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Distribution of the gyromitrin mycotoxin in the lorchel family assessed by a pre-column-derivatization and ultra high-performance liquid chromatography method

View ORCID ProfileAlden C. Dirks, View ORCID ProfileOsama G. Mohamed, Pamela Schultz, View ORCID ProfileAndrew N. Miller, View ORCID ProfileAshootosh Tripathi, View ORCID ProfileTimothy Y. James
doi: https://doi.org/10.1101/2022.08.08.503034
Alden C. Dirks
aDepartment of Ecology and Evolutionary Biology, University of Michigan, Ann Arbor, MI, USA
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  • For correspondence: adirks@umich.edu
Osama G. Mohamed
bNatural Products Discovery Core, Life Sciences Institute, University of Michigan, Ann Arbor, MI, USA
cPharmacognosy Department, Faculty of Pharmacy, Cairo University, Cairo, Egypt
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Pamela Schultz
bNatural Products Discovery Core, Life Sciences Institute, University of Michigan, Ann Arbor, MI, USA
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Andrew N. Miller
dIllinois Natural History Survey, University of Illinois Urbana-Champaign, Champaign, IL, USA
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Ashootosh Tripathi
bNatural Products Discovery Core, Life Sciences Institute, University of Michigan, Ann Arbor, MI, USA
eDepartment of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, MI, USA
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Timothy Y. James
aDepartment of Ecology and Evolutionary Biology, University of Michigan, Ann Arbor, MI, USA
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ABSTRACT

Gyromitrin (acetaldehyde N-methyl-N-formylhydrazone) and its homologs are deadly mycotoxins produced most infamously by the lorchel (also known as false morel) Gyromitra esculenta, which is paradoxically consumed as a delicacy in some parts of the world. There is much speculation about the presence of gyromitrin in other species of the lorchel family (Discinaceae), but no studies have broadly assessed its distribution. Given the history of poisonings associated with the consumption of G. esculenta and G. ambigua, we hypothesized that gyromitrin evolved in the last common ancestor of these taxa and would be present in their descendants with adaptive loss of function in the nested truffle clade, Hydnotrya. To investigate this hypothesis, we developed a sensitive analytical derivatization method for the detection of gyromitrin using 2,4-dinotrobenzaldehyde as the derivatization reagent. In total, we analyzed 66 specimens for the presence of gyromitrin over 105 tests. Moreover, we sequenced the nuc rDNA ITS1-5.8S-ITS2 region (ITS barcode) and nuc 28S rDNA to assist in species identification and to infer a supporting phylogenetic tree. We detected gyromitrin in all tested specimens from the G. esculenta group as well as G. leucoxantha. This distribution is consistent with a model of rapid evolution coupled with horizontal transfer, which is typical for secondary metabolites. We clarified that gyromitrin production in Discinaceae is both discontinuous and more limited than previously thought. Further research is required to elucidate the gyromitrin biosynthesis gene cluster and its evolutionary history in lorchels. KEYWORDS: 2,4-dinitrobenzaldehyde, Gyromitra spp., Hydnotrya spp., Discinaceae, Pezizales, Schiff bases, UHPLC-DAD analysis

Competing Interest Statement

The authors have declared no competing interest.

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The copyright holder for this preprint is the author/funder, who has granted bioRxiv a license to display the preprint in perpetuity. It is made available under a CC-BY-NC-ND 4.0 International license.
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Posted August 08, 2022.
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Distribution of the gyromitrin mycotoxin in the lorchel family assessed by a pre-column-derivatization and ultra high-performance liquid chromatography method
Alden C. Dirks, Osama G. Mohamed, Pamela Schultz, Andrew N. Miller, Ashootosh Tripathi, Timothy Y. James
bioRxiv 2022.08.08.503034; doi: https://doi.org/10.1101/2022.08.08.503034
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Distribution of the gyromitrin mycotoxin in the lorchel family assessed by a pre-column-derivatization and ultra high-performance liquid chromatography method
Alden C. Dirks, Osama G. Mohamed, Pamela Schultz, Andrew N. Miller, Ashootosh Tripathi, Timothy Y. James
bioRxiv 2022.08.08.503034; doi: https://doi.org/10.1101/2022.08.08.503034

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