EP2830585A2 - Composition topique comprenant des oligosaccharides sulfatés bioactifs et utilisations cosmétiques - Google Patents

Composition topique comprenant des oligosaccharides sulfatés bioactifs et utilisations cosmétiques

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Publication number
EP2830585A2
EP2830585A2 EP13722557.9A EP13722557A EP2830585A2 EP 2830585 A2 EP2830585 A2 EP 2830585A2 EP 13722557 A EP13722557 A EP 13722557A EP 2830585 A2 EP2830585 A2 EP 2830585A2
Authority
EP
European Patent Office
Prior art keywords
treatment
units
oligosaccharides
sulfate
polysaccharides
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP13722557.9A
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German (de)
English (en)
Inventor
Claire-Marie Grizaud
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sederma SA
Original Assignee
Sederma SA
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Filing date
Publication date
Application filed by Sederma SA filed Critical Sederma SA
Publication of EP2830585A2 publication Critical patent/EP2830585A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the invention relates to a topical composition
  • a topical composition comprising bioactive sulfated oligosaccharides obtained by enzymatic cleavage of polysaccharides from green algae of the ulva genus.
  • Cosmetic uses of this composition are also the subject matter of the present invention.
  • the present invention thus concerns in particular the cosmetics industry that manufactures and/or uses products for the treatment of the skin, scalp, mucous membranes and appendages (such as hair, eyelashes, eyebrows, nails, body hairs) of mammals, animals or humans, to improve their appearance and/or global condition.
  • cosmetics industry that manufactures and/or uses products for the treatment of the skin, scalp, mucous membranes and appendages (such as hair, eyelashes, eyebrows, nails, body hairs) of mammals, animals or humans, to improve their appearance and/or global condition.
  • the cosmetics industry is increasing demand for new products, particularly for new active ingredients that are derived from plant material to come within the scope of a sustainable development approach in comparison with a synthetic or chemical way of manufacturing.
  • Algae are thus an abundant source of raw material valued in many fields such as food, pharmaceuticals and cosmetics.
  • algae are already widely used but mainly for thickening or gelling properties of their extracts which contain mainly polysaccharides.
  • Polysaccharides form also a particularly interesting molecule class especially because they contain sequences similar to some bioactive oligomers.
  • the Applicant has found particular interest in green algae and more particularly in ulva genus, and in the ulva lactuca species. It is known that polysaccharides from algae of ulva genus include in particular osidic units of iduronic acid (IdqpA) and rhamnose 3 sulfate (Rha/*3 sulfate) having an interesting potential for therapeutic or cosmetic applications (WO2009/016275). The Applicant has found particular interest in the two types of ulva polysaccharides that can be extracted from green algae walls of the ulva genus and containing such osidic units:
  • the « GlcpA » units correspond to glucuronic acid units.
  • glucuronan type sequences can also be found, but in minority. These sequences contain enchainments of glucuronic acid units:
  • Glucuronan polysaccharide comprising in majority glucuronan osidic sequences containing enchainments of glucuronic acid units
  • An enzyme from the lyase class is capable of causing cleavage of the glycosidic bond between the osidic units according to a ⁇ elimination reaction (or transelimination).
  • a ulvan-lyase enzyme is adapted to cleave more particularly the osidic bond between G cpA and Rha/*3 sulfate and between IdopA and Rha/*3, whereas a glucuronan-lyase enzyme is more particularly adapted to cleave the osidic bond between owing:
  • This cleavage 1986 shows saccharidic molecule fragments, oligosaccharides, having at the created non-reducing terminal end, a heterocycle having an ethylenic bond between carbon 4 and carbon 5, this residue corresponding to a 4-deoxy-(hex-4-ene) pyranosyluronic acid.
  • the apparition of this ethylene bond and the dosage of the formed products can be monitored by UV spectroscopy at 235nm.
  • Cleaved oligosaccharides consist of oligo-ulvans and oligo-glucuronans. The proportion of each depends on the proportion of each of the starting glucuronan andulvan polysaccharides contacted with the enzymatic mixture.
  • a microorganism referenced CNCM 1-3776 is used to produce an enzyme mixture having a double enzymatic activity, ulvan lyase and glucuronan lyase, allowing thus to obtain a mixture of oligo-glucuronans and oligo-ulvans having a polymerisation degree (DP) inferior to 25 and with good yields for industrial production.
  • a DP corresponds to a diholoside unit (containing two oses).
  • sequence [->4)-P-D-GlcpA-(l ->4)-a-L-Rha/73 sulfate-(l ->] n corresponds to a DP of 1, comprising one glucose/rhamnose diholoside unit.
  • the aim of the present invention is to overcome this lack.
  • the present invention provides a topical composition comprising:
  • said oligosaccharides been obtained according to an enzymatic cleavage process according to a ⁇ - elimination reaction of polysaccharides extracted from green algae of the ulva genus comprising:
  • the polymerisation degree (DP) is measured by a ionic chromatography method.
  • the mean weight of the fraction is 6 kD measured by CPC/DEDL (centrifugal partition chromatography) with a sulfatation content of 13 to 17%.
  • this selected oligosaccharide fraction has a biological activity particularly interesting on skin cells, in particular anti-inflamatory, anti-radical, de-pigmenting effects on molecules of the dermal extracellular matrix (such as collagen 1 , collagen 4 and fibronectin), on epidermal extracellular matrix (hyaluronic acid). These tests are detailed below in the description.
  • the present invention thus encompasses the use of the topical composition as recited above for a non- therapeutic cosmetic treatment of the skin and its appendages, in particular a depigmenting and/or anti-radical and/or anti- inflammatory treatment and/or a treatment to stimulate the molecules of the dermal extracellular matrix and/or to stimulate the molecules of the epidermal extracellular matrix and/or a moisturizing and/or anti-aging treatment.
  • a non- therapeutic cosmetic treatment of the skin and its appendages in particular a depigmenting and/or anti-radical and/or anti- inflammatory treatment and/or a treatment to stimulate the molecules of the dermal extracellular matrix and/or to stimulate the molecules of the epidermal extracellular matrix and/or a moisturizing and/or anti-aging treatment.
  • a non- therapeutic cosmetic treatment of the skin and its appendages in particular a depigmenting and/or anti-radical and/or anti- inflammatory treatment and/or a treatment to stimulate the molecules of the dermal extracellular matrix and/
  • Specific skin diseases can also be aimed, such as stretch marks, redness, reactive skin.
  • Skin treatments can include soothing, healing, etc.
  • polysaccharides from ulva lactuca algae are used.
  • the process is limited to the cleavage of ulvan polysaccharides priorly removed from glucuronan type polysaccharides and thus comprising mostly aldobiuronic sequences, the oligosaccharide mixture obtained being thus enriched in oligo-ulvans.
  • the obtaining process is preferably used consisting of:
  • the microorganism preferentially comes from the above mentioned bacterial strain referenced CNCM 1-3776, filed and recorded at the "Collection Nationale de Cultures de Microorganismes" (CNCM) at the Institut Pasteur, 25 rue du Dondel Roux, F-75724 Paris cedex 15 (FR), belonging to the University of Picardie Jules Verne, Chemin du Thil, F-80025 Amiens (FR).
  • CNCM Collection Nationale de Cultures de Microorganismes
  • micro-organisms can be used of the Flavobacteriaceae family, or Ochrobactrum and Rhizobium genus (including Rhizobium meliloti NCIMB 40472).
  • the oligosaccharides can be used in combination with one or more additional active ingredients, preferably to provide a range of wider cosmetic properties.
  • the additional active ingredients are used either to reinforce or to supplement activity.
  • the additional active ingredients can be for example selected from lightening agents, anti-redness, anti-spots, calming, for treating reactive or sensitive skins, UV sunscreens, moisturizing, humectant, exfoliating, smoothing, toning, firming, volumizing, anti-aging, anti-wrinkles and fine lines, improving the mechanical and elastic properties, skin radiance, detoxifying actives, anti-hair-growth, acting on cutaneous barrier, anti-acne, action of sebum secretion, matifying, unifying, antiinflammatory, anti-oxidant, anti-radical, anti-glycation, for eye contour (dark circles and under eye bags), promoting blood circulation, peptides, vitamins etc.
  • These active ingredients can be obtained from plant materials such as plant extracts or products of plant cell culture or fermentation.
  • oligosaccharides of the present invention can be combined advantageously with oligo-glucuronans, in particular the acetylated oligo-glucuronans disclosed in the patent application WO20120067327 and sold under the trade name SubliskinTM by Sederma.
  • oligo-glucuronans in particular the acetylated oligo-glucuronans disclosed in the patent application WO20120067327 and sold under the trade name SubliskinTM by Sederma.
  • They are oligomer compounds of D-glucuronic acid or D-glucuronate with a ⁇ (1-4) sequence according to the following formula (
  • each ring of glucuronic acid of formula (I) comprising an acetylation degree comprised between 8,7 ⁇ 0,5 and 9,2 ⁇ 0,5% in weight of 0-CO-CH 3 groups with regard to the weight of the glucuronic acid ring and a polymerisation degree comprised between 18 and 19 ⁇ 2.
  • These oligomer compounds act at the level of dermal and epidermal elasticity and increase the dermo-epidermal cohesion in order to fight against skin ageing, wrinkles, fine lines, tactile and/or visible skin discontinuities, loss of firmness, of elasticity and tonus, and to fight against cutaneous tissue deformability. They also act on skin hydration.
  • B3 vitamin compounds like niacinamide and tocopherol, retinoid compounds such as retinol, hexamidine, a-lipoic acid, resveratrol or DHEA, peptides, including N-acetyl-Tyr-Arg-O-hexadecyl, Pal-VGVAPG (SEQ ID NO: 1), Pal-KTTKS (SEQ ID NO: 2), Pal-GHK, Pal-KM0 2 K and Pal-GQPR (SEQ ID NO: 3) can be combined with the oligosaccharides of the present invention.
  • the present invention also aims a topical treatment method of the skin and its appendages, comprising the topical application to the skin and/or the appendages of an effective amount of a composition according to the invention comprising the oligosaccharides as recited above.
  • Topical treatment means according to the invention an application that is intended to act where it is applied: skin, mucous membranes, skin appendages.
  • Improvements in the appearance and general condition of the skin, mucous membranes, and appendages can be obtained by topical application on a regular basis such as daily.
  • the topical composition is preferably applied once daily for a period of at least a week, but it can be applied during periods of 2, 4, 8 or 12 weeks.
  • the topical composition is preferably applied to the face and neck, but can be applied to any part of skin requiring an aesthetic improvement, where the composition remains on the skin area to be treated, and preferably is not removed or flushed from the skin.
  • compositions of the present invention and the methods are suitable for use to treat skin conditions of the skin in many areas of the skin, including without limitation, the face, forehead, lips, neck, neckline, arms, hands, body, legs, knees, feet, chest, back, buttocks, and others.
  • One of the major advantages of the present invention resides in the ability whenever necessary or desirable to be able to apply local selective "gentle" treatments through this topical, non-invasive method of application.
  • anti-wrinkle use for example it may be applied very locally using a syringe or micro-canula.
  • the cosmetic treatment method according to the invention can be combined with one or more other treatment methods targeting the skin such as lumino-therapy, heat or aromatherapy treatments.
  • devices with several compartments or kits may be proposed to achieve the method described above which may include for example and non-restrictively, a first compartment containing a composition comprising the oligosaccharides of the invention, and in a second compartment a composition containing another active ingredient and/or excipient, the compositions contained in the said first and second compartments in this case being considered to be a combination composition for simultaneous, separate or stepwise use in time, particularly in one of the treatment methods recited above.
  • a mixture of polysaccharides comprised in the walls of ulva lactuca genus algae is heat extracted. After elimination of the insoluble elements, the pH of the extract is lowered to 2 with diluted acid in order to form a precipitate comprising glucuronic acid residues. The solution is thus recovered and brought to a neutral pH around 7. The solution is then purified, for example by ultrafiltration and precipitated with alcohol. The glucuronan polysaccharide fraction is thus eliminated and an ulvan polysaccharide is obtained comprising essentially aldobiuronic sequences, the glucuronan sequence left being in minority and the one integrated within the ulvan polysaccharide.
  • the aim is here to subject only the ulvan polysaccharide to enzymatic cleavage in order to recover oligo-ulvans in majority (a mixture enriched in oligo-ulvan) but it goes without saying that the process can also according to a variant be achieved on an ulvan and glucuronan polysaccharide mixture.
  • the mean molecular weight of the ulvan polysaccharide is determined by sterical exclusion chromatography coupled to a light diffusion detector in line with a refractometer (SEC-MALLS technolocy, for « Size Exclusion Chromatography Coupled to Multi-angle Laser-Light-Scattering »); this mean weight is 6.10 5 .
  • an enzymatic substance is prepared having potentially a double enzymatic activity: ulvan- lyase and glucuronan- lyase.
  • the strain is grown on a mineral minimal nutritive medium comprising: NaCl: 22g; Na 2 S0 4: 3.7g; KC1: 0.6g; KBr: O. lg; MgCl 2 ,6H 2 0: lOg; CaCl 2 ,2H 2 0: 2.94g; NaHC0 3 : 0.16g; NaN0 3 : 25mg; NaH 3 P0 4 ,12H 2 0: 5mg and H 2 0 QSP 1 liter; at a pH of 7.2.
  • the ulvan polysaccharide as prepared above (2g/L) is added to this nutrient medium as a carbone source substrate.
  • the strain capable of degrading this ulvan polysaccharide, is isolated on a petri dish containing the same nutrient medium supplemented with agar. After incubation, colonies of strain, which metabolize the substrate by degrading it according by ⁇ -elimination and which are the most developed, are gathered.
  • the CNCM 1-3776 strain is inoculated in a 2 liters capacity bioreactor, filled with 1.5 liters of a mineral medium: NaCl: 22g; Na 2 S0 4 : 3.7g; KC1 0.6g; KBr: O.lg; MgCl 2 ,7H 2 0: 5mg; NaN0 3 : 25 mg; NaH 3 P0 4 ,12H 2 0, H 2 0 qs 1 liter; at pH of 7.2 and supplemented with yeast extrac l g/L; peptone: 5 g/L and ulvan polysaccharide of (2g/L).
  • a mineral medium NaCl: 22g; Na 2 S0 4 : 3.7g; KC1 0.6g; KBr: O.lg; MgCl 2 ,7H 2 0: 5mg; NaN0 3 : 25 mg; NaH 3 P0 4 ,12H 2 0, H 2 0 qs 1 liter; at pH
  • Incubation is preferably carried out between 25 and 35°C under stirring for an average duration of 48 hours.
  • concentration of enzyme mixture (ulvan-lyase and glucuronan-lyase) in the culture medium of the strain increases and therefore the enzymatic activity of the culture medium increases as well.
  • the culture medium is then cleared of the bacteria after incubation followed by addition of ammonium sulfate (60% w/v) to precipitate the proteins contained therein. This is followed by centrifugation of the precipitated culture medium and recovering of the protein base which is then reintroduced into about 10 ml of a buffer solution of Tris/HCl 20 mM at pH 7.5.
  • the enzyme substance obtained above is applied to a substrate solution at 50g of ulvan polysaccharide for 1 liter of enzymatic solution.
  • the degradation experience is carried out at 20-30°C for a 3 hours incubation period (theoretically ranging from 1 to 72h).
  • the oligosaccharides have a polymerization degree DP comprised between 2 and 10, an average weight of 6kD and a sulfate ratio of 16.6%.
  • FHN are grown until confluence. At this stage, they are put in contact with the products to be tested for 24h, then the cell mat are irradiated (UVB 70mJ/cm2) and contacted again with the products for 24 hours. The amounts of synthesized PGE2, IL-6 and IL-8 are measured in the culture supernatants by ELISA assay.
  • ECM epidermal extracellular matrix
  • Human keratinocytes (HaCat) are cultured for 24h in plates. The cells are contacted or not with the products to be tested for 3 days. The culture supernatants are removed and the hyaluronic acid amount is assayed. Retinoic acid is used as a positive control.
  • FHN are seeded in well plates. After 24 hours of attachment, the cells are contacted for 24h with the products. Products are removed and the mats are rinsed. Cells are loaded for 30min with a "DCFH- DA" probe which becomes fluorescent in the presence of ROS (reactive oxygen species). After rinsing, the cells were placed again in contact with the products and the stress agent (800 ⁇ H 2 O 2 ) for 2 hours. A fluorescence reading is used to estimate the amount of ROS present in the cells.
  • ROS reactive oxygen species
  • FHN are grown in plate for 24 hours.
  • the cells are contacted or not with the products to be tested for 3 days.
  • the synthesis of collagen 1, collagen 4 and fibronectin is assessed by ELISA.
  • Mouse melanoma cells (B16) are cultured in plates in DMEMc medium (DULBECCO'S Modified Eagle Medium) + 10% FCS (fetal calf serum). After 24 hours of attachment, the cells are contacted with the products to evaluate in the same medium for 48 h. At the end of the contact, the culture media were removed and the total melanin was assayed by spectrophotometry.
  • DMEMc medium DULBECCO'S Modified Eagle Medium
  • FCS fetal calf serum
  • physiologically acceptable medium means according to the present invention, without limitation, an aqueous or hydro-alcoholic solution, a water-in-oil emulsion, an oil-in-water emulsion, a micro-emulsion, an aqueous gel, an anhydrous gel, a serum, a dispersion of vesicles or a powder.
  • physiologically acceptable means that the compositions are suitable for topical or transdermal use, in contact with mucous membranes, appendages (nails, hair, body hair), scalp and skin of mammals, particularly human, without risk of toxicity, incompatibility, instability, allergic response, and others.
  • the "physiologically acceptable medium” forms what is commonly called the excipient of the composition.
  • the choice of excipient of the composition is made according to the constraints of the oligosaccharides (stability, solubility, etc.), and if necessary according to the dosage form intended further for the composition.
  • the oligosaccharides of the invention may be incorporated into the composition by means of an aqueous solution, or be dissolved by the usual physiologically acceptable solubilizers, for example and without limiting to this list: ethanol, propanol, isopropanol, propylene glycol, glycerin, butylene glycol, or polyethylene glycol or any combination thereof. It may also be interesting to solubilize the extract with emulsifiers.
  • an aqueous or hydro-alcoholic solution is used as the physiologically acceptable medium.
  • the effective quantity of oligosaccharides depends on various factors such as the age, the condition of the patient, etc.
  • An effective amount means a not toxic amount enough to achieve the desired effect, which the skilled person is able to adapt.
  • compositions for the present invention are generally prepared by conventional methods well known to one skilled in the art. Such methods may involve a mixture of ingredients in one or more steps to obtain a uniform state, with or without heating, cooling, etc.
  • the different galenic forms that may contain the oligosaccharides of the invention can be all forms i.e. creams, lotions, milks or creams ointments, gels, emulsions, dispersions, solutions, suspensions, cleansers, foundations, anhydrous preparations (sticks in particular lip balm, body and bath oils), shower and bath gels, shampoo and hair care lotions, milks or creams for skin care or hair, cleansing lotions or milks, sunscreen lotions, milks or creams, artificial tanning lotions, milks or creams, pre shave, shaving or aftershave creams, foams, gels or lotions, makeup, lipstick, mascara or nail polish, skin essences, serums, adhesive or absorbent materials, transdermal patches, or emollient powders, lotions, milks or creams, sprays, body and bath oils, foundation basis, ointment, emulsion, colloid, compact suspension or solid, pencil, sprayable formulation, brushable, blush, red, eye
  • compositions may also be in the form of lipsticks intended either to color the lips or to prevent them from chapping, or makeup for eyes, eyes- shadows and foundations for the face.
  • compositions for the invention can include cosmetics, personal care products and pharmaceutical preparations.
  • a composition in the form of foam or in the form of aerosol compositions also comprising a pressurized propellant can be considered.
  • the oligosaccharides according to the present invention may be used in the form of solution, dispersion, emulsion, paste, or powder, individually or as a premix or vehicled individually or as a premix in vectors such as macro-, micro-, or nanocapsules, macro-, micro- or , nanospheres, liposomes, oleosomes or chylomicrons, macro-, micro-, or nanoparticles or macro-, micro or nanosponges, micro- or nanoemulsions, or adsorbed on organic polymer powders, talcs, bentonites, spores or exines, and other inorganic or organic supports.
  • vectors such as macro-, micro-, or nanocapsules, macro-, micro- or , nanospheres, liposomes, oleosomes or chylomicrons, macro-, micro-, or nanoparticles or macro-, micro or nanosponges, micro- or nanoemulsions, or adsorbed on organic poly
  • the oligosaccharides according to the present invention may be used in any form whatsoever, in a form bound to or incorporated in or absorbed in or adsorbed on macro-, micro-, and nanoparticles, or macro-, micro-, and nano-capsules, for the treatment of textiles, natural or synthetic fibers, wools, and any materials that may be used for clothing or underwear for day or night, handkerchiefs or cloths, intended to come into contact with the skin, to exert their cosmetic effect via this skin/textile contact and to permit continuous topical delivery.
  • CTFA International cosmetic ingredient dictionary & handbook (13th Ed. 2010)
  • Cosmetic, Toiletry, and Fragrance Association, Inc. Washington, D.C.
  • CTFA Cosmetic, Toiletry, and Fragrance Association
  • additional ingredients can be synthetic or natural such as plants extracts, or come from bio- fermentation process.
  • Further skin care and hair care active ingredients that are particularly useful combined with the composition can be found in SEDERMA commercial literature and on the website www.sederma.fr.
  • betain betain, glycerol, Actimoist Bio 2TM (Active organics), AquaCacteenTM (Mibelle AG Cosmetics), AquaphylineTM (Silab), AquaregulKTM (Solabia), CarcilineTM (Greentech), CodiavelaneTM (Biotech Marine), DermafluxTM (Arch Chemicals, Inc), Hydra'FlowTM (Sochibo), Hydromoist LTM (Symrise), RenovHyalTM (Soliance), SeamossTM (Biotech Marine), ArgirelineTM (trade name of the acetyl hexapeptide-3 of Lipotec), spilanthol or an extract of Acmella oleracea known under the name Gatuline ExpressionTM, an extract of Boswellia serrata known under the name BoswellinTM, Deepaline PVBTM (Seppic), Syn-AKETM (Pentapharm), AmelioxTM, BioxiliftTM (Silab), Subl
  • extracts of Ivy in particular English Ivy (Hedera Helix), of Bupleurum chinensis, of Bupleurum Falcatum, of arnica (Arnica Montana L), of rosemary (Rosmarinus officinalis N), of marigold (Calendula officinalis), of sage (Salvia officinalis L), of ginseng (Panax ginseng), of Zingiber zerumbet sm., of ginko biloba, of St.
  • Camelia sinensis of Imperata cylindrica, of Glaucium Flavum, of Cupressus Sempervirens, of Polygonatum multiflorum, of loveyly hemsleya, of Sambucus Nigra, of Phaseolus lunatus, of Centaurium, of Macrocystis Pyrifera, of Turnera Diffusa, of Anemarrhena asphodeloides, of Portulaca pilosa, of Humulus lupulus, of Coffea Arabica, of Ilex Paraguariensis, or of Zingimber Zerumbet Smith.
  • compositions of the present invention may include peptides, including, without limitation, the di-, tri-, terra-, penta-and hexapeptides and their derivatives.
  • concentration of the additional peptide, in the composition ranges from lxl0 ⁇ 7 % and 20%, preferably from lxl0 "6 % and 10%, preferably between lxl0 "5 % and 5% by weight.
  • peptide refers to peptides containing 10 amino acids or less, their derivatives, isomers and complexes with other species such as a metal ion (e.g. copper, zinc, manganese, magnesium, and others).
  • a metal ion e.g. copper, zinc, manganese, magnesium, and others.
  • peptides refers to both natural peptides and synthetic peptides. It also refers to compositions that contain peptides and which are found in nature, and/or are commercially available.
  • Suitable dipeptides for use herein include but are not limited to Carnosine (beta-AH), YR, VW, NF, DF, KT, KC, CK, KP, KK or TT.
  • Suitable tripeptides for use herein include, but are not limited to RKR, HGG, GHK, GKH, GGH, GHG, KFK, KPK, KMOK, KM0 2 K or KAvaK.
  • Suitable tetrapeptides for use herein include but are not limited to RSRK (SEQ ID NO: 4), GQPR (SEQ ID NO: 5) or KTFK (SEQ ID NO: 6).
  • Suitable pentapeptides include, but are not limited to KTTKS (SEQ ID NO: 7).
  • Suitable hexapeptides include but are not limited to GKTTKS (SEQ ID NO: 8) and VGVAPG (SEQ ID NO: 9).
  • Suitable peptides for use herein include, but are not limited to: lipophilic derivatives of peptides, preferably palmitoyl derivatives, and metal complexes as aforementioned (e.g. copper complex of the tripeptide HGG).
  • Preferred dipeptide include for example N-Palmitoyl-beta-Ala-His, N-Acetyl-Tyr- Arg-hexadecylester (CalmosensineTM, IdealiftTM from Sederma).
  • Preferred tripeptide derivatives include for example N-Palmitoyl-Gly-Lys-His, and Pal-Gly-His-Ly, (Pal-GKH and Pal-GHK from Sederma), the copper derivative of HGG (LaminTM from Sigma), Lipospondin (N-Elaidoyl-KFK) and its analogs of conservative substitution, N-Acetyl-RKR-NH 2 (Peptide CK+), N-Biot-GHK (from Sederma), Pal-KM0 2 K (Matrixyl Synthe6TM from Sederma) and derivatives thereof.
  • Suitable tetrapeptide derivatives for use according to the present invention include, but are not limited to, N- pal-GQPR (SEQ ID NO: 3) (from Sederma), suitable pentapeptide derivatives for use herein include, but are not limited to, Pal-KTTKS (SEQ ID NO: 2) (available as MatrixylTM from Sederma), Pal- YGGF-X (SEQ ID NO: 10) with X Met or Leu or mixtures thereof.
  • Suitable hexapeptide derivatives for use herein include, but are not limited to, Pal- VGVAPG (SEQ ID NO: 1) and derivatives thereof.
  • the mixture of Pal-GHK and Pal-GQPR (SEQ ID NO: 3) (MatrixylTM 3000, Sederma) can also be mentioned.
  • compositions commercially available containing a tripeptide or a derivative include Biopeptide-CLTM, MaxilipTM, BiobustylTM, ProcapilTM and MatrixylTMsynthe'6TM of Sederma.
  • compositions commercially available preferred sources of tetrapeptides include RiginTM, EyelissTM, MatrixylTM Reloaded and Matrixyl 3000TM which contain between 50 and 500 ppm of Pal-GQPR (SEQ ID NO: 3) and an excipient, proposed by Sederma.
  • peptides can be mentioned as well as additional active ingredients: VialoxTM, Syn-akeTM or Syn-CollTM (Pentapharm), Hydroxyprolisilane CNTM (Exsymol), ArgirelineTM, LeuphasylTM, AldenineTM, TrylgenTM, EyeserylTM, SerilesineTM or DecorinylTM (Lipotec), CollaxylTM or QuintescineTM (Vincience), BONT-L-PeptideTM (lnfinitec Activos), CytokinolTMLS (Laboratoires Serobi GmbH/Cognis), KollarenTM, IP2000TM or MelipreneTM (lnstitut Europeen de Biologie Cellulaire), NeutrazenTM (Innovations), ECM-ProtectTM (Atrium Innovations), Timp-PeptideTM or ECM ModulineTM (lnfmitec Activos).

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  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une composition topique comprenant : -un mélange d'oligosaccharides sulfatés bioactifs présentant un degré de polymérisation (DP) compris entre 2 et 10, et - un milieu physiologiquement acceptable ; lesdits oligosaccharides étant obtenus selon un procédé de clivage enzymatique selon une réaction de β-élimination de polysaccharides extraits d'algues vertes du genre ulva comprenant des séquences aldobiuroniques et des séquences glucuronane, au moyen d'une enzyme de type ulvane lyase adaptée au clivage de la liaison osidique entre les unités de Glcp A et de Rhap3 sulfate et entre les unités Idop A et Rhap3, et au moyen d'une enzyme de type glucuronane lyase adaptée au clivage de la liaison osidique entre deux unités Glcp A. Une telle composition présente une activité cosmétique particulièrement intéressante sur les cellules cutanées, notamment des effets anti-inflammatoires, anti-radicaux, de dépigmentation et des effets sur des molécules de la matrice extracellulaire dermique (telles que le collagène 1, le collagène 4 et la fibronectine), sur des molécules de la matrice extracellulaire épidermique (acide hyaluronique). Applications : antivieillissement et hydratation
EP13722557.9A 2012-03-30 2013-03-28 Composition topique comprenant des oligosaccharides sulfatés bioactifs et utilisations cosmétiques Withdrawn EP2830585A2 (fr)

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FR1252940A FR2988606B1 (fr) 2012-03-30 2012-03-30 Composition topique comprenant des oligosaccharides sulfates bioactifs et utilisations cosmetiques
PCT/IB2013/052516 WO2013144909A2 (fr) 2012-03-30 2013-03-28 Composition topique comprenant des oligosaccharides sulfatés bioactifs et utilisations cosmétiques

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EP2830585A2 true EP2830585A2 (fr) 2015-02-04

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Families Citing this family (5)

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Publication number Priority date Publication date Assignee Title
FR3011248B1 (fr) * 2013-09-27 2021-05-21 Sederma Sa Procede d'obtention d'oligosaccharides bioactifs clives, micro-organisme pour sa mise en œuvre, oligosaccharides obtenus et leur utilisation cosmetique
FR3020570B1 (fr) * 2014-04-30 2017-07-21 Pierre Fabre Dermo-Cosmetique Association d'un acide hyaluronique et d'un polysaccharide sulfate
KR20170118885A (ko) * 2015-03-26 2017-10-25 이엘씨 매니지먼트 엘엘씨 각질세포의 지질 함유량 증가를 위한 조성물
FR3057770B1 (fr) * 2016-10-21 2019-07-19 Seprosys Utilisation d'un extrait d'ulve comme agent cosmetique anti-age
FR3075644B1 (fr) * 2017-12-27 2020-08-28 Oreal Oligosaccharides sulfates et leurs utilisations cosmetiques

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FR2868253B1 (fr) * 2004-03-30 2006-07-21 Cie Financiere Et De Participa Utilisation des ulvanes comme activateurs des reactions de defense des plantes et de resistance contre des contraintes biotiques ou abiotiques
FR2917750B1 (fr) * 2007-06-22 2013-02-08 Univ Picardie Procede de clivage enzymatique de polysaccharides issus des algues
FR2961526B1 (fr) * 2010-06-18 2012-09-07 Centre Nat Rech Scient Ulvane lyase, procede de fabrication et utilisations
EP2593546A4 (fr) 2010-07-16 2014-01-01 Valorisation Recherche Ltd Partnership Purification par affinité d'arn dans des conditions d'origine sur la base de l'interaction lambda boîteb/n peptide

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WO2013144909A3 (fr) 2014-03-06
WO2013144909A2 (fr) 2013-10-03
FR2988606B1 (fr) 2014-08-08
FR2988606A1 (fr) 2013-10-04

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