Antitrypanosomal triterpenoid with an ε-lactone E-ring from Salvia urmiensis.

Mahdi Moridi Farimani, Samad Nejad Ebrahimi, Peyman Salehi, Mir Babak Bahadori, Ali Sonboli, Hamid Reza Khavasi, Stefanie Zimmermann, Marcel Kaiser, Matthias Hamburger

Journal: Journal of natural products 2013;76(9):1806-9

PMID: 24007549

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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.

Address: Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University , G. C., Evin, Tehran, Iran.

DOI: 10.1021/np400337a

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MeSH Terms: Crystallography, X-Ray, Inhibitory Concentration 50, Iran, Lactones, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Oleanolic Acid, Parasitic Sensitivity Tests, Plasmodium falciparum, Salvia, Stereoisomerism, Triterpenes, Trypanosoma brucei rhodesiense