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.
Rinkel J, Babczyk A, Wang T, Stadler M, Dickschat JS. Volatiles from the hypoxylaceous fungi Hypoxylon griseobrunneum and Hypoxylon macrocarpum. Beilstein J Org Chem. 2018 Dec 4;14:2974-2990. doi: 10.3762/bjoc.14.277. eCollection 2018. PubMed PMID: 30591821; PubMed Central PMCID: PMC6296411.
Keywords: volatiles from Hypoxylon griseobrunneum and Hypoxylon macrocarpum, hypoxylaceous fungi, polyketide biosynthesis, 2,4,5-trimethylanisole, ascomycetes.