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Planta Med 2024; 90(07/08): 554-560
DOI: 10.1055/a-2235-0009
Biological and Pharmacological Activity
Original Papers

Oxidation Study of Oleocanthal and Oleacein Induced by Oxone[ # ]

Lemonia Antoniadi
1   Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece
,
Apostolis Angelis
1   Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece
,
Ioannis K. Kostakis
2   Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece
,
Leandros A. Skaltsounis
1   Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece
› Author AffiliationsThe research work was cofinanced by the Hellenic Foundation for Research and Innovation (HFRI) under the 3rd Call for HFRI PhD Fellowships (Fellowship Number: 5266) and by the European Regional Development Fund of the European Union and Greek national funds through the Operational Program Competitiveness, Entrepreneurship and Innovation, under the call RESEARCH –CREATE –INNOVATE (project code: T2EDK-02423).
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Abstract

A selective Oxone-induced oxidation of oleocanthal and oleacein, the two main secoiridoids of olive oil, to their bis-oxidized products is described. This protocol is based on a Baeyer-Villiger mechanism and the concentration of Oxone in the final solution. The bis-oxidation of the aldehydic compounds could be extended for the synthesis of various semisynthetic analogs. The obtained acids exhibit strong antioxidant activity, being efficient free radical scavengers.

Key words

Oleocanthal - oleacein - oleocanthanonic acid - oleaceinonic acid - Olea europaea - Oleaceae - Baeyer-Villiger oxidation - antioxidant activity

# This work is dedicated to Professors Rudolf Bauer, Chlodwig Franz, Brigitte Kopp, and Hermann Stuppner for their invaluable contributions and commitment to Austrian Pharmacognosy.


Supporting Information

    NMR and HRMS spectra of compounds 14 and 15 (Figs. 1S–21S), analysis of 1H NMR spectrum of crude extract of entry 6 (Fig. 22S), Oxone-induced oxidation of EDA (6) (Figs. 23S–29S), NMR data of isomer E (17) and isomer Z (18) (Table 1S and Fig. 28S), and DPPH radical scavenging activity of pure compounds and equations for the determination of IC50 values of the pure compounds (Fig. 30S and Table 2S) are available as Supporting Information.

  • Supporting Information


Publication History

Received: 30 September 2023

Accepted after revision: 14 December 2023

Article published online:
06 June 2024

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