Phytochemical Profile and Apoptotic Activity of Onopordum cynarocephalum

Carmen Formisano; Daniela Rigano; Alessandra Russo; Venera Cardile; Silvia Caggia; Nelly Apostolides Arnold; Angela Mari; Sonia Piacente; Sergio Rosselli; Felice Senatore; Maurizio Bruno

doi:10.1055/s-0032-1315259

Planta Medica, Table of Contents

Planta Med 2012; 78(15): 1651-1660
DOI: 10.1055/s-0032-1315259

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Phytochemical Profile and Apoptotic Activity of Onopordum cynarocephalum

Authors

Carmen Formisano

¹Department of Chemistry of Natural Products, University of Naples Federico II, Naples, Italy
Daniela Rigano

¹Department of Chemistry of Natural Products, University of Naples Federico II, Naples, Italy
Alessandra Russo

²Department of Drug Sciences, Biochemistry Section, University of Catania, Catania, Italy
Venera Cardile

³Department of Bio-medical Sciences, University of Catania, Catania, Italy
Silvia Caggia

³Department of Bio-medical Sciences, University of Catania, Catania, Italy
Nelly Apostolides Arnold

⁴Faculty of Agronomic Sciences, University of Saint Esprit, Kaslik (Beyrouth), Lebanon
Angela Mari

⁵Department of Pharmaceutical and Biomedical Sciences, University of Salerno, Salerno, Italy
Sonia Piacente

⁵Department of Pharmaceutical and Biomedical Sciences, University of Salerno, Salerno, Italy
Sergio Rosselli

⁶Department of Molecular and Biomolecular Science and Technology, Organic Chemistry Section, University of Palermo, Palermo, Italy
Felice Senatore

¹Department of Chemistry of Natural Products, University of Naples Federico II, Naples, Italy
Maurizio Bruno

⁶Department of Molecular and Biomolecular Science and Technology, Organic Chemistry Section, University of Palermo, Palermo, Italy

Abstract

A phytochemical investigation of acetone and chloroform extracts of the aerial parts of Onopordum cynarocephalum Boiss. et Blanche was carried out. It led to the isolation of two new sesquiterpenes, the elemane aldehyde (2) and the eudesmane (11), together with 15 known compounds: two lignans (1 and 15) and 13 sesquiterpenes (3–10, 12–14, 16, 17). The structures were elucidated by spectroscopic analyses, especially 1D and 2D NMR spectra. The anti-growth effect against three human melanoma cell lines, M14, A375, and A2058, of the different extracts and compounds of O. cynarocephalum was also investigated. Among them, the chloroform extract exhibited the strongest biological activity, while the most active compounds were the lignan arctigenin (1), and the sesquiterpenes, compounds 3, 5, and 6 belonging to the elemane type, and 7 belonging to the eudesmane type. Our data also demonstrate that acetone and chloroform extracts induce, in the A375 cell line, apoptotic cell death that could be related to an overall action of the compounds present, but in particular to the lignans arctigenin (1) and the sesquiterpenes compounds 3–8 and 16. In fact, these molecules were able to induce a high DNA fragmentation, correlated to a significant increase of the caspase-3 enzyme activity. Furthermore, apoptosis appears to be mediated, at least in part, via PTEN activity and the inhibition of Hsp70 expression.

Key words

Onopordum cynarocephalum - Asteraceae - sesquiterpenes - melanoma - apoptosis - heat shock protein 70

Full Text

References

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