Chemical Properties
Off-White Crystalline Powder
Uses
A metabolite of Tryptophan (T947200).
Hazard
A reproductive hazard.
Definition
ChEBI: 5-Hydroxytryptophol is a member of indoles.
Biological Activity
5-hydroxy tryptophol is a metabolite of tryptophan.tryptophan (encoded by the codon ugg) is an α-amino acid that is used in the biosynthesis of proteins. tryptophan has an α-amino group, an α-carboxylic acid group, and a side chain indole, demonstrating it as a non-polar, aromatic amino acid. tryptophan is critical in humans, but the body cannot synthesize it and therefore tryptophan must be obtained from the diet. tryptophan is also found to be a precursor to the neurotransmitters serotonin and melatonin.
in vitro
in previous studies, 5-hydroxy tryptophol was identified as a metabolite of tryptophan that was formed by the alcohol dehydrogenase-catalyzed reduction of the serotonin intermediate, 5-hydroxyindoleacetaldehyde. moreover, depending on the tissue nad/nadh ratio, the acetaldehyde intermediate could also be oxidized by aldehyde dehydrogenase to form 5-hydroxyindoleacetic acid. therefore, the ratio of 5-hydroxy tryptophol to 5-hydroxyindoleacetic acid could be used as a biomarker for recent alcohol consumption [1,2].
References
[1] yokoyama, m. t. and carlson, j.r. dissimilation of tryptophan and related indolic compounds by ruminal microorganisms in vitro. appl.microbiol. 27(3), 540-548 (1974).
[2] beck, o. ,stephanson, n.,btthcer, m., et al. biomarkers to disclose recent intake of alcohol: potential of 5-hydroxytryptophol glucuronide testing using new direct uplc-tandem ms and elisa methods. alcohol & alcoholism 42(4), 321-325 (2007).
