tryptophol

Tryptophol can be found in Pinus sylvestris needles{{cite journal|doi=10.1007/BF00394569|title=Biosynthesis and metabolism of indole-3-ethanol and indole-3-acetic acid by Pinus sylvestris L. Needles|year=1984|last1=Sandberg|first1=Göran|journal=Planta|volume=161|issue=5|pages=398–403|pmid=24253838|bibcode=1984Plant.161..398S |s2cid=23500542}} or seeds.{{cite journal|doi=10.1111/j.1399-3054.1987.tb02876.x|title=Dynamics of indole-3-acetic acid and indole-3-ethanol during development and germination of Pinus sylvestris seeds|year=1987|last1=Sandberg|first1=Goran|last2=Ernstsen|first2=Arild|last3=Hamnede|first3=Marianne|journal=Physiologia Plantarum|volume=71|issue=4|pages=411–418}}

It is produced by the trypanosomal parasite (Trypanosoma brucei) in sleeping sickness (African trypanosomiasis).{{cite journal|doi=10.1016/0306-4492(78)90091-6|title=The biological effects of tryptophol (indole-3-ethanol): Hemolytic, biochemical and behavior modifying activity|year=1978|last1=Richard Seed|first1=John|last2=Seed|first2=Thomas M.|last3=Sechelski|first3=John|journal=Comparative Biochemistry and Physiology C|volume=60|issue=2|pages=175–185|pmid=28889}}

Tryptophol is found in wine{{cite journal|doi=10.1016/0308-8146(86)90009-9|title=Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes|year=1986|last1=Gil|first1=C.|last2=Gómez-Cordovés|first2=C.|journal=Food Chemistry|volume=22|pages=59–65}} and beer as a secondary product of ethanol fermentation{{cite journal|pmid=4954284|year=1965|last1=Ribéreau-Gayon|first1=P|last2=Sapis|first2=JC|title=On the presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation|volume=261|issue=8|pages=1915–6|journal=Comptes Rendus de l'Académie des Sciences, Série D}} (Article in French) (a product also known as congener) by Saccharomyces cerevisiae.

It is also an autoantibiotic produced by the fungus Candida albicans.{{cite journal|pmid=5762768|year=1969|last1=Lingappa|first1=BT|last2=Prasad|first2=M|last3=Lingappa|first3=Y|last4=Hunt|first4=DF|last5=Biemann|first5=K|title=Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans|volume=163|issue=3863|pages=192–4|journal=Science|doi=10.1126/science.163.3863.192|bibcode=1969Sci...163..192L|s2cid=12430791}}

It can also be isolated from the marine sponge Ircinia spiculosa.{{cite journal |pmid=10856636 |year=2000 |first1=İlkay |last1=Erdoğan |last2=Sener |first2=B |last3=Higa |first3=T |title=Tryptophol, a plant auxin isolated from the marine sponge Ircinia spinulosa|volume=28|issue=8|pages=793–794|journal=Biochemical Systematics and Ecology|doi=10.1016/S0305-1978(99)00111-8|bibcode=2000BioSE..28..793E }}

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.{{cite journal |url= http://www.jbc.org/content/88/3/659.full.pdf |title= A synthesis of tryptophol |author= Richard W. Jackson (1930) |journal= Journal of Biological Chemistry |volume= 88 |issue= 3 |pages= 659–662}} Tryptophan is first deaminated to 3-indolepyruvate. It is then decarboxylated{{cite journal|pmid=12499363|year=2003|last1=Dickinson|first1=JR|last2=Salgado|first2=LE|last3=Hewlins|first3=MJ|title=The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae|volume=278|issue=10|pages=8028–34|doi=10.1074/jbc.M211914200|journal=The Journal of Biological Chemistry|doi-access=free}} to indole acetaldehyde by indolepyruvate decarboxylase. This latter compound is transformed to tryptophol by alcohol dehydrogenase.[http://biocyc.org/YEAST/NEW-IMAGE?type=PATHWAY&object=PWY-5081 Pathway: tryptophan degradation VIII (to tryptophol) at BioCyc.org]

It is formed from tryptophan, along with indole-3-acetic acid in rats infected by Trypanosoma brucei gambiense.{{cite journal|doi=10.1093/infdis/131.4.459|title=Short-Term Metabolism of \14C]Tryptophan in Rats Infected with Trypanosoma brucei gambiense|year=1975|last1=Stibbs|first1=H. H.|last2=Seed|first2=J. R.|journal=Journal of Infectious Diseases|volume=131|issue=4|pages=459–62|pmid=1117200}}

An efficient conversion of tryptophan to indole-3-acetic acid and/or tryptophol can be achieved by some species of fungi in the genus Rhizoctonia.{{cite journal|title=Efficient Conversion of L-Tryptophan to Indole-3-Acetic Acid and/or Tryptophol by Some Species of Rhizoctonia|author= Toshiko Furukawa, Jinichiro Koga, Takashi Adachi, Kunihei Kishi and Kunihiko Syono|journal= Plant Cell Physiol.|year= 1996 |volume= 37 |issue= 7 |pages= 899–905|url=http://pcp.oxfordjournals.org/content/37/7/899.short|doi=10.1093/oxfordjournals.pcp.a029037|doi-access= free|url-access= subscription}}

In Cucumis sativus (cucumber), the enzymes indole-3-acetaldehyde reductase (NADH) and indole-3-acetaldehyde reductase (NADPH) use tryptophol to form (indol-3-yl)acetaldehyde.{{cite journal |vauthors=Brown HM, Purves WK |date= 1976 |title= Isolation and characterization of indole-3-acetaldehyde reductases from Cucumis sativus |journal= J. Biol. Chem. |volume= 251 |pages= 907–13 |pmid= 2607 |issue= 4|doi= 10.1016/S0021-9258(17)33779-1 |doi-access= free }}

The unicellular alga Euglena gracilis converts exogenous tryptophol to two major metabolites: tryptophol galactoside and an unknown compound (a tryptophol ester), and to minor amounts of indole-3-acetic acid, tryptophol acetate, and tryptophol glucoside.{{cite journal|pmid=16663965|year=1984|last1=Laćan|first1=G|last2=Magnus|first2=V|last3=Jericević|first3=B|last4=Kunst|first4=L|last5=Iskrić|first5=S|title=Formation of Tryptophol Galactoside and an Unknown Tryptophol Ester in Euglena gracilis|volume=76|issue=4|pages=889–93|pmc=1064400|journal=Plant Physiology|doi=10.1104/pp.76.4.889}}

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. These compounds may play a role in physiological sleep mechanisms.{{cite journal |doi= 10.1016/0024-3205(70)90220-1 |title= Tryptophol, 5-hydroxytryptophol and 5-methoxytryptophol induced sleep in mice |year= 1970 |last1= Feldstein |first1= A. |last2= Chang |first2= F.H. |last3= Kucharski |first3= J.M. |journal= Life Sciences |volume= 9 |issue= 6 |pages= 323–9 |pmid= 5444013}} It may be a functional analog of serotonin or melatonin, compounds involved in sleep regulation.

Tryptophol shows genotoxicity in vitro.{{cite journal |doi= 10.2478/10004-1254-62-2011-2090 |title= Assessment of Tryptophol Genotoxicity in Four Cell Lines in Vitro: A Pilot Study with Alkaline Comet Assay |year= 2011 |last1= Kosalec |first1= Ivan |last2= Ramić |first2= Snježana |last3= Jelić |first3= Dubravko |last4= Antolović |first4= Roberto |last5= Pepeljnjak |first5= Stjepan |last6= Kopjar |first6= Nevenka |journal= Archives of Industrial Hygiene and Toxicology |volume= 62|issue= 1 |pages= 41–49 |pmid= 21421532 |url= http://hrcak.srce.hr/file/97775 |doi-access= free }}

Tryptophol is a quorum sensing molecule for the yeast Saccharomyces cerevisiae.{{cite journal|doi=10.1039/B913579K|title=Transcriptional control of the quorum sensing response in yeast|year=2010|last1=Wuster|first1=Arthur|last2=Babu|first2=M. Madan|journal=Molecular BioSystems|volume=6|pages=134–41|pmid=20024075|issue=1}} 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.

In the case of trypanosome infection, tryptophol decreases the immune response of the host.{{cite journal |doi= 10.1007/BF01990212 |title= The effects of tryptophol on immune responses and its implications toward trypanosome-induced immunosuppression |year= 1976 |last1= Ackerman |first1= S. B. |last2= Seed |first2= J. R. |journal= Experientia |volume= 32 |issue= 5 |pages= 645–7 |pmid= 776647|s2cid= 12695689 }}

As it is formed in the liver after ethanol ingestion or disulfiram treatment, it is also associated with the study of alcoholism.{{cite journal|doi=10.1111/j.1471-4159.1981.tb00428.x|title=Reduction in Brain Glucose Utilization Rate after Tryptophol (3-Indole Ethanol) Treatment|year=1981|last1=Cornford|first1=Eain M.|last2=Crane|first2=Paul D.|last3=Braun|first3=Leon D.|last4=Bocash|first4=William D.|last5=Nyerges|first5=Anthony M.|last6=Oldendorf|first6=William H.|author6-link = William H. Oldendorf|journal=Journal of Neurochemistry|volume=36|issue=5|pages=1758–65|pmid=7241135|s2cid=9169087}} 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.{{cite journal|doi=10.1016/0024-3205(77)90237-5|title=Tryptophol levels in mice injected with pharmacological doses of tryptophol, and the effect of pyrazole and ethanol on these levels|year=1977|last1=Seed|first1=John Richard|last2=Sechelski|first2=John|journal=Life Sciences|volume=21|issue=11|pages=1603–10|pmid=600013}}

It is a growth promoter of cucumber hypocotyl segments.{{cite journal|pmc=1086576|year=1967|last1=Rayle|first1=DL|last2=Purves|first2=WK|title=Isolation and Identification of Indole-3-Ethanol (Tryptophol) from Cucumber Seedlings|volume=42|issue=4|pages=520–524|journal=Plant Physiology|doi=10.1104/pp.42.4.520|pmid=16656532}} The auxinic action in terms of embryo formation is even better for tryptophol arabinoside on Cucurbita pepo hypocotyl fragments.{{cite journal|doi=10.1111/j.1399-3054.1985.tb02342.x|title=Induction of embryogenic callus in Cucurbita pepo hypocotyl explants by indole-3-ethanol and its sugar conjugates|year=1985|last1=Jelaska|first1=Sibila|last2=Magnus|first2=Volker|last3=Seretin|first3=Mira|last4=Lacan|first4=Goran|journal=Physiologia Plantarum|volume=64|issue=2|pages=237–242}}

• Wine chemistry

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{{Alcohols}}

Category:Auxins

Category:Human drug metabolites

Category:Hypnotics

Category:Indoles

Category:Hydroxyethyl compounds