One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor
- PMID: 24568174
- DOI: 10.1021/np401010x
One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor
Abstract
The dialdehydes oleacein (2) and oleocanthal (4) are closely related to oleuropein (1) and ligstroside (3), the two latter compounds being abundant iridoids of Olea europaea. By exploiting oleuropein isolated from the plant leaf extract, an efficient procedure has been developed for a one-step semisynthesis of oleacein under Krapcho decarbomethoxylation conditions. Highlighted is the fact that 5-lipoxygenase is a direct _target for oleacein with an inhibitory potential (IC50: 2 μM) more potent than oleocanthal (4) and oleuropein (1). This enzyme catalyzes the initial steps in the biosynthesis of pro-inflammatory leukotrienes. Taken together, the methodology presented here offers an alternative solution to isolation or total synthesis for the procurement of oleacein, thus facilitating the further development as a potential anti-inflammatory agent.
Similar articles
-
Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves.J Nat Prod. 2020 Jun 26;83(6):1735-1739. doi: 10.1021/acs.jnatprod.0c00086. Epub 2020 May 22. J Nat Prod. 2020. PMID: 32441936
-
Oleuropein and oleacein may restore biological functions of endothelial progenitor cells impaired by angiotensin II via activation of Nrf2/heme oxygenase-1 pathway.Phytomedicine. 2013 Sep 15;20(12):1088-94. doi: 10.1016/j.phymed.2013.05.002. Epub 2013 Jun 25. Phytomedicine. 2013. PMID: 23809250
-
Anticancer Effects of Secoiridoids-A Scoping Review of the Molecular Mechanisms behind the Chemopreventive Effects of the Olive Tree Components Oleocanthal, Oleacein, and Oleuropein.Nutrients. 2024 Aug 18;16(16):2755. doi: 10.3390/nu16162755. Nutrients. 2024. PMID: 39203892 Free PMC article. Review.
-
Antimicrobial activity of Olea europaea Linné extracts and their applicability as natural food preservative agents.Int J Food Microbiol. 2017 Jun 19;251:48-66. doi: 10.1016/j.ijfoodmicro.2017.03.019. Epub 2017 Mar 28. Int J Food Microbiol. 2017. PMID: 28395179 Review.
-
Cultivar influence on variability in olive oil phenolic profiles determined through an extensive germplasm survey.Food Chem. 2018 Nov 15;266:192-199. doi: 10.1016/j.foodchem.2018.06.002. Epub 2018 Jun 4. Food Chem. 2018. PMID: 30381176
Cited by
-
Influence of Oleacein, an Olive Oil and Olive Mill Wastewater Phenolic Compound, on Caenorhabditis elegans Longevity and Stress Resistance.Foods. 2024 Jul 5;13(13):2146. doi: 10.3390/foods13132146. Foods. 2024. PMID: 38998651 Free PMC article.
-
An Appraisal of the Oleocanthal-Rich Extra Virgin Olive Oil (EVOO) and Its Potential Anticancer and Neuroprotective Properties.Int J Mol Sci. 2023 Dec 10;24(24):17323. doi: 10.3390/ijms242417323. Int J Mol Sci. 2023. PMID: 38139152 Free PMC article. Review.
-
Effects of Dietary Oleacein Treatment on Endothelial Dysfunction and Lupus Nephritis in Balb/C Pristane-Induced Mice.Antioxidants (Basel). 2023 Jun 19;12(6):1303. doi: 10.3390/antiox12061303. Antioxidants (Basel). 2023. PMID: 37372034 Free PMC article.
-
Solid acid-catalyzed one-step synthesis of oleacein from oleuropein.Sci Rep. 2023 May 22;13(1):8275. doi: 10.1038/s41598-023-35423-x. Sci Rep. 2023. PMID: 37217598 Free PMC article.
-
Effects of Oleacein, a New Epinutraceutical Bioproduct from Extra Virgin Olive Oil, in LPS-Activated Murine Immune Cells.Pharmaceuticals (Basel). 2022 Oct 28;15(11):1338. doi: 10.3390/ph15111338. Pharmaceuticals (Basel). 2022. PMID: 36355509 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Chemical Information
