Indole-3-carbaldehyde has reactivity typical of aromatic aldehydes. It can is easily oxidized to indole-3-carboxylic acid. It condenses with nitromethane in a Henry reaction to give 3-nitrovinyl indole.
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Antifungal propertiesedit
Indole-3-carbaldehyde has antifungal properties, and partially accounts for the protection from chytridiomycosis seen in amphibian species which carry Janthinobacterium lividum on their skin.[8]
Referencesedit
^Dileep, C. S; Abdoh, M. M. M; Chakravarthy, M. P; Mohana, K. N; Sridhar, M. A (2012). "1H-Indole-3-carbaldehyde". Acta Crystallographica Section E. 68 (11): o3135. doi:10.1107/S1600536812040573. PMC3515237. PMID 23284457.
^ abcdefghijkZhang LS, Davies SS (April 2016). "Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions". Genome Med. 8 (1): 46. doi:10.1186/s13073-016-0296-x. PMC4840492. PMID 27102537. Lactobacillus spp. convert tryptophan to indole-3-aldehyde (I3A) through unidentified enzymes [125]. Clostridium sporogenes convert tryptophan to IPA [6], likely via a tryptophan deaminase. ... IPA also potently scavenges hydroxyl radicals Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
^ abIndole-3-carboxaldehyde. United States National Library of Medicine – National Center for Biotechnology Information. 11 November 2017. Retrieved 17 November 2017. {{cite encyclopedia}}: |work= ignored (help)
^ROMANI LUIGINA, TERESA ZELANTE (2013). "Tryptophan catabolites from microbiota engage aryl hydrocarbon receptor and balance mucosal reactivity via interleukin-22". Immunity. 39 (2): 372–385. doi:10.1016/j.immuni.2013.08.003. PMID 23973224.
^Wikoff WR, Anfora AT, Liu J, Schultz PG, Lesley SA, Peters EC, Siuzdak G (March 2009). "Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites". Proc. Natl. Acad. Sci. U.S.A. 106 (10): 3698–3703. Bibcode:2009PNAS..106.3698W. doi:10.1073/pnas.0812874106. PMC2656143. PMID 19234110. Production of IPA was shown to be completely dependent on the presence of gut microflora and could be established by colonization with the bacterium Clostridium sporogenes. IPA metabolism diagram
^"3-Indolepropionic acid". Human Metabolome Database. University of Alberta. Retrieved 12 June 2018.
^Chyan YJ, Poeggeler B, Omar RA, Chain DG, Frangione B, Ghiso J, Pappolla MA (July 1999). "Potent neuroprotective properties against the Alzheimer beta-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid". J. Biol. Chem. 274 (31): 21937–21942. doi:10.1074/jbc.274.31.21937. PMID 10419516. S2CID 6630247. [Indole-3-propionic acid (IPA)] has previously been identified in the plasma and cerebrospinal fluid of humans, but its functions are not known. ... In kinetic competition experiments using free radical-trapping agents, the capacity of IPA to scavenge hydroxyl radicals exceeded that of melatonin, an indoleamine considered to be the most potent naturally occurring scavenger of free radicals. In contrast with other antioxidants, IPA was not converted to reactive intermediates with pro-oxidant activity.
^Brucker, Robert M.; Harris, Reid N.; Schwantes, Christian R.; Gallaher, Thomas N.; Flaherty, Devon C.; Lam, Brianna A.; Minbiole, Kevin P. C. (2008-11-01). "Amphibian chemical defense: antifungal metabolites of the microsymbiont Janthinobacterium lividum on the salamander Plethodon cinereus". Journal of Chemical Ecology. 34 (11): 1422–1429. doi:10.1007/s10886-008-9555-7. ISSN 0098-0331. PMID 18949519. S2CID 9712168.
December 18, 2023
indole, carbaldehyde, also, known, indole, aldehyde, formylindole, metabolite, dietary, tryptophan, which, synthesized, human, gastrointestinal, bacteria, particularly, species, lactobacillus, genus, biologically, active, metabolite, which, acts, receptor, ago. Indole 3 carbaldehyde I3A also known as indole 3 aldehyde and 3 formylindole is a metabolite of dietary L tryptophan which is synthesized by human gastrointestinal bacteria particularly species of the Lactobacillus genus 2 3 I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells in turn stimulating the production of interleukin 22 which facilitates mucosal reactivity 4 3 2 Indole 3 carbaldehyde NamesIUPAC name 1H Indole 3 carbaldehydeOther names 3 Formylindole Indole 3 carboxaldehyde Indole 3 aldehydeIdentifiersCAS Number 487 89 83D model JSmol Interactive imageBeilstein Reference 5 21 08 00246ChEMBL ChEMBL147741ChemSpider 9838ECHA InfoCard 100 006 969EC Number 207 665 8PubChem CID 10256UNII 7FN04C32UOCompTox Dashboard EPA DTXSID5060069InChI InChI 1S C9H7NO c11 6 7 5 10 9 4 2 1 3 8 7 9 h1 6 10HKey OLNJUISKUQQNIM UHFFFAOYSA NSMILES C1 CC C2C C1 C CN2 C OPropertiesChemical formula C 9H 7N OMolar mass 145 161 g mol 1Melting point 198 C 388 F 471 K StructureCrystal structure OrthorhombicSpace group Pca21Lattice constant a 14 076 b 5 8059 c 8 6909 1 Lattice volume V 710 3Formula units Z 4HazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Biosynthesis in humans and cellular effects 2 Chemistry 3 Antifungal properties 4 ReferencesBiosynthesis in humans and cellular effects editTryptophan metabolism by human gastrointestinal microbiota vte nbsp Tryptophan Clostridiumsporogenes Lacto bacilli Tryptophanase expressingbacteria IPA I3A Indole Liver Brain IPA I3A Indole Indoxylsulfate AST 120 AhR Intestinalimmunecells Intestinalepithelium PXR Mucosal homeostasis TNF a Junction protein coding mRNAs L cell GLP 1 T J Neuroprotectant Activation of glial cells and astrocytes 4 Hydroxy 2 nonenal levels DNA damage Antioxidant Inhibits b amyloid fibril formation Maintains mucosal reactivity IL 22 production Associated with vascular disease Oxidative stress Smooth muscle cell proliferation Aortic wall thickness and calcification Associated with chronic kidney disease Renal dysfunction Uremic toxin Kidneys nbsp This diagram shows the biosynthesis of bioactive compounds indole and certain other derivatives from tryptophan by bacteria in the gut 2 Indole is produced from tryptophan by bacteria that express tryptophanase 2 Clostridium sporogenes metabolizes tryptophan into indole and subsequently 3 indolepropionic acid IPA 5 a highly potent neuroprotective antioxidant that scavenges hydroxyl radicals 2 6 7 IPA binds to the pregnane X receptor PXR in intestinal cells thereby facilitating mucosal homeostasis and barrier function 2 Following absorption from the intestine and distribution to the brain IPA confers a neuroprotective effect against cerebral ischemia and Alzheimer s disease 2 Lactobacillaceae Lactobacillus s l species metabolize tryptophan into indole 3 aldehyde I3A which acts on the aryl hydrocarbon receptor AhR in intestinal immune cells in turn increasing interleukin 22 IL 22 production 2 Indole itself triggers the secretion of glucagon like peptide 1 GLP 1 in intestinal L cells and acts as a ligand for AhR 2 Indole can also be metabolized by the liver into indoxyl sulfate a compound that is toxic in high concentrations and associated with vascular disease and renal dysfunction 2 AST 120 activated charcoal an intestinal sorbent that is taken by mouth adsorbs indole in turn decreasing the concentration of indoxyl sulfate in blood plasma 2 Chemistry editIndole 3 carbaldehyde has reactivity typical of aromatic aldehydes It can is easily oxidized to indole 3 carboxylic acid It condenses with nitromethane in a Henry reaction to give 3 nitrovinyl indole This section is empty You can help by adding to it November 2017 Antifungal properties editIndole 3 carbaldehyde has antifungal properties and partially accounts for the protection from chytridiomycosis seen in amphibian species which carry Janthinobacterium lividum on their skin 8 References edit Dileep C S Abdoh M M M Chakravarthy M P Mohana K N Sridhar M A 2012 1H Indole 3 carbaldehyde Acta Crystallographica Section E 68 11 o3135 doi 10 1107 S1600536812040573 PMC 3515237 PMID 23284457 a b c d e f g h i j k Zhang LS Davies SS April 2016 Microbial metabolism of dietary components to bioactive metabolites opportunities for new therapeutic interventions Genome Med 8 1 46 doi 10 1186 s13073 016 0296 x PMC 4840492 PMID 27102537 Lactobacillus spp convert tryptophan to indole 3 aldehyde I3A through unidentified enzymes 125 Clostridium sporogenes convert tryptophan to IPA 6 likely via a tryptophan deaminase IPA also potently scavenges hydroxyl radicals Table 2 Microbial metabolites their synthesis mechanisms of action and effects on health and diseaseFigure 1 Molecular mechanisms of action of indole and its metabolites on host physiology and disease a b Indole 3 carboxaldehyde United States National Library of Medicine National Center for Biotechnology Information 11 November 2017 Retrieved 17 November 2017 a href Template Cite encyclopedia html title Template Cite encyclopedia cite encyclopedia a work ignored help ROMANI LUIGINA TERESA ZELANTE 2013 Tryptophan catabolites from microbiota engage aryl hydrocarbon receptor and balance mucosal reactivity via interleukin 22 Immunity 39 2 372 385 doi 10 1016 j immuni 2013 08 003 PMID 23973224 Wikoff WR Anfora AT Liu J Schultz PG Lesley SA Peters EC Siuzdak G March 2009 Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites Proc Natl Acad Sci U S A 106 10 3698 3703 Bibcode 2009PNAS 106 3698W doi 10 1073 pnas 0812874106 PMC 2656143 PMID 19234110 Production of IPA was shown to be completely dependent on the presence of gut microflora and could be established by colonization with the bacterium Clostridium sporogenes IPA metabolism diagram 3 Indolepropionic acid Human Metabolome Database University of Alberta Retrieved 12 June 2018 Chyan YJ Poeggeler B Omar RA Chain DG Frangione B Ghiso J Pappolla MA July 1999 Potent neuroprotective properties against the Alzheimer beta amyloid by an endogenous melatonin related indole structure indole 3 propionic acid J Biol Chem 274 31 21937 21942 doi 10 1074 jbc 274 31 21937 PMID 10419516 S2CID 6630247 Indole 3 propionic acid IPA has previously been identified in the plasma and cerebrospinal fluid of humans but its functions are not known In kinetic competition experiments using free radical trapping agents the capacity of IPA to scavenge hydroxyl radicals exceeded that of melatonin an indoleamine considered to be the most potent naturally occurring scavenger of free radicals In contrast with other antioxidants IPA was not converted to reactive intermediates with pro oxidant activity Brucker Robert M Harris Reid N Schwantes Christian R Gallaher Thomas N Flaherty Devon C Lam Brianna A Minbiole Kevin P C 2008 11 01 Amphibian chemical defense antifungal metabolites of the microsymbiont Janthinobacterium lividum on the salamander Plethodon cinereus Journal of Chemical Ecology 34 11 1422 1429 doi 10 1007 s10886 008 9555 7 ISSN 0098 0331 PMID 18949519 S2CID 9712168 Retrieved from https en wikipedia org w index php title Indole 3 carbaldehyde amp oldid 1111228154, wikipedia, wiki, book, books, library,
