# US 12,006,524 B2 · Method for producing urolithins > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,006,524 B2 - Document ID: US12006524B2 - Status: Granted - Kind: B2 - Application number: 16/473,385 - Filed: 2017-12-26 - Published: 2019-10-24 - Granted: 2024-06-11 - Earliest claimed: 2016-12-26 - Assignees: Daicel Corporation - Applicants: Daicel Corporation - Inventors: Masatake Kudoh; Takanori Nakajima; Hiroaki Yamamoto - Web page: https://patentgrep.com/patent/US12006524B2 ## CPC - C12P 7/22: aromatic - C12P 17/06: containing a six-membered hetero ring, e.g. fluorescein - A23L 33/105: Plant extracts, their artificial duplicates or their derivatives - C12N 1/205: Bacterial isolates - A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs - C12R 2001/01: Bacteria or Actinomycetales {; using bacteria or Actinomycetales} - C12R 2001/145: Clostridium - C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)} - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) - C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00) - A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION - C12R: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS ## Abstract An object of the present invention is to provide a method for eliminating the hydroxyl group at the 9-position of a urolithin to produce another kind of urolithin. This object is achieved by a method for producing a second urolithin, including Step (a): allowing, in a solution containing a first urolithin, a microorganism having an ability to produce the second urolithin from the first urolithin to produce the second urolithin from the first urolithin. ## Claims ### Claim 1 A method for producing a second urolithin represented by the following General Formula (2), comprising the following Step (a): Step (a): allowing, in a solution containing a first urolithin represented by the following General Formula (1), a microorganism having an ability to produce the second urolithin represented by the following General Formula (2) from the first urolithin to produce the second urolithin from the first urolithin wherein R1 to R7 each represent a hydroxyl group, a hydrogen atom, or a methoxy group, and at least one of R1 to R7 represents a hydroxy group wherein R1 to R7 are identical to the R1 to R7, respectively, of the first urolithin represented by the General Formula (1), wherein the only microorganism in said solution having an ability to produce the second urolithin from the first urolithin is a microorganism belonging to the genus Clostridium. ### Claim 2 (depends on 1) The production method according to claim 1, wherein the combination of the first urolithin and the second urolithin is a combination of urolithin M5 and urolithin E, respectively, a combination of urolithin M6 and urolithin M7, respectively, a combination of urolithin C and urolithin A, respectively, or a combination of isourolithin A and urolithin B, respectively. ### Claim 3 (depends on 1) The production method according to claim 1, wherein the microorganism belonging to the genus Clostridium is at least one selected from the group consisting of a microorganism belonging to Clostridium bolteae, a microorganism belonging to Clostridium asparagiforme, and a microorganism belonging to Clostridium citroniae. ### Claim 4 (depends on 3) The production method according to claim 3, wherein the microorganism belonging to Clostridium bolteae is at least one selected from the group consisting of the Clostridium bolteae JCM 12243 strain, DSM 15670 strain, and DSM 29485 strain. ### Claim 5 (depends on 3) The production method according to claim 3, wherein the microorganism belonging to Clostridium asparagiforme is the Clostridium asparagiforme DSM 15981 strain. ### Claim 6 (depends on 3) The production method according to claim 3, wherein the microorganism belonging to Clostridium citroniae is the Clostridium citroniae DSM 19261 strain. ### Claim 7 (depends on 2) The production method according to claim 2, wherein the combination of the first urolithin and the second urolithin is a combination of urolithin C and urolithin A, respectively. ### Claim 8 (depends on 7) The production method according to claim 7, wherein the urolithin C is obtained by allowing, in a solution containing a raw material of urolithin C, a microorganism having an ability to produce urolithin C from the raw material of urolithin C that is different from said Clostridium having an ability to produce the second urolithin from the first urolithin to produce urolithin C from the raw material of urolithin C. ### Claim 9 (depends on 7) The production method according to claim 7, further comprising the following Step (b1): Step (b1): allowing, in a solution containing a raw material of urolithin C, a microorganism having an ability to produce urolithin C from the raw material of urolithin C that is different from said Clostridium having an ability to produce the second urolithin from the first urolithin to produce urolithin C from the raw material of urolithin C; wherein the Step (a) and the Step (b1) are carried out in the same system. ### Claim 10 (depends on 8) The production method according to claim 8, wherein the microorganism having an ability to produce urolithin C from the raw material of urolithin C is a microorganism belonging to the genus Gordonibacter. ### Claim 11 (depends on 10) The production method according to claim 10, wherein the microorganism belonging to the genus Gordonibacter is a microorganism belonging to Gordonibacter pamelaeae and/or a microorganism belonging to Gordonibacter urolithinfaciens. ### Claim 12 (depends on 11) The production method according to claim 11, wherein the microorganism belonging to Gordonibacter pamelaeae is the Gordonibacter pamelaeae DSM 19378 strain. ### Claim 13 (depends on 11) The production method according to claim 11, wherein the microorganism belonging to Gordonibacter urolithinfaciens is the Gordonibacter urolithinfaciens DSM 27213 strain. ### Claim 14 (depends on 8) The production method according to claim 8, wherein the raw material of urolithin C is ellagic acid and/or ellagitannin. ### Claim 15 (depends on 1) The production method according to claim 1, wherein the Step (a) is carried out in an environment with a gas phase containing hydrogen. ### Claim 16 (depends on 15) The production method according to claim 15, wherein the ratio of the hydrogen in the gas phase is not less than 0.5% and not more than 20%. ### Claim 17 (depends on 7) The production method according to claim 7, wherein, in the Step (a), the solution containing urolithin C further contains at least one selected from the group consisting of inclusion compounds of α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin. ### Claim 18 (depends on 9) The production method according to claim 9, wherein, in the Step (b1), the solution containing the raw material of urolithin C further contains at least one selected from the group consisting of inclusion compounds of α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin.