It was first described by
Felix Ehrlich in 1912. Ehrlich demonstrated that yeast attacks the natural amino acids essentially by splitting off carbon dioxide and replacing the amino group with hydroxyl. By this reaction,
tryptophan gives rise to tryptophol.[9] Tryptophan is first deaminated to
3-indolepyruvate. It is then decarboxylated[10] to
indole acetaldehyde by
indolepyruvate decarboxylase. This latter compound is transformed to tryptophol by
alcohol dehydrogenase.[11]
Tryptophol and its derivatives 5-hydroxytryptophol and 5-methoxytryptophol, induce
sleep in mice. It induces a sleep-like state that lasts less than an hour at the 250 mg/kg dose.[16] These compounds may play a role in physiological sleep mechanisms.[17] It may be a
functional analog of
serotonin or
melatonin, compounds involved in sleep regulation.
Tryptophol is a
quorum sensing molecule for the yeast Saccharomyces cerevisiae.[19] It is also found in the bloodstream of patients with chronic trypanosomiasis. For that reason, it may be a
quorum sensing molecule for the trypanosome parasite.[18]
In the case of trypanosome infection, tryptophol decreases the immune response of the host.[20]
As it is formed in the liver after
ethanol ingestion or
disulfiram treatment, it is also associated with the study of
alcoholism.[1][16]Pyrazole and
ethanol have been shown to inhibit the conversion of exogenous tryptophol to
indole-3-acetic acid and to potentiate the sleep-inducing hypothermic effects of tryptophol in mice.[21]
^Sandberg G, Ernstsen A, Hamnede M (1987). "Dynamics of indole-3-acetic acid and indole-3-ethanol during development and germination of Pinus sylvestris seeds". Physiologia Plantarum. 71 (4): 411–418.
doi:
10.1111/j.1399-3054.1987.tb02876.x.
^Richard Seed J, Seed TM, Sechelski J (1978). "The biological effects of tryptophol (indole-3-ethanol): Hemolytic, biochemical and behavior modifying activity". Comparative Biochemistry and Physiology C. 60 (2): 175–185.
doi:
10.1016/0306-4492(78)90091-6.
PMID28889.
^Gil C, Gómez-Cordovés C (1986). "Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes". Food Chemistry. 22: 59–65.
doi:
10.1016/0308-8146(86)90009-9.
^Ribéreau-Gayon P, Sapis JC (1965). "On the presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation". Comptes Rendus de l'Académie des Sciences, Série D. 261 (8): 1915–6.
PMID4954284. (Article in French)
^Richard W. Jackson (1930).
"A synthesis of tryptophol"(PDF). Journal of Biological Chemistry. 88 (3): 659–662.{{
cite journal}}: CS1 maint: numeric names: authors list (
link)
^Wuster A, Babu MM (2010). "Transcriptional control of the quorum sensing response in yeast". Molecular BioSystems. 6 (1): 134–41.
doi:
10.1039/B913579K.
PMID20024075.
^Ackerman SB, Seed JR (1976). "The effects of tryptophol on immune responses and its implications toward trypanosome-induced immunosuppression". Experientia. 32 (5): 645–7.
doi:
10.1007/BF01990212.
PMID776647.
S2CID12695689.
^Seed JR, Sechelski J (1977). "Tryptophol levels in mice injected with pharmacological doses of tryptophol, and the effect of pyrazole and ethanol on these levels". Life Sciences. 21 (11): 1603–10.
doi:
10.1016/0024-3205(77)90237-5.
PMID600013.
^Jelaska S, Magnus V, Seretin M, Lacan G (1985). "Induction of embryogenic callus in Cucurbita pepo hypocotyl explants by indole-3-ethanol and its sugar conjugates". Physiologia Plantarum. 64 (2): 237–242.
doi:
10.1111/j.1399-3054.1985.tb02342.x.