Chemical synthesis of culmorin metabolites and their biologic role in culmorin and acetyl-culmorin treated wheat cells

Wéber, Júlia; Václavíková, Marta; Wiesenberger, Gerlinde; Haider, Maximilian; Hametner, Christian; Fröhlich, Johannes; Berthiller, Franz; Adam, Gerhard; Mikula, Hannes; Fruhmann, Philipp

doi:10.1039/c7ob02460f

Cited by 19 publications

(17 citation statements)

References 45 publications

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“…fungi, F. culmorum (name giving) for example. Its toxicological properties are poorly described in the literature, but the LD 50 is estimated for mice from 250-1000 µg kg −1 BW [46]. At the moment, the role of sambucinol, a major metabolite of F. culmorum, is unknown.…”

Section: Discussionmentioning

confidence: 99%

Fullerol C60(OH)24 Nanoparticles Affect Secondary Metabolite Profile of Important Foodborne Mycotoxigenic Fungi In Vitro

Kovač

Šarkanj

Borišev

et al. 2020

Toxins

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Despite the efforts to control mycotoxin contamination worldwide, extensive contamination has been reported to occur in food and feed. The contamination is even more intense due to climate changes and different stressors. This study examined the impact of fullerol C60(OH)24 nanoparticles (FNP) (at 0, 1, 10, 100, and 1000 ng mL−1) on the secondary metabolite profile of the most relevant foodborne mycotoxigenic fungi from genera Aspergillus, Fusarium, Alternaria and Penicillium, during growth in vitro. Fungi were grown in liquid RPMI 1640 media for 72 h at 29 °C, and metabolites were investigated by the LC-MS/MS dilute and shoot multimycotoxin method. Exposure to FNP showed great potential in decreasing the concentrations of 35 secondary metabolites; the decreases were dependent on FNP concentration and fungal genus. These results are a relevant guide for future examination of fungi-FNP interactions in environmental conditions. The aim is to establish the exact mechanism of FNP action and determine the impact such interactions have on food and feed safety.

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Section: Discussionmentioning

confidence: 99%

Fullerol C60(OH)24 Nanoparticles Affect Secondary Metabolite Profile of Important Foodborne Mycotoxigenic Fungi In Vitro

Kovač

Šarkanj

Borišev

et al. 2020

Toxins

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“…Culmorin (CAS: 18374-83-9) is a natural colorless metabolite found in various Fusarium species [ 8 , 20 , 70 , 71 ], with C 15 H 26 O 2 as its molecular structure ( Figure 5 ), first isolated by Ashley et al [ 8 ] and later established by Barton et al [ 11 ]. Culmorin is defined as a longifolene sesquiterpene diol with a tricyclo-[6.3.0.0] undecane skeleton [ 72 ], and its molecular weight is 238.3 g/mol [ 73 ]. It seems to be biosynthesized from trans -farnesyl pyrophosphate [ 70 ] and compounds closely related include hydroxyculmorins, culmorone, and hydroxyculmorone [ 74 , 75 , 76 ].…”

Section: Major F Graminearum Pigmentsmentioning

confidence: 99%

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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“…Among them, FA (179.0974 Da) and its derivatives fusarinol (165.1181 Da) and 9,10-dehydro-FA (177.0799 Da) were detected. Other putatively identified SMs were bikaverin (382.1126 Da), a tetracyclic benzoxanthone whose genetic base is reported to be clustered to FA [44,45], and culmorin (238.1446 Da), a sesquiterpenoid which is often associated with trichothecene production [46,47]. Among the identified compounds, the LC-MS Q-TOF analysis revealed that fusarinol was predominantly produced in CDB, in dark as well as in light conditions, while 9,10-dehydro-FA accumulated in PDB and MK.…”

Section: Metabolome Analysismentioning

confidence: 99%

The Shifting Mycotoxin Profiles of Endophytic Fusarium Strains: A Case Study

et al. 2019

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Fusarium species are known to establish manifold interactions with wild and crop plants ranging from pathogenicity to endophytism. One of the key factors involved in the regulation of such relationships is represented by the production of secondary metabolites. These include several mycotoxins, which can accumulate in foodstuffs causing severe health problems to humans and animals. In the present study, an endophytic isolate (A1021B), preliminarily ascribed to the Fusarium incarnatum-equiseti species complex (FIESC), was subjected to biochemical and molecular characterization. The metabolomic analysis of axenic cultures of A1021B detected up to 206 compounds, whose production was significantly affected by the medium composition. Among the most representative products, fusaric acid (FA), its derivatives fusarinol and 9,10-dehydro-FA, culmorin and bikaverin were detected. These results were in contrast with previous assessments reporting FIESC members as trichothecene rather than FA producers. However, molecular analysis provided a conclusive indication that A1021B actually belongs to the species Fusarium babinda. These findings highlight the importance of phylogenetic analyses of Fusarium species to avoid misleading identifications, and the opportunity to extend databases with the outcome of metabolomic investigations of strains from natural contexts. The possible contribution of endophytic strains in the differentiation of lineages with an uneven mycotoxin assortment is discussed in view of its ensuing impact on crop productions.

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Chemical synthesis of culmorin metabolites and their biologic role in culmorin and acetyl-culmorin treated wheat cells

Cited by 19 publications

References 45 publications

Fullerol C60(OH)24 Nanoparticles Affect Secondary Metabolite Profile of Important Foodborne Mycotoxigenic Fungi In Vitro

Fullerol C60(OH)24 Nanoparticles Affect Secondary Metabolite Profile of Important Foodborne Mycotoxigenic Fungi In Vitro

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

The Shifting Mycotoxin Profiles of Endophytic Fusarium Strains: A Case Study

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