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Simultaneous characterization of prenylated flavonoids and isoflavonoids in Psoralea corylifolia L. by liquid chromatography with diode‐array detection and quadrupole time‐of‐flight mass spectrometry
Author(s) -
Xu MeiJuan,
Wu Bin,
Ding Tao,
Chu JiHong,
Li ChangYin,
Zhang Jun,
Wu Ting,
Wu Jian,
Liu ShiJia,
Liu ShenLin,
Ju WenZheng,
Li Ping
Publication year - 2012
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.6361
Subject(s) - chemistry , psoralea corylifolia , mass spectrometry , protonation , prenylation , chromatography , stereochemistry , ion , organic chemistry , medicine , alternative medicine , pathology , enzyme
RATIONALE Prenylated flavonoids and isoflavonoids are widely distributed throughout the plant kingdom, with many biological effects. Psoralea corylifolia , which contains many kinds of prenylated components, has been widely used as a medicinal plant in Asia and India for thousands of years. The goal of this study was to characterize the components in P. corylifolia using a liquid chromatography with diode‐array detection and quadrupole time‐of‐flight mass spectrometry (LC‐DAD/Q‐TOF‐MS) method, and to elucidate the fragmentation behavior of the different prenyl substituent groups and their appropriate characteristic pathways in positive ion mode. METHODS The calculated accurate masses of the protonated molecules, the fragment ions, the retention behavior, and the data from UV spectra were used for identification of the components in P. corylifolia . RESULTS A total of 45 compounds, including 43 prenylated components, were identified or tentatively identified in P. corylifolia . Different diagnostic fragment ions and neutral losses were observed in different prenyl substructures: neutral loss of 56 Da (C 4 H 8 ) and a fragment ion at m/z 69 (C 5 H 9 + ) were generated by a prenyl chain; neutral losses of 42 Da (C 3 H 6 ), 54 Da (C 4 H 6 ), 15 Da (CH 3 •) and 16 Da (CH 4 ) were observed in a ring‐closed prenyl group; neutral losses of 72 Da (C 4 H 8 O), 60 Da (C 2 H 4 O 2 ), 58 Da (C 3 H 6 O) and 18 Da (H 2 O) were detected in a 2,2‐dimethyl‐3,4‐dihydroxydihydropyran ring; neutral losses of 72 Da (C 4 H 8 O), 60 Da (C 3 H 8 O) and 18 Da (H 2 O) were yielded from a 2,2‐dimethyl‐3‐hydroxydihydropyran ring, a 2‐(1‐hydroxy‐1‐methylethyl)dihydrofuran ring or a 1‐hydroxy‐3‐methylbut‐3‐enyl chain. CONCLUSIONS This method can be applied for analysis of prenylated components in P. corylifolia and other herbal medicines. Copyright © 2012 John Wiley & Sons, Ltd.