Síntese e caracterização química do composto isocariolânico (8R,9R)-8-metoxi-isocariolan-9-ol como potencial agente antimicrobiano

Abstract

Organic synthesis is a fundamental process in chemistry, responsible for the construction or transformation of organic compounds from simpler precursors. This approach enables the creation of molecules with varying levels of complexity. Among these molecules, sesquiterpenes with an isocaryolane-type skeleton stand out, as they exhibit relevant structural features and have attracted scientific interest due to their potential fungistatic effect against the phytopathogen Botrytis cinerea. In this context, the present study aimed to perform the synthesis, purification, structural characterization and evaluation of the antimicrobial activity of the isocaryolane compound (8R,9R)-8-methoxy-isocaryolan-9-ol. The product was purified using chromatographic techniques and its structure was elucidated by Nuclear Magnetic Resonance spectroscopy. The antimicrobial activity was assessed against Gram-positive bacteria such as Staphylococcus aureus, Enterococcus faecium and Enterococcus faecalis, as well as Gram-negative bacteria including Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumoniae, as well as yeasts such as Candida albicans, Candida tropicalis, Candida glabrata, Candida dubliniensis, Candida parapsilosis, Candida krusei and Cryptococcus gattii were also tested using the Minimum Inhibitory Concentration assay. The results revealed significant antimicrobial potential of the synthesized compound, particularly against the Gram-positive bacteria Enterococcus faecium and Enterococcus faecalis, and the yeast Candida krusei, microorganisms frequently associated with hospital-acquired infections and resistance to conventional antimicrobial agents. Thus, the relevance of the compound is reinforced as a promising candidate for the development of new therapeutic alternatives, especially in the context of the growing challenge of microbial resistance.