Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596366
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Antinflammatory sesquiterpene compounds from the aerial parts of Onopordum illyricum L.

C Formisano
1   Department of Pharmacy, University of Naples “Federico II”, via D. Montesano 49, 80131 Naples, Italy
,
D Rigano
1   Department of Pharmacy, University of Naples “Federico II”, via D. Montesano 49, 80131 Naples, Italy
,
C Sirignano
1   Department of Pharmacy, University of Naples “Federico II”, via D. Montesano 49, 80131 Naples, Italy
,
C Sanna
2   Department of Life and Environmental Sciences, University of Cagliari, Cagliari, Italy
,
M Ballero
2   Department of Life and Environmental Sciences, University of Cagliari, Cagliari, Italy
,
F Esposito
2   Department of Life and Environmental Sciences, University of Cagliari, Cagliari, Italy
,
E Tramontano
2   Department of Life and Environmental Sciences, University of Cagliari, Cagliari, Italy
,
O Taglialatela-Scafati
1   Department of Pharmacy, University of Naples “Federico II”, via D. Montesano 49, 80131 Naples, Italy
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

 

The genus Onopordum L. includes about 50 species belonging to the tribe Cardueae (Asteraceae). Plants of the genus Onopordum have been employed traditionally for their antibacterial, hemostatic, hypotensive properties and for the treatment of skin cancer. Some biological activities of Onopordum species include the augmentation of the NK cell activity and the inhibition of TNF-α and nitric oxide in murine endothelial cells [1]. The metabolites isolated from Onopordum species include sesquiterpenoids, flavonoids, acetylenic compounds, steroids, triterpenes, lipids and nitrogen containing compounds [2]. O. illyricum L. is widely distributed along the Mediterranean coast of Italy where it grows wild and is called “Cardo maggiore”. The investigation on ethyl acetate extract of this plant led to the isolation of 6 sesquiterpenes: three (1-3) belonging to elemane type, two (4-5) belonging to germacrane type and one eudesmane (6). These 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.

The structure-activity relationships (SAR) have been rationalized in the light of the NMR spectroscopy-based cysteamine assay [3].

Zoom Image

Keywords: Onopordum, sesquiterpene lactones, antinflammatory, cysteamine assay.

References:

[1] Abuharfeil NM, Salim M, Von Kleist S. Augmentation of natural killer cell activity in vivo against tumour cells by some wild plants from Jordan. Phytother Res 2001; 15: 109 – 113

[2] Bruno M, Maggio A, Rosselli S, Safder M, Bancheva S. The metabolites of the genus Onopordum (Asteraceae): chemistry and biological properties. Curr Org Chem 2011; 15: 888 – 927

[3] Appendino G, Minassi A, Collado JA, Pollastro F, Chianese G, Taglialatela-Scafati O, Ayyari M, Garcia V, Munoz E. The Thia-Michael Reactivity of Zerumbone and Related Cross-Conjugated Dienones: Disentangling Stoichiometry, Regiochemistry, and Addition Mode with an NMR-Spectroscopy-Based Cysteamine Assay. Eur J Org Chem 2015; 17: 3721 – 3726