title: Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC.
abstract: For the provision of oleocanthal (OLC), a phenolic compound with very promising pharmacological properties, isolation from olive oil is a very important option. Due to the compound's sensitivity to decomposition upon exposure to oxygen and light, a very gentle isolation method has been developed under use of high performance countercurrent chromatography (HPCCC). By partition of olive oil between hexane and methanol, an extract enriched in phenolics was prepared and subjected to a two-step HPCCC separation under use of heptane-EtOAc-MeOH-H2O mixtures in normal-phase and reverse phase mode, respectively. With this method, the isolation of tyrosol, hydroxytyrosol, and the mixture of (3S,4E)- and (3S,4Z)-OLC was achieved in approx. 70 min for each step. By one- and two-dimensional NMR-experiments and LC-MS, the equilibrium of (3S,4E)- and (3S,4Z)-OLC in such olive oil extracts has unambiguously been proven for the first time.
authors.affiliation: Department of Pharmacognosy, University of Vienna, Vienna, Austria. Electronic address: hamid-reza.adhami@univie.ac.at.
authors.forename: Hamid-Reza
authors.initials: HR
authors.lastname: Adhami
authors.affiliation: Department of Pharmacognosy, University of Vienna, Vienna, Austria.
authors.forename: Martin
authors.initials: M
authors.lastname: Zehl
authors.affiliation: Department of Pharmacognosy, University of Vienna, Vienna, Austria.
authors.forename: Christina
authors.initials: C
authors.lastname: Dangl
authors.affiliation: Department of Pharmacognosy, University of Vienna, Vienna, Austria.
authors.forename: Dominic
authors.initials: D
authors.lastname: Dorfmeister
authors.affiliation: Department of Pharmacognosy, University of Vienna, Vienna, Austria.
authors.forename: Marco
authors.initials: M
authors.lastname: Stadler
authors.affiliation: Department of Medicinal Chemistry, University of Vienna, Vienna, Austria.
authors.forename: Ernst
authors.initials: E
authors.lastname: Urban
authors.affiliation: Brunel Institute for Bioengineering, Brunel University, Uxbridge, UK.
authors.forename: Peter
authors.initials: P
authors.lastname: Hewitson
authors.affiliation: Brunel Institute for Bioengineering, Brunel University, Uxbridge, UK.
authors.forename: Svetlana
authors.initials: S
authors.lastname: Ignatova
authors.affiliation: Department of Pharmacognosy, University of Vienna, Vienna, Austria.
authors.forename: Liselotte
authors.initials: L
authors.lastname: Krenn
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003377:Countercurrent Distribution / Q000379:methods*; D000081004:Cyclopentane Monoterpenes; D000069463:Olive Oil / Q000032:analysis*; D010636:Phenols / Q000737:chemistry*; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry; D010938:Plant Oils / Q000032:analysis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000081004:Cyclopentane Monoterpenes; D000069463:Olive Oil; D010636:Phenols; D010938:Plant Oils; C011867:4-hydroxyphenylethanol; C503534:oleocanthal; D010626:Phenylethyl Alcohol
keywords: HPCCC; Hydroxytyrosol; Oleocanthal; Olive oil; Phenolics; Tyrosol