Phaseollin formation and metabolism in Phaseolus vulgaris

Woodward, Michael D.

doi:10.1016/0031-9422(80)85139-9

Cited by 57 publications

(20 citation statements)

References 50 publications

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“…3B). This compound has been observed by the plant Phaseolus vulgaris after fungal infection (32) and has been used in chemical synthesis for substituted pterocarpans (27).…”

Section: Discussionmentioning

confidence: 99%

Biotransformation of Natural and Synthetic Isoflavonoids by Two Recombinant Microbial Enzymes

Seeger

González

Cámara

et al. 2003

Appl Environ Microbiol

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Isolation and synthesis of isoflavonoids has become a frequent endeavor, due to their interesting biological activities. The introduction of hydroxyl groups into isoflavonoids by the use of enzymes represents an attractive alternative to conventional chemical synthesis. In this study, the capabilities of biphenyl-2,3-dioxygenase (BphA) and biphenyl-2,3-dihydrodiol 2,3-dehydrogenase (BphB) of Burkholderia sp. strain LB400 to biotransform 14 isoflavonoids synthesized in the laboratory were investigated by using recombinant Escherichia coli strains containing plasmid vectors expressing the bphA1A2A3A4 or bphA1A2A3A4B genes of strain LB400. The use of BphA and BphB allowed us to biotransform 7-hydroxy-8-methylisoflavone and 7-hydroxyisoflavone into 7,2,3-trihydroxy-8-methylisoflavone and 7,3,4-trihydroxyisoflavone, respectively. The compound 2-fluoro-7-hydroxy-8-methylisoflavone was dihydroxylated by BphA at ortho-fluorinated and meta positions of ring B, with concomitant dehalogenation leading to 7,2,3,-trihydroxy-8-methylisoflavone. Daidzein (7,4-dihydroxyisoflavone) was biotransformed by BphA, generating 7,2,4-trihydroxyisoflavone after dehydration. Biotransformation products were analyzed by gas chromatography-mass spectrometry and nuclear magnetic resonance techniques.

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“…3B). This compound has been observed by the plant Phaseolus vulgaris after fungal infection (32) and has been used in chemical synthesis for substituted pterocarpans (27).…”

Section: Discussionmentioning

confidence: 99%

Biotransformation of Natural and Synthetic Isoflavonoids by Two Recombinant Microbial Enzymes

Seeger

González

Cámara

et al. 2003

Appl Environ Microbiol

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“…This, coupled with kinetic labeling The biosynthesis of the phytoalexins in Phaseolus vulgaris may proceed by a very similar route to that elucidated in M. saliva, the main differences between Schemes 8, 9, and 10 being the existence of the 5-hydroxy isoflavonoid pathway and the predominance of isoprenylation rather than methylation as the major substitution process after the initial Cls stage in P. vulgaris. Most of the evidence for the reaction sequences in Schemes 9 and 10 has come from studies on the isolation of minor isoflavonoid components from P. vulgaris endocarp tissue challenged with Monilinia fmcticola (189,(204)(205)(206). This work has led to the proposal of a pathway to kievitone involving 2'-hydroxylation of genistein (I), oxidation to the isoflavanone [to yield dalbergioidin (XLIIa)], and finally isoprenylation of the A ring (205).…”

Section: Conversion Of Isoflavones To Pterocarpans and Furthermentioning

confidence: 97%

“…These occur in both induced phytoalexins and constitutive isoflavonoids. There may be one free prenyl group as in kievitone (IV), phaseollidin (XII), or wighteone (111), two free groups as in the di-prenyl genisteins (2 12), or prenyl groups cyclized to o-hydroxy groups resulting in the 2,2-dimethylchromen ring structures of, for example, phaseollin (189). In addition to the above stages of prenyl addition, there is also the question of whether the enzymes are specific for the two distinct A-ring hydroxylation patterns encountered, or for the position (8-,6-, or 3'-, isoflavone numbering) of insertion of the prenyl group.…”

Section: Conversion Of Isoflavones To Pterocarpans and Furthermentioning

confidence: 99%

Phytoalexins: Enzymology and Molecular Biology

Dixon¹,

Dey²,

Lamb

1983

Advances in Enzymology - And Related Areas of Molecular Biology

222

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“…Glycinol is therefore assigned the 6aS, laS configuration, (Fig. 1), based on comparison with other (-)-pterocarpans showing maxima in their optical rotary dispersion or circular dichroism spectra in this region (10,23).…”

Section: Methodsmentioning

confidence: 99%

Host-Pathogen Interactions

Weinstein¹,

Hahn²,

Albersheim³

1981

Plant Physiol.

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A previously unrecognized phytoalexin has been isolated from soybean cotyledons that had been infected with bacteria or exposed to ultraviolet light. The phytoalexin has been purified to homogeneity by silica gel flash chromatography and high pressure liquid chromatography. It has been structurally characterized by its ultraviolet, circular dichroism and nuclear magnetic resonance spectra, polarimetry, and its mass spectrometric fragmentation pattern. The phytoalexin, (6aS,llaS)-3,6a,9-trihydroxypterocarpan, is a compound that had previously been detected in CuCI2-treated soybeans and is structurally related to the previously identified soybean phytoalexins glycerollins I to IV. It is proposed that the trivial name glycinol be used for this phytoalexin. Glycinol is a broad spectrum antibiotic capable of prolonging the lag phase of growth of all six bacteria examined, namely Erwinia carotovora, Pseudomonas glycinea (races 1 and 3), Escherichia coli, Xanthomonasphaseoli, and Bacillus subtilis. Glycinol also inhibits the growth of the fungi Phytophthora megasperma f. sp. glycinea (race 1), Saccharomyces cerevisiae, and Cladosporium cucwmerinum. Glycinol is a static agent against the six bacterial species listed above and against S. cerevisiae, and appears to be static against the other fungi examined. As with other phytoalexins, there is no correlation between the pathogenicity of a microorganism and its sensitivity to glycinol.Phytoalexins are low mol wt antimicrobial compounds produced by plants in response to challenge by microorganisms. These compounds accumulate at the site of infection and are involved in the plant's defense response to potential pathogens (3,8,14).The accumulation of the pterocarpan phytoalexins, glyceollin4 (Fig. 1), by soybean (Glycine max) in response to fungal attack has been well documented (12). In vitro studies have shown glyceollin to be inhibitory to the growth of both bacteria and fungi (1,11,12 for which we propose the trivial name glycinol. This pterocarpan has been previously observed as a quantitatively minor constituent in CuCl2-treated soybean cotyledons, although no antifungal activity was recognized to be associated with it (18). The present study describes an improved isolation procedure for the pterocarpan leading to mg quantities of the crystalline compound. We present also the results of our studies of the effect of glycinol on growth of a variety of microorganisms. MATERIALS AND METHODSPlant Material. Certified quality soybean seed (Glycine max [L.] Merr. cv. Wayne) was obtained from Wilkens Seed Co.Pontiac, IL. The seed was stored in closed containers at 4 C and hand sorted for soundness before planting. The sorted seeds were planted at a density of about 75 g seed/tray (40 x 30 x 9 cm) on a 2-cm layer of potting soil (Bacto Potting Medium, Michigan Peat Co., Houston, TX) overlaying a water-soaked 4-cm layer of vermiculite (W. R. Grace and Co., Cambridge, MA). The seed was then overlayed with a 2 cm layer of vermiculite, and watered with 400 ml deionized H20/...

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Phaseollin formation and metabolism in Phaseolus vulgaris

Cited by 57 publications

References 50 publications

Biotransformation of Natural and Synthetic Isoflavonoids by Two Recombinant Microbial Enzymes

Biotransformation of Natural and Synthetic Isoflavonoids by Two Recombinant Microbial Enzymes

Phytoalexins: Enzymology and Molecular Biology

Host-Pathogen Interactions

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