The Synthesis and Antibacterial Activity of Analogs of Citrinin and Dihydrocitrinin

Chemistry and Biology of Mycotoxins and Related Fungal Metabolites

“…Starting from the degradation product 77 , several partial syntheses of optically active and racemic citrinin ( 2 ) have been described, , involving a subsequent carboxylation/formylation strategy. Warren et al extended this method to other aldehydes and ketones and received a series of analogues for the establishment of structure−activity relationships …”

Antimicrobial Potential of Extracts from <em>Penicillium purpurogenum</em> Isolated from Aquatic Environment in the Amazon and Identification of Citrinin Derivatives

“…However, the distinctions between compound 2 and dihydrocitrinin are the presence of the hydrogen signal at δ 1.25 (3H, d J=6.7 Hz), bonded to carbon at δ 18.4 ppm (C-9), and the shift in the chemical shift of C-1 in the structures, changing from δ 58.69 ppm to δ 77.9 ppm, indicating a characteristic CH group attached to an oxygen atom. Therefore, it is suggested that compound 2 is 1-methyldihydrocitrinine (Appendix A Figure A8) [37,38]. This compound, 1-methyldihydrocitrinine, was described as a product of synthetic origin, with citrinin as its precursor [38].…”

“…Therefore, it is suggested that compound 2 is 1-methyldihydrocitrinine (Appendix A Figure A8) [37,38]. This compound, 1-methyldihydrocitrinine, was described as a product of synthetic origin, with citrinin as its precursor [38]. In the absence of additional references pertaining to this compound, this represents the inaugural documentation of its acquisition through fungal biosynthesis within the Penicillium genus It is noteworthy that citrinin and its derivatives are compounds with a relatively straightforward production process, easy identification, and isolation [32].…”

“…In the absence of additional references pertaining to this compound, this represents the inaugural documentation of its acquisition through fungal biosynthesis within the Penicillium genus It is noteworthy that citrinin and its derivatives are compounds with a relatively straightforward production process, easy identification, and isolation [32]. Moreover, they exhibit various biological activities, including antibacterial effects [24,38], which is highly relevant in the current context where certain microorganisms like Staphylococcus aureus and Enterococcus spp. have developed resistance to specific antibiotics [40].…”

“…Studies involving semisynthesis, wherein citrinin was used to derive its derivatives, indicate that the antimicrobial activity of the derivative might surpass that of the precursor. In consideration of these findings, certain investigations undertook structural modifications, specifically entailing C-1 substitutions of citrinin, positing that the incorporation of alkyl or benzyl substituents may confer heightened antimicrobial activity in comparison to the unaltered citrinin [38].…”