Composition or oat extract containing avenanthramide and beta-glucan

Abstract

To provide a method for preparing an Avena sativa extract.SOLUTION: A method includes a step of extracting an Avena sativa supply source at a temperature 30 to 80°C by using at least one kind of an aqueous extract solvent (extracting agent) containing water and an organic solvent to obtain an extraction mixture or a suspension, a step of removing an insoluble Avena sativa supply source and an organic solvent to obtain an aqueous extract, a step of allowing the aqueous extract to pass through an adsorbent in an adsorption device to adsorb components of the aqueous extract, and a step of eluting an adsorption component of the aqueous extract from an adsorbent by using at least one kind of an elution solvent to obtain an eluate, but does not include a step of membrane filtration.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention generally comprises at least one avenanthramide compound or analog thereof and A composition comprising at least one β-glucan compound in a predetermined ratio and having a low salt content. In addition, the present invention relates to a method for preparing such an oat extract. and a method for producing the same, an oat extract obtained by said method, and food, dietary supplements, cosmetics, Use of said composition or oat extract for the preparation of pharmaceutical or veterinary preparations. Finally, the present invention relates to a food, a dietary supplement, a chemical product containing said composition or oat extract. It relates to cosmetic, pharmaceutical or veterinary preparations. [Background technology]

[0002] Poaceae, also known as Gramineae, is a family of grasses. The grasses are a large and nearly ubiquitous family of monocotyledonous flowering plants. Grasses are an economically important family of plants. They have been used as livestock feed for 6,000 years. Grain of grasses, e.g., wheat, rice, maize (corn), barley, , sorghum, millet and oats have been the most important food crops for humans and remain It seems that this is the case.

[0003] Grains contain many unique substances among their bioactive compounds, e.g., edible fiber (Arabino Silane, β-glucan, cellulose, lignin and lignans), sterols, tocopherols Excellent source of vitamins, tocotrienols, phenolics, vitamins and trace elements It is the source.

[0004] Phenolic compounds have antioxidant properties and inhibit reactive oxygen species (i.e., superoxide) Degenerative diseases involving ions, hydroxyl radicals, and peroxy radicals (e.g., heart disease and A common definition of a phenolic compound is one or Any compound containing a benzene ring with multiple hydroxyl groups. acids, flavonoids, condensed tannins, coumarins and alkylresorcinols are examples. In cereals, these compounds are primarily located within the pericarp, which dehulls the kernel to produce the bran. Phenolic compounds can be concentrated by flavonoids (flavonols). , subclassified into flavones, isoflavones, anthocyanins, flavanols, and flavanones Phenolic compounds can be grouped into flavonoids (which are often referred to as flavonoids) and non-flavonoids. Phenolic compounds can exist in the isolated phenolic or glycosidic form. They tend to be relatively polar, usually pure or aqueous alcohols, e.g., ethanol and methyl It is soluble in alcohol or aqueous acetone. It is the most soluble in many phenolic compounds in grains (e.g., Some phenolic acids and flavonoids have also been reported in fruits and plants. The phenols are specific to one plant species, e.g., oat avenanthramides [Dykes et al., Cereal Foods World, 2007, pp. 105-111 Among cereal grains, only oats contain avenanthramides. These compounds It is an anti-pathogenic compound, produced by plants in response to exposure to pathogens, such as fungi.

[0005] Among them, β-glucan is the main fraction of edible fiber in cereals. β-glucan in barley, oats, rye and wheat grains The average total contents of arsenic were 4.0-7.0%, 2.2-7.8%, 1.2-2.9% and and 0.4-1.4%. (1→3), (1→4), commonly known as β-glucan -β-D-glucan is a D-glucopyranoside linked by a single β-(1→3)-glycosidic linkage. by β-(1→4)-glycosidic bonds separating every second, third, or fourth glycosidic unit The structure of β-glucan is composed of linked D-glucopyranose residues. Determines the properties (solubility in water, viscosity and gel formation) and functional characteristics. For example, it reduces the incidence of coronary heart disease, lowering serum LDL cholesterol and Reduces lipid levels, decreases blood pressure, improves insulin sensitivity, and It has many benefits, including controlling blood sugar levels and possessing antioxidant and anti-inflammatory activity. [Siurek et al., Food Science and Technology I nternational, 2012, Vol. 18(No. 6), pp. 559-568].

[0006] Oat has two main species, Avena sativa L. and Avena nu da L. (synonyms Avena sativum by Gillet and Magne) a subsp. nuda (L.), and Avena sativa by Koern A. sativa is found in oats ( Also known as common oat or hulled oat, it is grown in cold temperate climates, especially It is cultivated mainly in the cold, moist regions of Northern Europe and North America. A. nuda is a The husk is removed when the crop is collected, giving it a husk-free threshing property similar to wheat. Hulled oats are also known as naked oats or dehulled oats. represent the majority of oat production on a large scale, although naked oats are the most This excludes China, where it is also a common species.

[0007] Avenanthramides (hereafter referred to as Avns or the single avenanthramide compound Av) n) is a phenol containing anthranilic acid and hydroxycinnamic acid moieties. Both A. sativa and A. nuda oats contain naturally occurring phenolic amides. Oats are a group of middlings (see Table 1). Oats are a group of approximately 40 different varieties of Avena sativa. These are present in both oat kernels and leaves. The most abundant is Avn A (N -(4'-hydroxycinnamoyl)-5-hydroxyanthranilic acid), Avn B( N-(4'-hydroxy-3'-methoxycinnamoyl)-5-hydroxyanthranil acid), and Avn C (N-(3',4'-dihydroxycinnamoyl)-5-hydroxybenzoyl See Figure 1 and Table 1. These Avns are constitutive They are primarily expressed in the kernel and appear in almost all ground fractions, but their highest concentrations are in the bran. occurs in the outer layer of the seed and kernel [Boz H., Czech Journal of Food Sciences, 2015, Vol. 33(No. 5): pp. 399-404]. The total content of avenanthramides (Avns) in oat grain varied with cultivar and agronomic treatment. It was found that the concentration was approximately 2 to 700 mg / kg (0.0002 to 0.07%) depending on the Aliarova M. et al., Journal of the Brazilian Ch. emical Society, 2015, Vol. 26(No. 11), pp. 2369-2378 Ji].

[0008] Avns exhibited strong antioxidant activity both in vitro and in vivo, as well as in cells. The development of oxidative dysfunction and oxidative stress-related diseases, such as neurodegenerative and cardiovascular diseases, possess anti-inflammatory, anti-irritant, anti-atherogenic and anti-proliferative activities that may prevent or limit the growth of and provides additional protection against skin irritation, aging, CHD and cancer. The study demonstrated [Perrelli A. et al., Oxidative Medicine and Cellular Longevity, 2018, DOI:10.1155 / 2018 / 6015351].

[0009] The antioxidant activity of Avns was significantly enhanced by the typical cereal components ferulic acid, gentisic acid, and p-hydroxybenzoic acid. Protocatechuic acid, hydroxybenzoic acid, silicon dioxide The antioxidant activity of citric acid was found to be 10 to 30 times higher than that of vanillic acid, vanillic acid, and vanillin. Avns differ in antioxidant activity, with Avn C having the highest activity, followed by Avn B and A. This was followed by vn A. Avns-enriched oat extract inhibited LDL oxidation in vitro. Oat antioxidants lower serum cholesterol and LDL cholesterol Potential to reduce cardiovascular risk by inhibiting oxidation and peroxidation This has been confirmed in both animal studies and human clinical trials. Consumption of these foods not only increases the risk of colon cancer due to their high fiber content, but also due to Avns. Another study showed that Avns-enriched oat extract can reduce the risk of It has been shown to inhibit atherosclerosis and activation of the NF-kB transcription factor , NF-kB transcription factor is a regulator of infection and inflammation [Hueseyin Boz, Phenolic Amides (Avenanthramides) in Oats- A Review, Czech J.Food Sci., Vol. 33, 2015(No. 5), Pages 399-404]

[0010] Extraction of Avns from oats can be carried out using various solvent compositions, e.g., pure or diluted Ethanol and methanol were used. Extraction procedures are performed using, for example, naked oat, 50% aqueous ethanol, etc. under controlled heat. achieved [Tong L et al., Journal of Integrative Agr iculture, 2014, vol. 13, p. 1809].

[0011] Maliarova, M. et al., Journal of the Brazilian Chemical Society, 2015, Vol. 26(11), 2369-2378 Page describes the extraction of Avns from naked oat bran using methanol, ethanol, The efficiency of the ethanol and isopropanol was compared. The optimum conditions for the highest yield of Avns were The methanol concentration was 70%, the extraction temperature was 55°C, and the extraction time was 165 minutes.

[0012] In oats, the main component of soluble fiber is oat β-glucan. Glucans are located within the endosperm cell wall, which is adjacent to the aleurone layer in the lower aleurone layer. The process of isolating and purifying oat β-glucan is extremely difficult. The extraction method for oat β-glucan is based on its solubility in hot water and alkaline solution. Purification is based on, for example, separating co-extracted proteins by isoelectric precipitation, and and ammonium sulfate, 2-propanol, or ethanol to extract β-glucan. This can be achieved by precipitation. [Daou C. and Zhang H. , Comprehensive Reviews in Food Science a nd Food Safety, 2012, Volume 11, Pages 355-365].

[0013] Cereal phenolic and β-glucan compounds have potent beneficial biological activities. This makes these compounds suitable for topical and / or topical application for humans and animals. It is a valuable and highly interesting compound for cosmetic, nutritional and health uses for oral application. However, phenolic compounds (e.g., Avns) or the extraction process aimed at preparing an extract rich in β-glucan compounds. The problem described so far is that enrichment of only one of the two substance classes can be achieved. These different solubility characteristics and resulting extractability make These compounds are extractable with different solvents and therefore usually occur in different extracts or extract fractions. β-glucans occur in the aqueous extract, and phenolic compounds occur in pure or aqueous extracts. Occurs in alcohol (e.g., ethanol and methanol) or aqueous acetone extracts Furthermore, they are present in oat kernels in very different concentration ranges, i.e. The average total content of Avns was approximately 0.0002-0.07%, and the average content of β-glucan was approximately 0.0002-0.07%. The average total content is approximately 2.2 to 7.8%.

[0014] Both substance classes have extremely interesting biological benefits, e.g., antioxidant and anti-inflammatory activity. Therefore, the stronger and more pronounced overall activity of the cereal extracts was due to the similarity of both classes of compounds. It can be expected that it will sometimes be obtained from extracts or extract fractions containing it.

[0015] EP1185241A2 and EP1522304A2 are based on 1 to 1500 parts per million (p described the preparation of an Avn-enriched oat extract containing Avn of 10 ... Oat extract was prepared by extracting oatmeal with 50% aqueous ethanol at 40°C for 30 minutes. , adjusting the pH to 2.5 (Example 1) or 3.5 (Example 2) using 1N hydrochloric acid; Ethanol was added, followed by 10 4 The molecular weight cutoff value (MWCO, Example 1 The extract was clarified by membrane filtration through a membrane of 5000 MWCO (Example 2). The resulting Avn-enriched extract contains less than 0.01% by weight of β-glucan. Therefore, oat β-glucan [Si urek et al., Food Science and Technology Intern National, 2012, Vol. 18 (No. 6), pp. 559-568] is described It is removed by membrane filtration at a cutoff value.

[0016] Ren et al., Journal of Agricultural and Food C hemistry, 2011, vol. 59, pp. 206-211. academy of Agricultural Sciences(Beijing, C Preparation of Avn-enriched extract (ARE) from naked oat (Avena sativa L.) provided by Dried and washed oats are processed in a mill to produce oat bran. The oat bran samples were dissolved in ethanol / water / acetic acid (80:2) with a solid-liquid ratio of 1:8. Extraction was performed with 0:0.1 v / v / v) at 40°C for 2 hours, followed by centrifugation at 1250g for 10 minutes. The supernatant was filtered and the solid residue was further extracted twice at 40°C using the same solvent. All three extracted supernatants were pooled, concentrated, and then loaded onto AB-8 resin. The AB-8 resin was washed with 0.1% acetic acid, followed by 95% ethanol. The absorbed Avns were eluted from the column by spraying the ethanol fraction and or using chromatographic grade purity standards, the resulting ARE powder was purified by HP Three major Avns were identified: Avn C (=Bc), Avn A ( =Bp), and Avn B(=Bf) are 6.07%, 4.37% and 5.36%. β-glucan can be extracted with water or alkaline aqueous solution. Therefore, the obtained Avn-enriched extract (ARE) also contains a significant amount of β-glucan. It cannot be expected that it will have. Summary of the Invention [Problem to be solved by the invention]

[0017] Therefore, the primary goal of the present invention is to provide improved beneficial effects due to the presence of both substance classes. Novel compositions containing Avns and β-glucans having beneficial biological activities and properties providing an oat extract, and simultaneously providing oat Avens and β-glucans; This allows for enrichment of both substance classes in one extract fraction. and thereby providing an extract fraction with improved beneficial biological activities and properties. Ideally, the resulting extract fractions would contain both The resulting extract fractions contain the substance classes in approximately equal concentration ranges. or in a pharmaceutically acceptable liquid or solid carrier or in a food or dietary supplement The use of compatible solvents and carriers makes it easy and safe to use and administer. The formulation should be provided in a fixed, easily storable liquid or solid form. [Means for solving the problem]

[0018] Oat Avena sativa and β-glucan enriched in this manner were extracted using a specific extraction process. This can be achieved by a subsequent adsorption / desorption step using a suitable adsorption resin. It was surprisingly discovered that

[0019] In a first aspect, the present invention provides a method for treating atopic dermatitis comprising administering to a subject a therapeutically effective amount of at least one avenanthramide or analog thereof, A composition or ember comprising or consisting of at least one β-glucan and a salt an oat extract, based on the dry weight of the composition or the dry weight of the oat extract, - at least one avenanthramide or its analogue or all avenanthramides or its analogue relative to at least one β-glucan or total β-glucan the ratio is 1:4 to 4:1, in particular 1:3 to 3:1; - a salt content of less than or equal to 1.0% by weight, in particular less than or equal to 0.5% by weight; The present invention relates to a composition or an oat extract.

[0020] In a second aspect, the present invention provides a method for preparing an oat extract, comprising the steps of: (1) preparing an oat source; (2) Oat feed using at least one extraction solvent (extractant) at a temperature of 30-80°C extracting the source to obtain an extract mixture or suspension; (3) removing the extracted insoluble oat source from the extraction mixture or suspension to form an extract; Step to obtain; (4) removing the organic extractant from the extract to obtain an aqueous extract; (5) preparing and conditioning the adsorbent and providing the adsorbent in the adsorption device; P; (6) The aqueous extract is passed through an adsorbent in an adsorption device to adsorb the components of the aqueous extract. Top; (7) Eluting the adsorbed components of the aqueous extract from the adsorbent using at least one elution solvent. obtaining an eluate; and (8) Optionally removing the elution solvent from the eluate to obtain an oat extract fraction. The present invention relates to a method comprising:

[0021] In a third aspect, the present invention relates to an oat extract obtainable using the method according to the invention. Regarding the items.

[0022] In a fourth aspect, the present invention provides a skin care product for skin care, scalp care, hair care, or nail care. As a dermatological cosmetic or for skin conditions, intolerant and sensitive skin, skin irritation, skin redness , wheals, pruritus (itching), skin aging, wrinkle formation, loss of skin volume, loss of skin elasticity, Prevention of pigmented spots, pigmentation disorders, or dry skin, i.e., dry skin that requires skin moisturizing; The present invention relates to the use of a composition or an oat extract according to the present invention in and / or in the treatment of

[0023] In a fifth aspect, the present invention relates to a method for treating skin or keratinopathy, in particular blisters, and to a method for treating ... inflammatory, immunoallergic, atherogenic, dry or hypertrophic conditions associated with In the prevention and / or treatment of skin or keratinopathy having a proliferative component or in the prevention and / or treatment of skin diseases associated with increased ROS production, or Serum in the prevention and / or treatment of cardiovascular disease, allergic reactions, coronary heart disease To reduce blood pressure, to reduce LDL cholesterol and lipid levels in the blood to improve insulin sensitivity and enable blood sugar control, The present invention relates to a composition or an oat extract according to the present invention for use.

[0024] In a sixth aspect, the present invention provides a food, dietary supplement, cosmetic, pharmaceutical or veterinary preparation. The present invention relates to the use of a composition or an oat extract according to the invention for the preparation of a medicament for treating a stomach ulcer.

[0025] Finally, the present invention relates to a food, nutritional supplement, or a pharmaceutical product comprising a composition or an oat extract according to the present invention. For food, cosmetic, pharmaceutical or veterinary preparations. [Brief explanation of the drawings]

[0026] [Figure 1] FIG. 1 shows particle size distribution of spray dried oat extract fractions combined with maltodextrin DE17-20.

[0027] [Figure 2] FIG. 1 shows particle size distribution of spray-dried oat extract fractions combined with maltodextrin DE8.

[0028] [Figure 3] 1 is an HPLC chromatogram of the dried ethanol eluate of Example 7.

[0029] [Figure 4] 1 is an HPLC chromatogram of the dried methanol / water eluate of an oat straw extract according to Example 14 of WO2004 / 047833A1. DETAILED DESCRIPTION OF THE INVENTION

[0030] The present invention is set forth in the appended claims. The present invention and preferred modifications thereof, other objects and advantages are also set forth below in conjunction with the accompanying examples and drawings. This will become clear from the detailed description below.

[0031] In a first aspect, the present invention provides a method for treating atopic dermatitis comprising administering to a subject a therapeutically effective amount of at least one avenanthramide or analog thereof, A composition or ember comprising or consisting of at least one β-glucan and a salt an oat extract, based on the dry weight of the composition or the dry weight of the oat extract, - at least one avenanthramide or its analogue or all avenanthramides or its analogue relative to at least one β-glucan or total β-glucan The ratio is in the range of 1:4 to 4:1, particularly 1:3 to 3:1; - a salt content of less than or equal to 1% by weight, in particular less than or equal to 0.5% by weight, The present invention relates to a composition or an oat extract.

[0032] The composition or oat extract according to the invention comprises at least one avenanthramide or or its analogs and at least one β-glucan as its main component or It consists of these.

[0033] The phrase "at least one," when used in this record, refers to a composition or an emblem. The extract may contain, for example, one avenanthramide or more than one avenanthramide. or, for example, one β-glucan or more than one Furthermore, "at least one of the β-glucans" means that the β-glucan can be contained. The phrase "one" when applied to a list refers to any set of items identified in the list. It means combination.

[0034] The composition according to the first aspect of the invention comprises the specified components described in more detail below. It is prepared by combining the ingredients.

[0035] The extract according to the first aspect of the invention is prepared from oats. The species are Avena sativa L. and Avena nuda L. (synonyms: Avena sativa subsp. nuda by Gillet and Magne (L.) and Avena sativa var. nuda (L.) by Koern A. sativa is grown on common oat or hulled oats. A. nuda is also known as 'nbaku'. The husk is removed when the crop is collected. Therefore, it is known as naked oats or dehulled oats. and can be separated into constituent fractions including oat kernels, husks and trichomes. In a preferred variant, the starting material for the oat extract is Avena sativa species. or ground or unground kernels or seeds of the Avena nuda species It's a straw man.

[0036] Within the context of the present invention, the term "oat extract" generally refers to a compound obtained from oats. The term "extract" is intended to encompass any compound or mixture of compounds that contains any enzyme. Bak seeds, fresh or dried, or parts thereof, such as kernels, husks, trichomes or can be obtained by extraction from oat straw. By modifying the composition of the extraction solvent, , altering the composition of the extract and thereby increasing or decreasing its biological activity. The research by Collins that resulted in U.S. Patent No. 5,169,660 For the first time, it has been discovered that avenanthramides occur naturally and can be extracted from oat kernels. I was able to show this.

[0037] Within the context of the present invention, the term "avenanthramide" (anthranilic acid amide) refers to It is found in oats (Avena sativa) and in the eggs of the cabbage white butterfly (Pie ris brassicae and P. rapae) and fungus-infected carnations Phenolic alkalogen compounds also found in Dianthus caryophyllus It is thought to mean a member of the Ido group.

[0038] The avenanthramides in the compositions of the present invention are isolated and purified from natural sources, such as cereal grains. Avenanthramides can be purified and are most highly concentrated in the peripheral regions or in the husk or straw. More than 50 distinct avenanthramides appear to be isolated from oat kernels. [Collins, Journal of Agricultural nd Food Chemistry, Vol. 37 (1989), pp. 60-66].

[0039] Avns can be represented by the following general formula 1: [ka]

[0040] Table 1 below lists naturally occurring, isolated and / or synthetic Avns based on general formula 1. Here is an example:

[0041] [Table 1]

[0042] The most abundant avenanthramide in oats is avenanthramide A (2p, AF-1 or or Bp), avenanthramide B (2f, also known as AF-2 or Bf) ), avenanthramide C (also known as 2c, AF-6 or Bc), avenanthramide L (non-Collins abbreviation; CAS number 172549-38-1) (avenanthramide O (Colli avenanthramide P (also known as 2fd) or 2pd), avenanthramide P (also known as 2fd) and and avenanthramide Q (also called 2cd). Several studies have shown that these natural The product has anti-inflammatory, antioxidant, anti-pruritic, anti-irritant and anti-atherogenic activity. This demonstrates that:

[0043] Alternatively, naturally occurring avenanthramide compounds isolated from natural sources may also be useful. They can also be produced by mechanical synthesis. Methods of synthesis known in the art are described, for example, in U.S. Pat. No. 6,096,770 and U.S. Patent No. 6,127,392, Japanese Patent No. J6001 9754 and Hungarian Patent No. HU200996B.

[0044] The synthetic avenanthramide substances prepared above were similar to the corresponding naturally occurring avenanthramides extracted from oats. It is identical to the avenanthramide compound.

[0045] The non-naturally occurring avenanthramide analogs in the compositions of the present invention have the following formula 2: [ka] (wherein m=0, 1, 2 or 3, p=0, 1 or 2, and n=0, 1 or 2, However, when n=1 or 2, p+m>0, When n=1 or 2, R 1 and R 2 represents H in each pair. or other chemical bonds together (e.g., as cinnamic acid derivatives), When m=1, 2, or 3, each X independently represents OH, Oalkyl, or Oacyl. Represents, When p=1 or 2, each Y independently represents OH, Oalkyl, or Oacyl. , When p+m>0, at least one of X and Y is selected from the group consisting of OH and O acyl. provided that the compound is selected from the group consisting of R 3 is -H or alkyl (especially -CH3, or other alkyl groups with 2 to 30 carbon atoms) In this context, R 3 The corresponding pharmaceutically acceptable (Also -H for acceptable salts) and has important biological properties, as described, for example, in WO2004 / 0478 33A1 or WO2007 / 062957A1 It has been completed.

[0046] Particularly preferred compounds of formula 2 according to the present invention are n=1 or 2 and p+m>0, and / or p+m>0, and at least one of X or Y, X and Y is OH and O The compound is selected from the group consisting of:

[0047] Particularly preferably, n=1 and p+m>2, provided that at least one of X and Y Formula 2, provided that at least two are selected together from the group including OH and Oalkyl. The compound is used.

[0048] n=1 and m=1, 2 or 3, provided that at least one X is OH and and / or provided that P=1 or 2. with the proviso that at least one Y is selected from the group consisting of OH and Oalkyl It is also preferred to use compounds of formula 2 in which

[0049] If n has the value 1, then R 1 and R 2 are each preferably H, with the proviso that R 1 and R 2 It is also possible for the groups to join together into another chemical bond.

[0050] Formula 2 and WO2004 / 047833A1 or WO2007 / 062957A1 Regarding the definition of the specific avenanthramide compounds disclosed, the corresponding disclosures in the above documents are The disclosure is incorporated herein by reference.

[0051] The avenanthramide analog compound of formula 2 is preferably [ka] [ka] [ka] [ka] is selected from the group consisting of:

[0052] The above examples essentially relate to compounds of formula 2 where n=1.

[0053] However, the use of compounds of formula 2 where n=0 is also often preferred, in which case m+ p=0 or m+p>1 or 2, provided that among the substituents X and Y, are selected from the group consisting of OH and Oalkyl. is preferred.

[0054] [ka] [ka] [ka] It is particularly preferred to use compounds of formula 2 (n=0) selected from the group comprising:

[0055] Particularly preferred are compounds represented by these structural formulas, where R 3 is always H be.

[0056] Instead of these preferred compounds, in each case, R 3 is CH3, or Use the corresponding compounds, which are straight-chain or branched alkyls with 2 to 30 carbon atoms. It is also preferable to

[0057] From the above avenanthramide analogues, compound number 8 (dihydroavenanthramide D ) and number 27 are particularly preferred.

[0058] In addition to the naturally occurring avenanthramides and non-naturally occurring avenanthramide analogs described above, , N-(4'-hydroxycinnamoyl)-3-hydroxyanthranilic acid (YAvn I) and N-(3'-4'-dihydroxycinnamoyl)-3-hydroxyanthranilic acid Production of novel avenanthramide analogues in recombinant yeast, including valeric acid (YAvn II) These encode the major proteins involved in the biosynthesis of phenolic esters. Two plant genes (4cl-2 from tobacco and hc from artichoke) Engineering Saccharomyces cerevisiae strains using Notably, YAVN I and YAVN II were generated by They share structural similarities with Avn A and Avn C, respectively.

[0059] In the context of the present invention, naturally occurring avenanthramides obtained from natural sources or synthetically produced Naturally occurring avenanthramides are preferred and may be used as well.

[0060] The term "avenanthramide or its analogue" refers to the various isomers that exist. , especially the naturally occurring trans- and cis-isomers, e.g., upon exposure to light. Photoisomerization-induced cis-isomerized double bonds (formula 1 or 2 with n=1) or has one or two cis-isomeric double bonds (formula 1 or 2 with n=2) It is intended to include avenanthramides and the like.

[0061] In particular, within the context of the present invention, avenanthramides are represented by general formula 1 and defined in Table 1 avenanthramide compounds, or any isomer thereof Avenanthramide analogs are represented by general formula 2 and its definitions as described above. avenanthramide analogue compound or any isomer thereof .

[0062] In a preferred variant of the invention according to the first aspect, the composition comprises avenanthramides A, B, At least one avenant rami selected from the group consisting of C, G, H, K, L and R Includes do.

[0063] In another variation, the composition of the present invention comprises avenanthramides A, B, C, G, H, K, L ( Non-Collins abbreviation; CAS number 172549-38-1) (Avenanthramide O (Collins two, three, or four selected from the group consisting of R or even more mixtures of different avenanthramides. The mixture or combination of avenanthramides may therefore contain any one of the following combinations of avenanthramides: It can contain: A / B; A / C; A / G; A / H; A / K; A / L; A / R; B / C;B / G;B / H;B / K;B / L;B / R;C / G;C / H;C / K;C / L;C / R;G / H;G / K;G / L;G / R;H / K;H / L;H / R;K / L;K / R;L / R;A / B / C;A / B / G;A / B / H;A / B / K;A / B / L;A / B / R;A / C / G;A / C / H;A / C / K;A / C / L;A / C / R;A / G / H;A / G / K ;A / G / L;A / G / R;A / H / K;A / H / L;A / H / R;A / K / L;A / K / R;A / L / R;B / C / G;B / C / H;B / C / K, B / C / L;B / C / R;C / G / H;C / G / K, C / G / L;C / G / R, G / H / K;G / H / L;G / H / R ;H / K / L, H / K / R;K / L / R;A / B / C / G;A / B / C / H;A / B / C / K;A / B / C / L;A / B / C / R;A / C / G / H;A / C / G / K;A / C / G / L;A / C / G / R;A / G / H / K;A / G / H / L;A / G / H / R;A / H / K / L;A / H / K / R;A / K / L / R;B / C / G / H;B / C / G / K;B / C / G / L;B / C / G / R;C / G / H / K;C / G / H / L;C / G / H / R;G / H / K / L;G / H / K / R and H / K / L / R.

[0064] However, the most preferred mixtures of avenanthramides are A / B, A / C, B / C and A / It is B / C.

[0065] In addition to the above avenanthramide compound or avenanthramide combination, the composition may also comprise avenanthramide. Nanthramides A, B, C, G, H, K, L (non-Collins abbreviations; CAS number 172549- 38-1) (also known as avenanthramide O (Collins abbreviation) or 2pd) and R One or more avenanthramides other than avenanthramide D, E, FU, X , Y (also called 2), AA, CC, or OO, or any remaining Avena identified in Table 1 The composition may further comprise any of the following compounds:

[0066] Oats according to the first aspect of the invention, obtainable by the method described in detail below. The extract contains avenanthramides A, B, C, G, H, K, and L (non-Collins abbreviations; CAS no. 172549-38-1) (also known as O (Collins abbreviation) or 2pd) and R The compound contains at least one avenanthramide selected from the group consisting of:

[0067] In another variation, the oat extract contains avenanthramides A, B, C, F, G, H, L ( Non-Collins abbreviation; CAS No. 172549-38-1) (O (Collins abbreviation) or 2p and R, It contains a mixture of different avenanthramides than The product or combination may include any of the following combinations of avenanthramides: :A / B;A / C;A / G;A / H;A / K;A / L;A / R;B / C;B / G;B / H;B / K;B / L;B / R;C / G;C / H;C / K;C / L;C / R;G / H;G / K;G / L;G / R;H / K;H / L;H / R;K / L;K / R;L / R;A / B / C; A / B / G;A / B / H;A / B / K;A / B / L;A / B / R;A / C / G;A / C / H;A / C / K;A / C / L;A / C / R;A / G / H;A / G / K;A / G / L;A / G / R;A / H / K;A / H / L;A / H / R;A / K / L;A / K / R;A / L / R; B / C / G;B / C / H;B / C / K, B / C / L;B / C / R;C / G / H;C / G / K, C / G / L; C / G / R, G / H / K; G / H / L; G / H / R; H / K / L, H / K / R;K / L / R;A / B / C / G;A / B / C / H;A / B / C / K;A / B / C / L;A / B / C / R;A / C / G / H;A / C / G / K;A / C / G / L;A / C / G / R;A / G / H / K;A / G / H / L;A / G / H / R;A / H / K / L;A / H / K / R;A / K / L / R;B / C / G / H;B / C / G / K;B / C / G / L;B / C / G / R;C / G / H / K;C / G / H / L;C / G / H / R;G / H / K / L;G / H / K / R and H / K / L / R.

[0068] However, the most preferred mixtures of avenanthramides in oat extract are A / B and A / C. , B / C and A / B / C.

[0069] In addition to the above avenanthramide compound or avenanthramide combination, oat extract are avenanthramides A, B, C, G, H, K, L (non- Collins abbreviation; CAS number 172549-38-1) (O (Collins abbreviation) or 2pd (also referred to as R) and one or more avenanthramides other than R, e.g., avenanthramide Amides D, E, FU, X, Y (also called 2), AA, CC or OO or those specific to Table 1 The composition may further comprise any of the remaining avenanthramide compounds defined above.

[0070] At least one avenanthramide or avenanthramide as described above in the composition or oat extract, the dry weight of the composition or oat extract The preferred variants may be present in a concentration or total amount of 0.5 to 7.0% by weight, based on the dry weight of the product. In its compounded form, the composition or oat extract contains at least one avenanthramide or avenanthramide. a mixture of venanthramides based on the dry weight of the composition or the dry weight of the oat extract , in a concentration or total amount of 1.0 to 6.5 wt. %, and even more preferably in a concentration or total amount of 2.0 to 5.0 wt. Contains by volume % concentration or total amount.

[0071] In a preferred variant, the total amount of avenanthramides in the composition or oat extract is 1.1 to 2.5 times higher than the total amount of venanthramides A, B and C, and even more preferably The total amount of avenanthramides is 1.3 to 2.0 times the total amount of avenanthramides A, B, and C. expensive.

[0072] The composition or oat extract further comprises at least one β-glucan compound. Beta-glucans are commonly named β-glucans and are naturally found in the cell walls of cereals, bacteria and fungi. Polymeric β-D-glucose occurs naturally and exhibits significantly different physiochemical properties depending on the source. In cereals (oats and barley), β-glucans are mixed bonds. It is composed of (1→3)(1→4)-β-D-glucose units, while mushrooms In yeast and yeast, β-glucans consist of (1→3)(1→6)-β-D-glucose units. It consists of mixed bonds.

[0073] β-Glucans consist of one β-( by a β-(1→4) glycosidic bond / linkage that separates at a 1→3) glycosidic bond / linkage Consists of linked D-glucopyranose residues. Consists of three and four glucose residues. The resulting cellulose-like fragments are designated DP3 and DP4, respectively.

[0074] The main component of oat soluble fiber is a linear polysaccharide (1→3), (1→4)-β-D-glucan. These glucans are usually called β-glucans. DA, DP3 value 54.2~60.9, DP4 value 33.8~36.7 and DP3 / DP4 The ratio is 1.5 to 2.3 [Siurek et al., Food Science and Te chnology International, 2012, Vol. 18(No. 6), 559~ Page 568].

[0075] Within the context of the present invention, at least the β-glucan is a mixed β-(1→3)-β-(1→ 4) glucans having a 4-linked glucopyranosyl backbone and having different molecular weights; However, they are preferably derived from a cereal source, and even more preferably from an oat source. is derived from

[0076] Beta-glucan has been shown to reduce serum LDL cholesterol and cholesterol levels, which may contribute to the development of coronary heart disease. reduces blood pressure, improves insulin sensitivity, and and blood sugar control, as well as many other benefits such as antioxidant and anti-inflammatory activity It is known that

[0077] The amount of β-glucan present in the composition or oat extract according to the invention may vary depending on the composition. Between 1.0 and 3.3% by weight, based on the dry weight of the oat extract or the dry weight of the oat extract. In a preferred variant, at least one β-glucan or all β-glucan The concentration of 1.5 to 2.8 based on the dry weight of the composition or the dry weight of the oat extract. % by weight, and even more preferably 1.7 to 2.6% by weight.

[0078] At least one avenanthramide or its analog in the composition or oat extract Whole or whole avenanthramide or its analogue and at least β-glucan or whole The concentration of β-glucan is at least one avenanthramide or its analogue or total At least one β-glucan or total β-glucan of avenanthramide or its analogue The weight ratio of the sugar to the sugar is selected or adjusted to be in the range of 1:4 to 4:1. In a preferred variant, the composition or oat extract contains at least one avenanthrene. avenanthramide or its analogue or all avenanthramide or its analogue and at least β-glucan or total β-glucan is used in a ratio of 1:3 to 3:1, more preferably 1:2 to A weight ratio in the range of 2:1 and even more preferably in the range of 1:1.5 to 1.5:1 The most preferred composition or oat extract comprises at least one avenant rami. at least one of avenanthramide or its analogues or all avenanthramide or its analogues The concentration of β-glucan or total β-glucan is almost equal, i.e., 1:1. The composition or oat extract is in the ratio.

[0079] The composition or oat extract according to the first aspect of the invention has a very low salt content, i.e. i.e., compared with prior art avenanthramide / β-glucan compositions or oat extracts. When used in a food additive, the salt content is 1.0% by weight or less, based on the dry weight of the composition or oat extract. The salt content is preferably Na + , K. + , Mg 2+ , Ca 2+ , Cl - , S O4 2- and PO4 3- consisting essentially of cations and anions selected from the group consisting of In a preferred variant, the salt content in the composition or in the oat extract is even more low, 0.5% by weight or less, based on the dry weight of the composition or the dry weight of the oat extract; Even more preferably, it is 0.25% by weight or less.

[0080] Such a low salt content is advantageous. On the other hand, oil-in-water (o / w) emulsions are the most popular. In such emulsions, the external phase is water and The aqueous phase contains water-soluble components, and the internal phase contains oil and oil-soluble components. High concentrations of ionized materials (cations and anions) can destabilize the emulsion interface. Therefore, lowering the salt content is considered beneficial for emulsion stability. On the other hand, metal ions can be used in, for example, ingredients used in personal care products. They are important for chemical processes and the performance of many products because they can catalyze the decomposition of Therefore, reducing the metal cation content will improve the safety of the product and its ingredients. It can be considered qualitatively beneficial.

[0081] The composition or oat extract according to the first aspect of the invention has a relatively low content of free amino acids. The total content of free amino acids is preferably 0.5 to 1.5% by weight. The content is preferably in the range of 0.5 to 1.0% by weight, more preferably 0.6 to 0.9% by weight. or in the amino acid fraction of oat extract, phenylalanine and tryptophan is the most predominant amino acid.

[0082] L-phenylalanine and tryptophan are essential α-amino acids, which are Phenylanine and tryptophan are synthesized de novo in humans and other animals. This means that nutrients cannot be obtained through the body and must be obtained through the body.

[0083] L-phenylalanine is a natural precursor to tyrosine, a monoamine neurotransmitter. The substances catecholamines dopamine, norepinephrine (noradrenaline), and epinephrine It is further converted into nephrin (adrenaline) or into the skin pigment melanin. Human epidermis is responsible for the biosynthesis of all catecholamines. It depends on the availability of L-tyrosine, which is synthesized from L-phenylalanine.

[0084] L-phenylalanine is found in food products (e.g., eggs, chicken, liver, beef, milk, chicken, etc.). can be introduced with a nutritional supplement (e.g., aspartame), It is produced industrially using Escherichia coli. L-phenylalanine has been shown to be effective in treating different disorders (e.g., depression, attention deficit hyperactivity disorder). It is widely used in medicine for the treatment of osteoarthritis, Parkinson's disease, chronic pain, osteoarthritis, and rheumatoid arthritis. It is being done.

[0085] Tryptophan, which is required for normal growth, is used in protein synthesis and Cotinamide (vitamin B6), serotonin, melatonin, tryptamine, kynurenine, 3-hydroxykynurenine, and several bioavailable acids, including quinolinic acid and xanthurenic acid Serves as an in vivo precursor for the biologically active compound.

[0086] In another preferred variant of the invention according to its first aspect, the composition or oat extract comprises: based on the dry weight of the composition or the dry weight of the oat extract, - 0.5 to 7.0% by weight, preferably 1.0 to 6.5% by weight of total avenanthramides, Preferably avenanthramides A, B and C; - 1.0 to 3.3% by weight, preferably 1.5 to 2.8% by weight, of total β-glucans; - not more than 1.0% by weight, preferably not more than 0.5% by weight, of salt; - 0.5 to 1.5% by weight, preferably 0.6 to 0.9% by weight, of total free amino acids; - more than 0.05% by weight, preferably more than 0.075% by weight, of phenylalanine; and more than 0.25% by weight, preferably more than 0.3% by weight, of tryptophan It comprises or consists of:

[0087] The composition or oat extract according to the first aspect of the invention may be prepared as described above. , by means of radical scavenging activity, as demonstrated in Example 4 below. exhibiting excellent antioxidant capacity, thereby making the composition or oat extract beneficial as an antioxidant The composition or oat extract according to the present invention has a ABTS assay At least 70% or even more radical scavenging activity when In a preferred variant of the invention, the composition or oat extract according to the invention has Radical scavenging activity of at least 90% and more preferably at least 95% It has.

[0088] The term "antioxidant" as used herein refers to the ability to inhibit oxidizable substrate molecules (e.g., oxidizable biological molecules or oxidizable indicators) in mixtures or structures containing In some cases, the oxidation of an oxidizable substrate molecule is significantly delayed, prevented, or even inhibited. Antioxidants are compounds or compositions that inhibit the production of biologically important reactive free radicals or other reactions. reactive oxygen species (e.g., O 2- , H2O2, HOCl, ferryl, peroxyl, peroxy by scavenging or preventing the formation of nitrites and alkoxyl species by blocking or converting free radicals or other reactive oxygen species into less reactive species It can act by catalytically converting it into

[0089] Enriched with avenanthramide and β-glucan, ideally containing almost all of the two substances. A composition or oat extract having equal concentrations is improved by the presence of both substances. The composition or oat extract exhibits beneficial biological activities and properties, such as antioxidant capacity. The product may be cosmetically or pharmaceutically acceptable, as demonstrated in the examples below. The use of a liquid or solid carrier provides stability (i.e., oxidation and light stability). Provided in an easily storable liquid or solid form that is easy to use and administer (demonstrating stability) It can be provided.

[0090] In a second aspect, the present invention provides a method for preparing an oat extract, comprising the steps of: (1) preparing an oat source; (2) Extracting the oat source using at least one extraction solvent at a temperature of 30-80°C; obtaining an extraction mixture or suspension; (3) removing the extracted insoluble oat source from the extraction mixture or suspension to form an extract; Step to obtain; (4) removing the organic extractant from the extract to obtain an aqueous extract; (5) preparing and conditioning the adsorbent and providing the adsorbent in the adsorption device; P; (6) The aqueous extract is passed through an adsorbent in an adsorption device to adsorb the components of the aqueous extract. Top; (7) Eluting the adsorbed components of the aqueous extract from the adsorbent using at least one elution solvent. obtaining an eluate; and (8) Optionally removing the elution solvent from the eluate to obtain an oat extract fraction. The present invention relates to a method comprising:

[0091] In the first step of the method according to the invention, an oat source of any oat species, fresh or dried parts thereof, such as kernels, husks, trichomes or oat straw The two main species of oat are Avena sativa L. . and Avena nuda L. (synonyms: Gillet and Mag Avena sativa subsp. nuda (L.) and Koern by ne Avena sativa var. nuda (L.) is one example. Tiva is also known as common oat or hulled oat A. nuda is similar to naked oats or oats because the husk is removed when the crop is collected. Oats are known as dehulled oats. Oats are processed to remove the oat kernels, husks, and In a preferred variant, the enzyme can be separated into constituent fractions containing endothelial cells and trichomes. The starting material for the Baku extract is Avena sativa or Avena nucifera. It is crushed or uncrushed grain or oat straw of the da species.

[0092] Extracts obtained from whole grain, i.e., unmilled grain, are not equivalent to extracts obtained from milled grain. The results showed that the total content of avenanthramides A to C was higher than that of the extracts used in the study. In contrast, the β-glucan content of extracts from crushed grains is higher than that of whole grains, i.e. higher than the extract from unmilled grain.

[0093] In the second step, at least one extractant is used to extract the soluble matter described above. Any one of the oat sources listed in the table is extracted to obtain an extract mixture or suspension. The extraction is preferably carried out with stirring or by using a shaker.

[0094] To advantageously extract oat sources and enrich them in avenanthramides and β-glucans The extractant (extractant) is selected from the group consisting of a mixture of water and an organic solvent, and the organic solvent is Preferably, it is a solvent suitable for foodstuffs or cosmetics or pharmaceutical preparations. Such solvents are not suitable or compatible for the preparation of food, cosmetic or pharmaceutical preparations. It should not be.

[0095] In a more preferred variant, the extraction solvent comprises a mixture of water and alcohol or acetone. The alcohol is preferably methanol, ethanol, n-propanol, isopropanol. n-butanol, isobutanol, t-butanol and mixtures thereof, i.e. The most preferred extraction solvents for the extraction step of the present invention are selected from the group consisting of: (Extractant) is methanol, ethanol, n-propanol, isopropanol or acetone or any mixture of said solvents, each of which is miscible with water. The use of pure water as an extraction solvent is not recommended because water does not extract β-glucan. The use of pure organic solvents is also not favored due to the simultaneous extraction of triglycerides.

[0096] The mixing ratio of water to organic solvent in the extraction solvent, preferably the mixing ratio of water to alcohol, The ratio of acetone to water or the ratio of acetone to water is determined based on the extraction solvent. , in the range of 10:90 to 90:10 (v / v), preferably 20:80 to 80:20 (v / v), and most preferably in the range of 30:70 to 70:30 (v / v). do.

[0097] Particularly preferred extraction solvents (extractants) are methanol / water (3:7), methanol / water (1 :1), methanol / water (7:3), ethanol / water (3:7), ethanol / water (1: 1), ethanol / water (1:4), ethanol / water (7:3), isopropanol / water ( 3:7), isopropanol / water (1:1), isopropanol / water (7:3), acetonitrile The extraction solvents were acetone / water (3:7), acetone / water (1:1), and acetone / water (7:3). The oat extract obtained by the solvent (extractant) contains Avns and β-glucans as described above. Contains the beneficial ratios described (see Example 13 and Table 20).

[0098] To improve the extraction yield, the oat source is heated at 30 to 80°C, preferably 40 to 70°C. More preferably, the extract is made at a temperature in the range of 50 to 60°C. The results showed that the extraction yield increased with increasing temperature between 40 and 70°C. The total content of avenanthramides A to C increases in parallel between 40 and 60°C, but Extraction from crushed oats is achieved at temperatures between 50 and 60°C. This gives the best results in terms of efficiency and avenanthramide content and is therefore preferred. Extraction from uncrushed oat kernels at temperatures of 50-60°C yields avenanthramide A. This results in a higher content of C.

[0099] In an optional version of the method according to the invention, the extracted mixture obtained in the extraction step The mixture or suspension is preferably cooled to room temperature.

[0100] Additionally, the extraction step preferably involves extracting soluble materials from the oat source for a sufficiently long time. Extraction over a period of at least 2 hours ensures beneficial and maximum extract yield. This is done to obtain the rate.

[0101] To exhaust the extraction process, the extraction step can be repeated and the extracted enzyme The source of the bacteria is extracted using an extraction solvent having the same or different composition as the first extraction solvent. It can be extracted again with a fresh extraction solvent, for example, by using an extraction solvent with a different polarity. This allows for a wider range of materials to be extracted. It can be extracted three times or even three times. In this case, the extracts produced from the extraction step The mixture is combined.

[0102] The resulting extract mixture or suspension contains two fractions: (a) those soluble in the extracting solvent; (b) a liquid fraction containing extracted oat material; and (b) extracted oat material that is insoluble in the extraction solvent. A solid fraction containing an oat source.

[0103] In the following steps of the method according to the second aspect of the invention, both the liquid and solid fractions of the extract are The extracted insoluble oat source is also separated, i.e., the extracted insoluble oat source is separated from the extraction mixture or suspension. This separation step can be carried out by sedimentation, extraction, or the like, using known methods and conditions. This can be done by draining, filtering or centrifugation. The solid fraction is separated from the liquid fraction by centrifugation and filtration. Contains soluble oat substances, e.g., avenanthramides, β-glucans, salts, and amino acids. Has.

[0104] Prior to the next step and the adsorption step, the organic components of the extraction solvent (extractant) are distilled. is largely or completely removed, preferably under vacuum, from the extract obtained in the preceding step. By doing this, an aqueous extract is obtained. The aqueous extract contains at most 5% (v / v The aqueous extract thus obtained may optionally be diluted with water to The aqueous extract thus obtained is then subjected to the following adsorption step: Process it with.

[0105] In the fifth step of the method according to the second aspect of the present invention, an adsorbent is provided and It will be moved to its new location.

[0106] In accordance with the present invention, any suitable adsorbent material (adsorbent) commonly provided for adsorption / desorption processes may be used. Adhesives) can be used in step (5) of the method according to the invention.

[0107] Polymeric adsorbent resins have specific properties and selectivities for the purification and extraction of target molecules. Polymeric adsorbents exhibit defined pore structures and high surface areas. The polymeric adsorbent is a spherical synthetic polymer having the following structure. They interact with molecules in different ways depending on pH, competing molecules, solvents, etc. Hydrophobicity of synthetic adsorbents The solubility is controlled by the chemical structure of the resin and is of paramount importance when selecting an appropriate sorbent for a target compound. Aromatic polystyrene adsorbents, such as PuroSorb™ and Macronet® resin has a strong affinity for hydrophobic molecules.

[0108] Apparatus suitable for the present invention generally comprises a column made of glass or stainless steel. The internal volume is usually from several milliliters to several thousand liters, preferably 1 to 500 liters. More preferably, it is in the range of 20 to 400 liters.

[0109] Preferred adsorbent materials (adsorbents) for use in columns according to the present invention include various cross-linked polymers. vinyl benzene, preferably ethyl vinyl benzene and divinyl benzene, vinyl pyrrolidone and divinyl benzene Vinylbenzene, vinylpyridine and divinylbenzene, styrene and divinylbenzene polymers, copolymers of acrylic acid, divinylbenzene and aliphatic dienes, as well as , and other polymers, such as, preferably, polycyclic aromatics, polystyrene, poly(meth)acrylic Also included are acrylate, polypropylene, polyester and polytetrafluoroethylene. can be.

[0110] Among these, examples of preferred adsorbents for use in the method according to the invention include polymers, e.g. For example, styrene-divinylbenzene copolymers having trialkylammonium groups in the chloride form. polymers such as Lewatit®, and polystyrene polymers or acrylic and Amberlite, a hydroxyl ester-based polymer.

[0111] Before transferring the adsorbent to the adsorption unit, the adsorbent is preferably washed to optimize the adsorption capacity of the adsorbent. Prepare in water according to the manufacturer's instructions.

[0112] In the adsorption step of the method according to the invention, water containing the extracted soluble oat material is The soluble extract is applied to the column and passed through the adsorbent in the adsorption device, thereby separating the soluble oat extract. Adsorbents for substances such as avenanthramides and β-glucans derived from oat sources Adsorb onto the surface.

[0113] The selectivity of the adsorbent material allows for the addition of inorganic salts, e.g., Na + , K. + , Mg 2+ and Ca 2+ cations and Cl - , SO4 2- and PO4 3- The anions are present in trace amounts on the adsorbent material. It is adsorbed only to a certain extent and remains mainly in the extract that passes through the column.

[0114] In another preferred embodiment of the adsorption step in the process according to the invention, the aqueous extract stream is The flow rate is adjusted to within the range of 1 to 20 l / m during at least part of the adsorption procedure. Within the flow rate parameter, the local flow rate between the adsorbent material and the extracted oat material in the extraction liquid is The flow rate is preferably 2.5 to 15 l / min, more preferably 1.5 to 2.5 l / min. It is in the range of 5 to 10 l / min.

[0115] In another preferred embodiment of the adsorption process in the method according to the invention, the temperature of the extraction liquid is , in the range of 10 to 70°C for at least part of the adsorption procedure. The temperature range of 20 to 60°C is more preferable, and the temperature range of 20 to 50°C is more preferable. A temperature range of 0.5 to 100°C is particularly preferred.

[0116] The adsorption step was performed by passing the aqueous extract through the column at a gravity-induced flow rate. In another preferred embodiment, the adsorption step is carried out using counter pressure. The counter pressure inside the adsorbent is in the range of 0.1 to 4.0 bar during the adsorption procedure. The back pressure on the side is generated when the extract is pumped through the adsorber in step (5) of the adsorption procedure. This is the pressure generated by the resistance of the adsorbent material when it is loaded. Counterpressures in the range 0.8 to 1.5 bar are preferred, with the range 0.8 to 1.5 bar being particularly preferred.

[0117] In the next step of the method according to the second aspect of the invention, the adsorbent material resulting from the extraction liquid is The adsorbent is desorbed by elution with at least one elution solvent to obtain an eluate.

[0118] Adsorbed oat substances, particularly at least one avenanthramide or its analogues and The elution solvent for advantageously desorbing at least β-glucan is an organic solvent or a mixture with water. The organic solvent is preferably selected from the group consisting of food or cosmetic It goes without saying that such solvents are suitable for food, pharmaceutical or pharmaceutical preparations. It must be suitable and compatible for the preparation of cosmetic or pharmaceutical preparations.

[0119] The organic elution solvent is preferably methanol, ethanol, n-propanol, isopropyl alcohol, or the like. butanol, n-butanol, isobutanol, t-butanol, acetone or any of these Any mixture or combination thereof is selected from the group consisting of methanol, ethanol and and isopropanol are preferably used as elution solvents. The preferred elution solvents are ethanol and isopropanol. It is used either in pure form or in any mixture with water.

[0120] The mixing ratio of water to the organic solvent, preferably water to the alcohol, is in any case In this case, the ratio of the elution solvent to the resulting elution solvent is preferably in the range of 10:90 to 90:10 (v / v). The ratio is in the range of 20:80 to 80:20 (v / v), most preferably 30:70 to 70:30 (v / v). v / v).

[0121] In a preferred variant, the desorption step in the method according to the invention is a single, i.e. pure, This is carried out using a pure elution solvent, with pure ethanol being the most preferred.

[0122] One preferred variant of the desorption step according to the invention is to adjust the flow rate within the range of 1 to 20 l / m. In this context, the flow rate parameter is a function of the adsorption material and The flow rate is preferably 2.5 to 1. 5 l / min, more preferably in the range of 5 to 10 l / min.

[0123] In another preferred variant, the temperature of the elution solvent in the desorption step in the process according to the invention is The temperature parameter ranges from 10 to 70°C during at least part of the desorption step. It also contributes jointly to the local distribution coefficient between the adsorbent and the elution solvent. A temperature range of 20 to 50°C is particularly preferable.

[0124] The desorption step in the method according to the present invention comprises the step of: In another preferred variant, the desorption step is carried out by passing the desorbent through a column. The device is characterized by a back pressure inside the device ranging from 0.05 to 2.0 bar during the process. is generated by the resistance of the adsorbent material when the elution solvent is pumped through the adsorption device. The pressure at which the pressure is applied is indicated by a manometer. A counter pressure in the range of 0.1 to 1.5 bar is preferred. The pressure is preferably in the range of 0.2 to 1.0 bar, and particularly preferably in the range of 0.2 to 1.0 bar.

[0125] According to another preferred embodiment of the adsorption and desorption process in the method according to the invention, the adsorption The attachment and detachment procedures can be in the same direction or in opposite directions.

[0126] According to the desorption step in the method according to the second aspect of the present invention, An eluate containing the adsorbed and desorbed materials resulting from the filtration is obtained.

[0127] The eluate thus obtained, preferably the alcoholic eluate, can be used as such in food, nutritional supplements, etc. It can be used in the preparation of food, cosmetic, pharmaceutical or veterinary preparations. The solvent may be partially or completely removed from the eluate to obtain a concentrated or dried oat extract fraction. The elution solvent is preferably removed by vacuum evaporation or distillation.

[0128] In a preferred variant of the method according to the invention, the column and the adsorbent are Between the desorption step (7) and the desorption step (8), non-absorbed material is removed from the adsorbent by washing with water, and then In the method step, a pure oat extract is produced. Optionally, excess oat extract in the adsorption device is The water is removed by vacuum or by blowing nitrogen through an adsorbent.

[0129] The method according to the second aspect of the present invention comprises administering at least one avenanthramide or its analogue a soluble β-glucan, a soluble β-glucan derivative, and a salt thereof. The resulting oat extract fraction contains at least one avenanthramide or its derivatives. or all avenanthramides or their analogs, at least against β-glucans The weight ratio of the total β-glucan to the total β-glucan is in the range of 1:4 to 4:1, preferably 1:3 In the range of 1:2 to 3:1, more preferably 1:2 to 2:1, and even more preferably 1:2 to 2:1. The most preferred oat extract comprises at least one of avenanthramide or its analogues or all avenanthramide or its analogues, The concentration of at least one β-glucan or the total β-glucan is approximately equal, The salt content of the oat extract is 1:1. is not more than 1.0% by weight, in particular not more than 0.5% by weight, based on the dry weight of the oat extract .

[0130] Surprisingly, an oat extract enriched in oat avenanthramides and β-glucans The article may be modified by substituting the extraction step with an adsorption-desorption step using an adsorption resin within the context of the method according to the invention. In this case, avenanthramide and Ideally, avenanthramide and β-glucan are present in almost equal concentrations. Combined the beneficial biological activities and properties of both β-glucans in one extract fraction An oat extract is provided.

[0131] In a third aspect of the invention, there is provided a method for producing a cellulose derivative comprising the steps of: An oat extract is provided, with reference to its components, preferred variants, properties and beneficial effects. For further details, please refer to the detailed description of the composition or oat extract according to the first aspect of the invention. stomach.

[0132] As demonstrated by the following examples, the oat flour obtained by the method according to the invention The extract fraction may be prepared using a cosmetically or pharmaceutically approved liquid or solid carrier. It is provided in a stable, easily storable liquid or solid form that is easy to use and administer. It can be provided.

[0133] Another beneficial effect was observed in oat extract fractions enriched with avenanthramides and β-glucans. The advantage is that it can be combined with a liquid or solid carrier and spray dried. Spray-dried solid powders or granules have the advantage of being easy to handle and administer. Spray drying is very convenient as it requires only a very short exposure to high temperatures (less than 1 minute). Spray drying is a fairly gentle drying technique and is therefore particularly suitable for sensitive ingredients. It is also a relatively inexpensive technique that allows for the drying of low viscosity solutions with little dry matter. Spray drying is a well-established drying technique available on a commercial scale. This allows for the use of excipients that affect product parameters, such as dextrin or It is also possible to use cyclodextrin, other modified starches or gum arabic.

[0134] The particle size can also be adjusted depending on the respective needs and requirements, e.g., spray bed drying techniques. to produce smaller particles (0.07 It can also accommodate particles from around 0.5 mm to larger particles (around 0.4 mm). This allows the preparation of a free-flowing, almost dust-free powder.

[0135] Spray-dried oat extract enriched in avenanthramides and β-glucans The fractions are also resistant to oxidative degradation and to photoinduced degradation, as demonstrated by the examples below. Completely stable against volatile decomposition.

[0136] The composition or oat extract according to the invention preferably contains a polyol, e.g. 1,2-propanediol (Prop), a known compound commonly used as a component in food products, propylene glycol), 1,3-propanediol, 1,2-butanediol, 1,3- Butanediol (butylene glycol), 1,2-pentanediol, 1,2-hexane The diols and glycerol are used alone or in combination as a mixture with water. As clearly shown in Example 9, glycerol and 1,2-pentanedioic acid Avenanthramide and β-glucan enriched oat extract fraction combined with ethanol The compounds are stable against oxidative and light-induced degradation. The oat extract fraction enriched in β-glucan was also significantly higher than the extracts obtained by conventional techniques. It has a bright color.

[0137] The presence of both avenanthramide and β-glucan at almost equal concentrations, and avenanthramide The enhanced antioxidant, anti-inflammatory, anti-pruritic, anti-irritant and anti-inflammatory properties of both thramide and β-glucan The avenanthramide and β-glucan-enriched compositions according to the present invention have anti-atherogenic and anti-inflammatory properties. The oat extract fraction or the oat extract composition may be used in the prevention and treatment of skin disorders. These compounds can be advantageously used in cosmetic or pharmaceutical applications. These antioxidant and strong cholesterol-lowering properties of avenanthramide and β-glucan Due to their low triglyceride and triglyceride lowering properties, the compositions and oat extract fractions according to the present invention also Prevention and / or treatment of skin diseases associated with increased ROS production, or cardiovascular diseases and It can be advantageously used in the prevention and / or treatment of allergic reactions.

[0138] Thus, a fourth aspect of the present invention provides a composition or oat flakes according to the first aspect of the present invention. The extract is for cosmetic or pharmaceutical use.

[0139] Due to their improved beneficial biological activities and properties, avenanthramide and β-glucan Due to the presence of both hydroxybenzoates and hydroxybenzoates, the composition or oat extract according to the first aspect of the invention In skin care, scalp care, hair care, nail care, or for skin conditions, intolerances, and Sensitive skin, skin irritation, skin redness, wheals, pruritus (itching), skin aging, wrinkle formation, skin Loss of volume, loss of skin elasticity, pigmented spots, pigmentation abnormalities, or dry skin, i.e., skin that needs moisturizing. Suitable to be beneficial for the prevention and / or treatment of dry skin in need thereof.

[0140] In addition, the composition or oat extract according to the first aspect of the present invention may be used to treat skin disorders or corneal ulcers. Interstitial diseases, preferably barrier-related, inflammatory, immunoallergic, atherogenic , prevention of skin diseases or keratin diseases having components of dry or hyperproliferative type and / or in the treatment or prevention of skin diseases associated with increased ROS production and / or or in the treatment or prevention of cardiovascular disease, allergic reactions, coronary heart disease and and / or reducing serum LDL cholesterol and lipid levels during treatment. for reducing blood pressure and improving insulin sensitivity. and are suitable for beneficial use to enable control of blood glucose levels.

[0141] Skin or keratin disorders include eczema, psoriasis, seborrhea, dermatitis, erythema, pruritus (itching), ear inflammation, irritation, fibrosis, lichen planus, pityriasis rosea, tinea versicolor, autoimmune blistering diseases, urticarial, angiodermal and allergic skin reactions, and wound healing, and / or skin damage associated with increased ROS production. Skin diseases include atopic dermatitis, neurodermatitis, psoriasis, rosacea, acneiform rash, asteatosis and Xerosis is selected from the group consisting of:

[0142] The use of the composition or oat extract for each of these purposes comprises administering to a subject a therapeutically effective amount of The addition of the composition or oat extract provides the substance with its respective therapeutic activity. This corresponds to a method for

[0143] Within the context of the present invention, an effective amount of a composition is an amount that provides a benefit, e.g., a disorder, disease or condition to be treated. The amount of each active ingredient is sufficient to result in a reduction of the symptoms associated with the condition. When applied to a combination, the term refers to the amounts of the combined active ingredients that result in a benefit. .

[0144] Due to its remarkable radical scavenging activity and therefore antioxidant effect, the first The composition or oat extract according to this embodiment can be used in the preparation of a food, dietary supplement or veterinary product. It is appropriate to be beneficial to the manufacturing.

[0145] The composition or oat extract according to the present invention can be used in conventional foods, dietary supplements, cosmetics, pharmaceuticals, It can be easily incorporated into pharmaceutical or veterinary preparations.

[0146] Thus, a final aspect of the present invention is a composition or an oat extract according to the present invention, comprising: and / or foods, dietary supplements, cosmetics, pharmaceuticals obtained using the method according to the invention In a preferred variant of the invention, the composition according to the invention or Functional foods containing oat extract are effective ingredients for preventing or reversing the above disorders. It is provided as.

[0147] In a preferred variant, the food, dietary supplement, cosmetic, pharmaceutical or veterinary preparation comprises the compound of the present invention. Using the method described above, the amount of the compound is preferably 0.0001 to 10% by weight, more preferably 0.0001 to 10% by weight, based on the total weight of the composition. Preferably, the amount is 0.0005 to 5% by weight, most preferably 0.001 to 1% by weight. The composition comprises or is obtained from an oat extract.

[0148] Within this context, the composition or oat extract according to the invention or the composition according to the invention also or cosmetic or pharmaceutical preparations containing oat extracts, For example, other synergistically enhancing substances, such as those described and exemplified in detail below. , anti-inflammatory, antibacterial or antifungal, redness-relieving or itching-relieving properties substances, emollients, moisturizers and / or cooling agents and / or antioxidants, preservatives , (metal) chelating agents, penetration enhancers, and / or cosmetic or pharmaceutically acceptable salts. It is also possible, and in some cases advantageous, to combine the compound with suitable excipients.

[0149] Active agent means a substance or compound that confers a primary utility to a composition or formulation. Examples of such active substances include antioxidants, preservatives, (metal) chelating agents, penetration enhancers. Excipients are substances that are used to make cosmetics or pharmaceuticals as a result of processing or manufacturing. Refers to the inert substance used to formulate a drug.

[0150] Skin conditions or diseases are often characterized by dry skin, scratchy skin, skin lesions or inflammation. Therefore, the composition or oat extract or the composition or oat extract according to the present invention Cosmetic and / or pharmaceutical preparations containing the extract are particularly advantageous in that they have skin moisturizing and and / or moisture-retaining agents, cooling agents, osmolytes, keratolytic agents, nutrients, anti-inflammatory antibacterial or antifungal and / or redness-relieving or itching-relieving properties and / or emollients.

[0151] Itching occurs with particular intensity when the skin is dry. Skin moisturization and / or hydration The use of a retention agent can significantly alleviate itching. Oat extract or the composition according to the present invention or cosmetics containing oat extract or The pharmaceutical preparations are also particularly advantageous with one or more skin moisturizing and / or moisture-retaining substances. Therefore, the composition or oat extract according to the present invention can be combined with Alternatively, the cosmetic or pharmaceutical preparation may also contain the following moisturizing and / or moisture-retaining substances: May contain: sodium lactate, urea, urea derivatives, alcohol, glycol Cerol, diols, e.g., propylene glycol, hexylene glycol, 1,2- Pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol or the above diols mixtures of 1,2-hexanediol and 1,2-octanediol, Lagen, elastin or hyaluronic acid, diacyl adipate, petrolatum, urocanin Acid, lecithin, panthenol, phytantriol, lycopene, (pseudo)ceramide, glycol Cosphingolipids, cholesterol, phytosterols, chitosan, chondroitin sulfate Acids, lanolin, lanolin esters, amino acids, alpha hydroxy acids (e.g., citric acid) , lactic acid, malic acid) and their derivatives, monosaccharides, disaccharides and oligosaccharides, e.g., glucosides, saccharides, galactose, fructose, mannose, fructose and lactose, polysaccharides Sugars, such as R-glucans, especially 1,3-1,4-β-glucans derived from oats; alpha-hydroxy fatty acids, triterpene acids, such as betulinic acid or ursolic acid, as well as algae extracts.

[0152] Depending on the substance, the concentration of moisture-retaining regulator used may vary depending on the type of ready-to-use cosmetic or pharmaceutical product. It is between 0.1 and 10% (m / m) based on the total weight of the final product, preferably 0.5 These data are particularly relevant for the geological processes that are advantageously used. hexylene glycol, 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol and 1,2-decanediol, as well as 1,2-hexanediol Applied to a mixture of Sandiol and 1,2-octanediol.

[0153] The use of cooling agents can relieve itching. Extract or composition according to the invention or cosmetics or pharmaceuticals containing oat extract The preparations can also be particularly advantageously combined with one or more cooling agents. Preferred individual cooling agents for use within the framework of the present invention are listed below. Those skilled in the art can add many other cooling agents to this list; The cooling agents may also be used in combination with each other: l-menthol, d-menthol, Racemic menthol, menthone glycerol acetal (trade name: Frescolat) Menthyl lactate (trade name: Frescolat® ML; Lactic Acid Menthyl is preferably l-menthyl lactate, especially l-menthyl l-lactate), Substituted menthyl-3-carboxamides (e.g., menthyl-3-carboxylic acid N-ethylamide) ), 2-isopropyl-N-2,3-trimethylbutanamide, substituted cyclohexane carboxylic acid Voxamide, 3-menthoxypropane-1,2-di ol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl Carbonate, N-acetylglycine menthyl ester, isopulegol, hydroxycaprylate Menthyl carboxylate esters (e.g., menthyl 3-hydroxybutyrate), succinate Nomenthyl, 2-mercaptocyclodecanone, menthyl 2-pyrrolidin-5-one carbo xylate, 2,3-dihydroxy-p-menthane, 3,3,5-trimethylcyclohexyl Sanon glycerol ketal, 3-menthyl-3,6-di- and trioxaalkanoic acid ate, 3-menthyl methoxyacetate and icilin.

[0154] Due to their specific synergistic effects, preferred cooling agents are l-menthol and d-menthol. , racemic menthol, menthone glycerol acetal (trade name: Frescolat ( MGA), menthyl lactate (preferably l-menthyl lactate, especially l-menthyl l lactate (trade name: Frescolat® ML), substituted menthyl-3- Carboxamides (e.g., menthyl-3-carboxylic acid N-ethylamide), 2-isopropyl Pyr-N-2,3-trimethylbutanamide, Substituted Cyclohexanecarboxamide, 3- Methoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2 -hydroxypropyl menthyl carbonate and isopulegol.

[0155] Particularly preferred cooling agents are l-menthol, racemic menthol, and menthone glycerol. Acetal (trade name: Frescolat® MGA), menthyl lactate (preferred or l-menthyl lactate, especially l-menthyl l-lactate (trade name: Frescolat (registered trademark)ML), 3-methoxypropane-1,2-diol, 2-hydroxyethyl These are 2-hydroxypropylmenthyl carbonate and 2-hydroxypropylmenthyl carbonate.

[0156] Very particularly preferred cooling agents are l-menthol, menthone glycerol acetal ( Trade name: Frescolat® MGA) and menthyl lactate (preferably l- Menthyl lactate, especially l-menthyl l-lactate (trade name: Frescolat (registered trademark) Mark)ML).

[0157] Depending on the substance, the concentration of the freshening agent used may vary depending on the final product of the ready-to-use cosmetic or pharmaceutical product. Preferably, the amount is between 0.01 and 20% by weight, particularly preferably between 0.1 and 20% by weight, based on the total weight of the composition. 5% by weight.

[0158] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing the compound may also be used in combination with one or more osmolytes. Examples of osmolytes that can be mentioned here include sugar alcohols (myo-inositol, mannitol, sorbitol), quaternary amines, e.g., taurine , Choline, Betaine, Betaine Glycine, Ectoine, Diglycerol Phosphate, Phosphate phospholylcholine or glycerophosphorylcholine, amino acids such as glutamine, glycerol, Synthin, Alanine, Glutamate, Aspartate or Proline, Phosphatidylcholine , phosphatidylinositol, inorganic phosphates, and polymers of the foregoing compounds, e.g., These include substances from the group comprising proteins, peptides, polyamino acids and polyols. All osmolytes simultaneously have a skin moisturizing effect.

[0159] Preferably, a keratolytic substance is also combined with the composition according to the invention or with the oat extract. Keratolytic compounds include the large group of alpha hydroxy acids. For example, salicylic acid is preferably used.

[0160] For example, for the topical cosmetic or pharmaceutical treatment of dry and / or itchy skin, In cosmetic or pharmaceutical preparations containing the composition or oat extract according to the invention , especially high percentages of nutritional substances also reduce transepidermal water loss due to lipophilic components. In a preferred embodiment, the cosmetic or pharmaceutical preparation comprises one or more or multi-nutritional animal and / or vegetable fats, and oils, e.g., olive oil , sunflower oil, refined soybean oil, palm oil, sesame oil, rapeseed oil, almond oil, borage Oil, evening primrose oil, coconut oil, shea butter, jojoba oil, sperm whale oil, tallow, cow's milk leg oil and lard, and optionally other nutritious components, e.g., 8 to 30 The fatty alcohols used herein include fatty alcohols having C atoms of It can be either saturated or unsaturated and either straight chain or branched. Nutrient substances which can be particularly preferably combined with the mixtures according to the invention are also particularly suitable for use in ceramics. Here, we present a novel compound, N-acylsphingosine (Sphingosine), which significantly improves the water retention capacity of the stratum corneum. fatty acid amides of cingosine) or synthetic analogues of such lipids (so-called pseudoceramides) ceramides, which are understood to mean phospholipids, such as soybean lecithin, egg lecithin, and cephalin; as well as petrolatum, paraffin oil and silicone oil, the latter Among these are dialkyl- and alkylarylsiloxanes, e.g., dimethylpolysiloxanes. phenyl and methylphenyl polysiloxanes and their alkoxylated and quaternized derivatives Includes conductors.

[0161] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing other anti-inflammatory active compounds or anti-redness and It may contain active compounds that exhibit anti-itch activity. Within this context, any anti-inflammatory activity and compounds that relieve redness and itching, and are useful in cosmetic and / or dermatological applications. Any active compound suitable or customary for the purpose can be used. The anti-inflammatory active compounds and the active compounds that relieve redness and / or itching are steroidal anti-inflammatory substances of the steroid class, such as hydrocortisone, dexamethasone, Dexamethasone phosphate, methylprednisolone, or cortisone. The effect can be expanded by adding other steroidal anti-inflammatory drugs. Anti-inflammatory drugs, such as: oxicams, e.g., piroxicam or tenoxicam; salicylate aspirin, Disalcid®, Solprin® or fendosal; acetic acid derivatives, such as diclofenac, fenclofenac, inclofenac, domethacin, sulindac, tolmetin, or clindanac; fenamates, such as mefe namic acid, meclofenamic acid, flufenamic acid or niflumic acid; propionic acid derivatives, e.g. For example, ibuprofen, naproxen, benoxaprofen; or pyrazoles, for example , phenylbutazone, oxyphenylbutazone, febranone or azapropazone Alternatively, natural anti-inflammatory substances and anti-inflammatory agents may be used to treat redness and / or itching. Substances that alleviate irritation can also be used. Plant extracts, special highly active plant extract fractions Furthermore, extremely pure active substances isolated from plant extracts can be used. Aloe vera, Commiphora species, Rubia species, willow, willow grass, saffron Uga, Marigold, Arnica, Glycyrrhiza species, Echinacea species, Extracts, fractions and active substances derived from Rubus species and pure substances, such as Bisa, among others Borol, apigenin, apigenin-7-glucoside, gingerol, e.g., [6]- Gingerol, paradols, e.g., [6]-paradol, boswellic acid, phytosterol Particularly preferred are glycyrrhizin, glabridin, and licochalcone A. Preparations containing release inhibitors also contain mixtures of two or more anti-inflammatory active compounds. It is possible.

[0162] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing the active compound may also contain the active compound for preservative purposes. and are suitable or customary for cosmetic and / or dermatological applications, and advantageously Examples include, among others, benzoic acid, its esters and salts; propionic acid and its salts; salicylic acid; Sorbic acid and its salts; 2,4-hexanoic acid (sorbic acid) and its salts; Formaldehyde and paraformaldehyde; 2-hydroxybiphenyl ether and its salts; 2- Zinc sulfide pyridine N-oxide; inorganic sulfites and bisulfites; sodium iodate sodium; chlorobutanol; 4-hydroxybenzoic acid and its salts and esters; dehy 1,6-Bis(4-amidino-2-bromophenoxy)-n-hexane; Formic acid; and its salts; sodium salt of ethylmercury-(II)-thiosalicylic acid; phenylmercury and and its salts; 10-Undecylenic acid and its salts; 5-amino-1,3-bis(2-ethyl) (hexyl)-5-methylhexahydropyrimidine;5-Bromo-5-nitro-1,3- Dioxane; 2-Bromo-2-nitro-1,3-propanediol; 2,4-Dichlorobenzyl N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl) alcohol Urea;4-Chloro-m-cresol;2,4,4'-trichloro-2'-hydroxy- Diphenyl ether; 4-chloro-3,5-dimethylphenol; 1,1'-methylene- Bis(3-(1-hydroxymethyl-2,4-dioximidazolidin-5-yl)urea Poly(hexamethylenebiguanide) hydrochloride; 2-phenoxyethanol; Hexa Methylenetetramine; 1-(3-chloroallyl)-3,5,7-triaza-1-azonia Adamantane chloride; 1-(4-chloro-phenoxy)-1(1H-imidazole-1 -yl)-3,3-dimethyl-2-butanone;1,3-bis(hydroxymethyl)-5, 5-Dimethyl-2,4-imidazolidinedione;Benzyl alcohol;Octopiro x (registered trademark); 1,2-dibromo-2,4-dicyanobutane; 2,2'-methylene-bi 6-Bromo-4-chlorophenol; Bromochlorophene; 5-chloro-2-methyl 2-methyl-3(2H)-isothiazolinone and 2-methyl-3(2H)-isothiazolinone Mixture of magnesium chloride and magnesium nitrate; 2-benzyl-4-chlorophenol 2-Chloroacetamide; Chlorhexidine; Chlorhexidine acetate; Chlorhexidine gluconate Lorhexidine;Chlorhexidine hydrochloride;1-phenoxy-propan-2-ol;N- Alkyl (C12-C22) trimethylammonium bromides and chlorides; 4,4- Dimethyl-1,3-oxazolidine; N-hydroxymethyl-N-(1,3-di(hydro) (Oxymethyl)-2,5-dioxoimidazolidin-4-yl)-N'-hydroxymethyl Urea; 1,6-bis(4-amidinophenoxy)-n-hexane and its salts; Gluta Aldehyde 5-ethyl-1-aza-3,7-dioxabicyclo(3.3.0)octane ;3-(4-chlorophenoxy)-1,2-propanediol;Hyamine;Alkyl( C8-C18) dimethylbenzylammonium chloride;Alkyl(C8-C18)dimethylbenzylammonium chloride dimethylbenzylammonium bromide; alkyl(C8-C18)dimethylbenzylammonium bromide Benzyl hemiformal; 3-iodo-2-propynyl butyl carboxylate Preservatives such as carbamate; or sodium ((hydroxymethyl)amino)acetate Any preservative selected from the group consisting of:

[0163] Other antibacterial or antifungal active substances may also be added to the composition or oat extract or the present invention. and a cosmetic or pharmaceutical preparation containing a composition or an oat extract according to the present invention. and can be advantageously used in cosmetic and / or dermatological applications. Any conventional antibacterial or antifungal active substance can be used. In addition to the large group of other products that are advantageous here, there are also those related to cosmetics, e.g. Contains triclosan, climbazole, octoxyglycerin, Octirox (registered trademark) (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1 H)-pyridone 2-aminoethanol salt), chitosan, farnesol, monolauric acid glycerol or a combination of the foregoing substances, which are useful for, among others, underarm odor, foot odor It is used against dandruff or itchy skin.

[0164] Composition or oat extract or a composition or oat extract according to the present invention The cosmetic and / or pharmaceutical preparations also contain one or more emollients. and suitable or customary for cosmetic and / or pharmaceutical applications. any emollient, such as alpha-bisabolol, azulene, guaiazulene, 18 -β-glycyrrhetinic acid, allantoin, aloe vera juice or gel, Hamame Extract of Witch Hazel (Witch Hazel), Echinacea species, Cent ella asiatica, Chamomile, Arnica monatana, Glyc yrrhiza species, algae, seaweed and Calendula officinalis, if and vegetable oils, such as sweet almond oil, baobab oil, olive oil and panthenol Contains ethanol, laureth-9, trideceth-9 and 4-t-butylcyclohexanol It is possible.

[0165] In addition, the composition or oat extract or the composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing the exudates also contain antiperspirants to control body odor. They can be used particularly advantageously in combination with antiperspirant active compounds (antiperspirants). As sweat-inhibiting active compounds, in particular aluminum salts, such as aluminum chloride, chlorohydrate However, zinc, magnesium or zinc salts are not suitable for this purpose. The use of ammonium compounds can also be advantageous. Aluminum salts and, to a somewhat lesser extent, However, aluminum / zirconium salt combinations are used in cosmetic antiperspirants and dermatological Partially neutralized aluminum hydroxide has proven useful in antiperspirants. It is also noted that hydroxychloride is better tolerated by the skin but is less effective. Materials other than aluminum salts can also be used, for example (a) Protein precipitants, such as formaldehyde, among others, which cause the surface sealing of sweat glands (b) topical anesthetics; (c) methylaldehyde, natural and synthetic tanning agents, and trichloroacetic acid; drugs, such as dilute solutions of lidocaine, prilocaine, or mixtures thereof, (c) X, A or are Y-type zeolites, which also act as sweat secretion reducers and adsorbents of malodors; and (d) botulinum toxin (a toxin produced by the bacterium Chlostridium botulinum) ), and also in hyperhidrosis (pathological increase in sweat secretion), its action is to reduce sweat secretion It is based on irreversible blockade of the release of the associated transmitter, acetylcholine.

[0166] Combinations with (metal) chelating agents may also be used in the compositions or oat extracts or in the invention. Advantageous in cosmetic or pharmaceutical preparations containing a composition or oat extract according to the present invention. and suitable or customary for cosmetic and / or dermatological applications. Any metal chelating agent can be used. Preferred (metal) chelating agents include α -hydroxy fatty acids, phytic acid, lactoferrin, alpha-hydroxy acids, e.g., among others , gluconic acid, glyceric acid, glycolic acid, isocitric acid, citric acid, lactic acid, malic acid , mandelic acid, tartaric acid, as well as humic acid, bile acids, bile extract, bilirubin, biliberin EDTA, EGTA and their derivatives. The use of a laxative is in accordance with the present invention. To improve the stability of cosmetic or pharmaceutical preparations containing barley extract.

[0167] For use, the compositions according to the invention or preparations containing an oat extract are suitable for use in cosmetics and and apply to the skin and / or hair in a sufficient amount in a manner customary for cosmetic and dermatological products. In this context, compositions containing the mixture according to the invention which also function as sunscreens are also suitable. The cosmetic and dermatological preparations used therein offer certain advantages. Advantageously, these preparations At least one UVA filter and / or at least one UVB filter and and / or at least one inorganic pigment. In this context, the preparation may contain, for example, Preparations of this type, for example, solutions, water-in-oil (W / O) emulsions, oil-in-water (O / W) emulsions or multiple emulsions, such as water-in-oil-in-water (W / O / W) emulsions, gels, hydrogels, It comes in a variety of forms, typically used for dispersions, solid sticks, or aerosols. It is possible.

[0168] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing substances that absorb UV radiation in the UVB range are advantageously In combination with the above, the total amount of filter material is, for example, 0.0% by weight based on the dry weight of the preparation. 1 to 40% (m / m), preferably 0.1 to 10% (m / m), particularly 1.0 to 5.0% ( A cosmetic preparation that protects hair and / or skin from all UV rays, These can also act as sunscreens for hair. If the preparations according to the invention contain UVB filter substances, these are oil-soluble and Advantageous oil-soluble UVB filters include: 3-benzylidene camphor derivatives, preferably 3-(4-methylbenzylidene) camphor camphor, 3-benzylidene camphor; 4-aminobenzoic acid derivatives, preferably 2-ethyl Hexyl 4-(dimethylamino)benzoate, Amyl 4-(dimethylamino)benzoate cinnamates, preferably 2-ethylhexyl 4-methoxycinnamate; Isopentyl 4-methoxycinnamate; salicylic acid esters, preferably salicylic acid 2 -Ethylhexyl, 4-isopropylbenzyl salicylate, homomenthyl salicylate; Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2- Hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4 -Methoxybenzophenone; benzalmalonic acid esters, preferably di(2-ethylhexyl) 4-Methoxybenzalmalonate, 2,4,6-Trianilino-(p-carbo-2 '-Ethyl-1'-hexyloxy)-1,3,5-triazine. Advantageous water-soluble UVB filter As a filter, salts of 2-phenylbenzimidazole-5-sulfonic acid, e.g. Sodium, potassium or triethanolammonium salts, as well as sulfonic acids per se; sulfonic acid derivatives of benzophenone, preferably 2-hydroxy-4-methoxy Benzophenone-5-sulfonic acid and its salts; sulfones of 3-benzylidene camphor Acid derivatives, such as 4-(2-oxo-3-bornylidenemethyl)benzenesulfonic acid, 2-Methyl-5-(2-oxo-3-bornylidene-methyl)sulfonic acid and its derivatives salts, and 1,4-di(2-oxo-10-sulfo-3-bornylidenemethyl)-benzene and its salts (the corresponding 10-sulfato compounds, e.g., the corresponding sodium salts, ammonium salts and triethanolammonium salts), and benzene-1,4-di(2- 10-oxo-3-bornylidenemethyl-10-sulfonic acid.

[0169] UVA filters, such as those commonly contained in cosmetic preparations, are utilized. These substances are preferably derivatives of dibenzoylmethane, especially 1-(4'-tert-butylphenyl)-3-(4'-methoxyphenyl)propane- 1,3-dione and 1-phenyl-3-(4'-isopropylphenyl)propane-1 ,3-dione. The amount used for UVB combination can be similar. .

[0170] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations having, for example, the components normally found in such preparations may also advantageously be Other cosmetic auxiliaries used, such as antioxidants, perfume oils, antifoaming agents, colorants, pigments, thickeners, surface-active substances, emulsifiers, plasticizing substances, wetting and / or moisture-retaining substances substances, fats, oils, waxes or other conventional constituents of cosmetic preparations, e.g. alcohol , polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives. Suitable or customary for cosmetic and / or dermatological applications. any imaginable antioxidants, perfume oils, antifoaming agents, coloring agents, pigments with coloring action, thickeners , surface-active substances, emulsifiers, plasticizing substances, wetting and / or moisture-retaining substances, fats, oils, Waxes, alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicones Corn derivatives may be used herein in accordance with the present invention.

[0171] The high content of treatment substances is a key ingredient in this formulation for topical, preventative or cosmetic treatment of the skin. It is generally advantageous in compositions according to the invention or preparations containing oat extract. According to a new embodiment, the composition comprises one or more animal and / or plant treated fats and Oils, such as olive oil, sunflower oil, refined soybean oil, palm oil, sesame oil, natto Palm oil, almond oil, borage oil, evening primrose oil, coconut oil, shea butter, jojoba oil, macadamia oil Skull oil, beef tallow, beef foot oil and lard, and optionally other processed ingredients, e.g. For example, the fatty alcohol used herein contains a C8 to C30 fatty alcohol. saturated or unsaturated and straight-chain or branched aliphatic alcohols, e.g., decanol; decanoyl, decenol, octanol, octenol, dodecanol, dodecenol, octadiol Enol, decadienol, dodecadienol, oleyl alcohol, ricinoleyl alcohol Cole, erucic alcohol, stearyl alcohol, isostearyl alcohol, cetyl Alcohol, lauryl alcohol, myristyl alcohol, arachidyl alcohol, caprylic / capric triglyceride Capric alcohol, capric alcohol, linoleyl alcohol, linolenyl alcohol and behenyl alcohol, as well as these Guerbet alcohols. This list may be expanded, if desired, to include other structurally and chemically related alcohols. The fatty alcohols are preferably derived from naturally occurring fatty acids, usually fatty acids. They are prepared by reduction from the corresponding esters of naturally occurring fats and fatty oils. Fatty alcohol fractions formed by, for example, beef tallow, peanut oil, rapeseed oil, cottonseed oil , soybean oil, sunflower oil, palm kernel oil, linseed oil, corn oil, castor oil, rapeseed oil , sesame oil, cocoa butter and cocoa fat can also be used.

[0172] Treatments that can be preferably combined with the composition or oat extract according to the invention Other substances that may be mentioned include: ceramides, N-acylsphingosines, (fatty acid amides of sphingosine) or synthetic analogues of such lipids ( so-called pseudo-ceramides), which significantly improve the water-retaining capacity of the stratum corneum; lecithin, e.g. soybean lecithin, egg lecithin and cephalin; vaseline, paraffin and silicone oils, the latter especially dialkyl- and alkylaryl-siloxanes , for example, dimethylpolysiloxane and methylphenylpolysiloxane, and These include alkoxylated and quaternized derivatives.

[0173] Hydrolyzed animal and / or plant proteins may also be used in compositions or enzymes according to the invention. It can be advantageously added to preparations containing barley extract. , especially elastin, collagen, keratin, milk protein, soy protein, oat Protein, pea protein, almond protein and wheat protein fraction or Hydrolyzed proteins and their condensation products with fatty acids, as well as quaternized hydrolyzed proteins Proteins are mentioned, and the use of hydrolyzed vegetable proteins is preferred.

[0174] Cosmetic or dermatological preparations containing the composition according to the invention or the oat extract are dissolved If it is a liquid or lotion, solvents that can be used include: Water or aqueous solutions; fatty oils, fats, waxes and other natural and synthetic fatty bodies, preferably The fatty acids and alcohols with low C numbers, such as isopropanol and propylene glycol, Esters with cholesterol or glycerol, or with fatty alcohols with low C numbers Esters with alkanoic acids or fatty acids; alcohols, diesters with low carbon numbers alcohols or polyols, and their ethers, preferably ethanol, isopropanol, ethanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and and similar products. Mixtures of the above solvents are particularly used. In the case of alcoholic solvents, water can be an additional constituent.

[0175] Composition or oat extract or a composition or oat extract according to the present invention The cosmetic or pharmaceutical preparations containing the same may also contain antioxidants, and / or any antioxidant suitable or customary for dermatological applications. Advantageously, the antioxidant is an amino acid (e.g., glycine, histidine, tyrosine, thiamin, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives Derivatives and peptides thereof, such as D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g., anserine), carotenoids, carotenes (e.g., α-carotene), carotene, β-carotene, lycopene) and their derivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid), gold thioglucose, propylthiouracil and other thiols ( For example, thioredoxin, glutathione, cysteine, cystine, cystamine, and the like. Glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and laurate lyl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl and glyceryl esters dilauric thiodipropionate, distearic thiodipropionate, and their salts thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, Nucleotides, nucleosides and salts) and sulfoximine compounds (e.g., butionyl Homocysteine ​​sulfoximine, buthionine sulfone, penta-, heptagonist thionine sulfoximine) (these are tolerated at very low doses), Additionally, (metal) chelating agents, such as alpha-hydroxy fatty acids, palmitic acid, phytic acid , lactoferrin, alpha-hydroxy acids (e.g., citric acid, lactic acid, malic acid), humic acid , bile acids, bile extract, bilirubin, biliverdin, EDTA, EGTA and Derivatives, unsaturated fatty acids and their derivatives (e.g., gamma-linolenic acid, linoleic acid, oleic acid, leic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives Vitamin C and its derivatives (e.g., ascorbyl palmitate, magnesium phosphate) ascorbyl acetate), tocopherols and their derivatives (e.g. , vitamin E acetate), vitamin A and its derivatives (e.g., vitamin A palmitate benzoin resin, coniferyl benzoate, rutinic acid and its derivatives, Ferrulic acid and its derivatives, butylhydroxytoluene , butylhydroxyanisole, nordihydroguaiacinic acid, nordihydroguaiare acetic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its Derivatives, zinc and its derivatives (e.g., ZnO, ZnSO4), selenium and its derivatives selenium methionine, stilbenes and their derivatives (e.g., stilbe trans-stilbene oxide), as well as derivatives of the active compounds (e.g. For example, salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids. ), for example selected from the group consisting of those suitable according to the present invention.

[0176] Composition or oat extract or a composition or oat extract according to the present invention Cosmetics or pharmaceutical preparations containing vitamins and vitamin precursors may also contain and any vitamin D3 suitable or customary for cosmetic and / or dermatological applications. Vitamins and vitamin precursors, e.g. For example, tocopherols, vitamin A, nicotinic acid and nicotinamide, and other B-complex vitamins Particular mention may be made here of vitamins, in particular biotin, and vitamin C. Other examples within this group that are preferred include pantothenyl alcohol and its derivatives, In particular its esters and ethers, and cationic pantothenyl alcohol Derivatives of pantothenyl alcohol, such as pantothenyl alcohol triacetate, pantothenyl alcohol Pantothenyl ether and its monoacetate, and also cationic pantothenyl ether Alcohol derivatives are also included.

[0177] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations having the above properties may also contain active compounds with whitening action. and any skin whitening agent suitable or customary for cosmetic and / or dermatological applications. Active compounds which can be used in accordance with the invention are: Among them, whitening stilbene derivatives, kojic acid, hydroquinone, arbutin, Ascorbic Acid, Magnesium Ascorbyl Phosphate, Resorcinol, Licorice Root Extract and their constituents glabridin or licochalcone A, or Rumex and R extract from amulus species, extract from pine species (Pinus) or extract from Vitis species Extracts are included.

[0178] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic preparations having a skin-tanning action may also contain active compounds having a skin-tanning action. Any skin tan that is suitable or customary for cosmetic and / or dermatological use may be used. A cleaning active compound may be used. Dihydroxyacetone (DHA; 1,3-dihydroxyacetone) DHA can be mentioned here as an example. The dimer may be present in either form, and the proportion of the dimer may be predominant in the crystalline form. be.

[0179] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing mono-, di- and oligosaccharides, e.g., glutamic acid ... It may also contain glucose, galactose, fructose, mannose, and lactose. Cut.

[0180] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing the compounds may also contain plant extracts, which It is usually prepared by extracting the whole plant, although in individual cases the flowers and / or The compounds may be prepared solely from leaves, wood, bark or roots. In particular, with regard to plant extracts, fdeklaration kosmetischer Mittel(Guide t o the Declaration of Constituents of Cos. metic agents), Industrieverband Koerperpf Legemittel und Waschmittel eV(IKW)(Ind ustrial Association for Toiletries and D Published by the German Chamber of Commerce, Frankfurt, 3rd edition, listed in the table beginning on page 44. Particularly advantageous extracts include those derived from aloe, Hamamelis, algae, Oak bark, willow herb, nettle, dead nettle, hops, chamomile, yarrow , arnica, calendula, burdock root, horsetail, hawthorn, linden blossom, cucumber berries, almonds, pine needles, horse chestnut, sandalwood, juniper, coconut, mango Go, apricot, orange, lemon, lime, grapefruit, apple, green tea, grapefruit Roots seeds, wheat, oats, barley, sage, thyme, basil, rosemary, birch Nobile, mallow, cardamom, willow bark, sedge, coltsfoot, and billow Among these, particularly preferred extracts include: water hyacinth, ginseng, and ginger root. Ingredients include aloe vera, chamomile, algae, rosemary, calendula, ginseng, and chili. Cucumber, sage, nettle, linden blossom, arnica and Hamamelis Mixtures of two or more plant extracts may also be used. Extraction agents that can be used to prepare the product include water, alcohol, and Preferred alcohols in this context include lower alcohols, e.g. For example, ethanol and isopropanol, but polyhydric alcohols, e.g., ethylene glycol Also preferred are ethanol, propylene glycol and butylene glycol, specifically only In accordance with the present invention, the plant extract is preferably used both as a sole extractant and in a mixture with water. can be used in pure or diluted form.

[0181] Composition or oat extract or a composition or oat extract according to the present invention Cosmetic or pharmaceutical preparations containing crystalline or microcrystalline solids, such as inorganic When micropigments are incorporated into the preparations according to the invention, they can be anionic, cationic, non-ionic, The surfactant may contain ionic and / or amphoteric surfactants. Surfactants are amphiphilic substances that can dissolve organic, non-polar substances. They are generally classified according to the nature and charge of the functional moiety. Four groups can be differentiated here: Anionic surfactants, cationic surfactants, amphoteric surfactants and nonionic surfactants Agent.

[0182] Anionic surfactants usually contain carboxylate, sulfate, or sulfonate groups In aqueous solution, they form negatively charged organic imines in acidic or neutral media. Cationic surfactants are mostly based on the presence of a quaternary ammonium group. In aqueous solution, they are positively charged organic imines in acidic or neutral media. Amphoteric surfactants contain both anionic and cationic groups, but Depending on the pH value, they behave like anionic or cationic surfactants in aqueous solution. They have a positive charge in a strongly acidic medium and a negative charge in an alkaline medium. In contrast, in the pH range, they are zwitterions. Polyether chains are non-ionic interfaces. Typical of surfactants: Nonionic surfactants do not form ions in aqueous media.

[0183] Anionic surfactants which can be used to advantage include: acyla amino acids (and their salts), such as acyl glutamates, e.g., acyl glutamine Sodium Palmitoyl Aspartate, Di-TEA-Palmitoyl Aspartate and Caprylic / Capric Acid monosodium glutamate; acyl peptides, such as palmitoyl hydrolyzed milk protein, Sodium Cocoyl Hydrolyzed Soy Protein and Sodium Cocoyl Hydrolyzed Collagen sodium / potassium; sarcosinates, e.g., myristoyl sarcosine, lauroyl sarcosine Sodium Lauroyl Sarcosinate and Sodium Cocoyl Sarcosinate; Urates, such as sodium lauroyl taurate and methyl cocoyl sodium taurate acyl lactylates, such as lauroyl lactylate and caproyl lactylate; Alaninates; carboxylic acids and derivatives, e.g., lauric acid, aluminum stearate magnesium alkanolate and Zinc undecylate; ester carboxylic acids, such as calcium stearoyl lactylate , laureth-6 citrate and PEG-4 sodium lauramidocarboxylate; ether Carboxylic acids, such as sodium laureth-13 carboxylate and PEG-6 cocamide carboxil sodium phosphate; phosphate esters and salts, such as DEA-oleth-10 phosphate and dilaureth-4 phosphate; sulfonic acids and salts, for example, acyl isethionate, e.g. For example, sodium / ammonium cocoyl isethionate; alkyl aryl sulfonates Alkyl sulfonates, such as sodium coco monoglyceride sulfonate, olefins ( C12-14) Sodium Sulfonate, Sodium Lauryl Sulfoacetate, and PEG-3 Cocamide magnesium sulfate; sulfosuccinates, such as dioctyl sodium sulfosuccinate Succinate, Disodium Laureth Sulfosuccinate, Disodium Lauryl Sulfosuccinate and sulfosuccinic acid undecylenamide MEA-disodium; and sulfate esters, For example, alkyl ether sulfates, such as sodium laureth sulfate and ammonium laureth sulfate Sodium, Magnesium Laureth Sulfate, MIPA Laureth Sulfate, TIPA Laureth Sulfate, Sodium pareth sulfate and C12-13 sodium pareth sulfate, and alkyl sulfate, e.g. For example, sodium lauryl sulfate, ammonium lauryl sulfate, and TEA lauryl sulfate.

[0184] Cationic surfactants that can be advantageously used include alkylamines, alkyl These include imidazoles, ethoxylated amines and quaternary surfactants.

[0185] Quaternary surfactants are surfactants that contain at least one alkyl or aryl group covalently bonded to four alkyl or aryl groups. Contains 1 N atom, which gives it a positive charge regardless of the pH value. Alkyl betaines, Alkylamidopropyl betaine and alkylamidopropyl hydroxysulfane ( The cationic surfactants used are preferably Also preferred are the group of quaternary ammonium compounds, in particular benzyltrialkylammonium chlorides. ammonium or benzyltrialkylammonium bromide, for example, benzyldimethylammonium chloride tearylammonium, as well as alkyltrialkylammonium salts such as cetearyl chloride; Cetyltrimethylammonium or cetyltrimethylammonium bromide, alkyldichloride Methylhydroxyethylammonium or alkyldimethylhydroxyethylammonium bromide ammonium, dialkyldimethylammonium chloride or dialkyldimethylammonium bromide ammonium, alkylamidoethyltrimethylammonium ether sulfate, alkylpi pyridinium salts, such as laurylpyridinium chloride or cetylpyridinium chloride, iminopyridinium salts, Dazoline derivatives and compounds of cationic nature, such as amine oxides, e.g., arsenic alkyl dimethyl amine oxide or alkyl aminoethyl dimethyl amine oxide Cetyltrimethylammonium salts can be used with particular advantage. do.

[0186] Amphoteric surfactants which can be used advantageously include acyl / dialkylethylenediamines. amines, such as sodium acylamphoacetate, disodium acylamphodipropionate, Disodium alkylamphodiacetate, sodium amphohydroxypropyl acyl sulfonate Um, disodium acylamphodiacetate and sodium acylamphopropionate;N - alkyl amino acids, e.g. aminopropyl alkyl glutamides, alkyl amino propyl Sodium alkylimidodipropionate and lauroamphocarboxyglycerin Nate is one example.

[0187] Nonionic surfactants which can be advantageously used include alcohols; alkanols; Amides, e.g., cocamide MEA / DEA / MIPA, amine oxides, e.g., cocoa amidopropylamine oxide; ethylene oxide of carboxylic acids, glycerol, sorbitan or or other alcohols; esters, e.g., ethoxylated Ethoxylated / propoxylated alcohols, ethoxylated / propoxylated esters, ethoxylated / propoxylated Propoxylated glycerol esters, ethoxylated / propoxylated cholesterol, ethoxy Ethoxylated / Propoxylated Triglyceride Esters, Ethoxylated / Propoxylated Lanolin, Ethoxylated Propoxylated / propoxylated polysiloxanes, propoxylated POE ethers and alkylpolysiloxanes Glycosides, such as lauryl glucoside, decyl glucoside and coconut glucoside; glycerol esters and ethers; polyglycerol esters, diglycerol esters, Monoglycerol esters; methyl glucose esters; esters of hydroxy acids. can be done.

[0188] anionic and / or amphoteric surfactants and one or more nonionic surfactants The use of surfactants in combination with the histamine release inhibitors according to the invention is also advantageous. In preparations containing the agent, at a concentration between 1 and 98% (m / m) based on the dry weight of the preparation It can exist.

[0189] Composition or oat extract or a composition or oat extract according to the present invention The cosmetic or pharmaceutical preparations may also be in a form suitable for topical application, for example as a lotion. formulations, aqueous or aqueous-alcoholic gels, vesicle dispersions, or simple or complex As emulsions (O / W, W / O, O / W / O or W / O / W), liquid, semi-liquid or solids, e.g. milk, cream, gel, cream-gel, paste or syrup; They can also be formulated into a medicament, optionally packaged as an aerosol. These compositions may be applied in the form of a mousse or spray. It is prepared by the method.

[0190] To prepare emulsions, the oil phase can be advantageously chosen from the following group of substances: minerals Oils, mineral waxes; fatty oils, fats, waxes and other natural and synthetic fatty bodies, preferably Preferably, fatty acids and alcohols with low carbon numbers, such as isopropanol and propylene. Esters with glycol or glycerol, or with fatty alcohols and low carbon numbers esters of alkanoic or fatty acids; alkyl benzoates; silicone oils; For example, dimethylpolysiloxane, diethylpolysiloxane, diphenylpolysiloxane and mixed forms thereof. Advantageously, saturated and / or cyclic alkylenes with a chain length of 3 to 30 C atoms. or unsaturated, branched and / or linear alkanecarboxylic acids with a chain of 3 to 30 C atoms Esters with saturated and / or unsaturated, branched and / or straight chain alcohols having a aromatic carboxylic acids and saturated and / or unsaturated carboxylic acids with a chain length of 3 to 30 C atoms It is possible to use from the group of esters with mono-, branched and / or linear alcohols. Preferred ester oils include isopropyl myristate and isopropyl palmitate. Isopropyl stearate, Isopropyl oleate, n-butyl stearate, n-Hexyl urate, n-decyl oleate, isooctyl stearate, stearin Isononyl isononanoate, Isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethyl Hexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate oleyl, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and synthetic, semi-synthetic and natural mixtures of such esters, such as jojoba oil. can be.

[0191] The oil phase may also contain branched and straight chain hydrocarbons and waxes, silicone oils, dialkyl ethers, Groups including esters, saturated or unsaturated, branched or straight chain alcohols, and fatty acid triglycerides The group including amides, in particular saturated and unsaturated olefins with a chain length of 8 to 24, especially 12 to 18, carbon atoms. and / or unsaturated, branched and / or straight chain alkanecarboxylic acid triglycerides The fatty acid triglycerides may be advantageously selected from synthetic and semi-synthetic fatty acid triglycerides. and natural oils, such as olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, It may be advantageously selected from the group comprising coconut oil, palm oil, coconut oil, palm kernel oil, etc. Any blend of such oil and wax components may also be used to advantage. In some cases, waxes, e.g., cetyl palmitate, are used as the only lipid component of the oil phase. It is also advantageous to use 2-ethylhexyl isostearate, octyl isostearate, Ludodecanol, isotridecyl isononanoate, isoeicosane, 2-ethyl coconut oil fatty acid Hexyl, C12-15 alkyl benzoate, caprylic / capric triglyceride, and dicaprylyl ether. A mixture of alkyl and 2-ethylhexyl isostearate, C12-15 alkyl benzoate and A mixture of isotridecyl isononanoate and C12-15 alkyl benzoate, isostearyl isononanoate, A mixture of 2-ethylhexyl isononanoate and isotridecyl isononanoate is particularly advantageous. The hydrocarbons paraffin oil, squalane and squalene can also be used advantageously. The oil phase may also advantageously contain or be composed entirely of cyclic or linear silicone oils. However, in addition to one or more silicone oils, the addition of other oil phase components may be used. A content of cyclomethicone (e.g., decamethylcyclopentasiloxane) is preferably used. Siloxanes can be advantageously used as silicone oils. However, other silicones oils, such as undecamethylcyclotrisiloxane, polydimethylsiloxane and poly Poly(methylphenylsiloxane) can also be used advantageously. A mixture of isotridecyl nonanoate and cyclomethicone and 2-ethyl isostearate Mixtures of xyls are also particularly advantageous.

[0192] of a composition according to the invention or a preparation containing an oat extract and provided in the form of an emulsion The aqueous phase contains alcohols, diols or polyols with low C numbers, and these ethers ether, preferably ethanol, isopropanol, propylene glycol, glycerol , ethylene glycol, ethylene glycol monoethyl or monobutyl ether, proton Pyrene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol Monomethyl or monoethyl ethers of methyl alcohol and similar products, as well as products with low C numbers alcohols, such as ethanol, isopropanol, 1,2-propanediol, It may contain glycerol and in particular one or more thickening agents, the thickening agent being silicon dioxide. the group including cellulose, aluminum silicate, polysaccharides and their derivatives, for example, hyaluronic acid; Xanthan gum, hydroxypropyl methylcellulose, and particularly preferably polyacrylate. polyacrylates from the group comprising acrylates, preferably from the group comprising the so-called Carbopols, e.g. , Carbopol types 980, 981, 1382, 2984, and 5984, respectively. They can be advantageously selected on their own or in combination.

[0193] The composition according to the invention or the composition containing an oat extract and provided in the form of an emulsion is also or oat extract or cosmetic or pharmaceutical preparations are cosmetic or pharmaceutical preparations Advantageously, it contains one or more emulsifiers commonly used in the art to prepare do.

[0194] The composition according to the present invention or the composition containing oat extract or the oat extract The cosmetic or pharmaceutical preparation may also comprise a cosmetically or pharmaceutically acceptable carrier, For example, it may include one of the following commonly used in the art (these including but not limited to): lactose, glucose, sucrose, sorbitol, mannitol, Starch, acacia gum, calcium phosphate, alginate, gelatin, calcium silicate Ingredients: cellulose, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methyl Cellulose, methyl hydroxybenzoate, propyl hydroxybenzoate, talc , magnesium stearate, mineral oil, etc. Cosmetics or pharmaceutical preparations may also contain the above-mentioned components. In addition to the ingredients, it may contain lubricants, wetting agents, sweeteners, flavoring agents, emulsifiers, suspending agents, preservatives, etc. Suitable pharmaceutically acceptable carriers and formulations can be found in Remington's Pharmaceuticals and Medical Devices. It is described in detail in Harmaceutical Sciences (19th ed., 1995). It is being done.

[0195] Pharmaceutical preparations may be administered orally or parenterally. When administered, the pharmaceutical composition may be administered by intravenous injection, subcutaneous injection, intramuscular injection, intraperitoneal injection, or topical administration. It can be administered by oral administration, cutaneous administration, nasal administration, etc.

[0196] The appropriate dose of the pharmaceutical preparation according to the present invention may vary depending on, for example, the formulation method, age, weight, sex, etc. the condition or disease caused by the drug, food, time of administration, route of administration, rate of excretion and patient sensitivity. It can be formulated in a variety of ways depending on factors such as:

[0197] The pharmaceutical compositions according to the present invention are provided in unit dosage form and are readily available to those of ordinary skill in the art to which the present invention pertains. The method can be more easily carried out by using pharmaceutically acceptable carriers and / or excipients. The compound may be prepared by using the compound.

[0198] The present invention will now be described in detail with reference to the following examples, which are not intended to be limiting unless otherwise specified. The invention is not limited by or to the following examples, which are intended to be illustrative of the invention. It is not going to be. [Example]

[0199] Examples of the present invention are described below. However, the invention is not limited to the detailed examples. This is not to be construed as meaning that [Example]

[0200] Extraction of milled and unmilled naked oat (Avena nuda) kernels. The plant material is usually crushed, crushed, or cut into small pieces to make it more complete. Thus, crushed and uncrushed naked oat kernels allow for extraction. The extractions were compared.

[0201] 100 grams of organic naked oat kernels (Salomon variety, Bohlenser Muehle and grown in Germany) in whole or crushed form, 300g The rum was extracted with 50% aqueous ethanol (w / w) at 60°C for 2 hours with stirring. The mixture was cooled to room temperature and the grains were separated from the extract by centrifugation and filtration. The extraction solvent was removed in vacuum using a porator, and the resulting dry extract was weighed to determine the extraction yield. It was decided that:

[0202] on an ODS-AQ column (YMC) using an acetonitrile / water / 0.1% formic acid gradient. Quantify Avns in the dried extract by HPLC at 330 nm and analyze with Megazyme. Use a β-glucan assay kit (mixed binding) according to the manufacturer's instructions to measure β-glucan. The acetylcholine and monomeric glucose were quantified.

[0203] This assay kit is suitable for cereals such as oats and barley, and products derived from these grains, e.g. For example, the mixed-linkage (1→3, 1→4) β-glucan found in oat fiber products, malt, and beer It is specific to Kan.

[0204] Assay principle: The sample is suspended in a pH 6.5 buffer, hydrated, and then purified The filtrate was then incubated with lichenase enzyme and filtered. An aliquot of the filtrate was then purified. The resulting D-glucose was then completely hydrolyzed using β-glucosidase. Then, glucose oxidase / peroxidase reagent is used to determine the level of ATP.

[0205] [Table 2]

[0206] Aqueous ethanolic extracts from whole grain (unmilled) were obtained from milled grain. The total content of Avns A-C in the obtained extract was 1.9 times higher (5900 ppm vs. 3091 ppm). The results show that the aqueous ethanol from the crushed grains contains ethanol. The β-glucan content of the maltodextrin extract was 0.1g / L and 0.2g / L, respectively. - 2.4 times higher glucan content than unmilled, naked oat whole kernel extract , a much simpler, faster and therefore cheaper method of extracting plant material from the extract after extraction. It has the added benefit of allowing separation. [Example]

[0207] Extraction of milled and unmilled oat (Avena sativa) grains.

[0208] 50 grams of oat kernels (Max variety, grown in Germany), whole or ground The mixture was crushed and then soaked in 300 grams of 50% aqueous ethanol (w / w) for 2 hours at different temperatures. The mixture was cooled to room temperature and the grains were extracted by centrifugation and filtration. The extractant was removed in vacuo using an evaporator to obtain a dry extract. The A in the dried extract was weighed to determine the extraction yield. vns was quantified.

[0209] [Table 3]

[0210] For crushed oat kernels, the extraction yield increased with increasing temperature, from 3.5 to 4.5°C. The results show that the solubility of Avns A to C increases from 5% at 70°C to 4.4% at 70°C. The content increases in parallel from 1880 ppm at 40°C to 2056 ppm at 60°C. , and then decreases to 1894 ppm at 70°C. Therefore, based on the yield and Avn content, Extraction of crushed oats at temperatures between 50 and 60°C gives the best results.

[0211] The most suitable temperature for the extraction of uncrushed oat kernels is 60°C, which is higher than that of crushed oat kernels. The dried extract had a 2.0-fold higher Avns A-C content than the extract obtained from wheat grain. brought about. [Example]

[0212] Avena nuda (naked oat) kernel containing Avns and β-glucans Preparation of extract fractions

[0213] 1000 grams of unmilled organic naked oat kernels (Bohlenser M ühle and grown in Germany; the same batch as used in Example 1) 2000 grams of 50% aqueous ethanol (w / w) was used and stirred at 60°C for 2 hours. The mixture was cooled to room temperature, and the kernels were centrifuged and separated from the extract by filtration. The extracted grain was then resuspended in another 1500 grams of 50% aqueous ethanol (w / w). Perform a second extraction with stirring for 2 hr at 60 °C, and extract as described above. The extracts from the two extractions were combined to obtain 2700 grams. Dry the extract by removing the extraction solvent from a 118 gram aliquot using a microwave oven. The substance content and extraction yield were determined, resulting in 1.57 grams of dry extract. This corresponded to a dry extract yield of 3.6% by weight.

[0214] Remove the ethanol from the remaining extract using an evaporator under vacuum. The dry matter content of the resulting aqueous extract was determined and 100 grams of Add 1000 grams of water to obtain a 3.0 wt% solution. The pH was adjusted to 3.0 and the precipitate that formed was removed by centrifugation.

[0215] 250 grams of Lewatit (registered trademark) washed and reconstituted in water according to the manufacturer's instructions VP OC1064MD PH resin (Lanxess) was placed in an open glass tube with a diameter of 4 cm. The solution was packed into a column and the aqueous extract was poured into it. The column was then washed with 300 grams of water and the resin was removed by vacuum or Excess water was removed by blowing nitrogen through the flask. Then, 600 grams of ethanol was added. The adsorbed extractive components were eluted from the resin using a filter.

[0216] The filtrate and wash water were combined and freeze-dried to obtain 20 grams of dry water fraction. This corresponded to a yield of 2.0% by weight based on oat kernels.

[0217] The ethanol was removed from the ethanolic eluate by vacuum to give 7.5 grams of dry ethanol. A mol fraction was obtained, corresponding to a yield of 0.8% by weight based on oat kernels. .

[0218] The dried extract fractions were characterized as described in Example 1.

[0219] [Table 4]

[0220] The dried ethanol eluate fraction was 5.4 times higher than the dried aqueous ethanol extract. Contains higher Avns content (total Avns A~C content 22239ppm vs. 4134ppm). The results show that it does.

[0221] Surprisingly, the dried ethanol eluate fraction also showed that β-glucan was water soluble. Even as dried, the beta-glucan content was 2.7 times higher than that of the aqueous ethanol extract. The total content of Avns A-C is 2.2 times higher than that of the filtered water fraction. % by weight (22239 ppm) and a β-glucan content of 2.8% by weight. Interestingly, the ethanol eluate fractions were found to contain both substance classes in the same extract fraction. also contain very similar contents.

[0222] The dried aqueous ethanolic extract and dried ethanol eluate fractions were also their cation and anion content by ion chromatography, and Free amino acids were analyzed by HPLC using post-column ninhydrin derivatization. It was.

[0223] [Table 5]

[0224] As can be seen from the determined cations and anions (0.24% vs. 5.40% total) The salt content in the dried ethanol eluate fraction was 0.1% of that in the dried aqueous ethanol extract. The results show that the salt content is much lower than that of the medium.

[0225] This has two advantages: on the one hand, oil-in-water (o / w) emulsions are widely used in commercial personal care products; This is the most popular type of emulsion. In such emulsions, the external phase is aqueous, The internal phase contains water and water-soluble components, while the internal phase contains oil and oil-soluble components. Ionized materials (cations and anions) can destabilize the emulsion interface. Adding an emulsion to an emulsified material destabilizes the emulsion, allowing the materials therein to be separated or purified. This is a common strategy used in water treatment plants to reduce salt content. Lowering the temperature can be considered beneficial to emulsion stability.

[0226] On the other hand, metal ions can cause the degradation of ingredients used in personal care products, for example. Because they can catalyze chemical processes and the performance of many products, Therefore, the reduction of the metal cation content has a strong effect on the product and This may be considered beneficial for ingredient stability.

[0227] The dried ethanol eluate fraction was four times smaller than the dried aqueous ethanol extract. Results also show that it contains less total free amino acids (2.44 vs. 0.60%) Interestingly, however, the dried ethanol eluate fraction was significantly higher than the dried aqueous ethanol. Contains 3.8 times more phenylalanine and 4.3 times more tryptophan than ethanol extract Contains [Example]

[0228] ABTS assay

[0229] Since Avns and β-glucans are known to exhibit antioxidant efficacy, ABT Radical scavenging of the extract and extract fractions obtained in Example 3 using the S assay The activity was determined.

[0230] The antioxidant capacity of the test substances was measured with the help of ABTS assay. -Bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) with potassium persulfate The blue-green radical cation ABTS was converted by the antioxidant (test substance). ) is added to reduce the radical cation, resulting in a color change, which can be measured photometrically at 734 nm. It was decided that.

number

[0231] The IC50 was calculated from the inhibition [%] of radical formation in a series of dilutions of the test sample. is the concentration at which radical formation is inhibited by 50%. The results are shown in Table 6.

[0232] [Table 6]

[0233] Comparison of IC50 values ​​was performed using dried ethanol eluate fractions compared to dried aqueous ethanol. It was 5.7 times more active than the extract and 9.1 times more active than the dried filtered water fraction. is doing. [Example]

[0234] Avena nuda (naked oat) kernel containing Avns and β-glucans Preparation of extract fractions - pH 3.0 vs. unadjusted pH

[0235] 501 grams of unmilled organic naked oat kernels (Salomon variety, Bo purchased from Hlenser Muehle and grown in Germany; used in Examples 1 or 3 (a different batch from the one used) used 800 grams of 50% aqueous ethanol (w / w). The mixture was extracted with stirring at 60°C for 2 hours and then extracted twice as described in Example 3. The extracts from the two extractions were combined to give 1070 grams. Dry matter content by removing the extraction solvent by vacuum from a 115 g aliquot The extraction yield was determined, resulting in 1.54 grams of dry extract. This corresponded to a dry extract yield of 2.9 wt%.

[0236] The remaining extract was divided into two parts. The first part contained: (A) Using an evaporator, ethanol was removed from 485 grams of extract by vacuum. (6.5 grams of dry extract) to obtain 130 grams, which was diluted by adding water. The pH was then adjusted to 1.0. The pH was adjusted to 3.0 by means of hydrochloric acid.

[0237] 250 grams of Lewatit (registered trademark) washed and reconstituted in water according to the manufacturer's instructions VP OC1064MD PH resin (Lanxess) was placed in a 4 cm diameter glass column. The solution was filled into a container and the pH-adjusted aqueous extract was added to it. The resulting filtrate was reloaded onto the column twice. The column was then reloaded with 200 grams of of water and excess water is removed by vacuum or by blowing nitrogen through the resin. The adsorbed extractive components were then removed from the resin using 600 grams of ethanol. Eluted.

[0238] The filtrate and wash water were combined and freeze-dried to obtain 4.0 grams of dry water fraction. This corresponded to a yield of 1.8% by weight based on oat kernels.

[0239] The ethanol was removed from the ethanolic eluate by vacuum to give 2.1 grams of dry ethanol. This corresponds to a yield of 1.0% by weight based on oat kernels. Ta.

[0240] In the second part: (B) Add another 485 grams of extract (6.5 grams of dry extract) to the same The resulting mixture was treated as follows to obtain 500 grams of aqueous extract (1.3% by weight dry matter). The pH value of the solution was 6.4 and was not adjusted.

[0241] 250 grams of Lewatit (registered trademark) washed and reconstituted in water according to the manufacturer's instructions VP OC1064MD PH resin (Lanxess) was placed in a 4 cm diameter glass column. The column was filled with the aqueous extract without pH adjustment. The adsorption and elution were recorded in (A). was carried out as described.

[0242] The filtrate and wash water were combined and freeze-dried to obtain 4.4 grams of dry water fraction. This corresponded to a yield of 2.0% by weight based on oat kernels.

[0243] The ethanol was removed from the ethanolic eluate by vacuum to give 2.0 grams of dry ethanol. A mol fraction was obtained, corresponding to a yield of 0.9% by weight based on oat kernels. .

[0244] The dried extract and ethanol eluate fractions were characterized as described above. The results are summarized in Table 7.

[0245] [Table 7]

[0246] Both dried ethanol eluate fractions were significantly higher in ethanol than the dried aqueous ethanol extract. The results show that the aqueous extract shows a higher Avns content without pH adjustment. The dried ethanol eluate fraction obtained from the aqueous extract with pH 3 The dried ethanol eluate fractions had 3.1-fold and 2.7-fold higher Avns A, respectively. ~C total content (10544 and 9146 ppm vs. 3363 ppm).

[0247] However, the dried ethanol eluate fraction obtained from the aqueous extract without pH adjustment showed a pH Compared to the one adjusted to 3, the total content of Avns A to C was 20% (1.2 times) higher. Contains (10544 vs 9146 ppm).

[0248] Surprisingly, the dried ethanol eluate fraction also contained β-glucan as a water-soluble product. , 1.9-fold (A) and 1.8-fold (B) higher β- Contains glucan content.

[0249] Avns A~C total content 1.05% by weight (10544ppm), β-glucan content The dried ethanol extract obtained without pH adjustment from the aqueous extract had 2.21 wt.% Interestingly, both substance classes were separated from the dried extract obtained at pH 3.0. It contains a similar amount of ethanol to the ethanol eluate fraction (B).

[0250] In addition to the above experiments, a solution containing approximately 500 parts per million of Avns A to C was prepared. Two grams of 1,3-propanediol were extracted from (A) and (B). In addition to the dried ethanol eluate fractions, each weighing 109 milligrams, a reddish-brownish A solution is obtained, which is easy to use and handle, for example in cosmetic preparations.

[0251] The ABTS assay described in Example 4 was used to determine the dryness of the two ethanolic The antioxidant capacity of the ethanol eluate fractions was determined, and the results are shown in Table 8.

[0252] [Table 8]

[0253] Comparison of IC50 values ​​revealed that both dried ethanol eluate fractions had similar antioxidant capacity. It has been shown to show. [Example]

[0254] Avena nuda (naked oat) kernel containing Avns and β-glucans Preparation of extract fractions - Whole grain (unmilled) and milled grain (no pH adjustment) Compare the extracts of

[0255] Use 1200 grams of 50% aqueous ethanol (w / w) and stir at 60°C for 2 hours. 500 grams of unmilled organic naked oat kernels (Bohlenser purchased from Muehle and cultivated in Germany; The samples (different batches from the previous batch) were extracted twice as described in Example 3. The yield was determined as described in Example 5. This resulted in an extraction yield of 2.8 wt. %.

[0256] Ethanol was removed from the aqueous ethanolic extract and additional water was added to prepare the extract described in Example 5. As shown, an aqueous extract was obtained with a dry matter content of approximately 1% by weight.

[0257] 250 grams of Lewatit (registered trademark) washed and reconstituted in water according to the manufacturer's instructions VP OC1064MD PH resin (LANXESS) was placed in a 4 cm diameter glass column. The solution was filled into a 100 ml container and the aqueous extract (whose pH value was not adjusted) was poured into it. The filtrate was passed through the column at a flow rate of 1 ml / min. The obtained filtrate was applied to the column twice. and ethanol elution was carried out as described in Example 5.

[0258] The yield of filtrate and ethanol extract based on oat kernels was determined by drying. The concentrations were found to be 2.0 and 0.7 wt %, respectively.

[0259] The entire process was repeated with crushed grain: Extraction of whole grain (uncrushed) 0.6 grams of dried ethanol eluate from the sample was stirred at 30°C for 49 minutes. gram of glycerol in a 1:1 (wt / wt) mixture of water. The s content was determined by HPLC.

[0260] The dried extract, dried extract fraction and glycerol / water solution were prepared as described above. The results are summarized in Table 9.

[0261] [Table 9]

[0262] The adsorption step, when performed on extracts obtained using crushed grain, The results clearly show that neither s- nor β-glucan enrichment was obtained as expected. Components from the inner part of the oat kernel that are released prevent adsorption, thereby fractionating and A Interferes with vns enrichment.

[0263] The dried ethanol eluate fraction from the whole grain (unmilled) extract was Similarly, the total Avns A-C content was 3.1 times higher (8311 ppm vs. 2722 ppm). m), 3.1 times higher Avn L content (792 ppm vs. 256 ppm) and 2.2 times higher It contains a lower beta-glucan content (2.08 vs. 0.96%). [Example]

[0264] Scale up

[0265] A mixture of 860 kg of ethanol (96.5% by volume) and 800 kg of water was used. 500 kg (kilograms) of unmilled organic naked oat kernels (Oliver Seeds, purchased from Bohlenser Mühle and cultivated in Germany; Examples 1, 3, 5 (or a different batch than that used in 6) was extracted at 55-60°C for 2 hours. After separation of the liquid, the extraction of the extracted oat kernels was repeated using equal amounts of ethanol and water. After separation of the extract from the extracted grain, the two extracts were combined and an aliquot was dried. The extraction yield was determined as described in Example 5 by allowing the extract to stand for 2. It was found to be 6% by weight.

[0266] Ethanol was removed from the aqueous ethanolic extract by vacuum distillation and additional water was added. An aqueous extract with a dry matter content of approximately 0.5-1.0% by weight was obtained.

[0267] Lewatit® VP OC1064MD PH resin (Lanxess) The aqueous extract obtained (with an unadjusted pH value) was poured into a packed 20 liter steel column. The solution was then washed and conditioned in water according to the manufacturer's instructions. The remaining water was then removed by vacuum or by blowing nitrogen through the column. The column was then removed by sorption using 140 kg of ethanol (96.5% by volume). The adsorbed extractive components were eluted.

[0268] Yield of ethanol eluate based on oat grain by drying aliquots was determined and the yield was found to be 0.2 wt%.

[0269] An acetonitrile / water / 0.1% formic acid gradient was used to separate the eluates on an ODS-AQ column (YMC) ( The dried ethanol was analyzed on the AmazonSL ion trap in positive and negative ion modes. The ethanol eluate was analyzed for Avn by HPLC-DAD-MS measurement. These are summarized in Table 10.

[0270] The HPLC chromatogram of the dried ethanol eluate at 300–360 nm is shown in Fig. 3 is shown in.

[0271] [Table 10-1] [Table 10-2]

[0272] Glycerol and water are common cosmetic solvents, so glycerol and water were used as ethanol. Direct addition of the ethanol to the elution solution followed by removal of the ethanol is simple and less time consuming. A low energy consumption, glycerol / water based solution preparation method.

[0273] Glycerol 99.5% and water were added to the ethanol elution solution, and the ethanol was distilled under vacuum. Potassium sorbate was then added and the mixture was thawed for preservation purposes. The mixture was adjusted to a pH between 4.5 and 3.5 by means of lactic acid. 1% Ethylenediaminetetraacetic acid in a mixture of 0.8% by weight glycerol and 0.2% by weight potassium sorbate Finally, the solution was filtered on a filter plate to obtain a clear to slightly A slightly cloudy liquid was obtained, which makes it easy to formulate in general cosmetic preparations. , resulting in a cosmetically acceptable product that is easy to use.

[0274] The dried extract, dried ethanol eluate fraction and glycerol / water solution were added. The results are summarized in Table 11.

[0275] [Table 11]

[0276] When run on a production scale, Avns A-C content is only 1614 ppm. As can be seen, even if the oats used contained relatively low amounts of Avns, The adsorption step converts Avns into Avns A-C at 16020 parts per million as expected. The results clearly show that the β-glucan was enriched for β-glucan.

[0277] The β-glucan content was also enriched in this case, with comparable contents after the adsorption step. Extract fraction containing large amounts of Avns (1.60 wt%) and β-glucan (1.65 wt%) minutes were generated.

[0278] Using different batches of 250 kg of naked oat kernels from the same manufacturer, The process was repeated, maintaining the ratio of grain to extraction solvent, as described above. , the dry matter content of Avns in the ethanol eluate fractions relative to the glycerol and water By adjusting the amount, a total of 100 to 120 parts per million of Avns A to C can be obtained. A glycerol / water-based solution of the ethanol eluate fraction was prepared. The results of the two extractions are shown below. The comparison is shown in Table 12.

[0279] [Table 12]

[0280] As can be seen from the above results, the enrichment of Avns obtained in the adsorption step was observed at low and high A Efficacy of oat kernel extracts with both vns A-C contents (1614 vs. 5758 ppm) is achieved effectively.

[0281] Mineral content was assessed by IC for the dried extract and dried ethanol eluate fractions. The results are shown in Table 13.

[0282] [Table 13]

[0283] These results are consistent with those given in Example 3. Salt reduces emulsion stability. It is known that cations are known to catalyze oxidation reactions, so the observed mineral The reduction of RAL (cations and anions) is particularly beneficial for preparative applications. [Example]

[0284] Ember with 1,2-pentanediol and enriched Avn and β-glucan Liquid solution of extract fraction

[0285] Dry matter content 0.75 wt% and Avns A-C content in dry matter 16020p 100 grams of oat ethanol obtained as described in Example 7 having a pH of 1.5. An aliquot of the eluate was diluted with 50 grams of 99.5% glycerol, 5 grams of 1,2-pentaerythritol, and 100% glycerol. Mix with 100g of benzoxanthate (Hydrolite-5, Symrise) and 30g of water. The ethanol was removed by vacuum and water was added to the resulting solution to obtain 100 grams. The solution was filtered on a filter plate to obtain a slightly enriched solution of Avns and β-glucans. A cloudy, yellow-brown liquid oat extract fraction was produced, which contained 10% Avns A to C. 5 ppm (15 parts per million Avn C, 43 parts per million Avn A, 47 parts per million Avn n B), and was characterized by an Avn L content of 7 ppm and 0.02% β-glucan. [Example]

[0286] Stability testing of liquid oat extract fraction solutions containing different Avn

[0287] Enzyme obtained by membrane filtration (thus removing β-glucan; supplied by Ceapro) A glycerol / water-based solution of barley extract fractions containing the same Avns A-C total The glycerol content of the ethanol eluate fractions obtained in Examples 7 and 8 was 0.01g and 0.01g, respectively. The oxidative and light stability of the roll / water based solutions was evaluated.

[0288] The liquid was exposed to 5 bar oxygen at 70°C for 24 hours using an Oxipress device. or a Xenotest 440 device (60W, 1294kJ / m 2 , wavelength 300 The sample was irradiated for 6 hours using a UV-cut filter (UV-400 nm).

[0289] Before and after treatment, the content of Avns was determined by HPLC and the color was measured colorimetrically ( Hach Lange Lico690 device).

[0290] [Table 14]

[0291] The cation-containing β-glucan-enriched β-glucan-containing β-glucan derivatives obtained according to Example 7 were The oat extract fractions with reduced content were subjected to oxidative degradation using Av purchased from Ceapro. The results clearly show that the product is more stable than the n-enriched product, which is The process removes antioxidant β-glucan from the Avn-enriched product purchased from Ceapro. This is because the oxidative decomposition catalyst cations are removed, whereas the oxidative decomposition catalyst cations are not removed. This is particularly observable in terms of size and discoloration.

[0292] As can be seen from the Lab color values ​​shown in Table 15, The glycerol / water based solution of hand-prepared oats also has a darker color.

[0293] [Table 15]

[0294] Oats with enriched Avns and β-glucans as obtained according to Example 7 The extract fraction also removes β-glucan and removes cations, which are protective against light-induced degradation. The results showed that the Avn-enriched product purchased from Ceapro was slightly more stable than the Avn-enriched product purchased from Ceapro. This is particularly observable in the Avn C content. [Example]

[0295] Spray-dried oat extract fraction

[0296] Dry matter content 0.75 wt% and Avns A-C content in dry matter 16020p 220 grams of oat ethanol obtained as described in Example 7 having a pH of 1.5. To an aliquot of the eluate was added 440 grams of water. Then, 198 grams of corn-derived Maltodextrin DE17-20 was dissolved in aqueous ethanol solution to produce a slightly cloudy solution. A homogeneous yellowish solution was obtained, which was then spray dried to give the product shown in Figure 1. 160g with a particle size distribution (Mastersizer 2000, Malvern) In Figure 1, 10% of the particles had a diameter of d(0.1) = 2.868 μm. 50% of the particles have d(0.5) = 8.518 μm, and 90% of the particles have d(0.9 ) = 18.294 μm, and the specific surface area is 1.34 m 2 / g.

[0297] The same experiment was repeated using corn-derived maltodextrin DE8, and the results are shown in Figure 2. 160 with a particle size distribution (Mastersizer 2000, Malvern) gram of white powder was produced. In Figure 2, 10% of the particles had a d(0.1) of 4.440 μm. , 50% of the particles have d(0.5) = 11.022 μm, and 90% of the particles have d(0 .9) = 22.736 μm, and the specific surface area is 0.96 m 2 / g.

[0298] [Table 16]

[0299] Using the same drying technique, an oat ethanol fraction concentrated powder was prepared: 1200 g Maltodextrin DE17-20 was dissolved in 1500g of water. The resulting clear solution contained 802 ppm Avn C, 1429 ppm Avn A, 2203 ppm Avn B (total Avn A-C = 4434 ppm) and 202 ppm Avn L, Oat flour in ethanol / water 1:1 (w / w) obtained using the method described 300 g of a 10 wt % solution of the ethanol eluate was added under stirring. The homogeneous brownish solution was spray dried to give 196 ppm Avn C, 36 0 ppm Avn A, 562 ppm Avn B (total Avns A~C = 1118 ppm) pm) and 63 ppm Avn L, color values: L*=91.60, a*=-0. 970 g of a light beige powder was obtained, characterized by 12 and b*=11.36.

[0300] Spray-dried solid powders or granules have the advantage of being easy to handle and administer. Spray drying requires only a very short exposure to high temperatures (less than 1 minute). is a very gentle drying technique, which makes spray drying suitable for sensitive ingredients. It is also a relatively cheap technique, hence low amounts of dry matter and low viscosity. Spray drying is a well-established drying technique and is commercially available. are available on a large scale, thereby affecting product parameters, e.g. , dextrin or cyclodextrin, other modified starches or gum arabic It is also possible.

[0301] The particle size can also be adjusted depending on the respective needs and requirements, e.g., spray bed drying techniques. to produce smaller particles (0.07 It can accommodate particles from around 0.5 mm to larger particles (around 0.4 mm). allows the preparation of a free-flowing, almost dust-free powder. [Example]

[0302] Stability of spray-dried oat extract fractions enriched in Avns and β-glucans sex

[0303] Spray-dried enriched with Avns and β-glucan as obtained in Example 10 The oxidative and photostability of the oat extract fractions were evaluated using an Oxipress device. by exposing them to 5 bar oxygen at 60°C for 72 hours using Xen otest440 device (60W, 1294kJ / m 2 , wavelength 300-400nm) These were then irradiated for 6 hours and evaluated.

[0304] Before and after treatment, the content of Avns was determined by HPLC and the color was measured colorimetrically. Ta.

[0305] [Table 17]

[0306] Spray enriched with Avns and β-glucan as obtained according to Example 10 The dried oat extract fraction showed no change in color, with the Avns content remaining unchanged. The results clearly show that the compound is completely stable against oxidative degradation since it is not oxidized.

[0307] [Table 18]

[0308] Spray enriched with Avns and β-glucans, as obtained according to Example 10 - The dried oat extract fraction showed no change in color and the Avns content was not affected. The results clearly show that the compound is completely stable to light exposure since it has not been subjected to any chemical modification.

[0309] Ethanolic acid spray-dried on maltodextrin DE8 obtained according to Example 10 For the eluates, comparable results were obtained for oxidation and light exposure. This indicates that the DE value of lutodextrin does not affect stability. [Example]

[0310] Extraction of Avena sativa kernels containing Avns and β-glucans. Preparation of output fractions - pH 3.0 vs. unadjusted pH

[0311] In the first and second extractions, 1800 and 1200 grams of 50% aqueous ethanol were used. Each solution was stirred at 60°C for 2 hours using 950 ml of ethanol (w / w). grams of unmilled organic oat kernels (Nordlicht Naturkost (obtained from the University of California, San Diego and cultivated in Germany) was extracted twice as described in Example 3. The extraction yield was determined as described in, which resulted in an extraction yield of 2.2 wt.%. It resulted.

[0312] The remaining 1920 grams of extract was divided into two portions. The first portion contained: (A) Ethanol was removed from 990 g of extract by vacuum using an evaporator. (9.4 grams of dry extract) to obtain 400 grams. Dilution by adding water The pH value was then adjusted to 800 grams of aqueous extract (1.2% by weight of dry matter). , adjusted to 3.0 by means of hydrochloric acid.

[0313] 250 grams of Lewatit (registered trademark) washed and reconstituted in water according to the manufacturer's instructions VP OC1064MD PH resin (Lanxess) was placed in a 4 cm diameter glass column. The solution was filled into a container and the pH-adjusted aqueous extract was added to it. The resulting filtrate was applied to the column twice. Wash with ram water and remove excess water by vacuum or by blowing nitrogen through the resin. The absorbed extractive components were then removed by rinsing the resin with 600 grams of ethanol. It was eluted from

[0314] The filtrate and wash water were combined and freeze-dried to obtain 4.5 grams of dry water fraction. This corresponded to a yield of 1.1% by weight based on oat kernels.

[0315] The ethanol was removed from the ethanolic eluate by vacuum to give 3.0 grams of dry ethanol. A mol fraction was obtained, corresponding to a yield of 0.7% by weight based on oat kernels. .

[0316] In the second part: (B) Another 930 grams of extract (8.8 grams of dry extract) was added to the same solution as described in (A). The extract was treated as described above to obtain 800 grams of aqueous extract (1.1% by weight dry matter). The pH value of the solution was not adjusted.

[0317] 250 grams of Lewatit (registered trademark) washed and reconstituted in water according to the manufacturer's instructions VP OC1064MD PH resin (Lanxess) was placed in a 4 cm diameter glass column. The column was filled with the aqueous extract without pH adjustment. The study was carried out as described above.

[0318] The filtrate and wash water were combined and freeze-dried to obtain 6.3 grams of dry water fraction. This corresponds to a yield of 1.6% by weight based on oat kernels.

[0319] The ethanol was removed from the ethanolic eluate by vacuum to give 2.1 grams of dry ethanol. This corresponds to a yield of 0.5% by weight based on oat kernels. It was.

[0320] The dried extract and fractions were characterized as described above. The results are shown in Table 19. It is summarized.

[0321] [Table 19]

[0322] Both dried ethanol eluate fractions were compared to the dried aqueous ethanol extract. The results show that the aqueous extract without pH adjustment exhibits a higher Avns content. The dried ethanol eluate fraction obtained from the ethanol extract contained 3.8 times higher total Avns A-C content. The dried ethanol eluate fraction from the aqueous extract adjusted to pH 3 had a pH of 3.0. 2x higher Avns A-C total content (5294 and 4189 ppm vs. 1385 ppm) Contains.

[0323] However, the dried ethanol eluate fractions obtained from the aqueous extract without pH adjustment showed a pH Compared to the aqueous extract adjusted to 3, the total content of Avns A-C was 26% (1.26 times) higher. Contains 5294 ppm vs. 4189 ppm.

[0324] Surprisingly, the dried ethanol eluate fraction (A) also contained water-soluble β-glucan. 2.2 times higher β-glucan content than the dried aqueous ethanol extract, if any Contains: [Example]

[0325] Extraction of unground naked oats (Avena nil) using different extraction solvents (extractants) uda) Grain extraction

[0326] 100 g of naked oat kernels (purchased from Bohlenser Mühle, Germany) Oliver) with 300g of extractant (w / The mixture was cooled to room temperature, centrifuged, and filtered. The extracted grain was separated from the extractant by using a second portion of 300 g of extractant. The mixture was extracted again at 55°C for 2 hours, and the extract was separated from the kernels as described above. The two extracts were combined and the extraction solvent was removed under vacuum using an evaporator. The extract was removed and the resulting dry extract was weighed to determine the extraction yield. Next, Avns were quantified in the dried extracts.

[0327] [Table 20]

[0328] Extraction with water alone resulted in low Avns content and undetectable β-glucan. The results clearly show that a suitable extract cannot be obtained by using a mixture of organic solvents and water. All of the extracts obtained were suitable because they contained both Avns and β-glucans. , and therefore, they are fractionated by an adsorption step as previously described in the Examples. This is generally appropriate. The extract yield is between 2.2 and 3.7%. Between 0.25 and 2.73% β-glucan and between 752 and 4348 ppm Avns It contained the sum of A to C. [Example]

[0329] Oat extract according to the present invention (Example 7) and extract according to WO2004 / 047833A1 Comparison of Tapir Extracts:

[0330] Oats cultivated as described in Example 3 of WO2004 / 047833A1 Extraction of anthranilamide-containing extracts from straw (Avena sativa) Out:

[0331] 143 kg of ethanol / water 7:3 (v / v) was added to 9 kg of cultivated oat straw. The mixture is macerated at room temperature for 3 days. After filtration, the extract is concentrated under vacuum to the aqueous phase (17. 4kg, solid content: 2.5%; avenanthramides A, B and C in dry extract Total: 0.093%).

[0332] The aqueous solution was stirred with Amberlite XAD-16 (270 g). Extract in portions (2 kg). Separate the adsorption resin through a frit, wash with water and Elute with ethanol / water 1:1 (v / v). The combined eluates are stripped of solvent under vacuum. Dry extract: 8.5g; Sum of avenanthramides A, B and C: 1.2%.

[0333] The dried extract was dissolved in ethanol / water 1:1 (v:v) and Upon dilution with 1 (v / v), the avenanthramide content, i.e., total avenanthramide A , B and C are adjusted to 500 ppm.

[0334] As described in the literature, oat straw also contains β-glucan: Hager Rom 2006, Hagers Handbuch der Drogen und Arzn eistoffe: Avena stramentum (oat straw): Ingredients: Carbohydrate Compounds, β-glucan [8], cellulose, xylan and oligosaccharides kestose, neokestose Tos, Bifulcose, Neobifulcose;[7] avenalin

[53] , pectin 0.8 %

[17] or D.M. Gibeaut et al., Plant Physiol., 1990 , Vol. 94, pp. 411-416: Oats, and therefore also oat straw pulvinus of leaf-sheath [= base of leaf or leaf-like part of plant that promotes growth-independent actions It contains beta-glucan in the tissues surrounding the skin (Wikipedia).

[0335] [Table 21] Process according to Example 7 (76.4% vs. Example 3 in WO2004 / 047833) oat source by using only 25.2% of the oat feedstock. The comparison clearly shows that the recovery of nanthramide is much more efficient.

[0336] For Avns, ODS-AQ column (YMC) (in positive and negative ion modes) Acetonitrile / water / 0.1% formic acid on a Bruker Esquire ion trap Using a gradient, the oat straw extract according to WO2004 / 047833A1 was dried. The eluate of methanol / water 1:1 (v / v) was analyzed by HPLC-DAD-MS measurement. The results are summarized in Table 22.

[0337] HPLC of the dried methanol / water 1:1 (v / v) eluate at 328-332 nm The C chromatogram is shown in Figure 4. [Table 22] [Example]

[0338] Avenanthramide, β-glucan and salt contents in oat extract fractions

[0339] [Table 23]

[0340] The binding of at least one avenanthramide or all avenanthramides to β-glucan The weight ratio is in the range of 0.25:1 to 4:1, more preferably in the range of 0.3:1 to 3:1. do.

[0341] [Table 24]

[0342] The salt content in the oat extract is less than 1% by weight, in particular less than 0.5% by weight. [Example]

[0343] Formulation example

[0344] In Formulation Examples 1 to 11, the following two perfume oils PFO1 and PFO2 were used as fragrances. (DPG = dipropylene glycol)

[0345] [Table 25]

[0346] Table 26

[0347] Table 27-1 Table 27-2 Table 27-3 Table 27-4 Table 27-5 Table 27-6 Table 27-7 Table 27-8 Table 27-9 Table 27-10 Table 27-11 Table 27-12

[0348] Table 28

[0349] Table 29

[0350] Table 30

[0351] Table 31

[0352] Table 32

[0353] Table 33

Claims

1. 1. A method for preparing an oat extract, comprising: (1) providing an oat source; (2) extracting the oat source using at least one aqueous extraction solvent (extractant) comprising water and an organic solvent at a temperature of 30-80°C to obtain an extraction mixture or suspension; (3) removing the extracted insoluble oat source from the extraction mixture or suspension to obtain an aqueous extract; (4) removing the organic solvent from the aqueous extract to obtain an aqueous extract; (5) preparing and conditioning the adsorbent and providing the adsorbent in an adsorption device; (6) passing the aqueous extract through an adsorbent in an adsorption device to adsorb components of the aqueous extract; (7) Eluting the adsorbed components of the aqueous extract from the adsorbent using at least one elution solvent to obtain an eluate. wherein the method does not include a step of membrane filtration.

2. Further steps: (8) Removing the dissolution solvent from the eluate to obtain an oat extract. The method of claim 1 , comprising:

3. Between steps (6) and (7), (i) washing the adsorbent in the adsorption device with water to obtain wash water; and (ii) Removing excess water in the adsorber 3. A method for preparing the oat extract of claim 1 or 2, further comprising:

4. 4. The method according to any one of claims 1 to 3, wherein the selected oat source is milled or unmilled grain or oat straw of the species Avena sativa or Avena nuda.

5. 5. The method according to any one of claims 1 to 4, wherein the at least one aqueous extraction solvent is selected from the group consisting of mixtures of water and organic solvents suitable for foodstuffs or cosmetic or pharmaceutical preparations.

6. 6. The method of any one of claims 1 to 5, wherein the extraction step is carried out at a temperature in the range of 40 to 70°C.

7. 7. The method of any one of claims 1 to 6, wherein the adsorbent is selected from the group consisting of crosslinked polystyrene, ethylvinylbenzene and divinylbenzene, vinylpyrrolidone and divinylbenzene, vinylpyridine and divinylbenzene, copolymers of styrene and divinylbenzene, acrylic acid, copolymers of divinylbenzene and aliphatic dienes, polycyclic aromatics, polystyrene, poly(meth)acrylates, polypropylene, polyesters, and polytetrafluoroethylene.

8. 8. The method according to any one of claims 1 to 7, wherein the at least one dissolution medium is selected from the group consisting of organic solvents suitable for foodstuffs or cosmetics or pharmaceutical preparations, the organic solvent being selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, acetone or any mixtures thereof, i.e. combinations, or each in a mixture with water.

9. 9. The method of any one of claims 1 to 8, wherein the oat extract comprises 1.0 to 3.3% by weight of β-glucan, based on the dry weight of the oat extract.

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