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…

Making sense of available information for climate change adaptation and building resilience into wine production systems across the world

Effects of climate change on viticulture systems and winemaking processes are being felt across the world. The IPCC 6thAssessment Report concluded widespread and rapid changes have occurred, the scale of recent changes being unprecedented over many centuries to many thousands of years. These changes will continue under all emission scenarios considered, including increases in frequency and intensity of hot extremes, heatwaves, heavy precipitation and droughts. Wine companies need tools and models allowing to peer into the future and identify the moment for intervention and measures for mitigation and/or avoidance. Previously, we presented conceptual guidelines for a 5-stage framework for defining adaptation strategies for wine businesses. That framework allows for direct comparison of different solutions to mitigate perceived climate change risks. Recent global climatic evolution and multiple reports of severe events since then (smoke taint, heatwave and droughts, frost, hail and floods, rising sea levels) imply urgency in providing effective tools to tackle the multiple perceived risks. A coordinated drive towards a higher level of resilience is therefore required. Recent publications such as the Australian Wine Future Climate Atlas and results from projects such as H2020 MED-GOLD inform on expected climate change impacts to the wine sector, foreseeing the climate to expect at regional and vineyard scale in coming decades. We present examples of practical application of the Climate Change Adaptation Framework (CCAF) to impacts affecting wine production in two wine regions: Barossa (Australia) and Douro (Portugal). We demonstrate feasibility of the framework for climate adaptation from available data and tools to estimate historical climate-induced profitability loss, to project it in the future and to identify critical moments when disruptions may occur if timely measures are not implemented. Finally, we discuss adaptation measures and respective timeframes for successful mitigation of disruptive risk while enhancing resilience of wine systems.

Modulation of berry composition by different vineyard management practices

High concentration of sugars in grapes and alcohol in wines is one of the consequences of climate change on viticulture production in several wine-growing regions. In order to investigate the possibilities of adaptation of vineyard management practices aimed to reduce the accumulation of sugar during the maturation phase without reducing the accumulation of anthocyanins in grapes, a study with severe shoot trimming, shoot thinning, cluster thinning and date of harvest was conducted on Merlot variety in Istria region (Croatia), under the Mediterranean climate. Four factors which may affect grape maturation and its composition at harvest were investigated in a two-years experiment; severe shoot trimming applied at veraison when >80% of berries changed colour (in comparison to untreated control), shoot thinning (0 and 30%), cluster thinning (0 and 30%), and the date of harvest (early and standard harvest dates). Shoot thinning had no significant impact on berry composition, despite the obtained reduction in yield per vine. Lower Brix in grapes were obtained with earlier harvest date and if no cluster thinning was applied, although at the same time a reduction in the concentration of anthocyanins in berries was observed in these treatments. On the other hand, if severe shoot trimming was applied when >80% of berries changed colour, a reduction of Brix was obtained without a negative impact on berry anthocyanins concentration. We conclude that in cases when undesirably high sugar concentrations at harvest are expected, severe shoot trimming at 80% veraison may effectively be used in order to obtain moderate sugar concentration in berries together with the adequate phenolic composition.

The concept of terroir: what place for microbiota?

Microbes play key roles on crop nutrient availability via biogeochemical cycles, rhizosphere interactions with roots as well as on plant growth and health. Recent advances in technologies, such as High Throughput Sequencing Techniques, allowed to gain deeper insight on the structure of bacterial and fungal communities associated with soil, rhizosphere and plant phyllosphere. Over the past 10 years, numerous scientific studies have been carried out on the microbial component of the vineyard. Whether the soil or grape compartments have been taken into account, many studies agree on the evidence of regional delineations of microbial communities, that may contribute to regional wine characteristics and typicity. Some authors proposed the term “microbial terroir” including “yeast terroir” for grapes to describe the connection between microbial biogeography and regional wine characteristics. Many factors are involved in terroir including climate, soil, cultivar and human practices as well as their interactions. Studies considering “microbial terroir” greatly contributed to improve our knowledge on factors that shape the vineyard microbial structure and diversity. However, the potential impact of “microbial terroir” on wine composition has yet not received strong scientific evidence and many questions remain to be addressed, related to the functional characterization of the microbial community and its impact on plant physiology and grape composition, the origins and interannual stability of vineyard microbiota, as well as their impact on wine sensorial attributes. The presentation will give an overview on the role of microbiota as a terroir component and will highlight future perspectives and challenges on this key subject for the wine industry.

Assessment of climate change impacts on water needs and growing cycle on grapevine in three DOs of NE Spain

This study assessed the suitability of grapevine growing in three DOs (Empordà, Pla de Bages and Penedès) of Catalonia (NE Spain) over the 21st century. For this purpose, an estimation of water needs and agroclimatic and phenological indicators was made. Climate change impacts were estimated at 1 km pixel resolution using temperature and precipitation projections from several general circulation models (GCM) and two climate change scenarios: RCP 4.5 (stabilization scenario) and RCP 8.5 (worst-case scenario). Potential crop evapotranspiration (following FAO procedure) and a daily water balance considering soil water holding capacity were used to estimate actual evapotranspiration of vines and, finally, water needs. Dynamics would be similar in the three DOs studied although the magnitude of impact differs. Water needs would be 2 and 3 times greater (ranging from 0 to more than 1500 m3/ha) than current water needs at both climate change scenarios. Moreover, blooming date would advance from 3 to 6 weeks, harvest date from 1 to 2.5 months, resulting in growing cycles from 10 to 80 days shorter. It should also be noted that frost risk would decrease from 6 to 76%, the number of days with temperatures above 30ºC during ripening would rise from 48 to 500% and tropical nights (minimum temperature >20ºC) at ripening would increase from 28 to 150%, depending on the scenario and the DOs. The impacts of climate change in the three DOs could result in significant limitations for grapevine cultivation and wine production if adaptive strategies are not applied. This result could serve as a basis for the design of specific and particular adaptation strategies to improve and maintain vineyards in the DOs studied and could be extrapolated to similar DOs and regions.

Leaf vine content in nutrients and trace elements in La Mancha (Spain) soils: influence of the rootstock

The use of rootstock of American origin has been the classic method of fighting against Phylloxera for more than 100 years. For this reason, it is interesting to establish if different rootstock modifies nutrient composition as well as trace elements content that could be important for determining the traceability of the vine products. A survey of four classic rootstocks (110-Richter, SO4, FERCAL and 1103-Paulsen) and four new ones (M1, M2, M3 and M4) provided by Agromillora Iberia. S.L.U., all of them grafted with the Tempranillo variety, has been carried out during 2019. The eight rootstocks were planted in pots of 500 cc, on three soils with very different characteristics from Castilla-La Mancha (Spain). In the month of July, the leaves were collected and dried in a forced air oven for seven days at 40ºC. Then, the samples were prepared for the analysis determination, carried out by X-Ray fluorescence spectrometry. The results obtained showed that in the case of content in mineral elements in leaf, separated by soil type, we can report the importance of few elements such as Si, Fe, Pb and, especially, Sr. The rootstock does not influence the composition of the vine leaf for the studied elements that are the most important in determining the geochemical footprint of the soil. The influence of the soil can be discriminated according to some elements such as Fe, Pb, Si and, especially, Sr.