Classification of commercial cultivars of Humulus lupulus L. (hop) by chemometric pixel analysis of two dimensional nuclear magnetic resonance spectra

Metabolomics

Volumn 10, Issue 1, 2014, Pages 21-32

  Farag, Mohamed A ^a,b   Mahrous, Engy A ^a   Lübken, Tilo ^b   Porzel, Andrea ^b   Wessjohann, Ludger ^b  

^a CAIRO UNIVERSITY   (Egypt)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

2D NMR metabolomics; Bitter acids; HMBC; Humulus lupulus L. hop; Pixel analysis; Principal component analysis; Quality control

Indexed keywords

PLANT RESIN;

ARTICLE; CHEMOMETRIC ANALYSIS; DATA PROCESSING; HETERONUCLEAR MULTIPLE BOND CORRELATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMULUS LUPULUS; METABOLITE; MULTIVARIATE ANALYSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRINCIPAL COMPONENT ANALYSIS; QUALITY CONTROL;

HUMULUS LUPULUS;

EID: 84892482239     PISSN: 15733882     EISSN: 15733890     Source Type: Journal    
DOI: 10.1007/s11306-013-0547-4     Document Type: Article

References (25)

1. Agnolet, S., Jaroszewski, J. W., Verpoorte, R., & Staerk, D. (2010). H-1 NMR-based metabolomics combined with HPLC-PDA-MS-SPE-NMR for investigation of standardized Ginkgo biloba preparations. Metabolomics, 6, 292-302. doi: 10. 1007/s11306-009-0195-x.
2. Bertelli, D., Lolli, M., Papotti, G., Bortolotti, L., Serra, G., & Plessi, M. (2010). Detection of honey adulteration by sugar syrups using one-dimensional and two-dimensional high-resolution nuclear magnetic resonance. Journal of Agricultural and Food Chemistry, 58, 8495-8501. doi: 10. 1021/jf101460t.
3. Biendl, M., & Pinzl, C. (2008). Hops and health. Uses - Effects - History. Wolznach: German Hop Museum Wolznach.
4. Borremans, F., De Potter, M., & De Keukeleire, D. (1975). Carbon-13 NMR spectroscopy of hop bitter substances. Organic Magnetic Resonance, 7, 415-417. doi: 10. 1002/mrc. 1270070904.
5. Donarski, J. A., Jones, S. A., & Charlton, A. J. (2008). Application of cryoprobe 1H nuclear magnetic resonance spectroscopy and multivariate analysis for the verification of corsican honey. Journal of Agricultural and Food Chemistry, 56, 5451-5456. doi: 10. 1021/jf072402x.
6. Dumas, M. E., Maibaum, E. C., Tigue, C., et al. (2006). Assessment of analytical reproducibility of 1H NMR spectroscopy based metabolomics for large-scale epidemiological research: The INTERMAP study. Analytical Chemistry, 78, 2199-2208. doi: 10. 1021/ac0517085.
7. Farag, M. A., Porzel, A., Schmidt, J., & Wessjohann, L. A. (2012a). Metabolite profiling and fingerprinting of commercial cultivars of Hummulus lupulus L. (hop)-A comparison of MS and NMR methods in metabolomics. Metabolomics, 8, 492-507. doi: 10. 1007/s11306-011-0335-y.
8. Farag, M. A., Porzel, A., & Wessjohann, L. A. (2012b). Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC-MS, LC-MS and 1D NMR techniques. Phytochemistry, 76, 60-72. doi: 10. 1016/j. phytochem. 2011. 12. 010.
9. Farag, M. A., & Wessjohann, L. A. (2012). Metabolome classification of commercial Hypericum perforatum (St. John's Wort) preparations via UPLC-qTOF-MS and chemometrics. Planta Medica, 78, 488-496. doi: 10. 1055/s-0031-1298170.
10. Gray, D. E., Pallardy, S. G., Garrett, H. E., & Rottinghaus, G. E. (2003). Effect of acute drought stress and time of harvest on phytochemistry and dry weight of St. John's wort leaves and flowers. Planta Medica, 69, 1024-1030. doi: 10. 1055/s-2003-45150.
11. Hansel, R., Wohlfart, R., & Schmidt, H. (1982). The sedativ-hypnotic principle of hops. Planta Medica, 45, 224-228. doi: 10. 1055/s-2007-971377.
12. Khatib, A., Wilson, E. G., Kim, H. K., Supardi, M., Choi, Y. H., & Verpoorte, R. (2007). NMR assignment of iso-alpha-acids from isomerised extracts of Humulus lupulus L. cones. Phytochemical Analysis, 18, 371-377. doi: 10. 1002/pca. 991.
13. Kim, H. K., Choi, Y. H., Erkelens, C., Lefeber, A. W., & Verpoorte, R. (2005). Metabolic fingerprinting of Ephedra species using 1H-NMR spectroscopy and principal component analysis. Chemical & Pharmaceutical Bulletin, 53(1), 105-109.
14. Kim, H. K., Choi, Y. H., & Verpoorte, R. (2010). NMR-based metabolomic analysis of plants. Nature Protocols, 5(3), 536-549. doi: 10. 1038/nprot. 2009. 237.
15. Kim, H. K., Choi, Y. H., & Verpoorte, R. (2011). NMR-based plant metabolomics: where do we stand, where do we go? Trends in Biotechnology, 29, 267-275. doi: 10. 1016/j. tibtech. 2011. 02. 001.
16. Liang, Y. S., Choi, Y. H., Kim, H. K., Linthorst, H. J. M., & Verpoorte, R. (2006). Metabolomic analysis of methyl jasmonate treated Brassica rapa leaves by 2-dimensional NMR spectroscopy. Phytochemistry, 67, 2503-2511. doi: 10. 1016/j. phytochem. 2006. 08. 018.
17. Malowicki, M. G., & Shellhammer, T. H. (2005). Isomerization and degradation kinetics of hop (Humulus lupulus) acids in a model wort-boiling system. Journal of Agricultural and Food Chemistry, 53, 4434-4439. doi: 10. 1021/jf0481296.
18. Rasmussen, B., Cloarec, O., Tang, H., Staerk, D., & Jaroszewski, J. W. (2006). Multivariate analysis of integrated and full-resolution 1H-NMR spectral data from complex pharmaceutical preparations: St. John's wort. Planta Medica, 72(6), 556-563.
19. Ratcliffe, R. G., & Shachar-Hill, Y. (2001). Probing Plant Metabolism with NMR. Annual Review of Plant Physiology and Plant Molecular Biology, 52, 499-526.
20. Stacklies, W., Redestig, H., Scholz, M., Walther, D., & Selbig, J. (2007). pcaMethods-A bioconductor package providing PCA methods for incomplete data. Bioinformatics, 23, 1164-1167. doi: 10. 1093/bioinformatics/btm069.
21. van Cleemput, M., Cattoor, K., De Bosscher, K., Haegeman, G., De Keukeleire, D., & Heyerick, A. (2009). Hop (Humulus lupulus)-derived bitter acids as multipotent bioactive compounds. Journal of Natural Products, 72, 1220-1230. doi: 10. 1021/np800740m.
22. van der Kooy, F., Maltese, F., Choi, Y. H., Kim, H. K., & Verpoorte, R. (2009). Quality control of herbal material and phytopharmaceuticals with MS and NMR based metabolic fingerprinting. Planta Medica, 75, 763-775. doi: 10. 1055/s-0029-1185450.
23. Wang, Y., Tang, H. R., Nicholson, J. K., et al. (2004). Metabolomic strategy for the classification and quality control of phytomedicine: A case study of chamomile flower (Matricaria recutita L.). Planta Medica, 70, 250-255. doi: 10. 1055/s-2004-815543.
24. Yang, S. Y., Kim, H. K., Lefeber, A. W. M., et al. (2006). Application of two-dimensional nuclear magnetic resonance spectroscopy to quality control of ginseng commercial products. Planta Medica, 72, 364-369. doi: 10. 1055/s-2005-916240.
25. Zhang, X., Liang, X., Xiao, H., & Xu, Q. (2004). Direct characterization of bitter acids in a crude hop extract by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Journal of the American Society for Mass Spectrometry, 15, 180-187. doi: 10. 1016/j. jasms. 2003. 09. 014.