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Oleocanthal Quantification Using 1H NMR Spectroscopy And molecules Article Oleocanthal Quantification Using 1H NMR Spectroscopy and Polyphenols HPLC Analysis of Olive Oil from the Bianchera/Belica Cultivar Martina Starec, Antonella Calabretti, Federico Berti and Cristina Forzato * Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Trieste, via L. Giorgieri 1, 34127 Trieste, Italy; [email protected] (M.S.); [email protected] (A.C.); [email protected] (F.B.) * Correspondence: [email protected] Abstract: The cultivar Bianchera is an autochthonous variety from the eastern part of northern Italy, but it is also cultivated in the Slovenian and Croatian peninsula of Istria where it is named Belica (Slovenia) and Bjelica (Croatia). The properties of oleocanthal, a natural anti-inflammatory ibuprofen-like compound found in commercial monocultivar extra virgin olive oils, were determined by means of both quantitative 1H NMR (qNMR) and HPLC analyses, where qNMR was identified as a rapid and reliable method for determining the oleocanthal content. The total phenolic content (TPC) was determined by means of the Folin–Ciocalteau method and the major phenols present in the olive oils were also quantified by means of HPLC analyses. All these analyses confirmed that the cultivar Bianchera was very rich in polyphenols and satisfied the health claim provided by the EU Commission Regulation on the polyphenols content of olive oils and their beneficial effects on human health. Citation: Starec, M.; Calabretti, A.; Keywords: olive oil; polyphenols; Folin-Ciocalteau; oleocanthal; qNMR; HPLC Berti, F.; Forzato, C. Oleocanthal Quantification Using 1H NMR Spectroscopy and Polyphenols HPLC Analysis of Olive Oil from the Bianchera/Belica Cultivar. Molecules 1. Introduction 2021, 26, 242. https://doi.org/ Extra virgin olive oil (EVOO) is one of the most valuable vegetable oils, part of the 10.3390/molecules26010242 Mediterranean diet and is appreciated for its organoleptic properties, as well as for its nutritional value. Several benefits have been attributed to the consumption of olive oil, Academic Editors: Adele Papetti and such as antioxidant properties, prevention in cardiovascular disease, chemoprevention, Roberto Fabiani lower incidence of neurological disorders and neurodegeneration and protection towards Received: 20 November 2020 inflammatory bowel diseases [1]. Accepted: 28 December 2020 Most of these properties are due to the phenolic compounds present in extra virgin Published: 5 January 2021 olive oil, such as hydroxytyrosol, oleuropein and oleocanthal, which are part of the 2% un- saponifiable fraction. This minor fraction contains several compounds of different classes, Publisher’s Note: MDPI stays neu- such as hydrocarbons (squalene, β-carotene), sterols (β-sitosterol, campesterol), fatty alco- tral with regard to jurisdictional clai- hols, triterpenes (uvaol, erythrodiol, maslinic acid, oleanolic acid), tocopherols, pigments, ms in published maps and institutio- nal affiliations. waxes and polyphenols (oleuropein, hydroxytyrosol, oleocanthal). Different from the other vegetable oils, EVOO is very rich in phenolic compounds since the olive fruit is a reservoir of them. Nevertheless, they are also present in the leaves of the Olea europea tree, as well as in pomace, the waste product of olive oil production. The presence of antioxidant Copyright: © 2021 by the authors. Li- compounds in waste products, such as leaves from pruning and pomace, means that there censee MDPI, Basel, Switzerland. is a great interest in their recovery since natural extracts with antioxidant activity can be This article is an open access article used as additives to enhance the quality and the duration of the product [2]. distributed under the terms and con- The two phenolic alcohols, namely, tyrosol 1 and hydroxytyrosol 2, as well as their ditions of the Creative Commons At- derivatives (Figure1), have received particular attention since they are considered natural tribution (CC BY) license (https:// antioxidants and, in 2011, their beneficial effects were recognised by the EFSA (European creativecommons.org/licenses/by/ Food Safety Authority), which verified the cause and effect relationship between the 4.0/). Molecules 2021, 26, 242. https://doi.org/10.3390/molecules26010242 https://www.mdpi.com/journal/molecules Molecules 2021, 26, x FOR PEER REVIEW 2 of 22 Molecules 2021, 26, 242 Food Safety Authority), which verified the cause and effect relationship2 of between 22 the con- sumption of polyphenols and the prevention of the lipoperoxidation of low density lipo- proteins (LDL). In particular, a daily intake of at least 5 mg of polyphenols (tyrosol, hy- consumption of polyphenols and the prevention of the lipoperoxidation of low density lipoproteinsdroxytyrosol (LDL). and In their particular, derivatives) a daily intakeprovides of at these least 5 beneficial mg of polyphenols effects (EU (tyrosol, Commission Reg- hydroxytyrosolulation 432/2012). and their derivatives) provides these beneficial effects (EU Commission RegulationThe secoiridoid 432/2012). derivatives of tyrosol and hydroxytyrosol, namely, ligstroside 3 and oleuropeinThe secoiridoid 4, are derivativesonly present of tyrosol in the and plant hydroxytyrosol, family Oliaceae namely, and ligstroside they 3containand the elenolic oleuropein 4, are only present in the plant family Oliaceae and they contain the elenolic acid skeleton,acid skeleton, together together with a glucose with mojetya glucose (Figure mojety1)[ 3]. (Figure These compounds 1) [3]. These are responsible compounds are respon- forsible some for of some the organoleptic of the organoleptic properties of properties EVOO, such of as EVOO, bitterness such and pungency.as bitterness and pungency. Figure 1. 1.Chemical Chemical structures structures of phenols of phenols1–4. 1–4. Olive fruit is rich in oleuropein and ligstroside but during the extraction process, due to enzymaticOlive fruit or chemical is rich reactions in oleuropein that can and occur ligstroside during the workingbut during process, the they extraction seem process, due to beenzymatic degraded or first chemical to ligstroside reactions aglicon that5 and can oleuropein occur during aglicon the6 (by working the action process, of they seem βto-glucosidases be degraded present first into the ligstroside skin and in aglicon the olive 5 kernel) and oleuropein and second toaglicon the monoalde- 6 (by the action of β- hydicglucosidases forms p-HPEA-EA present in (p -hydroxyphenylthe skin and in ethyl the alcohololive kernel) elenolic and acid second aldehyde) to7 theand monoaldehydic 3,4-DHPEA-EA (3,4-dihydroxyphenyl ethyl alcohol elenolic acid aldehyde) 8 as differ- entforms diastereoisomers p-HPEA-EA due (p to-hydroxyphenyl the ring opening andethyl ring alcohol closure elenolic of the hemiacetal acid aldehyde) group 7 and 3,4- (FigureDHPEA-EA2) . The open(3,4-dihydroxyphenyl forms of the hemiacetals ethyl5 and alcohol6 were recently elenolic determined acid aldehyde) and named 8 as different di- oleokoronalastereoisomers11 and due oleomissional to the ring12 opening, respectively and [ 4ring] (Figure closure3). To of obtain the hemiacetal the two di- group (Figure aldehydic2). The open forms, forms namely, of oleocanthal the hemiacetals9 and oleacein 5 and10 ,6 hydrolysis were recently of the methyl determined ester and named and a decarboxylation reaction have to occur. These two steps could be reached either enzymaticallyoleokoronal or11 chemically and oleomissional due to the acidic 12, respectively aqueous conditions [4] (Figure of the extraction. 3). To obtain To our the two dialde- knowledge,hydic forms, no specificnamely, enzymes oleocanthal have been 9 and isolated oleacein till now 10 [5,]. hydrolysis of the methyl ester and a decarboxylationThe content of reaction phenols in have EVOO to occur. depends These on several two steps factors, could such asbe thereached type of either enzymat- cultivar,ically or climate, chemically ripeness due of the to olivesthe acidic at harvesting, aqueous storage conditions and the extractionof the extraction. pro- To our cess. The phenolic profile of cultivar Koroneiki from Greece was recently determined by knowledge, no specific enzymes have been isolated till now [5]. Magiatis et al., who considered different factors, such as harvest time, malaxation temper- ature andThe malaxationcontent of time, phenols where in different EVOO trends depends were observedon several [6]. factors, From the such study as of the type of cul- thetivar, malaxation climate, process, ripeness the authorsof the olives suggested at aharvesting, biosynthetic stor pathwayage forand oleocanthal the extraction and process. The oleaceinphenolic through profile the of formation cultivar of Koroneiki oleokoronal andfrom oleomissional Greece was and recently a subsequent determined step of by Magiatis removalet al., who of the considered methyl group different that is catalysed factors, by such a methylesterase. as harvest time, Furthermore, malaxation the same temperature and authors determined that these transformations are strongly dependent on the variety of olivemalaxation oil. time, where different trends were observed [6]. From the study of the malax- ation process, the authors suggested a biosynthetic pathway for oleocanthal and oleacein through the formation of oleokoronal and oleomissional and a subsequent step of removal of the methyl group that is catalysed by a methylesterase. Furthermore, the same authors determined that these transformations are strongly dependent on
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