title: Antitrypanosomal triterpenoid with an ε-lactone E-ring from Salvia urmiensis.
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.
authors.affiliation: Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University , G. C., Evin, Tehran, Iran.
authors.forename: Mahdi
authors.initials: M
authors.lastname: Moridi Farimani
authors.forename: Samad
authors.initials: S
authors.lastname: Nejad Ebrahimi
authors.forename: Peyman
authors.initials: P
authors.lastname: Salehi
authors.forename: Mir Babak
authors.initials: MB
authors.lastname: Bahadori
authors.forename: Ali
authors.initials: A
authors.lastname: Sonboli
authors.forename: Hamid Reza
authors.initials: HR
authors.lastname: Khavasi
authors.forename: Stefanie
authors.initials: S
authors.lastname: Zimmermann
authors.forename: Marcel
authors.initials: M
authors.lastname: Kaiser
authors.forename: Matthias
authors.initials: M
authors.lastname: Hamburger
mesh_terms: D018360:Crystallography, X-Ray; D020128:Inhibitory Concentration 50; D007492:Iran; D007783:Lactones / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects; D027544:Salvia / Q000737:chemistry*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects
chemical_list: D007783:Lactones; D014315:Triterpenes; C585008:urmiensolide; D009828:Oleanolic Acid; C036380:beta-amyrin