Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
  • A61K31/19—Carboxylic acids, e.g. valproic acid
  • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
  • A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P3/00—Drugs for disorders of the metabolism

Definitions

• the invention relates to a new use of a food, cosmetic and / or pharmaceutical composition containing petroselinic acid.
• compositions contain, at a more or less high concentration, a fatty phase generally consisting of at least one oil, a fatty material and / or a wax, for example in the form of emulsions of the water type. -in-oil or oil-in-water, oily gels, and oily solutions.
• Oils generally constitute a significant proportion of this fatty phase and can be of very varied origins. They may especially be vegetable, animal, mineral oils or even synthetic oils. Among these oils, vegetable oils constitute a class of choice because the current trend is more oriented towards the use of products of natural origin. These vegetable oils generally consist of triglycerides of fatty acids.
• Vegetable essential oils are clearly distinguished from vegetable oils. Indeed, essential oils are odoriferous products obtained from a vegetable material, generally by steam entrainment. An essential oil extracted from an ombélliffère cannot therefore contain a vegetable oil, and in particular cannot contain petroselinic acid (Afifi et al., Vet. Med. J., Giza, 42 (3), 85-92, 1994; patent RU2027440 by A. Leontev et al .; patent CS24821 by O. Krejsa et al.).
• the duration and extent of inflammation can be modulated by controlling the metabolism of leukotriene B4. For this, one can either control its degradation, or either interfere with the leukotriene B4 receptors.
• EP709084 (L'Oreal) describes that a cosmetic or dermatological composition containing a vegetable oil rich in petroselinic acid is particularly indicated for moisturizing dry skin. This hydrating effect has nothing to do with an anti-inflammatory effect, or even a modulator of lipid metabolism.
• EPI 16439 discloses that certain fatty acids, including petroselinic acid, have a strong activity of inhibiting 5 ⁇ -reductase from the bacterial flora of the scalp, and can therefore be used in tonic products for the hair treatment. The action of these fatty acids is therefore limited to the bacterial flora of the scalp. It is thus never suggested that petroselinic acid can act directly on the surface tissues of humans by preventing inflammation, or even by modulating the lipid metabolism of these tissues (thanks to the activation of catabolism not ⁇ - oxidation). As proof, EPI 16439 recommends using oleic acid for this purpose, while the latter is inactive against inflammation (see Example 1 below).
• US4097604 (Oxford Hill) indicates that a salt of different fatty acids, in particular petroselinic acid, is active against pathogens of the oral cavity, thus making it possible to reduce the incidence of these bacteria on the appearance of periodontoses. The action of these fatty acids is therefore limited to the oral flora. It is thus never suggested that petroselinic acid can act directly on the surface tissues of man by preventing inflammation, or even by modulating the lipid metabolism of these tissues.
• US4097604 recommends to use for this purpose preferably oleic acid, while this fatty acid is inactive against inflammations (see Example 1 below).
• EP355842 (Sansho Seiyaku) describes a care cream intended to prevent pigmentation caused by an overproduction of melanin, said cream possibly containing petroselinic acid. This effect on pigmentation, however, has nothing to do with an anti-inflammatory and / or modulating effect on lipid metabolism.
• FR2631235 (Sandoz) describes compositions suitable for dermal application in the treatment of an autoimmune skin disease or for promoting hair growth. These compositions contain as active principle of cyclosporine, and as vehicle of the active principle, a fatty acid including petroselinic acid.
• the prior art is silent about the activity and metabolism of petroselinic acid in human surface tissues, especially on the skin or keratinocytes.
• the present invention thus relates to the treatment of human surface tissues with petroselinic acid in order to reduce inflammatory responses, and / or even to modulate the metabolism of lipids.
• the present invention thus relates to the use of petroselinic acid, native or esterified, for the preparation of a composition intended to be able to treat or prevent inflammation and / or modulate the metabolism of lipids in the surface tissues of the man.
• the surface tissues of man can be the cells constituting the skin, the scalp, the eye, or the oral, buccal, nasal or vaginal mucous membranes, for example.
• modulation of lipid metabolism is meant more particularly the catabolism of lipid mediators linked to inflammation, differentiation, proliferation and / or the barrier function of surface tissues.
• inflammation of the surface tissues must be understood as the physiological phenomenon involving the production of pro-inflammatory cytokines, such as TNF ⁇ , by the cells of the surface tissues, for example keratinocytes and epithelial corneal cells, and the cells of the immune system contained in these tissues (lymphocytes, Langerhans cells, ect ). Inflammation can result from infection, allergy, wound, autoimmune disease, and exposure to radiation and / or irritants and / or sensitizers, for example example.
• pro-inflammatory cytokines such as TNF ⁇
• Petroselinic acid can thus be used in particular for the treatment or prophylaxis of diseases of the skin or scalp, in particular against inflammations linked to psoriasis, erythema (sunburn), eczema, seborrheic dermatitis , Valopecia areata, yeast, acne or other dermatoses, for example.
• Applications can also be extended to inflammations of the eye (inflammation of the cornea) and mucous membranes, in particular the oral, nasal, oral and vaginal mucosa.
• the composition can be applied directly to surface tissue so that petroselinic acid can diffuse through and be assimilated therein.
• This composition can also be injected under the surface tissues, for example by means of a subcutaneous injection.
• the application of petroselinic acid is considered to be topical, that is, applied directly to, or under, the surface tissue.
• This composition can also be administered orally so that petroselinic acid can act on the mucous membranes (the oral, esophageal, stomach and intestinal mucosa), and / or it can pass into the blood circulation and be supplied directly to cells in the skin, eye, or mucous membranes, for example.
• petroselinic acid can act on the mucous membranes (the oral, esophageal, stomach and intestinal mucosa), and / or it can pass into the blood circulation and be supplied directly to cells in the skin, eye, or mucous membranes, for example.
• This composition can also be applied in the nasal passages, by means of a diffuser, a gel and / or a physiological liquid conventionally intended for the washing of the nasal passages.
• Petroselinic acid also called ⁇ -6-cis-octadecenoic acid (18: ln-12)
• ⁇ -6-cis-octadecenoic acid 18: ln-12
• petroselinic acid esters are also potentially activators of peroxisomal ⁇ - oxidation.
• other fatty acids activators of peroxisomal ⁇ -oxidation such as palmitic acid or oleic acid, in the native or esterified state, are recognized to be activators of peroxisomal ⁇ -oxidation (Schmidt and ai, Lipids, 3_1_, 1 115-1124, 1996).
• Petroselinic acid can thus be esterified with glycerol (mono-, di- or tri-acyl), an alcohol such as methyl and ethyl alcohols, a sugar, a tocopherol, a tocotrienol, a sterol or even a fatty alcohol, example.
• the composition can thus comprise an oil from an umbelliferous plant rich in petroselinic acid.
• oil rich in petroselinic acid means an oil containing at least 40% of petroselinic acid.
• Umbelliferae are plants whose flowers are arranged in umbels.
• the species preferably used in the invention are coriander, chervil, carrot, celery, cumin and dill.
• the umbelliferous oil used according to the invention is extracted from the seed of this umbelliferous plant, for example by grinding or pressing, then refining.
• Umbelliferous oil has a petroselinic acid content which varies depending on the umbelliferous seed from which it is extracted. For the same umbelliferous plant, the petroselinic acid content also varies according to the country of origin of the umbelliferous plant and according to the extraction which can be more or less complete.
• coriander seed oil contains about 75 to 90% petroselinic acid
• cumin seed oil contains about 55 to 65% o
• carrot seed oil about 55 to 65%
• parsley seed oil about 40 to 50%
• fennel seed oil about 55 to 65%
• chervil seed oil about 50 to 70%
• seed oil celery about 45 to 60%
• dill seed oil about 75 to 85%, these percentages being given relative to the total weight of the composition.
• the oil can be used in the composition according to the invention at a concentration ranging from 0.01 to 50% by weight relative to the total weight of the composition, for example, and preferably from 0.2 to 20%.
• the quantity of petroselinic acid sufficient and necessary to observe an anti-inflammatory effect or Modulator of lipid metabolism can vary considerably.
• the invention also relates to the use of petroselinic acid in an amount sufficient for the treatment or prevention of inflammation and / or for the modulation of lipid metabolism in surface tissues.
• the subject of the invention is also the use of petroselinic acid, in particular contained in an umbelliferous oil, to prepare a dosage form normally used for topical application or for oral hygiene, and especially in the form of solutions oily, alcoholic or hydroalcoholic, gels, water-in-oil or oil-in-water emulsions, having the appearance of a cream or gel, optionally capable of foaming, in the form of an aerosol, or also in the form of vesicular dispersions containing ionic and / or nonionic lipids.
• These dosage forms are, in any case, prepared according to the usual methods of the cosmetic fields considered.
• This composition can in particular constitute a composition for cleaning, protecting, treating or caring for the scalp, for the face, for the neck, for the hands or for the body (for example in the form of day creams, night, make-up removing creams, sun creams or oils, oils for the body or the face, cleansing milks, cleansing milks, body milks), a makeup composition (for example foundation), an artificial tanning composition, a composition for the bath, a shampoo composition (treatment of the scalp), or a composition for oral hygiene (mouthwash, toothpaste, putty), for example.
• a composition for cleaning, protecting, treating or caring for the scalp, for the face, for the neck, for the hands or for the body for example in the form of day creams, night, make-up removing creams, sun creams or oils, oils for the body or the face, cleansing milks, cleansing milks, body milks
• a makeup composition for example foundation
• an artificial tanning composition for the bath
• a shampoo composition treatment of the scalp
• a composition for oral hygiene mouthwash, toothpaste
• this composition can be a capsule, a capsule, an emulsion, an ointment, an infectious composition under the skin, an ointment, a syrup, a diffuser, an eye drop, a shampoo or a bath mouth, containing petroselinic acid, in particular contained in an umbelliferous oil, intended for the treatment or prophylaxis of the skin, the eye or the mucous membranes, for example.
• the various possible dosage forms are, in any case, prepared according to the usual methods of the pharmaceutical fields considered.
• this composition can be any ingestible composition, liquid or solid, containing petroselinic acid, in particular contained in an umbelliferous oil.
• This composition can be a sauce such as a salad dressing, a table oil, a mayonnaise, an ice cream, a pastry composition, a filling or spread, for example.
• keratinocytes naturally express proteins and enzymes involved in inflammatory responses after treatment with pro-inflammatory agents, such as phorbol esters. Among the proteins and enzymes thus produced, one can thus count superoxide dismutase (SOD), and type I collagenase and tumor necrosis factor alpha (TNF ⁇ ), for example.
• SOD superoxide dismutase
• TNF ⁇ tumor necrosis factor alpha
• TPA 12-O-tetradecanoylphorbol acetate
• the immortalized keratinocyte lines DK2, DK7, FK2 described in PCT / EP96 / 05812 (Nestlé Products Company) were used for this purpose.
• the FK2 and DK2 lines were also deposited, on October 5, 1995, under the Budapest Treaty, at the DSM (Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH, Mascheroder Weg lb, D-38124 Braunschweig, Germany) and were seen assign the deposit numbers DSM ACC2240 and DSM ACC2238 respectively.
• the immortalized HaCaT keratinocyte line described by Boukamp et al was also used (J. Cell.
• TNF ⁇ are commercially available (BioSource Inter., US, catalog number
• the cells are incubated for 2 times 2 days (renewal of the medium after the first 2 days) in NR-2 medium rich in calcium (CaCl 2, 1.5 mM) containing 1 mg / ml of BSA and a fatty acid given (lOO ⁇ M of oleic acid 18: ln-9; lOO ⁇ M of petroselinic 18: 1 n-12) or an equivalent amount of 0 solvent used for fatty acids (ethanol: control).
• CaCl 2, 1.5 mM calcium
• a fatty acid given lOO ⁇ M of oleic acid 18: ln-9; lOO ⁇ M of petroselinic 18: 1 n-12
• ethanol control
• HBSS buffer Hanks Balanced Sait Solution, Biofluids No. 325
• BSA Bactet's Staline
• the cells are then detached in 1 ml HBSS, centrifuged, and the cells D extracted in a mixture of hexane and isopropanol 2/1 (v / v) containing 0.01% of 2,6-di- tert-butyl-p-cresol.
• the phospholipids are then separated by thin layer chromatography (stlica gel 60) with a mixture of chloroform and acetone 96/4 (v / v) as eluent.
• the phospholipid fatty acids are then esterified by heating in a solution containing 10% BF3-methanol.
• the methyl esters are then separated, quantified by gas-liquid chromatography with detection by an ionized flame. Esters are identified by comparison with appropriate controls.
• SOD superoxide dismutase
• TNF ⁇ tumor necrosis factor alpha
• epithelial cells of the human colon in culture, primary and immortalized are subjected in-vitro to an inflammatory treatment with TPA.
• the immortalized line is that described in EP96201064.1 (Nestlé Products Company) which was deposited, under the Budapest Treaty, with the Deutsche Sammlung von Mikroorganismen und Zellkulturen, Mascheroder Weg lb, D-38124 Braunschweig, Germany, on 16 April 1996, where it received deposit number DSM ACC2258.
• the effect of petroselinic acid on the production of TNF ⁇ by the cells of the colon is determined when these are subjected to an irritant treatment.
• Culture medium B50 Biofluids
• EP96201064.1 is used for this purpose. The results of the tests are comparable to those presented in Example 1.
• Epithelial cells of the human cornea naturally express proteins and enzymes involved in inflammatory responses after treatment with pro-inflammatory agents, such as phorbol esters.
• pro-inflammatory agents such as phorbol esters.
• collagenase I easily detectable marker: Bazan et ai, Proc. Natl. Acad. Sci. USA, 90, 8678-8682, 1993
• c-fos see Bazan et ai
• the arachidonic intermediaries 12-HETE and 12-HETrE Conners et ai, Inves. Ophth. & Visu. Sci., 36, 828-840,
• epithelial cells of the human cornea in culture primary or immortalized, are subjected in-vitro to an inflammatory treatment with TPA.
• the immortalized line is that described in
• KGM-1 medium KBM medium from Clonetics, US, further comprising 0.15 mM CaCh, 30 ⁇ g / ml of bovine pituitary gland extract, 0.5 ⁇ g / ml of hydrocortisone , 5 ⁇ g / ml insulin, 10 ⁇ g / ml transferin, 10 ng / l murine epidermal growth factor (EGF), 10,000 U / ml penicillin and 10,000 U / ml
• the effect of petroselinic acid on the production of collagenase I by the cells of the cornea is determined, when these are subjected to an irritant treatment.
• the expression of collagenase can be detected by PCR, by Westem-Blot or by Elisa.
• the RNA is extracted from the sensitized cells, and the presence of collagenase I mRNA is detected by PCR with a primer derived from the DNA sequence of collagenase I (Genebank: n ° X05231 ).
• the sensitized culture medium is recovered, it is concentrated with an Amicon30® filter, the proteins are separated by electrophoresis on an SDS-Page polyacrylamide gel, they are transferred by Western-blot to a filter, the filter is subjected to a first anti-collagenase I antibody (Cortex Biochem, US, n ° 60338P), to a second antibody coupled to a peroxidase (Pierce, US, n ° 31400), then to the peroxidase substrate .
• a first anti-collagenase I antibody Cortex Biochem, US, n ° 60338P
• a second antibody coupled to a peroxidase Pieris
• Example 4 Body milk (oil-in-water emulsion)
• Glyceryl stearate / PEG-100 stearate (Arlacel 165 sold by the company ICI) (emulsifier) 1%
• Aqueous phase Aqueous phase :
• Carbomer (carbopol 941 sold by Goodrich) (gelling agent) 0.3% Triethanolamine (neutralizing agent) 0.3%
• Preservative 0.3% Water qs 100% The emulsion is prepared by incorporating the oily phase into the aqueous phase with stirring. A body milk is obtained which provides good protection of the skin against inflammation.
• Aqueous phase Xanthan gums (gelling agent) 0.2% Polysacrylamide / isoparaffin C13-C14 / leureth-7 (Sepigel 305 sold by the company Seppic) (gelling agent) 0.8%
• the emulsion is prepared as in Example 4. A white fluid is obtained, which provides good protection to the skin against inflammation.
• phase A Water qs 100%
• Phase B is heated to 65 ° C and poured into phase A with stirring, then the mixture is cooled.
• a smooth, nourishing white cream is obtained, which provides good protection of the skin against inflammation.

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• 1997
  • 1997-07-05 EP EP97111374A patent/EP0888773A1/de not_active Withdrawn
• 1998
  • 1998-07-02 BR BR9810121-8A patent/BR9810121A/pt not_active IP Right Cessation
  • 1998-07-02 AU AU84459/98A patent/AU8445998A/en not_active Abandoned
  • 1998-07-02 EP EP98935087A patent/EP0999831A1/de not_active Withdrawn
  • 1998-07-02 JP JP11508231A patent/JP2000511942A/ja not_active Ceased
  • 1998-07-02 WO PCT/FR1998/001420 patent/WO1999002149A1/fr not_active Ceased
  • 1998-07-02 CA CA002294817A patent/CA2294817A1/fr not_active Abandoned

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