Volatiles from the hypoxylaceous fungi <i>Hypoxylon griseobrunneum</i> and <i>Hypoxylon macrocarpum</i>

Rinkel, Jan; Babczyk, Alexander; Wang, Tao; Stadler, Marc; Dickschat, Jeroen S.

doi:10.3762/bjoc.14.277

Cited by 8 publications

(8 citation statements)

References 43 publications

(49 reference statements)

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“…With the upcoming genomic era in the study of this diverse genus, H. invadens may turn out to become an interesting model species for further ecological, physiological and phylogenomic assessment. Another task for the future would be the biological characterization of the volatile secondary metabolites, which had not been included in the previous study [ 11 ]. Notably, these volatiles were identified as terpenoids (e.g., α -muurolene, α -amorphene and α -cadinene), and chlorinated aromatic compounds, but no naphthoquinone derivatives were found among the volatile metabolites of H. invadens .…”

Section: Discussionmentioning

confidence: 99%

“…Notably, these volatiles were identified as terpenoids (e.g., α -muurolene, α -amorphene and α -cadinene), and chlorinated aromatic compounds, but no naphthoquinone derivatives were found among the volatile metabolites of H. invadens . [ 11 ].…”

Section: Discussionmentioning

confidence: 99%

“…We were able to obtain a culture from the ascospores of the holotype specimen of H. invadens that can now be studied in-depth for its physiological and ecological traits, including secondary metabolite production. In a previous study we have checked the cultures of H. invadens and H. macrocarpum [ 8 ], and the only reported metabolites from those species are several volatile organic compounds (VOC) [ 10 , 11 ] that were investigated by GC-MS analysis and total synthesis after observation of a strong odor originating from mycelia grown on oatmeal agar [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

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Phylogenetic Assignment of the Fungicolous Hypoxylon invadens (Ascomycota, Xylariales) and Investigation of its Secondary Metabolites

et al. 2020

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The ascomycete Hypoxylon invadens was described in 2014 as a fungicolous species growing on a member of its own genus, H.fragiforme, which is considered a rare lifestyle in the Hypoxylaceae. This renders H.invadens an interesting target in our efforts to find new bioactive secondary metabolites from members of the Xylariales. So far, only volatile organic compounds have been reported from H.invadens, but no investigation of non-volatile compounds had been conducted. Furthermore, a phylogenetic assignment following recent trends in fungal taxonomy via a multiple sequence alignment seemed practical. A culture of H.invadens was thus subjected to submerged cultivation to investigate the produced secondary metabolites, followed by isolation via preparative chromatography and subsequent structure elucidation by means of nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). This approach led to the identification of the known flaviolin (1) and 3,3-biflaviolin (2) as the main components, which had never been reported from the order Xylariales before. Assessment of their antimicrobial and cytotoxic effects via a panel of commonly used microorganisms and cell lines in our laboratory did not yield any effects of relevance. Concurrently, genomic DNA from the fungus was used to construct a multigene phylogeny using ribosomal sequence information from the internal transcribed spacer region (ITS), the 28S large subunit of ribosomal DNA (LSU), and proteinogenic nucleotide sequences from the second largest subunit of the DNA-directed RNA polymerase II (RPB2) and β-tubulin (TUB2) genes. A placement in a newly formed clade with H.trugodes was strongly supported in a maximum-likelihood (ML) phylogeny using sequences derived from well characterized strains, but the exact position of said clade remains unclear. Both, the chemical and the phylogenetic results suggest further inquiries into the lifestyle of this unique fungus to get a better understanding of both, its ecological role and function of its produced secondary metabolites hitherto unique to the Xylariales.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phylogenetic Assignment of the Fungicolous Hypoxylon invadens (Ascomycota, Xylariales) and Investigation of its Secondary Metabolites

et al. 2020

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“…Moreover, this study also resulted in the recognition of Muscodor/Induratia and the related genus Emarcea as a unique phylogenetic lineage for which the new family Induratiaceae has been erected [117]. Interestingly, these fungi were never studied for the production of nonvolatile secondary metabolites and even the identity of the compounds that were detected by database aided GC-MS analytics often remains dubious [103,[118][119][120]. The Induratiaceae certainly deserve further studies of their secondary metabolome, including the identification of metabolites that show pronounced production in dual antagonist cultures.…”

Section: Benzenoids and Lactones From Xylariaceae (Fig 7)mentioning

confidence: 99%

Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Becker

Stadler

2020

J Antibiot

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The families Xylariaceae and Hypoxylaceae (Xylariales, Ascomycota) represent one of the most prolific lineages of secondary metabolite producers. Like many other fungal taxa, they exhibit their highest diversity in the tropics. The stromata as well as the mycelial cultures of these fungi (the latter of which are frequently being isolated as endophytes of seed plants) have given rise to the discovery of many unprecedented secondary metabolites. Some of those served as lead compounds for development of pharmaceuticals and agrochemicals. Recently, the endophytic Xylariales have also come in the focus of biological control, since some of their species show strong antagonistic effects against fungal and other pathogens. New compounds, including volatiles as well as nonvolatiles, are steadily being discovered from these ascomycetes, and polythetic taxonomy now allows for elucidation of the life cycle of the endophytes for the first time. Moreover, recently high-quality genome sequences of some strains have become available, which facilitates phylogenomic studies as well as the elucidation of the biosynthetic gene clusters (BGC) as a starting point for synthetic biotechnology approaches. In this review, we summarize recent findings, focusing on the publications of the past 3 years.

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“…However, all these compounds have been detected to be emitted by other fungal species [38][39][40][41]. Interestingly, 2-phenylethanol has been shown to have antifungal properties against Penicillium species [41].…”

Section: Discussionmentioning

confidence: 99%

Weapons against Themselves: Identification and Use of Quorum Sensing Volatile Molecules to Control Plant Pathogenic Fungi Growth

et al. 2022

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Quorum sensing (QS) is often defined as a mechanism of microbial communication that can regulate microbial behaviors in accordance with population density. Much is known about QS mechanisms in bacteria, but fungal QS research is still in its infancy. In this study, the molecules constituting the volatolomes of the plant pathogenic fungi Fusarium culmorum and Cochliobolus sativus have been identified during culture conditions involving low and high spore concentrations, with the high concentration imitating overpopulation conditions (for QS stimulation). We determined that volatolomes emitted by these species in conditions of overpopulation have a negative impact on their mycelial growth, with some of the emitted molecules possibly acting as QSM. Candidate VOCs related to QS have then been identified by testing the effect of individual volatile organic compounds (VOCs) on mycelial growth of their emitting species. The antifungal effect observed for the volatolome of F. culmorum in the overpopulation condition could be attributed to ethyl acetate, 2-methylpropan-1-ol, 3-methylbutyl ethanoate, 3-methylbutan-1-ol, and pentan-1-ol, while it could be attributed to longifolene, 3-methylbutan-1-ol, 2-methylpropan-1-ol, and ethyl acetate for C. sativus in the overpopulation condition. This work could pave the way to a sustainable alternative to chemical fungicides.

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Volatiles from the hypoxylaceous fungi Hypoxylon griseobrunneum and Hypoxylon macrocarpum

Cited by 8 publications

References 43 publications

Phylogenetic Assignment of the Fungicolous Hypoxylon invadens (Ascomycota, Xylariales) and Investigation of its Secondary Metabolites

Phylogenetic Assignment of the Fungicolous Hypoxylon invadens (Ascomycota, Xylariales) and Investigation of its Secondary Metabolites

Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Weapons against Themselves: Identification and Use of Quorum Sensing Volatile Molecules to Control Plant Pathogenic Fungi Growth

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