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

Biochemical and Biophysical Research Communications

Volumn 352, Issue 4, 2007, Pages 953-959

  Pereira, Lourivaldo S ^a   Silva Jr , Pedro I ^b   Miranda, M Terêsa M ^a   Almeida, Igor C ^a   Naoki, Hideo ^c   Konno, Katsuhiro ^b   Daffre, Sirlei ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b INSTITUTO BUTANTAN   (Brazil)

^c Okinawa Health Biotechnology Research Development Center   (Japan)

Author keywords

Acylpolyamine; Amine oxidase; Antimicrobial molecule; Arachnids; Catalase; Hydrogen peroxide; Immune system; Laccase; Spermidine; Spider

Indexed keywords

ANTIINFECTIVE AGENT; BISACYLPOLYAMINE N1,N8 BIS(2,5 DIHYDROXYBENZOYL)SPERMIDINE; GENTISIC ACID; HYDROGEN PEROXIDE; MYGALIN; NATURAL PRODUCT; SPERMIDINE DERIVATIVE;

ACANTHOCURRIA GOMESIANA; ANTIBACTERIAL ACTIVITY; ARTICLE; BLOOD CELL; DRUG ISOLATION; DRUG PURIFICATION; ESCHERICHIA COLI; ISOLATION PROCEDURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SPIDER; STRUCTURE ACTIVITY RELATION; TANDEM MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; ANTI-BACTERIAL AGENTS; CANDIDA ALBICANS; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESCHERICHIA COLI; HEMOCYTES; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROCOCCUS LUTEUS; MOLECULAR STRUCTURE; SPERMIDINE; SPIDERS;

ACANTHOSCURRIA GOMESIANA; ANIMALIA; ARACHNIDA; ARANEAE; ESCHERICHIA COLI;

EID: 33845437048     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2006.11.128     Document Type: Article

References (30)

1. Nappi A.J., and Ottaviani E. Cytotoxicity and cytotoxic molecules in invertebrates. Bioessays 22 (2000) 469-480
2. N.A. Ratcliffe, M.M.A. Whitten, Vector Immunity, in: S.H. Gillespie, L. Smith, G.L. Osbourn, A. (Eds.), Microbe-vector Interactions in Vector-borne Diseases, Cambridge University Press, Cambridge, 2004, pp. 240-271.
3. Leem J.Y., Nishimura C., Kurata S., Shimada I., Kobayashi A., and Natori S. Purification and characterization of N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine, a novel antibacterial substance of Sarcophaga peregrina (flesh fly). J. Biol. Chem. 271 (1996) 13573-13577
4. Leem J.Y., Jeong I.J., Park K.T., and Park H.Y. Isolation of p-hydroxycinnamaldehyde as an antibacterial substance from the saw fly, Acantholyda parki S. FEBS Lett. 442 (1999) 53-56
5. Chiou S.J., Kotanen S., Cerstiaens A., Daloze D., Pasteels J.M., Lesage A., Drijfhout J.W., Verhaert P., Dillen L., Claeys M., De Meulemeester H., Nuttin B., De Loof A., and Schoofs L. Purification of toxic compounds from larvae of the gray fleshfly: the identification of paralysins. Biochem. Biophys. Res. Commun. 246 (1998) 457-462
6. Meylaers K., Cerstiaens A., Vierstraete E., Baggerman G., Michiels C.W., De Loof A., and Schoofs L. Antimicrobial compounds of low molecular mass are constitutively present in insects: characterisation of beta-alanyl-tyrosine. Curr. Pharm. Des. 9 (2002) 159-174
7. Kuhn-Nentwig L. Antimicrobial and cytolytic peptides of venomous arthropods. Cell. Mol. Life Sci. 60 (2003) 2651-2668
8. Silva Jr. P.I., Daffre S., and Bulet P. Isolation and characterization of gomesin, an 18-residue cysteine-rich defense peptide from the spider Acanthoscurria gomesiana hemocytes with sequence similarities to horseshoe crab antimicrobial peptides of the tachyplesin family. J. Biol. Chem. 275 (2000) 33464-33470
9. Fazio M.A., Oliveira Jr. V.X., Bulet P., Miranda M.T., Daffre S., and Miranda A. Structure-activity relationship studies of gomesin: importance of the disulfide bridges for conformation, bioactivities, and serum stability. Biopolymers 84 (2006) 205-218
10. Lorenzini D.M., Fukuzawa A.H., Silva Jr. P.I., Machado-Santelli G., Bijovsky A.T., and Daffre S. Molecular cloning, expression analysis and cellular localization of gomesin, an anti-microbial peptide from hemocytes of the spider Acanthoscurria gomesiana. Insect Biochem. Mol. Biol. 33 (2003) 1011-1016
11. Lorenzini D.M., Silva Jr. P.I., Fogaca A.C., Bulet P., and Daffre S. Acanthoscurrin: a novel glycine-rich antimicrobial peptide constitutively expressed in the hemocytes of the spider Acanthoscurria gomesiana. Dev. Comp. Immunol. 27 (2003) 781-791
12. Mandard N., Bulet P., Caille A., Daffre S., and Vovelle F. The solution structure of gomesin, an antimicrobial cysteine-rich peptide from the spider. Eur. J. Biochem. 269 (2002) 1190-1198
13. Harwood C.R., and Archibald R.A. Growth, maintenance and general techniques. In: Harwood C.R., and Cutting S.M. (Eds). Molecular Biology Methods for Bacillus (1990), John Wiley and Sons Ltd. 1-26
14. Skinner W.S., Adams M.E., Quistad G.B., Kataoka H., Cesarin B.J., Enderlin F.E., and Schooley D.A. Purification and characterization of two classes of neurotoxins from the funnel web spider, Agelenopsis aperta. J. Biol. Chem. 264 (1989) 2150-2155
15. Quistad G.B., Suwanrumpha S., Jarema M.A., Shapiro M.J., Skinner W.S., Jamieson G.C., Lui A., and Fu E.W. Structures of paralytic acylpolyamines from the spider Agelenopsis aperta. Biochem. Biophys. Res. Commun. 169 (1990) 51-56
16. Adams M.E., Herold E.E., and Venema V.J. Two classes of channel-specific toxins from funnel web spider venom. J. Comp. Physiol. [A]. 164 (1989) 333-342
17. Quistad G.B., Reuter C.C., Skinner W.S., Dennis P.A., Suwanrumpha S., and Fu E.W. Paralytic and insecticidal toxins from the funnel web spider, Hololena curta. Toxicon 29 (1991) 329-336
18. Bulet P., Hetru C., Dimarcq J.L., and Hoffmann D. Antimicrobial peptides in insects; structure and function. Dev. Comp. Immunol. 23 (1999) 329-344
19. Sharmin S., Sakata K., Kashiwagi K., Ueda S., Iwasaki S., Shirahata A., and Igarashi K. Polyamine cytotoxicity in the presence of bovine serum amine oxidase. Biochem. Biophys. Res. Commun. 282 (2001) 228-235
20. Agostinelli E., Arancia G., Vedova L.D., Belli F., Marra M., Salvi M., and Toninello A. The biological functions of polyamine oxidation products by amine oxidases: perspectives of clinical applications. Amino Acids 27 (2004) 347-358
21. Alexandre G., and Zhulin I.B. Laccases are widespread in bacteria. Trends Biotechnol. 18 (2000) 41-42
22. Bolton J.L., Trush M.A., Penning T.M., Dryhurst G., and Monks T.J. Role of quinones in toxicology. Chem. Res. Toxicol. 13 (2000) 135-160
23. Guillen F., Munoz C., Gomez-Toribio V., Martinez A.T., and Jesus Martinez M. Oxygen activation during oxidation of methoxyhydroquinones by laccase from Pleurotus eryngii. Appl. Environ. Microbiol. 66 (2000) 170-175
24. 2+. Eur. J. Biochem. 268 (2001) 4787-4793
25. Tait G.H. The identification and biosynthesis of siderochromes formed by Micrococcus denitrificans. Biochem. J. 146 (1975) 191-204
26. Bergeron R.J., Burton P.S., McGovern K.A., St Onge E.J., and Streiff R.R. Synthesis, absorption, and toxicity of N1,N8-bis(2,3-dihydroxybenzoyl)spermidine, a potent iron chelator. J. Med. Chem. 23 (1980) 1130-1133
27. Bhargava K.K., Grady R.W., and Cerami A. New compounds: N1,N8-bis(2,3-dihydroxybenzoyl) spermidine and analogs as potential iron-chelating drugs. J. Pharm. Sci. 69 (1980) 986-989
28. Jacobs A., White G.P., and Tait G.P. Iron chelation in cell cultures by two conjugates of 2,3-dihydroxybenzoic acid (2,3-DHB). Biochem. Biophys. Res. Commun. 74 (1977) 1626-1630
29. Bergeron R.J., Elliott G.T., Kline S.J., Ramphal R., and St James III L. Bacteriostatic and fungostatic action of catecholamide iron chelators. Antimicrob. Agents Chemother. 24 (1983) 725-730
30. Travis J. Reviving the antibiotic miracle?. Science 264 (1994) 360-362