High Performance Liquid Chromatographic Separation of Isoflavones and Structural Elucidation of Isoflavone 7-O-glucoside 6″-malonates from Cicer arietinum

Köster, Johannes; Strack, Dieter; Barz, Wolfgang

doi:10.1055/s-2007-969907

Cited by 85 publications

(46 citation statements)

References 20 publications

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“…The present study does not allow us to define the mechanisms by which high concentrations of cells or their products inhibit hyphal growth. In addition to producing stimulatory compounds, suspension-cultured cells can also accumulate a number of antifungal compounds, either as normal cell metabolites or in response to biotic and environmental elicitation (Hahlbrock & Grisebach, 1979;Takeya & Itokawwa, 1982;Kabayashi & Ohat, 1983;Koster, Strack & Barz, 1983;Ingham, Tahara & Dziedzic, 1988;Lamb et al, 1989). VA mycorrhizal fungi are considered to be non-pathogenic in nature, but they are capable of causing a host response before penetration (Gemma & Koske, 1988), typical host defense responses in the first stages of the interaction (Spanu et al, 1989), and host accumulation of antifungal phenolic compounds (Morandi, Bailey & Gianinazzi-Pearson, 1984) capable of reducing hyphal growth (Siqueira, 1983;Wacker, Safir & Stephens, 1989).…”

Section: Discussionmentioning

confidence: 99%

Stimulation of hyphal growth of the VA mycorrhizal fungus Gigaspora margarita by suspension‐cultured Pueraria phaseoloides cells and cell products

Paula

Siqueira

1990

New Phytologist

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SUMMARYThe efFects of suspension-cultured Pueraria phaseoloides Benth. (pueraria) cells and cell products on growth of hyphae of the VA mycorrhizal fungus Gigaspora margarita Becker & Hall in liquid media were examined. Addition of 6-d-old cell cultures of pueraria cells at a concentration of 25 cells ml"^ of medium caused a 3-9-fold increase in hyphal growth. Higher cell concentrations resulted in less growth stimulation. Cell exudates or extracts (cell products) at a concentration of 25 [A rs\V^ of medium also stimulated hyphal growth. Successive cell additions, or transfer of the spores into fresh media containing pueraria cells, resulted in no additional hyphal growth. Spores soaked in exudates or extracts showed faster and more vigorous growth when plated on an agar medium than those soaked in a control solution. It is suggested that suspension-cultured pueraria cells stimulate hyphal growth of VA mycorrhizal fungi by accumulating and leaking very active metabolites into the medium.

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Section: Discussionmentioning

confidence: 99%

Stimulation of hyphal growth of the VA mycorrhizal fungus Gigaspora margarita by suspension‐cultured Pueraria phaseoloides cells and cell products

Paula

Siqueira

1990

New Phytologist

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“…The ethylacetate fractions were brought to dryness and the residue was dissolved in 2 00 (il methanol. These extracts were used for analysis and quantifi cation of the phenolic compounds by HPLC-techniques as described earlier [12,32].…”

Section: Isolation O F Phenolic Constituents Fro M Protoplasts and Vamentioning

confidence: 99%

“…Several classes of secondary constituents, D-conflgurated amino acids, endproducts of pesticide degradation and interme diates of phytohormon production were described as malonyl conjugates [10,11]. 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].…”

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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“…Initial surveys testing for the presence of nod-gene inducer conjugates in roots used more rigorous precautions to preserve fragile molecules (17). Differences from the above protocol included extraction of48-h-old roots with cold (<00C) acetone and drying under N2 at 15°C or less.…”

Section: Isolation and Purification Of Flavonoidsmentioning

confidence: 99%

Concurrent Synthesis and Release of nod-Gene-Inducing Flavonoids from Alfalfa Roots

Maxwell

Phillips

1990

Plant Physiol.

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Flavonoid signals from alfalfa (Medicago sativa L.) induce transcription of nodulation (nod) genes in Rhizobium meliloti. Alfalfa roots release three major nod-gene inducers: 4',7-dihydroxyflavanone, 4',7-dihydroxyflavone, and 4,4'-dihydroxy-2'-methoxychalcone. The objective of the present study was to define temporal relationships between synthesis and exudation for those flavonoids. Requirements for concurrent flavonoid biosynthesis were assessed by treating roots of intact alfalfa seedlings with [U-14C]-L-phenylalanine in the presence or absence of the phenylalanine ammonia-lyase inhibitor L-2-aminoxy-3-phenylpropionic acid (AOPP). In the absence of AOPP, each of the three flavonoids in exudates contained 14C. In the presence of AOPP, 14C labeling and release of all the exuded nod-gene inducers were reduced significantly. AOPP inhibited labeling and release of the strongest nod-gene inducer, methoxychalcone, by more than 90%. Experiments with excised cotyledons, hypocotyls, and roots incubated in solution showed that the flavonoids could be synthesized in and released from each organ. However, the ratio of the three flavonoids in exudates from intact plants was most similar to the ratio recently synthesized and released from excised roots. A portion of recentiy synthesized flavonoid aglycones was found conjugated, presumably as glycosides, in root extracts and may have been involved in the release process. Data from root extracts showed that formononetin, an isoflavonoid which does not induce nod genes, was present in conjugated and aglycone forms but was not released by normal intact roots. In contrast, roots stressed with CuCI2 did release the aglycone formononetin. Thus, the release process responsible for exudation of nod-gene inducers appears to be specific rather than a general phenomenon such as a sloughing off of cells during root growth. The synthesis and specific concurrent release of flavonoid nod-gene inducers in this study is consistent with the physiological requirement for nodule formation of the 3-day-old seedlings used.Alfalfa (Medicago sativa L.), an important leguminous forage crop, forms N2-fixing root nodules in association with the soil bacterium Rhizobium meliloti. Early events of alfalfa nodule formation require expression of nodulation genes including nodDABC on the megaplasmid of R. meliloti (6,15). Transcription of nodABC is induced through the cooperative action of the protein product of the nodD gene and components of root and seed exudates (21). Luteolin, '

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High Performance Liquid Chromatographic Separation of Isoflavones and Structural Elucidation of Isoflavone 7-O-glucoside 6″-malonates from Cicer arietinum

Cited by 85 publications

References 20 publications

Stimulation of hyphal growth of the VA mycorrhizal fungus Gigaspora margarita by suspension‐cultured Pueraria phaseoloides cells and cell products

Stimulation of hyphal growth of the VA mycorrhizal fungus Gigaspora margarita by suspension‐cultured Pueraria phaseoloides cells and cell products

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

Concurrent Synthesis and Release of nod-Gene-Inducing Flavonoids from Alfalfa Roots

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