New isobaric lignans from Refined Olive Oils as quality markers for Virgin Olive Oils

Food Chemistry

Volumn 219, Issue , 2017, Pages 148-157

  Cecchi, Lorenzo ^a   Innocenti, Marzia ^a   Melani, Fabrizio ^a   Migliorini, Marzia ^b   Conte, Lanfranco ^c   Mulinacci, Nadia ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b Laboratorio Chimico Merceologico   (Italy)

^c UNIVERSITY OF UDINE   (Italy)

Author keywords

(+) 1 Acetoxypinoresinol; (+) Pinoresinol; Bleaching; HPLC TOF; Lampante Olive Oil; Olive oil frauds

Indexed keywords

ATMOSPHERIC PRESSURE; BLEACHING; CLEANING; MOLECULAR DYNAMICS; REFINING;

(+)-1-ACETOXYPINORESINOL; (+)-PINORESINOL; EXTRA VIRGIN OLIVE OIL; HPLC-TOF; OIL REFINING PROCESS; REFINED OIL; REFINING PROCESS; VIRGIN OLIVE OIL;

OLIVE OIL;

1-ACETOXYPINORESINOL; FURAN DERIVATIVE; LIGNAN; OLIVE OIL; PINORESINOL;

CHEMISTRY; FOOD QUALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ITALY; SPAIN; TUNISIA;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FOOD QUALITY; FURANS; ITALY; LIGNANS; OLIVE OIL; SPAIN; TUNISIA;

EID: 84988498955     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2016.09.132     Document Type: Article

References (35)

1. Andrewes, P., Busch, J.L.H.C., De Joode, T., Groenewegen, H., Alexandre, H., Sensory properties of virgin olive oil polyphenols: Identification of deacetoxy-ligstroside aglycon as a key contributor to pungency. Journal of Agricultural and Food Chemistry 51 (2003), 1415–1420.
2. Ballus, C.A., Quirantes-Piné, R., Bakhouche, A., de Oliveira da Silva, L.F., de Oliveira, A.F., Coutinho, E.F.,.. Godoy, H.T., Profile of phenolic compounds of Brazilian virgin olive oils by rapid resolution liquid chromatography coupled to electrospray ionization time-of-flight mass spectrometry (RRLC-ESI-TOF-MS). Food Chemistry 170 (2015), 366–377.
3. Beauchamp, G.K., Keast, R.S.J., Morel, D., Lin, J., Pika, J., Han, Q.,.. Lee, C., Phytochemistry: Ibuprofen-like activity in extra-virgin olive oil. Nature 437 (2005), 45–46.
4. Bendini, A., Cerretani, L., Carrasco-Pancorbo, A., Gòmez-Caravaca, A.M., Segura-Carretero, A., Fernandez-Gutierrez, A., Lercker, G., Phenolic molecules in virgin olive oils: a survey of their sensory properties, health effects, antioxidant activity and analytical methods. Molecules 12 (2007), 1679–1719.
5. Bonoli, M., Bendini, L., Cerretani, L., Lercker, G., Qualitative and semiqualitative analysis of phenolic compounds in extra virgin olive oils as a function of the ripening degree of olive fruits by different analytical techniques. Journal of Agricultural and Food Chemistry 52 (2004), 7026–7032.
6. Brenes, M., Garcia, A., Rios, J.J., Garcia, P., Garrido, A., Use of 1-acetoxypinoresinol to authenticate Picual olive oils. Journal of the American Oil Chemists Society 77 (2002), 715–720.
7. Brenes, M., Hidalgo, F.J., Garcia, A., Rios, J.J., Garcia, P., Zamora, R., Garrido, A., Pinoresinol and 1-acetoxy-pinoresinol, two new phenolic compounds identified in olive oil. Journal of the American Oil Chemists’ Society 29:1 (2000), 139–146.
8. Buckland, G., Gonzalez, C.A., The role of olive oil in disease prevention: A focus on the recent epidemiological evidence from cohort studies and dietary intervention trials. British Journal of Nutrition 113:2 (2015), 94–101.
9. Case, D.A., Darden, T.A., Cheatham, T.E. III, Simmerling, C.L., Wang, J., Duke, R.E.,.. Kollman, P.A., AMBER 9. 2006, University of California, San Francisco, USA.
10. Cecchi, L., Migliorini, M., Cherubini, C., Giusti, M., Zanoni, B., Innocenti, M., Mulinacci, N., Phenolic profiles, oil amount and sugar content during olive ripening of three typical Tuscan cultivar to detect the best harvesting time for oil production. Food Research International 54 (2013), 1876–1884.
11. Cecchi, L., Migliorini, M., Cherubini, C., Innocenti, M., Mulinacci, N., Whole lyophilized olives as sources of unexpectedly high amounts of secoiridoids: the case of three Tuscan cultivars. Journal of Agricultural and Food Chemistry 63 (2015), 1175–1185.
12. Coccia, A., Bastianelli, D., Mosca, L., Monticolo, R., Panuccio, I., Carbone, A.,.. Lendaro, E., Extra virgin olive oil phenols suppress migration and invasion of T24 human bladder cancer cells through modulation of matrix metalloproteinase-2. Nutrition and Cancer 66:6 (2014), 946–954.
13. Cohen, L.A., Epstein, M., Pittman, B., Rivenson, A., The influence of different varieties of olive oil on N-methylnitrosourea (NMU) induced mammary tumorigenesis. Anticancer Research 20 (2000), 2307–2312.
14. Covas, M.I., Nyyssonen, K., Poulsen, H.E., Kaikkonen, J., Zunft, H.J., Kiesewetter, H.,.. Marrugat, J., The effect of polyphenols in olive oil on heart disease risk factor: A randomized trial. Annals of Internal Medicine 145 (2006), 333–341.
15. EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA) Scientific opinion on the substantiation of health claims related to polyphenols in olive oil and protection of LDL particles from oxidative damage. EFSA Journal, 9(4), 2011, 2033 < http://www.efsa.europa.eu/en/efsajournal/pub/2033.htm>.
16. European Regulation (EU) No. 1308/13, On establishing a common organization of the markets in agricultural products. Official Journal of the European Union L347 (2013), 671–854.
17. Fini, L., Hotchkiss, E., Fogliano, V., Graziani, G., Romano, M., de Vol, E.B.,.. Selgrad, M., Chemopreventive properties of pinoresinol-rich olive oil involve a selective activation of the ATM-p53 cascade in colon cancer cell lines. Carcinogenesis 29:1 (2008), 139–146.
18. Frankel, E.N., Nutritional and biological properties of extra virgin olive oil. Journal of Agricultural and Food Chemistry 59 (2011), 785–792.
19. Garcìa, A., Ruiz-Mendez, M.V., Romero, C., Brenes, M., Effect of refining on the phenolic composition of crude olive oils. Journal of the American Oil Chemists Society 2 (2006), 159–164.
20. Grossi, C., Rigacci, S., Ambrosini, S., Ed Dami, T., Luccarini, I., Traini, C.,.. Stefani, M., The polyphenol oleuropein aglycone protects mice against Aβ plaque pathology. PLoS One 8:8 (2013), 1–13.
21. Gutièrrez-Rosales, F., Rios, J.J., Gomèz-Rey, L., Main polyphenols in the bitter taste of virgin olive oil. Structural confirmation by on-line-high-performance-liquid-chromatography electrospray ionization mass spectrometry. Journal of Agricultural and Food Chemistry 51 (2003), 6021–6025.
22. Migliorini, M., Cecchi, L., Cherubini, C., Trapani, S., Cini, E., Zanoni, B., Understanding degradation of phenolic compounds during olive oil processing by inhibitor addition. European Journal of Lipid Science and Technology 114 (2012), 942–950.
23. Migliorini, M., Cherubini, C., Cecchi, L., Zanoni, B., (Trans.) Degradazione dei composti fenolici durante la conservazione dell'olio extra vergine di olive, 2013, La Rivista Italiana delle Sostanze Grasse, XC, 71–80.
24. Mongan, J., Case, D.A., McCammon, J.A., Constant pH molecular dynamics in generalized born implicit solvent. Journal of Computational Chemistry 25 (2004), 2038–2048.
25. Oliveras-Lopéz, M.J., Innocenti, M., Giaccherini, C., Ieri, F., Romani, A., Mulinacci, N., Study of the phenolic composition of Spanish and Italian monocultivar extra virgin olive oil: Distribution of lignans, secoiridoidic, simple phenols and flavonoids. Talanta 73 (2007), 726–732.
26. Oliveras-Lopéz, M.J., Innocenti, M., Ieri, F., Giaccherini, C., Romani, A., Mulinacci, N., HPLC/DAD/ESI/MS detection of lignans from Spanish and Italian Olea europaea L. fruits. Journal of Food Composition and Analysis 21:1 (2008), 62–70.
27. Onofri A. (2007). Routine statistical analysis of field experiments by using an Excel extension. 6th National Conference of the Italian Biometric Society June, 20–22; Pisa, Italy.
28. Onufriev, A., Bashford, D., Case, D.A., Exploring protein native states and large-scale conformational changes with a modified generalized born model. Proteins 55 (2004), 383–394.
29. Owen, R.W., Haubner, R., Wurtele, G., Hull, W.E., Spiegelhalder, B., Bartsch, H., Olives and olive oil in cancer prevention. European Journal of Cancer Prevention 13:4 (2004), 319–326.
30. Owen, R.W., Mier, W., Giacosa, A., Hull, W.E., Spiegelhalder, B., Bartsch, H., Identification of lignans as major components in the phenolic fraction of olive oil. Clinical Chemistry 46:7 (2000), 976–988.
31. Salvini, S., Sera, F., Caruso, D., Giovannelli, L., Visioli, F., Saieva, C.,.. Palli, D., Daily consumption of a high-phenol extra-virgin olive oil reduces oxidative DNA damage in postmenopausal women. British Journal of Nutrition 95 (2006), 742–751.
32. Servili, M., Sordini, B., Esposto, S., Urbani, S., Veneziani, G., Di Maio, I.,.. Taticchi, A., Biological activities of phenolic compounds of extra virgin olive oil. Antioxidants 3:1 (2014), 1–23.
33. Tena, N., Wang, S.C., Aparicio-Ruiz, R., Garcìa-Gonzalez, D.L., Aparico, R., In-depth assessment of analytical methods for olive oil purity, safety, and quality characterization. Journal of Agricultural and Food Chemistry 63 (2015), 4509–4526.
34. Wang, J.M., Wang, W., Kollman, P.A., Case, D.A., Automatic atom type and bond type perception in molecular mechanical calculations. Journal of Molecular Graphics and Modelling 25 (2006), 247–260.
35. Wang, J.M., Wolf, R.M., Caldwell, J.W., Kollman, P.A., Case, D.A., Development and testing of a general amber force field. Journal of Computational Chemistry 25 (2004), 1157–1174.