ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)