Antiprotozoal Activity-Based Profiling of a Dichloromethane Extract from Anthemis nobilis Flowers

Autor: Matthias Hamburger, Isidor Ismajili, Maria De Mieri, Giannicola Monteleone, Marcel Kaiser
Rok vydání: 2017
Předmět:
Bridged-Ring Compounds
Trypanosoma brucei rhodesiense
Circular dichroism
Sesterterpenes
medicine.drug_class
Stereochemistry
Trypanosoma cruzi
Plasmodium falciparum
Antiprotozoal Agents
Pharmaceutical Science
Flowers
010402 general chemistry
Sesquiterpene lactone
Sesquiterpene
01 natural sciences
Analytical Chemistry
Lactones
Sesquiterpenes
Germacrane
chemistry.chemical_compound
Drug Discovery
medicine
Animals
Potency
Anthemis
Furans
Dichloromethane
Polycyclic Sesquiterpenes
Pharmacology
chemistry.chemical_classification
Methylene Chloride
Molecular Structure
biology
010405 organic chemistry
Organic Chemistry
biology.organism_classification
Trypanocidal Agents
0104 chemical sciences
Complementary and alternative medicine
chemistry
Chamaemelum
Antiprotozoal
Molecular Medicine
Sesquiterpenes
Leishmania donovani
Zdroj: Journal of Natural Products. 80:459-470
ISSN: 1520-6025
0163-3864
DOI: 10.1021/acs.jnatprod.6b00980
Popis: A dichlomethane extract of Anthemis nobilis flower cones showed promising in vitro antiprotozoal activity against Trypanosoma brucei rhodesiense and Leishmania donovani, with IC50 values of 1.43 ± 0.50 and 1.40 ± 0.07 μg/mL, respectively. A comprehensive profiling of the most active fractions afforded 19 sesquiterpene lactones, including 15 germacranolides, two seco-sesquiterpenes, one guaianolide sesquiterpene lactone, and one cadinane acid. Of these, 13 compounds were found to be new natural products. The compounds were characterized by extensive spectroscopic data analysis (1D and 2D NMR, HRMS, circular dichroism) and computational methods, and their in vitro antiprotozoal activity was evaluated. The furanoheliangolide derivative 15 showed high potency and selectivity in vitro against T. b. rhodesiense bloodstream forms (IC50 0.08 ± 0.01 μM; SI 63). In silico calculations were consistent with the drug-like properties of 15.
Databáze: OpenAIRE
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