Valorization of Oleuropein via Tunable Acid‐Promoted Methanolysis

Cavaca, Lídia A. S.; Rodrigues, Catarina A. B.; Simeonov, Svilen P.; Gomes, Rafael F. A.; Coelho, Jaime A. S.; Romanelli, Gustavo Pablo; Sathicq, Ángel Gabriel; Martínez, José Javier Pérez-Fadón; Afonso, Carlos A. M.

doi:10.1002/cssc.201800980

Cited by 9 publications

(5 citation statements)

References 29 publications

(24 reference statements)

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“…Olive and human gut microbiota β-glucosidases play critical roles in BPseco downstream conversion during olive fruit maturation, olive mill processing, and the biological metabolism that is responsible for the potential bioactives of extra virgin olive oil and table olives [ 31 , 32 ]. Additionally, olive BPseco pathways to the cleavage of bis-acetal bonds within glucose and secoiridoid subunits and promotes acid methanolysis [ 33 ]. Although molecular dynamics and Austin Model 1 (AM1) level computational mapping of oleuropein have been developed, the downstream mechanisms are not fully understood [ 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Probing Downstream Olive Biophenol Secoiridoids

Sivakumar

Uccella

Gentile

2018

IJMS

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Numerous bioactive biophenol secoiridoids (BPsecos) are found in the fruit, leaves, and oil of olives. These BPsecos play important roles in both the taste of food and human health. The main BPseco bioactive from green olive fruits, leaves, and table olives is oleuropein, while olive oil is rich in oleuropein downstream pathway molecules. The aim of this study was to probe olive BPseco downstream molecular pathways that are alike in biological and olive processing systems at different pHs and reaction times. The downstream molecular pathway were analyzed by high performance liquid chromatography coupled with electrospray ionization mass spectrometry (HPLC-ESI/MS) and typed neglected of different overlap (TNDO) computational methods. Our study showed oleuropein highest occupied molecular orbital (HOMO) and HOMO-1 triggered the free radical processes, while HOMO-2 and lowest unoccupied molecular orbital (LUMO) were polar reactions of glucoside and ester groups. Olive BPsecos were found to be stable under acid and base catalylic experiments. Oleuropein aglycone opened to diales and rearranged to hydroxytyrosil-elenolate under strong reaction conditions. The results suggest that competition among olive BPseco HOMOs could induce glucoside hydrolysis during olive milling due to native olive β-glucosidases. The underlined olive BPsecos downstream molecular mechanism herein could provide new insights into the olive milling process to improve BPseco bioactives in olive oil and table olives, which would enhance both the functional food and the nutraceuticals that are produced from olives.

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Section: Introductionmentioning

confidence: 99%

Probing Downstream Olive Biophenol Secoiridoids

Sivakumar

Uccella

Gentile

2018

IJMS

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“…Nowadays, flow reactions are gaining considerable interest due to their numerous advantages, such as higher safety, better mixing, more efficient heat transfer, chemoselectivity, reactions under extreme conditions (temperature, pressure), photochemical and electrochemical transformations, and easy scale-out. − The combination of flow chemistry and supported catalysis can additionally increase the process sustainability due to easier recyclability of the catalyst and higher product purity . In line with our previous studies under flow conditions, − we explored the possibility to apply the Adler–Becker reaction under flow conditions, in a way to improve reaction yields, minimize side reactions, and also facilitate the isolation step of spiroepoxydienones since these compounds can be quite unstable.…”

Section: Introductionmentioning

confidence: 86%

One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow

Rosatella

Afonso

2022

ACS Omega

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The Adler–Becker reaction is a useful approach for the oxidative dearomatization of salicylic alcohols to spiroepoxydienones and has been applied in the total synthesis of several natural products. Despite the advantages, the substrate and product instability under the reaction conditions can decrease the reaction efficiency, leading to lower yields. Herein, we report the Adler–Becker reaction in a continuous flow for the transformation of reduced salicylaldehydes into spiroepoxydienones in a one-pot approach. For that, a heterogeneous oxidant based on periodate is developed, leading to an efficient continuous flow process, with higher productivity and shorter reaction times, when compared with batch conditions.

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“…In this study, the treatment of table olives with aqueous lye (NaOH) solution provoked the cleavage of the oleuropein/ligstroside ester bond, releasing an elenolic acid glucose fragment and a phenol moiety (tyrosol from ligstroside and hydroxytyrosol from oleuropein) [ 34 ]. Elenolic acid glucose was also susceptible to hydrolysis, generating glucose, which could be transformed into valuable platform compounds (LA and HMF) [ 19 ], as shown in Figure 1 .…”

Section: Methodsmentioning

confidence: 99%

Valorization of Wastewater from Table Olives: NMR Identification of Antioxidant Phenolic Fraction and Microwave Single-Phase Reaction of Sugary Fraction

et al. 2021

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The table olive industry is producing a huge amount of wastewater, which is a post-processing cost and an environmental concern. The present study aims to valorize this processing by-product to obtain a value-added product, thereby enhancing resource efficiency and contributing to achieving sustainable development goals (SDGs). In this sense, a chemical reaction-based platform was developed to obtain valuable components, such as levulinic acid (LA) and 5-hydromethylfurfural (HMF). The products were then analyzed using NMR identification of the antioxidant phenolic fraction and microwave single-phase reaction of the sugary fraction. According to the results, the highest concentration of phenolic compounds does not correspond to the sample directly obtained from NaOH treatment (S1), indicating that water washing steps (S2–S5) are fundamental to recover phenolic substances. Moreover, glucose was presented in the sugary fraction that can be transformed into levulinic acid by a single-phase reaction under microwave irradiation. The information provided in this manuscript suggests that the wastewater from the olive processing industry can be valorized to obtain valuable products.

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Valorization of Oleuropein via Tunable Acid‐Promoted Methanolysis

Cited by 9 publications

References 29 publications

Probing Downstream Olive Biophenol Secoiridoids

Probing Downstream Olive Biophenol Secoiridoids

One-Pot Transformation of Salicylaldehydes to Spiroepoxydienones via the Adler–Becker Reaction in a Continuous Flow

Valorization of Wastewater from Table Olives: NMR Identification of Antioxidant Phenolic Fraction and Microwave Single-Phase Reaction of Sugary Fraction

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