Topical Compositions Containing Phosphorylated Polyphenols

Abstract

The present invention provides topical compositions containing phosphorylated polyphenols in combination with a topically acceptable carrier. The compositions of the invention provide a means for delayed delivery of the polyphenol to keratinous tissues, such as skin, hair and nails, with enzymes of the keratinous tissue dephosphorylating the polyphenol, and returning it to its native active form. The compositions are particularly useful in the regulation of skin conditions.

1 . A topical composition for application to a keratinous tissue, comprising at least one phosphorylated polyphenol in combination with a cosmetically or pharmaceutically acceptable carrier. 
     
     
         2 . The composition of  claim 1  in which the polyphenol is a compound of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4 , R 5  each independently of each other is hydrogen, hydroxide, carboxyl, Z, OZ or COOZ, provided that least one of the substituents R 1 , R 2 , R 3 , R 4 , R 5  is a hydroxyl group or carboxyl group, Z being an alkyl chain consisting of 1-10 carbon atoms or being CHCHCOOY with Y=hydrogen or an alkyl chain of 1-4 carbon atoms. 
     
     
         3 . The composition of  claim 2  in which the compound is selected from the group consisting of catechol, pyrogallol, guaiacol, resorcinol, and 1,4-hydroquinone; pyrogallol and topically acceptable hydroxyacids and esters thereof, hydroxycinnamic acids and topically acceptable esters thereof, where one R group is a vinylic acid or ester thereof; mixtures thereof, plant extracts containing such compounds, and mixtures thereof. 
     
     
         4 . The composition of  claim 3  in which the compound is selected from the group consisting of gallic acid, methyl gallate, ethyl gallate, propyl gallate, octyl gallate, p-coumaric acid, caffeic acid, ferulic acid, salicylic acid, sinaptic acid, chlorogenic acid, curcumins, and analogues thereof in which the carboxylic acid group is esterified with a C1-C10 alcohol, and mixtures thereof. 
     
     
         5 . The composition of  claim 1  in which at least one polyphenol is a phosphorylated condensed tannin. 
     
     
         6 . The composition of  claim 5  in which the condensed tannin is a topically acceptable phosphorylated flavonoid, stilbene, or phloroglucinol. 
     
     
         7 . The composition of  claim 6  in which the condensed tannin is a phosphorylated flavonoid, or mixtures thereof. 
     
     
         8 . The composition of  claim 7  in which the flavonoid is selected from the group consisting of phosphorylated forms of flavanones, chalcones, flavones, isoflavones, flavonols, flavanols, coumarins, chromones, dicoumarols, chromanones, and chromanols. 
     
     
         9 . The composition of  claim 5  in which the compound is a phosphorylated stilbene. 
     
     
         10 . The composition of  claim 9  in which the compound is a phosphorylated resveratrol or a phosphorylated resveratrol derivative 
     
     
         11 . The composition of  claim 1 , in which the polyphenol is provided in the form of a phosphorylated plant extract. 
     
     
         12 . The composition of  claim 11 , in which the polyphenol is provided in the form of a plant extract selected from the group consisting of phosphorylated extracts of  Eucalyptus, Acacia, Quebracho, Pinus, Gingko, Lespedeza, Passiflora, Silybum, Citrus, Hamamelis, Thymus, Chamaemelum, Achillea, Equisetum, Sophora, Fagopyrum, Sambucus, Betula, Vitis, Crataegus, Ratanhia, Lythrum, Acacia, Cupressus, Vaccinium, Ribes, Centaurea, Rosa, Hibiscus, Camellia, Malva, Podophyllum, Schizandra, Gaiacum, Theobroma, Arctostaphylos, Glycine, Cynara, Rosmarinus, Orthosiphon, Solidago, Punica, Lithospermum, Curcuma, Aesculus, Melilotus, Ammi, Hieracium, Angelica, Asperula,  Chinese gallnut, grape seed, grape skin, green tea, black tea, white tea, pomegranate, cocoa, red wine, Persimmon, citrus fruits, soy beans, and mixtures thereof. 
     
     
         13 . The composition of  claim 1  in which the phosphorylated phenol is a phosphorylated hydrolysable tannin. 
     
     
         14 . The composition of  claim 1  in which the polyphenol is selected from the group consisting of phosphorylated forms of catechol, DL-3,4-dihydroxyphenylalanine, DL-DOPA, catecholamines, 3-hydroxytyramine, dopamine, phloroglucinol, phenolic acids, caffeic acid, dihydrocaffeic acid, ferulic acid, protocatechuic acid, chlorogenic acid, isochlorogenic acid, gentisic acid, homogentisic acid, gallic acid, hexahydroxydiphenic acid, ellagic acid, rosmarinic acid, lithospermic acid, curcumin; polyhydroxylated coumarins, polyhydroxylated lignans, neolignans; silymarin, apigenol, luteolol, quercetin, quercetagin, quercetagetin, chrysin, myricetin, rhamnetin, genistein, morin, gossypetin, kaempferol, rutin, naringin, narigenin, hesperitin, hesperidin, diosmin, diosmoside, amentoflavone, fisetin, vitexin, isoliquirtigenin, hesperidin methylchalcone, taxifoliol, silybin, silychristin, silydianin, catechin, epicatechin, gallocatechin, catechin gallate, gallocatechin gallate, epicatechin gallate, epigallocatechin gallate, epigallocatechin, glucogallin; proanthocyanidin, propyl gallate, isoamyloctyl gallate, dodecyl gallate, penta-O-galloyl glucose, tannic acid, gallotannin, ellagitannin, shikimic acid, salicylic acid, resveratrol (3,4′,5′-trihydroxystilbene); plant extracts containing one or more of these compounds; and mixtures thereof. 
     
     
         15 . The composition of  claim 1  which comprises a phosphorylated resveratrol or a phosphorylated resveratrol derivative. 
     
     
         16 . The composition of  claim 1  which comprises at least one skin benefit agent selected from the group consisting of astringents, antioxidants, free radical scavengers, anti-acne agents, antimicrobial agents, antifungal agents, chelating agents, anti-aging agents, anti-wrinkle agents, analgesics, skin lightening agents, skin conditioning agents, anti-irritants, anti-inflammatories, anti-cellulite agents, humectants, emollients, organic sunscreens, inorganic sun protecting agents, chemical exfoliating agents, physical exfoliating agents, self-tanning agents, biologically active peptides; and mixtures thereof. 
     
     
         17 . A method of regulating skin condition comprising applying to the skin a composition comprising at least one phosphorylated polyphenol in combination with a topically acceptable carrier. 
     
     
         18 . The method of  claim 17  in which the skin condition to be treated is selected from the group consisting of eczema, seborrhea, psoriasis, xerosis, neoplastic growths, dermatitis, folliculitis, rosacea and acne. 
     
     
         19 . The method of  claim 17  in which the skin condition to be treated is one or more signs of skin aging. 
     
     
         20 . The method of  claim 19  in which the polyphenol is selected from the group consisting of phosphorylated flavonoids, stilbenes and mixtures thereof. 
     
     
         21 . The method of  claim 20  in which the flavonoid is selected from the group consisting of phosphorylated form of flavanones, chalcones, flavones, isoflavones, flavonols, flavanols, coumarins, chromones, dicoumarols, chromanones, and chromanols. 
     
     
         22 . The method of  claim 19  in which the polyphenol is a phosphorylated resveratrol or a phosphorylated resveratrol derivative. 
     
     
         23 . A method of regulating the effects of reactive oxygen species on a cell of a keratinous tissue which comprises applying to the cell a composition comprising at least one phosphorylated polyphenol and a topically acceptable carrier. 
     
     
         24 . A method of delayed delivery of a polyphenol to the skin comprising applying the polyphenol to the skin in phosphorylated form. 
     
     
         25 . A method for rendering water-soluble a water-insoluble polyphenol which comprises phosphorylating the insoluble polyphenol to an extent sufficient to render the polyphenol water-soluble. 
     
     
         26 . The method of  claim 25  in which the polyphenol is resveratrol or a resveratrol derivative.