CN115428936A - Masking agent for improving bitter taste of food and preparation method and application thereof - Google Patents
Masking agent for improving bitter taste of food and preparation method and application thereof Download PDFInfo
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- CN115428936A CN115428936A CN202210986000.8A CN202210986000A CN115428936A CN 115428936 A CN115428936 A CN 115428936A CN 202210986000 A CN202210986000 A CN 202210986000A CN 115428936 A CN115428936 A CN 115428936A
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- 235000019658 bitter taste Nutrition 0.000 title claims abstract description 46
- 235000013305 food Nutrition 0.000 title claims abstract description 39
- 230000000873 masking effect Effects 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 50
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 235000019606 astringent taste Nutrition 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000005119 centrifugation Methods 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- DLRVVLDZNNYCBX-CQHUIXDMSA-N alpha-D-Galp-(1->6)-alpha-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)O1 DLRVVLDZNNYCBX-CQHUIXDMSA-N 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 22
- 239000001116 FEMA 4028 Substances 0.000 claims description 17
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 17
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 17
- 229960004853 betadex Drugs 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 claims description 15
- 102000005840 alpha-Galactosidase Human genes 0.000 claims description 14
- 108010030291 alpha-Galactosidase Proteins 0.000 claims description 14
- VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 claims description 10
- 238000004108 freeze drying Methods 0.000 claims description 10
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims description 10
- 239000001685 glycyrrhizic acid Substances 0.000 claims description 10
- 229960004949 glycyrrhizic acid Drugs 0.000 claims description 10
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims description 10
- 235000019410 glycyrrhizin Nutrition 0.000 claims description 10
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 230000010355 oscillation Effects 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 239000006228 supernatant Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 239000007853 buffer solution Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000000105 evaporative light scattering detection Methods 0.000 claims description 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 5
- 230000000415 inactivating effect Effects 0.000 claims description 5
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical group O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000002953 preparative HPLC Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 239000000523 sample Substances 0.000 claims description 5
- 239000012488 sample solution Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 244000269722 Thea sinensis Species 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 229920001184 polypeptide Polymers 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 235000019640 taste Nutrition 0.000 description 4
- 235000006468 Thea sinensis Nutrition 0.000 description 3
- 235000020279 black tea Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 235000001727 glucose Nutrition 0.000 description 3
- 150000002304 glucoses Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 235000015205 orange juice Nutrition 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 235000013616 tea Nutrition 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 244000130270 Fagopyrum tataricum Species 0.000 description 1
- 235000014693 Fagopyrum tataricum Nutrition 0.000 description 1
- 102000002464 Galactosidases Human genes 0.000 description 1
- 108010093031 Galactosidases Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 description 1
- VHLJDTBGULNCGF-UHFFFAOYSA-N Limonin Natural products CC1(C)OC2CC(=O)OCC23C4CCC5(C)C(CC(=O)C6OC56C4(C)C(=O)CC13)c7cocc7 VHLJDTBGULNCGF-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 description 1
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 description 1
- 229940025878 hesperidin Drugs 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- KBDSLGBFQAGHBE-MSGMIQHVSA-N limonin Chemical compound C=1([C@H]2[C@]3(C)CC[C@H]4[C@@]([C@@]53O[C@@H]5C(=O)O2)(C)C(=O)C[C@@H]2[C@]34COC(=O)C[C@@H]3OC2(C)C)C=COC=1 KBDSLGBFQAGHBE-MSGMIQHVSA-N 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
Classifications
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention provides a masking agent for improving food bitterness and astringency, and a preparation method and application thereof, aiming at the problem that different products have different bitterness, a unique cave structure of multi-branched cyclodextrin is utilized to adsorb and embed bitter substances, so that the effect of improving the bitterness is achieved. The method for improving the bitter taste is simple and convenient to operate, can achieve the purpose of better removing the bitter taste without additionally adding a process, and has better application prospect in food.
Description
Technical Field
The invention belongs to the technical field of food development and utilization, and relates to a masking agent for improving food bitterness and astringency, and a preparation method and application thereof.
Background
The sense of taste is a sensation which food stimulates and produces the taste organochemical system in the oral cavity of a human, which provides sensory information extremely important to food, and is very important to food intake. The taste can be divided into five sensory forms of sweet, bitter, sour, salty and fresh. Bitterness is one of five basic tastes and may cause an aversive reaction. The bitter substances in the food are basically all naturally-occurring components, such as soybean polypeptide, limonin and hesperidin in orange juice, and catechin in tea, and have the functions of resisting oxidation and the like, but the bitter taste affects the taste of the product, and the intake of the food by part of people is limited.
For the removal of bitterness and astringency, there are examples of cyclodextrin used in the industry, and among the currently commercially available cyclodextrins, there are α -cyclodextrin containing 6 glucoses, β -cyclodextrin containing 7 glucoses, and γ -cyclodextrin containing 8 glucoses. The cyclodextrin can remove the bitter taste to a certain extent, however, a homogenizing process is usually added for embedding, the cyclic part of the cyclodextrin is small, only a small part of micromolecule bitter substances can be embedded, and the macromolecular bitter substances are difficult to embed.
Disclosure of Invention
Aiming at the technical problems, the invention provides a masking agent for improving the bitter taste of food and a preparation method and application thereof.
The specific technical scheme is as follows:
a masking agent for improving food bitterness comprises multi-branched cyclodextrin.
The preparation method of the masking agent for improving the bitter taste of the food comprises the following steps:
s1, mixing dry powder beta-cyclodextrin and 6-O-alpha-D-galactopyranosyl-D-glucose in a container, adding glycyrrhizic acid buffer solution, and stirring to dissolve the beta-cyclodextrin and the 6-O-alpha-D-galactopyranosyl-D-glucose;
s2, dripping alpha-galactosidase liquid and cyclodextrin glycosyltransferase liquid into the mixture obtained in the S1;
s3, putting the container into a constant-temperature oscillator, and carrying out synthetic reaction under the oscillation condition;
s4, after the reaction is finished, putting the container into boiling water to soak for 2-3 min, and fully inactivating the alpha-galactosidase and the cyclodextrin glycosyltransferase;
s5, placing the inactivated mixed solution into a centrifugal tube for centrifugation, and taking supernatant after the centrifugation is finished;
s6, separating and purifying the supernatant obtained by centrifugation by using preparative high performance liquid chromatography to obtain a multi-branched cyclodextrin solution;
s7, freeze-drying the multi-branched cyclodextrin solution to obtain multi-branched cyclodextrin powder.
In S1, the use amount of the materials is as follows:
the mol ratio of the beta-cyclodextrin to the 6-O-alpha-D-galactopyranosyl-D-glucose is 1: 1-2;
the addition amount of glycyrrhizic acid is 2.6-3.7% of the total mass of the S1 mixture.
In S2, the material consumption is as follows:
the dosage of the alpha-galactosidase is 21.3-28.4U per g of 6-O-alpha-D-galactopyranosyl-D-glucose;
the dosage of the cyclodextrin glycosyltransferase is 18.5-26.7U per g of 6-O-alpha-D-galactopyranosyl-D-glucose.
In S3, the reaction conditions are as follows: the temperature is 25-30 ℃, the time is 35-70 h, and the oscillation speed is 150-200 r/min.
In S4, the centrifugation conditions are as follows: the centrifugal speed is 2400-3000 r/min, and the centrifugal time is 2.5-3.5 min.
In S6, the separation and purification conditions are as follows: prepC18 OBD 5 μm,19mm × 150mm chromatography column, SEDEX75 evaporative light scattering detector, waters1525 binary HPLC pump;
the sample injection amount is 1-1.5 mL, and the column temperature is 20-25 ℃;
the mobile phase is methanol water solution with the volume concentration of 1-3 percent, and the flow rate is 2.0-3.0 mL/min;
the split ratio is 25: 1-30: 1;
the sample solution was collected corresponding to characteristic peak a.
In S7, the freeze-drying conditions were: the temperature is minus 40 ℃, the vacuum degree is less than or equal to 12Pa, and the drying time is 24-48 h.
The application of the masking agent for improving the bitter and astringent taste of food is used for improving the bitter and astringent taste of food.
A method for improving food bitterness comprises adding the masking agent into food with bitterness, and stirring.
The bitter food can be soybean polypeptide, marine protein peptide, orange juice, guiling jelly, tartary buckwheat tea, black tea, etc.
In order to achieve better shielding effect, the addition amount of the multi-branched cyclodextrin is 0.1-10% of the food quality.
The multi-branched cyclodextrin is prepared by taking beta-cyclodextrin and 6-O-alpha-D-galactopyranosyl-D-glucose as raw materials. The multi-branched cyclodextrin has a unique cave structure, and can adsorb and embed substances with bitter and astringent taste, thereby achieving the effect of improving the bitter and astringent taste. The method for improving the bitter taste is simple and convenient to operate, can achieve the purpose of better removing the bitter taste without additionally adding a process, and has better application prospect in food.
Detailed Description
The present invention will be further understood from the following specific examples of the present invention, which should not be construed as limiting the scope of the present invention.
Example 1
A masking agent for improving food bitterness comprises multi-branched cyclodextrin.
The preparation method of the masking agent for improving the bitter taste of the food comprises the following steps:
s1, mixing dry powder beta-cyclodextrin and 6-O-alpha-D-galactopyranosyl-D-glucose in a container, adding a glycyrrhizic acid buffer solution, and stirring to dissolve the beta-cyclodextrin and the 6-O-alpha-D-galactopyranosyl-D-glucose;
the material consumption is:
the mol ratio of the beta-cyclodextrin to the 6-O-alpha-D-galactopyranosyl-D-glucose is 1: 1.2;
the addition amount of glycyrrhizic acid is 2.6% of the total mass of the S1 mixture.
S2, dripping alpha. Adding galactosidase solution and cyclodextrin glycosyltransferase solution into the mixture obtained in S1;
the material consumption is:
the dosage of the alpha-galactosidase is 21.5U per g of 6-O-alpha-D-galactopyranosyl-D-glucose;
per g of 6-O-alpha-D-galactopyranosyl. D-glucose and cyclodextrin glycosyltransferase were used in an amount of 22.5U.
S3, placing the container into a constant-temperature oscillator, and carrying out synthetic reaction under the oscillation condition; the reaction conditions are as follows: the temperature is 25 ℃, the time is 48h, and the oscillation speed is 150r/min.
S4, after the reaction is finished, putting the container into boiling water to soak for 3min, and fully inactivating the alpha-galactosidase and the cyclodextrin glycosyltransferase;
s5, placing the inactivated mixed solution into a centrifugal tube for centrifugation, and taking supernatant after the centrifugation is finished; the centrifugation conditions were: the centrifugation speed is 3000r/min, and the centrifugation time is 3min.
S6, separating and purifying the supernatant obtained by centrifugation by using preparative high performance liquid chromatography to obtain a multi-branched cyclodextrin solution;
the separation and purification conditions are as follows: prepC18 OBD 5 μm,19mm × 150mm column, SEDEX75 evaporative light scattering detector, waters1525 binary HPLC pump;
the sample injection amount is 1.5mL, and the column temperature is 25 ℃;
the mobile phase is methanol water solution with the volume concentration of 1-3%, and the flow rate is 3.0mL/min;
the split ratio is 25: 1;
the sample solution was collected corresponding to characteristic peak a.
S7, freeze-drying the multi-branched cyclodextrin solution to obtain multi-branched cyclodextrin powder. The freeze-drying conditions were: the temperature is minus 40 ℃, the vacuum degree is less than or equal to 12Pa, and the drying time is 48h.
Example 2
A masking agent for improving bitterness of food comprises multi-branched cyclodextrin.
The preparation method of the masking agent for improving the bitter taste of the food comprises the following steps:
s1, mixing dry powder beta-cyclodextrin and 6-O-alpha-D-galactopyranosyl-D-glucose in a container, adding a glycyrrhizic acid buffer solution, and stirring to dissolve the beta-cyclodextrin and the 6-O-alpha-D-galactopyranosyl-D-glucose;
the material consumption is:
the mol ratio of the beta-cyclodextrin to the 6-O-alpha-D-galactopyranosyl-D-glucose is 1: 2;
the addition amount of glycyrrhizic acid was 3.5% of the total mass of the S1 mixture.
S2, dripping alpha-galactosidase liquid and cyclodextrin glycosyltransferase liquid into the mixture obtained in the S1;
the material consumption is:
the dosage of alpha-galactosidase is 24.3U per g of 6-O-alpha-D-galactopyranosyl-D-glucose;
the cyclodextrin glycosyltransferase was used in an amount of 20.6U per g of 6-O-. Alpha. -D-galactopyranosyl-D-glucose.
S3, putting the container into a constant-temperature oscillator, and carrying out synthetic reaction under the oscillation condition; the reaction conditions are as follows: the temperature is 25 to DEG C, the time is 70h, and the oscillation speed is 150r/min.
S4, after the reaction is finished, putting the container into boiling water to soak for 2min, and fully inactivating the alpha-galactosidase and the cyclodextrin glycosyltransferase;
s5, placing the inactivated mixed solution into a centrifuge tube for centrifugation, and taking supernatant after the centrifugation is finished; the centrifugation conditions were: the centrifugation speed is 2400r/min, and the centrifugation time is 3.5min.
S6, separating and purifying the supernatant obtained by centrifugation by using preparative high performance liquid chromatography to obtain a multi-branched cyclodextrin solution;
the separation and purification conditions are as follows: prepC18 OBD 5 μm,19mm × 150mm chromatography column, SEDEX75 evaporative light scattering detector, waters1525 binary HPLC pump;
the sample introduction amount is mL, and the column temperature is 25 ℃;
the mobile phase is methanol water solution with the volume concentration of 1 percent, and the flow rate is 3.0mL/min;
the split ratio is 30: 1;
the sample solution was collected corresponding to characteristic peak a.
S7, freeze-drying the multi-branched cyclodextrin solution to obtain multi-branched cyclodextrin powder. The freeze-drying conditions were: the temperature is minus 40 ℃, the vacuum degree is less than or equal to 12Pa, and the drying time is 24h.
Example 3
A masking agent for improving food bitterness comprises multi-branched cyclodextrin.
The preparation method of the masking agent for improving the bitter taste of the food comprises the following steps:
s1, mixing dry powder beta-cyclodextrin and 6-O-alpha-D-galactopyranosyl-D-glucose in a container, adding a glycyrrhizic acid buffer solution, and stirring to dissolve the beta-cyclodextrin and the 6-O-alpha-D-galactopyranosyl-D-glucose;
the material consumption is:
the mol ratio of the beta-cyclodextrin to the 6-O-alpha-D-galactopyranosyl-D-glucose is 1: 1.5;
the addition amount of glycyrrhizic acid was 3.2% of the total mass of the S1 mixture.
S2, dripping alpha-galactosidase liquid and cyclodextrin glycosyltransferase liquid into the mixture obtained in the S1;
the material consumption is:
the dosage of alpha-galactosidase is 28.4U per g of 6-O-alpha-D-galactopyranosyl-D-glucose;
the cyclodextrin glycosyltransferase was used in an amount of 18.8U per g of 6-O-. Alpha. -D-galactopyranosyl-D-glucose.
S3, putting the container into a constant-temperature oscillator, and carrying out synthetic reaction under the oscillation condition; the reaction conditions are as follows: the temperature is 30 ℃, the time is 35h, and the oscillation speed is 150r/min.
S4, after the reaction is finished, putting the container into boiling water to soak for 2min, and fully inactivating the alpha-galactosidase and the cyclodextrin glycosyltransferase;
s5, placing the inactivated mixed solution into a centrifuge tube for centrifugation, and taking supernatant after the centrifugation is finished; the centrifugation conditions were: the centrifugation speed is 2400r/min, and the centrifugation time is 2.5min.
S6, separating and purifying the supernatant obtained by centrifugation by using preparative high performance liquid chromatography to obtain a multi-branched cyclodextrin solution;
the separation and purification conditions are as follows: prepC18 OBD 5 μm,19mm × 150mm chromatography column, SEDEX75 evaporative light scattering detector, waters1525 binary HPLC pump;
the sample introduction amount is 1.5mL, and the column temperature is 25 ℃;
the mobile phase is methanol water solution with the volume concentration of 1 percent, and the flow rate is 2.0mL/min;
the split ratio is 25: 1;
the sample solution was collected corresponding to characteristic peak a.
S7, freeze-drying the multi-branched cyclodextrin solution to obtain multi-branched cyclodextrin powder. The freeze-drying conditions were: the temperature is minus 40 ℃, the vacuum degree is less than or equal to 12Pa, and the drying time is 48h.
Weighing 1 g of soybean polypeptide and 99 g of water in a beaker, and uniformly stirring. The resulting solution was bitter in aftertaste.
Weighing 1 g of soybean polypeptide, 0.5 g of masking agent multi-branched cyclodextrin and 98.5 g of water in a beaker, and uniformly stirring. The obtained solution has no obvious bitter taste.
2 g of black tea leaves are weighed in a beaker, 250 g of boiling water is added, and the solution is tasted after 3 minutes, and the obtained solution has obvious bitter taste.
2 g of black tea leaves and 1 g of multi-branched cyclodextrin are weighed in a beaker, 250 g of boiling water is added, and the solution is tasted after 3 minutes, and has no obvious bitter taste.
The masking agent multi-branched cyclodextrin is larger than other commercially available cyclodextrin cyclic parts, has a unique cave structure, and can adsorb more bitter substances with different molecular sizes, so that the bitter taste is improved.
Although the present invention has been described in detail by the above examples, such description is for illustrative purposes only and should not be construed as limiting the spirit and scope of the present invention as claimed in the appended claims. In addition, the above-described embodiments are for illustrative purposes only, and various modifications may be made thereto, and those skilled in the art will appreciate that the modifications also fall within the scope of the present invention.
Claims (10)
1. A masking agent for improving the bitterness of food, characterized by comprising a multi-branched cyclodextrin.
2. The method for preparing a masking agent for improving bitterness and astringency of food as claimed in claim 1, comprising the steps of:
s1, mixing dry powder beta-cyclodextrin and 6-O-alpha-D-galactopyranosyl-D-glucose in a container, adding glycyrrhizic acid buffer solution, and stirring to dissolve the beta-cyclodextrin and the 6-O-alpha-D-galactopyranosyl-D-glucose;
s2, dripping alpha-galactosidase liquid and cyclodextrin glycosyltransferase liquid into the mixture obtained in the S1;
s3, putting the container into a constant-temperature oscillator, and carrying out synthetic reaction under the oscillation condition;
s4, after the reaction is finished, putting the container into boiling water to soak for 2-3 min, and fully inactivating the alpha-galactosidase and the cyclodextrin glycosyltransferase;
s5, placing the inactivated mixed solution into a centrifugal tube for centrifugation, and taking supernatant after the centrifugation is finished;
s6, separating and purifying the supernatant obtained by centrifugation by using preparative high performance liquid chromatography to obtain a multi-branched cyclodextrin solution;
s7, freeze-drying the multi-branched cyclodextrin solution to obtain multi-branched cyclodextrin powder.
3. The method for preparing a masking agent for improving bitter and astringent taste of food according to claim 1, wherein the amount of the material in S1 is as follows:
the mol ratio of the beta-cyclodextrin to the 6-O-alpha-D-galactopyranosyl-D-glucose is 1: 1-2;
the addition amount of glycyrrhizic acid is 2.6-3.7% of the total mass of the S1 mixture.
4. The method for preparing a masking agent for improving bitter and astringent taste of food as claimed in claim 1, wherein the amount of the material in S2 is:
the dosage of alpha-galactosidase is 21.3-28.4U per g of 6-O-alpha-D-galactopyranosyl-D-glucose;
the dosage of the cyclodextrin glycosyltransferase is 18.5-26.7U per g of 6-O-alpha-D-galactopyranosyl-D-glucose.
5. The method for preparing a masking agent for improving bitterness and astringency of food as claimed in claim 1, wherein in S3, the reaction conditions are: the temperature is 25-30 ℃, the time is 35-70 h, and the oscillation speed is 150-200 r/min.
6. The method for preparing a masking agent for improving bitterness and astringency of food according to claim 1, wherein in S4, the centrifugation conditions are as follows: the centrifugal speed is 2400-3000 r/min, and the centrifugal time is 2.5-3.5 min.
7. The method for preparing a masking agent for improving bitterness and astringency of food as claimed in claim 1, wherein in S6, the conditions of separation and purification are as follows: prepC18 OBD 5 μm,19mm × 150mm column, SEDEX75 evaporative light scattering detector, waters1525 binary HPLC pump;
the sample introduction amount is 1-1.5 mL, and the column temperature is 20-25 ℃;
the mobile phase is methanol water solution with volume concentration of 1-3%, and the flow rate is 2.0-3.0 mL/min;
the split ratio is 25: 1-30: 1;
the sample solution was collected corresponding to characteristic peak a.
8. The method for producing a masking agent for improving bitterness and astringency of food according to claim 1, wherein in S7, the freeze-drying conditions are as follows: the temperature is minus 40 ℃, the vacuum degree is less than or equal to 12Pa, and the drying time is 24-48 h.
9. Use of the masking agent for improving food bitterness and astringency according to claim 1, for improving food bitterness and astringency.
10. A method for improving the bitter taste of food is characterized in that: the masking agent for improving bitterness and astringency of food according to claim 1, which is added to a food having bitterness and astringency and stirred uniformly.
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|---|---|---|---|---|
| CN101280332A (en) * | 2008-05-09 | 2008-10-08 | 江南大学 | Enzymatic preparation of alpha-galactosyl-beta-cyclodextrin |
| CN106498007A (en) * | 2016-11-18 | 2017-03-15 | 四川理工学院 | A kind of preparation method of γ cyclodextrin |
| US20190194708A1 (en) * | 2017-05-16 | 2019-06-27 | Jiangnan University | Method for Preparing Branched Cyclodextrin and Application thereof |
| KR20220086162A (en) * | 2020-12-16 | 2022-06-23 | 대상 주식회사 | Beverage composition comprising highly branched cyclic dextrin |
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- 2022-08-12 CN CN202210986000.8A patent/CN115428936A/en active Pending
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|---|---|---|---|---|
| CN101280332A (en) * | 2008-05-09 | 2008-10-08 | 江南大学 | Enzymatic preparation of alpha-galactosyl-beta-cyclodextrin |
| CN106498007A (en) * | 2016-11-18 | 2017-03-15 | 四川理工学院 | A kind of preparation method of γ cyclodextrin |
| US20190194708A1 (en) * | 2017-05-16 | 2019-06-27 | Jiangnan University | Method for Preparing Branched Cyclodextrin and Application thereof |
| KR20220086162A (en) * | 2020-12-16 | 2022-06-23 | 대상 주식회사 | Beverage composition comprising highly branched cyclic dextrin |
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