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…

Understanding graft union formation by using metabolomic and transcriptomic approaches during the first days after grafting in grapevine

Since the arrival of Phyloxera (Daktulosphaira vitifolia) in Europe at the end of the 19th century, grafting has become essential to cultivate Vitis vinifera. Today, grafting provides not only resistance to this aphid, but it used to adapt the cultivars according to the type of soil, environment, or grape production requirements by using a panel of rootstocks. As part of vineyard decline, it is often mentioned the importance of producing quality grafted grapevine to improve vineyard longevity, but, to our knowledge, no study has been able to demonstrate that grafting has a role in this context. However, some scion/rootstock combinations are considered as incompatible due to poor graft union formation and subsequently high plant mortality soon after grafting. In a context of climate change where the creation of new cultivars and rootstocks is at the centre of research, the ability of new cultivars to be grafted is therefore essential. The early identification of graft incompatibility could allow the selection of non-viable plants before planting and would have a beneficial impact on research and development in the nursery sector. For this reason, our studies have focused on the identification of metabolic and transcriptomic markers of poor grafting success during the first days/week after grafting; we have identified some correlations between some specialized metabolites, especially stilbenes, and grafting success, as well as an accumulation of some amino acids in the incompatible combination. The study of the metabolome and the transcriptome allowed us to understand and characterise the processes involved during graft union formation.

Geospatial trends of bioclimatic indexes in the topographically complex region of Barolo DOCG

Barolo DOCG is an economically important wine producing region in Northwest Italy. It is a small region of approximately 70 km2 gross area. The topography is very complex with steep sloped hills ranging in elevation from below 200 m to 550 m. Barolo DOCG wine is made exclusively from the Nebbiolo grape. Bioclimatic indexes are often used in viticulture to gain a better understanding of broader climate trends which can be compared temporally and geographically. These indexes are also used for identifying potential phenological timing, growing region suitability, and potential risks associated with expected climatic changes. Understanding how topography influences bioclimatic indexes can help with understanding of mesoscale climate behaviour leading to improved decision making and risk management strategies. The average monthly maximum and minimum temperatures, the Cool Night Index, the Huglin Index, and the monthly diurnal range (from July to October) were calculated using data from 45 weather stations within a 40 km radius of the Barolo DOCG growing area between the years 1996 and 2019. Linear and multiple regression models were developed using independent variables (elevation, aspect, slope) extracted from a digital elevation model to identify significant relationships. Bioclimatic indexes were then kriged with external drift using independent variables that showed significant relationships with the bioclimatic index using a 100 m resolution grid. The maximum monthly temperatures and the Huglin Index showed consistent significant negative relationships with elevation in all years. The minimum monthly temperatures showed no relationship with elevation but in some months a small but significant relationship was observed with aspect. Due to the lack of a relationship between minimum monthly temperatures and elevation compared to the significant relationship between maximum monthly temperatures and elevation, monthly diurnal range had a negative relationship with elevation.

Investigating the impact of grape exposure and UV radiations on rotundone in Vitis vinifera L. Tardif grapes under field trial conditions

Rotundone is the main aroma compound responsible for peppery notes in wines whose biosynthesis is negatively affected by heat and drought. Through the alteration of precipitation regime and the increase in temperature during maturation, climate change is expected to affect wine peppery typicality. In this context there is a demand for developing sustainable viticultural strategies to enhance rotundone accumulation or limit its degradation. It was recently proposed that ultraviolet (UV) radiations could stimulate rotundone production. The aim of this study was to investigate under field trial conditions the impact of grape exposure and UV treatments on rotundone in Vitis vinifera L. Tardif, an almost extinct grape variety from south-west France that can express particularly high rotundone levels. Four different treatments were compared in 2021 to a control treatment using a randomised complete block design with three replications per treatment. Grape exposure was manipulated through early or late defoliation. Leaf and laterals shoots were removed at Eichorn Lorenz growth stages 32 or 34 on the morning-sun side of the canopy. During grape maturation, UV radiations were either reduced by 99% by installing UV radiation-shielding sheets, or applied four times using the Boxilumix™ non thermal device (Asclepios Tech, Tournefeuille) with the aim of activating plant signalling pathway. Loggers displayed in solar radiation shields were used to assess the effect of such shielding sheets on air temperature within the bunch zone. The composition of grapes subjected to these treatments will be soon analysed for their rotundone content and basic classical laboratory analyses. Grapes will be harvested to elaborate wines under standardized small-scale vinification conditions (60kg) that will be assessed by a trained sensory panel.

Analysis of some environmental factors and cultural practices that affect the production and quality of the Manto Negro, Callet and Prensal Blanc varieties

45 non irrigated vineyards distributed in the DO (Denomination) Pla i Llevant de Mallorca and the DO Binissalem Mallorca were used to investigate the characteristics of production and quality and their relationships certain environmental factors and cultural practices. The grape varieties investigated are autochthonous to the island of Mallorca, Manto Negro and Callet as red and Prensal Blanc as white. All plants were measured for four consecutive years in the main production and quality parameters. Among the environmental factors, the type of soil has been studied, more specifically its water retention capacity, the planting density, the age of the vineyard and the level of viral infection. The presence or absence of virus seems to have no effect on any component studied in the varieties studied. For the white variety Prensal Blanc age is negatively correlated with production and the number of bunches, nevertheless it does not cause any effect on the required quality parameters. However, for the red varieties Callet and Manto Negro, the age of the plantation is the variable that best correlates with the quality parameters, therefore the old vines should be the object of preservation by the viticulturists and winemakers in order to guarantee its contribution to the quality of the wines made with these varieties.

Extreme canopy management for vineyard adaptation to climate change: is it a good idea?

Climate change constitutes an enormous challenge for humankind and for all human activities, viticulture not being an exception. Long-term strategic changes are probably needed the most, but growers also need to deal with short-term changes: summers that are getting progressively warmer, earlier harvest dates and higher pH in musts and wines. In the last 10-15 years, a relevant corpus of research is being developed worldwide in order to evaluate to which extent extreme canopy management operations, aimed at reducing leaf area and, thus, limiting the source to sink ratio, could be useful to delay ripening. Although extreme canopy management can result in relevant delays in harvest dates, longer term studies, as well as detailed analysis of their implications on carbohydrate reserves, bud fertility and future yield are desirable before these practices can be recommended.