Essential Oils from Monarda fistulosa: Chemical Composition and Activation of Transient Receptor Potential A1 (TRPA1) Channels

Abstract

Little is known about the pharmacological activity of Monarda fistulosa L. essential oils. To address this issue, we isolated essential oils from the flowers and leaves of M. fistulosa and analyzed their chemical composition. We also analyzed the pharmacological effects of M. fistulosa essential oils on transient receptor potential (TRP) channel activity, as these channels are known targets of various essential oil constituents. Flower (MEOFl) and leaf (MEOLv) essential oils were comprised mainly of monoterpenes (43.1% and 21.1%) and oxygenated monoterpenes (54.8% and 77.7%), respectively, with a high abundance of monoterpene hydrocarbons, including p-cymene, γ-terpinene, α-terpinene, and α-thujene. Major oxygenated monoterpenes of MEOFl and MEOLv included carvacrol and thymol. Both MEOFl and MEOLv stimulated a transient increase in intracellular free Ca2+ concentration ([Ca2+]i) in TRPA1 but not in TRPV1 or TRPV4-transfected cells, with MEOLv being much more effective than MEOFl. Furthermore, the pure monoterpenes carvacrol, thymol, and β-myrcene activated TRPA1 but not the TRPV1 or TRPV4 channels, suggesting that these compounds represented the TRPA1-activating components of M. fistulosa essential oils. The transient increase in [Ca2+]i induced by MEOFl/MEOLv, carvacrol, β-myrcene, and thymol in TRPA1-transfected cells was blocked by a selective TRPA1 antagonist, HC-030031. Although carvacrol and thymol have been reported previously to activate the TRPA1 channels, this is the first report to show that β-myrcene is also a TRPA1 channel agonist. Finally, molecular modeling studies showed a substantial similarity between the docking poses of carvacrol, thymol, and β-myrcene in the binding site of human TRPA1. Thus, our results provide a cellular and molecular basis to explain at least part of the therapeutic properties of these essential oils, laying the foundation for prospective pharmacological studies involving TRP ion channels.

Herbicide Potential of Selected Essential Oils From Plants of Lamiaceae and Asteraceae Families

“…hirtum essential oils. ese results agree with previously reported data (Ghosh et al, 2020;Mancini et al, 2014;Semerdjieva et al, 2020). e essential oil profile of T. longedentatus was reported in our previous study (Aneva et al, 2019).…”

“…Similarly, Artemisia campestris was selected because there are data for the phytotoxic potential of other Artemisia species (Benvenuti et al, 2017;Kaur et al, 2010). Monarda fistulosa has been reported to contain carvacrol (Ghosh et al, 2020). Citral isomers (geranial and neral) have been found to be substances with strong herbicidal effects (Dayan et al, 2012).…”

Polyphenols and Pharmacological Screening of a Monarda fistulosa L. dry Extract Based on a Hydrodistilled Residue By-Product

“…ex Lag. , and M. punctata L. ( Fraternale et al, 2006 ; Zhilyakova et al, 2009 ; Geffre et al, 2011 ; Tabanca et al, 2013 ; Thompson et al, 2013 ; Li et al, 2014 ; Mattarelli et al, 2017 ; Shanaida et al, 2018b ; Deepika et al, 2020 ; Ghosh et al, 2020 ; Marchioni et al, 2020 ).…”

Synthesis, molecular docking, ADMET study and in vitro pharmacological research of 7-(2-chlorophenyl)-4-(4-methylthiazol-5-yl)-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-dione as a promising non-opioid analgesic drug

“…4). Since its discovery, this TRPA1 ion channel structure has become a promising target for in silico screening and development of novel non-covalent antagonists and other selective small molecule inhibitors (Mihai et al 2019, Ghosh et al 2020.…”

“…Despite numerous docking studies based on the electron cryo-microscopy structure of TRPA1 ion channel deposited as PDB code 3J9P, a mechanistic understanding of ligand-receptor interactions has been claimed to have a lack of high-resolution details. Therefore, the high-resolution structure of human TRPA1 has recently been re-measured using cryo-electron (cryo-EM) microscopy of nanodisc-reconstituted ligand-free receptor and TRPA1 in complex with some covalent antagonists at 2.8 -3.1 Å resolution (Ghosh et al 2020).…”