Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical Perspective
Oleacein (Olea) and Oleocanthal (Oleo) are two phenolic compounds found in olive oil. Cell and animal studies have shown these two compounds can modulate inflammation, cancer, and neurodegenerative diseases. Unfortunately, the study of the pharmacokinetics of these two compounds appears difficult du...
Saved in:
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/7/1645 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850184503840997376 |
|---|---|
| author | Daniel Di Risola Davide Laurenti Francesca Ferraro Alessia Ciogli Simone Manetto Yuri Gazzilli Rodolfo Federico Antonio Francioso Luciana Mosca Roberto Mattioli |
| author_facet | Daniel Di Risola Davide Laurenti Francesca Ferraro Alessia Ciogli Simone Manetto Yuri Gazzilli Rodolfo Federico Antonio Francioso Luciana Mosca Roberto Mattioli |
| author_sort | Daniel Di Risola |
| collection | DOAJ |
| description | Oleacein (Olea) and Oleocanthal (Oleo) are two phenolic compounds found in olive oil. Cell and animal studies have shown these two compounds can modulate inflammation, cancer, and neurodegenerative diseases. Unfortunately, the study of the pharmacokinetics of these two compounds appears difficult due to their high reactivity with primary amines. Indeed, the presence of primary amines in culture media and biological fluids raises the question as to whether the observed biological effects are attributable to the parent compounds or to their amine derivatives. In the present work, we investigated the adduct formation between Olea or Oleo and tris(hydroxymethyl)aminomethane (Tris), a well-known primary amine used primarily as a buffer system, showing that the reaction kinetics were extremely rapid. In addition, we assessed whether the newly formed Tris adducts, i.e., Olea-Tris and Oleo-Tris, retained their antioxidant capacity by means of the ABTS and DPPH radical scavenging assays, showing that their activity was partially maintained. Finally, we evaluated the anti-inflammatory activity of these adducts on murine BV-2 microglial cells stimulated with lipopolysaccharide (LPS) and kept in an amine-free culture medium, showing how the biological response varied as the compound was degraded. Taken together, these data demonstrate that the biological effects reported in the literature are mainly due to the amino-derivatives of Olea and Oleo rather than the polyphenols derived from their breakdown (tyrosol and hydroxytyrosol). |
| format | Article |
| id | doaj-art-9dddcfc8eaf14726857ba3e821faf198 |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-9dddcfc8eaf14726857ba3e821faf1982025-08-20T02:17:01ZengMDPI AGMolecules1420-30492025-04-01307164510.3390/molecules30071645Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical PerspectiveDaniel Di Risola0Davide Laurenti1Francesca Ferraro2Alessia Ciogli3Simone Manetto4Yuri Gazzilli5Rodolfo Federico6Antonio Francioso7Luciana Mosca8Roberto Mattioli9Department of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyDepartment of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyDepartment of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyDepartment of Chemistry and Technology of Drugs, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyDepartment of Chemistry and Technology of Drugs, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyDepartment of Chemistry and Technology of Drugs, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyActive-Italia S.r.l., Via delle Terme Deciane 10, 00153 Rome, ItalyDepartment of Bioscience and Technology for Food Agriculture and Environment, University of Teramo, 64100 Teramo, ItalyDepartment of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyDepartment of Biochemical Sciences “A. Rossi Fanelli”, Sapienza University of Rome, pl.e Aldo Moro 5, 00185 Rome, ItalyOleacein (Olea) and Oleocanthal (Oleo) are two phenolic compounds found in olive oil. Cell and animal studies have shown these two compounds can modulate inflammation, cancer, and neurodegenerative diseases. Unfortunately, the study of the pharmacokinetics of these two compounds appears difficult due to their high reactivity with primary amines. Indeed, the presence of primary amines in culture media and biological fluids raises the question as to whether the observed biological effects are attributable to the parent compounds or to their amine derivatives. In the present work, we investigated the adduct formation between Olea or Oleo and tris(hydroxymethyl)aminomethane (Tris), a well-known primary amine used primarily as a buffer system, showing that the reaction kinetics were extremely rapid. In addition, we assessed whether the newly formed Tris adducts, i.e., Olea-Tris and Oleo-Tris, retained their antioxidant capacity by means of the ABTS and DPPH radical scavenging assays, showing that their activity was partially maintained. Finally, we evaluated the anti-inflammatory activity of these adducts on murine BV-2 microglial cells stimulated with lipopolysaccharide (LPS) and kept in an amine-free culture medium, showing how the biological response varied as the compound was degraded. Taken together, these data demonstrate that the biological effects reported in the literature are mainly due to the amino-derivatives of Olea and Oleo rather than the polyphenols derived from their breakdown (tyrosol and hydroxytyrosol).https://www.mdpi.com/1420-3049/30/7/1645oleaceinoleocanthaloleo-trisolea-trisadduct stability |
| spellingShingle | Daniel Di Risola Davide Laurenti Francesca Ferraro Alessia Ciogli Simone Manetto Yuri Gazzilli Rodolfo Federico Antonio Francioso Luciana Mosca Roberto Mattioli Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical Perspective Molecules oleacein oleocanthal oleo-tris olea-tris adduct stability |
| title | Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical Perspective |
| title_full | Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical Perspective |
| title_fullStr | Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical Perspective |
| title_full_unstemmed | Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical Perspective |
| title_short | Spontaneous Reaction of Oleacein and Oleocanthal with Primary Amines: A Biochemical Perspective |
| title_sort | spontaneous reaction of oleacein and oleocanthal with primary amines a biochemical perspective |
| topic | oleacein oleocanthal oleo-tris olea-tris adduct stability |
| url | https://www.mdpi.com/1420-3049/30/7/1645 |
| work_keys_str_mv | AT danieldirisola spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT davidelaurenti spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT francescaferraro spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT alessiaciogli spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT simonemanetto spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT yurigazzilli spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT rodolfofederico spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT antoniofrancioso spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT lucianamosca spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective AT robertomattioli spontaneousreactionofoleaceinandoleocanthalwithprimaryaminesabiochemicalperspective |