Panurgines, novel antimicrobial peptides from the venom of communal bee Panurgus calcaratus (Hymenoptera: Andrenidae)
- 514 Downloads
Three novel antimicrobial peptides (AMPs), named panurgines (PNGs), were isolated from the venom of the wild bee Panurgus calcaratus. The dodecapeptide of the sequence LNWGAILKHIIK-NH2 (PNG-1) belongs to the category of α-helical amphipathic AMPs. The other two cyclic peptides containing 25 amino acid residues and two intramolecular disulfide bridges of the pattern Cys8–Cys23 and Cys11–Cys19 have almost identical sequence established as LDVKKIICVACKIXPNPACKKICPK-OH (X=K, PNG-K and X=R, PNG-R). All three peptides exhibited antimicrobial activity against Gram-positive bacteria and Gram-negative bacteria, antifungal activity, and low hemolytic activity against human erythrocytes. We prepared a series of PNG-1 analogs to study the effects of cationicity, amphipathicity, and hydrophobicity on the biological activity. Several of them exhibited improved antimicrobial potency, particularly those with increased net positive charge. The linear analogs of PNG-K and PNG-R having all Cys residues substituted by α-amino butyric acid were inactive, thus indicating the importance of disulfide bridges for the antimicrobial activity. However, the linear PNG-K with all four cysteine residues unpaired, exhibited antimicrobial activity. PNG-1 and its analogs induced a significant leakage of fluorescent dye entrapped in bacterial membrane-mimicking large unilamellar vesicles as well as in vesicles mimicking eukaryotic cell membrane. On the other hand, PNG-K and PNG-R exhibited dye-leakage activity only from vesicles mimicking bacterial cell membrane.
KeywordsAntimicrobial peptides Wild bee venom CD spectroscopy Large unilamellar vesicles Electron microscopy
This work was supported by the Grant Agency of the Charles University no. 645012, Czech Science Foundation, Grant no. 203/08/0536, and by research project RVO 61388963 of the Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic. We thank our technical assistants Mrs. Hana Hulačová and Mrs. Lenka Borovičková for their help with peptide synthesis. We also thank Gale A. Kirking at English Editorial Services, s.r.o. for assistance with the English.
Conflict of interest
The authors declare that they have no conflict of interest.
- Čeřovský V, Buděšínský M, Hovorka O, Cvačka J, Voburka Z, Slaninová J, Borovičková L, Fučík V, Bednárová L, Votruba I, Straka J (2009) Lasioglossins: three novel antimicrobial peptides from the venom of the eusocial bee Lasioglossum laticeps (Hymenoptera: Halictidae). ChemBioChem 10:2089–2099CrossRefPubMedGoogle Scholar
- Konno K, Hisada M, Fontana R, Lorenzi CCB, Naoki H, Itagaki Y, Miwa A, Kawai N, Nakata Y, Yasuhara T, Neto JR, de Azevedo WF Jr, Palma MS, Nakajima T (2001) Anoplin, a novel antimicrobial peptide from the venom of the solitary wasp Anoplius samariensis. Biochim Biophys Acta 1550:70–80CrossRefPubMedGoogle Scholar
- Konno K, Hisada M, Naoki H, Itagaki Y, Fontana R, Rangel M, Oliveira JS, Cabrera MPS, Neto JR, Hide I, Nakata Y, Yasuhara T, Nakajima T (2006) Eumenitin, a novel antimicrobial peptide from the venom of the solitary eumenine wasp Eumenes rubronotatus. Peptides 27:2624–2631CrossRefPubMedGoogle Scholar
- Konno K, Rangel M, Oliveira JS, dos Santos Cabrera MP, Fontana R, Hirata IY, Hide I, Nakata Y, Mori K, Kawano M, Fuchino H, Sekita S, Neto JR (2007) Decoralin, a novel linear cationic α-helical peptide from the venom of the solitary eumenine wasps Oreumenes decoratus. Peptides 28:2320–2327CrossRefPubMedGoogle Scholar
- Lohner K, Blondele SS (2005) Molecular mechanisms of membrane perturbation by antimicrobial peptides and the use of biophysical studies in the design of novel peptide antibiotics. Comb Chem High T Scr 8:241–256Google Scholar
- Monincová L, Slaninová J, Voburka Z, Hovorka O, Fučík V, Borovičková L, Bednárová L, Buděšínský M, Straka J, Čeřovský V (2009) Novel biologically active peptides from the venom of the solitary bee Macropis fulvipes (Hymenoptera: Melittidae). In: Slaninová J (ed) Collection symposium series, institute of organic chemistry and biochemistry, vol 11. Academy of Sciences of the Czech Republic, Prague, pp 77–80Google Scholar
- Monincová L, Buděšínský M, Slaninová J, Hovorka O, Cvačka J, Voburka Z, Fučík V, Borovičková L, Bednárová L, Straka J, Čeřovský V (2010) Novel antimicrobial peptides from the venom of the eusocial bee Halictus sexcinctus (Hymenoptera: Halictidae) and their analogs. Amino Acids 39:763–775CrossRefPubMedGoogle Scholar
- Shailesh S, Neelam S, Sandeep K, Gupta GD (2009) Liposomes: a review. J Pharm Res 2:1163–1167Google Scholar