US20180271119A1 - Acid composition comprising a phycocyanin - Google Patents

Acid composition comprising a phycocyanin Download PDF

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US20180271119A1
US20180271119A1 US15/762,659 US201615762659A US2018271119A1 US 20180271119 A1 US20180271119 A1 US 20180271119A1 US 201615762659 A US201615762659 A US 201615762659A US 2018271119 A1 US2018271119 A1 US 2018271119A1
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phycocyanin
acidic
composition according
acidic composition
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Olivier CAGNAC
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Fermentalg SA
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P21/00—Preparation of peptides or proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/58—Colouring agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/185—Vegetable proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/46—Addition of dyes or pigments, e.g. in combination with optical brighteners using dyes or pigments of microbial or algal origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/14—Extraction; Separation; Purification
    • C07K1/145—Extraction; Separation; Purification by extraction or solubilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/405—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from algae
    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
    • C12P17/165—Heterorings having nitrogen atoms as the only ring heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention concerns an acidic composition, particularly an acidic food composition, comprising at least one acidic-pH-stable phycocyanin.
  • pH resistance or stability is measured herein as a less than 10% loss of colouring, after a minimum exposure of 10 minutes at acidic pH. pH stability can be measured by other methods, such as physical characterization of the phycocyanins within the acidic compositions as a function of time.
  • the present invention concerns an acidic composition, particularly an acidic food composition, which can comprise at least one acidic-pH-resistant phycocyanin.
  • said phycocyanin can be a phycobiliprotein whose apoprotein can comprise at least the protein of SEQ ID NO 1 or SEQ ID 2 or a variant thereof.
  • the acidic composition particularly the acidic food composition, comprises an acidic-pH-resistant phycocyanin whose ⁇ -subunit apoprotein consists of SEQ ID NO 1 (accession number YP_009051179.1) and whose ⁇ -subunit apoprotein consists of SEQ ID 2 (accession number YP_009051180.1) or variants thereof.
  • a protein sequence corresponding to a reference sequence in this case the protein represented by SEQ ID NO 1 or SEQ ID NO 2 or SEQ NO 3 or SEQ NO 4, modified by one or more substitutions, insertions or deletions of one or more amino acids of the reference sequence and which has the same functional properties as said reference sequence.
  • the variants according to the invention have at least 83% sequence identity with the ⁇ subunits of the phycocyanin, and at least 82% with the beta subunits of the phycocyanin.
  • the variants according to the invention have at least 90% identity with the ⁇ (SEQ ID NO 1) and ⁇ (SEQ ID NO 2) subunits.
  • the variants advantageously have at least 89% sequence identity with the ⁇ subunits of the allophycocyanin, and at least 90% with the ⁇ subunits of the allophycocyanin.
  • polypeptide can be modified by substitution, insertion and/or deletion of at least one amino acid without substantially modifying the function thereof.
  • the phycocyanin or variants thereof useful, alone or mixed with an allophycocyanin or variants thereof, in acidic compositions, particularly in acidic food compositions can be obtained by culture of a natural organism naturally expressing the phycocyanin or the variant thereof of interest or by culture of an organism genetically transformed to express the phycocyanin or the variant thereof of interest selected for its capacity to produce said phycocyanin or variants thereof.
  • Exemplary natural organisms naturally expressing a phycocyanin useful in the compositions according to the invention or the variant thereof of interest include algae (or microalgae) of the order Cyanidiales.
  • the acidic composition particularly the acidic food composition, comprises an acidic-pH-resistant phycocyanin from natural organisms such as algae or microalgae of the order Cyanidiales, in particular from natural organisms of the families Cyanidiaceae or Galdieriaceae.
  • the acidic composition particularly the acidic food composition, comprises an acidic-pH-resistant phycocyanin from natural organisms which belong to the genera Cyanidioschyzon, Cyanidium, Galdieria , advantageously selected from the species of the genera Cyanidium and Galdieria
  • the acidic composition comprises an acidic-pH-resistant phycocyanin from natural organisms selected from the species Cyanidioschyzon merolae 10D, Cyanidioschyzon merolae DBV201 , Cyanidium caldarium, Cyanidium daedalum, Cyanidium maximum, Cyanidium partitum, Cyanidium rumpens, Galdieria daedala, Galdieria maxima, Galdieria partita, Galdieria sulphuraria.
  • an acidic-pH-resistant phycocyanin from natural organisms selected from the species Cyanidioschyzon merolae 10D, Cyanidioschyzon merolae DBV201 , Cyanidium caldarium, Cyanidium daedalum, Cyanidium maximum, Cyanidium partitum, Cyanidium rumpens, Galdieria daedala, Galdieria maxima, Galdieria partita, Galdieria sulphuraria.
  • the preferred form of the acidic composition, particularly the acidic food composition, according to the invention comprises an acidic-pH-resistant phycocyanin from a natural microalga such as Galdieria sulphuraria, Cyanidium caldarium or Cyanidioschyzon merolae . More preferentially, the acidic-pH-resistant phycocyanin comes from a natural microalga selected from Galdieria sulphuraria and Cyanidium caldarium.
  • an organism transformed to express the phycocyanin or the variant thereof of interest selected for its capacity to produce said phycocyanin or variants thereof mention may be made of a microorganism transformed so as to express the apoprotein of SEQ ID NO 1 and/or SEQ ID NO 2 and/or SEQ ID NO 3 and/or SEQ ID NO 4, said microorganism also comprising the biosynthetic pathways necessary for the production of the chromophore and for the binding thereof to the apoprotein.
  • Yeasts in particular may be mentioned as microorganisms that can be modified to produce the phycocyanin and/or allophycocyanin used in the food compositions according to the invention.
  • Such an industrial culture can advantageously be carried out in large-volume (i.e., 1,000-litre, 10,000-litre, 20,000-litre, 100,000-litre) fermenters.
  • the culture can be carried out under the conditions known to those skilled in the art. It can be carried out in batch mode, in fed-batch mode or in continuous mode.
  • the object of the invention is to provide a composition in which the phycocyanin is stable at acidic pH.
  • acidic composition is meant, according to the invention, any composition comprising a mineral or organic acid and a phycocyanin.
  • Said composition can be liquid, fluid or viscous, pasty or solid, which has an acidic pH and into which an acidic-pH-resistant phycocyanin is incorporated.
  • the composition according to the invention is an aqueous liquid composition, optionally in gel form, or a pasty or solid composition designed to be dissolved in an aqueous solution or in a solid or pasty composition comprising water.
  • the acidic composition pasty or solid composition intended to be employed and/or stored in a humid environment.
  • the mineral or organic acids useful in the compositions according to the invention are well-known to those skilled in the art.
  • Exemplary mineral acids include in particular carbonic, phosphoric, hydrochloric, sulphuric, perchloric, sulphonic and nitric acids.
  • Exemplary organic acids include in particular citric, lactic, malic, tartaric, succinic acids, advantageously citric acid.
  • the acidic food compositions according to the invention are well-known to those skilled in the art. They can comprise a carrier which can comprise structural components associated with active compounds identified for their nutritive supply or for their health properties which benefit humans or animals.
  • the acidic food composition according to the invention can also comprise food additives such as texturing agents, flavouring agents, preservatives, or any components well-known to those skilled in the art.
  • the carrier can comprise water and/or proteins and/or fats and/or fibre and/or sugars.
  • the components of the carrier may have only structural properties, but they are generally known for their nutritive supply.
  • the acidic food composition according to the invention can be ready-to-use or in the form of a food additive to be added to a solid, pasty or liquid preparation in order to prepare the edible food.
  • the acid will preferably be selected from the list of acidifiers authorized for foods, in particular carbonic, phosphoric, citric, malic, tartaric and lactic acids, more particularly citric acid.
  • the phycocyanin in a solid, liquid or pasty acidic composition according to the invention, can be incorporated, for example, in powder form.
  • Said acidic composition, particularly said acidic food composition may thus be in any known conventional form such as creams, gels, foams, pastes, etc.
  • Exemplary solid food compositions include cakes or biscuits, dry food for cooking, soluble powders, gelatinous solid compositions (jelly), foams etc.
  • said liquid acidic composition can be an aqueous composition into which the phycocyanin is dissolved. It can be in the form of a ready-to-use composition or a liquid concentrate for dilution, notably to be ingested or to be added to a solid food either for its preparation or for its ingestion, for example a concentrated liquid “topping” composition to be applied to a cake to give it colour.
  • a concentrated liquid “topping” composition to be applied to a cake to give it colour.
  • liquid acidic composition according to the invention can be of varying viscosity and optionally comprise additives such as viscosity agents, gelling agents, and other structuring additives known to those skilled in the art and typical for the preparation of liquid food compositions.
  • the phycocyanin content in said composition can be consistent with the practice of those skilled in the art as regards colouring.
  • the phycocyanin content can be from 2.5 mg/L to 2,500 mg/L, preferentially from 25 mg/L to 300 mg/L.
  • the phycocyanin content can generally be from 25 mg/L to 300 mg/L, preferentially from 50 mg/L to 100 mg/L.
  • the phycocyanin content can generally be from 250 mg/L to 2,500 mg/L, preferentially from 500 mg/L to 1,000 mg/L.
  • the phycocyanin content can generally be from 0.01 mg/g to 10 mg/g, preferentially from 0.1 mg/g to 5.0 mg/g, more preferentially from 0.25 mg/g to 2.5 mg/g.
  • FIG. 1 describes the amino acid sequences of the Galdieria sulphuraria phycocyanin and allophycocyanin apoproteins with:
  • FIG. 2 presents the stability curve as a function of pH of the phycocyanins extracted from Galdieria sulphuraria (UTEX2919) and Cyanidioschyzon merolae (ACUF 199) whose apoprotein sequence consists of SEQ ID NO 1 or a variant, in relation to the stability curve of the spirulina -derived phycocyanin Linablue®.
  • FIG. 3 represents colour change over time of an acidic beverage comprising phycocyanin.
  • W0, W2, W4 and W6 week 0, 2, 4 and 6.
  • the cultures are carried out in 1- to 2-L-useful-volume reactors with computer-controlled automated systems.
  • Culture pH is regulated by adding base (14% ammonia solution (wNH 3 /w)) and/or acid (4 N sulphuric acid solution).
  • Culture temperature is set to 37° C.
  • the culture is illuminated by baffles equipped with a system of white LEDs or blue LEDs (455 nm) in a way similar to that described in patent WO 2014/174182. Tracking of cell growth is carried out at different times by measuring absorbance at 800 nm. And a measurement of the dry mass is carried out by filtration.
  • Phycocyanin is then extracted according to a modification of the protocol described by Moon et al., 2014 (op. cit.). Said modification consists in replacing the phosphate buffer used to solubilize phycocyanin with demineralized water.
  • An extract (also called “phycocyanin extract” or “crude extract”) which comprises, in addition to the phycocyanin of interest, other water-soluble proteins, is thus obtained.
  • the phycocyanin extract can have several possible qualities depending on the method of extraction and/or purification used. For example, a crude extract will contain a higher amount of water-soluble proteins, other than phycocyanin, than that found in a purified extract.
  • purified extract is meant a crude extract of which a portion of the water-soluble proteins have been removed by ultrafiltration, hollow-fibre filtration, or ion-exchange chromatography, methods known to those skilled in the art, while retaining the phycocyanin.
  • Purity index is traditionally expressed by calculating the ratio of the absorbance of the solution at 618 nm (specific absorbance of phycocyanin) to that at 280 nm, the specific absorbance of aromatic amino acids giving an idea of the total protein level. The lower this ratio, the higher the amount of proteins other than phycocyanin in the solution.
  • the crude extract was purified using the KrosFlo® tangential flow filtration system from Spectrum® Labs.
  • Example 3 Stability Study of Phycocyanin Extracted from Strains Galdieria sulphuraria (UTEX#2919) and Cyanidioschyzon merolae (ACUF199) and Spirulina ( Arthrospira ) platensis as a Function of pH
  • the tests are carried out by taking as reference the data of the commercial product LineBlue® (http://www.dlt-spl.co.jp/business/en/ spirulina /linablue.html) from the company DIC Lifetec Co., Ltd. (Tokyo, Japan), which is a phycocyanin extracted from Spirulina ( Arthrospira ) platensis.
  • LineBlue® http://www.dlt-spl.co.jp/business/en/ spirulina /linablue.html
  • the pH is gradually lowered by adding 5% citric acid solution (Sigma 251275) to the phycocyanin preparation.
  • 5% citric acid solution Sigma 251275
  • a sample of the phycocyanin solution is collected and its absorbance measured at 618 nm, 10 minutes after lowering the pH to the desired value.
  • Phycocyanin extracted from Galdieria sulphuraria [(- ⁇ -)] exhibits very good pH-resistance compared with that of Spirulina , with less than 10% loss of pigmentation up to pH 2.75 (98.25% of its colouring at pH 3, 92.4% at pH 2.75), the loss increasing as of pH 2.5 (79% at pH 2.5; 75% at pH 2.25; 46% at pH 2).
  • Phycocyanin extracted from strain Spirulina platensis [(- ⁇ *-)] exhibits only 90% of its colouring at pH 4, 80% at pH 3.8; 60% at pH 3.6; 38% at pH 3.4.
  • Phycocyanin extracted from Spirulina platensis starts to precipitate as of pH 3.8.
  • Galdieria sulphuraria or Cyanidioschyzon merolae phycocyanins are more resistant to acidic pH than that extracted from Spirulina.
  • the isoelectric point of the ⁇ - and ⁇ -subunit apoproteins of phycocyanins and allophycocyanins whose sequence comparison was carried out was determined by the computational procedure described by Patrickios and Yamasaki (1995).
  • PCC 7418 (WP_015227201.1) 130/162 (80%) 3.786 Geitlerinema sp. PCC 7407 120/162 (74%) 3.936 (WP_015173541.1) Nostoc sp.
  • PCC 7120 (WP_010994705.1) 130/162 (80%) 3.978 ⁇ subunit of Phycocyanin from (# accession) Galdieria sulphuraria (YP_009051180.1) 171/171 (100%) 4.112 Cyanidium caldarium (AAB34027.2) 169/171 (99%) 4.112 Cyanidioschyzon merolae (NP 848987.1) 141/171 (82%) 4.112 Arthrospira maxima CS328 (EDZ96897.1) 130/171 (76%) 3.966 Spirulina platensis (1HA7 B) 130/170 (76%) 3.966 Arthrospira jenneri fz (AEV40871.1) 130/171 (76%) 4.062 Cyanobacterium stanieri PCC 7202 135/171 (79%) 3.966 (AFZ46321.1) Halothece sp.
  • PCC 7418 (WP 015227202.1) 133/171 (78%) 4.074 Geitlerinema sp. PCC 7407 138/171 (81%) 4.12 (WP 015173542.1) Nostoc sp. PCC 7120 (BAB72486.1) 141/170 (83%) 4.159
  • Example 5 Stability Over Time in a Beverage
  • the stability test in acid medium over time for the phycocyanin extracted from strain UTEX#2919 was carried out by adding the phycocyanin to a lemonade beverage (pH 2.95; as described in example 6: beverage 1). After adding 0.025 ⁇ of phycocyanin the apoprotein sequence of which consists of variant of SEQ ID NO 1, the beverage was exposed to a day/night cycle (16 h/8 h) with artificial light for 6 weeks, at room temperature.
  • Example 6 Examples of Acidic Beverages in Liquid Form Comprising Phycocyanin
  • Beverages containing phycocyanin can have the following composition:
  • Beverage 1 Soda Beverage:
  • Example 7 Solid Acidic Composition Comprising Phycocyanin: Acidic Sweet

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US15/762,659 2015-09-25 2016-09-22 Acid composition comprising a phycocyanin Pending US20180271119A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR1559072 2015-09-25
FR1559072A FR3041653B1 (fr) 2015-09-25 2015-09-25 Procede de culture d'algues, particulierement d'algues rouges unicellulaires (arus)
FR1653525A FR3041505B1 (fr) 2015-09-25 2016-04-21 Composition acide comprenant au moins une phycocyanine stable a ph acide
FR1653525 2016-04-21
PCT/EP2016/072583 WO2017050918A1 (fr) 2015-09-25 2016-09-22 Composition acide comprenant une phycocyanine

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US15/762,806 Active US11162126B2 (en) 2015-09-25 2016-09-22 Method for the culture of unicellular red algae

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EP3692806A1 (fr) 2019-02-11 2020-08-12 GNT Group B.V. Boisson colorée ayant un ph neutre
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BE1027165B1 (fr) * 2019-03-12 2020-11-03 B Blue Nutraceuticals Composition liquide comprenant de la phycocyanine
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EP3939437A1 (fr) 2020-07-17 2022-01-19 GNT Group B.V. Composition comprenant un extrait de spiruline

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CN116349890A (zh) 2023-06-30
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FR3041505A1 (fr) 2017-03-31
US11162126B2 (en) 2021-11-02
FR3041653A1 (fr) 2017-03-31
EP3353282A1 (fr) 2018-08-01
CA2998973A1 (fr) 2017-03-30
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