(L.) Bernh.-Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from Essential Oil.

Motivated by the ethnopharmacological use of , in the present study, the antimicrobial potential of the extracted essential oil was investigated against a panel of eighteen microorganism strains. Additionally, anti-acetylcholinesterase and antispasmodic (isolated rat distal colon) activities, general acute toxicity ( model), and immunomodulatory properties (cytotoxicity on isolated mouse macrophages) were studied. Detailed analyses of the essential oil led to the identification of 3-methoxycuminyl 2-methylbutanoate (a new natural product) and 3-methoxycuminyl 3-methylbutanoate (a rare natural product). The obtained esters and intermediates in the synthesis of the starting alcohol (3-methoxycuminol) were subjected to a battery of 1D- and 2D-NMR experiments. The synthesized esters were additionally characterized by GC-MS, IR, and UV-Vis. The synthesized compounds (ten in total) were biologically tested in the same way as the extracted essential oil. The obtained low acute toxicity and promising antimicrobial potential suggest that the essential oil might partially explain the ethnopharmacological application of plant material for the treatment of gastrointestinal infections.