AU629801B2 - Composition based on hydrated lipid lamellar phases or liposomes containing tyrosine or a tyrosine derivative and cosmetic or pharmaceutical composition, in particular dermatological composition, with pigmenting activity, containing it - Google Patents

Abstract

The invention concerns a composition based on hydrated lipid lamellar phases or liposomes. Said phases or said liposomes contain, at least in part, tyrosine or a tyrosine derivative, such as a salt or an ester. Said composition is useful for the preparation of cosmetic or pharmaceutical compositions, in particular dermatological compositions, in particular for promoting tanning of the skin, improving the complexion or slowing down the formation of grey hairs.

Description

K

I I--I OPI DATE 14/06/89 ORGANIS AOJP DATE 20/07/89 APPL. ID 27121 88

PCT

PCT NUMBER PCT/FR88/00569 DEMANDE INTERNATIONALE PUBLIEE EN VERTU DU TRAITE DE COOPERATION EN MATIERE DE BREVETS (PCT) (51) Classification internationale des brevets 4 (11) NumBro de publication internationale: WO 89/ 04651 A61K7/00, 7/42, 7/13 Al (43) Date de publication internationale: Ier juin 1989 (01.06.89) (21) Numiro de la demande internationale: PCT/FR88/00569 (74) Mandataires: PORTAL, G6rard etc.; Cabinet Beau de Lomenie, 55, rue d'Amsterdam, F-75008 Paris (FR).

(22) Date de dip6t international: 23 novembre 1988 (23.11.88) (81) Etats disignts: AU, BR, JP, KR, US, (31) NumBro de la demande prioritaire: 87/16524 Publie (32) Date de priorit6: 27 novembre 1987 (27.11.87) Avec rapport de recherche internationale.

(33) Pays de priorit6: FR (71) DBposant (pour tous les Etats designs sauf US): LVMH RECHERCHE [FR/FR]; 48-50, rue de Seine, F-92704 Colombes C6dex (FR).

(72) Inventeurs; et Inventeurs/Diposants (US seulement) MEYBECK, Alain [FR/FR]; Les Pcissons Apt. 242, 20 ter, rue de Bzons, F-92400 Colombes DUMAS, Marc [FR/ FR]; 63, boulevard Gambetta, F-92700 Colombes

(FR).

62O 1 (54)Title: COMPOSITION BASED ON HYDRATED LIPID LAMELLAR PHASES OR LIPOSOIvIES CONTAI- NING TYROSINE OR A TYROSINE DERIVATIVE AND COSMETIC OR PHARMACEUTICAL COM- POSITION, IN PARTICULAR DERMATOLOGICAL COMPOSITION, WITH PIGMENTING ACTIVI- TY, CONTAINING IT (54) Titre: COMPOSITION A BASE DE PHASES LAMELLAIRES LIPIDIQUES HYDRATEES OU DE LIPO- SOMES CONTENANT DE LA TYROSINE OU UN DERIVE DE TYROSINE ET COMPOSITION COS- METIQUE OU PHARMACEUTIQUE, NOTAMMENT DERMATOLOGIQUE, A ACTIVITE PIGMEN- TANTE, L'INCORPORANT (57) Abstract The invention concerns a composition based on hydrated lipid lamellar phases or liposomes. Said phases or said liposomes contain, at least in part, tyrosine or a tyrosine derivative, such as a salt or an ester. Said composition is useful for the preparation of cosmetic or pharmaceutical compositions, in particular dermatological compositions, in particular for promoting tanning of the skin, improving the complexion or slowing down the formation of grey hairs.

(57) Abrig6 L'invention concerne une composition i base de phases lamellaires lipidiques hydrathes ou de liposomes. Cette composition est caract6ris6e en ce que lesdites phases lamellaires lipidiques hydrat~es on lesdits liposomes contiennent au moins en partie de la tyrosine ou un driv6 de tyrosine, tel qu'un sel, ou un ester. Cette composition trouve notamment application pour la pr6paration de compositions cosm6tiques ou pharmaceutiques, notamment dermatologiques, destinees en particulier 4 favoriser le bronzage de la peau, ameliorer le teint ou ralentir I'apparition des cheveux gris.

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i 4iR 1 j I I Composition based on hydrated lipid lamellar phases or liposomes containing tyrosine or a tyrosine derivative and a cosmetic or pharmaceutical composition, in particular dermatological with pigmenting activity, incorporating it.

The subject of the present invention is a composition based on hydrated lipid lamellar phases or 'iposomes, containing tyrosine or a tyrosine derivative.

The invention finds application in particular in the cosmetic or pharmaceutical, and in particular dermatological, field for the development of compositions with pigmenting activity, capable of being used to accelerate the tanning of the skin, improve the complexion or retard the appearance of grey hair.

It is known that melanin pigments, responsable in particular for the black colour of the skin and hair, have a macromolecular structure, the predominant chemical units of which are formed from precursors, and in particular from tyrosine.

The article of PRAKASH C. JOSHI et al., Biochem. Biophys.

Res. Commun. (1987) 142 pages 265 to 274, recalls the biochemical mechanism for the conversion of tyrosine into melanin.

Thus, for a long time attempts have been made to develop cosmetic products based on tyrosine, destined in particular to promote the tanning of the skin and the pigmentation of hair.

However, tyrosine exhibits a certain hydrophilic character and penetrates with very great difficulty through the corneous layer to the level of the melanocytes. In consequence, research has been oriented towards products in which tyrosine is present in a modified form, both from the chemical and physical points of view.

It is in this way that the French patent FR-A-2 439 013 recommends the utilization of a salt complex of L-tyrosine with at least one aminoacid chosen from among arginine, ornithine, citrulline, lysine or hydroxylysine. The authors have shown that the salt complex just mentioned has an unexpected effect of activating tyrosinase naturally present in the epidermis.

;1 1 2 Similarly, the document DE-2 932 923 discloses cosmetic compositions containing a tyrosine-arginine-urocanate complex, acting as promoter of melanin.

Cosmetic compositions have also been developed incorporating combinations of various compounds, among which tyrosine appears (FR-A-2 252 841 and US-3 899 288).

Similarly, the document EP-124 077 discloses a composition destined to retard the appearance of grey hair. It is indicated there that the results obtained with this composition are better if a solution containing tyrosine is used prior to this composition.

Finally, the patent US-4 453 941 describes the utilization of a specific derivative of tyrosine possessing a side chain capable of forming an indole nucleus, in combination with an aminoacid and an oxidant.

Thus for a long time there has existed a prejudice against the utilization of tyrosine alone in cosmetic compositions.

This prejudice was confirmed recently by an article of C. JAWORSKI et al., published in "Journal of the American Academy of Dermatology" 1987, vol, 16, 4, pages 769-771. The authors have not observed any significant effect of the compositions tested containing tyrosine on the acceleration of tanning of the skin. In addition, they point out that it is doubtful that tyrosine, a polar molecule, can pass through the corneum and thus penetrate to the basal layer of the epidermis where the melanocytes are located.

The use of hydrated lipid lamellar phases or liposomes in pharmaceutical compositions or cosmetic compositions, in which various active principles are incorporated (EP-B1-0 087 993) has also been known for a long time.

In opposition to the existing prejudice, the authors of the present invention have conducted research and demonstrated in a quite unexpected manner the fact that tyrosine or its derivatives, such as its salts or its esters, make it possible to obtain a measurable increase in the amount of melanin induced in the skin by ultraviolet rays when x

Z

1 3 they are incorporated in a hyarated lipid lamellar phase or in liposomes.

This discovery makes possible the development of cosmetic or pharmaceutical compositions incorporating tyrosine or one of its derivatives.

Thus it is possible to deduce from this in a way a potentiation effect of the activity of tyrosine and its derivatives as a result of their incorporation in hydrated lipid lamellar phases or in liposomes.

Thus, the present invention has the effect of resolving the new technical problem consisting of tho provision of a novel formulation based on tyrosine or one of its derivatives, such as its salts or its esters, making it possible to potentiate their efficacy in order to permit their utilization in cosmetic or pharmaceutical, and in particular dermatological, compositions with pigmenting activity.

Thus, in accordance with a first feature, the present invention provides a composition based on hydrated lipid lamellar phases, or liposomes, preferably for the preparation of cosmetic or pharmaceutical compositions, characterized in that the said hydrated lipid lamellar phases or the said liposomes contain at least in part tyrosine or a derivative of tyrosine, such as a salt or an ester.

In the present description and the claims, the term "lipid" in the expression "lipid lamellar phase" covers all substances containing a so-called fatty carbon chain, usually more than 5 carbon atoms.

According to the invention, amphiphilic lipids are used, i.e.

those constituted of molecules possessing a hydrophilic group, indiscriminately ionic or non-ionic, and a lipophilic group, such amphiphilic lipids being capable of forming lipid lamellar phases in the presence of an aqueous phase. In particular, among such lipids may be cited: the phqspholipids, the phosphoaminolipids, the glycolipids, the polyoxyethylene fatty alcohols, the esters of polyols possibly of polyoxyethylene. Such substances are constituted for example by egg or soya lecithin, phosphatidylserine, sphingomyelin, a cerebroside or an oxyethylene derivative of polyglycerol stearate.

More particularly, tyrosine is L-tyrosine, and the tyrosine derivative mentioned earlier is chosen from among the group of compounds constituted by an alkaline L-tyrosinate or alkaline earth L-tyrosinate as for example sodium or calcium L-tyrosinate, methyl L-tyrosinate, q thyl L-tyrosinate, stearyl L-tyrosinate and a compound obtained from _V 1 i 4 L-tyrosine and D glucose.

As different reaction compounds can be prepared from D glucose, all such compounds are included in the scope of the invention, taken individually or as a mixture. On the market, is found a mixture of these reaction compounds of D glucose with L-tyrosine, in particular a mixture of esters, under the name "glucose tyrosinate".

The incorporation of tyrosine or its derivatives into the hydrated lipid lamellar phases or into liposomes can be carried out according to known procedures. These latter are chosen more particularly depending on the more or less lipophilic character or more or less hydrophilic character of the compound to be incorporated.

According to a preferred embodiment of the composition based on hydrated lipid lamellar phases or liposomes, a method of preparation described in the document EP-B1-O 087 993 is chosen, if necessary in combination with a method described in the document EP-Bl-O 107 559.

Thus, it is for example possible to include tyrosine or the tyrosine derivative in hydrated lipid lamellar phases or liposomes in the following manner: Step 1 An amphiphilic lipid, hydrogenated or not, such as soya lecithin, is dissolved in an organic solvent with a relatively low boiling point, for example lower than 100°C at atmospheric pressure, such as dichloromethane or methanol. A hydrophobic lipid, such as a sterol, like cholesterol or B-sitosterol, and advantageously an antioxidant like 4-tocopherol may also be dissolved.

The amount of hydrophobic lipid must usually not exceed 0.2 times the amount of amphiphilic lipid by weight.

Step 2 Tyrosine or the tyrosine derivative is then dispersed in the solution obtained. The relative proportions of lipid on the one hand and of tyrosine or the tyrosine derivative on the other are included between 8:2 and 9.9:0.1, by weight. Preferably, the mixture is stirred for 30 min at room temperature.

Step 3-A The mixture obtained at the end of the second step is introduced into a rotary flask and evaporated by heating on a watert i l-_l bath, under reduced pressure if required.

After evaporation, the lipid film deposited on the walls is taken up with shaking in water or in a suitable aqueous solution such as a buffer solution containing 0.8 of NaCI and 1.5 of NaH 2

PO

4 called "phosphate buffer".

Preferably the amount of water or aqueous solution is at least equal to eight times the amount of lipid contained in the flask by weight.

A suspension of liposomes is thus obtained which can then be homogenized by appropriate means such eas, for example, ultrasonics.

Step 3-B According to a variant of the process for the preparation of the composition of the invention, the procedure described in the document EP-B1-0 087 993 is used, which includes the spraying of the mixture obtained at the end of the second step, followed by the dispersion of the lipid powder thus produced in a predetermined quantity of water or aqueous solution of substances to be encapsulated.

Hydrated lipid lamellar phases or a suspension of liposomes are obtained depending on whether one has chosen to disperse the lipid powder in a little or a great deal of the aqueous medium as is set out in the European document mentioned earlier.

The dispersion of lamellar phases or liposomes can then be homogenized, for example according to the procedure described in the document EP-B1-O 107 559.

Steps 3-C and 3-D According to another variant, tyrosine or the tyrosine derivative is introduced directly into the aqueous medium in which the lipid phase will be dispersed.

For that, the organic solution obtained at the end of step 1 is evaporated, either (step 3-C) by means of a rotary flask as indicated in step 3-A, or (step 3-D) by means of a sprayer as indicated in step 3-B. The lipid film or lipid powder obtained, respectively, is then dispersed in an aqueous solution of tyrosine or tyrosine derivative.

3 Lipid lamellar phases or liposomes then form which contain L i at least in part the substances dissolved in the water.

It is then possible to homogenize by means of the procedures mentioned earlier.

Advantageously, the dispersions of hydrated lipid lamellar phases or the suspensions of liposomes obtained in steps 3 above, can be gelified for example by mixing them with a gel prepared separately, such as a gel of a vinyl polymer.

In accordance with a second feature, the present invention also relates to a cosmetic or pharmaceutical, and especially dermatological, composition with pigmenting activity, characterized in that it comprises a composition based on hydrated lipid lamellar phases or liposomes, such as previously defined.

Preferably, the proportion by weight of tyrosine or the tyrosine derivative is comprised between 0.001 and 10 and preferably between 0.05 and 2 by weight, with respect to the total weight of the said cosmetic or pharmaceutical composition.

Other aims, properties and advantages of the invention will become more clearly apparent in the light of the explanatory description which follows, done with reference to several illustrative examples which will in no way limit the scope of the invention. In these examples, percentages are given by weight, unless indicated otherwise.

Example 1: Preparation of hydrated lipid lamellar phases containing L-tyrosine (method A) 1.8 g of hydrogenated soya lecithin and 0.06 g of &t-tocopherol are dissolved in 20 ml of dichloromethane, then 0.2 g of L-tyrosine are dispersed in this solution.

This mixture is evaporated under reduced pressure (about 200 mm of mercury) in a rotary flask heated at 45 0

C.

The lipid film obtained is taken up in 98 g of the solution called "phosphate buffer" mentioned earlier (pH equal to about with gentle shaking for 3 h.

An aqueous suspension of liposomes is obtained after homogenization with ultrasonics (10 min, 100 W).

This suspension is then gelified by mixing it with an equal weight of a Carbopol 940 R gel prepared in a standard manner at a I i 7 concentration of 5 by weight.

About 200 g of a gelified composition based on liposomes is thus obtained, the tyrosine content of which is 0.1 by weight of this composition.

Example 2: Preparation of hydrated lipid lamellar phases containing L-tyrosine (method B) 36 g of soya lecithin, 0.5 g of c6-tocopherol and then 4 g of B-sitosterol are dissolved in 300 ml of dichloromethane. The solution thus obtained is sprayed at 65 0 C as described in the patent 087 993 so as to produce an intimate mixture of the two lipid constituents in the form of a fine powder.

Furthermore, 0.35 g of L-tyrosine are dissolved in 900 ml of the solution called "phosphate buffer" previously mentioned (pH equal to about The sprayed lipid powder is then dispersed in the solution obtained by means of a magnetic stirrer for 3 h, then the dispersion is made up to 1000 g with distilled water, so as to obtain a suspension of liposomes of the following composition: Soya lecithin 36 g 8-sitosterol 4 g b-tocopherol 0.5 g L-tyrosine 0.35 g aqueous excipient to give 1000 g This composition is homogenized by means of a homogenizer under pressure, for example according to the procedure described in patent EP-B1-0 107 559.

Example 3: Preparation of hydrated lipid lamellar phases containing the methyl ester of L-tyrosine As in example 1, the procedure uses 1.8 g of hydrogenated soya lecithin, 0.2 g of the methyl ester of L-tyrosine and 0.06 g of &-tocopherol which are dissolved in 80 ml of methanol. This solution is evaporated under reduced pressure (about 200 mm of mercury) in a rotary flask at about 56°C. The lipid film is taken up by 98 g of the solution called "phosphate buffer" mentioned earlier (pH equal to about r After homogenization with ultrasonics for 10 mn at 100 W and (Ldd, i -I :111~~~1 8 with magnetic stirring for 3 hours, a suspension of liposomes is obtained containing methyl L-tyrosinate which can be gelified with a Carbopol 940 R gel. The mean size of the liposomes, measured with a Nano-Sizer

R

is 85.2 nm.

Example 4: Preparation of hydrated lipid lamellar phases containing "glucose tyrosinate" g of a commercial solution of "glucose tyrosinate" (20 aqueous-alcoholic solution) is diluted in 15 ml of methanol. 25 ml of a solution of 3.8 g of soya lecithin, 0.2 g of B-sitosterol and 0.1 g of &-tocopherol in dichloromethane are added to it.

The solution obtained is sprayed at'75°C as described in the European patent EP-Bl-0 087 993 so as to produce 5 g of powder of the lipid mixture. The lipid powder is dispersed in 47.5 g of demineralized water, with moderate stirring for 2 h. A suspension of lipid lamellar phases is obtained which is homogenized by ultrasonics for 10 min at 100 W in an icebath.

The 50 g of homogenized suspension of liposomes obtained are then gelified by the addition of 50 g of a 1 Carbopol 940 R gel.

The size of the liposomes, measured with a Nano-Sizer is 145.5 0.8 nm.

Example 5: Demonstration of the pigmenting activity of the tyrosine included in liposomes.

In order to study the pigmenting activity of these compositions according to the invention, an attempt was made to demonstrate the increase of melanogenesis in the mouse in vivo.

This type of experiment was performed on C3H mice by daily applications of the product to be tested, followeu by irradiation.

3 Groups of 6 mice were used. The first group (referred to hereafter as "non-irradiated control") was subjected neither to administration of the product nor to irradiation with U.V.

The second group (referred to hereafter as "irradiated control") was not subjected to administration of the product but was subject to daily irradiation with U.V. 5 days per week for three weeks.

Finally, the third group was subjected to a daily application 3 of the product to be tested followed by irradiation with under ';II the same conditions as the second group.

In order to carry out this experiment, the product obtained in the form of a gel in example 2 was applied to the tail of the mice for 5 days per week for 3 weeks. The product is applied in a quantity of about 0.2 ml (varying according to the length of the tail) about 1/4 of an hour before irradiation.

At the time of each irradiation, the mice of groups 2 and 3 have their tail exposed for 150 s at a distance of 26.5 cm from a 2500 W xenon OSRAMR lamp equipped with a water filter in order to suppress 7ong wavelengths and a WG 320 filter in order Co filter the U.V.C. The electrical intensity was adjusted to,54 A, and the powers of irradiation of U.V.B. and U.V.A. are 3 m% and 22 mW, respectively.

The mice of the three groups are then sacrificed, two fragments of tail skin are taken from each of them by biopsy which are immersed in a 2N solution of sodium bromide for 3 h at ambiant temperature in order to separate the epidermis.

Pieces of epidermis are removed with the aid of forceps, then they are rinsed for 1 min with distilled water, dried and weighed.

Thus, for each mouse, it is possible to measure the melanin formed with the first fragment and carry out a microscopic observation on the second fragment.

A-Measurement of the melanin formed.

The dried and weighed fragments of epidermis are subjected to digestion with trypsin at 37°C for 48 h.

A filtration is then carried out as is a centrifugation at 3000 rev/min for 30 min.

The melanin pellet of each mouse is recovered and suspended in a quantity of distilled water necessary for the measurement of the optical density.

The optical density is measured in a standard manner at 400 nm.

The values recorded are then related to 100 mg of weight of sampled epidermis and a mean value of the optical density is determined which is the only one to be taken into consideration.

i j T V *o 1 1 i L C i r The results of these measurements are given in table I below.

This table contains the measurement of the optical density for each mouse as well as the mean of these densities for each group (values underlined).

It is very clearly apparent that the amount of melanin formed, linked to the value of the optical density, is much larger for the mice of the third group which received an application of the composition of example 2, namely a composition based on liposomes containing tyrosine, before each irradation.

B-Microscopic observation of the fragments of.epidermis.

By means of these observations, an attempt is made to characterize the appearance of the epidermis in the three groups of mice by visualizing the melanocytes in particular.

The visualization of the melanocytes is carried out according to the method referred to as the DOPA reaction, according to the technique described by Renato J. STARICCO and Hermann PINKUS (Journal of Investigative Dermatology, 1956 pages 33-45).

The fragments of epidermis taken and treated as indicated above are incubated in a buffered solution of 0.1 dl-dopa at 37°C for 1 h. This incubation medium is then changed and incubation is continued for 6 to 7 h.

Fhe epidermises are then fixed with 10 formol overnight, then dehydrated with absolute alcohol, lightened with toluene and finally mounted between a glass slide and a coverslip, in order to be photographed at an enlargement X 475.

As an appendix, three photographs are shown corresponding to each of the groups with the same numbering system and selected as a function of their representativeness.

Photo 1 (control) the melanocytes are quite small, their dendrites are few in number and short. The background is transparent.

Photo 2 (control the melanocytes exhibit a larger number of dendrites than in Photo 1, some of them are much longer and 3 the background is slightly grey.

b /r 7 \7 ,y.

cw_ L L- 11 Photo 3 (composition ex. 2 the melanocytes are much bigger than in the previous two photos, the dendrites are at the same time numerous, longer and above all thicker. The background is grey, sprinkled with dark grains constituted by the released melanin.

Thus, it is obvious that the composition based on liposomes containing tyrosine has brought about a very marked increase in the activity of the melanocytes in the mice of group 3.

This in vivo experiment in the mouse clearly demonstrates the stimulating activity of the compositions according to the invention on melanogenesis as well as their value for the preparation of cosmetic or dermatological compositions with pigmenting activity.

TABLE I CONTROL CONTROL Composition example 2 U.V.

U.V.

275 335 494 221 682 826 381 520 955 224 624 433 293 588 545 492 423 278,8 540,1 612,6 Example 6 Cosmetic composition in gel form The composition according to example 1 can be utilized as it is as a cosmetic composition in the form of a gel.

This gel is applied daily to prepare the skin for the sun.

This treatment is preferably practiced eight days before any exposure SFA-'k to the sun.

i i 12 Example 7 Sun cosmetic composition A gelified suspension of liposomes according to example 4 is prepared with the following composition: Soya lecithin 3.8 g B-sitosterol 0.2 g &-tocopherol 0.1 g "glucose tyrosinate" 1 g gelified aqueous excipients to give 100 g This suspension is mixed with an equal volume of an oil-inwater emulsion prepared separately in a standard manner and containing an U.V. filter such as Parsol MCX at a concentration of 3 The composition obtained can be used as a sun tan milk.

Example 8: Cosmetic composition in the form of a lotion.

A gelified suspension of liposomes according to the procedure described in example 1 is prepared by using, however, a

R

Carbopol 940 gel two times less concentrated and a composition defined as follows: hydrogenated soya lecithin 9 g L-tyrosine 1 g gelified. aqueous excipients perfumes to give 100 g This lotion, applied morning and evening to the scalp, retards the appearance of grey hair.

Example 9: Cream for improving the complexion Soya lecithin 2 g b-tocopherol 0.06 g L-tyrosine 0.2 g excipients for oil-in-water emulsion to give 100 g A suspension of liposomes according to example 1, on the one hand, and an oil-in-water emulsion, on the other are prepared separately.

These two preparations are then mixed in the ratio of one volume of suspension of liposomes for three volumes of emulsion.

The cream obtained applied daily to the face, preferably in the morning, restores the complexion.

I

Claims (11)

1. Composition comprising hydrated lipidic amphiphilic lamellar phases or liposomes, wherein the hydrated lipidic amphiphilic lamellar phases or the liposomes comprise from 0.001 to 10% by weight, with respect to the total weight of the composition, of tyrosine or of a tyrosine derivative other than a tyrosine salt with a basic amino acid, said composition also comprising a pharmaceutically or cosmetically acceptable carrier.

2. Composition according to claim 1 wherein the hydrated lipidic amphiphilic lamellar phases or the liposomes comprise from 0.05% to 2% by weight, with respect to the total weight of the composition, of tyrosine or of a tyrosine derivative, excluding tyrosine salts with at least one basic amino acid.

3. Composition according to claim 1 or claim 2, wherein the tyrosine derivative is selected from a tyrosine salt and a tyrosine ester.

4. Composition according to any one of claims 1 to 3, 20 wherein the tyrosine is L-tyrosine.

5. Composition according to any one of claims 1 to 3, wherein the tyrosine derivative is selected from the group consisting of alkaline or alkaline-earth L-tyrosinate, sodium or calcium L-tyrosinate, methyl L-tyrosinate, ethyl 25 L-tyrosinate, stearyl L-tyrosinate, and of a compound obtained from L-tyrosine and from glucose.

6. Composition according to any one of claims 1 to said composition further containing beta-sitosterol.

7. Cosmetic or pharmaceutical composition according to 30 any one of claims 1 to 6 wherein the said composition has pigmenting activity.

8. Composition according to any one of claims 1 to 7 for pharmaceutical or cosmetic application. i i. i i i i_ i:- 14

9. Composition according to any one of claims 1 to 7 for dermatological application.

A method of pigmenting selected areas of the epidermis, comprising applying on said selected areas of the epidermis an effective amount of a composition comprising hydrated lipidic amphiphilic lamellar phases or liposomes containing as active ingredient a tyrosine component selected from the group consisting of a tyrosine and a tyrosine derivative other than a tyrosine salt with a basic amino acid.

11. The method of pigmentation according to claim 11, wherein the pigmentation is effected by a composition according to any one of claims 1 to 6. DATED THIS 18TH DAY OF AUGUST 1992 LVMH RECHERCHE By Its Patent Attorneys GRIFFITH HACK CO Fellows Institute of Patent S 20 Attorneys of Australia o o o Ti PATENT OF INVENTION Composition based on hydrated lipid lamellar phases or liposomes containing tyrosine or a tyrosine derivative and a cosmetic or pharmaceutical, and in particular dermatological, composition with pigmenting activity incorporating it. Invention Alain MEYBECK Marc DUMAS L V M H RESEARCH (Economic Interest Group) DESCRIPTIVE ABSTRACT The invention relates to a composition based on hydrated lipid lamellar phases or liposomes. This composition is characterized in that the said hydrated lipid lamellar phases or the said liposomes contain at least in part tyrosine or a tyrosine derivative, such as a salt or an ester. This composition finds application notably in the preparation of cosmetic or pharmaceutical, and in particular dermatological, compositions intended in particular to promote the tanning of the skin, improve the complexion or retard the appearance of grey hair. i S 2 f L I EEAC 1 /cnoi Intres ECITV