title: Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis.
abstract: Characteristic for cruciferous plants is their production of N- and S-containing indole phytoalexins with disease resistance and cancer-preventive properties, previously proposed to be synthesized from indole independently of tryptophan. We show that camalexin, the indole phytoalexin of Arabidopsis thaliana, is synthesized from tryptophan via indole-3-acetaldoxime (IAOx) in a reaction catalyzed by CYP79B2 and CYP79B3. Cyp79B2/cyp79B3 double knockout mutant is devoid of camalexin, as it is also devoid of indole glucosinolates [Zhao, Y., Hull, A. K., Gupta, N. R., Goss, K. A., Alonso, J., Ecker, J. R., Normanly, J., Chory, J. & Celenza, J. L. (2002) Genes Dev. 16, 3100-3112], and isotope-labeled IAOx is incorporated into camalexin. These results demonstrate that only CYP79B2 and CYP79B3 contribute significantly to the IAOx pool from which camalexin and indole glucosinolates are synthesized. Furthermore, production of camalexin in the sur1 mutant devoid of glucosinolates excludes the possibility that camalexin is derived from indole glucosinolates. CYP79B2 plays an important role in camalexin biosynthesis in that the transcript level of CYP79B2, but not CYP79B3, is increased upon induction of camalexin by silver nitrate as evidenced by microarray analysis and promoter-beta-glucuronidase data. The structural similarity between cruciferous indole phytoalexins suggests that these compounds are biogenetically related and synthesized from tryptophan via IAOx by CYP79B homologues. The data show that IAOx is a key branching point between several secondary metabolic pathways as well as primary metabolism, where IAOx has been shown to play a critical role in IAA homeostasis.
authors.affiliation: Center for Molecular Plant Physiology and Department of Plant Biology, Royal Veterinary and Agricultural University, Thorvaldsensvej 40, DK-1871 Frederiksberg C, Copenhagen, Denmark. egl@wzw.tum.de
authors.forename: Erich
authors.initials: E
authors.lastname: Glawischnig
authors.forename: Bjarne Gram
authors.initials: BG
authors.lastname: Hansen
authors.forename: Carl Erik
authors.initials: CE
authors.lastname: Olsen
authors.forename: Barbara Ann
authors.initials: BA
authors.lastname: Halkier
mesh_terms: D017360:Arabidopsis / Q000201:enzymology / Q000235:genetics* / Q000378:metabolism*; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism; D004790:Enzyme Induction / Q000187:drug effects; D017353:Gene Deletion; D020869:Gene Expression Profiling; D018506:Gene Expression Regulation, Plant / Q000187:drug effects; D007211:Indoles / Q000378:metabolism*; D020411:Oligonucleotide Array Sequence Analysis; D010091:Oximes / Q000378:metabolism*; D018515:Plant Leaves / Q000235:genetics / Q000378:metabolism; D011401:Promoter Regions, Genetic / Q000235:genetics; D012835:Silver Nitrate / Q000494:pharmacology; D013844:Thiazoles / Q000378:metabolism*; D000094162:Phytoalexins
chemical_list: D003577:Cytochrome P-450 Enzyme System; D007211:Indoles; D010091:Oximes; D012835:Silver Nitrate; D013844:Thiazoles; C102405:camalexin; D000094162:Phytoalexins; C467098:indole-3-acetaldoxime