Next Article in Journal
Correction: Zhen, Z. et al. NaCl Inhibits Citrinin and Stimulates Monascus Pigments and Monacolin K Production. Toxins 2019, 11, 118
Next Article in Special Issue
Candida utilis ATCC 9950 Cell Walls and β(1,3)/(1,6)-Glucan Preparations Produced Using Agro-Waste as a Mycotoxins Trap
Previous Article in Journal
Molecular Docking and Dynamics Simulation Studies Predict Munc18b as a Target of Mycolactone: A Plausible Mechanism for Granule Exocytosis Impairment in Buruli Ulcer Pathogenesis
Previous Article in Special Issue
Harmful Effects and Control Strategies of Aflatoxin B1 Produced by Aspergillus flavus and Aspergillus parasiticus Strains on Poultry: Review
Open AccessArticle

Evidence for Naturally Produced Beauvericins Containing N-Methyl-Tyrosine in Hypocreales Fungi

1
Plant-Pathogen Interaction Team, Department of Pathogen Genetics and Plant Resistance, Institute of Plant Genetics of the Polish Academy of Sciences, Strzeszyńska 34, 60-479 Poznań, Poland
2
Norwegian Veterinary Institute, P.O. Box 750 Sentrum, 0106 Oslo, Norway
*
Author to whom correspondence should be addressed.
Toxins 2019, 11(3), 182; https://doi.org/10.3390/toxins11030182
Received: 27 February 2019 / Revised: 21 March 2019 / Accepted: 22 March 2019 / Published: 26 March 2019
(This article belongs to the Special Issue Fungal Infestations in Humans, Animals, Crops)
Beauvericin is a depsipeptide mycotoxin. The production of several beauvericin analogues has previously been shown among various genera among Hypocreales fungi. This includes so-called beauvenniatins, in which one or more N-methyl-phenylalanine residues is exchanged with other amino acids. In addition, a range of “unnatural” beauvericins has been prepared by a precursor addition to growth medium. Our aim was to get insight into the natural production of beauvericin analogues among different Hypocreales fungi, such as Fusarium and Isaria spp. In addition to beauvericin, we tentatively identified six earlier described analogues in the extracts; these were beauvericin A and/or its structural isomer beauvericin F, beauvericin C, beauvericin J, beauvericin D, and beauvenniatin A. Other analogues contained at least one additional oxygen atom. We show that the additional oxygen atom(s) were due to the presence of one to three N-methyl-tyrosine moieties in the depsipeptide molecules by using different liquid chromatography–mass spectrometry-based approaches. In addition, we also tentatively identified a beauvenniatin that contained N-methyl-leucine, which we named beauvenniatin L. This compound has not been reported before. Our data show that N-methyl-tyrosine containing beauvericins may be among the major naturally produced analogues in certain fungal strains. View Full-Text
Keywords: beauvericin; beauvenniatin; depsipeptide; Fusarium; Isaria; Paecilomyces; mycotoxin beauvericin; beauvenniatin; depsipeptide; Fusarium; Isaria; Paecilomyces; mycotoxin
Show Figures

Figure 1

MDPI and ACS Style

Urbaniak, M.; Stępień, Ł.; Uhlig, S. Evidence for Naturally Produced Beauvericins Containing N-Methyl-Tyrosine in Hypocreales Fungi. Toxins 2019, 11, 182.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop