Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

Scholarly Works

• Yang, D.; Ye, Y.; Sun, J.; Wang, J.-S.; Huang, C.; Sun, X. Occurrence, transformation, and toxicity of fumonisins and their covert products during food processing. Critical reviews in food science and nutrition 2022, 64, 3660–3673. doi:10.1080/10408398.2022.2134290
• Kis, P.; Mastihubová, M. A sustainable approach to phenylethanoid glycopyranosides: Study of glycosylations promoted by zinc salts. Sustainable Chemistry and Pharmacy 2021, 24, 100537. doi:10.1016/j.scp.2021.100537
• Humpf, H.-U.; Rychlik, M.; Cramer, B. Modified Mycotoxins: A New Challenge?. Encyclopedia of Food Chemistry; Elsevier, 2019; pp 393–400. doi:10.1016/b978-0-08-100596-5.21802-7
• Jana, N.; Nanda, S. Resorcylic acid lactones (RALs) and their structural congeners: recent advances in their biosynthesis, chemical synthesis and biology. New Journal of Chemistry 2018, 42, 17803–17873. doi:10.1039/c8nj02534g
• Lorenz, N.; Dänicke, S.; Edler, L.; Gottschalk, C.; Lassek, E.; Marko, D.; Rychlik, M.; Mally, A. A critical evaluation of health risk assessment of modified mycotoxins with a special focus on zearalenone. Mycotoxin research 2018, 35, 27–46. doi:10.1007/s12550-018-0328-z
• Bryła, M.; Waśkiewicz, A.; Ksieniewicz-Woźniak, E.; Szymczyk, K.; Jędrzejczak, R. Modified Fusarium Mycotoxins in Cereals and Their Products-Metabolism, Occurrence, and Toxicity: An Updated Review. Molecules (Basel, Switzerland) 2018, 23, 963. doi:10.3390/molecules23040963
• Borzekowski, A.; Drewitz, T.; Keller, J.; Pfeifer, D.; Kunte, H.-J.; Koch, M.; Rohn, S.; Maul, R. Biosynthesis and characterization of zearalenone-14-sulfate, zearalenone-14-glucoside and zearalenone-16-glucoside using common fungal strains. Toxins 2018, 10, 104. doi:10.3390/toxins10030104
• Knutsen, H. K.; Barregård, L.; Bignami, M.; Brüschweiler, B. J.; Ceccatelli, S.; Cottrill, B.; Dinovi, M.; Edler, L.; Grasl-Kraupp, B.; Hogstrand, C.; Hoogenboom, L.; Nebbia, C.; Oswald, I. P.; Petersen, A.; Rose, M.; Roudot, A.-C.; Schwerdtle, T.; Vleminckx, C.; Vollmer, G.; Wallace, H. M.; Dall'Asta, C.; Gutleb, A. C.; Metzler, M.; Parent-Massin, D.; Binaglia, M.; Steinkellner, H.; Alexander, J. Appropriateness to set a group health based guidance value for nivalenol and its modified forms. EFSA journal. European Food Safety Authority 2017, 15, 1–46. doi:10.2903/j.efsa.2017.4751
• Michlmayr, H.; Varga, E.; Lupi, F.; Malachová, A.; Hametner, C.; Berthiller, F.; Adam, G. Synthesis of Mono- and Di-Glucosides of Zearalenone and α-/β-Zearalenol by Recombinant Barley Glucosyltransferase HvUGT14077. Toxins 2017, 9, 58. doi:10.3390/toxins9020058
• Warth, B.; Braun, D.; Ezekiel, C. N.; Turner, P. C.; Degen, G. H.; Marko, D. Biomonitoring of Mycotoxins in Human Breast Milk: Current State and Future Perspectives. Chemical research in toxicology 2016, 29, 1087–1097. doi:10.1021/acs.chemrestox.6b00125
• Walravens, J.; Mikula, H.; Rychlik, M.; Asam, S.; Devos, T.; Ediage, E. N.; Di Mavungu, J. D.; Jacxsens, L.; Van Landschoot, A.; Vanhaecke, L.; De Saeger, S. Validated UPLC-MS/MS Methods To Quantitate Free and Conjugated Alternaria Toxins in Commercially Available Tomato Products and Fruit and Vegetable Juices in Belgium. Journal of agricultural and food chemistry 2016, 64, 5101–5109. doi:10.1021/acs.jafc.6b01029
• Hoogenboom, L. Scientific opinion: Appropriateness to set a group health-based guidance value for zearalenone and its modified forms. EFSA Journal 2016, 14. doi:10.2903/j.efsa.2016.4425
• Guan, S.; Zhao, L.; Jin, H.; Shan, N.; Han, W.; Wang, S.; Shan, Y. Binding modes of phosphotriesterase-like lactonase complexed with δ-nonanoic lactone and paraoxon using molecular dynamics simulations. Journal of biomolecular structure & dynamics 2016, 35, 273–286. doi:10.1080/07391102.2016.1142899
• Christensen, H.; Oscarson, S.; Jensen, H. H. Common side reactions of the glycosyl donor in chemical glycosylation. Carbohydrate research 2015, 408, 51–95. doi:10.1016/j.carres.2015.02.007
• Berthiller, F.; Brera, C.; Crews, C.; Iha, M. H.; Krsha, R.; Lattanzio, V. M.; MacDonald, S.; Malone, R.; Maragos, C. M.; Solfrizzo, M.; Stroka, J.; Whitaker, T. B. Developments in mycotoxin analysis: an update for 2013-2014. World Mycotoxin Journal 2015, 8, 5–35. doi:10.3920/wmj2014.1840
• Bolte, B.; Basutto, J. A.; Bryan, C. S.; Garson, M. J.; Banwell, M. G.; Ward, J. S. Modular total syntheses of the marine-derived resorcylic Acid lactones cochliomycins a and B using a late-stage nozaki-hiyama-kishi macrocyclization reaction. The Journal of organic chemistry 2014, 80, 460–470. doi:10.1021/jo5024602

Explore citations to this article at