Τίτλος:
One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor
Γλώσσες Τεκμηρίου:
Αγγλικά
Περίληψη:
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. © 2014 The American Chemical Society and American Society of Pharmacognosy.
Συγγραφείς:
Vougogiannopoulou, K.
Lemus, C.
Halabalaki, M.
Pergola, C.
Werz, O.
Smith, A.B.
Michel, S.
Skaltsounis, L.
Deguin, B.
Περιοδικό:
Tropical Journal of Natural Product Research
Εκδότης:
American Chemical Society
Λέξεις-κλειδιά:
iridoid; lipoxygenase inhibitor; oleacein; oleuropein; unclassified drug, article; chemical structure; drug determination; drug isolation; olive tree; one pot synthesis; plant leaf; proton nuclear magnetic resonance, Aldehydes; Anti-Inflammatory Agents; Arachidonate 5-Lipoxygenase; Glucosides; Humans; Iridoids; Lipoxygenase Inhibitors; Molecular Structure; Olea; Phenols; Plant Extracts; Plant Leaves; Pyrans
