Next Article in Journal
GPCR Modulation of Thieno[2,3-b]pyridine Anti-Proliferative Agents
Next Article in Special Issue
Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga
Previous Article in Journal
Metabolomics Strategy Using High Resolution Mass Spectrometry Reveals Novel Biomarkers and Pain-Relief Effect of Traditional Chinese Medicine Prescription Wu-Zhu-Yu Decoction Acting on Headache Modelling Rats
Previous Article in Special Issue
Anti-Proliferative Activity of Triterpenoids and Sterols Isolated from Alstonia scholaris against Non-Small-Cell Lung Carcinoma Cells
Article Menu
Issue 12 (December) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(12), 2252; https://doi.org/10.3390/molecules22122252

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

1
Pharmaceutical Biology, Pharmazentrum, University of Basel, Klingelbergstrasse 50, 4056 Basel, Switzerland
2
Molecular Modeling, Pharmazentrum, University of Basel, Klingelbergstrasse 50, 4056 Basel, Switzerland
3
Department of Medical Parasitology & Infection Biology, Swiss Tropical and Public Health Institute, Socinstrasse 57, 4000 Basel, Switzerland
4
University of Basel, Petersplatz 1, 4001 Basel, Switzerland
*
Authors to whom correspondence should be addressed.
Received: 16 November 2017 / Revised: 13 December 2017 / Accepted: 13 December 2017 / Published: 18 December 2017
(This article belongs to the Special Issue Diversity of Terpenoids)
View Full-Text   |   Download PDF [2496 KB, uploaded 18 December 2017]   |  

Abstract

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. View Full-Text
Keywords: sesquiterpene lactones; epoxygermacranolides; acid-catalyzed rearrangement; mechanism of reaction; anti-protozoal activity sesquiterpene lactones; epoxygermacranolides; acid-catalyzed rearrangement; mechanism of reaction; anti-protozoal activity
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

De Mieri, M.; Smieško, M.; Ismajili, I.; Kaiser, M.; Hamburger, M. Acid-Induced Rearrangement of Epoxygermacranolides: Synthesis of Furanoheliangolides and Cadinanes from Nobilin. Molecules 2017, 22, 2252.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top