Solid-phase extraction gas chromatography-ion trap-mass spectrometry qualitative method for evaluation of phenolic compounds in virgin olive oil and structural confirmation of oleuropein and ligstroside aglycons and their oxidation products.
Phenolic compounds in Spanish virgin olive oil were analyzed by GC-MS after an SPE diol cartridge extraction and clean-up procedure. Posterior derivatization to trimethylsilyl (TMS) ethers using a mixture of hexamethyldisilazane:dimethylclorosilane (HMDS:DMCS) in pyridine (3:1:9) was performed. Several compounds were detected and 21 of them were identified. Free phenols such as hydroxytyrosol, tyrosol, tyrosyl and hydroxytyrosyl acetate, and aldehydic and dialdehydic forms of elenolic acid linked to tyrosol and hidroxytyrosol were the most abundant compounds. Likewise, oxidation products coming from the aldehydic and dialdehydic forms of elenolic acid, and of ligstroside and oleuropein aglycons, were detected, and their structure confirmed by other mass spectrometry technique, i.e., HPLC-APCI-MS. Individual oxidation products were isolated from an oxidized sample by preparative HPLC, converted to TMS ethers and re-analyzed by GC-MS. When necessary and for identification purposes, selective ion monitoring, namely, GC-MS-SIM, was employed. This is the first time that structures of oxidized forms are determined by GC-MS.
Ríos
J J
JJ
Instituto de la Grasa (CSIC), Departamento Caracterización y Calidad de los Alimentos, Avda Padre García Tejero 4, 41012 Sevilla, Spain.
Gil
M J
MJ
Gutiérrez-Rosales
F
F
D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D005960:Glucosides / Q000737:chemistry*; D057888:Iridoid Glucosides; D039823:Iridoids; D015394:Molecular Structure; D000069463:Olive Oil; D010084:Oxidation-Reduction; D010636:Phenols / Q000032:analysis*; D010938:Plant Oils / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
D005960:Glucosides; D057888:Iridoid Glucosides; D039823:Iridoids; D000069463:Olive Oil; D010636:Phenols; D010938:Plant Oils; D011714:Pyrans; C002769:oleuropein; C445380:ligstroside