FR2825627A1 - Citrus blossom bud extract with high citroflavonoid content, useful in cosmetic or pharmaceutical compositions, e.g. for protecting sensitive skin, treating acne, rosaceae or combating wrinkles - Google Patents

Abstract

A new citrus blossom bud extract (A) contains citroflavonoids (I) at a concentration of 0.1-500 g/kg. An Independent claim is included for the production of a citrus blossom bud extract, including the stage of solid-liquid extraction of the buds in a polar solvent.

Description

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EXTRACT OF CITRUS FLORAL BUTTONS, USE AND COMPOSITION COMPRISING SAID EXTRACT
The invention relates to an extract of citrus flower buds. It also relates to the various uses of said extract, as well as compositions comprising said extract. Citrus, belonging to the family Rutaceae, are small evergreen trees or shrubs, often with dense crowns. Citrus flowers are white and strongly scented. The fruits are very particular berries, whose skin consists of two layers (flavedo and albedo) and whose juicy pulp is divided into segments. Citrus or citrus fruits are among the oldest fruit species. They were already grown in China in the 2nd century BC The most important species of the genus Citrus are (subspecies and associated varieties): - Citrus sinensis (sweet orange) - Citrus aurantium (bitter orange bitter orange) - Citrus aurantium ssp bergamia ( bergamot) - Citrus limon (lemon) - Citrus limetta (sweet lime) - Citrus aurantiifolia (acid lime) - Citrus maxima (grapefruit) - Citrus reticulata (mandarin) without this list being limiting.

 In the remainder of the description and in the claims, by the expression "flower buds", we designate flowers in the state of buds, that is to say not yet open.

 Citrus, bitter orange and sweet orange are more particularly known. The bitter orange, also referred to as bitter orange, is known by various Latin names such as Citrus Aurantium L. Amara variety,

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 Aurantium. It is also known as Citrus amara or Citrus bigaradia and Citrus vulgaris. The bigaradier is to distinguish from the sweet orange, known under the Latin name Citrus sinensis or Citrus Aurantium L. variety Dulcis, whose fruits, unlike those of the bitter orange, are edible. These two trees have been widely studied and their fruits, leaves and flowers have found many applications. Highly used for their essential oils, they are also a source of pectin and flavonoids. Thus, for example, the fruit pulp of the sweet orange tree contains an acidulated juice, rich in vitamin C and vitamin P, which is used for the manufacture of refreshing syrup. By expression (mechanical process) of the orange fresh epicarp produced by the sweet orange tree, we obtain the essential oil of sweet orange, also called "essence of Portugal", to distinguish from the expression of the Fresh epicarp of orange produced by the bitter orange, which allows to obtain the essential oil of bitter orange or "essence of curacao".

 By steaming, the leaves of the sweet orange tree give "the essence of Petitgrain of Portugal", while those of the bitter orange give "the essence of Petitgrain Bigarade". By hydrodistillation, the fresh orange blossom flowers give "the essence of Neroli Portugal", while those of the bitter orange give "the essence of Petitgrain Bigarade".

 The water of orange blossom is obtained by hydrodistillation of the flowers of bitter orange. Two phases are collected in the essencier, respectively an upper phase constituted by the essence of Neroli bigarade, and a lower phase constituted by the water of orange blossom containing a small part of essence of Neroli Bigarade dissolved.

 Citroflavonoids, or bioflavonoids, or vitamin P, are particularly abundant in the pericarp of citrus fruit. Most of these citroflavonoids belong to the group of flavanones and present themselves, the most

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 often in the form of glycosides, in particular diholosides formed from rhamnose and glucose, which is called rutinosis and neohesperidosis. These are the major citroflavonoids which are, for example, naringin, narirutine, neohesperidin, hesperidin, neeriocitrin, eriocitrin, neoponcitrin, poncitrin, eriodictin. Each citrus species is characterized by a group of defined flavanones. Thus, the sweet orange contains mainly hesperidin and narirutin, neoriocitrin, hesperidin, while lemon contains hesperidin and eriocitrin, naringin pomelo, mandarin orange citronitrin and hesperidin. All these citroflavonoids have a number of properties such as: - anti-oxidant, scavenger of free radicals, anti-inflammatory, - venotonic action (vitamin P action, ie decrease in the permeability of the capillaries and increase of their resistance), stimulating action of protein synthesis; - Inhibitory effect of enzymes such as elastase ...

 The Applicant has found that, quite surprisingly, the solid / liquid cold extraction of citrus flower buds followed by a solid / liquid separation step made it possible to obtain an extract rich in citroflavonoids. It is also quite surprising to note that the content of citroflavonoids obtained according to this process is stable over time, thus making an extract with particularly interesting applications, particularly in the fields of pharmacy and cosmetics.

 The invention therefore relates to an extract of citrus flower buds, which is characterized in that it contains citroflavonoids in a concentration of between 0.1 g / kg and 500 g / kg of extract.

 Of course, the extract of the invention can be in liquid or solid form.

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 When the flower bud extract is in liquid form, it has a total solids content of between 5 and 100 g / kg, advantageously between 10 and 30 g / kg, preferably between 11 and 13 g / kg.

In this case, the concentration of citroflavonoids in said extract is between 0.1 and 20 g / kg (in g of citroflavonoids per kg of liquid extract), preferably between 2.5 and 4 g / kg.

 When the flower bud extract is in dry form, it then has a dry matter content of flower buds of between 100 and 1000 g / kg, preferably between 300 and 600 g / kg. In this case, the concentration of citroflavonoids is between 5 and 500 g / kg, advantageously between 50 and 200 g / kg.

agent conservateur dans une concentration comprise entre 1 et 10 g/l, avantageusement comprise entre 5 et 7 g/1 ainsi qu'éventuellement au moins un agent anti-oxydant dans une concentration comprise entre 0,5 et 10 g/l, avantageusement comprise entre 1 et 2 g/l. In order to have a stable liquid extract over time not only in terms of bacterial contamination, but also in terms of physical stability and color, the extract of the invention also comprises at least one

preserving agent in a concentration of between 1 and 10 g / l, advantageously between 5 and 7 g / l and optionally at least one anti-oxidant agent in a concentration of between 0.5 and 10 g / l, advantageously between 1 and 2 g / l.

 As a microbiological preserving agent, a preserving agent preferably chosen from the group of parabens (parahydroxybenzoate in the form of salts or not) is used. For example, the preservative is a mixture of Phenonipg and Nipastatg sodium.

 As an antioxidant, an antioxidant chosen from the group of organic acids (ascorbic acid, citric acid, gallic acid, etc.) is preferably used.

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 In a preferred embodiment, the extract is an extract of flower buds of bitter orange.

 The invention also relates to the method of manufacturing the citrus flower bud extract described above.

 This method is characterized in that it comprises a step of solid / liquid extraction of said flower buds in a polar solvent.

 The solid / liquid extraction step is selected from the techniques of maceration, digestion, percolation, extraction assisted by microwaves, ultrasound for example.

 In an advantageous embodiment, the solid / liquid extraction step consists of a cold maceration.

 According to another characteristic of the process, the ratio flower buds / polar solvent is between 1/99 and 20/80 (by weight).

 In practice, the flower buds of citrus come in the form of unopened flower buds, which means that they are picked before full blossoming of the flower. The buttons used during the extraction step may be in the fresh state or in the dry state in whole or milled form.

 To avoid any degradation of hydrolysable active substances, the extraction step is preferably carried out as already said cold, advantageously at a temperature between 3 and 10 C. The extraction time under these conditions is between 5 and 30 hours, and preferably 20 hours.

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 As already stated, the extraction is carried out in a polar solvent that can be used in a topical cosmetic application, thus in an aqueous or alcoholic or glycolic medium. In practice, the polar solvent is chosen from the group comprising water, ethanol, glycols such as propylene glycol, butylene glycol, alone or as a mixture.

 According to another characteristic of the process, the extraction step is carried out under stirring and under a nitrogen atmosphere, so as to promote the extraction of the active compounds while protecting said compounds from oxidation due to oxygen in the atmosphere. 'air. The solid / liquid extraction step is then advantageously followed by a solid / liquid separation step for removing the cake.

This step may be carried out according to different methods, such as, for example, draining, pressing, spinning, centrifugation or filtration. In an advantageous embodiment, the extract is then subjected to at least one clarification step, for example by filtration on plates, by membrane filtration, tangential filtration, or by centrifugation. The clarified extract may optionally be subsequently concentrated, so as to obtain a concentrated liquid form. The concentration step may be carried out for example by vacuum evaporation or reverse osmosis.

 In an advantageous embodiment, the clarification or concentration steps are followed by a sterilizing filtration step, preferably at 0.22 μm. The extract can then be packaged in sterile packaging or not. In the case of non-sterile packaging and to improve the stability of the extract, it is possible to incorporate in the extract obtained before the sterilizing filtration step at least one microbiological preservative and optionally at least one antioxidant in a proportion preferably of between 1 and 20 g / l relative to the total volume of the extract.

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 The extract can be used as such, that is to say in liquid form according to the method described above. When it is desired to obtain a dry form, the extract obtained at the end of the liquid / solid separation or clarification or concentration step is then dried. In practice, the liquid extract, with or without a preservative and with or without a texturing agent such as maltodexins, glucose syrups, is dried by lyophilization, atomization, or evaporation under vacuum.

 As already stated, such a method makes it possible to obtain an extract rich in citroflavonoids having particularly advantageous properties, so that it can be used in particular as an anti-radical, anti-inflammatory, venotonic and veno-active agent by decreasing the permeability of the capillaries. enhancing resistance, but also stimulating protein synthesis and extracellular matrix

Among the citroflavonoids contained in the extract, there are in particular neohesperidin, naringin, hesperidin, eriocitrin and narirutin.

 Thus, for example, the anti-radical and anti-inflammatory effect make it possible to envisage a use as a protective agent with regard to environmental stress, pollution and exogenous aging, as a protective agent for sensitive skin, or as a coactive agent in solar products. The venotonic effect makes it possible to envisage use as anti-oedematous, for example for the eye contour, as a decongestant, as a draining agent for example in slimming products, but also as an anticouperosis agent. Finally, the stimulatory effect of the protein synthesis and the elements of the extracellular matrix, as well as the inhibitory effect of enzymes makes it possible to envisage an anti-aging, anti-wrinkle and tonic use of the cutaneous elasticity.

 Such an extract, in liquid or solid form, may be incorporated in a cosmetic or pharmaceutical composition.

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 The invention therefore also relates to a cosmetic or pharmaceutical composition comprising the extract described above.

 In practice, said composition comprises an extract concentration in liquid form of between 0.5 and 20%, advantageously 5 to 10% by weight.

 Of course, the extract may be incorporated into the composition with any conventional formulation excipient, in particular with any acceptable pharmaceutical or cosmetic vehicle. The composition will generally be formulated to be applied to the skin in the form of, for example, milk, gel, cream, serum, microemulsions, etc.

 The invention and the advantages resulting therefrom will emerge more clearly from the following exemplary embodiments in support of the appended figures.

 FIG. 1 represents the anti-inflammatory activity of the extract of the invention on a keratinocyte culture by assaying the release of PGE2 induced by an inflammatory agent.

 Figure 2 shows the influence of the extract on the production of MDA by endothelial cells subjected to UVB irradiation.

Figure 3 shows the stimulating activity of the protein synthesis of the extract of the invention on fibroblasts.

A / Preparation of the Extract of the Invention in Liquid Form A maceration is carried out at 4 ° C. of 5% of coral flower buds milled in 95% of softened water with continuous mechanical stirring, and under a nitrogen atmosphere for 20 hours. .

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 The residues or extraction cakes are then drained. The extract is then filtered by several successive stages of filtration on plates. The microbiological preservatives are then added: PHENONIP 0.4% + 0.1% Nipastat sodium with stirring and then citric acid. The extract is finally filtered on a membrane of 0.22 m and then conditioned under nitrogen.

 The extract obtained has a limpid amber appearance with a characteristic odor of buds of bitter orange flowers. The dry matter content, excluding preservatives, is 10 to 17 g / l. The total flavonoid concentration expressed relative to neohesperidin is 3.2 g / l. The flavonoid assay is a standard aluminum chloride colorimetric method and reads absorbance using a visible UV spectrophotometer at a wavelength of 386 nm.

Citroflavonoids can also be identified and quantified individually by HPLC. The extract obtained contains the following citroflavonoids:

<Tb>
<tb> Neohesperidine <SEP>: <SEP> 1.67 <SEP> g / 1
<tb> Naringin <SEP>: <SEP> 1.09 <SEP> g / 1
<tb> Hesperidin <SEP>: <SEP> 0.21 <SEP> g / 1
<tb> Neoeriotrithin <SEP>: <SEP> 0.15 <SEP> g / 1
<tb> Narirutin <SEP>: <SEP> 0, <SEP> 11 <SEP> g / 1
<Tb>

This extract has excellent physicochemical and microbiological stability over time.

BI Properties of the extract
All activity evaluation tests were performed on the lyophilized form of the extract of the invention.

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a) Activité anti-radicalaire
L'activité anti-radicalaire de l'extrait de l'invention a été mis en évidence in vitro en milieu acellulaire, vis-à-vis de l'anion superoxyde et du radical hydroxyle comparativement à deux témoins, respectivement la rutine et l'acide chlorogénique. L'activité anti-radical superoxyde de l'extrait est appréciée par la mesure du taux de réduction du NBT en absence et en présence du produit. Les vitesses de réduction du NBT par le radical superoxyde sont suivies à 556 nm en utilisant le système phenazine méthosulfate/NADH, comme source de radicaux superoxydes. L'activité anti-radical hydroxyle de l'extrait est appréciée par la mesure colorimétrique du taux de formaldéhyde formé par réaction du radical OH sur le DMSO, en absence et en présence de produit. Le système PMS-NADH, en présence de traces de fer, est utilisé comme source de radicaux hydroxyles.

a) Anti-radical activity
The anti-radical activity of the extract of the invention was demonstrated in vitro in acellular medium, with respect to the superoxide anion and the hydroxyl radical compared to two controls, respectively rutin and chlorogenic acid. The anti-radical superoxide activity of the extract is appreciated by measuring the rate of reduction of NBT in the absence and presence of the product. The rates of reduction of NBT by the superoxide radical are monitored at 556 nm using the phenazine methosulfate / NADH system as a source of superoxide radicals. The anti-hydroxyl radical activity of the extract is assessed by the colorimetric measurement of the level of formaldehyde formed by reaction of the OH radical on DMSO, in the absence and in the presence of product. The PMS-NADH system, in the presence of traces of iron, is used as a source of hydroxyl radicals.

- activité anti-anion superoxyde CE 50 = 65 p. g par ml CE 50 rutine = 50 zu par ml (CE 50 = concentration efficace 50) - activité anti-radical hydroxyle CE 50 = 26 J. lg par ml CE 50 acide chlorogénique = 18 J. lg par ml

Les résultats obtenus montrent que l'extrait de l'invention est capable d'inhiber de manière dépendante l'activité des radicaux superoxyde et hydroxyle. The results are shown below:

superoxide anionic activity EC 50 = 65 p. g per ml EC 50 rutin = 50 zu per ml (EC 50 = effective concentration 50) - anti-hydroxyl radical activity EC 50 = 26 J. lg per ml EC 50 chlorogenic acid = 18 J. lg per ml

The results obtained show that the extract of the invention is capable of inhibiting the activity of the superoxide and hydroxyl radicals in a dependent manner.

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 Moreover, the concentrations effective to inhibit 50% of the activity of these radicals are similar to those of the selected reference inhibitors.

 As already stated, this anti-radical property makes the extract of the invention an extract which can be used as a protector of cutaneous cells with respect to environmental stresses and in particular UV, but also with respect to pollution, phenomena stimulating the formation of free radicals.

This anti-radical effect therefore makes the extract of the invention usable in protective and day care products, and solar products.

-Inflammatory. ~ Anti activity b) Anti-inf.ammatpirc activity
To evaluate the anti-inflammatory activity of the extract of the invention, the effects of this extract on the release of prostaglandin E2 (PGE) by human keratinocytes in monolayer culture stimulated by the antiinflammatory agent Phorbol Myristate Acetate are determined.

 A specific inflammatory reaction is triggered by activating the keratinocytes with PMA (Phorbol Myristate Acetate) and then measuring the production of PGE2 by ELISA technique.

 The cells were cultured in the presence of the product under test for 24 hours.

The media were then replenished with fresh media containing or without the product and in the presence or absence of phorbol 12myristate 13-acetate anti-inflammatory agent (1 μg / ml final, PMA, Sigma P1585). After 24 h of culture, the cell mats were observed and the media were harvested and frozen. Cell viability was assessed by quantification of the metabolic activity of cells (mitochondrial dehydrogenases) by measurement of MTT hydrolysis in

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 each plate. After thawing and centrifugation of the media, the PGE2 concentrations were measured using an ELISA kit (R & D Systems, ref DE0100), according to the protocol recommended by the supplier.

 As shown in Figure 1, PMA stimulated PGE2 by a factor of 16. The 0.1 and 0.02% extract of the invention makes it possible to significantly reduce this release of PGE2 in a dose-dependent manner (30% and 66%, respectively, of the control).

This anti-inflammatory activity can be the same as previously used to fight against environmental stresses, insofar as they promote the expression of many epidermal mediators capable of conditioning the development of inflammation, but also to fight against any erythema chemical, actinic or physical, or for the treatment of sensitive and hyper-reactive skin. cActiyite. vemoprgtectnce
The evaluation of the effect of the extract of the invention with respect to the protection of the capillary wall was carried out in vitro on endothelial cells. This protective effect was determined by measuring the antiradical activity of the extract by assaying Malondialdehyde (MDA) after UV irradiation. MDA is one of the essential markers of cytotoxicity induced by oxidative stress processes. It comes from the chain reaction triggered inside cell membranes by free radicals.

 The assay was performed on human endothelial cells grown in monolayer. Vitamin E (25 μM) was taken as a positive reference.

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Different lots have been constituted:

<Tb>
<tb> Batch <SEP> 0 <SEP> control <SEP> negative <SEP> without <SEP> irradiation
<tb> Batch <SEP> 1 <SEP> control <SEP> negative <SEP> with <SEP> irradiation
<tb> Batch <SEP> 2 <SEP> control <SEP> positive <SEP> Vitamin <SEP> E <SEP> without <SEP> irradiation
<tb> Batch <SEP> 3 <SEP> control <SEP> positive <SEP> Vitamin <SEP> E <SEP> with <SEP> irradiation
<tb> Batches <SEP> 4 <SEP> and <SEP> 5 <SEP> Batches <SEP> treated <SEP> with <SEP> extract <SEP> at <SEP> concentrations <SEP> 1 <SEP> and <SEP> 10
<tb> ug / ml, <SEP> without <SEP> irradiation
<tb> Lots <SEP> 6 <SEP> and <SEP> 7 <SEP><SEP> Lots processed <SEP> with <SEP> extract <SEP> at <SEP> concentrations <SEP> 1 <SEP> and <SEP><SEP> 10
<tb> ug / ml, <SEP> with <SEP> irradiation
<Tb>

The treated and irradiated batches were immediately subjected to a UVB dose of 100 mJ / cm 2 after treatment of the cells and then incubated for 24 hours.

 The measurement of the MDA after extraction is done by measuring the fluorescence after separation of the MDA-TBA complex by HPLC.

 The results obtained reveal that in the absence of UV, thus of oxidative stress, the extract according to the invention does not modify the level of basal MDA. On the other hand, the extract has a protective effect vis-à-vis the free radicals generated by the UV since the level of MDA released is significantly decreased compared to the irradiated control (20 and 26% protection respectively at concentrations of 10 g / ml and 1 μg / ml). This protective effect is at least similar to that obtained with Vitamin E.

 The extract of the invention, by its venotonic and venoprotective effect, can be used as already said, to protect and strengthen the cutaneous capillary network, in particular to improve the radiance of the complexion and the condition of the blotchy skin, but also as anti-oedematous, decongestant, draining, for example for the eye area or in slimming products.

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d / Stimulation of metabolism
The stimulating activity of the metabolism was evaluated on human dermal fibroblasts in monolayer culture. The effect of the product on the synthesis of cellular proteins and extracellular matrix was measured. This synthesis was followed by measuring the incorporation into the neosynthesized proteins of an animated radioactive precursor acid, tritiated leucine, in the presence and in the absence of the extract of the invention, compared to a reference control, the EGF (Epidermal Growth Factor). The fibroblasts cultured in 10% FCS medium are incubated for 72 hours with different concentrations of the extract of the invention (50, 150,300, 450 μg / ml).

 Tritiated leucine (H-Leucine) is then added to the culture medium.

After a 24 hour incubation period, the neosynthesized proteins are extracted by suitable techniques and the incorporation of the radioactive precursor into these macromolecules is measured by liquid scintillation.

 The results (FIG. 3) show that the extract of the invention stimulates protein synthesis of fibroblasts. This effect is inversely proportional to the range of concentrations tested and significant for concentrations of 0.005 and 0.015% (respectively + 35 and + 25% relative to the control).

 The extract of the invention, by its stimulating effect of protein synthesis, can be used as already said, as anti-wrinkle active, anti-aging, to fight against endogenous skin aging, but also as a tonic and stimulant of skin elasticity.

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CI Compositions cosmétiques incorporant l'extrait de l'invention 1/CREME PROTECTRICE JOUR

CI Cosmetic Compositions Incorporating the Extract of the Invention 1 / PROTECTIVE CREAM DAY

<Tb>
<tb> Designation <SEP> INCI <SEP>% <SEP> p / p
<tb> TEFOSE 2561 <SEP> (1) <SEP> PEG-6 <SEP> stearate <SEP> (and) <SEP> ceteth-20 <SEP> (and) <SEP> 5.00
<tb> glyceryl <SEP> stearate <SEP> (and) <SEP> steareth-20
<tb> SOFCUTOL <SEP> (g) <SEP> B <SEP> (1) <SEP> Ethoxydiglycol <SEP> behenate <SEP> 5, <SEP> 00
<tb> MOD <SEP> (1) <SEP> octyldodecyl <SEP> myristate <SEP> 5, <SEP> 00
<tb> CEVENYLS <SEP> (L) <SEP> Oil <SEP> of <SEP> seed <SEP> of <SEP> Borage <SEP> 2, <SEP> 00
<tb> CETYL <SEP> ALCOHOL <SEP> Cetyl <SEP> Alcohol <SEP> 2, <SEP> 00
<tb> DOW <SEP> CORNING <SEP> 200 <SEP> FLUID <SEP> 350 <SE> CS <SEP> Dimethicone <SEP> 5, <SEP> 00
<tb> FITODERM <SEP> (3) <SEP> Squalane <SEP> 3, <SEP> 00
<tb> PHENONIP <SEP> (4) <SEP> Phenoxyethanol <SEP> (and) <SEP> methylparaben <SEP> 0.5
<tb> (and) <SEP> butylparaben <SEP> (and) <SEP> ethylparaben
<tb> (and) <SEP> propylparaben
<tb> WATER <SEP> DEMINERALIZED <SEP> Water <SEP> 62, <SEP> 30
<tb> GLYCERIN <SEP> Glycerin <SEP> 4, <SEP> 30
<tb> CARBOPOLULATE <SEP> 10 <SEP> (5) <SEP> Carbomer <SEP> 0, <SEP> 15
<tb> RHODICARE <SEP> D <SEP> (6) <SEP> Gum <SEP> of <SEP> Xanthan <SEP> 0, <SEP> 25
<tb> SODIUM <SEP> HYDROXIDE <SEP> (10 <SEP>% <SEW> SO) <SEP> Hydroxide <SEP> of <SEP> sodium <SEP> 0, <SEP> 30
<tb> EXTRACT <SEP> FROM <SEP> THE INVENTION <SEP> 5, <SEP> 00
<tb> PERFUME <SEP> FLAIRITA <SEA> NO <SEP> 5 <SEP> (7) <SEP> 0, <SEP> 20
<Tb>
Manufacturers: 1 / GA TTEFOSSE SA 2 / DOW CORNING 3 / HISPANO QUIMICA4 / NIPA5 / BF GOODRICH
6 / RHONE POULENC 7 / PAYAN AND BERTRAND 2 / MILK SKIN CUTTERS

<Tb>
<tb> Designation <SEP>% <SEP> p / p
<tb> PLUROLOSTEARIC <SEP> WL <SEP> 1009 <SEP> (1) <SEP> Polyglyceryl-6 <SEP> Distearate <SEP> 5, <SEP> 00
<tb> CETEARYL <SEP> ALCOHOL <SEP> Cetearyl <SEP> alcohol <SEP> 1.00
<tb> SHEA <SEP> BUTTER <SEP> Shea <SEP> Butter <SEP> 2, <SEP> 00
<tb> LABRAFACXCC <SEP> (1) <SEP> Caprylic / Capric <SEP> Triglyceride <SEP> 12.00
<tb> CEVENYLQD <SEP> (1) <SEP> Oil <SEP> of <SEP> Seed <SEP> of <SEP> Borage <SEP> 2.00
<tb> PHENONIP <SEP> (2) <SEP> Phenoxyethanol <SEP> (and) <SEP> methylparaben <SEP> 0.60
<tb> (and) <SEP> butylparaben <SEP> and) <SEP> ethylparaben
<tb> (and) <SEP> propylparaben
<tb> EXTRACT <SEP> ORIGINAL <SEP> LEMON <SEP> (1) <SEP> Citrus <SEP> medica <SEP> limomum <SEP> (Lemon) <SEP> 71,10
<tb> Water <SEP> of <SEP> fruit
<tb> SOLANACE <SEP> STARCH <SEP> (3) <SEP> Starch <SEP> of <SEP> apple <SEP> of <SEP> soil <SEP> modified <SEP> 1.00
<tb> KELTROL <SEP> T <SEP> (4) <SEP> Gum <SEP> of <SEP> xanthan <SEP> 0, <SEP> 30
<tb> EXTRACT <SEP> FROM <SEP> THE INVENTION <SEP> 5, <SEP> 00
<Tb>
Manufacturers: I / GATTEFOSSE SA 2 / NIPA 3 / NATIONAL STARCH AND CHEMICAL LTD 4 / KELCO

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3 / GEL CONTOUR OF THE EYES

<Tb>
<tb> Designation <SEP>% <SEP> p / p
<tb> WATER <SEP> DEMINERALIZED <SEP> Water <SEP> 82, <SEP> 70
<tb> PHENONIP <SEP> (2) <SEP> Phenoxyethanol <SEP> (and) <SEP> methylparaben <SEP> 0.50
<tb> (and) <SEP> butylparaben <SEP> (and) <SEP> ethylparaben
<tb> (and) <SEP> propylparaben
<tb> GLYCERIN <SEP> Glycerin <SEP> 10, <SEP> 00
<tb> CARBOPOL <SEP> 940 <SEP> (3) <SEP> Carbomer <SEP> 0, <SEP> 60
<tb> SODIUM <SEP> HYDROXIDE <SEP> (10% <SE> SOL.) <SEP> Hydroxide <SEP> from <SEP> sodium <SEP> 1.20
<tb> EXTRACT <SEP> FROM <SEP> THE INVENTION <SEP> 5, <SEP> 00
<Tb>
Manufacturers: 1 / GATTEFOSSE SA 2 / NIPA 3 / BF GOODRICH

Claims (1)

11 Citrus flower bud extract, characterized in that it contains citroflavonoids in a concentration of between 0.1 and 500 g / kg by weight of extract.  2 / extract according to claim 1, characterized in that when it is in liquid form, the concentration of citroflavonoids is between 0.1 and 20 g / kg.  3 / extract according to claim 1, characterized in that when it is in dry form, the concentration of citroflavonoids is between 5 and 500 g / kg.  4 / extract according to claim 1, characterized in that when it is in liquid form, it further contains at least one preservative and at least one antioxidant.  5 / extract according to claim 1, characterized in that the flower buds are flower buds of bitter orange.  6 / A method of manufacturing an extract of citrus flower buds, characterized in that it comprises a step of solid / liquid extraction of said flower buds in a polar solvent.  7 / A method according to claim 6, characterized in that the flower buds are in the fresh state or in the dry state in whole form or crushed.  8 / A method according to claim 6, characterized in that the solid / liquid extraction step consists of a cold maceration. <Desc / Clms Page number 18>  9 / A method according to claim 6, characterized in that the polar solvent is selected from the group consisting of water, ethanol, glycol, alone or in mixture.  10 / A method according to claim 6, characterized in that the solid / liquid separation step consists of dewatering, pressing, spinning, centrifugation or filtration.  11 / A method according to claim 6, characterized in that the solid / liquid separation step is followed by at least one clarification step.  12 / A method according to claim 11, characterized in that the clarification step is followed by a concentration step.  13 / A method according to one of claims 11 or 12, characterized in that the clarification or concentration steps are followed by a sterilizing filtration step.  14 / A method according to one of claims 6 or 12, characterized in that the extract is then dried by lyophilization, atomization, evaporation under vacuum.  15 / extract according to claim 1, used for its antiradical and anti-inflammatory properties, as a protector against environmental stresses and exogenous aging, as a protector of sensitive skin or as a coactive in sun products.  16 / extract according to claim 1, used for its venotonic and veinoprotective properties as anti-oedematous, decongestant, draining and anti-couperose agent. <Desc / Clms Page number 19>  17 / extract according to claim 1, used for its stimulatory properties of protein synthesis and elements of the extracellular matrix as an anti-aging agent, anti-wrinkle and toning of cutaneous elasticity.  18 / cosmetic or pharmaceutical composition characterized in that it comprises the extract according to claim 1.  19 / Composition according to claim 17, characterized in that it contains between 0.5 and 20% of extract in liquid form by weight.  DEPOSITOR G G TTEFOSSE S. A. LAWYER: LAURENT and CHARRAS