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Abstract
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.
Highlights
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
The most severe attacks of D. sapinea are historically reported in pine plantations affected by environmental stresses such as hail and drought in the southern hemisphere, where its infections are involved in large-scale die-back and tree mortality.[1]
Despite the ecological impact of D. sapinea outbreaks worldwide and the resulting economic losses caused to conifer plantations and timber production, studies on the virulence factors involved in the pathogenesis process and biochemical targets are still limited.[6]
Summary
Compounds 1 and 2 caused 96% and 51% of larval mortality in a brine shrimp (Artemia salina L.) assay[17] at 200 μg/mL, whereas at the other two concentrations (100 and 50 μg/mL). Larval mortality was less than 20% for 1, while 2 was inactive. Dihydrofuranones and epoxide derivatives are well known as natural occurring compounds[18] and as fungal phytotoxins,[19] pinofuronoxins A (1) and B (2) have a unique combination of functional groups. They showed similar phytotoxic activity but a different antifungal and zootoxic activity. The different antifungal and zootoxic activity could be ascribed to the different absolute and relative configuration of the epoxy ring
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