Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate

Rohmer, Michel; Knani, M'hamed; Simonin, Pascale; Sutter, Bertrand; Sahm, Hermann

doi:10.1042/bj2950517

Cited by 1,073 publications

(728 citation statements)

References 62 publications

(68 reference statements)

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“…Because there is no signal from marrubiin that could be used as internal standard, the evaluation of "$C enrichment was made by comparison of both spectra as reported for ubiquinones [11].…”

Section: Evaluation Of 13 C-enrichment In Marrubiinmentioning

confidence: 99%

“…IPP, which is formed via the acetate-mevalonate pathway, is labelled in positions C-2, C-4 and C-5 (Scheme 1). The alternative pathway as proposed by Rohmer et al for Eubacteria [11,12] starts with pyruvate and glyceraldehyde 3-phosphate from glycolysis and leads via a hypothetical linear condensation product to IPP labelled at positions C-1 and C-5 (Scheme 2). Because each glucose molecule is degraded into two trioses the label from [1-"$C]glucose is diluted in a ratio 1 : 1.…”

Section: Labelling Of Isoprenoids From [1-13 C]glucosementioning

confidence: 99%

“…More than 80 % of this marrubiin was biosynthesized during the cultivation. The enrichment of carbon atoms in ["$C]marrubiin was investigated by means of "$C-NMR spectroscopy [11]. A reference spectrum was recorded from 15 mg of unlabelled marrubiin, which was purified from leaves of field-grown plants.…”

Section: Scheme 1 Labelling Of Ipp From [1-13 C]glucose Via the Acetamentioning

confidence: 99%

“…A few years ago incorporation experiments showed an irregular labelling pattern of hopanes of the triterpenoid series in some Eubacteria [10]. This led to the discovery of an alternative pathway of isoprenoid formation, with triose phosphate units as the precursors [11,12]. There was a first report in 1994 on the biosynthesis of ginkgolides in Ginkgo biloba, which showed that there might exist a similar alternative pathway in the plant kingdom [13].…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Knöß

Reuter

Zapp

1997

Biochemical Journal

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The biosynthesis of the furanic labdane diterpene marrubiin has been studied in plantlets and shoot cultures of Marrubium vulgare(Lamiaceae). The use of [2-14C]acetate, [2-14C]pyruvate, [2-14C]mevalonic acid and [U-14C]glucose incorporation experiments showed that the labelling of sterols in etiolated shoot cultures of M. vulgare was in accordance with their biosynthesis via the acetate–mevalonate pathway. In contrast, the incorporation rates of these precursors into the diterpene marrubiin could not be explained by biosynthesis of this compound via the acetate–mevalonate pathway. Cultivation of etiolated shoot cultures of M. vulgare on medium containing [1-13C]glucose and subsequent 13C-NMR spectroscopy of marrubiin led to the conclusion that the biosynthesis of marrubiin follows a non-mevalonate pathway. All isoprenic units of 13C-labelled marrubiin were enriched in those carbons that correspond to positions 1 and 5 of a putative precursor isopentenyl diphosphate. This labelling pattern from [1-13C]glucose is consistent with an alternative pathway via trioses, which has already been shown to occur in Eubacteria and Gymnospermae. The labdane skeleton is a precursor of many other skeletal types of diterpenes. Therefore it becomes obvious that in connection with the few known examples of a non-mevalonate pathway to isoprenoids the formation of some isoprenoids in plants via a non-mevalonate pathway might be quite common.

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Section: Evaluation Of 13 C-enrichment In Marrubiinmentioning

confidence: 99%

Section: Labelling Of Isoprenoids From [1-13 C]glucosementioning

confidence: 99%

Section: Scheme 1 Labelling Of Ipp From [1-13 C]glucose Via the Acetamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Knöß

Reuter

Zapp

1997

Biochemical Journal

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“…The MVA pathway has been extensively studied since its discovery in the 1950s, and has been reviewed in detail [1,3]. Different from the MVA pathway, the MEP pathway was first identified in bacteria about 15 years ago and later in plants [6,10]. Currently, all the enzymes involved in the MEP pathway have been identified.…”

Section: Introductionmentioning

confidence: 99%

Disruption of the 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) gene results in albino, dwarf and defects in trichome initiation and stomata closure in Arabidopsis

Xing

Miao

et al. 2010

Cell Res

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1-Deoxy-d-xylulose-5-phosphate reductoisomerase (DXR) is an important enzyme involved in the 2-C-methyl-d-erythritol-4-phosphate (MEP) pathway which provides the basic five-carbon units for isoprenoid biosynthesis. To investigate the role of the MEP pathway in plant development and metabolism, we carried out detailed analyses on a dxr mutant (GK_215C01) and two DXR transgenic co-suppression lines, OX-DXR-L2 and OX-DXR-L7. We found that the dxr mutant was albino and dwarf. It never bolted, had significantly reduced number of trichomes and most of the stomata could not close normally in the leaves. The two co-suppression lines produced more yellow inflorescences and albino sepals with no trichomes. The transcription levels of genes involved in trichome initiation were found to be strongly affected, including GLABRA1, TRANSPARENT TESTA GLABROUS 1, TRIPTYCHON and SPINDLY, expression of which is regulated by gibberellic acids (GAs). Exogenous application of GA 3 could partially rescue the dwarf phenotype and the trichome initiation of dxr, whereas exogenous application of abscisic acid (ABA) could rescue the stomata closure defect, suggesting that lower levels of both GA and ABA contribute to the phenotype in the dxr mutants. We further found that genes involved in the biosynthetic pathways of GA and ABA were coordinately regulated. These results indicate that disruption of the plastidial MEP pathway leads to biosynthetic deficiency of photosynthetic pigments, GAs and ABA, and thus the developmental abnormalities, and that the flux from the cytoplasmic mevalonate pathway is not sufficient to rescue the deficiency caused by the blockage of the plastidial MEP pathway. These results reveal a critical role for the MEP biosynthetic pathway in controlling the biosynthesis of isoprenoids.

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Engineered isoprenoid pathway enhances astaxanthin production inEscherichia coli

Wang

Liao

1999

Biotechnol. Bioeng.

155

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The isoprenoid pathway is a versatile biosynthetic network leading to over 23,000 compounds. Similar to other biosynthetic pathways, the production of isoprenoids in microorganisms is controlled by the supply of precursors, among other factors. To engineer a host that has the capability to supply geranylgeranyl diphosphate (GGPP), a common precursor of isoprenoids, we cloned and overexpressed isopentenyl diphosphate (IPP) isomerase (encoded by idi) from Escherichia coli and GGPP synthase (encoded by gps) from the archaebacterium Archaeoglobus fulgidus. The latter was shown to be a multifunctional enzyme converting dimethylallyl diphosphate (DMAPP) to GGPP. These two genes and the gene cluster (crtBIYZW) of the marine bacterium Agrobacterium aurantiacum were introduced into E. coli to produce astaxanthin, an orange pigment and antioxidant. This metabolically engineered strain produces astaxanthin 50 times higher than values reported before. To determine the rate‐controlling steps in GGPP production, the IDI‐GPS pathway was compared with another construct containing idi, ispA (encoding farnesyl diphosphate (FPP) synthase in E. coli), and crtE (encoding GGPP synthase from Erwinia uredovora). Results show that the conversion from FPP to GGPP is the first bottleneck, followed sequentially by IPP isomerization and FPP synthesis. Removal of these bottlenecks results in an E. coli strain providing sufficient precursors for in vivo synthesis of isoprenoids. © 1999 John Wiley & Sons, Inc. Biotechnol Bioeng 62: 235–241, 1999.

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Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate

Cited by 1,073 publications

References 62 publications

Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

Disruption of the 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) gene results in albino, dwarf and defects in trichome initiation and stomata closure in Arabidopsis

Engineered isoprenoid pathway enhances astaxanthin production inEscherichia coli

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