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The reducing potential of plant extracts in the green synthesis of nanoparticles has been associated with their phytochemicals. Although pharmacologically inactive, a norlignan diglucoside “hypoxoside” (HP) occurs in large quantities in the extract of <i>Hypoxis hemerocallidea</i> (HE). In this work, HP was isolated from HE where both were used in the biosynthesis of the corresponding silver nanoparticles (HP-AgNPs and HE-AgNPs). The AgNPs were fully characterized using various physicochemical techniques and their antimicrobial and anticancer properties were evaluated. Transmission electron microscopy (TEM) revealed sizes of 24.3 ± 4 nm for the HE-AgNPs and 3.9 ± 1.6 nm for the HP-AgNPs. The HE-AgNPs demonstrated enhanced anti-bactericidal effects on <i>Escherichia coli</i> and <i>Salmonella enterica</i> with a minimum inhibitory concentration (MIC) value of 1.95 µg/mL, competing well with the standard drug. The cytotoxic activity showed that the HE-AgNPs reduced cell viability with an IC50 of 0.81 and 4.0 µg/mL, respectively, for the U87 and U251 cells, while the HP-AgNPs displayed 0.20 and 0.55 µg/mL for both cell lines, respectively. Furthermore, while the HE-AgNPs were selective to U87 alone, the HP-AgNPs were selective to both glioblastoma cells tested. The study demonstrated the ability of a single phytoconstituent (hypoxoside), not only as the chief bioreductant in the extract, but also as a standalone reducing and capping agent, producing ultra-small, spherical, and monodispersed AgNPs with enhanced biological properties.