Anti-aging composition

Abstract

The present invention relates to a composition comprising at least one first compound of formula (I) or a polymer of said first compound and at least one second compound of formula (I), formula (II) or formula (III), wherein the second compound of formula (I) is different from the first compound of formula (I). TIFF2025507164000065.tif106170

Description

[Technical field]

[0001] The present invention relates to compositions useful as cosmetics or dietary supplements, particularly anti-aging or antioxidant cosmetics or dietary supplements. [Background technology]

[0002] Finding solutions to maintain a youthful appearance despite aging has been a concern throughout human history, however, it is only recently that active anti-aging cosmetic ingredients have been discovered that have proven effective in reducing the visible signs of aging rather than simply camouflaging them.

[0003] Of these active ingredients, peptides have been particularly successful in the current anti-aging market, with an increasing number of double-blind, placebo-controlled studies establishing their effectiveness on human skin.

[0004] As an example, the palmitoyl pentapeptide palmitoyl-lysine-threonine-threonine-lysine-serine (pal-KTTKS) is a synthetic substance designed as a topical agent to stimulate collagen production and thus provide anti-wrinkle benefits to the skin. Following a 12-week double-blind, placebo-controlled, split-face, left-right randomized clinical trial evaluating two topical products: a moisturizer control product and the same moisturizer product containing 3 ppm of pal-KTTKS, pal-KTTKS demonstrated significant improvement in reducing wrinkles / fine lines compared to the placebo control in both quantitative technical analysis and expert image analysis (Robinson et al. (2005) International Journal of Cosmetic Science 27:155-160).

[0005] However, the cost of these peptides remains a challenge, especially when the peptides have low potency and when higher concentrations are required to achieve efficacy. In addition, there is an increasing demand from consumers for cosmetic or nutritional products that are not only effective but also of non-synthetic origin.

[0006] Therefore, there remains a need for alternative anti-ageing active ingredients suitable for cosmetic or nutritional applications. Summary of the Invention

[0007] The present invention arises from the unexpected discovery by the inventors that the combination of the compounds of formulae I.1a, I.4a, I.6a, I.7a, and I.8a with the compounds of formulae I.12, II.1, II.2, II.3a, and II.5 can inhibit the farnesylation of prelamin A, a surrogate marker of progerin accumulation, and thus has anti-aging and antioxidant effects, and can therefore alleviate other age-related metabolic defects. The inventors also showed that the combination of compounds I.1a, II.1, and II.3a has a synergistic effect on increasing the LC3II / I ratio and increasing the amount of lamin B1 in human skin fibroblasts, thereby demonstrating the synergistic anti-aging effect of this combination.

[0008] Accordingly, the present invention provides a composition comprising a compound of formula (I): TIFF2025507164000002.tif46170{In the formula, R1 and R4 are the same or different and represent -H, -OH, or -OCH3; R2 and R3 are the same or different and are -H, -OH, -OSOH, -O-hexoside, or -OR 31 , -O-CO-R 31 , or -CH2O-CO-R 31 [In the formula, R 31 represents a saturated or unsaturated, linear or branched aliphatic group containing 1 to 30 carbon atoms, which may be substituted with at least one =O, -OH, or -COOH group; or R2 and R3 taken together represent the following formula (Ia) or (Ib): TIFF2025507164000003.tif35170[In the formula, R7 represents -H, -OH, -OCH3, or an aryl group containing 5 to 8 carbon atoms, which may be substituted with at least one -OH group or an oxyalkyl group containing 1 to 5 carbon atoms; R8 represents -H, -OH, or -OCH3. TIFF2025507164000004.tif46170[where, R9, R 10 , R 11 and R 12 are the same or different and represent -H, -OH, or -OCH3. represents a group of one of R5 and R6 represents -H, -OH or -OCH3, and the other represents a linear or branched aliphatic group, optionally substituted with at least one =O, -OH or -COOH group, or a group of formula (Ic): TIFF2025507164000005.tif41170[In the formula, n=0 or 1, k=0 or 1, where when k=1 the ring is aromatic (Ar) and when k=0 the ring is not aromatic; When k=0, m=1, and when k=1, m=0. X represents -O-, -CH- or -CH2-; R 13 is -O-, the group R 23 Or group -OR 23 -(In the formula, R 23 represents a saturated or unsaturated, linear or branched aliphatic group containing 1 to 5 carbon atoms, which may be substituted with at least one =O group; R 14 is -H, -OH, -OCH3 or the following formula (Id): TIFF2025507164000006.tif47170 (in the formula, R 19 , R 20 , R 21 and R 22are the same or different and represent -OH, -CHOH, an alkyl group containing 1 to 5 carbon atoms, or an oxyalkyl group containing 1 to 5 carbon atoms. represents a group of - R 15 , R 16 , R 17 and R 18 are the same or different, -H, -OH, -OSOH, -CHOH, -COOH, -O-glucuronide, -OR 30 , -O-CO-R 30 or -CH2O-CO-R 30 (In the formula, R 30 represents a saturated or unsaturated, linear or branched aliphatic group containing 1 to 30 carbon atoms, which may be substituted with at least one =O, -OH, or -COOH group. or A first compound represented by formula (I), the following formula (II) or the following formula (III): TIFF2025507164000007.tif45170[In the formula, - a represents a single bond or a double bond, - Y represents -O- or -CO-; - W represents -CH2- or -CO-; - R 24 represents an aryl group containing 5 to 8 carbon atoms, optionally substituted with at least one -OH, -OCH, -O-hexoside or -O-glucuronide group; R 25 represents -H, -OH, or an oxycarbonylaryl group containing 6 to 9 carbon atoms, optionally substituted with at least one -OH, -OCH3, -O-hexoside or O-glucuronide group, or R 24 and R 25 are aryl groups containing 6 carbon atoms which may be substituted together with the carbon atom to which they are attached by at least one -OH or -CHOH group; a represents a double bond; - R 26 , R 27 and R 28are the same or different and represent -H, -OH, -OCH3, -O-hexoside or O-glucuronide, - R 29 is -H, -OH or the following formula (IIa): TIFF2025507164000008.tif46170], TIFF2025507164000009.tif57170[In the formula, - j=0 or 1, where when j=1 the ring is aromatic (Ar) and when j=0 the ring is not aromatic, When j=0, m=1, and when j=1, m=0. - When j=1, R 32 represents an alkyl group having 1 to 5 carbon atoms, and when j=0, R 32 is R 33 together with the following formula (IIIa): TIFF2025507164000010.tif37170 (in the formula, n=0 or 1, R 45 represents -H or -CH3, R 46 represents -CHOH or a group (IIIb) or (IIIc) of the formula: represents TIFF2025507164000011.tif70170, R 47 and R 48 are the same or different and represent -H or -OH. represents a group of - R 34 , R 35 , R 38 , and R 43 are the same or different and represent -H or -CH3, - R 36 represents -H, R 42 represents -CH3 or R 36 and R 42 together represent a group of the formula -O-CO-, - R 37 represents -H or -O-hexoside, - b represents a single bond or a double bond, - R 39 represents -CH3, and R 40 represents -H or R 39 and R 40 together with the following formula (IIId): TIFF2025507164000012.tif35170 represents the base, -R 41 is -H, -OH, or the following formula (IIIe) or (IIIf): TIFF2025507164000013.tif129170 represents the base, - R 44 represents -H or -OH] and a polymer with at least one second compound of wherein the second compound of formula (I) is different from the first compound of formula (I), or a cosmetically or nutritionally acceptable salt or ester thereof. Regarding.

[0009] In one embodiment of the present invention, the composition as defined above further comprises at least one third compound of formula (I), (II) or (III), with the proviso that the third compound is different from the first compound and the second compound.

[0010] The present invention also relates to the use of a composition as defined above as a cosmetic agent or as a dietary supplement for humans or animals, in particular as an anti-aging or antioxidant cosmetic agent or dietary supplement.

[0011] The present invention also relates to the cosmetic use of a composition as defined above for reducing at least one sign of skin ageing.

[0012] The present invention also relates to the use of at least one first compound of formula (I) as defined above, or at least one polymer in combination with said first compound and with at least one second compound of formula (I), of formula (II) as defined above, or of formula (III) as defined above, as a cosmetic agent or nutraceutical, in particular an anti-aging or antioxidant cosmetic agent or nutraceutical, wherein the second compound of formula (I) is different from the first compound of formula (I).

[0013] The present invention also relates to the cosmetic use of at least one first compound of formula (I) as defined above, or at least one polymer comprising said first compound in combination with at least one second compound of formula (I), of formula (II) as defined above, or of formula (III) as defined above, wherein the second compound of formula (I) is different from the first compound of formula (I), for reducing at least one sign of skin ageing. [Brief description of the drawings]

[0014] [Figure 1] Photograph of a Western blot of proteins revealed by anti-lamin A / C, anti-prelamin A and anti-HDJ2 ​​antibodies after extraction from human skin fibroblasts cultured in the presence of the following compounds: 1: DMSO (negative control) 2: alendronate / pravastatin (positive control) 3: alendronate 4: alendronate / compound I.1a 5: alendronate / compound I.7a 6: alendronate / compound I.6a 7: alendronate / compound I.4a 8: alendronate / compound I.8a 9: DMSO 10: alendronate / pravastatin 11: pravastatin 12: pravastatin / compound II.1 13: pravastatin / compound II.3a 14: pravastatin / compound II.2 15: pravastatin / compound I.12 16: pravastatin / compound II.5 [Diagram 2]LC3II / I protein ratio (vertical axis, percent change from negative control) in human skin fibroblasts exposed to the following substances: 1: Compound I.1a alone 2: Compound II.1 alone 3: Compound II.3a alone 4: Combination of Compound I.1a + Compound II.1 + Compound II.3a Lane 5 represents the theoretically expected effect observed in the case of additive effect of the compounds (addition of the effects of Compound I.1a alone, Compound II.1 alone, and Compound II.3a alone). [Diagram 3] Amount of lamin B1 (vertical axis, percent change from negative control) in human skin fibroblasts exposed to the following substances: 1: Compound I.1a alone 2: Compound II.1 alone 3: Compound II.3a alone 4: Combination of Compound I.1a + Compound II.1 + Compound II.3a Lane 5 represents the theoretically expected effect observed in the case of additive effect of the compounds (addition of the effects of Compound I.1a alone, Compound II.1 alone and Compound II.3a alone). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] As intended herein, the term "comprise" is synonymous with "contain" or "include." When a subject matter is said to comprise one or more features, it is meant that the subject matter may include features other than the features mentioned. Conversely, the phrase "consisting of" is synonymous with "consisting of." When a subject matter is said to comprise one or more features, it is meant that the subject matter does not include features other than the features mentioned.

[0016] As will be appreciated by those skilled in the art, all stereochemical configurations of the compounds according to the invention are intended to be covered by the formulae shown herein. In particular, as intended herein, when no bond configuration is specified, the bond may represent either an up bond, a down bond, or a mixture of the two, particularly a 1 / 1 mixture of the two.

[0017] In the formulae described herein, the arrows represent the bond through which the group is attached to the compound that contains it.

[0018] As intended herein, an -O-hexoside group refers to a hexose group linked by an -O- bond. By way of example, an -O-hexoside group according to the invention can be represented by the formula: TIFF2025507164000014.tif38170Preferably, the -O-hexoside group is an -O-glucoside group. Preferably, the -O-glucoside group is represented by one of the following formulae: TIFF2025507164000015.tif38170

[0019] As intended herein, an -O-glucuronide group is represented by one of the following formulas: TIFF2025507164000016.tif37170

[0020] As intended herein, an oxyalkyl group can be represented as an --O-alkyl group.

[0021] Preferred alkyl groups according to the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, and t-butyl groups.

[0022] As intended herein, an oxycarbonylaryl group may be represented as an -O-CO-aryl group, where CO represents C=O.

[0023] As intended herein, a "cosmetically or nutritionally acceptable salt or ester" is a salt or ester of a compound of formula (I), (II), or (III) as defined above, which is suitable for cosmetic or nutritional use.

[0024] Preferred cosmetically or nutritionally acceptable salts according to the present invention are selected from the group consisting of hydrochloride, chloride, hydrobromide, bromide, iodide, phosphate / diphosphate, sulfate, tartrate, citrate, maleate, acetate, mesylate, pamoate (embonate), sodium, potassium, calcium, meglumine, zinc, lithium, and magnesium.

[0025] Preferred cosmetically or nutritionally acceptable esters according to the invention are formed between at least one hydroxyl (-OH) group of a compound of formula (I), (II) or (III) according to the invention and at least one carboxylic acid of formula HOOC-R, where R represents a saturated or unsaturated, linear or branched aliphatic group containing from 1 to 30 carbon atoms, optionally substituted with at least one =O, -OH or -COOH group.

[0026] First Compound Preferably, the first compound is selected from the group consisting of compounds of the formula: TIFF2025507164000017.tif46170, wherein A1, A2 and A3 may be the same or different and represent -OH, -OSOH, -O-glucuronide, or -O-CO-A4, where A4 represents a saturated or unsaturated, straight or branched chain aliphatic group containing 1 to 30 carbon atoms, optionally substituted with at least one =O, -OH, or -COOH group; TIFF2025507164000018.tif255170TIFF2025507164000019.tif159170

[0027] Preferably, the compounds of formula (I.1) above have one of the following combinations of substituents: TIFF2025507164000020.tif46170

[0028] Preferably, the compounds of formula (I.2) above have one of the following substituent combinations: TIFF2025507164000021.tif54170

[0029] Preferably, the compounds of formula (I.3) above have one of the following substituent combinations: TIFF2025507164000022.tif15170

[0030] The polymer of the first compound according to the invention is preferably a polymer of a compound of formula (I.1), (I.2) or (I.3), in particular as described in WO 99 / 03816, which is hereby incorporated by reference.

[0031] Preferably, the compound of formula (I.4) has the following formula (I.4a) (CAS number 327-97-9): TIFF2025507164000023.tif47170

[0032] Preferably, the compound of formula (I.6) has the following formula (I.6a) (CAS number 4773-96-0): TIFF2025507164000024.tif34170

[0033] Preferably, the compound of formula (I.7) has the following formula (I.7a) (CAS number 13241-33-3): TIFF2025507164000025.tif58170

[0034] Preferably, the compound of formula (I.8) has the following formula (I.8a) (CAS number 10236-47-2): TIFF2025507164000026.tif55170

[0035] Second Compound Preferably, the second compound is selected from the group consisting of compounds of the formula: TIFF2025507164000027.tif229170[In the formula, B1 represents -OH, -OCH3 or -O-glucuronide, B2 represents -OH or -OCH3, B3 represents -H or -OH; B4 is -OH, -O-glucuronide or a group of the formula: TIFF2025507164000028.tif37170 (wherein B6 represents -OH, -OCH3, or -O-glucuronide) represents B5 is -OH, -O-hexoside or -O-glucuronide; [TIFF2025507164000029.tif172170TIFF2025507164000030.tif216170TIFF2025507164000031.tif72170]

[0036] Preferably, the compound of formula (I.12) above has the following formula (I.12a) (CAS number 10338-51-9): TIFF2025507164000032.tif36170

[0037] Preferably, the compounds of formula (II.3) above have one of the following substituent combinations: TIFF2025507164000033.tif20170

[0038] Preferably, the compound of formula (II.3) above is represented by the following formula (II.3a): TIFF2025507164000034.tif57170

[0039] Preferably, the compounds of formula (II.4) above have one of the following substituent combinations: TIFF2025507164000035.tif226170TIFF2025507164000036.tif86170

[0040] Preferably, the compound of formula (II.6) above has the following formula (II.6a) (CAS number 28608-75-5): TIFF2025507164000037.tif63170

[0041] Preferably, the compound of formula (III.2) has the following formula (III.2a) (CAS number 41753-43-9): TIFF2025507164000038.tif88170

[0042] Preferably, the compound of formula (III.3) above has the following formula (III.3a) (CAS number 22427-39-0): TIFF2025507164000039.tif95170

[0043] Preferably, the compound of formula (III.4) is represented by the following formula (III.4a) (CAS number 34540-22-2): TIFF2025507164000040.tif91170

[0044] composition Preferably, the composition as defined above comprises at least two different compounds selected from the following pairs of compounds: TIFF2025507164000041.tif70170

[0045] Preferably, the compositions defined above, in particular compositions comprising at least two different compounds selected from the pairs defined in Table A, further comprise at least a third compound selected from the group consisting of compounds of the respective formulae I.1, I.2, I.3, I.4, I.5, I.6, I.7., I.8, I.9, I.10, I.11, I.12, II.1, II.2, II.3, II.4, II.5, II.6, III.1, III.2, III.3, and III.4, with the proviso that the third compound is different from the first compound and the second compound.

[0046] Preferably, the composition as defined above comprises at least two different compounds, or at least three different compounds, each selected from: a compound of formula (I.1), (I.2) or (I.3), - a compound of formula (II.1), and - a compound of formula (II.3) or (II.4).

[0047] Most preferably, the composition as defined above comprises: a compound of formula (I.1), (I.2) or (I.3), - a compound of formula (II.1), and - a compound of formula (II.3) or (II.4).

[0048] Even more preferably, the composition as defined above comprises: - compounds of formula (I.1), in particular of formula (I.1a); - a compound of formula (II.1), and - compounds of formula (II.3), in particular of formula (II.3a).

[0049] Preferably, the composition as defined above comprises: - compounds of formula (I.4), in particular of formula (I.4a); compounds of formula (I.6), in particular of formula (I.6a), and - a compound of formula (II.1) or of formula (II.5).

[0050] Preferably, the composition as defined above comprises: - compounds of formula (I.4), in particular of formula (I.4a); - a compound of formula (II.1), and - a compound of formula (II.5).

[0051] Preferably, the composition as defined above comprises from 0.001 g to 5 g, more preferably from 0.01 g to 2.5 g, most preferably from 0.1 g to 1 g of total weight of the compound of formula (I), (II) and / or (III) as defined above.

[0052] Preferably, the composition as defined above comprises from 0.01% (w / w) to 100% (w / w) of the total weight of the compounds of formulae (I), (II) and / or (III) as defined above, more preferably from 0.05% (w / w) to 20% (w / w), most preferably from 0.1% (w / w) to 5% (w / w) of the total weight of the composition.

[0053] Preferably, the composition as defined above comprises from 70% (w / w) to 90% (w / w) of the compound of formula (II.3) or (II.4) relative to the total weight of the compounds of formulae (I), (II) and / or (III) as defined above in the composition.

[0054] Preferably, the composition as defined above comprises from 5% (w / w) to 15% (w / w) of compounds of formula (I.1), (I.2) or (I.3) relative to the total weight of compounds of formula (I), (II) and / or (III) as defined above in the composition.

[0055] Preferably, the composition as defined above comprises from 5% (w / w) to 15% (w / w) of the compound of formula (II.1) relative to the total weight of the compounds of formulae (I), (II) and / or (III) as defined above in the composition.

[0056] Most preferably, the composition as defined above comprises, relative to the total weight of the compound of formula (I.1), (I.2) or (I.3), the compound of formula (II.1) and the compound of formula (II.3) or (II.4), - from 5% (w / w) to 15% (w / w), in particular from 8% (w / w) to 10% (w / w) of a compound of formula (I.1), (I.2) or (I.3), - from 5% (w / w) to 15% (w / w), in particular from 8% (w / w) to 10% (w / w), of a compound of formula (II.1), and - 70% (w / w) to 90% (w / w), in particular 80% (w / w) to 84% (w / w) of a compound of formula (II.3) or (II.4) Includes.

[0057] Even more preferably, the composition as defined above comprises, relative to the total weight of the compound of formula (I.1), the compound of formula (II.1) and the compound of formula (II.3), - 5% (w / w) to 15% (w / w), in particular 8% (w / w) to 10% (w / w) of a compound of formula (I.1), in particular of formula (I.1a) - from 5% (w / w) to 15% (w / w), in particular from 8% (w / w) to 10% (w / w), of a compound of formula (II.1), and - 70% (w / w) to 90% (w / w), in particular 80% (w / w) to 84% (w / w) of a compound of formula (II.3), in particular of formula (II.3a) Includes.

[0058] Preferably, the compounds of formulae (I), (II) and (III) as defined above are contained in at least one plant extract.

[0059] As intended herein, the plant extract may be from the whole plant or from plant parts such as leaves, flowers, fruits, skins, stems, bark, or roots, e.g. grape juice. As intended herein, the plant extract may be obtained by applying at least one of the following to the plant or plant parts: crushing, pressing, percolation in an aqueous or organic solvent, e.g. water, and / or passing through an aqueous or organic solvent, e.g. water. If a solvent is used, the solvent may be cold, e.g. 10°C to 30°C, or hot, e.g. 50°C to 200°C, liquid or gas. The plant extract may be a crude extract or a purified extract. The plant extract may be concentrated. In particular, the plant extract may be purified and / or concentrated to increase the content in at least one compound of formula (I), (II), or (III) as defined above. As intended herein, the compound of formula (I), (II), or (III) as defined above may be isolated and / or purified from the plant extract.

[0060] Preferably, the composition as defined above is a cosmetic composition.

[0061] Preferably, the composition as defined above is a nutritional composition or a food supplement, in particular intended for human or animal consumption, i.e. a nutritional composition or a food supplement for humans or animals. P.24,l.2-4

[0062] Preferably, the composition as defined above further comprises at least one cosmetically or nutritionally acceptable carrier or additive.

[0063] As contemplated herein, a cosmetically acceptable carrier or additive is one that is compatible with the skin, preferably of a pleasant color, fragrance, and consistency, and does not cause discomfort such as tingling, redness, or other discomfort that may discourage consumers from using it.

[0064] Cosmetically acceptable carriers or additives according to the invention include, inter alia, diluents, dispersants, gelling agents, solid emollients, gums, resins, solvents, fillers such as modified and polymerized starches, or metal stearates, preservatives, essential oils, pearlescent agents, colorants, odor absorbers, pH adjusters or neutralizers, thickeners, absorption promoters, and in particular ethanol and / or phospholipids, flavorings or fragrances, mineral pigments such as iron oxides, oils such as oils or fats of vegetable origin, fats of animal origin, synthetic oils, silicone oils (cyclomethicone), fluorine-containing oils, fatty alcohol esters (cetyl alcohol), waxes, modified clays, bentones, fatty acid metal salts, hydrophobized silica, polyethylene, mica, and / or other substances used in cosmetics.

[0065] The cosmetic composition according to the invention may be a care or make-up product, for example in the form of a serum, lotion, cream, milk, water or oil gel, hydrogel, mask, stick, patch, oil, ointment, wax, foam, toner, care solution, balm, foundation, spray, eye shadow, lipstick, paste, ointment, shampoo or conditioner.

[0066] When the cosmetic composition according to the invention is intended to be administered topically to the skin, it may be in the form of any preparation conventionally used for topical application, in particular in the form of an aqueous solution, an aqueous alcoholic solution, an oil-in-water emulsion (O / W) or a water-in-oil emulsion (W / O), or a multiple emulsion (triple: W / O / W or O / W / O), or a micro- or nano-emulsion.

[0067] When the composition is in aqueous form, in particular a dispersion, emulsion or aqueous solution, it may contain an aqueous phase which may comprise water, floral water, fruit water and / or mineral water.Preferably, the fruit water is selected from the group consisting of lemon fruit water, orange fruit water, grapefruit fruit water, pomelo fruit water, apricot fruit water, tomato fruit water, mango fruit water, cucumber fruit water, pineapple fruit water, raspberry fruit water, tangerine fruit water, apple fruit water and blueberry fruit water.

[0068] The cosmetic composition of the present invention may further comprise other active molecules such as vitamins, sunscreens and sunblocks, anti-aging actives, anti-wrinkle agents (especially peptides), antioxidants, whitening agents, self-tanning ingredients, tanning accelerators, lifting ingredients, slimming agents, firming ingredients, moisturizing ingredients, peeling ingredients, sebum regulating agents, mattifying agents, etc. Preferably, the cosmetic composition may comprise anti-aging actives, anti-wrinkle agents and / or antioxidants, lifting ingredients, firming ingredients and / or moisturizing ingredients. Generally, the skilled person can select and adapt the amount of additional active molecules such that the properties of the composition of the present invention are not diminished by their addition.

[0069] As intended herein, a nutritionally acceptable carrier or additive refers to a food ingredient suitable for human or animal consumption.

[0070] Preferably, the nutritionally acceptable carrier or additive according to the invention is selected from the group consisting of antifoaming agents, emulsifiers, hardening agents, gelling agents, humectants, mineral salts, stabilizers, thickening agents, and texturizing agents. Preferably, the antifoaming agents are selected from the group consisting of polyethylene glycol and triethyl citrate. Preferably, the emulsifiers are selected from lecithin, sorbitan monostearate, and ammonium salts of phosphatidic acid. The hardening agents are preferably selected from the group consisting of calcium chloride, calcium gluconate, and calcium sulfate. The gelling agents are preferably selected from the group consisting of agar, calcium alginate, and carrageenan. The humectants are preferably selected from the group consisting of glycerin, glycerol, lactitol, and polyethylene oxide; the mineral salt is copper sulfate. Preferably, the stabilizers are selected from the group consisting of xanthan gum, guar gum, and bleached starch. The thickening agents are preferably selected from the group consisting of tannin, sodium alginate, and pectin. Preferably, the texturizing agent is selected from the group consisting of phosphates, sodium tripolyphosphate, sodium hexametaphosphate, and sodium pyrophosphate.

[0071] The nutritional composition according to the invention may further comprise at least one supplementary ingredient. Preferably, the supplementary ingredient is selected from the group consisting of vitamins, minerals, fiber, vegetable oils, fatty acids, amino acids, flavorings, colorings, antioxidants, sweeteners, flavor enhancers, acidifiers, preservatives, sequestrants, flavor enhancers, sugar, flour, prebiotics, salt, water, and antimicrobial agents. Preferably, the vitamins are selected from the group consisting of B vitamins including niacin, vitamin C, and vitamin E. The flavorings are preferably selected from the group consisting of oleoresins and aquaresins. The colorings are preferably selected from the group consisting of curcumin, brilliant blue, tartrazine, and ferrous gluconate. Preferably, the antioxidants are selected from the group consisting of nitrates, nitrites, ascorbyl palmitate, and calcium ascorbate. Preferably, the sweetening agents are selected from the group consisting of sorbitol, alitame, aspartame, saccharin, calcium saccharin, and corn syrup. The flavour enhancer is preferably selected from the group consisting of acetic acid, citric acid and fumaric acid. The acidifying agent is preferably lactic acid. The preservative is preferably selected from the group consisting of sodium nitrate, benzoic acid, sodium benzoate, tocopherol, ascorbic acid, niacin, riboflavin and thiamine. The sequestrant is preferably potassium gluconate. The flavour enhancer is preferably selected from the group consisting of spices or oleoresins extracted therefrom, herbs, vegetables, essential oils, sodium nitrate, water, salt, sugar and flavourings. The antimicrobial agent is preferably selected from the group consisting of lactic acid, citric acid, acetic acid, sodium diacetate, acidified sodium chloride or calcium sulfate, activated lactoferrin, sodium or potassium lactate or a bacteriocin such as nisin.

[0072] use As intended herein, "in combination" or "in combination" means that a first compound as defined above is administered simultaneously, together, i.e., to the same administration site, or separately or at different times, with a second compound, provided that there is at least a partial overlap between the period during which the first compound as defined above exerts its effect on the individual and the period during which the second compound exerts its effect on the individual.

[0073] Preferably, at least two different compounds selected from the following pairs of compounds are used as defined above: TIFF2025507164000042.tif70170

[0074] Preferably, in the above defined use, in particular when at least two different compounds selected from the pairs defined in Table B are used, at least a third compound is used which is selected from the group consisting of the compounds of the respective formulae I.1, I.2, I.3, I.4, I.5, I.6, I.7., I.8, I.9, I.10, I.11, I.12, II.1, II.2, II.3, II.4, II.5, II.6, III.1, III.2, III.3 and III.4, with the proviso that the third compound is different from the first compound and the second compound.

[0075] Preferably, at least one compound of formula (I), (II) or (III) is used as defined above in combination with a first compound and a second compound, with the proviso that the third compound is different from the first compound and the second compound.

[0076] In a preferred embodiment, each a compound of formula (I.1), (I.2) or (I.3), - a compound of formula (II.1), and - a compound of formula (II.3) or (II.4) At least two different compounds, or at least three different compounds selected from, are used as defined above.

[0077] Most preferably, a compound of formula (I.1), (I.2) or (I.3), - a compound of formula (II.1), and - a compound of formula (II.3) or (II.4), is used as defined above.

[0078] Even more preferably, - compounds of formula (I.1), in particular of formula (I.1a); - a compound of formula (II.1), and - compounds of formula (II.3), in particular of formula (II.3a) is used as defined above.

[0079] Preferably, - compounds of formula (I.4), in particular of formula (I.4a); compounds of formula (I.6), in particular of formula (I.6a), and a compound of formula (II.1) or of formula (II.5) is used as defined above.

[0080] Preferably, - compounds of formula (I.4), in particular of formula (I.4a); - a compound of formula (II.1), and - a compound of formula (II.5) is used as defined above.

[0081] As intended herein, an anti-aging agent relates to an agent that prevents, alleviates, attenuates, relieves, or treats the physical effects of aging.

[0082] As intended herein, an antioxidant refers to an agent that prevents, alleviates, attenuates, reduces, or treats the physical effects of oxidative stress.

[0083] The compositions and compound combinations according to the present invention are useful for reducing at least one sign of skin aging.

[0084] As intended herein, "signs of skin aging" refer to skin defects resulting from the deterioration of skin components due to chronic factors such as mechanical stress, oxidative stress, and / or photo-stress. In particular, skin aging can be the result of chrono-aging and / or photo-aging. "Chrono-aging" refers to skin defects resulting from aging. "Photo-aging" refers to skin defects resulting from exposure of skin to light, particularly UV rays, more particularly UV-A or UV-B rays.

[0085] The at least one sign of skin aging may in particular be at least one wrinkle or a decrease in skin elasticity. In particular, the at least one sign of skin aging is at least one sign of facial skin aging.

[0086] The at least one sign of skin ageing which is reduced by the present invention is preferably selected from the group consisting of at least one wrinkle, in particular at least one expression and / or mechanical wrinkle, more particularly forehead wrinkles, glabellar wrinkles, crow's feet, bunny lines, under-nose wrinkles, nasolabial folds, tear troughs, marionette lines, geniolabial folds and neck wrinkles.

[0087] The invention is further illustrated by the following non-limiting figures and examples. EXAMPLES

[0088] Example 1 Topical administration of an alendronate-pravastatin composition to the face of human volunteers demonstrated anti-skin aging effects by reducing crow's feet and restoring volume to the cheeks in a double-blind, randomized, placebo-controlled study, which is believed to be mediated, at least in part, by inhibiting the synthesis of farnesyl pyrophosphate, the precursor of the farnesyl group that anchors the pro-aging factor progerin (Scaffidi & Misteli (2006) Science 312:1059-1063) to the nuclear membrane in cells of aged subjects.

[0089] Inhibition of progerin farnesylation has been shown to reduce the toxicity and pro-aging effects of progerin (Glynn & Glover (2005) Human Molecular Genetics 14: 2959-2969; Varela et al. (2008) Nature Medicine 14: 767-772). Farnesylated progerin sequesters and mislocalizes NRF2 in the nuclear lamina, reducing NRF2 transcriptional activity and, consequently, increasing chronic oxidative stress (Kubben et al. (2016). Cell 165, 1361-1374).

[0090] Next, we evaluated the ability of various test compounds to replace either alendronate or pravastatin in inhibiting farnesylation of prelamin A and HDJ2, which exhibit anti-aging and antioxidant effects.

[0091] Materials and Methods Test Compounds The following compounds were tested: TIFF2025507164000043.tif255170TIFF2025507164000044.tif223170

[0092] Test compounds were obtained from Euromedex, Zouffelweiersheim, France for I.1a and from Sigma, Saint-Quentin-Fallavier, France for I.4a, I.6a, I.7a, I.8a, I.12a, II.1, II.2, II.3a, and II.5. Test compounds were diluted in DMSO.

[0093] Alendronate and pravastatin were obtained from AbMole / Euromedex, Zouffelweiersheim, France, and Alsachim, Illkirch-Graffenstaden, France, respectively. Alendronate and pravastatin were diluted in H2O.

[0094] cell culture Control skin-derived human fibroblasts (AG13334) were obtained from the Coriell Institute. Cells were maintained in culture according to the supplier's information at 37° C. in a humidified atmosphere containing 5% CO2.

[0095] Fibroblasts were cultured for 72 hours without changing the medium.

[0096] To assess cell viability, cells were treated with test compounds at concentrations ranging from 1 pM to 1000 μM for 72 hours. Each test compound was combined with alendronate (10 μM) or pravastatin (10 μM).

[0097] To assess efficacy, cells were treated with alendronate or pravastatin (10 μM) in combination with the highest non-toxic dose or half the concentration of the test compounds (compound I.1a, 50 μM; compound I.7a, 500 μM; compound I.6a, 500 μM; compound I.4a, 500 μM; compound I.8a, 1000 μM; compound II.1, 60 μM; compound II.3a, 500 μM; compound II.2, 30 μM; compound I.12a, 500 μM; compound II.5, 250 μM).

[0098] The following combinations were tested: 1: DMSO (negative control) 2: Alendronate / Pravastatin (positive control) 3: Alendronate 4: Alendronate / Compound I.1a 5: Alendronate / Compound I.7a 6: Alendronate / Compound I.6a 7: Alendronate / Compound I.4a 8: Alendronate / Compound I.8a 9:DMSO 10: Alendronate / Pravastatin 11:Pravastatin 12: Pravastatin / Compound II.1 13. Pravastatin / Compound II.3a 14.Pravastatin / Compound II.2 15.Pravastatin / Compound I.12 16.Pravastatin / Compound II.5

[0099] Ritonavir (4 μM) and lopinavir (20 μM) were added in all test conditions to improve the lower limit of detection of prenylated prelamin A in Western blots.

[0100] Assessment of cell viability and cytotoxicity The assay was performed in 96-well microplates. After 72 h of treatment, cells were washed once with 100 μL of DPBS (calcium-free, magnesium-free). Then, 100 μl of PrestoBlue solution (Life Technologies) diluted to 10% in DPBS was added to each well. Plates were incubated for 30 min at 37°C. Fluorescence intensity was measured in a multiwell plate reader (Glomax microplate reader, Promega, Charbonnières-les-Bains, France) using a green filter (excitation 525 nm / emission 580-640 nm). Fluorescence intensity values ​​were analyzed with Prism software (GraphPad, San Diego, CA).

[0101] Protein extraction Total fibroblast protein was extracted after 72 h treatment with 100 μL NP40 (Invitrogen) and 1X protease and phosphatase inhibitor cocktail (Life Technologies). Lysates were incubated on ice for 30 min and vortexed at 10 min intervals. Finally, they were sonicated 4 times (20 s each) and centrifuged at 13000 rpm for 10 min at 4°C.

[0102] Protein concentrations were determined by the BCA™ Protein Assay (Life Technologies).

[0103] antibody The following antibodies were used in this study: rabbit monoclonal anti-lamin A / C (ab108922, 1 / 1000, Abcam, Amsterdam, The Netherlands), mouse monoclonal anti-prelamin A (MABT858, Millipore, Molsheim, France), mouse monoclonal anti-HDJ2 ​​(MA5-12748, Thermoscientific, France). Secondary antibodies conjugated with IR-Dye 800CW or 680 were used according to the manufacturer's instructions (926-32213 and 926-68072, 1 / 5000, Li-COR Biosciences).

[0104] Western blotting Protein lysates were separated on NuPAGE™ Novex™ 8% Bis-Tris Midi Protein Gels (Life Technologies) and transferred to Immobilon-FL PVDF membranes (Millipore, Molsaimes, France). Membranes were blocked for 1 h with 1:1 diluted blocking buffer for near-fluorescent Western blotting (Rockland, Le Perret, France). Blocked membranes were incubated overnight at 4°C with primary antibody anti-prelamin A, then washed and incubated with conjugated secondary antibodies for 1 h at room temperature. This step was then repeated with primary and conjugated secondary antibodies for HDJ2 and LMNA / C.

[0105] Bound antibodies were detected and analyzed with an Odyssey Imaging System (Li-COR Biosciences, Bad Homburg, Germany) according to the manufacturer's instructions. Revert Protein Stain (Li-COR Biosciences) was used as a total protein loading control.

[0106] result The result is Figure 1 As shown in.

[0107] Prelamin A and non-farnesylated HDJ2 are absent in the negative control(s) (DMSO) in lanes 1 and 9, and essentially absent in lane 3 for alendronate and 11 for pravastatin alone.

[0108] In contrast, the alendronate / pravastatin combination (positive control, lanes 2 and 10) shows a strong band for prelamin A. Indeed, prelamin A accumulates because inhibition of farnesylation prevents its maturation to lamin A. A clear band is also seen for non-farnesylated HDJ2.

[0109] Combinations of test compounds I.1a, I.4a, I.6a, I.7a, and I.8a (lanes 4, 7, 6, 5, and 8, respectively) with alendronate, and compounds I.12, II.1, II.2, II.3a, and II.5 (lanes 15, 12, 14, 13, and 16, respectively) with pravastatin also showed clear bands for prelamin A and non-farnesylated HDJ2, suggesting inhibition of farnesylation and therefore an anti-aging effect.

[0110] This also suggests that the combination of compounds I.1a, I.4a, I.6a, I.7a, and I.8a with compounds I.12, II.1, II.2, II.3a, and II.5 may provide inhibition of farnesylation as well as anti-aging and antioxidant effects.

[0111] Example 2 Autophagy is an evolutionarily conserved, lysosome-dependent catabolic process that degrades cytoplasmic components, including damaged organelles, protein aggregates, and lipid droplets, and recycles the components. Although autophagy plays an important role in maintaining cellular homeostasis in response to intracellular stress, the efficiency of autophagy decreases with age (Kitada et al. (2021) Nat Rev Endocrinol. 17:647-661). Conversely, activation of autophagy extends lifespan (Hansen et al. (2018) Nat Rev Mol Cell Biol. 9:579-593).

[0112] Activation of autophagy can be monitored through the conversion of microtubule-associated protein light chain 3I (LC3I) to LC3II, specifically by measuring the LC3II / LC3-I ratio (also called the LC3II / I ratio) by immunoblot analysis, whereby an increase in the ratio suggests increased autophagy (Klionsky et al. (2021) Autophagy 17:1-382).

[0113] Materials and Methods cell culture Control skin-derived human fibroblasts (AG13334) were obtained from the Coriell Institute. Cells were maintained in culture according to the supplier's information at 37° C. in a humidified atmosphere containing 5% CO2.

[0114] Fibroblasts were cultured for 72 hours without changing the medium.

[0115] To assess efficacy, cells were treated for 72 h with the test molecules alone or in combination (compound I.1a, 50 μM; compound II.1, 60 μM; compound II.3a, 500 μM). For detection of prenylated prelamin A, ritonavir (4 μM) and lopinavir (20 μM) were added to all test conditions and negative controls.

[0116] The following conditions were tested: 1: Compound I.1a alone 2: Compound II.1 alone 3: Compound II.3a alone 4: Combination of Compound I.1a + Compound II.1 + Compound II.3a 5: Theoretical effect of added compounds (Compound I.1a + Compound II.1 + Compound II.3)

[0117] Protein extraction Total fibroblast protein was extracted after 72 h treatment with 100 μL NP40 (Invitrogen) and 1X protease and phosphatase inhibitor cocktail (Life Technologies). Lysates were incubated on ice for 30 min and vortexed at 10 min intervals. Finally, they were sonicated 4 times (20 s each) and centrifuged at 10000 g for 10 min at 4°C.

[0118] Protein concentrations were determined with the Pierce™ BCA Protein Assay (Life Technologies).

[0119] antibody The following antibodies were used in this study: mouse monoclonal anti-LC3β (sc271625, 1 / 200, Santa Cruz, Heidelberg, Germany). Secondary antibodies conjugated with IR-Dye 800CW were used according to the manufacturer's instructions (926-32212, 1 / 5000, Li-COR Biosciences).

[0120] Western blotting Protein lysates were separated on NuPAGE™ Novex™ 8% Bis-Tris Midi Protein Gels (Life Technologies) and transferred to Immobilon-FL PVDF membranes (Millipore, Molsaimes, France). Membranes were blocked for 1 h with 1:1 diluted blocking buffer for near-fluorescent Western blotting (Rockland, Le Perret, France). Blocked membranes were incubated overnight at 4°C with primary antibody anti-LC3β, then washed and incubated with conjugated secondary antibody for 1 h at room temperature.

[0121] Bound antibodies were detected and analyzed with an Odyssey imaging system (Li-COR Biosciences, Bad Homburg, Germany) according to the manufacturer's instructions. LC3II and LC3I were detected.

[0122] Results were expressed as the percentage change in LC3II / I ratio from the negative control.

[0123] result The result is Figure 2 As shown in.

[0124] It can be seen that the combination of tested compounds I.1a, II.1, and II.3a increased the LC3 II / I ratio compared to the negative control (DMSO) (lane 5), which was greater than would be expected from the addition of the respective increases in the LC3 II / I ratio obtained with each compound alone (lane 6).

[0125] Thus, the effect of the tested combination of compounds I.1a, II.1, and II.3a on the activation of autophagy in human dermal fibroblasts is superadditive, i.e. synergistic.

[0126] Therefore, the tested combination is expected to exert an anti-ageing effect on the skin.

[0127] Example 3 Depletion of lamin B1 from the nuclear envelope is a key event during senescence. Lamin B1 is essential for maintaining the structural integrity of the nucleus. However, this integrity is lost in senescent cells, allowing cytoplasmic chromatin fragments to be released outside the nucleus, which is thought to promote SASP via the cGAS / STING pathway (Gonzalez-Gualda et al. (2021) The FEBS Journal 288:56-80). Loss of lamin B1 is a hallmark of senescent cells in senescent cells (Wang et al. (2017) Sci Rep. 7:15678).

[0128] Loss of lamin B1 can be detected by immunoassays and can be detected by imaging or immunoblotting.

[0129] Materials and Methods cell culture Control skin-derived human fibroblasts (AG13334) were obtained from the Coriell Institute. Cells were maintained in culture according to the supplier's information at 37° C. in a humidified atmosphere containing 5% CO2.

[0130] Fibroblasts were cultured for 72 hours without changing the medium.

[0131] To assess efficacy, cells were treated for 72 h with the test molecules alone or in combination (compound I.1a, 50 μM; compound II.1, 60 μM; compound II.3a, 500 μM). For detection of prenylated prelamin A, ritonavir (4 μM) and lopinavir (20 μM) were added to all test conditions and negative controls.

[0132] The following conditions were tested: 1: Compound I.1a alone 2: Compound II.1 alone 3: Compound II.3a alone 4: Combination of Compound I.1a + Compound II.1 + Compound II.3a 5: Theoretical effect of added compounds (Compound I.1a + Compound II.1 + Compound II.3a)

[0133] Protein extraction Total fibroblast protein was extracted after 72 h treatment with 100 μL NP40 (Invitrogen) and 1X protease and phosphatase inhibitor cocktail (Life Technologies). Lysates were incubated on ice for 30 min and vortexed at 10 min intervals. Finally, they were sonicated 4 times (20 s each) and centrifuged at 10000 g for 10 min at 4°C.

[0134] Protein concentrations were determined with the Pierce™ BCA Protein Assay (Life Technologies).

[0135] antibody The following antibodies were used in this study: rabbit polyclonal anti-lamin B1 (ab16048, 1 / 1000, Abcam, Amsterdam, The Netherlands). Secondary antibodies conjugated with IR-Dye 680RD were used according to the manufacturer's instructions (926-68073, 1 / 5000, Li-COR Biosciences).

[0136] Western blotting Protein lysates were separated on NuPAGE™ Novex™ 8% Bis-Tris Midi Protein Gels (Life Technologies) and transferred to Immobilon-FL PVDF membranes (Millipore, Molsaimes, France). Membranes were blocked for 1 h with 1:1 diluted blocking buffer for near-fluorescent Western blotting (Rockland, Le Perret, France). Blocked membranes were incubated overnight at 4°C with primary antibody anti-lamin B1, then washed and incubated with conjugated secondary antibody for 1 h at room temperature.

[0137] Bound antibodies were detected and analyzed with an Odyssey Imaging System (Li-COR Biosciences, Bad Homburg, Germany) according to the manufacturer's instructions. All bands detected with anti-Lamin B1 were considered specific (see KO-validated antibodies). Revert Protein Stain (Li-COR Biosciences) was used as a total protein loading control.

[0138] Results were expressed as percent change from the lamin B1 negative control.

[0139] result The result is Figure 3 As shown in.

[0140] It can be seen that the tested combination of compounds I.1a, II.1, and II.3a increased the amount of lamin B1 compared to the negative control (DMSO) (lane 5) and this was greater than would be expected from the addition of the respective increases in lamin B1 obtained with each compound alone (lane 6).

[0141] Thus, the effect of the tested combination of compounds I.1a, II.1 and II.3a on reversing the signs of aging in human skin fibroblasts is superadditive, ie synergistic.

[0142] Therefore, the tested combination is expected to exert an anti-aging effect on the skin.

Claims

1. A composition, the following formula (I): {During the ceremony, - R １ and R ４ These are the same or different -H, -OH, or -OCH ３ This represents, -R ２ and R ３ are the same or different and are -H, -OH, -OSO ３ H, -O-hexoside, or -O-R ３１ , -O-CO-R ３１ , or -CH ２ O-CO-R ３１ [wherein, R ３１ represents a saturated or unsaturated linear or branched aliphatic group containing 1 to 30 carbon atoms, which may be substituted with at least one =O, -OH, or -COOH group], or R ２ and R ３ together represent the following formula (Ia) or (Ib): [In the formula, R ７ is -H, -OH, -OCH ３ , or represents an aryl group containing 5 to 8 carbon atoms, which may be substituted with at least one -OH group or an oxyalkyl group containing 1 to 5 carbon atoms, R ８ These are -H, -OH, or -OCH ３ [Represents] [In the formula, R ９ , R １０ , R １１ and R １２ These are the same or different -H, -OH, or -OCH ３ [Represents] It represents the basis of, - R ５ and R ６ One of them is -H, -OH, or -OCH ３ The other represents a saturated or unsaturated linear or branched aliphatic group which may be substituted with at least one =O, -OH, or -COOH group, or the following formula (Ic): [In the formula, n = 0 or 1, k = 0 or 1, and when k = 1 the above ring is aromatic (Ar), and when k = 0 the above ring is not aromatic. When k=0, m=1, and when k=1, m=0. X is -O-, -CH-, or -CH ２ - represents, R １３ is -O-, base R ２３ or base-O-R ２３ - (wherein, R ２３ (represents a saturated or unsaturated linear or branched aliphatic group containing 1 to 5 carbon atoms, which may be substituted with at least one =O group.) R １４ is -H, -OH, -OCH ３ Or the following formula (Id): (In the formula, R １９ , R ２０ , R ２１ and R ２２ These are identical or different, -OH, -CH ２ OH represents an alkyl group containing 1 to 5 carbon atoms or an oxyalkyl group containing 1 to 5 carbon atoms. It represents the basis of, - R １５ , R １６ , R １７ and R １８ These are either the same or different, -H, -OH, -OSO ３ H, -CH ２ OH, -COOH, -O-glucuronide, -O-R ３０ , -O-CO-R ３０ or -CH ２ O-CO-R ３０ (In the formula, R ３０ (This represents a saturated or unsaturated linear or branched aliphatic group containing 1 to 30 carbon atoms, which may be substituted with at least one =O, -OH, or -COOH group.) at least one first compound, or a polymer of the first compound, and Formula (I), formula (II), or formula (III): [In the formula, - a represents a single bond or a double bond, - Y represents -O- or -CO-, - W is -CH ２ - or -CO- represents, - R ２４ is at least one -OH, -OCH ３ , represents an aryl group containing 5 to 8 carbon atoms, which may be substituted with an -O-hexoside or -O-glucuronide group, R ２５ is -H, -OH, or at least one -OH, -OCH ３ , represents an oxycarbonylaryl group containing 6 to 9 carbon atoms, which may be substituted with an -O-hexoside or O-glucuronide group, or R ２４ and R ２５ Together with the carbon atoms to which they are bonded, they form at least one -OH or -CH group. ２ It represents an aryl group containing six carbon atoms, which may be substituted with an OH group, and a represents a double bond. - R ２６ , R ２７ and R ２８ These are either the same or different -H, -OH, -OCH ３ , represents -O-hexoside or O-glucuronide, - R ２９ is -H, -OH, or the following formula (IIa): [Represents the basis of] [In the formula, - j = 0 or 1, when j = 1 the above ring is aromatic (Ar), and when j = 0 the above ring is not aromatic. When j=0, m=1, and when j=1, m=0. - When j = 1, R ３２ This represents an alkyl group having 1 to 5 carbon atoms, and when j = 0, R ３２ R ３３ Along with this, the following equation (IIIa): (In the formula, n = 0 or 1, R ４５ is -H or -CH ３ This represents, R ４６ is, -CH ２ OH or the following formula (IIIb) or (IIIc): It represents the basis of, R ４７ and R ４８ (These are either the same or different, representing -H or -OH.) It represents the basis of, - R ３４ , R ３５ , R ３８ , and R ４３ These are the same or different, -H or -CH ３ This represents, - R ３６ represents -H, and R ４２ ha-CH ３ It represents, or R ３６ and R ４２ Together, they represent the base of the formula -O-CO-, - R ３７ This represents a -H or -O-hexoside, - b represents a single bond or a double bond. - R ３９ ha-CH ３ Represents R ４０ -H represents -H, or R ３９ and R ４０ Together, they form the following equation (IIId): It represents the basis of, -R ４１ is -H, -OH, or the following formula (IIIe) or (IIIf): It represents the basis of, - R ４４ [This represents -H or -OH] At least one second compound of, or a cosmetically or nutritionally acceptable salt or ester thereof. A composition comprising, wherein the second compound of formula (I) is different from the first compound of formula (I).

2. The first compound is given by the following formula: [wherein, A １ , A ２ and A ３ are the same or different and each represents -OH, -OSO ３ H, -O-glucuronide, or -O-CO-A ４ (wherein, A ４ represents a saturated or unsaturated, straight-chain or branched aliphatic group containing 1 to 30 carbon atoms, which may be substituted with at least one =O, -OH, or -COOH group)], The composition according to claim 1, selected from the group consisting of the following compounds.

3. The second compound is given by the following formula: [In the formula, - B １ -OH, -OCH ３ , or -O-glucuronide, -B ２ represents -OH or -OCH ３ and - B ３ represents -H or -OH, - B ４ is -OH, -O-glucuronide, or the following formula: (In the formula, B ６ is -OH, -OCH ３ (or represents -O-glucuronide) It represents the basis of, - B ５ [This represents -OH, -O-hexoside, or -O-glucuronide] The composition according to claim 1, selected from the group consisting of the following compounds.

4. The composition according to claim 1, further comprising at least one third compound of formula (I), (II), or (III), provided that the third compound is different from the first and second compounds.

5. - Compounds of formula (I.1), (I.2), or (I.3), - Compounds of formula (II.1), and - Compounds of formula (II.3) or (II.4) The composition according to claim 1, comprising at least two different compounds, or at least three different compounds, selected from each of the above.

6. The composition according to claim 1, wherein the compounds of formulas (I), (II), and (III) are contained in at least one plant extract.

7. The composition according to claim 1, further comprising at least one cosmetically or nutritionally acceptable carrier or additive.

8. Use of the composition according to any one of claims 1 to 7 as a cosmetic or nutritional supplement for human or animal use, particularly as an anti-aging or antioxidant cosmetic or nutritional supplement.

9. Use of the composition according to any one of claims 1 to 7 as a cosmetic for reducing at least one sign of skin aging.

10. Uses of at least one first compound of formula (I) as defined in claim 1, or at least one polymer of the first compound, in combination with at least one second compound of formula (I), formula (II) as defined in claim 1, or formula (III) as defined in claim 1, in which the second compound of formula (I) is different from the first compound of formula (I).

11. A cosmetic use for reducing at least one sign of skin aging, comprising at least one first compound of formula (I) as defined in claim 1, or at least one polymer of the first compound, and at least one second compound of formula (I), formula (II) as defined in claim 1, or formula (III) as defined in claim 1, wherein the second compound of formula (I) is different from the first compound of formula (I).

12. The use according to claim 10, wherein the first compound is as defined in claim 2.

13. The use according to claim 10, wherein the second compound is as defined in claim 3.

14. The use according to claim 10, wherein at least one third compound of formula (I), (II), or (III) is further combined, provided that the third compound is different from the first and second compounds.

15. - Compounds of formula (I.1), (I.2), or (I.3), - Compounds of formula (II.1), and - Compounds of formula (II.3) or (II.4) The use according to claim 10, wherein at least two different compounds, or at least three different compounds, are selected from each of the above.

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