Evaluation of nonpolar metabolites in plant extracts by 13C NMR spectroscopy

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 21, 2011, Pages 11407-11416

  Palomino Schätzlein, Martina ^a   Escrig, Pablo V ^b   Boira, Herminio ^b   Primo, Jaime ^b   Pineda Lucena, Antonio ^a   Cabedo, Nuria ^b  

^a CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

Araujia; Euphorbia; hydrocarbons; metabolic profiling; Morus; multivariate analysis; quantitative 13C NMR; triterpenes

Indexed keywords

ARAUJIA; EUPHORBIA; METABOLIC PROFILING; MORUS; MULTI VARIATE ANALYSIS; QUANTITATIVE 13C NMR; TRITERPENES;

BIOMOLECULES; HYDROCARBONS; METABOLISM; METABOLITES; MULTIVARIANT ANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; SPECTRUM ANALYSIS;

PLANT EXTRACTS;

PLANT EXTRACT;

APOCYNACEAE; ARTICLE; CHEMISTRY; EUPHORBIA; EVALUATION; METABOLISM; METHODOLOGY; MORUS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF; SPAIN;

APOCYNACEAE; EUPHORBIA; MAGNETIC RESONANCE SPECTROSCOPY; MORUS; PLANT EXTRACTS; PLANT LEAVES; SPAIN;

APOCYNACEAE; ARAUJIA; EUPHORBIA; EUPHORBIA CHARACIAS; EUPHORBIACEAE; MORACEAE; MORUS (ANGIOSPERM);

EID: 80455140610     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2030902     Document Type: Article

References (39)

1. Aliferis, K. A.; Tokousbalides, M. C. Metabolomics in pesticide research and development: review and future perspectives Metabolomics 2011, 7, 35-53
2. Dixon, R. A.; Gang, D. R.; Charlton, A. J.; Fiehn, O.; Kuiper, H. A.; Reynolds, T. L.; Tjeerdema, R. S.; Jeffery, E. H.; German, J. B.; Ridley, W. P.; Seiber, J. N. Applications of metabolomics in agriculture J. Agric. Food Chem. 2006, 54, 8984-8994
3. Colquhoun, I. J. Use of NMR for metabolic profiling in plant systems J. Pestic. Sci. 2007, 32, 200-212
4. Riederer, M.; Schreiber, L. Protecting against water loss: analysis of the barrier properties of plant cuticles J. Exp. Bot. 2001, 52, 2023-2032
5. Koops, A. J.; Baas, W. J.; Groeneveld, H. W. The composition of phytosterols, latex triterpenols and wax triterpenoids in the seedling of Euphorbia lathyris L Plant Sci. 1991, 74, 185-191
6. Konno, K. Plant latex and other exudates as plant defense systems: roles of various defense chemicals and proteins contained therein Phytochemistry 2011, 72, 1510-1530
7. Medina, E.; Aguilar, G.; Gómez, M.; Aranda, J.; Medina, J. D.; Winter, K. Taxonomic significance of the epicuticular wax composition in species of the genus Clusia from Panama Biochem. Syst. Ecol. 2006, 34, 319-326
8. Kim, H. K.; Choi, Y. H.; Verpoorte, R. NMR-based metabolomic analysis of plants Nat. Protoc. 2010, 5, 536-549
9. Choi, Y. H.; Sertic, S.; Kim, H. K.; Wilson, E. G.; Michopoulos, F.; Lefeber, A. W. M.; Erkelens, C.; Kricun, S. D. P.; Verpoorte, R. Classification of Ilex species based on metabolomic fingerprinting using nuclear magnetic resonance and multivariate data analysis J. Agric. Food. Chem. 2005, 53, 1237-1245
10. Kovacs, H.; Moskau, D.; Spraul, M. Cryogenically cooled probes - a leap in NMR technology Prog. Nucl. Magn. Reson. Spectrosc. 2005, 46, 131-155
11. 13C NMR spectroscopy of urine for metabonomic studies Anal. Chem. 2002, 74, 4588-4593
12. Kubeczka, K. H.; Formácek, V. Essential Oils Analysis by Capillary Gas Chromatography and Carbon 13 NMR Spectroscopy, 2nd ed.; Wiley: New York, 2002.
13. 13C nuclear magnetic resonance spectroscopy for determining the different components of epicuticular waxes of olive fruit (Olea europea) Dritta cultivar Anal. Chim. Acta 2008, 624, 184-194
14. 13C NMR analysis of lignins with internal standards J. Agric. Food Chem. 2001, 49, 3573-3578
15. Dunn, W. B.; Bailey, N. J. C.; Johnson, H. E. Measuring the metabolome: current analytical technologies Analyst 2005, 130, 606-625
16. Sotak, C. H.; Dumoulin, C. L.; Levy, G. C. In Topics in Carbon-13 NMR Spectroscopy; Levy, G. C., Ed.; Wiley: New York, 1984; Vol 4, pp 91-121.
17. Cabrera, G. M.; Seldes, A. M. Hydroperoxycycloartanes from Tillandsia recurvata J. Nat. Prod. 1995, 58, 1920-1924
18. Bhattacharyya, J.; Barros, C. B. Triterpenoids of Cnidosculus urens Phytochemistry 1986, 25, 274-276
19. Yoshida, K.; Hirose, Y.; Imai, Y.; Kondo, T. Conformational analysis of cycloartenol, 24-methylenecycloartenol and their derivatives Agric. Biol. Chem. 1989, 53, 1901-1912
20. Wood, C. A.; Lee, K.; Vaisberg, A. J.; Kingston, D. G. I.; Neto, C. C.; Hammond, G. B. A bioactive spirolactone iridoid and triterpenoids from Himatanthus sucuuba Chem. Pharm. Bull. 2001, 49, 1477-1478
21. Ross, A.; Schlotterbeck, G.; Dieterle, F.; Senn, H. NMR spectroscopy techniques for application to metabonomics. In Handbook of Metabonomics and Metabolomics; Lindon, J. C.; Nicholson, J. K.; Holmes, E., Eds.; Elsevier: Amsterdam, The Netherlands, 2007; pp 99-100.
22. Wold, S.; Johansson, E.; Cocchi, M. PLS - partial least squares projections to latent structures. In 3D-QSAR in Drug Design: Theory, Methods and Applications; Kubinyi, H., Ed.; Escom Science: Leiden, The Netherlands, 1993; pp 523-550.
23. Jackson, J. E. A User's Guide to Principal Components; Wiley: New York, 1991.
24. Bylesjö, M.; Rantalainen, M.; Cloarec, O.; Nicholson, J. K.; Holmes, E.; Trygg, J. OPLS discriminant analysis: combining the strengths of PLS-DA and SIMCA classification J. Chemom. 2006, 20, 341-351
25. Bijlsma, S.; Bobeldijk, I.; Verheij, E. R.; Ramaker, R.; Kochhar, S.; Macdonald, I. A.; van Ommen, B.; Smilde, A. K. Large-scale human metabolomics studies: a strategy for data (pre-) processing and validation Anal. Chem. 2006, 78, 567-574
26. Wiklund, S.; Johansson, E.; Sjöström, L.; Mellerowicz, E. J.; Edlund, U.; Shockcor, J. P.; Gottfries, J.; Mortiz, T.; Trygg, J. Visualization of GC/TOF-MS-based metabonomics data for identification of biochemically interesting compounds using OPLS class models Anal. Chem. 2008, 80, 115-122
27. Wen, H.; Kang, S.; Song, Y.; Song, Y.; Sung, S. H.; Park, S. Differentation of cultivation sources of Ganoderma lucidum by NMR-based metabolomics approach Phytochem. Anal. 2009, 21, 73-79
28. 1H NMR-based metabolomics study J. Agric. Food Chem. 2010, 58, 10582-10589
29. Evilia, R. F. Quantitative NMR spectroscopy Anal. Lett. 2001, 34, 2227-2236
30. 13C NMR analysis of ethylene-1-octene copolymers Polymer 2003, 44, 3483-3489
31. González-Coloma, A.; López-Balboa, C.; Santana, O.; Reina, M.; Fraga, B. M. Triterpene-based plant defenses Phytochem. Rev. 2001, 10, 245-260
32. Hemmers, H.; Gülz, P. G.; Marner, F. J. Triterpenoids in epicuticular waxes of three European Euphorbia species Z. Naturforsch. 1988, 43C, 799-805
33. Böszörményi, A.; Szarka, Sz.; Héthelyi, É.; Gyurján, I.; László, M.; Simándi, B.; Szóke, É.; Lemberkovics, É. Triterpenes in traditional and supercritical-fluid extracts of Morus alba leaf and stem bark Acta Chromatogr. 2009, 21, 659-669
34. López de Medrano-Villar, M. J.; Bello, R.; Esplugues, J.; Primo-Yúfera, E.; Primo-Millo, J. Triterpenoid compounds from Araujia sericifera B. effects on the isolated uinea pig ileum Methods Find. Exp. Clin. Pharmacol. 1997, 19, 515-520
35. Akihisa, T.; Yasukawa, K.; Yamaura, M.; Ukiya, M.; Kimura, Y.; Shimizu, N.; Arai, K. Triterpene alcohol and sterol ferulates from rice bran and their anti-inflamatory effetcs J. Agric. Food Chem. 2000, 48, 2313-2319
36. Sousa, A. F.; Pinto, P. C. R. O.; Silvestre, A. J. D.; Neto, C. P. Triterpenic and other lipophilic components from industrial cork byproducts J. Agric. Food Chem. 2006, 54, 6888-6893
37. Guinda, A.; Rada, M.; Delgado, T.; Gutiérrez-Adánez, P.; Castellano, J. M. Pentacyclic triterpenoids from olive fruit and leaf J. Agric. Food Chem. 2010, 58, 9685-9691
38. Rivas Martínez, S. Bioclimatic belts of West Europe. Relations between bioclimate and plant ecosystems. In Environment and Quality of Life: Climate and Global Change; Duplessy, J. C.; Pons, A.; Fantechi, R., Eds.; Proc. Eur. School Clim. Nat. Hazards course, Arles, France; 1990; Commission of the European Communities: Luxembourg, 1991; pp 225-246.
39. Beckonert, O.; Keun, H. C.; Ebbels, T. M. D.; Bundy, J.; Holmes, E.; Lindon, J. C.; Nicholson, J. K. Metabolic profiling, metabolomic and metabonomic procedures for NMR spectroscopy of urine, plasma, serum and tissue extracts Nat. Protoc. 2007, 2, 2692-2703