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Antiprotozoal activity of diterpenoids isolated from Zhumeria majdae - absolute configuration by circular dichroism
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4604287
Author(s) Zadali, Reza; Ebrahimi, Samad Nejad; Tofighi, Zahra; Es-haghi, Ali; Hamburger, Matthias; Kaiser, Marcel; D'Ambola, Massimiliano; De Tommasi, Nunziatina; Hadjiakhoondi, Abbas
Author(s) at UniBasel Hamburger, Matthias
Kaiser, Marcel
Year 2020
Title Antiprotozoal activity of diterpenoids isolated from Zhumeria majdae - absolute configuration by circular dichroism
Journal DARU Journal of Pharmaceutical Sciences
Volume 28
Number 2
Pages / Article-Number 455-462
Keywords Abietane diterpenoids; Electronic circular dichroism; Lamiaceae; Malaria; Trypanosoma
Mesh terms Animals; Antiprotozoal Agents, pharmacology; Cell Line; Circular Dichroism; Diterpenes, pharmacology; Inhibitory Concentration 50; Iran; Leishmania donovani, drug effects; Molecular Structure; Phytochemicals, pharmacology; Plant Components, Aerial, chemistry; Plant Roots, chemistry; Plasmodium falciparum, drug effects; Rats; Salvia, chemistry; Trypanosoma, drug effects; Trypanosoma brucei rhodesiense, drug effects; Trypanosoma cruzi, drug effects
Abstract Zhumeria majdae, a unique species of the Zhumeria genus, is an endemic Iranian plant in the Lamiaceae family. Phytochemical investigation and biological activity of this plant are rarely reported. The current study aimed to find new antiprotozoal compounds from the roots of Z. majdae and to determine the absolute configuration of isolated compounds by circular dichroism. The extraction process from roots and aerial parts of Z. majdae was carried out by hexane, ethyl acetate and methanol followed by testing their antiprotozoal effects against Leishmania donovani, Trypanosoma brucei rhodesiense, T. cruzi, and Plasmodium falciparum, respectively. Structure elucidation was done using 1D and 2D NMR spectroscopy and HREIMS spectrometry. In addition, experimental and theoretical circular dichroism spectroscopy was used to establish absolute configuration. In comparison with aerial parts, the hexane extract from roots showed superior activity against T. b. rhodesiense, L. donovani and P. falciparum with IC50 values of 5.4, 1.6 and 2.1 μg/ml, respectively. From eight abietane-type diterpenoids identified in roots, six were reported for the first time in the genus Zhumeria. 11,14-dihydroxy-8,11,13-abietatrien-7-one (6) exhibited a promising biological activity against P. falciparum (IC50 8.65 μM), with a selectivity index (SI) of 4.6, and lanugon Q (8) showed an IC50 value of 0.13 μM and SI of 15.4 against T. b. rhodesiense. Altogether, according to the results, of 8 isolated compounds, dihydroxy-8,11,13-abietatrien-7-one (6) and lanugon Q (8) exhibited a promising activity against T. b. rhodesiense and P. falciparum. In conclusion, these compounds could be potential candidates for further analysis and may serve as lead compounds for the synthesis of antiprotozoal agents.
Publisher Springer
ISSN/ISBN 1560-8115 ; 2008-2231
URL https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/32394309/
edoc-URL https://edoc.unibas.ch/79463/
Full Text on edoc No
Digital Object Identifier DOI 10.1007/s40199-020-00345-w
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/32394309
ISI-Number WOS:000531774800001
Document type (ISI) Journal Article
 
   

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