{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T07:58:12Z","timestamp":1790927892978,"version":"4.1.0"},"reference-count":34,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T00:00:00Z","timestamp":1787443200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T00:00:00Z","timestamp":1787443200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2026,11,15]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:sec>\n                    <jats:title>Rationale<\/jats:title>\n                    <jats:p>Despite the well\u2010established metal\u2010chelating properties of 8\u2010hydroxyquinoline and related compounds, little is known about the interaction of furoquinoline alkaloids with biologically relevant metal ions. This study highlights the value of combining ESI\u2010MS, energy\u2010resolved mass spectrometry breakdown experiments, and DFT approaches to characterize metal\u2010binding properties of methoxy\u2010substituted furoquinoline alkaloids, enabling the differentiation of positional isomers through characteristic metal\u2010adduct formation and ion fragmentation.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Methods<\/jats:title>\n                    <jats:p>\n                      The complexation behavior of the studied alkaloids toward Mg\n                      <jats:sup>2+<\/jats:sup>\n                      , Ca\n                      <jats:sup>2+<\/jats:sup>\n                      , Co\n                      <jats:sup>2+<\/jats:sup>\n                      , Cu\n                      <jats:sup>2+<\/jats:sup>\n                      , and Zn\n                      <jats:sup>2+<\/jats:sup>\n                      was studied by electrospray ionization mass spectrometry in a micrOTOF Q II mass spectrometer. Energy\u2010resolved mass spectrometry breakdown experiments were performed to assess the relative stability of the observed adducts. Adduct profiles were graphically compared by PCA of the ESI\/MS dataset. Binding modes were evaluated by DFT calculations by B3LYP 6\u2010311+G(2d,3p).\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Results<\/jats:title>\n                    <jats:p>\n                      Quinolines\n                      <jats:bold>1<\/jats:bold>\n                      \u2010\n                      <jats:bold>5<\/jats:bold>\n                      yielded stable metal adducts with distinct profiles. Ligand oxidation to [M]\n                      <jats:sup>+.<\/jats:sup>\n                      and Cu(I) adduct formation occurred mainly for furoquinolines\n                      <jats:bold>1\u20103<\/jats:bold>\n                      . Methyl\u2010loss fragmentation characterized compounds with an 8\u2010methoxyquinoline motif. Isomeric furoquinolines showed markedly different metal\u2010binding adduct profiles. Flindersiamine\n                      <jats:bold>1<\/jats:bold>\n                      showed the strongest metal\u2010binding affinity, yielding intense [3M+Me]\n                      <jats:sup>2+<\/jats:sup>\n                      and [2M+Me]\n                      <jats:sup>2+<\/jats:sup>\n                      adducts, and DFT calculations support its ability to act as an N,O\u2010bidentate ligand.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Conclusions<\/jats:title>\n                    <jats:p>\n                      Metal\u2010adduct profiles obtained by ESI\u2010MS, supported by PCA analysis, provide a robust analytical framework for differentiating positional isomers of methoxy\u2010substituted furoquinoline alkaloids. ESI\u2010MS and DFT studies identified the 8\u2010methoxy substituent as a key determinant of metal complexation in furoquinoline alkaloids, revealing flindersiamine\n                      <jats:bold>1<\/jats:bold>\n                      as the strongest Cu\n                      <jats:sup>2+<\/jats:sup>\n                      \u2010binding ligand and providing a basis for future studies on the biological properties of these compounds.\n                    <\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.70162","type":"journal-article","created":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T05:14:48Z","timestamp":1787548488000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Complexation of Divalent Metals by Natural Furoquinoline Alkaloids: An Electrospray Mass Spectrometry and DFT 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