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Synthesis and biological activity of a cyclic hexapeptide from Dianthus superbus

Rajiv Dahiya

Department of Pharmaceutical Chemistry, Rajiv Academy for Pharmacy, PO Chattikara, Mathura, 281 001, Uttar Pradesh (UP), India

 

E-mail: rajivdahiya04@yahoo.co.in

Received: 10 October 2007  Revised: 19 January 2008  Accepted: 13 February 2008

Abstract: Plant-originated cyclopolypeptide (XIII) was synthesized by coupling of dipeptide Boc-l-asn(bzh)-l-phe-OH and tetrapeptide gly-l-leu-l-ala-l-tyr-OMe followed by cyclization of a linear hexapeptide segment. Structure elucidation of XIII was done on basis of detailed spectral analysis including FTIR, 1H NMR, 13C NMR, FAB MS and elemental analysis. From the results of pharmacological screening, it was concluded that XIII possesses high cytotoxic activity against DLA and EAC cell lines with CTC50 values of 15.1 μM and 18.6 μM, and potent antimicrobial activity against pathogenic fungi C. albicans with MIC of 6 μg mL−1. Moreover, XIII possesses moderate anthelmintic activity against earthworms M. konkanensis, P. corethruses, and Eudrilus sp. at 2 mg mL−1 dose level.

Keywords: dianthin A - cyclohexapeptide -  Dianthus superbus  - peptide synthesis - cytotoxicity - anthelmintic and antifungal activities

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-008-0052-9

 

Chemical Papers 62 (5) 527–535 (2008)

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