Importance of some minor compounds in olive oil authenticity and quality
Introduction
Well-established health effects and desirable sensory properties of olive oil are the major driving forces for the high economical value of this product. Major components of olive oil are triacylglycerols and this oil also contains various minor components such as chlorophylls, carotenoids, phenolic compounds and squalene (Yan, Oey, van Leeuwen, & van Ruth, 2018).
Minor components of virgin olive oil which does not need to go through refining steps are highly preserved during mechanical extraction (Olmo-García et al., 2019). Minor compounds are not only significant for physicochemical characteristics of the product, but they are also correlated with taste and nutritional value (Olmo-García et al., 2019). In addition, they are important markers for olive oil quality, purity and authenticity (Olmo-García et al., 2018; Tena, Wang, Aparicio-Ruiz, García-González, & Aparicio, 2015). Therefore, the concentrations and types of minor compounds are of great importance for both the consumers and the manufacturers (Olmo-García et al., 2018). The quality and quantity of these metabolites are affected by olive variety, growth conditions of olives, extraction and refining procedures of oil as well as storage conditions (Dais & Hatzakis, 2013).
Besides their health-promoting effects, minor components (volatiles, phenolic compounds, terpenoids, sterols, etc.) are also found to be more successful descriptors of olive oil compared to major metabolites due to the fact that it is hard to mimic minor compounds during preparation of illegal formulations (Dais & Hatzakis, 2013). Importance of minor compound composition has become even more significant since olive fruits have been started to be cultivated outside the Mediterranean zones. Even for the same olive type, differences in olive growth locations are also leading to compositional differences between oils obtained from relatively new areas and the products from traditional olive producer countries (Aparicio, Morales, Aparicio-Ruiz, Tena, & García-González, 2013). As a result, olive oils from new cultivation areas could be out of the limits set by official regulatory agencies mainly based on Mediterranean countries (Uncu, Ozen, & Tokatli, 2019). In addition, some traditional but minor cultivars, even grown in the Mediterranean region could still have chemical compounds out of the described limits (García González, Aparicio, & Aparicio-Ruiz, 2018). Thus, the data of the minor compounds of olive oils have become more valuable for statistical evaluation as a significant part of authentication studies (Dais & Hatzakis, 2013).
As a solution to these emerging problems, new chemical parameters mainly exploiting minor compounds of olive oil have been put into action as quality and/or authenticity indicators (Dais & Hatzakis, 2013). If the official and recently proposed methods are examined, it could be seen that methods that determine quality and adulteration in general are intertwined with each other. Therefore, effect of the various constituents of olive oil on the quality and authenticity are examined together in this review. Fatty acid alkyl esters (FAAEs), diacylglycerols (DAGs), natural color pigments, particularly pyropheophytins (PPPs) as the degradation product of chlorophylls and phenolic compounds are regarded as some of the potential quality and authenticity indicators of olive oil (European Commission, 2013).
Several recent reviews and studies in the literature provide information regarding the current regulations about olive oil as well as their methods of analysis (Bajoub, Bendini, Fernández-Gutiérrez, & Carrasco-Pancorbo, 2018; Conte et al., 2019; Tena et al., 2015). Some novel techniques (Surface-enhanced Raman spectroscopy (SERS), biosensors, microfluidic devices) have also been applied in olive oil authentication (Bremer, Smits, & Haasnoot, 2009; Deng et al., 2018; Du et al., 2019; McIntosh et al., 2016) and in determination of some bioactive compounds of olive oils especially polyphenolic content (Al Mughairy, Al-Lawati, & Suliman, 2019; Camerlingo, Portaccio, Delfino, & Lepore, 2019; Hammami, Kuliček, & Raouafi, 2016; Ramos, Contreras, & Macías, 2020). Some well-known minor compounds such as sterols, stigmastadienes, aliphatic hydrocarbons and phenolic compounds along with major compounds (triacylglycerols, fatty acid contents) which have official limits in regulations were evaluated in detail in the previous reviews (Aparicio, Conte, & Fiebig, 2013; Arvanitoyannis & Vlachos, 2007; Ben-Ayed, Kamoun-Grati, & Rebai, 2013; Boskou, 2008; García González et al., 2018; Montealegre, Alegre, & García-Ruiz, 2010) Olive oil is very rich in terms of phenolic compounds such as hydroxytyrosol, tyrosol and oleuropein. Because of the well-established health effects of these compounds they have been extensively studied and there are several reviews about these compounds (Alu'datt et al., 2017; Boskou, 2015) and literature reviews are even available on certain individual phenolic compounds (Parkinson & Keast, 2014; Wani et al., 2018). However, there is not any comprehensive and critical review in the literature focusing on emerging minor compounds, FAAES, DAGs and pigments, and emphasizing their importance in olive oil studies although many studies in the literature indicated their potential on different quality issues such as detection of different types of adulteration and determining olive grade or storage history. Therefore, it was aimed to review the several minor compounds (FAAEs, color compounds with their derivatives (e.g. PPPs), DAGs with derivatives (e.g. monochloropropanediol esters (MCPDEs) and glycidyl esters (GEs)) that have been studied in recent years in terms of the authenticity and quality of olive oil.
Section snippets
Recent problems regarding authentication of olive oils
Olive oil industry must deal with various authentication and quality problems. Mixing of various edible oils such as sunflower, canola and soybean oils with olive oil is one of the most common type of adulteration problems for olive oil. However, detection of these mixtures is becoming easier and faster. Therefore, fraudsters are constantly introducing new mixtures and causing new problems to oil industry. Despite the progresses in analytical methods, developments may still not be enough to
Application of minor components in quality and authentication studies
Minor components of olive oils have been quite useful in investigation of both quality issues such as monitoring of oxidation as well as the stability, storage history, and also different types of adulteration of olive oil (Dais & Hatzakis, 2013; Uncu & Ozen, 2019). Some of these issues were successfully addressed and included in official regulations as mentioned in the previous parts. Determination of some relatively new parameters (MCPDs, GEs, FAEEs, DAGs, and PPPs) are the emerging
Conclusion and future trends
In this review, several minor compounds of olive oils as pigments (including derivatives such as PPPs), DAGs with derivatives (comprising MCPDEs and GEs), and FAAEs were summarized through their latest applications in the olive oil field. FAAEs could provide detection of mildly refined olive oils in high quality olive oils if the adulterant initially has high FAAE content. DAGs, on the other hand, are effective as freshness indicators for olive oil. MCPDEs and GEs as the derivatives of DAGs
References (151)
- et al.
Detection of refined olive oil adulteration with refined hazelnut oil by employing NMR spectroscopy and multivariate statistical analysis
Talanta
(2010) - et al.
Investigating the impact of metal ions and 3D printed droplet microfluidics chip geometry on the luminol-potassium periodate chemiluminescence system for estimating total phenolic content in olive oil
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
(2019) - et al.
A review of phenolic compounds in oil-bearing plants: Distribution, identification and occurrence of phenolic compounds
Food Chemistry
(2017) - et al.
Decoloration kinetics of chlorophylls and carotenoids in virgin olive oil by autoxidation
Food Research International
(2014) - et al.
Thermal degradation kinetics of lutein, β-carotene and β-cryptoxanthin in virgin olive oils
Journal of Food Composition and Analysis
(2011) - et al.
Soft-deodorization of virgin olive oil: Study of the changes of quality and chemical composition
Food Chemistry
(2017) - et al.
Authenticity of olive oil: Mapping and comparing official methods and promising alternatives
Food Research International
(2013) - et al.
Quantifying binary and ternary mixtures of monovarietal extra virgin olive oils with UV–vis absorption and chemometrics
Sensors and Actuators B: Chemical
(2016) - et al.
Direct GC–(EI) MS determination of fatty acid alkyl esters in olive oils
Talanta
(2014) - et al.
Diacylglycerol isomers in extra virgin olive oil: Effect of different storage conditions
Food Chemistry
(2013)
High-performance liquid chromatographic analysis of chlorophylls, pheophytins and carotenoids in virgin olive oils: Chemometric approach to variety classification
Journal of Chromatography A
Quality assessment and authentication of virgin olive oil by NMR spectroscopy: A critical review
Analytica Chimica Acta
Copper chlorophyll in olive oils: Identification and determination by LIF capillary electrophoresis
Food Control
Ethyl esters versus fermentative organoleptic defects in virgin olive oil
Food Chemistry
A survey of ethanol content in virgin olive oil
Food Control
Putative markers of adulteration of extra virgin olive oil with refined olive oil: Prospects and limitations
Food Research International
Fatty acid ethyl esters (FAEE) in extra virgin olive oil: A case study of a quality parameter
LWT-Food Science and Technology
Fatty acid alkyl esters presence in olive oil vs. organoleptic assessment
Food Chemistry
A naphthoquinone/SAM-mediated biosensor for olive oil polyphenol content
Food Chemistry
Effect of olive storage conditions on Chemlali olive oil quality and the effective role of fatty acids alkyl esters in checking olive oils authenticity
Food Chemistry
Occurrence of 3-MCPD, 2-MCPD and glycidyl esters in extra virgin olive oils, olive oils and oil blends and correlation with identity and quality parameters
Food Control
Classification of Western Greek virgin olive oils according to geographical origin based on chromatographic, spectroscopic, conventional and chemometric analyses
Food Research International
Pigments in extra virgin olive oils produced in different mediterranean countries in 2014: Near UV-vis spectroscopy versus HPLC-DAD
LWT-Food Science and Technology
Four-way multivariate calibration using ultra-fast high-performance liquid chromatography with fluorescence excitation–emission detection. Application to the direct analysis of chlorophylls a and b and pheophytins a and b in olive oils
Chemometrics and Intelligent Laboratory Systems
Alkyl esters content and other quality parameters in oil mill: A response surface methodology study
European Journal of Lipid Science and Technology
Pheophytin α degradation products as useful indices in the quality control of virgin olive oil
Journal of the American Oil Chemists Society
Predicting extra virgin olive oil freshness during storage by fluorescence spectroscopy
Grasas Y Aceites
Does “Best Before” date embody extra-virgin olive oil freshness?
Journal of Agricultural and Food Chemistry
Thermal degradation kinetics of neoxanthin, violaxanthin, and antheraxanthin in virgin olive oils
Journal of Agricultural and Food Chemistry
Thermal degradation kinetics of chlorophyll pigments in virgin olive oils. 1. Compounds of series a
Journal of Agricultural and Food Chemistry
Mathematical model to predict the formation of pyropheophytin a in virgin olive oil during storage
Journal of Agricultural and Food Chemistry
Olive oil authentication
Oxidative stability of virgin olive oil: Evaluation and prediction with an adaptive neuro‐fuzzy inference system (ANFIS)
Journal of the Science of Food and Agriculture
Simultaneous analysis of natural pigments and E-141i in olive oils by liquid chromatography–tandem mass spectrometry
Analytical and Bioanalytical Chemistry
Implementation of physicochemical and sensory analysis in conjunction with multivariate analysis towards assessing olive oil authentication/adulteration
Critical Reviews in Food Science and Nutrition
Simulation of the visible spectra for edible virgin olive oils: Potential uses
Applied Spectroscopy
Extra virgin olive oil stored in different conditions: Focus on diglycerides
Italian Journal of Food Science
Improvement of the fourier transform near infrared method to evaluate extra virgin olive oils by analyzing 1, 2‐diacylglycerols and 1, 3‐diacylglycerols and adding unesterified fatty acids
Lipids
Olive oil authentication: A comparative analysis of regulatory frameworks with especial emphasis on quality and authenticity indices, and recent analytical techniques developed for their assessment. A review
Critical Reviews in Food Science and Nutrition
Ethanol in olive Fruit. Changes during ripening
Journal of Agricultural and Food Chemistry
How ‘ground‐picked’olive fruits affect virgin olive oil ethanol content, ethyl esters and quality
Journal of the Science of Food and Agriculture
An overview of the authentication of olive tree and oil
Comprehensive Reviews in Food Science and Food Safety
Rapid screening of fatty acid alkyl esters in olive oils by time domain reflectometry
Journal of Agricultural and Food Chemistry
Fatty acid methyl and ethyl esters as well as wax esters for evaluating the quality of olive oils
European Food Research and Technology
Determination of pigments in virgin and extra-virgin olive oils: A comparison between two near UV-vis spectroscopic techniques
Foods
Olive oil: Minor constituents and health
Olive and olive oil bioactive constituents
Biosensor immunoassay for traces of hazelnut protein in olive oil
Analytical and Bioanalytical Chemistry
Grade and labeling standards for olive oil, refined-olive oil and olive-pomace oil
Surface-enhanced Raman spectroscopy for monitoring extravirgin olive oil bioactive components
Journal of Chemistry
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