. The composition may be provided in a package sized to store a sufficient amount of the composition over the treatment period. The size, shape, and design of the package may vary widely.

[0093] Another aspect of the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention for non-therapeutic treatment of the skin. In some embodiments of the present invention, the non-therapeutic treatment is skin protection and / or regeneration. In other embodiments of the present invention, the non-therapeutic treatment is protecting and improving the condition and / or appearance of the skin. In other embodiments of the present invention, the non-therapeutic treatment is maintaining skin hydration. In other preferred embodiments, the non-therapeutic treatment is skin regeneration and / or protection, improving the condition and / or appearance of the skin, maintaining skin hydration.

[0094] In some embodiments, the present invention provides a method of non-therapeutic treatment of the skin, comprising applying to the skin an effective amount of the prebiotic composition of the present invention or the topical composition of the present invention. In a preferred embodiment, the non-therapeutic treatment is skin regeneration and / or protection. In another preferred embodiment, the non-therapeutic treatment is improving the condition and / or appearance of the skin. In another preferred embodiment of the present invention, the non-therapeutic treatment is maintaining skin hydration. In another preferred embodiment, the non-therapeutic treatment is skin regeneration and / or protection, improving the condition and / or appearance of the skin, maintaining skin hydration.

[0095] Another aspect of the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention for modulating the growth of at least one symbiotic bacterium (microorganism) on the skin. In a preferred embodiment, modulating is promoting or enhancing the growth of at least one symbiotic bacterium. In some embodiments, the probiotic bacteria is selected from the group consisting of Propionibacterium acnes, Corynebacterium tuberculostearicum, Streptococcus mitis, Streptococcus oralis, Streptococcus pseudopneumoniae, Streptococcus sanguinis, Micrococcus luteus, Staphylococcus epidermidis, Staphylococcus capitis, Veillonella parvula, and the like. In a preferred embodiment, the symbiotic bacterium is selected from the group consisting of Staphylococcus epidermidis.

[0096] Another aspect of the present invention provides a method of modulating the growth of at least one probiotic bacterium (microorganism) on the skin, comprising applying to the skin an effective amount of a prebiotic composition of the present invention or a topical composition of the present invention. In some embodiments, the probiotic bacterium is selected from the group consisting of Propionibacterium acnes, Corynebacterium tuberculostealicum, Streptococcus mitis, Streptococcus oralis, Streptococcus pseudopneumoniae, Streptococcus sanguinis, Micrococcus luteus, Staphylococcus epidermidis, Staphylococcus capitis, and Veillonella parvula. In a preferred embodiment, the probiotic bacterium is Staphylococcus epidermidis.

[0097] Another aspect of the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention to prevent dysbiosis. In a preferred embodiment, the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention to prevent dysbiosis on the external surface of the human or animal body, preferably on the external part of the skin of a human or animal. In some embodiments, such use of the prebiotic composition of the present invention or the topical composition of the present invention is a non-therapeutic use.

[0098] Another aspect of the invention provides a method for preventing dysbiosis, comprising applying an effective amount of a prebiotic composition of the invention or a topical composition of the invention to the skin. In a preferred embodiment, the invention provides a method for preventing dysbiosis on the external surface of the human or animal body, preferably the external part of the skin of a human or animal, comprising applying an effective amount of a prebiotic composition of the invention or a topical composition of the invention to the skin. In some embodiments, such use of the prebiotic composition of the invention or the topical composition of the invention is a non-therapeutic use.

[0099] Dysbiosis typically involves the loss of beneficial bacteria (microbes), such as commensal bacteria, and the proliferation of pathogenic bacteria (microbes).

[0100] Another aspect of the present invention provides the use of the prebiotic composition of the present invention or the topical composition of the present invention to stimulate the skin immune system. In a preferred embodiment, the stimulation of the skin immune system is obtained by increasing the proliferation and / or colonization of S. epidermidis on the skin or symbiotic bacteria (microorganisms) on the skin. In some embodiments, stimulating the skin immune system provides an immune boost to the outer surface of the human or animal body, such as the skin of a human or animal. In some embodiments, such use of the prebiotic composition of the present invention or the topical composition of the present invention is a non-therapeutic use.

[0101] Another aspect of the present invention provides a method for stimulating the skin immune system, comprising applying an effective amount of the prebiotic composition of the present invention or the topical composition of the present invention to the skin. In a preferred embodiment, the stimulation of the skin immune system is obtained by increasing the proliferation and / or colonization of S. epidermidis on the skin or commensal bacteria (microorganisms) on the skin. In some embodiments, stimulating the skin immune system provides an immune boost to the outer surface of the human or animal body, such as the skin of a human or animal. In some embodiments, such use of the prebiotic composition of the present invention or the topical composition of the present invention is a non-therapeutic use.

[0102] The prebiotic compositions of the present invention can be selectively utilized by microorganisms (bacteria) on and / or within the skin to provide health benefits, such as protection and / or regeneration of the skin and / or protection and improvement of the condition and / or appearance of the skin. Such prebiotic compositions can provide the health benefit of selective stimulation of beneficial commensal microorganisms competitively and to the detriment of the growth of opportunistic, undesirable, or pathogenic microorganisms. Such health benefits can include helping commensal, beneficial microorganisms to thrive on and / or within the skin. For example, in some embodiments, the prebiotic compositions of the present invention may promote the growth of the commensal bacteria Staphylococcus epidermidis (S. epidermidis) and / or other commensal bacteria. Health benefits can include protecting and promoting the balance and diversity of the microflora on and / or within the skin. Another health benefit can include promoting, restoring, strengthening, and maintaining the skin's defenses against excessive growth or infection by harmful microorganisms or against external toxicants. Such health benefits can include stimulating the release of antimicrobial peptides by keratinocytes in the skin. Another health benefit can include increasing the resistance of the skin to pathological conditions, including, but not limited to, dermatitis, acne, rosacea, eczema, and premature aging. Furthermore, such prebiotic compositions can improve the condition and / or appearance of the skin.

[0103] In some embodiments, by varying the parameters of the method of the invention for producing a prebiotic composition, it is possible to obtain a prebiotic composition that has only a prebiotic effect, or a prebiotic composition that has both a prebiotic effect and an anti-pathogenic effect, where an anti-pathogenic effect means that the composition inhibits the growth of pathogenic bacteria.

[0104] Colonization of skin microbiota with S. epidermidis may affect immune function of skin and / or reduce premature aging of skin. S. epidermidis promotes the recovery of healthy skin, in part, by preventing the colonization of skin microbiota by pathogenic microorganisms. S. epidermidis has also been shown to affect host immunity by boosting host immunity against S. aureus, activating mast cell-mediated immunity, suppressing uncontrolled inflammatory responses during wound healing, inducing the production of antimicrobial proteins by skin, and stimulating skin T cell maturation. Thus, S. epidermidis may cooperate with the host defense system and endogenous AMPs to protect the skin. Furthermore, the microbiota may represent a kind of filter for the environment, since most agents that come into contact with and / or penetrate the skin also come into contact with the microbiota.

[0105] In another embodiment, the prebiotic composition of the present invention applied to the skin may increase the colonization of S. epidermidis on the skin, thereby protecting the skin from premature aging, reducing signs of aging such as reducing hyperpigmentation, wrinkles, and inflammation, and improving the adaptive ability of the skin. The skin microbiota modulating composition may protect the skin from oxidative damage from the environment. Oxidative damage from ultraviolet radiation from the sun and air pollution can cause adverse effects on human skin, including sunburn, immunosuppression, and premature aging such as photoaging, which may be partially characterized by wrinkles, pigmentation changes, and loss of skin tone.

[0106] Without being limited by theory, it is believed that the health of the skin microbiota may be related to desirable skin function or appearance and / or may otherwise provide one or more skin care benefits. For example, by maintaining or improving the health of one or more members of the skin microbiota, it may be possible to maintain or improve the appearance, barrier function, moisture retention and / or other properties of the skin. In some cases, it may be desirable to target a particular area or areas of the skin for maintenance or improvement when the particular area or areas of the skin exhibit undesirable function and / or appearance. For example, it may be desirable to target a particular area of ​​the skin, such as the face (e.g., forehead, cheeks, and periorbital part of the face), hands and / or forearms, which may be more prone to damage by exposure to the environment (e.g., UV radiation, wind, pollution, oxidation, irritants) and / or may be more exposed to visible signs of intrinsic aging than some other areas of the skin.

[0107] The prebiotic composition or topical cosmetic composition disclosed herein may be suitable for use as a topical skin care product or cosmetic product (cosmetics), which may be applied as part of a user's daily makeup or personal care regimen. Additionally or alternatively, the prebiotic composition or topical cosmetic composition of the present invention may be used on an "as needed" basis. In certain embodiments, a skin care product, such as a moisturizing cream, lotion, or ointment, comprising at least one dermatologically acceptable carrier and an effective amount of the prebiotic composition of the present invention may be applied topically to one or more target areas of the user's skin (e.g., face, forearms, hands, or portions thereof) to provide skin care benefits in the target areas or otherwise improve the health and / or appearance of the skin. In certain embodiments, the prebiotic composition of the present invention may be incorporated into a color cosmetic, such as a foundation, which is applied to the user's face or a portion thereof as part of a daily beauty regimen.

[0108] In certain embodiments, certain areas of the skin may be identified as needing skin care benefits that can be addressed by the use of the prebiotic composition of the present invention or the topical cosmetic composition of the present invention. For example, areas of the face (e.g., nose, cheeks, forehead, chin, around the eyes), the front and back of the neck, on the hands, on the forearms, shoulders and / or major body folds may be identified as needing treatment with the prebiotic composition or topical cosmetic composition of the present invention. Of course, it should be understood that the prebiotic composition or topical cosmetic composition disclosed herein may be applied to any part of the skin on the body (e.g., feet, legs, back, upper arms, torso, buttocks) to provide cosmetic benefits, and such parts of the skin may be identified as target areas.

[0109] The topical cosmetic composition of the present invention may be applied one or more times per day as part of the user's regular beauty regimen (e.g., showering, applying makeup, applying moisturizers or other skin or hair care products). The topical cosmetic composition of the present invention may be applied multiple times per day, for example, once at the beginning of the day, once in the middle of the day, and / or once at the end of the day. In some cases, the topical cosmetic composition may be applied whenever the user applies or reapplies other cosmetic compositions, such as lipstick or mascara. In some cases, it may be desirable to apply the topical cosmetic composition of the present invention every other day, two or three times per week, once per week, once every two weeks, or once per month, as needed. It may be desirable to apply the topical cosmetic composition of the present invention such that at least a portion of the composition (e.g., the prebiotic portion) is present on the user's skin for at least one hour (e.g., 1 to 24 hours, 2 to 20 hours, 4 to 16 hours, or 8 to 12 hours). In certain embodiments, it may be desirable to apply the composition such that at least a portion of the composition is present on the skin for more than one day (e.g., 1-7 days, 2-6 days, 3-5 days, or even 4 days). In certain embodiments, it may be desirable to apply the topical cosmetic composition of the present invention at one or more of the frequencies described above for at least two consecutive or non-consecutive application periods. For example, the composition may be applied once a day for 2 consecutive days, 3 consecutive days, 4 consecutive days, 5 consecutive days, 6 consecutive days, or 7 consecutive days, or on non-consecutive days. In another example, the cosmetic composition may be applied every other day for a month or more.

[0110] Those skilled in the art will understand that the invention described herein may be subject to variations and modifications other than those specifically described. It is to be understood that the present invention includes all such variations and modifications to the extent that they do not depart from the spirit or essential characteristics thereof. The present invention also includes all of the steps, features, compositions and compounds mentioned or shown in this specification, individually or collectively, and any and all combinations or any two or more of said steps or features. Therefore, the present disclosure should be considered in all respects as illustrative and not restrictive, and the scope of the present invention is indicated by the appended claims, and all changes that come within the meaning and range of equivalents are intended to be embraced within the scope of the present invention.

[0111] The above description will be more fully understood with reference to the following examples, however, such examples are illustrative of methods of practicing the invention and are not intended to limit the application and scope of the invention. EXAMPLES

[0112] Preparation of Brewery Spent Grain (BSG) Extract Preparation of BSG-derived P1 500 g of brewer's spent grains (BSG) (dry basis) suspended in 3.75 L of water with ionic polymer catalyst "IP1" was stirred at 140°C for 1 hour. After reaction, the mixture was cooled to room temperature, filtered and the liquid phase was dried using a spray dryer. The resulting dry powder product was analyzed and used for activity testing. P1 contained 57.9% oligosaccharides, with 44.7% and 13.2% as arabinoxylan and glucan, respectively. See Table 1.

[0113] Preparation of BSG-derived P2 267 g of BSG (dry basis) suspended in 4 L of water was stirred at 90° C. for 1 hour. The mixture was then cooled to room temperature, filtered and the solid phase was resuspended in 2.850 L of water with "IP1" and stirred at 140° C. for 1 hour. After the reaction, the mixture was cooled to room temperature, filtered and the liquid phase was dried using a spray dryer. The resulting dry powder product P2 was analyzed and used for activity testing. P2 contained 62% oligosaccharides, with 51% and 11% as arabinoxylan and glucan, respectively. See Table 1.

[0114] Preparation of BSG-derived P3 200 g of BSG (dry basis) suspended in 1.5 L of water and 100 ml of ethanol was stirred at 145° C. for 1.5 hours with ionic polymer catalyst “IP1”. After reaction, the mixture was cooled to room temperature, filtered and the liquid phase was dried using a spray dryer. The resulting dry powder product was analyzed and used for activity testing. P3 contained 53.5% oligosaccharides, with 38.3% and 15.2% as arabinoxylan and glucan, respectively. See Table 1.

[0115] Preparation of BSG-derived P4 200 g of BSG (dry basis) suspended in 1.5 L of water with ionic polymer catalyst "IP1" was stirred at 140°C for 1 hour. After reaction, the mixture was cooled to room temperature and filtered. A certain amount of bentonite was added to the filtrate and the mixture was stirred at room temperature for 1 hour. The mixture was then filtered and the liquid phase was dried using a spray dryer. The resulting dry powder product was analyzed and used for activity testing. P4 contained 57% oligosaccharides, with 41.4% and 15.6% as arabinoxylan and glucan, respectively. See Table 1.

[0116] Preparation of BSG-derived P5 500 g of BSG (dry basis) suspended in 3.75 L of water with ionic polymer catalyst "IP1" was stirred at 140°C for 1 hour. After reaction, the mixture was cooled to room temperature, filtered and the remaining solid fraction in the presence of the catalyst was redispersed in water again and subjected to one more hydrolysis cycle. After cooling, the same type of operation was performed to complete the final hydrolysis cycle. After cooling, the resulting mixture was filtered and the liquid phase was dried using a spray dryer. The resulting dry powder product was analyzed and used for activity testing. P5 contained 52.9% oligosaccharides, with 48% and 4.9% as arabinoxylan and glucan, respectively. See Table 1.

[0117] [Table 1]

[0118] Preparation of BSG-derived P6 An ionic polymer IP-A5 was prepared consisting of a monomer of the following formula (I) and a monomer of the following formula VI. [ka]

[0119] IP-A5 was used for spent barley hydrolysis. 500 g of brewer's spent grains (BSG) (dry basis) suspended in 3.75 L of water with ionic polymer catalyst "IP-A5" was stirred at 130°C for 1.5 hours. After reaction, the mixture was cooled to room temperature, filtered and the liquid phase was dried using a spray dryer. The resulting product contained 40.3% oligosaccharides with 35.7% and 4.6% as arabinoxylan and glucan, respectively.

[0120] Preparation of BSG-derived P7 An ionic polymer IP-A6 was prepared from a monomer of the following formula (I) and a monomer of the following formula (VI). [ka]

[0121] IP-A6 was used for spent barley hydrolysis. 500 g of brewer's spent grains (BSG) (dry basis) suspended in 3.75 L of water with ionic polymer catalyst "IP-A6" was stirred at 130°C for 1.5 hours. After reaction, the mixture was cooled to room temperature, filtered and the liquid phase was dried using a spray dryer. The resulting product contained 61.5% oligosaccharides with 46.8% and 14.7% as arabinoxylan and glucan, respectively.

[0122] Activity Test A microbiological screening study on liquid broths was performed to evaluate the activity (bacterial growth) of five preparations (P1, P2, P3, P4 and P5) against two staphylococcal species, (1) Staphylococcus aureus (MRSA) ATCC 33591 as a potential skin pathogen, and (2) Staphylococcus epidermidis ATCC 12228 as a commensal strain in healthy skin. The experimental results are presented below with the aim to evaluate potential and strain-specific antibacterial or prebiotic activity against staphylococcal species and to test the hypothesis that ingredients may have a prebiotic effect (against S. epidermidis) while negatively affecting viability or growth rate (against S. aureus).

[0123] Prebiotic Verified To evaluate potential and strain-specific antibacterial or prebiotic activity against Staphylococcus species, microdilution assays (viable counts on agar plates) in liquid broth were performed using three different concentrations, ranging from 4% to 2% to 1%, for each component, compared to inulin and glucose as carbon source and prebiotic reference.

[0124] Each strain was inoculated into nutrient-poor medium supplemented with three concentrations of the test article and allowed to grow for up to 24 hours. Bacterial viability measurements were then performed on agar plates by viable count (CFU / mL) at 4 and 24 hours, corresponding to early exponential and stationary phases, respectively, to assess interference with bacterial growth. Each treatment was performed in triplicate.

[0125] Viable count (CFU / mL) growth rate checks were performed to quantify the number of remaining viable cells present in the test cultures, which were then expressed as Log values.

[0126] See results in Table 2.

[0127] [Table 2] (1) First start date, (2) Second start date

[0128] The negative control (NC, culture medium alone) and the positive control PC (inulin 4% and glucose 4%) showed similar growth to the inoculum number by 24 hours, thus confirming bacterial vitality and validating the test system.

[0129] For the BSG-derived components tested, the observed results reveal the following: · Bold (in the S. epidermidis section) indicates results where the number of CFUs was higher than both 4% glucose and inulin (carbon sources as prebiotic references). Light grey indicates results where the difference in the number of CFU obtained in the presence of test products (P2 at 1% and P3 at 2%) compared to the CFU obtained in the presence of glucose (4%) or inulin (4%) is greater than 0.5 Log (test products higher than control), which is considered as the minimal significant increase to define a prebiotic effect (bacterial growth).

[0130] A slight effect was observed at 24 h, which could be related to the high concentration of bacteria and the possible achievement of a stationary phase in bacterial growth. It should be noted that the bacterial viability measured at 4 and 24 h corresponds to the early exponential and stationary phases, respectively. The stationary phase (idiophase) is the stage where a microorganism stops its growth, often due to a growth-limiting factor such as the depletion of essential nutrients. The stationary phase results from a situation where the growth rate and the death rate are equal (the number of new cells created is limited by growth factors, so that the rate of cell growth matches the rate of cell death). Beyond this stage, a decline phase may have been initiated, where bacteria die due to lack of nutrients, making the 24 h interpretation less robust in terms of viable growth quantification.

[0131] All BSG-derived preparations (P1-P2-P3-P4-P5) demonstrated the ability to maintain S. aureus growth below the control (bacteriostatic effect). In particular, these results show that: · Bold (in the S. aureus section) indicates results where the number of CFUs was lower than with both 4% glucose and inulin (carbon sources as prebiotic references). · Bold italics indicate results where the difference in the number of CFU obtained in the presence of the test article compared to the CFU obtained in the presence of glucose (4%) or inulin (4%) exceeds 0.5 Log (test article lower than control), which is considered the minimal significant reduction to define antimicrobial effect (reduction in bacterial growth). A better antimicrobial effect was observed up to 4 hours, but by 24 hours only articles P3 (all concentrations) and P2 and P1 at 4% showed a significant antimicrobial effect against the control.

[0132] Anti-pathogen verification The following series of experiments was carried out with the aim of testing the hypothesis that the ingredients may have different effects on the bacterial species, in particular that the ingredients may have a prebiotic effect on S. epidermidis while adversely affecting the viability or growth rate of S. aureus.

[0133] Components were diluted in minimal growth medium at the three required concentrations to provide a low level inoculum (10 2 ) to a mixture of two Staphylococcus species (1:1 ratio) and allowed to grow for up to 24 hours. Then, viability measurements of each bacteria at 4 and 24 hours were performed by viable count (CFU / mL) on Chromoselect agar plates (which can distinguish between the two strains) to assess the effect on bacterial growth.

[0134] See results in Table 3.

[0135] [Table 3] (1) First start date, (2) Second start date

[0136] The negative control (NC, culture medium alone) for up to 4 hours showed growth that was not different from the inoculum number, thus confirming bacterial viability and the validity of the test system.

[0137] All preparations (P1-P2-P3-P4-P5-A82) showed the ability to maintain bacterial growth below the control for up to 4 hours (bacteriostatic effect) compared to the control. In particular, the results show that: · Bold (in the S. epidermidis section) indicates results where the number of CFU was higher than in the negative control (culture medium only). Light grey indicates results where the difference in the number of CFU obtained in the presence of the test article (2% P5 after 2 hours and 4% P4 after 4 hours) compared to the CFU obtained in the negative control exceeds 0.5 Log (test article higher than control), which is considered as the minimal significant increase to define a prebiotic effect (bacterial growth). · Bold (in the S. aureus section) indicates results where the number of CFU was lower than in the negative control (culture medium only). · Bold italics indicate results where the difference in the number of CFU obtained in the presence of the test products (P3 at all concentrations after 2 hours and at higher concentrations P1, P2, P3 and P4 at 4% after 4 hours) compared to the CFU obtained with the negative control exceeds 0.5 Log (test product lower than control), which is considered the minimum significant reduction to define the antibacterial effect (reduction in bacterial growth). Considering both the combined effects of prebiotic (growth increase) of S. epidermidis (0.71 Log increase) and antibacterial (growth reduction) of S. aureus (0.56 Log decrease), it can be concluded that P4 at 4% showed the best results after 4 hours of contact.

[0138] Conclusion Potential antibacterial activity against S. aureus and prebiotic effect against S. epidermidis: Considering a CFU difference of more than 0.5 Log against both controls (4% inulin and glucose) that is significant to define a prebiotic effect (increased bacterial growth) or an antibacterial effect (decreased bacterial growth), the best and most definitive outcome is P2 at a concentration of 1% after 4 hours of contact P3 at a concentration of 2% after 4 hours of contact was shown.

[0139] Considering a difference of more than 0.5 Log relative to the negative control as significant to define a prebiotic effect (increased bacterial growth) or an antimicrobial effect (reduced bacterial growth), better results regarding the combined effect of the two were shown by P4 at a concentration of 4% after 4 hours of contact.

[0140] Reconstructed Human Epidermis (RHE) Test The main aim of this study was to evaluate the potential efficacy of BSG-derived preparations on a more biologically relevant in vitro preclinical model based on colonized reconstituted human epithelium (RHE). Mainly, we focused on: I. Counteracting Staphylococcus aureus adhesion and its proliferation potential. The rationale was based on the possibility that the components could balance the inflammatory response induced by the bacteria, decreasing its adhesion and proliferation in the RHE model (inhibition test). II. Prebiotic effect of the three preparations versus Staphylococcus epidermidis (prebiotic test). The rationale was based on the potential of the ingredients to protect and biostimulate the normal skin microflora. III. Their biological impact on the germ-free RHE model. The rationale was based on the possibility that the components might enhance or balance the innate immune response.

[0141] For this study, the following BSG-derived preparations were used: Inhibitory and component effects: 1% P1, 2% P3, and 4% P4 Prebiotic effect: 1% A78, 2% P3, and 1% P5

[0142] SkinEthic(TM) Reconstituted Human Epidermis 0.5cm 2 is a reconstructed epidermis of normal human keratinocytes. The cells are grown on inert polycarbonate filters in synthetic medium (chemically defined medium) for 17 days. This model reproduces epidermal morphology and is fully characterized. Good barrier function, batch reproducibility and low variability in terms of permeability of probe molecules are described in the literature in comparison with human ex vivo models. RHE batches were tested for the absence of HIV1 and HIV2 antibodies, Hepatitis C antibodies and Hepatitis B antigen HB. The absence of bacteria, fungi and Mycoplasma was verified on donor-derived cells. Maintenance medium was tested for sterility.

[0143] Description of bacterial suspension preparation for RHE colonization Two days before the test, the bacterial strains (S. aureus and S. epidermidis) were inoculated daily onto culture media (BHI agar plates) and incubated under aerobic conditions at 37°C for at least 24 hours to obtain fresh cultures. On the day of colony formation, the bacterial strains were resuspended in sterile saline at the required concentration range. Each starting bacterial inoculum concentration was confirmed by spectrophotometric OD measurements and reached approximately 10 7 ~10 8 The solution was adjusted to obtain a range of UFC / mL (OD = 0.1). This was then diluted 10-fold to obtain 10 3 ~10 4 10 in UFC / tissue and prebiotic studies 4 ~10 5 A final range of UFC / tissue concentrations was obtained. The initial inoculum levels were also confirmed by 10-fold serial dilutions and viable counts on agar plates (BHI).

[0144] Description of treatments and colonization procedures For both inhibition and prebiotic, RHE were pretreated twice (50 μL and 30 μL, respectively, overnight and 1 h prior to colonization) on the apical part (spread directly on the tissue surface) and left to incubate at 37° C. (with 5% CO2) until colonization. Pretreated RHE dedicated to inhibition and prebiotic tests were colonized with 30 μL of previously obtained bacterial suspension (S. aureus for inhibition tests and S. epidermidis for prebiotic tests, respectively) and incubated at 37° C. (with 5% CO2) until the required time point (24 h). Non-colonized RHE sterilized specimens were pretreated twice (50 μL and 30 μL, respectively, overnight and 1 h prior to colonization) on the apical part (spread directly on the tissue surface) and left to incubate at 37° C. (with 5% CO2) until the required time point (24 h). At the end of the time points, apical debris and tissues were collected, homogenized, and then analyzed. For both inhibition and prebiotic studies: CFU, and qRT-PCR (gene expression) for TLR-2, b-defensin2, NOD-2 were performed. The following was known: ·TLR2 receptor is involved in innate immunity. It recognizes pathogen antigens and activates innate immunity through stimulation of NF-kB. Induction of DEFB2 by inflammatory stimuli and opportunistic pathogens supports the hypothesis that this peptide contributes to a dynamic host defense system. ·NOD-2 plays an important role in immune system function. In several types of immune system cells, it helps protect the body from foreign invaders such as bacteria and viruses. When triggered by certain substances produced by bacteria, the NOD2 protein activates NF-kB. NOD-2 also plays a role in autophagy.

[0145] See results in Table 4.

[0146] [Table 4]

[0147] The colony formation control (CNZ) showed growth above the inoculum number, thus confirming bacterial viability and the validity of the test system.

[0148] The reference control (REF, chlorexidine) showed no bacterial growth, thereby confirming bacterial susceptibility to the antimicrobial agents.

[0149] Compared to the colony formation control, preparations P3 at 2% and P4 at 4% demonstrated the ability to reduce bacterial growth. In particular, the results show that: · Bold indicates results where the number of CFUs was lower than the colony formation control. Bold italics indicate results where the difference between the number of CFU obtained in the presence of the test articles (P3 and P4) compared to the CFU obtained in the colony formation control exceeds 0.5 Log (test articles lower than control), which is considered the minimal significant reduction to define antibacterial efficacy (reduction in bacterial growth).

[0150] Based on the data shown in Figure 1, DEFB2 was upregulated in all lineages except NC (negative control). This antimicrobial protein is expressed when epidermal cells are stimulated by contact with microorganisms and is a dynamic component of the skin's local innate defense system. Its expression in RHE treated with BSG-derived components suggests that they may play a role in inducing the primary innate immune defense against infection. (J.-M. Schroder, J. Harder. Molecules in focus human beta-defensin-2. Int. J. Biochem. Cell Biol., 31 (1999), pp. 645-651; P. Zanger, J. Holzer, R. Schleucher, H. Scherbaum, B. Schittek and S. Gabrysch. Severity of Staphylococcus aureus Infection of the Skin Is Associated with Inducibility of Human β-Defensin 3 but Not Human β-Defensin 2. Infection and Immunity Vol. 78, No. 7 (2010), pp. 3112-3117).

[0151] NOD-2. No gene regulation was observed in all lineages, suggesting that the biological mechanism by which the BSG-derived preparations act is not based on the proinflammatory NfkB-dependent pathway.

[0152] TRL-2 was only upregulated in the presence of 4% test article P4. The protein encoded by this gene is a member of the Toll-like receptor (TLR) family that plays a fundamental role in pathogen recognition and innate immune activation. It is a cell surface protein that can form heterodimers with other TLR family members to recognize microbial-derived molecules.

[0153] Based on the data shown in Figure 2, DEFB2 was upregulated in all lines except NC (negative control) and colonization control (CNZ). This antimicrobial protein is expressed when epidermal cells are stimulated by contact with microorganisms and is a dynamic component of the skin's local innate defense system. Its expression in RHE treated with BSG-derived components suggests that they may have a role in inducing the main innate immune defense against infection, as already observed in the case of S. aureus.

[0154] No gene regulation was observed in all lineages, suggesting that the biological mechanism by which BSG-derived components act is not based on the proinflammatory NfkB-dependent pathway.

[0155] TLR-2 was not significantly expressed in all samples (revealed during PCR)

[0156] Conclusion S. aureus growth inhibition test Based on the results obtained by viable counts of both the apical and homogenate portions after 2 days as pretreatment, it can be stated that the best and most reliable results compared to the colonized series (CNZ) were shown by P3 at a concentration of 2% after 2 days as pretreatment and by P4 at a concentration of 4% after 2 days as pretreatment. S. aureus growth inhibition was confirmed by the results in colonized RHE by gene expression data where DEFB2, an antimicrobial protein involved in the innate immune response, was upregulated in the presence of the tested components. P4 at 4% induced a significant upregulation of the TRL-2 gene.

[0157] Prebiotic Testing: All three BSG-derived preparations determined the upregulation of befensin beta 2, a gene involved in innate immune activation and enhanced antibacterial properties, without activating the proinflammatory pathway based on the NOD-2 and TLR-2 genes.

Claims

1. A method for producing a prebiotic composition, a) A process of providing biomass, b) A step of optionally determining the content of lipids, proteins and / or carbohydrates in the biomass, c) A step of optionally pre-treating the biomass, wherein the optionally pre-treatment is a hot water pre-treatment at approximately 90°C. d) Optionally, a step of removing lipids and / or proteins from the biomass, e) A step of contacting the biomass with a catalyst in the presence of water and / or an organic solvent to form a reaction mixture, wherein the catalyst is an ionic polymer or a combination of ionic polymers, an ionic polypolymer network, an ionic polymer supported on a solid support, and / or a polymer film incorporating an ionic polymer. f) A step of heating the reaction mixture at 100°C to 150°C to decompose the biomass in the reaction mixture and produce a liquid phase and a solid phase, wherein the liquid phase contains the prebiotic composition and the solid phase contains residual biomass. g) A step of cooling the reaction mixture to room temperature, h) A step of isolating at least a portion of the liquid phase from the solid phase, i) A step of optionally adding one or more compounds selected from bentonite, charcoal, zeolite, amorphous silica and / or ion-exchange solvents to the isolated liquid phase, j) A step of recovering the prebiotic composition from the isolated liquid phase. The ionic polymer (IP) comprises a monomer of formula I, 【Chemistry 1】 or the first monomer of formula I 【Chemistry 2】 and, 【Transformation 3】 It consists of at least one second monomer selected from the group comprising, During the ceremony, n and m are independently selected from 1, 2, 3, 4, 5, and 6. z and w are independently selected from 0, 1, 2, and 3. Z １ Z ２ and Z ３ Each of them operates independently. 【Chemistry 4】 A cation selected from the group including, R1, R2, R3, R4, R5, R6, and R7 are each independently a bond, H, C １ ~C ６ alkyl, C １ ~C ６ allyl, -CH ２ -(CH ２ ) ｐ -O-(CH ２ ) ｑ -CH ３ , C １ ~C ６ alkoxy, C １ ~C ６ alkoxyalkyl, benzyl, -SO ３ H, -(CH ２ ) ｑ -SO ３ H, provided that two of R1, R2, R3, R4, R5, R6, and R7 are each a bond p and q are independently selected from 0, 1, 2, 3, 4, 5, and 6. L is an optional linker, and if present, each occurrence of L independently corresponds to H, a substituted or unsubstituted C. １ ~C ２０ Alkylene, C １ ~C ２０ Alkenylene, C １ ~C ２０ Alkynylene and substituted or unsubstituted C ５ ~C １０ Selected from aryls, the substituents are H, -SO ３ H, -COOH, -[P(=O)(OH) ２ ], -O-SO ３ H, -O-COOH, -O-[P(=O)(OH) ２ Selected from the group including ] A is an optional acidic group, and if present, each occurrence of A is independently H, -SO ３ H, -COOH, -[P(=O)(OH) ２ ], -O-SO ３ H, -O-COOH, -O-[P(=O)(OH) ２ ], -CH ２ - Selected from the group containing COOH, however, if z and w are 0, A exists in formula IV. X － is, F － , Cl － , Br － , I － , ClO ４ － BF ４ － , PF ６ － AsF ６ － SbF ６ － NO ２ － NO ３ － HSO ４ － SO ４ ２－ , PO ４ ３－ HPO ４ ２－ CF ３ CO ２ － CF ３ CO ３ － CO ３ ２－ CF ３ SO ３ － , C １ ~C ６ Carboxylate, CN － SCN － OCN － , CNO － , N ３ － Selected from the group including tosylate, mesylate, trifluoromethanesulfonate, trifluoroethanesulfonate, ditrifluoromethanesulfonylamino, doxate, and xylenesulfonate, Ra is C １ ~C ２４ It is alkyl, Rb and Rc are independently H and CH ３ Selected from the group that includes, or if none exist, Rd is C １ ~C ２４ alkylene optionally substituted by C １ ~C ２４ or C １ ~C ２４ alkyl, and Re and Rf are independent of each other, C １ ~C ２４ It is alkyl, Y is either N or O, however, if Y is O, then Rc does not exist. R is C １ ~C ２４ alkyl and C ５ ~C １０ selected from the group including aryl or absent, The ionic polypolymer network comprises one or more crosslinked ionic polymers (IP), The solid support has at least one surface comprising one or more ionic polymers (IPs) or an ionic polypolymer network, The polymer film incorporates one or more ionic polymers (IPs) or the ionic polypolymer network. method.

2. In the ionic polymer (IP), Z １ Z ２ and Z ３ Each of them operates independently. 【Transformation 5】 The method according to claim 1, wherein the cation is selected from the group including the group.

3. The second tourist of formula VI is 【Transformation 6】 The method according to claim 1 or claim 2.

4. The aforementioned ionic polymer (IP) is 【Transformation 7】 The method according to claim 1.

5. The method according to claim 1, wherein the biomass is used grain from a brewery.

6. A prebiotic composition obtained by the method described in claim 1.

7. An effective amount of the prebiotic composition according to claim 6, At least one dermatologically acceptable carrier and A topical cosmetic composition containing the following:

8. Use of the prebiotic composition according to claim 6 for non-therapeutic treatment of the skin.

9. The use according to claim 8, wherein the non-therapeutic treatment is skin protection and / or regeneration.

10. The use according to claim 8, wherein the non-therapeutic treatment is to protect and improve the condition and / or appearance of the skin.

11. The use according to claim 8, wherein the non-therapeutic treatment is to maintain skin hydration.

12. Use of the prebiotic composition according to claim 6 for regulating the growth of at least one symbiotic bacterium on the skin, comprising the step of applying an effective amount of the prebiotic composition according to claim 6 to the skin.

13. The use according to claim 12, wherein the symbiotic bacteria are selected from the group consisting of Propionibacterium acnes, Corynebacterium tuberculastearicum, Streptococcus mytis, Streptococcus oralis, Streptococcus pseudopneumoniae, Streptococcus sanguinis, Micrococcus luteus, Staphylococcus epidermides, Staphylococcus capitis, and Beironera parvula.

14. Use of the prebiotic composition according to claim 6 for preventing dysbiosis.

15. Use of the prebiotic composition according to claim 6 for stimulating the skin immune system.

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