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Phytochemical investigation of the ethanol extract of underground parts of <i>Iris tenuifolia</i> Pall. afforded five new compounds; an unusual macrolide termed moniristenulide (<b>1</b>), 5-methoxy-6,7-methylenedioxy-4-<i>O</i>-2′-cycloflavan (<b>2</b>), 5,7,2′,3′-tetrahydroxyflavanone (<b>3</b>), 5-hydroxy-6,7-dimethoxyisoflavone-2′-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>9</b>), 5,2′,3′-dihydroxy-6,7-dimethoxyisoflavone (<b>10</b>), along with seven known compounds (<b>4</b>–<b>8</b>, <b>11</b>–<b>12</b>). The structures of all purified compounds were established by analysis of 1D and 2D NMR spectroscopy and HR-ESI-MS. The antimicrobial activity of the compounds <b>1</b>–<b>3</b>, <b>5</b>, <b>9</b>, and <b>10</b> was investigated using the agar diffusion method against fungi, Gram-positive and Gram-negative bacteria. In consequence, new compound <b>3</b> was found to possess the highest antibacterial activity against <i>Enterococcus faecalis</i> VRE and <i>Mycobacterium vaccae</i>. Cell proliferation and cytotoxicity tests were also applied on all isolated compounds and plant crude extract in vitro with the result of potent inhibitory effect against leukemia cells. In particular, the newly discovered isoflavone <b>10</b> was active against both of the leukemia cells K-562 and THP-1 while <b>4</b>–<b>6</b> of the flavanone type compounds were active against only THP-1.