Medicarpin and maackiain 3-O-glucoside-6?-O-malonate conjugates are constitutive compounds in chickpea (Cicer arietinum L.) cell cultures

Weidemann, C.; Tenhaken, Raimund; Höhl, U.; Barz, Wolfgang

doi:10.1007/bf00193162

Cited by 26 publications

(7 citation statements)

References 11 publications

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“…Zea mays i RS1563 contains the dihydroflavonol 4-reductase (DFR) enzyme that catalyzes the reaction for flavan-4-ols biosynthesis that channels flux towards 3-deoxyanthocyanins production [51]. The model also accounts for isoflavone 7-O-glucosyltransferase (IF7GT) and associated reactions that are involved in the production of necessary intermediates for pterocarpin phytoalexin conjugates such as medicarpin 3-O-glucoside-6′-O-malonate (MeGM) and maackain 3-O-glucoside-6′-O-malonate (MaGM) involved in plant defense against fungal elicitation [52].…”

Section: Resultsmentioning

confidence: 99%

Zea mays iRS1563: A Comprehensive Genome-Scale Metabolic Reconstruction of Maize Metabolism

2011

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The scope and breadth of genome-scale metabolic reconstructions have continued to expand over the last decade. Herein, we introduce a genome-scale model for a plant with direct applications to food and bioenergy production (i.e., maize). Maize annotation is still underway, which introduces significant challenges in the association of metabolic functions to genes. The developed model is designed to meet rigorous standards on gene-protein-reaction (GPR) associations, elementally and charged balanced reactions and a biomass reaction abstracting the relative contribution of all biomass constituents. The metabolic network contains 1,563 genes and 1,825 metabolites involved in 1,985 reactions from primary and secondary maize metabolism. For approximately 42% of the reactions direct literature evidence for the participation of the reaction in maize was found. As many as 445 reactions and 369 metabolites are unique to the maize model compared to the AraGEM model for A. thaliana. 674 metabolites and 893 reactions are present in Zea mays iRS1563 that are not accounted for in maize C4GEM. All reactions are elementally and charged balanced and localized into six different compartments (i.e., cytoplasm, mitochondrion, plastid, peroxisome, vacuole and extracellular). GPR associations are also established based on the functional annotation information and homology prediction accounting for monofunctional, multifunctional and multimeric proteins, isozymes and protein complexes. We describe results from performing flux balance analysis under different physiological conditions, (i.e., photosynthesis, photorespiration and respiration) of a C4 plant and also explore model predictions against experimental observations for two naturally occurring mutants (i.e., bm1 and bm3). The developed model corresponds to the largest and more complete to-date effort at cataloguing metabolism for a plant species.

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Section: Resultsmentioning

confidence: 99%

Zea mays iRS1563: A Comprehensive Genome-Scale Metabolic Reconstruction of Maize Metabolism

2011

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“…Protoplast and vacuole extracts share a similar pattern of secondary com pounds (Fig. 3 A, 3B) indicating a common stor- age site for the malonylconjugates BGM, FG M , H G M , C G M [12,32] and the malonylglucosides of the phytoalexins medicarpin and maackiain [15]. Only low amounts of the isoflavone-glucosides BG and FG as well as their respective aglyca could be detected in the vacuolar extracts.…”

Section: Phenolic Constituents O F Chickpea Vacuolesmentioning

confidence: 85%

“…In addition to chickpea and other previously analyzed plants [12] very recent investigations also demonstrated that the isoflavones in soybean and alfalfa mainly accu mulate as 7-0-glucoside-6"-0-malonates [13,14]. Furthermore, the pterocarpan phytoalexins of chickpea cell suspension cultures have been found to accumulate as malonyl conjugates [15]. For apigenin-malonylglucoside in parsley [16] and the acylated anthocyanin of Daucus carota [ 17] pan malonylglucosides of chickpea has not been proven clearly until yet.…”

Section: Introductionmentioning

confidence: 99%

Isoflavone And Pterocarpan Malonylglucosides And ß - L,3 - Glucan - And Chitin-Hydrolases Are Vacuolar Constituents In Chickpea (Cicer Arietinum L.)

Mackenbrock

Vogelsang

Barz

1992

Zeitschrift Für Naturforschung C

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Cell suspension cultures of chickpea (Cicer arietinum L.) were used to prepare protoplasts and vacuoles. The vacuolar preparation revealed only slight contaminations of cytoplasmic marker enzymes. H PLC analysis of the vacuolar extract showed that the malonylglucosides of isoflavones, isoflavanones and pterocarpans are exclusively located in the vacuole. Experi ments designed to determine the subcellular localization of the isoflavone malonylglucoside: malonylesterase suggest an association of this enzyme with the vacuolar membrane. Finally, a ß-l,3-glucanase and a chitinase with basic isoelectric points were also found to be localized in the chickpea vacuoles.

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“…Our findings are consistent with reports linking conjugated defense-related phenolics with resistance in an increasing number of plants (Higgins et al, 1995). In fact, other studies have suggested that conjugated phytoalexins or conjugated phytoalexin precursors that are present constitutively in the cell prior to infection are more important for resistance than phytoalexins that are produced de novo in response to infection (Graham et al, 1990;Graham and Graham, 1991;Weidemann et al, 1991;Geibel and Feucht, 1993).…”

Section: Discussionmentioning

confidence: 99%

Evidence of Phytoalexins in Cucumber Leaves Infected with Powdery Mildew following Treatment with Leaf Extracts of Reynoutria sachalinensis

1997

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Phenolic compounds extracted from cucumber (Cucumis sativus 1.) leaves were separated and analyzed for their differential presente and fungitoxicity in relation to a prophylactic treatment with Milsana (Compo, Münster, Cermany) against powdery mildew (Sphaerotheca fuliginea). Based on our extraction and purification procedures, at least eight separate phenolic compounds with antifunga1 activity were identified as intrinsic components of cucumber plants. O f these compounds, six displayed a significant increase in concentration as a result of elicitation with Milsana, this being particularly evident when the plant was stressed by the pathogen. The combined amounts of these antifungal compounds in treated plants was nearly five times the leve1 found in control plants. One week after Milsana application, some of the antifungal compounds obtained through hydrolysis of their glycosidic links were also detected in their free form, indicating that they are likely liberated from conjugated phenolics by enzymatic hydrolysis in planta. To our knowledge, these results provide the first direct evidence that cucumber plants produce elevated levels of phytoalexins in response to an eliciting treatment after infection.

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Medicarpin and maackiain 3-O-glucoside-6?-O-malonate conjugates are constitutive compounds in chickpea (Cicer arietinum L.) cell cultures

Cited by 26 publications

References 11 publications

Zea mays iRS1563: A Comprehensive Genome-Scale Metabolic Reconstruction of Maize Metabolism

Zea mays iRS1563: A Comprehensive Genome-Scale Metabolic Reconstruction of Maize Metabolism

Isoflavone And Pterocarpan Malonylglucosides And ß - L,3 - Glucan - And Chitin-Hydrolases Are Vacuolar Constituents In Chickpea (Cicer Arietinum L.)

Evidence of Phytoalexins in Cucumber Leaves Infected with Powdery Mildew following Treatment with Leaf Extracts of Reynoutria sachalinensis

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