Concise Synthesis of Alternariol and Alternariol-9-monomethyl ether as well as their D3-Isotopologues

Synthesis ◽  
2021 ◽  
Author(s):  
Michael Sebald ◽  
Julian Gebauer ◽  
Matthias Koch
Keyword(s):  
Stable Isotope ◽  
Secondary Metabolites ◽  
Mutagenic Activity ◽  
Monomethyl Ether ◽  
Internal Standards ◽  
Stable Isotope Dilution ◽  
Isotope Dilution Assay ◽  
Dilution Assay ◽  
Food And Feed ◽  
Analytical Standards

Abstract Alternariol (AOH) and alternariol-9-monomethyl ether (AME) are two secondary metabolites of Alternaria fungi which can be found in various foodstuff like tomatoes, nuts, and grains. Due to their toxicity and potential mutagenic activity the need for the development of high-throughput methods for the supervision of AOH- and AME-levels is of increasing interest. As the availability of both native and labeled AOH and AME analytical standards is very limited we herein wish to present a novel concise approach towards their synthesis employing a ruthenium-catalyzed ortho-arylation as the key step. Finally, we demonstrate their suitability as internal standards in stable-isotope dilution assay (SIDA)-HPLC-MS/MS analysis commonly used for the quantification of the natural products in food and feed.

scholarly journals Development of a LC-MS/MS method using stable isotope dilution for the quantification of individual B6 vitamers in fruits, vegetables, and cereals

2020 ◽  
Vol 412 (26) ◽  
pp. 7237-7252
Author(s):  
Thomas Bachmann ◽  
Andrea Maurer ◽  
Michael Rychlik
Keyword(s):  
Stable Isotope ◽  
Isotope Dilution ◽  
Food Samples ◽  
Vitamin B ◽  
Internal Standards ◽  
Stable Isotope Dilution ◽  
Simultaneous Quantification ◽  
Isotope Dilution Assay ◽  
Dilution Assay ◽  
Detection And Quantification

Abstract Vitamin B6 comprises an important set of molecules tightly interwoven with the human amino acid, fatty acid, and carbohydrate metabolism. Analytical methods striving for the quantification of individual B6 vitamers so far mostly rely on methods based on HPLC in combination with fluorescence detection, but their application encounters multiple difficulties due to the chemical divergence of the single vitamers. The present study describes the development of a method based on LC-MS/MS and stable isotope dilution assay (SIDA) for the simultaneous quantification of five vitamers (PN, PL, PM, PMP, and PNG) of the B6 group in food samples. [13C3]-PN, [13C3]-PL, and [13C6]-PNG were applied as internal standards for the analysis of PN, PL, and PNG. PM and PMP were quantified via matrix-matched calibration referring to [13C3]-PN. The developed method was validated using starch matrix. The limits of detection and quantification ranged from 0.0028 to 0.02 mg/kg and from 0.0085 to 0.059 mg/kg, respectively, for all analytes. Calculated recoveries varied from 92 to 111%. Intra-injection precisions ranged from 0 to 9%, inter-day precisions from 4 to 10%, and intra-day precisions from 4 to 10%. A total of 14 plant-based food samples including fruits, vegetables, and cereals were examined for their content of vitamin B6 using the validated method. Furthermore, the first quantitation of PNG without enzymatic steps or divergent internal standards was undertaken utilizing LC-MS/MS and SIDA.

Quantitation of Rotundone in Grapefruit (Citrus paradisi) Peel and Juice by Stable Isotope Dilution Assay

2017 ◽  
Vol 65 (24) ◽  
pp. 5026-5033 ◽  
Author(s):  
Akira Nakanishi ◽  
Yusuke Fukushima ◽  
Norio Miyazawa ◽  
Keisuke Yoshikawa ◽  
Tomoko Maeda ◽  
...  
Keyword(s):  
Stable Isotope ◽  
Isotope Dilution ◽  
Stable Isotope Dilution Assay ◽  
Citrus Paradisi ◽  
Stable Isotope Dilution ◽  
Isotope Dilution Assay ◽  
Dilution Assay

scholarly journals Quantitative Analysis of 2-Aminoacetophenone in Off-Flavored Wines by Stable Isotope Dilution Assay

1996 ◽  
Vol 79 (2) ◽  
pp. 583-586 ◽  
Author(s):  
Bettina Dollmann ◽  
Dominicus Wichmann ◽  
Alfred Schmitt ◽  
Hans Koehler ◽  
Peter Schreier
Keyword(s):  
Quantitative Analysis ◽  
Stable Isotope ◽  
Isotope Dilution ◽  
Internal Standard ◽  
Stable Isotope Dilution Assay ◽  
Isotope Dilution Analysis ◽  
Model Experiments ◽  
Stable Isotope Dilution ◽  
Isotope Dilution Assay ◽  
Dilution Assay

Abstract Isotope dilution analysis was used to quantitate 2- aminoacetophenone in wines exhibiting the so- called untypical aging off-flavor. d3-Aminoacetophe- none was synthesized and used as isotopomeric internal standard. The method of quantitation was verified by several model experiments. In the off-flavored wines studied, amounts of 2-aminoacetophe none ranging from 0.7 to 12.8 μg/L were determined.

Quantitative Analysis of Beer Aromatic Alcohols Using Stable Isotope Dilution Assay

2002 ◽  
Vol 60 (2) ◽  
pp. 88-96 ◽  
Author(s):  
Jean-Pierre Dufour ◽  
Rana Wierda ◽  
Michelle Leus ◽  
Geert Lissens ◽  
Freddy Delvaux ◽  
...  
Keyword(s):  
Quantitative Analysis ◽  
Stable Isotope ◽  
Isotope Dilution ◽  
Stable Isotope Dilution Assay ◽  
Stable Isotope Dilution ◽  
Isotope Dilution Assay ◽  
Dilution Assay ◽  
Aromatic Alcohols

Development of a Stable Isotope Dilution Assay for Tenuazonic Acid

2011 ◽  
Vol 59 (7) ◽  
pp. 2980-2987 ◽  
Author(s):  
Stefan Asam ◽  
Yang Liu ◽  
Katharina Konitzer ◽  
Michael Rychlik
Keyword(s):  
Stable Isotope ◽  
Isotope Dilution ◽  
Stable Isotope Dilution Assay ◽  
Tenuazonic Acid ◽  
Stable Isotope Dilution ◽  
Isotope Dilution Assay ◽  
Dilution Assay
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