New furan derivatives from Annulohypoxylon spougei fungus

Abstract

Two new furan derivatives, annulofurans A-B (1–2), together with six known compounds were isolated from Annulohypoxylon spougei fungus. The structures were determined based on NMR and mass spectrometry data. The absolute configurations of annulofurans A-B were determined by Electronic Circular Dichroism (ECD) experiment and comparisons with the experimental ECD spectra of synthesized stereoisomers. The evaluation of the effects on radish and ruzi grass radicle elongation by the isolated compounds showed that annulofuran A affected radicle elongation of ruzi grass. The known 2-hydroxyphenylacetic acid methyl ester (7) had significant effects against both radish and ruzi grass radicle elongation, which were comparable to the commercial herbicide, glyphosate.

Graphical abstract

Keywords:

• Hypoxylaceae
• Annulohypoxylon sp.
• furan derivative
• 1,3-dioxolane ring

Acknowledgements

Financial support from the Development and Promotion of Science and Technology Talents Project (DPST) and the Centre of Excellence for Innovation in Chemistry (PERCH-CIC), Ministry of Higher Education, Science, Research and Innovation is gratefully acknowledged.

Disclosure statement

No potential conflict of interest was reported by the authors.