FR2822068A1 - Topical composition useful for combating skin aging comprises avocado furan lipids and natural isoflavones - Google Patents

Abstract

Topical composition comprises avocado furan lipids (I) and natural isoflavones (II). Topical composition comprises avocado furan lipids of formula (I) and natural isoflavones (II) in the form of aglycones of formula (IIa) and/or glycosides of formula (IIb): R = 11-19C alkyl with 0-3 double or triple bonds; R'1 = H or OH; R'2 = H or OMe; R'3 = OH; R'4 = H or OH; R'5 = H or OMe; R'6 = H.

Description

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Topical composition comprising a combination of furan lipids of avocado and isoflavones
The present invention relates to topical compositions containing a combination of furanic lipids of avocado and isoflavones to combat aging of the skin.

 The aging of the skin is often described as appearing in two ways. The first is chronological or intrinsic aging, while the second is extrinsic aging, namely aging caused by the environment; this is particularly the case of photoaging, namely the damage done to the skin because of the direct or indirect effects of ultraviolet light. Many other factors contribute to accelerate the endogenous aging of the skin. They include sun exposure, free radicals, some hormonal changes associated with old age and smoking.

 The compositions according to the present invention are useful for combating all these types of skin aging.

 The energetic aspect of cellular metabolism of the skin as a function of age has been studied by magnetic resonance spectroscopy of phosphorus 31p by L. Declercq et al, Influence of Age and Ultraviolet A Exposure upon Energy Metabolism of Human Skin Study by 31p Nuclear Magnetic Resonance Spectroscopy, XXIst IFSCC International Congress 2000, Berlin. The

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 Skin aging is associated with a loss of the optimum functions and energy reserve capacity of the skin and a decreased ability to respond to stimuli, resulting from changes occurring at the cellular level. For example, keratinocytes and fibroblasts show a decrease in life expectancy in vitro with age, certainly due to a decrease in the mitotic response. For example, chronic exposure to UV irradiation and other environmental factors increases the aging process of the skin and leads to disturbed expression of genes associated with proliferation and differentiation. Finally, another example of skin aging at the cellular level is the repair of the skin barrier after aggression, which is slow for older skin, the healing capacity is also slowed for older skin.

 The aging process gives rise at the cellular level to an accumulation of oxidative damage to essential molecules such as membrane lipids, proteins and DNA. Thus mitochondrial DNA mutations accumulate during this aging process and are significantly increased in photovielly skin. One of the main functions of mitochondria is to provide energy to the cells by a process of oxidative phosphorylation.

So the biological consequence of the accumulation of mitochondrial DNA mutations would be to reduce the ability of the cell to produce ATP. Inasmuch as the ability to respond to stimuli and

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 neutralizing the aggressions requires energy, the accumulation of mitochondrial DNA mutations could partly explain the reduced response capacity of senescent skins and in particular photovieillies.

 In particular, it was concluded from this article cited above that a repair treatment of the cutaneous barrier and which increases the self-defense of senescent skin leads to a reduced need for energy consumption under conditions of acute aggression (particularly exposure UVA). Thus, AMP allows the increase of cellular ATP and increases the synthesis of DNA in senescent fibroblasts.

 It has now been found that the application of a topical composition comprising a combination of furan lipids of avocado and isoflavones makes it possible to combat extrinsic or intrinsic aging of the skin, whatever its origin. Among the causes of this skin aging against which the composition according to the invention may be useful, mention may be made of UV irradiation, oxidizing aggressions in particular due to the environment and hormonal changes, in particular due to menopause.

 Moreover, the composition according to the invention may also be useful for facilitating the healing of the skin and treating burns of the skin.

 In particular, this combination makes it possible to restore the cellular energy level necessary for cellular metabolism by stimulating the metabolism of mitochondrial phosphorus.

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 The present invention relates to these topical compositions, to the associated cosmetic treatment method and to the use of this composition for the manufacture of a dermatological composition for improving the energetic metabolism of the senescent skin.

dans laquelle R est une chaîne linéaire hydrocarbonée en Cil-Clg, de préférence C13-Ci7, saturée ou comprenant une à trois insaturations éthyléniques et/ou acétyléniques. By furan lipids of avocado is meant according to the invention the components corresponding to formula (I):

wherein R is a C1-C18, preferably C13-C17, hydrocarbon linear chain, saturated or comprising one to three ethylenic and / or acetylenic unsaturations.

As a furanic lipid of avocado, mention may be made in particular of 2-furanyl-8-11-cis-heptadecadiene (INCI name = 2heptadecadienylfuran).
Very often the topical compositions according to the present invention contain, as avocado furan lipids, a mixture of components of formula (I), but they may also be present in pure form in the context of the present invention.

 These furanic avocado lipids can be obtained by chemical synthesis or extraction of leaves or fruit or distillation of avocado oil.

 One of the methods that can be implemented to obtain avocado furan lipids and which is the subject of the patent application PCT / FROO / 2601 consists of

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 subjecting an unsaponifiable fraction of avocado oil to a molecular distillation step.

 The unsaponifiable can be obtained by controlled drying of the fruit, extraction of the oil by cold pressure, preliminary molecular distillation of the oil before saponification with ethanolic potassium hydroxide, extraction of the unsaponifiable material in a countercurrent column with an organic solvent , filtration, washing and deodorization.

 The final molecular distillation step of the unsaponifiable is then carried out with temperature means set for a temperature of between 100 and 160 ° C. and pressure means set for a pressure of between 10 3 and 5. 10 -2 mm Hg .

 In particular, the temperature means are set for a temperature of between 100 and 140 ° C. and the pressure means are adjusted for a pressure of between 10 3 and 5. 10 -2 mmHg to obtain a distillate comprising mainly furan lipids. avocado. Indeed, by this method, polyhydroxy fatty alcohols of avocado can also be produced simultaneously.

 This molecular distillation step of the unsaponifiable, as well as any other molecular distillations that can be carried out in the process of the invention, as described above, are preferably carried out using a device chosen from the molecular distillers of the type centrifugal and molecular scraped film type devices.

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Molecular distillers of centrifugal type are known to those skilled in the art. For example, EP-0 493 144 discloses such a molecular distiller. In general, the product to be distilled is spread in a thin layer on the heated surface (hot surface) of a conical rotor rotating at high speed.

The distillation chamber is placed under vacuum. Under these conditions, there is evaporation and not boiling, from the hot surface, constituents of the unsaponifiable, the advantage being that the oil and the unsaponifiable (these products are deemed fragile) are not degraded during evaporation.

 The isoflavones that can be used according to the present invention are obtained by chemical synthesis or are natural substances extracted from natural products, in particular from plants such as soybean, clover, lupine, apple seeds, etc. Very often the topical compositions according to the present invention contain, as isoflavones, a mixture of different isoflavones, but they can also be present in pure form in the context of the present invention. In addition, the aglycone forms of the isoflavones and the glycosylated forms thereof are distinguished. These various forms are most often in a mixture. They are illustrated by the following formulas.

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Aglycone forms, of formula:

dans laquelle R'1 représente un atome d'hydrogène ou un groupe hydroxy, R'2 représente un atome d'hydrogène ou un groupe méthoxy et R'3 représente un groupe hydroxy.

in which R'1 represents a hydrogen atom or a hydroxyl group, R'2 represents a hydrogen atom or a methoxy group and R'3 represents a hydroxyl group.

dans laquelle R'4 représente un atome d'hydrogène ou un groupe hydroxy, R'5 représente un atome d'hydrogène ou un groupe méthoxy et R'6 représente un atome d'hydrogène. Advantageously, according to the present invention, R'l, Rf; and R'3 represent: R'l R'2 R3 Compound name HH OH Daidzein OH H OH Genistein H OCH3 OH Glycitein Glycosylated forms, of formula:

in which R'4 represents a hydrogen atom or a hydroxyl group, R'5 represents a hydrogen atom or a methoxy group and R'6 represents a hydrogen atom.

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Avantageusement, selon la présente invention R'4, R5 et R'6 représentent : R'4 R'5 R'6 Nom du composé H H H Daidzine OH H H Génistine H OCH3 H Glycitine
Les formes glycosylées des isoflavones sont les plus abondantes dans la nature.

Advantageously, according to the present invention R'4, R5 and R'6 represent: R'4 R'5 R'6 Name of the compound HHH Daidzine OH HH Genistin H OCH3 H Glycitin
The glycosylated forms of isoflavones are the most abundant in nature.

En particulier, la génistéine ou 4, 5, 7trihydroxyisoflavone utilisable selon la présente invention peut être un produit d'origine végétale et notamment de soja, titrant 85 à 90 % en poids de génistéine, notamment le produit commercialisé par la société Buckton Scott sous le nom"génistéine titrée à 85%". Preferred isoflavones are natural isoflavones such as genistein (1), daidzein or glycitein.

In particular, the genistein or 4,5,6-trihydroxyisoflavone that may be used according to the present invention may be a product of vegetable origin, and in particular of soybean, which assays 85 to 90% by weight of genistein, in particular the product marketed by the company Buckton Scott under the name name "85% titrated genistein".

Advantageously, the composition according to the present invention further comprises a peptide extract of lupine.

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This peptide extract of lupine can advantageously be obtained by the method described in the patent application published under the number WO00 / 62789: The lupine dry extract preferably comprises at least 70%, preferably at least 80% of peptides.

 These peptides are obtained by hydrolysis of the protein fraction of lupine.

 The hydrolysis can be carried out by any suitable means, including enzymatic hydrolysis.

éventuellement séparation de la fraction protéique, hydrolyse de la fraction protéique et récupération, éventuellement après filtration, de l'extrait protéique. A process for the preparation of such a lupine peptide extract comprises the following steps: preparation of a delipidated and ground lupine cake or a micronized lupine (lipid) flour, extraction of soluble protein and osic fractions or precipitation at pH acid (4 or 5) according to the isoelectric point,

optionally separation of the protein fraction, hydrolysis of the protein fraction and recovery, optionally after filtration, of the protein extract.

The lupine lipid or delipidated flours, the peptide extracts comprising the sugars may be used as peptide extract of lupine that may be included in the combination according to the present invention.

 Preferably, the peptide extract has the following amino acid composition (percent by weight based on the total weight of amino acids).

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<Tb>
<Tb>

Total amino acids <SEP>% / AA <SEP>
<tb> ASP <SEP> 11, <SEP> 3
<tb> GLU <SEP> 23, <SEP> 2
<tb> SER <SEP> 5, <SEP> 1
<tb> HIS <SEP> 1, <SEP> 7
<tb> GLY <SEP> 3, <SEP> 4
<tb> THR <SEP> 3, <SEP> 2
<tb> ALA <SEP> 2, <SEP> 8
<tb> ARG <SEP> 10, <SEP> 3
<tb> TYR <SEP> 6, <SEP> 1
<tb> CYS-CYS <SEP> 2, <SEP> 4
<tb> VAL <SEP> 3, <SEP> 8
<tb> MET <SEP> 0, <SEP> 2
<tb> PHE <SEP> 7, <SEP> 0
<tb> ILE <SEP> 3, <SEP> 3
<tb> LEU <SEP> 7, <SEP> 9
<tb> LYS <SEP> 3, <SEP> 7
<tb> PRO <SEP> 4, <SEP> 4
<Tb>

The composition according to the present invention may advantageously contain, as peptide extract of lupine, the product marketed by Pharmascience laboratories under the trade mark ACTIMP 193 &commat;.

 For simplification purposes, unless otherwise indicated, the topical composition is useful for dermatological or cosmetic purposes in what follows.

 The composition according to the invention comprises a cosmetically acceptable support, ie a carrier compatible with the skin, the mucous membranes, the nails, the hair and may be in any galenical form normally used for topical application, especially under form of an aqueous, hydroalcoholic or oily solution, an oil-in-water or water-in-oil or multiple emulsion, an aqueous or oily gel, a liquid anhydrous product, pasty or solid,

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 an oil dispersion in an aqueous phase using spherules, these spherules may be polymeric nanoparticles such as nanospheres and nanocapsules or better lipid vesicles of ionic and or nonionic type.

 This composition may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste, a mousse .

 It can optionally be applied to the skin in the form of an aerosol. It can also be in solid form, and for example in the form of a stick.

It can be used as a care product, as a cleaning product, as a makeup product or as a simple deodorant product.

 The composition of the invention may also contain the usual adjuvants in the cosmetic and dermatological fields, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, perfumes, fillers, filters , pigments, chelating agents, odor absorbers and dyestuffs. The amounts of these various adjuvants are those conventionally used in the fields under consideration, and for example from 0.01 to 20% of the total weight of the composition. These adjuvants, depending on their nature, can be introduced into the fatty phase, into the aqueous phase, into the lipid vesicles and or into the nanoparticles.

 When the composition of the invention is an emulsion, the proportion of the fatty phase can range from 5 to 80% by weight, and preferably from 5 to 50% by weight.

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 total of the composition. The oils, emulsifiers and coemulsifiers used in the composition in emulsion form are chosen from those conventionally used in the field under consideration. The emulsifier and the coemulsifier are present in the composition in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% of the total weight of the composition.

 As oils that may be used in the invention, mention may be made of mineral oils, oils of vegetable origin (apricot oil, sunflower oil, plum oil), oils of animal origin, synthetic oils and silicone oils. and fluorinated oils (perfluoropolyethers). It is also possible to use fatty alcohols (cetyl alcohol), fatty acids and waxes (beeswax) as fatty substances.

 As emulsifiers and coemulsifiers that can be used in the invention, mention may be made, for example, of fatty acid and polyethylene glycol esters such as PEG-40 stearate, PEG-100 stearate, fatty acid and polyol esters. such as glyceryl stearate and sorbitan tristearate.

 As hydrophilic gelling agents, mention may in particular be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as copolymers of acrylates / alkylacrylates, polyacrylamides, polysaccharides, natural gums and clays, and, as lipophilic gelling agents, it is possible to mention mention modified clays such as bentones, metal salts of fatty acids, hydrophobic silica and polyethylenes.

 The composition may contain other hydrophilic active agents such as proteins or hydrolysates of

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 protein, peptides (eg lupine) amino acids, polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts and hydroxy acids.

 As lipophilic active agents, it is possible to use retinol (vitamin A) and its derivatives, tocopherol (vitamin E) and its derivatives, essential fatty acids, ceramides, essential oils, salicylic acid and its derivatives.

composés de la famille des allylamines, les dérivés de glycine (hydroxyméthylglycinate de sodium par exemple), la piroctone olamine ou encore l'octopirox ; According to the invention, it is possible, inter alia, to associate at least one furanic lipid derivative of avocado and isoflavones with other active agents intended in particular for the prevention and / or treatment of cutaneous affections. Among these active agents, there may be mentioned by way of example: agents that modulate skin differentiation and / or proliferation and / or pigmentation such as retinoic acid and its isomers, retinol and its esters, vitamin D and its derivatives, phytoestrogens or kojic acid; antibacterials such as octanediol modulating agents bacterial adhesion to the skin and mucous membranes such as certain sugar derivatives; anti-fungal agents, in particular compounds belonging to the class of imidazoles or their salts,

compounds of the allylamine family, derivatives of glycine (sodium hydroxymethylglycinate for example), piroctone olamine or octopirox;

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- des apaisants tels que l'acide salicylique, le lupeol, l'allantoine et le Silanediol Salicylate ; des agents anti prurigineux comme la glycine ; - les agents kératolytiques tels que les acides alpha-et bêta-hydroxycarboxyliques ou bêtacétocarboxyliques, leurs sels, amides ou esters et plus particulièrement les hydroxy-acides tels que l'acide glycolique, l'acide lactique, l'acide salicylique, l'acide citrique et de manière générale les acides de fruits ; - les agents anti-radicaux libres, tels que l'alphatocophérol ou ses esters, les superoxyde dismutases, certains chélatants de métaux ou l'acide ascorbique et ses esters ; - les anti-séborrhéiques ; - les anti pelliculaires comme l'octopirox ou la pyrithione de zinc ;

- les anti-bactériens et les actifs présentant une activité antiacnéique ; des substances décrites comme présentant des effets anti-irritants, en particulier vis-à-vis de composés irritants éventuellement présents dans les compositions.

soothing agents such as salicylic acid, lupeol, allantoin and silanediol salicylate; anti-pruriginous agents such as glycine; keratolytic agents such as alpha-and beta-hydroxycarboxylic acids or beta-carboxylic acids, their salts, amides or esters and more particularly hydroxy acids such as glycolic acid, lactic acid, salicylic acid, acid citric and generally fruit acids; anti-free radical agents, such as alphatocopherol or its esters, superoxide dismutases, certain metal chelators or ascorbic acid and its esters; anti-seborrhoeic agents; anti-dandruff such as octopirox or zinc pyrithione;

anti-bacterials and active agents having anti-acne activity; substances described as having anti-irritant effects, in particular with respect to irritating compounds that may be present in the compositions.

 As actives, it is possible to use, in particular, moisturizers such as polyols (for example glycerine), vitamins (for example D-panthenol), anti-inflammatory agents, soothing agents (allantoin, cornflower water), filters UVA and UVB, mattifying agents and light-reflecting pigments such as mixtures of titanium and mica.

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It is also possible to add anti-wrinkle active agents with, for example, retinol and its derivatives (retinaldehyde), vitamins (vitamin C, D, B6), anti-gycatic agents and modulators of Heat Shock Protein.

 Since the skin consists of many other components than collagen and fibroblasts, it is advantageous when using the combination of furan lipids of avocado and isoflavones according to the invention, to promote at the same time the synthesis of these other components, for example lipids (by means of modulating agents for the synthesis of cutaneous lipids with, for example, lupine peptides, concentrates of vegetable oils such as sunflower) and or to promote the proliferation of other components such as keratinocytes.

 The topical compositions according to the invention typically comprise between 0.1 and 10% by weight (w / w), preferably between 0.5 and 5% in avocado furan lipid or a mixture thereof and between 0.01 and 10% (w / w) by weight of isoflavones, expressed as pure isoflavones or a mixture thereof, preferably between 0.01 and 5% based on the total weight of the topical composition.

 When the topical compositions according to the invention further contain peptide extract of lupine, it may be present between 0.1 and 5% by weight (w / w) relative to the total weight of the topical composition.

 Said compositions according to the invention may be chosen for day and / or night use on the face, body and hands.

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The topical compositions according to the invention have an effect of improving the energetic metabolism of the senescent skin. The first results can be obtained at the cellular energy level after a few hours of treatment with the compositions of the invention.

 The measurement of the energy status of the skin can advantageously be carried out by nuclear magnetic resonance spectroscopy (NMR) of Phosphorus 31.

 The nuclear magnetic resonance spectroscopy (NMR) of Phosphorus 31 is a non-invasive wo vivo method suitable for studying cutaneous oxidative metabolism. This method is particularly known in connection with the study of the viability of tissues attacked by burns (T. Nagel, The Slotted Crossover Surface Coil: A detector for in vivo NMR of Skin, Magnetit Resonance in Medicine 16, 252-268 (1990)) .

This same method by IP NMR spectroscopy, described in more detail in Example 9, has also been shown to be useful for measuring - ATP, which provides energy to cell structures and metabolic activity.
Phosphocreatine (PCr), which is a reserve of energy giving a phosphorus to ADP to obtain ATP. It is located in the epidermis and the papillary dermis, - Inorganic phosphorus (Pi), Thus phosphocreatine is responsible for reconstituting the ATP stores consumed during a period of cellular ischemia by supplying a phosphate group to the d ADP according to the reaction catalyzed by creatine phosphokinase:

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ADP + PCr ATP + Cr

Les rapports PCr/Pi et PCr/ATP sont un reflet du statut énergétique d'un tissu (ZEMTSOV,"Human in vivo 31P spectroscopy of skin : potentially a powerful tool for noninvasive study of metabolism in a cutaneous tissue". J Dermatol Surg Oncol. ; 15 (11) : 1207-11,1989). De même, ATP/Pi reflète le niveau d'énergie disponible.

ADP + PCr ATP + Cr

The ratios PCr / Pi and PCr / ATP are a reflection of the energy status of a tissue (ZEMTSOV, "Human in vivo 31P spectroscopy of skin: a potent tool for a noninvasive study of metabolism in a cutaneous tissue." J Dermatol Surg Oncol 15 (11): 1207-11, 1989). Similarly, ATP / Pi reflects the level of energy available.

 The following examples illustrate the present invention.

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Example 1: Care cream containing light-reflecting pigments

<Tb>
<tb> Ingredients <SEP>% <SEP> in <SEP> weight
<tb> Water <SEP> 4 <SEP> 8
<tb> Squalene5, <SEP> 3, '
<tb> Vaseline <SEP> 5, <SEP> 00
<tb> Glycerin <SEP> 5, <SEP> 00
<tb> Neopentanoate <SEP> Isodecylate <SEP> 5, <SEP> 00
<tb> Tetramethylhexanoate <SEP> 5.00
<tb> Cyclomethicone <SEP> 4.35
<tb> Alcohol <SEP> cetearyl <SEP> 2.89
<tb> Peptide <SEP> of <SEP> lupine <SEP> (l) <SEP> 2, <SEP> 00
<tb> Myristate <SEP> of <SEP> myrsityle2, <SEP> 00
<tb> Laureth-23 <SEP> 2.00
<tb> Silica <SEP> 1.59
<tb> 2-Heptadecadienylfuran <SEP> 1, <SEP> 00
<tb> Bee <SEP> Wax <SEP> 1, <SEP> 00
<tb> Gum <SEP> of <SEP> sclerotium1, <SEP> OC
<tb> PEG-6 <SEP> 0, <SEP> 90
<tb> Phenoxyethanol <SEP> 0.80
<tb> Polyacrylamide <SEP> 0.80
<tb> Stearate <SEP> of <SEP> Glycerol <SEP> 0.70
<tb> Dimethiconol <SEP> 0, <SEP> 65
<tb> Glucoside <SEP> of <SEP> cetearyl <SEP> 0, <SEP> 60
<tb> Fragrance <SEP> 0, <SEP> 50
<tb> Acetate <SEP> of <SEP> Tocopheryl <SEP> 0.50
<tb> Sorbate <SEP> of <SEP> potassium <SEP> 0, <SEP> 45
<tb> Methylparaben <SEP> 0, <SEP> 40
<tb> C13-C14 <SEP> isoparafine <SEP> 0, <SEP> 40
<tb> Oxide <SEP> of <SEP> titanium <SEP> 0, <SEP> 39
<tb> Propylparaben <SEP> 0, <SEP> 30
<tb> Ceteareth-33 <SEP> 0, <SEP> 195
<tb> Acid <SEP> citric0, <SEP> i <SEP> 4
<tb> Laureth-7 <SEP> 0, <SEP> 10
<tb> Palmitate <SEP> cetyl <SEP> 0.10
<tb> Cocoglycerides <SEP> 0.10
<tb> 4,5,7-trihydroxyisoflavone <SEP> 0.10
<tb> Disodium <SEP> EDTA <SEP> 0, <SEP> 10
<tb> Oxide <SEP> of <SEP> iron <SEP> 0, <SEP> 02
<tb> Hydroxide <SEP> of <SEP> sodium <SEP> 0, <SEP> 03
<tb> Acetate <SEP> of <SEP> Retinyl <SEP> 0.015
<tb> Linoleate <SEP> ethyl <SEP> 0, <SEP> 015
<tb> Linolenate <SEP> ethyl <SEP> 0, <SEP> 015
<Tb>
(1) ACTIMP &commat; 193 marketed by Pharmascience Laboratories

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Exemple 2 : Emulsion anti ride

Example 2 Anti Wrinkle Emulsion

<Tb>
<tb> Ingredients <SEP>% <SEP> in <SEP> weight
<tb> Water <SEP> QSP <SEP> 100
<tb> Squalene <SEP> 5, <SEP> 00
<tb> Vaseline <SEP> 5, <SEP> 00
<tb> Glycerin <SEP> 5, <SEP> 00
<tb> Neopentanoate <SEP> of isodecyl5, <SEP> 00
<tb> Tetraethylhexanoate <SEP> of <SEP> pentaerythrityl <SEP> 5.00
<tb> Cyclomethicone <SEP> 4, <SEP> 00
<tb> Alcohol <SEP> from <SEP> cetearyl <SEP> 3, <SEP> 00
<tb> Myristate <SEP> of <SEP> myristyl <SEP> 2, <SEP> 00
<tb> Laureth-23 <SEP> 2, <SEP> 00
<tb> Silica <SEP> 2, <SEP> 00
<tb> 2-Heptadecadienylfuran <SEP> 0.1 <SEP> to <SEP> 10
<tb> Bee <SEP> Wax <SEP> 1, <SEP> 00
<tb> Gum <SEP> of <SEP> sclerotium <SEP> 1, <SEP> 00
<tb> PEG-6 <SEP> 1, <SEP> 00
<tb> Polyacrylamide <SEP> 0, <SEP> 80
<tb> Stearate <SEP> of <SEP> Glyceryl <SEP> 0, <SEP> 70
<tb> Dimethiconol <SEP> 0, <SEP> 70
<tb> Glucoside <SEP> of <SEP> cetearyl <SEP> 0, <SEP> 60
<tb> C13-14 <SEP> Isoparaffin <SEP> 0, <SEP> 40
<tb> Citric acid <SEP><SEP> 0, <SEP> 14
<tb> Laureth-7 <SEP> 0, <SEP> 10
<tb> 4.5, <SEP> 7-Trihydroxyisoflavone <SEP> 0, <SEP> 01 <SEP> to <SEP> 10
<tb> Hydroxide <SEP> of <SEP> sodium <SEP> 0, <SEP> 03
<tb> System <SEP> conservative <SEP> QS
<tb> Perfume <SEP> QS
<Tb>

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Exemple 3 : Emulsion fluide anti-âge

Example 3: Anti-aging fluid emulsion

<Tb>
<tb> Ingredient <SEP> weight
<tb> Water <SEP> QSP <SEP> 100
<tb> Squalene <SEP> 5.00
<tb> Vaseline <SEP> 5.00
<tb> Glycerine <SEP> 5.00
<tb> Neopentanoate <SEP> Isodecylate <SEP> 5.00
<tb> Tetraethylhexanoate <SEP> 5.00
<tb> Cyclomethicone <SEP> 4.00
<tb> Alcohol <SEP> 3.00
<tb> Peptide <SEP> 10
<tb> Myristate <SEP> myristyle <SEP> 2.00
<tb> Laureth-23 <SEP> 2.00
<tb> Silica <SEP> 2.00
<tb> 2-Heptadecadienylfuran <SEP> 0.1 <SEP> to <SEP> 10
<tb> Bee <SEP> wax <SEP> 1.00
<tb> Gum <SEP> Sclerotium <SEP> 1.00
<tb> PEG-6 <SEP> 1.00
<tb> Polyacrylamide <SEP> 0.80
<tb> Stearate <SEP> Glycerol <SEP> 0.70
<tb> Dimethiconol <SEP> 0.70
<tb> Glucoside <SEP> cetearyl <SEP> 0.60
<tb> C13-14 <SEP> Isoparaffin <SEP> 0.40
<tb> Acid <SEP> 0.14
<tb> Laureth-7 <SEP> 0.10
<tb> Isoflavones <SEP> 10
<tb> Hydroxide <SEP> sodium <SEP> 0.03
<tb> System <SEP> conservative <SEP> QS
<tb> Perfume <SEP> QS
<Tb>
(1) ACTIMP (dz93 marketed by Pharmascience Laboratories

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Exemple 4 : Crème de jour anti-âge

Example 4: Anti-Aging Day Cream

<Tb>
<tb> Ingredient <SEP> Weight <SEP> in <SEP>%
<tb> Water <SEP> QSP <SEP> QO
<tb> Tetraethylhexanoate <SEP> of <SEP> pentaerythrityl <SEP> 5, <SEP> 00
<tb> Neopentanoate <SEP> Isodecylate <SEP> 5.00
<tb> Squalene <SEP> 3, <SEP> 00
<tb> Dextrine <SEP> 3.00
<tb> Cyclomethicone <SEP> 3, <SEP> 00
<tb> Alcohol <SEP> of <SEP> cetearyl <SEP> 2, <SEP> 50
<tb> Peptide <SEP> of <SEP> lupine <SEP> (1) <SEP> 0.1 <SEP> to <SEP> 10
<tb> Glycerin <SEP> 2, <SEP> 00
<tb> Laureth-23 <SEP> 2, <SEP> 00
<tb> Myristate <SEP> of <SEP> myristyle <SEP> 2.00
<tb> Cyclopentasiloxane <SEP> 2.00
<tb> Nylon-6 <SEP> 1.50
<tb> 2-Heptadecadienylfuran <SEP> 0.1 <SEP> to <SEP> 10
<tb> Glucoside <SEP> of <SEP> cetearyl <SEP> 0, <SEP> 60
<tb> Bee <SEP> Wax <SEP> 0, <SEP> 50
<tb> Citrate <SEP> of <SEP> sodium <SEP> 0, <SEP> 40
<tb> 4.5, <SEP> 7-Trihydroxyisoflavone <SEP> 0, <SEP> 01 <SEP> to <SEP> 10
<tb> Dimethiconol0, <SEP> 0
<tb> Stearate <SEP> of <SEP> Glyceryl0, <SEP> 35
<tb> Disodium <SEP> EDTA <SEP> 0, <SEP> 30
<tb> Hydroxide <SEP> of <SEP> sodium <SEP> 0, <SEP> 30
<tb> Arylate <SEP> crosspolymer <SEP> 0, <SEP> 25
<tb> Gum <SEP> xanthan <SEP> 0.15
<tb> Glucose <SEP> 0.12
<tb> Citric acid <SEP><SEP> 0.08
<tb> System <SEP> conservative <SEP> QS
<tb> Perfume <SEP> QS
<Tb>
(1) ACTIMP # 193 marketed by Pharmascience Laboratories

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Example 5: Water-in-oil emulsion for sunscreen

<Tb>
<tb> Ingredient <SEP> Weight <SEP> in <SEP>%
<tb> Water <SEP> QSP <SEP> 100
<tb> Triglyceride <SEP> Caprylic / Caprique <SEP> 15, <SEP> 20
<tb> Dioxide <SEP> of <SEP> Titanium <SEP> 5 <SEP> to <SEP> 20
<tb> Octyle Palmitate <SEP><SEP> 4, <SEP> 64
<tb> Glycerin4, <SEP> 5
<tb> Cyclomethicone <SEP> 4, <SEP> 0
<tb> Oxide <SEP> of <SEP> zinc <SEP> 1 <SEP> to <SEP> 15
<tb> Cetyl <SEP> Dimethicone <SEP> Copolyol3, <SEP> 50
<tb> 2-Heptadecadienylfuran <SEP> 0, <SEP> 1 <SEP> to <SEP> 10
<tb> Octanoate <SEP> of <SEP> cetearyl <SEP> 3, <SEP> 50
<tb> Peptide <SEP> of <SEP> lupine <SEP> (1) <SEP> 0, <SEP> 1 <SEP> to <SEP> 10
<tb> Benzoate <SEP> of <SEP> C12-15 <SEP> alkyl <SEP> 3, <SEP> 50
<tb> Hyaluronate <SEP> of <SEP> sodium <SEP> 2, <SEP> 00
<tb> 4.5, <SEP> 7-Trihydroxyisoflavone <SEP> 0, <SEP> 01 <SEP> to <SEP> 10
<tb> Dimethicone <SEP> of <SEP> cetyl <SEP> 1.50
<tb> Hydroxide <SEP> Stearate <SEP> of Aluminum <SEP> and <SEP> of <SEP> 1.00
<tb> Magnesium
<tb> Bee <SEP> Wax <SEP> 1, <SEP> 00
<tb> Isostearic <SEP> acid <SEP> 1.00
<tb> Chloride <SEP> from <SEP> Sodium <SEP> 1, <SEP> 00
<tb> Acetate <SEP> 0.50
<tb> Perfume <SEP> 0.38
<tb> Gum <SEP> guar <SEP> 0.30
<tb> Silica <SEP> 0, <SEP> 30
<tb> Octyldodecanol <SEP> 0.15
<tb> Oxides <SEP> of <SEP> iron <SEP> 0, <SEP> 13
<tb> Gluconate <SEP> from <SEP> zinc <SEP> 0, <SEP> 08
<tb> System <SEP> conservative <SEP> QS
<Tb>
(1) ACTIMP (dz93 marketed by Pharmascience Laboratories

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Exemple 6 : Formule d'un stick hydratant

Example 6: Formula of a moisturizing stick

<Tb>
<tb> Ingredient <SEP> Weight <SEP> in <SEP>%
<tb> Oil <SEP> of <SEP> ricinus <SEP> 23,00
<tb> Alcohol <SEP> Oleic <SEP> 20, <SEP> 00
<tb> Oil <SEP> of <SEP> palm <SEP> hydrogenated <SEP> 17,00
<tb> Wax <SEP> of <SEP> Candelilla <SEP> 11, <SEP> 00
<tb> Bee <SEP> Wax <SEP> 10.00
<tb> Oil <SEP> Mineral <SEP> 9.57
<tb> Methoxycinnamate <SEP> 4.00
<tb> Peptide <SEP> of <SEP> lupine <SEP> (1) <SEP> 0.1 <SEP> to <SEP> 10
<tb> 2-Heptadecadienylfuran <SEP> 0.1 <SEP> to <SEP> 10
<tb> Butter <SEP> of <SEP> shea butter2, <SEP> 00
<tb> 4, <SEP> 5, <SEP> 7-Trihydroxyisoflavone <SEP> 0, <SEP> 01 <SEP> to <SEP> 10
<tb> Quaternium-18 <SEP> Hectorite <SEP> l, <SEP> 10
<tb> Dioxide <SEP> 1.00
<tb> Acetate <SEP> of <SEP> Tocopheryl <SEP> 0.50
<tb> Carbonate <SEP> of <SEP> Propylene <SEP> 0.33
<tb> Perfume <SEP> QS
<Tb>

(1) ACTIMP &commat;193 commercialisé par les laboratoires Pharmascience

(1) ACTIMP &commat; 193 marketed by Pharmascience Laboratories

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Exemple 7 : Formule d'un stick pour la protection solaire

Example 7: Formula of a stick for sunscreen

<Tb>
<tb> Ingredient <SEP> Weight <SEP> in <SEP>%
<tb> Coconut Glycerides <SEP> Hydrogenated <SEP> 12, <SEP> 35
<tb> Oil <SEP> of <SEP> ricin <SEP> hydrogenated <SEP> 12,00
<tb> Triglyceride <SEP> Caprylic / Caprique <SEP> 10, <SEP> 15
<tb> Oil <SEP> of <SEP> ricin <SEP> 10.00
<tb> 2-Heptadecadienylfuran <SEP> 0, <SEP> 1 <SEP> to <SEP> 10
<tb> Cyclomethicone <SEP> 9, <SEP> 60
<tb> Dioxide <SEP> of <SEP> titanium <SEP> 8, <SEP> 36
<tb> Peptide <SEP> lupine <SEP> (1) <SEP> 0, <SEP> 1 <SEP> to <SEP> 0
<tb> Oleate <SEP> of <SEP> decylate <SEP> 7, <SEP> 62
<tb> 4.5, <SEP> 7-Trihydroxyisoflavone <SEP> 0, <SEP> 01 <SEP> to <SEP> 10
<tb> Wax <SEP> of <SEP> Candelilla <SEP> 7,00
<tb> Bee <SEP> Wax <SEP> 5, <SEP> 50
<tb> Octanoate <SEP> of <SEP> cetearyl <SEP> 5, <SEP> 20
<tb> Palmitate <SEP> of octyle3, <SEP> 13
<tb> Hydroxide <SEP> Stearate <SEP> Aluminum <SEP> and <SEP> from <SEP> 2.40
<tb> Magnesium
<tb> Oxide <SEP> of <SEP> zinc <SEP> 2, <SEP> 30
<tb> Dimethicone <SEP> of <SEP> cetyl <SEP> 1, <SEP> 50
<tb> Water <SEP> 0, <SEP> 60
<tb> Octyldodecanol0, <SEP> 58
<tb> Cetyl <SEP> Dimethicone <SEP> Copolyol <SEP> 0, <SEP> 50
<tb> Perfume <SEP> 0.25
<tb> Tocopherol <SEP> 0.08
<tb> Gluconate <SEP> from <SEP> zinc <SEP> 0, <SEP> 08
<tb> Hydrogenated <SEP> Palm <SEP> Glycerides <SEP> Citrate <SEP> 0.01
<Tb>
1) ACTIMP &commat; 193 marketed by Pharmascience Laboratories

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Exemple 8 : Formule d'un lait apaisant après soleil

Example 8: Formula of a soothing milk after sun

<Tb>
<tb> Ingredient <SEP> Pounds <SEP> in
<tb>%
<tb> Water <SEP> QSP <SEP> 100
<tb> Oil <SEP> Mineral <SEP> 6, <SEP> 00
<tb> Butter <SEP> of <SEP> Shea <SEP> 5, <SEP> 00
<tb> Oil <SEP> of <SEP> Jojoba <SEP> 4, <SEP> 00
<tb> Oil <SEP> corn <SEP> 4.00
<tb> Sebacate <SEP> 2.00
<tb> Alcohol <SEP> of <SEP> cetearyl <SEP> 1, <SEP> 60
<tb> Protein <SEP> of almond <SEP> hydrated <SEP> 1, <SEP> 50
<tb> 2-Heptadecadienylfuran <SEP> 0.1 <SEP> to <SEP> 10
<tb> Bisabolol <SEP> l, <SEP> 00
<tb> Sodium <SEP> PCA <SEP> 1, <SEP> 00
<tb> 4.5, <SEP> 7-Trihydroxyisoflavone <SEP> 0, <SEP> 01 <SEP> to <SEP> 10
<tb> Bee <SEP> Wax <SEP> 1, <SEP> 00
<tb> Coconut Glycerides <SEP> Hydrogenated <SEP> 1, <SEP> 00
<tb> PEG-40 <SEP> Stearate <SEP> 1, <SEP> 00
<tb> Polyacrylamide <SEP> 0, <SEP> 60
<tb> Acetate <SEP> of <SEP> Tocopheryl <SEP> 0, <SEP> 50
<tb> Glucoside <SEP> of <SEP> cetearyl <SEP> 0, <SEP> 40
<tb> C13-14 <SEP> Isoparaffin <SEP> 0, <SEP> 30
<tb> Carbomer <SEP> 0, <SEP> 25
<tb> Tromethamine <SEP> 0.15
<tb> Laureth-70, <SEP> 07500
<tb> Perfume <SEP> QS
<tb> System <SEP> conservative <SEP> QS
<Tb>
Example 9 Evaluation of the Composition of Example 1 on the Energy Properties of the Skin by Phosphorus NMR 31 METHODOLOGY Population and Mode of Selection The study was carried out on a population of 5 subjects.

These 5 subjects are healthy subjects, more than 55 years old,

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Females, menopausal without replacement therapy and with non-photoaging skin:
Average age: 59 years
Minimum age: 55 years
Maximum age: 65 years Application of the product On the first day of the experiment (TO), an application of the product was made on a surface of about 10x4 cm2 on the anterior surface of one of the wrists by the experimenter.

Then the application of the product was carried out by the volunteer twice a day (morning and evening) for 14 days.

These applications were performed on a wrist defined after randomization.

Choice of the test The subject was his own witness. A wrist received the product, the contralateral wrist being taken as an untreated reference. The study was non-comparative and conducted in open.

Course of the study Acquisitions controls were carried out before application of the product (TO), then at T + 3 hours, T + 7 hours, and T + 14 days. The control wrist was followed according to the same kinetics.

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 Duration of an acquisition (a forearm): 25 minutes.

Magnetic Resonance Imaging This test was designed to evaluate, over a period of 7 hours and 14 days, the effect on the skin metabolism of the application of the product of Example 1. The variations of the energy metabolism of the skin were determined by NMR spectroscopy of phosphorus 31 by measuring the relative concentrations of the main phosphorylated metabolites of the skin: inorganic phosphate (Pi), phosphocreatine (PCr), adenosine triphosphate (ATP). For reasons related to the NMR spectrometer geometry and measurement efficiency, the area of interest was taken at the anterior aspect of the wrist.

The spectroscopic acquisitions were carried out with a Biospec BMT 24/40 2.35 Tesla NMR spectrometer (Bruker, Germany), equipped with a proton-phosphorus double-tuned surface antenna developed by Spincontrol for in vivo NMR spectroscopy. skin. The subjects sat in a chair, arms extended laterally so that the wrist was in the center of the magnet. A restraint system has been used to achieve reproducible wrist positioning with respect to the surface antenna and to ensure close contact between the scanned area and the NMR signal receiving antenna while maintaining sufficient comfort for the duration of the acquisition (about 25 minutes, settings included).

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After tuning the antenna to the resonance frequency of the proton (100, 2 MHz), the homogeneity of the magnetic field was adjusted from the free precession signal of the water protons. The half-height width of the peak of the water (criterion representative of the homogeneity of the magnetic field) had to be less than 50 Hz.

paramètres suivants : impulsion radio-fréquence d'une durée de 250 As (tp) et de gain égal à 5, temps de récupération (TR) =1, 4 s, une gamme spectrale de 4000 Hz, un nombre d'accumulation (NS) égal à 600. Le signal RMN a été digitalisé par 4096 points. The surface antenna was then tuned to the phosphorus frequency (40.53 MHz) for final acquisition. The spectra were made with the

following parameters: radio-frequency pulse with a duration of 250 As (tp) and gain equal to 5, recovery time (TR) = 1, 4 s, a spectral range of 4000 Hz, an accumulation number (NS ) equal to 600. The NMR signal was digitized by 4096 points.

Data Analysis For analysis, the raw data (free precession signals) were transferred to a SUN workstation and processed with specific NMR data analysis software: Felix 95.0 (Biosym / MSI, San Diego, USA). USA).

In order to improve the signal-to-noise ratio of the NMR spectra, the free precession signal was multiplied by an exponential function (LB = 20) after application of the zero filling method. Subsequently the Fourier transformation, the phase and the baseline were corrected. The different peaks of the spectrum (Pi, PCr, aATP, ssATP, yATP,) were adjusted by Lorentzian functions and their surfaces determined by integration (the peak area being directly

<Desc / Clms Page number 29>

 proportional to the concentration of the molecule at the origin of the NMR signal). The pH of the skin was calculated from the chemical shifts of Pi and PCr with the experimental relationship of titration of phosphoric acid (MADDEN A., pH calibration curve at 1.5 Tesla, Phys Med Biol., 34 , 1289-1293, 1989) derived from the following Henderson-Hasselbach equation: pH = pKa + log (cm-3, 38/5, 70 - cr) where a is the chemical shift (in ppm) of Pi relative to at the peak of PCr taken as reference. The pKa of phosphoric acid is 6.70.

For each subject, surface measurements, PCr / Pi ratios (PCr peak area / Pi peak area), ATP / Pi, PCr / Ptotal, PCr / ATP, Pi / Ptotal, and ATP / Ptotal at different time were determined (where Ptotal is the sum of the areas of the peaks corresponding to the above-mentioned metabolites). The ratios of metabolites that represent relative concentrations make it possible to follow the evolution of the different metabolites over time. The variations of these ratios over time can also be determined using the percentages of variation calculated by taking the value at time TO as a reference according to: [(RT -RTo) / RTO * 100] where RT is the value of a ratio of metabolites at a given time T

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réalisée à TO, mais aucune analyse statistique des données n'a été réalisée du fait du faible échantillonnage. RTO is the value of the same ratio at time TO The data analysis was performed by comparing the measurements of the NMR parameters between the times T L3 hours, T + 7 hours, T + 14 days after application and measurement

performed at TO, but no statistical analysis of the data was performed due to low sampling.

RESULTS The interpretation of the results is based on the comparison between metabolite ratios.

The average results of the volunteers for the various reports gave rise to the following observations: - An increase at T + 3 hours of PCr / Pi (+ 9.1%), ATP / Pi (12.1%) after treatment with the product of Example 1.

pour ces mêmes rapports PCr/Pi (4, 3%), ATP/Pi (14, 5%), ainsi que pour le rapport ATP/Ptotal (5, 5%) après traitement par le produit de l'exemple 1. - These evolutions are also observed at T + 7 hours

for these same ratios PCr / Pi (4.3%), ATP / Pi (14.5%), as well as for the ATP / Ptotal ratio (5.5%) after treatment with the product of Example 1.

- In the long term (T + 14j), we also observe an increase in these ratios: PCr / Pi (5.3%), ATP / Pi (16.9%), and ATP / Ptotal (6.8%) after treatment with the product of Example 1.

On the other hand, for PCr / Ptotal, PCr / ATP and pH ratios, no significant variation was observed at different times after treatment with the product of Example 1.

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 - No variation was noted for the control wrist throughout the follow-up period.

The increase in PCr / Pi ratios (+ 9.1% at T + 3h), ATP / Pi (+ 16.9% at T + 14j) observed during treatment with the product of Example 1 can therefore be correlated. to an increase in the energy status of the skin. This implies at the same time that the Pi / Ptotal ratio must decrease, which has been observed at T + 3 hours (-8.5%), T + 7 hours (-7.3%) and T + 14 days (-8, 6%).

It therefore appears that the application of the product of Example 1 has resulted in an improvement in the energy status of the skin cells.

Claims (11)

 methoxy group and R'3 represents a hydroxy group and

 in which R'1 represents a hydrogen atom or a hydroxyl group, R'2 represents a hydrogen atom or a

 in which R is a C 1 -C 9 hydrocarbon linear chain, preferably C 1 -C 17 saturated or comprising one to three ethylenic and / or acetylenic unsaturations, present in the form of a mixture of these compounds of formula (I) or in pure form and the natural isoflavones are either in pure form or in the form of a mixture and are chosen from: - the isoflavones of aglycone forms, of formula (II):

1. A topical composition comprising a combination of avocado furan lipids and natural isoflavones, wherein the furan avocado lipids are compounds of formula (I): <Desc / Clms Page number 33>  in which R'4 represents a hydrogen atom or a hydroxyl group, R'5 represents a hydrogen atom or a methoxy group and R'6 represents a hydrogen atom.

 the isoflavones of glycosylated forms, of formula (IN 1):

2. Composition according to claim 1, characterized in that the isoflavones are chosen from Daidzein, Genistein, Glycitein, Daidzine, Genistin and Glycitin. 3. Composition according to claim 1 or 2, characterized in that it comprises, as avocado furan lipid, 2-furanyl-8-11-cis-heptadecadiene. 4. Composition according to any one of claims 1 to 3, characterized in that the avocado furan lipids are present between 0.1 and 10% by weight (w / w) and the isoflavones, expressed in pure isoflavones are present between 0.01 and 10% by weight (w / w) relative to the total weight of the topical composition. 5. Composition according to claim 4, characterized in that the avocado furan lipids are present between 0.5 and 5% by weight (w / w) and the isoflavones are present between 0.01 and 5% by weight (p p) relative to the total weight of the topical composition. <Desc / Clms Page number 34> 6. Composition according to any one of claims 1 to 5, characterized in that it further contains a peptide extract of lupine. 7. The composition as claimed in claim 6, characterized in that the peptide solids content of lupine comprises at least 70% of peptide. 8. Cosmetic treatment method for combating skin aging, characterized in that it consists in applying the composition according to any one of claims 1 to 7 on a senescent skin, having a burned area or requiring cicatrization. 9. Cosmetic treatment method according to claim 8, characterized in that the composition according to any one of claims 1 to 7 is applied to a senescent skin due to intrinsic or extrinsic aging. 10. Use of a topical composition according to any one of claims 1 to 7 for the preparation of a dermatological composition for improving the energetic metabolism of the senescent skin, having a burned area or requiring healing.  11. Use according to claim 10, characterized in that the dermatological composition is intended to improve cellular energy metabolism related to the metabolism of mitochondrial phosphorus.