SC‐0051, a 2‐benzoyl‐cyclohexane‐1,3‐dione bleaching herbicide, is a potent inhibitor of the enzyme <i>p</i>‐hydroxyphenylpyruvate dioxygenase

Schulz, A.; Ort, Oswald; Beyer, Peter; Kleinig, Hans

doi:10.1016/0014-5793(93)80013-k

Cited by 200 publications

(170 citation statements)

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“…AOX can oxidize the ubiquinone pool and uses molecular oxygen as a terminal acceptor. Interestingly, quinone involvement in phytoene desaturation is indicated by the fact that phytoene desaturation is impaired when bleaching cyclohexanedione herbicides (which inhibit the enzyme p-hydroxyphenylpyruvate dioxygenase in the quinone biosynthesis pathway) are applied to plants (Schultz et al, 1993) or when the gene for this enzyme is inactivated by mutation (Norris et al, 1995). In addition, molecular oxygen also has been proposed to be essential for carotene desaturation, at least in nonphotosynthetic plastids (Beyer et al, 1989).…”

Section: Functional Role Of Immentioning

confidence: 99%

Mutations in the Arabidopsis Gene IMMUTANS Cause a Variegated Phenotype by Inactivating a Chloroplast Terminal Oxidase Associated with Phytoene Desaturation

et al. 1999

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The immutans ( im ) mutant of Arabidopsis shows a variegated phenotype comprising albino and green somatic sectors. We have cloned the IM gene by transposon tagging and show that even stable null alleles give rise to a variegated phenotype. The gene product has amino acid similarity to the mitochondrial alternative oxidase. We show that the IM protein is synthesized as a precursor polypeptide that is imported into chloroplasts and inserted into the thylakoid membrane. The albino sectors of im plants contain reduced levels of carotenoids and increased levels of the carotenoid precursor phytoene. The data presented here are consistent with a role for the IM protein as a cofactor for carotenoid desaturation. The suggested terminal oxidase function of IM appears to be essential to prevent photooxidative damage during early steps of chloroplast formation. We propose a model in which IM function is linked to phytoene desaturation and, possibly, to the respiratory activity of the chloroplast. INTRODUCTIONIn plant cells, plastid differentiation is intimately linked to organogenesis and is affected by both developmental regulatory mechanisms and environmental conditions. The complex mechanisms involved in the phototransformation of the plastids of dark-grown seedlings (etioplasts) to photosynthetically active plastids (chloroplasts) have been described extensively (reviewed in Mullet, 1988;Taylor, 1989;Chory and Susek, 1994). Alternatively, developing grass tissues provide a unique system in which a gradient of developmental stages of cells and plastids (proplastids to chloroplasts) is present (Mullet, 1988;Bilang and Bogorad, 1996; Inada et al., 1996).Mutants visibly impaired in chloroplast differentiation can be selected by their pale green, yellow, or albino color. The chlorophyll-deficient mutant olive of Antirrhinum has this phenotype (Hudson et al., 1993). Not all of these mutants are altered directly in pigment synthesis. Putative functions can be proposed for mutated genes based on the similarity of their coding sequences to known proteins. The Arabidopsis mutant albino3 (Sundberg et al., 1997) is impaired in chloroplast membrane biogenesis, as suggested by amino acid sequence similarity between ALBINO3 and the yeast mitochondrial OXA1 protein involved in mitochondrial biogenesis. The Arabidopsis cla1 mutation (Mandel et al., 1996) identifies an enzyme also present in cyanobacteria. Mutations also have been described that affect the proplastid-tochloroplast transition. The dag mutant from Antirrhinum (Chatterjee et al., 1996) and dcl1 from tomato (Keddie et al., 1996) do not contain chloroplasts but rather plastids resembling nondifferentiated proplastids. These genes together with the PALE CRESS gene from Arabidopsis (Reiter et al., 1994) affect both chloroplast development and leaf architecture.One class of mutations gives rise to variegated plants that have a mutant phenotype in some sectors and a wild-type phenotype in others. The iojap (Han et al., 1992) mutant of maize or the chloroplast mutator in ma...

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Section: Functional Role Of Immentioning

confidence: 99%

Mutations in the Arabidopsis Gene IMMUTANS Cause a Variegated Phenotype by Inactivating a Chloroplast Terminal Oxidase Associated with Phytoene Desaturation

et al. 1999

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“…The only native purification achieved so far, from Capsicum chromoplasts (Hugueney et al, 1992), employed Tween 80 at a concentration above the critical micellar concentration (CMC) for solubilization. Also indicative for the membraneintegral localization of phytoene desaturase in Narcissus pseudonarcissus chromoplasts is the mechanistic sequence involving a redox chain using first membranebound quinones (Mayer eta/., 1990;Schulz et al, 1993) and then oxygen (Beyer et al, 1989), as intermediate and final electron acceptor, respectively. This mechanism involves a connection to a membrane-bound nicotinamide adenine dinucleotide (NAD)(P)H-dependent respiratory pathway, also employing quinones as redox-active components and influencing their redox state (Nievelstein etaL, 1995).…”

Section: Introductionmentioning

confidence: 99%

A novel, soluble form of phytoene desaturase from Narcissus pseudonarcissus chromoplasts is Hsp70‐complexed and competent for flavinylation, membrane association and enzymatic activation

Al‐Babili

Lintig

Haubruck³

et al. 1996

The Plant Journal

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112

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SummaryA cDNA coding for the carotenoid biosynthetic enzyme phytoene desaturase from Narcissus pseudonarcissus was cloned and the corresponding protein expressed in insect cells using the baculovirus system. Polyclonal antibodies raised against the recombinant protein allowed the detection of soluble and tightly membrane-bound populations of phytoene desaturase in the chromoplasts isolated from petals. The soluble form is enzymatically inactive and a constituent of a larger Hsp 7g-containing protein complex in the stroma, whereas the membrane-bound form is functional. In vitro, the soluble form is able to associate on to/into protein-free liposomal membranes made from chromoplast lipids, thereby gaining activity by binding added flavine adenine dinucleotide (FAD). Once bound to membranes, activated phytoene desaturase works independently of any added FAD, employing membrane-bound electron acceptors. FAD, however, exerts no positive effect on the membrane-association process, its role is confined to enzymatic activation. Although carotenoid accumulation is strongly induced during flower development, only very low concentrations of phytoene desaturase transcripts are detectable, while the corresponding protein accumulates in low, but measurable amounts, appearing in soluble and membrane-bound states. Poet-transcriptional mechanisms contribute significantly to carotenoid accumulation, as do factors determining the enzymatic activity of phytoene desaturase, for example by influencing the redox-state of membrane-bound electron acceptors.

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“…HPPDase has been purified from several mammalian and bacterial sources (Wada et al, 1975;Lindstedt et al, 1977;Roche et al, 1982;Endo et al, 1992), and in all cases the active enzyme was found to be a homodimer or, less commonly, a homotetramer, with subunits of approximately 40 to 48 kD. As a result of the central role HPPDase serves in aromatic amino acid metabolism in mammals and plastidic quinone synthesis in plants, a class of competitive inhibitors of HPPDases collectively known as triketones has been developed and used for a variety of clinical and agricultural purposes (Lindstedt et al, 1992;Schultz et al, 1993;Secor, 1994). In humans, the triketone 2-(2-nitro-4-trifluromethylbenzoyl)-1,3-cyclohexanedione and related compounds are used as an alternative to liver transplantation in patients with the otherwise fatal hereditary disorder tyrosinemia type I.…”

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confidence: 99%

“…In plants, triketones such as sulcotrione (2-[4-chloro-2-nitrobenzoyl]-5,5-dimethylcyclohexane-1,3-dione) are effective bleaching herbicides. Their mode of action arises from a direct inhibition of plastoquinone and tocopherol synthesis and an indirect inhibition of carotenoid desatu-ration (Mayonado et al, 1989;Schultz et al, 1993;Secor, 1994). The latter results in accumulation of the carotenoid biosynthetic intermediate phytoene and photooxidation of the plastid.…”

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confidence: 99%

Complementation of the Arabidopsispds1Mutation with the Gene Encodingp-Hydroxyphenylpyruvate Dioxygenase

1998

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Plastoquinone and tocopherols are the two major quinone compounds in higher plant chloroplasts and are synthesized by a common pathway. In previous studies we characterized two loci in Arabidopsis defining key steps of this biosynthetic pathway. Mutation of the PDS1 locus disrupts the activity of p-hydroxyphenylpyruvate dioxygenase (HPPDase), the first committed step in the synthesis of both plastoquinone and tocopherols in plants. Although plants homozygous for the pds1 mutation could be rescued by growth in the presence of homogentisic acid, the product of HPPDase, we were unable to determine if the mutation directly or indirectly disrupted HPPDase activity. This paper reports the isolation of a cDNA, pHPPD, encoding Arabidopsis HPPDase and its functional characterization by expression in both plants and Escherichia coli. pHPPD encodes a 50-kD polypeptide with homology to previously identified HPPDases, including 37 highly conserved amino acid residues clustered in the carboxyl region of the protein. Expression of pHPPD in E. coli catalyzes the accumulation of homogentisic acid, indicating that it encodes a functional HPPDase enzyme. Mapping of pHPPD and co-segregation analysis of the pds1 mutation and the HPPD gene indicate tight linkage. Constitutive expression of pHPPD in a pds1 mutant background complements this mutation. Finally, comparison of the HPPD genomic sequences from wild type and pds1 identified a 17-bp deletion in the pds1 allele that results in deletion of the carboxyterminal 26 amino acids of the HPPDase protein. Together, these data conclusively demonstrate that pds1 is a mutation in the HPPDase structural gene.

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SC‐0051, a 2‐benzoyl‐cyclohexane‐1,3‐dione bleaching herbicide, is a potent inhibitor of the enzyme p‐hydroxyphenylpyruvate dioxygenase

Cited by 200 publications

References 15 publications

Mutations in the Arabidopsis Gene IMMUTANS Cause a Variegated Phenotype by Inactivating a Chloroplast Terminal Oxidase Associated with Phytoene Desaturation

Mutations in the Arabidopsis Gene IMMUTANS Cause a Variegated Phenotype by Inactivating a Chloroplast Terminal Oxidase Associated with Phytoene Desaturation

A novel, soluble form of phytoene desaturase from Narcissus pseudonarcissus chromoplasts is Hsp70‐complexed and competent for flavinylation, membrane association and enzymatic activation

Complementation of the Arabidopsispds1Mutation with the Gene Encodingp-Hydroxyphenylpyruvate Dioxygenase

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