Plumbagin, Juglone, and Boropinal as Novel TRPA1 Agonists

Journal of Natural Products
Kerstin HillSalvatore Genovese

Abstract

A series of seven oxyprenylated phenylpropanoids and naphthoquinones were tested regarding their ability to activate transient receptor potential ankyrin subtype 1 channel (TRPA1). Three of the assayed compounds, namely, boropinal (3), juglone (5), and plumbagin (7), acted as strong modulators of TRPA1 channels with EC50 values of 9.8, 1.7, and 0.5 μM, respectively, as assessed by Ca(2+) assays. Moreover, the compounds elicited TRPA1 currents in electrophysiological whole cell recordings. We additionally provide evidence that plumbagin activated TRPA1-positive neurons isolated from mouse dorsal root ganglion neurons but did not affect sensory neurons from TRPA1-deficient mice. The high potencies of plumbagin and juglone to activate TRPA1 channels may explain the molecular basis of the mucosal irritant properties of these compounds as well as of related naphthoquinones and phytopreparations, as widely reported in the literature.

References

Nov 15, 2000·Journal of Natural Products·C ItoH Furukawa
Jan 16, 2007·Handbook of Experimental Pharmacology·J García-Añoveros, K Nagata
Jan 16, 2007·The Journal of Biological Chemistry·Kerstin Hill, Michael Schaefer
Jan 30, 2007·Nature Neuroscience·Sandra ZurborgPaul A Heppenstall
Sep 15, 2007·The Journal of Neuroscience : the Official Journal of the Society for Neuroscience·Yuji KarashimaBernd Nilius
Sep 15, 2009·Nature Neuroscience·Karel TalaveraThomas Voets
Feb 16, 2010·Archives of Biochemistry and Biophysics·Viola KlausLars-Oliver Klotz
Oct 20, 2010·Current Drug Targets·Salvatore Genovese, Francesco Epifano
Jun 24, 2011·Bioorganic & Medicinal Chemistry Letters·Céline BruyèreFrancesco Epifano
Apr 5, 2012·Bioorganic & Medicinal Chemistry Letters·Francesco EpifanoMatthew A Gray
Aug 31, 2012·Anti-cancer Agents in Medicinal Chemistry·Jin-Jian LuYi-Tao Wang
Jun 1, 2013·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Boyi LiuSven E Jordt
Jan 30, 2014·International Journal of Cancer. Journal International Du Cancer·Masahito ShimizuHisataka Moriwaki
Apr 24, 2014·Handbook of Experimental Pharmacology·Peter M Zygmunt, Edward D Högestätt
Jun 3, 2014·Journal of Ethnopharmacology·Ruchi Badoni SemwalAlvaro Viljoen
Jun 20, 2014·American Journal of Physiology. Cell Physiology·Hiroka SuzukiKatsuhiko Muraki
Dec 3, 2014·Bioorganic & Medicinal Chemistry Letters·Giorgio OrtarLuciano De Petrocellis

❮ Previous
Next ❯

Citations

Apr 11, 2017·The Journal of Organic Chemistry·Bernd Schmidt, Felix Wolf
Nov 2, 2019·Physiological Reviews·Karel TalaveraBernd Nilius
Sep 17, 2019·Clinical and Experimental Hypertension : CHE·Taseer AhmadAbdul Jabbar Shah
Apr 10, 2019·Antioxidants·Taseer Ahmad, Yuichiro J Suzuki

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.