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CC BY-NC-ND 4.0 · Planta Med 2022; 88(09/10): 805-813
DOI: 10.1055/a-1806-7815
Natural Product Chemistry and Analytical Studies
Original Papers

Oxidized Forms of Olive Oil Secoiridoids: Semisynthesis, Identification and Correlation with Quality Parameters[ # ]

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
,
Panagiotis Stathopoulos
1   Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece
,
Eirini-Maria Bata
2   PharmaGnose S. A., Oinofyta, Greece
,
Zoe Papoutsaki
1   Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece
,
Maria Halabalaki
1   Division of Pharmacognosy and Natural Products 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 AffiliationsSupported by: European Regional Development Fund (ERDF) and Greek national funds through the Operational Program "Competitiveness, Entrepreneurship and Innovation", under the call “RESEARCH – CREATE - INNOVATE” (project HOLEA code: 03816)
Supported by: European Union and project OliveNet-H2020-MSCA-RISE-2016 – “Bioactive compounds from Olea europaea: investigation and application in food, cosmetic and pharmaceutical industry” (Proposal Number: 734899) under the Horizon2020 framework
Supported by: European Union (ERDF) and Greek national funds through the Operational Program "Competitiveness, Entrepreneurship and Innovation", under the call “Strengthening research and Innovation Infrastructures” (Plant Up, project code:5002803)
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Abstract

Secoiridoids is the prominent chemical class of olive oil polar constituents and are characterized by significant biological properties. They are abundant in different chemical forms and relatively high concentrations compared to other components, while prone to oxidation due to their chemical motif. In recent years, oxidized derivatives of secoiridoids have been reported, either as natural constituents of olive oil or as components which are gradually formed in all stages of its production and storage. The mono-oxidized forms of oleocanthal and oleacein named as the respective acids have been recently isolated from olive oil and unambiguously structurally characterized. Other oxidized forms of elenolic acid or more complex secoiridoids, such as those of oleuropein and ligstroside aglycones are also sporadically mentioned in the literature. No further information is provided since they have not been isolated in pure form in order to be accurately identified. Most of the time, they are generally referred as oxidized forms of the parent compounds and commonly identified based on mass spectrometric data. In the current study, the semi-synthesis of the main oxidized olive oil secoiridoids, i.e., oleocanthalic acid, oleaceinic acid, EDA acid, carboxylic form of elenolic acid, carboxylic form of ligstroside aglycon, and carboxylic form of oleuropein aglycon is described starting from the corresponding aldehydic derivatives, using SeO2/H2O2 as oxidative agents. Furthermore, their presence in a number of Greek olive oils was investigated as well, as possible correlation thereof with quality parameters.

Key words

Oxidized Secoiridoid Compounds - Oleocanthal - Oleocanthalic acid - Semi-synthesis - Olive oil - Quality parameters - Olea europaea - Oleaceae

# Dedicated to Professor Dr. A. Douglas Kinghorn on the occasion of his 75th birthday.


Supporting Information

    The following are available as supporting information: NMR and HRMS spectra of compounds 1–3 and 7 – 9 (Fig. 1S – 30S), HRMS/MS spectra of MFOA, CFLA Oleacein and Oleocanthalic acid (Fig. 31S – 32S), identification of biophenols peaks according to T.20/Doc No 29 method of IOC (Table 1S), meta data of analyzed olive oil samples (Table 2S), and the comparison data on OO quality parameters and identification levels of oxidized secoiridoids (Table 3S).

  • Supporting Information


Publication History

Received: 25 November 2021

Accepted after revision: 01 February 2022

Accepted Manuscript online:
23 March 2022

Article published online:
01 July 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commecial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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