Classifications

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Definitions

• the invention relates to the use of at least one active principle for reducing the glycation of proteins that can be glycated in tissues, for example at the level of the skin or at the level of the tissue wall of a blood vessel or of an organ.
• the present invention relates to at least one substance that can be used topically or orally to act on proteins that can be glycated in tissues.
• the glycated proteins also called advanced glycation end products or AGEs (Advanced Glycation Endproducts) decrease in particular the flexibility, the elasticity, and the functionality of the skin.
• AGEs Advanced Glycation Endproducts
• the glycation process takes place in three stages:
• Maillard This reaction results in the formation of AGEs, better known as Maillard products.
• the rate of formation of these compounds is independent of the sugar concentration of the medium but depends on the duration of the hyperglycemia and the rate of protein turnover.
• the first two stages Schot base and Amadori rearrangement
• the third is irreversible and progresses regardless of blood glucose level.
• Proteins of the extracellular matrix whose lifespan in the body is very long, are affected by glycation. Glycation modifies the properties of these proteins, making them more resistant to proteolysis and preventing their renewal. Moreover, the
• AGEs induce the formation of molecular bridges between collagen fibers, making it more rigid and less soluble.
• AGEs could have other actions by binding to specific receptors present in macrophages, endothelial and mesangial cells, inducing the secretion of pro-inflammatory cytokines or growth factors.
• the importance of protein glycation has been underlined by the effect of drugs that inhibit glycation, resulting in slower aging of some functions in experimental animals. During diabetes mellitus, there is also an exaggerated glycation of proteins, linked to the rise in blood sugar.
• Aminoguanidine is a pharmaceutical substance derived from guanidine. It binds to the products of glycation forming a reactive compound, unfit for crosslinking. At the level of the kidney for example, she prevents the formation of AGEs in glomeruli and reduces by 90% the excretion of albumin in diabetics.
• US patent application 2007/060533 describes the use of inhibitors of AGE formation for the treatment of diabetes and various diseases related to the formation of AGEs. This field is not therefore that of cosmetics where alterations of the skin can not reasonably be considered as pathologies related to the formation of AGEs.
• anthocyanins are glycosylated.
• the application US 2007/0003536 describes in particular the topical application of a grape seed extract (vitis vinifera) in combination with phospholipids as anti-free radical agents, but does not describe an action on AGEs. The mechanisms are very different. Grape seed extract is described as an anti-hydroxyl agent. Here again, there is no link with an activity on EGAs.
• the main purpose of the invention is to solve the technical problem of providing active substances that make it possible to limit the formation of AGEs resulting from the chemical glycation of proteins.
• the present invention is intended in particular to solve this technical problem in the context of the provision of cosmetic, dermatological or pharmaceutical compositions preventing or combating the reduction of the elastic and plastic properties of the tissues, for example at the level of the skin, or at the level of the tissue wall of a blood vessel or an organ, and in particular the skin, especially during tissue aging or diabetes.
• the present invention also aims to provide a method for screening active ingredients having the properties mentioned above.
• the present invention is intended to solve the technical problem reliably, reproducibly, providing non-toxic active substances, particularly for the cosmetics industry, dermatology, dermo-pharmacy, or pharmacy preferably topically.
• the invention particularly aims to provide active ingredients derived from plants, and in particular to provide active ingredients with low toxicity and dermatologically acceptable.
• the present invention also aims to provide active ingredients whose preparation is inexpensive, and industrially reliable and simple.
• the present invention describes the use of an active substance that promotes the inhibition of the formation of AGEs for the preparation of a composition for preventing and / or combating the reduction of the elastic and plastic properties of tissues, such as, for example at the level of the skin, or at the level of the tissue wall of a blood vessel or an organ, and in particular of the skin.
• the present invention relates to the use of an active substance for the preparation of a composition for promoting inhibition of AGE formation.
• the present invention relates to the use of an active substance for the preparation of a composition for preventing and / or controlling the glycation of proteins in tissues, such as for example cutaneous level, or at the level of the tissue wall of a blood vessel or organ.
• Glycation is implicated in many age-related progressive diseases, such as vascular diseases (such as atherosclerosis), kidney disease, arthritis, diabetes complications, scarring, and so on. It is significant that diabetic complications due to glycation, can occur even at a younger age in diabetic individuals, whose average blood sugar concentration is higher than normal. In diabetic disease, in which the involvement of free radicals is widely documented, oxidative stress is directly related to hyperglycemia. Too much sugar in the blood oxidizes easily. This oxidation of sugars leads, among other things, to sugar / protein or glycation grafts. The increased glycated hemoglobin level in diabetes is the typical example.
• Glycation products whose rate is proportional to the level of blood glucose over a long period of time, are partly responsible for tissue aging, whose decline in elastic and plastic properties is one of the causes.
• the present invention relates to the use of an active substance for the preparation of a composition for preventing and / or controlling the glycation of proteins, especially at the cutaneous level, linked to the rise in blood sugar during diabetes mellitus.
• the present invention relates to the use of an active substance for the preparation of a composition for preventing and / or controlling the formation of AGEs in glomeruli, and in particular reducing the excretion of albumin in diabetic subjects.
• the composition is a cosmetic, dermopharmaceutical or pharmaceutical composition, preferably applicable by topically or administered orally, for example as a dietary supplement.
• the present invention also relates to a cosmetic composition, applicable topically or as a dietary supplement (nutraceutical), for preventing and / or combating the reduction of the elastic and plastic properties of tissues, and in particular of the skin, as in the case of a fight against and / or prevention of aging of a tissue, by inhibiting the formation of AGEs at the level of the tissue, comprising as active substance a substance promoting the inhibition of the formation of AGEs, optionally in combination with a substance for promote the protection of skin proteins such as aminoguanidine or guanidine, or a glycation inhibiting agent by mineralization, such as EDTA derivatives, phytic acid, azelaic acid, or an enzyme inhibitor such as pentosidine , or a substance capable of decreasing the level of sugar available to participate in the glycation reaction, such as carnosine, ascorbic acid or alph a-tocopherol.
• a cosmetic composition applicable topically or as a dietary supplement (nutraceutical),
• the present invention also relates to a pharmaceutical composition, for example applicable topically or administered orally, in particular for combating and / or preventing the decrease in the elastic and plastic properties of a tissue, and in particular cutaneous tissue, or of the tissue wall of a blood vessel or of an organ, by inhibiting the formation of AGEs at the level of the tissue, characterized in that it comprises as active substance a substance promoting the inhibition of the formation of AGEs, optionally in combination with a substance to promote the protection of tissue proteins, such as aminoguanidine or guanidine, or a glycation-inhibiting agent by mineralization, such as EDTA derivatives, phytic acid, azelaic acid, or an enzyme inhibitor such as pentosidine, or a substance capable of decreasing the sugar level available to participate in the glycation reaction, such as carnosine, ascorbic acid or alpha-tocopherol.
• a pharmaceutical composition for example applicable topically or administered orally, in particular for combating and / or preventing the decrease
• the active substance promoting the inhibition of the formation of AGEs is preferably chosen from an extract of a plant, whole or part thereof, selected from an extract of Epimedes, an extract of crimped sorrel, an extract of Sarsaparilla, an extract of native liana (Davilla rugosa) Guarana, preferably the seeds, a Cachou extract, a Sylmarin extract, a pine extract, a Rhubarb extract from china , an extract of Hawthorn, leucocyanidines, for example extracted from grape seeds, and in particular leucocyanidines containing proanthocyanins of structure (I), an extract of Aréquier, an extract of Blueberry, an extract of Elderberry, an extract of Walnut, a Willow extract, a salad extract, an extract of Lespedeza and their mixtures.
• a part of the plant chosen from a root, a rhizome, a stem, a bark, a flower, a fruit, a seed, a germ, and a leaf, preferably at 1-10.
• % (w / w) in a solvent or a mixture of solvents preferably a protic polar solvent, and preferably in water, an alcohol, a glycol, a polyol, a water / alcohol mixture, water / glycol, or water / polyol (such as water in mixture with ethanol, glycerol, butylene glycol or other glycols, such as xylitol etc.) from 100/0 to 0/100 (v / v).
• the extracts obtained are then preferably filtered or distilled to recover the soluble fraction which is then filtered.
• the active substance is advantageously the plant extract in a solvent, such as water, an alcohol, a polyol, a glycol, or a mixture thereof, preferably diluted to a concentration of between 0.01 and 10% (v / v ).
• the plant extracts according to the present invention are preferably chosen from the group consisting of: the epimedium (Epimedium brevicornum), preferentially the leaves, the kinked sorrel (Rumex crispus), preferably the root, the leaves and / or the bark , Sarsaparilla (Smilax ornata) - The native liana (Davilla rugosa), especially its leaves
• the indigenous liana extract (Davilla rugosa), in particular its leaves, is of greater interest for producing a cosmetic, pharmaceutical, in particular dermatological composition, in combination with a suitable cosmetic and / or pharmaceutical vehicle, especially dermatological vehicle. .
• a suitable cosmetic and / or pharmaceutical vehicle especially dermatological vehicle.
• Such a composition is particularly intended for topical application to prevent and / or fight against aging of the skin and its unsightly manifestations, in particular wrinkles, fine lines, furrows and improves the general condition of the skin.
• the native liana is therefore useful for performing a cosmetic or dermatological treatment of applying the vine extract of the natives to a part of the human body, preferably the skin to improve the appearance and / or condition.
• the present invention thus relates to the use of this indigenous liana extract for cosmetic applications for aesthetic purposes or for producing a pharmaceutical composition, especially dermatological, in particular to protect the skin against the harmful effects of environmental agents including pollutants and UV and / or repair.
• the active substance promoting the inhibition of the formation of AGEs is preferably chosen from the following characterized molecules: anthraquinone and its derivatives, preferentially 1,4-anthraquinone and 1-amino-2 hydroxymethylanthraquinone, 4-hydroxychalcone, an OPC (procyanidolic oligomers), such as strawberry OPC, or leucocyanidines or proanthocyanins of structure (I), prunin, catechol, 4-aminophenol, sodium erythrosine, and plant extracts containing them, and their mixtures.
• OPC procyanidolic oligomers
• the molecule characterized according to the invention is preferably chosen from the group consisting of 1,4-anthraquinone, 1-amino-2-hydroxymethylanthraquinone, 4-hydroxychalcone, strawberry OPC, proanthocyanines of structure (I), prunin and mixtures thereof,
• the active substance is proanthocyanine of structure (I), preferably those obtained from grape seeds, and in particular an extract thereof, said extract containing at least 90%, and preferably at least 95% by weight of the proanthocyanines of structure (I).
• the invention therefore relates to a plant extract containing at least 90%, and preferably at least 95% by weight of the proanthocyanines of structure (I), and preferably obtained from grape seeds.
• the strawberry OPC is obtained from the strawberry rhizome (Fragaria vesca), preferably in the form of an extract containing a mixture of oligomers of anthocyanidins, catechins, epicatechins and procyanidines, preferentially as dimers to hexamers.
• the strawberry rhizome Fraaria vesca
• an extract containing a mixture of oligomers of anthocyanidins, catechins, epicatechins and procyanidines preferentially as dimers to hexamers.
• the invention relates to the use as an active ingredient promoting the inhibition of the formation of AGEs of a substance chosen from an extract of a whole plant or a part thereof, chosen from: Guarana, Cachou , Sylmarin, Pine, Rhubarb of China,, Epimede, Hawthorn, Leucocyanidines, Arquier, Blueberry, Elder, Walnut, Willow, Kernel Pochard, Salad, Sarsaparilla, Liana of the natives and Lespedeza; and / or a compound selected from sodium erythrosine, 1,4-anthraquinone, catechol, 4-hydroxychalcone, 4-aminophenol, OPC (procyanidolic oligomers), such as strawberry OPC, or leucocyanidines or proanthocyanines of structure (I), prunin, and 1-amino-2-hydroxymethylanthraquinone, or a mixture of these substances, for the preparation of a cosmetic, nutraceutical or pharmaceutical composition.
• active substances those which inhibit at least 65% the formation of AGEs, and preferably at least 80%, are preferred, with reference to the inhibition produced by the aminoguanidine at 1.5 mM.
• the preferred active ingredients in the compositions are selected from the group consisting of an epimedal extract (Epimedium brevicornum), preferably the leaves, a kernel sorrel extract (Rumex crispus), preferentially the root, the leaves and / or the bark, an extract of sarsaparilla (Smilax ornata), preferentially the roots, a vine extract of natives (Davilla rugosa), in particular leaves, 1,4-anthraquinone, 4-hydroxychalcone, strawberry OPC, prunin or a combination of them.
• an epimedal extract Epimedium brevicornum
• a kernel sorrel extract Rax crispus
• sarsaparilla Similarx ornata
• a vine extract of natives Davilla rugosa
• 1,4-anthraquinone 4-hydroxychalcone
• strawberry OPC prunin or a combination of them.
• the active substance can be concentrated by lyophilization, atomization, etc.
• said substance is used at a concentration preferably between 0.001 and 10%, preferably between 0.01 and 5% and more particularly at 1% for plant extracts, and preferably between 1.10 "7 and 1%, preferably between 1.10" 7 and 1.10 "lo / o, still preferentially IOL" 5 and 1.10 "lo / o to the characterized molecules, by weight of the total composition, without this being limiting of the concentration to be used
• a cosmetic treatment method comprising the topical application, or the ingestion as a dietary supplement (nutraceutical), of a composition comprising as a cosmetic active ingredient at least one of the
• the present invention also relates to a method of treating the human body comprising the administration of a pharmaceutical composition mentioned above or cited hereinafter, preferably topically, to prevent and / or fight against the glycation of proteins in a tissue, especially when the blood sugar level rises and / or is high, as for example during diabetes. in particular a method for reducing the excretion
• the present invention also relates to a method for screening active ingredients that inhibit the formation of AGEs, comprising: a) contacting at least one type of glycated protein, a sugar and the substance to be screened for its activity with respect to the inhibition of the formation of AGEs; b) the selection of at least one active ingredient promoting the inhibition of the formation of AGEs.
• step a) comprises an incubation of at least one type of protein of the skin or of walls of blood vessels, for example a collagen, or of a bovine serum albumin with a reducing sugar (for example glucose, ribose or fructose) or an aldehyde under conditions allowing the formation of AGEs.
• the skin protein is human collagen, which makes it possible to verify that the active substances of the invention are active on a majority protein in the human skin.
• step b) comprises the incubation of at least one type of protein of the skin or walls of blood vessels or of a bovine serum albumin with a reducing sugar (for example ribose, glucose, or fructose) or an aldehyde in the presence of at least one substance to be screened at a temperature of between 40 and 60 ° C., preferably at approximately 50 ° C.
• a reducing sugar for example ribose, glucose, or fructose
• aldehyde aldehyde
• the compounds according to the present invention are prepared in the form of topical compositions, in particular of cosmetic, dermopharmaceutical, or pharmaceutical, dermatologically acceptable compositions.
• the excipient contains, for example, at least one compound chosen from the group consisting of preservatives, emollients, emulsifiers, surfactants, moisturizers, thickeners, conditioners, mattifying agents, stabilizers, antioxidants, texture agents, gloss agents, film formers, solubilizers, pigments, dyes, fragrances and sunscreens.
• excipients are preferably chosen from the group consisting of amino acids and their derivatives, polyglycerols, esters, polymers and cellulose derivatives, lanolin derivatives, phospholipids, lactoferrins, lactoperoxidases, stabilizers based on sucrose, vitamins E and its derivatives, natural and synthetic waxes, vegetable oils, triglycerides, unsaponifiables, phytosterols, vegetable esters, silicones and its derivatives, protein hydrolysates, Jojoba oil and its derivatives, lipo / water-soluble esters, betaines, aminoxides, plant extracts, sucrose esters, titanium dioxides, glycines, and parabens, and more preferably from the group consisting of butylene glycol, steareth-2, steareth-21, glycol-15 stearyl ether, cetearyl alcohol, phenoxyethanol, methylparaben, ethylparaben, propylparaben, butylpara
• compositions are formulated in a form chosen from the group consisting of an aqueous or oily solution, an aqueous cream or gel or an oily gel, in particular in a pot or in a tube, in particular a shower gel, a shampoo; a milk ; an emulsion, a microemulsion or a nanoemulsion, especially oil-in-water or water-in-oil or multiple or silicone; a lotion, in particular in a glass or plastic bottle or in a measuring or aerosol flask; a lightbulb ; a liquid soap; a dermatological bread; an ointment ; a mousse; an anhydrous product, preferably a liquid product, pasty or solid, for example in the form of a stick, especially in the form of lipstick.
• topical application means applying or vaporizing the composition according to the present invention on the surface of the skin.
• the terms "dermatologically acceptable”, used herein, mean that the composition or components thereof are suitable for use in contact with human skin without toxicity, incompatibility, instability, allergic response, or their equivalents, undue.
• the terms "promoting inhibition of AGE formation” mean that the substance makes it possible to reduce the formation of an advanced glycation product (AGE) of a protein capable of glycation in the presence of a sugar. It is preferred that the substance promoting the inhibition of the formation of AGEs makes it possible, for example, to obtain a fluorescence of at least 65% of that obtained in the presence of aminoguanidine at 1.5 mM and in the absence of the active substance favoring inhibition of the formation of AGEs, for example under the conditions of Example 1 below.
• binders biological additives, buffering agents, blowing agents, chelating agents, additives, biocides, denaturants, external analgesics, materials forming films, polymers, opacifying agents, pH adjusters, reducing agents, depigmenting or brightening agents (for example: hydroquinone, kojic acid, ascorbic acid, magnesium ascorbyl phosphate, ascorbyl glucosamine), conditioning agents (eg for example: humectants), skin-soothing agents and / or healing agents (eg panthenol and its derivatives (eg ethyl panthenol), aloe
• AGEs and in particular those selected from the group consisting of: - Aye Wiwii (Maprounea guyanensis), and preferably the leaves
• Cercopia (Cercopia obtusa), and preferably the leaves and / or buds, - Pyrole (Chimaphila umbellata). 3,5-Dimethoxy-4-hydroxycinnamic acid (sinapic acid)
• DOPAC 3,4-dihydroxyphenylacetic acid
• phloroglucinol 1,3,5-trihydroxybenzene
• the active substances stimulating cell proliferation and / or differentiation, having an anti-aging effect in particular the following molecules: NGF, alpha-MSH, beta-endorphin or their derivatives, in particular those described in the patent application FR2857874,
• FGF fibroblast growth factor
• FGF2 fibroblast growth factor 2
• Phytokine TM the active substances protecting fibroblast growth factor (FGF), in particular FGF2, in particular those described in the patent application on behalf of the Applicant published under No. GB244036, in particular an extract of Hibiscus Abelmoscus
• the active substances stimulating the activity and / or proliferation of fibroblasts in particular a fermented soybean peptide, in particular that marketed by the Applicant under the name Phytokine TM, advantageously in combination with an extract of Hibiscus Abelmoscus.
• Example 1 Inhibition of the formation of AGEs by plant extracts.
• a solution containing a protein and a reducing sugar is carried out in an extemporaneous manner as follows: a solution of bovine serum albumin (BSA) at a concentration of between 1.5 .mu.M and 1.5M, preferably between 15 .mu.M and 500 .mu.m, is incubated with a reducing sugar solution such as glucose, fructose, ribose, etc., preferably with glucose, at a concentration between 0.1M and 10M and preferably between 0.5M and 5M.
• BSA bovine serum albumin
• the plant extracts are obtained by macerating the plants (preferably root, rhizomes, stems, bark, flowers, fruits, seeds, seeds or leaves) at 1-10% (w / w) in a solvent or a mixture of solvents, advantageously chosen from water, an alcohol, a glycol, a polyol, or a mixture of water / (alcohol, glycol or polyol) (such as ethanol, glycerol, butylene glycol and other glycols, xylitol etc.) of 100/0 at 0/100 (v / v), and preferably in water.
• the extracts obtained are then filtered or distilled in order to recover the soluble fraction which is then filtered at 0.45 ⁇ m preferably to obtain the extract to be tested.
• the protein / reducing sugar solution prepared in 1 is incubated in the presence or absence (negative control) of an extract obtained in 2, at a temperature of between 40 and 60 ° C., preferably at about 50 ° C. for 1 to 5 weeks. preferably for 3 weeks.
• the active substances obtained by extraction according to the protocol described in paragraph 2- extracts are tested at a concentration of between 0.001 and 10%, preferably between 0.01 and 5% and more particularly at
• the positive control used is aminoguanidine at a concentration of between 15 .mu.M and 15OmM, preferably at a concentration of between 1.5 and 15 mM in water.
• the measurement of the AGEs inhibition is carried out by measuring the fluorescence (excitation wavelength between 350 and 375 nm preferably at 355 nm; emission wavelength between 420 and 450 nm, preferably at 430 nm). The inhibition is calculated by deducing the resulting value of the interaction of plant extracts with the molecules of the reaction medium (quenching).
• Plant extracts that inhibit the formation of AGEs under the conditions described are:
• % inhibition Fluorescence obtained with the active principle versus the fluorescence obtained with the positive control (aminoguanidine 1.5 mM), in%.
• the leucocyanidins of the present invention are an aqueous extract (preferably by maceration in water) from grape seeds and contain 95% of proanthocyanins corresponding to the following structure (I):
• Example 1 The preparation of a protein / sugar reducing solution is carried out according to the method described in Example 1 (paragraph 1).
• the molecules are tested at a concentration of between 1.10 "and 1.10 ⁇ lo 7 / o, and preferably between 1.10" and 5 IOL "1%, and in particular IOL" 1%, for example in water or DMSO.
• % inhibition Fluorescence obtained with the active principle versus the fluorescence obtained with the positive control (aminoguanidine 1.5 mM), in%.
• Example 1 The preparation of a protein / sugar reducing solution is carried out according to the method described in Example 1 (paragraph 1), with the use of human collagen instead of BSA.
• the extraction of human collagen is performed from a biopsy
• the collagen obtained in the form of a solution is incubated with a reducing sugar solution such as glucose, fructose, ribose and preferably with ribose.
• a reducing sugar solution such as glucose, fructose, ribose and preferably with ribose.
• the incubation concentrations are the same as described in the previous examples.
• grape seed extract containing 95% of proanthocyanidins of structure (I) has a very important activity compared to the glycosylated molecules of the prior art.
• different anthocyanins have been reported to be active to inhibit AGE formation.
• this finding does not generally take into account the "quenching" or noise of the signal generated by the absorption properties of certain wavelengths of the anthocyanins themselves, and is not related to an inhibitory activity of AGE formation. .
• the anthocyanins of US 2007/0060533, which can be used as inhibitors can be obtained by extraction to obtain large amounts of anthocyanins including berries.
• the inventors have tested the following berries in comparison with the leucosynidines of the invention:
• leucocaynidines of the invention have an activity much greater than that of the anthocyanins which are contained in the active berries according to the prior art.
• Examples 6 to 11 Anti-aging composition applicable topically
• Example 11 Use of the Products of the Invention in a Tablet, Ointment or Injection Formulation
• the active ingredient is obtained, for example, according to the extraction method described in the examples, followed by a drying step.
• the active ingredient is obtained, for example, according to the extraction method described in the examples, followed by a drying step.
• Phase A and Phase B are packaged in separate ampoules and mixed before use.

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• 2007
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