Secondary metabolites of Centaurea calolepis and evaluation of cnicin for anti-inflammatory, antioxidant, and cytotoxic activities.

Abstract

CONTEXT:

Centaurea L. (Astreaceae) species are used as herbal remedies in Turkey. Centaurea calolepis Boiss. is an endemic species of Anatolia that has not been subjected to phytochemical studies except essential oil analysis.

OBJECTIVE:

Secondary metabolite determination, isolation and structure elucidation of pure compounds were performed on C. calolepis. Cnicin, which is the main component of several Centaurea species, was tested for its in vitro anti-inflammatory, antioxidant and cytotoxic activities.

MATERIALS AND METHODS:

Chloroform and methanol extracts of the aerial parts of C. calolepis were subjected to isolation process using column chromatography. The structures of the compounds were characterized by 1D- and 2D-NMR experiments. Thin-layer chromatography and high performance liquid chromatography were used in determination of phenolics. Cnicin was subjected to a panel of cellular assays to test for inhibition of nuclear factor κB (NF-κB), inducible nitric oxide synthase (iNOS), reactive oxygen species and cytotoxicity.

RESULTS:

Cnicin, lucenin-2, schaftoside and 3-O-feruloylquinic acid were isolated from C. calolepis extracts. Vicenin-2, vitexin, isovitexin, homoorientin, rutin, orientin, luteolin-7-O-glycoside and chlorogenic acid were determined in fractions. Cnicin showed inhibition of NF-κB and inhibition of iNOS activity with IC₅₀ Values of 1.8 and 6.5 µM, respectively. Cytotoxic activity of cnicin was observed toward pig kidney epithelial (LLC-PK₁₁), human malignant melanoma (SK-MEL) and human ductal carcinoma (BT-549) cells with IC₅₀ values of 23.3, 14.0 and 18.3 µM, respectively.

DISCUSSION AND CONCLUSION:

This is the first detailed report of secondary metabolites of C. calolepis. Evaluation of biological activity of cnicin establishes the potential of this compound as an anti-inflammatory and cytotoxic agent.

• Authors: Sura Baykan Erel, Canan Karaalp, Erdal Bedir, Hanspeter Kaehlig, Sabine Glasl, Shabana Khan, Liselotte Krenn
• Journal: Pharmaceutical biology (Pharm Biol) Vol. 49 Issue 8 Pg. 840-9 (Aug 2011) ISSN: 1744-5116 [Electronic] England
• PMID: 21612369 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Anti-Inflammatory Agents
• Antineoplastic Agents
• Antioxidants
• Cytotoxins
• Glycosides
• NF-kappa B
• Plant Extracts
• Reactive Oxygen Species
• Sesquiterpenes
• cnicin
• Nitric Oxide Synthase Type II

Topics

• Animals
• Anti-Inflammatory Agents (chemistry, metabolism, pharmacology)
• Antineoplastic Agents (chemistry, metabolism, pharmacology)
• Antioxidants (chemistry, metabolism, pharmacology)
• Cell Line
• Cell Line, Tumor
• Centaurea (chemistry, metabolism)
• Cytotoxins (chemistry, metabolism, pharmacology)
• Glycosides (chemistry, isolation & purification)
• Haplorhini
• Humans
• NF-kappa B (antagonists & inhibitors, metabolism)
• Nitric Oxide Synthase Type II (drug effects, metabolism)
• Phytotherapy
• Plant Components, Aerial
• Plant Extracts (metabolism, pharmacology)
• Reactive Oxygen Species (metabolism)
• Sesquiterpenes (chemistry, metabolism, pharmacology)
• Swine
• Turkey