Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity

Giuseppe Savona, Gianfranco Fontana, Thomas E. Prisinzano, Christina M. Dersch, Benjamín Rodríguez, Richard B. Rothman

Risultato della ricerca: Article

28 Citazioni (Scopus)

Abstract

Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific k-opioid agonist. Several structural congeners of 1 isolated from Salvia splendens (2–8) together with a series of semisynthetic derivatives (9–24), some of which possess a pyrazoline structural moiety (9, 19–22), have been tested for affinity at human m, d, and k opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for k receptors suggesting that other natural neoclerodanes from different Salvia species may possess opioid affinity.
Lingua originaleEnglish
pagine (da-a)10041-10048
Numero di pagine8
RivistaTetrahedron
Volume64
Stato di pubblicazionePublished - 2008

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Salvia
salvinorin A
Diterpenes
Opioid Receptors
Opioid Analgesics
Mints
Mentha
Derivatives
neoclerodane

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cita questo

Savona, G., Fontana, G., Prisinzano, T. E., Dersch, C. M., Rodríguez, B., & Rothman, R. B. (2008). Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity. Tetrahedron, 64, 10041-10048.

Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity. / Savona, Giuseppe; Fontana, Gianfranco; Prisinzano, Thomas E.; Dersch, Christina M.; Rodríguez, Benjamín; Rothman, Richard B.

In: Tetrahedron, Vol. 64, 2008, pag. 10041-10048.

Risultato della ricerca: Article

Savona, G, Fontana, G, Prisinzano, TE, Dersch, CM, Rodríguez, B & Rothman, RB 2008, 'Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity', Tetrahedron, vol. 64, pagg. 10041-10048.
Savona, Giuseppe ; Fontana, Gianfranco ; Prisinzano, Thomas E. ; Dersch, Christina M. ; Rodríguez, Benjamín ; Rothman, Richard B. / Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of opioid receptor affinity. In: Tetrahedron. 2008 ; Vol. 64. pagg. 10041-10048.
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AU - Rodríguez, Benjamín

AU - Rothman, Richard B.

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AB - Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific k-opioid agonist. Several structural congeners of 1 isolated from Salvia splendens (2–8) together with a series of semisynthetic derivatives (9–24), some of which possess a pyrazoline structural moiety (9, 19–22), have been tested for affinity at human m, d, and k opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for k receptors suggesting that other natural neoclerodanes from different Salvia species may possess opioid affinity.

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