Incorporation of 1-[1-13C]Deoxy-d-xylulose in Chamomile Sesquiterpenes

Adam, Klaus-Peter; Thiel, Rolf; Zapp, Josef

doi:10.1006/abbi.1999.1346

Cited by 85 publications

(59 citation statements)

References 21 publications

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“…However, in the two latter studies, exogenous MVA was, to some extent, incorporated into plastids and used to produce plastidial isoprenoids. Under stress conditions, the export of MEP-derived intermediates might be required to satisfy the need for the production of defense-related sesquiterpenoids in the cytosolic compartment (Piel et al, 1998;Adam et al, 1999). Dudareva et al (2005) showed that, in the epidermis of snapdragon petals, only the plastid-localized MEP pathway is active in the formation of volatile terpenes and provides IPP precursors for both plastidial monoterpene and cytosolic sesquiterpene biosynthesis.…”

Section: Discussionmentioning

confidence: 99%

The Plastidial 2-C-Methyl-d-Erythritol 4-Phosphate Pathway Provides the Isoprenyl Moiety for Protein Geranylgeranylation in Tobacco BY-2 Cells

et al. 2009

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Protein farnesylation and geranylgeranylation are important posttranslational modifications in eukaryotic cells. We visualized in transformed Nicotiana tabacum Bright Yellow-2 (BY-2) cells the geranylgeranylation and plasma membrane localization of GFP-BD-CVIL, which consists of green fluorescent protein (GFP) fused to the C-terminal polybasic domain (BD) and CVIL isoprenylation motif from the Oryza sativa calmodulin, CaM61. Treatment with fosmidomycin (Fos) or oxoclomazone (OC), inhibitors of the plastidial 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway, caused mislocalization of the protein to the nucleus, whereas treatment with mevinolin, an inhibitor of the cytosolic mevalonate pathway, did not. The nuclear localization of GFP-BD-CVIL in the presence of MEP pathway inhibitors was completely reversed by all-transgeranylgeraniol (GGol). Furthermore, 1-deoxy-D-xylulose (DX) reversed the effects of OC, but not Fos, consistent with the hypothesis that OC blocks 1-deoxy-D-xylulose 5-phosphate synthesis, whereas Fos inhibits its conversion to 2-C-methyl-Derythritol 4-phosphate. By contrast, GGol and DX did not rescue the nuclear mislocalization of GFP-BD-CVIL in the presence of a protein geranylgeranyltransferase type 1 inhibitor. Thus, the MEP pathway has an essential role in geranylgeranyl diphosphate (GGPP) biosynthesis and protein geranylgeranylation in BY-2 cells. GFP-BD-CVIL is a versatile tool for identifying pharmaceuticals and herbicides that interfere either with GGPP biosynthesis or with protein geranylgeranylation.

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Section: Discussionmentioning

confidence: 99%

The Plastidial 2-C-Methyl-d-Erythritol 4-Phosphate Pathway Provides the Isoprenyl Moiety for Protein Geranylgeranylation in Tobacco BY-2 Cells

et al. 2009

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“…For example, IPP import into mitochondria (Lü tke-Brinkhaus et al, 1984) and exchange of IPP between the cytosol and plastid have been documented by inhibitor studies in Arabidopsis (Laule et al, 2003) and in vivo feeding studies in several plant systems, including tobacco BY-2 cultures (Hemmerlin et al, 2003), snapdragon (Antirrhinum majus) (Dudareva et al, 2005), chamomile (Chamaemelum nobile) (Adam et al, 1999), and lima bean (Phaseolus lunatus) (Piel et al, 1998). In vitro studies with isolated membranes also support the transport of IPP from plastids to the cytosol (and possibly DMAPP, albeit at very low levels) (Bick and Lange, 2003) and from the cytosol to plastids (Kreuz and Kleinig, 1984;Soler et al, 1993;Flü gge and Gao, 2005).…”

Section: Single Mutants In Idi1 or Idi2 Are Rescued By The Remaining Idimentioning

confidence: 99%

The Arabidopsis thaliana Type I Isopentenyl Diphosphate Isomerases Are Targeted to Multiple Subcellular Compartments and Have Overlapping Functions in Isoprenoid Biosynthesis

et al. 2008

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To form the building blocks of isoprenoids, isopentenyl diphosphate (IPP) isomerase activity, which converts IPP to dimethylallyl diphosphate (DMAPP), appears to be necessary in cytosol, plastids, and mitochondria. Arabidopsis thaliana contains only two IPP isomerases (Isopentenyl Diphosphate Isomerase1 [IDI1] and IDI2). Both encode proteins with N-terminal extensions similar to transit peptides and are expressed in all organs, with IDI1 less abundant than IDI2. Examination of enhanced green fluorescent protein fusions established that IDI1 is mainly in the plastid, whereas IDI2 is mainly in the mitochondria. Both proteins are also in the cytosol as a result of their translation from naturally occurring shorter transcripts lacking transit peptides, as demonstrated by 59 rapid amplification of cDNA ends cloning. IPP isomerase activity in the cytosol was confirmed by uniform labeling of IPP-and DMAPP-derived units of the cytoplasmic isoprenoid product, sitosterol, when labeled mevalonate was administered. Analysis of mutant lines showed that double mutants were nonviable, while homozygous single mutants had no major morphological or chemical differences from the wild type except for flowers with fused sepals and underdeveloped petals on idi2 mutants. Thus, each of the two Arabidopsis IPP isomerases is found in multiple but partially overlapping subcellular locations, and each can compensate for the loss of the other through partial redundancy in the cytosol.

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“…The biosynthesis of IPP can proceed via two different pathways, namely the longestablished mevalonic acid (MVA) and the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathways, the reaction sequence of which has been characterized. 3 In plants, the MEP pathway appears generally operative for formation of monoterpenoids, diterpenoids, phytols and carotenoids. [4][5][6] The key regulatory step of the MVA pathway involves reduction of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) to mevalonate, with this being catalysed by the cytosolic enzyme HMG-CoA reductase (HMGR).…”

Section: Introductionmentioning

confidence: 99%

Biosynthetic origin of the isoprene units in chromenes of Piper aduncum (Piperaceae)

Leite¹,

Lopes²,

Kato

et al. 2007

J. Braz. Chem. Soc.

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Estudos metabólicos envolvendo a incorporação de D-glicose-[1-13 C] em folhas dePiper aduncum (Piperaceae) mostraram que as vias do mevalonato (MVA) e da triose-piruvato (MEP) estão envolvidas na biossíntese da unidade isoprênica presente no 2,2-dimetil-2H-1-cromeno-6-carboxilato de metila (1) e no 2,2-dimetil-8-(3'-metil-2'-butenil)-2H-1-cromeno-6-carboxilato de metila (2). O padrão de incorporação dos carbonos marcados com D-glicose-[1-13 C] destes cromenos foram determinados através de espectroscopia de RMN de 13 C quantitativo. Os resultados confirmaram que o compartimento biossintético de 1 e 2 pode ser o plastídio e/ou citosol, ou possivelmente um compartimento adicional, como o espaço entre a membrana e o plastídio.Metabolic studies involving the incorporation of [1-13 C]-D-glucose into intact leaves of Piper aduncum (Piperaceae) have indicated that both the mevalonate (MVA) and the pyruvate-triose (MEP) non-mevalonate pathways are implicated in the biosynthesis of isoprene moieties present in methyl 2,2-dimethyl-2H-1-chromene-6-carboxylate (1) and methyl 2,2-dimethyl-8-(3'-methyl-2'-butenyl)-2H-1-chromene-6-carboxylate (2). The pattern of incorporation of label from [1- 13C]-D-glucose into these chromenes was determined by quantitative 13 C NMR spectroscopy. The results confirmed that biosynthetic compartment of 1 and 2 could either be the plastid and/ or the cytosol or, possibly, an additional compartment such as the plastid inter-membrane space. Keywords:Piper aduncum, chromenes, [1-13 C]-D-glucose, mevalonate pathway, 2-C-methyl-D-erythritol-4-phosphate pathway IntroductionThe isoprenoids constitute a large class of natural products comprising more than 29,000 compounds. 1 In higher plants, isoprenoids play essential roles in membrane structure (sterols), redox chemistry (plastoquinones, ubiquinones), growth regulation (gibberellins, cytokinins, brassinosteroids and abscisic acid), defence mechanisms (phytoalexins) and free radical scavenging (carotenoids and tocopherols). 2 The common building blocks of all isoprenoids, the so-called 'isoprene units', is derived from isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). The biosynthesis of IPP can proceed via two different pathways, namely the longestablished mevalonic acid (MVA) and the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathways, the reaction sequence of which has been characterized. 3 In plants, the MEP pathway appears generally operative for formation of monoterpenoids, diterpenoids, phytols and carotenoids. [4][5][6] The key regulatory step of the MVA pathway involves reduction of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) to mevalonate, with this being catalysed by the cytosolic enzyme HMG-CoA reductase (HMGR). Plastidic IPP is derived, however, from MEP formed via the condensation of pyruvate and glyceraldehyde-3-phosphate (G3P) catalysed by 1-deoxy-D-xylulose-5-phosphate synthase (DXS). 2,6 The two pathways to IPP are thus compartmentalized in the cytosol and the plastid, respectively. However, they may function in the for...

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Incorporation of 1-[1-13C]Deoxy-d-xylulose in Chamomile Sesquiterpenes

Cited by 85 publications

References 21 publications

The Plastidial 2-C-Methyl-d-Erythritol 4-Phosphate Pathway Provides the Isoprenyl Moiety for Protein Geranylgeranylation in Tobacco BY-2 Cells

The Plastidial 2-C-Methyl-d-Erythritol 4-Phosphate Pathway Provides the Isoprenyl Moiety for Protein Geranylgeranylation in Tobacco BY-2 Cells

The Arabidopsis thaliana Type I Isopentenyl Diphosphate Isomerases Are Targeted to Multiple Subcellular Compartments and Have Overlapping Functions in Isoprenoid Biosynthesis

Biosynthetic origin of the isoprene units in chromenes of Piper aduncum (Piperaceae)

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