Cover Image

Facile access to oleuropein and hydroxytyrosol from Ligustrum vulgare-a plant material growing all over Eurasia

Josephine M Gießel, Anne Zaar, Renate Schäfer, Ahmed Al-Harrasi, René Csuk

Abstract


Leaves of Ligustrum vulgare are an alternative, sustainable source for oleuropein. Acidic hydrolysis of oleuropein furnishes hydroxytyrosol in good yield. This approach is one of the most convenient ways to access significant amounts of oleuropein as well as of hydroxytyrosol from plant material readily accessible all over the year and throughout Eurasia. Harvesting the leaves in winter doubles the amount of oleuropein that can be extracted from the plant material.

Full Text:

PDF

References


- J. J. Reyes, B. Villanueva, J. A. Lopez-Villodres, J. P. De La Cruz, L. Romero, M. D. Rodriguez-Perez, G. Rodriguez-Gutierrez, J. Fernandez-Bolanos, J. A. Gonzalez-Correa, Neuroprotective Effect of Hydroxytyrosol in Experimental Diabetes Mellitus, J. Agric. Food Chem. 2017, 65, 4378-4383.

- T. A. Wani, F. A. Masoodi, A. Gani, W. N. Baba, N. Rahmanian, R. Akhter, I. A. Wani, M. Ahmad, Olive oil and its principal bioactive compound: Hydroxytyrosol - A review of the recent literature, Trends Food Sci. Technol. 2018, 77, 77-90.

- M. Fito, M. Cladellas, R. de la Torre, J. Marti, M. Alcantara, M. Pujadas-Bastardes, J. Marrugat, J. Bruguera, M. C. Lopez-Sabater, J. Vila, M. I. Covas, Antioxidant effect of virgin olive oil in

patients with stable coronary heart disease: a randomized, crossover, controlled, clinical trial, Atherosclerosis 2005, 181, 149-158.

- M. Fito, R. Estruch, J. Salas-Salvado, M. A. Martinez-Gonzalez, F. Aros, J. Vila, D. Corella, O. Diaz, G. Saez, R. de la Torre, M.-T. Mitjavila, M. A. Munoz, R.-M. Lamuela-Raventos, V. Ruiz-Gutierrez, M. Fiol, E. Gomez-Gracia, J. Lapetra, E. Ros, L. Serra-Majem, M.-I. Covas, Effect of the Mediterranean diet on heart failure biomarkers: a randomized sample from the PREDIMED trial, Eur. J. Heart Failure, 2014,16, 543-550.

- J. Marrugat, M. I. Covas, M. Fito, H. Schroeder, E. Miro-Casas, E. Gimeno, M. C. Lopez-Sabater, R. De La Torre, M. Farre, Effects of differing phenolic content in dietary olive oils on lipids and LDL oxidation: A randomized controlled trial, Eur. J. Nutr. 2004, 43, 140-147.

- A. Pedret, U. Catalan, S. Fernandez-Castillejo, M. Farras, R. M. Valls, L. Rubio, N. Canela, G. Aragones, M. Romeu, O. Castaner, R. de la Torre, M. I. Covas, M. Fito, M. J. Motilva, R. Sola, Impact of virgin olive oil and phenol-enriched virgin olive oils on the HDL proteome in hypercholesterolemic subjects: a double blind, randomized, controlled, cross-over clinical trial (VOHF study), PLoS One 2015, 10, e0129160/0129161-e0129160/0129119.

- R. Takeda, T. Koike, I. Taniguchi, K. Tanaka, Double-blind placebo-controlled trial of hydroxytyrosol of Olea europaea on pain in gonarthrosis, Phytomedicine 2013, 20, 861-864.

- S. Tejada, S. Pinya, M. d. Mar Bibiloni, J. A. Tur, A. Pons, A. Sureda, Cardioprotective Effects of the Polyphenol Hydroxytyrosol from Olive Oil, Curr. Drug Targets 2017, 18, 1477-1486.

- E. Lopez-Huertas, J. Fonolla, Hydroxytyrosol supplementation increases vitamin C levels in vivo. A human volunteer trial, Redox Biol. 2017, 11, 384-389.

- B. Braam, M. Langelaar-Makkinje, A. Verkleij, H. Bluyssen, T. Verrips, H.A. Koomans, J. A. Joles, J. A. Post, Anti-oxidant sensitivity of donor age-related gene expression in cultured fibroblasts, Eur. J. Pharmacol. 2006, 542, 154-161.

- A. Facchini, S. Cetrullo, S. D'Adamo, F. Flamigni, S. Guidotti, M. Minguzzi, A. Facchini, R. M. Borzi, Hydroxytyrosol prevents increase of osteoarthritis markers in human chondrocytes treated with hydrogen peroxide or growth-related oncogene α, PLoS One 2014, 9, e109724.

- V. Konstantinidou, O. Khymenets, M. I. Covas, R. de la Torre, D. Munoz-Aguayo, R. Anglada, M. Farre, M. Fito, Time course of changes in the expression of insulin sensitivity-related gens after an acute load of virgin olive oil, OMICS 2009, 13, 431-438.

- F. Casamenti, M. Stefani, Olive polyphenols: new promising agents to combat aging-associated neurodegeneration, Expert Rev. Neurother. 2017, 17, 345-358.

- M. Debbabi, A. Zarrouk, M. Bezine, W. Meddeb, T. Nury, A. Badreddine, E. M. Karym, R. Sghaier, L. Bretillon, S. Guyot, M. Samadi, M. Cherkaoui-Malki, B. Nasser, M. Mejri, S. Ben-Hammou, M. Hammami, G. Lizard, Comparison of the effects of major fatty acids present in the Mediterranean diet (oleic acid, docosahexaenoic acid) and in hydrogenated oils (elaidic acid) on 7-ketocholesterol-induced oxiapoptophagy in microglial BV-2 cells, Chem. Phys. Lipids 2017, 207, 151-170.

- H. Gardener, M. R. Caunca, Mediterranean Diet in Preventing Neurodegenerative Diseases, Curr. Nutr. Rep. 2018, 7, 10-20.

- S. Azabou, W. Najjar, A. Ghorbel, S. Sayadi, Mild Photochemical Synthesis of the Antioxidant Hydroxytyrosol via Conversion of Tyrosol, J. Agric. Food Chem. 2007, 55, 4877-4882.

- K. Bernath-Levin, J. Shainsky, L. Sigawi, A. Fishman, Directed evolution of nitrobenzene dioxygenase for the synthesis of the antioxidant hydroxytyrosol, Appl. Microbiol. Biotechnol. 2014, 98, 4975-4985.

- R. Bernini, E. Mincione, M. Barontini, F. Crisante, Convenient Synthesis of Hydroxytyrosol and Its Lipophilic Derivatives from Tyrosol or Homovanillyl Alcohol, J. Agric. Food Chem. 2008, 56, 8897-8904.

- P. Bovicelli, R. Antonioletti, S. Mancini, S. Causio, G. Borioni, S. Ammendola, M. Barontini, Expedient synthesis of hydroxytyrosol and its esters, Synth. Commun. 2007, 37, 4245-4252.

- M. Brouk, A. Fishman, Improving process conditions of hydroxytyrosol synthesis by toluene-4-monooxygenase, J. Mol. Catal. B: Enzym. 2012, 84, 121-127.

- R. Capasso, A. Evidente, S. Avolio, F. Solla, A Highly Convenient Synthesis of Hydroxytyrosol and Its Recovery from Agricultural Waste Waters, J. Agric. Food Chem. 1999, 47, 1745-1748.

- D. Deffieux, P. Gossart, S. Quideau, Facile and sustainable synthesis of the natural antioxidant hydroxytyrosol, Tetrahedron Lett., 2014, 55, 2455-2458.

- J. C. Espin, C. Soler-Rivas, E. Cantos, F. A. Tomas-Barberan, H. J. Wichers, Synthesis of the Antioxidant Hydroxytyrosol Using Tyrosinase as Biocatalyst, J. Agric. Food Chem. 2001, 49, 1187-1193.

- I. Fernandez-Pastor, A. Fernandez-Hernandez, F. Rivas, A. Martinez, A. Garcia-Granados, A. Parra, Synthesis and Antioxidant Activity of Hydroxytyrosol Alkyl-Carbonate Derivatives, J. Nat. Prod. 2016, 79, 1737-1745.

- P. P. Liebgott, M. Labat, L. Casalot, A. Amouric, J. Lorquin, Bioconversion of tyrosol into hydroxytyrosol and 3,4-dihydroxyphenylacetic acid under hypersaline conditions by the new Halomonas sp. strain HTB24, FEMS Microbiol. Lett. 2007, 276, 26-33.

- K. Napora-Wijata, K. Robins, A. Osorio-Lozada, M. Winkler, Whole-Cell Carboxylate Reduction for the Synthesis of 3-Hydroxytyrosol, ChemCatChem. 2014, 6, 1089-1095.

- G. Piersanti, M. Retini, J. L. Espartero, A. Madrona, G. Zappia, An efficient, economical synthesis of hydroxytyrosol and its protected forms via Baeyer-Villiger oxidation, Tetrahedron Lett. 2011, 52, 4938-4940.

- J. Yang, J. X. Yang, F. Zhang, G. Chen, W. Pan, R. Yu, S. Wu, P. Tien, Design, synthesis and biological evaluation of small molecular polyphenols as entry inhibitors against H5N1, Bioorg. Med. Chem. Lett. 2014, 24, 2680-2684.

- Z. L. Zhang, J. Chen, Q. Xu, C. Rao, C. Qiao, Efficient Synthesis of Hydroxytyrosol from 3,4-Dihydroxybenzaldehyde, Synth. Commun. 2012, 42, 794-798.

- I. Andreadou, D. Benaki, P. Efentakis, S. I. Bibli, A.-I. Milioni, A. Papachristodoulou, A. Zoga, A. L. Skaltsounis, E. Mikros, E. K. Iliodromitis, The Natural Olive Constituent Oleuropein Induces Nutritional Cardioprotection in Normal and Cholesterol-Fed Rabbits: Comparison with Preconditioning, Planta Med. 2015, 81, 655-663.

- F. Hadrich, A. Mahmoudi, Z. Bouallagui, I. Feki, H. Isoda, B. Feve, S. Sayadi, Evaluation of hypocholesterolemic effect of oleuropein in cholesterol-fed rats, Chem.-Biol. Interact., 2016, 252, 54-60.

- Z. Janahmadi, A. A. Nekooeian, A. R. Moaref, M. Emamghoreishi, Oleuropein Offers Cardioprotection in Rats with Acute Myocardial Infarction, Cardiovasc. Toxicol. 2015, 15, 61-68.

- A. A. Nekooeian, A. Khalili, M. B. Khosravi, Oleuropein offers cardioprotection in rats with simultaneous type 2 diabetes and renal hypertension, Indian J. Pharmacol. 2014, 46, 398-403.

- S. H. Omar, Cardioprotective and neuroprotective roles of oleuropein in olive, Saudi Pharm. J. 2010, 18, 111-121.

- S. Al-Quraishy, M.S. Othman, M. A. Dkhil, A. E. Abdel Moneim, Olive (Olea europaea) leaf methanolic extract prevents HCl/ethanol-induced gastritis in rats by attenuating inflammation and augmenting antioxidant enzyme activities, Biomed. Pharmacother. 2017, 91, 338-349.

- I. Hassen, H. Casabianca, K. Hosni, Biological activities of the natural antioxidant oleuropein: Exceeding the expectation - A mini-review, J. Funct. Foods 2015, 18, 926-940.

- S. H. Omar, Olive: native of Mediterranean region and health benefits, Pharmacogn. Rev. 2008, 2, 135-142.

- A. R. Khalatbary, H. Ahmadvand, Neuroprotective effect of oleuropein following spinal cord injury in rats, Neurol. Res. 2012, 34, 44-51.

- S. Pourkhodadad, M. Alirezaei, M. Moghaddasi, H. Ahmadvand, M. Karami, B. Delfan, Z. Khanipour, Neuroprotective effects of oleuropein against cognitive dysfunction induced by colchicine in hippocampal CA1 area in rats, J. Physiol. Sci., 2016, 66, 397-405.

- H. Yu, P. Liu, H. Tang, J. Jing, X. Lv, L. Chen, L. Jiang, J. Xu, J. Li, Oleuropein, a natural extract from plants, offers neuroprotection in focal cerebral ischemia/reperfusion injury in mice, Eur. J. Pharmacol. 2016, 775, 113-119.

- O. Benavente-Garcia, J. Castillo, J. Lorente, M. Alcaraz, Radioprotective effects in vivo of phenolics extracted from Olea europaea L. leaves against X-ray-induced chromosomal damage: comparative study versus several flavonoids and sulfur-containing compounds, J. Med. Food 2002, 5, 125-135.

- R. Domitrovic, H. Jakovac, V. V. Marchesi, I. Sain, Z. Romic, D. Rahelic, Preventive and therapeutic effects of oleuropein against carbon tetrachloride-induced liver damage in mice, Pharmacol. Res. 2012, 65, 451-464.

- A. M. Hegazy, A. S. Abdel-Azeem, H. M. Zeidan, K. S. Ibrahim, E. M. el Sayed, Hypolipidemic and hepatoprotective activities of rosemary and thyme in gentamicin-treated rats, Hum. Exp. Toxicol. 2018, 37, 420-430.

- W. Hur, S. W. Kim, Y. K. Lee, J. E. Choi, S. W. Hong, M. J. Song, S. H. Bae, T. Park, S. J. Um, S. K. Yoon, Oleuropein reduces free fatty acid-induced lipogenesis via lowered extracellular signal-regulated kinase activation in hepatocytes, Nutr. Res. 2012, 32, 778-786.

- S. W. Kim, W. Hur, T. Z. Li, Y. K. Lee, J. E. Choi, S. W. Hong, K.-S. Lyoo, C. R. You, E. S. Jung, C. K. Jung, T. Park, S. J. Um, S. K. Yoon, Oleuropein prevents the progression of steatohepatitis to hepatic fibrosis induced by a high-fat diet in mice, Exp. Mol. Med. 2014, 46, e92.

- Y. Kim, Y. Choi, T. Park, Hepatoprotective effect of oleuropein in mice: mechanisms uncovered by gene expression profiling, Biotechnol. J. 2010, 5, 950-960.

- A. Mahmoudi, F. Hadrich, I. Feki, H. Ghorbel, Z. Bouallagui, R. Marrekchi, H. Fourati, S. Sayadi, Oleuropein and hydroxytyrosol rich extracts from olive leaves attenuate liver injury and lipid metabolism disturbance in bisphenol A-treated rats, Food Funct. 2018, 9, 3220-3234.

- J.-S. Cheng, C. T. Chou, Y. Y. Liu, W. C. Sun, P. Shieh, D. H. Kuo, C. C. Kuo, C. R. Jan,

W. Z. Liang, The effect of oleuropein from olive leaf (Olea europaea) extract on Ca2+ homeostasis, cytotoxicity, cell cycle distribution and ROS signaling in HepG2 human hepatoma cells, Food Chem. Toxicol. 2016, 91, 151-166.

- M. H. Elamin, S. S. Al-Maliki, Leishmanicidal and apoptotic activities of oleuropein on Leishmania major, Int. J. Clin. Pharmacol. Ther. 2014, 52, 880-888.

- M. Leri, R. Oropesa-Nunez, C. Canale, S. Raimondi, S. Giorgetti, E. Bruzzone, V. Bellotti, M. Stefani, M. Bucciantini, Oleuropein aglycone: A polyphenol with different targets against amyloid toxicity, Biochim. Biophys. Acta, Gen. Subj. 2018, 1862, 1432-1442.

- A. Papachristodoulou, M. Tsoukala, D. Benaki, S. Kostidis, K. Gioti, N. Aligiannis, H. Pratsinis, D. Kletsas, A.-L. Skaltsounis, E. Mikros, R. Tenta, Oleuropein is a powerful sensitizer of doxorubicin-mediated killing of prostate cancer cells and exerts its action via induction of autophagy, J. Cancer Res. Treat. 2016, 4, 61-68.

- P. Samara, N. Christoforidou, C. Lemus, A. Argyropoulou, K. Ioannou, K. Vougogiannopoulou, N. Aligiannis, E. Paronis, N. Gaboriaud-Kolar, O. Tsitsilonis, A.-L. Skaltsounis, New semi-synthetic analogs of oleuropein show improved anticancer activity in vitro and in vivo, Eur. J. Med. Chem. 2017, 137, 11-29.

- K. J. Park, W. S. Suh, L. Subedi, S. Y. Kim, S. U. Choi, K. R. Lee, Secoiridoid glucosides from the twigs of Syringa oblata var. dilatata and their neuroprotective and cytotoxic activities, Chem. Pharm. Bull. 2017, 65, 359-364.

- A. Casado-Diaz, J. Anter, S. Muller, P. Winter, J. M. Quesada-Gomez, G. Dorado, Transcriptomic analyses of the anti-adipogenic effects of oleuropein in human mesenchymal stem cells, Food Funct. 2017, 8 , 1254-1270.

- M. Scognamiglio, B. D'Abrosca, V. Fiumano, M. Golino, A. Esposito, A. Fiorentino, Seasonal phytochemical changes in Phillyrea angustifolia L.: Metabolomic analysis and phytotoxicity assessment, Phytochemistry Lett. 2014, 8, 163-170.

- A. Pieroni, P. Pachaly, An ethnopharmacological study on common privet (Ligustrum vulgare) and phillyrea (Phillyrea latifolia), Fitoterapia 2000, 71, S89-S94.

- E. Giner, M. C. Recio, J. L. Rios, R. M. Giner, Oleuropein Protects against Dextran Sodium Sulfate-Induced Chronic Colitis in Mice, J. Nat. Prod. 2013, 76, 1113-1120.

- Y. H. Kim, Y. J. Choi, M. K. Kang, E. J. Lee, D. Y. Kim, H. Oh, Y. H. Kang, Oleuropein Curtails Pulmonary Inflammation and Tissue Destruction in Models of Experimental Asthma and Emphysema, J. Agric. Food Chem. 2018, 66, 7643-7654.

- J. Park, J. S. Min, U. Chae, J. Y. Lee, K. S. Song, H. S. Lee, H. J. Lee, S. R. Lee, D. S. Lee, Anti-inflammatory effect of oleuropein on microglia through regulation of Drp1-dependent mitochondrial fission, J. Neuroimmunol. 2017, 306, 46-52.

- S.-J. Ryu, H. S. Choi, K. Y. Yoon, O. H. Lee, K. J. Kim, B. Y. Lee, Oleuropein Suppresses LPS-Induced Inflammatory Responses in RAW 264.7 Cell and Zebrafish, J. Agric. Food Chem. 2015, 63, 2098-2105.

- S. Bulotta, R. Corradino, M. Celano, M. D'Agostino, J. Maiuolo, M. Oliverio, A. Procopio, M. Iannone, D. Rotiroti, D. Russo, Antiproliferative and antioxidant effects on breast cancer cells of oleuropein and its semisynthetic peracetylated derivatives, Food Chem. 2011, 127, 1609-1614.

- J. Han, T. P. N. Talorete, P. Yamada, H. Isoda, Anti-proliferative and apoptotic effects of oleuropein and hydroxytyrosol on human breast cancer MCF-7 cells, Cytotechnology 2009, 59, 45-53.

- K. Vougogiannopoulou, C. Lemus, M. Halabalaki, C. Pergola, O. Werz, A.B. Smith, III, S. Michel, L. Skaltsounis, B. Deguin, One-Step Semisynthesis of Oleacein and the Determination as a 5-Lipoxygenase Inhibitor, J. Nat. Prod. 2014, 77, 441-445.

- A. D. Bianco, I. Muzzalupo, A. Piperno, G. Romeo, N. Uccella, Bioactive derivatives of oleuropein from olive fruits, J. Agr. Food Chem. 1999, 47, 3531-3534.

- A. D. Bianco, A. Piperno, G. Romeo, N. Uccella, NMR experiments of oleuropein biomimetic hydrolysis, J. Agr. Food. Chem. 1999, 47, 3665-3668.

- R. Briante, F. La Cara, F. Febbraio, R. Barone, G. Piccialli, R. Carolla, P. Mainolfi, L. De Napoli, M. Patumi, G. Fontanazza, R. Nucci, Hydrolysis of oleuropein by recombinant beta-glycosidase from hyperthermophilic archaeon Sulfolobus solfataricus immobilised on chitosan matrix, J. Biotechnol. 2000, 77, 275-286.

- R. Briante, F. La Cara, M. P. Tonziello, F. Febbraio, R. Nucci, Antioxidant activity of the main bioactive derivatives from oleuropein hydrolysis by hyperthermophilic beta-glycosidase, J. Agr. Food Chem. 2001, 49, 3198-3203.

- F. A. Mackellar, R. C. Kelly, E. E. Van Tamelen, C. Dorschel, Structure and Stereochemistry of Elenolic Acid, J. Am. Chem. Soc. 1973, 95, 7155




DOI: http://dx.doi.org/10.13171/mjc7318101113-csuk

Refbacks

  • There are currently no refbacks.


Copyright (c) 2018 Mediterranean Journal of Chemistry