Subscribe to RSS
DOI: 10.1055/s-0028-1088393
© Georg Thieme Verlag KG Stuttgart · New York
HPLC in Natural Product Analysis: The Detection Issue
Publication History
Received: July 31, 2008
Revised: October 14, 2008
Accepted: October 23, 2008
Publication Date:
14 January 2009 (online)
Abstract
High-performance liquid chromatography (HPLC) is a very powerful and versatile chromatographic technique for the separation of natural products (NPs) in complex matrices, such as crude extracts for selective detection and quantification or general profiling. The method is widespread and has been adapted to the analysis of a broad range of NPs generally without the need for complex sample preparation. The choice of the appropriate detection method in HPLC is crucial because of the diversity of NPs and the fact that there is no single technique for their efficient detection. In this review both qualitative and quantitative applications of HPLC with UV, DAD, FD, ECD, RID, FID, CL, ESLD, CAD, MS, MS-MS, and NMR are covered to provide a general, rather than an exhaustive, overview. The potential and limitations as well as some new trends in HPLC hyphenation are discussed.
Abbreviations
APCI:atmospheric pressure chemical ionisation
API:atmospheric pressure ionisation
APPI:atmospheric pressure photoionisation
CAD:charged aerosol detection
CapNMR:capillary NMR
CID:collision-induced dissociation
CL:chemiluminescence
DAD:photodiode array detection
ECD:electrochemical detection
EI:electron impact
ELSD:evaporative light scattering detection
ESI:electrospray ionisation
FD:fluorescence detection
FID:flame ionisation detection
FT:Fourier transform
HCA:hierarchical clustering analysis
HPLC:high-performance liquid chromatography
HR:high resolution
LOD:limit of detection
LOQ:limit of quantification
LR:low resolution
MS:mass spectrometry
MS-MS:tandem mass spectrometry
MSn:multiple-stage mass spectrometry
MVDA:multivariate data analysis
NI:negative ion
NMR:nuclear magnetic resonance
PCA:principal component analysis
PI:positive ion
Q:quadrupole
QQQ:triple quadrupole
RID:refractive index detection
SPE:solid-phase extraction
TOF:time of flight
UHPLC:ultra high-pressure liquid chromatography
UV:ultraviolet
Key words
high-performance liquid chromatography - detection - hyphenation - natural products - dereplication - plant extracts
References
- 1 Larsson J, Gottfries J, Muresan S, Backlund A. ChemGPS-NP: Tuned for navigation in biologically relevant chemical space. J Nat Prod. 2007; 70 789-94
- 2 Rochfort S. Metabolomics reviewed: A new ”Omics” platform technology for systems biology and implications for natural products research. J Nat Prod. 2005; 68 1813-20
- 3 Kingston D GI. High-performance liquid-chromatography of natural-products. J Nat Prod. 1979; 42 237-60
- 4 Natishan T K. Recent developments of achiral HPLC methods in pharmaceuticals using various detection modes. J Liq Chromatogr Relat Technol. 2004; 27 1237-316
- 5 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 1836-48
- 6 David F, Vanhoenacker G, Tienpont B, Francois I, Sandra P. Coupling columns and multidimensional configurations to increase peak capacity in liquid chromatography. Lc Gc Europe. 2007; 20 154-8
- 7 Wilson I D, Brinkman U AT. Hyphenation and hypernation - The practice and prospects of multiple hyphenation. J Chromatogr A. 2003; 1000 325-56
- 8 Scott R PW. Liquid chromatography detectors. Available at Chrom-Ed Book Series: Library4Science, http://www.library4science.com/ Accessed 2003
- 9 Gao X F, Dan M, Zhao A H, Xie G X, Jia W. Simultaneous determination of saponins in flower buds of Panax notoginseng using high performance liquid chromatography. Biomed Chromatogr. 2008; 22 244-9
- 10 Ozkan S A. LC with electrochemical detection. recent application to pharmaceuticals and biological fluids. Chromatographia. 2007; 66 S3-S13
- 11 Vial J, Jardy A. Study of the linear range in HPLC analyses with UV detection: Methodology and experimental application to the influence of the analyte UV spectrum. J High Resol Chromatogr. 1999; 22 217-21
- 12 Leitner A, Emmert J, Boerner K, Lindner W. Influence of solvent additive composition on chromatographic separation and sodium adduct formation of peptides in HPLC-ESI MS. Chromatographia. 2007; 65 649-53
- 13 Cimpan G, Gocan S. Analysis of medicinal plants by HPLC: Recent approaches. J Liq Chromatogr Relat Technol. 2002; 25 2225-92
- 14 United States Pharmacopeial Convention. The United States pharmacopeia USP 31 NF 26. Rockville, MD; United States Pharmacopeial Convention 2007: 3 volumes
- 15 European Pharmacopoeia 5.1, 5th edition. Strasbourg; Council of Europe 2002
- 16 Fuzzati N. Analysis methods of ginsenosides. J Chromatogr B. 2004; 812 119-33
- 17 Brolis M, Gabetta B, Fuzzati N, Pace R, Panzeri F, Peterlongo F. Identification by high-performace liquid chromatography-diode array detection-mass spectrometry and quantification by high performance liquid chromatography-UV absorbance detection of active constituents of Hypericum perforatum. . J Chromatogr A. 1998; 825 9-16
- 18 Tolonen A, Hohtola A, Jalonen J. Fast high-performance liquid chromatographic analysis of naphthodianthrones and phloroglucinols from Hypericum perforatum extracts. Phytochem Anal. 2003; 14 306-9
- 19 Hasler A, Sticher O, Meier B. Identification and determination of the flavonoid from Ginkgo biloba by high performance liquid chromatography. J Chromatogr. 1992; 605 41-8
- 20 Dubber M J, Kanfer I. High-performance liquid chromatographic determination of selected flavonols in Ginkgo biloba solid oral dosage forms. J Pharm Pharm Sci. 2004; 7 303-9
- 21 Sloley B D, Tawfik S R, Scherban K A, Tam Y K. Quality control analyses for ginkgo extracts require analysis of intact flavonol glycosides. J Food Drug Anal. 2003; 11 102-7
- 22 Chen P, Ozcan M, Harnly J. Chromatographic fingerprint analysis for evaluation of Ginkgo biloba products. Anal Bioanal Chem. 2007; 389 251-61
- 23 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 31-8
- 24 Li W K, Fitzloff J F. HPLC determination of flavonoids and terpene lactones in commercial Ginkgo biloba products. J Liq Chromatogr Relat Technol. 2002; 25 2501-14
- 25 Schotz K. Quantification of allergenic urushiols in extracts of Ginkgo biloba leaves, in simple one-step extracts and refined manufactured material (EGb 761). Phytochem Anal. 2004; 15 1-8
- 26 Ndjoko K, Wolfender J L, Hostettmann K. Determination of trace amounts of ginkgolic acids in Ginkgo biloba L. leaf extracts and phytopharmaceuticals by liquid chromatography-electrospray mass spectrometry. J Chromatogr B. 2000; 744 249-55
- 27 Fuzzati N, Pace R, Villa E. A simple HPLC-UV method for the assay of ginkgolic acids in Ginkgo biloba extracts. Fitoterapia. 2003; 74 247-56
- 28 Mohn T, Potterat O, Hamburger M. Quantification of active principles and pigments in leaf extracts of Isatis tinctoria by HPLC/UV/MS. Planta Med. 2007; 73 151-6
- 29 Bebrevska L, Bravo L, Vandervoort J, Pieters L, Vlietinck A, Apers S. Development and validation of an HPLC method for quality control of Pueraria lobata flower. Planta Med. 2007; 73 1606-13
- 30 Avula B, Joshi V C, Reddy N VL, Choi Y W, Khan L A. Simultaneous determination of eight coumarins in Angelica gigas and in various other Angelica species by high performance liquid chromatography and comparative micro-morphology study of Angelica species. Planta Med. 2007; 73 1509-16
- 31 Liang Z, Jiang Z, Ho H, Zhao Z. Comparative analysis of Oldenlandia diffusa and its substitutes by high performance liquid chromatographic fingerprint and mass spectrometric analysis. Planta Med. 2007; 73 1502-8
- 32 Ge G B, Zhang Y Y, Hao D C, Hu Y, Luan H W, Liu X B. et al . Chemotaxonomic study of medicinal Taxus species with fingerprint and multivariate analysis. Planta Med. 2008; 74 773-9
- 33 Grata E, Boccard J, Glauser G, Carrupt P A, Farmer E E, Wolfender J L. et al . 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 2268-78
- 34 Grata E, Boccard J, Guillarme D, Glauser G, Carrupt P A, Farmer E. et al . UPLC–TOF-MS for plant metabolomics: A sequential approach for wound marker analysis in Arabidopsis thaliana. . J Chromatogr B. 2008; 871 261-70
- 35 Jaimez J, Fente C A, Vazquez B I, Franco C M, Cepeda A, Mahuzier G. et al . Application of the assay of aflatoxins by liquid chromatography with fluorescence detection in food analysis. J Chromatogr A. 2000; 882 1-10
- 36 Braga S, de Medeiros F D, Oliveira E D, Macedo R O. Development and validation of a method for the quantitative determination of aflatoxin contaminants in Maytenus ilicifolia by HPLC with fluorescence detection. Phytochem Anal. 2005; 16 267-71
- 37 Klvana M, Chen J K, Lepine F, Legros R, Jolicoeur M. Analysis of secondary metabolites from Eschscholtzia californica by high-performance liquid chromatography. Phytochem Anal. 2006; 17 236-42
- 38 Kristl J, Veber M, Krajnicic B, Oresnik K, Slekovec M. Determination of jasmonic acid in Lemna minor (L.) by liquid chromatography with fluorescence detection. Anal Bioanal Chem. 2005; 383 886-93
- 39 Li F M, Zhang C H, Guo X J, Feng W Y. Chemiluminescence detection in HPLC and CE for pharmaceutical and biomedical analysis. Biomed Chromatogr. 2003; 17 96-105
- 40 Ohba Y, Kuroda N, Nakashima K. Liquid chromatography of fatty acids with chemiluminescence detection. Anal Chim Acta. 2002; 465 101-9
- 41 Zhang Q L, Cui H. Simultaneous determination of quercetin, kaempferol, and isorhamnetin in phytopharmaceuticals of Hippophae rhamnoides L. by high-performance liquid chromatography with chemiluminescence detection. J Sep Sci. 2005; 28 1171-8
- 42 LaCourse W R, Modi S J. Microelectrode applications of pulsed electrochemical detection. Electroanalysis. 2005; 17 1141-52
- 43 Guo C J, Cao G H, Sofic E, Prior R L. High-performance liquid chromatography coupled with coulometric array detection of electroactive components in fruits and vegetables: Relationship to oxygen radical absorbance capacity. J Agric Food Chem. 1997; 45 1787-96
- 44 Wang C Y, Xu J Y, Zhou G Y, Qu Q S, Yang G J, Hu X Y. Electrochemical detection coupled with high-performance liquid chromatography in pharmaceutical and biomedical analysis: A mini review. Comb Chem High Throughput Screen. 2007; 10 547-54
- 45 Skrinjar M, Kolar M H, Jelsek N, Hras A R, Bezjak M, Knez Z. Application of HPLC with electrochemical detection for the determination of low levels of antioxidants. J Food Comp Anal. 2007; 20 539-45
- 46 Ma L J, Zhang X Z, Zhang H P, Gan Y R. Development of a fingerprint of Salvia miltiorrhiza Bunge by high-performance liquid chromatography with a coulometric electrode array system. J Chromatogr B. 2007; 846 139-46
- 47 Casella I G, Colonna C, Contursi M. Electroanalytical determination of some phenolic acids by high-performance liquid chromatography at gold electrodes. Electroanalysis. 2007; 19 1503-8
- 48 Zhou Q, Zhu Y X, Hwa C A, Yagiz K, Morre D J, Morre D A. et al . Identification of the major vandloid component in Capsicum extract by HPLC-EC and HPLC-MS. Phytochem Anal. 2004; 15 117-20
- 49 Liu Z H, Sang S M, Hartman T G, Ho C T, Rosen R T. Determination of diarylheptanoids from Alpinia officinarum (lesser galangal) by HPLC with photodiode array and electrochemical detection. Phytochem Anal. 2005; 16 252-6
- 50 Ruckert U, Likussar W, Michelitsch A. Simultaneous determination of total hypericin and hyperforin in St. John's wort extracts by HPLC with electrochemical detection. Phytochem Anal. 2007; 18 204-8
- 51 Aaby K, Hvattum E, Skrede G. Analysis of flavonoids and other phenolic compounds using high-performance liquid chromatography with coulometric array detection: Relationship to antioxidant activity. J Agric Food Chem. 2004; 52 4595-603
- 52 Chan K L, Yuen K H, Jinadasa S, Peh K K, Toh W T. A high-performance liquid chromatography analysis of plasma artemisinin using a glassy carbon electrode for reductive electrochemical detection. Planta Med. 1997; 63 66-9
- 53 Wu Y T, Tsai T R, Lin L C, Tsai T H. Liquid chromatographic method with amperometric detection to determine acteoside in rat blood and brain microdialysates and its application to pharmacokinetic study. J Chromatogr B. 2007; 853 281-6
- 54 Joo K M, Park C W, Jeong H J, Lee S J, Chang I S. Simultaneous determination of two Amadori compounds in Korean red ginseng (Panax ginseng) extracts and rat plasma by high-performance anion-exchange chromatography with pulsed amperometric detection. J Chromatogr B. 2008; 865 159-66
- 55 Tiselius A, Claesson S. Adsorption analysis by means of interferometric study. Arkiv Kemi Minearl Geol. 1942; 15 1-6
- 56 Perez A G, Olias R, Espada J, Olias J M, Sanz C. Rapid determination of sugars, nonvolatile acids, and ascorbic acid in strawberry and other fruits. J Agric Food Chem. 1997; 45 3545-9
- 57 von Eggelkraut-Gottanka S G, Abu Abed S, Muller W, Schmidt P C. Quantitative analysis of the active components and the by-products of eight dry extracts of Hypericum perforatum L. (St John's wort). Phytochem Anal. 2002; 13 170-6
- 58 Ding C, Chen E Q, Zhou W J, Lindsay R C. A method for extraction and quantification of Ginkgo terpene trilactones. Anal Chem. 2004; 76 4332-6
- 59 Ford D L, Kennard W. Vaporization analyzer. J Oil Colour Chem Assoc. 1966; 49 299-313
- 60 Megoulas N C, Koupparis M A. Twenty years of evaporative light scattering detection. Crit Rev Anal Chem. 2005; 35 301-16
- 61 Guillarme D, Rudaz S, Schelling C, Dreux M, Veuthey J L. Micro liquid chromatography coupled with evaporative light scattering detector at ambient and high temperature: Optimization of the nebulization cell geometry. J Chromatogr A. 2008; 1192 103-12
- 62 Dubber M J, Kanfer I. Determination of terpene trilactones in Ginkgo biloba solid oral dosage forms using HPLC with evaporative light scattering detection. J Pharm Biomed Anal. 2006; 41 135-40
- 63 Vervoort N, Daemen D, Torok G. Performance evaluation of evaporative light scattering detection and charged aerosol detection in reversed phase liquid chromatography. J Chromatogr A. 2008; 1189 92-100
- 64 Gorecki T, Lynen F, Szucs R, Sandra P. Universal response in liquid chromatography using charged aerosol detection. Anal Chem. 2006; 78 3186-92
- 65 Russo R, Guillarme D, Bicchi C, Rudaz S, Veuthey J L. Evaluation of the coupling between ultra performance liquid chromatography and evaporative light scattering detector for selected phytochemical applications. J Sep Sci. 2008; 31 2377-87
- 66 Li P, Zeng L J, Li S L, Lin G. The extraction of imperialine and imperialine-3 beta-glucoside from Fritillaria pallidiflora Schrenk and quantitative determination by HPLC-evaporative light scattering detection. Phytochem Anal. 2002; 13 158-61
- 67 Kim S N, Ha Y W, Shin H, Son S H, Wu S J, Kim Y S. Simultaneous quantification of 14 ginsenosides in Panax ginseng C.A. Meyer (Korean red ginseng) by HPLC-ELSD and its application to quality control. J Pharm Biomed Anal. 2007; 45 164-70
- 68 Schaneberg B T, Molyneux R J, Khan I A. Evaporative light scattering detection of pyrrolizidine alkaloids. Phytochem Anal. 2004; 15 36-9
- 69 Cremin P A, Zeng L. High-throughput analysis of natural product compound libraries by parallel LC-MS evaporative light scattering detection. Anal Chem. 2002; 74 5492-500
- 70 Li J, Qi H, Qi L W, Yi L, Li P. Simultaneous determination of main phytoecdysones and triterpenoids in Radix Achyranthis Bidentatae by high-performance liquid chromatography with diode array-evaporative light scattering detectors and mass spectrometry. Anal Chim Acta. 2007; 596 264-72
- 71 Camponovo F F, Wolfender J L, Maillard M P, Potterat O, Hostettmann K. Evaporative light-scattering and thermospray mass-spectrometry – Alternative methods for detection and quantitative liquid-chromatographic determination of ginkgolides and bilobalide in Ginkgo biloba leaf extracts and phytopharmaceuticals. Phytochem Anal. 1995; 6 141-8
- 72 Deng F X, Zito S W. Development and validation of a gas chromatographic-mass spectrometric method for simultaneous identification and quantification of marker compounds including bilobalide, ginkgolides and flavonoids in Ginkgo biloba L. extract and pharmaceutical preparations. J Chromatogr A. 2003; 986 121-7
- 73 Dixon R W, Peterson D S. Development and testing of a detection method for liquid chromatography based on aerosol charging. Anal Chem. 2002; 74 2930-7
- 74 Gamache P H, McCarthy R S, Freeto S M, Asa D J, Woodcock M J, Laws K. et al . HPLC analysis of non-volatile analytes using charged aerosol detection. Lc Gc Europe. 2005; 18 345-9
- 75 Lisa M, Lynen F, Holcapek M, Sandra P. Quantitation of triacylglycerols from plant oils using charged aerosol detection with gradient compensation. J Chromatogr A. 2007; 1176 135-42
- 76 Guillarme D, Heinisch S, Gauvrit J Y, Lanteri P, Rocca J L. Optimization of the coupling of high-temperature liquid chromatography and flame ionization detection application to the separations of alcohols. J Chromatogr A. 2005; 1078 22-7
- 77 Foster M D, Synovec R E. Reversed phase liquid chromatography of organic hydrocarbons with water as the mobile phase. Anal Chem. 1996; 68 2838-44
- 78 Smith R M. Superheated water chromatography – A green technology for the future. J Chromatogr A. 2008; 1184 441-55
- 79 Guillarme D, Heinisch S. Detection modes with high temperature liquid chromatography – A review. Sep Purif Rev. 2005; 34 181-216
- 80 Cheng K W, Cheng F, Wang M. Liquid chromatography-mass spectrometry in natural product research. In: Colegate SM, Molyneux RJ, editors. Bioactive natural products: detection, isolation, and structural determination, 2nd edition. London: CRC. press; 2008 245-66
- 81 Niessen W MA. Liquid chromatography – mass spectrometry, 3 rd edition. Boca Raton: Taylor &. Francis; 2006 608 S
- 82 He X G. On-line identification of phytochemical constituents in botanical extracts by combined high-performance liquid chromatographic-diode array detection-mass spectrometric techniques. J Chromatogr A. 2000; 880 203-32
- 83 Games D E, Martinez F. Evaluation of the moving belt as an interface for high performance liquid chromatographic mass-spectrometric analysis of flavonoids aglycones. J Chromatogr. 1989; 474 372-80
- 84 Brewer T M, Castro J, Marcus R K. Particle beam sample introduction into glow discharge plasmas for speciation analysis. Spectrochim Acta Part B At Spectrosc. 2006; 61 134-49
- 85 Cappiello A, Famiglini G, Pierini E, Palma P, Trufelli H. Advanced liquid chromatography-mass spectrometry interface based on electron ionization. Anal Chem. 2007; 79 5364-72
- 86 Korfmacher W A. Principles and applications of LC-MS in new drug discovery. Drug Discov Today. 2005; 10 1357-67
- 87 Pisitkun T, Hoffert J D, Yu M J, Knepper M A. Tandem mass spectrometry in physiology. Physiology. 2007; 22 390-400
- 88 Williamson L N, Bartlett M G. Quantitative liquid chromatography/time-of-flight mass spectrometry. Biomed Chromatogr. 2007; 21 567-76
- 89 Jessome L L, Volmer D A. Ion suppression: A major concern in mass spectrometry. Lc Gc North America 2006: 83-9
- 90 Syage J A, Short L C, Cai S S. Atmospheric pressure photoionization – The second source for LC-MS?. Lc Gc North America. 2008; 26 286-300
- 91 Jean-Denis J B, Pezet R, Tabacchi R. Rapid analysis of stilbenes and derivatives from downy mildew-infected grapevine leaves by liquid chromatography-atmospheric pressure photoionisation mass spectrometry. J Chromatogr A. 2006; 1112 263-8
- 92 Gomez-Ariza J L, Garcia-Barrera T, Lorenzo F. Anthocyanins profile as fingerprint of wines using atmospheric pressure photoionisation coupled to quadrupole time-of-flight mass spectrometry. Anal Chim Acta. 2006; 570 101-8
- 93 Cai Y X, Kingery D, McConnell O, Bach A C. Advantages of atmospheric pressure photoionization mass spectrometry in support of drug discovery. Rapid Commun Mass Spectrom. 2005; 19 1717-24
- 94 Li L, Zhang J L, Sheng Y X, Guo D A, Wang Q, Guo H Z. Simultaneous quantification of six major active saponins of Panax notoginseng by high-performance liquid chromatography-UV method. J Pharm Biomed Anal. 2005; 38 45-51
- 95 Wang C Z, Aung H H, Ni M, Wu J A, Tong R B, Wicks S. et al . Red American ginseng: Ginsenoside constituents and antiproliferative activities of heat-processed Panax quinquefolius roots. Planta Med. 2007; 73 669-74
- 96 Wan J B, Yang F Q, Li S P, Wang Y T, Cui X M. Chemical characteristics for different parts of Panax notoginseng using pressurized liquid extraction and HPLC-ELSD. J Pharm Biomed Anal. 2006; 41 1596-601
- 97 Fuzzati N, Gabetta B, Jayakar K, Pace R, Peterlongo F. Liquid chromatography-electrospray mass spectrometric identification of ginsenosides in Panax ginseng roots. J Chromatogr A. 1999; 854 69-79
- 98 Luchtefeld R, Kostoryz E, Smith R E. Determination of ginsenosides Rb-1, R-c, and R-e in different dosage forms of ginseng by negative ion electrospray liquid chromatography-mass spectrometry. J Agric Food Chem. 2004; 52 4953-6
- 99 Kite G C, Howes M JR, Leon C J, Simmonds M SJ. Liquid chromatography/mass spectrometry of malonyl-ginsenosides in the authentication of ginseng. Rapid Commun Mass Spectrom. 2003; 17 238-44
- 100 Wang X, Sakuma T, Asajufa-adjaye E, Shiu G. Determination of ginsenosides in plant extracts from Panax ginseng and Panax quinquefolius by LC/MS/MS. Anal Chem. 1999; 71 1579-84
- 101 Wang Y, Pan J Y, Xiao X Y, Lin R C, Cheng Y Y. Simultaneous determination of ginsenosides in Panax ginseng with different growth ages using high-performance liquid chromatography-mass spectrometry. Phytochem Anal. 2006; 17 424-30
- 102 Ligor T, Ludwiczuk A, Wolski T, Buszewski B. Isolation and determination of ginsenosides in American ginseng leaves and root extracts by LC-MS. Anal Bioanal Chem. 2005; 383 1098-105
- 103 Xie G X, Plumb R, Su M M, Xu Z H, Zhao A H, Qiu M F. et al . Ultra-performance LC/TOF MS analysis of medicinal Panax herbs for metabolomic research. J Sep Sci. 2008; 31 1015-26
- 104 Ma X, Xiao H B, Liang X M. Identification of ginsenosides in Panax quinquefolium by LC-MS. Chromatographia. 2006; 64 31-6
- 105 Yu Z G, Gao X X, Zhao Y L, Chen X H, Bi K S. Simultaneous determination of components in preparation Naodesheng injection by high performance liquid chromatograph-atmospheric pressure chemical ionization mass spectrometry (HPLC-MS/APCI). Chem Pharm Bull. 2006; 54 588-90
- 106 Wang W, Wang G J, Xie H T, Sun J G, Zhao S, Jiang X L. et al . Determination of ginsenoside Rd in dog plasma by liquid chromatography-mass spectrometry after solid-phase extraction and its application in dog pharmacokinetics studies. J Chromatogr B. 2007; 852 8-14
- 107 Liu H, Huang Y, Wang Q, Zhang T, Song Y. Detection of saponins in extracts from the rhizomes of Paris species and prepared Chinese medicines by high performance liquid chromatography-electrospray ionization mass spectrometry. Planta Med. 2006; 72 835-41
- 108 Sun Y K, Li W K, Fitzloff J F, van Breemen R B. Liquid chromatography/electrospray tandem mass spectrometry of terpenoid lactones in Ginkgo biloba. . J Mass Spectrom. 2005; 40 373-9
- 109 Xie J S, Ding C G, Ge Q H, Zhou Z, Zhi X J. Simultaneous determination of ginkgolides A, B, C and bilobalide in plasma by LC-MS/MS and its application to the pharmacokinetic study of Ginkgo biloba extract in rats. J Chromatogr B. 2008; 864 87-94
- 110 Draper W M, Wijekoon D, McKinney M, Behniwal P, Perera S K, Flessel C P. Atmospheric pressure ionization LC-MS-MS determination of urushiol congeners. J Agric Food Chem. 2002; 50 1852-8
- 111 Betteridge K, Cao Y, Colegate S M. Improved method for extraction and LC-MS analysis of pyrrolizidine alkaloids and their N-oxides in honey: Application to Echium vulgare honeys. J Agric Food Chem. 2005; 53 1894-902
- 112 Ioset J R, Raoelison G E, Hostettmann K. Detection of aristolochic acid in Chinese phytomedicines and dietary supplements used as slimming regimens. Food Chem Toxicol. 2003; 41 29-36
- 113 Koh H L, Wang H, Zhou S, Chan E, Woo S O. Detection of aristolochic acid I, tetrandrine and fangchinoline in medicinal plants by high performance liquid chromatography and liquid chromatography/mass spectrometry. J Pharm Biomed Anal. 2006; 40 653-61
- 114 Careri M, Mangia A, Musci M. Overview of the applications of liquid chromatography mass spectrometry interfacing systems in food analysis: naturally occurring substances in food. J Chromatogr A. 1998; 794 263-97
- 115 Sashidhara K V, Rosaiah J N. Various dereplication strategies using LC-MS for rapid natural product lead identification and drug discovery. Nat Prod Commun. 2007; 2 193-202
- 116 Xing J, Xie C F, Lou H X. Recent applications of liquid chromatography-mass spectrometry in natural products bioanalysis. J Pharm Biomed Anal. 2007; 44 368-78
- 117 Wolfender J L, Ndjoko K, Hostettmann K. The potential of LC-NMR in phytochemical analysis. Phytochem Anal. 2001; 12 2-22
- 118 Duckett C J, Lindon J C, Walker H, Abou-Shakra F, Wilson I D, Nicholson J K. Metabolism of 3-chloro-4-fluoroaniline in rat using [C-14]-radiolabelling, F-19-NMR spectroscopy, HPLC-MS/MS, HPLC-ICPMS and HPLC-NMR. Xenobiotica. 2006; 36 59-77
- 119 Wolfender J L, Queiroz E F, Hostettmann K. The importance of hyphenated techniques in the discovery of new lead compounds from nature. Exp Opin Drug Discov. 2006; 1 237-60
- 120 Waridel P, Wolfender J L, Ndjoko K, Hobby K R, Major H J, Hostettmann K. Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. J Chromatogr A. 2001; 926 29-41
- 121 Wolfender J L, Queiroz E F, Hostettmann K. Development and application of LC/NMR techniques to the identification of bioactive natural products. In: Colegate SM, Molyneux RJ, editors. Bioactive natural products; detection, isolation and structural determination. London: CRC. press; 2008 143-90
- 122 Wilson I D, Brinkman U AT. Hype and hypernation: multiple hyphenation of column liquid chromatography and spectroscopy. Trends Anal Chem. 2007; 26 847-54
- 123 Hall C. Dictionary of natural products on CD-ROM:. Chapman & Hall 2008
- 124 Jaroszewski J W. Hyphenated NMR methods in natural products research, Part 1: Direct hyphenation. Planta Med. 2005; 71 691-700
- 125 Jaroszewski J W. Hyphenated NMR methods in natural products research, Part 2: HPLC-SPE-NMR and other new trends in NMR hyphenation. Planta Med. 2005; 71 795-802
- 126 Clarkson C, Madikane E V, Hansen S H, Smith P J, Jaroszewski J W. HPLC-SPE-NMR characterization of sesquiterpenes in an antimycobacterial fraction from Warburgia salutaris. . Planta Med. 2007; 73 578-84
- 127 Lambert M, Wolfender J L, Staerk D, Christensen B, Hostettmann K, Jaroszewski J W. Identification of natural products using HPLC-SPE combined with CapNMR. Anal Chem. 2007; 79 727-35
- 128 Louden D, Handley A, Taylor S, Lenz E, Miller S, Wilson I D. et al . Spectroscopic characterization and identification of ecdysteroids using high-performance liquid chromatography combined with on-line UV-diode array, FT-infrared and 1H-nuclear magnetic resonance spectroscopy and time of flight mass spectrometry. J Chromatogr A. 2001; 910 237-46
- 129 Ren D M, Guo H F, Wang S Q, Lou H X. Separation and structure determination of two diastereomeric pairs of enantiomers from Dracocephalum rupestre by high-performance liquid chromatography with circular dichroism detection. J Chromatogr A. 2007; 1161 334-7
- 130 Huber L, George S A. Diode array detection in HPLC. New York; Marcel Dekker 1993
-
131 Larsen T O, Hansen M AE. Dereplication and discovery of natural products by UV spectroscopy. In: Colegate SM, Molyneux RJ, editors
Bioactive natural products: detection, isolation, and structural determination, 2nd Edition . London; CRC Press 2008: 221-44 - 132 Robbins R J. Phenolic acids in foods: An overview of analytical methodology. J Agric Food Chem. 2003; 51 2866-87
- 133 Waridel P, Wolfender J L, Lachavanne J B, Hostettmann K. Identification of the polar constituents of Potamogeton species by HPLC-UV with post-column derivatization, HPLC-MS(n) and HPLC-NMR, and isolation of a new ent-labdane diglycoside. Phytochemistry. 2004; 65 2401-10
- 134 Bennett R N, Mellon F A, Foidl N, Pratt J H, Dupont M S, Perkins L. et al . Profiling glucosinolates and phenolics in vegetative and reproductive tissues of the multi-purpose trees Moringa oleifera L. (horseradish tree) and Moringa stenopetala L. J Agric Food Chem. 2003; 51 3546-53
- 135 Gobbo-Neto L, Lopes N P. Online identification of chlorogenic acids, sesquiterpene lactones, and flavonoids in the Brazilian arnica Lychnophora ericoides Mart. (Asteraceae) leaves by HPLC-DAD-MS and HPLC-DAD-MS/MS and a validated HPLC-DAD method for their simultaneous analysis. J Agric Food Chem. 2008; 56 1193-204
- 136 Yang M, Sun J, Lu Z, Chen G, Guan S, Liu X. et al .Phytochemical analysis of herbal medicines using liquid chromatography coupled with mass spectrometry. J Chromatogr A 2008: doi:10.1016/j.chroma.2008.08.097
- 137 Kussmann M, Affolter M, Nagy K, Holst B, Fay L B. Mass Spectrometry in nutrition: Understanding dietary health effects at the molecular level. Mass Spectrom Rev. 2007; 26 727-50
- 138 Wolfender J L, Rodriguez S, Hostettmann K. Liquid chromatography coupled to mass spectrometry and nuclear magnetic resonance spectroscopy for the screening of plant constituents. J Chromatogr A. 1998; 794 299-316
- 139 Suzuki H, Sasaki R, Ogata Y, Nakamura Y, Sakurai N, Kitajima M. et al . Metabolic profiling of flavonoids in Lotus japonicus using liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry. Phytochemistry. 2008; 69 99-111
- 140 Bonkanka C X, Smelcerovic A, Zuehlke S, Rabanal R M, Spiteller M, Sanchez-Mateo C D. HPLC-MS analysis and anti-oedematogenic activity of Hypericum grandifolium choisy (Hypericaceae). Planta Med. 2008; 74 719-25
- 141 Han J, Ye M, Xu M, Qiao X, Chen H L, Wang B R. et al . Comparison of phenolic compounds of rhubarbs in the section deserticola with Rheum palmatum by HPLC-DAD-ESI-MSn. Planta Med. 2008; 74 873-9
- 142 Hopfgartner G. Identification of metabolites by multi-instruments strategies (LC-MS-MS on various platforms). In: Niessen WMA, editor. Encyclopedia of mass spectrometry,Vol 8: Hyphenated methods. Oxford: Elsevier. Science; 2006 465-74
- 143 Sun F, He Q, Shi P Y, Xiao P G, Cheng Y Y. Characterization and identification of triterpenoid saponins in crude extracts from Clematis spp. by high-performance liquid chromatography/electrospray ionization with multi-stage tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007; 21 3743-50
- 144 Fuzzati N, Gabetta N, Strepponi I, Villa F. High-performance liquid chromatography–electrospray ionization mass spectrometry and multiple mass spectrometry studies of hyperforin degradation products. J Chromatogr A. 2001; 926 187-98
- 145 Cuyckens F, Claeys M. Mass spectrometry in the structural analysis of flavonoids. J Mass Spectrom. 2004; 39 1-15
- 146 Kuhn F, Oehme M, Romero F, Abou-Mansour E, Tabacchi R. Differentiation of isomeric flavone/isoflavone aglycones by MS2 ion trap mass spectrometry and a double neutral loss of CO. Rapid Commun Mass Spectrom. 2003; 17 1941-9
- 147 Biemann K. Sequencing of peptides by tandem mass spectrometry and high-energy collision induced dissociation. Methods Enzymol. 1990; 193 455-79
- 148 De Abreu M B, Dal Piaz F, Temraz A, Bader A, De Tommasi N, Braca A. Gypsins A-D from Gypsophila arabica. . J Nat Prod. 2008; 71 1336-42
- 149 Wolff J C, Eckers C, Sage A B, Giles K, Bateman R. Accurate mass liquid chromatography/mass spectrometry on quadrupole orthogonal acceleration time-of flight mass analyzers using switching between separate sample and reference sprays. 2. Applications using the dual-electrospray ion source. Anal Chem. 2001; 73 2605-12
- 150 Wolfender J L, Queiroz E F, Hostettmann K. Phytochemistry in the microgram domain – a LC-NMR perspective. Magn Reson Chem. 2005; 43 697-709
- 151 Yang Z. Online hyphenated liquid chromatography-nuclear magnetic resonance spectroscopy for drug metabolite and nature product analysis. Pharm Biomed Anal. 2006; 40 516-27
- 152 Cogne A L, Queiroz E F, Marston A, Wolfender J L, Mavi S, Hostettmann K. On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR. Phytochem Anal. 2005; 16 429-39
- 153 Exarchou V, Krucker M, van Beek T A, Vervoort J, Gerothanassis I P, Albert K. LC-NMR coupling technology: recent advancements and applications in natural products analysis. Magn Reson Chem. 2005; 43 681-7
- 154 Olson D L, Norcross J A, O′Neil-Johnson M, Molitor P F, Detlefsen D J, Wilson A G. et al . Microflow NMR: concepts and capabilities. Anal Chem. 2004; 76 2966-74
- 155 Hu J F, Garo E, Yoo H D, Cremin P A, Zeng L, Goering M G. et al . Application of capillary-scale NMR for the structure determination of phytochemicals. Phytochem Anal. 2005; 16 127-33
- 156 Glauser G, Guillarme D, Grata E, Boccard J, Thiocone A, Carrupt P A. et al . 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 90-8
- 157 Seger C, Sturm S. Analytical aspects of plant metabolite profiling platforms: Current standings and future aims. J Proteome Res. 2007; 6 480-97
- 158 Choi Y H, Choi H K, Peltenburg-Looman A MG, Lefeberz A WM, Verpoorte R. Quantitative analysis of ginkgolic acids from Ginkgo leaves and products using H-1-NMR. Phytochem Anal. 2004; 15 325-30
- 159 Tatsis E C, Exarchou V, Troganis A N, Gerothanassis I P. H-1 NMR determination of hypericin and pseudohypericin in complex natural mixtures by the use of strongly deshielded OH groups. Anal Chim Acta. 2008; 607 219-26
- 160 Huck C W, Abel G, Popp M, Bonn G K. Comparative analysis of naphthodianthrone and phloroglucine derivatives in St. John′s Wort extracts by near infrared spectroscopy, high-performance liquid chromatography and capillary electrophoresis. Anal Chim Acta. 2006; 580 223-30
- 161 Yang S Y, Kim H K, Lefeber A WM, Erkelens C, Angelova N, Choi Y H. et al . Application of two-dimensional nuclear magnetic resonance spectroscopy to quality control of ginseng commercial products. Planta Med. 2006; 72 364-9
- 162 Cardoso-Taketa A T, Pereda-Miranda R, Choi Y H, Verpoorte R, Villarreal M L. Metabolic profiling of the Mexican anxiolytic and sedative plant Golphimia glauca using nuclear magnetic resonance spectroscopy and multivariate data analysis. Planta Med. 2008; 74 1295-301
- 163 Potterat O, Hamburger M. Natural products in drug discovery – Concepts and approaches for tracking bioactivity. Curr Org Chem. 2006; 10 899-920
Jean-Luc Wolfender
Laboratory of Pharmacognosy and Phytochemistry
School of Pharmaceutical Sciences
University of Geneva
University of Lausanne
30 Quai Ernest-Ansermet
1211 Geneva 4
Switzerland
Phone: +41-22-379-3385
Fax: +41-22-379-3399
Email: jean-luc.wolfender@unige.ch