{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T08:20:50Z","timestamp":1790065250378,"version":"4.0.1"},"reference-count":22,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2013,5,7]],"date-time":"2013-05-07T00:00:00Z","timestamp":1367884800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2013,6,30]]},"abstract":"\n RATIONALE<\/jats:title>\n Several methylenedioxy chalcones, flavanones and flavones substituted with mono\u2010, di\u2010 and trimethoxy groups have been used in the treatment of proliferative conditions like cancer and inflammatory diseases. The application of these flavonoids in biology requires an analytical method to ensure a detailed knowledge of their structures after drug metabolism.<\/jats:p>\n <\/jats:sec>\n \n METHODS<\/jats:title>\n \n Electrospray ionization mass (ESI\u2010MS) and tandem mass (ESI\u2010MS\/MS) spectra were acquired using a Q\u2010TOF 2 instrument. Fragmentation patterns and their pathways were analyzed by CID\u2010MS\n 2\u20133<\/jats:sup>\n spectra acquired in a LXQ linear ion trap mass spectrometer using standard isolation and excitation procedures (activation\n q<\/jats:italic>\n value of 0.25, activation time of 30\u2009ms). ESI\u2010MS and ESI\u2010MS\n n<\/jats:sup>\n conditions: spray voltage 5\u2009kV, nitrogen 8.00 sheath gas flow rate (arb), heated capillary temperature 275\u00b0C, capillary voltage 10.99\u2009V; tube lens voltage 75.01\u2009V.\n <\/jats:p>\n <\/jats:sec>\n \n RESULTS<\/jats:title>\n \n The ESI\u2010MS\/MS spectra of chalcones were nearly identical to their corresponding isomeric flavanones with\n 0,\u03b1<\/jats:sup>\n A\n +<\/jats:sup>\n \/\n 1,3<\/jats:sup>\n A\n +<\/jats:sup>\n and\n 0,1'<\/jats:sup>\n B\n +<\/jats:sup>\n \/\n 1,4<\/jats:sup>\n B\n +<\/jats:sup>\n cleavages. Other common losses are of\n \u2022<\/jats:sup>\n CH\n 3<\/jats:sub>\n , H\n 2<\/jats:sub>\n O, HCHO and C\n 2<\/jats:sub>\n H\n 2<\/jats:sub>\n O. The characteristic loss of C\n 2<\/jats:sub>\n H\n 2<\/jats:sub>\n O and absence of a\n 0,\u03b1<\/jats:sup>\n B\n +<\/jats:sup>\n \/\n 1,3<\/jats:sup>\n B\n +<\/jats:sup>\n product ion allows to distinguish between the 2\u2010 or 4\u2010methoxy\u2010substituted chalcones and flavanones. Common losses of\n \u2022<\/jats:sup>\n CH\n 3<\/jats:sub>\n ,\n \u2022<\/jats:sup>\n CH\n 3<\/jats:sub>\n and\n \u2022<\/jats:sup>\n H, and C\n 2<\/jats:sub>\n H\n 2<\/jats:sub>\n O\n 2<\/jats:sub>\n characteristic for the presence of methylenedioxy groups were observed in flavones.\n <\/jats:p>\n <\/jats:sec>\n \n CONCLUSIONS<\/jats:title>\n \n The substitution pattern on the B\u2010ring leads to distinct base peak formation in the flavones. In addition, differentiation of isomers with methoxy substituents in\n ortho<\/jats:italic>\n and\n para<\/jats:italic>\n positions of the B\u2010ring was achieved using MS\/MS in chalcones and flavanones. This method will be helpful for identification of these compounds in biological mixtures. Copyright \u00a9 2013 John Wiley & Sons, Ltd.\n <\/jats:p>\n <\/jats:sec>","DOI":"10.1002\/rcm.6577","type":"journal-article","created":{"date-parts":[[2013,5,14]],"date-time":"2013-05-14T06:05:15Z","timestamp":1368511515000},"page":"1303-1310","source":"Crossref","is-referenced-by-count":13,"title":["Electrospray tandem mass spectrometry analysis of methylenedioxy chalcones, flavanones and flavones"],"prefix":"10.1002","volume":"27","author":[{"given":"Jos\u00e9 C. J. M. D. S.","family":"Menezes","sequence":"first","affiliation":[{"name":"Department of Chemistry & QOPNA University of Aveiro 3810\u2010193 Aveiro Portugal"},{"name":"Department of Chemistry Goa University, Taleigao Plateau Goa 403 206 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 A. S.","family":"Cavaleiro","sequence":"additional","affiliation":[{"name":"Department of Chemistry & QOPNA University of Aveiro 3810\u2010193 Aveiro Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shrivallabh P.","family":"Kamat","sequence":"additional","affiliation":[{"name":"Department of Chemistry Goa University, Taleigao Plateau Goa 403 206 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cristina M. R. F.","family":"Barros","sequence":"additional","affiliation":[{"name":"Department of Chemistry & QOPNA University of Aveiro 3810\u2010193 Aveiro Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M. Ros\u00e1rio M.","family":"Domingues","sequence":"additional","affiliation":[{"name":"Department of Chemistry & QOPNA University of Aveiro 3810\u2010193 Aveiro Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,5,7]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1093\/jn\/133.10.3248S"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/np9904509"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11130-004-0049-7"},{"key":"e_1_2_6_5_1","first-page":"3823","article-title":"Dietary flavone is a potent apoptosis inducer in human colon carcinoma cells","volume":"60","author":"Wenzel U.","year":"2000","journal-title":"Cancer Res."},{"key":"e_1_2_6_6_1","unstructured":"G. A.Potter P. C.Butler.3 4\u2010Methylenedioxy\u2010substituted chalcones as therapeutic agents.WO 2003028713 A2 2003."},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10637-006-5947-0"},{"key":"e_1_2_6_8_1","unstructured":"A.Bargiotti L.Bonomini M.Meninchincheri J.Moll P.Polucci C.Soncini E.Vanotti.Substituted benzopyranones as telomerase inhibitors.WO 2002074036 A2 2002."},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm00014a032"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.2010.01185.x"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1097\/00001756-200112040-00053"},{"key":"e_1_2_6_12_1","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1016\/S0022-3565(24)39224-9","article-title":"Polymethoxylated flavones in orange juice are inhibitors of P\u2010glycoprotein but not Cytochrome P450 3A4","volume":"293","author":"Takanaga H.","year":"2000","journal-title":"J. Pharmacol. Exp. 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