Table 1.
Flavonoid classes, bacterial conversion reactions, active human gut bacteria, their flavonoid substrates and resulting products.
| Flavonoid class | Conversion reaction | Species/straina (former reported name) | Substrate(s) | Product(s) | Reference |
|---|---|---|---|---|---|
| Flavonols / flavanonols | O-Deglycosylation | Bacteroides uniformis ATCC 8492T, B. uniformis strain | Rutin (quercetin-3-O-glucorhamnoside) | Quercetin | 85 |
| Bacteroides ovatus ATCC 8483T, B. ovatus strain | Rutin | Quercetin | 85 | ||
| Parabacteroides distasonis (Bacteroides distasonis) strain | Rutin | Quercetin-3-O-glucoside | 85 | ||
| Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside) | Kaempferol | ||||
| Enterococcus casseliflavus M1 | Isoquercetin (quercetin-3-O-glucoside) | Quercetin | 16 | ||
| Eubacterium ramulus DSM 16296 | Isoquercetin | Quercetin | 16,17 | ||
| Rutin | 3,4-Dihydroxyphenylacetic acid | ||||
| Enterococcus avium LY1 | Rutin | Quercetin | 38 | ||
| Bifidobacterium pseudocatenulatum B7003, B. longum ssp. infantis (B. infantis) B7875, B. catenulatum B7377, B. breve B7824 | Kaempferol-3-O-glucoside | Kaempferol | 31 | ||
| Blautia sp. MRG-PMF1 | Rutin | Quercetin | 36 | ||
| Bifidobacterium dentium K13 | Rutin | NDb | 32 | ||
| Enterococcus avium EFEL009 | Rutin | Isoquercetin, quercetin | 39 | ||
| C-Ring cleavage | Flavonifractor plautii (Clostridium orbiscindens) strains ATCC 49531, 257, 258 and 264 | Quercetin | 3,4-Dihydroxyphenylacetic acid | 86 | |
| Eubacterium ramulus DSM 16296 | Quercetin | Taxifolin, alphitonin, 3,4-dihydroxyphenylacetic acid, phloroglucinol, acetate, butyrate | 16,17,20 | ||
| Taxifolin | 3,4-Dihydroxyphenylacetic acid | ||||
| Kaempferol | 4-Hydroxyphenylacetic acid | ||||
| Eggerthella (Eubacterium) sp. SDG-2 | Taxifolin | α,2′,3,4,4′,6′-Hexahydroxydihydrochalcone | 56 | ||
| Flavonifractor plautii (Clostridium orbiscindens) I2 | Quercetin, taxifolin | 3,4-Dihydroxyphenylacetic acid | 21 | ||
| Flavones / flavanones | O-Deglycosylation | Parabacteroides distasonis (Bacteroides distasonis) JCM 5825T, Bacteroides uniformis JCM 5828, Bifidobacterium adolescentis JCM 1275, B. bifidum IFO 14252, Lactobacillus plantarum IAM 12477, L. acidophilus strain, L. buchneri strain, L. casei strain, L. leichmanii strain, Enterococcus faecalis (Streptococcus faecalis) IFO 12964, Lactococcus lactis (Streptococcus lactis) strain, Enterobacter cloacae IAM 12349 | Eriocitrin (eriodictyol-7-O-rutinoside) | Eriodictyol | 27 |
| Eubacterium ramulus DSM 16296 | Luteolin-7-O-glucoside | 3-(3,4-Dihydroxyphenyl)propionic acid | 17 | ||
| Strain CG19-1 | Luteolin-5-O-glucoside, luteolin-7-O-glucoside, luteolin-3′-O-glucoside | Luteolin | 37 | ||
| Apigenin-7-O-glucoside (apigetrin) | Apigenin | ||||
| Eubacterium cellulosolvens ATCC 43171T | Luteolin-7-O-glucoside, luteolin-3′-O-glucoside | Luteolin | 33 | ||
| Apigenin-7-O-glucoside | Apigenin | ||||
| Escherichia sp. 4 | Diosmetin-7-O-glucoside | Diosmetin | 58 | ||
| Blautia sp. MRG-PMF1 | Apigenin-7-O-glucoside | Apigenin | 36 | ||
| Hesperetin-7-O-rutinoside (hesperidin) | Hesperetin | ||||
| Bifidobacterium catenulatum ATCC 27539T, B. breve WC 0422, B. pseudocatenulatum strains WC 0400, WC 0401, WC 0403, WC 0407 and WC 0408 | Hesperetin-7-O-rutinoside | Hesperetin | 48 | ||
| Bifidobacterium dentium K13 | Isosakuranetin-7-O-neohesperidoside (poncirin) | ND | 32 | ||
| Naringenin-7-O-neohesperidoside (naringin) | ND | ||||
| Lactococcus sp MRG-IFC-1, Enterococcus sp. MRG-IFC-2, Lactococcus sp. MRG-IF-3 | Apigenin-7-O-glucoside | Apigenin | 40 | ||
| C-Deglycosylation | Strain CG19-1 | Luteolin-6-C-glucoside (homoorientin), luteolin-8-C-glucoside (orientin) | Luteolin | 37 | |
| Apigenin-8-C-glucoside (vitexin), apigenin-6-C-glucoside (isovitexin) | Apigenin | ||||
| Eubacterium cellulosolvens ATCC 43171T | Luteolin-6-C-glucoside | Luteolin | 33 | ||
| Apigenin-6-C-glucoside | Apigenin | ||||
| Enterococcus sp. 45 | Luteolin-8-C-glucoside | Luteolin | 50 | ||
| O-Demethylation | Eubacterium limosum strains DSM 20543T and LMG P23546 | Isoxanthohumol | 8-Prenylnaringenin | 51,52 | |
| Blautia sp. MRG-PMF1 | Hesperetin | Eriodictyol | 36 | ||
| 5,7-Dimethoxyflavone | 5,7-Dihydroxyflavone (chrysin) | ||||
| 5,7,4′-Trimethoxyflavone | 5,7,4′-Trihydroxyflavone (apigenin) | ||||
| Dehydroxylation | Escherichia sp. 4 | Diosmetin | Acacetin | 58 | |
| C-Ring cleavage | Clostridium butyricum IFO 13949T | Eriodictyol | 3-(3,4-Dihydroxyphenyl)propionic acid | 27 | |
| Eubacterium ramulus DSM 16296 | Luteolin, eriodictyol | 3-(3,4-Dihydroxyphenyl)propionic acid | 17,20 | ||
| Naringenin | 3-(4-Hydroxyphenyl)propionic acid | ||||
| Flavonifractor plautii (Clostridium orbiscindens) I2 | Luteolin, eriodictyol | 3-(3,4-Dihydroxyphenyl)propionic acid | 21 | ||
| Apigenin, naringenin | 3-(4-Hydroxyphenyl)propionic acid | ||||
| Strain CG19-1 | Luteolin | 3-(3,4-Dihydroxyphenyl)propionic acid | 37 | ||
| Apigenin | 3-(4-Hydroxyphenyl)propionic acid | ||||
| Dihydrochalcones | O-Deglycosylation | Eubacterium ramulus DSM 16296 | Hesperetin dihydrochalcone-4′-O-glucoside | Hesperetin dihydrochalcone | 34 |
| Cleavage | Eubacterium ramulus DSM 16296 | Phloretin | 3-(4-Hydroxyphenyl)propionic acid | 17 | |
| Hesperetin dihydrochalcone | 3-(3-Hydroxy-4-methoxyphenyl)propionic acid | 34 | |||
| Flavonifractor plautii (Clostridium orbiscindens) I2 | Phloretin | 3-(4-Hydroxyphenyl)propionic acid | 21 | ||
| Hesperetin dihydrochalcone | 3-(3-Hydroxy-4-methoxyphenyl)propionic acid | 34 | |||
| Isoflavones / isoflavanones | O-Deglycosylation | E. coli ATCC BAA-97 (strain HGH21) | Daidzin | Daidzein | 87 |
| Genistin | Genistein | ||||
| Eubacterium ramulus DSM 16296 | Genistin | Genistein | 35 | ||
| Bifidobacterium animalis strain, B. longum strain, B. pseudolongum strain | Daidzin, acetyldaidzin, malonyldaidzin | Daidzein | 30 | ||
| Bifidobacterium pseudocatenulatum B7003, B. longum ssp. infantis (B. infantis) B7875, B. catenulatum B7377, B. breve B7824 | Daidzin | Daidzein | 31 | ||
| Genistin | Genistein | ||||
| Glycitin | Glycitein | ||||
| Strain TM-40 | Daidzin | Daidzein | 75 | ||
| Bifidobacterium adolescentis strains DSM 18350, DSM 18353, MB 114, MB 237 and MB 243, B. bifidum strains MB 110 and 254, B. breve strains DSM 18352, MB 113, MB 234 and MB 235, B. longum ssp. infantis (B. infantis) MB 208, B. animalis ssp. lactis (B. lactis) MB 238, B. longum strains MB 201, MB 207, MB 217, MB 218 and MB 219, B. pseudocatenulatum MB 264, B. angulatum MB 223 | Daidzin | Daidzein | 28 | ||
| Strain CG19-1 | Daidzin | Daidzein | 37 | ||
| Genistin | Genistein | ||||
| Eubacterium cellulosolvens ATCC 43171T | Daidzin | Daidzein | 33 | ||
| Genistin | Genistein | ||||
| Blautia sp. MRG-PMF1, Lactococcus sp. MRG-IFC-1, Lactococcus sp. MRG-IF-3, Enterococcus sp. MRG-IFC-2 | Daidzin | Daidzein | 36,40 | ||
| Genistin | Genistein | ||||
| Sissotrin | Biochanin A | ||||
| Ononin | Formononetin | ||||
| Glycitin | Glycitein | ||||
| C-Deglycosylation | Strain PUE | Puerarin | Daidzein | 49 | |
| Strain CG19-1 | Puerarin | Daidzein | 37 | ||
| Lactococcus sp. MRG-IFC-1, Enterococcus sp. MRG-IFC-2 | Puerarin | Daidzein | 40 | ||
| O-Demethylation | Eubacterium limosum ATCC 8486T | Biochanin A | Genistein | 53 | |
| Formononetin | Daidzein | ||||
| Glycitein | 6,7,4′-Trihydroxyisoflavone | ||||
| Blautia sp. MRG-PMF1 | Biochanin A | Genistein | 36 | ||
| Formononetin | Daidzein | ||||
| Glycitein | 6,7,4′-Trihydroxyisoflavone | ||||
| Reduction | Bifidobacterium animalis strain, B. longum strain, B. pseudolongum strain | Daidzein | Equol | 30 | |
| Strain Julong 732 | Dihydrodaidzein | Equol | 76 | ||
| Strain TM-40 | Daidzein | Dihydrodaidzein | 75 | ||
| Slackia equolifaciens JCM 16059T | Daidzein | Equol | 49,64 | ||
| Genistein | 5-Hydroxy-equol | ||||
| Eggerthella sp. YY7918 | Daidzein, dihydrodaidzein | Equol | 66 | ||
| Adlercreutzia equolifaciens JCM 14793T | Daidzein | Equol | 67 | ||
| Slackia isoflavoniconvertens DSM 22006T | Daidzein | Equol | 68 | ||
| Genistein | 5-Hydroxy-equol | ||||
| Lactococcus garvieae 20–92 | Daidzein | Equol | 65 | ||
| Slackia sp. NATTS | Daidzein | Equol | 69 | ||
| C-Ring cleavage | Eubacterium ramulus DSM 16296 | Daidzein | O-Desmethylangolensin | 35 | |
| Genistein | 6′-Hydroxy-O-desmethylangolensin | ||||
| Eubacterium ramulus Julong 601 | Daidzein | O-Desmethylangolensin | 77 | ||
| Genistein | 2-(4-Hydroxyphenyl)propionic acid | ||||
| Strain SY8519 | Daidzein | O-Desmethylangolensin | 78 | ||
| O-Desmethylangolensin cleavage | Eubacterium ramulus DSM 16296 | 6′-Hydroxy-O-desmethylangolensin | Phloroglucinol, 2-(4-hydroxyphenyl)propionic acid | 35 | |
| Strain CG19-1 | 6′-Hydroxy-O-desmethylangolensin | Phloroglucinol, 2-(4-hydroxyphenyl)propionic acid | 37 | ||
| O-Desmethylangolensin | Resorcinol, 2-(4-hydroxyphenyl)propionic acid | ||||
| Flavan-3-ols | Dehydroxylation | Adlercreutzia equolifaciens JCM 14793T | (−)-Epigallocatechin | (2S,3S)-Flavan-3,3′,5,5′,7-pentol | 80 |
| (−)-Gallocatechin | (2R,3S)-Flavan-3,3′,5,5′,7-pentol | ||||
| C-Ring cleavage | Eggerthella (Eubacterium) sp. SDG-2 | (+)-Catechin, (+)-epicatechin | (2R)-1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 56 | |
| (−)-Catechin, (−)-epicatechin | (2S)-1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | ||||
| (−)-Gallocatechin, (−)-epigallocatechin | (2S)-1-(3,4,5-Trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | ||||
| Eggerthella lenta rK3 | (+)-Catechin, (−)-epicatechin | 1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 79 | ||
| Eggerthella lenta CAT-1 | (+)-Catechin | (2R)-1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 57 | ||
| (−)-Epicatechin | (2S)-1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | ||||
| Lactobacillus plantarum IFPL935 | (+)-Catechin, (−)-epicatechin | 1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 81 | ||
| (−)-Epicatechin-3-O-gallate | 1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol [includes ester cleavage] | ||||
| Slackia equolifaciens JCM 16059T | (−)-Epigallocatechin, (−)-gallocatechin | 1-(3,4,5-Trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 80 | ||
| Adlercreutzia equolifaciens JCM 14793T | (−)-Gallocatechin | 1-(3,4,5-Trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 80 | ||
| Dehydroxylation of the C-ring cleavage product | Eggerthella (Eubacterium) sp. SDG-2 | (2S)-1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | (2S)-1-(3-Hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 56 | |
| (2S)-1-(3,4,5-Trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | (2S)-1-(3,5-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | ||||
| Eggerthella lenta CAT-1 | (2S)-1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | (2S)-1-(3-Hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 57 | ||
| (2R)-1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | (2R)-1-(3-Hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | ||||
| Adlercreutzia equolifaciens JCM 14793T | 1-(3,4,5-Trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 1-(3,5-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 80 | ||
| Degradation of the C-ring cleavage product | Flavonifractor plautii strains DSM 6740 and aK2 | 1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol | 5-(3,4-Dihydroxyphenyl)-γ-valerolactone, 4-hydroxy-5-(3,4-dihydroxyphenyl)valeric acid | 79 | |
| Anthocyanins | O-Deglycosylation | Bifidobacterium animalis ssp. lactis (Bifidobacterium lactis) BB-12, Lactobacillus casei LC-01, L. plantarum IFPL722 | Malvidin-3-O-glucoside | Gallic acid, homogentisic acid, syringic acid | 29 |
Note.
a
Entries within each reaction type are listed in order of their publication year.
b
ND, not determined.