Tryptophol

Manufactured by Merck Group

Sourced in United States

Tryptophol is a chemical compound used in laboratory research. It is a naturally occurring indole derivative that can be synthesized. Tryptophol is commonly used as a research tool in various scientific studies.

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Lab products found in correlation

7 protocols using tryptophol

Tryptophan and Indole Metabolites Analysis

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Tryptophan (catalog no. DH357-2; Beijing Dingguo), tryptophol (catalog no. V900672; Sigma-Aldrich), and IAA (catalog no. DH171-5; Beijing Dingguo) were used in this study.

Wang Y., Deng Y.Z., Cui G., Huang C., Zhang B., Chang C., Jiang Z, & Zhang L.H. (2019). The AGC Kinase SsAgc1 Regulates Sporisorium scitamineum Mating/Filamentation and Pathogenicity. mSphere, 4(3), e00259-19.

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Cytotoxicity Assessment of Mycotoxin Mixtures

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For the cytotoxicity test, toxins were purchased from Sigma (St Quentin Fallavier, France): deoxynivalenol (DON) (purity > 98%), tryptophol (TRPT) (purity > 97%), apicidin (API) (purity > 98%) and emodin (EMO) (purity > 90%). Enniatins (ENNs) (A1, B, B1, purity > 99%), cyclo-(L-Pro-L-Tyr) (Cyclo) (purity > 98%), and brevianamide-F (BRV-F) (purity > 95%) were purchased from BioAustralis (Smithfield, Australia), beauvericin (BEA) (purity > 95%) and aurofusarin (AFN), (purity > 97%) were purchased from Santa Cruz Biotechnology (Dallas, TX, USA). All mycotoxins were dissolved in dimethyl sulfoxide (DMSO) (Sigma) to prepare stock solutions stored at −20 °C. Working dilutions were freshly prepared in cell culture medium for each experiment.
To convert the concentration in the pig feed into the concentration to which intestinal cells might be exposed, we assumed, as already done in previous studies [53 (link)], that mycotoxins were ingested in one meal, diluted in 1 L of gastrointestinal fluid and were entirely bioaccessible. Next, the ratio of DON to emerging mycotoxins was calculated based on three plausible scenarios according to the concentration of DON and emerging mycotoxins in the feed (Supplementary Table S1).
Several 3-fold dilutions of each individual toxin and mixtures at different ratios were performed to account for the concentrations present in feed.

Khoshal A.K., Novak B., Martin P.G., Jenkins T., Neves M., Schatzmayr G., Oswald I.P, & Pinton P. (2019). Co-Occurrence of DON and Emerging Mycotoxins in Worldwide Finished Pig Feed and Their Combined Toxicity in Intestinal Cells. Toxins, 11(12), 727.

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Tryptophol Antifungal Formulation Development

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Tryptophol (TOH; C10H11NO,), voriconazole (VOZ,), absolute ethanol (EtOH), Tween^™ 20, glycerin, propylene glycol, allantoin, phenoxyethanol, Acridine Orange/Ethidium Bromide (AO/EB), Sodium Lauryl Sulfate (SLS), and croton oil were purchased from Sigma-Aldrich (St. Louis, MO, USA). SEPIGEL 305^™ was purchased from Seppic Inc. (Fairfield, NJ, USA). Triethanolamine was purchased from Dow Chemical (Thailand). Deionized (DI) water used in all experiments was produced from in-house Milli-Q^® IQ 7000 Ultrapure Water System (EMD Millipore, Bedford, MA, USA). Sabouraud Dextrose Agar (SDA) and Potato Dextrose Agar (PDA) were purchased from Oxoid Ltd. (Hampshire, UK). Roswell Park Memorial Institute 1640 medium (RPMI-1640), Fetal Bovine Serum (FBS), Penicillin-streptomycin (Pen-strep), Phosphate-Buffered Saline (PBS), and Trypsin-EDTA were purchased from Gibco™ (Grand Island, NY, USA). MTT (3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) was purchased from Bio Basic Inc. (Canada). CytoPainter MitoGreen (#ab176830) was purchased from Abcam. CytoTox 96^® Non-Radioactive Cytotoxicity assay for measuring the release of lactate dehydrogenase (LDH) was purchased from Promega (Madison, WI, USA). All the reagents used in this study were of high purity or HPLC grade.

Kitisin T., Muangkaew W., Thitipramote N., Pudgerd A, & Sukphopetch P. (2023). The study of tryptophol containing emulgel on fungal reduction and skin irritation. Scientific Reports, 13, 18881.

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Quantification of Phenolic Compounds

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Ethyl gallate, 4-hydroxybenzaldehyde, vanillin, tyrosol, protocatechuic aldehyde, syringaldehyde, pyrogallol, 4-hydroxy-3-methoxycinnamaldehyde, 4-methylcatechol, tryptophol, ethyl 3,4-dihydroxycinnamate, 2,6-dimethoxyphenol, ethyl vanillate, homovanillyl alcohol, eugenol, 4-hydroxy-3-methoxyphenylacetone, salicylaldehyde, coniferyl alcohol, epi catechin, catechin, scopoletin, p-coumaric acid, caffeic acid, resveratrol, syringic acid, rutin, gallic acid, salicylic acid, protocatechuic acid, 2-methoxy-4-vinylphenol, 4-vinylphenol, 4-ethylguaiacol were purchased from Sigma-Aldrich (Steinheim, Germany). All chemicals were used in the highest purity available. Acetonitrile and methanol (gradient grade for liquid chromatography) were also purchased from Sigma-Aldrich. Deionized water was produced by Mili-Q^® Reference System (Merck KGaA, Darmstadt, Germany). Sodium chloride was purchased by Lach-Ner (Neratovice, Czech Republic). Standard solution of n-alkanes C8-C33 was purchased by CPAchem (Stara Zagora, Bulgaria). Technical gases, i.e., helium 4.6, hydrogen, and nitrogen, were purchased from Linde Gas (Prague, Czech Republic).

Kašpar M., Bajer T., Bajerová P, & Česla P. (2022). Comparison of Phenolic Profile of Balsamic Vinegars Determined Using Liquid and Gas Chromatography Coupled with Mass Spectrometry. Molecules, 27(4), 1356.

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Analysis of Polyphenolic Compounds

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Formic acid and HPLC grade methanol were purchased from VWR Prolabo (Fontenay-sous-Bois, France). Deionized water was obtained from a Milli-Q purification system (Millipore, Molsheim, France). Standard of trans-piceid was purchased from Selleckchem (Houston, TX, USA). Standards of caffeic acid, vanillic acid, gallic acid and ferulic acid were purchased from Fluka (Buchs, Switzerland). Standards of syringic acid, p-coumaric acid, protocatechuic acid, ethyl protocatechuate, tyrosol, tryptophol, tryptophan, trans-resveratrol, quercetin, catechin, epicatechin, epicatechin 3-gallate, taxifolin, oxidized and reduced glutathione were purchased from Sigma-Aldrich (St. Louis, MO, USA), as well as hydrochloric acid, phloroglucinol, L-ascorbic acid, and ammonium formiate. Standards of ethyl gallate, ethyl caffeate, tyrosine, hydroxytyrosol, epigallocatechin, malvidin 3-O-glucoside chloride, and malvidin 3,5-diglucoside chloride were purchased from Extrasynthese (Geney, France). Standards of trans-caftaric acid, quercetin glucoside and procyanidin dimers B1, B2, B3, B4, and trimer C1 were purchased from Phytolab (Vestenbergsgreuth, Germany).

Leborgne C., Lambert M., Ducasse M.A., Meudec E., Verbaere A., Sommerer N., Boulet J.C., Masson G., Mouret J.R, & Cheynier V. (2022). Elucidating the Color of Rosé Wines Using Polyphenol-Targeted Metabolomics. Molecules, 27(4), 1359.

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Quantitative Analysis of Fungal Quorum Sensing Metabolites

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We screened for four known fungal QS metabolites [tryptophol (3-(2-hydroxyethyl)indole), E-E farnesol, tyrosol (2-(4-hydroxyphenylethanol)), 2-phenylethanol; Sigma-Aldrich]. Primary stock solutions of these metabolites and 2-methylindole (Sigma-Aldrich) as internal standard (ISTD) were prepared in methanol at a concentration of 1,000 ng/μl. Working solutions were prepared in 0.075% formic acid in water/methanol (75/25) or in extracted TGhL medium.

Verbrugghe E., Adriaensen C., Martel A., Vanhaecke L, & Pasmans F. (2019). Growth Regulation in Amphibian Pathogenic Chytrid Fungi by the Quorum Sensing Metabolite Tryptophol. Frontiers in Microbiology, 9, 3277.

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Diverse Indole and Piperazine Derivatives

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Indole, tryptophan, tryptophol, Indole-3-acetic acid hydrazide, and 5-methyl-2-phenyl Indole were purchased from Sigma-Aldrich Korea (Seoul, Korea) and dissolved in dimethylsulfoxide (DMSO). Two different PLA₂ substrates, 1,2-bis (heptanoylthio) phosphatidylcholine (CP) for secretory PLA₂ (sPLA₂) activity and arachidonoyl thio-PC for cellular PLA₂ (cPLA₂) activity, were purchased from Cayman Chemical (Ann Arbor, MI, United States). Peptides cyclo-(l-leucyl-l-phenylalanyl) (cLF) and cyclo-(glycyl-l-leucyl) (cGL) were chemically synthesized. N-acetyl tryptamine (NAT) was purchased from Cayman Chemical. 3-Methyl-6-(phenylmethyl)-2,5-piperazinedione (MPP) was purchased from ChemFaces (Wuhan, Hubei, China). 3-Phenylmethyl-2,5-piperazinedione (PMP) was purchased from Toronto Research Chemicals (North York, Canada). N-(2-phenylethyl) acetamide (NPA) was kindly provided by Professor Helge Bode (Goethe University, Frankfurt, Germany). Hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione (HPA), hexahydro-3-(2-methylpropyl)-pyrrolo[1,2-a]pyrazine-1,4-dio ne (HMPP), and hexahydro-3-(phenylmethyl)- pyrrolo[1,2-a]pyrazine-1,4-dione (HPPP) were purchased from Interpharm (Koyang, Korea). Phosphate-buffered saline (PBS, pH 7.4) was prepared with 100 mM phosphoric acid. Anticoagulant buffer (ACB, pH 4.5) was prepared to contain 186 mM NaCl, 17 mM Na₂EDTA, and 41 mM citric acid.

Mollah M.M., Roy M.C., Choi D.Y., Hasan M.A., Al Baki M.A., Yeom H.S, & Kim Y. (2020). Variations of Indole Metabolites and NRPS-PKS Loci in Two Different Virulent Strains of Xenorhabdus hominickii. Frontiers in Microbiology, 11, 583594.

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