Application of UPLC-QTOF-MS in MSE mode for the rapid and precise identification of alkaloids in goldenseal (Hydrastis canadensis)

Analytical and Bioanalytical Chemistry

Volumn 406, Issue 6, 2014, Pages 1739-1749

  Le, Phuong Mai ^a   McCooeye, Margaret ^a   Windust, Anthony ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Alkaloid; Hydrastis canadensis; Quadrupole time of flight mass spectrometry; Steroid; Structural characterization; Ultra performance liquid chromatography

Indexed keywords

ELECTROSPRAY IONIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PLANT EXTRACTS;

HYDRASTIS CANADENSIS; QUADRUPOLE TIME OF FLIGHT MASS SPECTROMETRY; STEROID; STRUCTURAL CHARACTERIZATION; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

ALKALOIDS;

HYDRASTIS; HYDRASTIS CANADENSIS;

ALKALOID; PLANT EXTRACT;

ARTICLE; CHEMISTRY; ECONOMICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDRASTIS; MASS SPECTROMETRY; METHODOLOGY; TIME;

ALKALOIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDRASTIS; MASS SPECTROMETRY; PLANT EXTRACTS; TIME FACTORS;

EID: 84898047382     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-013-7558-x     Document Type: Article

References (37)

1. Wang D, Liu Z, Guo M, Liu S (2004) Structural elucidation and identification of alkaloids in Rhizoma coptidis by electrospray ionization tandem mass spectrometry. J Mass Spectrom 39:1356-1365
2. n. J Pharm Biomed Anal 37:437-446
3. Zhang Y, Shi Q, Shi P, Zhang W, Cheng Y (2006) Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry. Rapid Commun Mass Spectrom 20:2328-2342
4. Deevanhxay P, Suzukia M, Maeshibuy N, Lia H, Tanaka K, Hirose S (2009) Simultaneous characterization of quaternary alkaloids, 8-oxoprotoberberine alkaloids, and a steoid compound in Coscinium fenestratum by liquid chromatography hybrid ion trap time-of-flight mass spectrometry. J Pharm Biomed Anal 50:413-425
5. n. Anal Bioanal Chem 405(13):4487-4498
6. Shen Y, Zhang R, Moore RJ, Kim J, Metz TO, Hixson KK, Zhao R, Livesay EA, Udseth HR, Smith RD (2005) Automated 20 kpsi RPLC-MS and MS/MS with chromatographic peak capacities of 1000-1500 and capabilities in proteomics and metabolomics. Anal Chem 77:3090-3100
7. Nordstrom A, O'Maille G, Qin C, Siuzdak G (2006) Nonlinear data alignment for UPLC-MS and HPLC-MS based metabolomics: quantitative analysis of endogenous and exogenous metabolites in human serum. Anal Chem 78:3289-3295
8. Zhang J, Jin Y, Dong J, Xiao Y, Feng J, Xue X, Zhang X, Liang X (2009) Systematic screening and characteriation of tertiary and quaternary alkaloids from Corydalis yanhusuo W. T. Wang using ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry. Talanta 78:513-522
9. Han Z, Zheng Y, Chen N, Luan L, Zhou C, Gan L, Wu Y (2008) Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry. J Chromatogr A 1212(1-2):76-81
10. Wang HGS, Qian D, Qian Y, Duan J-A (2012) Comparative analysis of quinolizidine alkaloids from different parts of Sophora alopecuroides seeds by UPLC-MS/MS. J Pharm Biomed Anal 76-68:16-21
11. Zhou DY, Zhang XL, Xu Q, Xue XY, Zhang FF, Liang XM (2009) UPLC/Q-TOFMS/MS as a powerful technique for rapid identification of polymethoxylated flavones in Fructus aurantii. J Pharm Biomed Anal 50:2-8
12. Novak TJ, Grinberg N, Hartman B, Marcinko S, DiMichele L, Mao B (2010) LC/MS using a hybrid quadrupole time of flight mass spectrometer for impurity identification during process chemical development of a novel integrase inhibitor. J Pharm Biomed Anal 51:78-83
13. Li CM, Zhang XL, Xue XY, Zhang FF, Xu Q, Liang XM (2008) Structural characterization of iridoid glucosides by ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass Spectrom 22:1941-1954
14. Li SL, Song JZ, Choi FFK, Qiao CF, Zhou Y, Han QB, Xu HX (2009) Chemical profiling of Radix paeoniae evaluated by ultra-performance liquid chromatography/photo-diode-array/quadrupole time-of-flight mass spectrometry. J Pharm Biomed Anal 49:253-266
15. E; a new approach for generating molecular fragment information for biomarker structure elucidation. Rapid Commun Mass Spectrom 20:1989-1994
16. Rainville PD, Stumpf CL, Shockcor JP, Plumb RS, Nicholson JK (2007) Novel application of reversed-phase UPLC-TOF-MS for lipid analysis in complex biological mixtures: a new tool for lipidomics. J Proteome Res 6:552-558
17. E lipidomic analysis using a shotgun approach and its application to biomarker detection and identification in osteoarthritis patients. J Proteome Res 9:2377-2389
18. E analysis for quantification and identification of major carotenoid and chlorophyll species in algae. Anal Bioanal Chem 404:3145-3154
19. Scazoccio F, Cometa MF, Tomassini L, Palmery M (2001) Anterbacterial activity of Hydrastis canadensis extract and its major isolated alkaloids. Planta Med 67:561-564
20. Ettefagh KA, Burns JT, Junio HA, Kaatz GW, Cech NB (2011) Goldenseal (Hydrastis canadensis L.) extracts synergistically enhance the antibacterial activity of berberine vial efflux pump inhibition. Planta Med 77(8):835-840
21. Jalees R, Dillow JM, Carter SM, Chou J, Le B, Maisel AS (1999) Increased production of antigenspecific immunoglobulins G and M following in vivo treatment with the medicinal plants Echinacea angustifolia, Hydrastis canadensis. Immunol Lett 68:391-395
22. Hwang BY, Roberts SK, Chadwick LR, Wu CD, Kinghorn AD (2003) Antimicrobial constituents from goldenseal (the rhizomes of Hydrastis canadensis) against selected oral pathogens. Planta Med 69:623-627
23. Karmakar SR, Biswas SJ, Khuda-Bukhsh AR (2010) Anti-carcinogenic potentials of a plant extract (Hydrastis canadensis): I Evidence from in vivo studies in mice (Mus musculus). Asian Pac J Cancer Prev 11:545-551
24. Gentry EJ, Jampani HB, Kesharvarz-Shokri A, Morton MD, VanderVelde D, Telikepalli H, Mitscher LA (1998) Antitubercular natural products: Berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, β-hydrastine, and two new quinic acid esters, hydcandinic acid esters-1 and 2. J Nat Prod 61:1187-1193
25. Bolle P, Cometa MF, Palmery M, Tucci P (1998) Response of rabbit detrusor muscle to total extract and major alkaloids of Hydrastis canadensis. Phytother Res 12:S86-S88
26. Abdel-Haq H, Cometa MF, Palmery M, Leone MG, Silvestrini B, Saso L (2000) Relaxant effects of Hydrastis canadensis L. and its major alkaloids on guinea pig isolated trachea. Pharmacol Toxicol 87:218-222
27. Weber HA, Zart MK, Hodges AE, White KD, Barnes SM, Moody LA, Clark AP, Harris RK, Overstreet JD, Smith CS (2003) Method validation for determination of alkaloid content in goldenseal root powder. J AOAC Int 86:476-483
28. Weber HA, Zart MK, Hodges AE, Molloy HM, O'Brien BM, Moody LA, Clark AP, Harrris RK, Overstreet JD, Smith CS (2003) Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial supplies. J Agric Food Chem 51:7352-7358
29. Van Berkel GJ, Tomkins BA, Kerterz V (2007) Thin-layer chromatography/desorption electrospray ionization mass spectrometry: investigation of goldenseal alkaloids. Anal Chem 79:2778-2789
30. Jeong EK, Lee SY, Yu SM, Park NH, Lee HS, Yim YH, Hwang GS, Cheong C, Jung JH, Hong J (2012) Identification of structurally diverse alkaloids in Corydalis species by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 26(15):1661-1674
31. Messana I, Bue RL, Galeffi C (1980) The alkloids of Hydrastis canadensis L. (Ranunculaceae). Two new alkloids: hydrastidine and isohydrastidine. Gaz Chim Ital 110:539-543
32. Wu W, Moyer M (2004) Electrospray tandem mass spectrometry for structural characterization of aporphine-benzylisoquinoline alkaloids. Eur J Mass Spectrom 10:683-689
33. Gleye JAA, Stanislas E (1974) La Canadaline: Nouvel alcaloïde D'Hydrastis canadensis. Phytochemisty 13(3):675-676
34. Rasche F, Svatos A, Maddula RK, Bottcher C, Bocker S (2011) Computing fragmentation trees from tandem mass spectrometry data. Anal Chem 83:1243-1251
35. Hanaoka M, Nagami K, Imanishi T (1979) Transformation of (±)-ophiocarpine and (±)-13-epiophiocarpine to (±)-α- and (±)-β-hydrastine with complete retention of configuration. Chem Pharm Bull 27:1947-1948
36. Soriano MDPC, Shankaraiah N, Santos LS (2010) Short synthesis of noscapine, bicuculline, egenine, capnoidine, and corytensine alkaloids through the addition of 1-siloxy-isobenzofurans to imines. Tetrahedron Lett 51:1770-1773
37. Dinan L (2001) Phytoecdysteroids: biological aspects. Phytochemistry 57:325-339