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. 2019 May 24;11(5):1163. doi: 10.3390/nu11051163

Table 7.

Metabolites analyzed in urine after acute cocoa intervention studied with non-targeted methodologies.

Period (h) Purine Metabolites Polyphenol Metabolites Nicotinic Acid Metabolites Amino Acid Metabolites Others Reference
Baseline N-methylguanine - - - - [87]
0–6 3-methyluric acid
3-methylxanthine
3,7-dimethyluric acid
7-methyluric acid
7-methylxanthineAMMU (4)
Caffeine
Theobromine
3´-methoxy-4´-hydroxyphenyl valerolactone
3´-methoxy-4´-hydroxyphenyl valerolactone glucuronide
4-hydroxy-5-(3,4-dihydroxyphenyl)-valeric acid
5-(3´,4´-dihydroxyphenyl)-γ-valerolactone glucuronide
Epicatechin-O—sulfate
O-methyl epicatechin
Vanillic acid
Vanilloylglycine
Hydroxynicotinic acid Trigonelline Tyrosine 3,5-diethyl-2-methyl pyrazine
Cyclo(Ser-Tyr)
Cyclo(Pro-Pro)
Hydroxyacetophenone
[86]
3-methylxanthine
7-methylxanthine
Theobromine
Vanilloylglycine - - - [87]
3-methyluric acid
3-methylxanthine
3,7- dimethyluric acid
7-methyluric acid
7-methylxanthine
AMMU
Caffeine
Theobromine
3´-methoxy-4´-hydroxyphenyl valerolactone
3´-methoxy-4´-hydroxyphenyl valerolactone glucuronide
4-hydroxy-5-(3,4-dihydroxyphenyl)-valeric acid
5-(3´,4´-dihydroxyphenyl)--valerolactone sulfate
5-(3´,4´-dihydroxyphenyl)-valerolactone glucuronide
Hippurate
Epicatechin-O-sulfate
Vanilloylglycine
Hydroxynicotinic acid
N1-methylnicotinamide
Alanine
Arginine
Glycine
Tyrosine
Valine
2-hydroxyisobutyrate
3-hydroxyisobutyrate
3-hydroxyisovalerate
4-hydroxyphenyl acetate
Creatinine
Dimethylamine
Lactate
O-feruoylquinate
Pyruvate
[84]
6–12 3-methyluric acid
3-methylxanthine
3,7-dimethyluric acid
7-methyluric acid
7-methylxanthine
AMMU
Caffeine
Theobromine
3´-methoxy-4´-hydroxyphenyl valerolactone
3´-methoxy-4´-hydroxyphenyl valerolactone glucuronide
4-hydroxy-5-(3,4-dihydroxyphenyl)-valeric acid
5-(3´,4´-dihydroxyphenyl)-g-valerolactone glucuronide
5-(3´,4´-dihydroxyphenyl)-γ-valerolactone sulfate
5-(3´,4´-dihydroxyphenyl)-γ-valerolactone glucuronide
- - Cyclo(Ser-Tyr)
3,5-diethyl-2-methyl pyrazine
[86]
3-methylxanthine
7-methylxanthine
Theobromine
Dihydroxyphenyl valerolactone glucuronide - - Furoylglycine [87]
12–24 3-methyluric acid
3-methylxanthine
3,7-dimethyluric acid
7-methyluric acid
7-methylxanthine
AMMU
Theobromine
3´-methoxy-4´-hydroxyphenyl valerolactone
3´-methoxy-4´-hydroxyphenyl valerolactone glucuronide
4-hydroxy-5-(3,4-dihydroxyphenyl)-valeric acid
5-(3´,4´-dihydroxyphenyl)-g-valerolactone glucuronide
5-(3´,4´-dihydroxyphenyl)-γ-valerolactone glucuronide
- - Cyclo(Ser-Tyr) [86]
3-methylxanthine
7-methylxanthine
Theobromine
- - Xanthurenic acid - [87]

Notes: (4) AMMU means 6-amino-5-[N-methylformylamino]-1-methyluracil.