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Oxidative Stability of Virgin Olive Oils L Oxidative Stability of Virgin Olive Oils L. Cinquantaa,*, M. Estia, and M. Di Matteob aDepartment of Agricultural, Food, Environmental and Microbiological Science and Technology, University of Molise, 86100 Campobasso, Italy, and bDepartment of Chemical and Food Engineering, University of Salerno, 84084 Fisciano (SA), Italy ABSTRACT: An investigation was carried out on virgin olive oils important of which is oleuropein, present in the olives before of the Gentile (Larino), Gentile (Colletorto), Coratina, and Leccino extraction. Therefore, the phenol content of virgin olive oils varieties, harvested at different times, to assess their oxidation sta- depends on the fruits’ ripeness, variety, climatic conditions, bility. The olive oils were analyzed by means of peroxide, K232, and the oil extraction processes (2–6). Oxidative stability has and K270 values at 1, 6, 12, and 18 mon of storage in green bot- been correlated to the total hydrophilic phenols, to the ortho- tles, in the dark, at temperatures ranging from a mean of 6°C in diphenol compounds (7,8) such as 3,4-DHPEA, which in- winter to 12°C in summer. A subsample was also oven-tested at creases during olive maturation, and to the oleosidic forms of 75°C and then analyzed on a weekly basis using the same oxida- α tive parameters. The less ripe the olives (harvested in the same area 3,4-DHPEA (9). The antioxidant activity of -tocopherol has during 1 mon), the more resistant the olive oils were to forced oxi- been evaluated in olive oils and model systems (10). For in- dation. The amount of total phenols in the oils was found to be di- stance, the percentage contribution of the α-tocopherol to the rectly related, even if to a low degree, to the oleuropein content in oil’s stability, as measured by Rancimat, was estimated to be the olives and inversely related, to the same degree, to (3,4-dihy- less than that contributed by the composition of fatty acids droxyphenyl)ethanol. The latter is a derivative of oleuropein; (3,4- (24%), and substantially less than that contributed by pheno- dihydroxyphenyl)ethanol content increases as the olives ripen, but lic and orthodiphenolic compounds (51%) (11). it is very low in fresh virgin olive oils, owing to the hydrophilic na- Very little is known about the relationship between the ture of the phenolic alcohol, which goes mainly into the waste- phenolic composition of olives during maturation, and the water during processing. Among the varieties considered, Coratina stability of the oils. In a previous work, the authors studied oils showed the highest resistance to forced oxidation because of phenolic compounds in different olive varieties, taking into their high total phenol content. Paper no. J9785 in JAOCS 78, 1197–1202 (December 2001). account the degree of ripeness of the drupes (12). The aim of this present research was to assess the resistance to oxidation of virgin olive oils, typical of the area studied, obtained from KEY WORDS: (3,4-Dihydroxyphenyl)ethanol, K232, K270, oleuropein, olive variety, peroxide value, phenolic compounds, the above mentioned varieties, by evaluating the relationship thermal oxidation, virgin olive oil. between the phenolic compounds and the stability of the oils. This latter was analyzed by means of peroxide, K232, and K270 values at 1, 6, 12, and 18 months of storage. Moreover, a sub- Virgin olive oils are known to be more resistant to oxidation sample was also oven-tested at 75°C and then analyzed on a than other edible oils because of their content of natural an- weekly basis using the same oxidative parameters. tioxidants and lower unsaturation levels; the higher the num- ber of double bonds in fatty acids, the shorter is the induction EXPERIMENTAL PROCEDURES period for oil autoxidation, the main cause of their alteration. The stability of virgin olive oils is due to their natural pheno- Olive sampling and fruit analysis. The samples consisted of lic compounds, since these compounds are able to donate a olives (Olea europea L.) of the Gentile (Larino), Gentile (Col- hydrogen atom to the lipid radical formed during the propa- letorto), Coratina and Leccino varieties. [Gentile (Larino) and gation phase of lipid oxidation (1). Oleuropein, a glycosidic Gentile (Colletorto) are two distinctly different cultivars grown ester of elenolic acid, and (3,4-dihydroxyphenyl)ethanol (3,4- in the same province but under different soil and climate con- DHPEA = hydroxytyrosol), is the main phenolic compound ditions.] The drupes were hand-picked at different stages of in olives although it decreases notably during the course of ripeness in the Molise region in November 1995 and stored in ripening, and its content is negligible in the olive oils, where 25-kg plastic boxes for 24 h before processing. Sampling was derivatives of oleuropein hydrolysis during extraction domi- limited to the period when the olives are usually harvested and nate. For instance, glycosidases catalyze the hydrolysis of processed in the area considered. An unambiguous “olive oleuropein, with the production of oleuropein aglycon and the ripening index” to establish when to pick the drupes to obtain dialdehydic form of elenolic acid linked to 3,4-DHPEA. Nev- the best quality oils has not yet been devised; several that have ertheless, the resistance to oxidation is mainly due to pheno- been tried include the malic acid/citric acid ratio of drupes (13), lic compounds arising from the glycated precursors, the most the climacteric phase of olives (14), and/or the pigmentation or *To whom correspondence should be addressed at Department of Agricul- semipigmentation (the beginning of shift in skin color from tural, Food, Environmental and Microbiological Science and Technology, green to purple) of drupes (15). In our study, the maturation University of Molise, Via F. De Sanctis, 86100 Campobasso, Italy. E-mail: [email protected] index was determined according to the method proposed by the Copyright © 2001 by AOCS Press 1197 JAOCS, Vol. 78, no. 12 (2001) 1198 L. CINQUANTA ET AL. TABLE 1 Maturation Index, Hunter Color Values (L*, a*, b*)a, and Phenolic Compounds (mg/g)b of Olive Fruits at Different Harvest Times Harvest Maturation Varieties time Identification indexc L* a* b* 3,4-DHPEA Oleuropein Leccino 11/01/95 LecI 4.8 28.4 ± 3.4 −2.1 ± 0.1 1.9 ± 0.12 0.37 ± 0.05 0.97 ± 0.11 Leccino 11/15/95 LecII 4.5 31.0 ± 3.7 −1.8 ± 0.1 3.6 ± 0.29 0.60 ± 0.08 0.85 ± 0.09 Leccino 11/30/95 LecIII 4.9 27.2 ± 2.4 −2.4 ± 0.2 5.1 ± 0.3 0.72 ± 0.06 0.72 ± 0.08 Gentile (Larino) 11/01/95 GeLI 2.2 44.0 ± 3.2 −3.1 ± 0.2 12.2 ± 0.9 0.15 ± 0.03 1.12 ± 0.15 Gentile (Larino) 11/15/95 GeLII 2.6 42.7 ± 5.2 −6.5 ± 0.4 17.3 ± 1.5 0.48 ± 0.05 1.45 ± 0.19 Gentile (Larino) 11/30/95 GeLIII 3.9 38.1 ± 3.8 −1.8 ± 0.3 9.8 ± 0.8 0.62 ± 0.08 0.87 ± 0.09 Coratina 11/01/95 CorI 0.4 52.0 ± 4.8 −14.4 ± 0.9 24.7 ± 2.6 0.30 ± 0.06 1.44 ± 0.21 Coratina 11/15/95 CorII 0.8 53.6 ± 3.5 −19.5 ± 1.2 27.6 ± 2.2 0.47 ± 0.07 1.62 ± 0.18 Coratina 11/30/95 CorIII 0.7 48.8 ± 4.2 −17.6 ± 1.5 26.9 ± 2.5 0.52 ± 0.06 1.21 ± 0.16 Gentile (Colletorto) 11/01/95 GeCI 4.2 32.7 ± 4.3 1.0 ± 0.1 −0.1 ± 0.02 0.40 ± 0.07 2.08 ± 0.29 Gentile (Colletorto) 11/15/95 GeCII 4.9 29.3 ± 4.0 −0.5 ± 0.04 2.7 ± 0.16 0.97 ± 0.12 1.91 ± 0.21 Gentile (Colletorto) 11/30/95 GeCIII 4.8 30.7 ± 2.9 −3.8 ± 0.4 2.3 ± 0.28 1.10 ± 0.15 1.50 ± 0.19 aMeans ± standard deviations (SD) of 20 determinations. bMeans ± SD of three determinations. 3,4-DHPEA, (3,4-dihydroxyphenyl)ethanol, also known as hydroxytyrosol. cDetermined by the Jaèn index. National Institute of Agronomic Research of Spain (San Jaén flow rate was 1.3 mL min−1. The volume of injection was Station), which in brief consists of distributing randomly taken 20 µL. The eluates were detected by means of a photodiode samples of 100 olives in eight groups according to skin color. array at 280 nm (a wavelength at which phenolic compounds Maturation index values range from 0 (bright green) to 7 (pur- typically absorb) and 25°C. The mobile phase used was 2% ple) (16). Moreover, a colorimeter (CR-200b Chromometer, acetic acid in water (W) and methanol (M) for a total running Minolta, Japan) was used to assess the color of 20 fruit sam- time of 50 min, using the following gradients: from 97%W- ples to which the Hunter colorimetric system was applied (L*, 3%M to 80%W-20%M in 10 min, 60%W-40%M in 10 min, lightness; a*, redness; b*, yellowness). Detection and quantifi- 45%W-55%M in 15 min; and 0%W-100%M in 5 min until cation of phenolic compounds were carried out by HPLC the end of the run. analysis (12). The quantification of p-HPEA was carried out using the Olive sample processing. The virgin olive oil samples were external standard method, and the response factor of p-HPEA obtained by industrial processing; about 200 kg of olives from was used to quantify the 3,4-DHPEA.
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