Metabolites involved in oleuropein accumulation and degradation in fruits of Olea europaea L.: Hojiblanca and Arbequina varieties

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 24, 2010, Pages 12924-12933

  Gutierrez Rosales, Francisca ^a   Romero, María Paz ^b   Casanovas, María ^b   Motilva, María José ^b   Mínguez Mosquera, María Isabel ^a  

^a CSIC   (Spain)

^b UNIVERSITY OF LLEIDA   (Spain)

Author keywords

glucosidase; aglycones; elenolic acid; ligstroside; metabolism; oleoside 11 methyl ester; oleuropein; oleuropein precursors; Olive fruit; tyrosol

Indexed keywords

AGLYCONES; ELENOLIC ACID; GLUCOSIDASE; LIGSTROSIDE; OLEOSIDE-11-METHYL ESTER; OLEUROPEIN; OLIVE FRUIT; TYROSOL;

BIOCHEMISTRY; BIOSYNTHESIS; ENZYMES; ESTERIFICATION; ESTERS; FRUITS; METABOLISM; METABOLITES; PHENOLS; PHYSIOLOGY;

ENZYMATIC HYDROLYSIS;

BETA GLUCOSIDASE; GLUCOSIDE; OLEUROPEIN; PHENOL DERIVATIVE; PYRAN DERIVATIVE; VEGETABLE PROTEIN;

ARTICLE; CHEMISTRY; FRUIT; GROWTH, DEVELOPMENT AND AGING; METABOLISM; OLIVE TREE;

BETA-GLUCOSIDASE; FRUIT; GLUCOSIDES; OLEA; PHENOLS; PLANT PROTEINS; PYRANS;

OLEA EUROPAEA; OLEACEAE;

EID: 78650358116     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf103083u     Document Type: Article

References (27)

1. Amiot, M. J.; Fleuriet, A.; Macheix, J. J. Accumulation of oleuropein derivates during olive maturation Phytochemistry 1989, 28, 67-69
2. Amiot, M. J.; Fleuriet, A.; Macheix, J. J. Importance and evolution of phenolic compounds in olive during growth and maturation J. Agric. Food Chem. 1986, 34, 823-826
3. 1H-NMR study of phenolics in the vegetation water of three cultivars of Olea europaea: Similarities and differences J. Agric. Food Chem. 1996, 44, 2040-2048
4. Esti, M.; Cinquanta, L.; La Notte, E. Phenolic compounds in different olive varieties J. Agric. Food Chem. 1998, 46, 32-35
5. Ryan, D.; Antolovich, M.; Prenzler, P.; Robards, K.; Lavee, S. Biotransformations of phenolic compounds in Olea europaea L Sci. Hortic. (Amsterdam, Neth.) 2002, 92, 147-176
6. Ranalli, A.; Marchegiani, D.; Contento, S.; Girardi, F.; Nicolosi, M. P.; Brullo, M. D. Variations of iridoid oleuropein in Italian olive varieties during growth and maturation Eur. J. Lipid Sci. Technol. 2009, 111, 678-687
7. Morelló, J. R.; Romero, M. P.; Motilva, M. J. Effect of the maturation process of the olive fruit on the phenolic fraction of drupes and oils from Arbequina, Farga, and Morruts cultivars J. Agric. Food. Chem. 2004, 52, 6002-6009
8. Ryan, D.; Prenzler, P.; Lavee, S.; Antolovich, M.; Robards, K. Quantitative changes in phenolic content during physiological development of the olive (Olea europaea) cultivar Hardy's Mammoth J. Agric. Food Chem. 2003, 51, 2532-2538
9. Ryan, D.; Antolovich, M.; Herlt, T.; Prenzler, P. D.; Lavee, S.; Robards, K. Identification of phenolic compounds in tissues of the novel olive cultivar Hardy's Mammoth J. Agric. Food Chem. 2002, 50, 6716-6724
10. Inouye, H.; Ueda, S.; Inoue, K.; Takeda, Y. Biosynthesis of oleuropein-type secoiridoid glucosides by oleaceae Tetrahedron Lett. 1971, 43, 4073-4076
11. Inouye, H.; Ueda, S.; Inoue, K.; Takeda, Y. Studies on monoterpene glucosides and related natural products. XXIII. Biosynthesis of the secoiridoid glucosides, gentiopicroside, morroniside, oleuropein and jasminin Chem. Pharm. Bull. 1974, 22, 676-686
12. Damtoft, S.; Franzyk, H.; Jensen, S. R. Biosynthesis of secoiricoid glucosides in Oleaceae Phytochemistry 1993, 34, 1291-1299
13. Damtoft, S.; Franzyk, H.; Jensen, S. R. Biosynthesis of iridoids in Syringa and Fraxinus: Secoiridoid precursors Phytochemistry 1995, 40, 773-784
14. Damtoft, S.; Franzyk, H.; Jensen, S. R. Biosynthesis of iridoids in Syringa and Fraxinus: Carbocyclic iridoid precursors Phytochemistry 1995, 40, 785-792
15. Pérez, J. A.; Hernández, J. M.; Trujillo, J. M.; López, H. Iridoids and secoiridoids from Oleaceae. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: Amsterdam, The Netherlands, 2005; Vol. 32, Part 12, pp 303-368.
16. Soler-Rivas, C.; Espín, J. C.; Wichers, H. J. Oleuropein and related compounds J. Sci. Food Agric. 2000, 80, 1013-1023
17. Artajo, L. S.; Romero, M. P.; Morelló, J. R.; Motilva, M. P. Enrichment of refined olive oil with phenolic compounds: Evaluation of their antioxidant activity and their affect on the bitter index J. Agric. Food Chem. 2006, 54, 6079-6088
18. Ríos-Martin, J. J.; Gutiérrez-Rosales, F. Comparison of methods extracting phenolic compounds from lyophilised and fresh olive pulp LWT-Food Sci. Technol. 2010, 43, 1285-1288
19. Suárez, M.; Macià, A.; Romero, M. P.; Motilva, M. J. Improved liquid chromatography tandem mass spectrometry method for the determination of phenolic compounds in virgin olive oil J. Chromatogr., A 2008, 1214, 90-99
20. Romero-Segura, C.; Sanz, C.; Pérez, A. G. Purification and characterization of an olive fruit β-glucosidase involved in the biosynthesis of virgin olive oil phenolics J. Agric. Food Chem. 2009, 57, 7983-7988
21. Minguez-Mosquera, M. I.; Gandul-Rojas, B.; Gallardo-Guerrero, L. Measurement of chlorophyllase activity in olive fruit (Olea europaea) J. Biochem. 1994, 116, 263-268
22. Capasso, R.; Evidente, A.; Visca, C.; Gianfreda, L.; Maremonti, M.; Greco, G., Jr. Production of glucose and bioactive aglycone by chemical and enzymatic hydrolisis of purified oleuropein from Olea europea Appl. Biochem. Biotechnol. 1996, 61, 365-377
23. Obied, H. K.; Bedgood, D. R.; Prenzler, P. D.; Robards, K. Chemical screening of olive biophenol extracts by hyphenated liquid chromatography Anal. Chim. Acta 2007, 603, 176-189
24. Vierhuis, E.; Servili, M.; Baldioli, M.; Schols, H. A.; Voragen, A. G. J.; Montedoro, G. F. Effect of enzyme treatment during mechanical extraction of olive oil on phenolic compounds and polysaccharides J. Agric. Food Chem. 2001, 49, 1218-1223
25. Montedoro, G.; Servili, M.; Baldioli, M.; Selvaggini, R.; Miniati, E.; Macchioni, A. Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of the secoiridoid derivatives J. Agric. Food Chem. 1993, 41, 2228-2234
26. Fernández-Bolaños, J.; Rodríguez, R.; Guillén, R.; Jiménez, A.; Heredia, A. Activity of cell wall-associated enzymes in ripening olive fruit Physiol. Plant. 1995, 93, 651-658
27. Parr, A. J.; Bolwell, G. P. Phenols in the plant and in man. The potential for possible nutritional enhancement of the diet by modifying the phenols content or profile J. Sci. Food Agric. 2000, 80, 985-1012