Sesquiterpene Lactones from Vernonia tufnelliae: Structural Characterization and Biological Evaluation

• Published in: Journal of natural products (Washington, D.C.) Vol. 85; no. 7; pp. 1681 - 1690
• Main Authors: Bitchagno, Gabin Thierry M., Schüffler, Anja, Gross, Jonathan, Krumb, Matthias, Tane, Pierre, Opatz, Till
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society and American Society of Pharmacognosy 22-07-2022
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.2c00055

The genus Vernonia is an extremely rich source of biologically active sesquiterpene lactones. The present report describes the spectroscopic structure elucidation and the cytotoxic and antimicrobial properties of five hitherto unknown germacranolide-like sesquiterpenoids and several known compounds. These new derivatives include a compound (1) with an unprecedented 10/5/5/6 tetracyclic framework featuring a hexahydro-1H,3H,7H-furo­[3′,4′:3,4]­furo­[3,2-c]­pyridin-1-one core resulting from an intramolecular cyclization cascade involving a methacrylate substituent and a low molecular weight amine. Furthermore, an elemane–germacranolide hybrid (2) and three amino acid-derived lactones (3–5) were characterized. A plausible biosynthetic pathway to the key alkaloid is presented, while shielding tensor calculations using DFT in combination with the DP4+ method were applied to elucidate its stereostructure. The newly characterized compounds along with ten known sesquiterpene lactones and phenolic compounds have been isolated from Vernonia tufnelliae, a medicinal plant from the western region of Cameroon. Their structures were consistent with spectroscopic and spectrometric data recorded. The present report is the first investigation of the chemistry and biology of V. tufnelliae.