Glycosides of 2-C-methyl-d-erythritol from the fruits of anise, coriander and cumin

Kitajima, Junichi; Ishikawa, Toru; Fujimatu, Eiko; Kondho, Kyoko; Takayanagi, Tomomi

doi:10.1016/s0031-9422(02)00438-7

Cited by 35 publications

(18 citation statements)

References 7 publications

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“…As expected, these metabolites were inhibited in all phases but the effect was more evident at the ring stage (Table I). On the other hand, it has been described in plants that the MEP intermediate is used for the biosynthesis of other metabolites such as 2-Cmethyl-D-erythronolactone (70), glycosides (71), and ADP-ME (65). Because P. falciparum is metabolically very similar to plants regarding the presence of apicoplasts, it is possible that the parasites use the MEP intermediate to synthesize other products, as observed in plants.…”

Section: Discussionmentioning

confidence: 99%

The Methylerythritol Phosphate Pathway Is Functionally Active in All Intraerythrocytic Stages of Plasmodium falciparum

Cassera

Gozzo

D’Alexandri

et al. 2004

Journal of Biological Chemistry

123

130

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Malaria is one of the leading causes of morbidity and mortality in the tropics, with 300 to 500 million clinical cases and 1.5 to 2.7 million deaths per year. Nearly all fatal cases are caused by Plasmodium falciparum. The resistance of this parasite to conventional antimalarial drugs such as chloroquine is growing at an alarming rate and therefore new efficient drugs are urgently needed (1-3).In all organisms studied so far, the biosynthesis of isoprenoids such as dolichol, cholesterol, and ubiquinones depends on the condensation of the different numbers of isopentenyl diphosphate (IPP) 1 and dimethylallyl diphosphate units. In mammals and fungi, these units are derived from the classical mevalonate pathway (4). However, in higher plants, in several algae, in some eubacteria, and in P. falciparum the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway was described as the alternative non-mevalonate pathway for the synthesis of IPP (for reviews, see Refs. 5-10). This pathway starts with the condensation of pyruvate and glyceraldehyde 3-phosphate, which yields 1-deoxy-D-xylulose-5-phosphate (DOXP) as a key metabolite (11-17). The DOXP reductoisomerase then catalyzes the simultaneous intramolecular rearrangement and reduction of DOXP to form MEP (18 -22). The activity of this enzyme is specifically inhibited by fosmidomycin (23). Several reaction steps are necessary for the conversion of MEP to IPP. The downstream intermediates of MEP for this pathway are: 4-(cytidine-5-diphospho)-2-C-methyl-D-erythritol (CDP-ME) (24), 4-(cytidine-5-diphospho)-2-C-methyl-D-erythritol-2-phosphate (CDP-MEP), 2-C-methyl-D-erythritol-2,4-cyclodiphosphate (ME-2,4-cPP) (25, 26), and 4-hydroxy-3-methylbut-2-enyl pyrophosphate (27-31). IPP and dimethylallyl diphosphate are synthesized through independent routes in the late steps of the non-mevalonate pathway (32). These units are used for the biosynthesis of ubiquinones and dolichols, and for the prenylation of proteins and other products (33)(34)(35).Based on the sequence data provided by the malaria genome project (plasmodb.org), Jomaa and co-workers (21) identified two genes in P. falciparum that encode key enzymes of the MEP pathway: 1-deoxy-D-xylulose-5-phosphate synthase and 1-deoxy-D-xylulose-5-phosphate reductoisomerase. They also demonstrated that an amino-terminal signal sequence in 1-de- 1 The abbreviations and trivial names used are: IPP, isopentenyl diphosphate; MEP, 2-C-methyl-D-erythritol-4-phosphate; DOXP, 1-deoxy-D-xylulose-5-phosphate; DOX, 1-deoxy-D-xylulose; CDP-ME, 4-(cytidine-5-diphospho)-2-C-methyl-D-erythritol; CDP-MEP, 4-(cytidine-5-diphospho)-2-C-methyl-D-erythritol-2-phosphate; ME-2,4-cPP, 2-Cmethyl-D-erythritol-2,4-cyclodiphosphate; HPLC, high-performance liquid chromatography; ESI-QTOF-MS, ESI-quadrupole time-of-flight mass spectrometry; Q n , Coenzyme Q n .

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Section: Discussionmentioning

confidence: 99%

The Methylerythritol Phosphate Pathway Is Functionally Active in All Intraerythrocytic Stages of Plasmodium falciparum

Cassera

Gozzo

D’Alexandri

et al. 2004

Journal of Biological Chemistry

123

130

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“…those of ME glycosides (ME-glcs) previously identified in anise and cumin fruits (Kitajima et al, 2003). Based on the elucidated structures, the third unknown peak eluting at approximately 24 min in derivatized hds-3 extracts (Figure 2b) was deduced to be free ME (1).…”

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confidence: 88%

The diversion of 2‐C‐methyl‐d‐erythritol‐2,4‐cyclodiphosphate from the 2‐C‐methyl‐d‐erythritol 4‐phosphate pathway to hemiterpene glycosides mediates stress responses in Arabidopsis thaliana

et al. 2015

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Summary2‐C‐Methyl‐d‐erythritol‐2,4‐cyclodiphosphate (MEcDP) is an intermediate of the plastid‐localized 2‐C‐methyl‐d‐erythritol‐4‐phosphate (MEP) pathway which supplies isoprenoid precursors for photosynthetic pigments, redox co‐factor side chains, plant volatiles, and phytohormones. The Arabidopsis hds‐3 mutant, defective in the 1‐hydroxy‐2‐methyl‐2‐(E)‐butenyl‐4‐diphosphate synthase step of the MEP pathway, accumulates its substrate MEcDP as well as the free tetraol 2‐C‐methyl‐d‐erythritol (ME) and glucosylated ME metabolites, a metabolic diversion also occurring in wild type plants. MEcDP dephosphorylation to the free tetraol precedes glucosylation, a process which likely takes place in the cytosol. Other MEP pathway intermediates were not affected in hds‐3. Isotopic labeling, dark treatment, and inhibitor studies indicate that a second pool of MEcDP metabolically isolated from the main pathway is the source of a signal which activates salicylic acid induced defense responses before its conversion to hemiterpene glycosides. The hds‐3 mutant also showed enhanced resistance to the phloem‐feeding aphid Brevicoryne brassicae due to its constitutively activated defense response. However, this MEcDP‐mediated defense response is developmentally dependent and is repressed in emerging seedlings. MEcDP and ME exogenously applied to adult leaves mimics many of the gene induction effects seen in the hds‐3 mutant. In conclusion, we have identified a metabolic shunt from the central MEP pathway that diverts MEcDP to hemiterpene glycosides via ME, a process linked to balancing plant responses to biotic stress.

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“…Selective inhibition of aldose reductase [224] and reduction of advanced glycation end products and H 2 O 2 induced oxidative stress in human adipocytes [225] Polyacetylenes [228]. [229]. Monoterpenoids, glycosides, monoterpenoid glucoside sulfates, and aromatic compound glycosides [230] Antihyperglycemic, insulin-releasing, and insulin-like activity [231,232] 29…”

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confidence: 99%

Medicinal Plants from Jordan in the Treatment of Diabetes: Traditional Uses vs.In VitroandIn VivoEvaluations – Part 2

2011

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Glycosides of 2-C-methyl-d-erythritol from the fruits of anise, coriander and cumin

Cited by 35 publications

References 7 publications

The Methylerythritol Phosphate Pathway Is Functionally Active in All Intraerythrocytic Stages of Plasmodium falciparum

The Methylerythritol Phosphate Pathway Is Functionally Active in All Intraerythrocytic Stages of Plasmodium falciparum

The diversion of 2‐C‐methyl‐d‐erythritol‐2,4‐cyclodiphosphate from the 2‐C‐methyl‐d‐erythritol 4‐phosphate pathway to hemiterpene glycosides mediates stress responses in Arabidopsis thaliana

Medicinal Plants from Jordan in the Treatment of Diabetes: Traditional Uses vs.In VitroandIn VivoEvaluations – Part 2

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