Metabolic Products of Fungi. XXVIII. The Structure of Aurofusarin. (1)

Shibata, Shoji; Morishita, Eisaku; Takeda, Tadahiro; Sakata, Kiyomi

doi:10.1248/cpb.16.405

Cited by 11 publications

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“…Organic solvents can solve aurofusarin moderately, and it becomes yellow in acid and reddish in alkalis [ 12 ]. This is a plausible explanation for the color changes throughout F. graminearum ’s lifecycle ( Figure 1 ); perhaps the mold turns the medium increasingly alkaline and it causes aurofusarin to change its color to red.…”

Section: Major F Graminearum Pigmentsmentioning

confidence: 99%

“…There are very few studies comprehensively describing and relating F. graminearum surface colors and its pigments, their properties, and biosynthetic or genetic origin, though some were isolated during the 1930s–1960s [ 8 , 9 , 10 , 11 , 12 ]. There was also considerable chemical analysis of Fusarium pigmentation in the late 1970s and early 1980s, but this never tried to relate the compounds with the mold’s observable biological phenomena [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

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Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

Cambaza

2018

Foods

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Several studies have explored in depth the biochemistry and genetics of the pigments present in Fusarium graminearum, but there is a need to discuss their relationship with the mold’s observable surface color pattern variation throughout its lifecycle. Furthermore, they require basic cataloguing, including a description of their major features known so far. Colors are a viable alternative to size measurement in growth studies. When grown on yeast extract agar (YEA) at 25 °C, F. graminearum initially exhibits a whitish mycelium, developing into a yellow-orange mold by the sixth day and then turning into wine-red. The colors are likely due to accumulation of the golden yellow polyketide aurofusarin and the red rubrofusarin, but the carotenoid neurosporaxanthin also possibly plays a major role in the yellow or orange coloration. Torulene might contribute to red tones, but it perhaps ends up being converted into neurosporaxanthin. Culmorin is also present, but it does not contribute to the color, though it was initially isolated in pigment studies. Additionally, there is the 5-deoxybostrycoidin-based melanin, but it mostly occurs in the teleomorph’s perithecium. There is still a need to chemically quantify the pigments throughout the lifecycle, and analyze their relationships and how much each impacts F. graminearum’s surface color.

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Section: Major F Graminearum Pigmentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

Cambaza

2018

Foods

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“…This is the first study to qualitatively analyze aurofusarin production from the mycelia of F. graminearum samples grown in liquid media. Aurofusarin pigment was found to be insoluble in water and was obtained by repeated extraction with CHCl 3 from the dried mycelia of F. graminearum and F. culmorum, which were cultivated on Raulin-Thom broth (Shibata et al 1968). Burkhead (1990) used methylene chloride to extract aurofusarin from the dry mycelia of F. graminearum grown on soybean mealglucose liquid broth.…”

Section: Resultsmentioning

confidence: 99%

The effect of different carbon sources on phenotypic expression by Fusarium graminearum strains

Zhang

Wolf‐Hall

2010

Eur J Plant Pathol

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Two Fusarium graminearum strains were cultured in glucose yeast extract peptone broth or minimal medium broth to measure the production of mycelial biomass, pH, mycotoxins, and aurofusarin pigment, when limited to single carbon sources (at 1%), including xylan, cellulose, starch, or glucose. A random complete block design with factorial arrangement and analysis of variance at a significance level of 0.01 were employed to test for treatment differences. Overall, the F. graminearum strains produced significantly more biomass, deoxynivalenol, and aurofusarin with xylan than with cellulose. No significant differences were found in terms of 15-acetyldeoxynivalenol production from the four carbon sources. The presence of significant interactions between the strains, carbon sources, and media led to the following specific differences. In yeast extract peptone broth, R-9828 strain yielded significantly more deoxynivalenol production with xylan than cellulose and R-9832 produced significantly more mycelium (biomass) with xylan than cellulose. R-9828 strain yielded significantly more deoxynivalenol production than the R-9832 strain. Also in yeast extract peptone broth, cellulose led to significantly higher pH values than other carbons, which might be due to the limited ability of the Fusarium strains to utilize cellulose as an energy source. Aurofusarin was the only expressed analyte to show a significant difference in minimal medium broth, and R-9832 produced significantly more aurofusarin with xylan than with cellulose in the broth. These results suggest that xylan may induce Fusarium growth and deoxynivalenol production to assist the infection process and may support the theory that F. graminearum invades through xylan in the cell walls of cereals.

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“…It seems to be biosynthesized from trans-farnesyl pyrophosphate [70] and compounds closely related include hydroxyculmorins, culmorone, and hydroxyculmorone [74][75][76]. Technically, it is not a pigment in the sense that it has no color, as already mentioned, but it was initially isolated during pigment studies together with aurofusarin and rubrofusarin [12], possibly because they share some chemical properties. So far, the culmorin producing Fusarium species mentioned in the literature include F. graminearum, F. culmorum, F. crookwellense (F. cerealis), F. venenatum [79], and more recently, F. praegraminearum, a basal species of the F. graminearum complex [80].…”

Section: Culmorinmentioning

confidence: 98%

“…Aurofusarin is the only F. graminearum pigment produced under a deficiency of nitrogen, phosphorus, oxidative stress, and the inhibition of respiration [19]. Organic solvents can solve aurofusarin moderately, and it becomes yellow in acid and reddish in alkalis [12]. This is a plausible explanation for the color changes throughout F. graminearum's lifecycle ( Figure 1); perhaps the mold turns the medium increasingly alkaline and it causes aurofusarin to change its color to red.…”

Section: Aurofusarinmentioning

confidence: 99%

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

Cambaza

2018

Preprint

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Several studies explore in depth the biochemistry and genetics of the pigments present in Fusarium graminearum but there is a need to discuss about their relationship with the mold’s observable surface color pattern variation throughout its lifecycle. Furthermore, they require basic cataloguing and description of their major features known so far. Colors are a viable alternative to size measurement in growth studies. When grown on yeast extract agar (YEA) at 25 °C, F. graminearum initially exhibits a whitish mycelium, developing into a yellow-orange mold by the sixth day and then turning into wine-red. The colors are likely due to accumulation of the golden yellow polyketide aurofusarin and the red rubrofusarin, but the carotenoid neurosporaxanthin possibly play also a major role in the yellow or orange coloration. Torulene might contribute for red tones but it perhaps ends up being converted into neurosporaxanthin. Culmorin is also present but it does not contribute for the color, though it was initially isolated in pigment studies, and there is the 5-deoxybostrycoidin-based melanin, but it occurs mostly in the teleomorph’s perithecium. There is still a need to chemically quantify the pigments throughout the lifecycle, analyze their relationships and how much each impacts F. graminearum surface color.

show abstract

Metabolic Products of Fungi. XXVIII. The Structure of Aurofusarin. (1)

Cited by 11 publications

References 0 publications

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

The effect of different carbon sources on phenotypic expression by Fusarium graminearum strains

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

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