Epigallocatechin-3-O-gallate / Epigallocatechin / Epicatechin breakdown pathway (Homo sapiens)

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3'-methoxy-4'hydroxy-phenylacetic acid4-hydroxy-5(3',4'-didhydroxy-phenyl)-valeric acid4'-hydroxy-phenylacetic acid(-)-Epicatechin5-(3'-hydroxyphenyl)-gamma-valerolactone5-(3',4'-dihydroxyphenyl)-gamma-valerolactone4-hydroxybenzoic acidPyrogallolPyrocatechol5-(3',4',5'-trihydroxyphenyl)-gamma-valerolactone1-(3',4'-dihydroxyphenyl)-3-(2",4",6"-trihydroxy)propan-2-ol3-(3'-hydroxyphenyl)-propionic acid5-(3',5'-dihydroxyphenyl)-gamma-valerolactone(-)-Epigallocatechin3',4'-dihydroxy-phenylacetic acid(-)-Epigallocatechin-3-O-gallateGallic acidHippuric acid5-(4'-hydroxyphenyl)-gamma-valerolactone1-(3',4',5'-trihydroxyphenyl)-3-(2",4",6"-trihydroxy)propan-2-ol3-(3'-hydroxyphenyl)-hydracrylic acid21, 221, 222222224-hydroxy-5-(3',5'-dihydroxyphenyl)-valeric acid2222221, 22224-hydroxy-5-(3',4',5'-trihydroxyphenyl)-valeric acid24-hydroxy-5-(3'-hydroxyphenyl)-valeric acid22


Description

Schematic representation of the metabolism of flavan-3-ols in the human body. Full arrows represent a direct link (most likely one enzyme or step involved), whereas dashed arrows represent most likely several enzymes or steps. Please note that the structures are found in human urine as conjugates with glucuronide, sulfate, and/or methyl groups. Flavan-3-ols are compounds abundant in food products like green tea, red wine, and chocolate. As a result of many people consuming one or more of these food products, the (conjugated) breakdown products of flavan-3-ols are often encountered in human urine. The breakdown is mostly the result of gut microbes that convert the food metabolites through different routes towards small phenolic acids and eventually benzoic acid that readilly forms a conjugate with glycine to result in hippuric acid, a common gut microbial product. A complete list of the conjugates encountered in urine after tea intake can be found with the study of Van der Hooft et al. (2012).

The scheme was adapted from Roowi et al. (2010) based on the urinary compounds annotated and identified in the study by Van der Hooft et al. (2012).


Green tea flavan-3-ols: Colonic degradation and urinary excretion of catabolites by humans Roowi, Suri; Stalmach, Angelique; Mullen, William; Lean, Michael E. J.; Edwards, Christine A.; Crozier, Alan Journal of Agricultural and Food Chemistry (2010), 58 (2), 1296-1304 CODEN: JAFCAU; ISSN:0021-8561. (American Chemical Society)

Structural Elucidation and Quantification of Phenolic Conjugates Present in Human Urine after Tea Intake Justin J. J. van der Hooft, Ric C. H. de Vos, Velitchka Mihaleva, Raoul J. Bino, Lars Ridder, Niels de Roo, Doris M. Jacobs, John P. M. van Duynhoven, and Jacques Vervoort Analytical Chemistry 2012 84 (16), 7263-7271 DOI: 10.1021/ac3017339

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Ontology Terms

 

Bibliography

  1. Roowi S, Stalmach A, Mullen W, Lean ME, Edwards CA, Crozier A; ''Green tea flavan-3-ols: colonic degradation and urinary excretion of catabolites by humans.''; J Agric Food Chem, 2010 PubMed Europe PMC
  2. van der Hooft JJJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J; ''Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake.''; Analytical Chemistry, American Chemical Society, 2012 PubMed Europe PMC

History

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CompareRevisionActionTimeUserComment
107147view14:23, 17 September 2019MaintBotChEBI identifier normalization
106198view12:09, 16 August 2019MaintBotHMDB identifier normalization
86207view10:41, 6 July 2016JjjvanderhooftChecked arrows - added lit ref to tea compounds (Roowi et al)
86203view07:10, 6 July 2016MaintBotAdded missing HMDB prefixes in the IDs.
86202view07:08, 6 July 2016MaintBotModified description
86193view17:55, 5 July 2016JjjvanderhooftModified description
86192view17:53, 5 July 2016MaintBotOntology Term : 'classic metabolic pathway' added !
86191view17:53, 5 July 2016MaintBotOntology Term : 'xenobiotic metabolic pathway' added !
86190view17:42, 5 July 2016JjjvanderhooftModified description
86189view15:18, 5 July 2016JjjvanderhooftModified title
86188view15:15, 5 July 2016JjjvanderhooftVersion 1 (copied from paper)
86187view15:14, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86186view15:03, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86185view14:52, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86184view14:42, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86183view14:28, 5 July 2016JjjvanderhooftSpecify description
86182view14:27, 5 July 2016JjjvanderhooftSpecify description
86181view14:20, 5 July 2016JjjvanderhooftSpecify description
86180view14:12, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86179view14:02, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86178view13:51, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86177view13:39, 5 July 2016JjjvanderhooftPeriodical save, work in progress
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86175view13:18, 5 July 2016JjjvanderhooftPeriodical save, work in progress
86174view13:07, 5 July 2016JjjvanderhooftNew pathway

External references

DataNodes

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NameTypeDatabase referenceComment
(-)-EpicatechinMetaboliteCHEBI:90 (ChEBI)
(-)-Epigallocatechin-3-O-gallateMetaboliteCHEBI:4806 (ChEBI)
(-)-EpigallocatechinMetaboliteCHEBI:42255 (ChEBI)
1-(3',4',5'-trihydroxyphenyl)- 3-(2",4",6"-trihydroxy)propan-2-olMetabolite
1-(3',4'-dihydroxyphenyl)- 3-(2",4",6"-trihydroxy)propan-2-olMetabolite
3',4'-dihydroxy- phenylacetic acidMetaboliteHMDB0001336 (HMDB)
3'-methoxy-4'hydroxy- phenylacetic acidMetaboliteHMDB0000118 (HMDB)
3-(3'-hydroxyphenyl)- hydracrylic acidMetaboliteHMDB0002643 (HMDB)
3-(3'-hydroxyphenyl)- propionic acidMetaboliteHMDB0000375 (HMDB)
4'-hydroxy- phenylacetic acidMetaboliteHMDB0000020 (HMDB)
4-hydroxy-5(3',4'-didhydroxy- phenyl)-valeric acidMetaboliteHMDB0041679 (HMDB)
4-hydroxy-5-(3',4',5'-trihydroxyphenyl)- valeric acidMetabolite
4-hydroxy-5-(3',5'-dihydroxyphenyl)- valeric acidMetabolite
4-hydroxy-5-(3'-hydroxyphenyl)- valeric acidMetabolite
4-hydroxybenzoic acidMetaboliteHMDB0000500 (HMDB)
5-(3',4',5'-trihydroxyphenyl) -gamma-valerolactoneMetaboliteHMDB0041691 (HMDB)
5-(3',4'-dihydroxyphenyl) -gamma-valerolactoneMetaboliteCHEBI:89285 (ChEBI)
5-(3',5'-dihydroxyphenyl) -gamma-valerolactoneMetaboliteHMDB0029187 (HMDB)
5-(3'-hydroxyphenyl) -gamma-valerolactoneMetabolite
5-(4'-hydroxyphenyl) -gamma-valerolactoneMetabolite
Gallic acidMetaboliteCHEBI:30778 (ChEBI)
Hippuric acidMetaboliteCHEBI:18089 (ChEBI)
PyrocatecholMetaboliteCHEBI:18135 (ChEBI)
PyrogallolMetaboliteCHEBI:16164 (ChEBI)

Annotated Interactions

No annotated interactions

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