A platform chemical from soybean hulls: Unveiling the bioactive effects of levoglucosenone derivatives

Abstract

Soybean is one of the most extensively cultivated crops globally, and the soybean oil industry produces a significant amount of hulls annually. Utilizing this by-product to generate levoglucosenone through acid-catalyzed pyrolysis represents an environmentally friendly strategy to maximize the use of this crop and increase the value of the residue. This study explored the pyrolysis of soybean hulls to obtain the target enone and its application in the generation of new antifungal compounds. Halogenated derivatives were synthesized in a simple and straightforward manner and evaluated for antifungal activity against several Candida and Cryptococcus strains. Mechanistic studies investigated their interactions with ergosterol, impact on fungal cell wall synthesis, and inhibition of virulence factors. Biofilm formation assays were also conducted. Our results showed that the chloro derivative demonstrated the highest antifungal activity, exhibiting a remarkable minimum inhibitory concentration (MIC) and efficacy against both susceptible and resistant strains. It was also showed that the mode of action does not involve ergosterol bonding nor inhibition of cell wall synthesis. This study provides valuable insights into utilizing agricultural waste for developing bioactive compounds with pharmaceutical applications, contributing to the sustainable utilization of biomass resources in pharmaceutical research and development.