WO2016162648A1 - Procédé d'obtention de culture de cellules de l'algue rouge acrochaetium moniliforme; obtention d'un extrait de sa biomasse; utilisation en cosmétique - Google Patents
Procédé d'obtention de culture de cellules de l'algue rouge acrochaetium moniliforme; obtention d'un extrait de sa biomasse; utilisation en cosmétique Download PDFInfo
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- WO2016162648A1 WO2016162648A1 PCT/FR2016/050816 FR2016050816W WO2016162648A1 WO 2016162648 A1 WO2016162648 A1 WO 2016162648A1 FR 2016050816 W FR2016050816 W FR 2016050816W WO 2016162648 A1 WO2016162648 A1 WO 2016162648A1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/02—Algae
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- 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
- A61Q19/008—Preparations for oily skin
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G33/00—Cultivation of seaweed or algae
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/02—Algae
- A61K36/04—Rhodophycota or rhodophyta (red algae), e.g. Porphyra
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- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9706—Algae
- A61K8/9717—Rhodophycota or Rhodophyta [red algae], e.g. Porphyra
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/008—Preparations for oily hair
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/12—Unicellular algae; Culture media therefor
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/11—Preparation or pretreatment of starting material involving culturing conditions, e.g. cultivation in the dark or under defined water stress
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
Definitions
- the present invention relates to a new unialgal biomass extract of small-sized multicellular macroalgae cells, the process for its preparation as well as its use as a cosmetic active agent, and the cosmetic, pharmaceutical and dermopharmaceutical compositions for topical use comprising.
- human skin is the first image offered to others, improving its appearance is often a subject of concern for the human being.
- the skin is the reflection of a state of well-being, often associated with a clean / glowing skin, or, conversely, a state of tiredness and / or negligence, often associated with oily / shiny skin.
- Oily skin is linked to a biological phenomenon called hyper-seborrhea or hyper-secretion sebaceous, defined as an abnormally high production of sebum by the sebaceous gland of the skin.
- This sebum flowing to the surface of the skin, gives it this unsightly "shiny".
- This hyperseborrhea is usually associated with an excess of testosterone hormone, which, once in the sebaceous gland, is converted by 5-alpha reductase into dihydro-testosterone (DHT), which binds to the receptors present in the sebaceous cells and activates the synthesis of sebum.
- DHT dihydro-testosterone
- Hyperseborrhea is accompanied by follicular hyperkeratinization, characterized by an increase in the number of keratinocytes in the follicular infundibulum, which causes obstruction of the follicular canal and makes sebum flow difficult. This results in sebum accumulation which is beneficial to the development of the anaerobic bacterium Propionibacterium acnes. The latter will cause the appearance of an inflammatory phenomenon. All of these phenomena lead to the appearance of characteristic clinical signs, such as comedones, characterizing acne skin.
- Oily skin is thus a precursor to the phenomenon of acne vulgaris, commonly known as acne, which is a chronic inflammatory dermatosis of the exclusively human pilosebaceous follicle. Evolving usually by outbreaks, this pathology usually starts at puberty and stops at the end of adolescence. However, even though 85% of young people aged 12 to 24 are affected, requiring specific and adapted treatment, 12% of women and 3% of men up to age 44 also have acne, or at least skin oily with acne tendency.
- the active ingredients "dermo-purifying” can thus act on various phenomena: Hyper-seborrhea via agents intervening, inter alia, in the amount of DHT Follicular hyperkeratinization via agents limiting, inter alia, keratinocyte differentiation;
- decanediol-1,2 as an agent making it possible to reduce the concentration of sebum on the skin and the advantage of this use compared to that of antibiotics such as tetracycline or retinoids such as retinal or retinoic acid, to obtain a satisfactory dermo-purifying or anti-acne action.
- Algae are chlorophyll photosynthetic organisms living in water or very humid environments. They can develop in seawater, freshwater, brackish water, in stagnant, beaten or turbulent environments.
- the algae can be unicellular or multicellular, they can be brown, green or red and are classified according to cytological and biochemical characteristics. These organisms play an important role on a global scale because they form the basis of food webs and they are involved in the production of atmospheric oxygen and in the fixation of carbon dioxide.
- Macroalgae are eukaryotic multicellular algae, usually visible to the naked eye and often referred to as macrophytes. They can reproduce sexually or asexually; in some species these two modes of reproduction succeed each other during the life cycle.
- the life cycle can include a generation, an alternation of two generations or three generations. Monogenetic, digenetic or trigenetic cycles will be discussed respectively.
- the species may be in the form of gametophytes, sporophytes, carposporophyte or tetrasporophyte.
- these different forms of life can be of the same morphologies, therefore isomorphous, or of different heteromorphic morphologies.
- the difference in morphology can be very significant, making it impossible to attach two life forms to the same species for an uninformed person.
- a life form can be macroscopic and another form of life can be microscopic.
- the sporophyte of Undaria pinnatifida is nearly one meter long whereas the gametophyte of this alga is a few tens of micrometers.
- Macroalgae measure from a few tens of micrometers in the case of algae of the genus Acrochaetium to a hundred meters for the species Macrocystis pyrifera.
- the class of red algae also called Florideophyceae, is part of the phylum Rhodophytes.
- the Class of Floridaophyceae Red Algae includes Acrochaetial, Acrosymphytales, Ahnfeltiales, Balbianiales, Balliales, Batrachospermales, Bonnemaisoniales, Ceramiales, Colaconematales, Corallinales, Entwisleiales, Floridaophyceae incertae sedis, Gelidiales, Gigartinales, Gracilariales, Halymeniales, Hildenbrandiales, Nemaliales, Nemastomatales, Palmariales , Peyssonneliales, Pihiellales, Plocamiales, Rhodachlyales, Rhodogorgonales, Rhodymeniales, Sebdeniales, Sporolithales and Thoreales.
- the red algae contain pigments found in other plants, such as chlorophyll a and carotenoids, but their originality is in the presence of phycobiliproteins: allophycocyanin (blue), phycocyanin (blue) and phycoerythrin which gives the color red.
- phycobiliproteins allophycocyanin (blue), phycocyanin (blue) and phycoerythrin which gives the color red.
- the organization of chloroplasts differentiates red algae from Glaucophytes and Cyanobacteria.
- the pigmentation of the red alga depends in part on the wavelength of the light that reaches the algae. Deep red algae accumulate a large amount of phycoerythrin, a pigment that can absorb light at this depth. On the surface, the ratio of the red pigment decreases, compared to chlorophyll and other phycobiliproteins, they become greener despite their name; we are talking about chromatic adaptation.
- the Chinese patent application published under the number CN 102475664 A discloses a cosmetic composition containing algae fibers for adjusting sebum or pore contraction.
- the red algae Gelidium and Palmaria are the most described for use as a regulating agent for the condition of oily skin.
- Japanese Patent Application Publication No. P2005-47910 A discloses the use of different red algae, for example Gelidium amansii, Gelidium japonica and Palmaria palmata, for their inhibitory property of sebum secretion, in particular. cosmetic, in food or as medicine.
- the Chinese patent application published under the number CN 102525864 A discloses the use of a peptide derived from seafood, coupled with algal polysaccharides derived from Gelidium amansii, as well as a pearl powder as a whole. active anti-acne agent.
- Korean patent application published under the number 2007 089309 discloses a method for preparing a concentrate of Gelidium amansii, in order to obtain an oligosaccharide of a particular molecular size, having antimicrobial, antioxidant and anti-cancer properties.
- the red algae of the orders Gelidiales and Palmariales are not known only for their dermo-purifying properties.
- Korean Patent Application Publication No. 1409764 A discloses the use of a lactically fermented Gelidium amansii extract as an anti-wrinkle ingredient for use in cosmetics and nutrition.
- the French patent application published under number 2 91 1 278 discloses the use of a sugar-rich Palmaria palmata extract as a depigmenting cosmetic active ingredient.
- Hydrocolloids produced by algae such as Chondrus crispus, Kappaphycus spp. and Eucheuma denticulatum are mainly used as thickeners and gelling agents in food and cosmetics.
- the biomasses producing these polymers are of economic interest [Ronelie C. et al. in: “Non-enzymatic isolation of somatic cells from Kappaphycus spp. and Eucheuma denticulatum (Solieriaceae, Rhodophyta) "; Eur. J. Phycol. (2014), 49 (4): 486-492].
- Dawes et al discloses a method for obtaining a unialgal biomass of red algae cells Eucheuma denticulatum and Kappaphycus alvarezii; from a sample taken from the natural environment, its cultivation to harvest biomass [Clinton J. Dawes et al in: "Branch, micropropagule and tissue culture of the red algae Eucheuma denticulatum and Kappaphycus alvarezii farmed in the Philippines” , Jouanl of applied Phycology 3: 247-257, 1991]. The same goes for Myounghoon et al. in the case of the red alga Galdieria sulphuraria [Myounghoon et al. in: “Isolation and charactrization of thermostable phycocyanin from Galdieria sulphuraria", Korean J. Chem. Eng., 31 (3), 490-495]
- H. Stegenga et al. have isolated by culture samples of Chromastrum moniliforme, gametophytes and tetrasporophytes from these algae [H. Stegenga et al. in: "Remarks on the Audouinella microscopica (NAG) Woekerling complex, with a brief survey of the genus chromastrum papenfuss (Rhodophyta, Nemaliales)", Acta Bot, Neerl., 28 (4/5), August 1979, 289- 31 1]
- the Chinese patent application published under the number CN 103858745 A discloses the development of artificial Sytosiphon lomentaria cultures by controlling the steps of differentiation of the germinal plasma of the alga, to produce a mature monocular sporangia, then cause its sporulation for the purpose. to inoculate culture supports for producing at sea, Sytosiphon lomentaria macroscopic biomass.
- the Chinese patent application published under the number CN 103931482 A discloses a method for obtaining a thallus of the gametophyte of the red algae Porphyra yezoensis, which is used in human nutrition, especially for the making of makis, involving first of all the "in vitro" culture of the conchocelis phase of the seaweed in order to produce conchospores which will be fixed on a culture support to allow the growth of thalli at sea.
- the subject of the invention is a process for obtaining a unialgal biomass of small-sized multicellular macroalgae cells, comprising the following successive stages:
- small-sized multicellular macroalga is denoted in the method as defined above, a multicellular macroalga, measuring between 30 ⁇ and 3cm and organized into cell clusters.
- This small-sized multicellular macroalga is differentiated from a large-sized multicellular macroalga because the latter is between 5 cm and 20 cm and is organized in a tissue way.
- a particular sample taken from seawater be it a sample of seawater, a sample taken from the surface of solid substrates such as rocks, sand, shells, sediments or artificial supports such as a boat hull, a pontoon or a dike; it can also be a sample taken from the surface or inside other plants (epiphyte or endophyte) such as algae or marine plants, on the surface or inside of animals (epiphyte or endophyte ) such as sponges, cnidarians, procordates, echinoderms, molluscs, arthropods, annelids, or marine vertebrates.
- epiphyte or endophyte such as algae or marine plants
- animals epiphyte or endophyte
- A) of the process as defined above is generally very rich in biodiversity and contains a wide selection of living organisms such as small animals, protozoa, prokaryotic microalgae, eukaryotic microalgae and multicellular macroalgae.
- unialgal sample of multicellular macroalgae cells is meant in the process as defined above, a culture containing only one species of multicellular algae.
- the unialgal sample of small-sized multicellular macroalgae cells is obtained by isolating the target macroalgae from the other organisms the targeted algae.
- a means of physical separation there is for example the separation carried out by means of a glass pipette using the end of the capillary to cut out some small sized multicellular macroalgae cells, controlling the operation visually, under a microscope or under a binocular loupe. There is also the separation by successive dilution of the cells of the target species from the natural sample.
- a means of chemical separation there is for example the use of antibiotics to eliminate microalgae of the cyanobacterial type, or that of germanium dioxide to eliminate microalgae of the diatom type.
- isolation methods are combined to obtain the best possible isolation result. All isolation methods, physical and chemical, are carried out in translucent light-transmitting receptacles, containing sterile seawater, containing at least one source of nitrogen such as sodium nitrate (NaN0 3 ) to a concentration of between 50mg / dm 3 and 250mg / dm 3 with a preference for 150mg / dm 3 and a phosphorus source such as sodium dihydrogen phosphate (NaH 2 PO 4 ) at a concentration of between 5mg / dm 3 and 75mg / dm 3 with a preference for 50mg / dm 3 . It is also possible to add other mineral elements to the seawater, for example by adding a nutritive medium in the desired proportions, such as the Provasoli medium of the following composition:
- step B) of the process as defined above is carried out in a photobioreactor containing seawater containing at least one nitrogen source such as sodium nitrate (NaN0 3 ) at a concentration between 50mg / dm 3 and 250mg / dm 3 with a preference for 150mg / dm 3 and a phosphorus source such as sodium dihydrogen phosphate (NaH 2 PO 4 ) at a concentration of between 5mg / dm 3 and 75mg / dm 3 with a preference for 50mg / dm 3 .
- nitrogen source such as sodium nitrate (NaN0 3 ) at a concentration between 50mg / dm 3 and 250mg / dm 3 with a preference for 150mg / dm 3
- a phosphorus source such as sodium dihydrogen phosphate (NaH 2 PO 4 ) at a concentration of between 5mg / dm 3 and 75mg /
- the cultures are conducted in translucent culture tanks under air bubbling optionally enriched with carbon dioxide.
- the cultures are generally conducted at 10 ° C to 25 ° C with a preference for 17 ° C under constant illumination.
- step A) of the process as defined above is therefore repeated until a unialgal sample of small multicellular macroalgae cells of satisfactory quality is obtained.
- Stage C) of the process as defined above is generally carried out using a filter cloth with a cut-off threshold of between 25 ⁇ m and ⁇ ⁇ mm according to the size of the small-sized multicellular macroalgae grown in culture.
- Unialgal biomass culture of small-sized multicellular macroalgae cells is filtered, with seawater passing through the web and remaining biomass at its surface. The biomass retentate is then pressed to remove the free water still present.
- Step D) of the process as defined above is carried out by methods known to those skilled in the art. For example, it is possible to dry said unialgal biomass of small-sized multicellular macroalgae cells obtained in step C) of the process as defined above, and then grind and sieve it to obtain a powder of the desired average diameter.
- it relates to a method for obtaining a unialgal biomass of red algae cells from the class of Floridophyceae, in the subclass of Nemaliophycidae, of the order Acrochaetiales, of the genus Acrochaetium and of the species Acrochaetium moniliforme.
- step D) of the process as defined above said unialgal biomass of small-sized multicellular macroalgae cells obtained in step C) is frozen, freeze-dried and then ground to obtain the desired powder.
- the subject of the invention is also a method for preparing a glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells obtained by the process as defined above, characterized in that it comprises the following successive stages:
- step E) during which said unialgal biomass of small-sized multicellular macroalgae cells obtained in step C) or in step D) is dispersed with stirring in a water-glycol mixture at a rate of 1% mass at 20% by mass of biomass per 100% by mass of dispersion;
- step F) during which the dispersion obtained in step E) above, is separated into its immiscible phases, to obtain the expected glycolic extract.
- glycol used in the process as defined above there are in particular butylene glycol or 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,2-pentanediol, 1.5- pentanediol, 1, 2-hexanediol or 1,6-hexanediol.
- the glycol used is butylene glycol.
- the water to glycol volume ratio of the glycol water mixture used in the process as defined above is generally less than or equal to 1/1 and greater than or equal to 1/9 and more particularly less than or equal to 1/2 and greater than or equal to 1/6. If necessary or if desired this volume ratio is adjusted in the aforementioned range at the end of step E).
- a process for preparing a glycolic extract of a unialgal biomass of red algae cells from the class of Floridophyceae, in the sub- class of Nemaliophycidae, of the order Acrochaetiales, of the genus Acrochaetium and of the species Acrochaetium moniliforme obtained by the process as defined above, characterized in that it comprises the following successive stages:
- step E) during which the powder of said unialgal biomass of red algae cells from the class of Florideophyceae, in the subclass of Nemaliophycidae, of the order Acrochaetiales, of the genus Acrochaetium and of the Acrochaetium moniliforme species obtained in step D), is dispersed with stirring in a water-butylene glycol mixture whose mass content of butylene glycol (butylene glycol mass to total weight butylene glycol mass and water) is between 50% and 75%, at the rate of 2% by weight at 10% by mass of biomass per 100% by mass of dispersion; stirring maintained for one to two hours, then if necessary or if desired, the mass content of butylene glycol is adjusted to 40% by addition of water;
- step F during which the dispersion obtained in step E) above, is separated into its immiscible phases, to obtain the expected glycolic extract.
- step F) of the process as defined above the separation of the immiscible phases is carried out, by settling by gravity or by centrifugation.
- the obtained glycolic acid extract is filtered through a 0.2 ⁇ m cut-off filter to remove any particles in suspension and to obtain a clear solution.
- the subject of the invention is also a glycolic extract of a unialgal biomass of small-sized multicellular macroalgae cells obtained by the process comprising the following successive steps: A step A) of preparing a unialgal sample of small-sized multicellular macroalgal cells from a sample of macroalgae taken from the natural environment;
- step E) during which said unialgal biomass of small-sized multicellular macroalgal cells obtained in step C) or in step D) is dispersed with stirring in a water-glycol mixture at a rate of 1% by mass at 20% by mass of biomass per 100% by mass of dispersion;
- step F during which the dispersion obtained in the previous step E), is separated into its immiscible phases.
- the subject of the present invention is the glycolic extract as defined above, in which the glycol used is butylene glycol.
- the subject of the present invention is the glycolic extract as defined above, characterized in that the powder of said unialgal biomass of small-sized multicellular macroalgae cells is used at the same time.
- stage E) of the process for its preparation is a powder of said unialgal biomass of red algae cells from the class of Florideophyceae, in the subclass of Nemaliophycidae, of the order Acrochaetiales, of the genus Acrochaetium and of the species Acrochaetium moniliforme.
- the water-glycol mixture used is a water-butylene glycol mixture whose mass content of butylene glycol (ratio of butylene glycol mass to total weight of butylene glycol and water) is between 50% and 75%,
- the dispersion in said water-glycol mixture is carried out at a rate of 2% by weight to 10% by mass of biomass per 100% by mass of dispersion;
- the stirring is maintained for one to two hours, then if necessary or if desired, -
- the mass content of butylene glycol is adjusted to 40% by adding water.
- the subject of the invention is also the use of the glycolic extract of a unialgal biomass of small-sized multicellular macroalgae cells as defined above, in order to reduce the amount of sebum produced by human skin. and / or by the scalp, said use being in a cosmetic composition, and more particularly the use as defined above in which the glycolic extract of a unialgal biomass of small multicellular macroalgae cells is the glycolic extract of a unialgal biomass of red algae cells from the class of Floridophytae, in the subclass of Nemaliophycidae, of the order Acrochaetiales, of the genus Acrochaetium and of the species Acrochaetium moniliforme, as defined previously .
- the invention also relates to a method for the purpose of reducing the amount of sebum produced by human skin and / or the scalp, comprising at least one application step on said human skin and / or on said scalp of a cosmetic composition (C1) for topical use comprising at least one cosmetically acceptable excipient and an effective amount of the glycolic extract of a unialgal biomass of small-sized multicellular macroalgae cells as defined above; and more particularly a method as defined above, in which the glycolic extract of a unialgal biomass of small-sized multicellular macroalgae cells included in said composition (C1) is the glycolic extract of a unialgal biomass of red algae cells from the class of Floridophytae, in the subclass of Nemaliophycidae, of the order Acrochaetiales, of the genus Acrochaetium and of the species Acrochaetium moniliforme, as defined above.
- a cosmetic composition (C1) for topical use comprising at least one cosmetic
- the cosmetic compositions comprising said red algae glycolic extract as defined above make it possible to treat the cutaneous modifications related to the skin. state, called oily skin, or hair related to the state, called oily scalp and thus improve the aesthetics.
- the invention also relates to a cosmetic composition (C1) for topical use comprising at least one cosmetically acceptable excipient and an effective amount of the glycolic extract of a unialgal biomass of small-sized multicellular macroalgae cells as defined above. above ; and more particularly a composition (C1) as defined above in which the glycolic extract of a unialgal biomass of small-sized multicellular macroalgae cells is the glycolic extract of a unialgal biomass of red algal cells. from the class Floridophytae, in the subclass of Nemaliophycidae, order Acrochaetiales, genus Acrochaetium and species Acrochaetium moniliforme, as defined above.
- said composition (C1) is generally spread on the surface of the skin to be treated, then the skin is massaged a few moments.
- composition (C1) for topical use
- composition (C1) is implemented by application to the skin, whether it be a direct application or indirect application when said composition (C1) according to the invention is impregnated on a support intended to be brought into contact with the skin (paper, wipe, textile, transdermal device, etc.).
- composition (C1) object of the present invention means according to the directive of the Council of the European Economic Community N ° 76/768 / CEE of July 27, 1976 modified by the directive N 93/35 / EEC of 14 June 1993, that it includes any substance or preparation intended to be placed in contact with the various parts of the human body (epidermis, hair and hair system, nails, lips and genitals) or with the teeth and oral mucosa in view, exclusively and mainly, to clean, perfume, modify the appearance and / or correct body odor and / or protect or maintain them in good condition .
- the term "100% of the mass of said composition (C1)" is understood to mean a quantity of between 0.1% and 5%. % by mass, more particularly between 0.1% and 3% by weight, and even more particularly between 0.5% and 2% by weight of said glycolic extract of said unialgal biomass of small multicellular macroalgae cells.
- composition (C1) which is the subject of the present invention is generally in the form of an aqueous or hydroalcoholic or hydro-glycolic solution, in the form of a suspension, an emulsion, a microemulsion or a nano-emulsion, whether water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil, or in the form of a powder.
- composition (C1) which is the subject of the present invention may be packaged in a bottle, in a device of the "bottle” pump type, in pressurized form in an aerosol device, in a device provided with a perforated wall such as a grid or in a device provided with a ball applicator (called “roll-on").
- the glycolic extract of said unialgal biomass of small-sized multicellular macroalgal cells which is the subject of the present invention is associated with chemical additives usually used in the field of formulations for topical use, such as foaming surfactants and and / or detergents, thickening and / or gelling surfactants, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-solvents, hydrotropic agents, water thermal or mineral plasticizers, emulsifiers and coemulsifiers, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants, perfumes, essential oils preserving agents, conditioning agents, deodorant agents, whitening agents intended for the bleaching of hairs and skin, active principles intended to provide a treating and / or protective action with respect to the skin or the hair, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of active ingredients, exfoliating particles
- foaming and / or detergent surfactants that can be combined with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgal cells in the composition (C1) include anionic foaming and / or detergent surfactants. , cationic, amphoteric or nonionic.
- foaming and / or detergent anionic surfactants mention may be made of the alkali metal, alkaline earth metal, ammonium, amine or alkylalcohol salts of alkylether sulfates, alkyl sulphates, alkylamidoethers sulphates, alkylaryl polyether sulphates, monoglyceride sulphates, alpha-olefin sulphonates, paraffin sulphonates, alkyl phosphates, alkyl ether phosphates, alkyl sulphonates, alkylamide sulphonates, alkylaryl sulphonates, alkyl carboxylates alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, alkyl sarcosinates, acyl isethionates, N-acyl tau
- Amphoteric foaming and / or detergent surfactants include alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates.
- foaming and / or detergent cationic surfactants mention may be made especially of quaternary ammonium derivatives.
- alkylpolyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical containing from 8 to 16 carbon atoms, such as octyl polyglucoside or decyl polyglucoside.
- undecylenyl polyglucoside dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12-dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil”; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides; N-alkylamines.
- thickening and / or gelling surfactants that may be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include fatty esters of alkylpolyglycosides which may be alkoxylated.
- ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATE TM LT and GLUMATE TM DOE120; alkoxylated fatty esters such as PEG 150 pentaerythrityl tetrastearate marketed under the name CROTHIX TM DS53, PEG 55 propylene glycol oleate sold under the name ANTIL TM 141; fatty chain polyalkylene glycol carbamates such as PPG-14 laureth isophoryl dicarbamate marketed under the name ELFACOS TM T21 1, PPG-14 palmeth-60 hexyl dicarbamate sold under the name ELFACOS TM GT2125.
- ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATE
- thickening and / or gelling agents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgal cells in the composition (C1)
- linear polyelectrolyte polymers such as homopolymer of partially or totally salified acrylic acid, homopolymer of partially or totally salified methacrylic acid, homopolymer of 2-methyl-[(1-oxo-2) partially or completely salified (AMPS), copolymers of acrylic acid and AMPS, copolymers of acrylamide and AMPS, copolymers of vinylpyrrolidone and AMPS, copolymers of AMPS and (2-hydroxyethyl) acrylate, copolymers of AMPS and (2-hydroxyethyl) methacrylate, copolymers of AMPS and hydroxyethylacrylamide, copolymers of AMPS and N, N-dim acrylamide, copolymers of AMPS and N, N-dim acrylamide, copoly
- R ' 3 represents a hydrogen atom or a methyl radical
- R' 4 represents a linear or branched alkyl radical containing from eight to thirty carbon atoms and n represents a number greater than or equal to one and less than or equal to fifty .
- the polyelectrolytic polymers linear or branched or crosslinked that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1), can be in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder.
- the polyelectrolytic polymers linear or branched or crosslinked that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1), can be selected from the products marketed under the SIMULGEL TM EG, SIMULGEL TM EPG, SEPIGEL TM 305, SIMULGEL TM 600, SIMULGEL TM NS, SIMULGEL TM INS 100, SIMULGEL TM FL, SIMULGEL TM A, SIMULGEL TM SMS 88, SEPINOV TM EMT 10, SEPIPLUS TM 400, SEPIPLUS TM 265, SEPIPLUS TM S, SEPIMAX TM Zen, ARISTOFLEX TM AVC, ARISTOFLEX TM AVS, NOVEMER TM EC-1, NOVEMER TM EC 2, ARISTOFLEX TM HMB, COSMEDIA TM SP, FLOCARE TM AND 25, FLOCARE TM AND 75
- thickening and / or gelling agents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- thickening and / or gelling agents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- thickening and / or gelling agents that can be combined with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include cellulose, cellulose derivatives such as methyl cellulose, ethyl cellulose, hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.
- stabilizing agents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include microcrystalline waxes, and more particularly ozokerite, inorganic salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
- solvents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- organic solvents such as glycerol, diglycerol, and the like.
- thermal or mineral waters that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- thermal or mineral waters having a mineralization of at least 300 mg / l in particular Avene water, Vittel water, the waters of the Vichy basin, Uriage water, Roche Posay water, water from Bourboule, the water of Enghien-les-bains, the water of Saint-Gervais-les bains, the water of Néris-les-bains, the water of Allevard-les-bains, the water of Digne , Maizieres water, Neyrac-les-bains water, Lons le Saunier water, Rochefort water, Saint Christau water, Fumades water and Tercist water the baths.
- hydrotropic agents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- emulsifying surfactants that can be associated with the glycolic extract of said unialgal biomass of multicellular macroalgal cells of small size in the composition (C1) include nonionic surfactants, anionic surfactants, cationic surfactants.
- emulsifying nonionic surfactants which may be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- esters of fatty acids and of sorbitol like the products marketed under the MONTANE TM 40, MONTANE TM 60, MONTANE TM 70, MONTANE TM 80 and MONTANE TM 85 names; compositions comprising glycerol stearate and ethoxylated stearic acid between five moles and one hundred and fifty moles of ethylene oxide, such as the composition comprising stearic acid ethoxylated to one hundred and thirty-five moles of ethylene oxide and glycerol stearate marketed under the name SIMULSOL TM 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methyl glucoside esters; alkyl polyglycosides having
- anionic surfactants that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- Examples of cationic emulsifying surfactants that can be combined with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include aminoxides, quaternium-82 and the surfactants described. in the patent application WO 96/00719 and mainly those whose fatty chain comprises at least sixteen carbon atoms.
- Examples of opacifying and / or nacrating agents that may be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include sodium palmitate, stearate of sodium, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene distearate glycol, polyethylene glycol monostearate, polyethylene glycol distearate, and fatty alcohols having from twelve to twenty-two carbon atoms.
- texture agents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgal cells in the composition (C1)
- mention may be made of N-acylated amino acid derivatives such as lauroyl lysine marketed under the name AMINOHOPE TM LL, octenyl starch succinate sold under the name DRYFLO TM, myristyl polyglucoside marketed under the name MONTANOV TM 14, cellulose fibers, cotton fibers, fibers chitosan, talc, sericite, mica.
- deodorant agents that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- alkali silicates zinc salts such as sulphate zinc, zinc gluconate, zinc chloride, zinc lactate
- quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts
- glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2-decanediol; 1,3-propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSAN TM; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum zirconium tetrachlorohydrate
- oils which can be combined with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include mineral oils such as paraffin oil, lemon Vaseline oil, isoparaffins or mineral white oils; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, safflower oil,nadooulier oil, passionflower oil, hazelnut oil, palm oil, butter shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or vegetables ethoxylated vegetable oils; synthetic oils such as
- waxes that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1)
- candelilla ouricoury wax, Japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and solid fatty acids at room temperature; glycerides solid at room temperature.
- waxes is meant in the present application the compounds and / or mixtures of compounds insoluble in water, having a solid appearance at a temperature greater than or equal to 45 ° C.
- vitamins and their derivatives in particular their esters, such as retinol (vitamin A) and its esters (retinyl palmitate for example), ascorbic acid (vitamin C) and its esters, ascorbic acid sugar derivatives (such as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); the compounds showing a lightening or depigmenting action of the skin, such as ⁇ -undecylenoyl phenylalanine marketed under the name SEPIWHITE TM MSH, SEPICALM TM VG, mono-undecylenoyl phenylalanine glycerol monoester and / or diester, ⁇ -unde
- antioxidants that can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include EDTA and its salts, citric acid , tartaric acid, oxalic acid, BHA (butylhydroxyanisol), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINE TM GL 47S marketed by the Akzo Nobel company under the INCI name: Tetrasodium Glutamate Diacetate.
- sunscreens that can be combined with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1) include all those contained in the cosmetic directive 76/768 / EEC amended Annex VII.
- the family of benzoic acid derivatives such as the acids para-aminobenzoic acid (PABA), in particular the monoglycerol esters of PABA, the ethyl esters of ⁇ , ⁇ -propoxy PABA, the ethyl esters of ⁇ , ⁇ -diethoxy PABA, the ethyl esters of ⁇ , ⁇ -dimethyl PABA, the esters de, ⁇ -dimethyl PABA methyls, butyl esters of ⁇ , ⁇ -dimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate,
- l-camphor benzalkonium methosulfate camphor
- urocanic acid ethyl urocanate
- sulfonic acid derivatives such as sulfonic acid 2-phenyl benzimidazole-5 and its salts
- triazine derivatives such as hydroxyphenyl triazine, (ethylhexyloxy) (hydroxyphenyl) (4-methoxyphenyl) triazine, 2,4,6-trianillin- ⁇ -carbo-2'-ethylhexyl-1 ' -oxy) -1,3,5-triazine, 4,4 - ((6 - (((1,1-dimethylethyl) amino) carbonyl) phenyl) amino) -1,3,5-triazine-2, Benzoic acid 4-diyl diimino) bis (2-ethylhexyl) ester, 2-phenyl-5-
- inorganic screens which can be associated with the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells in the composition (C1), mention may be made of titanium oxides , zinc oxides, cerium oxide, zirconium oxide, iron oxides yellow, red or black, chromium oxides. These mineral screens can be micronized or not, having undergone or not surface treatments and may be presented in the form of aqueous or oily predispersions.
- the subject of the invention is also the glycolic extract of said unialgal biomass of small-sized multicellular macroalgae cells as defined above, for its use in a therapeutic treatment method aimed at reducing the quantity of sebum produced by human skin and or by the scalp, and more particularly the glycolic extract of a unialgal biomass of red algae cells from the class of Floridophytae, in the subclass of Nemaliophycidae, of the order Acrochaetiales, of the genus Acrochaetium and of the species Acrochaetium moniliforme, as defined above, for its use in a therapeutic treatment method intended to reduce the amount of sebum produced by the human skin and / or by the scalp.
- Extract A glycolic extract (in butylene glycol) of a culture of the alga Acrochaetium moniliforme obtained by the process according to the invention
- Extract B glycolic extract (in butylene glycol) of the alga Delesseria obtained from a lyophilizate of biomass of said algae;
- Extract C glycolic extract (in butylene glycol) of the alga Palmaria obtained from a lyophilizate of biomass of said algae;
- Extract D glycolic extract (in butylene glycol) of the alga gelidium obtained from a biomass lyophilizate of said algae.
- the model chosen to highlight the technical effect of our products is a model for studying the production of dihydrotestosterone (DHT), revealing the activity of the enzyme 5-oreductase, a highly targeted enzyme to determine the dermopurifying properties of cosmetic ingredients.
- DHT dihydrotestosterone
- This model is a cellular model, more robust than models on purified enzyme.
- Human fibroblasts of the dermal follicular papilla male, 22 years old were seeded in culture plates coated with collagen in the presence of a specific growth medium. After three days, they were pretreated for 24 hours with the positive reference [Finasteride (F) at 2 ⁇ and 1 ⁇ ] and each of the algae extracts to be tested (Table 2). The fibroblasts were then stimulated with 0.5 ⁇ testosterone before undergoing a 24-hour post-treatment. Each trial was done in sextuplicate.
- Viability was measured by a WST-8 reagent and testosterone transformation was then assessed by measuring intracellular (DHT) concentration. Viability was expressed relative to that of the control without testosterone (control T0). The amount of (DHT) was normalized by the viability results and then reported to the control condition with testosterone (0.5 ⁇ ) control (T1) to calculate a percent effect and also referred to control conditions with and without testosterone to calculate a percentage of protection.
- Extracts A extracts of a biomass of Acrochaetium moniliforme, obtained according to the process of the invention
- DHT a limiting effect of the production of DHT
- the method of the invention makes it possible to obtain an extract having a dermopurifying effect that is more interesting / differentiating than the other red algae whose dermopurifying properties have already been described.
- Solagum TM AX A mixture of acacia gum and xanthan gum used as an emulsifying agent and marketed by the company SEPPIC;
- Montanov TM 202 (INCI name: Arachidyl Alcohol & Behenyl Alcohol & Arachidyl Glucoside): Emulsifying agent marketed by the company SEPPIC;
- Ceiol TM OE (INCI name: Dicaprylyl ether): Fatty phase commercialized by the company
- Lanol TM P Glycol palmitate marketed by the company SEPPIC;
- Sepiplus TM 400 (INCI name: Polyacrylate-13 & Polyisobutene & Polysorbate 20): polymeric thickener marketed by the company SEPPIC;
- Euxyl TM PE9010 (INCI name: phenoxyethanol and ethylhexylglycerin): Preservative agent marketed by Schulcke & Mayr
- Sensiva TM PA40 (INCI name: Phenethyl Alcohol (and) Ethylhexylglycerin): antimicrobial agent marketed by Schulcke & Mayr
- Montanov TM 14 (INCI name: Myristyl Alcohol & Myristyl Glucoside): Emulsifying agent marketed by the company SEPPIC;
- Sepimax TM Zen (INCI name: polyacrylate crosspolymer-6): thickening, emulsifying and stabilizing agent;
- Aquaxyl TM (INCI name: Xylitylglucoside and Anhydroxylitol and Xylitol): moisturizing composition marketed by the company SEPPIC;
- Montanox TM 20 (INCI name: Polysorbate 20): oil-in-water type emulsifier sold by the company SEPPIC;
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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JP2017552969A JP6850732B2 (ja) | 2015-04-10 | 2016-04-08 | 紅藻アクロカエティウム・モニリフォルメ(Acrochaetium moniliforme)の細胞を培養するための方法、そのバイオマスの抽出物を得るための方法および化粧料におけるその使用 |
KR1020177031332A KR20180008437A (ko) | 2015-04-10 | 2016-04-08 | 아크로캐티움 모닐리포름 홍조류 세포의 배양 방법, 이의 바이오매스 추출물의 수득 방법, 및 미용 분야에서의 이들의 용도 |
US15/564,624 US11224627B2 (en) | 2015-04-10 | 2016-04-08 | Method for culturing cells of Acrochaetium moniliforme red algae, method for obtaining an extract of the biomass thereof, and use of same in cosmetics |
AU2016245317A AU2016245317B2 (en) | 2015-04-10 | 2016-04-08 | Method for culturing cells of acrochaetium moniliforme red algae, method for obtaining an extract of the biomass thereof, and use of same in cosmetics |
CN201680028349.3A CN107743394A (zh) | 2015-04-10 | 2016-04-08 | 用于培养串珠顶丝藻红藻的细胞的方法、用于获得其生物质的提取物的方法、以及其在化妆品中的用途 |
EP16731197.6A EP3280427A1 (fr) | 2015-04-10 | 2016-04-08 | Procédé d'obtention de culture de cellules de l'algue rouge acrochaetium moniliforme; obtention d'un extrait de sa biomasse; utilisation en cosmétique |
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FR1553106A FR3034780B1 (fr) | 2015-04-10 | 2015-04-10 | Procede d'obtention de culture de cellules de l'algue rouge acrochaetium moniliforme, methode d'obtention d'un extrait de sa biomasse et son utilisation en cosmetique |
FR1553106 | 2015-04-10 |
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PCT/FR2016/050816 WO2016162648A1 (fr) | 2015-04-10 | 2016-04-08 | Procédé d'obtention de culture de cellules de l'algue rouge acrochaetium moniliforme; obtention d'un extrait de sa biomasse; utilisation en cosmétique |
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US (1) | US11224627B2 (fr) |
EP (1) | EP3280427A1 (fr) |
JP (1) | JP6850732B2 (fr) |
KR (1) | KR20180008437A (fr) |
CN (1) | CN107743394A (fr) |
AU (1) | AU2016245317B2 (fr) |
FR (1) | FR3034780B1 (fr) |
WO (1) | WO2016162648A1 (fr) |
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2015
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- 2016-04-08 CN CN201680028349.3A patent/CN107743394A/zh active Pending
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2018154599A (ja) * | 2017-03-21 | 2018-10-04 | 株式会社シーボン | 化粧料 |
CN111411090A (zh) * | 2020-04-07 | 2020-07-14 | 珀莱雅化妆品股份有限公司 | 一种耐高温超氧化物歧化酶的制备方法及其应用 |
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US11224627B2 (en) | 2022-01-18 |
CN107743394A (zh) | 2018-02-27 |
FR3034780B1 (fr) | 2018-10-19 |
AU2016245317A1 (en) | 2017-11-09 |
JP2018512148A (ja) | 2018-05-17 |
EP3280427A1 (fr) | 2018-02-14 |
KR20180008437A (ko) | 2018-01-24 |
FR3034780A1 (fr) | 2016-10-14 |
JP6850732B2 (ja) | 2021-03-31 |
AU2016245317B2 (en) | 2022-02-17 |
US20180117106A1 (en) | 2018-05-03 |
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