Lyngbyazothrins A-D, antimicrobial cyclic undecapeptides from the cultured Cyanobacterium lyngbya sp.
Four novel cyclic undecapeptides, lyngbyazothrins A (1), B (2), C (3), and D (4), were isolated from the cultured Lyngbya sp. 36.91 as binary mixtures (1/2 and 3/4). Their structures were elucidated by analysis of 1D (1H and 13C) and 2D (COSY, TOCSY, ROESY, NOESY, HMQC, and HMBC) NMR spectra, ESIMSMS, ESITOFMS, and amino acid analyses. Three unusual amino acids were present and identified as 4-methoxyhomophenylalanine in 1 and 3, homophenylalanine in 2 and 4, and 3-amino-2,5,7,8-tetrahydroxy-10-methylundecanoic acid (Aound) in all compounds, while 3 and 4 have an additional N-acetyl-N-methyltyrosine unit. The mixture of lyngbyazothrins A (1) and B (2) shows only low antimicrobial activity against Micrococcus flavus, whereas the mixture of lyngbyazothrins C (3) and D (4) was active against Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, and Serratia marcescens. It seems that the acyl residue at C-5 of the Aound unit plays an important role in antimicrobial activity.
Zainuddin
Elmi N
EN
Institute of Pharmacy, Ernst-Moritz-Arndt-University, Friedrich-Ludwig-Jahnstrasse 17, D-17487 Greifswald, Germany.
Jansen
Rolf
R
Nimtz
Manfred
M
Wray
Victor
V
Preisitsch
Michael
M
Lalk
Michael
M
Mundt
Sabine
S
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D000458:Cyanobacteria / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008837:Micrococcus / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012706:Serratia marcescens / Q000187:drug effects
D000900:Anti-Bacterial Agents; D010456:Peptides, Cyclic