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Vitex negundo var. Cannabifolia (Sieb. et Zucc.) Hand.-Mazz. leaves and twigs were used to isolate a new phenyldihydronaphthalene-type lignan (1) along with twenty known compounds. Comprehensive spectroscopic techniques such as UV, IR, NMR, HR-ESI-MS, ORD and ECD were used to identify their structures. Quantum chemical computations were used to assign the absolute configurations (AC) of (1). Using DP4+ analysis, the computed chemical shifts were used to pinpoint relative configuration. Compounds (1–6) were tested for biological activities. Compound (5) significantly decreased the release of lactate dehydrogenase (LDH) by 38% at a concentration of 10 μM, demonstrating that compound (5) had significant anti-inflammatory effects on the activation of the NLRP3 inflammasome, while no compound was found potent at a concentration of 200 μM against tyrosinase. Additionally, the chemotaxonomic significance of the isolated compounds was studied. [Display omitted] • One new phenyldihydronaphthalene-type lignan along with twenty known compounds from Vitex negundo var. Cannabifolia. • Spectroscopic analyses and quantum chemistry calculations were used to elucidate structures. • Compound 5 inhibited the release of lactate dehydrogenase (LDH) by 38% at a concentration of 10 μM. • Chemotaxonomic significance of the isolated compounds was discussed. [ABSTRACT FROM AUTHOR]