�ber den Einflu� von Licht auf den Umsatz der Isoflavone Formononetin und Biochanin A in Cicer arietinum L.

Planta ◽  
1970 ◽  
Vol 90 (2) ◽  
pp. 191-202 ◽  
Author(s):  
W. Barz ◽  
Ch. Adamek
Keyword(s):  
Cicer Arietinum ◽  
Biochanin A ◽  
Cicer Arietinum L

scholarly journals Stoffwechsel aromatischer Pflanzeninhaltsstoffe I

1969 ◽  
Vol 24 (2) ◽  
pp. 234-239 ◽  
Author(s):  
Wolfgang Barz
Keyword(s):  
Cicer Arietinum ◽  
Half Life ◽  
Biochanin A ◽  
Pulse Labelling ◽  
Phaseolus Aureus ◽  
Cicer Arietinum L ◽  
Plant Products ◽  
Biological Half Life ◽  
Total Turnover ◽  
Secondary Plant

The turnover of the isoflavones, formononetin and biochanin A, in Cicer arietinum L. and of the isoflavone, daidzein, and the coumestan, coumestrol, in Phaseolus aureus Roxb. has been determined by pulse labelling. The biological half-life of formononetin, daidzein and coumestrol has been found to be approximately 50 hours, while the turnover of biochanin A appeared to be very slow. The excretion of all four plant products through the roots into the medium has been measured. Approximately 3 percent of the total turnover of isoflavones in the plants can be accounted for by excretion into the medium.The results are discussed in view of the concept that secondary plant products may well be subject to further metabolism.

Zur Biogenese der Isoflavone

1961 ◽  
Vol 16 (1) ◽  
pp. 2-5 ◽  
Author(s):  
Hans Grisebach ◽  
Gerhard Brandner
Keyword(s):  
Cicer Arietinum ◽  
Cinnamic Acid ◽  
Red Clover ◽  
Biochanin A ◽  
Cicer Arietinum L ◽  
The One

With the aid of cinnamic acid-[3-14C] and DL-Phenylalanine-[1-14C] it has been demonstrated that the biogenesis of both biochanin-A (5.7-Dihydroxy-4′-methoxyisoflavone) and formononetin (7-Hydroxy-4′-methoxyisoflavone) in chana germ (Cicer arietinum L.) involves a phenyl migration like the one which has been found to occur in the biogenesis of formononetin in red clover. 4.4′.6′-Trihydroxychalcone-4′-glucoside-[β-14C] is incorporated into formononetin but not into biochanin-A, the entire radioactivity being localized in C-2 of formononetin. Thus it has been proven that a C6-C3-C6 compound can be converted into an isoflavone. Acetate-[1-14C] is incorporated almost exclusively into ring A of formononetin.

Elicitor-induced Changes of Enzyme Activities Related to Isoflavone and Pterocarpan Accumulation in Chickpea (Cicer arietinum L.) Cell Suspension Cultures

1988 ◽  
Vol 43 (7-8) ◽  
pp. 536-544 ◽  
Author(s):  
Susanne Daniel ◽  
Walter Hinderer ◽  
Wolfgang Barz
Keyword(s):  
Cell Culture ◽  
Cell Suspension ◽  
Cicer Arietinum ◽  
Enzyme Activities ◽  
Cell Suspension Cultures ◽  
Suspension Cultures ◽  
Biochanin A ◽  
Primary Metabolism ◽  
Cicer Arietinum L ◽  
L Cell

The extractable activities of thirteen enzymes of primary and secondary metabolism have been measured in chickpea (Cicer arietinum L.) cell suspension cultures after treatment with an elicitor from the fungus Ascochyta rabiei (Pass.) Lab. The cell culture, derived from the A. rabiei resistant cultivar ILC 3279, constitutively accumulated the isoflavones biochanin A and formononetin together with their 7-O-glucosides and the 7-O-glucoside-6″-malonates. After elicitor application the cells rapidly form the pterocarpan phytoalexins medicarpin and maackiain. Among the enzymes of primary metabolism only the glucose 6-phosphate dehydrogenase exhibited a significant increase in activity with a maximum four hours after application of the elicitor. In phenylpropane metabolism the activities of phenylalanine ammonia lyase and chalcone synthase were enhanced by the elicitor and exhibited highest levels after four hours. In contrast the chalcone isomerase activity was not influenced by the elicitor. A substantial enhancement occurred with the isoflavone 7-O-glucosyltransferase activity eight hours after elicitor application. The results suggest that in this cell culture the elicitor-induced biosynthesis of pterocarpan phytoalexins was accompanied with a rapid and transient increase of those enzyme activities which are located at branching points of related pathways, i.e. pentose phosphate cycle, general phenylpropane metabolism, flavonoid formation and isoflavone conjugation.

scholarly journals Untersuchungen über den Einbau methylierter Vorstufen in die Isoflavone der Kichererbse

1967 ◽  
Vol 22 (6) ◽  
pp. 627-633 ◽  
Author(s):  
Wolfgang Barz ◽  
Hans Grisebach
Keyword(s):  
Cicer Arietinum ◽  
Cinnamic Acid ◽  
Late Stage ◽  
Incorporation Rate ◽  
Biochanin A ◽  
Cicer Arietinum L ◽  
Methoxycinnamic Acid

In order to determine at what stage in the biosynthesis of biochanin A (5.7-dihydroxy-4′-methoxyisoflavone) and formononetin (7-hydroxy-4′-methoxyisoflavone) the methylation of the 4′-hydroxygroup occurs, the incorporation of p-methoxy-cinnamic acid-[3-14C-methyl-T], 4-methoxy-2′.4′-dihydroxychalcone- [β-14C-methyl-T] and a number of unmethylated precursors into the isoflavones of chana seedlings (Cicer arietinum L.) was compared. p-Methoxy-cinnamic acid and 4.2′.4′-Trihydroxychalcone were found to be the best precursors. Although the incorporation of p-methoxy-cinnamic acid was very good (incorporation rate 6.2%) the T/14C ratio dropped by 95% upon incorporation into the isoflavones, a fact which showed that a rapid demethylation takes place in the plants.In addition, kinetic experiments were carried out with p-methoxycinnamic acid- [3-14C-methyl-14C-methyl-T] and 4-methoxy-2′.4′-dihydroxychalcone- [β-14C-methyl-14C-methyl-T]. But in this case also the rapid demethylation did not permit a definite conclusion to be drawn as to the stage in the biosynthesis at which the methylation step occurs. The very good incorporation of 4.2′.4′-trihydroxycalcone- [β-14C] into the isoflavones (5,3% incorporation, dilution 61), however, shows that methylation can occur at a late stage in the biosynthesis.

Stereospezifischer Einbau von (—)5.7.4′-Trihydroxyflavanon in Flavonoide und Isoflavone

1966 ◽  
Vol 21 (3) ◽  
pp. 201-205 ◽  
Author(s):  
L. Patschke ◽  
W. Barz ◽  
H. Grisebach
Keyword(s):  
Cicer Arietinum ◽  
Paper Chromatography ◽  
Incorporation Rate ◽  
Biochanin A ◽  
Cicer Arietinum L ◽  
Better Than

(±)5,7,4′-Trihydroxyflavanone-5-glucoside-[2-14C] was synthesized and the diastereomeric (+) and (-) glucosides were separated by paper chromatography. In buckwheat seedlings the incorporation rate of the (-) enantiomer into quercetin was 16 times higher and into cyanidin 3.6 times higher than that of the (+) compound. In chana seedlings (Cicer arietinum L.) the (-) compound was incorporated into biochanin A (5,7-dihydroxy-4′-methoxy-isoflavone) 14 times better than the (+) compound, whereas in agreement with earlier results the incorporation of both enantiomers into formononetin (7-hydroxy-4′-methoxy-isoflavone) was very low.The results prove the stereospecific incorporation of the naturally occuring (-) · 2 · S · 5.7.4′-trihydroxyflavanone into flavonoids and isoflavonoids. The incorporation of the (+) enantiomer is probably due to a racemization of this compound via the chalcone.

scholarly journals Cicer arietinum L. Sprouts’ Influence on Mineralization of Saos-2 and Migration of MCF-7 Cells

Molecules ◽  
2020 ◽  
Vol 25 (19) ◽  
pp. 4490
Author(s):  
Małgorzata Zakłos-Szyda ◽  
Ilona Gałązka-Czarnecka ◽  
Joanna Grzelczyk ◽  
Grażyna Budryn
Keyword(s):  
Biological Activity ◽  
Cicer Arietinum ◽  
Biochanin A ◽  
Cicer Arietinum L ◽  
Prevention Of Osteoporosis ◽  
And Migration ◽  
Induced Apoptosis ◽  
Factor Α ◽  
Necrosis Factor ◽  
Mcf 7

In the present study, we investigated the biological activity of four extracts obtained from Cicer arietinum L. sprouts. The fermentation of the sprouts with Lactobacillus casei and their incubation with β-glucosidase elevated the concentrations of isoflavonoids, especially coumestrol, formononetin and biochanin A. To study the biological activity of C. arietinum, the human osteosarcoma Saos-2 and human breast cancer MCF-7 cell lines were used. The extracts obtained from fermented sprouts exhibited the strongest ability to decrease intracellular oxidative stress in both types of cells. They augmented mineralization and alkaline phosphatase activity in Saos-2 cells, as well as diminished the secretion of interleukin-6 and tumor necrosis factor α. Simultaneously, the extracts, at the same doses, inhibited the migration of MCF-7 cells. On the other hand, elevated concentrations of C. arietinum induced apoptosis in estrogen-dependent MCF-7 cells, while lower doses stimulated cell proliferation. These results are important for carefully considering the use of fermented C. arietinum sprouts as a dietary supplement component for the prevention of osteoporosis.

Stoffwechsel aromatischer Pflanzeninhaltsstoffe II

1969 ◽  
Vol 24 (5) ◽  
pp. 638-642 ◽  
Author(s):  
Wolfgang Barz ◽  
Birgit Roth-Lauterbach
Keyword(s):  
Cicer Arietinum ◽  
Biochanin A ◽  
Pulse Labelling ◽  
Cicer Arietinum L

The incorporation of L-methionine- (methyl-14C) into isoflavones of young chana plants (Cicer arietinum L.) of various age was determined. The percent incorporation into biochanin A was highest in 7 day old plants and decreased with the age of the plants whereas the incorporation into formononetin remained fairly constant. The data provide further evidence for a turnover of formononetin.By simultaneous pulse labelling with L-methionine- (methyl-3H) and DL-phenylalanine- (1-14C) it could be shown that isoflavones are not subject to demethylation reactions.The results also demonstrate that the enzymes necessary for the formation of isoflavones and the metabolism of formononetin are qualitatively and quantitatively built up in young plants.

Über die Bedeutung der Isoflavanone bei der Isoflavonbiosynthese

1968 ◽  
Vol 23 (4) ◽  
pp. 494-504 ◽  
Author(s):  
Hans Grisebach ◽  
Harald Zilg
Keyword(s):  
Cicer Arietinum ◽  
Biochanin A ◽  
Substitution Pattern ◽  
Cicer Arietinum L ◽  
Isoflavone Biosynthesis

The occurrence of isoflavanones in Cicer arietinum was investigated. The presence of homoferreirin (5,7-dihydroxy-2′,4′-dimethoxyisoflavanone) was demonstrated but no isoflavanones with the same substitution pattern as the isoflavones occuring in this plant could be found. Soja seedlings (Soja hispida) are able to dehydrogenate dihydrodaidzein (7,4′-dihydroxyisoflavanone) to daidzein, as was shown with tritium labeled dihydrodaidzein. 7,4′-Dihydroxyflavanone- [2-14C] which was fed to the seedlings simultaneously with the dihydrodaidzein was incorporated into daidzein to about the same extent as dihydrodaidzein. Part of the daidzein is excreted into the medium by the seedlings.7,4′-Dihydroxyflavanone- [2-14C-3-T2] was synthesized. When this compound was incorporated into 7-hydroxy-4′-methoxyisoflavone (formononetin) in chana seedlings (Cicer arietinum L.) the T/14C ratio dropped by 99 per cent. In contrast, when 5,7,4′-trihydroxyflavanone- [2-14C-2-T] was incorporated into 5,7-dihydroxy-4′-methoxyisoflavone (biochanin A) the T/14C ratio stayed constant.The results are discussed in the light of possible mechanisms for the 2,3-aryl migration occurring during isoflavone biosynthesis and in relation to the biogenetic relation-ships of isoflavones and isoflavanones.

Further Characterization of Chickpea Isoflavone 7-O-Glucoside- 6"-O-malonate: malonylesterase: Evidence for a Highly Specific, Membrane-Bound Enzyme in Roots of Cicer arietinum L.

1987 ◽  
Vol 42 (3) ◽  
pp. 251-257 ◽  
Author(s):  
Walter Hinderer ◽  
Johannes Köster ◽  
Wolfgang Barz
Keyword(s):  
Enzyme Activity ◽  
Cicer Arietinum ◽  
Biochanin A ◽  
Cicer Arietinum L ◽  
Apparent Homogeneity ◽  
Malonyl Coa ◽  
Highly Sensitive ◽  
Membrane Bound

The specific malonylesterase from chickpea (Cicer arietinum L.), hydrolyzing biochanin A 7-O- glucoside-6″-O-malonate (BGM), has been purified to apparent homogeneity and characterized recently (Hinderer et al., Arch. Biochem. Biophys. 248, 570-578 [1986]). Its substrate specificity as well as the high molecular mass of the native enzyme were further investigated. The 5-deoxy- isoflavone conjugate corresponding to BGM, the formononetin 7-O-glucoside-6,,-O-malonate (FGM), was shown to be a substrate of the malonylesterase essentially as BGM. By contrast, methyl-BGM, a diester of malonic acid was a poor substrate. The purified enzyme completely lacked thioesterase activity with malonyl-CoA as substrate. The inability of the malonylesterase to hydrolyze synthetic acetyl or propionyl esters was further demonstrated with a highly sensitive fluorometric assay using esters of 4-methylumbelliferone. The enzyme-catalyzed hydrolysis of BGM was stimulated in the presence of dissociated carboxylic acids like citrate which was most effective at 30 mM and pH 7.5-8.0. The purified malonylesterase as well as the enzyme activity in crude extracts were totally excluded in gelchromatography with Ultrogel AcA 22. The enrichment of the enzyme activity in microsomal fractions gave strong evidence that the malonylesterase is membrane-bound in vivo. Stimulation of the enzyme activity in vitro by detergents indicates the presence of lipid material in the enzyme and the activity profiles obtained after sedimentation analyses suggest that purifica­tion of a distinct membrane-protein complex had been achieved.

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