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Characterization of Phenolic Compounds, Vitamin E and Fatty Acids from Monovarietal Virgin Olive Oils of “Picholine Marocaine” Cultivar

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Characterization of Phenolic Compounds, Vitamin E and Fatty Acids from Monovarietal Virgin Olive Oils of “Picholine Marocaine” Cultivar molecules Article Characterization of Phenolic Compounds, Vitamin E and Fatty Acids from Monovarietal Virgin Olive Oils of “Picholine marocaine” Cultivar Aziz Bouymajane 1,2, Yassine Oulad El Majdoub 2, Francesco Cacciola 3,* , Marina Russo 2,* , Fabio Salafia 2, Alessandra Trozzi 2, Fouzia Rhazi Filali 1, Paola Dugo 2,4 and Luigi Mondello 2,4,5,6 1 Team of Microbiology and Health, Laboratory of Chemistry-Biology Applied to the Environment, Faculty of Sciences, Moulay Ismail University, Zitoune Meknes BP 11201, Morocco; [email protected] (A.B.); fouzia.fi[email protected] (F.R.F.) 2 Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, 98168 Messina, Italy; [email protected] (Y.O.E.M.); fsalafi[email protected] (F.S.); [email protected] (A.T.); [email protected] (P.D.); [email protected] (L.M.) 3 Department of Biomedical, Dental, Morphological and Functional Imaging Sciences, University of Messina, 98125 Messina, Italy 4 Chromaleont s.r.l., c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, 98168 Messina, Italy 5 Department of Sciences and Technologies for Human and Environment, University Campus Bio-Medico of Rome, 00128 Rome, Italy 6 BeSep s.r.l., c/o Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, 98168 Messina, Italy * Correspondence: [email protected] (F.C.); [email protected] (M.R.); Tel.: +39-090-676-6570 (F.C.); +39-090-676-6567 (M.R.) Academic Editor: Pierluigi Plastina Received: 23 October 2020; Accepted: 16 November 2020; Published: 19 November 2020 Abstract: Olive oil is an important product in the Mediterranean diet, due to its health benefits and sensorial characteristics. Picholine marocaine is the most cultivated variety in Morocco. The present research aims to evaluate the phenolic compounds, vitamin E and fatty acids of commercial Picholine marocaine virgin olive oils (VOOs) from five different North Moroccan provinces (Chefchaouen, Taounate, Errachidia, Beni Mellal and Taza), using HPLC-photodiode array (PDA)/electrospray ionization (ESI)-MS, normal phase (NP)-HPLC/ fluorescence detector (FLD) and GC-flame ionization 1 detector (FID)/MS, respectively. The obtained results showed an average content of 130.0 mg kg− of secoiridoids (oleuropein aglycone, 10-hydroxy-oleuropein aglycone and ligstroside aglycone, 1 oleocanthal and oleacein), 108.1 mg kg− of phenolic alcohols (tyrosol and hydroxytyrosol), 1 1 34.7 mg kg− of phenolic acids (caffeic acid, ferulic acid and elenolic acid), and 8.24 mg kg− of flavonoids (luteolin, luteolin glucoside, apigenin). With regard to vitamin E, α-tocopherol was 1 1 the most abundant vitamin E (57.9 mg kg− ), followed by α-tocotrienol (2.5 mg kg− ), γ-tocopherol 1 1 (4.5 mg kg− ) and β-tocopherol (1.9 mg kg− ), while δ-tocopherol was not detected. Moreover, 14 fatty acids were found and, among them, oleic acid (76.1%), linoleic acid (8.1%) palmitic acid (8.7%) and stearic acid (2.5%) were the major fatty acids detected. Finally, heat map and principal component analysis allowed us to classify the studied provinces in terms of VOO chemical composition: Chefchaouen (tyrosol and hydroxytyrosol), Taounate (oleuropein aglycone), Errachidia (ferulic acid, w-3 and w-6), Beni Mellal (oleocanthal) and Taza (luteolin and oleic acid). Keywords: virgin olive oils; Picholine marocaine; phenolic compounds; vitamin E; fatty acids; HPLC-PDA/ESI-MS; NP-HPLC/FLD; GC-FID/MS Molecules 2020, 25, 5428; doi:10.3390/molecules25225428 www.mdpi.com/journal/molecules Molecules 2020, 25, 5428 2 of 14 1. Introduction In Morocco, olive cultivation represents a crucial socio-economic pillar, contributing up to 5% of agricultural gross domestic product and 15% of Moroccan agricultural foodstuff export [1]. The olive tree representsMolecules 65%2020, 25 (1,045,186, x FOR PEER REVIEW ha) of the tree growing area, of which 37% (384,528 ha)2 of 14 is irrigated, whereas 63% (660,658 ha) non-irrigated. Overall, 65% of olive production is destined for pressing, 25% for canning1. Introduction and 10% for losses and domestic consumption. In 2017, Morocco exports around 76% (70,000 tons)In Morocco, of table olive olive, cultivation 14% (128.00 represents tons) a crucial of olive socio-economic pomace andpillar, 10% contributing (88.00 tons)up to 5% of of olive oil [2]. Moreover,agricultural Moroccan gross olive domestic oil exports product are and mainly 15% of Moroccan intended agricultural for Spain, foodstuff Portugal, export Holland, [1]. The olive Italy, the USA tree represents 65% (1,045,186 ha) of the tree growing area, of which 37% (384,528 ha) is irrigated, and Asia [whereas2]. However, 63% (660,658 there ha) is lacknon-irrigated. of an adequate Overall, 65 database% of olive reflectingproduction theis destined quality for and pressing, compositional peculiarities25% of for olive canning oils. and This 10% could for losses have and negative domestic repercussions consumption. forIn 2017, the commercializationMorocco exports around of Moroccan olive oils due76% (70,000 to non-compliance tons) of table olive, with 14% the (128.00 requirements tons) of olive of pomace the international and 10% (88.00 olive tons) oilof olive council oil [2]. Olive[2]. oil Moreover, extraction Moroccan is carried olive oil out exports using are three mainly di intendedfferent for extraction Spain, Portugal, processes: Holland, (1) Italy, the the traditional USA and Asia [2]. However, there is lack of an adequate database reflecting the quality and discontinuouscompositional press process; peculiarities (2) the of two-phaseolive oils. decanterThis could process; have negative (3) the three-phaserepercussions decanterfor the process. In the traditionalcommercialization discontinuous of Moroccan press olive process, oils due the to olivesnon-compliance are picked, with leavesthe requirements are removed, of the olives are washed, crushed,international kneaded olive oil withcouncil the [2]. warm water (38 ◦C) (paste) and pressed (olive pomace and olive mill wastewater)Olive [ 3oil]. extraction Then, the is carried olive pomaceout using three is vertically different extraction centrifuged processes: or decanted (1) the traditional to obtain the oil. discontinuous press process; (2) the two-phase decanter process; (3) the three-phase decanter process. In the two-phaseIn the traditional decanter discontinuous process, the press water process, naturally the olives found are picked, in the leaves olive are is removed, used to olives produce are olive oil and olive millwashed, waste crushed, (liquid kneaded and with solid th wastes)e warm water after (38 centrifugation. °C) (paste) and pressed In the (olive three-phase pomace and decanter olive process, after beating,mill wastewater) the water [3]. is addedThen, the and olive the pomace centrifugation is vertically centrifuged is processed, or decanted producing to obtain olive the oil. oil, In olive mill wastewatertheand two-phase olive decanter solid mill process, wastes the water (olive naturally cakes) found [3,4]. in Furthermore, the olive is used into Morocco,produce olive the oil extraction and olive mill waste (liquid and solid wastes) after centrifugation. In the three-phase decanter of olive oilprocess, is done after mainly beating, using the water the is two-phase added and the decanter centrifugation process. is processe The maind, producing olive-growing olive oil, regions are locatedolive in mill northern wastewater central and olive Morocco: solid mill Fes-Mekneswastes (olive cakes) (346,000 [3,4]. Furthermore, ha), Marrakech-Safi in Morocco, (215,000the ha), Tanger-Tetouanextraction Al-Hoceima of olive oil is done (163,000 mainly ha),using Orientalthe two-phase (122,000 decanter ha), process. Beni The Mellal-Kenifra main olive-growing (80,000 ha), Rabat-Saléregions-Kenitra are (66,135located in ha), northern Souss-Massa central Morocco: (19,455 Fes-Meknes ha), Drâ (346,000a-Tafilalet ha), (16,000Marrakech-Safi ha), Casablanca-Settat (215,000 ha), Tanger-Tetouan Al-Hoceima (163,000 ha), Oriental (122,000 ha), Beni Mellal-Kenifra (80,000 ha), (15,000 ha),Rabat-Salé-Kenitra and Guelmin-Oued (66,135 ha), noun Souss-Massa (2000 (19,455 ha) [ha),2] (FigureDrâa-Tafilalet1). (16,000 Moreover, ha), Casablanca-Settat within such regions, the provinces(15,000 of Touanate,ha), and Guelmin-Oued Taza, Chefchaouen, noun (2000 Beni ha) [2] Mellal (Figure and 1). ErrachidiaMoreover, within have such a stronger regions, olive-growing the vocation andprovinces occupy of Touanate, productive Taza, Chefchaouen, olive areas Beni of 131.000 Mellal and ha, Errachidia 55.000 ha,have 43.000, a stronger 14.000 olive-growing ha and 3.000 ha, respectivelyvocation [5]. and occupy productive olive areas of 131.000 ha, 55.000 ha, 43.000, 14.000 ha and 3.000 ha, respectively [5]. Figure 1. Political map of Morocco. Figure 1. Political map of Morocco. The olive growing is dominated by Picholine marocaine cultivar (up to 96%), due to its high The oliveadaptability growing in bioclimatic is dominated stages by(plains,Picholine mountainous, marocaine arid cultivarand Saharan (up area), to 96%), organoleptic due to its high adaptability in bioclimatic stages (plains, mountainous, arid and Saharan area), organoleptic characteristics (medium green fruitiness, bitterness and balanced spiciness), the richness of the chemical and aromatic profiles and double purpose (production of olive oil and canned olive). Molecules 2020, 25, 5428 3 of 14 Furthermore,
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