Pinofuranoxins A and B, Bioactive Trisubstituted Furanones Produced by the Invasive Pathogen Diplodia sapinea

Two new bioactive trisubstituted furanones, named pinofuranoxins A and B (1 and 2), were isolated from Diplodia sapinea, a worldwide conifer pathogen causing severe disease. Pinofuranoxins A and B were characterized essentially by NMR and HRESIMS spectra, and their relative and absolute configuratio...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2021-09, Vol.84 (9), p.2600-2605
Main Authors: Masi, Marco, Di Lecce, Roberta, Marsico, Giulia, Linaldeddu, Benedetto Teodoro, Maddau, Lucia, Superchi, Stefano, Evidente, Antonio
Format: Article
Language:English
Subjects:
Animals
Artemia - drug effects
Ascomycota - chemistry
Basidiomycota - drug effects
Fungicides, Industrial - isolation & purification
Fungicides, Industrial - pharmacology
Furans - isolation & purification
Furans - pharmacology
Hedera - drug effects
Molecular Structure
Phaseolus - drug effects
Phytophthora - drug effects
Plant Diseases - microbiology
Quercus - drug effects
Tunisia
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Summary:Two new bioactive trisubstituted furanones, named pinofuranoxins A and B (1 and 2), were isolated from Diplodia sapinea, a worldwide conifer pathogen causing severe disease. Pinofuranoxins A and B were characterized essentially by NMR and HRESIMS spectra, and their relative and absolute configurations were assigned by NOESY experiments and computational analyses of electronic circular dichroism spectra. They induced necrotic lesions on Hedera helix L., Phaseolus vulgaris L., and Quercus ilex L. Compound 1 completely inhibited the growth of Athelia rolfsii and Phytophthora cambivora, while 2 showed antioomycetes activity against P. cambivora. In the Artemia salina assay both toxins showed activity inducing larval mortality.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.1c00365