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Journal articles on the topic 'Tryptophol'

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Author: Grafiati

Published: 10 March 2023

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1

Wu, Ju, Hussein Abou-Hamdan, Régis Guillot, Cyrille Kouklovsky, and Guillaume Vincent. "Electrochemical synthesis of 3a-bromofuranoindolines and 3a-bromopyrroloindolines mediated by MgBr2." Chemical Communications 56, no. 11 (2020): 1713–16. http://dx.doi.org/10.1039/c9cc09276e.

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2

Palmieri, Alessandro, and Marino Petrini. "Tryptophol and derivatives: natural occurrence and applications to the synthesis of bioactive compounds." Natural Product Reports 36, no. 3 (2019): 490–530. http://dx.doi.org/10.1039/c8np00032h.

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This report presents some fundamental aspects related to the natural occurrence and bioactivity of tryptophol as well as the synthesis of tryptophols and their utilization for the preparation of naturally occurring alkaloid metabolites embedding the indole system.

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3

Kosalec, Ivan, Snježana Ramić, Dubravko Jelić, Roberto Antolović, Stjepan Pepeljnjak, and Nevenka Kopjar. "Assessment of Tryptophol Genotoxicity in Four Cell Lines In Vitro: A Pilot Study with Alkaline Comet Assay." Archives of Industrial Hygiene and Toxicology 62, no. 1 (March 1, 2011): 41–49. http://dx.doi.org/10.2478/10004-1254-62-2011-2090.

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Assessment of Tryptophol Genotoxicity in Four Cell LinesIn Vitro: A Pilot Study with Alkaline Comet AssayTryptophol is an aromatic alcohol and secondary metabolite of the opportunistic fungusCandida albicans. Although its toxicity profile at cell level has been poorly investigated, recent data point to cytotoxic, cytostatic, and genotoxic effects in lymphocytes and the induction of apoptosis in leukaemic blood monocytes. In this pilot study we evaluated the genotoxicity of tryptopholin vitroon four permanent cell lines of animal and human origin: ovary cells, alveolar epithelium, liver cells, and blood monocytes using the alkaline comet assay. We selected cells that might be principal targets of tryptophol and other low-molecular geno(toxins) secreted byCandida albicansduring host invasion. Our results suggest that tryptophol appliedin vitroat 2 mmol L-1for 24 h damages DNA in HepG2, A549 and THP-1 cells, obviously due to bioactivation and/or decomposition of the parent compound, which results in the formation of more genotoxic compound(s) and production of reactive species that additionally damage DNA. On the other hand, notably lower levels of primary DNA damage were recorded in CHO cells, which lack metabolic activity. Future studies with tryptophol should look further into mechanisms involved in its toxic action and should focus on other cell types prone to infection withCandidaspp. such as vaginal epithelial cells or keratinocytes of human origin.

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4

WONGSUK, Thanwa, and Passanesh SUKPHOPETCH. "Effect of Quarum Sensing Molecules on Aspergillus fumigatus." Walailak Journal of Science and Technology (WJST) 17, no. 4 (April 19, 2019): 348–58. http://dx.doi.org/10.48048/wjst.2020.6172.

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Aspergillus fumigatus is an opportunistic fungal pathogen to which immunocompromised patients are especially susceptible. A. fumigatus can form biofilms both in vitro and in vivo. Quorum sensing molecules (QSMs) have activity against some fungi. This study aimed to determine the activity of the QSMs farnesol, tyrosol, phenylethanol and tryptophol against the growth A. fumigatus on solid media, and against its ability to form biofilms. The activity of each QSM against planktonic A. fumigatus growth was assessed using the CLSI M38-A2 broth microdilution assay, while QSM inhibition of A. fumigatus’s biofilm formation was measured in crystal violet, and 2, 3-bis (2-methoxy-4-nitro-5-sulfo-phenyl)-2H-tetrazolium-5-caboxanilide (XTT) assays. The QSMs reduced the colony diameter of the studied strains in a QSM-dependent pattern. Tryptophol showed the best effect and tyrosol showed the poorest effect. The minimum inhibitory concentrations (MICs) for farnesol, tyrosol, phenylethanol and tryptophol tested against A. fumigatus were > 32, > 32, 16 and 8 mM, respectively. The effective concentration each QSM required to inhibit A. fumigatus biofilm formation were higher than the planktonic MICs. In this study, the performance of QSMs against A. fumigatus ranked from best to worst as follows: tryptophol, phenylethanol, farnesol and tyrosol. Because of phenylethanol and tryptophol showed the strongest effect to the growth and biofilm formation of A. fumigatus. Therefore, the cytotoxic activities of phenylethanol and tryptophol in A549 cells (lung alveolar epithelial cells) were determined. However, phenylethanol and tryptophol induced A549 cell damage (at MIC level), as demonstrated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) and lactate dehydrogenase (LDH) assays.

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5

Khedkar, Vivek, Annegret Tillack, Manfred Michalik, and Matthias Beller. "Convenient synthesis of tryptophols and tryptophol homologues by hydroamination of alkynes." Tetrahedron 61, no. 32 (August 2005): 7622–31. http://dx.doi.org/10.1016/j.tet.2005.05.093.

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6

Cordente, Antonio G., Damian Espinase Nandorfy, Mark Solomon, Alex Schulkin, Radka Kolouchova, Ian Leigh Francis, and Simon A. Schmidt. "Aromatic Higher Alcohols in Wine: Implication on Aroma and Palate Attributes during Chardonnay Aging." Molecules 26, no. 16 (August 17, 2021): 4979. http://dx.doi.org/10.3390/molecules26164979.

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The higher alcohols 2-phenylethanol, tryptophol, and tyrosol are a group of yeast-derived compounds that have been shown to affect the aroma and flavour of fermented beverages. Five variants of the industrial wine strain AWRI796, previously isolated due to their elevated production of the ‘rose-like aroma’ compound 2-phenylethanol, were characterised during pilot-scale fermentation of a Chardonnay juice. We show that these variants not only increase the concentration of 2-phenylethanol but also modulate the formation of the higher alcohols tryptophol, tyrosol, and methionol, as well as other volatile sulfur compounds derived from methionine, highlighting the connections between yeast nitrogen and sulfur metabolism during fermentation. We also investigate the development of these compounds during wine storage, focusing on the sulfonation of tryptophol. Finally, the sensory properties of wines produced using these strains were quantified at two time points, unravelling differences produced by biologically modulating higher alcohols and the dynamic changes in wine flavour over aging.

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7

Xu, Jun, and Rongbiao Tong. "An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives." Green Chemistry 19, no. 13 (2017): 2952–56. http://dx.doi.org/10.1039/c7gc01341h.

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8

Gu, Quanli, Swarna Basu, and J. L. Knee. "Tryptophol Cation Conformations Studied with ZEKE Spectroscopy." Journal of Physical Chemistry A 111, no. 10 (March 2007): 1808–13. http://dx.doi.org/10.1021/jp067355a.

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9

Guzmán-López, Oswaldo, Ángel Trigos, Francisco J. Fernández, María de Jesús Yañez-Morales, and Gerardo Saucedo-Castañeda. "Tyrosol and tryptophol produced by Ceratocystis adiposa." World Journal of Microbiology and Biotechnology 23, no. 10 (April 25, 2007): 1473–77. http://dx.doi.org/10.1007/s11274-007-9392-9.

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10

Laćan, Goran, Volker Magnus, Šumski Šimaga, Sonja Iskrić, and Prudence J. Hall. "Metabolism of Tryptophol in Higher and Lower Plants." Plant Physiology 78, no. 3 (July 1, 1985): 447–54. http://dx.doi.org/10.1104/pp.78.3.447.

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11

Sanchez, Raquel, Walther Caminati, Juan C. López, and José L. Alonso. "The rotational spectra of conformers of biomolecules: Tryptophol." Chemical Physics Letters 414, no. 1-3 (October 2005): 226–29. http://dx.doi.org/10.1016/j.cplett.2005.08.071.

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12

Dubhashe, Yogeshwar R., Vishal M. Sawant, and Vilas G. Gaikar. "Process Intensification of Continuous Flow Synthesis of Tryptophol." Industrial & Engineering Chemistry Research 57, no. 8 (February 19, 2018): 2787–96. http://dx.doi.org/10.1021/acs.iecr.7b04483.

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13

Liu, Kun, Yuqi Deng, Wenxu Song, Chunlan Song, and Aiwen Lei. "Electrochemical Dearomative Halocyclization of Tryptamine and Tryptophol Derivatives." Chinese Journal of Chemistry 38, no. 10 (June 16, 2020): 1070–74. http://dx.doi.org/10.1002/cjoc.202000194.

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14

Iraqui, Ismaïl, Stéphan Vissers, Bruno André, and Antonio Urrestarazu. "Transcriptional Induction by Aromatic Amino Acids in Saccharomyces cerevisiae." Molecular and Cellular Biology 19, no. 5 (May 1, 1999): 3360–71. http://dx.doi.org/10.1128/mcb.19.5.3360.

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ABSTRACT Aromatic aminotransferase II, product of the ARO9 gene, catalyzes the first step of tryptophan, phenylalanine, and tyrosine catabolism in Saccharomyces cerevisiae. ARO9 expression is under the dual control of specific induction and nitrogen source regulation. We have here identified UASaro, a 36-bp upstream element necessary and sufficient to promote transcriptional induction of reporter gene expression in response to tryptophan, phenylalanine, or tyrosine. We then isolated mutants in which UASaro-mediated ARO9 transcription is partially or totally impaired. Mutations abolishingARO9 induction affect a gene called ARO80(YDR421w), coding for a Zn2Cys6 family transcription factor. A sequence highly similar to UASaro was found upstream from theYDR380w gene encoding a homolog of bacterial indolepyruvate decarboxylase. In yeast, this enzyme is postulated to catalyze the second step of tryptophan catabolism to tryptophol. We show that ARO9 and YDR380w(named ARO10) have similar patterns of transcriptional regulation and are both under the positive control of Aro80p. Nitrogen regulation of ARO9 expression seems not directly to involve the general factor Ure2p, Gln3p, Nil1p, Uga43p, or Gzf3p.ARO9 expression appears, rather, to be mainly regulated by inducer exclusion. Finally, we show that Gap1p, the general amino acid permease, and Wap1p (Ycl025p), a newly discovered inducible amino acid permease with broad specificity, are the main aromatic amino acid transporters for catabolic purposes.

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15

Luo, Kun, Caro-Lyne DesRoches, Anne Johnston, Linda J. Harris, Hui-Yan Zhao, and Thérèse Ouellet. "Multiple metabolic pathways for metabolism of l-tryptophan in Fusarium graminearum." Canadian Journal of Microbiology 63, no. 11 (November 2017): 921–27. http://dx.doi.org/10.1139/cjm-2017-0383.

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Fusarium graminearum is a plant pathogen that can cause the devastating cereal grain disease fusarium head blight in temperate regions of the world. Previous studies have shown that F. graminearum can synthetize indole-3-acetic acid (auxin) using l-tryptophan (L-TRP)-dependent pathways. In the present study, we have taken a broader approach to examine the metabolism of L-TRP in F. graminearum liquid culture. Our results showed that F. graminearum was able to transiently produce the indole tryptophol when supplied with L-TRP. Comparative gene expression profiling between L-TRP-treated and control cultures showed that L-TRP treatment induced the upregulation of a series of genes with predicted function in the metabolism of L-TRP via anthranilic acid and catechol towards the tricarboxylic acid cycle. It is proposed that this metabolic activity provides extra energy for 15-acetyldeoxynivalenol production, as observed in our experiments. This is the first report of the use of L-TRP to increase energy resources in a Fusarium species.

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16

Álvarez-Fernández, M. Antonia, Ilaria Carafa, Urska Vrhovsek, and Panagiotis Arapitsas. "Modulating Wine Aromatic Amino Acid Catabolites by Using Torulaspora delbrueckii in Sequentially Inoculated Fermentations or Saccharomyces cerevisiae Alone." Microorganisms 8, no. 9 (September 4, 2020): 1349. http://dx.doi.org/10.3390/microorganisms8091349.

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Yeasts are the key microorganisms that transform grape juice into wine, and nitrogen is an essential nutrient able to affect yeast cell growth, fermentation kinetics and wine quality. In this work, we focused on the intra- and extracellular metabolomic changes of three aromatic amino acids (tryptophan, tyrosine, and phenylalanine) during alcoholic fermentation of two grape musts by two Saccharomyces cerevisiae strains and the sequential inoculation of Torulaspora delbrueckii with Saccharomyces cerevisiae. An UPLC-MS/MS method was used to monitor 33 metabolites, and 26 of them were detected in the extracellular samples and 8 were detected in the intracellular ones. The results indicate that the most intensive metabolomic changes occurred during the logarithm cellular growth phase and that pure S. cerevisiae fermentations produced higher amounts of N-acetyl derivatives of tryptophan and tyrosine and the off-odour molecule 2-aminoacetophenone. The sequentially inoculated fermentations showed a slower evolution and a higher production of metabolites linked to the well-known plant hormone indole acetic acid (auxin). Finally, the production of sulfonated tryptophol during must fermentation was confirmed, which also may explain the bitter taste of wines produced by Torulaspora delbrueckii co-fermentations, while sulfonated indole carboxylic acid was detected for the first time in such an experimental design.

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17

Furukawa, T., J. Koga, T. Adachi, K. Kishi, and K. Syono. "Efficient Conversion of L-Tryptophan to Indole-3-Acetic Acid and/or Tryptophol by Some Species of Rhizoctonia." Plant and Cell Physiology 37, no. 7 (October 1, 1996): 899–905. http://dx.doi.org/10.1093/oxfordjournals.pcp.a029037.

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18

Khan, Mohd Faheem, Dua Saleem, and Cormac D. Murphy. "Regulation of Cunninghamella spp. biofilm growth by tryptophol and tyrosol." Biofilm 3 (December 2021): 100046. http://dx.doi.org/10.1016/j.bioflm.2021.100046.

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19

Yi, John T., and David W. Pratt. "Rotationally resolved electronic spectroscopy of tryptophol in the gas phase." Physical Chemistry Chemical Physics 7, no. 21 (2005): 3680. http://dx.doi.org/10.1039/b508610h.

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20

do Nascimento, A. L. V., W. R. Macedo, G. H. Silva, R. G. de Almeida Neto, M. G. Mendes, and P. E. R. Marchiori. "Physiological and agronomical responses of common bean subjected to tryptophol." Annals of Applied Biology 168, no. 2 (November 20, 2015): 195–202. http://dx.doi.org/10.1111/aab.12255.

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21

INAGAKI, Shyuichiro, Shigeru MORIMURA, Yueqin TANG, Hiroshi AKUTAGAWA, and Kenji KIDA. "Tryptophol Induces Death Receptor (DR) 5-Mediated Apoptosis in U937 Cells." Bioscience, Biotechnology, and Biochemistry 71, no. 8 (August 23, 2007): 2065–68. http://dx.doi.org/10.1271/bbb.70084.

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22

Erdoğan, İlkay, Bilge Şener, and Tatsuo Higa. "Tryptophol, a plant auxin isolated from the marine sponge Ircinia spinulosa." Biochemical Systematics and Ecology 28, no. 8 (October 2000): 793–94. http://dx.doi.org/10.1016/s0305-1978(99)00111-8.

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23

Liang, Xiao-Wei, Yue Cai, and Shu-Li You. "Asymmetric Fluorinative Dearomatization of Tryptophol Derivatives by Chiral Anion Phase-Transfer Catalysis." Chinese Journal of Chemistry 36, no. 10 (August 20, 2018): 925–28. http://dx.doi.org/10.1002/cjoc.201800319.

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24

Jin, Min, Chenxi Xu, and Xiaobo Zhang. "The effect of tryptophol on the bacteriophage infection in high-temperature environment." Applied Microbiology and Biotechnology 99, no. 19 (May 21, 2015): 8101–11. http://dx.doi.org/10.1007/s00253-015-6674-2.

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25

Barik, Sailen. "The Uniqueness of Tryptophan in Biology: Properties, Metabolism, Interactions and Localization in Proteins." International Journal of Molecular Sciences 21, no. 22 (November 20, 2020): 8776. http://dx.doi.org/10.3390/ijms21228776.

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Tryptophan (Trp) holds a unique place in biology for a multitude of reasons. It is the largest of all twenty amino acids in the translational toolbox. Its side chain is indole, which is aromatic with a binuclear ring structure, whereas those of Phe, Tyr, and His are single-ring aromatics. In part due to these elaborate structural features, the biosynthetic pathway of Trp is the most complex and the most energy-consuming among all amino acids. Essential in the animal diet, Trp is also the least abundant amino acid in the cell, and one of the rarest in the proteome. In most eukaryotes, Trp is the only amino acid besides Met, which is coded for by a single codon, namely UGG. Due to the large and hydrophobic π-electron surface area, its aromatic side chain interacts with multiple other side chains in the protein, befitting its strategic locations in the protein structure. Finally, several Trp derivatives, namely tryptophylquinone, oxitriptan, serotonin, melatonin, and tryptophol, have specialized functions. Overall, Trp is a scarce and precious amino acid in the cell, such that nature uses it parsimoniously, for multiple but selective functions. Here, the various aspects of the uniqueness of Trp are presented in molecular terms.

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26

INAGAKI, Shyuichiro, Shigeru MORIMURA, Kazunobu GONDO, Yuegin TANG, Hiroshi AKUTAGAWA, and Kenji KIDA. "Tryptophol, a novel apoptosis-inducing component produced in the process of ethanol fermentation." JOURNAL OF THE BREWING SOCIETY OF JAPAN 102, no. 3 (2007): 222–24. http://dx.doi.org/10.6013/jbrewsocjapan1988.102.222.

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27

Liu, Huan, Guangde Jiang, Xixian Pan, Xiaolong Wan, Yisheng Lai, Dawei Ma, and Weiqing Xie. "Highly Asymmetric Bromocyclization of Tryptophol: Unexpected Accelerating Effect of DABCO-Derived Bromine Complex." Organic Letters 16, no. 7 (March 25, 2014): 1908–11. http://dx.doi.org/10.1021/ol5004109.

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28

Gil, C., and C. Gómez-Cordovés. "Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes." Food Chemistry 22, no. 1 (January 1986): 59–65. http://dx.doi.org/10.1016/0308-8146(86)90009-9.

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29

Spanic, Valentina, Zorana Katanic, Michael Sulyok, Rudolf Krska, Katalin Puskas, Gyula Vida, Georg Drezner, and Bojan Šarkanj. "Multiple Fungal Metabolites Including Mycotoxins in Naturally Infected and Fusarium-Inoculated Wheat Samples." Microorganisms 8, no. 4 (April 17, 2020): 578. http://dx.doi.org/10.3390/microorganisms8040578.

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In this study, the occurrence of multiple fungal metabolites including mycotoxins was determined in four different winter wheat varieties in a field experiment in Croatia. One group was naturally infected, while the second group was inoculated with a Fusarium graminearum and F. culmorum mixture to simulate a worst-case infection scenario. Data on the multiple fungal metabolites including mycotoxins were acquired with liquid chromatography with mass spectrometry (LC-MS/MS) multi-(myco)toxin method. In total, 36 different fungal metabolites were quantified in this study: the Fusarium mycotoxins deoxynivalenol (DON), DON-3-glucoside (D3G), 3-acetyldeoxynivalenol (3-ADON), culmorin (CULM), 15-hydroxyculmorin, 5-hydroxyculmorin, aurofusarin, rubrofusarin, enniatin (Enn) A, Enn A1, Enn B, Enn B1, Enn B2, Enn B3, fumonisin B1, fumonisin B2, chrysogin, zearalenone (ZEN), moniliformin (MON), nivalenol (NIV), siccanol, equisetin, beauvericin (BEA), and antibiotic Y; the Alternaria mycotoxins alternariol, alternariolmethylether, altersetin, infectopyron, tentoxin, tenuazonic acid; the Aspergillus mycotoxin kojic acid; unspecific metabolites butenolid, brevianamid F, cyclo(L-Pro-L-Tyr), cyclo(L-Pro-L-Val), and tryptophol. The most abundant mycotoxins in the inoculated and naturally contaminated samples, respectively, were found to occur at the following average concentrations: DON (19,122/1504 µg/kg), CULM (6109/1010 µg/kg), 15-hydroxyculmorin (56,022/1301 µg/kg), 5-hydroxyculmorin (21,219/863 µg/kg), aurofusarin (43,496/1266 µg/kg). Compared to naturally-infected samples, Fusarium inoculations at the flowering stage increased the concentrations of all Fusarium mycotoxins, except enniatins and siccanol in Ficko, the Aspergillus metabolite kojic acid, the Alternaria mycotoxin altersetin, and unspecific metabolites brevianamid F, butenolid, cyclo(L-Pro-L-Tyr), and cyclo(L-Pro-L-Val). In contrast to these findings, because of possible antagonistic actions, Fusarium inoculation decreased the concentrations of the Alternaria toxins alternariol, alternariolmethylether, infectopyron, tentoxin, tenuazonic acid, as well as the concentration of the nonspecific metabolite tryptophol.

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Kitisin, Thitinan, Watcharamat Muangkaew, Sumate Ampawong, and Passanesh Sukphopetch. "Tryptophol Coating Reduces Catheter-Related Cerebral and Pulmonary Infections by Scedosporium apiospermum." Infection and Drug Resistance Volume 13 (July 2020): 2495–508. http://dx.doi.org/10.2147/idr.s255489.

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31

Yu, Jieqiang, Jun Jia, and Xingwang Wang. "Synthesis of a Type of Linear β,γ-Unsaturated α-Keto Tryptophol Ester Compounds." Chinese Journal of Organic Chemistry 40, no. 9 (2020): 2778. http://dx.doi.org/10.6023/cjoc202005051.

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32

Kwaśna, H., and P. Lakomy. "Stimulation of Armillaria ostoyae vegetative growth by tryptophol and rhizomorph produced by Zygorhynchus moelleri." Forest Pathology 28, no. 1 (January 1998): 53–61. http://dx.doi.org/10.1111/j.1439-0329.1998.tb01165.x.

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33

Shao, Lulu, Ping Wu, Liangxiong Xu, Jinghua Xue, Hanxiang Li, and Xiaoyi Wei. "Colletotryptins A–F, new dimeric tryptophol derivatives from the endophytic fungus Colletotrichum sp. SC1355." Fitoterapia 141 (March 2020): 104465. http://dx.doi.org/10.1016/j.fitote.2019.104465.

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34

Ayer, William A., Lois M. Browne, Meow-Chen Feng, Helena Orszanska, and Hussein Saeedi-Ghomi. "The chemistry of the blue stain fungi. Part 1. Some metabolites of Ceratocystis species associated with mountain pine beetle infected lodgepole pine." Canadian Journal of Chemistry 64, no. 5 (May 1, 1986): 904–9. http://dx.doi.org/10.1139/v86-149.

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Metabolites formed in still culture by Ceratocystisclavigera, C. ips, and C. huntii, three of the four Ceratocystis species associated with the blue stain disease of pine, have been identified. In addition to the ubiquitous fungal metabolites ergosterol, ergosterol peroxide, and fatty acids we have isolated succinic acid, β-phenethyl alcohol (1), tryptophol (2), prolylleucyl anhydride (3), tyrosol (4), 3-phenylpropane-1,2-diol (5), 6,8-dihydroxy-3-methylisocoumarin (8), 6,8-dihydroxy-3-hydroxymethylisocoumarin (9), p-hydroxybenzaldehyde (10), phenylacetic acid (11), p-hydroxyphenylacetic acid (12), phenyllactic acid (13), p-hydroxyphenyllactic acid (14), and 2,3-dihydroxybenzoic acid (15). The complex formed by chelation of iron with 2,3-dihydroxybenzoic acid may be responsible, at least in part, for the blue staining of the sapwood of diseased pine.

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35

Li, Mei, Zhaoxia Yang, Junguang Hao, Lianju Shan, and Jianjun Dong. "Determination of Tyrosol, 2-Phenethyl Alcohol, and Tryptophol in Beer by High-Performance Liquid Chromatography." Journal of the American Society of Brewing Chemists 66, no. 4 (September 2008): 245–49. http://dx.doi.org/10.1094/asbcj-2008-0914-01.

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36

Kumar, Anil, and Shipra Mital. "Electronic and photocatalytic properties of purine(s)-capped CdS nanoparticles in the presence of tryptophol." Journal of Molecular Catalysis A: Chemical 219, no. 1 (September 2004): 65–71. http://dx.doi.org/10.1016/j.molcata.2004.05.005.

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37

Zhu, Fei, and Min Jin. "The effects of a thermophile metabolite, tryptophol, upon protecting shrimp against white spot syndrome virus." Fish & Shellfish Immunology 47, no. 2 (December 2015): 777–81. http://dx.doi.org/10.1016/j.fsi.2015.10.015.

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38

Liu, Huan, Guangde Jiang, Xixian Pan, Xiaolong Wan, Yisheng Lai, Dawei Ma, and Weiqing Xie. "ChemInform Abstract: Highly Asymmetric Bromocyclization of Tryptophol: Unexpected Accelerating Effect of DABCO-Derived Bromine Complex." ChemInform 45, no. 37 (August 28, 2014): no. http://dx.doi.org/10.1002/chin.201437135.

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39

Rostoll-Berenguer, Jaume, Gonzalo Blay, José Pedro, and Carlos Vila. "9,10-Phenanthrenedione as Visible-Light Photoredox Catalyst: A Green Methodology for the Functionalization of 3,4-Dihydro-1,4-Benzoxazin-2-Ones through a Friedel-Crafts Reaction." Catalysts 8, no. 12 (December 12, 2018): 653. http://dx.doi.org/10.3390/catal8120653.

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A visible-light photoredox functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones through a Friedel-Crafts reaction with indoles using an inexpensive organophotoredox catalyst is described. The reaction uses a dual catalytic system that is formed by a photocatalyst simple and cheap, 9,10-phenanthrenedione, and a Lewis acid, Zn(OTf)2. 5W white LEDs are used as visible-light source and oxygen from air as a terminal oxidant, obtaining the corresponding products with good yields. The reaction can be extended to other electron-rich arenes. Our methodology represents one of the most valuable and sustainable approach for the functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones, as compared to the reported procedures. Furthermore, several transformations were carried out, such as the synthesis of the natural product cephalandole A and a tryptophol derivative.

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Habschied, Kristina, Rudolf Krska, Michael Sulyok, Bojan Šarkanj, Vinko Krstanović, Alojzije Lalić, Gordana Šimić, and Krešimir Mastanjević. "Screening of Various Metabolites in Six Barley Varieties Grown under Natural Climatic Conditions (2016–2018)." Microorganisms 7, no. 11 (November 6, 2019): 532. http://dx.doi.org/10.3390/microorganisms7110532.

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Climatic changes influence considerably the distribution and occurrence of different secondary metabolites in cereals. The aim of this investigation was to assess the changes in metabolite prevalence observed in six different winter barley varieties over a statistically significant period of three years by linking agro-climatic conditions with metabolite concentrations in chosen samples. The results showed that temperatures and precipitation levels varied during the observed timeframe and that the multi-toxin concentrations followed the trend of changing climatic conditions depending on the variety. All quantified (fungal) metabolites showed significant variations throughout the years and, for some (tryptophol and the cyclic dipeptides cyclo(L-Pro-L-Tyr) and cyclo(L-Pro-L-Val)), an unexpected, but clear connection can be made with temperature changes and precipitation levels during the growing season.

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Watanabe, Toshiro, Akira Yamamoto, Shiro Nagai, and Shigeru Terabe. "Simultaneous analysis of tyrosol, tryptophol and ferulic acid in commercial sake samples by micellar electrokinetic chromatography." Journal of Chromatography A 825, no. 1 (October 1998): 102–6. http://dx.doi.org/10.1016/s0021-9673(98)00684-0.

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Kitisin, Thitinan, Watcharamat Muangkaew, Sumate Ampawong, Nichapa Sansurin, Natthawut Thitipramote, and Passanesh Sukphopetch. "Development and efficacy of tryptophol-containing emulgel for reducing subcutaneous fungal nodules from Scedosporium apiospermum eumycetoma." Research in Pharmaceutical Sciences 17, no. 6 (2022): 707. http://dx.doi.org/10.4103/1735-5362.359437.

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Cai, Yichang, Yi Zhang, Han Bao, Jiaoyun Chen, Jianwen Chen, and Wankuan Shen. "Squalene Monooxygenase Gene SsCI80130 Regulates Sporisorium scitamineum Mating/Filamentation and Pathogenicity." Journal of Fungi 8, no. 5 (April 30, 2022): 470. http://dx.doi.org/10.3390/jof8050470.

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Sugarcane is an important sugar crop and energy crop worldwide. Sugarcane smut caused by Sporisorium scitamineum is a serious fungal disease that occurs worldwide, seriously affecting the yield and quality of sugarcane. It is essential to reveal the molecular pathogenesis of S. scitamineum to explore a new control strategy of sugarcane smut. Based on transcriptome sequencing data of two S. scitamineum strains Ss16 and Ss47, each with a different pathogenicity, our laboratory screened out the SsCI80130 gene predicted to encode squalene monooxygenase. In this study, we obtained the knockout mutants (ΔSs80130+ and ΔSs80130−) and complementary mutants (COM80130+ and COM80130−) of this gene by the polyethylene glycol-mediated (PEG-mediated) protoplast transformation technology, and then performed a functional analysis of the gene. The results showed that the deletion of the SsCI80130 gene resulted in the increased content of squalene (substrate for squalene monooxygenase) and decreased content of ergosterol (the final product of the ergosterol synthesis pathway) in S. scitamineum. Meanwhile, the sporidial growth rate of the knockout mutants was significantly slower than that of the wild type and complementary mutants; under cell-wall stress or oxidative stress, the growth of the knockout mutants was significantly inhibited. In addition, the sexual mating ability and pathogenicity of knockout mutants were significantly weakened, while the sexual mating ability could be restored by adding exogenous small-molecular signal substance cAMP (cyclic adenosine monophosphate) or tryptophol. It is speculated that the SsCI80130 gene was involved in the ergosterol biosynthesis in S. scitamineum and played an important role in the sporidial growth, stress response to different abiotic stresses (including cell wall stress and oxidative stress), sexual mating/filamentation and pathogenicity. Moreover, the SsCI80130 gene may affect the sexual mating and pathogenicity of S. scitamineum by regulating the ergosterol synthesis and the synthesis of the small-molecular signal substance cAMP or tryptophol required for sexual mating. This study reveals for the first time that the gene encoding squalene monooxygenase is involved in regulating the sexual mating and pathogenicity of S. scitamineum, providing a basis for the molecular pathogenic mechanism of S. scitamineum.

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Petrić, Jasenka, Bojan Šarkanj, Ibrahim Mujić, Aida Mujić, Michael Sulyok, Rudolf Krska, Drago Šubarić, and Stela Jokić. "Effect of pretreatments on mycotoxin profiles and levels in dried figs." Archives of Industrial Hygiene and Toxicology 69, no. 4 (December 1, 2018): 328–33. http://dx.doi.org/10.2478/aiht-2018-69-3147.

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AbstractThe aim of this explorative study was to investigate how effective drying preservation methods are in reducing mycotoxin content in figs. Dried autochthonous varieties of white and dark figs (Petrovača Bijela and Šaraguja, respectively) were analysed for mycotoxins using an LC-MS/MS “dilute and shoot” method capable of determining 295 fungal and bacterial secondary metabolites. Before drying in a cabinet dryer the figs were preserved with 0.5 % citric acid solution or 0.5 % ascorbic acid solution or 0.3 % L-cysteine solution or 0.2 % chestnut extract solution or 0.15 % Echinacea extract solution by immersion. We found nine metabolites: aflatoxin B1 (AFB1), ochratoxin A, ochratoxin alpha, kojic acid, emodin, altenuene, alternariol methyl ether, brevianamide F, and tryptophol. The most efficient preserver was L-cysteine (15 % reduction), while ascorbic acid favoured mycotoxin production (158 % increase). However, all pretreatment solutions reduced AFB1, which is a major fig contaminant.

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Kosalec, Ivan, Amalija Šafranić, Stjepan Pepeljnjak, Višnja Bačun-Družina, Snježana Ramić, and Nevenka Kopjar. "Genotoxicity of Tryptophol in a Battery of Short-Term Assays on Human White Blood Cells in vitro." Basic & Clinical Pharmacology & Toxicology 102, no. 5 (May 2008): 443–52. http://dx.doi.org/10.1111/j.1742-7843.2007.00204.x.

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Singkum, Pantira, Watcharamat Muangkaew, San Suwanmanee, Potjaman Pumeesat, Thanwa Wongsuk, and Natthanej Luplertlop. "Suppression of the pathogenicity of Candida albicans by the quorum-sensing molecules farnesol and tryptophol." Journal of General and Applied Microbiology 65, no. 6 (2019): 277–83. http://dx.doi.org/10.2323/jgam.2018.12.002.

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Bordiga, M., C. Lorenzo, F. Pardo, M. R. Salinas, F. Travaglia, M. Arlorio, J. D. Coïsson, and T. Garde-Cerdán. "Factors influencing the formation of histaminol, hydroxytyrosol, tyrosol, and tryptophol in wine: Temperature, alcoholic degree, and amino acids concentration." Food Chemistry 197 (April 2016): 1038–45. http://dx.doi.org/10.1016/j.foodchem.2015.11.112.

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Kuś, Piotr M., Sławomir Czabaj, and Igor Jerković. "Comparison of Volatile Profiles of Meads and Related Unifloral Honeys: Traceability Markers." Molecules 27, no. 14 (July 17, 2022): 4558. http://dx.doi.org/10.3390/molecules27144558.

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Volatile profiles of unifloral honeys and meads prepared in different ways (boiled-saturated, not boiled-unsaturated) were investigated by headspace solid-phase micro extraction (HS-SPME) and dehydration homogeneous liquid–liquid extraction (DHLLE) followed by GC-FID/MS analyses. The obtained data were analyzed by principal component analysis (PCA) to evaluate the differences between the investigated products. The volatile profiles of honey as well as the boiled and the not boiled meads prepared from it showed significant discrepancies. The meads contained more aliphatic acids and esters but fewer monoterpenes and aliphatic hydrocarbons than the honey. Significant/substantial differences were found between the boiled (more aliphatic alcohols and acids) and the not boiled meads (more aliphatic hydrocarbons and esters). Some compounds related to yeast metabolism, such as tryptophol, may be considered markers of honey fermentation. This research allowed us to identify chemical markers of botanical origin, retained and detectable in the meads: 4-isopropenylcyclohexa-1,3-diene-1-carboxylic acid and 4-(1-hydroxy-2-propanyl)cyclohexa-1,3-diene-1-carboxylic acid for linden; valeric acid, γ-valerolactone, p-hydroxybenzoic acid for buckwheat; 4-hydroxybenzeneacetic acid, homovanillic acid and trans-coniferyl alcohol for honeydew; and methyl syringate for canola.

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LANDETE, JOSÉ MARÍA, HÉCTOR RODRÍGUEZ, BLANCA DE LAS RIVAS, and ROSARIO MUÑOZ. "High-Added-Value Antioxidants Obtained from the Degradation of Wine Phenolics by Lactobacillus plantarum." Journal of Food Protection 70, no. 11 (November 1, 2007): 2670–75. http://dx.doi.org/10.4315/0362-028x-70.11.2670.

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Disposal of the waste from wine production has long been a problem for wineries, mainly because of the presence of phenolic compounds. In this study, we analyzed the antimicrobial activities of 10 wine phenolic compounds against Lactobacillus plantarum strains. Inhibition increased in this order: catechin = gallic acid < epicatechin = salicylic acid < methyl gallate = caffeic acid < ferulic acid = tryptophol < p-coumaric acid. The obtained results indicated that L. plantarum is able to grow in the presence of high concentrations of some wine phenolic compounds. Of the 10 compounds analyzed, only the hydroxycinnamic acids, gallic acid, and methyl gallate were metabolized by the four L. plantarum strains studied. Results also revealed that 4-vinylphenol and 4-vinylguaiacol are originated from p-coumaric and ferulic acids. These phenolic compounds are valuable intermediates in the biotechnological production of new fragrances. In addition, gallic acid and its ester, methyl gallate, are metabolized to produce the powerful antioxidant pyrogallol. Therefore, it might be possible to use L. plantarum strains to obtain high-added-value antioxidants from the degradation of phenolic compounds found in wine wastes.

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Ibrar, Aliya, Sumera Zaib, Tuncer Hökelek, Jim Simpson, Christopher John McAdam, Islam H. El Azab, Gaber A. M. Mersal, Mohamed M. Ibrahim, Antonio Frontera, and Imtiaz Khan. "Investigation of solid state architectures in tetrazolyl tryptophol stabilized by crucial aromatic interactions and hydrogen bonding: Experimental and theoretical analysis." Journal of Molecular Structure 1262 (August 2022): 133079. http://dx.doi.org/10.1016/j.molstruc.2022.133079.

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