• Korean Journal of Fisheries and Aquatic Sciences
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• v.49 no.6
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• pp.792-799
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• 2016

We isolated seven tryptamine-producing bacteria from commercial salted and fermented sand lance (Ammodytes personatus) sauces using an L-tryptophan decarboxylating medium. These tryptamine-producing bacteria, identified using an API kit and 16S rRNA analysis, included Lysinibacillus xylanilyticus (one strain), Lysinibacillus fusiformis (four strains), and Staphylococcus epidermidis (two strains). Lysinibacillus spp. produced the highest levels of tryptamine in culture broth containing 0.5% L-tryptophan, compared with 1.0% and 2.0% preparations. After 72 h of incubation, Staphylococcus epidermidis produced the highest levels of tryptamine ($60.50{\mu}g/mL$ and $664.86{\mu}g/mL$) in culture broth containing 2.0% L-tryptophan. While Lysinibacillus spp. comprised the dominant tryptamine-producing bacteria in sand lance sauces, Staphylococcus epidermidis also showed high tryptamine-producing activity. This is the first report on the isolation and identification of tryptamine-producing bacteria in sand lance sauces.

• Applied Biological Chemistry
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• v.19 no.2
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• pp.65-69
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• 1976

Methanolic extract of the common reed sprouts (Phragmites communis Trin.), unincubated or incubated at $27^{\circ}C$ in the dark, was subjected to thin layer chromatography for the indole compounds. Serotonin, tryptophan and tryptamine were the major indoles in the unincubated sprouts. At early stage of incubation of sprouts, however, serotonin and tryptamine decreased while other indoleamines increased. Tryptophan remained constant throughout the incubation periods. From the observation in the present study, it was speculated that serotonin be synthesized from tryptophan via tryptamine and in turn metabolized to bufotenine.

• Biomolecules & Therapeutics
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• v.31 no.2
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• pp.176-182
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• 2023

Among 14 subtypes of serotonin receptors (5-HTRs), 5-HT_2AR plays important roles in drug addiction and various psychiatric disorders. Agonists for 5-HT_2AR have been classified into three structural groups: phenethylamines, tryptamines, and ergolines. In this study, the structure-activity relationship (SAR) of phenethylamine and tryptamine derivatives for binding 5-HT_2AR was determined. In addition, functional and regulatory evaluation of selected compounds was conducted for extracellular signal-regulated kinases (ERKs) and receptor endocytosis. SAR studies showed that phenethylamines possessed higher affinity to 5-HT_2AR than tryptamines. In phenethylamines, two phenyl groups were attached to the carbon and nitrogen (R³ ) atoms of ethylamine, the backbone of phenethylamines. Alkyl or halogen groups on the phenyl ring attached to the β carbon exerted positive effects on the binding affinity when they were at para positions. Oxygen-containing groups attached to R³ exerted mixed influences depending on the position of their attachment. In tryptamine derivatives, tryptamine group was attached to the β carbon of ethylamine, and ally groups were attached to the nitrogen atom. Oxygen-containing substituents on large ring and alkyl substituents on the small ring of tryptamine groups exerted positive and negative influence on the affinity for 5-HT_2AR, respectively. Ally groups attached to the nitrogen atom of ethylamine exerted negative influences. Functional and regulatory activities of the tested compounds correlated with their affinity for 5-HT_2AR, suggesting their agonistic nature. In conclusion, this study provides information for designing novel ligands for 5-HT_2AR, which can be used to control psychiatric disorders and drug abuse.

• Journal of Integrative Natural Science
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• v.1 no.1
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• pp.14-18
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• 2008

A method for synthesizing o-carborane substituted tetrahydroindoles derivatives, starting from tryptamine, is described. In vitro studies showed the desired compounds 9 and 10 synthesized accumulate to high levels in B-16 melanoma cells with low cytotoxicity.

• Biomolecules & Therapeutics
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• v.28 no.1
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• pp.83-91
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• 2020

Tryptamines are monoamine alkaloids with hallucinogenic properties and are widely abused worldwide. To hasten the regulations of novel substances and predict their abuse potential, we designed and synthesized four novel synthetic tryptamine analogs: Pyrrolidino tryptamine hydrochloride (PYT HCl), Piperidino tryptamine hydrochloride (PIT HCl), N,N-dibutyl tryptamine hydrochloride (DBT HCl), and 2-Methyl tryptamine hydrochloride (2-MT HCl). Then, we evaluated their rewarding and reinforcing effects using the conditioned place preference (CPP) and self-administration (SA) paradigms. We conducted an open field test (OFT) to determine the effects of the novel compounds on locomotor activity. A head-twitch response (HTR) was also performed to characterize their hallucinogenic properties. Lastly, we examined the effects of the compounds on 5-HTR1a and 5-HTR2a in the prefrontal cortex using a quantitative real-time polymerase chain reaction (qRT-PCR) assay. None of the compounds induced CPP in mice or initiated SA in rats. PYT HCl and PIT HCl reduced the locomotor activity and elevated the 5-HTR1a mRNA levels in mice. Acute and repeated treatment with the novel tryptamines elicited HTR in mice. Furthermore, a drug challenge involving a 7-day abstinence from drug use produced higher HTR than acute and repeated treatments. Both the acute treatment and drug challenge increased the 5-HTR2a mRNA levels. Ketanserin blocked the induced HTR. Taken together, the findings suggest that PYT HCl, PIT HCl, DBT HCl, and 2-MT HCl produce hallucinogenic effects via 5-HTR2a stimulation, but may have low abuse potential.

• Bulletin of the Korean Chemical Society
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• v.24 no.5
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• pp.623-626
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• 2003

Nematophin and its analog incorporating tryptamine unit have been isolated and characterized from strain XRPC of a symbiotic bacterium Xenorhabdus nematophilus, which was newly isolated from Korean entomopathogenic nematodes. The stereoselective synthesis of these compounds was accomplished, and the relative configurations were determined. Nematophin exhibited potent antibacterial activities over several strains of methicillin-resistant S. aureus (MRSA) comparable to those of vancomycin.

• Journal of Microbiology and Biotechnology
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• v.29 no.10
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• pp.1636-1643
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• 2019

Two hydroxybenzoyl amines, 4-hydroxybenzoyl tyramine (4-HBT) and N-2-hydroxybenzoyl tryptamine (2-HBT), were synthesized using Escherichia coli. While 4-HBT was reported to demonstrate anti-atherosclerotic activity, 2-HBT showed anticonvulsant and antinociceptive activities. We introduced genes chorismate pyruvate-lyase (ubiC), tyrosine decarboxylase (TyDC), isochorismate synthase (entC), isochorismate pyruvate lyase (pchB), and tryptophan decarboxylase (TDC) for each substrate, 4-hydroxybenzoic acid (4-HBA), tyramine, 2-hydroxybenzoic acid (2-HBA), and tryptamine, respectively, in E. coli. Genes for CoA ligase (hbad) and amide formation (CaSHT and OsHCT) were also introduced to form hydroxybenzoic acid and amine conjugates. In addition, we engineered E. coli to provide increased substrates. These approaches led to the yield of 259.3 mg/l 4-HBT and 227.2 mg/l 2-HBT and could be applied to synthesize diverse bioactive hydroxybenzoyl amine conjugates.

• Food Science of Animal Resources
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• v.38 no.1
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• pp.152-161
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• 2018

This study aims to evaluate biogenic amine levels of bez sucuks (BS) produced with different meat:fat ratios. For this, three BS groups were manufactured with meat:fat ratios of 90:10 (BS10), 80:20 (BS20), and 70:30 (BS30). The pH and water activity values and biogenic amine amounts of sucuk samples were determined during processing and storage periods and the pH values of the initial mixtures of BS samples were in the range 5.51-5.74, decreasing to 4.72-4.94 by the $14^{th}$ day. The water activity values of BS samples showed significant decreases as a result of the drying stage and reached to range 0.913-0.935 on the $14^{th}$ day of processing (p<0.05). Although BS10 had the highest tyramine (434.12 mg/kg), histamine (5.69 mg/kg), cadaverine (12.48 mg/kg), putrescine (17.83 mg/kg), 2-phenylethylamine (15.43 mg/kg), and tryptamine (122.41 mg/kg) levels at the end of processing stage (p<0.05), spermine and spermidine levels did not differ between the BS samples due to their utilization of different meat:fat ratios (p>0.05). Similarly, the tryptamine (205.11 mg/kg), putrescine (43.57 mg/kg), and tyramine (766.23 mg/kg) levels of BS10 were higher than BS20 and BS30 samples at the end of storage (p<0.05). The results showed that BS10 with the highest meat ratio had the highest tryptamine, putrescine, and tyramine levels at the end of the processing and storage period.

• Journal of the Korean Society of Food Science and Nutrition
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• v.32 no.3
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• pp.320-324
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• 2003

The protein hydrolysis with 6 M formic acid containing 0.3% tryptamine was a superior method for amino acid analysis of standard amino acid and protein than 6 M HCI containing 0.3% tryptamine. The recoveries of standard amino acid after acid hydrolysis were more accurate in the 6 M formic acid hydrolysis than 6 M HCI hydrolysis, especially recovery of tryptophan showed higher values of 1.5 times than that of 6 M HCI hydrolysis. The results of analysis on the standard protein, bovine serum albumin, showed very similar values compared to the sequence analysis reported in the literature for the 6 M formic acid hydrolysis than 6 M HCI hydrolysis, especially in the tryptophan recovery as standard amino acid recovery. Butylthiocarbamyl - trimethylsilyl (BTC - TMS) derivatives of 22 standard amino acids were successfully resolved DB-17 capillary column. Excellent reproducibility of standard amino acid recovery and composition of bovine serum albumin were obtained with BTC-TMS derivatives.

• Journal of Environmental Health Sciences
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• v.46 no.3
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• pp.324-334
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• 2020

Objectives: This study was conducted to estimate the related health risk by investigating the content of biogenic amines (BAs) in commercial fermented alcoholic beverages. Methods: Ninety-seven samples, including takjus (34), fruit wines (26), distilled liquors (20) and beers (17) were purchased in Gangwon-do (Province) in 2019. The eight BAs (putrescine, cadaverine, spermine, spermidine, tyramine, β-phenylethylamine, histamine, and tryptamine) were analyzed by high performance liquid chromatograph (HPLC) after extraction (0.4 M HClO₄), pigment removal (carbon cartridge) and derivatization (1% dansylchloride). The health risk of exposure to BAs due to ingestion of commercial fermented alcoholic beverages was estimated as the margin of exposure (MOE). Results: Various BAs were detected in takju, fruit wine, distilled liquor and beer. Putrescine (not detected (ND)-12.60 mg/L), cadaverine (ND-5.45 mg/L), tyramine (ND-8.34 mg/L), β-phenylethylamine (ND-13.73 mg/L), histamine (ND-7.96 mg/L), and tryptamine (ND-19.00 mg/L) were found in takju. Putrescine (ND-15.34 mg/L), cadaverine (ND-7.90 mg/L), β-phenylethylamine (ND-3.06 mg/L), histamine (ND-9.68 mg/L), and tryptamine (ND-14.06 mg/L) were identified in fruit wine. Putrescine (less than limit of detection (