WAC 2022 banner
IVES 9 IVES Conference Series 9 WAC 9 WAC 2022 9 4 - WAC - Posters 9 Mechanistic insights into the bioavailability of oleocanthal and oleacein from olive oil in presence of wine active peptides and amino acids

Mechanistic insights into the bioavailability of oleocanthal and oleacein from olive oil in presence of wine active peptides and amino acids

Abstract

Oleocanthal (OC) and oleacein (OL) are highly bioactive secoiridoids found in olive oil at elevated concentrations, especially when it is produced from unripe olives (Olea europaea L.). Both compounds have been correlated with strong activities against serious diseases through recent clinical trials. The most important clinical trials have been performed in patients against chronic lymphocytic leukemia1, against mild cognitive impairment2 and against platelet aggregation of normal3 or diabetic patients. Carefully designed nutritional interventions in humans using olive oil with high OC/OL content or olive oil without OC/OL have provided strong evidence about the unique therapeutic role of those compounds. However, both compounds do not actually circulate in the body and cannot be found in any biological fluid. Recent studies have shown that OC and OL react spontaneously with plasma aminoacids like glycine to form new highly bioactive chemical entities like oleoglycine that circulate in the blood and can also reach the brain of experimental animals4. During our continuous effort to understand the mechanisms of action of OC/OL, we investigated the reactions of both compounds with aminoacids and peptides found in white wines5. During this study we screened the selectivity and the rate of this reaction, and we discovered new metabolites with unique structures and properties like oleocysteine (1a,b), oleoserine (2a,b) or oleoglutathione (3a,b). The synthesized metabolites were structurally elucidated using NMR and MS. OC/OL selectivity was assessed by competitive nucleophilic addition reactions with peptides and amino acids at pH=7 and 3.5, quantifying products and ratios by UHPLC-Q-ToF MS. The obtained results can shed light on the mechanism of action of OC/OL and more significantly explain their bioavailability.

1.        Rojas Gil AP, Kodonis I, Ioannidis A, Nomikos T, Dimopoulos I, Kosmidis G, Melliou E, Magiatis P. The Effect of Dietary Intervention With High-Oleocanthal and Oleacein Olive Oil in Patients With Early-Stage Chronic Lymphocytic Leukemia: A Pilot Randomized Trial. Front Oncol 2022; 5746.

2.        Agrawal K, Melliou E, Li X, Pedersen TL, Wang SC, Magiatis P, Newman JW, Holt RR. Oleocanthal-rich extra virgin olive oil demonstrates acute anti-platelet effects in healthy men in a randomized trial. J Funct Foods 2017;36: 84-93

3.        Tsolaki M, Lazarou E, Kozori M, Petridou N, Tabakis E, Lazarou I, Karakota M, Saoulidis I, Melliou E, Magiatis P. A Randomized Clinical Trial of Greek High Phenolic Early Harvest Extra Virgin Olive Oil in Mild Cognitive Impairment: The MICOIL Pilot Study. J Alzh Disease 2020; 78.

4.        Darakjian L, Rigakou A, Brannen A, Qusa MH, Tasiakou N, Diamantakos P, Reed MN, Panizzi P, Boersma MD, Melliou E, El Sayed KA, Magiatis P, Kaddoumi A. Spontaneous In Vitro and In Vivo Interaction of (−)-Oleocanthal with Glycine in Biological Fluids: Novel Pharmacokinetic Markers”. ACS Pharmacol Transl Sci 2021; 4: 179-192.

5.        Romanet, R., Bahut, F., Nikolantonaki, M., & Gougeon, R. D. (2020). Molecular Characterization of White Wines Antioxidant Metabolome by Ultra High Performance Liquid Chromatography High-Resolution Mass Spectrometry. Antioxidants (Basel), 9(2). https://doi.org/10.3390/antiox9020115.

DOI:

Publication date: June 27, 2022

Issue: WAC 2022

Type: Article

Authors

Kalyva F, Diamantakos P, Melliou E, Nikolantonaki M, Magiatis P

Presenting author

Kalyva F

UMR PAM, IUVV, Université Bourgogne-Franche-Comté

Tags

IVES Conference Series | WAC 2022

Citation

Related articles…

A better understanding of the climate effect on anthocyanin accumulation in grapes using a machine learning approach

The current climate changes are directly threatening the balance of the vineyard at harvest time. The maturation period of the grapes is shifted to the middle of the summer, at a time when radiation and air temperature are at their maximum. In this context, the implementation of corrective practices becomes problematic. Unfortunately, our knowledge of the climate effect on the quality of different grape varieties remains very incomplete to guide these choices. During the Innovine project, original experiments were carried out on Syrah to study the combined effects of normal or high air temperature and varying degrees of exposure of the berries to the sun. Berries subjected to these different conditions were sampled and analyzed throughout the maturation period. Several quality characteristics were determined, including anthocyanin content. The objective of the experiments was to investigate which climatic determinants were most important for anthocyanin accumulation in the berries. Temperature and irradiance data, observed over time with a very thin discretization step, are called functional data in statistics. We developed the procedure SpiceFP (Sparse and Structured Procedure to Identify Combined Effects of Functional Predictors) to explain the variations of a scalar response variable (a grape berry quality variable for example) by two or three functional predictors (as temperature and irradiance) in a context of joint influence of these predictors. Particular attention was paid to the interpretability of the results. Analysis of the data using SpiceFP identified a negative impact of morning combinations of low irradiance (lower than about 100 μmol m−2 s−1 or 45 μmol m−2 s−1 depending on the advanced-delayed state of the berries) and high temperature (higher than 25oC). A slight difference associated with overnight temperature occurred between these effects identified in the morning.

The impact of sustainable management regimes on amino acid profiles in grape juice, grape skin flavonoids, and hydroxycinnamic acids

One of the biggest challenges of agriculture today is maintaining food safety and food quality while providing ecosystem services such as biodiversity conservation, pest and disease control, ensuring water quality and supply, and climate regulation. Organic farming was shown to promote biodiversity and carbon sequestration, and is therefore seen as one possibility of environmentally friendly production. Consumers expect organically grown crops to be free from chemical pesticides and mineral fertilizers and often presume that the quality of organically grown crops is different or higher compared to conventionally grown crops. Integrated, organic, and biodynamic viticulture were compared in a replicated field trial in Geisenheim, Germany (Vitis vinifera L. cv. Riesling). Amino acid profiles in juice, grape skin flavonoids, and hydroxycinnamic acids were monitored over three consecutive seasons beginning 7 years after conversion to organic and biodynamic viticulture, respectively. In addition, parameters such as soil nutrient status, yield, vigor, canopy temperature, and water stress were monitored to draw conclusions on reasons for the observed changes. Results revealed that the different sustainable management regimes highly differed in their amino acid profiles in juice and also in their skin flavonol content, whereas differences in the flavanol and hydroxycinnamic acid content were less pronounced. It is very likely that differences in nutrient status and yield determined amino acid profiles in juice, although all three systems showed similar amounts of mineralized nitrogen in the soil. Canopy structure and temperature in the bunch zone did not differ among treatments and therefore cannot account for the observed differences in favonols. A different light exposure of the bunches in the respective systems due to differences in vigor together with differences in berry size and a different water status of the vines might rather be responsible for the increase in flavonol content under organic and biodynamic viticulture.

Delaying irrigation initiation linearly reduces yield with little impact on maturity in Pinot noir

When to initiate irrigation is a critical annual management decision that has cascading effects on grapevine productivity and wine quality in the context of climate change. A multi-site trial was begun in 2021 to optimize irrigation initiation timing using midday stem water potential (ψstem) thresholds characterized as departures from non-stressed baseline ψstemvalues (Δψstem). Plant material, vine and row spacing, and trellising systems were concomitant among sites, while vine age, soil type, and pruning systems varied. Five target Δψstem thresholds were arranged in an RCBD and replicated eight times at each site: 0.2, 0.4, 0.6, 0.8, and 1.0 MPa (T1, T2, T3, T4, and T5, respectively). When thresholds were reached, plots were irrigated weekly at 70% ETc. Yield components and berry composition were quantified at harvest. To better generalize inferences across sites, data were analyzed by ANOVA using a mixed model including site as a random factor. Across sites, irrigation was initiated at Δψstem = 0.24, 0.50, 0.65, 0.93, and 0.98 MPa for T1, T2, T3, T4, and T5, respectively. Consistent significant negative linear trends were found for several key yield and berry composition variables. Yield decreased by 12.9, 15.9, 19.5, and 27.4% for T2, T3, T4, and T5, respectively, compared to T1 (p < 0.0001) across sites that were driven by similarly linear reductions in berry weight (p < 0.0001). Comparatively, berry composition varied little among treatments. Juice total soluble solids decreased linearly from T1 to T5 – though only ranged 0.9 Brix (p = 0.012). Because producers are paid by the ton, and contracts simply stipulate a target maturity level, first-year results suggest that there is no economic incentive to induce moderate water deficits before irrigation initiation, regardless of vineyard site. Subsequent years will further elucidate the carryover effects of delaying irrigation initiation on productivity over the long term.

Vineyards and clay minerals: multi-technique analytical approach and correlations with soil properties

Purpose of this research is to quantitatively assess the mineral component of vineyard soils, with particular attention to the mineralogical analysis of clays, which represent an element of high importance in the vineyard culture as well as in general agriculture. An X-ray diffraction (XRD) / thermogravimetric (TG) multi-technique analytical approach was developed, tested on soil samples taken from vineyards around the world. This codified analytical procedure was necessary to obtain precise qualitative and quantitative mineralogical data, globally comparable to distinguish the geopedological identity of the vineyards. Soil samples from vineyards of various locations were analysed, in very different geological conditions. The bulk-rock quantitative phase analysis (QPA) was obtained by the Rietveld method while the detailed composition of the clay-sized fraction was determined by modelling of the oriented X-ray diffraction patterns. The research provided a precise classification of the mineral component of soils, distinguishing the mineral phases of the clays and the so-called mixed-layer clay minerals. We found that the content in mixed layers can be directly correlated with the water retention and the cation exchange capacity ​​of the soil, while the presence of other clayey minerals and phyllosilicates in this research did not affect this CEC parameter, which codes the fertility level of the soils. The study demonstrates that terroir, in particular soils formed in complex or very different geological conditions, can only be effectively interpreted by properly analysing its mineral phases, in particular the mixed-layer clay component. These are characteristic abiotic ecological indicators, which may have specific eco-physiological influences on the plant.

The impact of leaf canopy management on eco-physiology, wood chemical properties and microbial communities in root, trunk and cordon of Riesling grapevines (Vitis vinifera L.)

In the last decades, climate change required already adaptation of vineyard management. Increase in temperature and unexpected weather events cause changes in all phenological stages requiring new management tools. For example, defoliation can be a useful tool to reduce the sugar content in the berries creating differences in the wine profiles. In a ten-year field experiment using Riesling (Vitis vinifera L, planted 1986, Geisenheim, Germany), various mechanical defoliation strategies and different intensities were trialed until 2016 before the vineyard was uprooted. Wood was sampled from the plant compartments root, trunk, cordon and shoot for analyses of physicochemical properties (e.g. lignin and element content, pH, diameter), nonstructural carbohydrates and the microbial communities. The aim of the study was to investigate the influence of reduced canopy leaf area on the sink-source allocation into different compartments and potential changes of the fungal and prokaryotic wood-inhabiting community using a metabarcoding approach. Severe summer pruning (SSP) of the canopy and mechanical defoliation (MDC) above the bunch zone decreased the leaf area by 50% compared to control (C). SSP reduced the photosynthetic capacity, which resulted in an altered source-sink allocation and carbohydrate storage. With lower leaf area, less carbohydrates are allocated. This for example resulted in a decreased trunk diameter. Further, it affected the composition of the grapevine wood microbiota. SSP and MDC management changed significantly the prokaryotic community composition in wood of the root samples, but had no effect in other compartments. In general, this study found strong compartment and less management effects of the microbial community composition and associated physicochemical properties. The highest microbial diversities were identified in the wood of the trunk, and several species were recorded the first time in grapevine.