Biosynthesis of fomannoxin in the root rotting pathogen Heterobasidion occidentale.

Abstract:

:Fomannoxin is a biologically active benzohydrofuran, which has been suggested to be involved in the pathogenicity of the root rotting fungus Heterobasidion annosum sensu lato. The biosynthesis of fomannoxin was investigated through an isotopic enrichment study utilizing [1-¹³C]glucose as metabolic tracer. ¹³C NMR spectroscopic analysis revealed the labeling pattern and showed that the isoprene building block originates from the mevalonic acid pathway, whereas the aromatic motif is formed via the shikimic acid route by elimination of pyruvate from chorismic acid. A natural product, 4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde, was isolated and characterized, and was suggested to be a key intermediate in the biosynthesis of fomannoxin and related secondary metabolites previously identified from the H. annosum fungal species complex.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Hansson D,Menkis A,Olson K,Stenlid J,Broberg A,Karlsson M

doi

10.1016/j.phytochem.2012.08.008

subject

Has Abstract

pub_date

2012-12-01 00:00:00

pages

31-9

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(12)00375-5

journal_volume

84

pub_type

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