WO2023224086A1 - エクオールを含む食品組成物およびその製造方法 - Google Patents

エクオールを含む食品組成物およびその製造方法 Download PDF

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Publication number
WO2023224086A1
WO2023224086A1 PCT/JP2023/018548 JP2023018548W WO2023224086A1 WO 2023224086 A1 WO2023224086 A1 WO 2023224086A1 JP 2023018548 W JP2023018548 W JP 2023018548W WO 2023224086 A1 WO2023224086 A1 WO 2023224086A1
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Prior art keywords
acid
equol
food composition
group
adjusted
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English (en)
French (fr)
Japanese (ja)
Inventor
和也 三橋
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Daicel Corp
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Daicel Corp
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Priority to US18/867,148 priority Critical patent/US20250351853A1/en
Priority to JP2023561223A priority patent/JP7463627B1/ja
Priority to KR1020247036722A priority patent/KR102901581B1/ko
Priority to CN202380039147.9A priority patent/CN119173160A/zh
Publication of WO2023224086A1 publication Critical patent/WO2023224086A1/ja
Priority to JP2024049307A priority patent/JP2024075746A/ja
Priority to JP2024121889A priority patent/JP7566414B1/ja
Anticipated expiration legal-status Critical
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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/3533,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L11/00Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/05Mashed or comminuted pulses or legumes; Products made therefrom
    • A23L11/07Soya beans, e.g. oil-extracted soya bean flakes
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L11/00Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/30Removing undesirable substances, e.g. bitter substances
    • A23L11/34Removing undesirable substances, e.g. bitter substances using chemical treatment, adsorption or absorption
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L11/00Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/50Fermented pulses or legumes; Fermentation of pulses or legumes based on the addition of microorganisms
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L11/00Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/70Germinated pulse products, e.g. from soy bean sprouts
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/127Antibiotics
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00Microorganisms; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/20Bacteria; Culture media therefor
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/02Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00Function of food ingredients
    • A23V2200/06Function of food ingredients pH modification agent

Definitions

  • the present invention relates to a food composition containing equol, which is a pH-adjusted liquid food composition or a dried product thereof.
  • the present invention also relates to a method for producing the food composition.
  • Isoflavones which are abundant in leguminous plants such as soybeans and kudzu, are a class of polyphenols, and are flavonoids that have isoflavones as their basic skeleton. Recent research has shown that isoflavones have female hormone effects (estrogen) and antioxidant effects, and that ingesting isoflavones can lead to breast cancer, prostate cancer, osteoporosis, hypercholesterolemia, heart disease, menopausal symptoms, etc. It has been shown that it has a preventive effect.
  • Isoflavones exist, for example, in soybeans in the form of glycosides covalently bonded to sugars, such as daidzin, glycitin, and genistin, and in very small amounts in the form of aglycones. Only. Some of these glycosides are malonylated or acetylated. When these glycosides enter the human or animal body, they are converted into daidzein, glycitein, and genistein, respectively, by the action of digestive enzymes or ⁇ -glucosidase, an enzyme produced by intestinal bacteria. Become. Furthermore, it is known that daidzein is enzymatically converted to O-desmethylangolensin (O-DMA) or equol via dihydrodaidzein by the action of intestinal bacteria. It is being
  • Equol is known to have the highest estrogenic activity among these metabolites.
  • isoflavones there are individual differences in the metabolism of isoflavones, and as mentioned above, few people have intestinal bacteria that have the ability to ferment daidzein and produce equol, and the prevalence rate among Japanese people is approximately It has been revealed that this rate is 50%, and about 30% for Westerners. Therefore, there has been a problem in that people who do not have equol-producing bacteria cannot produce equol in their bodies even if they ingest leguminous foods such as soybeans.
  • Patent Documents 1 to 4 In order to overcome these problems, attempts have been made to produce equol in vitro using anaerobic microorganisms such as lactic acid bacteria (Patent Documents 1 to 4). A method to efficiently recover the produced equol is being sought.
  • Patent Document 5 aims to provide an equol-producing microorganism-containing composition that contains equol-producing microorganisms in a viable state that maintain equol-producing ability, and can stably maintain equol-producing ability even after storage, and uses pH control.
  • Patent Document 5 discloses that a pH adjuster may be added for this purpose, but does not disclose a specific pH adjuster. Further, the pH was adjusted in the anaerobic fermentation process, and the preferred pH was 4.6 or higher.
  • the above food composition which is a pH-adjusted liquid food composition containing equol, or a dried product thereof.
  • the pH is preferably 3 to 5, preferably 3 to 4.
  • the composition has its pH adjusted with one selected from the group consisting of organic acids and inorganic acids,
  • the organic acid is at least one selected from carbonic acid, hydrogen carbonate, citric acid, succinic acid, fumaric acid, lactic acid, gluconic acid, acetic acid, malic acid, ascorbic acid and benzoic acid
  • the inorganic acid is at least one selected from the group consisting of hydrochloric acid, sulfuric acid, and phosphoric acid.
  • the composition preferably contains at least one selected from the group of inorganic acids consisting of hydrochloric acid, sulfuric acid, and phosphoric acid.
  • the pH is preferably 7 to 11, preferably 10 to 11.
  • the pH of the composition is adjusted with one selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides. good.
  • the pH of the composition is adjusted with one selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium oxide, and magnesium hydroxide. It's good to have one.
  • a method for producing a liquid food composition comprising: obtaining a pH-adjusted liquid food composition containing equol.
  • the adjusted pH is preferably 3 to 5, preferably 3 to 4.
  • the pH adjuster has one selected from the group consisting of organic acids and inorganic acids,
  • the organic acid is at least one selected from carbonic acid, hydrogen carbonate, citric acid, succinic acid, fumaric acid, lactic acid, gluconic acid, acetic acid, malic acid, ascorbic acid and benzoic acid,
  • the inorganic acid is at least one selected from the group consisting of hydrochloric acid, sulfuric acid, and phosphoric acid.
  • the pH adjuster has at least one kind selected from the inorganic acid group consisting of hydrochloric acid, sulfuric acid, and phosphoric acid.
  • the adjusted pH is preferably 7 to 11, preferably 10 to 11.
  • the pH adjuster preferably has one selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides.
  • the pH adjuster is preferably one selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium oxide, and magnesium hydroxide.
  • the present invention it is possible to provide an equol-containing food composition that can further prevent microbial contamination and a method for producing the same. Moreover, the present invention can provide a method for producing an equol-containing food composition, which efficiently recovers produced equol in addition to or in addition to the above-described effects.
  • the present application provides a method for producing a liquid food composition, a method for producing a powdered food composition, and a powdered food composition that is a liquid food composition and a dried product thereof.
  • a method for producing a liquid food composition and a method for producing a powdered food composition will be explained, and then a powdered food composition that is a liquid food composition and a dried product thereof will be explained.
  • the method for producing a liquid food composition of the present invention includes: (A) a step of culturing at least one equol raw material selected from the group consisting of daidzein glycosides, daidzein, and dihydrodaidzein with a microorganism that assimilates the equol raw material and produces equol; and (B) the culturing step.
  • Step (A) is a step of culturing at least one equol raw material selected from the group consisting of daidzein glycosides, daidzein, and dihydrodaidzein with a microorganism that assimilates the equol raw material and produces equol.
  • the conditions of the culture step are not particularly limited as long as equol can be produced. For example, conventionally known conditions can be used, but the conditions are not limited thereto.
  • the equol raw material used in the method of the present invention can be in any form as long as it can literally be used as a raw material for equol.
  • the equol raw material may be in any form as long as it contains at least one selected from the group consisting of daidzein glycosides, daidzein, and dihydrodaidzein.
  • daidzein glycosides themselves, daidzein itself, or dihydrodaidzein itself, and products containing them, such as soybeans, soybean processed products, soybean hypocotyls, soybean hypocotyl processed products, such as soybean extracts, soybean embryos.
  • Examples include cox extract and purified soybean hypocotyl extract, and specifically, commercially available isoflavones may be used.
  • the method of the present invention uses microorganisms that have the ability to assimilate equol raw materials and produce equol.
  • the "ability to assimilate equol raw materials and produce equol” is sometimes simply referred to as "equol production ability" in this specification.
  • the microorganism having the ability to produce equol used in the method of the present invention is not particularly limited as long as it is a microorganism having the ability to produce equol from the above-mentioned equol raw material. Note that the equol raw material is determined in relation to the "equol production ability" of the microorganism.
  • a certain microorganism A does not have "equol-producing ability" for daidzein glycosides but has "equol-producing ability” for daidzein, the equol raw material of the microorganism A will be "daidzein.”
  • a step of converting daidzein glycosides into daidzein may be included before the step (A).
  • ethyl acetate For example, add ethyl acetate to the culture solution, stir vigorously, centrifuge, and remove the ethyl acetate layer. If necessary, the same operation can be performed on the same culture solution several times, and the ethyl acetate layers can be combined to obtain an equol extract.
  • This extract is concentrated to dryness using an evaporator under reduced pressure, and then dissolved in methanol. This can be filtered using a membrane such as a polytetrafluoroethylene (PTFE) membrane to remove insoluble materials, and the resultant sample can be used as a high performance liquid chromatography measurement sample. Examples of conditions for high performance liquid chromatography include, but are not limited to, the following.
  • microorganisms having the ability to produce equol include, but are not limited to, microorganisms classified into the following genera. Genus Adlercreutzia Genus Bacteroides Genus Bifidobacterium Genus Clostridium Genus Eggerthella Genus Enterococcus Genus Enterorhabdus Genus Eubacterium Genus Finegoldia Genus Lactobacillus Genus Lactococcus Genus Paraeggerthella Genus Pediococcus Genus Proteus Genus Sharpea Genus Slackia Genus Streptococcus Genus Veillonella
  • microorganisms having the ability to produce equol include, but are not limited to, the following microorganisms.
  • Adlercreutzia equolifaciens subsp. celatus Adlercreutzia equolifaciens subsp. equolifaciens Bacteroides ovatus Bifidobacterium breve Bifidobacterium longum Clostridium sp. Eggerthella sp. Enterococcus faecalis Enterococcus faecium Enterorhabdus mucosicola Eubacterium sp.
  • microorganisms classified in the family Eggerthellaceae for example, microorganisms classified in the family Eggerthellaceae, microorganisms classified in the family Bifidobacteriaceae, microorganisms classified in the family Clostridiaceae, and microorganisms classified in the family Clostridiaceae.
  • microorganisms classified in the family Coriobacteriaceae microorganisms classified in the family Enterococceae
  • microorganisms classified in the family Eubacteriaceae and microorganisms classified in the family Morganellaceae.
  • Microorganisms microorganisms classified in the family Peptoniphilaceae, microorganisms classified in the family Lactobacillaceae, microorganisms classified in the family Streptococceae, microorganisms classified in the family Veillonellaceae. Examples include classified microorganisms and related microorganisms.
  • Adlercreutzia Bacteroides, Bifidobacterium, Clostridium, Coriobacterium, Egasella, Enterococcus, Eubacterium, Finegordia, Lactobacillus, Lactococcus
  • the microorganisms are preferably classified into the genus Paraegacella, Pediococcus, Proteus, Sharpea, Thracia, Streptococcus, Veilonea, or related microorganisms thereof. More preferably, Adrecrautia aequorifaciens subsp. ceratus, Adrecrautia aequorifaciens subsp.
  • aequorifaciens Bacteroides obatus, Bifidobacterium breve, Bifidobacterium longum , Clostridium sp., Egasella sp., Enterococcus faecalis, Enterococcus faecium, Enterorhabdus mucosicola, Eubacterium sp., Finegordia magna, Lactobacillus fermentum, Lactobacillus intestinalis, Lactobacillus - Mucosae, Lactobacillus paracasei, Lactobacillus plantarum, Lactobacillus rhamnosus, Lactobacillus sp., Lactococcus garubiae, Lactococcus sp., Paraegasera sp., Pediococcus pentosaceus, Proteus mirabilis, Sharpea azabu Preferred are Thracia ensis, Thracia aequor
  • any of the microorganisms described below or related bacteria having similar species properties to these microorganisms can be particularly cited as more preferable anaerobic microorganisms.
  • Adlercreutzia equolifaciens subsp. celatus DSM 18785 strain
  • Adlercreutzia equolifaciens subsp. equolifaciens DSM 19450 strain
  • anaerobic microorganism can be obtained from the depository institution indicated by its deposit number. Each accession number indicates that the anaerobic microorganism has been deposited with the following depositary institution.
  • FERM International Patent Organism Depositary http://unit.aist.go.jp/pod/ci/index.html
  • DSM German Collection of Microorganisms and Cell Cultures http://www.dsmz.de/ KCCM Korean Culture Center of Microorganisms
  • anaerobic microorganisms capable of producing equol are cultured under conditions suitable for producing equol.
  • conditions suitable for equol production refer to conditions that maintain the survival and activity of anaerobic microorganisms having equol production activity. More specifically, it means that gas phase conditions (anaerobic conditions) that allow the survival of anaerobic microorganisms are maintained, and nutrients are provided to support the activity and proliferation of the anaerobic microorganisms.
  • gas phase conditions anaerobic conditions
  • Various medium compositions suitable for the survival of anaerobic microorganisms are known.
  • an appropriate medium composition for the above-mentioned anaerobic microorganisms capable of producing equol for example, BHI medium manufactured by Difco, the medium used in Examples, etc. can be used, but the medium is not limited thereto.
  • a water-soluble organic substance can be added to the culture medium used in the present invention as a carbon source.
  • water-soluble organic substances include, but are not limited to, the following compounds.
  • Sugars such as sorbose, fructose, glucose
  • Alcohols such as methanol
  • Organic acids such as valeric acid, butyric acid, propionic acid, acetic acid, and formic acid, or salts thereof.
  • the concentration of organic matter added to the medium as a carbon source can be adjusted as appropriate to efficiently grow anaerobic microorganisms in the medium.
  • a nitrogen source can be added to the medium.
  • various nitrogen compounds that can be used in normal fermentation can be used as the nitrogen source.
  • Preferred inorganic nitrogen sources are ammonium salts and nitrates. More preferred inorganic nitrogen sources are ammonium sulfate, ammonium chloride, ammonium phosphate, ammonium hydrogen phosphate, potassium nitrate and sodium nitrate.
  • preferred organic nitrogen sources include amino acids, yeast extract, peptones, meat extract, liver extract, and digested serum powder. More preferred organic nitrogen sources are arginine, cysteine, cystine, citrulline, lysine, yeast extract, and peptones.
  • organic or inorganic substances suitable for producing equol can also be added to the medium.
  • the growth and activity of anaerobic microorganisms can be enhanced in some cases by adding cofactors such as vitamins and inorganic compounds such as various salts to the culture medium.
  • cofactors such as vitamins and inorganic compounds such as various salts.
  • examples of microbial growth cofactors derived from inorganic compounds, vitamins, and animals and plants include the following.
  • the medium can be liquid, semi-solid, or solid.
  • a preferred medium form is a liquid medium.
  • the medium used in the present invention can contain dextrins. If anaerobic microorganisms are cultured in a medium containing dextrins, a liquid containing equol and dextrins can be prepared without contacting the culture with dextrins again after culturing. Dextrins can be added to the medium before or during the cultivation of the microorganism.
  • the medium used in the present invention can contain an antifoaming agent, preferably soybean oil, more preferably soybean oil containing vitamin E.
  • microorganisms particularly anaerobic microorganisms
  • a continuous fermentation system that can continuously supply a medium and substrate gas and has a mechanism for recovering the culture can also be used.
  • anaerobic microorganisms when using anaerobic microorganisms, it is preferable to prevent oxygen from entering the fermenter.
  • a commonly used fermenter can be used as is.
  • An anaerobic atmosphere can be created by replacing oxygen mixed into the fermenter with an inert gas such as nitrogen.
  • a stirrer or the like may be used to sufficiently stir the culture medium.
  • the substrate gas can also be supplied in the form of nanobubbles.
  • microorganisms can be cultured under normal pressure, but when pressurized, the pressurizing conditions are not particularly limited as long as the microorganisms can grow.
  • Preferred pressurizing conditions include, but are not limited to, a range of 0.2 MPa or less, for example, a range of 0.02 to 0.2 MPa.
  • the temperature of the culture tank is not particularly limited, but it is preferably 30°C to 40°C, more preferably 33°C to 38°C.
  • the culture time can be appropriately set depending on the amount of equol produced, the remaining amount of isoflavones, and the like. Examples include, but are not limited to, 8 to 120 hours, preferably 12 to 72 hours, particularly preferably 16 to 60 hours.
  • Step (B) is a step of adjusting the pH by adding a pH adjuster to the equol-containing culture solution obtained in step (A), that is, the culture step.
  • the pH of the culture solution is preferably adjusted to the acid side, and specifically, the pH is preferably adjusted to 3 to 5, preferably 3 to 4.
  • step (B) the pH of the culture solution is preferably adjusted to the alkaline side, and specifically, the pH is preferably adjusted to 7 to 11, preferably 10 to 11.
  • the pH of the culture solution is preferably adjusted to be alkaline in this way, specifically adjusting the pH to 7 to 11, especially 10 to 11, the microorganisms used in step (A) can be dissolved. In turn, the recovery efficiency of equol can be improved.
  • the pH adjuster when adjusting the pH to the alkaline side, preferably has one selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides.
  • examples of the pH adjuster for adjusting to the alkaline side include, but are not limited to, sodium hydroxide, potassium hydroxide, calcium hydroxide, calcium oxide, and magnesium hydroxide.
  • the method of the present invention for obtaining a liquid food composition includes steps other than the above steps (A) and (B).
  • You may. Examples include, but are not limited to, processes for removing microorganisms capable of producing equol, such as a centrifugation process and a membrane filtration process.
  • Step (C) is a step of drying the liquid obtained in the pH adjustment step (B).
  • the drying step can be performed by a conventionally known method. Examples include, but are not limited to, heat drying treatment, spray drying treatment, freeze drying treatment, fluidized bed drying, fluidized bed drying, and the like.
  • the heat drying process can be performed using, for example, a rotary drum dryer, the spray drying process can be performed using, for example, a spray dryer, and the freeze drying process can be performed using a freeze dryer. Any drying method may be used as long as it is capable of drying liquids.
  • the product obtained by drying may be subjected to pulverization treatment, if necessary.
  • the method of the present invention may include steps other than the above steps (A), (B), and (C).
  • steps (B) and before step (C) there is a step of heat-treating the pH-adjusted liquid obtained in step (B), and after the heat treatment step, unnecessary solid content is removed from the obtained liquid.
  • It may include a centrifugation step and/or a filtration step for removal.
  • step (B) when the pH is adjusted to an alkaline side, particularly to a pH of 10 to 11, the centrifugation step is not necessary, which is preferable since the number of steps can be reduced.
  • the composition includes a centrifugation step and/or a filtration step to remove unnecessary solids, a clear liquid can be obtained, resulting in a liquid food composition suitable for serving as a beverage.
  • the present application provides the above-mentioned food composition, which is a pH-adjusted liquid food composition or a dried product thereof, which is a food composition containing equol.
  • the food composition of the present invention can also be obtained by the method described above, but is not limited thereto.
  • liquid food composition When the liquid food composition is on the acid side, its pH is preferably 3 to 5, preferably 3 to 4. Further, when the liquid food composition is on the alkaline side, the pH thereof is preferably 7 to 11, preferably 10 to 11.
  • the present application also provides a dried pH-adjusted liquid food composition comprising equol.
  • pH is defined as follows. That is, if the pH when 50 g of the dried product is dissolved or suspended in 1 L of water is in the above range, that is, on the acid side, the pH is 3 to 5, preferably 3 to 4, or if it is on the alkaline side, The pH is preferably 7-11, preferably 10-11.
  • a glass diaphragm electrode can be suitably used for pH measurement, but a simple one such as a pH test paper can also be used.
  • the pH of the food composition is adjusted with one selected from the group consisting of organic acids and inorganic acids.
  • the food composition of the present invention will have one type selected from the group consisting of organic acids and inorganic acids.
  • organic acids include, but are not limited to, carbonic acid, hydrogen carbonate, citric acid, succinic acid, fumaric acid, lactic acid, gluconic acid, acetic acid, malic acid, ascorbic acid, and benzoic acid.
  • examples of inorganic acids include, but are not limited to, hydrochloric acid, sulfuric acid, and phosphoric acid.
  • Example 1 Preparation of preculture medium
  • Anaerobe Basal Broth manufactured by Thermo Scientific, catalog number CM0957B
  • ABB medium distilled water
  • gas replacement was performed with nitrogen gas, and sterilization was performed at 121° C. for 15 minutes.
  • Enzyme-treated soybean germ extract (containing aglyconized isoflavones: daidzein, glycitein, and genistein) was added to ABB medium containing ⁇ -cyclodextrin to a final concentration of 6 g/L, and 1 L was added to a 2 L fermenter. I noted it. Thereafter, gas replacement was performed with nitrogen gas, and sterilization was performed at 121° C. for 15 minutes.
  • pH adjustment process The main culture fluid in which equol production was confirmed was collected into a glass container, the pH was adjusted, and sterilization was performed by heating. For comparison, sterilization by heating was performed without pH adjustment. 1) By adding citric acid to the main culture solution, the pH was lowered to 3, 4, and 5, and sterilization was performed by heating. 2) Furthermore, by adding hydrochloric acid to the main culture solution, the pH was lowered to 3, 4, and 5, and sterilization was performed by heating. 3) Also, by adding sodium hydroxide to the main culture solution, the pH was raised to 8, 9, 10, and 11, and sterilization was performed by heating.
  • Example 3 In Example 1, the following steps were carried out after the pH adjustment step. (Centrifugal sedimentation separation process) After pH adjustment, the heat-sterilized culture solution was placed in a 40 mL centrifuge tube, insoluble components were precipitated using a centrifuge, and the supernatant was collected.
  • Equol and isoflavones in the filtrate were analyzed by HPLC method. The results are shown in Table 3. Table 3 shows that by making alkaline in the pH adjustment step, the isoflavone concentration can be improved and the recovery rate of isoflavones to the filtrate can be increased. Isoflavones other than equol are also expected to have physiological activity, so increasing the concentration of isoflavones can be expected to have effects that cannot be achieved with equol alone.
  • Example 4 In Example 1, the following drying process was performed after the pH adjustment process. Further, in Example 3, after the filtration step was performed, the following drying step was performed. (drying process) The filtrate was subjected to lyophilization and the powder was collected.
  • Example 6 Example 3 was carried out in the same manner as in Example 3, except that Asaccharobacter celatus DSM 18785 was used instead of Adlercreutzia equolifaciens DSM 19450 strain. The results are shown in Table 6. Table 6 shows that by making alkaline in the pH adjustment step, the isoflavone concentration can be improved and the recovery rate of isoflavones to the filtrate can be increased. Isoflavones other than equol are also expected to have physiological activity, so increasing the concentration of isoflavones can be expected to have effects that cannot be achieved with equol alone.
  • Example 7 (Preparation of preculture medium) Anaerobe Basal Broth (manufactured by Thermo Scientific, catalog number CM0957B) was dissolved in a predetermined amount of distilled water (ABB medium), and 1 L was dispensed into a 2 L pressurized fermenter. Thereafter, gas replacement was performed with nitrogen gas, and sterilization was performed at 121° C. for 15 minutes. (Preparation of main culture medium) After crushing the soybean germ, tap water was added to give a concentration of 100 g/L, and 1 L was dispensed into a 2 L fermenter.
  • ABB medium distilled water
  • enzyme was added and the isoflavone glycosides contained were aglyconized by stirring at 50°C overnight, and then arginine was added to give a concentration of 1 g/L, the gas was replaced with nitrogen gas, and the mixture was stirred at 50°C overnight. Sterilized in 15 minutes.
  • Example 7 was carried out in the same manner as in Example 7, except that Asaccharobacter celatus DSM 18785 was used instead of Adlercreutzia equolifaciens DSM 19450 strain. The results are shown in Table 8. Similarly to Example 7, when soybean germ is used as a raw material, equol and isoflavones are also present in the precipitate, but by making it alkaline in the pH adjustment step, the isoflavone concentration and equol concentration in the precipitate decrease, and the concentration in the supernatant decreases. It was found that the isoflavone concentration and equol concentration were improved, and the recovery rate of isoflavones could be increased.
  • the recovery rate of equol can be increased, and isoflavones other than equol are also expected to have physiological activity, so by increasing the concentration of isoflavones, effects that cannot be achieved with equol alone can be expected.
  • a clear aqueous solution By removing the water-insoluble soybean germ by centrifugation, a clear aqueous solution can be recovered, making it more suitable for beverages.

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CN202380039147.9A CN119173160A (zh) 2022-05-19 2023-05-18 包含雌马酚的食品组合物及其制造方法
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CN102159092B (zh) 2008-09-19 2016-03-16 大塚制药株式会社 含有维持了雌马酚产生能力的雌马酚产生微生物的发酵制品及其制备方法
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JP2014233259A (ja) * 2013-06-04 2014-12-15 株式会社ダイセル エクオール以外のイソフラボン類の含有量が低いエクオール含有組成物
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WO2025181921A1 (ja) * 2024-02-27 2025-09-04 株式会社ダイセル エクオールおよび5-ヒドロキシエクオールの製造方法

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