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A new glucosyl flavone, 5,7,2′,5′-tetrahydroxyflavone 7-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside, named loeflingiin, together with apigenin 6-<i>C</i>-glucoside (isovitexin), coumarins citropten and isompinellin, triterpenoids betulin and betulinic acid, and a mixture of phytosterols β-sitosterol, stigmasterol and campesterol were isolated for the first time from the leaves of wild <i>Plantago loeflingii</i> L. (<i>Plantaginaceae</i>) collected in the Iraqi Kurdistan region. The plant is used by local people to treat wounds and as a vulnerary remedy. The structures of isolated compounds were determined by spectroscopic analysis. The activities of isovitexin and loeflingiinon the viability of breast (MCF7), ovarian (BG-1), endometrial (Ishikawa), and mesothelioma (IST-MES1) human cancer cells and two normal cell lines were determined with an MTT assay. Notably, the new 7-<i>O</i>-glucosyl flavone showed effects higher than cisplatin against the Ishikawa and IST-MESI cell lines. The significant biological activities exhibited by all the compounds isolated from <i>P. loeflingii</i> provided scientific evidence to support the use of the plant in the Kurdish traditional medicine.