WO2021246392A1 - 乳酸菌増殖促進剤 - Google Patents

乳酸菌増殖促進剤 Download PDF

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WO2021246392A1
WO2021246392A1 PCT/JP2021/020796 JP2021020796W WO2021246392A1 WO 2021246392 A1 WO2021246392 A1 WO 2021246392A1 JP 2021020796 W JP2021020796 W JP 2021020796W WO 2021246392 A1 WO2021246392 A1 WO 2021246392A1
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lactic acid
residues
peptide
amino acid
total number
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French (fr)
Japanese (ja)
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直人 内田
雅信 切田
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Asahi Group Holdings Ltd
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Asahi Group Holdings Ltd
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Priority to US17/920,598 priority Critical patent/US20230151057A1/en
Priority to CN202180034794.1A priority patent/CN115551991A/zh
Priority to AU2021282621A priority patent/AU2021282621A1/en
Priority to JP2022528836A priority patent/JP7802665B2/ja
Priority to EP21818873.8A priority patent/EP4159742A4/en
Publication of WO2021246392A1 publication Critical patent/WO2021246392A1/ja
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    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K4/00Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
    • C07K4/06Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof from fungi
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    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06008Dipeptides with the first amino acid being neutral
    • C07K5/06017Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043Leu-amino acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06139Dipeptides with the first amino acid being heterocyclic
    • C07K5/06165Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
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    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
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    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0821Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • C07K5/0823Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Pro-amino acid; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10Tetrapeptides
    • C07K5/1002Tetrapeptides with the first amino acid being neutral
    • C07K5/1005Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/101Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10Tetrapeptides
    • C07K5/1024Tetrapeptides with the first amino acid being heterocyclic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04Linear peptides containing only normal peptide links
    • C07K7/06Linear peptides containing only normal peptide links having 5 to 11 amino acids
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    • 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
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    • 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
    • C12N1/38Chemical stimulation of growth or activity by addition of chemical compounds which are not essential growth factors; Stimulation of growth by removal of a chemical compound
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12RINDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00Microorganisms ; Processes using microorganisms
    • C12R2001/01Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/225Lactobacillus
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12RINDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00Microorganisms ; Processes using microorganisms
    • C12R2001/01Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/225Lactobacillus
    • C12R2001/23Lactobacillus acidophilus
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12RINDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00Microorganisms ; Processes using microorganisms
    • C12R2001/01Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/225Lactobacillus
    • C12R2001/24Lactobacillus brevis
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12RINDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00Microorganisms ; Processes using microorganisms
    • C12R2001/01Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/225Lactobacillus
    • C12R2001/25Lactobacillus plantarum

Definitions

  • the present invention relates to a lactic acid bacterium growth promoter.
  • Lactic acid bacteria are known to exhibit complex auxotrophy.
  • the yield of the obtained lactic acid bacteria may vary due to the variation in the quality of the medium raw material and the like.
  • factors that promote the growth of lactic acid bacteria and the like have been proposed.
  • International Publication No. 2017/034011 proposes a growth agent for intestinal useful bacteria containing a specific cyclodipeptide.
  • International Publication No. 2011/0277719 proposes a growth-promoting agent for Lactobacillus genus Lactobacillus containing ⁇ -caseinoglyco macropeptide as an active ingredient.
  • An object of the present invention is to provide a lactic acid bacterium growth promoting agent having a lactic acid bacterium growth promoting action.
  • the first aspect is a first peptide having a total number of residues of 9 or less and having a hydrophobic amino acid residue at the C-terminal, and a hydrophobic amino acid residue having a total number of residues of 9 or less and having a hydrophobic amino acid residue with respect to the total number of residues.
  • a lactic acid bacterium growth promoter containing at least one peptide selected from the group consisting of a second peptide having a ratio of the total number of groups and proline residues of 2/3 or more.
  • the hydrophobic amino acid residue is alanine (A), glycine (G), valine (V), isoleucine (I), leucine (L), phenylalanine (F), tyrosine (Y), tryptophan (W). ), Amino acid residues selected from the group consisting of methionine (M) and cysteine (C), from the group consisting of alanine (A), glycine (G), phenylalanine (F) and tyrosine (Y). It may be a residue of the selected amino acid.
  • the first peptide has a total number of residues of 6 or less, and the hydrophobic amino acid residue is an amino acid residue selected from the group consisting of phenylalanine (F) and tyrosine (Y). It's okay.
  • the first peptide may have a ratio of the total number of hydrophobic amino acid residues and proline residues to the total number of residues to be 2/3 or more.
  • the second peptide may have a ratio of the total number of hydrophobic amino acid residues and proline residues to the total number of residues of 3/4 or more. In one embodiment, the second peptide may have a total number of residues of 4 or less. In one embodiment, the second peptide may consist of hydrophobic amino acid residues and proline residues. In one embodiment, the second peptide may have a hydrophobic amino acid residue at the C-terminus.
  • a lactic acid bacterium growth promoting agent having a lactic acid bacterium growth promoting action.
  • each component in the composition is the total amount of the plurality of substances present in the composition when a plurality of substances corresponding to each component are present in the composition, unless otherwise specified. means.
  • embodiments of the present invention will be described in detail. However, the embodiments shown below exemplify a lactic acid bacterium growth promoter for embodying the technical idea of the present invention, and the present invention is not limited to the lactic acid bacterium growth promoter shown below.
  • the lactic acid bacterium growth promoter may contain at least one first peptide having a total number of residues of 9 or less and having a hydrophobic amino acid residue at the C-terminal.
  • the lactic acid bacterium growth promoter has a total number of residues of 9 or less, and the ratio of the total number of hydrophobic amino acid residues and proline residues to the total number of peptide residues is 2/3 or more. It may contain at least one of the peptides.
  • Peptides having a specific composition have a lactic acid bacterium growth effect.
  • the lactic acid bacterium growth promoting agent can exhibit an excellent lactic acid bacterium growth promoting effect.
  • amino acids in the present specification include amino acids used for protein synthesis, and they are preferably L-amino acids.
  • Amino acids used for protein synthesis are 20 kinds of amino acids encoded as codons on a gene.
  • Amino acids used in protein synthesis include hydrophobic amino acids, hydrophilic amino acids and proline (P).
  • Hydrophobic amino acids include aliphatic hydrophobic amino acids consisting of alanine (A), glycine (G), valine (V), isoleucine (I) and leucine (L), and phenylalanine (F), tyrosine (Y) and tryptophan.
  • hydrophilic amino acids include a basic hydrophilic amino acid composed of lysine (K), arginine (R) and histidine (H), an acidic hydrophilic amino acid composed of aspartic acid (D) and glutamine (E), and serine. It contains a neutral hydrophilic amino acid consisting of (S), threonine (T), aspartic acid (N) and glutamine (Q).
  • proline (P) is imino acid and may be referred to as a special amino acid in the present specification.
  • amino acids that make up the peptide contained in the lactic acid bacteria growth promoter are the above 20 amino acids used for protein synthesis; in addition to the amino acids used for protein synthesis, selenocysteine, pyrrolicin, N-formylmethionine, pyroglutamic acid, cystine, and hydroxy.
  • Amino acids that may constitute proteins including amino acids produced by post-translational modifications such as proline, hydroxylysine, tyrosin, O-phosphoserine; ⁇ -alanine, sarcosine, ornithine, citrulin, creatine, ⁇ -aminobutyric acid (GABA), opain, It may contain amino acids such as trimethylglycine, which are not normally contained in proteins.
  • the total number of residues of the first peptide and the second peptide contained in the lactic acid bacterium growth promoter may be 9 residues or less, preferably 8 residues or less, 7 residues or less, 6 residues or less, and 5 residues, respectively. It is less than a group or less than 4 residues.
  • the total number of residues of the first peptide and the second peptide may be 2 or more, preferably 3 or more, or 4 or more, respectively.
  • the total number of residues of the first peptide and the second peptide may be the same or different.
  • the first peptide has a hydrophobic amino acid residue at the C-terminal.
  • the hydrophobic amino acid residues possessed by the first peptide at the C-terminal are alanine (A), glycine (G), valine (V), isoleucine (I), leucine (L), phenylalanine (F), tyrosine (Y), and the like. It may be at least one selected from the group consisting of tryptophan (W), methionine (M) and cysteine (C).
  • the hydrophobic amino acid residue possessed by the first peptide at the C-terminal is preferably at least one selected from the group consisting of alanine (A), glycine (G), phenylalanine (F) and tyrosine (Y). , More preferably at least one selected from the group consisting of phenylalanine (F) and tyrosine (Y).
  • the first peptide may have a total number of residues of 6 or less and may have at least one hydrophobic amino acid residue selected from the group consisting of phenylalanine (F) and tyrosine (Y) at the C-terminus. ..
  • the first peptide is the ratio of the total number of hydrophobic amino acid residues and proline residues to the total number of residues ((number of hydrophobic amino acid residues + number of proline residues) / total number of residues; hereinafter, "specific residue”.
  • the "base ratio") may be 2/3 or more, and the specific residue ratio is preferably 3/4 or more.
  • the first peptide contains a peptide in which any one or two residues are inserted, deleted, substituted or added in the amino acid sequence of the following specific example and has a lactic acid bacterium growth promoting action. It's okay to have it.
  • the lactic acid bacterium growth promoter may contain the first peptide alone or in combination of two or more.
  • the second peptide has a total number of residues of 9 or less, and the ratio of the total number of hydrophobic amino acid residues and proline residues to the total number of residues of the peptide (specific residue ratio) is 2/3 or more. Yes, preferably the specific residue ratio is 3/4 or more, or 1.
  • the specific residue ratio of 1 means that the second peptide is composed of only hydrophobic amino acid residues and proline residues.
  • the total number of residues of the second peptide may be 6 or less, preferably 4 or less.
  • the total number of residues of the second peptide may be 2 or more, preferably 3 or more.
  • the second peptide may have a hydrophobic amino acid residue at the C-terminal.
  • Hydrophobic amino acid residues in the second peptide are alanine (A), glycine (G), valine (V), isoleucine (I), leucine (L), phenylalanine (F), tyrosine (Y), tryptophan (W).
  • Methionine (M) and cysteine (C) may be at least one selected from the group.
  • the hydrophobic amino acid residue in the second peptide is preferably at least one selected from the group consisting of alanine (A), glycine (G), phenylalanine (F) and tyrosine (Y), and more preferably. It is at least one selected from the group consisting of phenylalanine (F) and tyrosine (Y).
  • the second peptide includes a peptide in which any one residue or two residues are inserted, deleted, substituted or added in the amino acid sequence of the following specific example and has a lactic acid bacterium growth promoting action. It's okay to have it.
  • the lactic acid bacterium growth promoter may contain the second peptide alone or in combination of two or more.
  • the lactic acid bacterium growth promoter may further contain at least one of other peptides having a lactic acid bacterium growth action in addition to at least one selected from the group consisting of the first peptide and the second peptide. Specific examples of other peptides are shown below, but the present invention is not limited thereto.
  • the lactic acid bacterium growth promoter may contain other peptides alone or in combination of two or more.
  • the peptide contained in the lactic acid bacterium growth promoter may be selected, for example, by differential analysis of the components of the lactic acid bacterium culture medium having different production lots. Difference analysis of components can be performed, for example, using liquid chromatography-mass spectrometry (LC-MS).
  • LC-MS liquid chromatography-mass spectrometry
  • Examples of the lactic acid bacteria in the present specification include species belonging to Lactobacillus and Lactobacillus, such as Lactobacillus gasseri (for example, FERM BP-11331), Lactobacillus acidophilus (FERM BP-9481), and Lactobacillus. ⁇ Lactobacillus amylovorus (FERM BP-11255), Lactobacillus curvatus (NITE P-02033), Lactobacillus plantarum, Lactobacillus blevis (Lactobacillus brevis) casei), Lactobacillus paracasei, Lactobacillus rhamnosus, Lactobacillus helveticus, Lactobacillus fermentum, Lactobacillus fermentum, Lactobacillus fermentum Lactobacillus plantarum, Lactobacillus salivarius, Lactobacillus reuteri, Lactobacillus johnsonii, Lactobacillus johnsonii, Lactobacillus john
  • the lactic acid bacterium may be at least one selected from the group consisting of Lactobacillus gasseri, Lactobacillus acidophilus, Lactobacillus amyloboras, Lactobacillus carbatas, Lactobacillus plantum and Lactobacillus brevis. ..
  • the growth promoting effect of lactic acid bacteria by the lactic acid bacterium growth promoting agent may be larger than, for example, 100%, preferably 105% or more, 110% or more, or 120% or more when the growth rate of the control is 100%. May be.
  • the growth promoting effect of lactic acid bacteria can be evaluated by the rate of increase in the number of cells after anaerobic culture at 37 ° C. for 18 hours by adding a lactic acid bacterium growth promoting agent to the medium at 0.25 mg / mL.
  • the peptide contained in the lactic acid bacterium growth promoter can be obtained, for example, by allowing an appropriate protease to act on a protein such as food. It can also be obtained by separating from meat extract, yeast extract and the like. Furthermore, it can also be obtained by chemical synthesis. A commonly used method can be appropriately adopted for the chemical synthesis of the peptide.
  • the lactic acid bacterium growth promoter can be used for the production of lactic acid bacteria, the production of fermented products using lactic acid bacteria, and the like.
  • lactic acid bacteria are cultured in an appropriate medium to which a lactic acid bacterium growth promoter is added in a predetermined amount.
  • the amount of the lactic acid bacterium growth promoter added to the medium may be, for example, 0.001 mg / mL or more and 25 mg / mL or less, preferably 0.01 mg / mL or more and 10 mg / mL or less, and more preferably 0.1 mg. / ML or more and 2.5 mg / mL or less.
  • meat extract, yeast extract, soymilk, skim milk powder, sucrose, inorganic salts and the like can be appropriately selected and contained in the medium in a predetermined amount.
  • the temperature can be set to about 25 ° C. or higher and about 40 ° C. or lower
  • the pH can be set to about 5 or higher and about 6.5 or lower
  • anaerobic conditions such as a nitrogen gas atmosphere can be used.
  • the initial concentration of lactic acid bacteria may be, for example, 1 ⁇ 10 4 or more / mL medium, preferably 1 ⁇ 10 5 or more / mL medium.
  • the culture time may be, for example, 4 hours or more, preferably 6 hours or more and 48 hours or less.
  • the culture method can be appropriately selected from commonly used culture methods such as static culture, stirring culture, and shaking culture. Lactic acid bacteria can be recovered from the culture medium after culturing using a separation device such as centrifugation.
  • Examples of fermented products using lactic acid bacteria include fermented milk and silage.
  • Fermented milk can be obtained by adding lactic acid bacteria and a lactic acid bacterium growth promoter to milk and fermenting the milk with lactic acid.
  • Silage is an animal feed in which green-cut forage crops (grass, corn, etc.) are packed in silos, lactic acid fermented, and stored.
  • the present invention also includes the use of a lactic acid bacterium growth promoter in the production of lactic acid bacteria or the production of fermented products using lactic acid bacteria.
  • another aspect of the present invention comprises the use of at least one peptide selected from the group consisting of the first peptide and the second peptide in the production of a lactic acid bacterium growth promoter, the first peptide and the second peptide in the lactic acid bacterium culture.
  • the use of at least one peptide selected from the group also includes at least one peptide selected from the group consisting of first and second peptides used in lactic acid bacteria culture.
  • Example 1 Proliferation-promoting effect on Lactobacillus gasseri (FERM BP-11331) Twenty-eight candidate peptides shown in the following sequences were prepared by chemical synthesis. The candidate peptide was added to the modified MRS medium at 0.25 mg / mL to prepare a medium for evaluation. The lactic acid bacterium Lactobacillus gasseri was inoculated in the prepared evaluation medium at 1.0 ⁇ 10 7 cells / mL, and cultured at a temperature of 37 ° C. and a culture time of 18 hours.
  • the culture broth after culturing was collected, and the particle concentration (pieces / mL) was measured using a particle counting analyzer (CDA-1000, Sysmex) as a characteristic value as an index of cell growth.
  • the rate of increase (%) was determined when the value of the control using the peptide-free medium was set to 100%. The results are shown in the table below.
  • Example 2 Proliferation-promoting effect on Lactobacillus acidophilus (FERM BP-9481)
  • Lactobacillus acidophilus was used instead of Lactobacillus gasseri.
  • the growth promoting effect on lactic acid bacteria was evaluated. The results are shown in the table below.
  • Example 3 Proliferation-promoting effect on Lactobacillus amylobolus (FERM BP-11255)
  • Lactobacillus amyloboras was used instead of Lactobacillus gasseri.
  • the growth promoting effect on lactic acid bacteria was evaluated. The results are shown in the table below.
  • Example 4 Proliferation-promoting effect on Lactobacillus carbatas (NITE P-02033)
  • Lactobacillus carbatas was used instead of Lactobacillus gasseri.
  • the growth promoting effect on lactic acid bacteria was evaluated. The results are shown in the table below.
  • Example 5 Growth-promoting effect on Lactobacillus plantarum
  • the growth promotion effect on lactic acid bacteria was the same as in Example 1 except that Lactobacillus plantarum was used instead of Lactobacillus gasseri for the eight candidate peptides shown in the sequence below. The effect was evaluated. The results are shown in the table below.
  • Example 6 Growth-promoting effect on Lactobacillus brevis The growth-promoting effect on lactic acid bacteria was exhibited in the same manner as in Example 1 except that Lactobacillus brevis was used instead of Lactobacillus gasseri for the eight candidate peptides shown in the sequence below. evaluated. The results are shown in the table below.
  • Example 7 A dipeptide (LF) was used as the peptide, and the growth promoting effect on lactic acid bacteria was evaluated in the same manner except that the addition concentration was changed to 0.1 mg / mL, 0.25 mg / mL or 1.0 mg / mL. The results are shown in the table below.

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PCT/JP2021/020796 2020-06-02 2021-06-01 乳酸菌増殖促進剤 Ceased WO2021246392A1 (ja)

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Application Number Priority Date Filing Date Title
US17/920,598 US20230151057A1 (en) 2020-06-02 2021-06-01 Lactic acid bacteria growth promoter
CN202180034794.1A CN115551991A (zh) 2020-06-02 2021-06-01 乳酸菌增殖促进剂
AU2021282621A AU2021282621A1 (en) 2020-06-02 2021-06-01 Lactic acid bacteria growth promoter
JP2022528836A JP7802665B2 (ja) 2020-06-02 2021-06-01 乳酸菌増殖促進剤
EP21818873.8A EP4159742A4 (en) 2020-06-02 2021-06-01 LACTIC ACID BACTERIA GROWTH PROMOTER

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Cited By (1)

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WO2024038345A1 (en) * 2022-08-19 2024-02-22 Lubrizol Advanced Materials, Inc. Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes

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