Chemical Constituents of the Aerial Parts ofDaucus carotasubsp.hispidusGrowing in Tunisia

Abstract

Three known polyol menthane monoterpenoids, namely, (4 R)-1- p-menthen-6,8-diol (1), (4 R)-1- p-menthen-4,7-diol (2), and (1 R,2 R,4 R)- p-menthane-1,2,4-triol (3), and 6 known phenolics (4-9), in addition to β-sitosterol 3- O-glucoside (10), were isolated from the aerial parts of Daucus carota subsp. hispidus (Ball) Heywood (Family: Apiaceae) growing in Tunisia. The structures of the isolated compounds were established depending upon the spectroscopic techniques including one and two-dimensional nuclear magnetic resonance (1D, and 2D NMR) and high resolution mass spectroscopy (HRMS). The absolute configuration of the compounds 1 to 3 was determined using experimental circular dichroism (CD) for the first time. Compounds 1 to 3 were reported for the first time from this plant. Compounds 1 to 3 exhibited no antimicrobial and antioxidant activity using superoxide dismutase-like activities. Compounds 2 and 3 exhibited weak activity, while 1 showed negative cytotoxic activity against human mouth squamous carcinoma (HSC-2) and human cervical cells (HeLa) cancer cells.