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Seven commercial hop (Humulus lupulus L.) oils originating from a selection of North American hop varieties (Amarillo, Azacca, Cascade, Centennial, Chinook, Saaz, and Ahhhroma) and six homemade hop oils hydrodistilled from the same commercial hop pellets (except Ahhhroma) were compared. Seven terpenes regarded as hop oil markers (i.e., α-pinene, β-pinene, β-myrcene, β-ocimene, limonene, β-caryophyllene, and α-humulene) and methyl heptanoate were identified and quantified by GC–MS and GC-FID. The antioxidant potential of the commercial hop oil samples was evaluated using electron paramagnetic resonance (EPR) spectroscopy, while their components' antibacterial (against Aliivibrio fischeri) and enzyme (α-glucosidase and lipase) inhibition activities were screened using high-performance thin-layer chromatography (HPTLC)-based assays. A distinct feature of five of the commercial hop oils (except Saaz and Ahhhroma) was relatively high contents of β-myrcene (between 4.21 and 6.40 µg mg−1 hop oil). Azacca, Cascade, and Centennial hydrodistilled oils had perceptibly higher contents of β-caryophyllene than the rest, and most of them (except Chinook) contained relatively high amounts of α-humulene. Differences between the terpene profiles of the commercial and homemade hydrodistilled hop oils suggested that the commercial hop oils were derived from hop cones in a process different from hydrodistillation. The oils showed relatively low antioxidant potential, comparable to that of popular beers and white wines. The highest antioxidant potential was observed in Ahhhroma oil, while it was very low in Centennial oil, and no antioxidant potential was observed in Cascade and Saaz oils. The developed streamlined workflow, including parallel HPTLC-directed bioassays and HPTLC—TLC–MS Interface—SPME–GC–MS, enabled the identification of β-myrcene, dimyrcenes, β-farnesene, and 2-methylbutyl isobutyrate as anti-obesity compounds and β-farnesene, β-myrcene, and 2-methylbutyl isobutyrate as weak antibacterial hop oil components. [ABSTRACT FROM AUTHOR]