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Cereulide has a greater complexation ability with metal ions than valinomycin and also exhibits a K<jats:sup>+<\/jats:sup>\u2010ion\u2010selective ionophore property at lower concentrations than valinomycin.<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p><jats:p>Cereulide and valinomycin are both 36\u2010membered cyclic depsipeptides with 12 stereogenic centers that have a very similar sequence of cyclo [\u2010<jats:sc>D<\/jats:sc>\u2010<jats:italic>O<\/jats:italic>\u2010Leu\u2010<jats:sc>D<\/jats:sc>\u2010Ala\u2010<jats:sc>L<\/jats:sc>\u2010<jats:italic>O<\/jats:italic>\u2010Val\u2010<jats:sc>L<\/jats:sc>\u2010Val\u2010]<jats:sub>3<\/jats:sub> and cyclo [\u2010<jats:sc>D<\/jats:sc>\u2010<jats:italic>O<\/jats:italic>\u2010Val\u2010<jats:sc>D<\/jats:sc>\u2010Val\u2010<jats:sc>L<\/jats:sc>\u2010<jats:italic>O<\/jats:italic>\u2010Ala\u2010<jats:sc>L<\/jats:sc>\u2010Val\u2010]<jats:sub>3<\/jats:sub>, respectively. Cereulide is an emetic toxin produced by <jats:italic>Bacillus cereus<\/jats:italic> through an unusual non\u2010ribosomal peptide synthesis (NRPS), whereas valinomycin, produced by <jats:italic>Streptomyces fulvissimus<\/jats:italic>, is a known antibiotic drug. Both compounds are known as K<jats:sup>+<\/jats:sup>\u2010ion\u2010selective ionophores and cause a potassium\u2010dependent drop in the transmembrane potential of mitochondria, arising from the uptake of a K<jats:sup>+<\/jats:sup>\u2010ion\u2010charged ionophore complex. Such compounds may affect mitochondrial function. In the three\u2010dimensional structure of cereulide and valinomycin, cereulide has a vertical and horizontal mirror\u2010image\u2010like structure as is the case in valinomycin. The only difference is the side chains which are linked to a similar framework. Through the current <jats:sup>1<\/jats:sup>H\u2005NMR spectroscopy and metal\u2010complexation studies, we found that cereulide had a higher complexation ability to metal ions compared to valinomycin. Cereulide exhibited the K<jats:sup>+<\/jats:sup>\u2010ion\u2010selective ionophore property at a lower concentration than valinomycin. X\u2010ray crystallographic analyses of the cereulide and valinomycin H<jats:sup>+<\/jats:sup> form were compared, and revealed that the higher structures of both compounds also showed similarity in the crystal structures. The structure of cereulide\u2013H<jats:sup>+<\/jats:sup> form was found to be in agreement with the structure obtained by a combination of NMR spectroscopy and molecular\u2010mechanics calculations, which afforded reasonable dihedral angles at the local\u2010minimum\u2010energy conformation of the cereulide\u2013K<jats:sup>+<\/jats:sup>\u2010ion complex.<\/jats:p>","DOI":"10.1002\/asia.200900011","type":"journal-article","created":{"date-parts":[[2009,4,3]],"date-time":"2009-04-03T09:18:59Z","timestamp":1238750339000},"page":"688-698","source":"Crossref","is-referenced-by-count":31,"title":["Higher Structure of Cereulide, an Emetic Toxin from <i>Bacillus cereus<\/i>, and Special Comparison with Valinomycin, an Antibiotic from <i>Streptomyces fulvissimus<\/i>"],"prefix":"10.1002","volume":"4","author":[{"given":"Arthit","family":"Makarasen","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenji","family":"Yoza","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Minoru","family":"Isobe","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,4,28]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6968.1994.tb07071.x"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijfoodmicro.2006.09.031"},{"key":"e_1_2_6_4_2","first-page":"409","volume-title":"Foodborne Pathogens","author":"Granum P. 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