Dialdehyde sesquiterpenes and other terpenoids as vanilloids

Arpad Szallasi, T. Bíró, Shayan Modarres, Luigi Garlaschelli, Marlen Petersen, Andreas Klusch, Giovanni Vidari, Mikael Jonassohn, Salvatore De Rosa, Olov Sterner, Peter M. Blumberg, James E. Krause

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

Selected naturally occurring unsaturated dialdehyde sesquiterpenes and related bioactive terpenoids were assayed for vanilloid-like activity. Out of the 25 compounds tested, eight inhibited completely the specific binding of [3H]resiniferatoxin by rat spinal cord membranes: binding affinities ranged from 0.6 μM for cinnamodial to 19.0 μM for hebelomic acid F. These values were comparable to the binding affinity of capsaicin (2.7 μM). With the exception of four ligands, compounds that inhibited resiniferatoxin binding to rat spinal cord membranes were also pungent on the human tongue where they showed cross-tachyphylaxis with capsaicin. As expected from their reactive nature, these compounds possess additional sites of action, as reflected in the complex behavior of the stimulation of calcium influx by cinnamodial and cinnamosmolide at high concentrations. This observation might explain the unexpectedly weak membrane depolarization by cinnamodial compared to capsaicin. We conclude that a range of sesquiterpene dialdehydes and related terpenoids, both pungent and non-pungent, may function as vanilloids. These compounds may represent a new chemical lead for the development of vanilloid drugs, structurally unrelated to either capsaicin or resiniferatoxin. Copyright (C) 1998 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)81-89
Number of pages9
JournalEuropean Journal of Pharmacology
Volume356
Issue number1
DOIs
Publication statusPublished - Aug 28 1998

Fingerprint

Sesquiterpenes
Capsaicin
Terpenes
Membranes
Spinal Cord
Tachyphylaxis
Tongue
Ligands
Calcium
Acids
Pharmaceutical Preparations
resiniferatoxin
cinnamodial

Keywords

  • Capsaicin
  • Dialdehyde, unsaturated
  • Resiniferatoxin
  • Vanilloid receptor

ASJC Scopus subject areas

  • Cellular and Molecular Neuroscience
  • Pharmacology

Cite this

Szallasi, A., Bíró, T., Modarres, S., Garlaschelli, L., Petersen, M., Klusch, A., ... Krause, J. E. (1998). Dialdehyde sesquiterpenes and other terpenoids as vanilloids. European Journal of Pharmacology, 356(1), 81-89. https://doi.org/10.1016/S0014-2999(98)00514-7

Dialdehyde sesquiterpenes and other terpenoids as vanilloids. / Szallasi, Arpad; Bíró, T.; Modarres, Shayan; Garlaschelli, Luigi; Petersen, Marlen; Klusch, Andreas; Vidari, Giovanni; Jonassohn, Mikael; De Rosa, Salvatore; Sterner, Olov; Blumberg, Peter M.; Krause, James E.

In: European Journal of Pharmacology, Vol. 356, No. 1, 28.08.1998, p. 81-89.

Research output: Contribution to journalArticle

Szallasi, A, Bíró, T, Modarres, S, Garlaschelli, L, Petersen, M, Klusch, A, Vidari, G, Jonassohn, M, De Rosa, S, Sterner, O, Blumberg, PM & Krause, JE 1998, 'Dialdehyde sesquiterpenes and other terpenoids as vanilloids', European Journal of Pharmacology, vol. 356, no. 1, pp. 81-89. https://doi.org/10.1016/S0014-2999(98)00514-7
Szallasi A, Bíró T, Modarres S, Garlaschelli L, Petersen M, Klusch A et al. Dialdehyde sesquiterpenes and other terpenoids as vanilloids. European Journal of Pharmacology. 1998 Aug 28;356(1):81-89. https://doi.org/10.1016/S0014-2999(98)00514-7
Szallasi, Arpad ; Bíró, T. ; Modarres, Shayan ; Garlaschelli, Luigi ; Petersen, Marlen ; Klusch, Andreas ; Vidari, Giovanni ; Jonassohn, Mikael ; De Rosa, Salvatore ; Sterner, Olov ; Blumberg, Peter M. ; Krause, James E. / Dialdehyde sesquiterpenes and other terpenoids as vanilloids. In: European Journal of Pharmacology. 1998 ; Vol. 356, No. 1. pp. 81-89.
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