Structural and biological characterization of one antibacterial acylpolyamine isolated from the hemocytes of the spider Acanthocurria gomesiana.
We have isolated a 417Da antibacterial molecule, named mygalin, from the hemocytes of the spider Acanthoscurria gomesiana. The structure of mygalin was elucidated by tandem mass spectrometry (MS/MS) and by two spectroscopic techniques, nuclear magnetic resonance (NMR) and ultraviolet (UV) spectroscopy. Mygalin was identified as bis-acylpolyamine N1,N8-bis(2,5-dihydroxybenzoyl)spermidine, in which the primary amino groups of the spermidine are acylated with the carboxyl group of the 2,5-dihydroxybenzoic acid. Mygalin was active against Escherichia coli at 85muM, being this activity inhibited completely by catalase. Therefore, the antibacterial activity of mygalin was attributed to its production of hydrogen peroxide (H(2)O(2)). The putative mechanisms of formation of H(2)O(2) from mygalin are discussed. To our knowledge this is the first report of one bis-acylpolyamine with antibacterial activity purified from animal source.
Pereira
Lourivaldo S
LS
Parasitology Department, Biomedical Sciences Institute, São Paulo University, Av Prof Lineu Prestes, 1374, 05508-900 São Paulo, SP, Brazil.
Silva
Pedro I
PI
Miranda
M Terêsa M
MT
Almeida
Igor C
IC
Naoki
Hideo
H
Konno
Katsuhiro
K
Daffre
Sirlei
S
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D004926:Escherichia coli / Q000187:drug effects; D006434:Hemocytes / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D016982:Micrococcus luteus / Q000187:drug effects; D015394:Molecular Structure; D013095:Spermidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013112:Spiders / Q000737:chemistry*
D000900:Anti-Bacterial Agents; C518064:N1,N8-bis(2,5-dihydroxybenzoyl)spermidine; D013095:Spermidine