Isolation and Purification of Isoflavones and Isoflavone Glycosides from Dalbergia sissoo Leaves and In silico Evaluation for Anti-aging Potential

Abstract

Dalbergia sissoo Roxb., rich in isoflavones and isoflavone glycosides, is widely used to treat osteogenic effects, pain, and other diseases. This study employed simple procedures based on preparative reversed-phase high-pressure liquid chromatography (prep-RP-HPLC) for large-scale isolation of isoflavones and isoflavone glycosides present in Dalbergia sissoo leaves (DSL). The seven compounds were isolated from the ethanolic extract by the preparative HPLC–PDA method, and their purity was > 95%. The authors carried out an in silico analysis to find possible anti-aging compounds. Isolated compounds biochanin-A-7-O-[β-Dapiofuranosyl-(1–5)-β-D-apiofuranosyl-(1–6)-β-D-glucopyranoside (DS2) and biochanin-A-7-O [β-D-apiofuranosyl-(1–6)-β-D-glycopyranoside (DS3) demonstrated docking scores of −10.466 and −9.430 with docking energies of -81.864 and -77.531 kcal/mol, respectively, to the Hyaluronidase enzyme. For the Collagenase enzyme, they showed docking scores of −10.734 and −10.777 with docking energies of −107.102 and −98.317 kcal/mol, respectively. Against the Tyrosinase enzyme, Compounds DS2 and DS3 had docking scores of −7.333 and −7.993 with docking energies of −59.933 and −84.825 kcal/mol, respectively. For the elastase enzyme, they exhibited docking scores of −9.840 and −7.993 with docking energies of −68.490 and −84.815 kcal/mol, respectively. This study found that the isolation and purification method is simple and produces neat chromatograms with good selectivity and reproducibility. At the same time, docking results revealed that the compounds exhibited anti-aging properties.

Graphical abstract