CN113201230B - Monascus pigment product and preparation method thereof - Google Patents

Monascus pigment product and preparation method thereof Download PDF

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CN113201230B
CN113201230B CN202011547679.8A CN202011547679A CN113201230B CN 113201230 B CN113201230 B CN 113201230B CN 202011547679 A CN202011547679 A CN 202011547679A CN 113201230 B CN113201230 B CN 113201230B
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pigment
pigments
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orange
product
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CN113201230A (en
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陈勉华
王晶
郭佳
杨曼红
王笑
张妍
谭晓铭
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Tianjin University of Science and Technology
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    • 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
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C20/00—Cheese substitutes
    • A23C20/02—Cheese substitutes containing neither milk components, nor caseinate, nor lactose, as sources of fats, proteins or carbohydrates
    • A23C20/025—Cheese substitutes containing neither milk components, nor caseinate, nor lactose, as sources of fats, proteins or carbohydrates mainly containing proteins from pulses or oilseeds
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    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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    • 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
    • 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
    • A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40—Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42—Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/428—Addition of flavours, spices, colours, amino acids or their salts, peptides, vitamins, yeast extract or autolysate, nucleic acid or derivatives, organic acidifying agents or their salts or acidogens, sweeteners, e.g. sugars or sugar alcohols; Addition of alcohol-containing products
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    • 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
    • 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
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    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0096—Purification; Precipitation; Filtration
    • 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

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Abstract

The invention provides a monascus pigment product, which is obtained by extracting a fermentation product containing monascus orange pigment and yellow pigment by using an organic solvent to obtain an extraction product, and enriching the orange pigment and the yellow pigment from the extraction product, wherein the orange pigment is one or more of orange pigment O1 and O2, the yellow pigment is one or more of yellow pigment Y1 and Y2, and the fermentation product is red yeast rice. The invention also provides a method for preparing the monascus pigment product, which comprises the steps of extracting a fermentation product containing monascus orange pigment and yellow pigment by using an organic solvent to obtain an extraction product, and enriching the orange pigment and the yellow pigment from the extraction product to obtain the monascus pigment product. The product can be widely applied to the food and non-food coloring field as a yellow colorant or a red colorant.

Description

Monascus pigment product and preparation method thereof
Technical Field
The invention relates to a pigment product and a preparation method thereof, in particular to a monascus pigment product and a preparation method thereof.
Background
Red rice is prepared by fermenting Monascus in solid or liquid state on rice, and is called red rice because it is rich in red pigment. The monascus pigment obtained by extracting the pigment (mainly aiming at the red pigment) from the solid or liquid fermented monascus and spray drying is called monascus, and the monascus product obtained by solid fermentation on a rice substrate is called monascus. Monascus pigment has been used for thousands of years in China, and is widely used for coloring meat products represented by ham and bean products represented by fermented red bean curd.
The pigment components in the red yeast for food coloring are complex, and the document reports that the structure analysis of the red yeast has been completed and the red yeast pigments exceed 60 types, wherein the common pigments mainly comprise two orange pigments (red monascus pigment, orange pigment O1 for short; red yeast red pigment Monascorubrine, orange pigment O2 for short); two kinds of yellow pigments (Monascin, Y1 for short; ankaflavin, Y2 for short); two red pigments (Rubropunctamine, R1 for short; monascorubramine, R2 for short).
Although the monascus pigment contains a plurality of pigment components, the red yeast for coloring the red hue is most widely applied at present. GB1886.19-2015 and GB1886.181-2016 regarding red yeast rice and monascus red standards all tend to have red pigment as the main measurement index: the extraction solvent adopts 70% ethanol, which is most suitable for extracting red pigment (in red orange yellow monascus pigment, the polarity of the red pigment is generally higher than that of yellow and orange), and the detection wavelengths of the red yeast rice and the red yeast rice are respectively 505nm and 495 +/-10 nm, which are close to the maximum absorption wavelength of various red pigments. The measurement standard for monascus pigment of 9 th edition published in 2018 of japan, food additives official manual, adopts a detection wavelength of 480-520nm, and the pigment extraction solvent is 95% ethanol and water (1. In the existing evaluation method for the color value of the red yeast product, the extraction of the red pigment is concerned, and the detection and utilization of orange pigment and yellow pigment, especially the detection and utilization of the orange pigment O1 and O2 are ignored.
Orange O1 and orange O2 are not only good sources of orange colorants, but also can be used as red colorants by reacting with amino acids. In studies on orange O1 and O2, it was found that it can react with amino acids and other nitrogen-containing compounds to form red pigments. Orange pigments O1 and O2 are used as precursor compounds to synthesize various derivative pigments.
Citrinin is a hepato-toxic mycotoxin, and minimizing the amount of citrinin in food or food additives is a major concern for those skilled in the art. At present, the conventional method is to carry out gene modification on monascus and knock out a key gene pksCT for synthesizing citrinin, so that the yield of the citrinin is reduced; or various additives are added in the fermentation process to reduce the content of the citrinin in the fermentation product. Both of them have problems of complicated operation and decreased pigment yield.
How to realize the remarkable reduction of the haematochrome while enriching the orange pigment and the yellow pigment by the red yeast rice and the remarkable reduction of the haematochrome and the citrinin while enriching the orange pigment and the yellow pigment become the problems to be solved for developing a new type of pigment product when the red yeast rice also contains the citrinin.
Disclosure of Invention
The invention provides a monascus pigment product containing orange pigment and yellow pigment, which is obtained by extracting red yeast rice (containing other pigments) by using an organic solvent to enrich the orange pigment and the yellow pigment and remove or obviously reduce other pigments.
The invention provides a preparation method of a monascus pigment product containing orange pigment and yellow pigment, which is characterized in that red yeast rice (containing other pigments) is extracted by using an organic solvent, and the removal or the obvious reduction of other pigments can be realized while the orange pigment and the yellow pigment are enriched.
The invention also provides application of the monascus color product containing orange color and yellow color as a red coloring agent and a yellow coloring agent.
The invention provides a preparation method of a monascus pigment product containing red pigment, which is characterized in that red yeast rice (containing other pigments) is extracted by using an organic solvent, and the removal or the obvious reduction of other pigments can be realized while the red pigment is enriched.
The invention provides a method for preparing monascus pigment products containing orange pigments or yellow pigments, which is characterized in that red yeast rice (containing other pigments) is extracted by using an organic solvent, and the removal or the obvious reduction of other pigments can be realized while the orange pigments or the yellow pigments are enriched.
The monascus pigment product containing the orange pigment and the yellow pigment is obtained by extracting a fermentation product containing the orange pigment and the yellow pigment by using an organic solvent to obtain an extraction product and enriching the orange pigment and the yellow pigment from the extraction product, wherein the orange pigment is one or more of orange pigment O1 and O2, the yellow pigment is one or more of yellow pigment Y1 and Y2, and the fermentation product is monascus rice.
In the scheme of the application, the monascus pigment product containing the orange pigment and the yellow pigment is obtained by enriching the orange pigment and the yellow pigment in the extracted product and simultaneously removing or obviously reducing other pigments in the extracted product, wherein the other pigments comprise one or more of red pigment and citrinin, and the red pigment is one or more of red pigment R1 and red pigment R2. The scheme in the application is suitable for the red yeast rice containing citrinin and the red yeast rice not containing citrinin. The red yeast rice which does not contain citrinin and contains red pigment can be enriched with O1, O2, Y1 and Y2, and the red pigment can be obviously reduced, so that a yellow-tone pigment product containing 4 pigment mixtures of O1, O2, Y1 and Y2 is obtained. For red yeast rice containing citrinin and haematochrome, the scheme of the application can enrich O1, O2, Y1 and Y2, and meanwhile, the haematochrome and the citrinin are obviously reduced. One of the final goals of the protocol of the present application is to obtain monascus color products with yellow hues containing orange colors O1, O2, Y1 and Y2.
Further, the organic solvent contains one or more of dichloromethane, ethanol, petroleum ether, ethyl acetate, lower alcohols other than ethanol, chloroform, acetonitrile, formic acid, acetic acid, and phosphoric acid.
In the scheme of the invention, after the organic solvent extraction, the extraction product is refined by silica gel column chromatography to enrich the orange pigment and the yellow pigment.
The process of refining the extraction product by silica gel column chromatography to enrich the orange pigment and the yellow pigment comprises eluting the silica gel column by using an elution solvent to collect the orange pigment and the yellow pigment and simultaneously remove other pigments, wherein the other pigments comprise one or more of haematochrome and citrinin, the haematochrome is one or more of haematochrome R1 and R2, the elution solvent is a mixture of dichloromethane and methanol, and the ratio of the dichloromethane to the methanol is 50: 0-1 (v/v), or the elution solvent is a mixture of trichloromethane and methanol, and the ratio of trichloromethane to methanol is 50:0 to 1 (v/v). Further, methanol may be replaced with other lower alcohols.
In the scheme of the application, whether each pigment (for example, mixed pigment bands of orange pigments O1 and O2 and yellow pigments Y1 and Y2) is eluted or not can be observed visually in the elution process; or using elution collection criteria conventional in the art, as would be achievable by one skilled in the art.
The invention also provides a preparation method of the monascus pigment product containing the orange pigment and the yellow pigment, the method comprises the steps of extracting a fermentation product containing the orange pigment and the yellow pigment by using an organic solvent to obtain an extraction product, and enriching the orange pigment and the yellow pigment from the extraction product to obtain the monascus pigment product, wherein the orange pigment is one or more of orange pigment O1 and O2, the yellow pigment is one or more of yellow pigment Y1 and Y2, and the fermentation product is red yeast rice.
Further, the enrichment of orange pigment and yellow pigment from the extraction product comprises: and enriching the orange pigment and the yellow pigment in the extraction product, and simultaneously removing or obviously reducing other pigments in the extraction product, wherein the other pigments comprise one or more of red pigment and citrinin, and the red pigment is one or more of red pigment R1 and R2.
In one embodiment of the present invention, the organic solvent contains one or more of dichloromethane, ethanol, petroleum ether, ethyl acetate, lower alcohols other than ethanol, chloroform, acetonitrile, formic acid, acetic acid, and phosphoric acid.
In one embodiment of the present invention, the organic solvent is a complex solvent of petroleum ether and ethyl acetate, or petroleum ether and dichloromethane. Further, in the composite solvent, the proportion of the petroleum ether is 50-85 v/v%. Further, the proportion of petroleum ether is 50% -75v/v%. In an aspect of the invention, the petroleum ether boiling range may be 30-60 ℃ or 60-90 ℃. Preferably the petroleum ether boiling range is from 60 to 90 ℃.
The organic solvent may be a combination solvent of petroleum ether, dichloromethane and formic acid. Further, in the combined solvent of petroleum ether, dichloromethane and formic acid, the ratio of petroleum ether to dichloromethane is 1-2:1 (v/v), and the content of formic acid is 0.1-0.3v/v%.
The organic solvent may be a combined solvent of ethanol and formic acid. Further, in the combined solvent of the ethanol and the formic acid, the content of the formic acid is 0.1-0.3v/v%, and the ethanol is 90-100% ethanol.
Further, in the process of extracting the red yeast rice by using the organic solvent, the ratio of the red yeast rice to the organic solvent is 1-50 g/mL.
The concentration of the organic solvent, for example, ethanol may be 80% or more ethanol; the dichloromethane concentration was 100%. Further, the volume ratio of dichloromethane in the combined solvent may be 50% or less.
Furthermore, the organic solvent extraction can be performed by standing extraction, or the organic solvent extraction also comprises ultrasonic-assisted extraction for 5-30min while adding the organic solvent to extract the red yeast rice, so as to obtain an ultrasonic-assisted extracting solution. Further, the frequency of the ultrasound may be, for example, 200W to 800W.
Further, the method further comprises the step of refining the supernatant of the ultrasonic auxiliary extracting solution by silica gel column chromatography. The supernatant can be obtained, for example, by centrifuging the ultrasound-assisted extraction solution at 3500r/min for 10min and collecting the supernatant.
In the preparation method of the monascus color product containing orange color and yellow color, the silica gel column chromatography refining comprises the following steps:
1) Mixing the supernatant with silica gel at a ratio of 1-2 g silica gel/1 g dry extract (the content of the dry extract can be obtained, for example, by taking 10ml of the supernatant, drying by solvent evaporation, and weighing the obtained dry extract) to obtain a mixture 1;
2) The mixture 1 was loaded on a silica gel column, and the ratio (w/w) of silica gel for separation to loaded silica gel was controlled to 5 to 30, and the mixture was purified by a column chromatography method using dichloromethane: methanol =50: eluting 0-1 (v/v) to obtain monascus pigment solution rich in O1, O2, Y1 and Y2;
3) And (3) drying the monascus pigment solution rich in O1, O2, Y1 and Y2 by rotary evaporation to obtain a monascus pigment product rich in O1, O2, Y1 and Y2 and with the content of the red pigment obviously reduced or without the red pigment.
In the purification process, the silica gel may have a particle size of 200 to 500 mesh, or 300 to 400 mesh, for example. Furthermore, the particle size of the silica gel for separation and the silica gel for loading may be the same or different, for example, the particle size of the silica gel for loading may be 100 to 200 mesh, and the particle size of the silica gel for separation may be 200 to 500 mesh.
Further, the conditions for the rotary evaporation drying may be, for example, 30 to 50 ℃.
The invention also provides the application of monascus pigment products containing orange pigment and yellow pigment (namely products containing products of orange pigments O1 and O2 and yellow pigments Y1 and Y2) as red coloring agents and yellow coloring agents.
The monascus pigment product containing the orange pigment and the yellow pigment is used as a yellow colorant under an acidic condition and is used as a red colorant under an alkaline condition.
The invention provides a preparation method of a monascus pigment product containing red pigment (namely a red pigment product containing monascus red pigments R1 and R2), which comprises the following steps:
1) Extracting a fermentation product containing red pigment by using an organic solvent to obtain an extraction product, and enriching the red pigment from the extraction product, wherein the red pigment comprises one or more of red pigments R1 and R2, and the fermentation product is red yeast rice;
2) The enriching of the red pigment from the extraction product comprises: refining the extracted product obtained in the step 1) by using a silica gel column chromatography to enrich the red pigment in the extracted product and simultaneously remove or obviously reduce other pigments in the extracted product, wherein the other pigments comprise one or more of orange pigment, yellow pigment and citrinin, the orange pigment is one or more of orange pigment O1 and O2, and the yellow pigment is one or more of yellow pigment Y1 and Y2.
In the preparation method for preparing the monascus pigment product containing the haematochrome, the silica gel column chromatography refining comprises the following steps:
1) Mixing the supernatant with silica gel at a ratio of 1-2 g silica gel/1 g dry extract (the content of the dry extract can be obtained, for example, by taking 10ml of the supernatant, drying by solvent evaporation, and weighing the obtained dry extract) to obtain a mixture 1;
2) The mixture 1 was loaded on a silica gel column, and the ratio (w/w) of silica gel for separation to loaded silica gel was controlled to 5 to 30, and the mixture was purified by a column chromatography method using dichloromethane: methanol =50: eluting the monascus pigment solution rich in O1, O2, Y1 and Y2 by 0-1 (v/v), and then eluting the silica gel column by using anhydrous methanol to obtain the monascus pigment solution rich in R1 and R2;
3) And (3) drying the monascus pigment solution rich in R1 and R2 by rotary evaporation.
The application also provides a preparation method of the monascus pigment product containing orange pigment or yellow pigment, which comprises the following steps:
1) Extracting a fermentation product containing orange pigment and yellow pigment by using an organic solvent to obtain an extraction product, enriching the orange pigment and the yellow pigment from the extraction product, wherein the orange pigment is one or more of orange pigment O1 and O2, the yellow pigment is one or more of yellow pigment Y1 and Y2, and the fermentation product is red yeast rice,
2) Said enriching orange and yellow pigments from said extraction product comprises: refining the extraction product obtained in the step 1) by using silica gel column chromatography so as to enrich the orange pigment and the yellow pigment in the extraction product and simultaneously remove or obviously reduce other pigments in the extraction product, wherein the other pigments comprise one or more of haematochrome and citrinin, and the haematochrome is one or more of haematochrome R1 and R2;
3) And respectively purifying one or more of the orange pigments O1 and O2 or one or more of the yellow pigments Y1 and Y2 from the enriched orange pigments and yellow pigments by preparative liquid chromatography.
In the preparation method for preparing the monascus pigment product containing the orange pigment or the yellow pigment, the silica gel column chromatography refining method has the same steps as the silica gel column chromatography refining method in the preparation method for preparing the monascus pigment product containing the orange pigment and the yellow pigment.
The scheme of the invention has the following advantages:
1) The method for preparing the monascus pigment product is suitable for the monascus rice containing citrinin and not containing citrinin, can enrich O1, O2, Y1 and Y2 for the monascus rice containing no citrinin, can realize the obvious reduction of the red pigment, and obtains the monascus pigment product containing orange pigments O1, O2, Y1 and Y2 and having yellow hue.
2) Aiming at red yeast rice containing citrinin, the enrichment of O1, O2, Y1 and Y2 is realized, the contents of citrinin and haematochrome are obviously reduced, the pollution problem of the citrinin which is a monascus fermentation product is economically and effectively solved, and the red yeast strains which have high O1, O2, Y1 and Y2 yield and are accompanied with high citrinin content can also be safely applied to food additives and other coloring fields (such as hair dyeing, printing and the like);
3) Compared with the method of extracting by using 70% ethanol in national standard, the method for preparing the monascus pigment product has the advantages that even the extracted product is rich in O1, O2, Y1 and Y2, the extraction yield is not high, and because the red pigment is also extracted simultaneously, the color tone of the final product can be slightly red or the yellow color tone is not pure due to the interference of the red pigment. In the scheme of the application, the method for extracting the enriched O1, O2, Y1 and Y2 by adopting the independent dichloromethane, the independent 90-100% ethanol, the independent ethyl acetate, the independent trichloromethane or the combined solvent has higher yield than the method for extracting the enriched O1, O2, Y1 and Y2 by adopting the national standard 70% ethanol. The petroleum ether is added into the combined solvent to replace partial dichloromethane or ethyl acetate, so that the effect of removing haematochrome and citrinin is obviously improved compared with the effect of extracting single dichloromethane, single trichloromethane or ethyl acetate, and the extraction cost can be reduced.
4) In the scheme, the organic solvent extraction product is refined by further utilizing silica gel column chromatography after the organic solvent column chromatography is adopted, compared with the single organic solvent extraction, the haematochrome can be completely removed, and if the red yeast rice contains citrinin, the citrinin can be correspondingly removed.
5) The monascus pigment product provided by the invention is used as a yellow colorant under an acidic condition and is used as a red colorant under an alkaline condition.
6) The monascus pigment product provided by the invention is used as a red colorant for coloring nitrogen-containing foods represented by free amino acid, basic dyes and paints; as yellow coloring agents for coloring acid dyes, paints, carbonated beverages, candies, plastic containers, packaging materials, and the like; the monascus pigment product can also be used as a yellow colorant for food coloring after being embedded by a proper wall material (containing no nitrogen or not reacting with a nitrogen-containing compound); can be used for coloring in cosmetic (hair dyeing, nail dyeing, etc.), printing and dyeing, and paint industries.
Drawings
FIG. 1 shows a high performance liquid chromatogram of red yeast rice pigment components containing monascus red pigments R1 and R2 (1 and 2), yellow pigments Y1 and Y2 (3 and 4) and orange pigments O1 and O2 (5 and 6);
FIG. 2 shows the spectra and mass spectra of the monascus red pigments R1, R2 (1, 2), the yellow pigments Y1, Y2 (3, 4) and the orange pigments O1, O2 (5, 6).
Detailed Description
In the scheme of the invention, the red yeast rice containing the monascus orange pigments O1 and O2, the yellow pigments Y1 and Y2 and the red pigments R1 and R2 is commercially available red yeast rice containing the monascus orange pigments O1 and O2, the yellow pigments Y1 and Y2 and the red pigments R1 and R2, for example, a red yeast rice product purchased from gutian county in Fujian province, which can be realized by using a conventional screening means for a person skilled in the art.
Example 1 screening of fermentation products rich in Monascus aurantium, yellow and red pigments
Red yeast rice containing monascus orange pigment, yellow pigment and red pigment is screened from commercially available red yeast rice products (red yeast rice purchased from the county of Fujian province) by adopting high performance liquid chromatography and mass spectrometry.
Crushing 5g of a commercial red yeast rice product, transferring the red yeast rice product into a conical flask, adding 70% ethanol solution according to the ratio of the red yeast rice product to ethanol 1 to 10 g/mL, carrying out ultrasonic assisted extraction for 5 to 30min, centrifuging the extract at 3500r/min for 10min, taking supernatant, filtering the supernatant through a 0.22-micron organic filter, and carrying out HPLC detection.
HPLC detection conditions are as follows: column Cosmosil Packed Column (4.6 μm,4.6ID × 250 mm), mobile phase consisting of a phase water (0.1% formic acid) and B phase acetonitrile, gradient elution: phase B (0-12min, 60-90%, 12-25min, 90%,27-30min: 410nm, column temperature: at 25 ℃.
And (3) detecting the accurate molecular weight of the pigment by adopting an LCMS-IT-TOF mass spectrometer.
HPLC combined with LCMS-IT-TOF detection shows that: the molecular weight and the characteristic spectral absorption peak of the 6 pigments meet the relevant literature records: red pigment R1: (1; yellow pigment Y1 (3); orange pigment O1 (5.
FIG. 1 shows a high performance liquid chromatogram of red yeast rice containing monascus red pigments R1 and R2 (1 and 2), yellow pigments Y1 and Y2 (3 and 4), and orange pigments O1 and O2 (5 and 6). FIG. 2 shows the spectrograms and mass spectrograms of the monascus red pigments R1, R2 (1, 2), the yellow pigments Y1, Y2 (3, 4) and the orange pigments O1, O2 (5, 6).
Of course, the person skilled in the art can also screen the fermentation product containing orange pigment and yellow pigment, or the fermentation product containing red pigment, as required, and this can be achieved by the above method.
EXAMPLE 2 preparation of Monascus pigment products containing orange and yellow pigments in accordance with the present application
In this example, the red yeast rice screened in example 1 may be used, or commercially available red yeast rice containing monascus orange pigments O1 and O2, yellow pigments Y1 and Y2, and red pigments R1 and R2 may be used.
1) Organic solvent extraction: crushing 5g of red yeast rice containing red yeast orange pigments O1 and O2, yellow pigments Y1 and Y2 and red pigments R1 and R2, transferring the red yeast rice into a conical flask, adding 100% dichloromethane solution according to the proportion of the red yeast rice to dichloromethane 1 to 20g/mL, carrying out ultrasonic assisted extraction for 5 to 30min at an ultrasonic frequency of 200w, centrifuging the extracting solution at 3500R/min for 10min, and taking the supernatant into a new centrifugal tube;
2) Refining by silica gel column chromatography: the silica gel for separation and the silica gel for loading may be those commercially available from Michelin corporation, for example, column chromatography silica gel having a size of 300-400 mesh, available from C820914. The chromatography column is a Flash chromatography device (Flash chromatography) which can be manually pressurized. One skilled in the art can use a medium pressure chromatographic separation device instead of a flash column chromatographic device as desired.
Volatilizing 10ml of the supernatant obtained in the step 1) by using a solvent, and weighing the obtained dry matter to obtain the approximate content of the dry matter in each ml of the supernatant; and uniformly mixing the obtained supernatant with silica gel according to the proportion of 1-2 g of silica gel per 1 g of dry matter, volatilizing the solvent, loading into a silica gel column, controlling the ratio (w/w) of the silica gel for separation to the loaded silica gel to be about 5-30, and reacting the mixture with dichloromethane: methanol =50: and (v/v) eluting to obtain a monascus pigment solution rich in monascus orange pigments O1 and O2 and yellow pigments Y1 and Y2, and performing rotary evaporation and drying to obtain a monascus pigment product rich in monascus orange pigments O1 and O2 and yellow pigments Y1 and Y2, free of haematochrome and possibly citrinin.
0.1 g of the obtained monascus pigment product was taken and the pigment content was detected by the HPLC method of example 1.
Example 3 preparation of Monascus pigment products containing orange and yellow pigments of the present application
1) Organic solvent extraction: crushing 5g of red yeast rice containing monascus orange pigments O1 and O2, yellow pigments Y1 and Y2 and red pigments R1 and R2, transferring the crushed red yeast rice into a conical flask, and mixing the red yeast rice and an organic solvent according to a material-liquid ratio of 1-30 g/mL, wherein the organic solvent is: petroleum ether: ethyl acetate =1-5:1 (v/v) of the solvent composition, performing ultrasonic-assisted extraction for 5-30min, centrifuging at an ultrasonic frequency of 300w and a ultrasonic frequency of 3500r/min for 10min, and taking the supernatant into a new centrifuge tube.
The contents of the centrifuge tube were measured by HPLC method of example 1.
EXAMPLE 4 preparation of Monascus pigment products containing orange and yellow pigments according to the present application
1) Organic solvent extraction: crushing 5g of red yeast rice containing monascus orange pigments O1 and O2, yellow pigments Y1 and Y2 and red pigments R1 and R2, transferring the crushed red yeast rice into a conical flask, and mixing the red yeast rice and an organic solvent according to a material-liquid ratio of 1-30 g/mL, wherein the organic solvent is petroleum ether: dichloromethane =1-3:1 (v/v) of the solvent composition, performing ultrasonic-assisted extraction for 5-30min, centrifuging at an ultrasonic frequency of 300w and a ultrasonic frequency of 3500r/min for 10min, and taking the supernatant into a new centrifuge tube.
The contents of the centrifuge tube were measured by HPLC method of example 1.
EXAMPLE 5 preparation of Monascus pigment products containing orange and yellow pigments according to the present application
1) Organic solvent extraction: crushing 5g of red yeast rice containing monascus orange pigments O1 and O2, yellow pigments Y1 and Y2 and red pigments R1 and R2, transferring the crushed red yeast rice into a conical flask, and mixing the red yeast rice and an organic solvent according to a material-liquid ratio of 1-30 g/mL, wherein the organic solvent is petroleum ether: dichloromethane =1-2:1 (v/v), adding a composite solvent of 0.1-0.3v/v% formic acid, performing ultrasonic-assisted extraction for 5-30min, performing centrifugation at an ultrasonic frequency of 300w and a ultrasonic frequency of 3500r/min for 10min, and taking the supernatant into a new centrifuge tube.
The contents of the centrifuge tube were measured by HPLC method of example 1.
EXAMPLE 6 preparation of Monascus pigment products containing orange and yellow pigments in accordance with the present application
1) Organic solvent extraction: crushing 5g of red yeast rice containing monascus orange pigments O1 and O2, yellow pigments Y1 and Y2 and red pigments R1 and R2, transferring the red yeast rice into a conical flask, adding 90-100% ethanol according to the proportion of the red yeast rice to the ethanol 1 being 5-15 g/mL, adding 0.3-0.5v/v% formic acid, carrying out ultrasonic-assisted extraction for 5-30min at the ultrasonic frequency of 300w, then centrifuging the extracting solution at 3500R/min for 10min, and taking the supernatant into a new centrifugal tube.
The contents of the substances in the centrifuge tube were measured by HPLC method of example 1.
EXAMPLE 7 preparation of Monascus pigment products containing orange and yellow pigments, or Monascus pigment products containing red pigments, of the present application
1) Organic solvent extraction: crushing 5g of red yeast rice containing red yeast orange pigments O1 and O2 and yellow pigments Y1 and Y2, transferring the red yeast rice into a conical flask, adding 70% ethanol solution according to the proportion of 5-15 g/mL of red yeast rice and ethanol 1, performing ultrasonic assisted extraction for 5-30min at the ultrasonic frequency of 300w, centrifuging the extracting solution at 3500r/min for 10min, and taking the supernatant into a new centrifugal tube.
2) Refining by silica gel column chromatography: refining the concentrated and dried extract by silica gel column chromatography, which comprises dissolving the concentrated and dried extract in anhydrous ethanol, and mixing with silica gel at a weight ratio of 1:1, volatilizing the solvent, loading into a silica gel column, controlling the ratio (w/w) of silica gel for separation to loaded silica gel to be about 5-30, and mixing with dichloromethane to methanol =50: eluting 0-1 (v/v) to obtain a monascus pigment solution component 1 rich in monascus orange pigments O1 and O2 and yellow pigments Y1 and Y2, and then eluting the red pigment remained in the chromatographic column by using anhydrous methanol to obtain a red pigment solution component 2.
The component 1 and the component 2 are respectively rotated and evaporated, after drying, the pigment is measured by the HPLC method of the embodiment 1, the citrinin is measured by the GB5009.222-2016 detection method, and the monascus pigment product 2 which is rich in monascus orange pigments O1 and O2 and yellow pigments Y1 and Y2, does not contain the monascus pigment 1 and the citrinin, and has 280mg in total and significantly reduced (compared with the comparative example 1) in total is 660mg in total is obtained.
This example illustrates that silica gel column chromatography can efficiently separate and prepare monascus pigment product 1 and monascus red pigment product 2 from a monascus pigment mixture, wherein the yellow hue is removed from the red pigment.
EXAMPLE 8 preparation of Monascus pigment products containing orange or yellow pigments
1) Organic solvent extraction, as per example 2;
2) Purification by silica gel column chromatography was carried out as in example 2;
3) And respectively purifying one or more of the orange pigments O1 and O2 or one or more of the yellow pigments Y1 and Y2 from the enriched orange pigments and yellow pigments by preparative liquid chromatography.
The step 3) specifically comprises the following steps: dissolving 1 g of the monascus pigment product obtained in step 2) of the embodiment 2 and enriched by column chromatography in 15ml of chromatographic acetonitrile, and simultaneously separating and purifying O1, O2, Y1 and Y2 by preparative liquid chromatography. The mobile phase consists of phase A water (0.1% formic acid) and phase B (80% -100% acetonitrile), isocratic elution or gradient elution is carried out at the flow rate of 10ml/min, and an ultraviolet detector is used for detecting the wavelength: 410nm. The purified pigment was checked for purity by HPLC as in example 1.
Comparative example 1 preparation of Monascus pigment product
1) Organic solvent extraction: 5g of red yeast rice containing monascus orange pigments O1 and O2 and yellow pigments Y1 and Y2 are crushed and transferred into a conical flask, 70% ethanol solution is added according to the proportion of 5-15 g/mL of red yeast rice and ethanol 1 for ultrasonic-assisted extraction for 5-30min, then the extract is centrifuged at 3500r/min for 10min, the supernatant is taken and put into a new centrifugal tube, and the pigment content is detected by the HPLC method of example 1.
Comparative example 2 preparation of Monascus pigment product
1) Organic solvent extraction: crushing 5g of red yeast rice containing O1 and O2, transferring the red yeast rice into a conical flask, adding 100% dichloromethane solution according to the ratio of the red yeast rice to dichloromethane 1 to 10-20g/mL, extracting for 5-30min with the assistance of ultrasonic waves, centrifuging the extracting solution for 10min at 3500r/min, taking the supernatant into a new centrifugal tube, and detecting the pigment content in the monascus pigment product by the HPLC method of example 1.
Comparative example 3 preparation of Monascus pigment product
1) Organic solvent extraction: crushing 5g of red yeast rice containing monascus orange pigments O1 and O2 and yellow pigments Y1 and Y2, transferring the red yeast rice into a conical flask, adding 100% ethyl acetate solution according to the proportion of the red yeast rice to the ethyl acetate 1 to 20g/mL, carrying out ultrasonic-assisted extraction for 5-30min, then centrifuging the extracting solution at 3500r/min for 10min, taking the supernatant into a new centrifugal tube, and detecting the pigment content in the pigment product by the HPLC method of example 1.
Comparative example 4 preparation of Monascus pigment product
1) Organic solvent extraction: crushing 5g of red yeast rice containing monascus orange pigments O1 and O2 and yellow pigments Y1 and Y2, transferring the red yeast rice into a conical flask, adding a petroleum ether solution according to the ratio of the red yeast rice to the petroleum ether 1 being 10-20g/mL, carrying out ultrasonic-assisted extraction for 5-30min, then centrifuging the extracting solution at 3500r/min for 10min, taking the supernatant into a new centrifugal tube, and detecting the pigment content in the red yeast rice by HPLC.
Results of the experiment
Comparison of extraction schemes for refining organic solvent extract products by silica gel column chromatography
1. The monascus pigment products prepared in the examples were subjected to pigment content measurement according to the following method, and the results are shown in table 1.
The same amount of the extract liquid was extracted from each example, and after evaporating the solvent, the extract liquid was diluted 50 times with acetonitrile by chromatography, and the pigment content was measured by using the HPLC detection conditions of example 1.
2. The same amount of extract liquid in each example is respectively absorbed, after the solvent is volatilized, acetonitrile is redissolved by the same volume chromatography, the citrinin is determined by referring to the GB5009.222-2016 detection method, and the result is listed in the table 1.
TABLE 1
Figure BDA0002856142090000121
Figure BDA0002856142090000131
As can be seen from the results in table 1, the present application adopts a single organic solvent extraction different from the prior art, adopts a column chromatography step, and adopts a complex solvent extraction, all obtaining significant effects:
1) The application has the following independent organic solvent extraction effects: compared with comparative example 1 (a single 70% ethanol extraction method in the prior art), single 90-100% ethanol (example 6), single dichloromethane (comparative example 2) and single ethyl acetate (comparative example 3), the monascus pigment products containing the orange pigment and the yellow pigment are remarkably improved, and the contents of citrinin and haematochrome are remarkably reduced.
2) The method adopts the column chromatography step effect: as can be seen from comparison of comparative example 1 with products 1 and 2 of example 7, the addition of a column chromatography step compared to comparative example 1 (prior art 70% ethanol extraction alone process) can enrich the desired pigment on the one hand and significantly reduce or remove other pigments than the desired enriched pigment on the other hand. For the preparation of monascus pigment products containing orange pigment and yellow pigment, the single organic solvent extraction (example 6, comparative examples 2-3) can achieve at least 80% reduction of citrinin (example 6 has the minimum reduction of about 84%), but complete removal of both the red pigment and citrinin is achieved in example 2 and complete removal of both the red pigment and citrinin is achieved in example 7, product 1. Aiming at the preparation of the monascus pigment product containing the red pigment (product 2 in example 7), compared with the comparative example 1 (the prior art adopts a single 70% ethanol extraction method), the yield of the red pigment is greatly improved after column chromatography is added, orange pigment and yellow pigment are completely removed, and the content of citrinin is obviously reduced.
3) This application adopts compound solvent extraction effect: compared with the comparative example 1 (the prior art single 70% ethanol extraction method), the single petroleum ether (the comparative example 4) is used for extracting monascus pigment products containing orange pigments and yellow pigments, although the extracted products do not contain the red pigments and citrinin, the extraction rates of the orange pigments and the yellow pigments are lower, the petroleum ether and dichloromethane or ethyl acetate are combined to be used as a composite solvent for extraction (the examples 3-4), the extraction rates of the orange pigments and the yellow pigments can be obviously improved, and the red pigments and the citrinin are obviously reduced compared with the comparative example 1 (the prior art single 70% ethanol extraction method). When petroleum ether, dichloromethane and formic acid are used as a composite solvent (example 5) for extraction, the extraction rates of orange pigment and yellow pigment are remarkably improved, the citrinin content is remarkably reduced compared with that of comparative example 1, and the red pigment is completely removed.
3. The monascus pigment product provided by the application is used for detecting color tone under different pH conditions
Taking a proper amount of the monascus pigment product prepared in example 2, dissolving the monascus pigment product in 70% ethanol, and using a cunica minolta CM-3600D spectrocolorimeter and a CIEL * a * b * (CIELAB) color model, in lightness L * And chromaticity coordinate a * 、b * To represent the position of the colors in the color space, and to numerically describe the various colors visible to the human eye. L denotes the brightness of the color (L × =0 denotes black, L × =100 denotes white), a positive values indicate red, negative values indicate green; positive values indicate yellow and negative values indicate blue.
Table 2 monascus color product provided herein was evaluated for hue at different pH
Figure BDA0002856142090000141
Under the alkaline environment of pH 9.0, 11.0 and 13.0, the b value (yellowness) of the monascus pigment is obviously reduced, the hue angle is reduced to be a negative value, two maximum absorption peaks exist at 400nm and 520nm, and the hue is purple red. Under the acidic environment of pH1, 2, 3 and 4, the b value (yellowness) of the monascus pigment is obviously increased, the hue angle reaches more than 70, the maximum absorption peak is at 470nm, and the hue is bright yellow. The above data illustrate that the monascus pigment products provided herein can be used as red and yellow colorants in the food and non-food coloring applications, respectively, under different pH environments.
4. Compared with commercial monascus color added in meat products, the monascus color product provided by the application has color tone and light stability after being colored
The monascus pigment product (A) prepared in the embodiment 2 of the application is dissolved in 70% ethanol, and an appropriate amount of the monascus pigment (A) and a commercially available monascus pigment (B) are respectively added to every 100 g of minced pork, and are respectively marked as A after being fully and uniformly mixed 0 And B 0 Measuring color tone, standing at room temperature for 30 minutes, respectively marking as A 1 And B 1 Measuring the color tone, and respectively marking as A after 12 hours of illumination 2 And B 2 And measuring the color tone. Color evaluation was performed using a Konika-Mentada CM-3600D spectrocolorimeter, and the results are shown in Table 3: the monascus pigment product prepared in example 2 was added to the minced pork a 0 Has an initial red (a) of 10.78, and after 30 minutes at room temperature, A 1 The redness (a) rapidly rises to 16.54, and the color of the meat paste is changed from slight yellow to bright red, which is similar to the color of the meat paste added with the monascus red pigment. After 12 hours of illumination A 2 And B 2 The redness and the color difference angle of the meat emulsion are respectively 7.33,58.25 and 5.4, 69.49, which shows that the red tone and the light stability of the meat emulsion added with the monascus pigment A are superior to those of the meat emulsion added with the commercial monascus red pigment B.
Therefore, the monascus pigment product (a) can be used as a red colorant for meat products instead of the commercially available monascus red pigment.
TABLE 3 Monascus pigment product (A) and commercially available Monascus pigment (B) added to meat products for comparison with Red Monascus coloring and color tone light stability
Figure BDA0002856142090000151
5. Color tone comparison of monascus pigment products provided herein with commercial monascus red colored white fermented bean curd
Fully dissolving the monascus pigment product A and commercial monascus red (namely monascus pigment product B) provided by the application with 75% ethanol respectively, properly diluting, adding 50 mu L of the diluted monascus red into 1 g of fermented bean curd, fully and uniformly mixing, placing the fermented bean curd before and after the same amount of coloring on a cover glass, and respectively collecting the fermented bean curd L before and after the coloring by a Coriolis CM-700d spectrocolorimeter * a * b * The results are shown in Table 4: the white rot cream color angle is 83.53, and the white rot cream color is light yellow; the value of a is obviously increased, the value of b is obviously reduced, the hue angle is reduced to 17.36, and the product is dark red (the color after the product reacts with amino acid in food). Similar to the color tone of the commercial red yeast red coloring white fermented bean curd.
TABLE 4 comparison of the color tone of Monascus pigment product A and commercially available Monascus red pigment (B) added to white curd
Figure BDA0002856142090000161
6. The monascus pigments O1, O2, Y1, Y2 prepared in example 8 (purity greater than 90% by HPLC) were dissolved in 70% ethanol, respectively, the pH of the solution was adjusted to 1-14, and L was measured by cuneatam CM-700d spectrocolorimeter * a * b * The results of the hue change of O1 and O2 under different pH environments are shown in Table 5: under the acidic and weak alkaline environment with pH of 1-7, the monascus pigment b value (yellowness) gradually decreases, the hue angle reaches above 70, and the hue is bright yellow. The color tone is purple red. Under the alkaline environment of pH 8-14, the b value (yellowness) of monascus pigment is obviously reduced, the hue angle is gradually reduced to a negative value, and the color is changed into purpleRed in color. The results of the hue change of Y1 and Y2 under different pH environments are shown in Table 6: y1 and Y2 are yellow green, and the color tone does not change obviously under different pH environments. This example illustrates that the major contributors to the hue and hue change in different pH environments of the mixed extract of monascus pigment rich in O1, O2, Y1, Y2 are orange pigments O1, O2.
TABLE 5 hue change of O1 and O2 under different pH environments
Figure BDA0002856142090000162
TABLE 6 hue change of Y1 and Y2 under different pH environments
Figure BDA0002856142090000171

Claims (3)

1. The application of monascus pigment products containing orange pigments and yellow pigments as red coloring agents and yellow coloring agents is characterized in that the monascus pigment products are obtained by extracting fermentation products containing the orange pigments and the yellow pigments by using an organic solvent to obtain extraction products, and the extraction products are enriched in the orange pigments and the yellow pigments, the orange pigments are one or more of orange pigments O1 and O2, the yellow pigments are one or more of yellow pigments Y1 and Y2, and the fermentation products are red yeast rice;
the monascus pigment product is obtained by enriching the orange pigment and the yellow pigment in the extracted product and removing other pigments in the extracted product, wherein the other pigments comprise haematochrome and citrinin, and the haematochrome is one or more of haematochrome R1 and R2;
the organic solvent is dichloromethane or 70% ethanol;
after the organic solvent extraction, refining the extraction product by using silica gel column chromatography to enrich the orange pigment and the yellow pigment;
the process of refining the extraction product by silica gel column chromatography to enrich the orange pigment and the yellow pigment comprises eluting the silica gel column by an elution solvent to collect the orange pigment and the yellow pigment and remove other pigments simultaneously, wherein the other pigments comprise haematochrome and citrinin, the haematochrome is one or more of haematochrome R1 and R2,
the elution solvent is a mixture of dichloromethane and methanol, and the ratio of dichloromethane to methanol is 50:0 to 1 (v/v).
2. The use according to claim 1, wherein said monascus color product containing orange and yellow pigments acts as a yellow colorant under acidic conditions and as a red colorant under alkaline conditions.
3. A method for preparing a monascus pigment product containing orange pigment and yellow pigment, the method comprising extracting a fermentation product containing orange pigment and yellow pigment with an organic solvent to obtain an extraction product, and enriching orange pigment and yellow pigment from the extraction product to obtain the monascus pigment product, wherein the orange pigment is one or more of orange pigment O1 and O2, the yellow pigment is one or more of yellow pigment Y1 and Y2, and the fermentation product is red yeast rice;
enriching orange pigment and yellow pigment from the extraction product, including enriching the orange pigment and yellow pigment in the extraction product, and removing other pigments in the extraction product at the same time, wherein the other pigments include haematochrome and citrinin, and the haematochrome is one or more of haematochrome R1 and R2;
the organic solvent is dichloromethane or 70% ethanol;
after the organic solvent extraction, the step of refining the extraction product by utilizing silica gel column chromatography to enrich the orange pigment and the yellow pigment is also included;
the process of refining the extraction product by silica gel column chromatography to enrich the orange pigment and the yellow pigment comprises eluting the silica gel column by an eluting solvent to collect the orange pigment and the yellow pigment and remove other pigments simultaneously, wherein the other pigments comprise haematochrome and citrinin, the haematochrome is one or more of haematochrome R1 and R2,
the elution solvent is a mixture of dichloromethane and methanol, and the ratio of dichloromethane to methanol is 50:0 to 1 (v/v).
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