Terpenoid Constituents of Perovskia artemisioides Aerial Parts with Inhibitory Effects on Bacterial Biofilm Growth

Abstract

Perovskia artemisioides is a perennial and aromatic plant distributed in the Baluchestan region of Iran. In the present work, an n-hexane extract of P. artemisioides aerial parts showed excellent capabilities to both inhibit the formation of biofilms by different Gram-positive and Gram-negative pathogens and block the cell metabolism within microbial biofilms. To correlate the activity of the extract with the biologically active compounds present, first an analytical approach based on LC-HRMS/MSn was carried out. The metabolite profile obtained guided the isolation of 21 compounds, among which two sesquiterpenes (8 and 9) and one diterpene (10) were found to be new. The antimicrobial activity of the isolated compounds was evaluated by determining how they were able not only to reduce the growth of different Gram-positive and Gram-negative human bacteria and phytopathogens but also to inhibit the formation of biofilms by these bacteria and affect the metabolism of microbial cells present within the biofilms. With the aim of correlating the activity exhibited by the extract with the concentration levels of the constituent compounds, a quantitative determination was carried out by an analytical approach based on LC-ESI/QTrap/MS.

Anti-inflammatory Activity of Tanshinone-Related Diterpenes from Perovskia artemisioides Roots

“…In particular, the MS/MS spectra of compounds 3 , 5 , 6 , 15 , and 18 showed the loss of H 2 O [M + H-18] + due to the enolic rearrangement of a carbonyl group, and the additional loss of CO from this fragment ion gave the ion [M + H-46] + , in agreement with the literature data for tanshinone derivatives . Peaks corresponding to compounds 7 , 8 , 12 , 14 , 17 , 19 , and 22 – 24 showed a fragmentation pattern typical of abietane derivatives as previously reported in P. artemisioides aerial parts . However, the molecular formula of compounds 2 , 9 , 10 , 11 , 16 , and 20 could not be attributed to diterpenoids previously reported in the literature.…”

“…A C 18 reversed-phase (RP) column (150 mm × 2.00 mm) Luna C 18 5 μm (Waters, Milford, MA) at a flow rate of 0.2 mL/min was selected, with water plus 0.1% formic acid and acetonitrile plus 0.1% formic acid used as phases A and B, respectively. For the experimental conditions and HPLC gradient, the same conditions as previously reported for Perovskia artemisioides aerial parts were used . The autosampler was set to inject 4 μL of n -hexane extract (0.5 mg/mL).…”

“…Perovskia is a small genus of the family Lamiaceae, comprising nine species distributed mainly in the rocky areas of central Asia . In traditional medicine, extracts of Perovskia species are used as remedies for their antibacterial, anti-inflammatory, stomachic, expectorant, and carminative activities . Previous phytochemical investigations resulted in the occurrence of diterpenoid derivatives belonging to the abietane, icetexane, and isopimarane classes. , Among the isolated abietanes, tanshinones are 20-norditerpenes with an abietane-type skeleton characterized by a phenanthrenequinone core, including ortho -quinone and para -quinone derivatives .…”

Investigation of the Composition, Antimicrobial, Antioxidant, and Cytotoxicity Properties of Salvia abrotanoides Essential Oil

“…e metabolites of S. abrotanoides have been used in traditional medicine, including the improvement of fever [24], antidiabetic [25], rheumatic pain [26], chronic hepatitis B virus (HBV), and leishmaniasis [27], and also other disorders like atherosclerosis, cardiovascular illness, liver, and cardiac fibrosis [28]. Likewise, it had particular role in Iranian traditional medical activity to heal leishmaniasis and skin disorders [21].…”

Brief overview of recently reported misassigned natural products and their in silico revisions enabled by DU8ML, a machine learning-augmented DFT computational NMR method

“…Carbon-13 NMR data for isocaryolane-1α,9β-diol ( 19 ), extracted from aerial parts of the plant Perovskia artemisioides 10 produced poor match with the computed chemical shifts. It was revised to 9-epimer 20 .…”