Antitrypanosomal Triterpenoid with an ε-Lactone E-Ring from Salvia urmiensis

Hamburger, Matthias

doi:10.1021/np400337a

Antitrypanosomal Triterpenoid with an ε-Lactone E-Ring from Salvia urmiensis

Date Issued

2013-01-01

Author(s)

Farimani, Mahdi Moridi

Ebrahimi, Samad Nejad

Salehi, Peyman

Bahadori, Mir Babak

Sonboli, Ali

Khavasi, Hamid Reza

Zimmermann, Stefanie

Kaiser, Marcel

Hamburger, Matthias

DOI

10.1021/np400337a

Abstract

A new triterpenoid, urmiensolide (1), was isolated from Salvia urmiensis. The structure was elucidated by a combination of 1D and 2D NMR, HRESIMS, and X-ray crystallographic analyses. The absolute configuration was established by comparison of experimental and simulated ECD spectra. Urmiensolide is the first pentacyclic triterpenoid bearing a ε-lactone E-ring. The compound showed in vitro antitrypanosoal activity with an IC50 value of 5.6 μM against the Trypanosoma brucei rhodesiense STIB 900 strain and a selectivity index of 33. A possible biosynthetic pathway of 1 from α-amyrin is proposed.