Grasas y Aceites, Vol 61, No 2 (2010)

Secoiridoids in olive seed: characterization of nüzhenide and 11-methyl oleosides by liquid chromatography with diode array and mass spectrometry


https://doi.org/10.3989/gya.087309

Sandra Silva
Instituto de Biologia Experimental e Tecnológica - Instituto de Tecnologia Química e Biológica - Faculdade de Farmácia de Lisboa, Portugal

Lucília Gomes
Instituto de Biologia Experimental e Tecnológica - Faculdade de Farmácia de Lisboa, Portugal

Fausto Leitão
Instituto Nacional de Recursos Biológicos I.P., Unidade de Recursos Genéticos, Ecofisiologia e Melhoramento de Plantas, Portugal

Maria Bronze
Instituto de Biologia Experimental e Tecnológica - Instituto de Tecnologia Química e Biológica - Faculdade de Farmácia de Lisboa, Portugal

Ana V. Coelho
Instituto de Tecnologia Química e Biológica - Universidade de Évora, Portugal

Luís Vilas Boas
Instituto de Biologia Experimental e Tecnológica - Instituto de Tecnologia Química e Biológica, Portugal

Abstract


The seed extracts of olive tree cultivars were analyzed by reverse phase HPLC with diode array detection and mass spectrometry. HPLC hyphenation with mass spectrometry (ESI source) in both polarity modes enabled the identification in olive seeds of nüzhenide and nüzhenide 11-methyl oleoside, among other 11-methyl oleosides, by means of MSn. The methods used allowed us to obtain olive seed profiles of phenolic components and to conclude that they are mainly secoiridoids. The quantification of detected phenolic secoiridoids was also achieved using ultraviolet detection (λ = 240 nm) which enabled comparison of the samples. Nüzhenide and nüzhenide 11-methyl oleoside were the major components detected in olive seeds of all the cultivars studied, but variations in individual components of olive seeds were verified among the cultivars. The results also support the existence of di and tri(11-methyl oleosides) of nüzhenide.

Keywords


Mass spectrometry; 11-Methyl oleosides; Nüzhenide; Olive seed; Phenolic compounds; Secoiridoids

Full Text:


PDF

References


Calis I, Hosny M, Lahloub MF. 1996. A secoiridoid glucoside from Fraxinus Angustifolia. Phytochemistry 41, 1557-1562. doi:10.1016/0031-9422(95)00815-2

Cardoso SM, Guyot S, Marnet N, Lopes-da-Silva J A, Renard CMGC, Coimbra MA. 2005. Characterization of phenolic extracts from olive pulp and olive pomace by electrospray mass spectrometry. J Sci. of Food Agric. 85, 21-32. doi:10.1002/jsfa.1925

Chien CT, Ling-Long KH, Shen YC, Zhang R, Chen SY, Yang JC, Pharis RP. 2004. Storage behaviour of Chionanthus retusus seed and asynchronous development of the radicle and shoot apex during germination in relation to germination inhibitors, including abscisic acis and four phenolic glucosides. Plant Cell Physiol. 45, 1158-1167. doi:10.1093/pcp/pch129 PMid:15509838

Jensen SR, Franzyk H, Wallander E. 2002. Chemotaxonomy of the Oleaceae: iridoids as taxonomic markers. Phytochemistry 60, 213-231. doi:10.1016/S0031-9422(02)00102-4

Maestro-Durán R, Cabello LR, Gutiérrez RV and Roncero VA. 1994. Glucósidos fenólicos amargos de las semillas del olivo (Olea europaea). Grasas y Aceites 45, 332-335.

He ZD, Dong H, Xu HX, Ye WC, Sun HD, But PPH. 2001. Secoiridoid constituents from the fruits of Ligustrum lucidum. Phytochemistry 56, 327-330. doi:10.1016/S0031-9422(00)00406-4

Koichi M, Kaneko A, Hosogai T, Kakuda R, Yaoita Y, Kikuchi M. 2002. Studies on the constituents of Syringa species. X. Five new iridoid glycosides from the leaves of Syringa reticulate (Blume) Hara. Chem. Pharm. Bull. 50, 493-497. doi:10.1248/cpb.50.493

Robards K, Prenzler PD, Tucke G, Swatsitang P, Glover W. 1999. Phenolic compounds and their role in oxidative processes in fruits. Food Chem. 66, 401-436. doi:10.1016/S0308-8146(99)00093-X

Ryan D, Robards K and Lavee S. 1999. Determination of phenolic compounds in olives by reversedphase chromatography and mass spectrometry. J. Chromatogr. A 832, 87-96. doi:10.1016/S0021-9673(98)00838-3

Ryan D, Antolovich M, Prenzler P, Robards K and Lavee S. 2002. Biotransformations of phenolic compounds in Olea europaea L. Sci. Hortic. 92, 147-176. doi:10.1016/S0304-4238(01)00287-4

Servili M, Baldioli M, Selvagini R, Macchioni A and Montedoro G. 1999. Phenolic compounds of olive fruit: on e- and two-dimensional nuclear magnetic resonance characterization of nüzhenide and its distribution in the constitutive parts of fruit. J. Agric. Food Chem. 47, 12-18. doi:10.1021/jf9806210 PMid:10563841

Servili M and Montedoro G. 2002. Contribution of phenolic compounds in virgin olive oil quality. European Journal of Lipid Science and Technology 104, 602-613. doi:10.1002/1438-9312(200210)104:9/10<602::AID-EJLT602>3.0.CO;2-X

Silva S. 2004. Phenolic compounds in samples of olive tree cultivars (Olea europaea L.). M.Sc. Thesis, Faculty of Pharmacy, Lisbon University, Lisbon, Portugal.




Copyright (c) 2010 Consejo Superior de Investigaciones Científicas (CSIC)

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.


Contact us grasasyaceites@ig.csic.es

Technical support soporte.tecnico.revistas@csic.es