The main aim of the
study was the biotransformation evaluation
of hesperidin for functionalization by 25 different nonhuman pathogenic
microorganisms. As a result, four metabolites were identified and
characterized. The structure of pinocembrin and naringenin from the
microbial transformation of hesperidin was determined initially with
LC/MS–MS. The metabolites eriodictyol and hesperetin were isolated,
and their molecular structure was determined by NMR and MS. Pinocembrin,
eriodictyol, and naringenin were characterized as new hesperidin microbial
transformation metabolites, to the best of our knowledge. In order
to evaluate the bioactivity, in vitro 5-lipoxygenase (5-LOX) enzyme
inhibition, antioxidant, antimicrobial, and acute toxicity evaluations
using the brine shrimp assay of hesperidin and its metabolites were
performed comparatively. According to antioxidant and anti-inflammatory
activity results, hesperetin metabolite was more active than naringenin
and hesperidin. The antimicrobial activity of hesperetin and naringenin
against the human pathogenic Staphylococcus aureus strain was relatively higher when compared with the substrate hesperidin.
In line with this result, biofilm activity of hesperetin and naringenin
against S. aureus with combination
studies using biofilm formation methods was carried out. The checkerboard
combination method was utilized for biofilm layering, also for the
first time in the present study. As an initial result, it was observed
that hesperidin and naringenin exerted a synergistic activity with
a fractional inhibitory concentration index (FICI) value of 1.063.
Considering the bioactivity of hesperidin, hesperetin, and naringenin
used as substrates are relatively nontoxic. The microbial and enzymatic
biotransformation of natural products such as hesperetin and its new
bioactive metabolites still have pharmacological potential, which
needs further experimentation at the molecular level..