Camalexin
Chemical compound
From Wikipedia, the free encyclopedia
Camalexin (3-thiazol-2-yl-indole) is a simple indole alkaloid found in the plant species Arabidopsis thaliana. This secondary metabolite functions as a phytoalexin to deter bacterial and fungal pathogens.[1]
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| Names | |
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| Preferred IUPAC name
3-(1,3-Thiazol-2-yl)-1H-indole | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.236.489 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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Structure
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.
Biosynthesis
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]