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(12) Patent Application Publication (10) Pub. No.: US 2004/0009197 A1 Derosa Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2004/0009197 A1 Derosa Et Al US 20040009197A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0009197 A1 DeRosa et al. (43) Pub. Date: Jan. 15, 2004 (54) USE OF RESVERATROLAS SUNSCREEN (30) Foreign Application Priority Data (76) Inventors: Mario DeRosa, Naples (IT); Mose Jun. 2, 2000 (IT) .............................. NA2OOOAOOOO37 Rossi, Naples (IT) Publication Classification Correspondence Address: Karen A Lowney (51) Int. Cl." ....................................................... A61K 7700 Estee Lauder (52) U.S. Cl. .............................................................. 424/401 125 Pinelawn Road Melville, NY 11747 (US) (57) ABSTRACT (21) Appl. No.: 10/296,725 Use of trans and cis resveratrol and their ether, ester, (22) PCT Filed: May 29, 2001 ethoxylated, glycosylated and hydroxylated derivatives as Sunscreens for protection against light having a wavelength (86) PCT No.: PCT/EP01/06103 of from 200 to 320 nm. US 2004/0009197 A1 Jan. 15, 2004 USE OF RESVERATROLAS SUNSCREEN nor discolored by ultraViolet radiation. A preparation con taining the Substance should be stable during Storage, have FIELD OF THE INVENTION no intrinsic odor, and be compatible with the commonly used cosmetic ingredients. 0001. The present invention relates to the use of resvera trol and the derivatives thereof as active principles for 0007 Sunscreen preparations which extend the time nec SUSCCCS. essary for the Sun to produce a Sunburn are commercially available. Such preparations contain Sunscreens, which are, BACKGROUND OF THE INVENTION almost eXclusively, Synthetic compounds, that absorb ultra 0002 There is an increasing demand and need for new Violet light at various wavelengths. Sunscreens which, while permitting skin tanning, help in 0008 UV-A radiation causes tanning, but is weak in preventing Sunburns and skin diseases caused by the UV causing reddening of the skin. About 20-50 joules/cm’ of StreSS. UV-A energy is required to produce one MED. The 0.003 Extensive studies have been made on the ultravio erythema reaction is maximal in intensity about 24 hours let radiations of Sunlight and Skylight reaching the Surface of after exposure. Suitably UV-A absorbing agents include the earth and on the effects of Such radiations on the human 2,4-dihydroxybenzophenone (Uvinul 400); 2-hydroxy-4- skin. UltraViolet energy absorbed by the human skin can methoxybenzophenone (oxybenzone, Spectra-Sorb UV9, produce an erythema reaction (redness), whose intensity is Uvinul M-40); 2,2,4,4-tetrahydroxybenzophenone (Uvinul dependent upon the amount of energy absorbed. It has been D50); 2,2'-dihydroxy-4,4'-dimethoxybenzophenone (Uvinul established that the radiations between 290 and 315 nm, D49); 2-ethylhexyl-2-cyano-3,3'-diphenylacrylate (Uvinul named UV-B, are responsible of erythema and of a substan N539); 2-ethylhexyl-4-phenyl-benzophenone carbonate tial portion of energy, which produces a retarded or indirect (Eusolex 3573); 2-hydroxy-4-methoxy-4'-methylbenzophe tanning. This is originated by the activation, between 48-72 none (mexenone, Uvistat 2211); 2-(2-hydroxy-5'-t-oc hours, of a massive Synthesis of melanin in melanocytes and tylphenyl)benzotriazole (Spectra-Sorb UV 5411); 2,2'-dihy by an increase of melanoSomes in all the Stratifications of droxy-4-methoxybenzophenone (dioxybenzone, Spectra cheratinocytes of malpighian. However the ultraViolet radia Sorb UV24); 2-hydroxy-4-(n-octyloxy)benzophenone tions having wavelength between 315 and 400 nm, named (octabenzone, SpectraSorb UV531), 4-phenylbenzophenone UV-A, promote a fast but labile tanning, which involves (Eusolex 3490); and 2-(2-hydroxy-5'-methylphenyl)benzo only the mature melanoSomes and not the melanocytes of tiazole (Tinuvin P). The UV-A absorbing compounds are the basal Zone. Ultraviolet radiation emits different quanti present in the final product in concentration from about 0.5% ties of energy and therefore produces an erythema reaction to about 10% by weight of the formulation. The amount will at different time intervals after exposure. The minimal vary according to the particular agent Selected and whether amount of UV associated energy required to produce a the formulation is intended to minimize or permit tanning. perceptible redness reaction of the skin is termed “Minimal The preferred UV-A absorbing agent is 2-hydroxy-4-meth Erythema Dose” or MED. oxybenzophenone alone or in combination with 2,2'-dihy 0004. The tanning ability is genetically predetermined droxy-4-methoxybenzophenone. and is related to the capacity to produce the melanin pig 0009 UV-B radiation causes the Sunburn reaction that ment, within the pigment cells, when stimulated by UV-B also stimulates pigmentation (tanning) of the skin. Approxi and UV-A. The extent of any erythemal response is a mately 0.02-0.05 joules/cm of UV-B energy is required to function of the Skin color and thus less time is required to produce one MED. The erythema reaction is maximal in produce a MED in light skinned than in dark skinned intensity at about 6-20 hours after exposure. Suitable UV-B individuals. The most rapid way to cause tanning, is to allow absorbing agents include 4-(dimethylamino)benzoic acid the Sun to produce erythema of the skin. The erythema ethyl ester; and isopropyl p-aminobenzoate, 4-(dimethy Sufficient to induce a tanning, yet not So Severe as to cause lamino)benzoic acid-2-ethylhexyl ester (Escalol 507); pain, requires only half the time of the exposure necessary 4-(dimethylamino)benzoic acid pentyl ester (Escalol 506); to produce a painful Sunburn. Sun tanning can occur at the glyceryl p-aminobenzoate (Escalol 106) and isobutyl p-ami UV-A wavelengths but it slowly develops under natural nobenzoate (Cycloform). The UV-B absorbing agent/s are conditions. Tanning, most commonly, develops after the present in the final product in concentration from 1% to 15% exposure to the UV-B band with Sunburn. by weight of the formulation. The amount will vary accord 0005. During the past forty years, a great number of ing to the particular agent Selected and the degree of chemical compounds have been Screened for their filtering protection desired in the final product. The preferred UV-B effects in the UV range and utilized in cosmetic formulations absorbing agent is 4-(dimethylamino)benzoic acid, 2-ethyl for reducing the absorbed UV dose while modulating the hexyl ester. erythema and tanning processes. The goal is to obtain a good 0010 For human application, ultraviolet UV-B and UV-A tanning with the minimal injury to the exposed skin. Screens are incorporated in various cosmetic oil carriers, oily 0006 Whether or not a substance absorbs light in the Solutions, oil lotions, and creams. Additionally, compounds ultraViolet range and is also a usable Sunscreen for the Such as hydroxyaldehydes, in particular dihydroxyacetone, human skin depends on Several factors. In addition to the imidazole and various imidazole derivatives Such as 4-(hy high filtering effectiveness in the erythemal range (UV-B droxymethylimidazole), may be incorporated in the formu range), it should also be compatible with the skin and the lation to provide an artificial tanning with ultraViolet pro mucous membrane and must be not toxic. Finally the tection, i.e. pigmentation of the Skin which resembles substance should be chemically stable and neither be altered natural melanin pigmentation in appearance only. US 2004/0009197 A1 Jan. 15, 2004 0011 Up to now ultraviolet UV-B and UV-A screens are 0022 Resveratrol (3,4,5-trihydroxyStilbene) is a phenolic of Synthetic origin and have had only the physical role of Stilbene and the parent glycosydes are called polydatin or preventing the skin damages of UV exposure. piceid. The trans isomer occurs in a narrow range of Sper 0012. The present invention provides multifunctional matophytes, including principally Vines, peanuts and pine Sunscreens, that conjugate an efficient and Selective filtering trees. ReSVeratrol is classified as a phytoalexin and its of UV-B radiation with specific biological actions in pre Synthesis in plants is induced by StreSS, in particular UV venting the skin damageS associated to the UV exposure, irradiation. ReSVeratrol is also a potent anti-oxidant, in vivo comprising as active ingredients resveratrol and the ether, preventing free radical propagation. ester, ethoxylated, glycosylated and hydroxylated deriva tives thereof. 0023 The high resveratrol content in the rhizomes of the 0013 More particularly, the present invention relates to plant Poligonum cuspidatum, makes this compound now compositions for the topical application, containing cis or easily available. trans resveratrol or derivatives thereof, of formula (I) 0024. In vivo and in vitro experiments have shown that resveratrol possesses many biological attributes: a) is a potent anti-oxidant and a vasorelaxing compound and exerts OR a cardiovascular protection (The Lancet, 341:1103-1104, 1993; Neuroreport, 8:1499-1502, 1997; Chim Pharm Bull, 12:128-129, 1996; Arch Pharm Res, 13:132-135, 1990; Thrombosis and Gaemostasis, 76:818-819, 1996); b) has an anti-inflammatory action, inhibiting lypoxygenase and cyclooxygenase (Science, 267: 1782-1788, 1995); c) acts as an antimutagen, by inhibiting the cellular events associated with tumor initiation, promotion and progression (Chem Pharm Bull, 30:1766-70, 1982; Science, 267: 1782-1788, RO 1995; Am J Enol Vitic, 46:159-165, 1996; Science, 275:218 Natural trans resveratrol R1-R4 = H 220, 1997; Cancer Res, 54:5848-5855, 1994; Anticancer Res, 14:1775-1778, 1995; Anal Biochem, 169:328-336, 0014) wherein: 1988; Proc Natl AcadSci USA, 91:3147-3150, 1994; Proc 0015 R, R2, R are H, C-C alkyl groups, option Natl AcadSci USA, 72:1848-1851, 1975; Carcinogenesis, ally Substituted by OH groups and optionally com 8:541-545, 1987). prising one or more double bonds, C-C acyl 0025 None of the recent patents on the use of resveratrol groups, optionally Substituted by OH groups and in pharmaceutical and cosmetic applications (WO9959561; optionally comprising one or more double bonds, a WO9958119; EP0773020; FR2766176; WO9904747) relate -(CH-CH-O), H group where n is an integer to the field of this invention.
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