235
Views
9
CrossRef citations to date
0
Altmetric
Research Article

Enzymatic synthesis of tyrosol and hydroxytyrosol β-d-fructofuranosides

, &
Pages 18-24 | Received 18 Aug 2017, Accepted 26 Dec 2017, Published online: 05 Jan 2018

References

  • Anter J, Tasset I, Demyda-Peyras S, Ranchal I, Moreno-Millan M, Romero-Jimenez M, Muntane J, Luque de Castro MD, Munoz-Serrano A, Alonso-Moraga A. 2014. Evaluation of potential antigenotoxic, cytotoxic and proapoptotic effects of the olive oil by-product “alperujo” hydroxytyrosol, tyrosol and verbascoside. Mutat Res Genet Toxicol Environ Mutagen 772:25–33.
  • Bernini R, Merendino N, Romani A, Velotti F. 2013. Naturally occurring hydroxytyrosol: synthesis and anticancer potential. Curr Med Chem 20:655–670.
  • Bi Y, Wang Z, Mao Y, Zheng S, Zhang H, Shi H. 2012. Ionic liquid effects on the activity of β-glycosidase for the synthesis of salidroside in co-solvent systems. Chin J Catal 33:1161–1165.
  • Deng Y, Wang Q, Liu X, Wang Y, Ding Z. 2011. Dose-dependent pharmacokinetics of tyrosol galactoside as an anti-fatigue drug in rats. Arzneimittelforschung 61:435–438.
  • Dudíková J, Mastihubová M, Mastihuba V, Kolarova N. 2007. Exploration of transfructosylation activity in cell walls from Cryptococcus laurentii for production of functionalised β-d-fructofuranosides. J Mol Catal B Enzym 45:27–33.
  • Galano A, Alvarez-Idaboy JR, Francisco-Márquez M, Medina ME. 2012. A quantum chemical study on the free radical scavenging activity of tyrosol and hydroxytyrosol. Theor Chem Acc 131:1173–1184.
  • Griffith BR, Langenhan JM, Thorson JS. 2005. ‘Sweetening’ natural products via glycorandomization. Curr Opin Biotechnol 16:622–630.
  • Guan S, Feng H, Song B, Guo W, Xiong Y, Huang G, Zhong W, Huo M, Chen N, Lu J, Deng X. 2011. Salidroside attenuates LPS-induced pro-inflammatory cytokine responses and improves survival in murine endotoxemia. Int Immunopharmacol 11:2194–2199.
  • Han T. 2013. Effects of salidroside pretreatment on expression of tumor necrosis factor-alpha and permeability of blood–brain barrier in rat model of focal cerebralischemia-reperfusion injury. Asian Pac J Trop Med 6:156–158.
  • Khymenets O, Joglar J, Clapés P, Parella T, Covas MI, de la Torre R. 2006. Biocatalyzed synthesis and structural characterization of monoglucuronides of hydroxytyrosol, tyrosol, homovanillic alcohol, and 3-(4’-hydroxyphenyl)propanol. Adv Synth Catal 348:2155–2162.
  • Li HB, Ge Y, Zheng XX, Zhang L. 2008. Salidroside stimulated glucose uptake in skeletal muscle cells by activating AMP-activated protein kinase. Eur J Pharmacol 588:165–169.
  • Liang XQ, Xie P, Zhang Y, Shi T, Wang QJ, Yan TH. 2010. Effects of salidroside on myocardial ischemia/reperfusion injury in rats. Chin J Nat Med 8:127–131.
  • Potocká E, Mastihubová M, Mastihuba V. 2015. Enzymatic synthesis of tyrosol glycosides. J Mol Catal B Enzym 113:23–28.
  • Qi T, Gu G, Xu L, Xiao M, Lu L. 2017. Efficient synthesis of tyrosol galactosides by the β-galactosidase from Enterobacter cloacae B5. Appl Microbiol Biotechnol 101:4995–5003.
  • Shi T, Chen H, Jing L, Liu X, Sun X, Jiang R. 2011. Development of a kilogram-scale synthesis of salidroside and its analogues. Synth Commun 41:2594–2600.
  • Shi T, Feng S, Xing J, Wu Y, Li X, Zhang N, Tian Z, Liu S, Zhao M. 2012. Neuroprotective effects of salidroside and its analogue tyrosol galactoside against focal cerebral ischemia in vivo and H2O2-induced neurotoxicity in vitro. Neurotox Res 21:358–367.
  • Smrtičová H, Čanigová M, Mastihubová M, Mastihuba V. 2011. Enzymatic preparation of melibiose and alkyl β-d-fructofuranosides by commercial lactase. J Mol Catal B Enzym 72:53–56.
  • Sun C, Wang Z, Zheng Q, Zhang H. 2012. Salidroside inhibits migration and invasion of human fibrosarcoma HT1080 cells. Phytomedicine 19:355–363.
  • Trincone A, Pagnotta E, Tramice A. 2012. Enzymatic routes for the production of mono- and di-glucosylated derivatives of hydroxytyrosol. Bioresour Technol 115:79–83.
  • Wang H, Ding Y, Zhou J, Sun X, Wang S. 2009. The in vitro and in vivo antiviral effects of salidroside from Rhodiola rosea L. against coxsackievirus B3. Phytomedicine 16:146–155.
  • Wu YL, Lian LH, Jiang YZ, Nan JX. 2009. Hepatoprotective effects of salidroside on fulminant hepatic failure induced by d-galactosamine and lipopolysaccharide in mice. J Pharm Pharmacol 61:1375–1382.
  • Yu HL, Xu JH, Lu WY, Lin GQ. 2007. Identification, purification and characterization of β-glucosidase from apple seed as a novel catalyst for synthesis of O-glucosides. Enzyme Microb Technol 40:354–361.
  • Yu HL, Xu JH, Lu WY, Lin GQ. 2008. Environmentally benign synthesis of natural glycosides using apple seed meal as green and robust biocatalyst. J Biotechnol 133:469–477.
  • Yuan Y, Wu SJ, Liu X, Zhang LL. 2013. Antioxidant effect of salidroside and its protective effect against furan-induced hepatocyte damage in mice. Food Funct 4:763–769.
  • Zhang J, Liu A, Hou R, Zhang J, Jia X, Jiang W, Chen J. 2009. Salidroside protects cardiomyocyte against hypoxia-induced death: a HIF-1alpha-activated and VEGF-mediated pathway. Eur J Pharmacol 607:6–14.
  • Zhang Z, Xiao B, Chen Q, Lian X-Y. 2010. Synthesis and biological evaluation of caffeic acid 3,4-dihydroxyphenethyl ester. J Nat Prod 73:252–254.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.