Acid-Induced Rearrangement of Epoxygermacranolides: Synthesis of Furanoheliangolides and Cadinanes from Nobilin

Autor: Matthias Hamburger, Martin Smieško, Isidor Ismajili, Maria De Mieri, Marcel Kaiser
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Trypanosoma brucei rhodesiense
epoxygermacranolides
Pharmaceutical Science
Sesquiterpene lactone
01 natural sciences
Analytical Chemistry
Sesquiterpenes
Germacrane
chemistry.chemical_compound
Drug Discovery
Lewis acids and bases
Lewis Acids
chemistry.chemical_classification
sesquiterpene lactones
acid-catalyzed rearrangement
mechanism of reaction
anti-protozoal activity
Molecular Structure
Chemistry
Lewis acid catalysis
Chamaemelum
Chemistry (miscellaneous)
Molecular Medicine
Sesquiterpenes
Bridged-Ring Compounds
Sesterterpenes
Stereochemistry
Trypanosoma cruzi
Plasmodium falciparum
Antiprotozoal Agents
010402 general chemistry
Catalysis
Article
lcsh:QD241-441
Inhibitory Concentration 50
lcsh:Organic chemistry
Biosynthesis
Molecule
Reactivity (chemistry)
Parthenolide
Physical and Theoretical Chemistry
Furans
Polycyclic Sesquiterpenes
Plant Extracts
010405 organic chemistry
Organic Chemistry
0104 chemical sciences
Cyclization
Leishmania donovani
Zdroj: Molecules; Volume 22; Issue 12; Pages: 2252
Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
Molecules, Vol 22, Iss 12, p 2252 (2017)
ISSN: 1420-3049
DOI: 10.3390/molecules22122252
Popis: The acid-induced rearrangement of three epoxyderivatives of nobilin 1, the most abundant sesquiterpene lactone in Anthemis nobilis flowers, was investigated. From the 1,10-epoxyderivative 2, furanoheliangolide 5 was obtained, while the 4,5-epoxy group of 3 did not react. Conversely, when the 3-hydroxy function of nobilin was acetylated (12), the 4,5-epoxy derivative did cyclize into cadinanes (15 and 16) under Lewis acid catalysis. The reactivity of the 4,5- and 1,10-epoxy derivatives of nobilin (2 and 3) was compared with that of parthenolide, and rationalized on the basis of quantum chemical calculations. All isolated reaction products were fully characterized by spectroscopic and computational methods, and their in vitro anti-protozoal activity was evaluated. The paper could provide new insights into the biosynthesis of this class of natural products.
Databáze: OpenAIRE
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