Oxidation Study of Oleocanthal and Oleacein Induced by Oxone

Lemonia Antoniadi; Apostolis Angelis; Ioannis K. Kostakis; Leandros A. Skaltsounis

doi:10.1055/a-2235-0009

Planta Medica, Inhaltsverzeichnis

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

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece

,

Apostolis Angelis

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece

,

Ioannis K. Kostakis

²Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece

,

Leandros A. Skaltsounis

¹Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimioupoli Zografou, Athens, Greece

› Institutsangaben

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

Volltext

Referenzen

References
1 Covas MI, Fitó M, de la Torre R. Minor bioactive olive oil components and health: key data for their role in providing health benefits in humans. Olive Olive Oil Bioact Const 2015; 31-52
2 Visioli F, Bernardini E. Extra virgin olive oilʼs polyphenols: biological activities. Curr Pharm Des 2011; 17: 786-804
3 Vichi S, Cortés-Francisco N, Caixach J. Insight into virgin olive oil secoiridoids characterization by high-resolution mass spectrometry and accurate mass measurements. J Chromatogr A 2013; 1301: 48-59
4 International Olive Council. Determination of biophenols in olive oils by HPLC. COI/T20/Doc No 29/Rev1 2017; 29: 1-8
5 Nikou T, Witt M, Stathopoulos P, Barsch A, Halabalaki M. Olive oil quality and authenticity assessment aspects employing FIA-MRMS and LC-Orbitrap MS metabolomic approaches. Frontiers in Public Health 2020; 8: 1-20
6 Angelis A, Antoniadi L, Stathopoulos P, Halabalaki M, Skaltsounis LA. Oleocanthalic and oleaceinic acids: New compounds from Extra Virgin Olive Oil (EVOO). Phytochem Lett 2018; 26: 190-194
7 Esposito Salsano J, Pinto D, Rodrigues F, Saba A, Manera C, Digiacomo M, Macchia M. Oleocanthalic acid from extra-virgin olive oil: Analysis, preparative isolation and radical scavenging activity. Journal of Food Composition and Analysis 2022; 105: 104-160
8 Nikou T, Karampetsou KV, Koutsoni OS, Papaioanou V, Skaltsounis AL, Dotsika E, Halabalaki M. Pharmacokinetics and metabolism of oleocanthal, a natural anti-inflammatory agent of olive oil. Planta Med 2022; 88: 1452-1453
9 Antoniadi L, Angelis A, Stathopoulos P, Bata EM, Papoutsaki Z, Halabalaki M, Skaltsounis LA. Oxidized forms of olive oil secoiridoids: Semisynthesis, identification and correlation with quality parameters. Planta Med 2022; 88: 805-813
10 Mannam S, Sekar G. CuCl catalyzed oxidation of aldehydes to carboxylic acids with aqueous tert-butyl hydroperoxide under mild conditions. Tetrahedron Lett 2008; 49: 1083-1086
11 Agrawal MK, Adimurthy S, Ghosh PK. Oxidative esterification of benzaldehyde and deactivated aromatic aldehydes with N-bromosuccinimide-pyridine. Synth Commun 2012; 42: 2931-2936
12 Bernini R, Coratti A, Provenzano G, Fabrizi G, Tofani D. Oxidation of aromatic aldehydes and ketones by H₂OH₂/CHH₃ReOH₃ in ionic liquids: a catalytic efficient reaction to achieve dihydric phenols. Tetrahedron 2005; 61: 1821-1825
13 Grill JM, Ogle JW, Miller SA. An efficient and practical system for the catalytic oxidation of alcohols, aldehydes, and α,β-unsaturated carboxylic acids. J Org Chem 2006; 71: 9291-9296
14 Reddy KR, Venkateshwar M, Maheswari CU, Prashanthi S. Catalytic oxidative esterification of aldehydes and alcohols using KI-TBHP. Synth Commun 2010; 40: 186-195
15 Webb KS, Ruszkay SJ. Oxidation of aldehydes with Oxone^® in aqueous acetone. Tetrahedron 1998; 54: 401-410
16 Desai LV, Malik HA, Sanford MS. Oxone as an inexpensive, safe, and environmentally benign oxidant for C–H bond oxygenation. Org Lett 2006; 8: 1141-1144
17 Travis BR, Sivakumar M, Hollist GO, Borhan B. Facile oxidation of aldehydes to acids and esters with Oxone. Org Lett 2003; 5: 1031-1034
18 ten Brink GJ, Arends IW, Sheldon RA. The Baeyer-Villiger reaction: New developments toward greener procedures. Chem Rev 2004; 104: 4105-4123
19 Axiotis E, Angelis A, Antoniadi L, Petrakis EA, Skaltsounis LA. Phytochemical analysis and dermo-cosmetic evaluation of Cymbidium sp. (Orchidaceae) cultivation by-products. Antioxidants (Basel) 2021; 11: 1-6
20 Vontzalidou A, Dimitrakoudi SM, Tsoukalas K, Zoidis G, Chaita E, Dina E, Cheimonidi C, Trougakos IP, Lambrinidis G, Skaltsounis AL, Mikros E, Aligiannis N. Development of stilbenoid and chalconoid analogues as potent tyrosinase modulators and antioxidant agents. Antioxidants 2022; 11: 1593

Zusatzmaterial

Ergänzendes Material

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

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