Indole-3-carboxaldehyde
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Indole-3-carboxaldehyde

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Indole-3-carboxaldehyde is a tryptophan metabolite from Streptomyces staurosporeus and it is a chemical constituent from Inula wissmanniana. Indole-3-carboxaldehyde and other tryptophan metabolites play an important role in mammalian gut immune homeostasis.

Category
Amino Aldehydes
Catalog number
BAT-002694
CAS number
487-89-8
Molecular Formula
C9H7NO
Molecular Weight
145.16
Indole-3-carboxaldehyde
IUPAC Name
1H-indole-3-carbaldehyde
Synonyms
1H-Indole-3-carboxaldehyde; 1H-Indol-3-yl carboxaldehyde; 1H-Indole-3-aldehyde; 1H-Indole-3-carbaldehyde; 1H-Indole-3-methanal; 3-Formyl-1H-indole; 3-Formylindole; 3-Indolylformaldehyde; Indole-3-aldehyde; Indole-3-carbaldehyde; Indole-3-carboxylaldehyde; Indole-3-formaldehyde; NSC 10118; β-Indolylaldehyde
Related CAS
246045-99-8 (Deleted CAS)
Appearance
Light yellow to off white crystalline powder
Purity
≥95%
Density
1.278±0.06 g/cm3
Melting Point
194-200°C
Boiling Point
339.1±15.0°C at 760 Torr
Storage
Store at 2-8°C
Solubility
Soluble in Water
InChI
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI Key
OLNJUISKUQQNIM-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2)C=O
1.Plant-Derived Exosomal MicroRNAs Shape the Gut Microbiota
Cell Host Microbe. 2018 Nov 14;24(5):637-652.e8. doi: 10.1016/j.chom.2018.10.001.
The gut microbiota can be altered by dietary interventions to prevent and treat various diseases. However, the mechanisms by which food products modulate commensals remain largely unknown. We demonstrate that plant-derived exosome-like nanoparticles (ELNs) are taken up by the gut microbiota and contain RNAs that alter microbiome composition and host physiology. Ginger ELNs (GELNs) are preferentially taken up by Lactobacillaceae in a GELN lipid-dependent manner and contain microRNAs that target various genes in Lactobacillus rhamnosus (LGG). Among these, GELN mdo-miR7267-3p-mediated targeting of the LGG monooxygenase ycnE yields increased indole-3-carboxaldehyde (I3A). GELN-RNAs or I3A, a ligand for aryl hydrocarbon receptor, are sufficient to induce production of IL-22, which is linked to barrier function improvement. These functions of GELN-RNAs can ameliorate mouse colitis via IL-22-dependent mechanisms. These findings reveal how plant products and their effects on the microbiome may be used to target specific host processes to alleviate disease.
2.Targeting whole body metabolism and mitochondrial bioenergetics in the drug development for Alzheimer's disease
Acta Pharm Sin B. 2022 Feb;12(2):511-531. doi: 10.1016/j.apsb.2021.06.014.
Aging is by far the most prominent risk factor for Alzheimer's disease (AD), and both aging and AD are associated with apparent metabolic alterations. As developing effective therapeutic interventions to treat AD is clearly in urgent need, the impact of modulating whole-body and intracellular metabolism in preclinical models and in human patients, on disease pathogenesis, have been explored. There is also an increasing awareness of differential risk and potential targeting strategies related to biological sex, microbiome, and circadian regulation. As a major part of intracellular metabolism, mitochondrial bioenergetics, mitochondrial quality-control mechanisms, and mitochondria-linked inflammatory responses have been considered for AD therapeutic interventions. This review summarizes and highlights these efforts.
3.Indole-3-carboxaldehyde regulates RSV-induced inflammatory response in RAW264.7 cells by moderate inhibition of the TLR7 signaling pathway
J Nat Med. 2021 Jun;75(3):602-611. doi: 10.1007/s11418-021-01506-0.
Human respiratory syncytial virus (RSV) is highly contagious and the leading cause of severe respiratory tract illness in infants, elderly, and immunocompromised individuals. Toll-like receptor 7 (TLR7), a pattern recognition receptor recognising the ssRNA of RSV, activates proinflammatory pathways and triggers secretion of interferons (IFNs). On the one hand, the inflammatory responses help clear out virus. On the other hand, they lead to severe lung damage. Banlangen is a traditional Chinese herbal medicine commonly prescribed for respiratory virus infection treatment, but the mechanisms of action and active components remain largely unknown. In the present study, we investigated the effects of the main active components of total alkaloids from banlangen (epigoitrin, indole-3-carboxaldehyde, indole-3-acetonitrile and 4-methoxyindole-3-acetonitrile) on the RSV-induced inflammatory responses in mouse macrophage cells (RAW264.7). Our results demonstrated that RSV-induced IFN-α excessive secretion was moderately inhibited by indole-3-carboxaldehyde through downregulation of mRNA expression in a dose-dependent manner, in comparison, the inhibitory effects of ribavirin were too strong. Furthermore, we revealed that indole-3-carboxaldehyde suppressed transcription of IFN-α by inhibiting RSV-induced TLR7 expression in RAW264.7 cells. Additionally, indole-3-carboxaldehyde inhibited RSV-induced NF-κB signalling activation in a TLR7-MyD88-dependent manner. Together, our findings suggest that indole-3-carboxaldehyde inhibited RSV-induced inflammatory injury by moderate regulation of TLR7 signaling pathway and did not significantly affect the viral clearance competence of the innate immune system.
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