Über den Abbau von Chalkonen und Isoflavonen in pflanzlichen Zellsuspensionskulturen / Degradation of Chalcones and Isoflavones in Plant Cell Suspension Cultures

Berlin, Jochen; Kiss, P.; Müller‐Enoch, Dieter; Gierse, Dieter; Barz, Wolfgang; Janistyn, Boris

doi:10.1515/znc-1974-7-813

Cited by 17 publications

(11 citation statements)

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“…Feeding experiments with labeled isoflavones in cell cultures have shown that turnover may be explained by assuming catabolic reactions to occur (8).…”

Section: Izmentioning

confidence: 99%

“…Such demethylation reactions are regarded as initial steps in degradation reactions of N-methylphenylurea herbicides, phenylethylamine alcaloids such as hordenine (see Fig. 9), p-O-methyl benzoic and cinnamic acids (9) or isoflavone aglycones (8).…”

Section: Demethylation Reactionsmentioning

confidence: 99%

“…Such reactions have so far never been observed in O-demethylation studies in cell cultures. With several different substrates (7,8,29) the liberated O-methylgroups were quantitatively oxidized to C02.…”

Section: Demethylation Reactionsmentioning

confidence: 99%

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Catabolism of Endogenous and Exogenous Compounds by Plant Cell Cultures

Barz¹

1977

Proceedings in Life Sciences

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A. IntroductionMany reports in the literature over the past decade have established that higher plants possess a much greater capacity than previously expected for the degradation of a wide variety of organic compounds (3,19,23,55). These observations are of special interest in the field of secondary plant constituents because such compounds were generally regarded as storage products without any further metabolism during the life time of a plant (49, 54). The present concept, however, holds that. the majority of plant products is in a state of permanent metabolism with concomitant synthesis and degradation of both primary and secondary constituents. Therefore, stationary concentrations of plant products are the result of the ratio of the rate of synthesis and turnover (steady-state-concentrations) (for details see 3,5,70).Turnover of plant products in plants primarily consists of two types of reactions (1) complete degradative pathways leading to primary constituents and finally CO 2 and (2) polymerisation reactions where organic material is tightly bound into cell wall and membrane structures. The ratio of these two reactions depends upon both the availability of enzymes and the chemical structure of the compounds involved. Cell cultures offer many advantages for the elucidation of catabolic pathways. The reliable absence of microorganisms and the ease of physiological manipulation of cells with phytohormones and various other molecular effectors require special emphasis (4, 5).In the context of biotechnological application of cell cultures the phenomenon of degradation of cellular constituents is of twofold importance:1. Extensive production of secondary constituents should best occur without any loss of intermediates or endproducts by degradative reactions, 2. Applicable biotransformations with cell cultures require high rate of substrate conversion with subsequent protection of product from catabolic reactions.Turnover of endogenous and catabolism of exogenous compounds will separately be discussed because of possible differences in the metabolism of endogenously formed and exogenously applied compounds. Compartmentalization of cells may hinder exogenous compounds to reach t~e natural. site of cellular metabolism but rather lead to unphysiolog~cal react~ons, altered pathways or the preferential formation of storage products (34,63

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“…Feeding experiments with labeled isoflavones in cell cultures have shown that turnover may be explained by assuming catabolic reactions to occur (8).…”

Section: Izmentioning

confidence: 99%

Section: Demethylation Reactionsmentioning

confidence: 99%

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Catabolism of Endogenous and Exogenous Compounds by Plant Cell Cultures

Barz¹

1977

Proceedings in Life Sciences

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“…6 ist das Abbauschema von Chalkonen und den ihnen isomeren Flavanonen gezeigt. Durch formale Spaltung zwischen der Carbonylgruppe und dem A-Ring entstehen Zimtsauren, deren weiterer Abbau zu den dem B-Ring entsprechenden Benzoesauren fiihrt (JANISTYN et al, 1971;BERLIN et al, 1974). Durch Venvendung spezifisch Ring-A-markierter Substrate konnten wir zeigen, daB sowohl die Phloroglucinringe wie auch die Resorcinringe einem vollstandigen Abbau unterliegen.…”

Section: Abb 5: Abbauwege Von Flavonolen In Pflanzlichen Zellsuspensunclassified

Abbau Von Aromatischen Und Heterocyclischen Pflanzeninhaltsstoffen Durch Zellsuspensionskulturen

Barz¹

1975

Planta Med

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After an analysis of the difficulties in the elucidation of catabolic pathways inhigher plants the advantages of cell suspension ctiltures as experimental systems are described. I t could be demonstrated that flavonols, chalcones, flavanones, aurones and phenylethylamines are degraded by variotls cell suspension cultures with the intermediate formation of benzoic acids. The most recent evidence for ring fission reactions in higher plant cells is compared with, microbial pathways. Experiments are described which show that anaerobic conditions favour glycosilation of phenols due to inhibition o f degradative reactions. The importance of phenolase depending polymerisation reactions of phenols and their structural requirements are discussed. Finally cell suspension cultures o f . higher plants are shown to be suitable systems for degradative studies o f nucleotides and coenzyms. Diese Arbeit mochte pflanzliche Zellsuspensionskulturen als geeignete experimentelle Systeme fiir die Aufklarung kataboler Stoffwechselwege in Pflanzen vorstellen.Der Abbau von Pflanzeninhaltsstoffenganz besonders der von aromatischen und heterocyclischen Verbindungen des Sekundarstoffwechselsdurch die synthetisierende Pflanze selbst ist ein recht neuer Aspekt der pflanzlichen Biochemie. Die urspriinglich weit verbreitete Auffassung, daB sekundare Inhaltsstoffe metabolisch inaktive Stoffwechselendprodukte darstellen (z. B. REZNIK, 1960; MOTHES, 1969) ist vielfaltig widerlegt worden (BARZ und HOSEL, 1975). Wir miissen heute annehmen, da!3 in sehr vielen, wenn in nicht allen aktiv wachsenden Pflanzenteilen gleichzeitig Synthese und weiterfiihrender Abbau von sekundaren Inhalts-Heruntergeladen von: University of British Columbia. Urheberrechtlich geschützt.

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“…Der Abbau glykosidischer Naturstoffe durch Pflanzen und Mikroorganismen wird oft mit einer Abspaltung der Zuckerreste durch spezifische Glykosidasen eingeleitet (PODSTOLSKI und LEWAK, 1970;HAY et al, 1961). Vor kurzer Zeit wurden auch für die Isoflavone der Kichererbse, für die bereits Umsatz und Abbau festgestellt worden war (BARZ, 1969;BARZ und HOSEL, 1971;BERLIN et al, 1974) HOSEL, in Vorbereitung). Junge Kichererbsenpflanzen enthalten danach in betrachtlicher Menge p-Monoglukosidasen, die spezifisch die Spaltung von'Isoflavon-7-O-B-glukosiden katalysieren.…”

Section: Introductionunclassified

AUSBILDUNG UND VERTEILUNG VON ISOFLAVON–7–O–β–GLYKOSID SPEZIFISCHEN β–GLYKOSIDASEN INCICER ARIETINUM

Hösel¹

1976

Planta Med

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Various P-glycosidases, specific for the hydrolysis of isoflavone 7-O-p-glycosides, have been detected in the garbanzo bean, C i c e r a r i e t i n u m L. ,6-Monoglucosidases are present within the different plant organs in comparable activity whereas j3-diglycosidases are found in the leaves only. Both ,ô-glycosidase activities develop in the earliest States of plant growth, probably by protein de novo synthesis. A correlation between p-glycosidases and isofïavones present in garbanzo bean plants is discussed.

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Über den Abbau von Chalkonen und Isoflavonen in pflanzlichen Zellsuspensionskulturen / Degradation of Chalcones and Isoflavones in Plant Cell Suspension Cultures

Cited by 17 publications

References 0 publications

Catabolism of Endogenous and Exogenous Compounds by Plant Cell Cultures

Catabolism of Endogenous and Exogenous Compounds by Plant Cell Cultures

Abbau Von Aromatischen Und Heterocyclischen Pflanzeninhaltsstoffen Durch Zellsuspensionskulturen

AUSBILDUNG UND VERTEILUNG VON ISOFLAVON–7–O–β–GLYKOSID SPEZIFISCHEN β–GLYKOSIDASEN INCICER ARIETINUM

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