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…

‘Cabernet Sauvignon’ (Vitis vinifera L.) berry skin flavonol and anthocyanin composition is affected by trellis systems and applied water amounts

Trellis systems are selected in wine grape vineyards to mainly maximize vineyard yield and maintain berry quality. This study was conducted in 2020 and 2021 to evaluate six commonly utilized trellis systems including a vertical shoot positioning (VSP), two relaxed VSPs (VSP60 and VSP80), a single high wire (SH), a high quadrilateral (HQ), and a guyot (GY), combined with three levels of irrigation regimes based on different crop evapotranspiration (ETc) replacements, including a 25% ETc, 50% ETc, and 100% ETc. The results indicated SH yielded the most fruits and accumulated the most total soluble solids (TSS) at harvest in 2020, however, it showed the lowest TSS in the second season. In 2020, SH and HQ showed higher concentrations in most of the anthocyanin derivatives compared to the VSPs. Similar comparisons were noticed in 2021 as well. SH and HQ also accumulated more flavonols in both years compared to other trellis systems. Overall, this study provides information on the efficacy of trellis systems on grapevine yield and berry flavonoid accumulation in a currently warming climate.

Bioclimatic shifts and land use options for Viticulture in Portugal

Land use, plays a relevant role in the climatic system. It endows means for agriculture practices thus contributing to the food supply. Since climate and land are closely intertwined through multiple interface processes, climate change may lead to significant impacts in land use. In this study, 1-km observational gridded datasets are used to assess changes in the Köppen–Geiger and Worldwide Bioclimatic (WBCS)

Diagnosis of soil quality and evaluation of the impact of viticultural practices on soil biodiversity in a vineyard in southwestern France

Viticulture is facing two major changes – climate change and agroecological transition. In both cases, soil quality is seen as a lever to move towards a more sustainable viticulture. However, soil biological quality is little considered in the implementation of viticultural practices. Gascogn’Innov (2017-2022) is an Operational Group funded by the European Innovation Partnership for Agriculture. As such, it brings together winegrowers from the south-west of France, scientists, advisors and technicians, around a project focused on viticultural soil biological functioning and the design of technical routes more respectful toward soil heritage. To achieve this, the project aims to acquire references on the impact of viticultural practices on soil biology from a dynamic way, and to test a methodology to integrate information provided by the soil bioindicators to manage farming systems. A set of indicators of soil biological quality are evaluated in the project: microorganisms (bacteria and fungi abundance and diversity), fauna (abundance and diversity of nematodes and earthworms), physico-chemical characteristics, soil structure assessment and degradation rate of organic matter. Based on a network of 13 plots that have been subject to an initial diagnosis in 2017, several agronomical practices to restore soil fertility are experimented to redesign the cropping system (for instance plant cover, organic matter inputs, reduction of herbicides, mineral fertilizers). System redesign was made in collaboration by winegrowers and an interdisciplinary group of experts (agronomists, biologists). Several indicators are measured on vine and soil at each vintage to assess vine health and productivity. At the end of the project (2021), a final diagnosis was carried out. Gascogn’Innov allowed to create a regional database on the quality of wine-growing soils, which permitted to evaluate the effect of practices according to soil types. Especially, decreasing the intensity of tillage and increasing the duration and diversity of grass coverage tends to increase the abundance of all the organisms studied. This project confirmed the value of soil biological quality indicators to drive the sustainability of practices, but also highlighted the key-role of expertise, in both agronomy and soil biology, to help winegrowers understand and appropriate their soil quality diagnoses.

Sustainable fertilisation of the vineyard in Galicia (Spain)

Excessive fertilization of the vineyard leads to low quality grapes, increased costs and a negative impact on the environment. In order to establish an integrated management system aimed at a sustainable fertilization of the vineyards, nutritional reference levels were established. For this purpose, 30 representative vineyards of the Albariño variety were studied, in which soil and petiole analyses were carried out for two years and grape yield and quality at harvest were measured. In both years of study, soil pH, calcium, sodium and cation exchange capacity were positively correlated with calcium content and negatively correlated with manganese in grapes. Irrigated vineyards had higher levels of aluminium in soil and lower levels of calcium in petiole. Climatic conditions were very different in the years of the study. The year 2019 was colder than usual, in 2020 there was a marked water stress with high summer temperatures. This resulted in medium-high acidity in grapes in 2019 and low acidity in 2020, with sugar levels being similar both years. A very marked decrease in must amino nitrogen was observed in 2020, with ammonia nitrogen remaining stable. The correlation of acidity and sugar values in grapes with soil and petiole analysis data made it possible to establish reference levels for the nutritional diagnosis of the Albariño variety in this region. Based on these results, an easy-to-use TIC application is currently being created for grapegrowers, aimed at improving the sustainability of the vineyard through reasoned fertilization. This study has now been extended to other Galician vine varieties.

Impact of changes in pruning practices on vine growth and yield

A gradual decline in vineyards has been observed over the past twenty years worldwide. This might be explained by the climate change, practices change or the increase of dieback diseases. To increase the longevity of vines, we studied the impact of different pruning strategies in four adult and four young vineyards located in France and Spain. In France, vineyards were planted with Cabernet franc on 3309C while Spanish trials were planted with Tempranillo grafted on 110R. Vegetative expression, yield, quality of berries and wood vessels conductivity were measured. The distribution of vegetative expression, yield and berry composition between primary and secondary vegetation were quantified. Finally, tomography was used to evaluate the implication of the treatments on sap flows.
First results show that i) the respectful pruning leads to an increase of 30 to 50% more secondary shoots than the aggressive pruning in France and between 15 and 20% in Spain, ii) there is no major effect on the yield over the first two years following the implementation of the new pruning practices, although the proportion of clusters from suckers is higher on the respectful pruning method. On young vines, the development of the trunk according to a respectful pruning leads to a loss of harvest 2 years after planting. This is due to the removal, on the future trunk, of the green suckers which carrying bunches. This operation carried out in spring rather than during winter pruning, would promote a better leaf / fruit balance when the plant comes into production, and could lead to better hydraulic conduction in the vessels of the trunk. Maintaining these trials for several years will provide more robust data to assess the impact of these practices on the vines over the long term.