7-Hydroxytryptophan

7-Hydroxytryptophan
Names
IUPAC name
2-amino-3-(7-hydroxy-1H-indol-3-yl)propanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH 5-Hydroxytryptophan
  • InChI=1S/C11H12N2O3/c12-8(11(15)16)4-6-5-13-10-7(6)2-1-3-9(10)14/h1-3,5,8,13-14H,4,12H2,(H,15,16)
    Key: VQSRKJZICBNQJG-UHFFFAOYSA-N
  • C1=CC2=C(C(=C1)O)NC=C2CC(C(=O)O)N
Properties
C11H12N2O3
Molar mass 220.228 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Not to be confused with 5-Hydroxytryptophan or 7-Hydroxytryptamine.

7-Hydroxytryptophan (7-HTP) is a non-proteinogenic amino acid. It is also a 5-hydroxytryptophan (5-HTP) positional isomer, a L-tryptophan derivative, structurally belonging to the hydroxytryptophan family, and a substituted tryptophan with a hydroxyl group at position 7 of the indole ring. It is not a precursor of serotonin. 7-Hydroxytryptophan is a metabolite detected in human urine.

It has been investigated for its role as a precursor in melanin-related oxidative processes.[1][2]

7-Hydroxytryptophan is found in human urine, but its formation pathway in the body is unknown.

Natural occurrence

7-Hydroxytryptophan is present in the mussel adhesive protein Pvfp-1 of Perna viridis as a post-translationally modified tryptophan residue. This modified residue exhibits redox activity, potentially substituting for DOPA.[3]

7-Hydroxytryptophan was first identified in fungi and was isolated from the fruiting bodies of the fungus Cortinarius purpurascens, where it can serve as a precursor for the synthesis of azepino-indole alkaloids (so-called purpurascenins A–C) via the Pictet–Spengler reaction.[4]

7-Hydroxytryptophan in archaea

7-hydroxytryptophan has been identified as a rare post-translational modification in the active site of the enzyme MCR (methyl-coenzyme M reductase) in methanotrophic archaea (ANME-MCR group) But the role of ANME is assumed to be that 7-hydroxytryptophan compensates for the lack of arginine methylation.[5]

Metabolism

In normal tissues, 7-HTP either remains metabolically inactive or is incorporated into normal amino acid metabolism pathways without the formation of toxic products.

In tumor cells expressing tryptophan hydroxylase, 7-hydroxytryptophan is enzymatically converted in situ into the toxic compound 5,7-dihydroxytryptamine (5,7-DHT). This metabolite induces apoptosis selectively in serotonin-producing tumor cells. And also interferes with the autocrine ability to synthesize serotonin. The conversion of 7-HTP to 5,7-DHT is completely inhibited by the specific tryptophan hydroxylase inhibitor para-chlorophenylalanine (Fenclonine).[6][7]

Pharmacology

Oxidase from the gill plates of mussels (Mytilus edulis) is able to oxidize 7-Hydroxytryptophan and other related compounds, whereas mammalian ceruloplasmin has almost no effect on the compounds.[8]

See also

References

  1. ^ Smaniotto, Anna; Comai, Stefano; Bertazzo, Antonella; Costa, Carlo V. L.; Allegri, Graziella; Seraglia, Roberta; Traldi, Pietro (2006). "A mass spectrometric investigation on the possible role of tryptophan and 7-hydroxytryptophan in melanogenesis". Journal of Mass Spectrometry: JMS. 41 (7): 921–930. doi:10.1002/jms.1051. ISSN 1076-5174. PMID 16810640.
  2. ^ PubChem. "7-Hydroxytryptophan". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-18.
  3. ^ Zhao, Hua; Sagert, Jason; Hwang, Dong Soo; Waite, J. Herbert (2009-08-28). "Glycosylated hydroxytryptophan in a mussel adhesive protein from Perna viridis". The Journal of Biological Chemistry. 284 (35): 23344–23352. doi:10.1074/jbc.M109.022517. ISSN 0021-9258. PMC 2749108. PMID 19584055.
  4. ^ Lam, Yen T. H.; Hoppe, Jana; Dang, Quang N.; Porzel, Andrea; Soboleva, Alena; Brandt, Wolfgang; Rennert, Robert; Hussain, Hidayat; Davari, Mehdi D.; Wessjohann, Ludger; Arnold, Norbert (2023-06-23). "Purpurascenines A-C, Azepino-Indole Alkaloids from Cortinarius purpurascens: Isolation, Biosynthesis, and Activity Studies on the 5-HT2A Receptor". Journal of Natural Products. 86 (6): 1373–1384. doi:10.1021/acs.jnatprod.2c00716. ISSN 1520-6025. PMID 37306303.
  5. ^ "Hydroxytryptophan - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2026-02-23.
  6. ^ Walther, Diego J.; Peter, Jens-Uwe; Bader, Michael (2002-06-15). "7-Hydroxytryptophan, a novel, specific, cytotoxic agent for carcinoids and other serotonin-producing tumors". Cancer. 94 (12): 3135–3140. doi:10.1002/cncr.10592. ISSN 0008-543X. PMID 12115345.
  7. ^ Walther, Diego J.; Peter, Jens-Uwe; Bader, Michael (2002-06-15). "7-hydroxytryptophan, a novel, specific, cytotoxic agent for carcinoids and other serotonin-producing tumors". Cancer. 94 (12): 3135–3140. doi:10.1002/cncr.10592. ISSN 0008-543X. PMID 12115345.
  8. ^ Blaschko, H.; Levine, W. G. (1960). "A comparative study of hydroxyindole oxidases". British Journal of Pharmacology and Chemotherapy. 15 (4): 625–633. doi:10.1111/j.1476-5381.1960.tb00290.x. ISSN 0366-0826. PMC 1482277. PMID 19108143.
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