644985-85-3Relevant articles and documents
Efficient lipase-catalyzed synthesis of new lipid antioxidants based on a catechol structure
Torres De Pinedo,Pe?alver,Rondón,Morales
, p. 7654 - 7660 (2005)
Lipid antioxidants phenolic saturated fatty acid esters were synthesized in high yields and short reaction times using the corresponding ethyl fatty acid esters, lipase from Candida Antarctica, vacuum and no solvent. Phenolic esters with mono- and polyunsaturated fatty acids (EPA and DHA) were also prepared.
Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides
Sakakura, Ayaka,Pauze, Martin,Namiki, Atsuhiro,Funakoshi-Tago, Megumi,Tamura, Hiroomi,Hanaya, Kengo,Higashibayashi, Shuhei,Sugai, Takeshi
, p. 185 - 191 (2019/02/05)
Fatty acid monoesters of hydroxytyrosol [2-(3,4-dihydroxyphenyl)ethanol] were synthesized in two steps from tyrosol (4-hydroxyphenylethanol) by successive Candida antarctica lipase B-catalyzed chemoselective acylation on the primary aliphatic hydroxy group over phenolic hydroxy group in tyrosol, and 2-iodoxybenzoic acid (IBX)-mediated hydroxylation adjacent to the remaining free phenolic hydroxy group. Examination of their suppression effects on nitric oxide production stimulated by lipopolysaccharides in RAW264.7 cells showed that hydroxytyrosol butyrate exhibited the highest inhibition (IC50 7.0 μM) among the tested compounds.
Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses
Botta, Giorgia,Bizzarri, Bruno Mattia,Garozzo, Adriana,Timpanaro, Rossella,Bisignano, Benedetta,Amatore, Donatella,Palamara, Anna Teresa,Nencioni, Lucia,Saladino, Raffaele
, p. 5345 - 5351 (2015/11/11)
Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.
Lipophilic hydroxytyrosol esters: Fatty acid conjugates for potential topical administration
Procopio, Antonio,Celia, Christian,Nardi, Monica,Oliverio, Manuela,Paolino, Donatella,Sindona, Giovanni
, p. 2377 - 2381 (2012/01/15)
Hydroxytyrosol is a potent antioxidant natural molecule isolated from olive leaves and fruits. The presence of three hydroxy groups in its structure poses a limit for the topical application of this lead compound. A set of hydroxytyrosol conjugates with fatty acids at different molecular weights were synthesized under mild conditions. The topical delivery features of this new set of antioxidant molecules were evaluated as a function of their permeation profiles through the human stratum corneum and viable epidermis membranes. A dependence on their partition coefficients, their molecular weights, and their isometric configurations was then postulated. Encouraging results prompt further investigations on the polyfunctional role that hydroxytyrosol conjugates could have as agents in both anti-inflammatory and antioxidant therapies.
