The main aims of
this investigation were the isolation of dimeric
naphthoquinones, a new class of dinaphthodiospyrols (1–7), from chloroform fractions and screening them for antibacterial,
antifungal, and antioxidant potential. The susceptibility of the isolated
compounds, namely, dinaphthodiospyrol A (1), dinaphthodiospyrol
B (2), dinaphthodiospyrol C (3), dinaphthodiospyrol
D (4), dinaphthodiospyrol E (5), dinaphthodiospyrol
F (6), and dinaphthodiospyrol G (7) was
assessed for antibacterial potential using well diffusion methods.
The isolated compounds showed excellent antibacterial activity against
selected bacterial strains, including Gram-positive Bacillus subtilis, Streptococcus epidermis, and Bacillus subtilis, and Gram-negative
bacteria Klebsiella pneumonia with
the zones of inhibition 6 to 26 nm. The standard drug Imipenem showed
a maximum inhibitory zone 30 to 35 nm. Similarly, the isolated compounds
were screened for antifungal properties, which showed an excellent
reduction in the growth of selected fungal strain including Candida albicans, Aspergillus flavus, Fusarium solani, Trichyton logifusus, Microsporum canis
, and
Candida glabrata. Among all the screened compounds, 7 exhibited good
activity (30–49 mm), followed by compounds 5 and 6, (35–46 mm), while
compounds 1–4 showed a moderate effect (8–28 mm) against the selected fungal strain against
miconazole which showed potent effects (101–110.98
mm). The isolated compounds were also screened for 1, 1-diphenyl-2-picrylhydrazyl
(DPPH) activity. In vitro-based free radical was employed using ascorbic
acid as a standard antioxidant. The tested compounds (1–7) exhibited significant antioxidant activity in a concentration-dependent
manner. The dinaphthodiospyrol 7 exhibited 97.32% scavenging
activity, followed by dinaphthodiospyrol 6, 92.01%, and
compounds 5 and 4 with 89.90 and 88.43%
scavenging activity at 100 μg/mL, respectively; ascorbic acid
showed 96.45% scavenging effect. Furthermore, docking analysis was
performed to know the exact binding mode of the tetra-substituted
derivatives of dinaphthodiospyrols to the selected target proteins.
From the docking analysis, it was found that the docking results are
well correlated with the experimental observations. In conclusion,
the dinaphthodiospyrols exhibited excellent antibacterial, antifungal,
and free radical scavenging potential.