Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves

Sarikaki, Georgia; Christoforidou, Nikoleta; Gaboriaud‐Kolar, Nicolas; Smith, Amos B.; Kostakis, Ioannis K.; Skaltsounis, Alexios‐Léandros

doi:10.1021/acs.jnatprod.0c00086

Cited by 25 publications

(15 citation statements)

References 32 publications

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“…This can be explained by possible biotransformation from OL to OLC during the drying process. Sarikaki et al [ 45 ] has already proposed a mechanism for this conversion. This would include cleavage of the methyl ester, followed by a loss of the sugar and an opening of the secologanoside ring, leading to a seco -dialdehyde derivative, which is susceptible to decarboxylation.…”

Section: Resultsmentioning

confidence: 99%

Olive Pomace Phenolic Compounds Stability and Safety Evaluation: From Raw Material to Future Ophthalmic Applications

et al. 2021

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Nowadays, increasing interest in olive pomace (OP) valorization aims to improve olive’s industry sustainability. Interestingly, several studies propose a high-value application for OP extracts containing its main phenolic compounds, hydroxytyrosol and oleuropein, as therapy for ocular surface diseases. In this work, the stability and accessibility of OP total phenolic and flavonoid content, main representative compounds, and antioxidant activity were assessed under different pretreatment conditions. Among them, lyophilization and supercritical CO2 extraction were found to increase significantly most responses measured in the produced extracts. Two selected extracts (CONV and OPT3) were obtained by different techniques (conventional and pressurized liquid extraction); Their aqueous solutions were characterized by HPLC-DAD-MS/MS. Additionally, their safety and stability were evaluated according to EMA requirements towards their approval as ophthalmic products: their genotoxic effect on ocular surface cells and their 6-months storage stability at 4 different temperature/moisture conditions (CPMP/ICH/2736/99), together with pure hydroxytyrosol and oleuropein solutions. The concentration of hydroxytyrosol and oleuropein in pure or extract solutions was tracked, and possible degradation products were putatively identified by HPLC-DAD-MS/MS. Hydroxytyrosol and oleuropein had different stability as standard or extract solutions, with oleuropein also showing different degradation profile. All compounds/extracts were safe for ophthalmic use at the concentrations tested.

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Section: Resultsmentioning

confidence: 99%

Olive Pomace Phenolic Compounds Stability and Safety Evaluation: From Raw Material to Future Ophthalmic Applications

et al. 2021

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“…Sarikaki and co-workers 54 took a biomimetic approach from natural extracts of olive leaves, starting from oleuropein 4, oleocanthal 7, oleacein 8 and four analogues (Figure 10). The modifications associated with the syntheses of the analogues were introduced in the alkyl chain and the phenol moiety.…”

Section: Oleocanthalmentioning

confidence: 99%

“…The analogues 178 and 184 had already been described by Smith's group 48 (Figure 9). Sarikaki et al 54 designed a procedure that is well suited for the multigram obtention of many oleocanthal analogues and thus for the exploration of the structure−activity relationships for biological evaluation. In fact, 10 g of dialdehyde analogues could be obtained from 10 kg of olive leaves.…”

Section: Oleocanthalmentioning

confidence: 99%

“…The group also tested several inorganic salts but it was clearly evident that NaCl was the best one, also considering its low toxicity and large availability. 62 Sarikaki et al 54 also described a strategy to obtain oleacein 8. The group employed the same biomimetic procedure used for the obtention of oleocanthal 7; acetylated hydroxytyrosol 173 was used (Scheme 17) instead of acetylated tyrosol for the esterification.…”

Section: Oleaceinmentioning

confidence: 99%

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Phenolic Compounds from Virgin Olive Oil: Approaches for Their Synthesis and Analogues

Martins

Bronze

Ventura

2022

J. Agric. Food Chem.

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Virgin olive oil (VOO) is the main fat consumed by populations in the Mediterranean basin, and phenolic compounds, minor components of this fat, are known to be responsible for diverse health benefits when consumed in a regular diet. According to numerous investigations, these benefits are mostly related to phenols such as tyrosol and hydroxytyrosol and secoiridoid derivatives such as ligstroside, oleuropein, oleocanthal and oleacein. These compounds are present in low concentrations, and for some of them, standards are not commercially available, hampering studies on the mechanisms underlying their biological activity. In order to contribute to a better knowledge of the bioactivity of these compounds and their metabolites, they must be available with high purity and in sufficient amounts for the assays. Chemical synthesis has been considered a convenient way to obtain these compounds. This Review will focus on the synthesis of representative VOO compounds, namely, ligstroside, oleuropein, oleocanthal, oleacein and analogues.

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“…A few years later, the same group obtained oleocanthal in 10 steps with a 14% of overall yield by a modified protocol . Several alternative strategies have been reported over the years, but none have shown better results. − Actually, the first semisynthetic alternative to oleocanthal was recently proposed by Sarikaki et al, and its preparation step started both from pure oleuropein and the olive leaf extract, passing through the enzymatic hydrolysis of dimethyl ligstroside as an intermediate, and reaching oleocanthal with, respectively, 11% and 6% overall yields. The merit of the method was to attempt a gram-scale protocol to obtain oleocanthal, but the proposed pathway did not allow obtaining ligstroside or its aglycone.…”

Section: Introductionmentioning

confidence: 99%

Green Semisynthetic Cascade to Ligstroside, Ligstroside Aglycone, and Oleocanthal

Mancuso

Costanzo

Bonacci

et al. 2021

ACS Sustainable Chem. Eng.

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Ligstroside, ligstroside aglycone, and oleocanthal are extra virgin olive oil (EVOO) bioactive phenols poorly represented in olive leaves. Semisynthetic pathways to achieve them, starting with largely available natural precursors, are proposed as alternative solution with respect to their low effective extraction or total synthesis. In the present work, we propose the first green chemocatalytic method to obtain, in the same semisynthetic cascade, ligstroside, ligstroside aglycone, and oleocanthal starting from oleuropein. The sustainability of the method was assessed by building the synthesis trees, while the green credentials of each step were analyzed through the CHEM21 toolkit, thus allowing consequent considerations on the large-scale feasibility.

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Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves

Cited by 25 publications

References 32 publications

Olive Pomace Phenolic Compounds Stability and Safety Evaluation: From Raw Material to Future Ophthalmic Applications

Olive Pomace Phenolic Compounds Stability and Safety Evaluation: From Raw Material to Future Ophthalmic Applications

Phenolic Compounds from Virgin Olive Oil: Approaches for Their Synthesis and Analogues

Green Semisynthetic Cascade to Ligstroside, Ligstroside Aglycone, and Oleocanthal

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