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Mar. Drugs 2016, 14(12), 228; doi:10.3390/md14120228

First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge

1
Laboratory of Peptide Research and Development, School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad and Tobago
2
Department of Pharmacy, Mewar University, Gangrar, Chittorgarh, Rajasthan 312901, India
3
Department of Pharmacy, College of Health Sciences, Mizan-Tepi University, Mizan Teferi 5140, Ethiopia
4
Department of Pharmacy, College of Medical and Health Sciences, Wollega University, P.O. Box 395 Nekemte, Ethiopia
These two authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Russell Kerr
Received: 9 August 2016 / Revised: 9 December 2016 / Accepted: 12 December 2016 / Published: 15 December 2016
(This article belongs to the Special Issue Marine Fungal Natural Products)
View Full-Text   |   Download PDF [466 KB, uploaded 15 December 2016]   |  

Abstract

A natural heptacyclopeptide, stylissamide G (7), previously isolated from the Bahamian marine sponge Stylissa caribica from the Caribbean Sea, was synthesized via coupling of the tetrapeptide l-phenylalanyl-l-prolyl-l-phenylalanyl-l-proline methyl ester with the tripeptide Boc-l-leucyl-l-isoleucyl-l-proline, followed by cyclization of the linear heptapeptide fragment. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FT-IR, 1H NMR, 13C NMR and mass spectrometry. Results of pharmacological activity studies indicated that the newly synthesized cycloheptapeptide displayed good anthelmintic potential against Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea at 2 mg/mL and in addition, potent antifungal activity against pathogenic Candida albicans and dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL. View Full-Text
Keywords: stylissamide G; cycloheptapeptide; Stylissa caribica; peptide synthesis; macrocyclization; pharmacological activity; marine sponge stylissamide G; cycloheptapeptide; Stylissa caribica; peptide synthesis; macrocyclization; pharmacological activity; marine sponge
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MDPI and ACS Style

Dahiya, R.; Singh, S.; Sharma, A.; Chennupati, S.V.; Maharaj, S. First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge. Mar. Drugs 2016, 14, 228.

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