Hydroxytyrosol

Hydroxytyrosol
Names
IUPAC name
4-(2-Hydroxyethyl)-1,2-benzenediol
Other names
3-Hydroxytyrosol
3,4-dihydroxyphenylethanol (DOPET)
Dihydroxyphenylethanol
2-(3,4-Di-hydroxyphenyl)-ethanol (DHPE)
3,4-dihydroxyphenolethanol (3,4-DHPEA)[1]
Identifiers
10597-60-1 YesY
ChEBI CHEBI:68889 N
ChEMBL ChEMBL485747 N
ChemSpider 74680 YesY
Jmol 3D model Interactive image
PubChem 82755
Properties
C8H10O3
Molar mass 154.163193 g/mol
Appearance Clear, faint yellow to yellow liquid
Boiling point 174 °C (345 °F; 447 K)
5 g/100 ml (25 °C)
Hazards
Main hazards Causes skin irritation.

Causes serious eye irritation.

May cause respiratory irritation.

Safety data sheet
R-phrases R36/37/38
S-phrases S26, S37/39
Related compounds
Related alcohols
 ethanol, phenol, tyrosol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Hydroxytyrosol is a phenylethanoid, a type of phenolic phytochemical with antioxidant properties in vitro. In nature, hydroxytyrosol is found in olive leaf and olive oil, in the form of its elenolic acid ester oleuropein and, especially after degradation, in its plain form.

Oleuropein, along with oleocanthal, are responsible for the bitter taste of extra virgin olive oil. Hydroxytyrosol itself in pure form is a colorless, odorless liquid. The olives, leaves and olive pulp contain large amounts of hydroxytyrosol (compared to olive oil), most of which can be recovered to produce hydroxytyrosol extracts. However, it was found that black olives, such as common canned variety, containing iron(II) gluconate contained very little of the original hydroxytyrosol, as iron salts are catalysts for its oxidation.[2]

Hydroxytyrosol can also be produced endogenously as it is a product of dopamine oxidative metabolism known as DOPET (3,4-dihydroxyphenylethanol).[3][4]

Effects

In vitro studies

An olive oil fraction containing hydroxytyrosol can inhibit platelet aggregation and eicosanoid (thromboxane B2) formation in vitro.[5] In basic research, hydroxytyrosol had evidence for antimicrobial and antibiotic properties.[6][7]

In preliminary laboratory research, oleuropein had activity as an agonist of the G-protein estrogen receptor.[8]

In vivo studies

Studies have shown that a low dose of hydroxytyrosol reduces the consequences of sidestream smoke-induced oxidative stress in rats.[9]

Ex vivo data provide the first evidence of possible neuroprotective effects of oral hydroxytyrosol intake. Both ex vivo and in vitro studies identified mitochondria as one target for hydroxytyrosol effects in the brain.[10][11]

Metabolism

Hydroxytyrosol undergoes phase II metabolism reactions. The enzymes implicated in these reactions are 5'-diphosphoglucuronosyl transferases (UGTs), sulfotransferases (SULT), and catechol-O-methyltransferase (COMT). The major HT metabolites described in humans are 3- and 4-O-glucuronide conjugates, as well as the corresponding sulfates. A minor metabolic pathway is the COMT-catalyzed conversion of hydroxytyrosol into homovanillyl alcohol.[3]

See also

References

  1. ↑ M. Baldioli, M. Servili, G. Perretti and G. F. Montedoro (1996). "Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil". Journal of the American Oil Chemists' Society 73 (11): 1589–1593. doi:10.1007/BF02523530.
  2. ↑ Vincenzo Marsilio, Cristina Campestre, Barbara Lanza (July 2001). "Phenolic compounds change during California-style ripe olive processing". Food Chemistry 74 (1): 55–60. doi:10.1016/S0308-8146(00)00338-1.
  3. 1 2 Rodríguez-Morató, J.; Xicota, L.; Fitó, M.; Farré, M.; Dierssen, M.; de la Torre, R. (2015). "Potential Role of Olive Oil Phenolic Compounds in the Prevention of Neurodegenerative Diseases". Molecules 20 (3): 4655–80. doi:10.3390/molecules20034655. PMID 25781069.
  4. ↑ Ramirez-Tortose, M. Carmen; Pulido-Moran, Mario; Granados-Principal, Sergio; Gaforio, José J.; Quiles, José L. (2014). Hydroxytyrosol as a Component of the Mediterranean Diet and Its Role in Disease Prevention. London, UK: Elsevier. pp. 205–15. ISBN 978-0-12-407849-9.
  5. ↑ Petroni, A.; Blasevich, M.; Salami, M.; Papini, N.; Montedoro, G. F.; Galli, C. (1995). "Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil". Thrombosis Research 78 (2): 151–60. doi:10.1016/0049-3848(95)00043-7. PMID 7482432.
  6. ↑ Bisignano, G; Tomaino, A; Lo Cascio, R; Crisafi, G; Uccella, N; Saija, A (1999). "On the in-vitro antimicrobial activity of oleuropein and hydroxytyrosol". The Journal of pharmacy and pharmacology 51 (8): 971–4. doi:10.1211/0022357991773258. PMID 10504039.
  7. ↑ Capasso, R; Evidente, A; Schivo, L; Orru, G; Marcialis, M. A.; Cristinzio, G (1995). "Antibacterial polyphenols from olive oil mill waste waters". The Journal of applied bacteriology 79 (4): 393–8. doi:10.1111/j.1365-2672.1995.tb03153.x. PMID 7592132.
  8. ↑ Prossnitz, Eric R.; Barton, Matthias (2014). "Estrogen biology: New insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology 389 (1-2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207.
  9. ↑ Visioli F, Galli C, Plasmati E, et al. (2000). "Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress". Circulation 102 (18): 2169–71. doi:10.1161/01.cir.102.18.2169. PMID 11056087.
  10. ↑ Schaffer S, Podstawa M, Visioli F, et al. (2007). "Hydroxytyrosol-rich olive wastewater extract protects brain cells in vitro and ex vivo". Journal of Agricultural and Food Chemistry 55 (13): 5043–5049. doi:10.1021/jf0703710.
  11. ↑ Schaffer S, Müller WE, Eckert GP (2010). "Cytoprotective effects of olive wastewater extract and its main constitute hydroxytyrosol in PC12 cells". Pharmacol. Res. 62 (4): 322–327. doi:10.1016/j.phrs.2010.06.004. PMID 20600919.
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