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Ustiloxins are a kind of cyclopeptide mycotoxins produced by rice false smut pathogen Villosiclava virens, which seriously threatens the safe production of rice and health of humans and animals. Hydroxylation, a biotransformation reaction that regio- and stereoselectively introduces a hydroxyl group into the molecule catalyzed by the hydroxylase produced by organisms, has been considered an efficient way to detoxify mycotoxins. In this study, the endophytic fungus Petriella setifera Nitaf10 was found to be able to detoxify ustiloxin A, the main toxic component in V. virens. In addition to the two main transformed products previously identified, ustiloxins A1 and A2, an additional transformed product was obtained by using cell-free extract (CFE) of P. setifera Nitaf10 prepared with 5 mmol/L of pH 9.0 carbonate-buffered solution (CBS). It was structurally characterized as a novel ustiloxin analog named 13-hydroxy ustiloxin A (1) by analysis of the 1D and 2D NMR and HRESIMS spectra as well as by comparison with known ustiloxins. Biotransformation reaction of ustiloxin A was found to proceed via hydroxylation, and was possibly catalyzed by the intracellular hydroxylase in the CFE. The cytotoxic and phytotoxic activities of 13-hydroxy ustiloxin A (1) were much weaker than those of ustiloxin A. Detoxification of ustiloxin A by hydroxylation of P. setifera will be an efficient strategy. Full article

Ustiloxins are a group of cyclopeptide mycotoxins produced by rice false smut pathogen Villosiclava virens (anamorph: Ustilaginoidea virens) which seriously threaten the safety production of rice and the health of humans and livestock. Ustiloxin A, accounting for 60% of the total ustiloxins, is the main toxic component. Biotransformation, a process of modifying the functional groups of compounds by means of regio- or stereo-specific reactions catalyzed by the enzymes produced by organisms, has been considered as an efficient way to detoxify mycotoxins. In this study, the endophytic fungus Petriella setifera Nitaf10 was found to be able to detoxify ustiloxin A through biotransformation. Two transformed products were obtained by using the cell-free extract (CFE) containing intracellular enzymes of P. setifera Nitaf10. They were structurally characterized as novel ustiloxin analogs named ustiloxins A1 (1) and A2 (2) by analysis of the 1D and 2D NMR and HRESIMS spectra as well as by comparison with known ustiloxins. The cytotoxic activity of ustiloxins A1 (1) and A2 (2) was much weaker than that of ustiloxin A. The biotransformation of ustiloxin A was found to proceed via oxidative deamination and decarboxylation and was possibly catalyzed by the intracellular amine oxidase and oxidative decarboxylase in the CFE. An appropriate bioconversion was achieved by incubating ustiloxin A with the CFE prepared in 0.5 mol/L phosphate buffer (pH 7.0) for 24 to 48 h. The optimum initial pH values for the bioconversion of ustiloxin A were 7–9. Among eight metal ions (Co²⁺, Cu²⁺, Fe³⁺, Zn²⁺, Ba²⁺, Ca²⁺, Mg²⁺ and Mn²⁺) tested at 5 mmol/L, Cu²⁺, Fe³⁺ and Zn²⁺ totally inhibited the conversion of ustiloxin A. In conclusion, detoxification of ustiloxin A through oxidative deamination and decarboxylation is an efficient strategy. Full article

The phytochemical constituents of apple waste were established as potential antifungal agents against four crops pathogens, specifically, Botrytis sp., Fusarium oxysporum, Petriella setifera, and Neosartorya fischeri. Crude, purified extracts and fractions of apple pomace were tested in vitro to evaluate their antifungal and antioxidant properties. The phytochemical constituents of the tested materials were mainly represented by phloridzin and quercetin derivatives, as well as previously undescribed in apples, monoterpene–pinnatifidanoside D. Its structure was confirmed by 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopic analyses. The fraction containing quercetin pentosides possessed the highest antioxidant activity, while the strongest antifungal activity was exerted by a fraction containing phloridzin. Sugar moieties differentiated the antifungal activity of quercetin glycosides. Quercetin hexosides possessed stronger antifungal activity than quercetin pentosides. Full article