Analysis of minor flavonoids in Piper hostmannianum var. berbicense using liquid chromatography coupled with atmospheric pressure chemical ionization mass spectrometry.
The fragmentations of hydroxylated flavanones, chalcones and dihydrochalcones were investigated by direct loop injection using an ion trap mass spectrometry equipped with atmospheric pressure chemical ionization (APCI) probe. Some of them have been isolated from the leaves of Piper hostmannianum var. berbicense and standards were used to confirm their fragmentation behaviour. In negative ion mode, fragmentations of these three types of flavonoids revealed specific diagnostic ions which allowed us to identify aglycones in a crude plant extract. The major fragment ion obtained in MS/MS experiment for methoxylated chalcones is the neutral loss of a methyl radical whereas a H(2)O molecule is lost in the case of methoxylated dihydrochalcones. Methoxylated chalcones and flavanones isomers could be differentiated by the relative intensity ratio of [M-H-CH(3)]*(-) and [M-H-C(2)H(2)O](-) ions. Based on UV and MS data, a decision tree that includes UV lambda(max) absorptions and MS/MS diagnostic ions was built in order to obtain structural information of unknown compounds present in the extract. This tree was used to identify flavonoids in the ethyl acetate extract of P. hostmannianum var. berbicense leaves after analysis by high-performance liquid chromatography-diode array detection-atmospheric pressure chemical ionization ion trap multistage mass spectrometry. A total of 11 flavonoids were tentatively characterized based on the MS fragmentations pattern observed in MS(n) experiments.
Portet
Bénédicte
B
Université de Toulouse, UMR-152 IRD-UPS Laboratoire de Pharmacochimie des Substances Naturelles et Pharmacophores Redox, Faculté des Sciences Pharmaceutiques, Université Paul-Sabatier, F-31062 Toulouse cedex 09, France. benedicte.portet@voila.fr
Fabre
Nicolas
N
Rozenberg
Raoul
R
Habib-Jiwan
Jean-Louis
JL
Moulis
Claude
C
Quetin-Leclercq
Joëlle
J
D002853:Chromatography, Liquid / Q000379:methods*; D005419:Flavonoids / Q000737:chemistry*; D031701:Piper / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
D005419:Flavonoids; D010936:Plant Extracts