Syntheses and Antibacterial Evaluation of New Penicillium Metabolites Gregatins G and Thiocarboxylics C.
Franziska GillschFredrick MbuiUrsula BilitewskiRainer SchobertPublished in: Chemistry & biodiversity (2023)
Two pairs of side-chain epimeric 3-methoxycarbonyl-dihydrofuran-4-ones with structures purported for thiocarboxylics C 1/2 and gregatins G 1/2 , isolated from Penicillium sp. Sb62, were synthesised for the first time in five steps and 17-25 % yield. Key steps were a Suzuki cross-coupling, a Yamaguchi esterification, and a base-induced Knoevenagel-type condensation. The optimum protecting group for the 10-OH group in the dienyl side-chain, orthogonal to necessary protecting groups on O-10 of the furanone, was found to be t-butyldiphenylsilyl (TBDPS). The specific rotations of our synthetic products deviated markedly from those reported for the natural isolates. In contrast to the isolates, the synthetic products were not active against Escherichia coli and Staphylococcus aureus bacteria.
Keyphrases
- staphylococcus aureus
- escherichia coli
- genetic diversity
- biofilm formation
- high glucose
- magnetic resonance
- ms ms
- diabetic rats
- high resolution
- endothelial cells
- silver nanoparticles
- magnetic resonance imaging
- computed tomography
- pseudomonas aeruginosa
- oxidative stress
- methicillin resistant staphylococcus aureus
- anti inflammatory
- wound healing
- essential oil