Indole-3-carbaldehyde (I3A), also known as indole-3-aldehyde and 3-formylindole, is a
metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism.
The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
of dietary which is synthesized by
human gastrointestinal bacteria, particularly species of the ''
Lactobacillus''
genus.
I3A is a
biologically active
In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or ph ...
metabolite which acts as a
receptor agonist at the
aryl hydrocarbon receptor in intestinal
immune cells, in turn stimulating the production of
interleukin-22
Interleukin-22 (IL-22) is protein that in humans is encoded by the ''IL22'' gene.
Structure
IL-22 is an α-helical cytokine. IL-22 binds to a heterodimeric cell surface receptor composed of IL-10R2 and IL-22R1 subunits. IL-22R is expressed o ...
which facilitates mucosal reactivity.
Biosynthesis in humans and cellular effects
Chemistry
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.
Antifungal properties
Indole-3-carbaldehyde has antifungal properties, and partially accounts for the protection from
chytridiomycosis seen in amphibian species which carry
Janthinobacterium lividum
''Janthinobacterium lividum'' is an aerobic organism, aerobic, Gram-negative bacteria, Gram-negative, soil-dwelling bacterium that has a distinctive dark-violet (almost black) color, due to a compound called violacein, which is produced when gly ...
on their skin.
References
{{reflist, 30em
Amino acid derivatives
Indoles
Aromatic aldehydes