Identification of six new <i>Alternaria</i> sulfoconjugated metabolites by high‐resolution neutral loss filtering

Kelman, Megan J.; Renaud, Justin B.; Seifert, Keith A.; Mack, Jonathan; Sivagnanam, Kumaran; Yeung, Ken K.‐C.; Sumarah, Mark W.

doi:10.1002/rcm.7286

Cited by 30 publications

(20 citation statements)

References 35 publications

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“…Recently, the formation of these two and an additional six new sulfoconjugated metabolites in cultures of Alternaria sp. was described by Kelman et al [49]. The Alternaria isolates hereby were inoculated in liquid culture as well as rice and Cheerios (American brand of breakfast cereals).…”

Section: Discussionmentioning

confidence: 99%

Spotlight on the Underdogs—An Analysis of Underrepresented Alternaria Mycotoxins Formed Depending on Varying Substrate, Time and Temperature Conditions

Zwickel

Kahl

Klaffke

et al. 2016

Toxins

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Alternaria (A.) is a genus of widespread fungi capable of producing numerous, possibly health-endangering Alternaria toxins (ATs), which are usually not the focus of attention. The formation of ATs depends on the species and complex interactions of various environmental factors and is not fully understood. In this study the influence of temperature (7 °C, 25 °C), substrate (rice, wheat kernels) and incubation time (4, 7, and 14 days) on the production of thirteen ATs and three sulfoconjugated ATs by three different Alternaria isolates from the species groups A. tenuissima and A. infectoria was determined. High-performance liquid chromatography coupled with tandem mass spectrometry was used for quantification. Under nearly all conditions, tenuazonic acid was the most extensively produced toxin. At 25 °C and with increasing incubation time all toxins were formed in high amounts by the two A. tenuissima strains on both substrates with comparable mycotoxin profiles. However, for some of the toxins, stagnation or a decrease in production was observed from day 7 to 14. As opposed to the A. tenuissima strains, the A. infectoria strain only produced low amounts of ATs, but high concentrations of stemphyltoxin III. The results provide an essential insight into the quantitative in vitro AT formation under different environmental conditions, potentially transferable to different field and storage conditions.

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Section: Discussionmentioning

confidence: 99%

Spotlight on the Underdogs—An Analysis of Underrepresented Alternaria Mycotoxins Formed Depending on Varying Substrate, Time and Temperature Conditions

Zwickel

Kahl

Klaffke

et al. 2016

Toxins

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“…Moreover, the DIA approach allows the use of fragment ions for quantification [75]. Application of DIA and DDA in analysis of mycotoxins was demonstrated in several recent studies [76,77].…”

Section: High-resolution (Lc-hrms) Approaches For the Targeted Determmentioning

confidence: 99%

Advanced LC–MS-based methods to study the co-occurrence and metabolization of multiple mycotoxins in cereals and cereal-based food

Malachová

Stranska-Zachariasova

Václavíková

et al. 2017

Anal Bioanal Chem

130

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Liquid chromatography (LC) coupled with mass spectrometry (MS) is widely used for the determination of mycotoxins in cereals and cereal-based products. In addition to the regulated mycotoxins, for which official control is required, LC-MS is often used for the screening of a large range of mycotoxins and/or for the identification and characterization of novel metabolites. This review provides insight into the LC-MS methods used for the determination of co-occurring mycotoxins with special emphasis on multiple-analyte applications. The first part of the review is focused on targeted LC-MS approaches using cleanup methods such as solid-phase extraction and immunoaffinity chromatography, as well as on methods based on minimum cleanup (quick, easy, cheap, effective, rugged, and safe; QuEChERS) and dilute and shoot. The second part of the review deals with the untargeted determination of mycotoxins by LC coupled with high-resolution MS, which includes also metabolomics techniques to study the fate of mycotoxins in plants.

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“…2). [26][27][28][29] CUL is a longifolene sesquiterpene with a tricyclo-[6.3.0.0] undecane skeleton and the core structure appears in several other natural products such as longifolene or longiborneol. Several strategies for the synthesis of CUL and its core structure have been reported.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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The Fusarium metabolite culmorin (1) is receiving increased attention as an "emerging mycotoxin". It co-occurs with trichothecene mycotoxins and potentially influences their toxicity. Its ecological role and fate in plants is unknown. We synthesized sulfated and glucosylated culmorin conjugates as potential metabolites, which are expected to be formed in planta, and used them as reference compounds. An efficient procedure for the synthesis of culmorin sulfates was developed. Diastereo- and regioselective glucosylation of culmorin (1) was achieved by exploiting or preventing unexpected acyl transfer when using different glucosyl donors. The treatment of a wheat suspension culture with culmorin (1) revealed an in planta conversion of culmorin into culmorin-8-glucoside (6) and culmorin acetate, but no sulfates or culmorin-11-glucoside (7) was found. The treatment of wheat cells with the fungal metabolite 11-acetylculmorin (2) revealed its rapid deacetylation, but also showed the formation of 11-acetylculmorin-8-glucoside (8). These results show that plants are capable of extensively metabolizing culmorin.

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Identification of six new Alternaria sulfoconjugated metabolites by high‐resolution neutral loss filtering

Cited by 30 publications

References 35 publications

Spotlight on the Underdogs—An Analysis of Underrepresented Alternaria Mycotoxins Formed Depending on Varying Substrate, Time and Temperature Conditions

Spotlight on the Underdogs—An Analysis of Underrepresented Alternaria Mycotoxins Formed Depending on Varying Substrate, Time and Temperature Conditions

Advanced LC–MS-based methods to study the co-occurrence and metabolization of multiple mycotoxins in cereals and cereal-based food

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

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