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Antitrypanosomal Triterpenoid with an ε-Lactone E-Ring from Salvia urmiensis
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 2184946
Author(s) Farimani, Mahdi Moridi; Ebrahimi, Samad Nejad; Salehi, Peyman; Bahadori, Mir Babak; Sonboli, Ali; Khavasi, Hamid Reza; Zimmermann, Stefanie; Kaiser, Marcel; Hamburger, Matthias
Author(s) at UniBasel Kaiser, Marcel
Hamburger, Matthias
Ebrahimi, Samad
Zimmermann, Stefanie
Year 2013
Title Antitrypanosomal Triterpenoid with an ε-Lactone E-Ring from Salvia urmiensis
Journal Journal of natural products
Volume 76
Number 9
Pages / Article-Number 1806-9
Mesh terms Crystallography, X-Ray; Inhibitory Concentration 50; Iran; Lactones, chemistry; Molecular Conformation; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oleanolic Acid, metabolism; Parasitic Sensitivity Tests; Plasmodium falciparum, drug effects; Salvia, chemistry; Stereoisomerism; Triterpenes, pharmacology; Trypanosoma brucei rhodesiense, drug effects
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.
Publisher American Chemical Society
ISSN/ISBN 0163-3864
edoc-URL http://edoc.unibas.ch/dok/A6183919
Full Text on edoc No
Digital Object Identifier DOI 10.1021/np400337a
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/24007549
Document type (ISI) Journal Article
 
   

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29/03/2024