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Olive oil is considered one of the most valuable vegetable oils and is highly appreciated by consumers for its specific and distinguishable taste and aroma, as well as its nutritional value. Sterols and triterpene diols are important carriers of bioactive properties of olive oil and are responsible for some of the beneficial effects of its consumption on human health, such as lowering serum LDL-cholesterol levels and significantly reducing the risk of cardiovascular diseases. The concentration of total sterols and the proportions of particular sterols and triterpene diols are among the parameters used to verify and prove the authenticity of olive oil in accordance with the EU and other countries’ regulations. Finally, their composition has been shown to have high discrimination potential for ensuring traceability with respect to variety, geographical origin, harvest date, and other factors. For these reasons, the research on sterols and triterpene diols in olive oil is an ever-growing field of scientific interest with great practical importance. This review focuses on all the important aspects of sterols and triterpene diols in olive oil, from their chemical structure, biosynthesis, occurrence and role in plants, health benefits, and their use in official controls of olive oil purity and authenticity, to a conclusive survey on the recent findings about the effects of different factors of influence on their content and composition, with a detailed comparative analysis of studies that investigated the effects of the two most important factors, variety and ripening degree.

With the aim to investigate the influence of post-harvest olive fruit storage temperatures on virgin olive oil production parameters, composition and quality, Istarska bjelica (IB) and Rosinjola (RO) fruits were stored for seven days at room temperature (RT), +4 &deg, C and &minus, 20 &deg, C prior to oil production. Lower temperatures delayed post-harvest maturation of IB fruits. Theoretical oil content did not change depending on the storage temperature, while the highest oil yield and extractability index were obtained after storage at RT. Chlorophylls decreased in IB-RT and in IB-20. A decrease in the sensory quality of oils was detected after fruit storage at RT and &minus, C, while the refrigeration temperature of +4 &deg, C preserved it. Regarding the content of fatty acid ethyl esters, an increase was observed in IB-RT oils. Storage at RT increased the content of waxes, while the lower temperatures partially suppressed this phenomenon. In oils of both cultivars, storage at +4 &deg, C preserved the concentration of most phenolic compounds at a level more similar to that of the fresh oil when compared to the other two treatments. In the production conditions, when prolonged fruit storage is necessary, refrigeration seems to be the most suitable option.

The interactive effects of ripening degree, malaxation duration and temperature on Oblica cv. (Olea europaea L.) virgin olive oil phenols, volatiles, and sensory quality were investigated. Olives were picked at three ripening degrees with International Olive Council indices of 0.68, 2.48 and 4.10, and processed by malaxation at 22 and 30 °C, and at both temperatures for 30 and 60 min. Ripening exhibited the strongest effect, and malaxation duration the weakest. Phenols were generally found to decrease during ripening; however 3,4-DHPEA-EDA and p-HPEA-EDA increased. Similar behaviour was observed for (E)-2-hexenal. Higher malaxation temperature induced an increase in particular important phenols and C6 alcohols, while C6 aldehydes mostly decreased. Interactions between the factors were established, mostly between ripening degree and malaxation temperature: the effect of the latter was most pronounced for ripe olives, especially for 3,4-DHPEA-EDA, p-HPEA-EDA and C6 volatiles. Sensory attributes were generally in agreement with the chemical composition.

Despite having an interesting native olive gene pool and a rapidly emerging olive oil industry, monovarietal extra virgin olive oils (EVOO) from Croatia are relatively unexplored. To investigate the inter-varietal diversity of typical volatile and phenolic profiles of Croatian EVOO, 93 samples from six olive (Olea europaea L.) varieties were subjected to gas chromatography-ion trap mass spectrometry (GC-IT-MS) and ultra-performance liquid chromatography with diode array detection (UPLC-DAD), respectively. Quantitative descriptive sensory analysis was also performed. Analysis of variance extracted many relevant exclusive or partial discriminators between monovarietal EVOOs among the identified volatile compounds and phenols. Successful differentiation model with a 100% correct classification was built by linear discriminant analysis, while the most typical volatiles for each monovarietal EVOO were confirmed by partial least squares discriminant analysis. Diverse typical sensory attributes among the EVOOs were tentatively ascribed to the variations in the composition of volatiles and phenols. It was proven that the approach that comprises GC-IT-MS and UPLC-DAD analysis may provide additional objective information about varietal origin and typicity which successfully complement those obtained by sensory analysis. The approach was characterized as universal in nature, with a significant potential to contribute in strengthening the varietal identities and position on the market of monovarietal and Protected Denomination of Origin (PDO) EVOO.

The aim of this study was to characterize monovarietal olive oils obtained from two less known autochthonous cultivars (Bova and Buža puntoža) on the basis of sterols, triterpene dialcohols and fatty acids profile for the first time, and three monovarietal olive oils obtained from the most widespread autochthonous cultivars (Buža, Istarska bjelica and Rosinjola) grown in Istria, Croatia. β-sitosterol, Δ-5-avenasterol and campesterol were the most abundant sterols in all samples. Campesterol, β-sitosterol and Δ-5-avenasterol most significantly differentiated investigated oils. Bova oil had the highest amount of total sterols (2964 ± 458 mg/kg). Istarska bjelica oil had a peculiar sterol composition with exceptionally low β-sitosterol (67%), high Δ-5-avenasterol (27%) and the highest triterpene dialcohols percentages. Rosinjola and Istarska bjelica oils had the highest monounsaturated fatty acids level, Buža oil had the highest polyunsaturated fatty acids level, while Bova oil showed the highest level of saturated fatty acids. Tested oils obtained from the most abundant cultivars fulfilled all the demands of the current EU regulation required for virgin olive oil regarding sterols, triterpene dialcohols and fatty acids, but Bova and Buža puntoža oil slightly exceeded the upper limit for linolenic acid. Since cultivar is the source of natural variation of sterols, triterpene dialcohols and fatty acids in virgin olive oils, the knowledge about the content of these particular compounds in different monovarietal oils from autochthonous cultivars is important to determine possible disagreements with the demands of the current legislation required for virgin olive oils, in order to anticipate possible false results indicating adulteration.

To investigate if the anecdotal varietal typicity concepts for two monovarietal virgin olive oils (VOO) can be scientifically supported and explained, VOO samples were sorted according to typicity grade and related to sensory and compositional data for volatiles and phenols. Clear inter-varietal, as well as intra-varietal boundaries between more and less typical samples were established by univariate and multivariate statistics. A variety-typical complex odor was related to a complex VOO volatile composition with relatively high amounts of lipoxygenase-derived compounds, accompanied by hydrocarbons, terpenes, and benzenoids. A simpler odor, described mostly as green and typical for the other monovarietal VOO, coincided with the lower amounts of the same volatiles. The intensity of bitterness and pungency was mostly in correlation with the amount of major phenols. Two monovarietal VOOs were clearly distinguished with respect to their variety-typical expression of pungency: the one described as gradually increasing was tentatively related to pinoresinol, while the other, described as immediately strong and burning, was assumed to originate mainly from p-HPEA-EDA. Intra-varietal typicity grades correlated with hedonic liking, as well as with general VOO positive sensory attributes related to key volatiles and phenols.

Despite their importance as bioactive compounds and authentication parameters in olive oil, the response of policosanol aliphatic alcohols to even the most influential sources of variability is practically unknown. To investigate policosanol variation in olive oil as a result of variety, ripening, and oil storage temperature, 36 samples were subjected to gas chromatographic (GC-FID) and mass spectrometric (GC-MS) analysis, and results were processed by univariate (ANOVA) and multivariate (SLDA) statistics. The concentration (mg/100 g) and relative amount (%) of pentacosanol accounted for the most variation due to variety. The largest influence of ripening was observed for pentacosanol (%) and docosanol (%). Docosanol, tricosanol, and tetracosanol amounts mostly increased during ripening, whereas those of pentacosanol, hexacosanol, heptacosanol, and octacosanol decreased in Črna and Rosinjola oils, whereas Buža showed different patterns in some cases. Variations as a result of storage were lower and inconsistent. Results suggest that the investigated olive oils retained the bulk of their health beneficial features of policosanol origin throughout shelf-life. Relatively successful differentiation of oils achieved by multivariate models pointed to the potential use of policosanol alcohols as chemical indicators of varietal origin which are independent on ripening degree, and vice versa, applicable both for fresh and stored oils.

Sterols and triterpene diols in olive oil as indicators of variety and degree of ripening derived from three olive varieties and produced at three different harvesting periods were studied. In order to test the stability of the proposed indicators, oils obtained were stored for 12 months at three different temperatures. Thirty-six samples in total were subjected to GC analysis and results were processed by multivariate chemometric methods (MANOVA, PCA, and SLDA). Campesterol, β-sitosterol, Δ(7)-campesterol/Δ(5,24)-stigmastadienol, clerosterol, uvaol, and campestanol/Δ(7)-avenasterol were established as the indicators of variety of fresh oils, while when stored oils were included in the model, the final three compounds were substituted by 24-methylene-cholesterol/stigmasterol. The most important variables for differentiating fresh oils according to degree of ripening were Δ(7)-campesterol/β-sitosterol, uvaol/stigmasterol, clerosterol/Δ(5)-avenasterol and sitostanol/uvaol, while stored oils were differentiated by campestanol/stigmasterol, erythrodiol, stigmasterol/Δ(7)-campesterol, Δ(5)-avenasterol, 24-methylene-cholesterol/β-sitosterol and 24-methylene-cholesterol. Results demonstrated that sterols and triterpene diols can be used as indicators of variety and degree of ripening among virgin olive oils.

To investigate the variability of 4-monomethylsterols and 4, 4′-dimethylsterols in olive oil as a result of variety, ripening, and storage temperature, 36 samples were subjected to gas chromatography with flame ionization detection (GC-FID) and with mass spectrometric detection (GC-MS), and results were processed by univariate and multivariate statistics. Relative amounts (percent) of β-amyrin, cycloartenol, and 24-methylenecycloartanol accounted for the most variation due to variety, while citrostadienol (percent) and 24-methylenecycloartanol (milligrams per 100 g) were strongly affected by ripening. Multivariate statistics differentiated olive oils regardless of storage conditions, which implied the possibility to use 4-monomethyl- and 4, 4′-dimethylsterols as indicators of variety and ripening degree for fresh and stored oils. Absolute changes in 4-monomethyl- and 4, 4′-dimethylsterols after storage were of a much smaller magnitude, meaning the investigated olive oils essentially retained health-beneficial features that derive from these compounds. Relative changes caused by storage were specific for each storage temperature and were useful in discriminating oils by linear discriminant analysis.