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Poly-Electrophilic Sesquiterpene Lactones from Vernonia amygdalina: New Members and Differences in Their Mechanism of Thiol Trapping and in Bioactivity.

Abstract
In addition to known compounds, the leaves of Vernonia amygdalina afforded the new sesquiterpene lactones 14-O-methylvernolide (2), 3'-deoxyvernodalol (6), and vernomygdalin (8). These and related compounds were evaluated for modulation of a series of thiol trapping-sensitive transcription factors (NF-κB, STAT3, and Nrf2), involved in the maintenance of the chronic inflammatory condition typical of human degenerative diseases. Vernolide (1) emerged as a potent inhibitor of STAT3 and NF-κB and showed cytostatic activity toward the prostate cancer cell line DU45, arresting the cell cycle at the S phase. The exomethylene lactones are characterized by multiple Michael acceptor sites, as exemplified by vernolide (1) and vernodalol (5). By using the nuclear magnetic resonance-based cysteamine assay, the most reactive thiophilic site could be identified in both compounds, and competitive experiments qualified vernolide (1) as being more thiophilic than vernodalol (5), in agreement with the results of the pharmacological assays.
AuthorsAnnamaria Sinisi, Estrella Millán, Solomon M Abay, Annette Habluetzel, Giovanni Appendino, Eduardo Muñoz, Orazio Taglialatela-Scafati
JournalJournal of natural products (J Nat Prod) Vol. 78 Issue 7 Pg. 1618-23 (Jul 24 2015) ISSN: 1520-6025 [Electronic] United States
PMID26115003 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Lactones
  • NF-E2-Related Factor 2
  • NF-kappa B
  • NFE2L2 protein, human
  • STAT3 Transcription Factor
  • Sesquiterpenes
  • Sulfhydryl Compounds
  • vernodalol
  • vernolide
  • Cysteamine
Topics
  • Cell Cycle (drug effects)
  • Cysteamine (chemistry)
  • Humans
  • Lactones (chemistry, isolation & purification, pharmacology)
  • Molecular Structure
  • NF-E2-Related Factor 2 (drug effects)
  • NF-kappa B (drug effects)
  • Plant Leaves (chemistry)
  • STAT3 Transcription Factor (drug effects)
  • Sesquiterpenes (chemistry, isolation & purification, pharmacology)
  • Sulfhydryl Compounds (chemistry, pharmacology)
  • Vernonia (chemistry)

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