| Summary: | Indigenous to Lebanon, <i>Origanum syriacum</i> L. and <i>Cousinia libanotica</i> D.C. are notable plants in the Middle East, with <i>O. syriacum</i> known for its aromatic qualities and <i>C. libanotica</i> being less explored. Both plants have a significant role in traditional medicine for treating various ailments. This study aimed to evaluate the phytochemical composition and biological properties of the extracts from these plants. The extracts were obtained through cold maceration with solvents of increasing polarity. The ethyl acetate extract of <i>O. syriacum</i> exhibited the highest total polyphenol content. High-performance liquid chromatography (HPLC) identified fifteen compounds in both <i>C. libanotica</i> and <i>O. syriacum</i> extracts, whereas gas chromatography–mass spectrometry (GC-MS) analysis unveiled 179 volatile compounds. Notably, the <i>O. syriacum</i>-MeOH extract showed moderate antioxidant activity. Both plants’ methanolic extracts demonstrated significant anti-Alzheimer’s potential. The <i>O. syriacum</i>-dichloromethane and <i>C. libanotica</i>-cyclohexane extracts displayed the highest cytotoxicities against the HCT-116 cell line. For anti-proliferative activity against the Caco-2 cell line, the <i>O. syriacum</i>-methanol and <i>C. libanotica</i>-cyclohexane extracts were the most effective. This study provides valuable insights into the phytochemistry and potential therapeutic applications of extracts from these two oriental plant species.
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