WO2010115472A2 - Composition topique pour l'éclaircissement de la peau - Google Patents

Composition topique pour l'éclaircissement de la peau Download PDF

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Publication number
WO2010115472A2
WO2010115472A2 PCT/EP2009/054331 EP2009054331W WO2010115472A2 WO 2010115472 A2 WO2010115472 A2 WO 2010115472A2 EP 2009054331 W EP2009054331 W EP 2009054331W WO 2010115472 A2 WO2010115472 A2 WO 2010115472A2
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WO
WIPO (PCT)
Prior art keywords
composition
skin
extract
composition according
rumex
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PCT/EP2009/054331
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English (en)
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WO2010115472A3 (fr
Inventor
Eve Merinville
Aurelie Laloeuf
Geraldine Bouvry
Adam Muggleton
Anthony V. Rawlings
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Oriflame Cosmetics S.A.
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Priority to PCT/EP2009/054331 priority Critical patent/WO2010115472A2/fr
Publication of WO2010115472A2 publication Critical patent/WO2010115472A2/fr
Publication of WO2010115472A3 publication Critical patent/WO2010115472A3/fr

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    • 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
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9706—Algae
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

  • Topical skin lightening composition Topical skin lightening composition
  • the present invention relates to cosmetic compositions, in particular topical compositions for dermatological skin lightening and/or for preventing skin tanning.
  • Dermatological compositions for use in skin lightening and skin darkening are well known.
  • the cosmetic treatment of skin to produce a visible even-tone has been practiced widely in many parts of the world.
  • the use of plant-derived extracts and salves to whiten or brighten dark coloured skin has traditionally been very popular among Asian, African, and South American cultures.
  • the even toning of age-related dark spots, skin pigmentation, freckles, and other skin pigmentation disorders with skin lightening products is also gaining popularity among people of light-coloured skin.
  • the colour of human skin is differentiated by the nature and quantity of natural pigment, melanin, present in the epidermal layers of skin.
  • melanin present in the epidermal layers of skin.
  • the formation of melanin from the amino acid tyrosine involves several biogenetic steps mediated initially by the enzyme tyrosinase. Tyrosine is first oxidized by tyrosinase to dihydroxyphenylalanine (I-dopa), then to dopaquinone. Dopaquinone is then converted into eumelanin (black, white, and Asian skin types; skin colour dependent on the quantity of eumelanin in skin), or phaeomelanin (red- haired skin types). This conversion proceeds through the intermediate formation of leucodopachrome and dopachrome (eumelanin), or cysteinyldopa (phaeomelanin).
  • compositions to lighten or whiten skin colour or skin tone which may include natural and synthetic actives, are well known in the art. Many skin whitening or lightening compositions are commercially available. Many of these include ingredients which have been shown to be tyrosinase inhibitors.
  • U.S. Patent No. 6,521,267 of Fytochem describes a Rumex extract, which is a blend of tyrosinase inhibiting extracts from dictotyledonous plant species, including Rumex occidentalis , Rumex pseudonatromatus , Rumex stenophyllus, Rumex maritimus and Rumex Crispus, indigenous to Canada and compositions containing the extracts for the treatment of skin, particularly skin lightening.
  • Tyrostat-9 is a skin whitening product which is commercially available from Fytochem and which contains the Rumex extract, described by the INCI/CTFA regulation as Rumex occidentalis extract.
  • EP 0 662 946 describes novel polyunsaturated dioic acids having between 8 and 16 carbon atoms (inclusive), including 8-hexadecene-l,16-dicarboxylic acid and their use in the treatment of skin for medical and cosmetic purposes, such as acne treatment and skin lightening.
  • 8-hexadecene-l,16-dicarboxylic acid is commercially available under the trademark O.D.A White from Croda/Sederma.
  • U.S. Patent Publication No. 2007041931 describes topical compositions comprising soy products and dioic acids and their use in skin lightening, for improving the appearance of the skin and for treating hyperpigmentation, in particular for improving the appearance of age spots.
  • U.S. Patent Publication No. 2008152604 describes cosmetic or dermatological preparations which are comprised of 0.01 to 5% by weight of a dicarboxylic acid selected from the group consisting of 8-hexadecene-l,16-dicarboxylic acid, decanedioic acid, nonanedioic acid and combinations thereof and from 0.01 to 5% by weight of ascorbic acid, salts of ascorbic acid, ascorbic acid derivatives and combinations thereof.
  • These preparations provide skin- lightening and/or hair-lightening preparations which inhibit melanin biosynthesis.
  • the use of ascorbic acid is known to have the disadvantage that it is an unstable compound and may degrade in formulation.
  • EP 1 940346 describes the preparation of personal care compositions comprising skin and/or hair care actives for regulating the condition of mammalian keratinous tissue, particularly in the preparation of skin lightening compositions.
  • Specified compositions may contain 8- hexadecene-1 ,16-dicarboxylic acid in combination with a range of other cosmetic actives.
  • U.S. Patent Publication No. 20050019279 describes cosmetic or dermatological preparations comprising at least one UV filtering substance and 8-hexadecene-l,16-dicarboxylic acid.
  • the invention concerns a method of using the preparation to treat or prevent undesired skin aging, skin pigmentation, or skin pigment disorders, and a method of using the preparation to lighten or prevent undesired pigmentation of the hair.
  • the formulations described in this patent aim to improve the skin lightening effect by adding sunscreens to reduce skin tanning.
  • hydrobezophenones are exemplified as sunscreen agents in the patent, the use of benzophenone derivatives in general, are widely unfavoured for use in cosmetic preparations due to their association with reported cases of allergic skin reactions.
  • hydroquinone One of the best-known active substances for de -pigmentation is hydroquinone. It does not inhibit melanin biosynthesis, rather it bleaches existing melanin. Hydroquinone has been reported to exhibit serious side effects when used. This has led to it being permitted only in limited concentrations in some countries, and to it being completely forbidden for applications in cosmetic products in other countries.
  • Alternative skin lightening substances currently being used of natural origin include arbutin (from the leaves of the common bearberry, Arctostaphylos uva urs ⁇ ), liquorice extract (from liquorice root), ascorbic acid (vitamin C from citrus fruits) and their derivatives, as well as kojic acid (from carbohydrate solutions under the effect of certain bacteria).
  • U.S. Patent No. 5,279,834 describes a cosmetic or pharmaceutical composition, containing hydroquinone and kojic acid or a derivative thereof, especially the salts or esters thereof in their use as topical skin-lightening formulations.
  • Kojic acid is known to have an uncertain safety profile and has been reported to induce the sensitization of human skin.
  • U.S. Patent No. 5,980,904 describes a skin-whitening composition that includes bearberry extract and a reducing agent to boost the skin whitening efficacy of the bearberry extract.
  • U.S. Patent No. 5,916,915 discloses certain ascorbic acid derivatives for skin whitening applications whilst U.S. 5,824,327 discloses the use of certain derivatives of kojic acid, which are suitable as tyrosinase inhibiting skin-whitening agents.
  • a number of skin whitening compositions have become commercially available, most of which are tyrosinase inhibitors.
  • Gattefosse for example, markets 'Gatulin Whitening', which is a mixture of Aspergillus Orizae and Liquorice extracts.
  • Gattefosse also markets 'Synerlight', which is a mixture of Sophora root extract, kiwi water and ascorbic acid, and 'Mulberry Extract', for skin whitening applications.
  • Sederma market the product, 'Etioline', which is a mixture of Mitracarpus scaber extract and bearberry (Arctostaphylus uva ursi) extract and is a skin whitening tyrosinase inhibitor.
  • Sederma also market the skin-whitening compositions, 'Melaslow' and 'Melaclear', both of which are based on tyrosinase inhibitors.
  • Silab market the tyrosinase inhibiting compositions, 'Dermalight', based on nasturtium petals and 'Clariskin' derived from a wheat germ extract whilst Alpafior offers "Gigawhite", a skin whitening composition based on a mixture of several tyrosinase inhibiting botanical extracts including Malva sylvestris, Mentha piperita, Primula veris, Alchemilla vulgaris, Veronica officinalis, Melissa officinalis, and Achillea millefolium.
  • the invention provides a cosmetic composition for skin lightening comprising:
  • the composition according to the invention may comprise a topical composition comprising a combination of an extract of at least one Rumex plant species and 8-hexadecene-l,16- dicarboxylic acid. It has now been discovered, totally surprisingly and unexpectedly, that the use of a combination of an extract of at least one Rumex plant species and 8-hexadecene- 1 ,16-dicarboxylic acid makes it possible to prepare a cosmetic composition, in particular a dermatological composition, where the combination of actives exhibits a synergistic effect in skin whitening activity.
  • the composition according to the invention demonstrates a synergistic inhibition of melanin synthesis.
  • the composition when applied to the skin lightens the skin colour. The extent of the lightening effect observed is greater than the mere additive effect that would be expected to be observed by the combination of actives. This synergistic effect observed is a surprising and unexpected technical effect.
  • composition according to the invention suitably comprises a blend of two or more extracts of Rumex plant species.
  • the blend of Rumex extract may be obtained from a blend of extracts from the Rumex plant species indigenous to Canada, including Rumex occidentalis, Rumex pseudonatromatus, Rumex stenophyllus , Rumex maritimus and Rumex Crispus.
  • the extract may be obtained from the Rumex plant or plant part.
  • Rumex occidentalis is also known as Western field dock.
  • the Rumex occidentalis extract may be obtained from the plant or plant part, for example, the leaves, stem, flowers or root.
  • the extract used in accordance with the present invention is obtained from the flowering aerials and fruiting aerials of Rumex occidentalis .
  • Rumex pseudonatromatus is also known as Field dock.
  • the Rumex pseudonatromatus extract may be obtained from the plant or plant part, for example, the leaves, stem, flowers or root.
  • the extract used in accordance with the present invention is obtained from the fruiting aerials and fruits of Rumex pseudonatromatus. Rumex stenophyllus is also known as Narrow-leaved dock.
  • the Rumex stenophyllus extract may be obtained from the plant or plant part, for example, the leaves, stem, flowers or root.
  • the extract used in accordance with the present invention is obtained from the fruits of Rumex stenophyllus .
  • Rumex maritimus is also known as Golden dock.
  • the Rumex maritimus extract may be obtained from the plant or plant part, for example, the leaves, stem, flowers or root.
  • the extract used in accordance with the present invention is obtained from the fruiting aerials of Rumex maritimus.
  • Rumex Crispus is also known as Curled dock.
  • the Rumex Crispus extract may be obtained from the plant or plant part, for example, the leaves, stem, flowers or root.
  • the extract used in accordance with the present invention is obtained from the fruiting aerials of Rumex Crispus.
  • the composition suitably comprises a blend of Rumex plant extract in an amount in the range 0.002% to 5% (w/w).
  • the composition may comprise 8-hexadecene-l,16-dicarboxylic acid in an amount in the range 0.05% to 5% (w/w).
  • the skilled person will appreciate that the amounts of each of the actives present in the composition can be selected according to the requirements for the end product.
  • the dermatologically acceptable carrier may be selected from the group consisting of water, liquid or solid emollients, humectants and solvents. The skilled person will appreciate that other suitable carriers could also be used.
  • the dermatologically acceptable carrier forms between 5% to 99.9%, preferably from 25% to 90% by weight of the composition.
  • the carrier can, in the absence of other cosmetic adjuncts, form the balance of the composition.
  • composition according to the invention may further comprise agents selected from the group consisting of silicones, emulsifiers, thickeners, powders, film formers, rheology modifying agents, propellants and combinations thereof. It will be appreciated by the person skilled in the art that the composition may comprise any other suitable adjuncts.
  • the composition may further include adjuncts such as fragrance, opacifiers, preservatives, colourants, pigments, buffers, chelating agents, sensory enhancers, etc.
  • the composition may further comprise skin-care actives such as UV filters (such as Ethylhexyl Methoxycinnamate, Octocrylene, Ethylhexyl Salicylate, Butyl Methoxydibenzoylmethane, Titanium Dioxide or Phenylbenzimidazol Sulfonic Acid, for example), anti-ageing actives (for example vitamins or proteins), anti-wrinkle actives, moisturising actives, antioxidants, skin purifying actives, peeling agents, sebum reducing agents, mattifying agents, anti-perspirant actives, surfactants and other cleansing agents, delivery enhancers and the like.
  • skin-care actives such as UV filters (such as Ethylhexyl Methoxycinnamate, Octocrylene, Ethylhexyl Salicylate, Butyl Methoxydibenzoylmethane, Titanium Dioxide or Phenylbenzimidazol Sulfonic Acid, for
  • Skin lightening agents such as inhibitors of protein kinase A, inhibitors of protein kinase C- beta, inhibitors of GTP-cyclohydrolase-1, melanin concentration hormone receptor agonists, phenylalanine uptake inhibitors, ionotropic and metabotropic glutamate receptor antagonists and mixtures thereof, may also be included in the composition according to the invention.
  • the composition further comprises one or more skin care actives selected from the group consisting of alpha-hydroxy acids, beta-hydroxy acids, polyhydroxy acids, hyaluronic acid, algae extracts, peptides, vitamin C derivatives, conjugated linoleic acid, allantoin, retinoids, resorcinol derivatives, alpha-arbutin, tannins, fiavanoids, ellagic acid, gallic acid and mixtures thereof.
  • skin care actives selected from the group consisting of alpha-hydroxy acids, beta-hydroxy acids, polyhydroxy acids, hyaluronic acid, algae extracts, peptides, vitamin C derivatives, conjugated linoleic acid, allantoin, retinoids, resorcinol derivatives, alpha-arbutin, tannins, fiavanoids, ellagic acid, gallic acid and mixtures thereof.
  • composition according to the invention may further comprise a therapeutically effective amount of Adenophora stricta extract.
  • Adenophora stricta extract is a skin lightening agent derived from Adenophora stricta miq. (commonly known as 'Lady Bells' or "Na Sha Shen").
  • Adenophora stricta extract may be obtained from the plant or plant part, for example, the leaves, stem, flowers or root.
  • the extract used in accordance with the present invention is obtained from the roots of Adenophora sticta miq.
  • the vehicle may be formulated to improve the delivery of the actives to the skin.
  • the topical composition according to the present invention may be prepared in a manner well known in the art of preparing skin care products.
  • the active components are generally incorporated in a dermatologically acceptable vehicle or carrier.
  • the active components can suitably first be dissolved or dispersed in a portion of the water or another solvent or liquid to be incorporated in the composition.
  • the composition according to the invention may be in the form of conventional skin-care products.
  • the composition is in the form of an emulsion, cream, lotion, milk, serum, concentrate or gel.
  • the composition may be in the form of an emulsion, such as the oil-in-water, water-in-oil, silicone-in-water, water-in-silicone types, or a multiple emulsion such as a triple emulsion (for example water/oil/water (W/O/W) emulsion) or a Phase Inversion Temperature (P.I.T.) emulsion or the like.
  • compositions may also be in the form of a gel, a solution, a dispersion (for example a hydro -dispersion or lipo-dispersion), a paste or a solid (for example, a solid stick).
  • a dispersion for example a hydro -dispersion or lipo-dispersion
  • a paste or a solid for example, a solid stick
  • the compositions may be in the form of an alcohol-based system or an aerosol.
  • the composition is in the form of an emulsion, in particular an oil-in-water emulsion or a water-in-oil emulsion.
  • the composition may alternatively be in the form of conventional skin-care products such as a gel, gel-cream, milk, oil (for example massage oil), scrub, powder, mask or the like.
  • the composition may also be in the form of a soap or a cleanser (such as a facial cleanser), a shampoo, a shower or bath gel.
  • the composition may also be a colour cosmetic product such as a foundation, a base for make-up, a concealer, a mascara or a lipstick. It may also be incorporated into a wrap or film, a mask, a patch, a cloth or blanket, a pad, a sheet, a wipe or the like.
  • the product is a leave-on topical product, that is, a product to be applied to the skin without a deliberate rinsing step soon after its application to the skin.
  • the composition may be packaged in any suitable manner such as a jar, a bottle, a tube, a pump, a pump dispenser-tube, an aerosol or foam dispensing pump, a roll-ball, a stick, a brush or a sachet, for example. It may also be incorporated in a capsule, an ampoule or a pipette (for example a dropper system).
  • the invention also provides for the use of (i) a therapeutically effective amount of an extract of at least one Rumex plant species; (ii) a therapeutically effective amount of 8-hexadecene- 1 ,16-dicarboxylic acid; and (iii) a dermatologically acceptable carrier, in the manufacture of a cosmetic composition for skin lightening.
  • the invention also provides a cosmetic method for lightening the skin, comprising applying the composition as described herein to the skin in the morning and/or evening.
  • dermatologically acceptable carrier means that the carriers described are suitable for use in contact with mammalian keratinous tissue without causing any adverse effects such as undue toxicity, incompatibility, instability, allergic response, for example.
  • terapéuticaally effective amount means an amount effective to inhibit melanin production and thereby causing a skin lightening effect.
  • Figure 1 shows a graph highlighting the percentage of melanin content remaining in skin equivalents (reconstructed tanned epidermis) after successive treatments with actives used in the composition according to the invention.
  • the present invention relates to cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological changes in skin.
  • Such changes include undesired pigmentation, local hyperpigmentation and incorrect pigmentation (such as dark spots, age/liver spots and freckles), the inhibition of natural pigmentation and for the purely cosmetic lightening of relatively large areas of skin, to help brighten skin and even out skin tone.
  • Problems with skin hyperpigmentation have a wide variety of causes and are accompanying phenomena of many biological processes, for example UV radiation (for example, freckles, ephelides), genetic disposition, incorrect pigmentation of the skin during wound healing or scarring or skin aging (Lentigines seniles).
  • the present invention addresses an identified need for improved dermatological skin lightening and/or whitening compositions by providing a topical cosmetic composition which demonstrates a synergistic effect on the inhibition of melanin synthesis.
  • Melanogenesis is the complex physiological process that leads to melanin formation.
  • Melanin is the dark pigment responsible for skin color.
  • the initiation of melanogenesis in the skin is caused by various types of stimuli, both external and internal, such as, UV radiation, free radicals, hormones and irritation (paracrine and endocrine factors).
  • Melanocytes and keratinocytes are the two types of epidermal cells involved in melanogenesis for which melanocytes represent the main machinery and keratinocytes are the epidermal carrier of melanin responsible for visible skin color.
  • the spatial organisation of melanocytes and keratinocytes allows optimum cell-to-cell contact in order to maximise the efficacy of the epidermal melanin unit (1 melanocyte for 36 keratinocytes).
  • Melanocytes are multi-dendritic cells present in the innermost layer of the epidermis layer. They are responsible for production of melanin and its transfer to surrounding keratinocytes via their dendrites. Melanin formation is a complex enzymatic process that requires the presence of tyrosinase and tyrosinase-related proteins 1 and 2 (TYRP 1, TYRP 2). The biosynthetic pathway for melanin starts with the hydroxylation of tyrosine to 3-4 dihydroxyphenylalanine (DOPA) and continues with the oxidation of DOPA into Dopaquinone. These steps are fully dependent on tyrosinase activity and stability.
  • DOPA dihydroxyphenylalanine
  • melanins which consists of two types of melanin, namely, eumelanin, an insoluble black-brown pigment, and pheomelanin, a somewhat soluble and red-yellow pigment.
  • TYRP 1 and 2 are involved in this second phase of melanin production.
  • TYRP 1 is thought to stabilise tyrosinase therefore increasing its half-life.
  • the ratio TYRP 1:2 will affect the ratio of eumelanin and pheomelanin produced and therefore influence global skin colour.
  • Keratinocytes express a specific trans-membranar receptor from the protease-activated receptor (PAR) family: PAR- 2. Once activated by trypsin and other factors, PAR-2 induces the phagocytosis of melanosomes by keratinocytes, allowing the enrichment in melanin of the lower epidermal layers to happen, encouraged by the dynamic cell renewal.
  • PAR-2 protease-activated receptor
  • composition according to the invention comprises a combination of an extract of at least one Rumex plant species and S-hexadecene-l J ⁇ -dicarboxylic acid, together with a dermatologically acceptable carrier. This particular combination of actives demonstrates a surprising synergistic effect on the inhibition of melanin synthesis.
  • Rumex extract acts on melanogenesis by competitive inhibition of tyrosinase. Further data suggests Rumex extract is able to bind onto the enzyme's active site, thereby inhibiting the substrate reduction which normally leads to melanin production (Simonot D., McCoIl J and Thome D. Cosmetic & Toiletries magazine 2002, March, 117 (3):51-56). The data also shows that combining two other well-known skin lightening ingredients, kojic acid and arbutin, with Rumex extract, does not create any synergistic effect and remains inconclusive.
  • Rumex extract as used in the present invention, demonstrates synergistic activity on skin lightening when combined with another skin lightening agent, such as 8-hexadecene-l,16-dicarboxylic acid, for example.
  • the peroxisome proliferator-activated receptor is a transcription factor belonging to the family of ligand-inducible nuclear receptors, which are able to influence the transcription of a target gene. PPARs are thought to influence melanogenesis initiation, especially the PPAR subtype ⁇ has been found in melanoma cells and melanocytes. (M ⁇ ssner R., Schulz U., Kr ⁇ ger U. et al. J Invest Dermatol 2002; 119:576-582).
  • ⁇ -hexadecene-l j ⁇ -dicarboxylic acid is a PPAR ⁇ agonist and has been shown to influence normal skin pigmentation this way. Its binding ability onto PPAR ⁇ decreases tyrosinase mRNA production, which, in turn, leads to the reduction in the tyrosinase levels. As a result, the capacity of melanocytes to synthesise melanin is diminished. (Wiechers JW., Rawlings AV., Garcia C. et al. Int J Cosmetic Sci 2005, 27:123-132).
  • AsA ascorbic acid
  • DHICA 5,6-dihydroxyindole-2-carboxylic acid
  • Magnesium L ascorbic - 2 phosphate is a stabilised form of Vitamin C and remains its most potent and used derivative.
  • MgAP reduces skin pigmentation by indirectly reducing melanocytes dendricity and thereby melanosome transfer (Regnier M., Tremblaye C. Pigment Cell Res. 2005; 18:389-390).
  • These dramatic morphological changes of melanocytes are keratinocytes mediated.
  • the ability of melanosomes to be trafficked along dendrites and then transferred to the keratinocytes is of critical importance for skin pigmentation.
  • Compounds like AsA and soy products target this specific phase of melanogenesis in order to affect skin color.
  • the skilled person will appreciate that the mechanism of action of soy products, AsA and its derivatives on melanogenesis is clearly different from the mechanism of action of Rumex extract.
  • Skin equivalents were purchased from MatTek Corporation (USA). They consist of normal, human-derived epidermal keratinocytes (NHEK) and melanocytes (NHM), which have been cultured to form a multilayered, three-dimensional and highly differentiated model of the human epidermis. The NHM undergo spontaneous melanogenesis leading to visible tissue pigmentation. Overall the skin equivalent is a useful in vitro model for the evaluation of agents designed to influence skin pigmentation. In addition it exhibits in vzvo-like morphological and ultrastructural characteristics which are uniform and highly reproducible. All of the pigmentation machinery is included in this model and can therefore be responsive to materials that affect any of the pigmentation targets.
  • the Skin Equivalent inserts were received from MatTek after three weeks of differentiation and placed in 6-well plates containing maintenance media (MatTek). They were then placed in the incubator (37 0 C and 5% CO 2 ) for an hour in order to get them ready for the treatment phase.
  • the Rumex extract used in this example refers to the blend of indigenous Canadian plants extracts described herein, that is, Rumex occidentalis, Rumex pseudonatromatus , Rumex stenophyllus, Rumex maritimus and Rumex Crispus.
  • 8-hexadecene-l ,16-dicarboxylic acid stock solution was made up in an aqueous solution containing 5% of DMSO. Then, active test compounds were made up to the appropriate concentration directly in fresh maintenance media. To test for synergy, 8-hexadecene-l,16- dicarboxylic acid stock solution and Rumex extract were combined into the fresh maintenance media at the concentration indicated, for treatment on the skin equivalents.
  • Negative control treatment was included at 0.06mg/mL as a separate treatment.
  • Negative control treatment consisted of 0.1% DMSO (as this was the vehicle carrier for 8-hexadecene-l ,16-dicarboxylic acid).
  • the skin lightening effect of a compound on skin equivalents is measurable by quantifying the melanin remaining into the tissue (melanocytes specifically) after treatment and comparing it to the untreated control. This gives the percentage of melanin synthesis inhibition for a specific compound.
  • Pure melanin is soluble in strong base (NaOH). Solutions of different concentrations of melanin (Sigma Aldrich) were prepared: 0, 10, 25, 50 and lOO ⁇ M/mL of melanin for standard curve establishment. Skin equivalents were carefully detached from their inserts and rinsed several times in PBS, then carefully dried with a dry cloth. Each tissue was placed in an individual ImL tube to which ImL of strong base solution was added. Tubes were heated at 100 0 C for 45 min to allow the melanin extraction. Once the content of the tubes was well homogenized and had cooled down, 150 ⁇ L (in duplicate) was pipetted from each tube and transferred into a 96- well plate. The same was done for the standard curve solutions.
  • the colour intensity of the solutions due to melanin was determined by measuring the light absorbance at 495nm with a microplate reader. The amount of melanin was then determined by extrapolating the melanin standard curve. The less melanin there is, the more effective the compound for skin lightening is. In the analysis of the results, the background melanin production observed in the negative control was deducted from the treatment conditions.
  • the graph in Figure 1 shows the percentage of melanin content remaining in Skin Equivalents (Reconstructed Tanned Epidermis) after successive treatments with various ingredients (and controls).
  • Control corresponds to the untreated control and it still contains 100% of melanin at the end of the experiment. It represents the null effect for a skin lightening ingredient.
  • Example 2 The following are examples of formulations that may be prepared in accordance with the present invention.
  • Example 2 The following are examples of formulations that may be prepared in accordance with the present invention.
  • the formulation below describes an oil-in-water emulsion with SPF protection (for example a cream or a lotion) incorporating the inventive composition which is suitable for the methods and uses according to the present invention.
  • SPF protection for example a cream or a lotion
  • the percentages indicated are by weight of the composition unless stated otherwise.
  • composition below describes a cleansing system (face/body wash, hair wash) incorporating the inventive composition which is suitable for the methods and uses according to the present invention.
  • the percentages indicated are by weight of the composition unless stated otherwise.
  • composition below describes a hydro -alcoholic system (for example a serum) incorporating the inventive composition which is suitable for the methods and uses according to the present invention.
  • the percentages indicated are by weight of the composition unless stated otherwise.
  • the formulation below describes a lipo-alcoholic system (for example a serum) incorporating the inventive composition which is suitable for the methods and uses according to the present invention.
  • the percentages indicated are by weight of the composition unless stated otherwise.
  • the formulation below describes a tinted water-in-oil product (for example a foundation) with SPF protection, incorporating the inventive composition which is suitable for the methods and uses according to the present invention.
  • the percentages indicated are by weight of the composition unless stated otherwise.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Mycology (AREA)
  • Microbiology (AREA)
  • Botany (AREA)
  • Dermatology (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une composition topique pour l'éclaircissement/le blanchiment de la peau comprenant (i) une quantité thérapeutiquement efficace d'un extrait d'au moins une espèce végétale de Rumex, (ii) une quantité thérapeutiquement efficace d'acide 8-hexadécène-1,16-dicarboxylique, et (iii) un véhicule dermatologiquement acceptable. L'association des principes actifs dans la composition démontre un effet synergique sur l'inhibition de la production de mélanine.
PCT/EP2009/054331 2009-04-09 2009-04-09 Composition topique pour l'éclaircissement de la peau WO2010115472A2 (fr)

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PCT/EP2009/054331 WO2010115472A2 (fr) 2009-04-09 2009-04-09 Composition topique pour l'éclaircissement de la peau

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Application Number Priority Date Filing Date Title
PCT/EP2009/054331 WO2010115472A2 (fr) 2009-04-09 2009-04-09 Composition topique pour l'éclaircissement de la peau

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WO2010115472A2 true WO2010115472A2 (fr) 2010-10-14
WO2010115472A3 WO2010115472A3 (fr) 2011-01-13

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160015614A1 (en) * 2013-03-11 2016-01-21 Beiersdorf Ag Compositions of alkylamidothiazoles and uv-filter substances
US20200155442A1 (en) * 2014-03-10 2020-05-21 Mary Kay Inc. Skin lightening compositions
CN111658568A (zh) * 2020-07-20 2020-09-15 广州葆雀化妆品有限公司 一种滋养活肤水及其制备方法
US10780041B2 (en) 2011-12-19 2020-09-22 Mary Kay Inc. Combination of plant extracts to improve skin tone
CN116813676A (zh) * 2023-06-29 2023-09-29 中国科学院昆明植物研究所 酸模属植物提取物和活性化合物及其制备方法和应用

Citations (1)

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US6521267B1 (en) * 1998-06-08 2003-02-18 Fytokem Prtoducts, Inc. Tyrosinase inhibitors from plants

Patent Citations (1)

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US6521267B1 (en) * 1998-06-08 2003-02-18 Fytokem Prtoducts, Inc. Tyrosinase inhibitors from plants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WIECHERS J W ET AL: "OCTADECENEDIOIC ACID FOR A MORE EVEN SKIN TONE", COSMETICS & TOILETRIES, WHEATON, IL, US, vol. 117, no. 7, 1 July 2002 (2002-07-01), pages 55-68, XP009038160, ISSN: 0361-4387 cited in the application *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10780041B2 (en) 2011-12-19 2020-09-22 Mary Kay Inc. Combination of plant extracts to improve skin tone
US11865202B2 (en) 2011-12-19 2024-01-09 Mary Kay Inc. Combination of plant extracts to improve skin tone
US20160015614A1 (en) * 2013-03-11 2016-01-21 Beiersdorf Ag Compositions of alkylamidothiazoles and uv-filter substances
US20200155442A1 (en) * 2014-03-10 2020-05-21 Mary Kay Inc. Skin lightening compositions
CN111658568A (zh) * 2020-07-20 2020-09-15 广州葆雀化妆品有限公司 一种滋养活肤水及其制备方法
CN116813676A (zh) * 2023-06-29 2023-09-29 中国科学院昆明植物研究所 酸模属植物提取物和活性化合物及其制备方法和应用
CN116813676B (zh) * 2023-06-29 2024-03-19 中国科学院昆明植物研究所 酸模属植物提取物和活性化合物及其制备方法和应用

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