A compound isolated from <i>Olea europaea L.</i>

Veer, W. L. C.; Gerris, V.; Ribbers, J. E.; Oud, P. J.; Ree, P. J. van; Beyerman, H. C.; Bontekoe, J. S.

doi:10.1002/recl.19570761013

Cited by 5 publications

(6 citation statements)

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“…Phenolics found in olive fruit, which have been shown to have antimicrobial activity, such as p-hydroxybenzoic, vanillic, caffeic, protocatechuic, syringic and p-coumaric acids, oleuropein, quercetin, tyrosol, hydroxytyrosol, elenolic acid, etc. (Veer et al 1957;Fleming et al 1969Fleming et al , 1973Mateos et al 2001;Medina et al 2006). The chromatographic techniques frequently used to determine phenolic compounds in olive fruit and leaves are gas chromatography (GC) and liquid chromatography (HPLC).…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity and Chemical Constitutions of Olea Europaea L. Leaf Extracts

Korukluoğlu

Şahan

Yiğit

et al. 2010

Journal of Food Processing and Preservation

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The in vitro antimicrobial activity of aqueous, acetone, diethyl ether and ethyl alcohol extracts of olive leaves (Olea europaea L.) was studied. The aqueous extract of olive leaves had no antibacterial effect against the test microorganisms, whereas acetone extract showed inhibitory effect on Salmonella enteritidis, Bacillus cereus, Klebsiella pneumoniae, Escherichia coli, Enterococcus faecalis, Streptococcus thermophilus and Lactobacillus bulgaricus. Furthermore, the antimicrobial activities of some phenolic compounds against microorganisms were tested. The most effective compound was found to be oleuropein while syringic acid was found ineffective. The characterization of phenolic compounds in different extracts determined by high performance liquid chromatography‐air pressure chemical ionization‐mass spectrometry detector (HPLC‐APCI‐MSD GC‐MS) gas chromatography‐mass spectrometry (GC‐MS). The acetone and the ethyl alcohol extracts had the most and the least oleuropein content, respectively. PRACTICAL APPLICATIONS In recent years the extracts of many plant species have become popular, and attempts to characterize their bioactive principles have gained speed for many pharmaceutical and food‐processing applications. Especially, antimicrobial properties of plants have revived as a consequence of current problems associated with the use of chemical preservatives. Because of consumers' negative perspectives of synthetic preservatives, attention is shifting toward natural alternatives. The findings suggest that olive leaf extracts and their phenolic compounds have good potential as antibacterial substances in food preservation as they may be more acceptable to consumers and the regulatory agencies in comparison with synthetic chemical compounds.

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Section: Introductionmentioning

confidence: 99%

Antibacterial Activity and Chemical Constitutions of Olea Europaea L. Leaf Extracts

Korukluoğlu

Şahan

Yiğit

et al. 2010

Journal of Food Processing and Preservation

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“…The name 'elenolide' had already been given in 1957 to a lactone obtained after acidification of olive leaves and fruit extracts. 9 The structure corresponding to that lactone was elucidated in 1961 and the geometry of the double bond was proposed as Z. 10,11,13 The E isomer described herein had been chemically synthesized 10 without substantial NMR description and, interestingly, it had never been recorded as an ingredient of olive oil and it had never been completely characterized by NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…The elenolide was in the form of colorless needle-shaped crystals in accordance with literature data. [9][10][11] The purity of the isolated elenolide was checked by 1 H-NMR spectroscopy and was found to be >95%. The complete NMR data of elenolide are provided in Table 1.…”

Section: Elenolide Isolationmentioning

confidence: 99%

“…The structure of elenolide is possibly derived biosynthetically from precursors such as oleomissional (9) and oleokoronal (10), 7 coming respectively from oleuropein (1) and ligstroside (2). Hydrolytic or enzymatic removal of the hydroxytyrosol or tyrosol moiety, respectively, can lead to structure 13, which is in equilibrium with structure 14.…”

Section: Biosynthetic Pathway Of Elenolidementioning

confidence: 99%

“…1 If an olive oil contains at least 5 mg hydroxytyrosol and its derivatives (oleuropein complex and tyrosol) per daily dose of 20 g, it can be considered as beneficial for consumers health and specifically for protection against oxidative stress. [2][3][4] A variety of compounds related to oleuropein (1) and ligstroside (2), such as oleacein (3), 5 oleocanthal (4), 5 oleuropein and ligstroside aglycons (5,6) 6 and their dialdehydic, monoaldehydic and enolic forms (known also as oleuropeindials (7), ligstrodials (8), oleomissional (9) and oleokoronal (10)), 7 have been recognized as belonging to the class of phenols that are measured in order to support the above health claim. 8 A reliable analytical method based on 1D quantitative nuclear magnetic resonance (qNMR) spectroscopy has been recently developed to measure the concentration of all the compounds mentioned in the regulation with a simple experiment, avoiding the formation of artifacts and providing the necessary data for certification of the health claim.…”

Section: Introductionmentioning

confidence: 99%

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S‐(E)‐Elenolide: a new constituent of extra virgin olive oil

et al. 2019

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BACKGROUND: Extra virgin olive oil is a food with a recognized health claim in the EU related to its phenolic content. Based on nuclear magnetic resonance (NMR) analysis, we observed for the first time that most high-phenolic olive oils also contain significant quantities of another potential beneficial ingredient, S-(E)-elenolide, which is a non-phenolic compound related to oleuropein or ligstroside. Elenolide had only been found in olive leaves and fruits as the Z isomer or had been synthesized and had been recognized as an antihypertensive agent. RESULTS: (E)-Elenolide was isolated from olive oil and its structure was elucidated and completely characterized for the first time using 1D and 2D NMR and gas chromatography-mass spectrometry. In addition, we developed a method of quantitative measurement based on qNMR. Investigation of 2120 olive oil samples showed that elenolide was present in the majority of samples, in quantities ranging from 0 to 2821 mg kg −1 . Although elenolic acid, which is a hydrated derivative of elenolide, had been reported as an olive oil ingredient, this is the first time that elenolide has proved to be transformed to elenolic acid after reaction with water. Finally, it was found that the quantity of elenolide in olive oil depends on the quantity of water remaining in the olive oil during storage. CONCLUSION: S-(E)-Elenolide is a new important substance of olive oil and could be used as marker of high-quality oils with low water content. Quantitative determination of elenolide with GC-MSThe calibration curve for the GC-MS measurements was constructed using the following concentrations: 560, 280, 140, 70, 35 and 17.5 mg kg −1 (provided as supporting information). The elenolide peak was integrated at 14.4 min, corresponding to a 224 amu molecular ion. Syngaldehyde in acetonitrile (0.5 mg mL −1 ) was used as internal standard.J Sci Food Agric 2019; 99: 5319-5326

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Les iridoïdes et séco-iridoïdes: Répartition, structure, propriétés, biosynthèse

Plouvier

Favre-Bonvin

1971

Phytochemistry

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A compound isolated from Olea europaea L.

Cited by 5 publications

References 0 publications

Antibacterial Activity and Chemical Constitutions of Olea Europaea L. Leaf Extracts

Antibacterial Activity and Chemical Constitutions of Olea Europaea L. Leaf Extracts

S‐(E)‐Elenolide: a new constituent of extra virgin olive oil

Les iridoïdes et séco-iridoïdes: Répartition, structure, propriétés, biosynthèse

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