(12) United States Patent (10) Patent No.: US 7,008,929 B2 Rubinstenin Et Al
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USOO70O8929B2 (12) United States Patent (10) Patent No.: US 7,008,929 B2 Rubinstenin et al. (45) Date of Patent: Mar. 7, 2006 (54) SAPOGENIN-BASED TREATMENT (56) References Cited (75) Inventors: Gilles Rubinstenn, Paris (FR); Bruno U.S. PATENT DOCUMENTS Buan, Bagnolet (FR) 5,607,693 A 3/1997 Bonte et al. (73) Assignee: L'Oreal, Paris (FR) 5,723,149 A 3/1998 Bonte et al. 6,294,157 B1 9/2001 Rubinstenin et al. 6,331.535 B1 12/2001 Tuloup et al. (*) Notice: Subject to any disclaimer, the term of this 6,528,043 B1 3/2003 Rubinstenin et al. patent is extended or adjusted under 35 2002/0O2818.6 A1 3/2002 Rubinstenin et al. U.S.C. 154(b) by 175 days. 2004/0005370 A1 1/2004 Breton 2004/0028757 A1 (21) Appl. No.: 10/393,989 2/2004 Cals-Grierson, et al. FOREIGN PATENT DOCUMENTS (22) Filed: Mar. 24, 2003 FR 2813.194 * 3/2002 (65) Prior Publication Data * cited by examiner US 2003/0216327 A1 Nov. 20, 2003 Primary Examiner James O. Wilson ASSistant Examiner-Ganapathy Krishnan Related U.S. Application Data (74) Attorney, Agent, or Firm-Oblon, Spivak, McClelland, (60) Provisional application No. 60/374,159, filed on Apr. Maier & Neustadt, P.C. 22, 2002. (57) ABSTRACT (30) Foreign Application Priority Data Apr. 2, 2002 (FR) ................................... O2 04O72 The present invention relates to the use of a Sapogenin, chosen from diosgenin and he cogenin, and/or of a plant (51) Int. Cl. extract containing at least one of these Sapogenins. A pre A6 IK3I/704 (2006.01) ferred use is the treatment of oligoseborrheic dry skin. (52) U.S. Cl. ........................................... 514/26; 514/33 Another preferred use is the treatment of dry scalp. Com (58) Field of Classification Search .................. 514/26, positions containing these Sapogenins are also described. 514/33 See application file for complete Search history. 10 Claims, No Drawings US 7,008,929 B2 1 2 SAPOGENIN-BASED TREATMENT acceptable compounds which make it possible to effectively Stimulate the Sebaceous function for the purpose of treating REFERENCE TO PRIORAPPLICATIONS oligoseborrheic dry skin. This application claims priority to U.S. provisional appli DETAILED DESCRIPTION OF THE cation 60/374,159, filed Apr. 22, 2002, and to French patent INVENTION application 0204072 filed Apr. 2, 2002, both of which are incorporated herein by reference. The inventors have discovered, with Surprise, that Some Sapogenins make it possible to Satisfy this need. FIELD OF THE INVENTION Sapogenins are compounds resulting from the acid hydrolysis (generally in the presence of hydrochloric acid or The present invention relates to the use of a Sapogenin Sulphuric acid in boiling aqueous medium) or enzyme chosen from diosgenin and he cogenin (including a mixture hydrolysis (generally for approximately 5 days at approxi thereof), and/or of a plant extract containing one or both of mately 37° C), conventionally followed by extraction with these specific Sapogenins. A preferred use is the treatment of 15 an apolar organic Solvent, of Saponosides, which have func oligoseborrheic dry skin. Another preferred use is the treat tionalized heterocides, of very high molecular weight, ment of dry Scalp. Compositions containing these Sapo present in the tubers of certain plants. AS Sources of Sapono genins are also described. Sides, mention may be made of the plants of the family The Sapogenin and composition thereof may be used for DioScoreaccae, Such as DioSCOrea composita, DioScorea cosmetic purposes, for example for treating drying out of the deltoides, Dioscorea floribunda, Dioscorea Sylvatica, skin, in particular after menopause, or for dermatological Dioscorea spiculiflora and Dioscorea villosa, which are rich purposes, for example for the treatment of disorders asso in dioScin; and the plants of the Agave family. ciated with oligoseborrheic dry skin, in particular forms of Among the Sapogenins, medicagenic acid and Medicago dermatitis. extracts containing Same have been described as useful in 25 the treatment of dry skins resulting from insufficient cell BACKGROUND OF THE INVENTION renewal (U.S. Pat. No. 5,273,149). It was not suggested however that other Sapogenins, Such as diosgenin and heco Many women, from the age of thirty five, and more genin, could have any effect on oligoseborrheic dry skins. particularly after menopause, frequently complain of drying This type of skin requires indeed using compounds that out of their skin, and of the manifestations of discomfort or Stimulate Sebum production. unaesthetic manifestations which result therefrom (desqua Similarly, FR-2802 412 discloses a composition intended mation, dull complexion, atonia of the skin). Now, this to moisturize in particular the skin, after exposure to infrared drying out is due, as is now known, to a decrease in the radiation. The composition contains, as active principle, a production of Sebum with age. placental extract and also, as antimicrobial and anti-inflam Moreover, children in whom the sebaceous function is not 35 matory agents, Sapogenins, including ruscogenin and hed yet active often exhibit Signs of dry skin. eragenin. However, these compositions are applied to skin Sebum is the natural product of the Sebaceous gland which has been dehydrated by evaporation of water due to which, along with the Sweat produced by the eccrine or the heating caused by exposure to infrared radiation, and not aprocrine glands, constitutes a natural moisturizer for the to oligoseborrheic skin. epidermis. It consists essentially of a more or less complex 40 Diosgenin has already been described as an anti-inflam mixture of lipids. Conventionally, the Sebaceous gland pro matory (Yamada et al., Am. J. Physiol., 273:G355-G364, duces Squalene, triglycerides, aliphatic waxes, cholesterol 1997), as a Slimming agent, by virtue of its action on waxes and possibly free cholesterol (Stewart, M. E., Semin. adipocytes (WO 00/30603), as a collagenase inhibitor and as Dermatol. 11, 100–105 (1992)). The action of bacterial an antimicrobial agent which can be used in the treatment of lipases converts a varying portion of the triglycerides to free 45 various pathological conditions with an infectious compo fatty acids. nent, including acne and seborrheic dermatitis (DE-198 41 The Sebocyte constitutes the competent cell of the Seba 795). ceous gland. The production of Sebum is associated with the Moreover, the inventors have described various compo programme of terminal differentiation of this cell. During Sitions comprising Sapogenins, including diosgenin, which this differentiation, the metabolic activity of the sebocyte is 50 can be used, among others, in the treatment of cutaneous essentially centred around the biosynthesis of lipids (lipo aging (U.S. Ser. No. 2002/0028.186; U.S. Pat. No. 6,331, genesis), and more precisely around the neosynthesis of 535; FR-2811561; and FR-2811567). fatty acids and the Squalene. Thus, to the inventors knowledge, it has never been A compound making it possible to Stimulate the produc Suggested to use diosgenin or hecogenin in the treatment of tion of the lipids constituting sebum, by the cells of the 55 oligoseborrheic dry skins. Sebaceous gland (sebocytes), would therefore be of definite In addition, extracts of DioScorea tokoro, which contain value for the treatment of oligoseborrheic dry skin, i.e. skin dioScin, have been described as effective for moisturizing exhibiting a sebum content of less than 100 tug/cm’ on the the skin and thus softening it. Thus, document JP-10 194947 forehead. discloses an extract of DioScorea tokoro prepared by extrac For this purpose, in patent U.S. Pat. No. 4,496.556, the 60 tion using water, alcohol or acetone at a temperature of use of DHEA, a Steroid Secreted by the adrenal glands, or between 0 and 50° C., preferably 0° C. This extract is esters thereof, administered topically, has been proposed in described as being of use for improving the SupplemeSS and order to increase the production of Sebum. the moisturization of the Skin due to the glycoproteins which However, for regulatory reasons, it is not always possible it contains. It is also thought to have a Suppressive effect on to use this type of compound in the cosmetics field. In 65 Sebaceous Secretion. addition, it is not Sufficiently effective on oligoSeborrheic As regards document JP-2000 143 488, it discloses a skin. There remains therefore the need to have cosmetically composition for preventing and improving drying out of the US 7,008,929 B2 3 4 skin, comprising an extract of a plant chosen from a long list, is preferentially prepared from plant material originating including DioScorea tokoro maduino and DioSCOrea gracil from the DioSCOrea villosa and DioSCOrea opposita Species. lima miq., which are Sources of Saponisides. Here again, the Such an extract is in particular available from the company extraction method comprises simply immersing the plant in ACTIVE ORGANICS under the commercial names Actigen a Solvent at ambient temperature, followed by Steps of 5 Y(R) and Actiphyte Mexican Wild Yam(R). It can, as a varia filtration and of drying, and the extract thus obtained can be tion, be obtained from the company OSST under the com considered as containing the Saponosides of the plant. mercial name Wild Yam P. E.(R) or from the company Similarly, document WO 00/13693 describes an anti ALBAN MULLER under the commercial name Extrait sec pollution plant complex having a moisturizing effect, which contains in particular Saponoside-containing plants as anti igname Sauvage(E) wild yam dry extract. oxidants. These plants are extracted by grinding, maceration Hecogenin is available from the company SIGMA. It can in an aqueous-alcoholic Solvent at less than 50 C. and also be obtained by extraction of leaves from Agave of the filtration. Hechtia texensis Species, according to a method similar to Thus, the extraction methods described in these docu that described above for diosgenin.