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Planta Med 2021; 87(05): 383-394
DOI: 10.1055/a-1264-0572
Biological and Pharmacological Activity
Original Papers

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

Luis Apaza Ticona 
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
,
Olga M. Palomino 
2   Department of Pharmacology, Pharmacognosy and Botany, Faculty of Pharmacy, University Complutense of Madrid, Madrid, Spain
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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.

Key words

Tropaeolaceae - Tropaeolum tuberosum - alkamides - vanilloid - analgesic - TRPV1

Supporting Information

    1H- and 13C- NMR, 1H-1H COSY, HSQC, HMQC, HMBC, and MS spectra for the different fractions assayed in this study, together with isolated compounds 1 and 2, are provided as Supporting Information (Figs. 1S–23S). The activity data of the T. tuberosum fractions from the different samples are also provided as Supporting Information (Tables 1S–4S).

  • Supporting Information


Publikationsverlauf

Eingereicht: 10. April 2020

Angenommen nach Revision: 07. September 2020

Artikel online veröffentlicht:
02. Oktober 2020

© 2020. Thieme. All rights reserved.

Georg Thieme Verlag KG
Stuttgart · New York

 

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