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Their primary sequences were established as H\u2010Val\u2010Asn\u2010Trp\u2010Lys\u2010Lys\u2010Val\u2010Leu\u2010Gly\u2010Lys\u2010Ile\u2010Ile\u2010Lys\u2010Val\u2010Ala\u2010Lys\u2010NH<jats:sub>2<\/jats:sub> (LL\u2010I), H\u2010Val\u2010Asn\u2010Trp\u2010Lys\u2010Lys\u2010Ile\u2010Leu\u2010Gly\u2010Lys\u2010Ile\u2010Ile\u2010Lys\u2010Val\u2010Ala\u2010Lys\u2010NH<jats:sub>2<\/jats:sub> (LL\u2010II) and H\u2010Val\u2010Asn\u2010Trp\u2010Lys\u2010Lys\u2010Ile\u2010Leu\u2010Gly\u2010Lys\u2010Ile\u2010Ile\u2010Lys\u2010Val\u2010Val\u2010Lys\u2010NH<jats:sub>2<\/jats:sub> (LL\u2010III). These lasioglossins exhibited potent antimicrobial activity against both Gram\u2010positive and Gram\u2010negative bacteria, low haemolytic and mast cell degranulation activity, and a potency to kill various cancer cells in vitro. The lasioglossin CD spectra were measured in the presence of trifluoroethanol and sodium dodecyl sulfate solution and indicated a high degree of \u03b1\u2010helical conformation. NMR spectroscopy, which was carried out in trifluoroethanol\/water confirmed a curved \u03b1\u2010helical conformation with a concave hydrophobic and convex hydrophilic side. To understand the role of this bend on biological activity, we studied lasioglossin analogues in which the Gly in the centre of the molecule was replaced by other amino acid residues (Ala, Lys, Pro). The importance of the N\u2010terminal part of the molecule to the antimicrobial activity was revealed through truncation of five residues from both the N and C termini of the LL\u2010III peptide. C\u2010terminal deamidation of LL\u2010III resulted in a drop in antimicrobial activity, but esterification of the C terminus had no effect. Molecular modelling of LL\u2010III and the observed NOE contacts indicated the possible formation of a bifurcated H\u2010bond between hydrogen from the Lys15 CONH peptide bond and one H of the C\u2010terminal CONH<jats:sub>2<\/jats:sub> to the Ile11 oxygen atom. Such interactions cannot form with C\u2010terminal esterification.<\/jats:italic><\/jats:p>","DOI":"10.1002\/cbic.200900133","type":"journal-article","created":{"date-parts":[[2009,7,9]],"date-time":"2009-07-09T22:16:28Z","timestamp":1247177788000},"page":"2089-2099","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":92,"title":["Lasioglossins: Three Novel Antimicrobial Peptides from the Venom of the Eusocial Bee <i>Lasioglossum laticeps<\/i> (Hymenoptera: Halictidae)"],"prefix":"10.1002","volume":"10","author":[{"given":"V\u00e1clav","family":"\u010ce\u0159ovsk\u00fd","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Milo\u0161","family":"Bud\u011b\u0161\u00ednsk\u00fd","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Old\u0159ich","family":"Hovorka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Josef","family":"Cva\u010dka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zden\u011bk","family":"Voburka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ji\u0159ina","family":"Slaninov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lenka","family":"Borovi\u010dkov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladim\u00edr","family":"Fu\u010d\u00edk","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucie","family":"Bedn\u00e1rov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ivan","family":"Votruba","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jakub","family":"Straka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,8,12]]},"reference":[{"key":"e_1_2_8_1_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2672.2007.03498.x"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt1267"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/bip.20286"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1038\/415389a"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00109-006-0143-4"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.2478\/s11535-007-0010-5"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1080\/02713680590968637"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2796.2003.01278.x"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2796.2003.01228.x"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1124\/pr.55.1.2"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/1097-0282(2000)55:1<4::AID-BIP30>3.0.CO;2-M"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-0282(1998)47:6<451::AID-BIP4>3.0.CO;2-F"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkn823"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00018-003-3106-8"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.peptides.2008.02.007"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-4838(01)00271-0"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.peptides.2006.04.013"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.peptides.2007.09.017"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M100216200"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200800476"},{"key":"e_1_2_8_21_2","first-page":"17","volume-title":"Teil III, Naturkundliches Jahrbuch der Stadt Linz","author":"Ebmer A. 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