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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemical synthesis*
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Aldehydes / chemistry
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Aldehydes / isolation & purification*
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Aldehydes / pharmacology
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Anti-Inflammatory Agents / chemical synthesis*
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / pharmacology
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Arachidonate 5-Lipoxygenase / metabolism*
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Cyclopentane Monoterpenes
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Glucosides / metabolism
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Humans
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Iridoid Glucosides
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Iridoids / analysis
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Iridoids / metabolism
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Lipoxygenase Inhibitors / pharmacology*
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Molecular Structure
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Olea / chemistry*
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Phenols / chemical synthesis*
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Phenols / chemistry
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Phenols / isolation & purification*
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Phenols / pharmacology
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Plant Extracts / pharmacology
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Plant Leaves / metabolism
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Pyrans / metabolism
Substances
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Aldehydes
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Anti-Inflammatory Agents
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Cyclopentane Monoterpenes
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Glucosides
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Iridoid Glucosides
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Iridoids
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Lipoxygenase Inhibitors
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Phenols
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Plant Extracts
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Pyrans
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oleacein
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oleuropein
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ligstroside
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oleocanthal
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Arachidonate 5-Lipoxygenase