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J. Antibiot. 61(3): 149157, 2008
THE JOURNAL OF
ORIGINAL ARTICLE
ANTIBIOTICS
Essramycin: A First Triazolopyrimidine Antibiotic Isolated from Nature
Mervat M. A. El-Gendy, Mohamed Shaaban, Khaled A. Shaaban, Ahmed M. El-Bondkly, Hartmut Laatsch
Received: May 29, 2007 / Accepted: March 4, 2008 Japan Antibiotics Research Association
Abstract In the course of our screening program for new bio-active compounds, a novel triazolopyrimidine antibiotic, essramycin (1), was obtained from the culture broth of the marine Streptomyces sp., isolate Merv8102. Structure 1 was established by intensive NMR studies and by mass spectra. The compound is antibacterially active with MIC of 2 to 8m g/ml against Gram-positive and Gram-negative bacteria, while it showed no antifungal activity. The fermentation and isolation, as well as the structure elucidation and biological activity of 1 are described.
Keywords essramycin, triazolopyrimidine, marine Streptomyces sp.
Introduction
In spite of some technical specialities on handling [1], microorganisms derived from marine environments are widely recognized as a rising source of novel natural products [2 4]. In recent years, numerous metabolites possessing uncommon structures and potent bioactivity
have been isolated from strains of bacteria and fungi collected from diverse marine environments, such as animals, plants and sediments [5]. Triazolopyrimidines are synthetic heterocycles with valuable bioactivity [6 9]:
They are useful therapeutics, especially for the treatment and prevention of cardiovascular diseases and in particular for the treatment of hypertension, cardiac insufciency and diseases of the arterial wall, especially atherosclerosis [10]. They are known also as smooth muscle cell growth inhibitors [11] and are efcient analgesic and anti-inammatory agents [12]. However, compounds of this type have never been described as natural products so far.
In our program to investigate secondary metabolites from the marine environment, microbial strains collected from the sediments of the Mediterranean Sea at the Egyptian coast were investigated. The crude extracts obtained from the culture media of Streptomyces sp. isolate Merv8102 showed a potent activity against the bacteria Escherichia coli (ATCC 10536), Pseudomonas aeruginosa (ATCC 10145), Bacillus subtilis (ATCC 6051), Staphylococcus aureus (ATCC 6538), and Micrococcus luteus (ATCC 9341). Additionally, a moderate antifungal
K. A. Shaaban, H. Laatsch: Department of Organic and Biomolecular Chemistry, University of Gttingen, Tammannstrasse 2, D-37077 Gttingen, Germany,M. M. A. El-Gendy: Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical...