Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer

Marco Masi, Liliya V. Frolova, Xiaojie Yu, Véronique Mathieu, Alessio Cimmino, Annelise De Carvalho, Robert Kiss, Snezna Rogelj, Alexander Pertsemlidis, Alexander Kornienko, Antonio Evidente

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Abstract

A new alkaloid, belonging to the pretazettine group of Amaryllidaceae alkaloids, was isolated from dried bulbs of Narcissus jonquilla quail and named jonquailine. Its structure, including the absolute configuration, was elucidated using various NMR, ECD and ESI MS techniques. Initial biological evaluation revealed significant antiproliferative effects against glioblastoma, melanoma, uterine sarcoma and non-small-cell lung cancer cells displaying various forms of drug resistance, including resistance to apoptosis and multi-drug resistance. Jonquailine was also found to synergize with paclitaxel in its antiproliferative action against drug-resistant lung cancer cells. The results obtained compared with literature data also showed that the hydroxylation at C-8 is an important feature for the anticancer activity but this seems unaffected by the stereochemistry or the acetalization of the lactol.

Original languageEnglish (US)
Pages (from-to)41-48
Number of pages8
JournalFitoterapia
Volume102
DOIs
StatePublished - Apr 2015

Keywords

  • Alkaloids
  • Amaryllidaceae
  • Antiproliferative effects
  • Cancer cells
  • Jonquailine
  • Narcissus jonquilla quail

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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    Masi, M., Frolova, L. V., Yu, X., Mathieu, V., Cimmino, A., De Carvalho, A., Kiss, R., Rogelj, S., Pertsemlidis, A., Kornienko, A., & Evidente, A. (2015). Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer. Fitoterapia, 102, 41-48. https://doi.org/10.1016/j.fitote.2015.01.009