Simultaneous screening and identifying four categories of particular flavonoids in the leaves of Murraya exotica L. by HPLC-DAD-ESI-MS-MS.

Polymethoxylated flavonoids (PMFs), the particular flavonoid subclass in which all or almost all hydroxyls are capped by methylation, have high oral bioavailability and various activities. A sensitive high-performance liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI-MS-MS) method was established to screen and identify the PMFs in the leaves of Murraya exotica. Eight PMF standards, including two polymethoxylated flavones, two polymethoxylated flavanones, two polymethoxylated chalcones and two PMF glycosides, were first to be analyzed in positive mode by collision-induced dissociation MS-MS. On the basis of the ESI-MS, characterizations were deduced, and in the results of the extracted ion chromatogram MS-MS experiment, 26 PMFs, including 18 flavones, five flavanones or chalcones and three PMF glycosides, were screened out from the complex extract of the leaves of M. exotica. Among them, 24 PMFs were hydroxylated polymethoxyflavonoids, whereas the rest were all permethoxylated PMFs. This was the first systematic report on the presence of PMFs in the leaves of M. exotica. The results indicated that the established analytical method could be adopted as a rapid, effective technique for the structural characterization of PMFs from the complex extracts of traditional Chinese medicines.

[1]  E. Middleton,et al.  Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro. , 1991, Cancer letters.

[2]  W. Gabryelski,et al.  Structural identification of highly polar nontarget contaminants in drinking water by ESI-FAIMS-Q-TOF-MS. , 2006, Analytical chemistry.

[3]  Wen Huang,et al.  Quality evaluation of Rhizoma Belamcandae (Belamcanda chinensis (L.) DC.) by using high-performance liquid chromatography coupled with diode array detector and mass spectrometry. , 2009, Journal of chromatography. A.

[4]  F. Song,et al.  Structural characterization and identification of dibenzocyclooctadiene lignans in Fructus Schisandrae using electrospray ionization ion trap multiple-stage tandem mass spectrometry and electrospray ionization Fourier transform ion cyclotron resonance multiple-stage tandem mass spectrometry. , 2008, Analytica chimica acta.

[5]  P. Kefalas,et al.  Analysis of antioxidant compounds in sweet orange peel by HPLC-diode array detection-electrospray ionization mass spectrometry. , 2005, Biomedical chromatography : BMC.

[6]  P. Tu,et al.  Glycosides of flavone methyl ethers from Murraya paniculata , 2012 .

[7]  P. Negi,et al.  Antibacterial Activity of Citrus reticulata Peel Extracts , 2000, Zeitschrift fur Naturforschung. C, Journal of biosciences.

[8]  B. Domon,et al.  A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates , 1988, Glycoconjugate Journal.

[9]  M. Yano,et al.  Antiproliferative activity of flavonoids on several cancer cell lines. , 1999, Bioscience, biotechnology, and biochemistry.

[10]  E. Middleton,et al.  Differential inhibition of proliferation of human squamous cell carcinoma, gliosarcoma and embryonic fibroblast‐like lung cells in culture by plant flavonoids , 1992, Anti-cancer drugs.

[11]  J. Brodbelt,et al.  Structural characterization and isomer differentiation of chalcones by electrospray ionization tandem mass spectrometry. , 2003, Journal of mass spectrometry : JMS.

[12]  P. Tu,et al.  Characterization of seventy polymethoxylated flavonoids (PMFs) in the leaves of Murraya paniculata by on-line high-performance liquid chromatography coupled to photodiode array detection and electrospray tandem mass spectrometry. , 2011, Journal of pharmaceutical and biomedical analysis.

[13]  Hong Yang,et al.  [Isolation and purification of flavones from Murraya exotica L. by high-speed counter-current chromatography]. , 2010, Se pu = Chinese journal of chromatography.

[14]  Z. Abliz,et al.  Characteristic fragmentation behavior of some glucuronide-type triterpenoid saponins using electrospray ionization tandem mass spectrometry. , 2005, Rapid communications in mass spectrometry : RCM.

[15]  A. Theriault,et al.  Citrus polymethoxylated flavones improve lipid and glucose homeostasis and modulate adipocytokines in fructose-induced insulin resistant hamsters. , 2006, Life sciences.

[16]  Ying-Jan Wang,et al.  5-Hydroxy-3,6,7,8,3',4'-hexamethoxyflavone induces apoptosis through reactive oxygen species production, growth arrest and DNA damage-inducible gene 153 expression, and caspase activation in human leukemia cells. , 2007, Journal of agricultural and food chemistry.

[17]  P. Mouly,et al.  Simultaneous separation of flavanone glycosides and polymethoxylated flavones in citrus juices using liquid chromatography. , 1998, Journal of chromatography. A.

[18]  P. Traldi,et al.  The ion-trap mass spectrometer in ion structure studies. The case of [MH]+ ions from chalcone , 1991 .

[19]  R. Rouseff,et al.  Quantitation of polymethoxylated flavones in orange juice by high-performance liquid chromatography. , 1979, Journal of chromatography.

[20]  Chi-Tang Ho,et al.  Hydroxylated polymethoxyflavones and methylated flavonoids in sweet orange (Citrus sinensis) peel. , 2006, Journal of agricultural and food chemistry.

[21]  M. Alcaraz,et al.  Cytotoxicity and Antiproliferative Activities of Several Phenolic Compounds Against Three Melanocytes Cell Lines: Relationship Between Structure and Activity , 2004, Nutrition and cancer.

[22]  T. Walle Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? , 2007, Seminars in cancer biology.