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Oleocanthal (P-HPEA-EDA) (Pubchem CID: Virgin Olive Oil, Showing High Variability That Was Significantly Due to the Cultivar

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Oleocanthal (P-HPEA-EDA) (Pubchem CID: Virgin Olive Oil, Showing High Variability That Was Significantly Due to the Cultivar Food Chemistry 266 (2018) 192–199 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Cultivar influence on variability in olive oil phenolic profiles determined T through an extensive germplasm survey H. Mihoa, C.M. Díeza, A. Mena-Bravob,c,d, V. Sánchez de Medinab, J. Morala,g, E. Melliouf, ⁎ P. Magiatisf, L. Ralloa, D. Barrancoa, F. Priego-Capoteb,c,d, a Department of Agronomy, Campus of Rabanales, University of Cordoba, Spain b Department of Analytical Chemistry, Campus of Rabanales, University of Cordoba, Spain c Agroalimentary Excellence Campus (ceiA3), Campus of Rabanales, University of Cordoba, Spain d Maimonides Institute of Biomedical Research (IMIBIC), Reina Sofia University Hospital, Spain f Laboratory of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, University of Athens, Greece g Plant Pathology Department, University of California Davis, Davis, USA ARTICLE INFO ABSTRACT Chemical compounds studied in this article: Despite the evident influence of the cultivar on olive oil composition, few studies have been devoted to exploring Hydroxytyrosol (PubChem CID: 82755) the variability of phenols in a representative number of monovarietal olive oils. In this study, oil samples from 80 Oleacein (3,4-DHPEA-EDA) (PubChem CID: cultivars selected for their impact on worldwide oil production were analyzed to compare their phenolic com- 18684078) position by using a method based on LC–MS/MS. Secoiridoid derivatives were the most concentrated phenols in Oleocanthal (p-HPEA-EDA) (PubChem CID: virgin olive oil, showing high variability that was significantly due to the cultivar. Multivariate analysis allowed 16681728) discrimination between four groups of cultivars through their phenolic profiles: (i) richer in aglycon isomers of Oleuropein aglycon (3,4-DHPEA-EA) fl (PubChem CID: 124202093) oleuropein and ligstroside; (ii) richer in oleocanthal and oleacein; (iii) richer in avonoids; and (iv) oils with Luteolin (PubChem CID: 5280445) balanced but reduced phenolic concentrations. Additionally, correlation analysis showed no linkage among Apigenin (PubChem CID: 5280443) aglycon isomers and oleocanthal/oleacein, which can be explained by the enzymatic pathways involved in the Keywords: metabolism of both oleuropein and ligstroside. Phenolic compounds Cultivar Germplasm Oleocanthal Oleacein Oleuropein aglycon Ligstroside aglycon LC-MS/MS 1. Introduction (Piroddi et al., 2017). VOO composition is characterized by saponifiable and unsaponifiable fractions. The saponifiable fraction represents ap- The olive tree, Olea europaea subsp. europaea var. sativa, was likely proximately 98% of the olive components and includes triglycerides, domesticated approximately 6000 years ago in the Middle East from its fatty acids, phospholipids, waxes and sterol esters. The unsaponifiable wild ancestor Olea europaea subsp. europaea var. sylvestris,(Besnard fraction, approximately 2% of the total composition, encompasses a et al., 2013). Currently, more than 11 million hectares of olives are complex set of minor compounds (approximately 230 compounds) grown in 47 countries worldwide (International Olive Council, 2015). pertaining to various chemical families including aliphatic and tri- However, olive growing is still based on a vast number of traditional terpenic alcohols, sterols, hydrocarbons, phenols, tocopherols, esters, olive cultivars, with complex genetic relationships among them (Diez pigments, and volatile components such as aldehydes, ketones and al- et al., 2015). cohols (Servili et al., 2013). The preservation of this composition is Virgin olive oil (VOO) is demonstrated to be endowed with healthy guaranteed by the extraction process performed using physical methods properties, thanks to its monounsaturated fatty acids profile and a at relatively low temperatures (approximately 28 °C) and without the plethora of multiple minor components with biological properties addition of chemical solvents. ⁎ Corresponding author at: Department of Analytical Chemistry, Campus of Rabanales, University of Cordoba, Spain. E-mail address: [email protected] (F. Priego-Capote). https://doi.org/10.1016/j.foodchem.2018.06.002 Received 8 February 2018; Received in revised form 25 May 2018; Accepted 3 June 2018 Available online 04 June 2018 0308-8146/ © 2018 Elsevier Ltd. All rights reserved. H. Miho et al. Food Chemistry 266 (2018) 192–199 Among the minor components of VOO, phenols are worthy of at- genotype on the VOO phenolic profiles. tention due to their (i) health properties (Piroddi et al., 2017); (ii) as- sociation with organoleptic attributes such as oil pungency and bitter- 2. Material and methods ness (Bendini et al., 2007); (iii) contribution to VOO shelf-life (Silva, Pinto, Carrola, & Paiva-Martins, 2010); (iv) uniqueness, supported by 2.1. Experimental location and vegetal material the fact that some families are exclusive of the Oleaceae family and few other dicotyledonous families (Carranco, Farrés-Cebrián, Saurina, & Vegetal material was collected from the World Olive Germplasm Núñez, 2018; Ryan, Antolovich, Prenzler, Robards, & Lavee, 2002); Bank of Cordoba (WOGB) (CAP-UCO-IFAPA), specifically in the col- Servili et al., 2016); and (v) high concentration in VOO (Servili et al., lection located at the University of Cordoba (Cordoba, Spain, 2016). Given the great variability of phenolic families, the role of se- 37°55′56.5″ N, 4°43′13.3″ W and 173 m a.s.L.). The olive trees were coiridoids, conjugated forms of hydroxytyrosol and tyrosol, is notable. planted in 2011 in a North-South orientation with 7 m between rows − This group of compounds is the most concentrated in olive oil and is and 6 m between trees (238 trees ha 1). This collection includes 368 widely studied due to evidence of its healthy properties (Piroddi et al., olive cultivars from 22 countries, which were identified and authenti- 2017). The group includes oleuropein and ligstroside aglycon isomers cated by morphological and molecular methods, so all them are true to and the decarboxymethylated dialdehyde forms of oleuropein and lig- type (Trujillo, Ojeda, Urdiroz, & Potter, 2014). stroside aglycons, better known as oleacein (3,4-DHPEA-EDA) and The climate of the area where the WOGB is located is typically oleocanthal (p-HPEA-EDA), respectively. Beauchamp and colleagues Mediterranean; the average annual precipitation from 2001 to 2016 reported the natural non-steroidal anti-inflammatory activity of oleo- was 635.6 mm, with a summer drought with < 30 mm of precipitation canthal due to its ibuprofen-like cyclooxygenase (COX-1 and COX-2) from June to September. The precipitation in 2014 and 2015 was 635.3 inhibiting capacity (Beauchamp et al., 2005). Oleacein has also shown and 770 mm, respectively. The average potential evapotranspiration antioxidant activity similar to oleocanthal (Czerwińska, Kiss, & (ETP) from 2001 to 2016 was 1261.9 mm, while the average annual, Naruszewicz, 2014). It appears that the healthy properties of VOO maximum and minimum temperatures for the same period were 18.2, phenols are attributed individually and not to the total phenolic content 47.2, and 0.0 °C, respectively (Villalobos & Testi, 2017). The collection (Agrawal et al., 2017; Yakhlef et al., 2018). area is characterized by vertisol soil with a texture of 41% sand, 6% silt, There is increasing social interest in VOO as a functional food; for and 53% clay. The soil was approximately 40 cm deep, with 0.6% or- instance, consumers are willing to pay up to 6.02 €/L more for VOO ganic matter content. The collection was irrigated from May to Sep- labelled with functional health claims compared to the unlabeled pro- tember, applying 100 m3 per ha per week (2000 m3 of water per year) duct (Casini, Contini, Marinelli, Romano, & Scozzafava, 2014). Nu- using drip irrigation. Foliar fertilization (2% potassium nitrate) was merous studies supporting the health properties of olive oil have re- applied four times per year during November (after harvesting), March, cently pushed the European Food Safety Authority (EFSA) to approve May and September. several health claims on the commercial label of VOOs that meet spe- A set of 80 olive cultivars were selected during the 2015–2016 crop cific quality requirements. The claim ‘‘olive oil phenols contribute to season according to their importance for the worldwide olive oil pro- the protection of blood lipids from oxidative stress’’ can be included on duction, their geographical origin, and fruit availability (Table 1). We the label when the VOO contains at least 5 mg as the sum of hydro- also studied 25 same cultivars during two consecutive seasons, xytyrosol and its derivatives (e.g., oleuropein complex and tyrosol) per 2014–2015 and 2015–2016, to estimate the reproducibility of the re- 20 g of olive oil (EFSA, 2011). sults. Fruit were independently collected from two olive trees per cul- As mentioned elsewhere, phenols also contribute to the organoleptic tivar, and the VOO was extracted in each case. Therefore, each cultivar properties of VOO (Angerosa et al., 2004). The bitter taste is particu- provided two independent biological samples yielding a total number of larly related to the aglycon forms (Bendini et al., 2007), whereas the 160 samples (80 cultivars × 2 trees = 160 samples). presence of oleocanthal and oleacein has been linked to the pungency of VOO, which might be described as biting tactile sensations, which are 2.2. Sampling and VOO extraction characteristic of some VOOs (Barbieri, Bendini,
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