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Electrospray tandem mass spectrometry analysis of methylenedioxy chalcones, flavanones and flavones

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dc.contributor.author Menezes, J.C.J.M.D.S.
dc.contributor.author Cavaleiro, J.A.S.
dc.contributor.author Kamat, S.P.
dc.contributor.author Barros, C.M.R.F.
dc.contributor.author Domingues, M.R.M.
dc.date.accessioned 2015-06-04T03:47:21Z
dc.date.available 2015-06-04T03:47:21Z
dc.date.issued 2013
dc.identifier.citation Rapid Communications in Mass Spectrometry. 27(12); 2013; 1303-1310. en_US
dc.identifier.uri http://dx.doi.org/10.1002/rcm.6577
dc.identifier.uri http://irgu.unigoa.ac.in/drs/handle/unigoa/2879
dc.description.abstract Several methylenedioxy chalcones, flavanones and flavones substituted with mono-, di- 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. Electrospray ionization mass (ESI-MS) and tandem mass (ESI-MS/MS) spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns and their pathways were analyzed by CID-MS2-3 spectra acquired in a LXQ linear ion trap mass spectrometer using standard isolation and excitation procedures (activation q value of 0.25, activation time of 30?ms). ESI-MS and ESI-MSn conditions: spray voltage 5?kV, nitrogen 8.00 sheath gas flow rate (arb), heated capillary temperature 275 degrees C, capillary voltage 10.99?V; tube lens voltage 75.01?V. The ESI-MS/MS spectra of chalcones were nearly identical to their corresponding isomeric flavanones with 0,alpha A+/1,3A+ and 0,1'B+/1,4B+ cleavages. Other common losses are of CH3, H2O, HCHO and C2H2O. The characteristic loss of C2H2O and absence of a 0, alpha B+/1,3B+ product ion allows to distinguish between the 2- or 4-methoxy-substituted chalcones and flavanones. Common losses of CH3, CH3 and H, and C2H2O2 characteristic for the presence of methylenedioxy groups were observed in flavones. The substitution pattern on the B-ring leads to distinct base peak formation in the flavones. In addition, differentiation of isomers with methoxy substituents in ortho and para positions of the B-ring was achieved using MS/MS in chalcones and flavanones. This method will be helpful for identification of these compounds in biological mixtures. en_US
dc.publisher Wiley en_US
dc.subject Chemistry en_US
dc.title Electrospray tandem mass spectrometry analysis of methylenedioxy chalcones, flavanones and flavones en_US
dc.type Journal article en_US
dc.identifier.impf y


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