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Title: Structural and biological characterization of one antibacterial acylpolyamine isolated from the hemocytes of the spider Acanthocurria gomesiana

Abstract

We have isolated a 417 Da 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 85 {mu}M, being this activity inhibited completely by catalase. Therefore, the antibacterial activity of mygalin was attributed to its production of hydrogen peroxide (H{sub 2}O{sub 2}). The putative mechanisms of formation of H{sub 2}O{sub 2} from mygalin are discussed. To our knowledge this is the first report of one bis-acylpolyamine with antibacterial activity purified from animal source.

Authors:
 [1];  [2];  [3];  [1];  [4];  [2];  [5]
  1. Parasitology Department, Biomedical Sciences Institute, Sao Paulo University, Av Prof Lineu Prestes, 1374, 05508-900 Sao Paulo, SP (Brazil)
  2. Center for Applied Toxinology, Butantan Institute, Sao Paulo 05503-900 (Brazil)
  3. Biochemistry Department, Chemistry Institute, Sao Paulo University, Av Prof Lineu Prestes, 748, 05508-900 Sao Paulo, SP (Brazil)
  4. Okinawa Health Biotechnology Research Development Center, 12-75 Suzaki, Gushikawa, Okinawa 904-2234 (Japan)
  5. Parasitology Department, Biomedical Sciences Institute, Sao Paulo University, Av Prof Lineu Prestes, 1374, 05508-900 Sao Paulo, SP (Brazil). E-mail: sidaffre@icb.usp.br
Publication Date:
OSTI Identifier:
20857975
Resource Type:
Journal Article
Resource Relation:
Journal Name: Biochemical and Biophysical Research Communications; Journal Volume: 352; Journal Issue: 4; Other Information: DOI: 10.1016/j.bbrc.2006.11.128; PII: S0006-291X(06)02617-9; Copyright (c) 2006 Elsevier Science B.V., Amsterdam, The Netherlands, All rights reserved; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
60 APPLIED LIFE SCIENCES; CATALASE; ESCHERICHIA COLI; HYDROGEN PEROXIDE; MASS SPECTROSCOPY; MOLECULES; NUCLEAR MAGNETIC RESONANCE; OXIDASES; SPERMIDINE; SPIDERS; ULTRAVIOLET RADIATION

Citation Formats

Pereira, Lourivaldo S., Silva, Pedro I., Miranda, M. Teresa M., Almeida, Igor C., Naoki, Hideo, Konno, Katsuhiro, and Daffre, Sirlei. Structural and biological characterization of one antibacterial acylpolyamine isolated from the hemocytes of the spider Acanthocurria gomesiana. United States: N. p., 2007. Web. doi:10.1016/j.bbrc.2006.11.128.
Pereira, Lourivaldo S., Silva, Pedro I., Miranda, M. Teresa M., Almeida, Igor C., Naoki, Hideo, Konno, Katsuhiro, & Daffre, Sirlei. Structural and biological characterization of one antibacterial acylpolyamine isolated from the hemocytes of the spider Acanthocurria gomesiana. United States. doi:10.1016/j.bbrc.2006.11.128.
Pereira, Lourivaldo S., Silva, Pedro I., Miranda, M. Teresa M., Almeida, Igor C., Naoki, Hideo, Konno, Katsuhiro, and Daffre, Sirlei. Fri . "Structural and biological characterization of one antibacterial acylpolyamine isolated from the hemocytes of the spider Acanthocurria gomesiana". United States. doi:10.1016/j.bbrc.2006.11.128.
@article{osti_20857975,
title = {Structural and biological characterization of one antibacterial acylpolyamine isolated from the hemocytes of the spider Acanthocurria gomesiana},
author = {Pereira, Lourivaldo S. and Silva, Pedro I. and Miranda, M. Teresa M. and Almeida, Igor C. and Naoki, Hideo and Konno, Katsuhiro and Daffre, Sirlei},
abstractNote = {We have isolated a 417 Da 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 85 {mu}M, being this activity inhibited completely by catalase. Therefore, the antibacterial activity of mygalin was attributed to its production of hydrogen peroxide (H{sub 2}O{sub 2}). The putative mechanisms of formation of H{sub 2}O{sub 2} from mygalin are discussed. To our knowledge this is the first report of one bis-acylpolyamine with antibacterial activity purified from animal source.},
doi = {10.1016/j.bbrc.2006.11.128},
journal = {Biochemical and Biophysical Research Communications},
number = 4,
volume = 352,
place = {United States},
year = {Fri Jan 26 00:00:00 EST 2007},
month = {Fri Jan 26 00:00:00 EST 2007}
}