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Molecules 2017, 22(6), 682; doi:10.3390/molecules22060682

Total Synthesis and Pharmacological Investigation of Cordyheptapeptide A

1
Institute of Pharmaceutical Sciences, Kurukshetra University, Kurukshetra 136119, Haryana, India
2
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
3
School of Pharmacy, College of Medicine and Health Sciences, University of Gondar, P.O. Box 196, Gondar 6200, Ethiopia
4
Department of Pharmacy, College of Medical and Health Sciences, Wollega University, P.O. Box 395, Nekemte, Ethiopia
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Nancy D. Turner
Received: 23 March 2017 / Revised: 17 April 2017 / Accepted: 18 April 2017 / Published: 27 May 2017
(This article belongs to the Collection Bioactive Compounds)
View Full-Text   |   Download PDF [638 KB, uploaded 27 May 2017]   |  

Abstract

The present investigation reports the synthesis of a phenylalanine-rich N-methylated cyclopeptide, cordyheptapeptide A (8), previously isolated from the insect pathogenic fungus Cordyceps sp. BCC 1788, accomplished through the coupling of N-methylated tetrapeptide and tripeptide fragments followed by cyclization of the linear heptapeptide unit. Structure elucidation of the newly synthesized cyclopolypeptide was performed by means of FT-IR, 1H-NMR, 13C-NMR, and fast atom bombardment mass spectrometry (FABMS), and screened for its antibacterial, antidermatophytic, and cytotoxic potential. According to the antimicrobial activity results, the newly synthesized N-Methylated cyclopeptide exhibited potent antibacterial activity against Gram-negative bacteria Pseudomonas aeruginosa and Klebsiella pneumoniae and antifungal activity against dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL, in comparison to the reference drugs, gatifloxacin and griseofulvin. In addition, cyclopolypeptide 8 displayed suitable levels of cytotoxicity against Dalton’s lymphoma ascites (DLA) and Ehrlich’s ascites carcinoma (EAC) cell lines. View Full-Text
Keywords: cordyheptapeptide A; solution-phase peptide synthesis; coupling; cytotoxicity; macrocyclization; biological activity; insect pathogenic fungus cordyheptapeptide A; solution-phase peptide synthesis; coupling; cytotoxicity; macrocyclization; biological activity; insect pathogenic fungus
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Kumar, S.; Dahiya, R.; Khokra, S.L.; Mourya, R.; Chennupati, S.V.; Maharaj, S. Total Synthesis and Pharmacological Investigation of Cordyheptapeptide A. Molecules 2017, 22, 682.

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