WO2023118005A1

WO2023118005A1 - Composition containing the combination of a c-glycoside and escin for the care of the eye area

Info

Publication number: WO2023118005A1
Application number: PCT/EP2022/086794
Authority: WO
Inventors: Franck JUCHAUX; Carine BALLIHAUT; Julien Laboureau
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2021-12-20
Filing date: 2022-12-19
Publication date: 2023-06-29
Anticipated expiration: 2024-06-20
Also published as: FR3130602A1

Abstract

The invention relates to the cosmetic use of a combination of at least one C- glycoside and escin for the care of the eye contour. The invention also relates to a cosmetic composition, particularly for treating the contour of the eyes, comprising, in a physiologically acceptable medium: from 1% to 10% by weight of active substance with respect to the total weight of the composition of at least one C-glycoside derivative, and, from 0.25 to 10% by weight of active substance with respect to the total weight of the composition of escin.

Description

DESCRIPTION

Composition containing the combination of a C-glycoside and escin for the care of the eye area

The present invention relates to the cosmetic use of a combination of at least one C-glycoside and escin for the care of the eye contour, particularly redness and/or edema of the periocular region, very particularly bags and/or dark rings in the periocular region.

The body in general is sensitive to external aggression from modern life (UV exposure, significant hygrometry and temperature variations, pollution, etc.). The response to this aggression can result inter alia in the onset of redness linked with local vasodilation or in the onset of local edema.

Furthermore, it is known that some skins are more sensitive than others to external aggression.

The eye contour region, due to its structures and its high innervation, represents a particularly sensitive anatomical site to aggression or to behavioral mechanical stress (friction). Its thin skin, depleted of skin lipids, is particularly sensitive to external aggression, exacerbated by loss of firmness and aging.

During inflammation located in the eye contour area, the endothelial cells located on the inner wall of the blood vessels can lose their property of impermeability to the passage of fluids on either side of the capillary walls. These circulation disorders give rise to the onset of eye bags or dark rings.

Following external aggression or stress and depending on the individuals, the eye contour quickly shows, with redness and/or itching, the effects of exacerbated vasodilation, and of temporary discomfort, and also with eye bags and/or dark rings and/or edema, of more persistent discomfort expressing greater metabolic exhaustion of the epidermis and dermis.

Besides these physiological data, it is known that merely from the cosmetic perspective, redness, dark rings and eye bags have always been considered unsightly, and that it has always been sought to conceal them, or remove them. Eye bags or dark rings can also appear with aging. Over time, the skin tissue located in this area slackens, the blood vessels become disorganized, which gives rise to poor circulation at the capillary vessels of this area.

An inflammatory reaction located in this area can also induce a rapid increase in microvascular fluid filtration, giving rise to fluid build-up and ultimately edema of inflammatory origin. This can give rise to pain, in addition to a cosmetic defect.

The formation of dark rings often occurs following a slowdown of blood microcirculation, particularly at night, which gives rise to a build-up of blood pigments in the connective tissue. Further, the lymphatic system, also slower at night, induces swelling of this skin. Such swelling, combined with age-related tissue slackening, can promote the formation of eye bags.

Moreover, in older subjects, natural rarefaction causing subcutaneous capillary vessel microcirculation disorders also gives rise to a yellowing (or dulling) of the face as a whole, and not only at the contour of the eye.

The products currently on the market essentially provide immediate effects and a sensory effect adapted to the eye contour area to treat eye bag, dark ring or edema problems. However, they provide few or no long-lasting effects, in particular on dark rings and/or eye bags associated with inflammatory and/or vascular mechanisms. Moreover, they do not enable simultaneous treatment of the signs of aging of keratin materials such as the skin, which are particularly manifested as a dulling of the skin, visibility of vessels and/or the appearance of wrinkles and lines.

Therefore, there is a need for an effective, long-term treatment of keratin materials, in particular the skin and particularly dark rings and/or eye bags and/or edema of the eye contour, which is also effective for reducing the signs of aging of keratin materials such as the skin, in particular wrinkles and lines.

This invention helps meet these expectations.

Surprisingly, the Applicant discovered that the specific combination of a C-glycoside derivative with escin helped strengthen the walls of blood vessels, and treat the signs of aging of keratin materials such as the skin. This helps reduce dark rings, and/or eye bags and/or edema particularly at the eye contour. Without seeking to be bound to any theory, the inventors discovered that a C-glycoside derivative formulated with escin, in given quantities, has a synergistic or potentiating effect, and makes it possible to limit endothelial tissue permeability, and therefore provide overall care of the eye contour.

Such a combination provides overall care of the skin, in particular the eye contour: indeed, it helps reduce dark rings and/or edema and/or signs of skin aging such as wrinkles and lines. These three major effects are obtained with the combination according to the invention.

Such a combination also enables an optimization of complexion homogeneity, a reduction in relief irregularities and imperfections and a reduction in wrinkles and lines. Finally, such a combination may have a benefit for reducing vascular skin problems on the face or body, which particularly manifest as a dulling of the skin, in particular observed pre- and post-menopause.

The invention thus relates to the cosmetic use of a combination of at least one C- glycoside and escin for the care of the eye contour.

"Care of the eye contour" means that the combination according to the invention makes it possible to reduce and/or minimize the appearance of defects around the eyes such as dark rings, eye bags and/or edema and/or makes it possible to reduce the signs of skin aging of the eye contour.

Preferably, such a combination is used to reduce skin relief irregularity, such as for example wrinkles and lines around the eye. Preferably, such a combination is used to reduce skin coloring defects linked with dark rings, and/or to improve the homogeneity of the complexion and/or skin glow; dark rings fade, and the complexion becomes more homogeneous.

The invention also relates to the cosmetic use of a combination of at least one C- glycoside and escin to reduce dulling of the skin of the entire face in older subjects.

"Older subject" means a subject, preferably human, aged at least 60 years, preferably at least 65 years, preferably at least 70 years.

Indeed, in older subjects, a yellowing or dulling of the skin, in particular the facial skin, is generally observed; the skin develops a parchment-like appearance, and becomes duller and loses its glow. The combination according to the invention makes it possible to revive the microcirculation. Through this action, the dulling of the facial skin lessens, and a certain glow is restored to the skin. Such uses are cosmetic and non-therapeutic.

The invention also relates to a cosmetic composition, particularly for treating the contour of the eyes, comprising, in a physiologically acceptable medium: from 1% to 10% by weight of active substance with respect to the total weight of the composition of at least one C-glycoside derivative, and, from 0.25 to 10% by weight of active substance with respect to the total weight of the composition of escin.

Preferably, the invention also relates to the cosmetic use of such a composition for the care of the eye contour.

The invention also relates to a non-therapeutic cosmetic care method for the eye contour, comprising the application on the eye contour area of a composition according to the invention.

Preferably, the cosmetic composition is used in different types of cosmetic substrates, such as galenic substrates, patches or masks. It can be incorporated into care routines or in treatments accompanying cosmetic procedures. It can also be part of the cosmetic procedure per se.

According to the invention, "synergistic or potentiating effect" is intended to describe a response or an effect resulting from an implementation of a combination of elements greater than the sum of the responses or effects resulting from the separate implementation of these elements.

According to the invention, "cosmetically acceptable substrate" means a substrate compatible with the skin, mucosa, nails, hair. This substrate can be in any galenic forms normally used for a topical application, particularly in the form of an aqueous, hydroalcoholic or oily solution, an oil-in-water or water-in-oil or multiple emulsion, an aqueous or oily gel, a liquid, pasty or solid anhydrous product, a dispersion of oil in an aqueous phase using spherules, these spherules optionally being polymeric nanoparticles such as nanospheres and nanocapsules or preferably ionic and/or non-ionic type lipidic vesicles.

According to the invention, "eye contour" means an area located around the eye, particularly under the eye and the upper eyelid. C-glycoside

The C-glycoside (or C-glycoside derivative) according to the invention preferably has the following general formula (I):

[Chem 1] — R

^S—/ (I) wherein:

- R represents:

- a saturated C1 to C20, in particular C1 to C10, or unsaturated C2 to C20, in particular C3 to C10, linear alkyl radical, or a saturated or unsaturated, C3 to C20, in particular C4 to C10, branched or cyclic alkyl radical;

- a linear saturated C1 to C20, in particular C2 to C10, or unsaturated C2 to C20, in particular C2 to C10, or branched or cyclic, saturated or unsaturated, C3 to C20, in particular C4 to C10, hydrofluoro- or perfluoro-alkyl radical;

- a phenyl or benzyl radical, the hydrocarbon chain forming said radicals optionally being, where applicable, interrupted by 1 , 2, 3 or more heteroatoms chosen from:

- an oxygen,

- a sulfur,

- a nitrogen, and

- a silicon, and optionally being substituted by at least one radical chosen from:

- -OR4,

- -SR4,

- -NR4R5,

- -COOR4,

- -CONHR4,

- -CN,

- a halogen atom,

- a C1 to C6 hydrofluoro- or perfluoro-alkyl radical, and/or

- a C3 to C8 cycloalkyl radical, and/or

- at least one C5 to C18 cycloalkyl, aryl, heterocyclic radical, optionally substituted, where R4 and R5 can represent, independently from one another, a hydrogen atom, or a saturated C1 to C30, particularly C3 to C12, or unsaturated C2 to C30, particularly C3 to C12 linear, or saturated or unsaturated C3 to C30, particularly C4 to C12, branched or cyclic alkyl, perfluoroalkyl or hydrofluoroalkyl radical; or a C6 to C10 aryl radical, - X represents a radical chosen from -CO-, -CH(OH)-, -CH(NH₂)-, and preferably a -CH(OH)- group;

- S represents a monosaccharide or a polysaccharide including up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of L and/or D series, said mono- or poly-saccharide being optionally substituted by a mandatorily free hydroxyl group, and optionally one or more optionally protected amine function(s), and

- the bond S-CH2-X represents a C-anomeric type bond, which can be a or p, and the physiologically acceptable salts thereof, the solvates thereof such as hydrates and the isomers thereof.

Within the scope of the present invention, "halogen" means chlorine, fluorine, bromine or iodine.

The term "aryl" denotes an aromatic ring system, such as phenyl, optionally substituted by one or more C1 -C4 alkyl radicals.

The term "C3 to C8 cycloalkyl" denotes an aliphatic ring system having from 3 to 8 carbon atoms, including for example cyclopropyl, cyclopentyl and cyclohexyl.

Among the alkyl groups suitable of the implementation of the invention, mention can particularly be made of the methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, secbutyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl, and allyl groups.

A C-glycoside derivative can comply with formula (I) for which S can represent a monosaccharide or a polysaccharide containing up to 6 sugar units, in pyranose and/or furanose form and L and/or D series, said mono- or polysaccharide having at least one mandatorily free hydroxyl function and/or optionally one or more mandatorily protected amine functions, X and R also retaining all of the definitions given above.

Advantageously, a monosaccharide according to the invention can be chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose, L-fucose, L-arabinose, L- rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D- glucosamine, N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose.

More specifically, a polysaccharide according to the invention containing up to 6 sugar units can be chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide associating a uronic acid chosen from D-iduronic acid or D-glucuronic acid with a hexosamine chosen from D-galactosamine, D-glucosamine, N-acetyl-D- galactosamine, N-acetyl-D-glucosamine, an oligosaccharide containing at least one xylose which can be advantageously chosen from xylobiose, methyl-p-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and particularly xylobiose which is composed of two xylose molecules bound by a 1 -4 bond.

More specifically, S can represent a monosaccharide chosen from D-glucose, D- xylose, L-fucose, D-galactose, D-maltose and particularly D-xylose.

According to an embodiment of the invention, a C-glycoside derivative complying with formula (I) can be used, for which R represents a saturated C1 to C20, in particular C1 to C10, or unsaturated C2 to C20, in particular C3 to C10, linear alkyl radical, or a saturated or unsaturated, C3 to C20 branched or cyclic alkyl radical; in particular C4 to C10, and optionally substituted as described above, S and X also retaining all of the definitions given above.

In particular, R can denote a C1 -C4, particularly C1 -C2, linear radical, optionally substituted by -OH, -COOH or -COOR”2, R”2 being a saturated C1-C4 linear alkyl radical, particularly methyl. In particular, R can denote a non-substituted C1 -C4, particularly C1 -C2, linear alkyl radical, in particular methyl.

Among the C-glycoside derivatives of formula (I), it is particularly possible to use those for which:

- R represents a saturated C1 to C20, in particular C1 to C10, or unsaturated C2 to C20, in particular C3 to C10, linear alkyl radical, or a saturated or unsaturated, C3 to C20, in particular C4 to C10, branched or cyclic alkyl radical and optionally substituted as described above;

- S represents a monosaccharide as described above, preferably D-glucose, D- xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;

- X represents a radical chosen from -CO-, -CH(OH)-, -CH(NH₂)-, and preferably a -CH(OH)- group.

More specifically, a C-glycoside derivative of formula (I) is used, for which:

- R denotes a C1 -C4, particularly C1 -C3, linear radical, optionally substituted by - OH, -COOH or -COOR”2, R”2 being a saturated C1-C4 linear alkyl radical, particularly methyl;

According to an embodiment, a C-glycoside derivative of formula (I) can be used, for which: - R denotes a non-substituted C1 -C4, particularly C1 -C2, linear alkyl radical, in particular methyl;

- X represents a group chosen from -CO-, -CH(OH)-, -CH(NH2)-, and preferably a - CH(OH)- group.

The acceptable salts for the non-therapeutic use of the compounds described in the present invention comprise conventional non-toxic salts of said compounds such as those formed from organic or inorganic acids. By way of example, mention can be made of the salts of mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acids, hydroiodic acid, phosphoric acid, boric acid. Mention can also be made of organic acid salts, which can include one or more carboxylic, sulfonic or phosphonic acid group(s). They can consist of linear, branched or cyclic aliphatic acids or indeed aromatic acids. These acids can further include one or more heteroatoms selected from O and N, for example in the form of hydroxyl groups. Mention can particularly be made of propionic acid, acetic acid, terephthalic acid, citric acid, and tartaric acid.

When the compound of formula (I) includes an acid group, the acid group(s) can be neutralized with a mineral base, such as LiOH, NaOH, KOH, Ca(OH)2, NH4OH, Mg(OH)2 or Zn(OH)2; or by an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine can include one or more nitrogen and/or oxygen atoms and can therefore include for example one or more alcohol functions; mention can particularly be made of amino-2-methyl-2- propanol, triethanolamine, dimethylamino-2-propanol, 2-amino-2-(hydroxymethyl)-1 ,3- propanediol. Mention can further be made of lysine or 3-(dimethylamino)propylamine.

The acceptable solvates for the compounds described in the present invention comprise conventional solvates such as those formed during the final preparation step of said compounds due to the presence of solvents. By way of example, mention can be made of solvates due to the presence of water or linear or branched alcohols such as ethanol or isopropanol.

Among the C-glycoside derivatives of formula (I), used according to the invention, the following are very particularly considered:

1 . C-p-D-xylopyranoside-n-propane-2-one;

2. C-a-D-xylopyranoside-n-propane-2-one;

3. 1 -[2-(3-hydroxy-propylamino)-propyl]- C- p -D-xylopyranose;

4. 1 -[2-(3-hydroxy-propylamino)-propyl]-C-a-D-xylopyranose; 5. C-p-D-xylopyranoside-2-hydroxy-propane;

6. C-a-D-xylopyranoside-2-hydroxy-propane;

7. C-p-D-xylopyranoside-2-amino-propane;

8. C-a-D-xylopyranoside-2-amino-propane;

9. C-p-D-xylopyranoside-2-phenylamino-propane;

10. C-a-D-xylopyranoside-2-phenylamino-propane;

11 . 3-methyl-4-(C-p-D-xylopyranoside)-butyric acid ethyl ester;

12. 3-methyl-4-(C-a-D-xylopyranoside)-butyric acid ethyl ester;

13. 6-(C-p-D-xylopyranoside)-5-keto-hexanoic acid;

14. 6-(C-a-D-xylopyranoside)-5-keto-hexanoic acid;

15. 6-(C-p-D-xylopyranoside)-5-hydroxy-hexanoic acid;

16. 6-(C-a-D-xylopyranoside)-5-hydroxy-hexanoic acid;

17. 6-(C-p-D-xylopyranoside)-5-amino-hexanoic acid;

18. 6-(C-a-D-xylopyranoside)-5-amino-hexanoic acid;

19. 6-(C-p-D-xylopyranoside)-5-phenylamino-hexanoic acid;

20. 6-(C-a-D-xylopyranoside)-5-phenylamino-hexanoic acid;

21. 1 -(C-p-D-xylopyranoside)-hexane-2,6-diol;

22. 1-(C-a-D-xylopyranoside)-hexane-2,6-diol;

23. 5-(C-p-D-xylopyranoside)-4-keto-pentanoic acid;

24. 5-(C-a-D-xylopyranoside)-4-keto-pentanoic acid;

25. 5-(C-p-D-xylopyranoside)-4-hydroxy-pentanoic acid;

26. 5-(C-a-D-xylopyranoside)-4-hydroxy-pentanoic acid;

27. 5-(C-p-D-xylopyranoside)-4-amino-pentanoic acid;

28. 5-(C-a-D-xylopyranoside)-4-amino-pentanoic acid;

29. 5-(C-p-D-xylopyranoside)-4-phenylamino-pentanoic acid;

30. 5-(C-a-D-xylopyranoside)-4-phenylamino-pentanoic acid;

31. 1-(C-p-D-xylopyranoside)-pentane-2,5-diol;

32. 1 -(C-a-D-xylopyranoside)-pentane-2,5-diol;

33. 1 -(C-p-D-fucopyranoside)-propane-2-one;

34. 1 -(C-a-D-fucopyranoside)-propane-2-one;

35. 1 -(C-p-L-fucopyranoside)-propane-2-one;

36. 1 -(C-a-L-fucopyranoside)-propane-2-one;

37. 1 -(C-p-D-fucopyranoside)-2-hydroxy-propane;

38. 1 -(C-a-D-fucopyranoside)-2-hydroxy-propane;

39. 1 -(C-p-L-fucopyranoside)-2-hydroxy-propane;

40. 1 -(C-a-L-fucopyranoside)-2-hydroxy-propane; 41 . 1 -(C-p-D-fucopyranoside)-2-amino-propane;

42. 1 -(C-a-D-fucopyranoside)-2-amino-propane;

43. 1 -(C-p-L-fucopyranoside)-2-amino-propane;

44. 1 -(C-a-L-fucopyranoside)-2-amino-propane;

45. 1 -(C-p-D-fucopyranoside)-2-phenylamino-propane;

46. 1 -(C-a-D-fucopyranoside)-2-phenylamino-propane;

47. 1 -(C-p-L-fucopyranoside)-2-phenylamino-propane;

48. 1 -(C-a-L-fucopyranoside)-2-phenylamino-propane;

49. 3-methyl-4-(C-p-D-fucopyranoside)-butyric acid ethyl ester;

50. 3-methyl-4-(C-a-D-fucopyranoside)-butyric acid ethyl ester;

51. 3-methyl-4-(C-p-L-fucopyranoside)-butyric acid ethyl ester;

52. 3-methyl-4-(C-a-L-fucopyranoside)-butyric acid ethyl ester;

53. 6-(C-p-D-fucopyranoside)-5-keto-hexanoic acid;

54. 6-(C-a-D-fucopyranoside)-5-keto-hexanoic acid;

55. 6-(C-p-L-fucopyranoside)-5-keto-hexanoic acid;

56. 6-(C-a-L-fucopyranoside)-5-keto-hexanoic acid;

57. 6-(C-p-D-fucopyranoside)-5-hydroxy-hexanoic acid;

58. 6-(C-a-D-fucopyranoside)-5-hydroxy-hexanoic acid;

59. 6-(C-p-L-fucopyranoside)-5-hydroxy-hexanoic acid;

60. 6-(C-a-L-fucopyranoside)-5-hydroxy-hexanoic acid;

61. 6-(C-p-D-fucopyranoside)-5-amino-hexanoic acid;

62. 6-(C-a-D-fucopyranoside)-5-amino-hexanoic acid;

63. 6-(C-p-L-fucopyranoside)-5-amino-hexanoic acid;

64. 6-(C-a-L-fucopyranoside)-5-amino-hexanoic acid;

65. 1 -(C-p-D-fucopyranoside)-hexane-2,6-diol;

66. 1-(C-a-D-fucopyranoside)-hexane-2,6-diol;

67. 1 -(C-p-L-fucopyranoside)-hexane-2,6-diol;

68. 1 -(C-a-L-fucopyranoside)-hexane-2,6-diol;

69. 5-(C-p-D-fucopyranoside)-4-keto-pentanoic acid;

70. 5-(C-a-D-fucopyranoside)-4-keto-pentanoic acid;

71 . 5-(C-p-L-fucopyranoside)-hexane-2,6-diol)-4-keto-pentanoic acid;

72. 5-(C-a-L-fucopyranoside)-hexane-2,6-diol)-4-keto-pentanoic acid;

73. 5-(C-p-D-fucopyranoside)-4-hydroxy-pentanoic acid;

74. 5-(C-a-D-fucopyranoside)-4-hydroxy-pentanoic acid;

75. 5-(C-p-L-fucopyranoside)-4-hydroxy-pentanoic acid;

76. 5-(C-a-L-fucopyranoside)-4-hydroxy-pentanoic acid; 77. 5-(C-p-D-fucopyranoside)-4-amino-pentanoic acid;

78. 5-(C-a-D-fucopyranoside)-4-amino-pentanoic acid;

79. 5-(C-p-L-fucopyranoside)-4-amino-pentanoic acid;

80. 5-(C-a-L-fucopyranoside)-4-amino-pentanoic acid;

81. 1-(C-p-D-fucopyranoside)-pentane-2,5-diol;

82. 1 -(C-a-D-fucopyranoside)-pentane-2,5-diol;

83. 1 -(C-p-L-fucopyranoside)-pentane-2,5-diol;

84. 1 -(C-a-L-fucopyranoside)-pentane-2,5-diol;

85. 1 -(C-p-D-glucopyranosyl)-2-hydroxy-propane;

86. 1 -(C-a-D-glucopyranosyl)-2-hydroxy-propane;

87. 1 -(C-p-D-glucopyranosyl)-2-amino-propane;

88. 1 -(C-a-D-glucopyranosyl)-2-amino-propane;

89. 1 -(C-p-D-glucopyranosyl)-2-phenylamino-propane;

90. 1 -(C-a-D-glucopyranosyl)-2-phenylamino-propane;

91. 3-methyl-4-(C-p-D-glucopyranosyl)-butyric acid ethyl ester;

92. 3-methyl-4-(C-a-D-glucopyranosyl)-butyric acid ethyl ester;

93. 6-(C-p-D-glucopyranosyl)-5-keto-hexanoic acid;

94. 6-(C-a-D-glucopyranosyl)-5-keto-hexanoic acid;

95. 6-(C-p-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

96. 6-(C-a-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

97. 6-(C-p-D-glucopyranosyl)-5-amino-hexanoic acid;

98. 6-(C-a-D-glucopyranosyl)-5-amino-hexanoic acid;

99. 6-(C-p-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

100. 6-(C-a-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

101. 1 -(C-p-D-glucopyranosyl)-hexane-2,6-diol;

102. 1 -(C-a-D-glucopyranosyl)-hexane-2,6-diol;

103. 6-(C-p-D-glucopyranosyl)-5-keto-pentanoic acid;

104. 6-(C-a-D-glucopyranosyl)-5-keto-pentanoic acid;

105. 6-(C-p-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

106. 6-(C-a-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

107. 6-(C-p-D-glucopyranosyl)-5-amino-pentanoic acid;

108. 6-(C-a-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

109. 6-(C-p-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

110. 6-(C-a-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

111. 1 -(C-p-D-glucopyranosyl)-pentane-2,5-diol;

112. 1 -(C-a-D-glucopyranosyl)-pentane-2,5-diol; 113. 1 -(C-p-D-galactopyranosyl)-2-hydroxy-propane;

114. 1 -(C-a-DD-galactopyranosyl)-2-hydroxy-propane;

115. 1 -(C-p-D-galactopyranosyl)-2-amino-propane;

116. 1 -(C-a-D-galactopyranosyl)-2-amino-propane;

117. 1 -(C-p-D-galactopyranosyl)-2-phenylamino-propane;

118. 1 -(C-a-D-galactopyranosyl)-2-phenylamino-propane;

119. 3-methyl-4-(P-D-galactopyranosyl)-butyric acid ethyl ester;

120. 3-methyl-4-(a-D-galactopyranosyl)-butyric acid ethyl ester;

121 . 6-(C-p-D-galactopyranosyl)-5-keto-hexanoic acid;

122. 6-(C-a-D-galactopyranosyl)-5-keto-hexanoic acid;

123. 6-(C-p-D-galactopyranosyl)-5-hydroxy-hexanoic acid;

124. 6-(C-a-D-galactopyranosyl)-5-hydroxy-hexanoic acid;

125. 6-(C-p-D-galactopyranosyl)-5-amino-hexanoic acid;

126. 6-(C-a-D-galactopyranosyl)-5-amino-hexanoic acid;

127. 6-(C-p-D-galactopyranosyl)5-phenylamino-hexanoic acid;

128. 6-(C-a-D-galactopyranosyl)5-phenylamino-hexanoic acid;

129. 1 -(C-p-D-galactopyranosyl)-hexane-2,6-diol;

130. 1 -(C-a-D-galactopyranosyl)-hexane-2,6-diol;

131 . 6-(C-p-D-galactopyranosyl)-5-keto-pentanoic acid;

132. 6-(C-a-D-galactopyranosyl)-5-keto-pentanoic acid;

133. 6-(C-p-D-galactopyranosyl)-5-hydroxy-pentanoic acid;

134. 6-(C-a-D-galactopyranosyl)-5-hydroxy-pentanoic acid;

135. 6-(C-p-D-galactopyranosyl)-5-amino-pentanoic acid;

136. 6-(C-a-D-galactopyranosyl)-5-amino-pentanoic acid;

137. 6-(C-p-D-galactopyranosyl)-5-phenylamino-pentanoic acid;

138. 6-(C-a-D-galactopyranosyl)-5-phenylamino-pentanoic acid;

139. 1 -(C-p-D-galactopyranosyl)-pentane-2,6-diol;

140. 1 -(C-a-D-galactopyranosyl)-pentane-2,6-diol;

141. 1 -(C-p-D-fucofuranosyl)-propane-2-one;

142. 1 -(C-a-D-fucofuranosyl)-propane-2-one;

143. 1 -(C-p-L-fucofuranosyl)-propane-2-one;

144. 1 -(C-a-L-fucofuranosyl)-propane-2-one;

145. 3'-(acetamido-C-p-D-glucopyranosyl)-propane-2'-on ;

146. 3'-(acetamido-C-a-D-glucopyranosyl)-propane-2'-one;

147. 1 -(acetamido-C-p-D-glucopyranosyl)-2-hydroxyl-propane;

148. 1 -(acetamido-C-p-D-glucopyranosyl)-2-amino-propane; 149. 1 -(acetamido-C-p-D-glucopyranosyl)-2-phenylamino-propane;

150. 1 -(acetamido-C-a-D-glucopyranosyl)-2-phenylamino-propane;

151 . 3-methyl-4-(acetamido-C-p-D-glucopyranosyl)- butyric acid ethyl ester

152. 3-methyl-4-(acetamido-C-a-D-glucopyranosyl)- butyric acid ethyl ester

153. 6-(acetamido-C-p-D-glucopyranosyl)-5-keto-hexanoic acid;

154. 6-(acetamido-C-a-D-glucopyranosyl)-5-keto-hexanoic acid;

155. 6-(acetamido-C-p-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

156. 6-(acetamido-C-a-D-glucopyranosyl)-5-hydroxy-hexanoic acid;

157. 6-(acetamido-C-p-D-glucopyranosyl)-5-amino-hexanoic acid;

158. 6-(acetamido-C-a-D-glucopyranosyl)-5-amino-hexanoic acid;

159. 6-(acetamido-C-p-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

160. 6-(acetamido-C-a-D-glucopyranosyl)-5-phenylamino-hexanoic acid;

161 . 1 -(acetamido-C-p-D-glucopyranosyl)-hexane-2,6-diol;

162. 1 -(acetamido-C-a-D-glucopyranosyl)-hexane-2,6-diol;

163. 6-(acetamido-C-p-D-glucopyranosyl)-5-keto-pentanoic acid;

164. 6-(acetamido-C-a-D-glucopyranosyl)-5-keto-pentanoic acid;

165. 6-(acetamido-C-p-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

166. 6-(acetamido-C-a-D-glucopyranosyl)-5-hydroxy-pentanoic acid;

167. 6-(acetamido-C-p-D-glucopyranosyl)-5-amino-pentanoic acid;

168. 6-(acetamido-C-a-D-glucopyranosyl)-5-amino-pentanoic acid;

169. 6-(acetamido-C-p-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

170. 6-(acetamido-C-a-D-glucopyranosyl)-5-phenylamino-pentanoic acid;

171 . 1 -(acetamido-C-p-D-glucopyranosyl)-pentane-2,5-diol;

172. 1 -(acetamido-C-a-D-glucopyranosyl)-pentane-2,5-diol.

By way of illustration and not limitation of the C-glycoside derivatives more specifically suitable for the invention, mention can particularly be made of the following compounds:

- C-p-D-xylopyranoside-n-propane-2-one,

- C-a- D-xylopyranoside-n-propane-2-one,

- C-p-D-xylopyranoside-2-hydroxy-propane,

- C-a- D-xylopyranoside-2-hydroxy-propane,

- 1 -(C-p-D-fucopyranoside)-propane-2-one,

- 1 -(C-a-D-fucopyranoside)-propane-2-one, - 1 -(C-p-L-fucopyranoside)-propane-2-one,

- 1 -(C-a-L-fucopyranoside)-propane-2-one,

- 1 -(C-p-D-fucopyranoside)-2-hydroxy-propane,

- 1 -(C-a-D-fucopyranoside)-2-hydroxy-propane,

- 1 -(C-p-L-fucopyranoside)-2-hydroxy-propane,

- 1 -(C-a-L-fucopyranoside)-2-hydroxy-propane,

- 1 -(C-p-D-Glucopyranosyl)-2-hydroxyl-propane,

- 1 -(C-a-D-Glucopyranosyl)-2-hydroxyl-propane,

- 1 -(C-p-D-galactopyranosyl)-2-hydroxyl-propane,

- 1 -(C-a-D-galactopyranosyl)-2-hydroxyl-propane

- 1 -(C-p-D-fucofuranosyl)-propane-2-one,

- 1 -(C-a-D-fucofuranosyl)-propane-2-one

- 1 -(C-p-L-fucofuranosyl)-propane-2-one,

- 1 -(C-a-L-fucofuranosyl)-propane-2-one,

- C-p-D-maltopyranoside-n-propane-2-one,

- C-a-D-maltopyranoside-n-propane-2-one

- C-p-D-maltopyranoside-2-hydroxy-propane,

- C-a-D-maltopyranoside-2-hydroxy-propane, isomers thereof or mixtures thereof.

Preferably, C-beta-D-xylopyranoside-2-hydroxy-propane or

C-alpha-D-xylopyranoside-2-hydroxy-propane is used, and more preferably C-beta-D-xylopyranoside-2-hydroxy-propane. Preferably, a C-glycoside of formula (I) suitable for the invention can be advantageously C-beta-D-xylopyranoside-2-hydroxy- propane, of which the INCI name is HYDROXYPROPYL TETRAHYDROPYRANTRIOL particularly sold under the name MEXORYL SBB® or MEXORYL SCN® by NOVEAL. MEXORYL SBB® for example contains 35% by weight of hydroxypropyl tetrahydropyrantriol in 40% by weight water and 25% propylene glycol.

The composition according to the invention comprises at least one C-glycoside derivative at a content of 1% to 10% by weight of active substance with respect to the total weight of the composition, and preferably from 2% to 9% by weight of active substance, and more specifically from 3% to 7% by weight of active substance.

A C-glycoside as defined above is used in combination with escin. Such a combination proves to be particularly advantageous in terms of effectiveness, particularly for overall cosmetic care of the eye contour. Escin

The composition according to the invention comprises escin. The escin can be of synthetic or natural origin.

Escin is a chemical molecule formed from a glucuronic acid and two sugars (glucose-xylose) bound to an aglycone, deglucoescin which has a molecular weight of 1131.24 g.mol’¹. It is a molecule found for example in plant extracts, particularly in horse chestnut extracts.

Synthetic origin means escin, in the pure state or in solution regardless of the concentration thereof in said solution, obtained by chemical synthesis.

Natural origin means escin, in the pure state or in solution regardless of the concentration thereof in said solution, obtained from a natural element and/or comprised therein such as for example a plant extract, particularly a horse chestnut extract.

By way of example, the escin according to the invention is marketed by Indena under the trade name 3030000 ESCIN FREE ACID®.

The composition according to the invention comprises escin at a content of 0.25 to 10% by weight of active substance with respect to the total weight of the composition, and preferably from 0.3% to 9% by weight of active substance, and more specifically from 0.3% to 3% by weight of active substance.

Physiologically acceptable medium

The composition according to the invention also comprises a physiologically acceptable medium. This physiologically acceptable medium can be chosen by a person skilled in the art based on their general knowledge according to the type of composition sought.

As a general rule, this medium can be anhydrous or aqueous. It can thus comprise an aqueous phase and/or a fatty phase.

Thus, preferably, said physiologically acceptable medium comprises an aqueous phase and/or a fatty phase.

A composition considered in the invention can be formulated in the form of a solid, semi-solid, or liquid emulsion.

Preferably, the composition according to the invention is an aqueous composition. "Aqueous composition" means any composition comprising at least 5% by weight of water with respect to the total weight of the composition and preferably from 5 to 99% by weight and even more preferably from 20 to 99% by weight.

Alternatively, preferably, the composition according to the invention is anhydrous. "Anhydrous composition" means any composition comprising less than 5% by weight of water with respect to the total weight of the composition and more preferably less than 1 % water, preferably less than 0.5% by weight of water, preferably any composition free from water.

A composition according to the invention can be administered topically.

For application to the skin, the composition can take the form in particular of an aqueous or oily solution; of a dispersion of the lotion or serum type; of an emulsion of liquid or semi-liquid consistency of the milk type obtained by dispersing a fatty phase in an aqueous phase (O/W), conversely (W/O), or triple O/W/O or W/O/W; of a suspension or emulsion of soft consistency of the cream or aqueous or anhydrous gel type; of microcapsules or microparticles; of ionic and/or non-ionic type vesicular dispersions.

When the composition comprises an aqueous phase, it comprises water, a floral water and/or a mineral water.

Said aqueous phase can further comprise one or more organic solvents such as a C1 -C8 alcohol, particularly ethanol, isopropanol, tert-butanol, n-butanol, pentanol, hexanol, polyols such as glycerin, propylene glycol, butylene glycol, capryl/caprylic glycol, isoprene glycol, polyethylene glycol and polyol ethers.

When the composition according to the invention is in the form of an emulsion, it can optionally further comprise a surfactant, preferably at a quantity of 0.01 to 30% by weight with respect to the total weight of the composition. The composition according to the invention can also comprise at least one co-emulsifier which can be chosen from oxyethylenated sorbitan monostearate, fatty alcohols such as stearyl alcohol or cetyl alcohol, or esters of fatty acids and polyols such as glyceryl stearate.

The composition according to the invention can also comprise a fatty phase, particularly consisting of fats that are liquid at 25°C, such as oils of animal, plant, mineral or synthetic origin, optionally volatile; fats that are solid at 25°C such as waxes of animal, plant, mineral or synthetic origin; pasty fats; gums; mixtures thereof. Volatile oils are generally oils having, at 25°C, a saturation vapor pressure at least equal to 0.5 millibar (or 50 Pa).

Among the constituents of the fatty phase, mention can be made of:

- cyclic volatile silicones having from 3 to 8 silicon atoms, preferably from 4 to 6,

- dimethylsiloxane/methylalkylsiloxane type cyclopolymers,

- linear volatile silicones having from 2 to 9 silicon atoms,

- volatile hydrocarbon oils, such as isoparaffins and particularly isododecane and fluorinated oils,

- polyalkyl(C1 -C20) siloxanes and particularly those with trimethylsilyl terminal groups, of which mention can be made of linear polydimethylsiloxanes and alkylmethylpolysiloxanes such as cetyldimethicone (CTFA name),

- silicones modified by aliphatic and/or aromatic groups, optionally fluorinated, or by functional groups such as hydroxyl, thiol and/or amine groups,

- phenylated silicone oils,

- oils of animal, plant or mineral origin, and particularly animal or plant oils formed by esters of fatty acid and polyols, in particular liquid triglycerides, for example, sunflower, corn, soybean, pumpkin, grape seed, sesame, hazelnut, apricot, almond or avocado oils; fish oils, glycerol tricaprocaprylate, or plant or animal oils of formula R1COOR2 wherein R1 represents the residue of a higher fatty acid including from 7 to 19 carbon atoms and R2 represents a branched hydrocarbon chain containing from 3 to 20 carbon atoms, for example, Purcellin oil; paraffin oil, petroleum jelly, perhydrosqualene, wheatgerm, calophyllum, sesame, macadamia, grape seed, rapeseed, coconut, peanut, palm, castor, jojoba, olive, argan or cereal germ oil; fatty acid esters; alcohols; acetylglycerides; alcohol or polyalcohol octanoates, decanoates or ricinoleates; fatty acid triglycerides; glycerides,

- fluorinated and perfluorinated oils,

- silicone gums,

- waxes of animal, plant, mineral or synthetic origin such as microcrystalline waxes, paraffin, petrolatum, petroleum jelly, ozokerite, montan wax; beeswax, lanolin and derivatives thereof; Candelilla, Ouricury, Carnauba, Japan wax, cocoa butter, cork fiber or sugar cane waxes; hydrogenated oils that are solid at 25°C, ozokerites, fatty esters and glycerides that are solid at 25°C; polyethylene, polymethylene waxes and waxes obtained by Fischer-Tropsch synthesis; hydrogenated oils that are solid at 25°C; lanolins; fatty acid esters that are solid at 25°C; silicone waxes; fluorinated waxes.

The composition according to the invention can also comprise usual adjuvants in the field in question, such as hydrophilic of lipophilic gelling agents, hydrophilic or lipophilic, particularly cosmetic or pharmaceutical, active agents, preservatives, antioxidants, perfumes, fillers, thickening polymers, sequestering agents, pigments, nacres, UV filters, odor absorbers and dyes. These adjuvants, depending on their nature, can be introduced in the fatty phase, in the aqueous phase and/or in lipid spherules.

The nature and quantity of these adjuvants can be chosen by a person skilled in the art, based on their general knowledge, so as to obtain the sought form for the composition. In any case, a person skilled in the art will take care to choose any additional compounds, and/or the quantity thereof, such that the advantageous properties of the composition according to the invention are not, or are substantially not, altered by the envisaged addition.

The compositions according to the invention can particularly be in the form of a composition intended for the care and/or treatment of dark rings, bags and/or edema in the periocular region.

Preferably, the compositions according to the invention are particularly in the form of:

- a product for the care, treatment, cleansing or protection of the skin of the face or body, such as a (day, night, moisturizing) care composition for the face or body; an antiwrinkle or anti-aging composition for the face; a mattifying composition for the face; a composition for irritated skins; a makeup removal composition; a particularly moisturizing optionally after-sun milk for the body;

- a sunscreen, artificial tanning (self-tanning) or after-sun care composition;

- a makeup product for the skin of the face, body or lips, such as a foundation, a tinted cream, a blusher or eye shadow, a free or compact powder, an anti-dark ring stick, a concealer stick, a lipstick, a lip care product.

The compositions according to the invention find a preferred application as a facial skin care composition, of the anti-dark ring or anti-aging type.

The composition used according to the invention can furthermore contain other active agents, and particularly at least one compound chosen from: moisturizing agents; anti-glycation agents; NO-synthase inhibitors; agents stimulating dermal or epidermal macromolecule synthesis and/or preventing the degradation thereof and/or involved in the organization thereof; agents stimulating fibroblast and/or keratinocyte proliferation or stimulating keratinocyte differentiation; agents involved in the energy metabolism; sun filters, and mixtures thereof.

"Moisturizing agent" means:

- either a compound acting on the barrier function, with a view to maintaining the hydration of the stratum corneum, or an occlusive compound. Mention can be made of ceramides, sphingoid-based compounds, lecithins, glycosphingolipids, phospholipids, cholesterol and derivatives thereof, phytosterols (stigmasterol, p-sitosterol, campesterol), essential fatty acids, 1 -2 diacylglycerol, 4-chromanone, pentacyclic triterpenes such as ursolic acid, petroleum jelly and lanolin;

- or a compound directly increasing the water content of the stratum corneum, such as trehalose and derivatives thereof, hyaluronic acid and derivatives thereof, glycerol, pentanediol, sodium pidolate, serine, xylitol, sodium lactate, glycerol polyacrylate, ectoin and derivatives thereof, chitosan, oligo- and polysaccharides, cyclic carbonates, N-lauroyl pyrrolidone carboxylic acid, and N-a-benzoyl-L-arginine; film-forming polymers,

- or a compound activating the sebaceous glands such as DHEA, the oxidized and/or 17-alkylated derivatives thereof, sapogenins and vitamin D and derivatives thereof.

"Anti-glycation agent" means a compound preventing and/or reducing glycation of skin proteins, in particular proteins of the dermis such as collagen. Examples of antiglycation agents are plant extracts from the Ericaceae family, such as a blueberry extract (Vaccinium angustifolium); ergothioneine and derivatives thereof; and hydroxystilbenes and derivatives thereof, such as resveratrol and 3,3',5,5'-tetrahydroxystilbene.

Examples of NO-synthase inhibitors suitable for use in the present invention particularly comprise a Vitis vinifera species plant extract which is particularly marketed by EUROMED under the name LEUCOCYANIDINES® grape seed extract, or by INDENA under the name LEUCOSELECT®, or finally by HANSEN under the name EXTRAIT DE MARC DE RAISIN; an Olea europaea species plant extract which is preferably obtained from olive leaves and is particularly marketed by VINYALS in dry extract form, or by BIOLOGIA & TECHNOLOGIA under the trade name EUROL BT; and a Gingko biloba species plant extract which is preferably a dry aqueous extract of this plant sold by BEAUFOUR under the trade name GINKGO BILOBA EXTRAIT STANDARD.

Of the active agents stimulating dermal macromolecules or preventing the degradation thereof, mention can be made of those acting: - either on collagen synthesis, such as Centella asiatica extracts; asiaticosides and derivatives; synthetic peptides such as iamin, biopeptide CL or palmitoyloligopeptide marketed by SEDERMA; peptides extracted from plants, such as soy hydrolysate marketed by COLETICA under the trade name PHYTOKINE®; and plant hormones such as auxins and lignans.

- or on elastin synthesis, such as Saccharomyces Cerivisiae extract marketed by BASF under the trade name CYTOVITIN®; and Macrocystis pyrifera algae extract marketed by SECMA under the trade name KELPADELIE®;

- or on glycosaminoglycan synthesis,

- or on fibronectin synthesis,

- or on metalloproteinase (MMP) synthesis such as more specifically MMP 1 , 2, 3, 9. Mention can be made of: Retinoids and derivatives, oligopeptides and lipopeptides, lipoaminoacids, malt extract marketed by BASF under the trade name COLLALIFT®; blueberry or rosemary extracts; lycopene; isoflavones, derivatives thereof or plant extracts containing them, in particular extracts of soy (marketed for example by ICHIMARU PHARCOS under the trade name FLAVOSTERONE SB®), red clover, flaxseed, kakkon or sage;

- or on ADAM protein (A Disintegrin And Metalloprotease) inhibition;

- or on the inhibition of serine proteases such as leukocyte elastase or cathepsin G. Mention can be made of: legume (Pisum sativum) seed peptide extract marketed by LSN under the trade name PARELASTYL®; heparinoids; and pseudodipeptides such as {2- [acetyl-(3-trifluoromethyl-phenyl)-amino]-3-methyl-butyrylamino} acetic acid.

The agents stimulating keratinocyte proliferation, suitable for use in the composition according to the invention, particularly comprise retinoids such as retinol and esters thereof, of which retinyl palmitate; phloroglucinol; walnut meal extracts marketed by GATTEFOSSE; and Solanum tuberosum extracts marketed by SEDERMA.

The agents stimulating keratinocyte differentiation comprise for example minerals such as calcium; lupine extract marketed by SILAB under the trade name Photopreventine®; sodium beta-sitosteryl sulfate marketed by SEPORGA under the trade name PHYTOCOHESINE®; and corn extract marketed by SOLABIA under the trade name PHYTOVITYL®; and lignans such as secoisolariciresinoL

By way of illustration of other active agents that can be considered according to the invention, mention can particularly made of agents acting on the energy metabolism: creatine-creatinine such as Tego Cosmo C 100 from Degussa, EUGLENA GRACILIS or Chronodyn extract from Sederma. Filling agents such as for example hyaluronic acid, lipids, dermal relaxing agents such as for example adenosine, Boswellic acid, aniseed extract particularly BIOXILIFT from Silab, dermal contracting agents such as for example DMAE (dimethylaminoethanol), THPED (N,N,N’,N’-tetrakis(2-hydroxypropyl)-ethylenediamine).

The invention is now illustrated by the following examples.

In the following examples 1 and 2, the C-glycoside used is C-beta-D-xylopyranoside- 2-hydroxy-propane (INCI name: hydroxypropyl tetrahydropyrantriol).

EXAMPLE 1 : VASCULAR HYPERPERMEABILITY INDUCED BY TNF-a TREATMENT

Materials and methods

Endothelial cells from dermal microvessels (HMVEC-d) were seeded in culture inserts pretreated with fibronectin, then the inserts were placed in 24-well culture plates. The cells were cultured for 7 days in culture medium (EGM-2 medium supplemented with 5% fetal calf serum (FCS)) with renewal of the culture medium after 1 and 4 days of culture. The culture medium was then replaced by test medium (EGM-2 medium supplemented with 0.2% bovine serum albumin (BSA)) containing or not (Untreated control), 1 pM of Dexamethasone (Pharmacological reference), or C-Glycoside (tested at 1 and 3 mM), or diosmin (tested at 1 and 3 pM), or escin (tested at 1 and 3 pM), or the combination of C- Glycoside + Escin (1 mM C-Glycoside + 1 pM Escin; 3 mM C-Glycoside + 3 pM Escin) or the combination of C-Glycoside + Diosmin (1 mM C-Glycoside + 1 pM Diosmin; 3 mM C- Glycoside + 3 pM Diosmin). After 24 hours of pre-incubation, the inflammation inducer (TNF-a at 1 ng/mL) was added and the cells were incubated for 24 more hours. All the treatments were carried out in n=3 and an unstimulated control was produced in parallel. At the end of incubation, the fluorescent tracer (FITC-Dextran) was added to the inserts (upper compartment) and the cultures were incubated for 1 hour. After incubation, the medium of the lower compartment was transferred to a 96-well plate and a fluorescence measurement was made ( _exc 485 nm, Z,_emm 535 nm) using a spectrofluorometer. A protection percentage was calculated accounting for the fluorescence measured under unstimulated control conditions and accounting for the fluorescence measured under the control conditions after inducing inflammation with TNF-a according to the formula:

Protection (%) — 100 X (RFUstimulated control ^— RFUsample) / (RFUstimulated control ^— RFUunstimulated control) The between-group comparisons were conducted using an unpaired Student's t- test. Effects of Dexamethasone, C-Glycoside, Diosmin, Escin and of C-Glycoside + Diosmin and C-

Glycoside + Escin combinations, on vascular hyperpermeability induced by TNF-a

[Table 1]

Results The results show that TNF-a treatment substantially increases the vascular permeability displayed by an increase in the diffusion of the fluorescent tracer (FITC- Dextran). Under these conditions, Dexamethasone tested at 1 pM, used as the pharmacological reference molecule, protected the cells significantly from the effects of TNF-a (57% protection, p < 0.001, Table 1 ). The effect of TNF-a on vascular permeability and the effect of Dexamethasone on vessel wall strengthening were expected and make it possible to validate the test.

Under the experimental conditions of this study, C-Glycoside tested at 1 and 3 mM, Escin tested at 1 and 3 pM and Diosmin tested at 1 and 3 pM did not exhibit a protective effect on hyperpermeability induced by TNF-a (Table 1 ), although Escin and diosmin had been described for these effects. Surprisingly and unexpectedly, the C-Glycoside + Escin combination exhibited a clear and concentration-dependent protective effect in respect of hyperpermeability induced by TNF-a (28% and 41% protection respectively, p < 0.05).

These results demonstrate a synergistic action between C-Glycoside and Escin for vessel wall strengthening and also show the specificity of this synergistic action. Indeed, no additional or synergistic effect was observed with Diosmin even though it is also described, in the same way as Escin, as strengthening the wall of vessels.

EXAMPLE 2: VASCULAR INFLAMMATION INDUCED BY TNF-a TREATMENT

Materials and methods

Endothelial cells from umbilical veins (HUVEC) were seeded in 96-well culture plates and incubated for 24 hours in culture medium (EGM-2 medium supplemented with 5% fetal calf serum (FCS)). The culture medium was then renewed with culture medium containing or not (Control), 1 pM of IKK Inhibitor X (Pharmacological reference, compound having the CAS number 431898-65-6), or C-Glycoside (tested at 1 and 3 mM), or diosmin (tested at 1 or 3 pM), or escin (tested at 1 and 3 pM), or the combination of C-Glycoside + Escin (1 mM C-Glycoside + 1 pM Escin; 3 mM C-Glycoside + 3 pM Escin), or the combination of C- Glycoside + Diosmin (1 mM C-Glycoside + 1 pM Diosmin; 3 mM C-Glycoside + 3 pM Diosmin). After 24 hours of pre-incubation, the inflammation inducer (TNF-a at 8 ng/mL) was added and the cells were incubated for 48 more hours. All the treatments were carried out in n=3 and an unstimulated control was produced in parallel. At the end of incubation, the culture media were collected and the quantity of IL-8 was quantified using an ELISA kit according to the supplier's recommendations. A protection percentage was calculated accounting for the quantity of IL-8 measured under unstimulated control conditions and accounting for the quantity of IL-8 measured under the control conditions after inducing inflammation with TNF-a according to the formula:

Protection (%) = 100 X (I L-8stimulated control ^— I L-8sample) I (I L-8stimulated control ^— RFUunstimulated control)

The between-group comparisons were conducted using an unpaired Student's t- test. Effects of Dexamethasone, C-Glycoside, Diosmin, Escin and of C-Glycoside + Diosmin and C- Glycoside + Escin combinations, on vascular inflammation induced by TNF-a

[Table 2]

Results

The results show that TNF-a treatment substantially increases IL-8 secretion by endothelial cells thus expressing the onset of inflammation. Under these conditions, IKK Inhibitor X tested at 10 pM, used as the pharmacological reference molecule, protected the cells significantly from inflammation induced by TNF-a (97% protection, p < 0.001). The effect of TNF-a on inflammation and the anti-inflammatory effect of IKK Inhibitor X were expected and make it possible to validate the test. Under the experimental conditions of this study, C-Glycoside tested at 1 and 3 mM, diosmin tested at 1 and 3 pM did not exhibit an anti-inflammatory effect unlike Escin tested at 3 pM which protected the endothelial cells by 24% (p<0.01) from inflammation induced by TNF-a. Surprisingly and unexpectedly, the 3 mM C-Glycoside + 3 pM Escin combination exhibited a clear protective effect greater than that observed with Escin alone (respectively 32% and 24% protection, p < 0.01).

This statistically significant (p<0.05) difference in effectiveness demonstrates and supports the synergistic activity between C-Glycoside and Escin.

These results also show that an anti-inflammatory effect is not enough to strengthen the wall of vessels. Although escin tested alone exhibits a clear protective effect, this effect does not present as a functional activity as observed with our combination.

EXAMPLE 3: Composition according to the invention

The following composition according to the invention was prepared: [Table 3]

Claims

27 CLAIMS

1. Cosmetic use of a combination of at least one C-glycoside and escin for the care of the eye contour.

2. Use according to claim 1 , to reduce and/or minimize dark rings, bags and/or edema around the eye, and/or to reduce the signs of the skin aging of the eye contour.

3. Use according to one of claims 1 or 2, to reduce skin coloring defects linked with dark rings, and/or to improve the homogeneity of the complexion and/or skin glow, and/or to reduce skin relief irregularities, and/or to reduce wrinkles and lines.

4. Cosmetic use of a combination of at least one C-glycoside and escin to reduce dulling of the skin of the entire face in older subjects.

5. Use according to one of claims 1 to 4, wherein the C-glycoside has the following general formula (I):

[Chem 1]

wherein:

- R denotes a non-substituted C1 -C4, particularly C1 -C2, linear alkyl radical, in particular methyl;

6. Cosmetic composition comprising, in a physiologically acceptable medium: from 1 to 10% by weight of active substance with respect to the total composition weight, of at least one C-glycoside, and, from 0.25 to 10% by weight of active substance with respect to the total composition weight, of escin.

7. Composition according to claim 6, wherein the C-glycoside has the following general formula (I):

[Chem 1] — R

^S—/ (I) wherein:

8. Composition according to claim 6 or 7, wherein the physiologically acceptable medium comprises an aqueous phase and/or a fatty phase.

9. Composition according to one of claims 6 to 8, wherein the C-glycoside is C-beta-D-xylopyranoside-2-hydroxy-propane.

10. Composition according to one of claims 6 to 9, wherein the C-glycoside is present at a content ranging from 2% to 9% by weight of active substance with respect to the total weight of the composition, and preferably from 3% to 7% by weight of active substance.

11. Composition according to one of claims 6 to 10, wherein escin is present at a content of 0.3% to 9% by weight of active substance with respect to the total weight of the composition, and preferably from 0.3% to 3% by weight of active substance.

12. Cosmetic use of a composition according to one of claims 6 to 1 1 , for the care of the eye contour.

13. Non-therapeutic cosmetic care method for the eye contour, comprising the application on the eye contour area of a composition according to one of claims 6 to 11 .