Abstract
The present study deals with the synthesis of a novel proline-rich cyclopeptide - gypsin B 7 via coupling of tripeptide units Boc-l-Tyr-l-Phe-l-Pro-OH and Gly-l-Leu-l-Pro-OMe utilizing two different carbodiimides, followed by cyclization of linear polypeptide fragment. Structure elucidation of newly synthesized peptide was done on basis of FT-IR, 1H-NMR, 13C-NMR, ESI-MS/MS data. From biological evaluation, it was concluded that cyclic hexapeptide 7 exhibited potent antidermatophyte activity against pathogenic Microsporum audouinii andTrichophyton mentagrophytes. Also, good bioactivity against pathogenicCandida albicans and gram-negative bacteria, and moderate antihelmintic activity against three species of earthworms was observed for newly synthesized cyclohexapeptide. Key words: Gypsophila arabica, cyclic hexapeptide, gypsin B, peptide coupling, antimicrobial activity, antihelmintic activity.
Highlights
Diverse reports in past literature have proved the potential of roots of plants to produce a range of natural products with different pharmacological activities (Tan and Zhou, 2006)
Good bioactivity against pathogenic Candida albicans and gram-negative bacteria, and moderate antihelmintic activity against three species of earthworms was observed for newly synthesized cyclohexapeptide
A novel cyclic hexapeptide, gypsin B has been isolated from roots of Gypsophila arabica (Caryophyllaceae) and its structure was elucidated from the spectroscopic and chemical evidence
Summary
Diverse reports in past literature have proved the potential of roots of plants to produce a range of natural products with different pharmacological activities (Tan and Zhou, 2006). As part of our continuing synthetic efforts on biologically active peptides (Dahiya et al, 2006; Dahiya and Kaur, 2007; Dahiya and Pathak, 2007; Dahiya and Sharma, 2008; Dahiya and Kumar, 2008; Dahiya et al, 2009; Dahiya and Gautam, 2010), the present investigation was aimed at the synthesis of a novel cyclic hexapeptide of plant origin. Keeping in view of significant bioactivities possessed by natural cyclopolypeptides (Dahiya and Pathak, 2006; Pathak and Dahiya, 2003), the above synthetic peptide was further subjected to antibacterial, antifungal and antihelmintic activity studies
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