Planta Med 2009; 75(7): 763-775
DOI: 10.1055/s-0029-1185450
Plant Analysis
Review
© Georg Thieme Verlag KG Stuttgart · New York

Quality Control of Herbal Material and Phytopharmaceuticals with MS and NMR Based Metabolic Fingerprinting

Frank van der Kooy1 , Federica Maltese1 , Young Hae Choi1 , Hye Kyong Kim1 , Robert Verpoorte1
  • 1Division of Pharmacognosy, Section of Metabolomics, Institute of Biology, Leiden University, Leiden, The Netherlands
Further Information

Publication History

received July 30, 2008 revised January 19, 2009

accepted February 2, 2009

Publication Date:
13 March 2009 (online)

Abstract

Metabolic fingerprinting techniques have received a lot of attention in recent years and the annual amount of publications in this field has increased significantly over the past decade. This increase in publications is due to improvements in the analytical performance, most notably in the field of NMR and MS analysis, and the increased awareness of the different applications of this growing field. Metabolomic fingerprinting or profiling is continuously being applied to new areas of research such as drug discovery from natural resources, quality control of herbal material, and discovering lead compounds. In this review the current state of the art of metabolic fingerprinting, focussing on NMR and MS technologies will be discussed. The application of these two analytical tools in the quality control of herbal material and phytopharmaceuticals forms the major part of this review. Finally we will look at the future developments and perspectives of these two technologies in the quality control of herbal material.

References

  • 1 Klayman D L. Qinghaosu (artemisinin): an antimalarial drug from China.  Science. 1985;  228 1049-1055
  • 2 Small E. Cannabis as a source of medicinals, nutraceuticals, and functional foods. Acharya SN, Thomas JE Advances in medicinal plant research. Kerala; Research Signpost 2007: 1-39
  • 3 Villas-Boas S G, Rasmussen S, Lane G A. Metabolomics or metabolite profiles?.  Trends Biotechnol. 2005;  23 385-386
  • 4 Goodacre R, Vaidyanathan S, Dunn W B, Harrigan G G, Kell D B. Metabolomics by numbers: acquiring and understanding global metabolite data.  Trends Biotechnol. 2004;  22 245-252
  • 5 Daviss B. Growing pains for metabolomics.  Scientist. 2005;  19 25-28
  • 6 Kubeczka K .-H, Formácek V. Essential oils: analysis by capillary gas chromatography and carbon 13-NMR spectroscopy. London; John Wiley & Sons Ltd. 1980
  • 7 Schripsema J, Verpoorte R. Investigation of extracts of plant cell cultures by proton nuclear magnetic resonances spectroscopy.  Phytochem Anal. 1991;  2 155-162
  • 8 Reily M D, Lindon J C. NMR spectroscopy: principles and instrumentation. Robertson DG, Lindon J, Nicholson JK, Holmes E Metabonomics in toxicity assessment. Boca Raton; CRC Press 2005: 75-104
  • 9 Seger C, Sturm S. Analytical aspects of plant metabolic profiling platforms: current standings and future aims.  J Proteome Res. 2007;  6 480-497
  • 10 Choi Y H, Kim H K, Verpoorte R. Metabolomics. Kayser O, Quax W Medicinal plant biotechnology from basic research to industrial applications. Weinheim; Wiley-VCH 2006: 9-28
  • 11 Pauli G F, Jaki B U, Lankin D C. Quantitative 1H NMR: development and potential of a method for natural products analysis.  J Nat Prod. 2005;  68 133-149
  • 12 Verpoorte R, Choi Y H, Kim H K. NMR-based metabolomics at work in phytochemistry.  Phytochem Rev. 2007;  6 3-14
  • 13 Breitling R, Ritchie S, Goodenowe D, Stewart M L, Barrett M P. Ab initio prediction of metabolic networks using Fourier transform mass spectrometry data.  Metabolomics. 2006;  2 155-164
  • 14 Jaki B U, Franzblau S G, Cho S H, Pauli G F. Development of an extraction method for mycobacterial metabolome analysis.  J Pharm Biomed Anal. 2006;  41 196-200
  • 15 Choi Y H, Kim H K, Hazekamp A, Erkelens C, Lefeber A WM, Verpoorte R. Metabolomic differentiation of Cannabis sativa cultivars using 1H NMR spectroscopy and principal component analysis.  J Nat Prod. 2004;  67 953-957
  • 16 Choi Y H, Tapias E C, Kim H K, Lefeber A WM, Erkelens C, Verhoeven J TJ, Brzin J, Zel J, Verpoorte R. Metabolic discrimination of Catharanthus roseus leaves infected by phytoplasma using 1H‐NMR spectroscopy and multivariate data analysis.  Plant Physiol. 2004;  135 2398-2410
  • 17 Choi Y H, Sertic S, Kim H K, Wilson E G, Michopoulos F, Lefeber A WM, Erkelens C, Kricun S DP, Verpoorte R. Classification of Ilex species based on metabolomic fingerprinting using NMR and multivariate data analysis.  J Agric Food Chem. 2005;  53 1237-1245
  • 18 Suhartono L, Van Iren F, De Winter W, Roytrakul S, Choi Y H, Verpoorte R. Metabolic comparison of cryopreserved and normal cells from Tabernaemontana divaricata suspension cultures.  Plant Cell Tissue Org Cult. 2005;  83 59-66
  • 19 Kim H K, Choi Y H, Erkelens C, Lefeber A WM, Verpoorte R. Metabolic fingerprinting of Ephedra species using 1H‐NMR spectroscopy and principal component analysis.  Chem Pharm Bull. 2005;  53 105-109
  • 20 Hendrawati O, Yao Q, Kim H K, Linthorst H JM, Erkelens C, Lefeber Choi A WMYH, Verpoorte R. Metabolic differentiation of Arabidopsis treated with methyl jasmonate using nuclear magnetic resonance spectroscopy.  Plant Sci. 2006;  170 1118-1124
  • 21 Liang Y-S, Choi Y H, Kim H K, Linthorst H JM, Verpoorte R. Metabolomic analysis of methyl jasmonate treated Brassica rapa leaves by two dimensional NMR spectroscopy and multivariate analysis.  Phytochemistry. 2006;  67 2503-2511
  • 22 Widarto H T, Van der Meijden E, Lefeber A WM, Erkelens C, Kim H K, Choi Y H, Verpoorte R. Metabolomic differentiation of Brassica rapa leaves attacked by herbivore using two dimensional nuclear magnetic resonance spectroscopy.  J Chem Ecol. 2006;  32 2417-2428
  • 23 Le Gall G, Colquhoun I J, Defernez M. Metabolite profiling using 1H NMR spectroscopy for quality assessment of green tea, Camellia sinensis (L.).  J Agric Food Chem. 2004;  52 692-700
  • 24 Ward J L, Harris C, Lewis J, Beale M H. Assessment of 1H‐NMR spectroscopy and multivariate analysis as a technique for metabolite fingerprinting of Arabidopsis thaliana.  Phytochemistry. 2003;  62 949-957
  • 25 Frédérich M, Choi Y H, Verpoorte R. Quantitative analysis of strychnine and brucine in Strychnos nux-vomica using 1H‐NMR.  Planta Med. 2003;  69 1169-1171
  • 26 Kruger N J, Troncoso-Ponce A T, Ratcliffe R G. 1H NMR metabolite fingerprinting and metabolomic analysis of perchloric acid extracts from plant tissues.  Nat Protoc. 2008;  3 1001-1012
  • 27 Rasmussen B, Cloarec O, Tang H, Staerk D, Jaroszewski J. Multivariate analysis of integrated and full-resolution 1H‐NMR spectral data from complex pharmaceutical preparations: St. John's wort.  Planta Med. 2006;  72 556-563
  • 28 Choi Y H, Choi H-K, Hazekamp A, Bermejo P, Schilder Y DC, Erkelens C, Verpoorte R. Quantitative analysis of bilobalide and ginkgolides from Ginkgo biloba leaves and ginkgo products using 1H‐NMR.  Chem Pharm Bull. 2003;  51 158-161
  • 29 Kim H K, Choi Y H, Chang W-T, Verpoorte R. Quantitative analysis of ephedrine analogues from Ephedra species using 1H‐NMR.  Chem Pharm Bull. 2003;  51 1382-1385
  • 30 Schripsema J, Erkelens C, Verpoorte R. Intra-and extracellular carbohydrates in plant cell cultures investiated by 1H‐NMR.  Plant Cell Rep. 1991;  9 527-530
  • 31 Beckwith-Hall B M, Thompson N A, Nicholson J K, Lindon J, Holmes E. A metabonomic investigation of hepatotoxicity using diffusion-edited 1H‐NMR spectroscopy of blood serum.  Analyst. 2003;  128 814-818
  • 32 Phalaraksh C, Lenz E M, Lindon J C, Nocholson J K, Farrant R D, Reynolds S E, Wilson I D, Osborn D, Weeks J M. NMR spectroscopic studies on the hemolymph of the tobacco hornworm, Manduca sexta: assignment of 1H and 13C NMR spectra.  Insect Biochem Mol Biol. 1999;  29 795-805
  • 33 Davis R A, Charlton A J, Godward J, Jones S A, Harrison M, Wilson J C. Adaptive binning: an improved binning method for metabolomics data using the undecimated wavelet transform.  Chemometr Intell Lab Syst. 2007;  85 144-154
  • 34 Kim H K, Choi Y H, Verpoorte R. Metabolomic analysis of Catharanthus roseus using NMR and principal component analysis. Saito K, Dixon RA, Willmitzer L Biotechnology in agriculture and forestry 57 plant metabolomics. Leipzig; Springer 2006: 261-276
  • 35 Defernez M, Colquhoun I J. Factors affecting the robustness of metabolite fingerprinting using 1H NMR spectra.  Phytochemistry. 2003;  62 1009-1017
  • 36 Forshed J, Schuppe-Koistinen I, Jacobsson S P. Peak alignment of NMR signals by means of a genetic algorithm.  Anal Chim Acta. 2003;  487 189-199
  • 37 Lee G-C, Woodruff D L. Beam search for peak alignment of NMR signals.  Anal Chim Acta. 2004;  513 413-416
  • 38 Eriksson L, Johansson E, Kettaneh-Wold N, Wold S. Multi- and megabariate data analysis. Principles and applications. Umeå; Umetrics 2001
  • 39 Berger S, Braun S. 200 and more NMR experiments. Weinheim; Wiley-VCH 2004
  • 40 Kemsley E K. Discriminant analysis and class modelling of spectroscopic data. Chichester; John Wiley 1998
  • 41 Lindon J C, Holmes E, Nicholson J K. Pattern recognition methods and applications in biomedical magnetic resonance.  Prog Nucl Magn Reson Spectrosc. 2001;  39 1-40
  • 42 Colquhoun I J. Use of NMR for metabolic profilind in plant systems.  J Pestic Sci. 2007;  32 200-212
  • 43 Keun H C, Ebbels T MD, Antti H, Bollard M E, Beckonert O, Holmes Lindon E JC, Nicholson J K. Improved analysis of multivariate data by variable stability scaling: application to NMR-based metabonomic profiling.  Anal Chim Acta. 2003;  490 265-276
  • 44 Viant M R. Improved methods for the acquisition and interpretation of NMR metabolomic data.  Biochem Biophys Res Commun. 2003;  310 943-948
  • 45 Wolters A M, Jayawickrama D A, Sweedler J V. Microscale NMR.  Curr Opin Chem Biol. 2002;  6 711-716
  • 46 Viel S, Capitani D, Mannina L, Segre A. Diffusion-ordered NMR spectroscopy: a versatile tool for the molecular weight determination of uncharged polysaccharides.  Biomacromolecules. 2003;  4 1843-1847
  • 47 Ambrus A, Friedrich K, Somogyi Á. Oligomerization of nitrophorins.  Anal Biochem. 2006;  352 286-295
  • 48 Politi M, Groves P, Chávex I, Canada F J, Jiménez-Barbero J. Useful application of DOSY experiments for the study of mushroom polysaccharides.  Carbohydr Res. 2006;  341 84-89
  • 49 Fraceto L F, Oyama Jr S, Nakaie C R, Spisni A, De Paula E, Pertinhez T A. Interaction of local anesthetics with a peptide encompassing the IV/SA‐S5 inler of the Na+ channel.  Biophys Chem. 2006;  123 29-39
  • 50 Zeng B, Zhu X, Cai S, Chen Z. Interactions between diperoxovanadate complex and amide ligands in aqueous solution.  Spectrochim Acta Part A. 2007;  67 202-207
  • 51 Kapur G S, Findeisen M, Berger S. Analysis of hydrocarbon mixtures by diffusion-ordered NMR spectroscopy.  Fuel. 2000;  79 1347-1351
  • 52 Rauter A P, Martins A, Borges C, Ferreira J, Justino J, Bronze M –R, Coelho A V, Choi Y H, Verpoorte R. Liquid chromatography–diode array detection–electrospray ionisation mass spectrometry/nuclear magnetic resonance analyses of the anti-hyperglycemic flavonoid extract of Genista tenera: structure elucidation of a flavonoid-C-glycoside.  J Chromatogr A. 2005;  1089 59-64
  • 53 Bradley S A, Krishnamurthy K, Hu H. Simplifying DOSY spectra with selective TOCSY edited preparation.  J Magn Reson. 2005;  172 110-117
  • 54 Lucas L H, Otto W, Larive C K. The 2D-J-DOSY experiment: resolving diffusion coefficients in mixtures.  J Magn Reson. 2002;  156 138-145
  • 55 Barjat A, Morris G A, Swanson A G. A three-dimensional DOSY-HMQC experiment for the high-resolution analysis of complex mixtures.  J Magn Reson. 1998;  131 131-138
  • 56 Wang Y, Tang H, Nicholson J K, Hylands P J, Sampson J, Whitcombe S, Stewart C G, Caiger S, Oru I, Holmes E. Metabolomic strategy for the classification and quality control of phytomedicine: a case study of chamomile flower (Matricaria recutita L.).  Planta Med. 2004;  70 250-255
  • 57 Frédérich M, Choi Y H, Angenot L, Harnischfeger G, Lefeber A WM, Verpoorte R. Metabolomic analysis of Strychnos nux-vomica, icaja and ignatii extracts by 1H nuclear magnetic resonance spectrometry and multivariate analysis techniques.  Phytochemistry. 2004;  65 1993-2001
  • 58 Yang S Y, Kim H K, Lefeber A WM, Erkelens C, Angelova N, Choi Y H, Verpoorte R. Application of two-dimensional nuclear magnetic resonance spectroscopy to quality control of ginseng commercial products.  Planta Med. 2006;  72 364-369
  • 59 Shin Y S, Bang K H, In D S, Kim O T, Hyun D Y, Ahn I O, Ku B C, Kim S W, Seong N S, Cha S W, Lee D, Choi H K. Fingerprinting analysis of fresh ginseng roots of different ages using H‐NMR spectroscopy and principal component analysis.  Arch Pharm Res. 2007;  30 1625-1628
  • 60 Kang J, Lee S, Kang S, Kwon H N, Park J H, Kwon S W, Park S. NMR-based metabolomics approach for the differentiation of ginseng (Panax ginseng) roots from different origins.  Arch Pharm Res. 2008;  31 330-336
  • 61 Tarachiwin L, Katoh A, Ute K, Fukusaki E. Quality evaluation of Angelica acutiloba Kitagawa roots by 1H NMR-based metabolic fingerprinting.  J Pharm Biomed Anal. 2008;  DOI: 10.1016/j.jpba
  • 62 Van der Kooy F, Verpoorte R, Marion Meyer J J. Metabolomic quality control of claimed anti-malarial Artemisia afra herbal remedy and A. afra and A. annua plant extracts.  South African J Bot. 2008;  74 186-189
  • 63 Bailey N JC, Sampson J, Hylands P J, Nicholson J K, Holmes E. Multi component metabolic classification of commercial feverfew preparations via high-filed 1H‐NMR spectroscopy and chemometrics.  Planta Med. 2002;  68 734-738
  • 64 Bilia A R, Bergonzi M C, Lazari D, Vincieri F F. Characterization of commercial kava-kava herbal drug and herbal drug preparations by means of nuclear magnetic resonance spectroscopy.  J Agric Food Chem. 2002;  50 5016-5025
  • 65 Bailey N JC, Wang Y L, Sampson J, Davis W, Whitcombe I, Hylands P J, Croft S L, Holmes E. Prediction of anti-plasmoidal activity of Artemisia annua extracts: application of 1H‐NMR spectroscopy and chemometrics.  J Pharm Biomed Anal. 2004;  35 117-126
  • 66 Roos G, Röseler C, Berger-BűterK, Simmen U. Classification and correction of St. John's wort extracts by nuclear magnetic resonance spectroscopy, multivariate data analysis and pharmacological activity.  Planta Med. 2004;  70 771-777
  • 67 Holmes E, Tang H, Wang Y, Seger C. The assessment of plant metabolite profiles by NMR-based methodologies.  Planta Med. 2007;  72 771-785
  • 68 Bedair M, Sumner L W. Current and emerging mass-spectrometry technologies for metabolomics.  Trends Anal Chem. 2008;  27 238-250
  • 69 García-Villalba R, León C, Dinelli G, Segura-Carretero A, Fernández-Gutiérrez A, Garcia-Cañas V, Cifuentes A. Comparative metabolomic study of transgenic versus conventional soybean using capillary electrophoresis–time-of-flight mass spectrometry.  J Chromatogr A. 2008;  1195 164-173
  • 70 Harris C S, Burt A J, Saleem A, Le P M, Martineau L C, Haddad P S, Bennett S AL, Arnason J T. A single HPLC‐PAD-APCI/MS method for the quantitative comparison of phenolic compounds found in leaf, stem, root and fruit extracts of Vaccinium angustifolium. .  Phytochem Anal. 2007;  18 161-169
  • 71 Grata E, Boccard J, Glauser G, Carrupt P-A, Farmer E E, Wolfender J-L, Rudaz S. Development of a two-step screening ESI‐TOF‐MS method for rapid determination of significant stress-induced metabolome modifications in plant leaf extracts: the wound response in Arabidopsis thaliana as a case study.  J Sep Sci. 2007;  30 2268-2278
  • 72 Vorst O, De Vos C HR, Lommen A, Staps R V, Visser R GF, Bino R J, Hall R D. A non-directed approach to the differential analysis of multiple LC–MS-derived metabolic profiles.  Metabolomics. 2005;  1 169-180
  • 73 De Vos R CH, Moco S, Lommen A, Keurentjes J JB, Bino R J, Hall R D. Untargeted large-scale plant metabolomics using liquid chromatography coupled to mass spectrometry.  Nat Protoc. 2007;  2 778-791
  • 74 Zeng Z D, Liang Y Z, Chau F T, Chen S, Daniel M KW, Chan C O. Mass spectral profiling: an effective tool for quality control of herbal medicines.  Anal Chim Acta. 2007;  604 89-98
  • 75 Pongsuwan W, Bamba T, Yonetani T, Kobayashi A, Fukusaki E. Quality prediction of Japanese green tea using pyrolyzer coupled GC/MS based metabolic fingerprinting.  J Agric Food Chem. 2008;  56 744-750
  • 76 Xie G, Plumb R, Su M, Xu Z, Zhao A, Qiu M, Long X, Liu Z, Jia W. Ultra-performance LC/TOF MS analysis of medicinal Panax herbs for metabolomic research.  J Sep Sci. 2008;  31 1015-1026
  • 77 Williams B J, Cameron C J, Workman R, Broeckling C D, Sumner L W, Smith J T. Amino acid profiling in plant cell cultures: an inter-laboratory comparison of CE‐MS and GC‐MS.  Electrophoresis. 2007;  28 1371-1379
  • 78 Timischl B, Dettmer K, Kaspar H, Thieme M, Oefner P J. Development of a quantitative, validated capillary electrophoresis-time of flight-mass spectrometry method with integrated high-confidence analyte identification for metabolomics.  Electrophoresis. 2008;  29 2203-2214
  • 79 Inbaraj B S, Lua H, Hung C F, Wu W B, Lin C L, Chen B H. Determination of carotenoids and their esters in fruits of Lycium barbarum Linnaeus by HPLC–DAD–APCI–MS.  J Pharm Biomed Anal. 2008;  47 812-818
  • 80 Thiocone A, Farmer E E, Wolfender J –L. Screening for wound-induced oxylipins in Arabidopsis thaliana by differential HPLC-APCI/MS profiling of crude leaf extracts and subsequent characterisation by capillary-scale NMR.  Phytochem Anal. 2008;  19 198-205
  • 81 Clarkson C, Strk D, Hansen S H, Smith P J, Jaroszewski J W. Identification of major and minor constituents of Harpagophytum procumbens (Devil's Claw) using HPLC‐SPE‐NMR and HPLC-ESIMS/APCIMS.  J Nat Prod. 2006;  69 1280-1288
  • 82 Aharoni A, De Vos C HR, Verhoeven H A, Maliepaard C A, Kruppa G, Bino R, Goodenowe D B. Nontargeted metabolome analysis by use of Fourier transform ion cyclotron mass spectrometry.  OMICS. 2002;  6 217-234
  • 83 Ohta D, Shibata D, Kanaya S. Metabolic profiling using Fourier-transform ion-cyclotron-resonance mass spectrometry.  Anal Bioanal Chem. 2007;  389 1469-1475
  • 84 Kang J, Zhou L, Sun J, Han J, Guo D-A. Chromatographic fingerprint analysis and characterization of furocoumarins in the roots of Angelica dahurica by HPLC/DAD/ESI‐MSn technique.  J Pharm Biomed Anal. 2008;  47 778-785
  • 85 Thysell E, Pohjanen E, Lindberg J, Schuppe-Koistinen I, Moritz T, Jonsson P, Antti H. Reliable profile detection in comparative metabolomics.  OMICS. 2007;  11 209-224
  • 86 Broeckling C D, Reddy I R, Duran A L, Zhao X, Sumner L W. MET-IDEA: data extraction tool for mass spectrometry-based metabolomics.  Anal Chem. 2006;  78 4334-4341
  • 87 Su J, Fu P, Shen Y, Zhang C, Liang M, Liu R, Li H, Zhang W. Simultaneous analysis of flavonoids from Hypericum japonicum Thunb. ex Murray (Hypericaceae) by HPLC‐DAD‐ESI/MS.  J Pharm Biomed Anal. 2008;  46 342-348
  • 88 Liu Q, Li H, Hang T. Identification of chemical components illegally mixed in traditional Chinese medicine preparations.  Zhongguo Yaoshi. 2007;  10 735-737
  • 89 Li Y, Hu Z, He L. An approach to develop binary chromatographic fingerprints of the total alkaloids from Caulophyllum robustum by high performance liquid chromatography/diode array detector and gas chromatography/mass spectrometry.  J Pharm Biomed Anal. 2007;  43 1667-1672
  • 90 Jensen A G, Ndjoko K, Wolfender J –L, Hostettmann K, Camponovo F, Soldati F. Liquid chromatography-atmospheric pressure chemical ionisation/mass spectrometry: a rapid and selective method for the quantitative determination of ginkgolides and bilobalide in ginkgo leaf extracts and phytopharmaceuticals.  Phytochem Anal. 2002;  13 31-38
  • 91 Tiberti L A, Yariwake J H, Ndjoko K, Hostettmann K. Identification of flavonols in leaves of Maytenus ilicifolia and M. aquifolium (Celastraceae) by LC/UV/MS analysis.  J Chromatogr B. 2007;  846 378-384
  • 92 Bruni R, Pellati F, Bellardi M G, Benvenuti S, Paltrinieri S, Bertaccini A, Bianchiet A. Herbal drug quality and phytochemical composition of Hypericum perforatum L. affected by ash yellows phytoplasma infection.  J Agric Food Chem. 2005;  53 964-968
  • 93 Kovacs H, Moskau D, Spraul M. Cryogenically cooled probes – a leap in NMR technology.  Prog Nucl Magn Reson Spectrosc. 2005;  46 131-155
  • 94 Schroeder F C, Gronquist M. Extending the scope of NMR spectroscopy with microcoil probes.  Angew Chem Int Ed Engl. 2006;  45 7122-7131
  • 95 Kopka J J. Current challenges and developments in GC‐MS based metabolite profiling technology.  Biotechnology. 2006;  124 312-322
  • 96 Exarchou V, Godejohann M, van Beek T A, Gerothanassis I P, Vervoort J. LC‐UV-solid-phase extraction-NMR‐MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano.  Anal Chem. 2003;  75 6288-6294
  • 97 Seger C, Godejohann M, Tseng L H, Spraul M, Girtler A, Sturm S, Stuppner H. LC‐DAD‐MS/SPE‐NMR hyphenation. A tool for the analysis of pharmaceutically used plant extracts: identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens. .  Anal Chem. 2005;  77 878-885
  • 98 Wolfender J L, Rodrigues S, Hostettmann K, Hiller W. Liquid chromatography/ultraviolet/mass spectrometric and liquid chromatography/nuclear magnetic resonance spectroscopic analysis of crude extract of Gentianaceae species.  Phytochem Anal. 1997;  8 97-104
  • 99 Ioset J R, Wolfender J L, Marston A, Gupta M P, Hostettmann K. Identification of two isomeric meroterpenoid naphtoquinones from Cordia linnaei by liquid chromatography-mass spectrometry and liquid chromatography-nuclear magnetic resonance spectroscopy.  Phytochem Anal. 1999;  10 137-142
  • 100 Queiroz E F, Wolfender J L, Atindehou K K, Traore D, Hostettmann K. On-line identification of the antifungal constituents of Erythrina vogelii by liquid chromatography with tandem mass spectrometry, ultraviolet adsorbance detection and nuclear magnetic resonance spectrometry combined with chroamtographic micro-fractionation.  J Chromatogr A. 2002;  974 123-134
  • 101 Cogne A L, Queiroz E F, Wolfender J L, Marston A, Mavi S, Hostettmann K. On-line identification of unstable catalpol derivatives from Jamesbrittenia fodina by LC‐MS and LC‐NMR.  Phytochem Anal. 2003;  14 67-73
  • 102 Ramm M, Wolfender J L, Queiroz E F, Hostettmann K, Hamburger M. Rapid analysis of nucleotide-activated sugars by high-performance liquid chromatography coupled with diode-array detection, electrospray ionization mass spectrometry and nuclear magnetic resonance.  J Chromatogr A. 2004;  1034 139-148
  • 103 Jaroszewski J W. Hyphenated NMR methods in natural products research, Part 1: direct hyphenation.  Planta Med. 2005;  71 691-700
  • 104 Glauser G, Guillarme D, Grata E, Boccard J, Thiocone A, Carrupt P A, Veuthey J-L, Rudaz S, Wolfender J-L. Optimized liquid chromatography–mass spectrometry approach for the isolation of minor stress biomarkers in plant extracts and their identification by capillary nuclear magnetic resonance.  J Chromatogr A. 2008;  1180 90-98
  • 105 Grata E, Boccard J, Guillarme D, Glauser G, Carrupt P A, Farmer E E, Wolfender J-L, Rudaz S. UPLC‐TOF‐MS for plant metabolomics: a sequential approach for wound marker analysis in Arabidopsis thaliana.  J Chromatogr B. 2008;  871 261-270
  • 106 Swartz M E. UPLC™: an introduction and review.  J Liq Chromatogr Rel Technol. 2005;  28 1253-1263
  • 107 Nguyen D TT, Guillarme D, Rudaz S, Veuthey J L. Fast analysis in liquid chromatography using small particle size and high pressure.  J Sep Sci. 2006;  29 1836-1848
  • 108 Guan J, Laia C M, Li S P. A rapid method for the simultaneous determination of 11 saponins in Panax notoginseng using ultra performance liquid chromatography.  J Pharm Biomed Anal. 2007;  44 996-1000
  • 109 Li P, Xu G, Li S P, Wang Y T, Fan T P, Zhao Q S, Zhang Q W. Optimizing ultraperformance liquid chromatographic analysis of 10 diterpenoid compounds in Salvia miltiorrhiza using central composite design.  J Agric Food Chem. 2008;  56 1164-1171
  • 110 Chen X J, Ji H, Zhang Q W, Tu P F, Wang Y T, Guo B L, Li S P. A rapid method for simultaneous determination of 15 flavonoids in Epimedium using pressurized liquid extraction and ultra-performance liquid chromatography.  J Pharm Biomed Anal. 2008;  46 226-235
  • 111 Johnson K A, Plumb R J. Investigating the human metabolism of acetaminophen using UPLC and exact mass oa-TOF MS.  J Pharm Biomed Anal. 2005;  39 805-810
  • 112 Wilson I D, Nicholson J K, Castro-Perez J, Granger J H, Johnson K A, Smith B W, Plumb R S. High resolution “ultra performance” liquid chromatography coupled to oa-TOF mass spectrometry as a tool for differential metabolic pathway profiling in functional genomic studies.  J Proteome Res. 2005;  4 591-598
  • 113 Nordström A, O'Maille G, Qin C, Siuzdak G. Nonlinear data alignment for UPLC‐MS and HPLC‐MS based metabolomics: quantitative analysis of endogenous and exogenous metabolites in human serum.  Anal Chem. 2006;  78 3289-3295
  • 114 Yu K, Little D, Plumb R, Smith B. High-throughput quantification for a drug mixture in rat plasma: a comparison of ultra performance liquid chromatography/tandem mass spectrometry with high-performance liquid chromatography/tandem mass spectrometry.  Rapid Commun Mass Spectrom. 2006;  20 544-552
  • 115 Jacob S S, Smith N W, Legido-Quigley C. Assessment of Chinese medicinal herb metabolite profiles by UPLC‐MS-based methodology for the detection of aristolochic acids.  J Sep Sci. 2007;  30 1200-1206
  • 116 Naidong W. Bioanalytical liquid chromatography tandem mass spectrometry methods on underivatized silica columns with aqueous/organic mobile phases.  J Chromatogr B. 2003;  796 209-224
  • 117 Tolstikov V V, Fiehn O. Analysis of highly polar compounds of plant origin: combination of hydrophilic interaction chromatography and electrospray ion trap mass spectrometry.  Anal Biochem. 2002;  301 298-307
  • 118 Kind T, Tolstikov V V, Fiehn O, Weiss R H. A comprehensive urinary metabolomic approach for identifying kidney cancer.  Anal Biochem. 2007;  363 185-195
  • 119 Dunn B W. Current trends and future requirements for the mass spectrometric investigation of microbial, mammalian and plant metabolomes.  Physiol Biol. 2008;  5 1-24
  • 120 Washburn M, Wolters D, Yates J. Large-scale analysis of the yeast proteome by multidimensional protein identification technology.  Nat Biotechnol. 2001;  19 242-247
  • 121 Wolters D, Washburn M, Yates J. An automated multidimensional protein identification technology for shotgun proteomics.  Anal Chem. 2001;  73 5683-5690
  • 122 Dugo P, Kumm T, Crupi M L, Cotroneo A, Mondello L. Comprehensive two-dimensional liquid chromatography combined with mass spectrometric detection in the analyses of triacylglycerols in natural lipidic matrixes.  J Chromatogr A. 2006;  1112 269-275
  • 123 Ryan D, Robards K. Analytical chemistry considerations in plant metabolomics.  Sep Purif Rev. 2006;  35 319-356
  • 124 Mondello L, Tranchida P Q, Dugo P, Dugo G. Comprehensive two-dimensional gas chromatography-mass spectrometry: a review.  Mass Spectrom Rev. 2008;  27 101-124
  • 125 Shellie R A, Marriott P J. Comprehensive two-dimensional gas chromatography-mass spectrometry analysis of Pelargonium graveolens essential oil using rapid scanning quadrupole mass spectrometry.  Analyst. 2002;  128 879-883
  • 126 Shellie R A, Marriot P J, Huie C W. Comprehensive two-dimensional gas chromatography (GC'GC) and GC'GC-quadrupole MS analysis of Asian and American ginseng.  J Sep Sci. 2003;  26 1185-1192
  • 127 Shellie R A, Welthagen W, Zrostlikova J, Spranger J, Ristow M, Fiehn O, Zimmermann R. Statistical methods for comparing comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry results: metabolomics analysis of mouse tissue extracts.  J Chromatogr A. 2005;  1086 83-90
  • 128 Hope J L, Prazen B J, Nilsson E J, Jack R M, Synovec R E. Comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry detection: analysis of amino acid and organic acid trimethylsilyl derivatives, with application to the analysis of metabolites in rye grass samples.  Talanta. 2005;  65 380-388
  • 129 Pierce K M, Hope J L, Hoggard J C, Synovec R E. Principal component analysis based method to discover chemical differences in comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry (GCxGC-TOFMS) separations of metabolites in plant samples.  Talanta. 2006;  70 797-804
  • 130 Verpoorte R, Choi Y H, Mustafa N R, Kim H K. Metabolomics: back to basics.  Phytochem Rev. 2008;  7 525-537
  • 131 Schad M, Mungur R, Fiehn O, Kehr J. Metabolic profiling of laser microdissected vascular bundles of Arabidopsis thaliana. .  Plant Methods. 2005;  1 1-10
  • 132 Schneider B, Hölscher D. Laser microdissection and cryogenic nuclear magnetic resonance spectroscopy: an alliance for cell type-specific metabolite profiling.  Planta. 2007;  225 763-770
  • 133 Li S H, Schneider B, Gershenzon J. Microchemical analysis of laser-microdissected stone cells of Norway spruce by cryogenic nuclear magnetic resonance spectroscopy.  Planta. 2007;  225 771-779

Dr. Frank van der Kooy

Division of Pharmacognosy
Section of Metabolomics
Institute of Biology
Leiden University

Einsteinweg 55

PO Box 9502

2300RA Leiden

Netherlands

Phone: + 31 7 15 27 44 71

Fax: + 31 7 15 27 45 11

Email: frank.vanderkooy@chem.leidenuniv.nl

    >