Hydroxytyrosol

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Structural formula
Structural formula of 3-hydroxytyrosol
General
Surname Hydroxytyrosol
other names
  • 2- (3,4-dihydroxyphenyl) ethanol
  • 3,4-dihydroxyphenethyl alcohol
  • DOPET
Molecular formula C 8 H 10 O 3
Brief description

yellow liquid

External identifiers / databases
CAS number 10597-60-1
EC number 600-704-3
ECHA InfoCard 100.114.418
PubChem 82755
ChemSpider 74680
DrugBank DB12771
Wikidata Q744577
properties
Molar mass 154.16 g mol −1
Physical state

liquid

boiling point

170-175 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hydroxytyrosol is a phytochemical compound from the phenolic acid family with very strong antioxidant properties, as evidenced by the ORAC value ( Oxygen Radical Absorbance Capacity ) 40,000 µmolTE / g. Hydroxytyrosol (HT) belongs to the large family of natural polyphenols , which consists of more than 10,000 molecular species and includes anthocyanins , flavonoids , secoiridoids (such as oleuropein and ligustroside), phenolic acids (hydroxytyrosol and tyrosol), stilbenes , the ellagitannins of pomegranate, etc. .

Occurrence

Ripe olives

Hydroxytyrosol occurs in the pulp of olives and is therefore also contained in the liquid that is created during the pressing of the olives (OMW Olive Mill Wastewaters, waste water from olive oil production, also called vegetation water ), as well as in virgin olive oil , albeit in a much lower concentration Polyphenols are generally more water-soluble than oil-soluble. While hydroxytyrosol can have a concentration of approx. 4–6 g / l in vegetation water, it reaches a maximum concentration of 0.7–0.8 g / l in olive oil.

effect

The polyphenolic phytocomplex in the olive and especially in the waste water from olive oil production, which is disposed of as an agricultural waste product in the soil, contains many dozen other bioactive molecules together with hydroxytyrosol, among others. a. Cyanidines, quercetin , gallic acid, tyrosol, oleuropein, verbascoside , ligustroside, oleocanthal, etc. This combination of polyphenols is characterized by a stronger biomedical effect than isolated hydroxytyrosol, since a synergetic interaction arises between the various polyphenols, as is the case with virgin olive oil and the vegetation water have shown. Thanks to a study that led to an international patent, it became possible to extract, clarify and concentrate the polyphenolic phytocomplex of the waste water from olive oil production and make the polyphenols available for industrial production.

Polyphenols come from the secondary metabolism of plants and mainly have a protective function against parasites and pathogens. As herbal defense agents, polyphenols are also able to counteract the development and reproduction of countless types of bacteria such as staphylococci , Escherichia coli and Klebsiella in the human organism. Hydroxytyrosol and the other natural polyphenols have innumerable biological activities and health-promoting effects in the prevention and treatment of age-related pathologies and counteracts the occurrence of tumors and cardiovascular diseases. The 2016 study by Piroddi, Albini et al. to vegetation water extracted from the Moraiolo olive variety in Tuscany ( Arezzo ) has shown an antiatherogenic effect of the polyphenolic phytocomplex. In the study by T. Rossi, D. Stefano, D. Pizzichini, A. Albini et al. positive effects of the polyphenols from olive pulp with regard to the growth, migration and invasion of in vitro cultivated tumor cells (rectal tumor cells) were recorded.

Hydroxytyrosol is one of the most intensely studied polyphenolic molecules thanks to the multitude of processes in which it exerts an antioxidant effect. It is in fact a powerful inhibitor of oxidative damage resulting from lipid peroxidation of cells, which is believed to be the main cause of free radical damage. Hydroxytyrosol has also been linked to reducing damage caused by oxidative stress, including epithelial cells, liver cells, and blood cells.

By inhibiting platelet aggregation, hydroxytyrosol improves blood flow and therefore has an antithrombotic and heart-protective effect. Hydroxytyrosol is also active in the brain, where it protects the neurons from oxidation, increases the potential of the mitochondrial membrane and thus makes the brain cells more reactive.

The oxidation process is the cause of some diseases of the cardiovascular system and metabolism. In particular, the oxidation of LDL cholesterol is the basis for the formation of atherosclerotic plaques, which impair the fluid dynamics of the blood vessels and lead to serious risks and diseases of the cardiovascular system. The effectiveness of the polyphenols contained in the pulp of olives and in olive oil against the oxidation process of LDL and in reducing the risk of cardiovascular diseases has been proven. Some of these studies (Eurolive) have led the EFSA ( European Food Safety Authority ) to stipulate that a daily intake of 5 mg hydroxytyrosol and its derivatives from virgin olive oil ensures an effective reduction in cardiovascular risk factors.

Individual evidence

  1. ↑ a b c d Data sheet 3-Hydroxytyrosol, ≥98% (HPLC) from Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
  2. ↑ Shmuel Yannai: Dictionary of Food Compounds with CD-ROM, Second Edition. CRC Press, 2012, ISBN 978-1-420-08352-1 , p. 519 ( limited preview in Google book search).
  3. ^ AN Li, S. Li, YJ Zhang, XR Xu, YM Chen, HB Li: Resources and biological activities of natural polyphenols. In: Nutrients. Volume 6, number 12, December 2014, pp. 6020-6047, doi : 10.3390 / nu6126020 , PMID 25533011 , PMC 4277013 (free full text) (review).
  4. ^ M. Pizzichini, C. Russo: Recupero integrale di tutte le componenti chimiche delle acque di vegetazione olearie ; Int. Patent W02005123603 (2005).
  5. ↑ HK Obied, MS Allen, DR Bedgood, PD Prenzler, K. Robards, R. Stockmann: Bioactivity and analysis of biophenols recovered from olive mill waste. In: Journal of Agricultural and Food Chemistry . Volume 53, Number 4, 2005, pp. 823-837, doi : 10.1021 / jf048569x , PMID 15712986 (review).
  6. ↑ HK Obied, PD Prenzler, et al .: Advances in Molecular Toxicology. 2012. James CF, Elsevier. Volume 6: 195-242.
  7. ↑ R. Capasso, A. Evidente, L. Schivo, G. Orru, MA Marcialis, G. Cristinzio: Antibacterial polyphenols from olive oil mill waste waters. In: The Journal of Applied Bacteriology . Volume 79, Number 4, 1995, pp. 393-398, PMID 7592132 .
  8. ↑ A. Tafesh, N. Najami, J. Jadoun, F. Halahlih, H. Riepl, H. Azaizeh: Synergistic antibacterial effects of polyphenolic compounds from olive mill wastewater. In: Evidence-based complementary and alternative medicine: eCAM. Volume 2011, 2011, p. 431021, doi : 10.1155 / 2011/431021 , PMID 21647315 , PMC 3106970 (free full text).
  9. ↑ M. Vaher, S. Ehala, M. Kaljurand: On-column capillary electrophoretic monitoring of rapid reaction kinetics for determination of the antioxidative potential of various bioactive phenols. In: Electrophoresis . Volume 26, number 4-5, 2005, pp. 990-1000, doi : 10.1002 / elps.200410086 , PMID 15714541 .
  10. ↑ M. Piroddi, A. Albini, R. Fabiani, L. Giovannelli, C. Luceri, F. Natella, P. Rosignoli, T. Rossi, A. Taticchi, M. Servili, F. Galli: Nutrigenomics of extra-virgin olive oil: A review. In: BioFactors. Volume 43, number 1, January 2017, pp. 17-41, doi : 10.1002 / biof.1318 , PMID 27580701 (review).
  11. ↑ Barbara Bassani, Teresa Rossi a. a .: Potential chemopreventive activities of a polyphenol rich purified extract from olive mill wastewater on colon cancer cells. In: Journal of Functional Foods. 27, 2016, p. 236, doi : 10.1016 / j.jff.2016.09.009 .
  12. ↑ C. Manna, S. D'Angelo, V. Migliardi, E. Loffredi, O. Mazzoni, P. Morrica, P. Galletti, V. Zappia: Protective effect of the phenolic fraction from virgin olive oils against oxidative stress in human cells. In: Journal of Agricultural and Food Chemistry. Volume 50, Number 22, October 2002, pp. 6521-6526, PMID 12381144 .
  13. ↑ L. Goya, R. Mateos, L. Bravo: Effect of the olive oil phenol hydroxytyrosol on human hepatoma HepG2 cells. Protection against oxidative stress induced by tert-butyl hydroperoxide. In: European Journal of Nutrition . Volume 46, Number 2, 2007, pp. 70-78, doi : 10.1007 / s00394-006-0633-8 , PMID 17200875 .
  14. ^ C. Manna, P. Galletti, V. Cucciolla, G. Montedoro, V. Zappia: Olive oil hydroxytyrosol protects human erythrocytes against oxidative damages. In: The Journal of Nutritional Biochemistry . Volume 10, Number 3, 1999, pp. 159-165, PMID 15539284 .
  15. ↑ V. Lavelli, G. Fregapane, MD Salvador: Effect of storage on secoiridoid and tocopherol contents and antioxidant activity of monovarietal extra virgin olive oils. In: Journal of Agricultural and Food Chemistry. Volume 54, Number 8, 2006, pp. 3002-3007, doi : 10.1021 / jf052918l , PMID 16608222 .
  16. ^ R. Priora, D. Summa, S. Frosali, A. Margaritis, D. Di Giuseppe, C. Lapucci, F. Ieri, FM Pulcinelli, A. Romani, F. Franconi, P. Di Simplicio: Administration of minor polar compound-enriched extra virgin olive oil decreases platelet aggregation and the plasma concentration of reduced homocysteine ​​in rats. In: The Journal of Nutrition. Volume 138, Number 1, January 2008, pp. 36-41, PMID 18156401 .
  17. ↑ CL Léger, MA Carbonneau, F. Michel, E. Mas, L. Monnier, JP Cristol, B. Descomps: A thromboxane effect of a hydroxytyrosol-rich olive oil wastewater extract in patients with uncomplicated type I diabetes. In: European Journal of Clinical Nutrition . Volume 59, Number 5, 2005, pp. 727-730, doi : 10.1038 / sj.ejcn.1602133 , PMID 15798774 .
  18. ↑ M. González-Santiago, E. Martín-Bautista, JJ Carrero, J. Fonollá, L. Baró, MV Bartolomé, P. Gil-Loyzaga, E. López-Huertas: One-month administration of hydroxytyrosol, a phenolic antioxidant present in olive oil, to hyperlipemic rabbits improves blood lipid profile, antioxidant status and reduces atherosclerosis development. In: Atherosclerosis . Volume 188, Number 1, 2006, pp. 35-42, doi : 10.1016 / j.atherosclerosis.2005.10.022 , PMID 16300770 .
  19. ↑ Sebastian Schaffer, Maciej Podstawa, Francesco Visioli, Paola Bogani, Walter E. Müller, Gunter P. Eckert: Hydroxytyrosol-Rich Olive Mill Wastewater Extract Protects Brain Cells in Vitro and ex Vivo. In: Journal of Agricultural and Food Chemistry. 55, 2007, p. 5043, doi : 10.1021 / jf0703710 .
  20. ↑ F. Visioli, G. Bellomo, G. Montedoro, C. Galli: Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. In: Atherosclerosis. Volume 117, Number 1, 1995, pp. 25-32, PMID 8546752 .
  21. ↑ SJ Rietjens, A. Bast, J. de Vente, GR Haenen: The olive oil antioxidant hydroxytyrosol Efficiently protects against the oxidative stress-induced impairment of the NObullet response of isolated rat aorta. In: American Journal of Physiology. Heart and Circulatory Physiology. Volume 292, Number 4, 2007, pp. H1931 – H1936, doi : 10.1152 / ajpheart.00755.2006 , PMID 17172277 .
  22. ^ S. Cicerale, L. Lucas, R. Keast: Biological activities of phenolic compounds present in virgin olive oil. In: International journal of molecular sciences. Volume 11, number 2, February 2010, pp. 458-479, doi : 10.3390 / ijms11020458 , PMID 20386648 , PMC 2852848 (free full text) (review).
  23. ^ MI Covas, R. de la Torre, M. Fitó: Virgin olive oil: a key food for cardiovascular risk protection. In: The British Journal of Nutrition . Volume 113 Suppl. 2, 2015, pp. S19-S28, doi : 10.1017 / S0007114515000136 , PMID 26148918 (review).