Olive Oil Research Articles

Protective effects of olive oil antioxidant phenols on mercury-induced phosphatidylserine externalization in erythrocyte membrane: Insights into scramblase and flippase activity

In several physiopathological processes, phosphatidylserine (PS), normally sequestered to the inner leaflet of the plasma membrane, becomes exposed to the cell surface. In erythrocytes (RBC), PS externalization is a crucial event for the removal of aged/damaged cells but can also be associated with increased prothrombotic activity. Structurally related olive oil antioxidants, including hydroxytyrosol (HT), are able to significantly reduce the percentage of PS-exposing RBC, when cells are exposed to toxic compounds such as the heavy metal mercury (Hg). The aim of the present study was to identify the molecular mechanisms underlying the protective effect, with a focus on two different phospholipid translocases, the ATP-dependent flippase ATP11C and the calcium-dependent scramblase PLSCR1, which are responsible for PS internalization and exposure, respectively. In addition to HT, its monophenol analogue, tyrosol, and its in vivo metabolite, homovanillic alcohol, were also tested. Our investigation revealed that exposure of human intact RBC to HgCl2 induced a decrease in flippase activity and an increase in scramblase activity, and that all the selected phenols restored the control activity, regardless of their different scavenging properties. Interestingly, all phenols restored the ATP level of control cells, which were significantly reduced by HgCl2 treatment. Conversely, no variation in intracellular calcium was observed under our experimental conditions. Additionally, all phenols restored the glutathione levels, significantly reduced in the presence of HgCl2. In line with the data on the enzymatic activity, Western blotting analysis indicated changes in the membrane expression of the two enzymes, alterations prevented by antioxidant pre-treatment. Finally, molecular docking analysis suggests that the tested antioxidants may be able to directly interact with ATP11C. Our findings provide an experimental basis for the use of olive oil bioactive compounds in nutritional/nutraceutical strategies for the prevention of Hg-related toxicity, particularly in relation to the cardiovascular tissues.

Qualitative Identification and Adulteration Quantification of Extra Virgin Olive Oil Based on Raman Spectroscopy Combined with Multi-task Deep Learning Model

Qualitative Identification and Adulteration Quantification of Extra Virgin Olive Oil Based on Raman Spectroscopy Combined with Multi-task Deep Learning Model

The Possibility of Using Oil Pomace as a Substitute for Walnuts (Juglans regia L.) in Muesli Bar Technology

The utilization of food industry waste to create innovative, high-quality products with reduced environmental impact is a growing trend in food technology. Walnut oil pomace, a byproduct of walnut oil production, is rich in nutrients and bioactive compounds, making it an excellent candidate for reuse in muesli bars as a replacement for walnuts. The aim of the study was to evaluate the possibility of replacing walnuts with oil pomace in muesli bar recipes and to assess whether the resulting product meets quality standards. Ground expeller walnut oil pomaces and aqueous extract were tested, with a bar containing ground walnuts serving as the reference sample. The bars were evaluated for sensory, physicochemical, and antioxidant properties, and their nutritional values were assessed. Results showed that the pomace-enriched bars exhibited satisfactory physicochemical properties, with texture, color, and safety (as measured by water activity and pH) comparable to the control bars. Sensory evaluations classified all bars as acceptable, with no significant differences in nutritional value. The study concludes that walnut pomace holds promise as a sustainable ingredient in food technology, potentially expanding product diversity while reducing environmental impact. This concept aligns with promoting sustainable practices in food manufacturing.

Study of the oxidative stability via Oxitest and Rancimat of phenolic-rich olive oils obtained by a sequential process of dehydration, expeller and supercritical CO2 extractions

The oxidative stability of olive oils extracted by different methods, i.e. conventional 2-phase extraction (cOO), and sequential extraction by expeller press (eOO) and supercritical CO2 (SCOO), was determined by using two accelerated oxidation methods, Oxitest and Rancimat, in the temperature range 90–160°C. The kinetic analyses carried out provided Arrhenius activation energies, enthalpies, entropies and Gibb’s free energies of activation, temperature coefficients, Q10 factors, and the oxidative stability indexes at 20°C (OSI20) for the different oils. A good correlation between the two techniques was obtained (r2 = 0.996). Oxitest showed, however, shorter induction times and less sample quantity (1 g vs. 3 g in Rancimat) requirements, suggesting that it could be a good and faster alternative to Rancimat for the evaluation of the oil oxidative stability. cOO showed OSI20 values of 38.5 and 42.5 months, by the Rancimat and Oxitest methods, respectively. Furthermore, eOO and SCOO showed OSI20 values of 43.3 and 138.6 months by Rancimat and 67 and 142 months by the Oxitest method, respectively. The strong correlation found between the phenolic content of the oils and their OSI20 values confirms that a higher oil phenolic content would improve the oxidative stability of the oils.

Energy, Macronutrients and Micronutrients Intake Among Pregnant Women in Lebanon: Findings from the Updated Lebanese National Food Consumption Survey (LEBANON-FCS)

Background: Pregnancy is a crucial period for maternal and fetal health, and in Lebanon, where cultural and economic factors influence dietary practices, there is an urgent need to evaluate the food consumption patterns and diet quality of pregnant women. Aim: To evaluate the food consumption patterns, energy intake, as well as macro- and micro-nutrient intake among a nationally representative sample of Lebanese pregnant women aged 18–49 years old. Methods: A cross-sectional study was carried out from March to October 2023, involving 500 pregnant women from all eight Lebanese governorates. Sociodemographic and medical information was gathered, food consumption was evaluated using a validated Food Frequency Questionnaire (FFQ) and three 24-h recall, and anthropometric measurements were recorded. Results: The current population did not meet the USDA healthy pattern recommendations for whole grain, seafood, dairy, nuts, seeds and soy products consumption but exceeded the guidelines for vegetables, meats, poultry, eggs, oils, and refined grains. According to Mediterranean diet guidelines, the sample fell short in recommended intakes for fruits, olives/nuts/seeds, eggs, and olive oil, while surpassing the recommended levels for potatoes, legumes, pulses, sweets, red meat, processed meat, and fish and seafood. None of the participants met the energy requirements for their trimester and age group. In terms of macronutrient intake, the requirements for protein, unsaturated fats, and fiber were not met, while intakes of fats and sugars were exceeded. Regarding micronutrients, the recommended levels were not fully achieved, with particularly low intakes of vitamin D and iodine, as well as inadequate adherence to recommendations for iron, calcium, vitamin A, vitamin E, zinc, and choline. Additionally, a third of the participants did not meet the recommended intakes for folate and vitamin B12. Conclusions: The findings reveal significant dietary inadequacies among the current population, with participants failing to meet essential recommendations for whole grains and key food groups, alongside insufficient energy intake for their trimesters and age groups. Critical micronutrient deficiencies, particularly in vitamin D, iodine, and B vitamins, highlight the urgent need for targeted nutritional interventions and public health initiatives to improve dietary practices among pregnant women in Lebanon.

Food Functional Powders with Redox Capacity and Antioxidant Properties Obtained from Food Losses and Waste of Olive Oil Industry

Food powders were produced from olive pomace (Coratina, COP, and Arbequina, AOP) using freeze-drying with maltodextrin (MD) and native corn starch (NS) as wall materials in varying proportions. Optical microscopy revealed that OP was partially recovered by MD and NS. COP presented a total polyphenol content (TPC) of 53.8 g GAE/kg; meanwhile, AOP was 31.9 g GAE/kg. Accordingly, powders obtained from COP presented higher TPC than those from AOP. NS allowed obtaining powders with higher TPC and antioxidant activity. The greatest encapsulation efficiency was achieved by using 15% MD, achieving values of 94.9% for COP and 89.4% for AOP. Hydroxytyrosol was identified as the predominant polyphenol in the powders. It was demonstrated that powders could be added to food formulations and withstand cooking temperatures up to 220 °C without suffering a significant thermal degradation. Chemometric analysis of MIR and NIR spectra evidenced that they are analytical techniques capable of differentiating OP varieties and wall material types, besides variations in OP concentration. Results derived from this study demonstrated that it is feasible to give added value to olive pomace, obtaining powders rich in antioxidants to be used as ingredients of functional foods.

Planting System and Cultivar Influence Olive Key-Pests Infestation in an Olive-Growing Vocated Area

Traditional and intensive planting systems have paved the way for the phenomenon of intensification, with the super high-density (SHD) system being the most prominent. This system has demonstrated high levels of profitability due to both the reduction in production costs achieved through complete mechanization and a significant increase in olive oil production per hectare, stemming from the more efficient utilization of resources such as light, water, and nutrients. The aim of this study was to evaluate, in a vocated olive-growing area, the phytosanitary status of a SHD olive orchard compared to a traditional one (TRD). The research focused on six key olive pests, considering the interaction between planting systems and eight cultivars in a semi-arid environment. The comparative analysis of pest infestations across the two planting systems revealed significant and complex patterns in pest population distribution and intensity. Overall, the planting system appeared to be the main factor influencing pest dynamics. The SHD olive orchard exhibited the highest infestation levels of Otiorhynchus cribricollis, Palpita unionalis, and Bactrocera oleae. Conversely, in the TRD system, the highest infestation levels of Saissetia oleae, Euphyllura olivina, and Prays oleae were observed. Moreover, the study highlighted a less pronounced effect of cultivars on the prevalence of all monitored key pests. These findings underscore the potential for developing more sustainable and effective pest management strategies tailored to specific planting systems. Furthermore, the results contribute to advancing eco-friendly control approaches and improving pest infestation management practices. Additional research will be necessary to deepen the understanding of these key pests and their interactions within different olive-growing systems.

In-situ Synthesis of Nickel Nanoparticles in Olive Oil and Study of Their Tribological Properties as Vegetable Oil Additives

In-situ Synthesis of Nickel Nanoparticles in Olive Oil and Study of Their Tribological Properties as Vegetable Oil Additives

Exploring the additive compatibility and tribological behavior of regular and high oleic soybean oil

As the demand for biobased lubricating oils continues to rise, there is a growing focus on exploring diverse oil types. Particularly noteworthy is the surge in demand for high oleic oils, which offer enhanced stability, and a richer oleic acid content compared to their regular oil counterparts. However, the performance of high oleic soybean oil (HOSO) with additives compared to regular soybean oil (RSO), remains unclear. This study is focused on revealing the compatibility of both regular soybean oil (RSO) and high oleic soybean oil (HOSO) with select antiwear and antioxidant additives, specifically zinc dialkyl dithiophosphate (ZDDP), and zinc dialkyl dithiocarbamate (ZDDC) combined with antimony dialkyldithiocarbamate (ADDC), along with a comparative performance analysis of these additives. Reciprocating friction, wear, and electrical contact resistance-based analyses were conducted to evaluate additive compatibility and wear mechanisms at room temperature lubrication conditions. Interestingly, it was observed that for the select additives, the compatibility with regular soybean oil (RSO) was better than that of high oleic soybean oil (HOSO). RSO with additives showed around 28% reduction of wear volume whereas, it was only 8% for HOSO with additives. Additional physiochemical property analyses were conducted on the lubricants to correlate the observed tribological behavior. The worn-out surfaces of the test samples were characterized thoroughly to reveal the dominant wear mechanisms.

Novel PCR-Based Technology for the Detection of Sunflower in Edible and Used Cooking Oils

Reliable detection of sunflower (Helianthus annuus) in edible and used cooking oil (UCO) is crucial for the sustainable production of food and biodiesel. In this study, a variety of sunflower oils (crude, cold pressed, extra virgin, refined, and UCO) were examined using different methods of DNA extraction and PCR amplification to develop an efficient technology for the identification of sunflower in oils. DNA extraction kits such as NucleoSpin Food, DNeasy mericon Food, and Olive Oil DNA Isolation as well as modified CTAB method were found to be able to isolate amplifiable genomic DNA from highly processed oils. Novel uniplex, double, and nested PCR systems targeting the sunflower-specific helianthinin gene were developed for efficient identification of sunflower. New sunflower DNA markers were revealed by uniplex PCRs. The combination of modified CTAB and nested PCR was demonstrated as a reliable, rapid, and cost-effective technology for detecting traces of sunflower in 700 μL of highly processed oil, including refined and used cooking oil. The study will contribute to both the food industry and the energy sector as developed methods can be used for oil authenticity testing in food and biodiesel production.

A study on the impact of industrial-scale refining on olive oil and olive pomace oil contamination with mineral oils

Mineral oil hydrocarbons (MOH), including saturated (MOSH) and aromatic (MOAH) hydrocarbons, are contaminants of petrogenic origin. On-line high-performance liquid chromatography (HPLC) – gas chromatography (GC) – flame ionization detector (FID) was used for determining MOH in olive oils (OOs) and olive pomace oils (OPOs) at different stages of the refining process and in samples from the Italian market. Deodorization reduced contamination by about 30 %, resulting in a significant reduction of endogenous n-alkanes generally up to n-C31. Comprehensive GC coupled to quadrupole time-of-flight (QTOF) mass spectrometry (MS) allowed investigating the effect of bleaching on a sample of OPO naturally contaminated with alkylated PAHs, demonstrating the removal capacity of this refining step on potentially carcinogenic genotoxic compounds derived from MOH contamination. OOs from the market contained on average 33.1 mg/kg of MOSH n-C10–50 and 3.3 mg/kg of MOAH, while OPOs contained on average 160.7 and 36.1 mg/kg of MOSH and MOAH, respectively.

Gold leaf electrodes for UV/Vis spectroelectrochemical determination of ortho-diphenols in extra virgin olive oil

A simple and easily replicable technique is here presented for assembling planar electrochemical cells based on gold-leaf electrodes using ordinary tools and a do-it-yourself approach. These devices have been profitably used to perform spectroelectrochemical measurements in the reflectance mode demonstrating for the first time how the use of gold-leaf electrodes can offer a viable and low cost alternative to traditionally used electrochemical platforms assembled by gold vapor deposition or screen printing.After optimization of fabrication parameters, the electrochemical and spectroelectrochemical characterization of these cells was performed by using potassium hexacyanoferrate(II) as redox probe.Then, hydroxytyrosol has been selected as model to develop an innovative and so far never presented spectroelectrochemical method for the determination and quantification of ortho-diphenol antioxidants in extra virgin olive oil. The results achieved allowed us to preliminary evaluate the electrochemical oxidation mechanism of hydroxytyrosol at gold leaf electrodes and then to select the best wavelength for its spectroelectrochemical determination.The approach developed enabled to evaluate hydroxytyrosol concentrations from both the electrochemical and spectroscopic signals with repeatable and comparable results. Comparison between electrochemical and optical determinations performed on real sample demonstrates that the two methods can be used indistinctively, proving that spectroelectrochemistry represents an autovalidated technique able to provide reliable results thanks to complementary information that are simultaneously obtained from electrochemistry and spectroscopy.

Antioxidant Effect of Extra Virgin Olive Oil and Apple Cider Vinegar in Type 2 Diabetic Rat Model

Antioxidant Effect of Extra Virgin Olive Oil and Apple Cider Vinegar in Type 2 Diabetic Rat Model

Antineuroinflammatory Potential of Uvaol Transformation Products by Three Fungal Species.

The prevalence of neurodegenerative diseases has increased in recent decades. Its exact pathogenesis is not yet fully understood, and only a few drugs can be used clinically to alleviate disease symptoms. Increasing evidence highlights plant-derived compounds are becoming a promising resource for mitigating the onset and progression of neurodegenerative diseases. Uvaol (1) is an ursane-type triterpenoid commonly found in olive leaves, fruits, and virgin olive oil. It is one of the rare compounds in olive oil that can penetrate the blood-brain barrier. Despite its potential neuroprotective activity, research on its structural variations and antineuroinflammatory properties remains sparse. This study explored the biotransformation of uvaol using three fungal species: Actinomucor elegans, Aspergillus flavus, and Circinella muscae. This process yielded 15 new compounds along with seven known ones. Their structures were determined through comprehensive spectroscopic analysis. Furthermore, the antineuroinflammatory activities of compounds were evaluated by using MTT and Griess assays. Notably, compound 9 was found to markedly suppress the transcriptional levels of inflammation-associated elements such as TNF-α, IL-1β, IL-6, iNOS, and COX-2 in BV-2 cells stimulated by lipopolysaccharides (LPS). Moreover, compound 9 also facilitated autophagy by upregulating ULK1 mRNA expression and downregulating the p62 protein. These results suggested that biotransformation was an effective approach for rapidly diversifying uvaol and providing a basal material for the discovery of candidates in treating neurodegenerative diseases.

Changes in the Composition, Antioxidant Activity, and Sensory Attributes of Olive Oil Used as a Storage Medium for Dried Tomato Preservation

Changes in the Composition, Antioxidant Activity, and Sensory Attributes of Olive Oil Used as a Storage Medium for Dried Tomato Preservation

Protective effect of astaxanthin on acute liver injury induced by α-amanitin in mice

Objective: To explore the protective effect of astaxanthin on acute liver injury induced by α-amanitin in mice. Methods: In June 2023, 42 healthy SPF male Kunming mice were selected. The mice were divided into blank control group, model (0.45 mg/kg α-amanitin) group, olive oil (10 ml/kg olive oil) group, low dose (20 mg/kg) astaxanthin group, medium dose (40 mg/kg) astaxanthin group, high dose (80 mg/kg) astaxanthin group and silybin (20 mg/kg) group by random number table method. Each group had 6 animals. Mice in the blank control group were intraperitoneally injected with 10 ml/kg normal saline, and mice in the other group were injected with α-amanitin. After that, the blank control group and model group were infused with 10 ml/kg normal saline, olive oil group and astaxanthin groups were given olive oil and astaxanthin according to dose by gavage, and silybin group was injected with silybin by dose. The drug was administered once every 12 h for a total of 4 doses. After 60 h, the mice were killed, the liver weight was weighed, and the liver index was calculated. The contents of aspartate aminotransferase (AST) and alanine aminotransferase (ALT) in serum of mice were detected, and the contents of superoxide dismutase (SOD), reduced glutathione (GSH), catalase (CAT), malondialdehyde (MDA) in liver tissues were also detected. One-way analysis of variance (ANOVA) was used to compare the difference of indexes among each group, and pairwise comparison was performed by Dunnett-t test. Results: The mice in the blank control group had smooth hair color, good spirit and normal behavior, while the mice in the other groups showed varying degrees of retardation and decreased diet, and no death occurred in each group. Body mass[ (26.67±1.51) g] and liver mass[ (1.23±0.14) g] in model group were significantly lower than those in blank control group [ (33.50±2.43) g and (1.87±0.16) g], and the differences were statistically significant (P<0.05). The liver index [ (5.39±0.32) %, (5.83±0.30) %, (5.75±0.24) % and (5.78±0.16) %] in low, medium and high dose astaxanthin groups and silybin group were significantly higher than those in model group [ (4.61±0.12) %], and the differences were statistically significant (P<0.05). Serum ALT and AST contents in model group [ (153.04±13.96) U/L and (59.08±4.03) U/L] were significantly higher than those in blank control group [ (13.77±1.29) U/L and (10.21±0.35) U/L], and the differences were statistically significant (P<0.05). The contents of CAT, GSH and SOD in liver tissues of model group [ (9.40±2.23) U/mgprot, (3.09±0.26) μmol/gprot and (48.94±3.13) U/mgprot] were significantly lower than those of blank control group [ (26.36±2.92) U/mgprot, (6.76±0.71) μmol/gprot and (89.89±4.17) U/mgprot], the differences were statistically significant (P<0.05). MDA content[ (6.33±0.24) nmol/mgprot] in liver tissue of model group was significantly higher than that of blank control group [ (0.91±0.21) nmol/mgprot], and the difference was statistically significant (P<0.05). The CAT contents[ (18.64±1.76) U/mgprot, (18.20±1.76) U/mgprot, and (15.54±1.36) U/mgprot] in liver tissues of low, medium and high dose astaxanthin groups were significantly higher than those of model group, with statistical significances (P<0.05). Compared with model group, SOD contents[ (72.16±7.44) U/mgprot, (93.18±5.28) U/mgprot, (103.78±7.07) U/mgprot, and (96.60±7.02) U/mgprot] in liver tissues of mice in low, medium and high dose astaxanthin groups and silybin group were significantly increased (P<0.05), MDA contents [ (4.30±0.84) U/mgprot, (3.66±0.28) U/mgprot, (2.96±0.29) U/mgprot, and (2.88±0.39) U/mgprot] were significantly decreased (P<0.05). Compared with model group, GSH content [ (7.90±1.25) μmol/gprot] in high dose astaxanthin group was significantly increased (P<0.05) . Conclusion: Astaxanthin may alleviate acute liver injury induced by α-amanitin by alleviating oxidative stress in mice liver.

Steadfast Bubbles: a Palestinian soap company’s journey to globalization

Learning outcomes By the end of this case study analysis, students are expected to understand the dynamics of global markets by identifying institutional voids in prospective export destinations using the framework by Khanna and Palepu; evaluate potential export destinations for Nablus Soap Company (NSC), taking into account the identified institutional voids and their implications for market entry. Formulate strategies for NSC to address institutional voids and manage exports effectively to the selected country. Assess various global expansion strategies beyond exporting for NSC, examining their respective advantages, disadvantages, and feasibility within the context of the company’s goals. Analyze the factors that contributed to NSC’s successful expansion into 72 countries, despite the longstanding challenges faced by Palestinians since 1948, including the recent impact of the 2023 situation in Gaza on the West Bank. Case overview/synopsis This case study provides students with an in-depth understanding of the Palestinian economy, focusing on the NSC, a small and medium enterprise in the olive soap industry. Founded by Mojtaba Tbeleh in 1971, NSC’s legacy spans 400 years. It is known for crafting handmade, 100% natural soap with olive oil as a key ingredient. As of November 2023, NSC has successfully expanded its exports to more than 72 countries. Despite this achievement, the company faces significant challenges due to various restrictions, particularly those imposed by occupying forces. The case study provides insights into NSC’s international expansion challenges, guiding students in understanding how institutional voids in potential expansion destinations impact market entry decisions. It encourages them to identify these voids select appropriate markets and formulate strategies to leverage NSC’s global expansion potential. Complexity academic level This case study is suitable for undergraduate- or postgraduate-level students. Supplementary materials Teaching notes are available for educators only. Subject code CSS 5: International business.

Microencapsulation, Cream Development, and Controlled Clinical Study of an Upcycled Polyphenolic Extract Combined with sh-Oligopeptide-1

Olive mills produce pomace as a by-product of olive oil production process, which has a negative environmental impact. In this study, the dry extract of pomace (OG2), rich in polyphenols, was used for cosmetic purposes. The polyphenolic extract was encapsulated together with sh-oligopeptide-1 using cellulose fibres by spray-drying technology. Cytotoxicity and antistress cell studies were carried out using a modified cell line (THP1). Based on the results, a single, randomised, self-controlled study was conducted to evaluate the cream in thirty healthy volunteers. Statistical analysis was performed using a paired samples t-test. Skin moisture increased in the treated forearm (p-value &lt; 0.000). There was an increase in elasticity in the treated forearm (p-value 0.042). TEWL decreased after one week of cream application (p-value 0.099). The results of this clinical study showed that the cream improved barrier function after one week of application on healthy skin.

The Antifungal Potential of Ozonated Extra-Virgin Olive Oil Against Candida albicans: Mechanisms and Efficacy.

The growing emergence of resistance mechanisms and side effects associated with antifungal agents highlight the need for alternative therapies. This study aims to investigate the antifungal potential of ozonated extra-virgin olive oil (EOO) against Candida albicans, with the goal of developing eco-friendly and highly effective treatments based on natural products. Antifungal activity was evaluated via cell viability and biofilm formation assays using Crystal Violet and Sytox green staining. The results showed that EOO reduced C. albicans viability in a dose-dependent manner, achieving over 90% cell death at a 3% (v/v) concentration. Transmission Electron Microscopy (TEM) revealed cell wall structural damage, and ROS levels increased by approximately 60% compared to untreated controls within 10 min of treatment. Additionally, the expression of autophagy-related genes atg-7 and atg-13was upregulated by 2- and 3.5-fold, respectively, after 15 min, suggesting a stress-induced cell death response. EOO also significantly inhibited hyphal formation and biofilm development, thus reducing C. albicans pathogenicity while preserving cell biocompatibility. EOO antifungal activity was also observed in the case of Candida glabrata. In conclusion, ozonated olive oil demonstrates potent antifungal activity against C. albicans by reducing cell viability, inhibiting hyphal and biofilm formation, and triggering oxidative stress and autophagy pathways. These findings position EOO as a promising alternative therapy for fungal infections.

Exploring the Biological Potential of Hydroxytyrosol and Derivatives: Synthetic Strategies and Evaluation of Antiproliferative, Antioxidant, and Antimicrobial Activities.

Phenolic compounds found in Extra Virgin Olive Oil (EVOO) have been associated with various health benefits. Bioavailability studies indicate that the phase I and II metabolites of these phenolic compounds can be detected in human urine and plasma following EVOO consumption. To contribute to the understanding of the biological potential of these phenolic compounds and their metabolites, this study delves into the synthesis, stability, and biological activities of hydroxytyrosol (HT), tyrosol (Tyr), and homovanillic alcohol (HVA), as well as their glucuronide, sulfate, and acetylated metabolites. For the first time, an effective synthesis was developed to allow the selective obtention of 3'- and 4'-glucuronides, as well as sulfates of HT. HT and its acetylated derivative emerged as the most potent compounds across antioxidant assessments, antiproliferative studies against human colorectal adenocarcinoma cell lines, and antimicrobial assays.