EP1082097A1 - Utilisation de sophorolipides comprenant des lactones diacetylees en tant qu'agent stimulateur du metabolisme des fibroblastes de la peau - Google Patents

Utilisation de sophorolipides comprenant des lactones diacetylees en tant qu'agent stimulateur du metabolisme des fibroblastes de la peau

Info

Publication number
EP1082097A1
EP1082097A1 EP99920934A EP99920934A EP1082097A1 EP 1082097 A1 EP1082097 A1 EP 1082097A1 EP 99920934 A EP99920934 A EP 99920934A EP 99920934 A EP99920934 A EP 99920934A EP 1082097 A1 EP1082097 A1 EP 1082097A1
Authority
EP
European Patent Office
Prior art keywords
sophorolipids
lactones
use according
fraction
purified
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99920934A
Other languages
German (de)
English (en)
French (fr)
Inventor
Frédérique BORZEIX CON AIX
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sophor SA
Original Assignee
IFP Energies Nouvelles IFPEN
Sophor SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IFP Energies Nouvelles IFPEN, Sophor SA filed Critical IFP Energies Nouvelles IFPEN
Publication of EP1082097A1 publication Critical patent/EP1082097A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic 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
    • A61K8/37—Esters of carboxylic 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • 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
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the invention relates to the use of at least one sophorolipid in lactone form, as an agent which stimulates the metabolism of fibroblast cells of the dermis of the skin. It is particularly applicable to the fields of cosmetology and dermatology.
  • Sophorolipids are glycolipids; they are produced by fermentation using yeasts of the Candida or Torulopsis type, such as Torulopsis magnoliae, Candida bombicola, Candida apicola or Candida bogoriensis.
  • sophorose 2-0- ⁇ -D- glucopyranosyl - ⁇ -D- glucopyranose.
  • This sugar can be acetylated in position 6 ′ and 6 "and it is linked by an acetal bond to a fatty hydroxy acid in position ⁇ or ⁇ -1.
  • the lipid fraction of sophorolipids is composed of several fatty hydroxy acids, which differ in the length of their chain, in the number and position of unsaturations, as well as in the position of hydroxylation.
  • fatty hydroxy acids which differ in the length of their chain, in the number and position of unsaturations, as well as in the position of hydroxylation.
  • For each of these hydroxy acids there are different structural forms which differ from each other, by lactonization (or not) of the sophorosis (mainly in position 4 ”) or even by acetylation (or not) of positions 6 'or 6 ".
  • the lipid sophorose mixtures produced by fermentation can be resolved and analyzed by high performance liquid chromatography with a gradient of elution of water and acetonitrile. We thus note the existence of about twenty individual compounds.
  • the sophorolipids in their raw form consist of a mixture of at least one sophorolipid in lactone form and at least one sophorolipid in acid form.
  • sophorolipids raw form and acid form concerning the fight against skin aging, namely their action as an anti-radical and anti-elastatic protective agent as well as their repairing, restructuring and firming action, have been described respectively in the applications.
  • WO 95/34282 and FR 96/16093 The properties of sophorolipids raw form and acid form concerning the fight against skin aging, namely their action as an anti-radical and anti-elastatic protective agent as well as their repairing, restructuring and firming action, have been described respectively in the applications.
  • WO 95/34282 and FR 96/16093 The properties of sophorolipids raw form and acid form concerning the fight against skin aging, namely their action as an anti-radical and anti-elastatic protective agent as well as their repairing, restructuring and firming action, have been described respectively in the applications.
  • WO 95/34282 and FR 96/16093 The properties of sophorolipids raw form and acid form concerning the fight against skin aging, namely their action as an anti-
  • patent EP-A-209,783, FR-2,735,979 discloses the technological background of sophorolipids in crude or acid form as agent stimulating the metabolism of dermal fibroblasts.
  • the mechanical properties of the skin are largely ensured by the collagen fibers which constitute the main fabric of the dermis matrix.
  • Collagens constitute a family of around twenty distinct proteins, half of which are represented in the dermis. These are proteins rich in proline and hydroxyproline, synthesized by fibroblasts.
  • the lactonic fraction of the sophorolipids was isolated and purified from the sophorohipid mixture obtained at the end of fermentation.
  • the purification is carried out by precipitation and crystallization from ethanol according to a protocol described inter alia by A. P Tulloch et al, (Can J. chem. 40, 1326 (1962)).
  • the lactone fraction obtained is a white solid.
  • the product analyzed by thin layer chromatography generally consists of 95% sophorolipids under a lactone torch, the majority of which is in the diacetylated lactone form.
  • the lactonic fraction can comprise at least 70% by weight of diacetylated lactones and more particularly at least 80% by weight. It is obtained by dissolving the crude sophorolipids in ethanol, crystallization then filtration and re-installation in ethanol then filtration. The collected product is washed and then dried
  • a lactonic fraction comprising a mixture of sophorolipid lactones corresponding to the formula below, in which R is an acetyl group, will preferably be used. and where R 1 represents a hydrogen atom or an alkyl group containing 1 to 9 carbon atoms when R 2 represents a chain containing 7 to 16 carbon atoms or R 1 is hydrogen or a methyl group when R 2 represents a saturated or unsaturated hydrocarbon chain having 12 to 17 carbon atoms.
  • the purified sophorolipid fraction in the mainly diacetylated lactone form is active as a restructuring and repairing agent for the connective tissue and therefore against skin aging. More precisely, it stimulates the neosynthesis of collagens in vitro and this, advantageously compared to the crude sophorolipid mixture obtained in fermentation.
  • the purified sophorolipid fraction can be used in ranges of concentrations varying from 0.01 ppm to 5% (w / w) in dry matter in formulation and in particular in emulsions of the water / oil, oil / water, gel, serum type, lotion, shampoo. Its use will be more particularly in ranges of concentrations varying from 50 ppm to 1% (w / w) in dry matter.
  • the lactone fraction thus purified can be used alone in formulation or in combination with the raw form sophorolipid mixture obtained at the end of fermentation, the pH of which will be between 3 and 7.5, or also with the sophorolipids in deacetylated acid form, prepared according Patent FR 96/16093, protonated and / or acidic form at least in part in the form of monovalent or divalent metal salts.
  • sophorolipids in deacetylated acid form can also be used in a derivative form, for example in the ester form.
  • they exhibit their fatty acid function at least in part esterified by reaction with a linear or branched alcohol of 1 to 18 carbon atoms and preferably 1 to 8 carbon atoms.
  • the latter may likewise be associated with the purified sophorolipid fraction described in this patent.
  • the raw sophorolipids can be used at a concentration varying from 0.01 ppm to 10% (w / w) in dry matter and more particularly from 80 ppm to 2% (w / p) in dry matter.
  • they can be used at a concentration varying from 1 ppm to 10% (w / w) of dry matter and preferably from 0.02% to 1% of dry matter .
  • sophorolipids it may be advantageous to combine the purified lactone fraction product mixed or not with other sophorolipids, with alpha or beta hydroxy acids of 2 to 7 carbon atoms (lactic, malic, tartaric, glycolic, citric, iso -citric, salicylic ...) salified or not and their esters whose beneficial role is widely described with regard to the renewal of the epidermis.
  • Raw sophorolipids have the following composition:
  • the crystals obtained are dissolved in ethanol and the solution is recrystallized at + 6 ° C for 16 hours. After filtration, the lactone fraction obtained is washed and dried.
  • the white solid obtained comprises 95% by weight of lactones, the distribution of which is as follows:
  • the product in powder form is used in an aqueous solution at 50 mg / 1, pH 5 ⁇ 0.5 for carrying out the tests.
  • the local tolerance of the purified product has been studied on explants of human skin. It was evaluated by a histological examination of the effects of the product on the morphology of the epidermis.
  • the explants were incubated for 18 h at 37 ° C. in an atmosphere containing 5% C0 2 in the presence of the purified sophorolipid fraction.
  • the histological observations of the explants under these conditions did not make it possible to highlight the morphological alteration. Also, the product thus tested can be considered non-irritant.
  • the ocular tolerance of the product was evaluated in vitro, according to the PREDISAFE method. This method demonstrated a high level of correlation with the Draize test and of reproducibility.
  • the toxicity score for sophorolipids in purified lactone form is less than 15 on an ocular tolerance scale arbitrarily graduated from 0 to 50.
  • the product is in class I, slightly irritant.
  • EXAMPLE 2 Comparative Effects of the Raw Form Sophorolipids and the Purified Lactone Fraction of the Sophorolipids on Collagen Neosynthesis in Cultures of Normal Human Dermal Fibroblasts.
  • Collagens are quantitatively the major proteins of the dermis.
  • Proline and hydroxyproline make up 30% of the amino acids that make up collagens (high percentage and much higher than that of most other fibroblastic proteins). Hydroxyproline is not an amino acid incorporated during the synthesis of collagens as it is for proline.
  • the fibroblasts were isolated from the operative residue of a tummy tuck performed in a 19 year old woman.
  • the cells were cultured in the fibroblast culture medium (MCF) at 37 ° C. in a humid atmosphere containing 5% of CO 2 until the monolayers meet.
  • MCF fibroblast culture medium
  • the culture medium used was the fibroblast culture medium (MCF), consisting of MEM / M199 (3/4, 1/4, v / v) supplemented with penicillin (50 IU / ml), streptomycin (50 ⁇ g / ml), sodium bicarbonate (0.2%, w / v) and FCS (10%, v / v).
  • MCF fibroblast culture medium
  • the fibroblast incubation medium (called MIF) with the products consists of MEM / M199 (3/4, 1/4, v / v) supplemented with penicillin (50 IU / ml), streptomycin (50 ⁇ g / ml ), sodium bicarbonate (0.2%, w / v) and FCS (2%, v / v). It contained 1 ⁇ Ci / ml of tritiated proline.
  • the purified lactone fraction was diluted in MIF medium and was tested at 0.02; 0.08 and 0.4 ⁇ g / ml (dry matter).
  • the raw form sophorolipids were tested at 0.08; 0.4 and 2 ⁇ g / ml.
  • Ascorbic acid was tested at 100 ⁇ g / ml (0.5 raM) in MIF medium.
  • the fibroblast cultures were incubated for 3 days at 37 ° C, in a humid atmosphere containing 5% CO 2 .
  • the incubation media were removed and the cell mats were rinsed with PBS.
  • the cells were then lysed by the action of ultrasound.
  • the DNA assay was carried out according to a fluorimetric method using the reagent HOECHST 33258.
  • the assay of the proteins of the cell lysate was carried out according to the Coomassie blue method described by Bradford. These assays ensure an adequate interpretation of the results obtained on the neosynthesis of collagens.
  • control group and treated groups were treated by a factor analysis of variance (ANOVA 1, p ⁇ 0.05), followed by a Dunnett test (p ⁇ 0.05). The effect of the products was thus compared with the control group.
  • Sophorolipids crude 0.08; 0.4 and 2 ⁇ g / ml increase the "cell layer collagens" by a factor 1.63; 1, 50 and 1, 44 respectively. At the same concentrations, they increase "secreted collagens" by a factor of 1.39; 1.29 and 1.18.
  • Sophorolipids Purified lactone fraction Acid, crude form ( ⁇ g / ml) ( ⁇ g / ml) Ascorbic
  • Sophorolipids Purified acid ( ⁇ g / ml) crude form ( ⁇ g / ml) ascorbic
  • Collagens are quantitatively the major proteins of the dermis, they play an important role vis-à-vis the structure of the latter and therefore, after synthesis must be secreted in the extracellular matrix
  • the purified lactone fraction has a stimulating effect on Collagen neosynthesis higher than that of the gross sophorolipid mixture and that of ascorbic acid
  • the purified fraction makes it possible to increase by a factor 2.55 the secretion of the new collagen fibers compared to the control against a factor of 1.39 obtained with the raw form sophorolipids and a factor 1.81 with ascorbic acid.
  • the purified fraction of sophorolipids in lactone form can be used in cosmetically and / or dermatologically acceptable media, that is to say compatible with the skin, mucous membranes, hair and scalp. It can be incorporated into all dosage forms suitable for topical application and in particular in the form of emulsions obtained by dispersion of a fatty phase in an aqueous phase (O / W) or vice versa (W / O), of water / silicone emulsion , emulsion with a lamellar structure.
  • the sophorolipid product in lactone form purified by its effect on the stimulation of the cells of the dermis is interesting for the formulation of anti-aging, repairing and restructuring products of the dermis.
  • the sophorolipids in purified lactone form may also be used as a preventive against aging of the skin and may be used in treatment or care creams for the face, for the hands, for the feet and for the body, and in body care milks, lotions and gels for the skin.
  • Tefose 2561 PEG-6 stearate / Ceteth-20 / Glyceryl stearate / Steareth-20
  • Cetiol V Decyl oleate
  • Sepigel 305 Polyacrylamide / C13-14 Isoparaffin / Laureth-7
EP99920934A 1998-05-29 1999-05-27 Utilisation de sophorolipides comprenant des lactones diacetylees en tant qu'agent stimulateur du metabolisme des fibroblastes de la peau Withdrawn EP1082097A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9806789A FR2779057B1 (fr) 1998-05-29 1998-05-29 Utilisation de sophorolipides comprenant des lactones diacetylees en tant qu'agent stimulateur du metabolisme des fibroblastes de la peau
FR9806789 1998-05-29
PCT/FR1999/001245 WO1999062479A1 (fr) 1998-05-29 1999-05-27 Utilisation de sophorolipides comprenant des lactones diacetylees en tant qu'agent stimulateur du metabolisme des fibroblastes de la peau

Publications (1)

Publication Number Publication Date
EP1082097A1 true EP1082097A1 (fr) 2001-03-14

Family

ID=9526853

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99920934A Withdrawn EP1082097A1 (fr) 1998-05-29 1999-05-27 Utilisation de sophorolipides comprenant des lactones diacetylees en tant qu'agent stimulateur du metabolisme des fibroblastes de la peau

Country Status (6)

Country Link
US (1) US6596265B1 (ja)
EP (1) EP1082097A1 (ja)
JP (1) JP2002516836A (ja)
CA (1) CA2333787A1 (ja)
FR (1) FR2779057B1 (ja)
WO (1) WO1999062479A1 (ja)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7262178B2 (en) * 2003-03-24 2007-08-28 Polytechnic University Treatment of sepsis and septic shock
FR2855752B1 (fr) * 2003-06-03 2005-08-26 Lvmh Rech Utilisation cosmetique des sophorolipides comme agents regulateurs de la masse adipeuse sous-cutanee et application a l'amincissement
WO2012167815A1 (en) * 2011-06-06 2012-12-13 Ecover Co-Ordination Center N.V. Sophorolactone compositions and uses thereof
BE1019942A3 (nl) 2011-06-06 2013-02-05 Ecover Belgium N V Verbeterde sophorolacton samenstellingen, werkwijze voor de bereiding en gebruiken.
FR2991688B1 (fr) * 2012-06-06 2015-05-22 Soliance Biosolubilisant
US11590231B2 (en) * 2017-07-27 2023-02-28 Locus Solutions Ipco, Llc Compositions for enhancing bioavailability of pharmaceuticals, supplements and ingested substances
EP3703724A1 (en) 2017-11-02 2020-09-09 NatureCeuticals Sdn. Bhd. Extract of orthosiphon stamineus, formulations, and uses thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3526417A1 (de) * 1985-07-24 1987-02-05 Wella Ag Kosmetische mittel mit einem gehalt an einem sophoroselipid-lacton sowie seine verwendung
FR2720941B1 (fr) * 1994-06-13 1996-08-23 Inst Francais Du Petrole Utilisation des sophorolipides et compositions cosmétiques et dermatologiques.
FR2735979B1 (fr) * 1995-06-28 1997-08-14 Inst Francais Du Petrole Utilisation comme substances therapeutiquement actives ou produits cosmetiques des sophorolipides, en particulier pour le traitement de la peau
FR2740779B1 (fr) * 1995-11-08 1997-12-05 Rhone Poulenc Chimie Composition a base d'enzyme et de sophorolipide sous forme lactone et son utilisation dans les formulations detergentes pour le lavage du linge
FR2757766B1 (fr) * 1996-12-27 1999-02-19 Inst Francais Du Petrole Utilisation des sophorolipides en tant qu'agent stimulateur du metabolisme des fibroblastes dermiques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9962479A1 *

Also Published As

Publication number Publication date
FR2779057B1 (fr) 2001-06-15
US6596265B1 (en) 2003-07-22
JP2002516836A (ja) 2002-06-11
WO1999062479A1 (fr) 1999-12-09
FR2779057A1 (fr) 1999-12-03
CA2333787A1 (fr) 1999-12-09

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