Volatiles from the hypoxylaceous fungi Hypoxylon griseobrunneum and Hypoxylon macrocarpum

Abstract

The volatiles emitted by the ascomycetes Hypoxylon griseobrunneum and Hypoxylon macrocarpum (Hypoxylaceae, Xylariales) were collected by use of a closed-loop stripping apparatus (CLSA) and analysed by GC–MS. The main compound class of both species were polysubstituted benzene derivatives. Their structures could only be unambiguously determined by comparison to all isomers with different substitution patterns. The substitution pattern of the main compound from H. griseobrunneum, the new natural product 2,4,5-trimethylanisole, was explainable by a polyketide biosynthesis mechanism that was supported by a feeding experiment with (methyl-2H3)methionine.

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

“…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 .…”

“…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 ].…”

“…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 ].…”

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

“…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.…”

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

“…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].…”