Planta Med
DOI: 10.1055/a-1264-0572
Original Papers

Identification of TRPV1 Ion Channels Agonists of Tropaeolum tuberosum in Human Skin Keratinocytes

1  Department of Organic Chemistry, Faculty of Sciences, University Autónoma of Madrid, Madrid, Spain
2  Department of Pharmacology, Pharmacognosy and Botany, Faculty of Pharmacy, University Complutense of Madrid, Madrid, Spain
,
Ángel Rumbero Sánchez
1  Department of Organic Chemistry, Faculty of Sciences, University Autónoma of Madrid, Madrid, Spain
,
Cristina Thiebaut Estrada
3  Department of Research and Development, COBIOSA, Madrid, Spain
,
2  Department of Pharmacology, Pharmacognosy and Botany, Faculty of Pharmacy, University Complutense of Madrid, Madrid, Spain
› Author Affiliations

Abstract

Tropaeolum tuberosum, commonly known as Mashua, is an herbal remedy used in traditional Andean medicine for the relief of kidney and bladder pain, as well as contusions. This study aimed to evaluate the fractions and isolated compounds from T. tuberosum with analgesic activity mediated by the transient receptor potential vanilloid-1 receptor. A bioguided phytochemical analysis based on NMR/MS was performed to identify the compounds of the n-heptane fractions from samples of purple tubers of T. tuberosum. The transient receptor potential vanilloid-1 agonist and antagonist activity were assessed through the measurement of intracellular Ca2+ in HEK001 cells. The chemical structure determination led to the identification of two alkamides: N-(2-hydroxyethyl)-7Z,10Z,13Z,16Z-docosatetraenamide (1) and N-oleoyldopamine (2). Both compounds induced increased intracellular calcium flow with IC50 values of 3.2 nM and 7.9 nM, respectively, thus activating the transient receptor potential vanilloid-1 receptor. Our research is the first report to show that these two compounds isolated from T. tuberosum can act as agonists of the transient receptor potential vanilloid-1 receptor, providing scientific evidence for the traditional use of this species in pain relief.

Supporting Information



Publication History

Received: 10 April 2020

Accepted after revision: 07 September 2020

Publication Date:
02 October 2020 (online)

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