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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Crystallography, X-Ray
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Inhibitory Concentration 50
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Iran
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Lactones / chemistry*
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oleanolic Acid / analogs & derivatives
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Oleanolic Acid / metabolism
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Parasitic Sensitivity Tests
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Plasmodium falciparum / drug effects
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Salvia / chemistry*
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Stereoisomerism
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Triterpenes* / chemistry
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Triterpenes* / isolation & purification
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Triterpenes* / pharmacology
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Trypanosoma brucei rhodesiense / drug effects
Substances
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Lactones
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Triterpenes
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urmiensolide
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Oleanolic Acid
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beta-amyrin