Structural characterization and biological activity of 3,4-dihydroxy-1,6-bis(3-methoxyphenyl)hexa-2,4-diene-1,6-dione (DBMPD) isolated from vegetable seeds

The increasing demand for the production and consumption of vegetables as part of a balanced diet has resulted in significant plant-based waste rich in phytochemicals, which has recently gained attention for its potential use as innovative ingredients in food, cosmetics, and pharmaceuticals. The current study presents the isolation and characterization of 3,4-Dihydroxy-1,6-bis(3-methoxyphenyl)hexa-2,4-diene-1,6-dione (DBMPD) from vegetable seed waste for evaluating its biological efficiency and applications. Comprehensive spectroscopic characterization of DBMPD was performed through Fourier transform infrared spectroscopy (FT-IR), UV-Vis, and NMR techniques in conjunction with Gaussian 09 computation software. Ground state molecular geometry, vibrational modes, and electronic orbital characteristics were derived through density functional theory (DFT) calculations employing the Becke, 3-parameter, Lee-Yang-Parr (B3LYP) exchange-correlation functional paired with the 6-311++G(d,p) basis set. The resulting computational data were further applied to map the energy profile and evaluate the chemical reactivity descriptors of DBMPD. In vitro antimicrobial activity of DBMPD was observed, with zones of inhibition of 17.3±0.5 mm and 19.6±1.1 mm against Proteus mirabilis . Additionally, the compound demonstrated significant 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity (21.8±0.6% to 45.4±1.5%) at a concentration of 10µg/mL ( p = 0.0079 ) and H 2 O 2 scavenging activity ranging from 22.8±1.6% to 45.4±1.5% at concentrations of 10µg/mL and 50µg/mL, respectively (p=0.005 , p<0.0001 ). Regarding antidiabetic effectiveness, DBMPD exhibited substantial glucosidase inhibitory activity at all concentrations ( p<0.001 ). Lastly, in silico molecular docking analysis, employing AutoDock software, revealed a binding free energy of −5.6 Kcal/mol and a computed inhibition constant (Ki) of 77.7347 M. These docking outcomes confirm that DBMPD forms a stable complex with the 3S35 breast cancer target protein, highlighting its prospective value as a lead molecule in anticancer drug development. Moreover, the observed antibacterial and antidiabetic activities highlight the potential of the bio/vegetable waste for applications in the pharmaceutical sector.