WO2021050394A1 - Bloqueurs du récepteur de goût amer et procédés pour leur identification - Google Patents

Bloqueurs du récepteur de goût amer et procédés pour leur identification Download PDF

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Publication number
WO2021050394A1
WO2021050394A1 PCT/US2020/049542 US2020049542W WO2021050394A1 WO 2021050394 A1 WO2021050394 A1 WO 2021050394A1 US 2020049542 W US2020049542 W US 2020049542W WO 2021050394 A1 WO2021050394 A1 WO 2021050394A1
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WO
WIPO (PCT)
Prior art keywords
equivalent
polypeptide
compound
seq
bitter
Prior art date
Application number
PCT/US2020/049542
Other languages
English (en)
Inventor
Guy Servant
Mark Williams
Lan Zhang
Original Assignee
Firmenich Incorporated
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich Incorporated filed Critical Firmenich Incorporated
Priority to EP20772185.3A priority Critical patent/EP3987288A1/fr
Priority to CN202080054943.6A priority patent/CN114207441A/zh
Priority to JP2022506268A priority patent/JP2022546204A/ja
Priority to BR112022001671A priority patent/BR112022001671A2/pt
Priority to US17/630,757 priority patent/US20220236254A1/en
Publication of WO2021050394A1 publication Critical patent/WO2021050394A1/fr

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
    • G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/566—Immunoassay; Biospecific binding assay; Materials therefor using specific carrier or receptor proteins as ligand binding reagents where possible specific carrier or receptor proteins are classified with their target compounds
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
    • G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
    • G01N2333/72—Assays involving receptors, cell surface antigens or cell surface determinants for hormones
    • G01N2333/726—G protein coupled receptor, e.g. TSHR-thyrotropin-receptor, LH/hCG receptor, FSH

Definitions

  • the disclosure provides a polypeptide sequence of SEQ ID NO: 2, or a functional fragment thereof, or a polypeptide sequence whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, to either of the foregoing.
  • the ingestible composition is a composition derived from citrus fruit. In some embodiments, the ingestible composition is a naturally occurring composition. In some other embodiments, the ingestible composition is a non-naturally occurring composition. In some such embodiments, the PMFs are selected from the group consisting of sinensetin, 4’-hydroxy-sinensetin, quercetogetin, nobiletin, tangeretin, heptamethoxyflavone, and any combinations thereof.
  • the bitter compounds are compounds that modulates (e.g., activates) a polypeptide sequence of SEQ ID NO: 2, or a functional fragment thereof, or a polypeptide sequence whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, to either of the foregoing.
  • the bitter compounds are limonoids, such as limonin, nomilin, nomilinic acid, or any combination thereof.
  • the bitter compounds are compounds that modulates (e.g., activates) a polypeptide sequence of SEQ ID NO: 2, or a functional fragment thereof, or a polypeptide sequence whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, to either of the foregoing.
  • the bitter compounds are limonoids, such as limonin, nomilin, nomilinic acid, or any combination thereof.
  • optional event means that the subsequently described event(s) may or may not occur. In some embodiments, the optional event does not occur. In some other embodiments, the optional event does occur one or more times.
  • polypeptide sequence corresponding to SEQ ID NO: 2 is: MITFLPIIFSILIVVIFVIGNFANGFIALVNSIEWVKRQKISFVDQILT ALA VSRV GLLWVLLLHWY ATQLNPAFY S VEVRIT AYNVWAVTNHFS S WLATSL SMFYLLRIANFSNLIFLRIKRRVKSVVLVILLGPLLFLVCHLFVINMDETVWTKEYEG NVTWKIKLRSAMYHSNMTLTMLANFVPLTLTLISFLLLICSLCKHLKKMQLHGKGSQ DPSTKVHIKALQTVTSFLLLCAIYFLSMIISVCNLGRLEKQPVFMFCQAIIFSYPSTHPFI LILGNKKLKQIFLSVLRHVRYWVKDRSLRLHRFTRGALCVF, using the standard single letter amino acid codes.
  • polypeptide sequences of the foregoing aspects and embodiments can be present in any suitable composition.
  • one or more polypeptide sequences of the foregoing aspects and embodiments is present in a non-naturally occurring composition, such as an in vitro assay.
  • the polypeptide sequences of the foregoing aspects and embodiments are expressed on the surface of cells, such as on the cells of a eukaryotic cell line.
  • the disclosure provides methods of identifying compounds that reduce bitter taste, the method comprising: introducing a test compound and a bitter compound to one or more taste receptor proteins, wherein the one or more taste receptor proteins are polypeptides that comprise: a polypeptide sequence of SEQ ID NO: 1, or a functional fragment thereof; a polypeptide sequence of SEQ ID NO: 2, or a functional fragment thereof; a polypeptide sequence of SEQ ID NO: 3, or a functional fragment thereof; a polypeptide sequence of SEQ ID NO: 4, or a functional fragment thereof; a polypeptide sequence of SEQ ID NO: 5, or a functional fragment thereof; or a polypeptide sequence whose sequence is at least 90% equivalent to any of the foregoing; and measuring a response of each of the one or more taste receptor proteins to the test compound by comparing an activity of the one or more taste receptor proteins to the bitter compound in the presence and the absence of the test compound.
  • the one or more taste receptor proteins are polypeptides that comprise: a polypeptide sequence of SEQ ID NO: 1,
  • the first taste receptor protein is a polypeptide that comprises a polypeptide sequence of SEQ ID NO: 2, or a polypeptide whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, thereto
  • the second taste receptor protein is a polypeptide that comprises a polypeptide sequence of SEQ ID NO: 3, or a polypeptide whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, thereto.
  • the introducing and measuring can involve any combination of four different taste receptor proteins, such as: a polypeptide that comprises a polypeptide sequence of SEQ ID NO: 1, a functional fragment thereof, or a polypeptide whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, to either of the foregoing; a polypeptide that comprises a polypeptide sequence of SEQ ID NO: 2, a functional fragment thereof, or a polypeptide whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, to either of the foregoing; a polypeptide that comprises a polypeptide sequence of SEQ ID NO: 3, a functional fragment thereof, or a polypeptide whose sequence is at least 90% equivalent, or at least 95% equivalent, or at least 97% equivalent, to either of the foregoing, and a polypeptide that comprises a polypeptide sequence of SEQ ID NO: 4, a functional fragment thereof, or a polypeptide whose sequence is at least 90% equivalent, or
  • the methods further comprise identifying an active test compound that reduces bitter taste based on the measured response.
  • the identified active test compound is one that antagonizes the binding of the bitter compound to one, two, three, four, or five of the taste receptor proteins.
  • the identified active test compound is a compound that antagonizes the binding of the bitter compound to one of the foregoing taste receptor proteins.
  • the identified active test compound is a compound that antagonizes the binding of the bitter compound to two of the foregoing different combinations of taste receptor proteins.
  • the identified active test compound is a compound that antagonizes the binding of the bitter compound to three of the foregoing different combinations of taste receptor proteins.
  • the disclosure provides uses of any identified or selected active compounds of the foregoing aspects, including any embodiments or combination of embodiments thereof, as set forth above. In certain related aspects, the disclosure provides uses of any identified or selected active compounds of the foregoing aspects, including any embodiments or combination of embodiments thereof, as set forth above, to enhance the sweetness of an ingestible composition. In some embodiments thereof, the ingestible composition comprises a sweetener, such as a caloric sweetener. In certain other related aspects, the disclosure provides uses of any identified or selected active compounds of the foregoing aspects, including any embodiments or combination of embodiments thereof, as set forth above, to reduce the sourness of an ingestible composition.
  • a sweetener such as a caloric sweetener
  • the disclosure provides methods of reducing the bitterness of an ingestible composition, comprising introducing an amount (such as a bitterness- reducing effective amount) of polymethoxyflavones (PMFs) to an ingestible composition.
  • the ingestible composition comprises one or more bitter compounds.
  • the ingestible composition is a composition derived from citrus fruit.
  • the ingestible composition is a naturally occurring composition. In some other embodiments, the ingestible composition is a non- naturally occurring composition.
  • compounds as disclosed and described herein, individually or in combination can be provided in a composition, such as an ingestible composition.
  • compounds as disclosed and described herein, individually or in combination can impart a more sugar- like temporal profile or flavor profile to a sweetener composition by combining one or more of the compounds as disclosed and described herein with one or more sweeteners in the sweetener composition.
  • compounds as disclosed and described herein, individually or in combination can increase or enhance the sweet taste of a composition by contacting the composition thereof with the compounds as disclosed and described herein to form a modified composition.
  • the sweetener is present in an amount from about 0.1% to about 12% by weight. In some embodiments, the sweetener is present in an amount from about 0.2% to about 10% by weight. In some embodiments, the sweetener is present in an amount from about 0.3% to about 8% by weight. In some embodiments, the sweetener is present in an amount from about 0.4% to about 6% by weight. In some embodiments, the sweetener is present in an amount from about 0.5% to about 5% by weight. In some embodiments, the sweetener is present in an amount from about 1% to about 2% by weight.
  • the sweetener may be a natural or synthetic sweetener that includes, but is not limited to, agave inulin, agave nectar, agave syrup, amazake, brazzein, brown rice syrup, coconut crystals, coconut sugars, coconut syrup, date sugar, fructans (also referred to as inulin fiber, fructo-oligosaccharides, or oligo-fructose), green stevia powder, stevia rebaudiana, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M and other sweet stevia-based glycosides, stevioside, stevioside extracts, honey, Jerusalem artichoke syrup, licorice root,
  • food and beverage products or formulations include sweet coatings, frostings, or glazes for such products or any entity included in the Soup category, the Dried Processed Food category, the Beverage category, the Ready Meal category, the Canned or Preserved Food category, the Frozen Processed Food category, the Chilled Processed Food category, the Snack Food category, the Baked Goods category, the Confectionery category, the Dairy Product category, the Ice Cream category, the Meal Replacement category, the Pasta and Noodle category, and the Sauces, Dressings, Condiments category, the Baby Food category, and/or the Spreads category.
  • the chewable composition may be gum, chewing gum, sugarized gum, sugar-free gum, functional gum, bubble gum including compounds as disclosed and described herein, individually or in combination.
  • the flavoring concentrate formulation is typically used by mixing with or diluted by one or more diluting medium, e.g., any consumable or ingestible ingredient or product, to impart or modify one or more flavors to the diluting medium.
  • a use process is often referred to as reconstitution.
  • the reconstitution can be conducted in a household setting or an industrial setting.
  • a frozen fruit juice concentrate can be reconstituted with water or other aqueous medium by a consumer in a kitchen to obtain the ready-to-use fruit juice beverage.
  • a soft drink syrup concentrate can be reconstituted with water or other aqueous medium by a manufacturer in large industrial scales to produce the ready-to-use soft drinks.
  • the flavored products set forth according to any of the foregoing embodiments also include, in certain embodiments, one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness, compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • additional flavor-modifying compounds such as compounds that enhance sweetness (e.g., hesperetin, naringenin, glucosylated steviol glycosides, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness, compounds that enhance saltiness, compounds that enhance a cooling effect, or any combinations of the foregoing.
  • the nucleating agent denotes an ingestibly acceptable compound or agent which is able to facilitate nucleation.
  • the presence of nucleating agent in the flavoring concentrate formulation can improve the mouthfeel of the frozen Blushes of a frozen slush and to help maintain the physical properties and performance of the slush at freezing temperatures by increasing the number of desirable ice crystallization centers.
  • nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Chemical & Material Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Cell Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Pathology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Physics & Mathematics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Toxicology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Peptides Or Proteins (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
  • Seasonings (AREA)

Abstract

La présente invention concerne de manière générale des procédés d'identification de composés qui bloquent les récepteurs de goût amer, en particulier les récepteurs de goût amer activés par certains composés couramment présents dans les extraits d'agrumes. L'invention concerne également des compositions comprenant de tels composés, et des procédés d'utilisation de ceux-ci.
PCT/US2020/049542 2019-09-09 2020-09-04 Bloqueurs du récepteur de goût amer et procédés pour leur identification WO2021050394A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP20772185.3A EP3987288A1 (fr) 2019-09-09 2020-09-04 Bloqueurs du récepteur de goût amer et procédés pour leur identification
CN202080054943.6A CN114207441A (zh) 2019-09-09 2020-09-04 苦味受体阻滞剂及其鉴定方法
JP2022506268A JP2022546204A (ja) 2019-09-09 2020-09-04 苦味受容体ブロッカー及びその同定方法
BR112022001671A BR112022001671A2 (pt) 2019-09-09 2020-09-04 Bloqueadores de receptores de sabor amargo e métodos de identificação destes
US17/630,757 US20220236254A1 (en) 2019-09-09 2020-09-04 Bitter taste receptor blockers and methods of their identification

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US201962897844P 2019-09-09 2019-09-09
US62/897,844 2019-09-09
EP19216401 2019-12-16
EP19216401.0 2019-12-16
US202063010655P 2020-04-15 2020-04-15
US63/010,655 2020-04-15

Publications (1)

Publication Number Publication Date
WO2021050394A1 true WO2021050394A1 (fr) 2021-03-18

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PCT/US2020/049542 WO2021050394A1 (fr) 2019-09-09 2020-09-04 Bloqueurs du récepteur de goût amer et procédés pour leur identification

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EP (1) EP3987288A1 (fr)
JP (1) JP2022546204A (fr)
CN (1) CN114207441A (fr)
BR (1) BR112022001671A2 (fr)
WO (1) WO2021050394A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023107904A1 (fr) * 2021-12-07 2023-06-15 Firmenich Incorporated Réduction du goût amer de protéines végétales et procédés de dosage et de criblage associés

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7320593B2 (ja) * 2021-12-28 2023-08-03 花王株式会社 デメチルノビレチンの製造方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6468576B1 (en) 2000-06-23 2002-10-22 Nestec S.A. Frozen slush liquid concentrate and method of making same
WO2004069191A2 (fr) * 2003-02-03 2004-08-19 Senomyx Inc. Couplage fonctionnel de t1rs et de t2rs par des proteines gi, et dosages a base de cellules pour l'identification de modulateurs de t1r et t2r
US20080187936A1 (en) * 2001-04-05 2008-08-07 Senomyx, Inc. Identification of bitter ligands that specifically activate human t2r receptors and related assays for identifying human bitter taste modulators
WO2012146584A2 (fr) 2011-04-29 2012-11-01 Symrise Ag Vanillyllignanes particulières et leur utilisation comme agents d'amélioration gustative
WO2013072332A1 (fr) * 2011-11-14 2013-05-23 Givaudan Sa Procédés d'utilisation d'antagonistes de récepteurs du goût amer
US20160069860A1 (en) * 2013-04-24 2016-03-10 Chromocell Corporation Assays for identifying compounds that modulate bitter taste

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6468576B1 (en) 2000-06-23 2002-10-22 Nestec S.A. Frozen slush liquid concentrate and method of making same
US20080187936A1 (en) * 2001-04-05 2008-08-07 Senomyx, Inc. Identification of bitter ligands that specifically activate human t2r receptors and related assays for identifying human bitter taste modulators
WO2004069191A2 (fr) * 2003-02-03 2004-08-19 Senomyx Inc. Couplage fonctionnel de t1rs et de t2rs par des proteines gi, et dosages a base de cellules pour l'identification de modulateurs de t1r et t2r
WO2012146584A2 (fr) 2011-04-29 2012-11-01 Symrise Ag Vanillyllignanes particulières et leur utilisation comme agents d'amélioration gustative
WO2013072332A1 (fr) * 2011-11-14 2013-05-23 Givaudan Sa Procédés d'utilisation d'antagonistes de récepteurs du goût amer
US20160069860A1 (en) * 2013-04-24 2016-03-10 Chromocell Corporation Assays for identifying compounds that modulate bitter taste

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MEYERHOF W. ET AL.: "The molecular receptive ranges of human TAS2R bitter taste receptors", CHEM. SENSES, vol. 35, no. 2, February 2010 (2010-02-01), pages 157 - 170, XP009139503 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023107904A1 (fr) * 2021-12-07 2023-06-15 Firmenich Incorporated Réduction du goût amer de protéines végétales et procédés de dosage et de criblage associés

Also Published As

Publication number Publication date
JP2022546204A (ja) 2022-11-04
EP3987288A1 (fr) 2022-04-27
BR112022001671A2 (pt) 2022-03-22
CN114207441A (zh) 2022-03-18

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