**10. References**

368 Olive Oil – Constituents, Quality, Health Properties and Bioconversions

Immediately following oil extraction from the olive fruit, there is potential for the phenolic quality of the oil to decline, via oxidation catalysed by oxygen (O2) and light (Kalua et al., 2006a, Morello, 2004). One study to date, has investigated the effect O2, light, and storage time have on oleocanthal concentration. In this study, oleocanthal concentration decreased somewhat (15 - 37%) over a 10-month storage period, depending on the storage conditions. The largest decrease was seen in EVOO stored under exposure to O2 and light (37%) and the smallest loss was found in the EVOO stored under O2 and light limiting conditions (15%). Oils stored under sole exposure to O2 or light were found to have a similar rate of oleocanthal degradation over the 10-month period (28% and 25% respectively) (Cicerale et al., 2011b).

In general, research has shown that olive oil phenolic compounds are subject to degradation upon the application of heat during cooking (Brenes et al., 2002, Gomez-Alonso et al., 2003). However, oleocanthal has demonstrated to be relatively stable upon heating when the

One study found a 20% decrease in oleocanthal (96.7 ± 8.5 to 77.5 ± 2.4 mg/kg) upon 12 frying operations (each frying operation 10 min in length, at a temperature of 180°C) (Gomez-Alonso et al., 2003). Similarly, another study observed a 24% decrease (41.5 ± 0.3 to 31.4 ± 0.1 mg/kg) in oleocanthal after heating at 180°C for 36 hr (Allouche et al., 2007). However, for EVOO which naturally contained a lower quantity of oleocanthal to begin with (7.9 ± 0.5 mg/kg), oleocanthal degradation was substantially higher at 71%. It appears that oleocanthal possesses an antioxidative effect, in that oleocanthal is able to withstand heating and therefore protect

Cicerale and co-workers (Cicerale et al., 2009b) also demonstrated oleocanthal to be stable upon heating at high temperatures (240°C) for extended periods of time (up to 90 min). The authors postulated that the minimal degradation of oleocanthal may be partially due to the chemical structure of this compound and subsequent antioxidant activity. The antioxidant capacity of phenolic compounds is dependent upon the number of hydroxyl groups bonded to the aromatic ring (Sroka and Cisowski, 2003). When free radicals are produced through oxidation, phenolic compounds with a higher number of hydroxyls and therefore increased antioxidant capacity, quickly diminish because they react rapidly with lipid radicals and are therefore consumed (Gomez-Alonso et al., 2003). Oleocanthal possesses one hydroxyl group. Moreover, the site of bonding and mutual position of hydroxyls in the aromatic ring was also postulated to play a role in the antioxidant potential of phenolic compounds (Sroka and Cisowski, 2003, Rice-Evans et al., 1996). Rice-Evans and co-workers (Rice-Evans et al., 1996) reported that a hydroxyl group in the *ortho* position in the aromatic ring results in increased antioxidant capacity compared to compounds with hydroxyl groups in the *meta* and *para* positions. Oleocanthal contains its one hydroxyl group in the *para* position. These structural features may help in explaining why a minimal degradation of oleocanthal was observed

In summary, EVOO a key component of the Mediterranean diet contains a number of phenolics, one being oleocanthal. The unique sensory qualities and anti-inflammatory actions

EVOO contains a considerable quantity of this compound initially.

itself to a greater degree when there is a higher concentration of it in EVOO.

**8.7 Storage of EVOO** 

**8.8 Domestic heat application** 

(Cicerale et al., 2009c).

**9. Perspectives and future directions** 


Oleocanthal: A Naturally Occurring Anti-Inflammatory Agent in Virgin Olive Oil 371

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Inflammatory Benefits of Virgin Olive Oil and the Phenolic Compound


**20** 

*Spain* 

*University of Seville* 

**Biological Properties of** 

 José G. Fernández-Bolaños, Óscar López, M. Ángeles López-García and Azucena Marset

**Hydroxytyrosol and Its Derivatives** 

Polyphenols are a wide family of compounds found in fruits and vegetables, wine, tea, cocoa, and extra-virgin olive oil, which exhibit strong antioxidant activity by scavenging different families of Reactive Oxygen Species (ROS). One of the most effective members of the polyphenol family in terms of free radical scavenging is hydroxytyrosol, 2-(3,4 dihydroxyphenyl)ethanol (Fernández-Bolaños et al., 2008), a simple phenol found

Hydroxytyrosol (HT) can be found in leaves and fruits of olive, extra virgin olive oil and it is specially abundant in olive oil mill wastewaters from where it can be recovered (Fernández-Bolaños et al., 2008; Sabatini, 2010). Hydroxytyrosol is a metabolite of oleuropein (Fig. 1), another major phenolic component of olive products; they both give to extra-virgin olive oil its bitter and pungent taste (Omar, 2010a). Hydroxytyrosol shows a broad spectrum of biological properties due to its strong antioxidant and radical-scavenging properties. More active than antioxidant vitamins and synthetic antioxidants, hydroxytyrosol exerts its

HO

Historically, olive tree leaves were used for traditional therapy by ancient civilizations. Extracts from olive tree leaves were found to have a positive effect on hypertension by the

Hydroxytyrosol Oleuropein

OH

O

HO HO

O

Me O

OH

<sup>O</sup> <sup>O</sup> OH

MeO O

antioxidant activity by transforming itself into a catechol quinone (Rietjens, 2007).

OH

**1. Introduction** 

predominantly in olive tree (*Olea europaea*).

OH

Fig. 1. Structures of hydroxytyrosol and oleuropein

**2. Biological activity of hydroxytyrosol** 

HO

