Temporal metabolomic analysis of O-glucoside phenolic compounds and their aglycone forms in olive tree and derived materials

Phytochemical Analysis

Volumn 20, Issue 3, 2009, Pages 221-230

  Luján, Rafael Japón ^a   Capote, Feliciano Priego ^a   de Castro, María Dolores Luque ^a  

^a UNIVERSITY OF CÓRDOBA   (Spain)

Author keywords

Liquid chromatography; Multiple reaction monitoring; Olive raw materials; Phytochemical analysis; Tandem mass spectrometry

Indexed keywords

CARBOHYDRATES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; PHENOLS; QUALITY CONTROL;

AGLYCONES; GLUCOSIDASE; MULTIPLE REACTION MONITORING; OLIVE RAW MATERIAL; PHENOLIC COMPOUNDS; PHYTOCHEMICAL; PHYTOCHEMICAL ANALYSE; TANDEM MASS SPECTROMETRY; TANDEM-MASS SPECTROMETRY; TARGET COMPOUND;

OLIVE OIL;

ACTEOSIDE; AGLYCONE; APIGENIN; APIGETRIN; BETA GLUCOSIDASE; HYDROXYTYROSOL; LUTEOLIN; LUTEOLIN 7 GLUCOSIDE; O GLUCOSIDE PHENOL DERIVATIVE; OLEUROPEIN; OLIVE OIL; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ISOLATION PROCEDURE; LIQUID CHROMATOGRAPHY; METABOLOMICS; NONHUMAN; OLIVE TREE; PHYTOCHEMISTRY; PLANT LEAF; PLANT STEM; SEASONAL VARIATION; SENSITIVITY AND SPECIFICITY; TANDEM MASS SPECTROMETRY;

EID: 65949090522     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.1118     Document Type: Article

References (45)

1. Aharoni A, De Vos CHR, Verhoeven HA, Maliepaard CA, Kruppa G, Bino R, Goodenowe DB. 2002. Nontargeted metabolome análisis by use of Fourier Transform Ion Cyclotron Mass Spectrometry, OMICS 6: 217-234.
2. Blount JW, Masoud S, Sumner LW, Huhman D, Dixon RA. 2002. Over-expression of cinnamate 4-hydroxylase leads to increased accumulation of acetosyringone in elicited tobacco cell-suspension cultures. Planta 214: 902-910.
3. Defernez M, Gunning YM, Parr AJ, Shepherd LVT, Davies HV, Colquhoun IJ. 2004. NMR and HPLC-UV profiling of potatoes with genetic modifications to metabolic pathways. J Agric Food Chem 52: 6075-6085.
4. Fabiani R, De Bartolomeo A, Rosignoli P, Servili M, Montedoro GF, Morozzi G. 2002. Cancer chemoprevention by hydroxytyrosol isolat from virgin olive oil through G(1) cell cycle arrest and apoptosis. Eur J Cancer Prev 11: 351-358.
5. Fiehn O, Kopka J, Trethewey RN, Willmitzer L. 2000a. Identification of uncommon plant metabolites based on calculation of elemental compositions using gas chromatography and quadrupole mass spectrometry. Anal Chem 72: 3573-3580.
6. Fiehn O, Kopka J, Dormann P, Altmann T, Trethewey RN, Willmitzer L. 2000b. Metabolite profiling for plant functional genomics. Nature Biotechnol 18: 1157-1161.
7. Gachon C, Langlois-Meurinne M, Saindrenan P. 2005. Plant secondary metabolism glycosyltransferases: the emerging functional analysis. Trends Plant Sci 10: 542-549.
8. Garratt LC, Linforth R, Taylor AJ, Lowe KC, Power JB, Davey MR. 2005. Metabolite fingerprinting in transgenic lettuce. Plant Biotechol J 3: 165-174.
9. Gee JM, DuPont MS, Rhodes MJC, Johnson IT. 1998. Quercetin glucosides interact with the intestinal glucose transport pathway. Free Radical Biol Med 25: 19-25.
10. Hamzehzarghani H, Kushalappa AC, Dion Y, Rioux S, Comeau A, Yaylayan V, Marshall WD, Mather DE. 2005. Metabolic profiling and factor analysis to discriminate quantitative resistance in wheat cultivars against fusarium head blight. Physiol Mol Plant Pathol 66: 119-133.
11. Hirai MY, Klein M, Fujikawa Y, Yano M, Goodenowe DB, Yamazaki Y, Kanaya S, Nakamura Y, Kitayama M, Suzuki H, Sakurai N, Shibata D, Tokuhisa J, Reichelt M, Gershenzon J, Papenbrock J, Saito K. Elucidation of gene-to-gene and metabolite-to-gene networks in Arabidopsis by integration of metabolomics and transcriptomics. 2005. J Biol Chem 280: 25590-25595.
12. Hollman PCH, Bijsman MNCP, van Gameren Y, Cnossen GPJ, de Vries JHM, Katan, MB. 1999. The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Radical Res 31: 569-573.
13. Japón-Luján R, Luque de Castro MD. 2006. Superheated liquid extraction of oleuropein and related biophenols from olive leaves. J Chromatogr A 1136: 185-191.
14. Japón-Luján R, Luque de Castro MD. 2007a. Small branches of olive tree: A source of biophenols complementary to olive leaves. J Agric Food Chem 55: 4585-4588.
15. Japón-Luján R, Luque de Castro MD. 2007b. Static-dynamic superheated liquid extraction of hydroxytyrosol and other biophenols from alperujo (a semisolid residue of the olive oil industry). J Agric Food Chem 55: 3629-3634.
16. Japón-Luján R, Luque-Rodríguez JM, Luque de Castro MD. 2006a. Dynamic ultrasound-assisted extraction of oleuropein and related biophenols from olive leaves. J Chromatogr A 1108: 76-82.
17. Japón-Luján R, Luque-Rodriguez JM, Luque de Castro MD. 2006b. Multivariate optimisation of the microwave-assisted extraction of oleuropein and related biophenols from olive leaves. Anal Bioanal Chem 385: 753-759.
18. Japón-Luján R, Priego-Capote F, Marinas A, Luque de Castro MD. 2008. Liquid chromatography/triple quadrupole tandem mass spectrometry with multiple reaction monitoring for optimal selection of transitions to evaluate nutraceuticals from olive-tree materials. Rap Comm Mass Spectrom 22: 855-864.
19. Jia L, Terabe S (eds). 2005. Metabolome Analysis. Springer: New York.
20. Kim MM, Kim SN. 2002. Applic. KR 2000-27738 200000523; Republic of Korean Kongkae Taeho Kongbo.
21. Kopka J, Fernie AR, Weckwerth W, Gibon Y, Stitt M. 2004. Metabolite profiling in plant biology: platforms and destinations. Genome Biology 5: 109-115.
22. Lenz EM, Bright J, Knight R, Wilson ID, Major H. 2004. A metabonomic investigation of the biochemical effects of mercuric chloride in the rat using H-1 NMR and HPLC-TOF/MS: time dependant changes in the urinary profile of endogenous metabolites as a result of nephrotoxicity. Analyst 129: 535-541.
23. Lindon JC, Nicholson JK (eds) 2007. The Handbook of Metabonomics and Metabolomics. Elsevier: Amsterdam.
24. Lindon JC, Nicholson JK, Holmes E, Antti H, Bollard ME, Keun H, Beckonert O, Ebbels TM, Reily MD, Robertson D, Stevens GJ, Luke P, Breau AP, Cantor GH, Bible RH, Niederhauser U, Senn H, Schlotterbeck G, Sidelmann UG, Laursen SM, Tymiak A, Car BD, Lehman-McKeeman L, Colet JM, Loukaci A, Thomas C. 2003. Contemporary issues in toxicology. The role of metabonomics in toxicology and its evaluation by the COMET project. Toxicol Applied Pharmacol 187: 137-146.
25. Luque de Castro MD, Japón-Luján R. 2006. State-of-the-art and trends in the analysis of oleuropein and derivatives. Trends Anal Chem 25: 501-510.
26. Merchant A, Richter A, Popp M, Adams M. 2006. Targeted metabolite profiling provides a functional link among eucalypt taxonomy, physiology and evolution. Phytochem 67: 402-408.
27. Mercier J. 1997. Phytochemistry of Fruits and Vegetables. Claredon: Oxford.
28. Morikawa T, Mizutani M, Aoki N, Watanabe B, Saga H, Saito S, Oikawa A, Suzuki, N. Sakurai, D. Shibata, A. Wadano, K. Sakata, D. Ohta. 2006. Cytochrome P450CYP710A encodes the sterol C-22 desaturase in Arabidopsis and tomato. Plant Cell 18: 1008-1022.
29. Morino K, Matsuda F, Miyazawa H, Sukegawa A, Miyagawa H, Wakasa K. 2005. Metabolic profiling of tryptophan-overproducing rice calli that express a feedback-insensitive alpha subunit of anthranilate synthase. Plant Cell Physiol 46: 514-521.
30. Patil SC, Singh VP, Satyanarayan PSV, Jain NK, Singh A, Kulkarni SK. 2003. Protective effect of flavonoids against aging-and lipopolysaccharide-induced cognitive impairment in mice. Pharmacology 69: 59-67.
31. Plumb RS, Granger JH, Stumpf CL, Johnson KA, Smith BW, Gaulitz S, Wilson ID, Castro-Pérez JA. 2005. A rapid screening approach to metabonomics using UPLC and oa-TOF mass spectrometry: application to age, gender and diurnal variation in normal/Zucker obese rats and black, white and nude mice. Analyst 130: 844-849.
32. Roessner U, Luedemann A, Brust D, Fiehn O, Linke T, Willmitzer L, Fernie AR. Metabolic profiling allows comprehensive phenotyping of genetically or environmentally modified plant systems. 2001. Plant Cell 13: 11-29.
33. Roessner U, Hegemann B, Lytovchenko A, Carrari F, Bruedigam C, Granot D, Fernie AR. 2003. Metabolic profiling of transgenic tomato plants overexpressing hexokinase reveals that the influence of hexose phosphorylation diminishes during fruit development. Plant Physiol 133: 84-99.
34. Rooney OM, Troke J, Nicholson JK, Griffin JL. 2003. High-resolution diffusion and relaxation-edited magic angle spinning H-1 NMR spectroscopy of intact liver tissue. Magn Reson Med 50: 925-930.
35. Sato S, Soga T, Nishioka T, Tomita M. 2004. Simultaneous determination of the main metabolites in rice leaves using capillary electrophoresis mass spectrometry and capillary electrophoresis diode array detection. Plant J 40: 151-163.
36. Schauer N, Fernie AR. 2006. Plant metabolomics: towards biological function and metabolism. Trends Plant Sci 11: 508-516.
37. Soga T, Ohashi Y, Ueno Y, Naraoka H, Tomita M, Nishioka T. 2003. Quantitative metabolome análisis using capillary electrophoresis mass spectrometry. J Proteome Res 2: 488-494.
38. Stitt M, Fernie AR. 2003. From measurements of metabolites to metabolomics: an 'on the fly' perspective illustrated by recent studies of carbon-nitrogen interactions. Curr Opin Biotechnol 14: 136-144.
39. Sweetlove LJ, Fernie AR. 2005. Regulation of metabolic networks: understanding metabolic complexity in the systems biology era. New Phytol 168: 9-23.
40. Takahashi T, Kobori M, Shinmoto H, Tsushida T. 1998. Structure-activity relationships of flavonoids and the induction of granulocytic - or monocytic - differentiation in HL60 human myeloid leukemia cells. Biosci Biotechnol Biochem 2: 2199-2204.
41. Theoharides TC, Kempuraj D, Iliopoulou BP. 2007. Mast cells, T cells, and inhibition by luteolin: implications for the pathogenesis and treatment of multiple sclerosis. Adv Exp Med Biol 601: 423-430.
42. Ulrich-Merzenich G, Zeitler H, Jobst D, Panek D, Vetter H, Wagner H. 2007. Application of the '-Omic-' technologies in phytomedicine. Phytomed 14: 70-82.
43. Urbanczyk-Wochniak E, Fernie AR. 2005. Metabolic profiling reveals altered nitrogen nutrient regimes have diverse effects on the metabolism of hydroponically-grown tomato (Solanum lycopersicum) plant. J Exp Botany 56: 309-321.
44. Zheng QS, Sun XL, Xu B, Li G, Song M. 2005a. Mechanisms of apigenin-7-glucoside as a hepatoprotective agent. Biomed Environ Sci 18: 65-70.
45. Zheng Q, Zhang Y, Zheng R, Guo D, Li C. 2005b. Effects of verbascoside and luteolin on oxidative damage in brain of heroin treated mice. Pharmazie 60: 539-544.