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, 3ß-hydroxy-7,8-dihydro-ß-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-ß-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.

Non-volatile compounds of Hyssopus cuspidatus Boriss and their antioxidant and antimicrobial activities.

Hyssopus cuspidatus is a famous spice and an aromatic vegetable. Few information could be available concerning its non-volatile chemical composition and bioactivities. Preliminary bioactive evaluations on the crude ethanol extract and its four fractions disclosed that the ethyl acetate fraction (EAF) exhibited antioxidant and antimicrobial bioactivities. LC-MS/MS analysis of EAF helped to identify sixty-four compounds, and phenolic compounds were the dominant components. Systematic separation and purification of EAF led to the isolation of thirty-four compounds. Six compounds were identified to be new and eighteen compounds were discovered from H. cuspidatus for the first time. Rosmarinic acid, methyl rosmarinate, butyl rosmarinate and salvigenin were the major components of EAF and their contents were determined. Most of isolated compounds exhibited significant or moderate antioxidant and antimicrobial activities. This research supported the edible application of H. cuspidatus and disclosed the potency of it as a natural antioxidant and antimicrobial food additive.