Cleavage of zearalenone by Trichosporon mycotoxinivorans to a novel nonestrogenic metabolite.

Applied and Environmental Microbiology
Elisavet VekiruRainer Schuhmacher

Abstract

Zearalenone (ZON) is a potent estrogenic mycotoxin produced by several Fusarium species most frequently on maize and therefore can be found in food and animal feed. Since animal production performance is negatively affected by the presence of ZON, its detoxification in contaminated plant material or by-products of bioethanol production would be advantageous. Microbial biotransformation into nontoxic metabolites is one promising approach. In this study the main transformation product of ZON formed by the yeast Trichosporon mycotoxinivorans was identified and characterized by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and LC-diode array detector (DAD) analysis. The metabolite, named ZOM-1, was purified, and its molecular formula, C(18)H(24)O(7), was established by time of flight MS (TOF MS) from the ions observed at m/z 351.1445 [M-H](-) and at m/z 375.1416 [M+Na](+). Employing nuclear magnetic resonance (NMR) spectroscopy, the novel ZON metabolite was finally identified as (5S)-5-({2,4-dihydroxy-6-[(1E)-5-hydroxypent-1-en-1-yl]benzoyl}oxy)hexanoic acid. The structure of ZOM-1 is characterized by an opening of the macrocyclic ring of ZON at the ketone group at C6'. ZOM-1 did not show estrogenic activity in a sensit...Continue Reading

References

Feb 1, 1991·Applied and Environmental Microbiology·S H el-SharkawayF T Halaweish
Jan 1, 1991·Applied and Environmental Microbiology·J Plasencia, C J Mirocha
May 1, 1990·Zentralblatt für Veterinärmedizin. Reihe B. Journal of veterinary medicine. Series B·M GareisB Gedek
Sep 1, 1986·Applied and Environmental Microbiology·H Kamimura
Apr 1, 1988·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·S el-Sharkawy, Y J Abul-Hajj
Sep 25, 2001·Toxicology·H S Hussein, J M Brasel
Feb 7, 2003·Applied and Environmental Microbiology·Rudolf MitterbauerGerhard Adam
Feb 25, 2003·Bioscience, Biotechnology, and Biochemistry·Hideaki KakeyaHiroyuki Osada
Oct 25, 2003·Journal of the American Dietetic Association·Ruby H CoxClark K Gaylord
Jun 9, 2004·Applied and Environmental Microbiology·Naoko Takahashi-AndoMakoto Kimura
Sep 9, 2004·Chemical Reviews·G-J ten BrinkR A Sheldon
Dec 23, 2004·Systematic and Applied Microbiology·Orsolya MolnarHansjoerg Prillinger
Dec 8, 2005·Applied and Environmental Microbiology·Kenneth C EhrlichDeepak Bhatnagar
May 23, 2006·Molecular Nutrition & Food Research·Gerd SchatzmayrEva Maria Binder
Oct 19, 2006·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Abdellah ZinedineJordi Mañes
Mar 3, 2007·Applied Microbiology and Biotechnology·Michihiko KataokaSakayu Shimizu
Jul 9, 2009·Analytical and Bioanalytical Chemistry·Franz BerthillerRudolf Krska
Jun 1, 2003·Mycotoxin Research·G SchatzmayrE M Binder

❮ Previous
Next ❯

Citations

Jul 21, 2011·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·G JardA Lebrihi
May 9, 2012·Biotechnology for Biofuels·Andrea de Souza MonteiroVera Lúcia Dos Santos
Jul 13, 2013·Journal of Chemical Ecology·Susan P McCormick
Jan 1, 2013·Journal of Hazardous Materials·Csilla KrifatonJózsef Kukolya
Feb 17, 2015·Journal of Basic Microbiology·Walter P PflieglerIstván Pócsi
Mar 21, 2015·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·Irene HahnFranz Berthiller
May 21, 2016·Frontiers in Microbiology·Ilse VanhoutteLeen De Gelder
Aug 25, 2016·Mycotoxin Research·Petr KarlovskyPierre Dussort
Feb 8, 2018·Journal of the Science of Food and Agriculture·Hina ShanakhatSilvana Cavella
Jan 25, 2018·Journal of the Science of Food and Agriculture·Shiau-Wei ChenHan-Tsung Wang
Apr 4, 2019·Frontiers in Microbiology·Nandhitha Venkatesh, Nancy P Keller
Nov 17, 2019·Toxins·Radmilo ČolovićLuciano Pinotti
Apr 4, 2021·Toxins·Ksenija NešićKrešimir Mastanjević
Jun 12, 2021·Critical Reviews in Microbiology·Amir ArastehfarArnaldo Lopes Colombo
May 6, 2011·Chemical Reviews·Hannes LeischPeter C K Lau

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.