Monoterpenoid derivatives from Hyssopus cuspidatus Boriss. and their bioactivities

Six undescribed monoterpenoids, together with twelve known compounds were isolated and identified from Hyssopus cuspidatus Boriss. Their structures were established by spectroscopic analysis, and the absolute configurations were established by ECD calculations and single-crystal X-ray diffraction crystallography. The isolated compounds were tested for their anti-inflammatory, antibacterial and antitumor activities. Most of the compounds showed potent anti-inflammatory activities. Among them, 3β-hydroxy-7,8-dihydro-β-ionone (8), oleanolic acid (17) and acetylpleamolic acid (18) showed strong anti-inflammatory activity against IL-6 and TNF-α in lipopolysaccharide (LPS) stimulated RAW 264.7 cells. Several compounds showed moderate inhibitory activities against Staphylococcus aureus, Candida albicans, and Escherichia coli. And (4S)-p-menth-l-ene-7,8-diol 8-O-β-D-glucopyranoside (16) showed antitumor activities against MCF-8 and HT-29 cell lines with IC₅₀ values of 93.39 ± 3.69 and 71.89 ± 2.94 μM, respectively. Oleanolic acid (17) showed moderate antitumor activity against HT-29 cell lines with an IC₅₀ value of 52.62 ± 1.63 μM. In this study, the discovery of anti-inflammatory, antibacterial and antitumor components from H. cuspidatus could benefit further development and utilization of this plant.