Background: Identification and quantification of mycotoxins produced by Fusarium species are important in controlling fungal diseases. Objectives: Potential of zearalenone, butenolide and fusarin C production was investigated in five Fusarium graminearum and five F. culmorum isolates at molecular level. Materials and Methods: Presence of PKS13, FG08079.1 and PKS10 genes, associated with produ...

Smoke plays an intriguing role in promoting the germination of seeds of many species following a fire. Recently, a bicyclic compound containing a condensed butenolide moiety, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), was reported as a potent germination promoter from plant-derived smoke. In this study, a related butenolide, 3,4,5-trimethylfuran-2(5H)-one (2), which inhibits germination and signif...

Density functional theory calculations have been employed to investigate the mechanism of gold(I)-catalysed rearrangements of cyclopropenes. Product formation is controlled by the initial ring-opening step which results in the formation of a gold-stabilised carbocation/gold carbene intermediate. With 3-phenylcyclopropene-3-methylcarboxylate, the preferred intermediate allows cyclisation via nuc...

A new butenolide, aspernolide D (1), and furandione, asperterone (2), together with four known butenolides, butyrolactones I-IV and aspernolide B, were obtained from cultures of the endophytic fungus Aspergillus terreus, isolated from the flowering plant Mammea siamensis. The structures of these compounds were elucidated by analysis of NMR spectroscopic and mass spectrometric data.

Native and promiscuous catalytic activities of flavin-dependent Old Yellow Enzymes (OYEs) reported to date are initiated by the reduced flavin upon electron transfer. As a rare exception, isomerization nonactivated C═C bond was shown be hydride-independent with two nonstereoselective yeast OYEs. Here, we report asymmetric prochiral model substrate, γ-methyl β,γ-butenolide, corresponding (R)- (S...

The arborescent bryozoan Bugulina neritina is a cosmopolitan fouling species in sub-tropical to sub-temperate waters. butenolide compound 5-octylfuran-2(5H)-one (hereafter named butenolide) reportedly inhibits larval settlement of B. , but its effect on the behavioral and transcriptomic responses remained unclear. We report that 10 μg mL -1 or higher concentration and/or prolonged treatment (10...

The compact tricyclic substructure of solanoeclepin A containing the cyclobutanone ring was prepared by using as the key step a highly regioselective intramolecular [2 + 2]-photocycloaddition reaction between one of the [small pi]-bonds of an allene and the CC double bond of a butenolide.

The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.

We report a concise synthesis of A-factor, the prototypical γ-butyrolactone signalling compound of Streptomyces bacteria. In analogy to enzymatic reactions in A-factor biosynthesis, our synthesis features a tandem esterification-Knoevenagel condensation yielding a 2-acyl butenolide and a surprising, chemoselective conjugate reduction of this α,β-unsaturated carbonyl compound using sodium cyanob...