Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 49, Issue 9, Pages 4214-4219Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf010373z
Keywords
3,4-dihydroxyphenylethyl 4-formyl-3-formylmethyl-4-hexenoate; 2,2-diphenyl-1-picrylhydrazyl radical; Olea europaea; Oleaceae; olive leaves; olive oil; oleuropein; oleuropein aglycon; secoiridoids
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Storage of olive (Olea europaea) leaves for 22 h at 37 degreesC in closed plastic bags caused the content of a nonglycosidic secoiridoid, 3,4-dihydroxyphenylethyl 4-formyl-3-formylmethyl-4-hexenoate (3,4-DHPEA-EDA) to rise from 15% to 50% of the phenolic extract with corresponding falls in the content of oleuropein and two oleuropeindials, which were identified as precursors of 3,4-DHPEA-EDA. Pure product was isolated from one set of stored olive leaves in a 0.16% yield. Storage of olive leaves under various conditions showed that the moisture present in closed plastic bags was important for the formation of 3,4-DHPEA-EDA. The time taken to reach the maximum concentration of the product varied widely for different samples of olive leaves, with a shorter time for the sample with lower initial oleuropein content. The oleuropeindial precursors of the product were readily hydrolyzed to carboxylic acid derivatives, which have been identified by NMR. The antiradical activity of 3,4-DHPEA-EDA, evaluated by scavenging of 2,2-diphenyl-1-picrylhydrazyl radicals, was comparable to that of alpha -tocopherol.
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