“…The white amorphous solid obtained gave IR, 1 H-NMR, 13 CNMR, and EIMS spectral data that agreed with data previously reported for TSL [7,8,18,20,31]. Spectral, chromatographic, and bioautographic comparisons with purchased TSL (4-hydroxyphenethyl alcohol, 98%, Aldrich) confirmed the identification of the isolated antifungal compound as TSL.…”
Enterobacter cloacae S11: T:07 (NRRL B-21050) is a promising biological control agent that has significantly reduced both fungal dry rot disease and sprouting in laboratory and pilot potato storages. The metabolites phenylacetic acid (PAA), indole-3-acetic acid (IAA), and tyrosol (TSL) were isolated from S11:T:07 liquid cultures provided with three different growth media. The bioactivities of these metabolites were investigated via thin-layer chromatography bioautography of antifungal activity, wounded potato assays of dry rot suppressiveness, and cored potato eye assays of sprout inhibition. Relative accumulations of PAA, IAA, and TSL in cultures were nutrient dependent. For the first time, IAA, TSL, and PAA were shown to have antifungal activity against the dry rot causative pathogen Gibberella pulicaris, and to suppress dry rot infection of wounded potatoes. Disease suppression was optimal when all three metabolites were applied in combination. Dosages of IAA that resulted in disease suppression also resulted in sprout inhibition. These results suggest the potential for designing culture production and formulation conditions to achieve a dual purpose biological control agent able to suppress both dry rot and sprouting of stored potatoes.
“…The white amorphous solid obtained gave IR, 1 H-NMR, 13 CNMR, and EIMS spectral data that agreed with data previously reported for TSL [7,8,18,20,31]. Spectral, chromatographic, and bioautographic comparisons with purchased TSL (4-hydroxyphenethyl alcohol, 98%, Aldrich) confirmed the identification of the isolated antifungal compound as TSL.…”
Enterobacter cloacae S11: T:07 (NRRL B-21050) is a promising biological control agent that has significantly reduced both fungal dry rot disease and sprouting in laboratory and pilot potato storages. The metabolites phenylacetic acid (PAA), indole-3-acetic acid (IAA), and tyrosol (TSL) were isolated from S11:T:07 liquid cultures provided with three different growth media. The bioactivities of these metabolites were investigated via thin-layer chromatography bioautography of antifungal activity, wounded potato assays of dry rot suppressiveness, and cored potato eye assays of sprout inhibition. Relative accumulations of PAA, IAA, and TSL in cultures were nutrient dependent. For the first time, IAA, TSL, and PAA were shown to have antifungal activity against the dry rot causative pathogen Gibberella pulicaris, and to suppress dry rot infection of wounded potatoes. Disease suppression was optimal when all three metabolites were applied in combination. Dosages of IAA that resulted in disease suppression also resulted in sprout inhibition. These results suggest the potential for designing culture production and formulation conditions to achieve a dual purpose biological control agent able to suppress both dry rot and sprouting of stored potatoes.
“…2 shows the absorption spectra between 440nm and 500nm of the samples prepared by passing the reaction mixtures of 3-HAT and oxyor met-haemoglobin through a column of Sephadex G-25 (fine grade). The eluates free of oxy-and met-haemoglobin showed spectra characteristic of authentic cinnabarinic acid, with a peak at 455 nm (Ishiguro et al, 1971). Our results are very consistent with those of Ishiguro et al (1971) in showing that a small amount of haemoglobin catalyses 3-HAT conversion into cinnabarinic acid in the presence of 0.1 Imm-Mn2 +.…”
Section: Resultssupporting
confidence: 92%
“…Then the reaction mixture was passed through a column (0.5 cm x 0cm) of Sephadex G-25 (fine grade) previously equilibrated with 10mM-phosphate buffer, pH 7.0. The orange-coloured solutions including 3-HAT and metabolic product of 3-HAT were identified spectrophotometrically (Ishiguro et al, 1971). The samples were also subjected to t.l.c.…”
Section: Methodsmentioning
confidence: 99%
“…3-Hydroxyanthranilic acid (3-HAT) is especially important as a precursor of NAD, and is firstly metabolized to 2-acroleyl 3-aminofumarate. However, haemoproteins such as catalase and haemoglobin have been shown to metabolize 3-HAT to cinnabarinic acid in the presence of Mn2 + (in the several-hundred-micromolar range) (Savage & Prinz, 1977;Ishiguro et al, 1971). The physiological significance of this metabolic process is not still clear.We have observed that 3-HAT oxidizes intracellular haemoglobin extensively when human erythrocytes are incubated with this compound.…”
3-Hydroxyanthranilic acid, a metabolite of tryptophan, was rapidly metabolized by human erythrocytes. The final product was determined to be cinnabarinic acid as detected by spectrophotometry, paper chromatography and t.l.c. The formation of cinnabarinic acid from 3-hydroxyanthranilic acid in the cells was markedly inhibited by CO when intracellular haemoglobin was in a ferrous state, and by cyanide when it was in a ferric state. Ferrous haemoglobin in erythrocytes was oxidized to (alpha 3+ beta 2+)2, (alpha 2+ beta 3+)2 and (alpha 3+ beta 3+)2 by 3-hydroxyanthranilic acid, and the oxidation rates were very high, like those of cinnabarinic acid formation, suggesting that the metabolism of 3-hydroxyanthranilic acid is coupled with oxidoreductive reactions of intracellular haemoglobin. This view was further confirmed by the findings that 3-hydroxyanthranilic acid was metabolized by ferrous or ferric haemoglobin and that ferrous and ferric haemoglobins were oxidized and reduced by the compound respectively. The significance of the metabolism of 3-hydroxyanthranilic acid and the oxidoreductive reactions of haemoglobin with this compound may be associated with the pathological conditions with increased 3-hydroxyanthranilic acid levels in the blood of diabetic subjects.
“…Slininger et al, 2004). Furthermore, tyrosol occurs in flowers of Osmanthus fragrans (Ishiguro et al, 1955), in the underground part of roseroot (Rhodiola rosea L., Crassulaceae) (Linh et al, 2000;Yousef et al, 2006) and in olive fruits (Olea europaea L., Oleaceae) (Giovannini et al, 1999).…”
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