**1. Introduction**

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

Visioli, F.; Caruso, D.; Plasmati, E.; Patelli, C.; Mulinacci, N.; Romani, A. et al. (2001).

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Hydroxytyrosol, as a Component of Olive Mill Waste Water, is Dose-Dependently Absorbed and Increases the Antioxidant Capacity of Rat Plasma. *Free Radical* 

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(2004). Bioavailability of Olive Oil Phenolic Compounds from Olive Oil and Oxidative/Antioxidative Status at Postprandial State in Humans. *Drugs under Experimental and Clinical Research*, Vol. 30, No. 5-6, (n.d.), pp. 207-212, ISSN 0378Research on the non-steroidal anti-inflammatory olive oil phenolic, (-)- decarboxymethyl ligstroside aglycone (more commonly known as oleocanthal) has supported speculation that this compound may confer some of the health benefits associated with the traditional Mediterranean diet. Oleocanthal elicits a peppery, stinging sensation at the back of the throat similar to that of the non-steroidal anti-inflammatory drug (NSAID), ibuprofen (Beauchamp et al., 2005) and this localized irritation is due to stimulation of the transient receptor potential cation channel A1 (TRPA1) (Peyrot des Gachons et al., 2011). The perceptual similarity between oleocanthal and ibuprofen spurred the hypothesis that these two compounds may possess similar pharmacological properties. Further investigation demonstrated that oleocanthal inhibits inflammation in the same way as ibuprofen, and moreover, is substantially more potent on a equimolar basis (Beauchamp et al., 2005). Subsequent studies have shown that oleocanthal exhibits various modes of action in reducing inflammatoryrelated disease, including neuro-degenerative disease (Pitt et al., 2009, Li et al., 2009), jointdegenerative disease (Iacono et al., 2010) and specific cancers (Elnagar et al., 2011). Therefore, long term consumption of extra virgin olive oil (EVOO) containing oleocanthal may contribute to the health benefits associated with the Mediterranean dietary pattern. This chapter summarizes the current knowledge on oleocanthal, in terms of its sensory and physiological properties, its extraction from the oil matrix and subsequent identification and quantification, and finally the factors that may influence the concentration of oleocanthal in EVOO.

#### **2. Olive oil, a hallmark of the Mediterranean diet**

The health benefits of following a Mediterranean eating pattern were first acknowledged in the Seven Countries Study (Keys, 1970). Thereafter over a period of 30 years, a number of investigators have reported that the Mediterranean diet is associated with low rates of degenerative diseases such as cardiovascular disease (CVD) (Estruch et al., 2006, Pitsavos et al., 2005), coronary heart disease (CHD) (Fung et al., 2009), stroke (Fung et al., 2009), certain types of cancers (La Vecchia, 2004, Dixon et al., 2007), diabetes (Martinez-Gonzalez et al., 2008), Alzheimer's disease (Scarmeas et al., 2009) and non-alcoholic fatty liver disease (Fraser et al., 2008). Research has also demonstrated that Mediterranean populations have

Oleocanthal: A Naturally Occurring Anti-Inflammatory Agent in Virgin Olive Oil 359

Miranda et al., 2010, Harper et al., 2006, Aguilera et al., 2004). In addition to oleic acid, EVOO contains a minor, yet significant phenolic fraction that other seed oils lack and this

Currently, 36 phenolic compounds have been identified in EVOO and studies (human, animal, *in vivo* and *in vitro*) have demonstrated that olive oil phenolics have positive effects on certain physiological parameters such as plasma lipoproteins, oxidative damage, inflammatory markers, platelet and cellular function, antimicrobial activity, and bone health (for review see (Cicerale et al., 2010)), possibly reducing the risk of chronic disease

The phenolic compound (-)- decarboxymethyl ligstroside aglycone was first reported in EVOO by Montedoro *et al.* (Montedoro and Servili, 1993) in 1993 (Figure 2). A decade after its discovery, Andrewes and colleagues (Andrewes et al., 2003) reported that decarboxymethyl ligstroside aglycone was responsible for the throat irritation and pungency elicited by some EVOOs. In 2005, Beauchamp *et al.* (Beauchamp et al., 2005) confirmed that the phenolic compound, decarboxymethyl ligstroside aglycone was indeed responsible for the throat irritation elicited by EVOOs post-ingestion. This confirmation was carried out by isolating the compound from various EVOOs and measuring the throat irritation elicited. However, at that stage, there was a possibility that co-elution of a minor component or a mixture of components along with decarboxymethyl ligstroside aglycone may collectively cause the localized throat irritation. Therefore, the authors chemically synthesized decarboxymethyl ligstroside aglycone and dissolved it in non-irritating corn oil. Throat irritation elicited by the synthesized decarboxymethyl ligstroside aglycone was found to be dose-dependent on the concentration of this phenolic in corn oil and mimicked that of EVOO containing this compound naturally. Decarboxymethyl ligstroside aglycone was thus deemed the sole throat irritant in EVOO and was named oleocanthal (*oleo* for olive,

O

The intake of EVOO is often associated with a peppery sting that is localized to the oropharyngeal region in the oral cavity (Figure 3). There is wide inter-individual variation in sensitivity to oleocanthal which can range from a slight irritation in the throat, to an irritation that is strong enough to produce a cough in those highly sensitive. Of particular

O

CHO

CHO

fraction has generated much interest regarding its health promoting properties.

development.

**4. Discovery of oleocanthal** 

*canth* for sting, and *al* for aldehyde) (Beauchamp et al., 2005).

HO

**5. Sensory properties of oleocanthal** 

Fig. 2. Oleocanthal structure

increased life expectancy (Hu, 2003, Visioli et al., 2005, Trichopoulou et al., 2005), reduced risk of developing disorders such as metabolic syndrome (Tortosa et al., 2007, Babio et al., 2008) and have decreased levels of systematic inflammation (Dai et al., 2009, Fragopoulou et al., 2010, Panagiotakos et al., 2009).

The traditional Mediterranean diet is defined as the pattern of eating observed in the olive growing areas of the Mediterranean region, namely Greece and Southern Italy in the 1960s. An integral component of this dietary pattern is the consumption of EVOO (Stark and Madar, 2002, Kok and Kromhout, 2004). EVOO, the pillar of Mediterranean recipes, is commonly incorporated into cooked dishes as well as in salads. Typically, the intake of EVOO ranges from 25 to 50 ml per day in the Mediterranean diet (Corona et al., 2009). Therefore, the apparent health benefits have been partially attributed to the dietary consumption of EVOO by Mediterranean populations. Figure 1 displays the Mediterranean diet pyramid featuring EVOO as a core component of this dietary pattern.

Fig. 1. Food pyramid reflecting the traditional Mediterranean diet. As depicted, EVOO is an integral food component of this diet residing in the consume 'daily' food group.
