Three New Ergot Alkaloids from the Fruiting Bodies of <i>Xylaria nigripes</i> (<scp>Kl</scp>.) <scp>Sacc</scp>.

Hu, Dawei; Li, Ming

doi:10.1002/cbdv.201600173

Cited by 19 publications

(9 citation statements)

References 22 publications

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“…All of these species have been isolated as endophytes or from decaying wood, while D. decipiens is also a symbiont of Xiphydria woodwasps [142], and X. nigripes is one of several termite-associated Xylaria species [150]. Xylanigripones are the first described ergot alkaloids from Xylariales and are produced by X. nigripes [151], and these compounds are the likely product of the X.…”

Section: Horizontal Transfer Of Anmentioning

confidence: 99%

Endophyte genomes support greater metabolic gene cluster diversity compared with non-endophytes inTrichoderma

Scott

Konkel

Gluck‐Thaler

et al. 2023

Preprint

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Trichodermais a cosmopolitan genus with diverse lifestyles and nutritional modes, including mycotrophy, saprophytism, and endophytism. Previous research has reported greater metabolic gene repertoires in endophytic fungal species compared to closely-related non-endophytes. However, the extent of this ecological trend and its underlying mechanisms are unclear. Some endophytic fungi may also be mycotrophs and have one or more mycoparasitism mechanisms. Mycotrophic endophytes are prominent in certain genera likeTrichoderma, therefore, the mechanisms that enable these fungi to colonize both living plants and fungi may be the result of expanded metabolic gene repertoires. Our objective was to determine what, if any, genomic features are overrepresented in endophytic fungi genomes in order to undercover the genomic underpinning of the fungal endophytic lifestyle. Here we compared metabolic gene cluster and mycoparasitism gene diversity across a dataset of thirty-eightTrichodermagenomes representing the full breadth of environmentalTrichoderma's diverse lifestyles and nutritional modes. We generated four newTrichoderma endophyticumgenomes to improve the sampling of endophytic isolates from this genus. As predicted, endophyticTrichodermagenomes contained, on average, more total biosynthetic and degradative gene clusters than non-endophytic isolates, suggesting that the ability to create/modify a diversity of metabolites potential is beneficial or necessary to the endophytic fungi. Still, once the phylogenetic signal was taken in consideration, no particular class of metabolic gene cluster was independently associated with theTrichodermaendophytic lifestyle. Several mycoparasitism genes, but no chitinase genes, were associated with endophyticTrichodermagenomes. Most genomic differences betweenTrichodermalifestyles and nutritional modes are difficult to disentangle from phylogenetic divergences among species, suggesting thatTrichodermagenomes maybe particularly well-equipped for lifestyle plasticity. We also consider the role of endophytism in diversifying secondary metabolism after identifying the horizontal transfer of the ergot alkaloid gene cluster toTrichoderma.

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Section: Horizontal Transfer Of Anmentioning

confidence: 99%

Endophyte genomes support greater metabolic gene cluster diversity compared with non-endophytes inTrichoderma

Scott

Konkel

Gluck‐Thaler

et al. 2023

Preprint

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“…( Vázquez et al. 2003 , Hu & Li 2017 ). Despite this fact, A. truncatum contains a BGC which shows striking similarities with the ergopeptine cluster from C. purpurea .…”

Section: Biosynthetic Diversity Of Selected Pathways In the Hypoxylaceaementioning

confidence: 99%

Secondary metabolite biosynthetic diversity in the fungal family Hypoxylaceae and Xylaria hypoxylon

Kuhnert

Navarro-Muñoz

Becker

et al. 2021

Studies in Mycology

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To date little is known about the genetic background that drives the production and diversification of secondary metabolites in the Hypoxylaceae . With the recent availability of high-quality genome sequences for 13 representative species and one relative ( Xylaria hypoxylon ) we attempted to survey the diversity of biosynthetic pathways in these organisms to investigate their true potential as secondary metabolite producers. Manual search strategies based on the accumulated knowledge on biosynthesis in fungi enabled us to identify 783 biosynthetic pathways across 14 studied species, the majority of which were arranged in biosynthetic gene clusters (BGC). The similarity of BGCs was analysed with the BiG-SCAPE engine which organised the BGCs into 375 gene cluster families (GCF). Only ten GCFs were conserved across all of these fungi indicating that speciation is accompanied by changes in secondary metabolism. From the known compounds produced by the family members some can be directly correlated with identified BGCs which is highlighted herein by the azaphilone, dihydroxynaphthalene, tropolone, cytochalasan, terrequinone, terphenyl and brasilane pathways giving insights into the evolution and diversification of those compound classes. Vice versa , products of various BGCs can be predicted through homology analysis with known pathways from other fungi as shown for the identified ergot alkaloid, trigazaphilone, curvupallide, viridicatumtoxin and swainsonine BGCs. However, the majority of BGCs had no obvious links to known products from the Hypoxylaceae or other well-studied biosynthetic pathways from fungi. These findings highlight that the number of known compounds strongly underrepresents the biosynthetic potential in these fungi and that a tremendous number of unidentified secondary metabolites is still hidden. Moreover, with increasing numbers of genomes for further Hypoxylaceae species becoming available, the likelihood of revealing new biosynthetic pathways that encode new, potentially useful compounds will significantly improve. Reaching a better understanding of the biology of these producers, and further development of genetic methods for their manipulation, will be crucial to access their treasures.

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“…Ergot Alkaloids: 2016 detection of 25 ergot alkaloids in cereal samples by LC-MS/MS [ 985 ]; comparison of ESI and APPI coupled with LC-MS for the analysis of ergot alkaloids [ 986 ]; HPLC-FLD method for detection of five ergot alkaloids (ergometrine, ergotamine, ergocornine, ergocrypine and ergocristine) in animal feed [ 987 ]; UHPLC-HRMS for screening of ergot alkaloids in animal feed [ 988 ]; determination of the bioactive alkaloids tabersonine, serpentine, vindoline, catharanthine, tryptamine, and vincamine in Apocynaceae plants (C. roseus and V. minor) by LC-MS/MS [ 989 ]; 2017 review [ 990 ]; MALDI-MSI for imaging distribution of alkaloids [ 991 ]; review [ 992 ]; determination of three new ergot alkaloids by HRMS [ 993 ]; determination of the total ergot alkaloids in rye using HPTLC-FLD [ 994 ]; response surface methodology for the identification, screening and optimization of fermentation factors to produce ergot alkaloids [ 995 ]; identification of a new species by molecular and ergot alkaloid profile analysis [ 996 ]; identification of alpha-CPA by UHPLC Triple-TOF HRMS [ 997 ]; NIR hyperspectral imaging for the detection of ergot bodies in cereal flour [ 998 ]; 2018 LAESI-MS for detection of ergot alkaloids [ 999 ]; testing of 122 samples of rye grains harvested in three different regions of Poland in 2016 and 2017 for ergot and its alkaloids [ 1000 ]; a total ergot alkaloid EIA compared with HPLC-FLD for the determination of total ergot alkaloids [ 1001 ]; multi-laboratory study to determine applicability of HPLC-FLD and HPLC-MS/MS for the determination of ergot alkaloids in rye-containing breads [ 1002 ]; review [ 1003 ]; UHPLC-FLD method for the quantification of the six major ergot alkaloids and their corresponding epimers [ 1004 ]; ergot alkaloids determination using spectrophotometry and TLC [ 1005 ]; review of IR spectroscopy for the detection of ergot alkaloids [ 1006 ]; 2019 protocol introducing lysergic acid diethylamide (LSD) for internal standardization of the analysis of ergot alkaloids by LC-FLD [ 1007 ]; 2D LC-MS/MS method for the simultaneous determination of 350 pesticides, 16 mycotoxins, 6 ergot alkaloids as well as the growth regulators Chlormequat and Mepiqua [ 1008 ]; NIR and ATR-FT/MIR spectroscopy for the determination of major ergot alkaloids [ 1009 ].…”

Section: Routine and Improved Analyses Of Abused Substancesmentioning

confidence: 99%

Interpol review of controlled substances 2016–2019

Jones

Comparin

2020

Forensic Science International: Synergy

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Three New Ergot Alkaloids from the Fruiting Bodies of Xylaria nigripes (Kl.) Sacc.

Cited by 19 publications

References 22 publications

Endophyte genomes support greater metabolic gene cluster diversity compared with non-endophytes inTrichoderma

Endophyte genomes support greater metabolic gene cluster diversity compared with non-endophytes inTrichoderma

Secondary metabolite biosynthetic diversity in the fungal family Hypoxylaceae and Xylaria hypoxylon

Interpol review of controlled substances 2016–2019

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