Isochorismate is an intermediate in 2,3-dihydroxybenzoic acid biosynthesis in Catharanthus roseus cell cultures

Muljono, Retno A. Budi; Scheffer, J. J. C.; Verpoorte, Robert

doi:10.1016/s0981-9428(02)01369-4

Cited by 27 publications

(14 citation statements)

References 10 publications

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“…Loescher and Heide (1994) showed that p-HBA is derived from the phenylalanine pathway, though it has been proposed that the presence of the chorismate pathway leading to this compound in plants is highly probable. Other C6C1 compounds such as SA and 2,3-DHBA were proven in some plants to be synthesized via the isochorismate pathway (Wildermuth et al 2001;Budi Muljono et al 2002;Mustafa et al unpublished results). In microorganisms, isochorismate is a precursor of SA and 2,3-DHBA.…”

Section: Biosynthesis Of C6c1mentioning

confidence: 99%

Phenolic compounds in Catharanthus roseus

Mustafa

Verpoorte

2007

Phytochem Rev

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Besides alkaloids Catharanthus roseus produces a wide spectrum of phenolic compounds, this includes C6C1 compounds such as 2,3-dihydoxybenzoic acid, as well as phenylpropanoids such as cinnamic acid derivatives, flavonoids and anthocyanins. The occurrence of these compounds in C. roseus is reviewed as well as their biosynthesis and the regulation of the pathways. Both types of compounds compete with the indole alkaloid biosynthesis for chorismate, an important intermediate in plant metabolism. The biosynthesis C6C1 compounds is induced by biotic elicitors.

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Section: Biosynthesis Of C6c1mentioning

confidence: 99%

Phenolic compounds in Catharanthus roseus

Mustafa

Verpoorte

2007

Phytochem Rev

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“…The involvement of isochorismate in the synthesis of this compound was further confirmed in transgenic tobacco plants overexpressing an ICS of Catharanthus roseus and accumulating higher amounts of phylloquinone (Verberne et al, 2007). C. roseus or members of the Rubiaceae family also use isochorismate as a precursor for compounds such as anthraquinone or dihydroxybenzoates (Muljono et al, 2002;Mustafa and Verpoorte, 2005). However, these molecules are taxon specific and so far have not been investigated in Arabidopsis.…”

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confidence: 96%

Characterization and Biological Function of the ISOCHORISMATE SYNTHASE2 Gene of Arabidopsis

et al. 2008

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“…Anthraquinones and naphthoquinones are typically elicitor-induced colored compounds, reported to have antioxidant, antimicrobial, and cytotoxic activities (15,16). More recently, it was found that, similar to bacteria, plants can also produce SA (17) and 2,3-dihydroxybenzoic acid (18) from IC, although there has been no evidence supporting plant production of siderophores incorporating SA or 2,3-dihydroxybenzoic acid.…”

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confidence: 99%

Arabidopsis Isochorismate Synthase Functional in Pathogen-induced Salicylate Biosynthesis Exhibits Properties Consistent with a Role in Diverse Stress Responses

Strawn

Marr

Inoue

et al. 2007

Journal of Biological Chemistry

217

146

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Salicylic acid (SA) is a phytohormone best known for its role in plant defense. It is synthesized in response to diverse pathogens and responsible for the large scale transcriptional induction of defense-related genes and the establishment of systemic acquired resistance. Surprisingly, given its importance in plant defense, an understanding of the underlying enzymology is lacking. In Arabidopsis thaliana, the pathogen-induced accumulation of SA requires isochorismate synthase (AtICS1). Here, we show that AtICS1 is a plastid-localized, stromal protein using chloroplast import assays and immunolocalization. AtICS1 acts as a monofunctional isochorismate synthase (ICS), catalyzing the conversion of chorismate to isochorismate (IC) in a reaction that operates near equilibrium (K eq ‫؍‬ 0.89). It does not convert chorismate directly to SA (via an IC intermediate) as does Yersinia enterocolitica Irp9. Using an irreversible coupled spectrophotometric assay, we found that AtICS1 exhibits an apparent K m of 41.5 M and k cat ‫؍‬ 38.7 min ؊1 for chorismate. This affinity for chorismate would allow it to successfully compete with other pathogen-induced, chorismate-utilizing enzymes. Furthermore, the biochemical properties of AtICS1 indicate its activity is not regulated by light-dependent changes in stromal pH, Mg 2؉ , or redox and that it is remarkably active at 4°C consistent with a role for SA in cold-tolerant growth. Finally, our analyses support plastidic synthesis of stress-induced SA with the requirement for one or more additional enzymes responsible for the conversion of IC to SA, because non-enzymatic conversion of IC to SA under physiological conditions was negligible.

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Isochorismate is an intermediate in 2,3-dihydroxybenzoic acid biosynthesis in Catharanthus roseus cell cultures

Cited by 27 publications

References 10 publications

Phenolic compounds in Catharanthus roseus

Phenolic compounds in Catharanthus roseus

Characterization and Biological Function of the ISOCHORISMATE SYNTHASE2 Gene of Arabidopsis

Arabidopsis Isochorismate Synthase Functional in Pathogen-induced Salicylate Biosynthesis Exhibits Properties Consistent with a Role in Diverse Stress Responses

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