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WO2016099261A1 - Photopigments bleus naturels, procédés pour leur production et leurs utilisations en tant que colorant - Google Patents

Photopigments bleus naturels, procédés pour leur production et leurs utilisations en tant que colorant Download PDF

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Publication number
WO2016099261A1
WO2016099261A1 PCT/NL2015/050867 NL2015050867W WO2016099261A1 WO 2016099261 A1 WO2016099261 A1 WO 2016099261A1 NL 2015050867 W NL2015050867 W NL 2015050867W WO 2016099261 A1 WO2016099261 A1 WO 2016099261A1
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WO
WIPO (PCT)
Prior art keywords
phycocyanin
coloring material
blue
blue pigment
merolae
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.)
Ceased
Application number
PCT/NL2015/050867
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English (en)
Inventor
Marc Jos Elise Cornelis Van Der Maarel
Marta MARTINEZ GARCIA
Fean Davisnujaya SARIAN
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.)
Rijksuniversiteit Groningen
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Rijksuniversiteit Groningen
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Publication of WO2016099261A1 publication Critical patent/WO2016099261A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • 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

Definitions

  • the invention relates to natural blue photopigments, methods for producing them and to uses thereof as colorant, in particular in food, confectionary, ice creams and beverages.
  • phycocyanin has been produced chemically and by protein engineering, and new purification procedures allow highly pure phycocyanin to be obtained at high yields. But the application of phycocyanin in food, as a dye, in cosmetics, as fluorescent marker, and other applications is limited as the currently commercially available natural phycocyanin dyes have a relatively low stability with respect to temperature, light, and/or air, resulting in the loss of its intense blue color. The stability can possibly be enhanced using certain chemicals or additives but this contradicts the natural origin of the phycocyanin and thus limits its use in many products.
  • Phycocyanins are accessory pigments of the light harvesting complex of a range of micro-algae and cyanobacteria. Phycocyanins have been associated with free-radical scavenging, inhibition of lipid oxidation, anti-inflammation, and improving weakened immune systems.
  • Phycocyanins are members of the phycobiliprotein family and are composed of a multimeric protein (a and b subunits; 70 tot 110 kDa) to which a chromophore is attached.
  • the chemical structure of the chromophore is very similar to bilirubin, a degradation product of heme.
  • the chromophore is the actual light-absorbing unit, with an absorption maximum of about 620 nm and an emission maximum at about 650 nm.
  • the protein part confers the thermostability to the phycocyanin, with maxima of 70°C reported for certain thermophilic cyanobacteria.
  • temperature at which this colorant can be used is about 50 to 60°C.
  • additives such as coloring compounds need to be added at an elevated temperature before the mixture solidifies in order to achieve a homogeneous mixture. This posses restrictions on the thermal properties of the additives.
  • An example are wine gums that are made from a mixture of gelatin and glucose syrup that are heated and thoroughly blended. As gelatin starts to solidify at temperatures of about 60 to 70°C, any color or flavour additive needs to be added above the gelation
  • the extremophilic red microalga Cyanidioschyzon merolae growing optimally at 55°C, contains a very thermostable blue pigment (presumably a phycocyanin) which is very thermostable, with a maximum temperature tolerance of 82°C, i.e. far above the optimal growth temperature of the organism, while at 85°C it is stable for at least a few seconds. It was found to be stable in the pH range of 3 to 8.
  • the blue pigment can be obtained very easily by washing cells with pure water. This results in a clean blue pigment extract with almost no contamination (purity factor of 12 and higher).
  • the invention provides a thermostable blue pigment obtained or obtainable from Cyanidioschyzon merolae. Also provided is a coloring material comprising the C. merolae blue pigment.
  • the blue pigment preferably has a thermal stability until at least 70°C, more preferably at least 75°C. For example, incubation of the pigment for up to 30 minutes at 70°C results in a remaining concentration (CR, %) of the pigment relative to the initial concentration of at least 95.
  • CR, % remaining concentration
  • C. merolae is a rhodophyte that can make phycocyanin
  • C. merolae phycocyanin is stable at temperatures far higher than the maximum growth temperature of this organisms (up to about 55/60°C).
  • Moriyama et al. (FEBS Journal 275, 2899- 2918) describe that the DNA polymerase enzyme from C. merolae is stable at 50°C but not at 60°C, which is clearly in line with the optimal
  • the blue pigment can be easily purified to a purity index of 5 or higher, preferably 8 or higher, more preferably 10 or higher.
  • the purity index is expressed as the ratio of A618 to A280, wherein A618 is the maximum absorbance of the blue pigment (the C. merolae phycocyanin) and A280 is the absorbance of total proteins. Colorants with purity factors of
  • the invention also provides a consumable comprising a coloring material comprising the thermostable blue pigment from C.
  • the consumable is for example a food or beverage product, preferably selected from the group consisting of neutraceuticals,
  • the C. merolae blue pigment is the sole colorant.
  • the blue pigment can be any colorant.
  • the blue pigment can be any colorant.
  • the blue pigment can be any colorant.
  • Exemplary food, confectionary, desert or beverage products include a (blue) sport drink, a (blue) soda drink, (blue) ice cream, a (blue) wine gum, a (blue) button-shaped candy or a (blue) jelly bean.
  • the C. merolae pigment is used for the manufacture of blue wine gums.
  • the pigment can be used for any other coloring application or in any other type of product, such as paints, cosmetic products, clothing items, leather products, and the like.
  • the invention relates to a method for providing a thermostable natural blue pigment.
  • the method comprises the steps of
  • the red alga Cyanidioschyzon merolae is a small (2 ⁇ in diameter), unicellular, photoautotrophic organism that inhabits sulphate-rich hot springs.
  • the organization of a C. merolae cell is very simple: it contains one each of the nucleus, the mitochondrion and the chloroplast, but has no rigid cell wall.
  • the cell also has a minimum set of membranous structures: simple architectures of the endoplasmic reticulum and the Golgi body, a single microbody (peroxisome), and a small number of lysosomes (vacuoles).
  • C. merolae strains are publicly available and can be obtained from culture collection, such as NIES (National Institute for Environmental Studies), Microbial Culture Collection, Biodiversity Resource Conservation Section, Center for Environmental Biology and Ecosystem Studies, Japan.
  • NIES National Institute for Environmental Studies
  • Microbial Culture Collection Microbial Culture Collection
  • Biodiversity Resource Conservation Section Center for Environmental Biology and Ecosystem Studies, Japan.
  • Cyanidioschyzon merolae strain NIES 1804 (De Luca, Taddei et Varano) is used.
  • Cyanidioschyzon merolae cells can be cultured using known procedures to provide a biomass. For example, they can be maintained by gyratory culture (130 rpm), in 2x Allen's medium at pH 2.3 and 42°C under continuous light.
  • Cultured cells can be harvested by centrifugation, after which the biomass is suspended in de-ionized (also referred to as "ultrapure") water. This treatment causes rupture of the cells by a hypo-osmotic shock, and release of their contents including the blue pigment.
  • De-ionized (DI) water is water in which the ions have been removed. Ions can be removed in a number of ways, for instance by using anion and cation exchange resins in a variety of configurations. This can yield up to 17 megohm water, which is very pure. Distillation will also remove ions.
  • the third and most commonly used technique is dual reverse osmosis (RO) which can also give ultra pure water.
  • RO reverse osmosis
  • the aqueous suspension is homogenized by vigorous mixing, e.g. by vortexing.
  • the cells are left for some time to macerate for a time period that is sufficient to extract the blue pigment from the cells.
  • Maceration is typically performed at room temperature for at least 10-30 minutes. Very good results were obtained upon prolonged maceration during one or more hours. Accordingly, in one embodiment a method of the invention comprises maceration for at least 2 hours, preferably at least 3 hours.
  • the cell suspension can be centrifuged to remove debris and the blue colored supernatant can be collected in a fresh tube.
  • the supernatant can be concentrated or partially or fully dried. Water can be removed by methods known in the art, such as by freeze-drying, mild vacuum evaporation, drying chamber.
  • the crude extract can be subjected to a further treatment to purify the blue pigment. As shown herein below, fractional ammonium sulphate precipitation was suitably used to obtain blue pigment having a purity index of more than 15.
  • purification comprises subjecting the crude extract to ammonium sulphate precipitation at about 40% saturation via addition of solid ammonium sulphate, and recovery of the blue pigment in the precipitate.
  • the invention also provides a natural blue pigment obtainable by a method according to the invention.
  • the pigment is characterized among others by a thermal stability of up to at least 70°C.
  • the blue pigment can withstand exposure to acidic pH.
  • the invention provides a natural thermostable acid resistant blue pigment.
  • a coloring material or natural blue pigment as provided herein finds its use in any type of (industrial) coloring process. In view of its unique characteristics, it is however advantageously used in an (industrial) process involving exposure of the coloring material or pigment to a temperature of at least 70°C and/or a pH below 5.5.
  • said exposure has a duration of at least 15 minutes, preferably at least 30 minutes, more preferably at least 1 hour.
  • said exposure has a duration of up to 60 seconds, preferably up to 45 seconds, more preferably up to 15 seconds.
  • the blue pigment of the invention is used in a process involving exposure to a temperature of at least 75°C, and / or to a pH below 5.
  • exemplary processes include pasteurization, incorporation in acidic beverages, and the preparation of wine gums.
  • Figure 1 Effect of different maceration times of C. merolae cells in pure water on phycocyanin yields.
  • Step 1 Crude extract; 2. Supernatant Fraction 0-20%; 3. Supernatant of fraction 20-40%; 4.
  • Figure 5 Effect of incubating phycocyanin extract at 80°C and different pH for up to 150 min on the CR (%) value.
  • Figure 6 Effect of incubating phycocyanin extract at pH values between 2.5 and 4 at 80°C for up to 150 sec.
  • the red unicellular microalgae Cyanidioschyzon merolae strain NIES 1804 was obtained from NIES (National Institiute for Environmental
  • Phycocyanin containing biomass was harvested by centrifugation at 10,000 g for 10 minutes at 4°C. Washed cell biomass was resuspended in ultrapure water. Resuspended cells were mixed well for 5 minutes and kept at 4 °C for 3 hours. The cell debris was removed by centrifugation at 15.000 x g for 10 minutes at 4 °C and blue colored supernatant was collected in fresh tubes.
  • Phycocyanin crude extracts were further purified through ammonium sulfate precipitation. Two cycles of the process were performed, with initial precipitation at 20% saturation, 40% saturation and followed by third step at 60% saturation. Solid ammonium sulfate was dissolved by stirring at 400 rpm and the precipitate was recovered by centrifugation at 10,000 g at 4°C for 30 minutes. The pellet was dissolved in 0.05 M acetate buffer pH 4.5. Spectroscopic estimation of phycocyanin
  • absorption of Phycocyanin and A280 is the absorbance of total protein.
  • concentration of phycocyanin using the following equation:
  • thermostability of the extracted phycocyanin the samples were incubated at 80°C, and the absorbance at 624 nm was measured at regular intervals (0-150 minutes).
  • Fig. 1 shows the effect of different maceration times of C. merolae cells in pure water on phycocyanin yields. Maceration of up to 90 minutes gives relatively low amounts of phycocyanin. Maceration of more than 90 minutes gives considerably higher amounts of free phycocyanin. Purification of phycocyanin
  • Fig. 2 shows the UV-VIS absorption spectra of phycocyanin isolated from Cyanidioschyzon merolae at each step of purification. Step 1. Crude extracts; 2. Supernatant Fraction 0-20%; 3. Supernatant of fraction 20-40%; 4. Precipitation of fraction 20-40%; 5. Supernatant of fraction 40-60%; and 6. Precipitation of fraction 40-60%.
  • Figure 3 shows the effect of different temperature on CR (%) of phycocyanin solution (incubation time: 30 minutes).
  • the phycocyanin solution was incubated for 30 min. at the indicated temperature, after which the solution was centrifuges and the absorption of the supernatant was measured at 624 nm.
  • the phycocyanin Up to 75°C, the phycocyanin is clearly soluble. Between 75°C and 85°C the blue colorant precipitates and the solution becomes more and more transparent. Above 85°C, the phycocyanin quickly precipitates. This result clearly demonstrates that the C. merolae phycocyanin is thermostable up to 80 to 82°C.
  • Figure 4 shows the solubility of C. merolae phycocyanin subjected to 80°C, pH 4.2 for up to 150 min.
  • Figure 5 shows the effect of incubating phycocyanin extract at 80°C and different pH for up to 150 min on the CR (%) value. Above pH 3 the extract is clearly more stable than at pH values lower than 3.
  • Figure 6 shows the effect of incubating phycocyanin extract at pH values between 2.5 and 4 at 80°C for up to 150 sec.
  • the C. merolae phycocyanin is stable at low pH values for a few seconds.
  • Figure 7 shows the effect of different pH and various time incubations at room temperature (+ 25°C) on crude phycocyanin concentration. This clearly demonstrates that even at low pH values the C. merolae phycocyanin is stable at room temperature, indicating that it can be used in beverages or food products with a low pH value that are stored at room temperature.
  • Blue gelatin wine gums shows the effect of incubating phycocyanin extract at pH values between 2.5 and 4 at 80°C for up to 150 sec.
  • the C. merolae phycocyanin is stable at low pH values for a few seconds.
  • Figure 7 shows the effect of different pH and various time incubations at room temperature (+ 25°C) on crude phycocyanin concentration. This clearly demonstrates that even at low pH values the C.
  • the light blue wine gums had acceptable texture and appearance. The blue color was evenly distributed and no precipitation was visible. The wine gums kept their blue color for at least 6 weeks when stored at room temperature.

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  • Life Sciences & Earth Sciences (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

L'invention concerne des photopigments bleus naturels, des procédés pour leur production et leurs utilisations en tant que colorant, en particulier dans des produits alimentaires, des confiseries, des crèmes glacées et des boissons. L'invention concerne une matière colorante comprenant un pigment bleu obtenu ou pouvant être obtenu à partir de Cyanidioschyzon merolae. Le pigment bleu a une stabilité thermique jusqu'à 70 °C au moins, et un facteur de pureté égal ou supérieur à 5, de préférence égal ou supérieur à 8, plus préférablement égal ou supérieur à 10. L'invention concerne également un procédé permettant de procurer un pigment bleu naturel thermostable issu de C. merolae.
PCT/NL2015/050867 2014-12-16 2015-12-16 Photopigments bleus naturels, procédés pour leur production et leurs utilisations en tant que colorant Ceased WO2016099261A1 (fr)

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EP14198287 2014-12-16

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017050918A1 (fr) * 2015-09-25 2017-03-30 Fermentalg Composition acide comprenant une phycocyanine
EP3375298A1 (fr) * 2017-03-17 2018-09-19 L'Abeille Composition liquide comprenant de la phycocyanine
WO2018178334A2 (fr) 2017-03-30 2018-10-04 Fermentalg Purification des phycobiliproteines
WO2018229365A1 (fr) * 2017-06-15 2018-12-20 Algama Procédé d'obtention d'une boisson alimentaire stabilisée à base de jus de fruits comprenant des extraits de microalgues et/ou des cyanobactéries
US11365387B2 (en) 2015-12-04 2022-06-21 Fermentalg Method for culturing unicellular red algae (URA) with milk permeate
RU2781831C2 (ru) * 2017-03-30 2022-10-18 Ферментальж Очистка фикобилипротеинов
WO2023112407A1 (fr) * 2021-12-13 2023-06-22 Dic株式会社 Cyanidioschyzon merolae pouvant proliférer de façon hétérotrophe dans l'obscurité, et son utilisation

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017050918A1 (fr) * 2015-09-25 2017-03-30 Fermentalg Composition acide comprenant une phycocyanine
FR3041505A1 (fr) * 2015-09-25 2017-03-31 Fermentalg Composition acide comprenant au moins une phycocyanine stable a ph acide
CN108431202A (zh) * 2015-09-25 2018-08-21 费尔曼塔格公司 包含藻青蛋白的酸性组合物
CN108431202B (zh) * 2015-09-25 2023-02-17 费尔曼塔格公司 包含藻青蛋白的酸性组合物
US11162126B2 (en) 2015-09-25 2021-11-02 Fermentalg Method for the culture of unicellular red algae
US12031120B2 (en) 2015-12-04 2024-07-09 Fermentalg Method for culturing unicellular red algae (URA) with milk permeate
US11365387B2 (en) 2015-12-04 2022-06-21 Fermentalg Method for culturing unicellular red algae (URA) with milk permeate
EP3375298A1 (fr) * 2017-03-17 2018-09-19 L'Abeille Composition liquide comprenant de la phycocyanine
FR3063875A1 (fr) * 2017-03-17 2018-09-21 L'abeille Composition liquide comprenant de la phycocyanine
JP2020512334A (ja) * 2017-03-30 2020-04-23 フェルメンタル フィコビリタンパク質の精製
WO2018178334A2 (fr) 2017-03-30 2018-10-04 Fermentalg Purification des phycobiliproteines
KR102902983B1 (ko) * 2017-03-30 2025-12-23 페르망탈그 피코빌리프로테인의 정제
IL269540B2 (en) * 2017-03-30 2025-01-01 Fermentalg Purification of phycobiliproteins
US12139516B2 (en) 2017-03-30 2024-11-12 Fermentalg Purification of phycobiliproteins
WO2018178334A3 (fr) * 2017-03-30 2018-11-22 Fermentalg Purification des phycobiliproteines
RU2781831C2 (ru) * 2017-03-30 2022-10-18 Ферментальж Очистка фикобилипротеинов
FR3064635A1 (fr) * 2017-03-30 2018-10-05 Fermentalg Purification des phycobiliproteines
IL269540B1 (en) * 2017-03-30 2024-09-01 Fermentalg Purification of phycobiliproteins
JP7313283B2 (ja) 2017-03-30 2023-07-24 フェルメンタル フィコビリタンパク質の精製
KR20190141135A (ko) * 2017-03-30 2019-12-23 페르망탈그 피코빌리프로테인의 정제
WO2018229365A1 (fr) * 2017-06-15 2018-12-20 Algama Procédé d'obtention d'une boisson alimentaire stabilisée à base de jus de fruits comprenant des extraits de microalgues et/ou des cyanobactéries
FR3067568A1 (fr) * 2017-06-15 2018-12-21 Algama Procede d’obtention d’une boisson alimentaire stabilisee a base de jus de fruits comprenant des extraits de microalgues et/ou des cyanobacteries
CN110753496A (zh) * 2017-06-15 2020-02-04 奥伽马公司 获得包含微藻和/或蓝细菌提取物的由果汁制成的稳定化食品饮料的方法
WO2023112407A1 (fr) * 2021-12-13 2023-06-22 Dic株式会社 Cyanidioschyzon merolae pouvant proliférer de façon hétérotrophe dans l'obscurité, et son utilisation

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