Tentative identification of phenolic compounds in olive pomace extracts using liquid chromatography-tandem mass spectrometry with a quadrupole- quadrupole-time-of-flight mass detector

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 46, 2012, Pages 11542-11550

  Peralbo Molina, Ángela ^a,b   Priego Capote, Feliciano ^a,b   Luque De Castro, María Dolores ^a,b  

^a UNIVERSITY OF CÓRDOBA   (Spain)

^b HOSPITAL UNIVERSITARIO REINA SOFÍA   (Spain)

Author keywords

olive pomace; Phenolic compounds; QqTOF mass analyzer; superheated liquid extraction; tandem mass spectrometry

Indexed keywords

MASS ANALYZERS; OLIVE POMACE; PHENOLIC COMPOUNDS; SUPERHEATED LIQUIDS; TANDEM MASS SPECTROMETRY;

AGRICULTURE; LEACHING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SOLVENT EXTRACTION; VEGETABLE OILS;

PHENOLS;

OLIVE OIL; PHENOL DERIVATIVE; PLANT EXTRACT; VEGETABLE OIL;

ARTICLE; CHEMISTRY; EQUIPMENT; EVALUATION; LIQUID CHROMATOGRAPHY; METHODOLOGY; OLIVE TREE; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, LIQUID; OLEA; PHENOLS; PLANT EXTRACTS; PLANT OILS; TANDEM MASS SPECTROMETRY;

EID: 84869465825     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf302896m     Document Type: Article

References (40)

1. European Food Safety Authority (EFSA). Scientific Opinion on the evaluation of the substances currently on the list in the annex to Commission Directive 96/3/EC as acceptable previous cargoes for edible fats and oils-Part II of III EFSA J. 2012, 5, 150
2. Lozano-Sánchez, J.; Giambanelli, E.; Quirantes-Pine, R.; Cerretani, L.; Bendini, A.; Segura-Carretero, A.; Fernández- Gutiéerrez, A. Wastes generated during the storage of extra virgin olive oil as a natural source of phenolic compounds J. Agric. Food Chem. 2011, 21, 11491-11500
3. Sampedro, I.; Aranda, E.; Martín, J.; García-Garrido, J. M.; García-Romera, I.; Ocampo, J. A. Saprobic fungi decrease plant toxicity caused by olive mill residues Appl. Soil Ecol. 2004, 2, 149-156
4. Lesage-Meessen, L.; Navarro, D.; Maunier, S.; Sigoillot, J. C.; Lorquin, J.; Delattre, M.; Simon, J. L.; Asther, M.; Labat, M. Simple phenolic content in olive oil residues as a function of extraction systems Food Chem. 2001, 4, 501-507
5. Priego-Capote, F.; Ruiz-Jiménez, J.; Luque de Castro, M. D. Fast separation and determination of phenolic compounds by capillary electrophoresis-diode array detection: Application to the characterisation of alperujo after ultrasound-assisted extraction J. Chromatogr., A 2004, 1-2, 239-246
6. Celma, A. R.; Rojas, S.; López, F.; Montero, I.; Miranda, T. Thin-layer drying behaviour of sludge of olive oil extraction J. Food Eng. 2007, 4, 1261-1271
7. Hinneburg, I.; Damien Dorman, H. J.; Hiltunen, R. Antioxidant activities of extracts from selected culinary herbs and spices Food Chem. 2006, 1, 122-129
8. Torres de Pinedo, A.; Peñalver, P.; Morales, J. C. Synthesis and evaluation of new phenolic-based antioxidants: Structure-activity relationship Food Chem. 2007, 1, 55-61
9. Joubert, E.; de Beer, D. Phenolic content and antioxidant activity of rooibos food ingredient extracts J. Food Compos. Anal. 2012, 1, 45-51
10. Owen, R. W.; Giacosa, A.; Hull, W. E.; Haubner, R.; Spiegelhalder, B.; Bartsch, H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil Eur. J. Cancer 2000, 10, 1235-1247
11. European Food Safety Autority (EFSA). Scientific Opinion on the substantiation of health claims related to polyphenols in olive and protection of LDL particles from oxidative damage (ID 1333, 1638, 1639, 1696, 2865), maintenance of normal blood HDL cholesterol concentrations (ID 1639), maintenance of normal blood pressure (ID 3781), "antiinflammatory properties" (ID 1882), "contributes to the upper respiratory tract health" (ID 3468), "can help to maintain a normal function of gastrointestinal tract" (3779), and "contributes to body defences against external agents" (ID 3467) pursuant to Article 13(1) of Regulation (EC) No 1924/2006 EFSA J. 2011, 9 (4) 2033-2058
12. Emilia, J. E.; Uwe, W.; Hannelore, D.; Planas, J. M., Cancer chemopreventive activity of hydroxytyrosol: A natural antioxidant from olives and olive oil. In Olives and Olive Oil in Health and Disease Prevention; Preedy, V. R.; Ross, R. W., Eds.; Academic Press: San Diego, CA, 2010; Chapter 144, pp 1295-1300.
13. Fernández-Pachón, M. S.; Villaño, D.; Troncoso, A. M.; García-Parrilla, M. C. Determination of the phenolic composition of sherry and table white wines by liquid chromatography and their relation with antioxidant activity Anal. Chim. Acta 2006, 1-2, 101-108
14. Fernández-Orozco, R.; Roca, M.; Gandul-Rojas, B.; Gallardo-Guerrero, L. DPPH-scavenging capacity of chloroplastic pigments and phenolic compounds of olive fruits (cv. Arbequina) during ripening J. Food Compos. Anal. 2011, 6, 858-864
15. Pohjamo, S. P.; Hemming, J. E.; Willfòr, S. M.; Reunanen, M. H. T.; Holmbom, B. R. Phenolic extractives in Salix caprea wood and knots Phytochemistry 2003, 2, 165-169
16. Benavente-García, O.; Castillo, J.; Lorente, J.; Ortuño, A.; Del Río, J. A. Antioxidant activity of phenolics extracted from Olea europaea L. leaves Food Chem. 2000, 4, 457-462
17. Japón-Luján, R.; Luque-Rodríguez, J. M.; Luque de Castro, M. D. Dynamic ultrasound-assisted extraction of oleuropein and related biophenols from olive leaves J. Chromatogr., A 2006, 1, 76-82
18. Japón-Luján, R.; Luque-Rodríguez, J.; Luque de Castro, M. Multivariate optimization of the microwave-assisted extraction of oleuropein and related biophenols from olive leaves Anal. Bioanal. Chem. 2006, 4, 753-759
19. Ansari, M. A.; Abdul, H. M.; Joshi, G.; Opii, W. O.; Butterfield, D. A. Protective effect of quercetin in primary neurons against Aβ(1-42): Relevance to Alzheimer's disease J. Nutr. Biochem. 2009, 4, 269-275
20. Oh, H.; Kim, D.-H.; Cho, J.-H.; Kim, Y.-C. Hepatoprotective and free radical scavenging activities of phenolic petrosins and flavonoids isolated from Equisetum arvense J. Ethnopharmacol. 2004, 2-3, 421-424
21. Herrero, M.; Temirzoda, T. N.; Segura-Carretero, A.; Quirantes, R.; Plaza, M.; Ibañez, E. New possibilities for the valorization of olive oil by-products J. Chromatogr., A. 2011, 1218 (42) 7511-7520
22. Gortzi, O.; Lalas, S.; Chatzilazarou, A.; Katsoyannos, E.; Papaconstandinou, S.; Dourtoglou, E. Recovery of natural antioxidants from olive mill wastewater using Genapol-X080 J. Am. Oil Chem. Soc. 2008, 2, 133-140
23. Luque-Rodríguez, J. M.; Luque de Castro, M. D.; Pérez-Juan, P. Dynamic superheated liquid extraction of anthocyanins and other phenolics from red grape skins of winemaking residues Bioresour. Technol. 2007, 14, 2705-2713
24. Luque-Rodríguez, J. M.; Pérez-Juan, P.; Luque de Castro, M. D. Extraction of polyphenols from vine shoots of Vitis vinifera by superheated ethanol-water mixtures J. Agric. Food Chem. 2006, 23, 8775-8781
25. Smith, C. A.; Want, E. J.; O'Maille, G.; Abagyan, R.; Siuzdak, G. XCMS: Processing mass spectrometry data for metabolite profiling using nonlinear peak alignment, matching, and identification Anal. Chem. 2006, 3, 779-787
26. Tautenhahn, R.; Bottcher, C.; Neumann, S. Highly sensitive feature detection for high resolution LC/MS BMC Bioinf. 2008, 1, 504
27. Quideau, S. Methods in Polyphenol Analysis. Edited by Celestino Santos-Buelga and Gary Williamson. Angew. Chem., Int. Ed. 2004, 4, 393-394
28. Vázquez-Martín, A.; Fernández-Arroyo, S.; Cufi, S.; Oliveras-Ferraros, C.; Lozano-Sánchez, J.; Vellón, L.; Micol, V.; Joven, J.; Segura-Carretero, A.; Menéndez, J. A. Phenolic secoiridoids in extra virgin olive oil impede fibrogenic and oncogenic epithelial-to- mesenchymal transition: Extra virgin olive oil as a source of novel antiaging phytochemicals Rejuvenation Res. 2012, 1, 3-21
29. El Riachy, M.; Priego-Capote, F.; Rallo, L.; Luque de Castro, M. D.; León, L. Phenolic profile of virgin olive oil from advanced breeding selections Span. J. Agric. Res. 2012, 2, 443-453
30. Sánchez de Medina, V.; Priego-Capote, F.; Jiménez-Ot, C.; Luque de Castro, M. D. Quality and stability of edible oils enriched with hydrophilic antioxidants from the olive tree: The role of enrichment extracts and lipid composition J. Agric. Food Chem. 2011, 21, 11432-11441
31. González-Rodríguez, J.; Pérez-Juan, P.; Luque de Castro, M. D. Superheated liquids for extraction of solid residues from winemaking processes Anal. Bioanal. Chem. 2003, 7-8, 1190-1195
32. González-Rodríguez, J.; Pérez-Juan, P.; Luque de Castro, M. D. Use of superheated liquids for the extraction of non-volatile compounds from wood: Liquid chromatography studies J. Chromatogr., A 2004, 1-2, 3-9
33. Lama-Muñoz, A.; Rodríguez-Gutiérrez, G.; Rubio-Senent, F. t.; Gómez-Carretero, A.; Fernández-Bolaños, J. New hydrothermal treatment of alperujo enhances the content of bioactive minor components in crude pomace olive oil J. Agric. Food Chem. 2011, 4, 1115-1123
34. Brenes, M.; García, A.; García, P.; Ríos, J. J.; Garrido, A. Phenolic compounds in Spanish olive oils J. Agric. Food Chem. 1999, 9, 3535-3540
35. Pérez, J. A.; Hernández, J. M.; Trujillo, J. M.; López, H. Iridoids and secoiridoids from Oleaceae. In Studies in Natural Products Chemistry; Atta ur, R., Ed.; Elsevier: Amsterdam, The Netherlands, 2005; Vol. 32, Part L, pp 303-363.
36. Garrido Fernández, A.; Fernández Díez, M. J.; Adams, M. R. Table Olives; Chapman and Hall: London, U.K., 1997.
37. Gil, F. S.; Busconi, M.; Da Camara Machado, A.; Fogher, C. Development and characterization of microsatellite loci from Olea europaea Mol. Ecol. Notes 2006, 4, 1275-1277
38. Ryan, D.; Prenzler, P. D.; 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, 9, 2532-2538
39. Omar, S. H. Oleuropein in olive and its pharmacological effects Sci. Pharm. 2010, 2, 133-154
40. Sugihara, N.; Arakawa, T.; Ohnishi, M.; Furuno, K. Anti- and pro-oxidative effects of flavonoids on metal-induced lipid hydroperoxide- dependent lipid peroxidation in cultured hepatocytes loaded with α-linolenic acid Free Radical Biol. Med. 1999, 11-12, 1313-1323