Generic placeholder image

Current Pharmaceutical Analysis


ISSN (Print): 1573-4129
ISSN (Online): 1875-676X

Research Article

Characterization and Identification of Isoflavonoids in the Roots of Millettia speciosa Champ. by UPLC-Q-TOF-MS/MS

Author(s): Dandan Yu and Xianrui Liang*

Volume 15, Issue 6, 2019

Page: [580 - 591] Pages: 12

DOI: 10.2174/1573412914666180608095922

Price: $65


Introduction: The root of Millettia speciosa Champ. (Leguminosae) is one of the wellknown traditional Chinese medicines abundant in phenolic compounds and plays important roles in the treatment of pain or numbness of the joints, blood deficiency sallow, chronic bronchitis and chronic hepatitis.

Objective: An ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) based chemical profiling approach was established for the separation and characterization of isoflavonoids in the roots of Millettia speciosa Champ.

Methods: The roots of Millettia speciosa Champ. were prepared by ethanol extraction followed by further extraction with chloroform. The extracts were analyzed by UPLC-Q-TOF-MS in positive and negative electrospray ion modes at different Collision Energy (CE) values.

Results: A total of 48 components were simultaneously detected, of which 38 components, including 21 isoflavones, 4 phenolic acids, 4 isoflavanones, 2 phenolic aldehydes, 2 flavanones, 1 aliphatic acid, 1 chalcone, 1 flavonol, 1 isoflavane and 1 pterocarpan were unambiguously identified or tentatively assigned based on the retention time, UV spectra, characteristic molecular ions, MS/MS fragmentation data and reference standards. The isomers of isoflavonoids were distinguished using accurate mass, the diagnostic fragmentations of C-ring and UV spectra. The major diagnostic fragment ions of isoflavonoids were observed and the corresponding fragmentation pathways were proposed.

Conclusion: This investigation provides important analysis data for further quality control, pharmacological and toxicological research on Millettia speciosa Champ.

Keywords: Fragment ions, isoflavonoids, isomers, Millettia speciosa, phenolic compounds, UPLC-Q-TOF-MS/MS.

Graphical Abstract
Editorial Board of Guangdong Food and Drug Administration. The standard of Chinese Materia Medica in Guangdong. Guangdong Science and Technology Press, Guangzhou; , 2004, pp. 31-32.
Li, R.R.; Chen, Z.K.; Gao, S.; Liang, S.W. Study progress of Millettia speciosa. Asia-Pac. Trad. Med, 2010, 6, 165-167.
Zhang, S.Y.; Yin, T.; Ling, X.M.; Liang, H.; Zhao, Y.Y. Interactions between thrombin and natural products of Millettia speciosa Champ. using capillary zone electrophoresis. Electrophoresis, 2008, 29, 3391-3397.
Zhao, X.N.; Liang, J.L.; Chen, H.B.; Liang, Y.E.; Guo, H.Z.; Su, Z.R.; Li, Y.C.; Zeng, H.F.; Zhang, X.J. Anti-fatigue and antioxidant activity of the polysaccharides isolated from Millettiae speciosae Champ. Leguminosae. Nutrients, 2015, 7, 8657-8669.
Zhao, X.N.; Wang, X.F.; Liao, J.B.; Guo, H.Z.; Yu, X.D.; Liang, J.L.; Zhang, X.; Su, Z.R.; Zhang, X.J.; Zeng, H.F. Antifatigue effect of Millettiae speciosae Champ (Leguminosae) extract in mice. Trop. J. Pharm. Res., 2015, 14(3), 479-485.
Yin, T.; Liang, H.; Wang, B.; Zhao, Y.Y. A new flavonol glycoside from Millettia speciosa. Fitoterapia, 2010, 81, 274-275.
Ding, P.; Qiu, J.Y.; Ying, G.; Dai, L. Chemical constituents of Millettia speciosa. Chin. Herb. Med., 2014, 6(4), 332-334.
Chen, D.L.; Liu, Y.Y.; Ma, G.X.; Zhu, N.L.; Wu, H.F.; Wang, D.L.; Xu, X.D. Two new rotenoids from the roots of Millettia speciosa. Phytochem. Lett., 2015, 12, 196-199.
Ali, A.A.; Velasquez, M.T.; Hansen, C.T.; Mohamed, A.I.; Bhathena, S.J. Modulation of carbohydrate metabolism and peptide hormones by soybean isoflavones and probiotics in obesity and diabetes. J. Nutr. Biochem., 2005, 16, 693-699.
Davis, J.; Kucuk, O.; Sarkar, F. Molecular effects of sony-isoflavone genistein in prostate cancer cells. J. Nutr., 2000, 130, 686S-687S.
Kenny, A.M.; Prestwood, K.M. Osteoporosis: Pathogenesis, diagnosis, and treatment in older adults. Rheum. Dis. Clin. N. Am., 2000, 26(3), 569-591.
Anthony, M.S. Sony and cardiovascular disease: Cholesterol lowering and beyond. J. Nutr., 2000, 130(3), 662S-663S.
Cornwell, T.; Cohick, W.; Raskin, I. Dietary phytoestrogens and health. Phytochemistry, 2004, 65, 995-1016.
Raju, K.S.R.; Kadian, N.; Taneja, I.; Wahajuddin, M. Phytochemical analysis of isoflavonoids using liquid chromatography coupled with tandem mass spectrometry. Phytochem. Rev., 2015, 14, 469-498.
Liang, X.R.; Xu, Q. Separation and identification of phenolic compounds in Bidens pilosa L. by ultra-high performance liquid chromatography with quadrupole time-of-flight mass spectrometry. J. Sep. Sci., 2016, 39, 1853-1862.
Yang, Y.X.; Wang, A.M.; Wang, Z.; Wang, Y.L.; Zhang, J.; Liu, J.H.; He, X.; Li, Y.J.; Hao, X.Y.; Liao, S.G. Chemical fingerprinting and multi-marker determination of the roots of Indigofera stachyoides by UHPLC-Q-TOF/MS. Curr. Pharm. Anal., 2015, 11(4), 260-268.
Hidau, M.K.; Singh, Y.; Shahi, S.; Mounnika, P.; Singh, S.K. LC-MS/MS assay for quantification of a novel antitubercular molecule S006-830: Pharmacokinetic and plasma protein binding studies in rats. Curr. Pharm. Anal., 2015, 11(1), 35-42.
Huang, W.W.; Hou, J.; Wang, M.Y.; Peng, C.S.; Peng, Y.; Li, X.B. Qualitative and quantitative analysis of constituents in Si-jun-zi tang decoction by HPLC-DAD-ELSD and HPLC-ESI-MS. Curr. Pharm. Anal., 2015, 11(2), 115-123.
Meng, Z.; Shi, Z.H.; Su, M.; Sun, H.W. In vitro metabolism analysis of sulfamerazine in mice liver by ultra performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry. Curr. Pharm. Anal., 2018, 14(1), 17-22.
Cai, T.; Guo, Z.Q.; Xu, X.Y.; Wu, Z.J. Recent (2000-2015) developments in the analysis of minor unknown natural products based on characteristic fragment information using LC-MS. Mass Spectrom. Rev., 2016, 9999, 1-15.
Ren, Q.; Ding, L.; Sun, S.S.; Wang, H.Y.; Qu, L. Chemical identification and quality evaluation of Lycopus lucidus Turcz by UHPLC-Q-TOF-MS and HPLC-MS/MS and hierarchical clustering analysis. Biomed. Chromatogr., 2017, 31, 1-12.
Liu, M.H.; Tong, X.; Wang, J.X.; Zou, W.; Cao, H.; Su, W.W. Rapid separation and identification of multiple constituents in traditional Chinese medicine formula Shenqi Fuzheng injection by ultra-fast liquid chromatography combined with quadrupole-time-of-flight mass spectrometry. J. Pharm. Biomed. Anal., 2013, 74, 141-155.
Klejdus, B.; Plaza, M.; Šnóblová, M.; Lojková, L. Development of new efficient method for isolation of phenolics from sea algae prior to their rapid resolution liquid chromatographic-tandem mass spectrometric determination. J. Pharm. Biomed. Anal., 2017, 135, 87-96.
Troalen, L.G.; Phillips, A.S.; Peggie, D.A.; Barran, P.E.; Hulme, A.N. Historical textile dyeing with Genista tinctorial L.: A comprehensive study by UPLC-MS/MS analysis. Anal. Methods, 2014, 6, 8915-8923.
Xu, T.T.; Yang, M.; Li, Y.F.; Chen, X.; Wang, Q.R.; Deng, W.P.; Pang, X.Y.; Yu, K.; Jiang, B.H.; Guan, S.H.; Guo, D.A. An integrated exact mass spectrometric strategy for comprehensive and rapid characterization of phenolic compounds in licorice. Rapid Commum. Mass Spectrom., 2013, 27, 2297-2309.
Manickavasagam, L.; Gupta, S.; Mishra, S.; Maurya, R.; Chattopadhyay, N.; Jain, G.K. LC-MS/MS method for simultaneous analysis of cladrin and equol in rat plasma and its application in pharmacokinetics study of cladrin. Med. Chem. Res., 2011, 20, 1566-1572.
Ye, M.; Yang, W.Z.; Liu, K.D.; Qiao, X.; Li, B.J.; Cheng, J.; Feng, J.; Guo, D.A.; Zhao, Y.Y. Characterization of flavonoids in Millettia nitida var. hirsutissima by HPLC/DAD/ESI-MSn. J. Pharm. Anal., 2012, 2, 35-42.
Zhang, J.; Xu, X.J.; Xu, W.; Huang, J.; Zhu, D.Y.; Qiu, X.H. Rapid characterization and identification of flavonoids in Radix Astragali by ultra-high-pressure liquid chromatography coupled with linear ion trap-orbitrap mass spectrometry. J. Chromatogr. Sci., 2015, 53, 945-952.
Gampe, N.; Darcsi, A.; Lohner, S.; Béni, S.; Kursinszki, L. Characterization and identification of isoflavonoid glycosides in the root of Spiny restharrow (Ononis spinosa L.) by HPLC-QTOF-MS, HPLC-MS/MS and NMR. J. Pharm. Biomed. Anal., 2016, 123, 74-81.
Liu, R.X.; Ye, M.; Guo, H.Z.; Bi, K.S.; Guo, D.A. Liquid chromatography/electrospray ionization mass spectrometry for the characterization of twenty-three flavonoids in the extract of Dalbergia odorifera. Rapid. Commum. Mass. Spectrom., 2005, 19, 1557-1565.

Rights & Permissions Print Export Cite as
© 2022 Bentham Science Publishers | Privacy Policy