A new iridoid glycoside; 6-O-β-D-xylopyranoside-shanzhiside methyl ester (1) along with six known compounds; shanzhiside methyl ester (2), lamalbid (3), geniposidic acid (4), theveside (5), verbascoside (6) and arenarioside (7) were isolated from the roots of Lantana montevidensis. The structures of the compounds were determined through 1D and 2D NMR spectroscopic data analysis, HRESIMS, electronic circular dichorism and UPLC-UV/MS method. The total extract, chloroformic (F1) and aqueous (F2) fractions together with the isolated compounds were tested for their antimicrobial, antiprotozoal, antiplasmodial, anti-inflammatory, monoamine oxidase inhibition and cell viability activities in addition to free radical scavenging activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The phenylpropanoid compounds (6 and 7) resulted in a potent antioxidant activity. Total methanolic extract together with the aqueous fraction (F2) showed decrease in reactive oxidative stress with 57 and 66%, respectively, while the chloroformic fraction (F1), together with the total methanolic extract, showed a decrease in iNOS with IC50 values 5 and 30 μg/mL, respectively. Compounds 1, 2, 3, 6, and 7 showed inhibition in the reactive oxidative stress with values 50, 60, 57, 63, and 52%, respectively. Both F1 and F2 fractions demonstrated measurable inhibition of MCF-7 breast cancer cell growth, with IC50 value 0.3 mg/mL. Compounds 2 and 7 showed mild monoamine oxidase inhibition. None of the tested compounds showed antimicrobial, antiplasmodial or antiprotozoal activity.