![]() | |
Names | |
---|---|
Preferred IUPAC name 3-(1,3-Thiazol-2-yl)-1H-indole | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.236.489 |
PubChem CID | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C11H8N2S | |
Molar mass | 200.26 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Camalexin (3-thiazol-2-yl-indole) is a simple indole alkaloid found in the plant Arabidopsis thaliana and other crucifers. The secondary metabolite functions as a phytoalexin to deter bacterial and fungal pathogens. [1]
The base structure of camalexin consists of an indole ring derived from tryptophan. The ethanamine moiety attached to the 3 position of the indole ring is subsequently rearranged into a thiazole ring.
While the biosynthesis of camalexin in planta has not been fully elucidated, most of the enzymes involved in the pathway are known and involved in a metabolon complex. [2] The pathway starts with a tryptophan precursor which is subsequently oxidized by two cytochrome P450 enzymes. [3] The indole-3-acetaldoxime is then converted to indole-3-acetonitrile by another cytochrome P450, CYP71A13. [1] A glutathione conjugate followed by a subsequent unknown enzyme is needed to form dihydrocamalexic acid. [4] [5] A final decarboxylation step by cytochrome P450 CYP71B15, also called phytoalexin deficient4 (PAD3) results in the final product, camalexin. [6] [7]
Camalexin is cytotoxic against aggressive prostate cancer cell lines in vitro . [8]