Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides

References

• Visioli F, Galli C. Olive oil phenols and their potential effects on human health. J Agric Food Chem. 1998;46:4292–4296.
   Web of Science ®Google Scholar
• Salami M, Galli C, De Angelis L, et al Formation of F2-isoprostanes in oxidized low density lipoprotein: inhibitory effect of hydroxytyrosol. Phamacol Res. 1995;31:275–279.
   PubMed Web of Science ®Google Scholar
• Petroni A, Blasevich M, Salami M, et al Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. Thromb Res. 1995;78:151–160.
   PubMed Web of Science ®Google Scholar
• Manna C, Galletti P, Cucciolla V, et al The protective effect of the olive oil polyphenol (3,4-dihydroxyphenyl)ethanol counteracts reactive oxygen metabolite-induced cytotoxicity in Caco-2 cells. J Nutr. 1997;127:286–292.
   PubMed Web of Science ®Google Scholar
• Kohyama N, Nagata T, Fujimoto S, et al Inhibition of arachidonate lipoxygenase activities by 2-(3,4-dihydroxyphenyl)ethanol, a phenolic compound from olives. Biosci Biotechnol Biochem. 1997;61:347–350.
   PubMed Web of Science ®Google Scholar
• Aruoma OI, Deiana M, Jenner A, et al Effect of hydroxytyrosol found in extra virgin olive oil on oxidative DNA damage and on low-density lipoprotein oxidation. J Agric Food Chem. 1998;46:5181–5187.
   Web of Science ®Google Scholar
• Manna C, Galletti P, Cucciolla V, et al Olive oil hydroxytyrosol protects human erythrocytes against oxidative damages. J Nutr Biochem. 1999;10:159–165.
   PubMed Web of Science ®Google Scholar
• Visioli F, Galli C, Plasmati E, et al Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress. Circulation. 2000;102:2169–2171.
   PubMed Web of Science ®Google Scholar
• Ragione FD, Cucciolla V, Borriello A, et al Hydroxytyrosol, a natural molecule occurring in olive oil, induces cytochrome c-dependent apoptosis. Biochem Biophys Res Commun. 2000;278:733–739.
   PubMed Web of Science ®Google Scholar
• Fabiani R, De Bartolomeo A, Rosignoli P, et al Cancer chemoprevention by hydroxytyrosol isolated from virgin olive oil through G1 cell cycle arrest and apoptosis. Eur J Cancer Prev. 2002;11:351–358.
   PubMed Web of Science ®Google Scholar
• Palmerini CA, Carlini E, Saccardi C, et al Activity of olive oil phenols on lymphomonocyte cytosolic calcium. J Nutr Biochem. 2005;16:109–113.
   PubMed Web of Science ®Google Scholar
• Schaffer S, Podstawa M, Visioli F, et al Hydroxytyrosol-rich olive mill wastewater extract protects brain cells in vitro and ex vivo. J Agric Food Chem. 2007;55:5043–5049.
   PubMed Web of Science ®Google Scholar
• Fabiani R, De Bartolomeo A, Rosignoli P, et al Virgin olive oil phenols inhibits proliferation of human promyelocytic leukemia cells (HL60) by inducing apoptosis and differentiation. J Nutr. 2006;136:614–619.
   PubMed Web of Science ®Google Scholar
• Guichard C, Pedruzzi E, Fay M, et al Dihydroxyphenylethanol induces apoptosis by activating serine/threonine protein phosphatase PP2A and promotes the endoplasmic reticulum stress response in human colon carcinoma cells. Carcinogenesis. 2006;27:1812–1827.
   PubMed Web of Science ®Google Scholar
• Takeda Y, Bui VN, Iwasaki K, et al. Influence of olive-derived hydroxytyrosol on the toll-like receptor 4-dependent inflammatory response of mouse peritoneal macrophages. Biochem Biophys Res Commun. 2014;446:1225–1230.
   PubMed Web of Science ®Google Scholar
• Funakoshi-Tago M, Sakata T, Fujiwara S, et al Hydroxytyrosol butyrate inhibits 6-OHDA-induced apoptosis through activation of the Nrf2/HO-1 axis in SH-SY5Y cells. Eur J Pharmacol. 2018;834:246–256.
   PubMed Web of Science ®Google Scholar
• Niino T, Tago K, Yasuda D, et al A 5-hydroxyoxindole derivative attenuates LPS induced inflammatory responses by activating the p38-Nrf2 signaling axis. Biochem Pharmacol. 2018;155:182–197.
   PubMed Web of Science ®Google Scholar
• Trujillo M, Mateos R, Dollantes de Teran L, et al Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. J Agric Food Chem. 2006;54:3779–3785.
   PubMed Web of Science ®Google Scholar
• Buisman GJH, Ctw VH, Kramer GFH, et al Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants. Biotechnol Lett. 1998;20:131–136.
   Web of Science ®Google Scholar
• Torres de Pinedo A, Peñalver P, Pérez-Victoria I, et al. Synthesis of new phenolic fatty acid esters and their evaluation as lipophilic antioxidants in an oil matrix. Food Chem. 2007;105:657–665.
   Web of Science ®Google Scholar
• Bernini R, Mincione E, Barontini M, et al Convenient synthesis of hydroxytyrosol and its lipophilic derivatives from tyrosol or homovanillyl alcohol. J Agric Food Chem. 2008;56:8897–8904.
   PubMed Web of Science ®Google Scholar
• Zhou D-Y, Sun Y-X SF. Preparation and antioxidant activity of tyrosol and hydroxytyrosol esters. J Funct Foods. 2017;37:66–73.
   Web of Science ®Google Scholar
• Honda T, Kubo S, Masuda T, et al. Synthesis and in vivo influenza virus-inhibitory effect of ester prodrug of 4-guanidino-7-O-methyl-Neu5Ac2en. Bioorg Med Chem Lett. 2009;19:2938–2940.
   PubMed Web of Science ®Google Scholar
• Nakazawa Y, Pauze M, Fukuyama K, et al Effect of hesperetin derivatives on the development of selenite-induced cataracts in rats. Mol Med Rep. 2018;18:1043–1050.
   PubMed Web of Science ®Google Scholar
• Torres de Pinedo A, Peñalver P, Rondón D, et al. Efficient lipase-catalyzed synthesis of new lipid antioxidants on a catechol structure. Tetrahedron. 2005;61:7654–7660.
   Web of Science ®Google Scholar
• Grasso S, Siracusa L, Spatafora C, et al Hydroxytyrosol lipophilic analogues: enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection. Bioorg Chem. 2007;35:137–152.
   PubMed Web of Science ®Google Scholar
• Capasso R, Cristinzio G, Evidente A, et al Isolation, spectroscopy and selective phytotoxic effects of polyphenols from vegetable waste waters. Phytochemistry. 1992;31:4125–4128.
   Web of Science ®Google Scholar
• DellaGreca M, Previtera L, Temussi F, et al Low-molecular-weight components of olive oil mill waste-waters. Phytochem Anal. 2004;15:184–188.
   PubMed Web of Science ®Google Scholar
• Allouche N, Fki I, Sayadi S. Toward a high yield recovery of antioxidants and purified hydroxytyrosol from olive mill wastewaters. J Agric Food Chem. 2004;52:267–273.
   PubMed Web of Science ®Google Scholar
• Capasso R, Evidente A, Avolio S, et al A Highly convenient synthesis of hydroxytyrosol and its recovery from agricultural waste waters. J Agric Food Chem. 1999;47:1745–1748.
   PubMed Web of Science ®Google Scholar
• Deffieux D, Gossart P, Quideau S. Facile and sustainable synthesis of the natural antioxidant hydroxytyrosol. Tetrahedron Lett. 2014;55:2455–2458.
   Web of Science ®Google Scholar
• Bovicelli P, Antonioletti R, Mancini S, et al Expedient synthesis of hydroxytyrosol and its esters. Synth Commun. 2007;37:4245–4252.
   Web of Science ®Google Scholar
• Bernini R, Mincione E, Crisante F, et al. A novel use of recyclable polymer-supported IBX: an efficient chemoselective and regioselective oxidation of phenolic compounds. The case of hydroxytyrosol derivatives. Tetrahedron Lett. 2009;50:1307–1310.
   Web of Science ®Google Scholar
• Fernández O, Tenllado D, Martín D, et al Immobilized lipases from Candida antarctica for producing tyrosyl oleate in solvent-free medium. Biocat Biotrans. 2012;30:245–254.
   Web of Science ®Google Scholar
• Pezzella A, Lista L, Napolitano A, et al An expedient one-pot entry to catecholestrogens and other catechol compounds via IBX-mediated phenolic oxygenation. Tetrahedron Lett. 2005;46:3541–3544.
   Web of Science ®Google Scholar