Synthesis and antioxidant evaluation of lipophilic oleuropein aglycone derivatives

Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high hydrophilicity and degradability. Thus, a set of oleuropein aglycone derivatives were synthesized by transacetylation under mild conditions with...

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Published inFood & function Vol. 8; no. 12; pp. 4684 - 4692
Main Authors Nardi, M, Bonacci, S, Cariati, L, Costanzo, P, Oliverio, M, Sindona, G, Procopio, A
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 13.12.2017
Subjects
2,2-diphenyl-1-picrylhydrazyl
antioxidant activity
Antioxidants
Catalysis
catalytic activity
cell lines
Cultivars
Degradability
Derivatives
extra-virgin olive oil
Fats
hydrophilicity
Lewis acid
Lewis acids
lipids
Lipophilic
Lipophilicity
moieties
Oils & fats
Oleuropein
Olive oil
olives
permeability
Phenolic compounds
Phenols
Online AccessGet full text
ISSN2042-6496
2042-650X
2042-650X
DOI10.1039/c7fo01105a

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Abstract Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high hydrophilicity and degradability. Thus, a set of oleuropein aglycone derivatives were synthesized by transacetylation under mild conditions with the aim of circumventing these drawbacks and making the active moiety in oleuropein suitable to be added to food fats. The oleuropein aglycone (closed ring form) is obtained by hydrolyzing oleuropein using Lewis acid catalysis. Then, the permeation profiles as well as the antioxidant capacity of the oleuropein aglycone derivatives were evaluated by ORAC, DPPH assays and by ROS formation using the SH-SY5Y cell line. The biological activities of the obtained compounds exhibited a dependence on their level of lipophilicity. A set of oleuropein aglycone derivatives were synthesized by transacetalization under mild and environmental friendly conditions. The antioxidant activities of the obtained compounds exhibited a dependence on their level of lipophilicity thus demonstrating their potential application as a preservative in fatty foods.
AbstractList Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high hydrophilicity and degradability. Thus, a set of oleuropein aglycone derivatives were synthesized by transacetylation under mild conditions with the aim of circumventing these drawbacks and making the active moiety in oleuropein suitable to be added to food fats. The oleuropein aglycone (closed ring form) is obtained by hydrolyzing oleuropein using Lewis acid catalysis. Then, the permeation profiles as well as the antioxidant capacity of the oleuropein aglycone derivatives were evaluated by ORAC, DPPH assays and by ROS formation using the SH-SY5Y cell line. The biological activities of the obtained compounds exhibited a dependence on their level of lipophilicity. A set of oleuropein aglycone derivatives were synthesized by transacetalization under mild and environmental friendly conditions. The antioxidant activities of the obtained compounds exhibited a dependence on their level of lipophilicity thus demonstrating their potential application as a preservative in fatty foods.
Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high hydrophilicity and degradability. Thus, a set of oleuropein aglycone derivatives were synthesized by transacetylation under mild conditions with the aim of circumventing these drawbacks and making the active moiety in oleuropein suitable to be added to food fats. The oleuropein aglycone (closed ring form) is obtained by hydrolyzing oleuropein using Lewis acid catalysis. Then, the permeation profiles as well as the antioxidant capacity of the oleuropein aglycone derivatives were evaluated by ORAC, DPPH assays and by ROS formation using the SH-SY5Y cell line. The biological activities of the obtained compounds exhibited a dependence on their level of lipophilicity.
Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high hydrophilicity and degradability. Thus, a set of oleuropein aglycone derivatives were synthesized by transacetylation under mild conditions with the aim of circumventing these drawbacks and making the active moiety in oleuropein suitable to be added to food fats. The oleuropein aglycone (closed ring form) is obtained by hydrolyzing oleuropein using Lewis acid catalysis. Then, the permeation profiles as well as the antioxidant capacity of the oleuropein aglycone derivatives were evaluated by ORAC, DPPH assays and by ROS formation using the SH-SY5Y cell line. The biological activities of the obtained compounds exhibited a dependence on their level of lipophilicity.Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high hydrophilicity and degradability. Thus, a set of oleuropein aglycone derivatives were synthesized by transacetylation under mild conditions with the aim of circumventing these drawbacks and making the active moiety in oleuropein suitable to be added to food fats. The oleuropein aglycone (closed ring form) is obtained by hydrolyzing oleuropein using Lewis acid catalysis. Then, the permeation profiles as well as the antioxidant capacity of the oleuropein aglycone derivatives were evaluated by ORAC, DPPH assays and by ROS formation using the SH-SY5Y cell line. The biological activities of the obtained compounds exhibited a dependence on their level of lipophilicity.
Author Cariati, L
Nardi, M
Costanzo, P
Procopio, A
Bonacci, S
Sindona, G
Oliverio, M
AuthorAffiliation Dipartimento di Chimica e Tecnologie Chimiche
Università "Magna Græcia" di Catanzaro
Dipartimento di Scienze della Salute
Università Telematica San Raffaele
Università della Calabria
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Snippet Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high...
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SubjectTerms 2,2-diphenyl-1-picrylhydrazyl
antioxidant activity
Antioxidants
Catalysis
catalytic activity
cell lines
Cultivars
Degradability
Derivatives
extra-virgin olive oil
Fats
hydrophilicity
Lewis acid
Lewis acids
lipids
Lipophilic
Lipophilicity
moieties
Oils & fats
Oleuropein
Olive oil
olives
permeability
Phenolic compounds
Phenols
Title Synthesis and antioxidant evaluation of lipophilic oleuropein aglycone derivatives
URI https://www.ncbi.nlm.nih.gov/pubmed/29160876
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