Structure-antibacterial relationship of nigericin derivatives

Two new polyether antibiotics 3, 5 together with three known ones 1, 2, 4 were isolated from Streptomyces hygroscopicus XM201. Based on the unambiguous NMR data assignments, their structures were determined to be 30-acetyl nigericin (1), 1-O-methyl-30-acetyl nigericin (2), 1,29-O-dimethyl-30-acetyl...

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Bibliographic Details
Published in:Chemistry of natural compounds 2009-05, Vol.45 (3), p.333-337
Main Authors: Wu, Zhaoxian, Bai, Linquan, Wang, Mingzi, Shen, Yuemao
Format: Article
Language:English
Subjects:
antibacterial properties
Bacillus cereus
Escherichia coli
Medicine
minimum inhibitory concentration
nigericin
nuclear magnetic resonance spectroscopy
Organic Chemistry
Pharmacy
Plant Sciences
Staphylococcus aureus
Streptomyces hygroscopicus
structure-activity relationships
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Summary:Two new polyether antibiotics 3, 5 together with three known ones 1, 2, 4 were isolated from Streptomyces hygroscopicus XM201. Based on the unambiguous NMR data assignments, their structures were determined to be 30-acetyl nigericin (1), 1-O-methyl-30-acetyl nigericin (2), 1,29-O-dimethyl-30-acetyl nigericin (3), nigericin (4), and 29-O-methyl abierixin (5), respectively. The antibacterial activities of the nigericin derivatives 1-4 were studied. Compounds 1 and 4 showed strong activities against Staphylococcus aureus ATCC25923 and Bacillus cereus 1126 with MIC of 0.25 μg/mL and 0.125 μg/mL, respectively. No inhibitory activities were observed against Escherichia coli CMCC44103 at a concentration of 25 μg/mL. Only 1 and 4 showed distinguished effects on the protoplast regeneration clones of B. cereus 1126 and E. coli CMCC44103 at a concentration of 1 μg/mL.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-009-9350-x