First Total Synthesis and Pharmacological Potential of a Plant Based Hexacyclopeptide

Document Type: Research article

Authors

1 Laboratory of Peptide Research and Development, School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad & Tobago, West Indies.

2 Department of Pharmacy, Faculty of Pharmaceutical Science, Mewar University, Gangrar, Chittorgarh, Rajasthan, India.

3 Department of Pharmaceutical Sciences, USF College of Pharmacy, University of South Florida, Tampa, FL 33612-4749, USA.

4 Department of Pharmaceutical Sciences, USF College of Pharmacy, University of South Florida, Tampa, FL 33612-4749, USA

5 Department of Pharmacogenomics, Bernard J. Dunn School of Pharmacy, Shenandoah University- ICPH Fairfax, Fairfax, VA 22031, USA

6 School of Pharmacy, College of Medicine and Health Sciences, University of Gondar, Gondar 196, Ethiopia.

7 Department of Pharmacy, College of Medical and Health Sciences, Wollega University, P.O. Box 395, Nekemte, Ethiopia.

8 Department of Pharmacognosy, Amity Institute of Pharmacy, Amity University, Gwalior, Madhya Pradesh, India.

Abstract

  A new bioactive proline-rich cyclohexapeptide - diandrine C (6), previously isolated from whole plant of Drymaria diandra (Caryophyllaceae), was synthesized through coupling reactions of tetrapeptide unit Boc-Gly-l-Pro-l-Tyr-l-Trp-OH with dipeptide unit l-Pro-Gly-OMe using N,N-diisopropylcarbodiimide (DIPC) as the coupling agent, followed by cyclization of linear hexapeptide unit under alkaline condition. Structure of cyclohexapeptidewas confirmed by means of chemical, and spectroscopic analyses and also was screened for its antimicrobial and anthelmintic properties. Bioevaluation results indicated that the newly synthesized hexacyclopeptide exhibited potent antimicrobial activity against Gram-negative bacteria Pseudomonas aeruginosa, Klebsiella pneumoniae and pathogenic Candida albicans at 6 mg/mL. Moderate to good level of antihelmintic activity against three earthworm species Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea was also observed at concentration of 2 mg/mL.
 

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