Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> Fungi
Beauvericin is a depsipeptide mycotoxin. The production of several beauvericin analogues has previously been shown among various genera among <i>Hypocreales</i> fungi. This includes so-called beauvenniatins, in which one or more <i>N</i>-methyl-phenylalanine residues is excha...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2019-03-01
|
| Series: | Toxins |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2072-6651/11/3/182 |
| _version_ | 1811279246596767744 |
|---|---|
| author | Monika Urbaniak Łukasz Stępień Silvio Uhlig |
| author_facet | Monika Urbaniak Łukasz Stępień Silvio Uhlig |
| author_sort | Monika Urbaniak |
| collection | DOAJ |
| description | Beauvericin is a depsipeptide mycotoxin. The production of several beauvericin analogues has previously been shown among various genera among <i>Hypocreales</i> fungi. This includes so-called beauvenniatins, in which one or more <i>N</i>-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 <i>Hypocreales</i> fungi, such as <i>Fusarium</i> and <i>Isaria</i> 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 <i>N</i>-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 <i>N</i>-methyl-leucine, which we named beauvenniatin L. This compound has not been reported before. Our data show that <i>N</i>-methyl-tyrosine containing beauvericins may be among the major naturally produced analogues in certain fungal strains. |
| first_indexed | 2024-04-13T00:51:21Z |
| format | Article |
| id | doaj.art-9cec10a84c554957a33b3591b70ca478 |
| institution | Directory Open Access Journal |
| issn | 2072-6651 |
| language | English |
| last_indexed | 2024-04-13T00:51:21Z |
| publishDate | 2019-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Toxins |
| spelling | doaj.art-9cec10a84c554957a33b3591b70ca4782022-12-22T03:09:52ZengMDPI AGToxins2072-66512019-03-0111318210.3390/toxins11030182toxins11030182Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> FungiMonika Urbaniak0Łukasz Stępień1Silvio Uhlig2Plant-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, PolandPlant-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, PolandNorwegian Veterinary Institute, P.O. Box 750 Sentrum, 0106 Oslo, NorwayBeauvericin is a depsipeptide mycotoxin. The production of several beauvericin analogues has previously been shown among various genera among <i>Hypocreales</i> fungi. This includes so-called beauvenniatins, in which one or more <i>N</i>-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 <i>Hypocreales</i> fungi, such as <i>Fusarium</i> and <i>Isaria</i> 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 <i>N</i>-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 <i>N</i>-methyl-leucine, which we named beauvenniatin L. This compound has not been reported before. Our data show that <i>N</i>-methyl-tyrosine containing beauvericins may be among the major naturally produced analogues in certain fungal strains.https://www.mdpi.com/2072-6651/11/3/182beauvericinbeauvenniatindepsipeptide<i>Fusarium</i><i>Isaria</i><i>Paecilomyces</i>mycotoxin |
| spellingShingle | Monika Urbaniak Łukasz Stępień Silvio Uhlig Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> Fungi Toxins beauvericin beauvenniatin depsipeptide <i>Fusarium</i> <i>Isaria</i> <i>Paecilomyces</i> mycotoxin |
| title | Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> Fungi |
| title_full | Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> Fungi |
| title_fullStr | Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> Fungi |
| title_full_unstemmed | Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> Fungi |
| title_short | Evidence for Naturally Produced Beauvericins Containing <i>N</i>-Methyl-Tyrosine in <i>Hypocreales</i> Fungi |
| title_sort | evidence for naturally produced beauvericins containing i n i methyl tyrosine in i hypocreales i fungi |
| topic | beauvericin beauvenniatin depsipeptide <i>Fusarium</i> <i>Isaria</i> <i>Paecilomyces</i> mycotoxin |
| url | https://www.mdpi.com/2072-6651/11/3/182 |
| work_keys_str_mv | AT monikaurbaniak evidencefornaturallyproducedbeauvericinscontaininginimethyltyrosineinihypocrealesifungi AT łukaszstepien evidencefornaturallyproducedbeauvericinscontaininginimethyltyrosineinihypocrealesifungi AT silviouhlig evidencefornaturallyproducedbeauvericinscontaininginimethyltyrosineinihypocrealesifungi |